RU2363699C2 - New aminopyridin derivative with inhibition activity in relation to syk - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: present invention refers to the aminopyridin compound of general formula (I)

or its salt wherein X¹, X², X³, Z, Y¹, Y² are carbon or nitrogen atom, R, R¹, R⁵, R⁶ are hydrogen atom, alkyl group, further see formula of the invention, and R⁷ is hydrogen or halogen atom, nitro or cyano group, -C_pH_2(p-1)(R^a1)(R^a2)-O-R^a3, -C(=O)-R^d1, 5-or 6-membered saturated heterocycle group, aromatic heterocycle group, -N(R^h1)(R^h2), further see formula of the invention. The invention refers also to the pharmaceutic composition thereof intended for treatment or prevention of allergic diseases, autoimmune diseases caused by malignant tumour, to the Syk inhibitor containing the compound of formula I and to the therapeutic and/or preventive agent.

EFFECT: compounds which not only possess high Syk inhibition activity but are selective Syk inhibitors are obtained and described.

24 cl, 24 ex, 2 tbl

Description

The present invention relates to a new derivative of aminopyridine having an inhibitory effect against Syk (spleen tyrosine kinase), and to a therapeutic agent for treating allergic diseases containing this compound as an active ingredient.

1. What is an allergic disease, such as bronchial asthma

An allergic reaction of the 1st type (immediate type), which plays a central role in allergic diseases such as bronchial asthma, allergic rhinitis, atopic dermatitis, is known to be triggered by the interaction of an exogenous antigen such as plant pollen or house dust and immunoglobulin E ( IgE) specific to it. The allergen that enters the body appears to helper T cells (Th cells) as class II HLA molecules and a peptide fragment by antigen presenting cells such as macrophages; Th cells are activated by antigenic stimulation through T cell receptors and produce cytokines such as interleukin-4. Thus, the production of a specific IgE antibody to the allergen by B cells is enhanced.

There are receptors that bind to a synthesized IgE antibody with high affinity on the surface of cells such as mast cells, basophils, monocytes; they are designated as high affinity IgE receptors (FcεRI). When the IgE associated with FcεRI cross-binds to a polyvalent antigen, it is activated and various types of mediators are released. In other words, it is assumed that signaling from FcεRI to the cell triggers an allergic disease such as bronchial asthma.

Among the mediators that release mast cells, there are pre-synthesized mediators, such as histamine, which are released from cells by degranulation, and mediators that are produced and released at an early stage of activation, such as arachidonic acid metabolites. When they affect the bronchi, the smooth muscles of the bronchi contract and the airways narrow due to swelling of the mucosa, secretion of mucus, etc., which leads to an asthmatic attack. When they affect the skin, inflammation, swelling and itching appear, which leads to the development of urticaria. When they act on the nasal mucosa, vascular permeability increases, blood fills and the nasal mucosa swells, which causes nasal congestion, which leads to allergic rhinitis, which causes sneezing and the release of large amounts of mucus caused by nervous stimulation. When such a reaction occurs in the digestive tract, the smooth muscles of the intestines contract and intestinal motility (peristalsis) is pathologically enhanced, leading to gastrointestinal allergies such as abdominal pain, vomiting, and diarrhea.

Among the mediators that release mast cells, there is also an eosinophilic chemotactic factor and cytokines, which are accompanied by transcription and are released due to protein synthesis with some delay. This is believed to be the cause of chronic inflammation (Non-Patent Document 1; Enshou-to-Men'eki (Inflammation and Immunity) vol. 7, No. 2, 1999, pp. 165-171). Activated by the eosinophilic chemotactic factor and mast cell cytokines, eosinophil, which has powerful toxic chemicals, is sent to the site of an allergic reaction and releases chemicals, causing tissue damage. If this reaction occurs in the bronchi, the mucosal epithelium is desquamated, facilitating the penetration of antigen, and the allergic reaction continues. As a result, asthma becomes refractory, while hyperresponsiveness of the airways increases, the airways become already due to swelling and mucus, breathing is difficult, etc. The pathological condition varies from manifestations in the form of chronic cough and sputum to a serious condition with severe, fatal seizures. The number of such patients is growing steadily, up to the present and is expected to continue to grow in the future; the development of effective pharmaceuticals is highly desirable.

2. Existing anti-asthma drugs

Currently, asthma inhalation steroid preparations are widely used as anti-inflammatory drugs, β-stimulants, such as prokaterol, and xanthine derivatives, such as aminophylline and theophylline, as bronchodilators. Inhaled steroids have a wide anti-inflammatory effect, their use as a therapeutic agent in asthma is widespread, but there is a need to learn the correct method of inhalation, as well as the existence of asthma patients resistant to steroid drugs (non-patent document 2; ASTHMA 13-1, 69-73 (2000), Non-Patent Document 3; Naika (Internal medicine) 81, 485-490 (1998)). Bronchodilators activate adenylate cyclase, an enzyme that synthesizes intracellular 3'5'-cyclic adenosine monophosphate (cAMP) or inhibits phosphodiesterase (PDE), an enzyme that breaks down cAMP in the smooth muscles of the respiratory tract, thereby increasing cAMP levels in cells and weakening smooth contraction respiratory tract muscles (Non-Patent Document 4; Naika (Internal medicine) 69, 207-214 (1992)). An increase in intracellular cAMP is known to inhibit the contraction of smooth muscle in the airways (non-patent document 5; Clin. Exp. Allergy, 22, 337-344 (1992), non-patent document 6; Drugs of the Future, 17, 799-807 (1992 )) and this is effective for improving asthma. However, xanthine derivatives are known to have systemic side effects, such as lowering blood pressure and cardiotonic effects (non-patent document 7; J. Cyclic Nucleotide and Protein Phosphorylation Res., 10, 551-564 (1985), non-patent document 8; J. Pharmacol. Exp. Ther., 257, 741-747 (1991)), and β-stimulants easily cause desensitization, while their increasing doses cause side effects such as trembling fingers and a heartbeat. Thus, the development of an effective therapeutic agent for the treatment of asthma, devoid of such side effects, is highly desirable.

3. Definition of Syk

FcεRI is a basic structure common with other immunoglobulin receptors (T-cell receptor, B-cell IgM receptor), and belongs to the superfamily, which is denoted by multi-chain immune recognition receptors. FcεRI has a heterotetrameric structure (αβγ ₂ ), consisting respectively of one α-chain, one β-chain and two γ-chains connected non-covalently in the transmembrane region. The FcεRI α-chain has two domains homologous to immunoglobulin (Ig) in the extracellular domain, and a domain homologous to immunoglobulin (Ig) of the C-terminal region binds IgE with high affinity (non-patent document 9; EJ Biol. Chem. 266, 1991, pp. 2639-2646). Its intracellular domain, however, is relatively short, and even if the intracellular domain of the C-terminus of the α-chain is cleaved, this will not cause changes in signal transmission. On the other hand, the extracellular domain of the γ chain is short, almost located in the cell, forming a homodimer due to SS bonds. Cleavage of the intracellular domain of γ-chains leads to interruption of signal transmission, thus γ-chains are involved in intracellular signal transmission. The β-chain has a 4-transmembrane structure, and both terminal regions, the N-terminal and C-terminal, are in the cell. The β-chain has the effect of amplification of signal transmission, while intracellular signal transmission is significantly weakened if the β-chain is removed. The β-chain and γ-chain do not have internal enzymatic activity, respectively, there is a domain with a specific peptide sequence (tyrosine-based immunoreceptor activating fragment - ITAM or ARAM antigen-receptor-activating fragment) based on two tyrosine residues in the intracellular domain. When they undergo tyrosine phosphorylation, they bind the non-receptor type protein tyrosine kinase (protein tyrosine kinase - PTK) SH domain (domain homologous to Srk) with high affinity.

When proteins are tyrosine phosphorylated by aggregation of FcεRI, non-receptor type PTKs such as Lyn, Syk and Btk, an adapter molecule such as Shc and Grb2, PI3K, etc. identified along with the β-chain FcεRI and γ-chain FcεRI.

Syk is a molecule belonging to the subfamily designated as the Syk family, along with ZAP-70, which is PTK, important in signaling via the T-cell receptor. It is not permanently linked to the FcεRI γ-chain, but is tightly bound to the ITAM γ-chain sequence, being tyrosine phosphorylated by Lyn after aggregation of FcεRI via its own SH2 domain. It is known that Syk undergoes autophosphorylation and phosphorylation by the Lyn enzyme upon binding to it, then Syk causes further allosteric structural changes that enhance its activity (Non-Patent Document 10; J. Biol. Chem. Vol. 270. pp.10498-10502, 1995) . Activated Syk induces adapter molecular complex formation and enzyme activation and transmits a signal in the usual way, such as phospholipase Cγ (PLC γ), MAP kinase (MAPK), which is used by many receptors.

Γ PLC tyrosine phosphorylates via Syk and phosphatidylinositol-4,5-diphosphate (PI-4,5-P ₂ ) is hydrolyzed to diacylglycerol (DAG) and inositol-1,4,5-triphosphate (IP ₃ ). DAG induces activation of protein kinase C (PKC), and activation of PKC induces degranulation in combination with an increase in intracellular calcium. In addition, Syk is associated with various adapter molecules that do not have kinase activity and contain only the SH2 domain, and activates the MAPK superfamily, and arachidonic acid metabolism is caused by phosphorylation of PLA ₂ . Activation of ERK, p38, JNK, etc. participates in the production of cytokines by mast cells through transcription factors such as AP1 (Non-Patent Document 11; J. Biol. Chem. Vol. 270, pp. 16333-16338, 1995).

Tyrosine phosphorylation of intracellular proteins and the reaction of phagocytosis, which are caused by stimulation of the receptor for immunoglobulin G (IgG) (FcγR), are reported to be significantly limited in macrophages obtained from Syk-deficient mice (non-patent document 12; Crowley, MT et al., J. Exp Med. 186: 1027-1039 (1997)). Thus, Syk plays an extremely important role in macrophage phagocytosis mediated through FcγR, while demonstrating its involvement in tissue damage caused by antibody-dependent cellular cytotoxicity (ADCC). Moreover, Syk is involved in B cell activation (e.g., Non-Patent Document 13; J. Biol. Chem., 1992, Vol.267, pp. 8613-8619 and Non-Patent Document 14; EMBO J., 1994, Vol.13, pp.1341-1349), in the survival of eosinophils induced by GM-CSF / IL-5 (e.g., non-patent document 15; J. Exp. Med., 1996, Vol.183, pp.1407-1414), in platelet activation, caused by stimulation of collagen (e.g., non-patent document 16; EMBO J., 1997, Vol.16, pp. 2333-2341).

Accordingly, a Syk inhibitor is expected to be useful as a therapeutic drug for the treatment of diseases that have arisen from immediate allergic reactions and delayed inflammatory reactions (e.g., bronchial asthma, allergic rhinitis, contact dermatitis, urticaria, food allergy, conjunctivitis and etc.), and diseases in which platelet activation is involved. In particular, it is believed to be very useful if it acts specifically against Syk without inhibiting Zap-70, which belongs to the same family and is expressed only in T cells.

4. Existing Syk Inhibitors

(1) A new compound is reported to be used as a pharmaceutical component having inhibitory activity against protein tyrosine kinases, especially tyrosine kinases of the Syk family, which is an imidazo [1,2-c] pyrimidine derivative and is represented by the following formula (Patent Document 1; Japanese Patent Laid-Open No. 2004-203748).

where R ¹ and R ² are hydrogen, lower alkyl, phenyl, which may be substituted, or heteroaryl, R ³ is hydrogen, lower alkyl, cycloalkyl, phenyl, which may be substituted, heteroaryl or aralkyl, and A is hydrogen lower alkyl, cycloalkyl, R ⁴ , heteroaryl, OR ⁵ , SR ⁵ or NR ⁶ R ⁷ .

(2) Abignente E. et al. discloses imidazo [1,2-c] pyrimidine derivatives having an anti-inflammatory effect, represented by the following general formula:

where R ^A represents carboxy, ethoxycarbonyl, carbamoyl or carboxymethyl; R ^B represents methyl or methoxy; and R ^C is methoxy and methyl or chlorine (e.g., Non-Patent Document 17; IL Farmaco, 1991, Vol. 46, pp. 1099-1110).

(3) In addition, Yura T. et al. discloses imidazo [1,2-c] pyrimidine derivatives useful as a Syk inhibitor represented by the following general formula:

where R ^D represents hydrogen, alkyl, carboxy, alkylcarbonyl or carbamoyl; R ^E represents —X ^A —R ^G , heterocyclyl, carbocyclyl or a fused ring; X ^A represents S, O or NH; R ^G represents aryl or heteroaryl; and R ^F is aryl or heteroaryl (See, for example, Patent Document 2; WO01 / 83485).

(4) As a compound having a Syk inhibitory effect, 2-anilinopyrimidine derivatives are described, represented by the following formula:

where Ar represents an aromatic ring group that may be substituted, and R ² represents H, halogen or a group represented by —X ¹ —R ^2a, respectively (See, for example, Patent Document 3; WO98 / 18782).

In addition, Pisiatannol has been reported, which is a natural product isolated from a plant (Non-Patent Document 18; J. Biol. Chem. 269: 29697-29703 (1994)).

(5) As a compound having a Syk inhibitory effect, a compound of the following formula is provided (see Patent Document 4; WO02096905A1). The compound provided herein, however, exhibits an inhibitory effect against multiple protein kinases and has an inhibitory effect against GSK3 and Aurora2 at the same level as with Syk.

(6) In addition, a compound represented by the following formula is also reported (Patent Document 5; WO2004016597A2).

(7) In addition, thiazole derivatives represented by the following formula have also been reported (Patent Document 6; WO2004087698A2).

(8) In addition, a compound represented by the following formula is also reported as a thiazole derivative (Patent Document 7; WO2004087699A2).

As stated above, to date, numerous Syk inhibitors have been reported, but these compounds have mainly a pyrimidine skeleton and, in addition, exhibit an inhibitory effect against numerous protein kinases and do not have high Syk specificity.

Each of the compounds presented above, from (1) to (8), inhibits not only Syk, but also ZAP-70 expression in T cells at the same level, and has poor selectivity.

5. Relatively known aminopyridine compounds

(1) A compound represented by the following formula is also reported (patent document 8; WO2004041810A1). However, the compound provided herein exhibiting inhibitory activity against numerous protein kinases, including Jak and selectivity for Syk, never has a satisfactory level.

(2) In addition, a diaminopyrimidine derivative is reported as a PKC-theta inhibitor represented by the following formula (Patent Document 9; WO2004067516A1).

(3) In addition, 2-substituted-4-heteroarylpyrimidine derivatives, as shown below, are known as cyclin-dependent kinase (CDK) inhibitors (Patent Document 10; Japanese Patent Laid-Open No. 2003-528872).

In the formula, X ¹ represents CH, X ² represents S; or one of X ¹ and X ² represents S, the other X ¹ and X ² represent N; Z represents NH, NHCO, NHSO ₂ , NHCH ₂ , CH ₂ , CH ₂ CH ₂ or CH = CH; R ¹ , R ² and R ³ independently represent H, alkyl, aryl, aralkyl, heterocycle, halogen, NO ₂ , CN, OH, alkoxy, aryloxy, NH ₂ , NH-R ', N- (R') (R ''), NH-COR ', NH-aryl, N- (aryl) ₂ , COOH, COO-R', COO-aryl, CONH ₂ , CONH-R ', CON- (R') (R '') , CONH-aryl, CON- (aryl) ₂ , SO ₃ H, SO ₂ NH ₂ , CF ₃ , CO-R ′ or CO-aryl, where the alkyl group, aryl group, aralkyl group, heterocyclic group and NH-aryl group may be substituted by one or more groups selected from halogen, NO ₂ , CN, OH, O-methyl, NH ₂ , COOH, CONH ₂ and CF ₃ ; at least one of the groups R ¹ and R ^{2 is} not H when X ¹ or X ² are S; R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ independently represent H, substituted or unsubstituted lower alkyl, halogen, NO ₂ , CN, OH, substituted or unsubstituted alkoxy, NH ₂ , NH-R ', alkylaryl, alkylheteroaryl, NH (C = NH) NH ₂ , N (R ') ₃ ⁺ , N- (R') (R ''), COOH, COO-R ', CONH ₂ , CONH-R', CON- (R ') (R''), SO ₃ H, SO ₂ NH ₂ , CF ₃ or (CH ₂ ) _n O (CH ₂ ) _m NR'R'', (CH ₂ ) _n CO ₂ (CH ₂ ) _m OR ''', where n is 0, 1, 2 or 3, m is 1, 2 or 3; and R ′, R ″ and R ″ ″ each independently represents an alkyl group, which may be the same or different.

[Patent Document 1] Japanese Patent Laid-Open No. 2004-203748

[patent document 2] WO01 / 83485

[patent document 3] WO98 / 18782

[patent document 4] WO02096905A1

[patent document 5] WO2004016597A2

[patent document 6] WO2004087698A2

[patent document 7] WO2004087699A2

[patent document 8] WO2004041810A1

[patent document 9] WO2004067516A1

[Patent Document 10] Japanese Patent Laid-Open No. 2003-528872

[non-patent document 1] Enshou-to-Men'eki (Inflammation and Immunity) vol. 7, No. 2, 1999, pp. 165-171

[Non-Patent Document 2] ASTHMA 13-1, 69-73 (2000)

[non-patent document 3] Naika (Internal medicine) 81, 485-490 (1998)

[non-patent document 4] Naika (Internal medicine) 69, 207-214 (1992)

[Non-Patent Document 5] Clin. Exp. Allergy, 22, 337-344 (1992)

[Non-Patent Document 6] Drugs of Future, 17, 799-807 (1992)

[Non-patent document 7] J. Cyclic Nucleotide and Protein Phosphorylation Res., 10, 551-564 (1985)

[Non-Patent Document 8] J. Pharmacol. Exp. Ther., 257, 741-747 (1991)

[Non-Patent Document 9] E. J. Biol. Chem. 266, pp. 2639-2646, 1991

[Non-Patent Document 10] J. Biol. Chem. Vol.270, pp. 10498-10502, 1995

[Non-Patent Document 11] J. Biol. Chem. Vol.270, pp. 16333-16338, 1995

[non-patent document 12] Crowley, M.T. et al., J. Exp. Med. 186: 1027-1039 (1997)

[Non-Patent Document 13] J. Biol. Chem., 1992, Vol. 267, pp. 8613-8619

[non-patent document 14] EMBO J., 1994, Vol.13, p.1341-1349

[Non-Patent Document 15] J. Exp. Med., 1996, Vol. 183, pp. 1407-1414

[Non-Patent Document 16] EMBO J., 1997, Vol.16, pp. 2333-2341

[Non-Patent Document 17] IL Farmaco, 1991, Vol. 46, pp. 1099-1110

[Non-Patent Document 18] J. Biol. Chem. 269: 29697-29703 (1994)

SUMMARY OF THE INVENTION

Tasks Solved by the Invention

The previously reported Syk inhibitors have low selectivity and show an inhibitory effect against multiple protein kinases, and therefore they are capable of inducing immune suppression of activity in addition to controlling the inflammatory response. In this regard, it is necessary to develop pharmaceutical preparations having not only a high inhibitory effect against Syk, but also high selectivity for Syk.

Accordingly, an object of the present invention, which should be provided, is a new compound that has a very high inhibitory activity against Syk.

Another object of the present invention, which should be provided, is a pharmaceutical composition containing such a compound as an active ingredient, more specifically, a Syk inhibitor, a drug against allergic diseases, a drug against bronchial asthma, a drug against allergic rhinitis, a drug against allergic dermatitis , drug against autoimmune diseases, medicine against rheumatoid arthritis, lek natural anti-systemic lupus erythematosus, anti-multiple sclerosis drug, anti-cancer drug, anti-B-lymphoma drug, B-lymphocytic leukemia and their pharmaceutical composition, for use in combination with other anti-allergic therapeutic drugs.

Problem Solving Tools

Intensive studies have been conducted of compounds that selectively inhibit Syk, and as a result, it was found that the new aminopyridine derivative represented by the following general formula (I) has a specific and excellent inhibitory effect against Syk and is useful as a therapeutic or prophylactic agent for treating diseases such like allergies in which Syk is involved. This conclusion led to the completion of the present invention.

Specifically, the present invention is as follows.

1. The aminopyridine compound represented by the following general formula (I):

where X ¹ represents

(1) —C (R ² ) = or

(2) a nitrogen atom;

X ² represents

(1) —C (R ² ) = or

(2) a nitrogen atom;

X ³ represents

(1) —C (R ⁴ ) = or

(2) a nitrogen atom;

Z represents

(1) a nitrogen atom or

(2) -C (R ⁶ ') =;

Y ¹ represents

(1) -CH = or

(2) a nitrogen atom;

Y ² represents

(1) -CH = or

(2) a nitrogen atom;

R represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group or

(3) an acyl group;

R ¹ represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group or

(3) a halogen atom;

R ² represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group or

(3) a halogen atom;

R ³ represents

(1) a hydrogen atom,

(2) a halogen atom,

(3) -N (R ³¹ ) (R ³² ),

where R ³¹ and R ³² represent a hydrogen atom or a C _1-6 alkyl group,

(4) a hydroxyl group,

(5) a C _1-6 alkoxy group, wherein a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a substituent selected from the following Aa group:

[Group Aa]

but. hydroxyl group

b. C _1-6 alkoxy group,

c. -N (R ³¹ ) (R ³² ),

where R ³¹ and R ³² have the meanings indicated above,

d. -COOR ³³ ,

where R ³³ represents a hydrogen atom or a C _1-6 alkyl group,

e. -CO-N (R ³¹ ) (R ³² ),

where R ³¹ and R ³² have the meanings indicated above, and

f. halogen atom

(6) an aralkoxy group,

(7) an acyl group,

(8) a saturated heterocyclic group or an aromatic heterocyclic group, wherein the heterocyclic group may be substituted with a C _1-6 alkyl group and the saturated heterocyclic group may partially have a double bond,

(9) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from the following Ab group:

[group Ab]

but. hydroxyl group

b. -COOR ³³ , where R ³³ has the meaning indicated above,

c. —CO — N (R ³¹ ) (R ³² ), wherein R ³¹ and R ³² are as defined above, and

d. halogen atom

(10) -COOR ³³ ,

where R ³³ has the meaning indicated above,

(11) -CO-N (R ³¹ ) (R ³² ), where R ³¹ and R ³² are as defined above, or

(12) a cyano group, or

R ³ together with R ² can form a group —C = CC = C—;

R ⁴ represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group or

(3) a nitro group;

R ⁵ represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group or a C _1-6 alkoxy group,

(3) -COOR ⁵¹ ,

where R ⁵¹ represents a hydrogen atom or a C _1-6 alkyl group, or

(4) a nitro group;

R ⁶ and R ^{6 '} may be the same or different and each represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group or a C _1-6 alkoxy group,

(3) -COOR ⁶¹ ,

where R ⁶¹ represents a hydrogen atom or a C _1-6 alkyl group,

(4) -N (R ⁶² ) (R ⁶³ ),

where R ⁶² and R ⁶³ may be the same or different and each represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy group or an acyl group,

(5) -CO-N (R ⁶² ) (R ⁶³ ),

where R ⁶² and R ⁶³ have the meanings indicated above, or

(6) an acyl group;

R ⁷ represents a hydrogen atom, a halogen atom, a nitro group, a cyano group or the following R ^a , R ^b , R ^c , R ^d , R ^e , R ^f , R ^g or R ^h ;

R ^a is —C _p H _{2 (p-1)} (R ^a1 ) (R ^a2 ) —OR ^a3 ,

Where

(1) p is an integer from 1 to 6,

(2) R ^a1 represents a hydrogen atom or a C _1-6 alkyl group,

(3) R ^a2 represents a hydrogen atom, a C _1-6 alkyl group, an aralkyl group or an aryl group, where the C _1-6 alkyl group, an aralkyl group and an aryl group may be substituted with a substituent respectively selected from the following Ba group:

[Group Ba]

but. hydroxyl group

b. carboxy group

c. C _1-6 alkoxycarbonyl group,

d. amino group

e. C _1-6 alkylamino group,

f. di-C _1-6 alkylamino group,

g. acyloxy group and

h. halogen atom.

(4) R ^a3 represents a hydrogen atom, an acyl group, —CON (R ^a31 ) (R ^a32 ), or

A C _1-6 alkyl group, where the alkyl group may be substituted with a C _1-6 alkoxycarbonyl group or —CON (R ^a31 ) (R ^a32 ),

where R ^a31 and R ^a32 may be the same or different and each represents

Hydrogen atom

Acyl group, where the acyl group may be substituted by a hydroxyl group or a carboxy group,

· A C _1-6 alkyl group (where the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group, a carbamoyl group, a C _1-6 alkylcarbamoyl group and a di C _1-6 alkylcarbamoyl group,

C _1-6 alkoxycarbonyl group or

· C _1-6 alkylsulfonyl group, or

R ^a31 and R ^a32 together with an adjacent nitrogen atom can form a 5- or 6-membered saturated heterocyclic group that has one or more nitrogen atoms, where the saturated heterocyclic group can be substituted by a hydroxyl group, an oxo group, an aralkylamino group or an acylamino group;

R ^b represents —C _p H _{2 (p-1)} (R ^b1 ) (R ^b2 ) -N- (R ^b3 ) (R ^b4 ),

Where

(1) p is an integer from 1 to 6,

(2) R ^b1 represents a hydrogen atom or a C _1-6 alkyl group,

(3) R ^b2 represents

but. hydrogen atom

b. an aralkyl group, wherein the aralkyl group may be substituted by a hydroxyl group, a C _1-6 alkoxy group which may be substituted by a hydroxyl group, an aralkyl group or —N (R ^b21 ) (R ^b22 ),

where R ^b21 and R ^b22 may be the same or different and each represents a hydrogen atom, a C _1-6 alkyl group, an acyl group, a carbonyl group, a C _1-6 alkoxycarbonyl group or an aralkoxycarbonyl group,

c. an aryl group, wherein the aryl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group or an aralkoxy group, or

d. C _1-6 alkyl group, where C _1-6 alkyl group may be substituted with a substituent selected from the following Ca group:

[Group Ca]

Hydroxyl group

Aralkoxy group,

-COOR ^b23 ,

where R ^b23 represents a hydrogen atom, a C _1-6 alkyl group or an aralkyl group,

· -N (R ^b21 ) (R ^b22 ), where R ^b21 and R ^b22 are as defined above, and

An aryl group, where aryl can be substituted with a substituent selected from a hydroxyl group, a C _1-6 alkoxy group, where a C _1-6 alkoxy group can be substituted with a hydroxyl group, an aralkoxy group, —N (R ^b21 ) (R ^b22 ) and an aralkoxycarbonylamino group,

where R ^b21 and R ^b22 have the meanings indicated above, and

(4) R ^b3 and R ^b4 may be the same or different and each represents

but. hydrogen atom

b. C _1-6 alkyl group wherein C _1-6 alkyl group may be substituted with a substituent selected from hydroxy, carboxy, C _1-6 alkoxycarbonyl group, a carbamoyl group, C _1-6 alkylcarbamoyl group and a di-C _1-6 alkylcarbamoyl groups

c. -COOR ^b41 ,

where R ^b41 represents a hydrogen atom, a C _1-6 alkyl group or an aralkyl group,

d. -COR ^b42 ,

where R ^b42 represents

· C _1-6 alkyl group, where C _1-6 alkyl group may be substituted by a substituent selected from

·· hydroxyl group,

·· carboxy groups,

·· C _1-6 alkoxycarbonyl group,

·· acyl group,

·· acyloxy groups,

·· amino groups and

·· acylamino groups,

· C _3-8 cycloalkyl group, where C _3-8 cycloalkyl group may be substituted by a hydroxyl group,

A 5- or 6-membered aromatic heterocyclic group having from 1 to 4 heteroatoms, where the heterocyclic group may be substituted with a C _1-6 alkyl group, or

An aryl group, wherein the aryl group may be substituted with a hydroxyl group,

e. —CO — N (R ^b43 ) (R ^b44 ), where R ^b43 and R ^b44 may be the same or different and each represents a hydrogen atom, a C _1-6 alkyl group or an acyl group, or

f. —SO ₂ —R ^b45 , where R ^b45 represents a C _1-6 alkyl group;

R ^c represents —C (= NR ^c1 ) —R ^c2 ,

Where

(1) R ^c1 represents

but. hydroxyl group

b. A C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the C _1-6 alkoxy group may be substituted with a hydroxyl group or a C _1-6 alkoxy group, or

c. an acyloxy group, and

(2) R ^c2 represents a C _1-6 alkyl group or an amino group;

R ^d is —C (═O) —R ^d1 ,

where R ^d1 represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group or a C _1-6 alkoxycarbonyl group,

(3) a hydroxyl group,

(4) a C _1-6 alkoxy group and

(5) -N (R ^d11 ) (R ^d12 ),

where R ^d11 and R ^d12 may be the same or different and each represents a substituent selected from the following group Da:

[Group Da]

but. hydrogen atom

b. C _1-6 alkoxy group,

c. C _3-8 cycloalkyl group, where the cycloalkyl group may be substituted by a hydroxyl group, and

d. A C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group or an amino group, or

R ^d11 and R ^d12 together with an adjacent nitrogen atom can form a 5- or 6-membered saturated heterocyclic group, which has one or more nitrogen atoms, where the saturated heterocyclic group can be substituted with C _1-6 alkyl groups, where the alkyl group can be substituted a carboxy group, or a carboxy group;

R ^e represents the following ring A:

where the ring A represents

A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms,

A 5- or 6-membered aromatic heterocyclic group containing from 1 to 4 heteroatoms,

· 9-12-membered condensed aromatic heterocyclic group having 1 or 2 heteroatoms, which may be partially saturated,

C _3-8 cycloalkyl group or

· C _7-11 spiroheterocycloalkyl group having 1 or 2 heteroatoms;

which may be substituted with a substituent respectively selected from the following group Ea:

[Group Ea]

but. -OR ^e1 where R ^e1 represents

Hydrogen atom

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a carboxy group or —CON (R ^e11 ) (R ^e12 ),

where R ^e11 and R ^e12 may be the same or different and each represents a hydrogen atom or a C _1-6 alkyl group,

Acyl group

Carbamoyl group or

Aralkyl group,

b. -COOR ^e2 ,

where R ^e2 represents a hydrogen atom or a C _1-6 alkyl group,

c. -CO-N (R ^e41 ) (R ^e42 ),

where R ^e41 and R ^e42 may be the same or different and each represents

Hydrogen atom

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C _1-6 alkoxy group, an amino group, a C _1-6 alkylamino group, a di-C _1-6 alkylamino group, a halogen atom, a carboxy group, a carbamoyl group, a C _1-6 alkylcarbamoyl group, a di-C _1-6 alkylcarbamoyl group, or a 5- or 6-membered saturated heterocyclic group or an aromatic heterocyclic group having 1 or 2 heteroatoms,

A hydroxyl group

C _1-6 alkoxy group,

· A C _5-6 cycloalkyl group, wherein a C _5-6 cycloalkyl group may be substituted by a hydroxyl group or a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted by a hydroxyl group, or

· C _1-6 alkylsulfonyl group,

d. -COR ^e3 ,

where R ^e3 represents

Hydrogen atom

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group and a C _1-6 alkylsulfonyl group,

A 5- or 6-membered saturated heterocyclic group or an aromatic heterocyclic group having 1 or 2 heteroatoms, where the saturated heterocyclic group or aromatic heterocyclic group may be substituted by a hydroxyl group, an oxo group, a carboxy group, a C _1-6 alkoxy group, where C _1-6 alkoxy group may be substituted with a carbamoyl group, a carbamoyl group, a carbamoyl group which may be substituted with a hydroxyl group, an acyl group, atsiloksigruppoy, amino, acylamino, acylamino wherein group may be substituted with a hydroxyl group or a carbamoyl group, C _1-6 alkylamino, di-C _1-6 alkylamino, C _1-6 alkylsulfonylamino, a 5- or 6-membered saturated heterocyclic group or an aromatic heterocyclic group and a C _1-6 alkyl group wherein the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C _1-6 alkoxy group, wherein the C _1-6 alkoxy group may be substituted with a carbamoyl group, an acylamino group and a carbamoyl group, or

· A C _5-6 cycloalkyl group or an aryl group, where the C _5-6 cycloalkyl group or an aryl group may be substituted by a hydroxyl group, an oxo group, a C _1-6 alkoxy group, a carbamoyl group, an acylamino group, an oxymino group or an acyloxy group,

e. oxo group

f. -N (R ^e51 ) (R ^e52 ),

where R ^e51 and R ^e52 may be the same or different and each represents

Hydrogen atom

· C _1-6 alkylsulfonyl group,

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C _1-6 alkoxy group and a carbamoyl group,

Acyl group, where the acyl group may be substituted by a hydroxyl group or a C _1-6 alkoxy group,

-CON (R ^e11 ) (R ^e12 ), or where R ^e11 and R ^e12 are as defined above,

-COR ^e511 ,

where R ^e511 represents a 5- or 6-membered saturated heterocyclic group containing at least one nitrogen atom, a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group or a C _5-6 cycloalkyl a group where the cycloalkyl group may be substituted by a hydroxyl group,

g. C _1-6 alkyl group, where C _1-6 alkyl group may be substituted with a substituent selected from the following Eb group:

[Group Eb]

Hydroxyl group

· A C _1-6 alkoxy group, where a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a carboxy group or —CO — N (R ^e11 ) (R ^e12 ), where R ^e11 and R ^e12 are as defined above ,

· -COOR ^e2 ,

where R ^e2 has the meaning indicated above,

-N (R ^e51 ) (R ^e52 ),

where R ^e51 and R ^e52 have the meanings indicated above,

-CO-N (R ^e51 ) (R ^e52 ),

where R ^e51 and R ^e52 have the meanings indicated above,

A halogen atom and

A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted by a hydroxyl group or a C _1-6 alkyl group,

h. - (CH ₂ ) _n -N (R ^e61 ) - (CH ₂ ) _m -CO (R ^e62 ),

where n and m are an integer equal to 0 or from 1 to 4, and n + m are from 1 to 6, R ^e61 represents a hydrogen atom or a C _1-6 alkyl group and R ^e62 represents C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted by hydroxyl group, C _1-6 alkoxy, amino, C _1-6 alkylamino or di-C _1-6 alkylamino group,

i. hydroxyimino group,

j. C _1-6 alkylsulfonyl group,

k. cyano group

l. A 5- or 6-membered saturated heterocyclic group (which may be partially unsaturated) containing 1 or 2 heteroatoms selected from a nitrogen atom and an oxygen atom, or a 5- or 6-membered aromatic heterocyclic group containing from 1 to 4 heteroatoms, selected from a nitrogen atom and an oxygen atom, wherein a saturated heterocyclic group and an aromatic heterocyclic group may be substituted by an oxo group or a C _1-6 alkyl group,

m. aminosulfonyl group and

n A C _1-6 alkylidene group, wherein the C _1-6 alkylidene group may be substituted with a halogen atom or a carboxy group;

R ^f represents a C _1-6 alkyl group or a C _2-6 alkenyl group, wherein said C _1-6 alkyl group and a C _2-6 alkenyl group may be substituted with a substituent selected from the following Fa group:

[Group Fa]

but. A C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the alkoxy group may be substituted with a carboxy group, a C _1-6 alkoxycarbonyl group or —CON (R ^f21 ) (R ^f22 ),

where R ^f21 and R ^f22 may be the same or different and each represents

Hydrogen atom

Acyl group, where the acyl group may be substituted by a hydroxyl group or a carboxy group,

C _1-6 alkoxycarbonyl group

-O-COOR ^f1 ,

where R ^f1 represents a hydrogen atom or a C _1-6 alkyl group,

· C _1-6 alkyl group,

where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group, a carbamoyl group,

· C _1-6 alkylsulfonyl group or

Carbamoyl group

b. -COOR ^f1 ,

where R ^f1 represents a hydrogen atom or a C _1-6 alkyl group,

c. -N (R ^f21 ) (R ^f22 ),

where R ^f21 and R ^f22 have the meanings indicated above,

d. -CON (R ^f21 ) (R ^f22 ),

where R ^f21 and R ^f22 have the meanings indicated above,

e. -N (R ^f23 ) CON (R ^f21 ) (R ^f22 ),

where R ^f23 represents a hydrogen atom or a C _1-6 alkyl group, and R ^f21 and R ^f22 have the meanings indicated above,

f. acyl group and

g. halogen atom;

R ^g is a substituent having ring B represented by the following formula (II):

wherein A is a linker selected from the group consisting of Ga:

[Group Ga]

- (CH ₂ ) _k -,

- - (CH ₂ ) _k -NR ^g1 - (CH ₂ ) _j -,

· - (CH ₂ ) _k -O- (CO) NR ^g1 - (CH ₂ ) _j -,

- - (CH ₂ ) _k - NR ^g1 (CO) - (CH ₂ ) _j -,

- - (CH ₂ ) _k - (CO) - (CH ₂ ) _j -,

- - (CO) -,

· - (CH ₂ ) _k -O- (CH ₂ ) _j -,

· - (CH ₂ ) _k -S- (CH ₂ ) _j -,

· - (CH ₂ ) _k -O- (CO) - (CH ₂ ) _j -,

- (CO) NR ^g1 - and

· - (CH ₂ ) _k -O- (CH ₂ ) _j (CO) - (CH ₂ ) _g -,

where k, j and g can be the same or different and represent an integer from 0 to 4, but k and j or k and g cannot be equal to 0 at the same time,

R ^g1 represents

·· hydrogen atom,

·· hydroxyl group,

·· C _1-6 alkoxy group,

·· an acyl group, where the acyl group may be substituted by a hydroxyl group or a carboxy group

·· C _3-8 cycloalkyl group, where the cycloalkyl group may be substituted

C _1-6 alkyl group, where the alkyl group may be substituted by a carboxy group,

·· aralkyl group or

·· C _1-6 alkyl group, where the alkyl group may be substituted with a hydroxyl group, —N (R ^g41 ) (R ^g42 ) or —CON (R ^g41 ) (R ^g42 ),

where R ^g41 and R ^g42 may be the same or different and represent

··· hydrogen atom,

··· an acyl group, where the acyl group may be substituted by a hydroxyl group,

··· aralkyl group,

··· C _1-6 alkylsulfonyl group or

··· C _1-6 alkyl group,

where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group, —N (R ^g51 ) (R ^g52 ) or —CO-N (R ^g51 ) (R ^g52 ),

where R ^g51 and R ^g52 may be the same or different and represent

···· hydrogen atom,

···· an acyl group, where the acyl group may be substituted by a hydroxyl group,

···· C _1-6 alkyl group,

where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, an acylamino group, a C _1-6 alkoxycarbonyl group or a halogen atom,

···· C _1-6 alkoxycarbonyl group,

···· C _1-6 alkylsulfonyl group or

···· C _3-8 cycloalkyl group, where the cycloalkyl group may be substituted by a hydroxyl group or a C _1-6 alkoxy group, or

R ^g51 and R ^g52 together with an adjacent nitrogen atom can form a 5- or 6-membered saturated heterocyclic group that has one or more nitrogen atoms, where the saturated heterocyclic group can be substituted by a hydroxyl group or a C _1-6 alkoxy group,

ring B is a ring selected from the following group Ha:

[Group Ha]

Aryl group

C _3-8 cycloalkyl group

A 5-7 membered saturated heterocyclic group having one or more nitrogen atoms,

A 5- or 6-membered aromatic heterocyclic group having at least one heteroatom, and

An 8-11 membered fused aromatic heterocyclic group having at least one heteroatom, and

ring B may be substituted with a substituent selected from the following group Ia:

[Group Ia]

but. -OR ^g2 ,

where R ^g2 represents

Hydrogen atom

· C _1-6 alkyl group or

Aralkyl group,

b. -COOR ^g3 ,

where R ^g3 represents

Hydrogen atom

· C _1-6 alkyl group or

An aralkyl group, wherein the alkyl group may be substituted with a hydroxyl group,

c. -N (R ^g41 ) (R ^g42 ),

where R ^g41 and R ^g42 have the meanings indicated above,

d. —CO — R ^g53 , where R ^g53 is

· C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group, a carboxy group or an acylamino group,

· A C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group or an oxo group,

A 5- or 6-membered saturated heterocyclic group containing at least one heteroatom, wherein the saturated heterocyclic group may be substituted with a hydroxyl group, a C _1-6 alkyl group or an oxo group,

An aryl group, where the aryl may be substituted by a hydroxyl group,

A 5- or 6-membered aromatic heterocyclic group containing at least one heteroatom,

An aralkyl group or

A 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms,

e. C _1-6 alkyl group, where C _1-6 alkyl group which may be substituted by hydroxyl group, C _1-6 alkoxy group, aralkoxy group, carboxy group, C _1-6 alkoxycarbonyl group, -CO-R ^g53 , where R ^g53 have the meanings the above, -N (R ^g51 ) (R ^g52 ) or -CO-N (R ^g51 ) (R ^g52 ),

where R ^g51 and R ^g52 have the meanings indicated above,

f. -CO-N (R ^g51 ) (R ^g52 ),

where R ^g51 and R ^g52 have the meanings indicated above.

g. C _1-6 alkylsulfonyl group,

h. oxo group

i. an aryl group, wherein the aryl group may be substituted with a hydroxyl group,

j. aralkyl group and

k. halogen atom; and

R ^h represents —N (R ^h1 ) (R ^h2 ),

where R ^h1 represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group, —N (R ^g51 ) (R ^g52 ), —CO-N (R ^g51 ) (R ^g52 ), where R ^g51 and R ^g52 are as defined above, a C _1-6 alkylsulfonyl group or a halogen atom,

(3) a C _2-6 alkenyl group,

(4) a C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group, or

(5) an aralkyl group,

R ^h2 represents

(1) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a substituent selected from the following group Ja:

[Group Ja]

Hydroxyl group

C _1-6 alkoxy group,

Carboxy group

· An aromatic carbocyclic group, where the aromatic carbocyclic group can be substituted by a hydroxyl group, a C _1-6 alkyl group, where the alkyl group can be substituted by a carboxy group, a halogen atom, a C _1-6 alkoxy group, a carboxy group, a C _1-6 alkoxycarbonyl group, C _{2 -6 an} alkenyl group, wherein the C _2-6 alkenyl group may be substituted with a carboxy group,

· C _3-8 cycloalkyl group, where the cycloalkyl group may be substituted by a carboxy group or an aralkoxy group,

A 5- or 6-membered aromatic heterocyclic group containing 1 or 2 heteroatoms, where the aromatic heterocyclic group may be substituted by a carboxy group,

A 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms,

-N (R ^g51 ) (R ^g52 ),

where R ^g51 and R ^g52 have the meanings indicated above,

-CON (R ^g51 ) (R ^g52 ),

where R ^g51 and R ^g52 have the meanings indicated above,

-COR ^g53 , where R ^g53 has the meanings indicated above, and

· -COOR ^g3 , where R ^g3 has the meaning indicated above,

(2) an acyl group, where the acyl group may be substituted by a hydroxyl group,

(3) a C _1-6 alkoxycarbonyl group,

(4) a C _2-6 alkenyl group, wherein the alkenyl group may be substituted with a carboxy group or a halogen atom,

(5) a C _3-8 cycloalkyl group where the cycloalkyl group may be substituted with a hydroxyl group, —COOR ^g3 , where R ^g3 is as defined above, —COR ^g53 , where R ^g53 is as defined above, ^{—CONR g51} R ^g52 where R ^g51 and R ^g52 each have the meaning indicated above, or a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group,

(6) a 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted with —COR ^g53 , where R ^g53 is as defined above, —COOR ^g3 , where R ^g3 is as indicated above, ^{—CONR g51} R ^g52 , where R ^g51 and R ^g52 each, has the meaning indicated above, or a C _1-6 alkylsulfonyl group, or

(7) an aromatic carbocyclic group, wherein the aromatic carbocyclic group may be substituted by a carboxy group, a C _1-6 alkyl group, where the alkyl group may be substituted by a carboxy group or a C _2-6 alkenyl group, where the alkenyl group may be substituted by a carboxy group,

or a pharmaceutically acceptable salt thereof.

2. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein Z represents a nitrogen atom.

3. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 2, wherein the aminopyridine compound according to claim 1 is an aminopyridine compound represented by the following general formula (Ia-1):

Where

X ¹ represents

(1) —C (R ² ) =;

X ² represents

(1) —C (R ³ ) = or

(2) a nitrogen atom;

X ³ represents

(1) —C (R ⁴ ) = or

(2) a nitrogen atom;

Y ¹ represents

(1) -CH = or

(2) a nitrogen atom;

R ¹ represents

(1) a hydrogen atom or

(2) a C _1-6 alkyl group;

R ² represents

(1) a hydrogen atom,

(2) a halogen atom or

(3) a C _1-6 alkyl group;

R ³ represents

(1) a hydrogen atom,

(2) a halogen atom,

(3) a C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the C _1-6 alkoxy group may be substituted with a substituent selected from the following group Aa-1:

[Group Aa-1]

but. hydroxyl group

b. C _1-6 alkoxy group,

c. -N (R ³¹ ) (R ³² ),

where R ³¹ and R ³² represent a hydrogen atom or a C _1-6 alkyl group,

d. halogen atom

(4) an aralkoxy group,

(5) an acyl group,

(6) a saturated heterocyclic group or an aromatic heterocyclic group, where the heterocyclic group may be substituted with a C _1-6 alkyl group, and the saturated heterocyclic group may partially have a double bond,

(7) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from the following Ab-1 group:

[Group Ab-1]

but. hydroxyl group

b. -COOR ³³ , where R ³³ represents a hydrogen atom or a C _1-6 alkyl group,

c. —CO — N (R ³¹ ) (R ³² ), wherein R ³¹ and R ³² are as defined above, and

d. a halogen atom, or

(8) a cyano group, or

R ³ together with R ² can form a group —C = CC = C—;

R ⁴ represents

(1) a hydrogen atom or

(2) a C _1-6 alkyl group;

R ⁶ represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group or a C _1-6 alkoxy group,

(3) -COOR ⁶¹ ,

where R ⁶¹ represents a hydrogen atom or a C _1-6 alkyl group,

(4) -N (R ⁶² ) (R ⁶³ ),

where R ⁶² and R ⁶³ may be the same or different and each represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy group or an acyl group,

(5) —CO — N (R ⁶² ) (R ⁶³ ), wherein R ⁶² and R ⁶³ are as defined above, or

(6) an acyl group; and

R ⁷ has the same meaning as described in claim 1 above.

4. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claims 1-3, wherein the aminopyridine compound according to claims 1-3 is an aminopyridine compound represented by the following general formula (Ia-2):

Where

X ² represents

(1) = C (R ³ ) - or

(2) a nitrogen atom;

R ² represents

(1) a hydrogen atom or

(2) a halogen atom;

R ³ represents

(1) a hydrogen atom,

(2) a halogen atom,

(3) a C _1-6 alkoxy group,

where the C _1-6 alkyl group in the C _1-6 alkoxy group may be substituted with a substituent selected from the following group Aa-2:

[Group Aa-2]

but. hydroxyl group and

b. halogen atom

(4) an acyl group,

(5) a saturated heterocyclic group or an aromatic heterocyclic group, wherein the heterocyclic group may be substituted with a C _1-6 alkyl group and the saturated heterocyclic group may partially have a double bond,

(6) a C _1-6 alkyl group which may be substituted with a substituent selected from the following Ab-2 group:

[Group Ab-2]

but. hydroxyl group and

b. halogen atom or

(7) a cyano group, or

R ³ together with R ² can form a group —C = CC = C—;

R ⁶ represents

(1) a hydrogen atom or

(2) a C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group;

R ⁷ represents a hydrogen atom or the following R ^a , R ^b , R ^c , R ^d , R ^e , R ^f , R ^g or R ^h ;

R ^a is —C _p H _{2 (p-1)} (R ^a1 ) (R ^a2 ) —OR ^a3 ,

Where

(1) p is an integer from 1 to 6,

(2) R ^a1 represents a hydrogen atom,

(3) R ^a2 represents

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, an acyloxy group, a C _1-6 alkylamino group or a di C _1-6 alkylamino group,

An aralkyl group, wherein the aralkyl group may be substituted with a hydroxyl group, a carboxy group or an acyloxy group, or

Aryl group

(4) R ^a3 represents a hydrogen atom, an acyl group or - (CO) N (R ^a31 ) (R ^a32 ),

where R ^a31 and R ^a32 may be the same or different and represent a hydrogen atom or a C _1-6 alkyl group;

R ^b represents —C _p H _{2 (p-1)} (R ^b1 ) (R ^b2 ) -N- (R ^b3 ) (R ^b4 ),

Where

(1) p is an integer from 1 to 6,

(2) R ^b1 represents a hydrogen atom,

(3) R ^b2 represents

but. an aralkyl group, wherein the aralkyl group may be substituted by a hydroxyl group, a C _1-6 alkoxy group which may be substituted by a hydroxyl group, an aralkoxy group or —N (R ^b21 ) (R ^b22 ),

where R ^b21 and R ^b22 represent a hydrogen atom, a C _1-6 alkyl group, an acyl group or an aralkoxycarbonyl group,

b. an aryl group, wherein the aryl group may be substituted with a hydroxyl group or an aralkoxy group, or

c. A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, an aralkoxy group, an aralkoxycarbonyl group, an amino group, an acyl group or an aralkylcarbonyl group,

(4) R ^b3 represents a hydrogen atom or a C _1-6 alkyl group,

(5) R ^b4 represents

but. hydrogen atom

b. A C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a carboxy group or a C _1-6 alkoxycarbonyl group,

c. -COR ^b32 ,

where R ^b32 represents a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group, an acyl group, a carboxy group,

C _1-6 alkoxycarbonyl group or acyloxy group, or

d. -CON (R ^b321 ) (R ^b322 ),

where R ^b321 and R ^b322 represent a hydrogen atom or a C _1-6 alkyl group;

R ^c represents —C (= NR ^c1 ) —R ^c2 ,

Where

(1) R ^c1 represents

but. hydroxyl group

b. A C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the C _1-6 alkoxy group may be substituted with a hydroxyl group, or

c. acyloxy group,

(2) R ^c2 represents a C _1-6 alkyl group;

R ^d is —C (═O) —R ^d1 ,

where R ^d1 represents

(1) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group or a C _1-6 alkoxycarbonyl group,

(2) a C _1-6 alkoxy group,

(3) a C _3-8 cycloalkyl group, wherein a C _3-8 cycloalkyl group may be substituted with a hydroxyl group,

(4) -N (R ^d11 ) (R ^d12 ),

where R ^d11 and R ^d12 may be the same or different and each represents

Hydrogen atom

C _1-6 alkoxy group or

· C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group or a C _1-6 alkoxycarbonyl group;

R ^e represents

A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms,

A 5- or 6-membered aromatic heterocyclic group having from 1 to 4 heteroatoms,

· 9-12-membered condensed aromatic heterocyclic group, which may be partially saturated, having 1 or 2 heteroatoms,

C _3-8 cycloalkyl group or

A C _7-11 spiroheterocycloalkyl group having 1 or 2 heteroatoms, and

each may be substituted with a substituent selected from the following group Ea-1:

[Group Ea-1]

but. -OR ^e1 where R ^e1 represents

Hydrogen atom

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a carboxy group or —CON (R ^e11 ) (R ^e12 ),

where R ^e11 and R ^e12 may be the same or different and each represents a hydrogen atom or a C _1-6 alkyl group,

Acyl group

Carbamoyl group or

Aralkyl group,

b. -COOR ^e2 ,

where R ^e2 represents a hydrogen atom or a C _1-6 alkyl group,

c. -CO-N (R ^e41 ) (R ^e42 ),

where R ^e41 and R ^e42 may be the same or different and each represents

Hydrogen atom

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C _1-6 alkoxy group, a di C _1-6 alkylamino group, a carboxy group, a halogen atom, a C _1-6 alkylcarbamoyl group and a 5- or 6-membered saturated heterocyclic group or aromatic heterocyclic group having 1 or 2 heteroatoms,

A hydroxyl group

C _1-6 alkoxy group,

Acyl group, where the acyl group may be substituted by a hydroxyl group,

A C _3-8 cycloalkyl group, wherein the C _3-8 cycloalkyl group may be substituted with a hydroxyl group, or

· C _1-6 alkylsulfonyl group,

d. -COR ^e3 ,

where R ^e3 represents a hydrogen atom, a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxy group, a carboxy group or a C _1-6 alkylsulfonyl group, a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, where a saturated heterocyclic group may be substituted by a hydroxyl group, a carboxy group, a C _1-6 alkyl group, an acyl group, a C _1-6 alkoxy group, a carbamoyl group, —N (R ^e41 ) (R ^e42 ), where R ^e41 and R ^e42 are as defined above, an acylamino group or an oxo group, C _3-8 cycloalk Flax group wherein C _3-8 cycloalkyl group may be substituted with a hydroxyl group, an aromatic hydrocarbon group, aromatic hydrocarbon group which may be substituted with a hydroxyl group or a 5- or 6-membered aromatic heterocyclic group having 1 or 2 heteroatoms,

e. oxo group

f. -N (R ^e51 ) (R ^e52 ),

where R ^e51 and R ^e52 may be the same or different and each represents

Hydrogen atom

· C _1-6 alkylsulfonyl group,

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group,

Acyl group, where the acyl group may be substituted by a hydroxyl group, or

-COR ^e511 ,

where R ^e511 represents a 5- or 6-membered saturated heterocyclic group containing at least one nitrogen atom, or a C _3-8 cycloalkyl group, where the C _3-8 cycloalkyl group may be substituted by a hydroxyl group,

g. C _1-6 alkyl group, where C _1-6 alkyl group may be substituted with a substituent selected from the following group Eb-1:

[Group Eb-1]

Hydroxyl group

· A C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the C _1-6 alkoxy group may be substituted with a carboxy group or —CO — N (R ^e11 ) (R ^e12 ), where R ^e11 and R ^e12 are as defined above,

· -COOR ^e2 ,

where R ^e2 has the meaning indicated above,

-N (R ^e51 ) (R ^e52 ),

where R ^e51 and R ^e52 have the meanings indicated above,

-CO-N (R ^e51 ) (R ^e52 ),

where R ^e51 and R ^e52 have the meanings indicated above,

A halogen atom and

A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms,

h. hydroxyimino group,

i. C _1-6 alkylsulfonyl group,

j. cyano group

k. A 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms selected from a nitrogen atom and an oxygen atom (which may be partially unsaturated and may be substituted by an oxo group or a C _1-6 alkyl group), or an aromatic heterocyclic group containing from 1 to 4 heteroatoms selected from a nitrogen atom and from an oxygen atom,

l. aminosulfonyl group and

m. A C _1-6 alkylidene group, wherein the C _1-6 alkylidene group may be substituted with a halogen atom or a carboxy group;

R ^f represents a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from the following Fa-1 group:

[Group Fa-1]

but. A C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the alkoxy group may be substituted with a carboxy group, a C _1-6 alkoxycarbonyl group or —CON (R ^f21 ) (R ^f22 ),

where R ^f21 and R ^f22 may be the same or different and each represents

Hydrogen atom

Acyl group, where the acyl group may be substituted by a hydroxyl group or a carboxy group,

C _1-6 alkoxycarbonyl group

-O-COOR ^f1 ,

where R ^f1 represents a hydrogen atom or a C _1-6 alkyl group,

· C _1-6 alkyl group,

where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group or a carbamoyl group,

· C _1-6 alkylsulfonyl group or

Carbamoyl group

b. -COOR ^f1 ,

where R ^f1 has the meaning indicated above,

c. -N (R ^f21 ) (R ^f22 ),

where R ^f21 and R ^f22 have the meanings indicated above,

d. -CON (R ^f21 ) (R ^f22 ),

where R ^f21 and R ^f22 have the meanings indicated above,

e. acyl group and

f. halogen atom;

R ^g represents a Deputy having a ring B 'represented by the following formula (IIa):

where A 'is a linker selected from the following group Ga-1:

[Group Ga-1]

- (CH ₂ ) _k -,

- - (CH ₂ ) _k -NR ^g1 - (CH ₂ ) _j -,

· - (CH ₂ ) _k -O- (CO) NR ^g1 - (CH ₂ ) _j -,

· - (CH ₂ ) _k -NR ^g1 (CO) - (CH ₂ ) _j -,

- - (CH ₂ ) _k -NR ^g1 - (CH ₂ ) _j -,

- - (CH ₂ ) _k - (CO) - (CH ₂ ) _j -,

- - (CO) -,

· - (CH ₂ ) _k -O- (CH ₂ ) _j -,

· - (CH ₂ ) _k -S- (CH ₂ ) _j -,

· - (CH ₂ ) _k -O- (CO) - (CH ₂ ) _j - and

· - (CH ₂ ) _k -O- (CH ₂ ) _j (CO) - (CH ₂ ) _g -,

where k, j and g can be the same or different and represent an integer from 0 to 4, but k and j or k and g cannot be equal to 0 at the same time,

R ^g1 represents

·· hydrogen atom,

·· an acyl group, where the acyl group may be substituted by a carboxy group or a hydroxyl group, or

·· C _1-6 alkyl group,

where the alkyl group may be substituted by a carboxy group,

ring B 'is a ring selected from the following Ha-1 group:

[Group Ha-1]

Aryl group

C _3-8 cycloalkyl group

A 5-7 membered saturated heterocyclic group having at least one nitrogen atom, where a saturated heterocyclic ring can form a fused ring with a phenyl group, and

A 5- or 6-membered aromatic heterocyclic group containing 1 or 2 heteroatoms, and

ring B 'may be substituted with a substituent selected from the following group Ia-1:

[Group Ia-1]

but. -OR ^g2 ,

where R ^g2 represents

Hydrogen atom

· C _1-6 alkyl group or

Aralkyl group,

b. -COOR ^g3 ,

where R ^g3 represents

A hydrogen atom or

· C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group,

c. -N (R ^g41 ) (R ^g42 ),

where R ^g41 and R ^g42 have the meanings indicated above,

d. —CO — R ^g53 , where R ^g53 is

· C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group, a carboxy group or an acylamino group,

· A C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group or an oxo group,

An aryl group, wherein the aryl group may be substituted with a hydroxyl group,

A 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted by a hydroxyl group, a C _1-6 alkyl group or an oxo group,

An aralkyl group or

A 5- or 6-membered aromatic heterocyclic group containing 1 or 2 heteroatoms,

e. A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group or —CO-R ^g53 , where R ^g53 has the meaning indicated above,

f. -CO-N (R ^g51 ) (R ^g52 ),

where R ^g51 and R ^g52 may be the same or different and represent

Hydrogen atom

Acyl group, where the acyl group may be substituted by a hydroxyl group,

· C _1-6 alkyl group,

where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, an acylamino group, a C _1-6 alkoxycarbonyl group or a halogen atom,

· C _1-6 alkylsulfonyl group,

C _1-6 alkoxycarbonyl group

Carbamoyl group or

· A C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group,

g. C _1-6 alkylsulfonyl group,

h. oxo group and

i. halogen atom; and

R ^h represents —N (R ^h1 ) (R ^h2 ),

where R ^h1 represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group, —N (R ^g51 ) (R ^g52 ), —CO-N (R ^g51 ) (R ^g52 ), C _1-6 alkylsulfonyl or a halogen atom,

where R ^g51 and R ^g52 have the meanings indicated above,

(3) a C _2-6 alkenyl group,

(4) a C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group, or

(5) an aralkyl group,

R ^h2 represents

(1) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from the following group Ja-1:

[Group Ja-1]

Hydroxyl group

C _1-6 alkoxy group,

Carboxy group

· An aromatic carbocyclic group, where the aromatic carbocyclic group can be substituted by a hydroxyl group, a C _1-6 alkyl group, where the alkyl group can be substituted by a carboxy group, a halogen atom, a C _1-6 alkoxy group, a carboxy group, a C _1-6 alkoxycarbonyl group, C _{2 -6 an} alkenyl group, wherein the C _2-6 alkenyl group may be substituted with a carboxy group,

· C _3-8 cycloalkyl group, where the cycloalkyl group may be substituted by a carboxy group or an aralkoxy group,

A 5- or 6-membered aromatic heterocyclic group containing 1 or 2 heteroatoms, where the aromatic heterocyclic group may be substituted by a carboxy group,

A 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms,

-N (R ^g51 ) (R ^g52 ) and

-CON (R ^g51 ) (R ^g52 ),

where R ^g51 and R ^g52 have the meanings indicated above,

(2) an acyl group, where the acyl group may be substituted by a hydroxyl group,

(3) a C _2-6 alkenyl group, wherein the alkenyl group may be substituted with a carboxy group or a halogen atom,

(4) a C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group, —COOR ^g3 , where R ^g3 is as defined above, —COR ^g53 , where R ^g53 is as defined above, ^{—CONR g51} R ^g52 where R ^g51 and R ^g52 each has the meaning indicated above, or a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group,

(5) a 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted with —COR ^g53 , where R ^g53 is as defined above, —COOR ^g3 , where R ^g3 is as indicated above, ^{—CONR g51} R ^g52 , where R ^g51 and R ^g52 each have the meaning indicated above, or a C _1-6 alkylsulfonyl group, or

(6) an aromatic carbocyclic group, wherein the aromatic carbocyclic group may be substituted with a carboxy group, a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group or a C _2-6 alkenyl group, where the alkenyl group may be substituted with a carboxy group.

5. An aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with paragraph 4 above, wherein

R ² represents a hydrogen atom,

R ³ represents a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group or a halogen atom,

R ⁶ represents a hydrogen atom, and

R ⁷ represents R ^e , R ^g or R ^h .

6. The aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with paragraph 5 above, wherein

R ⁷ represents R ^e , and

R ^e represents

(1) a 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted with a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group, -COR ^e3 , where R ^e3 represents A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, where a 5- or 6-membered saturated heterocyclic group may be substituted with a hydroxyl group or —CO — N (R ^e41 ) (R ^e42 ), where R ^e41 and R ^e42 may be the same or different and each represents a hydrogen atom ode or a C _1-6 alkyl group, or

(2) a C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group, -COR ^e3 , where R ^e3 is a 5- or 6-membered saturated heterocyclic group, having 1 or 2 heteroatoms, where the 5- or 6-membered saturated heterocyclic group may be substituted by a hydroxyl group or —CO-N (R ^e41 ) (R ^e42 ), where R ^e41 and R ^e42 may be the same or different and each is a hydrogen atom or a C _1-6 alkyl group.

7. An aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with paragraph 6 above, wherein

R ^e represents

(1) a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms represented by the following ring L, where the saturated heterocyclic group may be substituted with 1 or 2 identical or different substituents selected from a C _1-6 alkyl group, where alkyl the group may be substituted with a carboxy group, -COR ^e3 , where R ^e3 is a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, where the 5- or 6-membered saturated heterocyclic group may be substituted with a hydroxyl group or -CO- N (R ^e41 ) (R ^e42 ), where R ^e41 and R ^e42 may be the same or different and each represents a hydrogen atom or a C _1-6 alkyl group,

where the ring L represents a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, or

(2) a 5- or 6-membered cycloalkyl group, wherein the cycloalkyl group may be substituted with 1 or 2 identical or different substituents selected from a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group, -COR ^e3 , where R ^e3 represent a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, where the 5- or 6-membered saturated heterocyclic group may be substituted with a hydroxyl group or —CO — N (R ^e41 ) (R ^e42 ), where R ^e41 and R ^e42 may be the same or different and each represents a water atom oroda or C _1-6 alkyl group.

8. An aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with paragraph 5 above, wherein

R ^h represents —N (R ^h1 ) (R ^h2 ) and R ^h1 represents a C _1-6 alkyl group, R ^h2 represents a C _3-8 cycloalkyl group, where the cycloalkyl group represents —COOR ^g3 , where R ^g3 represents represents a hydrogen atom or a C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group.

9. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to the preceding claim 1, wherein the aminopyridine compound is selected from the following group of compounds.

(001) 1-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-2-one,

(002) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxylic acid,

(003) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(004) N-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(005) N- (2-hydroxyethyl) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide,

(006) methyl trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid methyl ester,

(007) trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid,

(008) (4-hydroxypiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone,

(009) N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) amine,

(010) N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,

(011) (S) -3-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one,

(012) tert-butyl ether, (S) -2,2-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-3 -carboxylic acid

(013) (S) -2-amino-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,

(014) (S) -4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one,

(015) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(016) trans-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] cyclohexanecarboxylic acid,

(017) 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,

(018) 2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,

(019) N- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} propionamide,

(020) N- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} acetamide,

(021) N- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyrazin-2-yl] thiazol-2-yl} acetamide,

(022) ethyl ester (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} acetic acid,

(023) (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,

(024) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanone,

(025) 5- [6- (4-methyl-pyridin-2-ylamino) -pyridin-2-yl] thiazole-2-carboxylic acid ethyl ester,

(026) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanone,

(027) (S) -5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} dihydrofuran-2-one,

(028) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanone O- (2-hydroxyethyl) oxime,

(029) N-methoxy-N-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carboxamide,

(030) N-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carboxamide,

(031) N-methyl-N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,

(032) (S) -5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-one,

(033) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentanoic acid,

(034) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentan-1-ol,

(035) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentanamide,

(036) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanol,

(037) oxime 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanone,

(038) N- {6- [2 - ((S) -1-aminoethyl) thiazol-5-yl] pyridin-2-yl} -N - ([4,4 '] bipyridinyl-2-yl) amine,

(039) N - ((S) -1- {5- [6 - ([4,4 '] bipyridinyl-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,

(040) N - ((S) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,

(041) (S) -2-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} propan-1-ol,

(042) N - ((S) -1- {5- [6- (isoquinolin-3-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,

(043) (4-methylpyridin-2-yl) - [6- (2-piperidin-4-ylthiazol-5-yl) pyridin-2-yl] amine,

(044) trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,

(045) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentylamine,

(046) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} butan-1-ol,

(047) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenol,

(048) 2-hydroxy-N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,

(049) 3 - ({5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carbonyl} amino) propionic acid,

(050) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) benzoic acid,

(051) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperidin-4-ol,

(052) 3,3-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} butan-1-ol,

(053) [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenyl] methanol,

(054) N - ((R) - (4-hydroxyphenyl) - {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} methyl) acetamide,

(055) N- (2-hydroxyethyl) -4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) benzamide,

(056) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) cyclohexanone,

(057) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) cyclohexanol,

(058) ((3R, 4S) -3,4-dihydroxypyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2 -yl} cyclohexyl) methanone,

(059) (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) - (piperazin-1-yl) methanone,

(060) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-1-carboxamide,

(061) 2-hydroxy-1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-1-yl) ethanone,

(062) trans-4- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid,

(063) 3- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-1-yl) -3-oxopropionic acid,

(064) N- (4-methylpyridin-2-yl) -N- {6- [2- (piperazin-1-ylmethyl) thiazol-5-yl] pyridin-2-yl} amine,

(065) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperidin-4-ylamine,

(066) N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} methanesulfonamide,

(067) N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) acetamide,

(068) trans-4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid,

(069) 2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,

(070) (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanol,

(071) trans-4- {5- [6- (isoquinolin-3-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid,

(072) trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethylamine,

(073) ((3R, 4S) -3,4-dihydroxypyrrolidin-1-yl) - [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol- 2-yl} ethyl) phenyl] methanone,

(074) N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) acetamide,

(075) N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) methanesulfonamide,

(076) 2-hydroxy-N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) acetamide,

(077) 2-hydroxy-N- [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenyl] acetamide,

(078) ((3R, 4S) -3,4-dihydroxypiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2 -yl} cyclohexyl) methanone,

(079) ((R) -3-hydroxypyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl ) methanone

(080) (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} phenyl) methanol,

(081) N- (4-methylpyridin-2-yl) -N- [6- (2-pyridin-3-ylmethylthiazol-5-yl) pyridin-2-yl] amine,

(082) N- (4-methylpyridin-2-yl) -N- {6- [2- (2-piperidin-4-yl-ethyl) thiazol-5-yl] pyridin-2-yl} -amine,

(083) N- (6- {2- [2- (1-methanesulfonylpiperidin-4-yl) ethyl] thiazol-5-yl} pyridin-2-yl) -N- (4-methylpyridin-2-yl) amine ,

(084) 2-hydroxy-1- [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) piperidin-1-yl] ethanone

(085) N- (2-hydroxyethyl) -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,

(086) N- (2-morpholin-4-yl-ethyl) -trans-4- {5- [6- (4-methyl-pyridin-2-ylamino) -pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,

(087) [3- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenyl] methanol,

(088) (3-hydroxypyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone,

(089) 4- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonyl) piperazin-2-one,

(090) ((R) -2-hydroxymethylpyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl ) methanone

(091) (4-aminopiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone,

(092) [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) piperidin-1-yl] - (piperidin-4- sludge) methanone,

(093) (trans-4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) - (4-hydroxypiperidin-1-yl) methanone,

(094) N- (4-hydroxypiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,

(095) N - [(R) -2-hydroxy-1- (3H-imidazol-4-ylmethyl) ethyl] -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2 -yl] thiazol-2-yl} cyclohexanecarboxamide,

(096) N - [(S) -2-hydroxy-1- (3H-imidazol-4-ylmethyl) ethyl] -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2 -yl] thiazol-2-yl} cyclohexanecarboxamide,

(097) N- (2-dimethylaminoethyl) -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,

(098) (3-aminopyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone,

(099) N- [1- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonyl) pyrrolidin-3-yl] methanesulfonamide,

(100) (3R, 4S) -1- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) pyrrolidin-3,4 diol

(101) trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonitrile,

(102) cis-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonitrile,

(103) (S) -5- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-one,

(104) (S) -1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,

(105) (S) -1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) ethanol,

(106) (S) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,

(107) (S) -5- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-one,

(108) 3- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) -4H- [1,2,4] oxazole -5-he

(109) N- (4-methylpyridin-2-yl) -N- (6- {2- [4- (1H-tetrazol-5-yl) cyclohexyl] thiazol-5-yl} pyridin-2-yl) amine ,

(110) (S) -5- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidin-2-one,

(111) N- (1,1-dimethyl-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,

(112) (S) -1- (5- {6- [4- (2-methyl- [1,3] dioxalan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2- sludge) ethanol,

(113) N-methyl-trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,

(114) N- (1,1-dimethyl-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) methanesulfonamide,

(115) trans-4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,

(116) trans-4- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,

(117) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} cyclohexanol,

(118) (S) -1- (5- {6- [4- (2-hydroxyethoxy) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) ethanol,

(119) (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} dimethylcarbamic acid ethyl ester ,

(120) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperazin-2-one,

(121) 4- (2-hydroxy-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenol,

(122) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethoxy} acetyl) piperazin-2-one,

(123) N - ((R) - (4-hydroxyphenyl) - {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} methyl) -N-methylacetamide,

(124) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperazin-2,6-dione,

(125) (S) -5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one,

(126) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperazin-2-one,

(127) N- (4-methylpyridin-2-yl) -N- [6- (2-morpholin-4-ylthiazol-5-yl) pyridin-2-yl] amine,

(128) 1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone,

(129) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-sulfonamide,

(130) N- (4-methoxypyridin-2-yl) -N- {6- [2- (morpholin-4-yl) thiazol-5-yl] pyridin-2-yl} amine,

(131) (3R, 4S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3,4-diol,

(132) N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} acetamide,

(133) N- [6- (4-methyl-2-morpholin-4-ylthiazol-5-yl) pyridin-2-yl] -N- (4-methylpyridin-2-yl) amine,

(134) N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,

(135) N-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-1-carboxamide,

(136) 1- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(137) N- {6- [2- (4-methoxypiperidin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine,

(138) N- {6- [2- (4-methylpiperazin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine,

(139) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ol,

(140) N-methyl-1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(141) 4- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-1-carbaldehyde,

(142) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-4-carboxylic acid methyl ester,

(143) 2-hydroxy-1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone,

(144) 1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) propan-1-one,

(145) N, N-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-1-carboxamide,

(146) 1- (4- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone,

(147) 1- (4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone,

(148) 4- (methyl- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid,

(149) 4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino)

cyclohexanecarboxamide,

(150) 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) -4H- [1,2,4 ] oxadiazol-5-one,

(151) N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-piperidin-4-ylamine,

(152) 4- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carbonyl) piperazin-2-one,

(153) N- (2,2-dimethoxyethyl) -N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,

(154) 1- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] ethanone

(155) 2-hydroxy-1- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine- 1-yl] ethanone,

(156) N-methyl-4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1 -

carboxamide

(157) N- {2- [4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine -1-yl] -2-oxoethyl} acetamide,

(158) (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetic acid,

(159) 2- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetamide,

(160) N-methyl-2- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetamide,

(161) N- (2-hydroxyethyl) -2- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1- il) acetamide,

(162) N-methyl-N-methylcarbamoylmethyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(163) N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-tetrahydropyran-4-ylamine,

(164) 4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] phenol,

(165) N - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) acetamide,

(166) (R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ylamine,

(167) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxylic acid,

(168) 2-hydroxy-N - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) acetamide ,

(169) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxamide,

(170) N-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxamide,

(171) N- (2-hydroxyethyl) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxamide,

(172) (R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ol,

(173) trans-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanol,

(174) N- {6- [2- (3-methoxymethylpiperidin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine,

(175) 2-hydroxy-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide,

(176) 2-hydroxy-N-methyl-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide ,

(177) N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) methanesulfonamide,

(178) N-methyl-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) methanesulfonamide,

(179) 2-hydroxy-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ylmethyl) acetamide,

(180) N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ylmethyl) acetamide,

(181) N-methyl- (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,

(182) N - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) methanesulfonamide,

(183) N- {6- [2 - ((R) -3-methoxypyrrolidin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine,

(184) N-methyl-4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino)

cyclohexanecarboxamide,

(185) N- (2-hydroxyethyl) -4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino )

cyclohexanecarboxamide,

(186) N- (2-acetylaminoethyl) -4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino )

cyclohexanecarboxamide,

(187) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-ylmethoxy)

acetic acid,

(188) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) methanol,

(189) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-ylmethoxy)

acetamide

(190) 4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(191) N-methyl-4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide,

(192) N-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-ylmethoxy)

acetamide

(193) N- (2-hydroxyethyl) -4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(194) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide,

(195) N-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide,

(196) N- (2-hydroxyethyl) -2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide ,

(197) N, N-diallyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,

(198) N- [2- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] acetamide,

(199) 2-hydroxy-N- [2- (N'-methyl- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] acetamide ,

(200) N- (4-methanesulfonylpiperidin-1-yl) -N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,

(201) N, N-dimethyl-4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine -one-

carboxamide

(202) (4-hydroxyphenyl) - [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine- 1-yl]

methanone

(203) 1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylamino} piperidin-1-yl) ethanone,

(204) 1- [4- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] ethanone

(205) N-methyl-2 - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yloxy) acetamide ,

(206) 1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(207) 1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(208) 2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethanol,

(209) N- (2-methoxyethyl) -N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,

(210) N- [2- (N '- (1-acetylpiperidin-4-yl) -N' - {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2- il} amino) ethyl] methanesulfonamide,

(211) 1- [4- (N- (2-hydroxyethyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine- 1-yl] ethanone,

(212) 1- [4- (N- (2-methoxyethyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine- 1-yl] ethanone,

(213) (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,

(214) N-methyl- (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,

(215) N- (2,2,2-trifluoroethyl) - (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin- 2-carboxamide

(216) (R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxylic acid,

(217) ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) methanol,

(218) (R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxamide,

(219) 1- [4- (N-ethyl-N- {5- [6- (4-methylpyridin-2-ylamino)

(220) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] ethanone,

(221) 1- {4- [N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N- (2,2,2-trifluoroethyl) amino] piperidin-1-yl} ethanone,

(222) 1- [4- (N- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-methylamino) piperidin-1-yl] ethanone ,

(223) 1- [4- (N- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-methylamino) piperidin-1-yl] - 2-hydroxyethanone,

(224) (R) -1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ol,

(225) (R) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ol,

(226) 4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxylic acid,

(227) (S) -1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,

(228) (S) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,

(229) 1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,

(230) 2- (N- (2-hydroxyethyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethanol,

(231) 2- [N- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N- (2-hydroxyethyl) amino] ethanol,

(232) (R) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxylic acid,

(233) 1- (5- {6- [4- (1-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-

carboxamide

(234) (R) -1- (5- {6- [4- (2-methyl- [1,3] dioxolan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2- il) pyrrolidin-3-ol,

(235) 1- (2- {6- [2 - ((R) -3-hydroxypyrrolidin-1-yl) thiazol-5-yl] pyridin-2-ylamino} pyridin-4-yl) ethanone,

(236) 4- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) -4-oxo-butyric acid,

(237) N-hydroxy- (R) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxamide,

(238) 4- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] -4-hydroxybutyric acid,

(239) (R) -1- (5- {6- [4- (1-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidin-3-ol,

(240) 2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetamide,

(241) (R) -1- (5- {6- [4- (2-methyl- [1,3] dioxolan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2- il) piperidine-3-carboxylic acid,

(242) (R) -1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxylic acid,

(243) (S) -1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,

(244) (1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) methanol,

(245) 1 - [(R) -3- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pyrrolidin- 1-yl]

ethanone

(246) (S) -1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxylic acid,

(247) (R) -1- (5- {6- [4- (2-methyl- [1,3] dioxolan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2- il) piperidin-3-

carboxamide

(248) ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) acetic acid,

(249) (S) -3-methyl-2- [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetylamino] butyric acid,

(250) 3- [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetylamino]

propionic acid

(251) [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetylamino] acetic acid,

(252) [1- (5- {6- [4- (2-methyl- [1,3] dioxolan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidine -4-yl]

acetic acid,

(253) (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(254) 4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid,

(255) ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yloxy) acetic acid,

(256) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-carboxylic acid,

(257) (R) -1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidin-3-ol,

(258) 4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) benzoic acid,

(259) (2S, 4R) -4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pyrrolidin-2 -

carboxylic acid

(260) {N-methyl-N- [2- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino ) acetyl] amino} acetic acid,

(261) 2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid,

(262) 3 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid,

(263) {4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] phenyl} acetic acid,

(264) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) acetic acid,

(265) (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) acetic acid,

(266) N- (4-methylpyridin-2-yl) -N- (6- {2 - [(R) -3- (1H-tetrazol-5-yl) piperidin-1-yl] thiazol-5-yl } pyridin-2-yl) amine,

(267) cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid,

(268) trans-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid,

(269) 4- [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] benzoic acid,

(270) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yloxy) acetic acid,

(271) (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) acetic acid,

(272) 4 - {[N-methyl-N- (5- {6- [4- (2-methyl- [1,3] dioxalan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) amino] methyl}

benzoic acid,

(273) 4 - [(N-dimethylcarbamoylmethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid,

(274) cis-4- (N-carbamoylmethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid,

(275) trans-4 - [(N-carbamoylmethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid

(276) 5 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] thiophen-2-

carboxylic acid

(277) 3-chloro-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid ,

(278) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethoxy} benzoic acid,

(279) 3-methoxy-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid ,

(280) 2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,

(281) 2 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] thiazol-4-

carboxylic acid

(282) [trans-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexyl] acetic acid,

(283) [cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexyl] acetic acid,

(284) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) cyclohexanecarboxylic acid,

(285) (4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(286) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -3,4-dihydro-2H-benzo [1,4] oxazin-8 -carboxylic acid

(287) {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethoxy} acetic acid,

(288) 4- [1-methyl-1- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] benzoic acid,

(289) [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) phenyl] acetic acid,

(290) (1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(291) trans-4 - [(N-benzyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid

(292) [trans-4- (N-benzyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexyl] acetic acid,

(293) trans-4 - [(N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid

(294) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

(295) fluoro- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ylidene) acetic acid,

(296) 5- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pentanoic acid,

(297) N- [2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetyl]

methanesulfonamide

(298) 4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) butyric acid,

(299) (1- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl)

acetic acid,

(300) (1- {5- [6- (5-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(301) (1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(302) trans-4- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino)

cyclohexanecarboxylic acid

(303) 3- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) phenyl] propionic acid,

(304) (E) -6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-ena acid,

(305) (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinolin-6-yl) acetic acid ,

(306) 3- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinolin-5-yl) propionic acid

(307) 5- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pentanoic acid,

(308) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylamino} pentanoic acid,

(309) 6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hexanoic acid,

(310) (Z) -2-fluoro-6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex -2-enoic acid

(311) (8- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -8-azabicyclo [3.2.1] oct-3-yl) acetic acid ,

(312) (8- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -8-azabicyclo [3.2.1] oct-3-yl) acetic acid ,

(313) (1- {5- [6- (4-cyanopyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(314) {4 - [(N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] phenyl}

acetic acid,

(315) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,

(316) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(317) 4- [1-methyl-1- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] benzoic acid,

(318) 3-methyl-6- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-ena acid,

(319) 3-methyl-6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-ena acid,

(320) (E) -6- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-eno acid,

(321) N- (2-hydroxyethyl) - (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,

(322) 2- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetamide,

(323) 3-methyl-2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) butylamide,

(324) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) ethanol,

(325) 5- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pentan-1-ol,

(326) (1- {5- [6- (pyrazin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(327) [1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl]

acetic acid,

(328) fluoro- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(329) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperidin-4-

carboxamide

(330) (1- {5- [6- (4-ethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(331) N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,

(332) N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N- (2-morpholin-4-yl-ethyl) amine,

(333) 2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} amino) acetamide,

(334) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) butyric acid,

(335) trans-4 - [(N-methyl-N- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid

(336) [1- (5- {6- [4- (2,2,2-trifluoroethoxy) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl]

acetic acid,

(337) 2-methyl-1- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) propan-2-ol ,

(338) 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) propionic acid,

(339) N- (2-hydroxyethyl) -4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino ) piperidin-1-

carboxamide

(340) 2-methyl-2- (1- {5- [6- (pyrazin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,

(341) 4 - [(N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} amino) methyl] benzoic acid,

(342) (1- {5- [6- (4-tert-butylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(343) (1- {5- [6- (4-isopropylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(344) 2-ylamino) pyridin-2-yl] thiazol-2-yl} -6-azaspiro [2.5] octane-1-carboxylic acid,

(345) 2- [1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl] -2-methylpropionic acid,

(346) 2-methyl-2- (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,

(347) fluoro- (1- {5- [6- (pyrazin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(348) fluoro- (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,

(349) [1- (5- {6- [4- (1-hydroxy-1-methylethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl] acetic acid ,

(350) 2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,

(351) 5- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) pentanoic acid and

(352) 2-methyl-2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} amino) propionamide.

10. Aminopyridine compound or its pharmaceutically acceptable salt, in accordance with the above paragraph 9, where the aminopyridine compound is selected from the following group of compounds:

(01) (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,

(02) cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} amino) cyclohexanecarboxylic acid,

(03) (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} piperidin-4-yl) acetic acid and

(04) (4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid.

11. An aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, wherein the aminopyridine compound is (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl ] thiazol-2-yl} pyrrolidin-2-carboxamide.

12. The aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with paragraph 10 above, wherein the aminopyridine compound is (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl } piperidin-4-yl) acetic acid.

13. The aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with paragraph 10 above, wherein the aminopyridine compound is (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2 -yl} piperidin-4-yl) acetic acid.

14. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to the preceding claim 1, wherein the aminopyridine compound is cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridine -2-yl) thiazol-2-yl} amino) cyclohexanecarboxylic acid.

15. The aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with the above as described in claim 1, wherein Z represents a carbon atom.

16. The aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with paragraph 15 above, wherein the aminopyridine compound in accordance with paragraph 1 above is an aminopyridine compound represented by the following general formula (Ib-1):

Where

X ¹ represents

(1) -CH = or

(2) a nitrogen atom;

Y ² represents

(1) -CH = or

(2) a nitrogen atom;

R represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group or

(3) an acyl group;

R ¹ represents

(1) a hydrogen atom or

(2) a halogen atom;

R ³ represents

(1) a hydrogen atom,

(2) a halogen atom,

(3) -N (R ³¹ ) (R ³² ),

where R ³¹ and R ³² represent a hydrogen atom or a C _1-6 alkyl group,

(4) a C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the C _1-6 alkoxy group may be substituted with a substituent selected from the following Aa-3 group:

[Group Aa-3]

but. hydroxyl group and

b. -N (R ³¹ ) (R ³² ),

where R ³¹ and R ³² have the meanings indicated above,

(5) an acyl group,

(6) a saturated heterocyclic group or an aromatic heterocyclic group, wherein the heterocyclic group may be substituted with a C _1-6 alkyl group and the saturated heterocyclic group may partially have a double bond,

(7) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from the following Ab-3 group:

[group Ab-3]

but. hydroxyl group

b. -COOR ³³ , where R ³³ represents a hydrogen atom or a C _1-6 alkyl group, and

c. —CO — N (R ³¹ ) (R ³² ), wherein R ³¹ and R ³² are as defined above, or

(8) —COOR ³³ , wherein R ³³ is as defined above;

R ⁵ represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group or

(3) -COOR ⁵¹ ,

where R ⁵¹ represents a hydrogen atom or a C _1-6 alkyl group;

R ⁶ and R ^{6 '} may be the same or different and each represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group or

(3) an acyl group; and

R ⁷ has the same meaning as described in claim 1 above.

17. An aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with paragraph 16 above, wherein the aminopyridine compound is an aminopyridine compound represented by the following general formula (Ib-2):

where R ³ represents

(1) a halogen atom,

(2) - N (R ³¹ ) (R ³² ),

where R ³¹ and R ³² represent a hydrogen atom or C _1-6 alkyl groups,

(3) a C _1-6 alkoxy group,

where the C _1-6 alkyl group in the C _1-6 alkoxy group may be substituted with a substituent selected from the following group Aa-4:

[Group Aa-4]

but. hydroxyl group and

b. -N (R ³¹ ) (R ³² ),

where R ³¹ and R ³² have the meanings indicated above,

(4) an acyl group,

(5) a saturated heterocyclic group, wherein the heterocyclic group partially has a double bond and may be substituted with a C _1-6 alkyl group,

(6) a C _1-6 alkyl group which may be substituted with a substituent selected from the following Ab-4 group:

[Group Ab-4]

but. hydroxyl group

b. -COOR ³³ , where R ³³ represents a hydrogen atom or a C _1-6 alkyl group, and

c. -CO-N (R ³¹ ) (R ³² ),

where R ³¹ and R ³² have the meanings indicated above, or

(7) -COOR ³³ ,

where R ³³ has the meaning indicated above;

R ⁵ represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group or

(3) -COOR ⁵¹ ,

where R ⁵¹ represents a hydrogen atom or a C _1-6 alkyl group;

R ⁶ and R ^{6 '} may be the same or different and each represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group which may be substituted by a hydroxyl group or a C _1-6 alkyl group which may be substituted by a C _1-6 alkoxy group, or

(3) an acyl group;

R ⁷ represents a hydrogen atom, a halogen atom, a nitro group, a cyano group or the following R ^a , R ^b , R ^c , R ^d , R ^e , R ^f , R ^g or R ^h ;

R ^a is —C _p H _{2 (p-1)} (R ^a1 ) (R ^a2 ) —OR ^a3 ,

Where

(1) p is an integer from 1 to 6,

(2) R ^a1 represents a hydrogen atom,

(3) R ^a2 represents a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group, a halogen atom, a carboxy group, and

(4) R ^a3 represents a hydrogen atom or an acyl group;

R ^b represents —C _p H _{2 (p-1)} (R ^b1 ) (R ^b2 ) -N- (R ^b3 ) (R ^b4 ),

Where

(1) p is an integer from 1 to 6,

(2) R ^b1 represents a hydrogen atom,

(3) R ^b2 represents a C _1-6 alkyl group,

(4) R ^b3 represents a hydrogen atom or a C _1-6 alkyl group and

(5) R ^b4 represents

but. hydrogen atom or

b. -CO R ^b42 ,

where R ^b42 represents a C _1-6 alkyl group;

R ^c represents —C (= NR ^c1 ) —R ^c2 ,

Where

(1) R ^c1 represents

but. hydroxyl group

b. A C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the C _1-6 alkoxy group may be substituted with a hydroxyl group or a C _1-6 alkoxy group, or

c. an acyloxy group, and

(2) R ^c2 represents a C _1-6 alkyl group or an amino group;

R ^d is —C (═O) —R ^d1 ,

where R ^d1 represents

(1) a hydrogen atom,

(2) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group,

(3) a hydroxyl group,

(4) a C _1-6 alkoxy group,

(5) -N (R ^d11 ) (R ^d12 ),

where R ^d11 and R ^d12 may be the same or different and represent

A hydrogen atom or

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by an amino group, a carboxy group or a hydroxyl group, or

R ^d11 and R ^d12 together with an adjacent nitrogen atom can form a 5- or 6-membered saturated heterocyclic ring, or

(6) a C _1-6 alkoxy group;

R ^e represents a 5- or 6-membered aromatic heterocyclic group having from 1 to 4 heteroatoms, where the aromatic heterocyclic group may be substituted with a C _1-6 alkyl group or oxo group;

R ^f represents a C _1-6 alkyl group or a C _2-6 alkenyl group, wherein said C _1-6 alkyl group and a C _2-6 alkenyl group may be substituted with a substituent selected from the following Fa-2 group:

[Group Fa-2]

but. -COOH,

b. - N (R ^f21 ) (R ^f22 ),

where R ^f21 and R ^f22 may be the same or different and represent

Hydrogen atom

Acyl group or

· C _1-6 alkyl group,

where the C _1-6 alkyl group may be substituted by a carboxy group, and

c. halogen atom.

R ^g represents a Deputy having a ring B "represented by the following formula (IIb);

where A "represents a linker selected from the following group Ga-2:

[Group Ga-2]

- (CH ₂ ) _k -,

· - (CH ₂ ) _k -NR ^g1 (CO) -,

- - (CH ₂ ) _k -NR ^g1 - (CH ₂ ) _j -,

· - (CH ₂ ) _k -O- (CO) -,

· - (CH ₂ ) _k -O-,

- (CO) -NR ^g1 - (CH ₂ ) _j -,

- - (CO) - and

· - (CO) -NR ^g1 -,

where k and j can be the same or different and represent an integer from 1 to 4,

R ^g1 represents

·· hydrogen atom,

·· an acyl group, where the acyl group may be substituted by a hydroxyl group or a carboxy group, or

·· C _1-6 alkyl group, where the alkyl group may be substituted

-CON (R ^g41 ) (R ^g42 ).

Ring B ″ is a ring selected from the following Ha-2 group:

[Group Ha-2]

Aromatic hydrocarbon group

· C _3-8 cycloalkyl group and

A 5-7 membered saturated heterocyclic group containing at least one nitrogen atom, where a saturated heterocyclic ring can form a fused ring with a phenyl group, and

ring B ″ may be substituted with a substituent selected from the following group Ia-2:

[Group Ia-2]

but. -OR ^g2 ,

(where R ^g2 represents

Hydrogen atom

· C _1-6 alkyl group or

An aralkyl group, and

b. -COOOR ^g3 ,

where R ^g3 represents

A hydrogen atom or

· C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group; and

R ^h represents —N (R ^h1 ) (R ^h2 ),

where R ^h1 represents a hydrogen atom and R ^h2 represents an acyl group, where the acyl group may be substituted by a hydroxyl group or a C _1-6 alkoxycarbonyl group.

18. The aminopyridine compound or a pharmaceutically acceptable salt thereof in accordance with the above as described in claim 1, wherein the aminopyridine compound is selected from the following group of compounds:

(01) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,

(02) 5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-carbaldehyde,

(03) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanol,

(04) ethyl 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} acetic acid,

(05) N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} acetamide,

(06) N-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxamide,

(07) {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} methanol,

(08) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,

(09) 1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,

(10) 5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxamide,

(11) 1- {5- [6- (6-isopropoxypyrimidin-4-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,

(12) N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} acetamide,

(13) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone O- (2-hydroxyethyl) oxime,

(14) N- (2-aminoethyl) -5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxamide,

(15) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} propan-1-one,

(16) {2- [6- (5-Acetylthiophen-2-yl) pyridin-2-ylamino] pyridin-4-yl} -acetic acid ethyl ester,

(17) 2- [6- (5-Acetylthiophen-2-yl) pyridin-2-ylamino] isonicotinic acid methyl ester,

(18) 1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiophen-2-yl) ethanol,

(19) N-hydroxy-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxyamidine,

(20) 1- (5- {6- [4- (2-hydroxyethoxy) pyridin-2-ylamino] pyridin-2-yl} thiophen-2-yl) ethanone,

(21) 1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,

(22) oxime 1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,

(23) {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} piperazin-1-ylmethanone,

(24) 1- (5- {6- [4- (4,4-dimethyl-4,5-dihydrooxazol-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiophen-2-yl)

ethanone

(25) 2,2-difluoro-3-hydroxy-3- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} propionic acid,

(26) 4 - [({5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid,

(27) 4 - [(N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid,

(28) trans-4 - [(N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl]

cyclohexanecarboxylic acid

(29) 3- (N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) propionic acid,

(30) 4 - [(N-isobutyryl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid and

(31) 4 - [(N- (2-hydroxyacetyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid .

19. A pharmaceutical composition comprising an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

20. Syk inhibitor containing an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

21. A therapeutic and / or prophylactic agent for the treatment of allergic diseases, comprising an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

22. A therapeutic and / or prophylactic agent for treating bronchial asthma, comprising an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

23. A therapeutic and / or prophylactic agent for the treatment of allergic rhinitis, containing an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

24. A therapeutic and / or prophylactic agent for the treatment of allergic dermatitis, containing an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

25. A therapeutic and / or prophylactic agent for the treatment of allergic conjunctivitis, comprising an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

26. A therapeutic and / or prophylactic agent for the treatment of autoimmune diseases, comprising an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

27. A therapeutic agent for the treatment of progressive deforming arthritis containing an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

28. A therapeutic agent for treating systemic lupus erythematosus containing an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

29. A therapeutic agent for the treatment of multiple sclerosis containing an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

30. A therapeutic agent for treating a malignant tumor containing an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

31. A therapeutic agent for treating B-lymphoma and B-cell leukemia, comprising an aminopyridine compound or a pharmaceutically acceptable salt thereof, as described above, as an active ingredient.

32. A therapeutic and / or prophylactic agent for the treatment of allergic diseases, containing a Syk inhibitor, as described in paragraph 20 above, in combination with another antiallergic agent.

Advantages of the Invention

The present invention relates to a new aminopyridine compound represented by the above general formula (I), or a pharmaceutically acceptable salt thereof, and a medicament containing it as an active ingredient.

These compounds of the present invention are useful as active ingredients in pharmaceutical preparations. Since these compounds of the present invention have an excellent inhibitory effect and selectivity for Syk, they are useful as a therapeutic or prophylactic agent for treating diseases that are associated with an allergic or inflammatory reaction and in which the involved Syk is the main etiological cause (asthma, runny nose , atopic dermatitis, contact dermatitis, urticaria, food allergies, conjunctivitis, elastic catarrh, etc.) diseases in which, in turn, ADCC (autoimmune hemolytic anemia, asthenic bulbar palsy, etc.), a blood clot formed by platelet aggregation, etc. are involved.

The best way of carrying out the invention

The definitions used in the present description are as follows. The meaning of the term, not defined in detail, follows the meaning commonly used in this field.

The term “halogen atom” refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and preferably it refers to a fluorine atom, a chlorine atom or a bromine atom.

The term “C _1-6 alkyl group” refers to a linear or branched alkyl group having from 1 to 6 carbon atoms and especially includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group , tert-butyl group, pentyl group, isopentyl group, tert-pentyl group, hexyl group, etc. Preferably, it relates to a linear or branched alkyl group having from 1 to 4 carbon atoms and in particular it relates to a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group etc.

The term “alkylene group” refers to an alkylene group which may be branched, having from 2 to 6 carbon atoms, and in particular includes a methylene group, a propylene group, an isopropylene group, a butylene group, a 2-methylpropylene group, etc.

The term “C _1-6 alkoxy group” refers to an alkyloxy group in which its alkyl part is a “C _1-6 alkyl group” as defined above, and in particular includes a methoxy group, ethoxy group, propoxy group, isopropyloxy group, butoxy group, isobutyloxy group, tert- butyloxy group, pentyloxy group, hexyloxy group, etc. Preferably, it refers to a “C _1-4 alkoxy group”.

The term “C _1-6 alkoxycarbonyl group” refers to an alkoxycarbonyl group in which its alkyl portion is a “C _1-6 alkoxy group” as defined above, and in particular includes a methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl group, isobutoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, isopentyloxycarbonyl group, 2-methylbutoxycarbonyl group ppu, neopentyloxycarbonyl group, 1-ethylpropoxycarbonyl group, hexyloxycarbonyl group, 4-methylpentyloxycarbonyl group, 3-methylpentyloxycarbonyl group, 2-methylpentyloxycarbonyl group, 1-methylpentyloxycarbonyl group, 3,3-dimethylbutyloxycarbonyl-1,2-dimethylbutyloxy-dimethylbutoxy a dimethylbutoxycarbonyl group, a 1,2-dimethylbutoxycarbonyl group, a 1,3-dimethylbutoxycarbonyl group, a 2,3-dimethylbutoxycarbonyl group or a 2-ethylbutoxycarbonyl group, etc. Preferably, it refers to a (C _1-4 alkoxy) carbonyl group, and more preferably it relates to a methoxycarbonyl group or ethoxycarbonyl group.

The term “C _1-6 alkylamino group” refers to a “C _1-6 alkyl group” as defined above, which is bonded to an amino group and, for example, includes a methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, a butylamino group, an isobutylamino group, sec-butylamino group, tert-butylamino group butylamino group, pentylamino group, isopentylamino group, 2-methylbutylamino group, neopentylamino group, 1-ethylpropylamino group, hexylamino group, isohexylamino group, 4-methylpentylamino group, 3-methylpentylamino group, 2-methylpentylamino pentylamino group, 3,3-dimethylbutylamino group, 2,2-dimethylbutylamino group, 1,1-dimethylbutylamino group, 1,2-dimethylbutylamino group, 1,3-dimethylbutylamino group, 2,3-dimethylbutylamino group, or 2-ethylbutylamino group, etc. Preferably, it relates to C _1-4 alkylamino groups, such as a methylamino group, an ethylamino group and a propylamino group.

The term “di-C _1-6 alkylamino group” refers to a group in which two “C _1-6 alkyl groups” as defined above are linked to an amino group and, for example, includes a di-C _1-6 alkylamino group such as a dimethylamino group, diethylamino group, N-ethyl-N-methylamino group, dipropylamino group, dibutylamino group, dipentylamino group or dihexylamino group, and preferably this refers to di-C _1-4 alkylamino group.

The term “C _1-6 alkylsulfonyl group” refers to a group in which a “C _1-6 alkyl group” as defined above is attached to a sulfonyl group and, for example, includes a methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, pentylsulfonyl group, isopentylsulfonyl group, 2-methylbutylsulfonyl group, neopentylsulfonyl group, 1-ethylpropyls a laphonyl group, a hexylsulfonyl group, an isohexylsulfonyl group, a 4-methylpentylsulfonyl group, a 3-methylpentylsulfonyl group, a 2-methylpentylsulfonyl group, a 1-methylpentylsulfonyl group, a 3,3-dimethylbutylsulfonyl group, 1,1-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group, 2,2-dimethylbutylsulfonyl group 1,2-dimethylbutylsulfonyl group, 1,3-dimethylbutylsulfonyl group, 2,3-dimethylbutylsulfonyl group or 2-ethylbutylsulfonyl group, etc. Preferably, it refers to a C _1-4 alkylsulfonyl group, such as a methylsulfonyl group.

The term “carbamoyl group” refers to a carbamoyl group, a C _1-6 alkylcarbamoyl group or a di-C _1-6 alkylcarbamoyl group.

The term “C _1-6 alkylcarbamoyl group” refers to a group in which one “C _1-6 alkyl group” as defined above is bonded to a carbamoyl group and, for example, includes an alkylcarbamoyl group such as a methylcarbamoyl group, an ethylcarbamoyl group, a propylcarbamoyl group group, isopropylcarbamoyl group, butylcarbamoyl group, isobutylcarbamoyl group, sec-butylcarbamoyl group, tert-butylcarbamoyl group, pentylcarbamoyl group, isopentylcarbamoyl group, 2-methylbutylcarbamoyl group, neo-butylcarbamoyl group pentylcarbamoyl group, 1-ethylpropylcarbamoyl group or hexylcarbamoyl group, and preferably this refers to a C _1-4 alkylcarbamoyl group.

The term “di-C _1-6 alkylcarbamoyl group” refers to a group in which two

“C _1-6 alkyl groups” as defined above are associated with a carbamoyl group and, for example, include a dialkylcarbamoyl group such as a dimethylcarbamoyl group, diethylcarbamoyl group, N-ethyl-N-methylcarbamoyl group, dipropylcarbamoyl group, dibutylcarbamoyl group, dipentyl or a dihexylcarbamoyl group, and preferably this relates to a di-C _1-4 alkylcarbamoyl group.

The term “cycloaliphatic hydrocarbon” refers to a saturated or unsaturated C _3-8 cycloaliphatic hydrocarbon group, for example a cycloalkyl group, cycloalkenyl group, cycloalkadienyl group, etc.

The terms “C _3-8 saturated hydrocarbon ring” and “C _3-8 cycloalkyl group” have the same meaning and refer to a saturated cycloalkyl group having from 3 to 8 carbon atoms, and, for example, include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group , cyclohexyl group, cycloheptyl group, cyclooctyl group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, bicyclo [3.2.1] octyl group, etc. Preferably, it refers to a 5-7 saturated cycloalkyl group, and in particular it relates to a cyclopentyl group, a cyclohexyl group and a cycloheptyl group.

The term “saturated hydrocarbon ring” as mentioned above may include a double bond in its part, and “cycloalkenyl”, etc. also included in the term “saturated hydrocarbon ring”.

The term “C _3-8 cycloalkenyl group” refers to a cycloalkenyl group having from 3 to 8 carbon atoms and a cycloalkenyl group containing at least one, preferably 1 or 2 double bonds. Particularly included are a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a 2,4-cyclohexadien-1-yl group, a 2,5-cyclohexadiene-1-yl group, a cycloheptenyl group and a cyclooctenyl group, etc. . Preferably, it relates to a 5-7 cycloalkenyl group.

The term “cycloalkyl C _1-6 alkyl group” refers to a C _1-6 alkyl group substituted with a “C _3-8 cycloalkyl group” as described above, and preferred examples include a cycloalkyl group having from 4 to 13 carbon atoms, for example cyclopropylmethyl a group, a cyclopropylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a cyclohexyl ethyl group, etc.

The term “aryl group” refers to an aromatic hydrocarbon group or an aromatic heterocyclic group, but represents an aromatic hydrocarbon group when it refers to simply referred to as “an aryl group”. An aromatic hydrocarbon ring may simply be referred to as an aromatic carbocyclic ring. The term "aromatic hydrocarbon group" refers to an aromatic hydrocarbon group having from 6 to 14 carbon atoms, and in particular it includes a phenyl group, a naphthyl group, a biphenyl group, an antryl group, an indenyl group, an azulenyl group, a fluorenyl group, a phenanthryl group, and t .d. Preferably, it relates to a phenyl group, a naphthyl group, a biphenyl group.

The terms “aromatic aliphatic hydrocarbon group” and “aralkyl group” have the same meaning and represent an aliphatic hydrocarbon group having from 7 to 14 carbon atoms, and in particular represents an aralkyl group, an arylalkenyl group, an arylalkynyl group, etc.

The term “aralkyl group” refers to a C _1-6 alkyl group substituted with an aryl group, as mentioned above, and preferred examples include

A C _7-10 phenylalkyl group such as a benzyl group, phenethyl group, 1-phenylethyl group, 1-phenylpropyl group, 2-phenylpropyl group, 3-phenylpropyl group, phenylbutyl group; biphenylmethyl group;

A C _11-13 naphthylalkyl group such as an α-naphthylmethyl group, α-naphthylethyl group, β-naphthylmethyl group, β-naphthylethyl group. It may be a C _8-10 phenylalkenyl group, such as a styryl group; a naphthylalkenyl group such as a 2- (2-naphthylvinyl) group.

The term “aralkoxy group” refers to an aralkoxy group in which its aralkyl moiety is an aralkyl group, as mentioned above, and includes, for example, a C _7-10 phenylalkoxy group, such as a benzyloxy group, a phenyloxy group, 1-phenyl-phenoxypropyl, 1-phenyl-phenylpropyl 3-phenylpropyloxy; phenylbutyloxy; biphenylmethoxy; A C _11-13 naphthylalkoxy group such as an α-naphthylmethoxy group, α-naphthylethyloxy group, β-naphthylmethyloxy group, β-naphthylethyloxy group.

The term “aralkoxycarbonylamino group” refers to an amino group substituted with an aralkoxycarbonyl group, and the aralkoxy portion of the aralkoxycarbonyl group is an aralkoxy group, as mentioned above. For example, benzyloxycarbonylamino group, phenethyloxycarbonylamino group, etc. are included.

The term “C _2-6 alkenyl group” refers to an alkenyl group having from 2 to 6 carbon atoms, and includes, for example, ethene group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-1-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 3- a hexenyl group, a 2,4-hexadienyl group and a 5-hexenyl group. Among these C _2-6 alkenyl groups, for example, a vinyl group or a propenyl group is particularly preferred.

The term “acyl group” refers to an aliphatic acyl group, an aromatic acyl group, or a heterocyclic acyl group in which a saturated or unsaturated hydrocarbon group or heterocyclic group is attached to a carbonyl group. In a narrow sense, it refers to an acyl group in which a hydrocarbon group is aliphatically bonded to a carbonyl group. In particular, a C _1-6 alkylcarbonyl group (for example, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovalery group, a pivaloyl group, a hexanoyl group); A C _2-7 alkenylcarbonyl group (e.g., a crotonyl group); A C _3-8 cycloalkylcarbonyl group (e.g., cyclobutanecarbonyl group, cyclopentanecarbonyl group, cyclohexanecarbonyl group, cycloheptanecarbonyl group); A C _3-8 cycloalkenylcarbonyl group (e.g., a 2-cyclohexenecarbonyl group); A C _6-14 arylcarbonyl group (e.g., an arylcarbonyl group such as a benzoyl group, an α-naphthoyl group, β-naphthoyl group, a halogenated arylcarbonyl group such as a 2-bromobenzoyl group, 4-chlorobenzoyl group, a lower alkyl alkyl group, such as a 2,4,6-trimethylbenzoyl group, a 4-toluoyl group, an alkoxylated lower alkoxy group, an aryl carbonyl group such as a 4-anisoyl group, a nitrated aryl carbonyl group such as a 4-nitrobenzoyl group, 2-nitro a benzoyl group, an alkoxycarbonylated arylcarbonyl group, such as a 2- (methoxycarbonyl) benzoyl group, an arylated arylcarbonyl group, such as a 4-phenylbenzoyl group); A C _7-14 aralkylcarbonyl group (e.g., benzylcarbonyl group, phenethylcarbonyl phenylpropylcarbonyl group, phenylbutylcarbonyl group); A C _8-13 arylalkenylcarbonyl group (e.g., a styrylcarbonyl group); A C _8-13 arylalkynylcarbonyl group (e.g., a phenylethynylcarbonyl group); aromatic heterocyclic carbonyl group (e.g., nicotinoyl group, isonicotinoyl group, furyl carbonyl group, thienyl carbonyl group, pyrimidinyl carbonyl group, benzofuranyl carbonyl group, 1H-indazolyl carbonyl group, quinolyl carbonyl group); non-aromatic heterocyclic carbonyl groups (e.g., pyrrolidinyl carbonyl group, piperidine carbonyl group, morpholine carbonyl group, thiomorpholine carbonyl group, piperazine carbonyl group, thiazolidinyl carbonyl group, hexamethylene iminyl carbonyl group, tetrahydroisole etc.) can serve as an example.

The term “acyloxy group” refers to a group in which an oxygen atom is bonded to an “acyl group” as mentioned above, and, for example, includes a benzoyloxy group, etc.

The term “acylamino group” refers to a group in which the “acyl group”, as mentioned above, is bonded to an atom of an amino group, and for example, it refers to a linear or branched lower aliphatic acylamino group having from 2 to 7 carbon atoms, such as an acetylamino group , propionylamino group, butyrylamino group, isobutyrylamino group, valerylamino group, isovalerylamino group, pivaloylamino group, hexanoylamino group, acryloylamino group, methacryloylamino group, crotonoylamino group.

The term “heterocyclic group” or “heterocycle” refers to a saturated ring (which may have a double bond in its part) or an aromatic ring having 1-4 heteroatoms selected from an oxygen atom, a nitrogen atom and a sulfur atom other than a carbon atom as an atom forming a ring, where the number of atoms forming a ring is 3-14. A “heterocyclic group” may be monocyclic or may form a fused ring with a cycloalkyl ring, such as a cyclohexyl ring, an aromatic hydrocarbon ring, such as a benzene ring or another heterocyclic ring.

The term “5-7 membered saturated heterocyclic group” refers to a “heterocyclic group” containing a 5-7 membered, preferably a 5 or 6 membered saturated ring.

The term “heterocyclic group”, which is a monocycle, includes, for example, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a 1,3,5-triazinyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, 1,2,4 a triazolyl group, a tetrazolyl group, a thienyl group, a furyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrolinyl group, a pyrrolidinyl group, imidazolidinyl th group, piperidyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, tetrahydropyranyl group, etc.

The “heterocyclic group which is a monocycle” mentioned above may be an “aromatic heterocyclic group” or may be a saturated ring (which may have a double bond in its part). The term “saturated heterocyclic group”, as used herein, is a so-called heterocyclic group not containing a double bond, as well as a heterocyclic group having a double bond in its part. Examples of said “saturated heterocyclic groups” include a pyrrolidinyl group (eg, a 2-pyrrolidinyl group, 3-pyrrolidinyl group), a pyrrolinyl group (eg, 2-pyrrolidin-3-yl), an imidazolyl group (eg, 2-imidazolin-4-yl ), a piperidyl group (e.g., 2-piperidyl group, 3-piperidyl group), piperazinyl group (e.g. 2-piperazinyl group), morpholinyl group (e.g. 3-morpholinyl group), tetrahydrofuryl group, tetrahydrothienyl group, pyrazolidinyl group, 1 3-d oxolanyl group, 1,3-oxathiolanyl group, oxazolidinyl group, thiazolidinyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, dioxanyl group, morpholinyl group, thiomorpholinyl group, 2-oxopyrrolidinyl group, 2-oxo-piperidinyl group, 2-oxo-piperidinyl group, 4-oxi piperidinyl group, 4-oxiopyrinyl dioxopiperidinyl group, etc.

The term “aromatic heterocyclic group (heteroaryl group)” refers to a 5-7-membered, preferably 5- or 6-membered, monocyclic aromatic heterocyclic group or a bicyclic or tricyclic aromatic heterocyclic group in which such a monocycle is fused to other rings, where the heterocyclic group contains, for example, from 1 to 5, preferably from 1 to 4 heteroatoms selected from an oxygen atom, a nitrogen atom and a sulfur atom other than the carbon atom that forms the ring.

Preferred examples of such an “aromatic heterocyclic group” (heteroaryl group) include a furyl group (eg, 2-furyl, 3-furyl), a thienyl group (eg, 2-thienyl, 3-thienyl), a pyridyl group (eg, 2-pyridyl, 3-pyridyl, 4-pyridyl), a pyrimidinyl group (e.g. 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl), a pyridazinyl group (e.g. 3-pyridazinyl, 4-pyridazinyl), a pyrazinyl group (e.g. 2-pyrazinyl), pyrrolyl group (e.g. 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl), imidazolyl group (e.g. 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl), a pyrazolyl group (e.g. 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl), an oxazolyl group (e.g. 2-oxazolyl, 4-oxazolyl , 5-oxazolyl), isoxazolyl group, thiazolyl group (e.g. 2-thiazolyl, 4-thiazolyl, 5-thiazolyl), isothiazolyl group, oxadiazolyl group (e.g. 1,2,4-oxadiazol-5-yl, 1,3 , 4-oxadiazol-2-yl), a thiadiazolyl group (e.g., 1,3,4-thiadiazol-2-yl), a triazolyl group (e.g., 1,2,4-triazol-1-yl, 1,2,4 triazol-3-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-three zol-4-yl), tetrazolyl group (e.g. tetrazol-1-yl, tetrazol-5-yl), quinolyl group (e.g. 2-quinolyl, 3-quinolyl, 4-quinolyl), quinazolyl group (e.g. 2- quinazolyl, 4-quinazolyl), quinoxalyl group (e.g. 2-quinoxalyl), benzofuryl (e.g. 2-benzofuryl, 3-benzofuryl), benzothienyl group (e.g. 2-benzothienyl, 3-benzothienyl), benzoxazolyl group (e.g. 2 -benzoxazolyl), a benzothiazolyl group (e.g., 2-benzothiazolyl), a benzimidazolyl group (e.g., benzimidazol-1-yl, benzimidazol-2-yl), indolyl groups (eg indol-1-yl, indol-3-yl), 1H-indazolyl group (eg, 1H-indazol-3-yl), 1H-pyrrolo [2,3-b] pyrazinyl group (eg, 1H-pyrrolo [2,3-b] pyrazin-2-yl), 1H-pyrrolopyridinyl group (for example, 1H-pyrrolo [2,3-b] pyridin-6-yl), 1H-imidazopyridinyl group (for example 1H-imidazo [4 , 5-b] pyridin-2-yl, 1H-imidazo [4,5-c] pyridin-2-yl), 1H-imidazopyrazinyl group (for example, 1H-imidazo [4,5-b] pyrazin-2-yl ), a triazinyl group, an isoquinolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, a benzotriazolyl group, etc.

The term “5- or 6-membered aromatic heterocyclic group or saturated heterocyclic group” particularly includes a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a 1,3,5-triazinyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, 1 , 2,4-triazolyl group, tetrazolyl group, thienyl group, furyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyrrolidinyl group, pi peridyl group, piperazinyl group, etc.

The “fused heterocyclic group” mentioned above may be partially saturated, and examples of the partially saturated fused heterocycle include an isochromanyl group (eg, 3-isochromanil, etc.), an indolinyl group (eg, 2-indolinyl, etc. ), an isoindolinyl group (e.g. 1-isoindolinyl, etc.), a 1,2,3,4-tetrahydro-2-quinolyl group, a 1,2,3,4-tetrahydro-3-isoquinolyl group, etc. .

Preferred examples of a “fused aromatic heterocyclic group” or a “fused heterocyclic group” include a benzofuranyl group, an isobenzofuranyl group, a benzo [b] thienyl group, an indolyl group, an isoindolyl group, a 1H-indazolyl group, a benzimidazolyl group, a benzoxazolyl benzoyl group, benzoyl benzotriazolyl group, quinolyl group, isoquinolyl group, cinnolyl group, quinazolyl group, quinoxalinyl group, phthalazyl group, naphtha ridinyl group, purinyl group, pteridinyl group, carbazolyl group, α-carbonyl group, β-carbonyl group, acridinyl group, phenoxazinyl group, phenothiazinyl group, phenazinyl group, phenoxathiinyl group, tiantrenyl group, indolysinyl group, 5,6,7,8,8 -tetrahydroquinolyl group, pyrrolo [1,2-b] pyridazinyl group, pyrazolo [1,5-a] pyridyl group, imidazo [1,2-a] pyridyl group, imidazo [1,5-a] pyridyl group, imidazo [ 1,2-b] pyridazinyl group, imidazo [1,2-a] pyrimidinyl group y, 1,2,4-triazolo [4,3-a] pyridyl, 1,2,4-triazolo [4,3-b] pyridazinyl group, etc.

The term “heterocycloalkyl group” is the same term as the term “saturated heterocyclic group”.

The term “C _7-11 spiroheterocycloalkyl group” refers to a group in which a heterocycloalkyl group mentioned above forms a spiro bond with a C _3-8 cycloalkyl group mentioned above or a heterocycloalkyl group mentioned above and, for example, includes azaspiro [2.3] hexyl group, azaspiro [2.4] heptyl group, azaspiro [3.4] octyl group, azaspiro [2.5] octyl group, azaspiro [3.5] nonyl group, azaspiro [4.4] nonyl group, azaspiro [4.5] decanyl group, azaspiro [5.5] undecanyl group etc.

The term “C _1-6 alkylidene group” refers to a group that is formed by the removal of two hydrogen atoms from one carbon atom of an alkane, and the free valency becomes part of a double bond, and includes, for example, methylidine, ethylidene, propylidene, butylidene, pentylidene, hexylidene etc.

The definition of each term is as stated above, and the following are particularly preferred. In addition, the substitution can occur as the same or different two or more substituents.

X ¹ , X ² and X ^{3 are} preferably -CH =, = C (R ³ ) - and -CH =, respectively.

For Y ¹ and Y ^2, either one of Y ¹ and Y ² R is preferably a nitrogen atom and more preferably both are carbon atoms (-CH =) at the same time.

Preferably R represents a hydrogen atom.

R ³ preferably represents a halogen atom, a hydroxyl group or a C _1-6 alkyl group (where the alkyl group may be substituted by an alkoxycarbonyl group or a C _1-6 alkoxy group), particularly preferably the C _1-6 alkyl group (where the alkyl group may be substituted by an alkoxycarbonyl group or a C _1-6 alkoxy group), and even more preferably, it relates to a methyl group.

Preferably R ⁵ represents a hydrogen atom.

R ⁶ and R ⁶ ′ are preferably hydrogen atoms or C _1-6 alkyl groups and are particularly preferably hydrogen atoms.

R ^{7 are} particularly preferably R ^e , R ^g or R ^h .

“P” in R ^a and R ^b is an integer from 1 to 6, and preferably an integer from 1 to 4. Especially when p is 1 in R ^a , R ^{a2 is} preferably a substituent other than a hydrogen atom, and when p is 2 or more, the substituent —OR ^{a3 is} preferably attached at the position from the 2nd to the 6th group —C _p H _{2 (p-1)} (R ^b1 ) (R ^b2 ) -.

Similarly, when p is 1 in R ^b , R ^{b2 is} preferably a substituent other than a hydrogen atom, and when p is 2 or more, the substituent -N- (R ^b3 ) (R ^b4 ) ^{3 is} preferably attached at position 2 to the 6th group

-C _p H _{2 (p-1)} (R ^b1 ) (R ^b2 ) -.

In R ^a, preferably R ^a1 represents a hydrogen atom and preferably R ^a2 represents a C _1-6 alkyl group, an aralkyl group or an aryl group (wherein said C _1-6 alkyl group, an aralkyl group and an aryl group may be substituted with a substituent selected from hydroxyl group or carboxy group), and preferably R ^a3 represents a hydrogen atom, an acyl group, a carbamoyl group represented by —CON (R ^a31 ) (R ^a32 ) or a C _1-6 alkyl group (where the alkyl group may be substituted with C _1-6 alkoxycarbonyl group and whether -CON (R ^a31 ) (R ^a32 )).

As for R ^a31 and R ^a32 , in particular a 5- or 6-membered saturated heterocyclic group together with an adjacent nitrogen atom and having one or more nitrogen atoms can serve as an example of a saturated heterocyclic group, as shown below:

In R ^b, preferably R ^b1 represents a hydrogen atom, and preferably

R ^b2 represents a phenyl group which may be substituted by a C _1-6 alkyl group which may be substituted by a substituent selected from the Ca group or a hydroxyl group, and preferably R ^b3 represents a hydrogen atom or a C _1-6 alkyl group, and preferably R ^b4 represents a hydrogen atom, an acyl group which may be substituted by a hydroxyl group or a C _1-6 alkylsulfonyl group.

R ^c1 , which is particularly preferred in R ^c , is a hydroxyl group or a C _1-6 alkoxy group (where the C _1-6 alkoxy group may be substituted with a hydroxyl group or a C _1-6 alkoxy group).

R ^d1 , which is preferred in R ^d , is a C _1-6 alkyl group, a C _1-6 alkoxy group or —N (R ^d11 ) (R ^d12 ). Furthermore, R ^d11 and R ^{d12 are} preferably hydrogen atoms, C _1-6 alkoxy groups or C _1-6 alkyl groups in the present description (where the C _1-6 alkyl group may be substituted by a hydroxyl group or a carboxy group).

Preferably, the ring A in R ^e is as follows.

Particularly preferred examples for the “5-6 membered saturated heterocyclic group having one to two heteroatoms” in ^Re include the following saturated heterocyclic groups

More specifically, the following groups are included.

Of these groups, the following saturated heterocyclic groups are particularly preferred, which are directly bonded to the thiazole ring or thiophene ring of the compound of the above general formula (I) through a nitrogen atom forming said saturated heterocyclic rings

Preferred examples of a “5- or 6-membered saturated heterocyclic group having from 1 to 4 heteroatoms” in ^Re include the following aromatic heterocyclic groups

Preferred examples of the “9-12 membered fused aromatic heterocyclic group having 1 or 2 heteroatoms that may be partially saturated” in R ^e include the following fused aromatic heterocyclic groups

The following condensed ring is also included.

Particularly preferred examples of the “C _3-8 cycloalkyl group” in ^Re include the following cycloalkyl group.

Preferred examples of the “C _7-11 spiroheterocycloalkyl group having 1 or 2 heteroatoms” in R ^e include the following spiroheterocycloalkyl group

Substituents for ring A are as shown in group Ea. Preferably, the substituents for ring A are as follows.

Preferred Examples for -OR ^e1  include

A hydroxyl group

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a carboxy group or —CON (R ^e11 ) (R ^e12 ) (where R ^e11 and R ^e12 may be the same or different and each represents a hydrogen atom or C _1-6 alkyl group),

Acyloxy group,

An aralkoxy group or

Carbamoyloxy group.

Preferred Examples for -COOR ^e2  include

A carboxy group or

· C _1-6 alkoxycarbonyl group.

Preferred Examples for —CO — N (R ^e41 ) (R ^e42 ) include

-CO-NO (R ^e41 ) (R ^e42 ), where R ^e41 and R ^e42 may be the same or different and each represents

Hydrogen atom

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C _1-6 alkoxy group, an amino group, a C _1-6 alkylamino group, a di-C _1-6 alkylamino group, a halogen atom, a carboxy group, a carbamoyl group, a C _1-6 alkylcarbamoyl group, a di-C _1-6 alkylcarbamoyl group, or a 5- or 6-membered saturated heterocyclic group or an aromatic heterocyclic group having 1 or 2 heteroatoms,

A hydroxyl group

C _1-6 alkoxy group,

· A C _5-6 cycloalkyl group, wherein a C _5-6 cycloalkyl group may be substituted by a hydroxyl group or a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted by a hydroxyl group; or

· C _1-6 alkylsulfonyl group.

A carbamoyl group is particularly preferred.

Preferred Examples for -COR ^e3  include

-COR ^e3 where R ^e3 represents

· A C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group and a C _1-6 alkylsulfonyl group,

A 5- or 6-membered saturated heterocyclic group or an aromatic heterocyclic group having 1 or 2 heteroatoms, where the saturated heterocyclic group and the aromatic heterocyclic group may be substituted with a substituent selected from a hydroxyl group, an oxo group, a carboxy group, a C _1-6 alkoxy group, where The C _1-6 alkoxy group may be substituted by a carbamoyl group, a carbamoyl group, where the carbamoyl group may be substituted by a hydroxyl group, an acyl group, an acyloxy group, an amino group, an acylamino Rupp, wherein acylamino group may be substituted with a hydroxyl group or a carbamoyl group, C _1-6 alkylamino, di-C _1-6 alkylamino, C _1-6 alkylsulfonylamino, a 5- or 6-membered saturated heterocyclic group or an aromatic heterocyclic group and C _{1- 6 by} an alkyl group, where a C _1-6 alkyl group may be substituted by a hydroxyl group, a C _1-6 alkoxy group, where a C _1-6 alkoxy group may be substituted by a carbamoyl group, an acylamino group and a carbamoyl group, or

· A C _5-6 cycloalkyl group or an aryl group, wherein the C _5-6 cycloalkyl group and the aryl group may be substituted with a hydroxyl group, an oxo group, a C _1-6 alkoxy group, a carbamoyl group, an acylamino group, an oxymino group or an acyloxy group.

In addition, preferred examples of a “5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms” in the above R ^e3 include the following heterocyclic groups

In addition, preferred examples of a “5- or 6-membered aromatic heterocyclic group having 1 or 2 heteroatoms” in the above R ^e3 include the following heterocyclic aromatic groups

In addition, preferred examples for —COR ^e3 in the above R ^e3 include the following

Preferred Examples for —N (R ^e51 ) (R ^e52 ) include

-N (R ^e51 ) (R ^e52 ), where R ^e51 and R ^e52 may be the same or different and each represents

Hydrogen atom

· C _1-6 alkylsulfonyl group,

· A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C _1-6 alkoxy group and a carbamoyl group,

-CON (R ^e11 ) (R ^e12 ),

where R ^e11 and R ^e12 have the meanings indicated above,

-COR ^e511 ,

where R ^e511 represents a 5- or 6-membered saturated heterocyclic group containing at least one nitrogen atom, a C _1-6 alkyl group (where

A C _1-6 alkyl group may be substituted by a hydroxyl group) or a C _5-6 cycloalkyl group, where the cycloalkyl group may be substituted by a hydroxyl group.

Preferred Examples for C _1-6 alkyl groups include

C _1-6 alkyl groups which may be substituted

Hydroxyl group

· A C _1-6 alkoxy group, a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a carboxy group or —CO — N (R ^e11 ) (R ^e12 ), and R ^e11 and R ^e12 are as defined above;

· -COOR ^e2 ,

where R ^e2 has the meaning indicated above,

-N (R ^e51 ) (R ^e52 ),

where R ^e51 and R ^e52 have the meanings indicated above,

-CO-N (R ^e51 ) (R ^e52 ),

where R ^e51 and R ^e52 have the meanings indicated above,

A halogen atom or

A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, wherein the saturated heterocyclic group may be substituted with a hydroxyl group or a C _1-6 alkyl group.

Particularly preferred is a C _1-6 alkyl group substituted with —COOR ^e2 , for example, a carboxymethyl group or an unsubstituted methyl group.

Preferred examples for a 5-6 membered saturated heterocyclic group (which may be partially saturated) containing 1 or 2 heteroatoms selected from a nitrogen atom and an oxygen atom, or an aromatic heterocyclic group containing from 1 to 4 heteroatoms selected from a nitrogen atom and from an oxygen atom, where a saturated heterocyclic group and an aromatic heterocyclic group may be substituted by an oxo group or C _1-6 alkyl group include

In addition, preferred substituents for ring A are an oxo group, a C _1-6 alkylsulfonyl group, and a cyano group.

k and l in the linker “A” of the group R ^g preferably have a value of 1 or 2, and k + l has a value of 2 to 4.

In addition, preferably ring B in R ^g is as follows.

Preferred examples of the “aryl group” in R ^g include a phenyl group.

Preferred examples of the “C _3-8 cycloalkyl group” in R ^g include the following C _3-8 cycloalkyl groups:

Preferred examples of a “5-7 membered saturated heterocyclic group having one or more nitrogen atoms” in R ^g include the following saturated heterocyclic groups:

Preferred examples of a “5-6 membered aromatic heterocyclic group having at least one heteroatom” in R ^g include the following aromatic heterocyclic groups:

Preferred examples of the “8-11 membered fused aromatic heterocyclic group having at least one heteroatom” in R ^g include the following fused aromatic heterocyclic groups:

R ^h1 in R ^h preferably represents a hydrogen atom or a C _1-6 alkyl group.

In addition, “aromatic carbocyclic ring group”, “5-6 membered aromatic heterocyclic group having 1 or 2 heteroatoms”, “C _3-8 cycloalkyl group” and “5-6 membered saturated heterocyclic group having 1 or 2 heteroatoms "in the Ja group for R ^h2 . Particularly preferred is a “C _3-8 cycloalkyl group”.

Preferred examples of the “aromatic carbocyclic group” in the Ja group for R ^h2 include phenyl groups.

Preferred examples of the “5-6 membered aromatic heterocyclic group having 1 or 2 heteroatoms” in the Ja group for R ^h2 include the following aromatic heterocyclic groups:

Preferred examples of the “5-6 membered saturated heterocyclic group having 1 or 2 heteroatoms” in the Ja group for R ^h2 include the following saturated heterocyclic groups

Preferred examples of the “C _3-8 cycloalkyl group” in (5) for R ^h2 include a cyclohexyl group. Particularly preferred is a cyclohexyl group substituted with a carboxy group.

Preferred examples of the “5-6 membered saturated heterocyclic group having 1 or 2 heteroatoms” in (6) for R ^h2 include the following saturated heterocyclic groups:

The definition of each term is described above, but for each symbol X ¹ , X ² , X ³ , Z, Y ¹ , Y ² , R, R ¹ , R ⁵ , R ⁶ , R ⁷ and various substituents, its narrower concept is defined in general the formula (I), as "preferably X ¹ , X ² , X ³ , Z, Y ¹ , Y ² , R, R ¹ , R ⁵ , R ⁶ , R ⁷ and various substituents", which is given in the specific following examples ( for example, “methyl group, ethyl group”, “phenyl group, naphthyl group”), and X ¹ , X ² , X ³ , Z, Y ¹ , Y ² , R, R ¹ , R ⁵ , R are particularly preferred ^6, R ⁷ and different substituent groups derived from compounds which de onstriruyut among them a particularly high inhibitory activity

(more than ++).

Preferred examples of the compounds of the present invention include the following compounds, where the number in parentheses is the number of the compound mentioned in the examples:

1-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyridin-2-one (compound A-1),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxylic acid (compound A-2),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide (compound A-3),

N-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide (compound A-4),

N- (2-hydroxyethyl) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide (compound A-5),

trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid methyl ester (compound A-6),

trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid (compound A-7),

(4-hydroxypiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone (compound A-8 ),

N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) amine (compound A-9),

N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide (compound A-10),

(S) -3-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one (compound A-11),

(S) -2,2-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidine-3-carboxylic acid tert-butyl ester ( compound A-12)

(S) -2-amino-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol (compound A-13),

(S) -4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one (compound A-14),

dihydrochloride (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-15),

trans-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid (compound A-16),

3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid (compound A-17),

2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid (compound A-18) ,

N- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} propionamide (compound A-19),

N- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} acetamide (compound A-20),

N- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyrazin-2-yl] thiazol-2-yl} acetamide (compound A-21),

(S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -acetic acid ethyl ester (compound A-25),

(S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol (compound A-26),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanone (compound A-27),

5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carboxylic acid ethyl ester (compound A-28),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanone oxime (compound A-30),

(S) -5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} dihydrofuran-2-one (compound A-33),

O- (2-hydroxyethyl) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanone (compound A-35),

N-methoxy-N-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carboxamide (compound A-46),

N-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carboxamide (compound A-47),

N-methyl - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide (compound A-52),

(S) -5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-one (compound A-55),

5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentanoic acid (compound A-69),

5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentan-1-ol (compound A-70),

5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentanamide (compound A-71),

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanol (compound A-73),

oxime 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanone (compound A-74),

N- {6- [2 - ((S) -1-aminoethyl) thiazol-5-yl] pyridin-2-yl} -N - ([4,4 '] bipyridinyl-2-yl) amine (compound A- 75)

N - ((S) -1- {5- [6 - ([4,4 '] bipyridinyl-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide (compound A-79),

N - ((S) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide (compound A-81),

(S) -2-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} propan-1-ol (compound A-82),

N - ((S) -1- {5- [6- (isoquinolin-3-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide (compound A-91),

(4-methylpyridin-2-yl) - [6- (2-piperidin-4-ylthiazol-5-yl) pyridin-2-yl] amine (compound A-92),

trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-111),

5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentylamine (compound A-128),

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} butan-1-ol (compound A-132),

4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenol (compound A-135),

2-hydroxy-N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide (compound A-147),

3 - ({5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carbonyl} amino) propionic acid (compound A-148),

4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) benzoic acid (compound A-151),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperidin-4-ol (compound A-152),

3,3-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} butan-1-ol (compound A-158),

[4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenyl] methanol (compound A-159),

N - ((R) - (4-hydroxyphenyl) - {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} methyl) acetamide (compound A-161),

N- (2-hydroxyethyl) -4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) benzamide (compound A-162),

4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) cyclohexanone (compound A-172),

4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) cyclohexanol (compound A-173),

((3R, 4S) -3,4-dihydroxypyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone (compound A-174),

(trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) - (piperazin-1-yl)

methanone (compound A-176),

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-1-carboxamide (compound A-182),

2-hydroxy-1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-1-yl) ethanone (compound A-187),

trans-4- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid (compound A-188),

3- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-1-yl) -3-oxopropionic acid hydrochloride (compound A-192) ,

N- (4-methylpyridin-2-yl) -N- {6- [2- (piperazin-1-ylmethyl) thiazol-5-yl] pyridin-2-yl} amine (compound A-194),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperidin-4-ylamine (compound A-197),

N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} methanesulfonamide (compound A-200),

N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) acetamide (compound A-202),

trans-4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid (compound A-204),

2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol (compound A-205),

(trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanol (compound A-211),

trans-4- {5- [6- (isoquinolin-3-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid (compound A-215),

trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethylamine (compound A-219),

((3R, 4S) -3,4-dihydroxypyrrolidin-1-yl) - [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl } ethyl) phenyl] methanone (compound A-223),

N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) acetamide (compound A-228),

N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl)

methanesulfonamide (compound A-229),

2-hydroxy-N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) acetamide (compound A-235),

2-hydroxy-N- [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenyl] acetamide (compound A-237) ,

((3R, 4S) -3,4-dihydroxypiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone (compound A-239),

((R) -3-hydroxypyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone ( compound A-241),

(4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} phenyl) methanol (compound A-243),

N- (4-methylpyridin-2-yl) -N- [6- (2-pyridin-3-ylmethylthiazol-5-yl) pyridin-2-yl] amine (compound A-248),

N- (4-methylpyridin-2-yl) -N- {6- [2- (2-piperidin-4-yl-ethyl) thiazol-5-yl] pyridin-2-yl} -amine (compound A-258),

N- (6- {2- [2- (1-methanesulfonylpiperidin-4-yl) ethyl] thiazol-5-yl} pyridin-2-yl) -N- (4-methylpyridin-2-yl) amine (compound A -260)

2-hydroxy-1- [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) piperidin-1-yl] ethanone (compound A-263),

N- (2-hydroxyethyl) -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-267),

N- (2-morpholin-4-yl-ethyl) -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-268) ,

[3- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenyl] methanol (compound A-277),

(3-hydroxypyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone (compound A-282 ),

4- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonyl)

piperazin-2-one (compound A-283),

((R) -2-hydroxymethylpyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone ( compound A-286),

(4-aminopiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone (compound A-290 ),

[4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) piperidin-1-yl] -

(piperidin-4-yl) methanone (compound A-295),

(trans-4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) - (4-hydroxypiperidin-1-yl) methanone (compound A-297 ),

N- (4-hydroxypiperidin-1-yl) -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-298) ,

N - [(R) -2-hydroxy-1- (3H-imidazol-4-ylmethyl) ethyl] -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-303),

N - [(S) -2-hydroxy-1- (3H-imidazol-4-ylmethyl) ethyl] -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-304),

N- (2-dimethylaminoethyl) -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-309),

(3-aminopyrrolidin-1-yl) trihydrochloride - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone (compound A- 311)

N- [1- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonyl)

pyrrolidin-3-yl] methanesulfonamide (compound A-312),

(3R, 4S) -1- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) pyrrolidin-3,4-diol ( compound A-314),

trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonitrile (compound A-316),

cis-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonitrile (compound A-317),

(S) -5- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-one (compound A-319),

(S) -1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol (compound A-320),

(S) -1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) ethanol (compound A-321),

(S) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol (compound A-322),

(S) -5- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-one (compound A-323),

3- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) -4H- [1,2,4] oxazol-5- he (compound A-325)

N- (4-methylpyridin-2-yl) -N- (6- {2- [4- (1H-tetrazol-5-yl) cyclohexyl] thiazol-5-yl} pyridin-2-yl) amine (compound A -326)

(S) -5- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidin-2-one (compound A-330),

N- (1,1-dimethyl-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide (compound A-334),

(S) -1- (5- {6- [4- (2-methyl- [1,3] dioxolan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) ethanol (compound A-335)

N-methyl-trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-336),

N- (1,1-Dimethyl-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) methanesulfonamide (compound A-337),

trans-4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-338),

trans-4- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide (compound A-339),

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} cyclohexanol (compound A-341),

(S) -1- (5- {6- [4- (2-hydroxyethoxy) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) ethanol (compound A-344),

(S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} dimethylcarbamic acid ethyl ester (compound A-345),

potassium carbonate 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperazin-2-one (compound A-351),

4- (2-hydroxy-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenol (compound A-362),

4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethoxy} acetyl) piperazin-2-one (compound A-370),

N - ((R) - (4-hydroxyphenyl) - {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} methyl) -N-methylacetamide (compound A- 372)

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperazin-2,6-dione (compound A-383),

(S) -5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one (compound A-409),

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperazin-2-one (compound A-416),

N- (4-methylpyridin-2-yl) -N- [6- (2-morpholin-4-ylthiazol-5-yl) pyridin-2-yl] amine (compound A-417),

1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone (compound A-419),

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-sulfonamide (compound A-421),

N- (4-methoxypyridin-2-yl) -N- {6- [2- (morpholin-4-yl) thiazol-5-yl] pyridin-2-yl} amine (compound A-422),

(3R, 4S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3,4-diol (compound A-423),

N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} acetamide (compound A-424),

N- [6- (4-methyl-2-morpholin-4-ylthiazol-5-yl) pyridin-2-yl] -N- (4-methylpyridin-2-yl) amine (compound A-425),

N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine (compound A-426),

N-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-1-carboxamide (compound A-427),

1- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide (compound A-429),

N- {6- [2- (4-methoxypiperidin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine (compound A-431),

N- {6- [2- (4-methylpiperazin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine (compound A-432),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ol (compound A-433),

N-methyl-1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide (compound A-436),

4- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-carbaldehyde (compound A-437),

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-1-carboxylic acid methyl ester (compound A-438),

2-hydroxy-1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone (compound A-439),

1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) propan-1-one (compound A-440),

N, N-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-1-carboxamide (compound A-441),

1- (4- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone (compound A-442),

1- (4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone (compound A-443),

4- (methyl- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid (compound A-444),

4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino)

cyclohexanecarboxamide (compound A-446),

3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) -4H- [1,2,4] oxadiazole- 5-one (compound A-450),

N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-piperidin-4-ylamine (compound A-452),

4- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carbonyl)

piperazin-2-one (compound A-453),

N- (2,2-dimethoxyethyl) -N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine (compound A-457) ,

1- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] ethanone (compound A-458)

2-hydroxy-1- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl ] ethanone (compound A-459),

N-methyl-4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-

carboxamide (compound A-460),

N- {2- [4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1- silt] -2-oxoethyl} acetamide (compound A-461),

dihydrochloride (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetic acid (compound A-464),

2- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetamide (compound A-465),

N-methyl-2- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetamide (compound A- 466)

N- (2-hydroxyethyl) -2- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetamide (compound A-468)

N-methyl-N-methylcarbamoylmethyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide (compound A-469),

N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-tetrahydropyran-4-ylamine (compound A-470),

4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] phenol (compound A-471),

N - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) acetamide (compound A-472),

(R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ylamine (compound A-473),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxylic acid (compound A-474),

2-hydroxy-N - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) acetamide (compound A -475)

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxamide (compound A-476),

N-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxamide (compound A-477),

N- (2-hydroxyethyl) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxamide (compound A-478),

(R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ol (compound A-479),

trans-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanol (compound A-480),

N- {6- [2- (3-methoxymethylpiperidin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine (compound A-481),

2-hydroxy-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide (compound A-482),

2-hydroxy-N-methyl-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide (compound A -483)

N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl)

methanesulfonamide (compound A-484),

N-methyl-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl)

methanesulfonamide (compound A-485),

2-hydroxy-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ylmethyl) acetamide (compound A-486),

N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ylmethyl) acetamide (compound A-487),

N-methyl- (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidine-2-carboxamide dihydrochloride (compound A-488),

N - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl)

methanesulfonamide (compound A-489),

N- {6- [2 - ((R) -3-methoxypyrrolidin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine (compound A- 490)

N-methyl-4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino)

cyclohexanecarboxamide (compound A-492),

N- (2-hydroxyethyl) -4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino)

cyclohexanecarboxamide (compound A-493),

N- (2-acetylaminoethyl) -4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino)

cyclohexanecarboxamide (compound A-494),

dihydrochloride (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-ylmethoxy)

acetic acid (compound A-497),

(1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) methanol (compound A-498),

2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-ylmethoxy)

acetamide (compound A-499),

4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide (compound A-500),

N-methyl-4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide (compound A-501),

N-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-ylmethoxy)

acetamide (compound A-502),

N- (2-hydroxyethyl) -4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide (compound A- 503)

2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide (compound A-504),

N-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide (compound A-505),

N- (2-hydroxyethyl) -2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide (compound A -506)

N, N-diallyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine (compound A-507),

N- [2- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] acetamide (compound A- 508)

2-hydroxy-N- [2- (N'-methyl- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] acetamide (compound A -509)

N- (4-methanesulfonylpiperidin-1-yl) -N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine (compound A- 510)

N, N-dimethyl-4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-

carboxamide (compound A-511),

(4-hydroxyphenyl) - [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl ] methanone (compound A-513),

1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylamino} piperidin-1-yl) ethanone (compound A-514),

1- [4- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] ethanone (compound A-515)

N-methyl-2 - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yloxy) acetamide (compound A -516)

1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide (compound A-517),

1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide (compound A-518),

2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethanol (compound A-519),

N- (2-methoxyethyl) -N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine (compound A-520),

N- [2- (N '- (1-acetylpiperidin-4-yl) -N' - {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino ) ethyl] methanesulfonamide (compound A-524),

1- [4- (N- (2-hydroxyethyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl ] ethanone (compound A-525),

1- [4- (N- (2-methoxyethyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl ] ethanone (compound A-526),

(S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide (compound A-528),

N-methyl- (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide (compound A-529),

N- (2,2,2-trifluoroethyl) - (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide (compound A-530)

(R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxylic acid (compound A-531),

((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) methanol (compound A-532),

(R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxamide (compound A-533),

1- [4- (N-ethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] ethanone (compound A-534),

1- {4- [N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N- (2,2,2-trifluoroethyl) amino] piperidine -1-yl} ethanone (compound A-535),

1- [4- (N- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-methylamino) piperidin-1-yl] ethanone (compound A -536)

1- [4- (N- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-methylamino) piperidin-1-yl] -2-hydroxyethanone (compound A-537)

(R) -1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ol (compound A-538),

(R) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ol (compound A-539),

4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxylic acid (compound A-540),

(S) -1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide (compound A-541),

(S) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide (compound A-542),

1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide (compound A-543),

2- (N- (2-hydroxyethyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethanol (compound A-544),

2- [N- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N- (2-hydroxyethyl) amino] ethanol (compound A-545),

(R) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxylic acid (compound A-546),

1- (5- {6- [4- (1-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-

carboxamide (compound A-547),

(R) -1- (5- {6- [4- (2-methyl- [1,3] dioxalan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidine -3-ol (compound A-548),

1- (2- {6- [2 - ((R) -3-hydroxypyrrolidin-1-yl) thiazol-5-yl] pyridin-2-ylamino} pyridin-4-yl) ethanone (compound A-549),

4- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) -4-oxo-butyric acid (compound A-551),

N-hydroxy- (R) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxamide (compound A-552),

4- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] -4- oxobutyric acid (compound A-553),

(R) -1- (5- {6- [4- (1-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidin-3-ol (compound A-554),

2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetamide (compound A-556),

(R) -1- (5- {6- [4- (2-methyl- [1,3] dioxalan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidine -3-

carboxylic acid (compound A-558),

(R) -1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxylic acid (compound A-560),

(S) -1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide (compound A-561),

(1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) methanol (compound A-562),

1 - [(R) -3- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pyrrolidin-1-yl ] ethanone (compound A-563),

(S) -1- {5- [6- (4-Acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidine-2-carboxylic acid dihydrochloride (compound A-564),

(R) -1- (5- {6- [4- (2-methyl- [1,3] dioxalan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidine -3-

carboxamide (compound A-565),

((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) acetic acid (compound A-567),

(S) -3-methyl-2- [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino dihydrochloride) acetylamino] butyric acid (compound A-568),

3- [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetylamino dihydrochloride]

propionic acid (compound A-570),

dihydrochloride [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetylamino] acetic acid (compound A-571) ,

dihydrochloride [1- (5- {6- [4- (2-methyl- [1,3] dioxalan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4 -il]

acetic acid (compound A-572),

dihydrochloride (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-573),

4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid dihydrochloride (compound A-574) ,

((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yloxy) -acetic acid dihydrochloride (compound A-575),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidine-3-carboxylic acid dihydrochloride (compound A-576),

(R) -1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidin-3-ol dihydrochloride (compound A-577) ,

4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) benzoic acid (compound A-578),

(2S, 4R) -4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pyrrolidin-2-

carboxylic acid (compound A-579),

dihydrochloride {N-methyl-N- [2- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetyl ] amino} acetic acid (compound A-580),

2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid (compound A-582) ,

3 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid dihydrochloride (compound A-586) ,

dihydrochloride {4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] phenyl} acetic acid (compound A -587)

(1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) acetic acid (compound A-588),

dihydrochloride (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) acetic acid (compound A-589),

N- (4-methylpyridin-2-yl) -N- (6- {2 - [(R) -3- (1H-tetrazol-5-yl) piperidin-1-yl] thiazol-5-yl} pyridin- 2-yl) amine (compound A-590),

cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid (compound A-591),

trans-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid (compound A-592),

4- [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] benzoic acid dihydrochloride (compound A- 593)

dihydrochloride (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yloxy) acetic acid (compound A-594),

(4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) acetic acid hydrochloride (compound A-595),

4 - {[N-methyl-N- (5- {6- [4- (2-methyl- [1,3] dioxalan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2 -yl) amino] methyl}

benzoic acid (compound A-596),

4 - [(N-dimethylcarbamoylmethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid dihydrochloride (compound A-597) ,

cis-4- (N-carbamoylmethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid (compound A-598),

trans-4 - [(N-carbamoylmethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid (compound A-599),

5 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] thiophen-2-

carboxylic acid (compound A-603),

3-chloro-4 dihydrochloride - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid (compound A-604),

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethoxy} benzoic acid (compound A-605),

3-methoxy-4 dihydrochloride - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid (compound A-606),

2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (compound A-607) ,

2 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] thiazol-4-

carboxylic acid (compound A-609),

[trans-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexyl] acetic acid (compound A-610 ),

[cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexyl] acetic acid (compound A-611 ),

4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) cyclohexanecarboxylic acid (compound A-612),

dihydrochloride (4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-613),

4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -3,4-dihydro-2H-benzo [1,4] oxazine-8-carboxylic acid (compound A-614)

{5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethoxy} acetic acid hydrochloride (compound A-615),

4- [1-methyl-1- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] benzoic acid dihydrochloride (compound A-616)

[4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) phenyl] acetic acid dihydrochloride (compound A-617) ,

dihydrochloride (1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-620),

trans-4 - [(N-benzyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid (compound A-622),

[trans-4- (N-benzyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexyl] acetic acid (compound A-624 ),

trans-4 - [(N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid (compound A-626),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroquinoline-5-carboxylic acid (compound A-627) ,

fluoro- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ylidene) acetic acid (compound A-631),

5- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pentanoic acid (compound A-632),

N- [2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetyl]

methanesulfonamide (compound A-633),

4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) butyric acid dihydrochloride (compound A-634),

dihydrochloride (1- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl)

acetic acid (compound A-635),

dihydrochloride (1- {5- [6- (5-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-636),

dihydrochloride (1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-637),

trans-4- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino)

cyclohexanecarboxylic acid (compound A-638),

3- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) phenyl] propionic acid (compound A-639 ),

(E) -6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2enoic acid dihydrochloride ( connection A-640),

(2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinolin-6-yl) acetic acid (compound A -641)

3- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinolin-5-yl) propionic acid ( connection A-642),

5- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pentanoic acid (compound A-643),

5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylamino} pentanoic acid (compound A-644),

6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hexanoic acid dihydrochloride (compound A-645),

(Z) -2-fluoro-6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2 dihydrochloride -enoic acid (compound A-647),

(8- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -8-azabicyclo [3.2.1] oct-3-yl) acetic acid (compound A -648)

(8- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -8-azabicyclo [3.2.1] oct-3-yl) acetic acid (compound A -649)

dihydrochloride (1- {5- [6- (4-cyanopyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-650),

{4 - [(N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] phenyl}

acetic acid (compound A-651),

2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid (compound A-652),

(1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-653),

4- [1-methyl-1- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] benzoic acid ( compound A-654),

3-methyl-6- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-enoic acid dihydrochloride ( compound A-655),

3-methyl-6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-enoic acid dihydrochloride ( compound A-656),

dihydrochloride (E) -6- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-enoic acid ( compound A-657),

N- (2-hydroxyethyl) - (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidine-2-carboxamide (compound A- 658)

2- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetamide (compound A-663),

3-methyl-2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) butylamide (compound A-668),

2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) ethanol (compound A-677),

5- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pentan-1-ol (compound A-678),

(1- {5- [6- (pyrazin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-680),

dihydrochloride [1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl]

acetic acid (compound A-681),

fluoro- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-684),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperidine-4-carboxamide (compound A-685),

dihydrochloride (1- {5- [6- (4-ethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-692),

N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine (compound A-693),

N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N- (2-morpholin-4-yl-ethyl) amine (compound A-695),

2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} amino) acetamide (compound A-697),

2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) butyric acid (compound A-698),

trans-4 dihydrochloride - [(N-methyl-N- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid (compound A-699),

dihydrochloride [1- (5- {6- [4- (2,2,2-trifluoroethoxy) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl]

acetic acid (compound A-700),

2-methyl-1- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) propan-2-ol (compound A -702)

3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) propionic acid (compound A-704),

N- (2-hydroxyethyl) -4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine- one-

carboxamide (compound A-705),

2-methyl-2- (1- {5- [6- (pyrazin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid dihydrochloride (compound A-707),

4 - [(N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} amino) methyl] benzoic acid (compound A-709),

dihydrochloride (1- {5- [6- (4-tert-butylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-710),

dihydrochloride (1- {5- [6- (4-isopropylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid (compound A-711),

6- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -6-azaspiro [2.5] octane-1-carboxylic acid (compound A-712),

2- [1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl] -2-methylpropionic acid (compound A-713),

2-methyl-2- (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid (compound A-714),

fluoro- (1- {5- [6- (Pyrazin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid dihydrochloride (compound A-715),

fluoro- (1- {5- [6- (Pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid dihydrochloride (compound A-716),

dihydrochloride [1- (5- {6- [4- (1-hydroxy-1-methylethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-

sludge] acetic acid (compound A-717),

2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid dihydrochloride (compound A-718 ),

5- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) pentanoic acid dihydrochloride (compound A-719),

2-methyl-2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} amino) propionamide (compound A-720),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone (compound B-1),

5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-carbaldehyde (compound B-2),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanol (compound B-3),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} -acetic acid ethyl ester (compound B-4),

N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} acetamide (compound B-10),

N-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxamide (compound B-11),

{5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} methanol (compound B-12),

1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone oxime (compound B-15),

1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone (compound B-17),

5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxamide (compound B-23),

1- {5- [6- (6-isopropoxypyrimidin-4-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone (compound B-30),

N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} acetamide (compound B-31),

O- (2-hydroxyethyl) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone (compound B-38),

N- (2-aminoethyl) -5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxamide (compound B-43),

oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} propan-1-one (compound B-51),

{2- [6- (5-Acetylthiophen-2-yl) pyridin-2-ylamino] pyridin-4-yl} -acetic acid ethyl ester (compound B-52),

2- [6- (5-Acetylthiophen-2-yl) pyridin-2-ylamino] isonicotinic acid methyl ester (compound B-53),

1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiophen-2-yl) ethanol (compound B-55),

N-hydroxy-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxyamidine (compound B-60),

1- (5- {6- [4- (2-hydroxyethoxy) pyridin-2-ylamino] pyridin-2-yl} thiophen-2-yl) ethanone (compound B-73),

1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone (compound B-74),

1- {5- [6- (4-Chloropyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone oxime (compound B-75),

{5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} piperazin-1-ylmethanone (compound B-84),

1- (5- {6- [4- (4,4-dimethyl-4,5-dihydrooxazol-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiophen-2-yl)

ethanone (compound B-87),

2,2-difluoro-3-hydroxy-3- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} propionic acid (compound B-109),

4 - [({5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid (compound B-116),

4 - [(N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid (compound B-119),

trans-4 - [(N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl]

cyclohexanecarboxylic acid (compound B-120),

3- (N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) propionic acid hydrochloride (compound B-124),

4 - [(N-isobutyryl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid (compound B-127) and

4 - [(N- (2-hydroxyacetyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid (compound B -128).

As for the salt of the compound represented by formula (I), pharmacologically acceptable salts are preferred, and examples thereof include a salt with an inorganic base, a salt with an organic base, a salt with an inorganic acid, a salt with an organic acid, a salt with a basic or acidic amino acid, and t .d.

Preferred examples of the inorganic base salt include, for example, a salt with an alkali metal such as sodium, potassium, a salt with an alkaline earth metal such as calcium, magnesium, as well as salts with aluminum, ammonium, etc.

Preferred examples of salts with an organic base include, for example, salts with trimethylamine, triethylamine, pyridine, picoline, ethanolamine, diethanolamine, triethanolamine, dicyclohexylamine, N, N-dibenzylethylenediamine, etc.

Preferred examples of the salt with an inorganic acid include, for example, salts with hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, etc.

Preferred examples of salts with an organic acid include, for example, salts with formic acid, acetic acid, trifluoroacetic acid, fumaric acid, oxalic acid, tartaric acid, maleic acid, citric acid, succinic acid, malic acid, methanesulfonic acid, benzenesulfonic acid toluenesulfonic acid, etc.

Preferred examples of a salt with a basic amino acid include, for example, salts with arginine, lysine, ornithine, and preferred examples of a salt with an acid amino acid include, for example, salts with aspartic acid, glutamic acid, etc.

The compound of the present invention has an excellent Syk inhibitory effect and is useful as a therapeutic agent for the treatment of allergic diseases or a therapeutic agent for autoimmune diseases.

When a compound of the present invention is used as a medicament for treating allergic diseases, especially a medicament for treating bronchial asthma, a medicament for treating allergic rhinitis, a medicament for treating allergic dermatitis, and a medicament for treating allergic conjunctivitis or a medicament for treating autoimmune diseases drug for the treatment of progressive deforming arthritis, Lek GOVERNMENTAL for the treatment of systemic lupus erythematosus, drug for treatment of multiple sclerosis, a medicament for the treatment of cancer, a medicament for treatment of B-lymphoma, B-cell leukemia; as a rule, it is administered systemically or locally, orally or parenterally.

More preferably, the compound (I) of the present invention or a salt thereof can be combined with a pharmaceutically acceptable carrier and administered orally or parenterally in the form of a solid preparation such as a tablet, capsule, granule and powder; or a liquid preparation, such as syrup and injection.

The introduction can be carried out in any form for oral administration in the form of tablets, pills, capsules, granules, powder, liquids, etc. or by parenteral administration by injection, such as intravenous infusion, intramuscular injection, in the form of a suppository or transdermal preparation. Parenteral administration includes intravenous, intramuscular, subcutaneous, tissue, intranasal, intradermal injection, drip, intracerebral, rectal, vaginal, intraabdominal, intraperitoneal, etc.

In the form of a solid composition for oral administration in accordance with the present invention, a tablet, powder, granule, etc. are used. In such a solid composition, one or more active substances are mixed with at least one inert solvent, for example, lactose, mannitol, glucose, hydroxypropyl cellulose, microcrystalline cellulose, starch, polyvinylpyrrolidone, magnesium aluminum metasilicate, etc. The composition may include additives in addition to an inert solvent, for example, a lubricant such as magnesium stearate, a disintegrating agent such as calcium carboxymethyl cellulose, a stabilizer such as lactose, a solubilizing agent such as glutamic acid or aspartic acid in accordance with a conventional method. The tablet or pill may be coated, as required, with a coating of sucrose, gelatin, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxypropyl methyl cellulose phthalate, macrosol, titanium dioxide, talc or a gastric soluble or enteric film.

The liquid composition for oral administration includes a pharmaceutically acceptable emulsion, a liquid preparation, a suspension, a syrup and an elixir, and may include a commonly used inert solvent, for example, purified water and ethanol. These compositions may include adjuvants, such as a solubilizing agent, a humectant, a suspending agent, a sweetener, a neutralizing agent, a flavoring agent and a preservative in addition to an inert solvent.

An injection for parenteral administration can be obtained by dissolving, suspending or emulsifying a predetermined amount of the active agent in an aqueous solution (e.g., distilled water for injection, saline, Ringer's solution, etc.) or an oil solvent (e.g., vegetable oil, such like olive oil, sesame oil, cottonseed oil, corn oil, propylene glycol, etc.) together with a dispersing agent (for example, Polysorbate 80, polyoxyethylene hydrogenated castor e oil 60, polyethylene glycol, carboxymethyl cellulose, sodium alginate, etc.), a preservative (e.g. methylparaben, propylparaben, benzyl alcohol, chlorobutanol, phenol, etc.), an isotonizing agent (e.g. sodium chloride, glycerin, D- mannitol, D-sorbitol, glucose, etc.) etc.

If necessary, additives, such as a solubilizer (e.g., sodium salicylate, sodium acetate, etc.), a stabilizer (e.g., human serum albumin, etc.), and an emollient (e.g., benzyl alcohol, etc.) can be used. .d.).

In addition, if necessary, a preservative, antioxidant, coloring agent, flavoring agent, sweetener, absorbent, hydrating agent and other additives may be included.

As a pharmaceutically acceptable carrier, various organic or inorganic excipients commonly used as pharmaceutical products may be mentioned. If necessary, in accordance with the traditional method, a filler, a lubricant, a binder, a disintegrating agent, which are respectively added to the solid preparation and a solvent, a solubilizer, a suspending agent, an isotonizing agent, a buffer, an emollient, which are respectively added to the liquid preparation, can be used. In addition, pharmaceutical additives such as a preservative, antioxidant, coloring agent, sweetener, absorbent, hydrating agent, etc. can be used.

Preferred examples of filler include lactose, corn starch, sucrose, D-mannitol, D-sorbitol, starch, dextrin, crystalline cellulose, low substituted hydroxypropyl cellulose, sodium carboxymethyl cellulose, gum arabic, glucose, silicon dioxide, etc.

Preferred examples of the antioxidant include, for example, sulfite salt, ascorbic acid, etc.

Preferred examples of the disintegrating agent include, for example, carboxymethyl cellulose, calcium carboxymethyl cellulose, sodium carboxymethyl starch, croscarmellose sodium, crospovidone, low substituted hydroxypropyl cellulose, hydroxypropyl starch, etc.

Preferred examples of the binder include, for example, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, polyvinylpyrrolidone, crystalline cellulose, sucrose, gum arabic powder, etc. The preferred binder is hydroxypropyl cellulose or polyvinylpyrrolidone. Polyvinylpyrrolidone is preferred, in particular when the active ingredient used in the present invention is metformin hydrochloride.

Preferred examples of the lubricant include, for example, magnesium stearate, calcium stearate, talc, colloidal silica, etc.

Preferred examples of the isotonizing agent include, for example, glucose, D-sorbitol, sodium chloride, glycerin, D-mannitol, etc.

Preferred examples of the pH of the regulatory agent include, for example, citrate, phosphate, carbonate, tartrate, fumarate, acetate, amino acid salt, etc.

Preferred examples of the solubilizer include, for example, polyethylene glycol, propylene glycol, D-mannitol, benzyl benzoate, ethanol, tris-aminomethane, cholesterol, triethanolamine, sodium carbonate, sodium citrate, etc.

As a preferred example of a solvent, for example, an injection solvent, alcohol, propylene glycol, macrogol, sesame oil, corn oil, olive oil, etc. can be used.

As a preferred example, a suspending agent, for example a surfactant such as stearyl triethanolamine, sodium lauryl sulfate, laurylaminopropionic acid, commercial lecithin, benzalkonium chloride, benzethonium chloride, glyceryl monostearate; a hydrophilic macromolecule such as polyvinyl alcohol, polyvinylpyrrolidone, sodium carboxymethyl cellulose, methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, for example, can be an example.

Preferred examples of emollients include, for example, benzyl alcohol, etc.

Preferred examples of the buffer include, for example, buffers such as phosphate, acetate, carbonate, citrate, etc.

Preferred examples of the preservative include, for example, p-hydroxybenzoic acid esters, chlorobutanol, benzyl alcohol, phenethyl alcohol, dehydroacetic acid, sorbic acid, etc.

The dose of the compound of the present invention varies depending on the subject of administration, route of administration, disease, general condition, etc., but when, for example, this dose refers to the oral administration to an adult allergy patient (about 60 kg weight), a single dose is typically from about 0.005 to 50 mg / kg body weight, preferably from 0.01 to 5 mg / kg body weight per dose, and more preferably, the dose is from 0.025 to 2 mg / kg body weight; preferably, this amount is administered once or several times a day.

In the case of oral administration, the usual suitable daily dose is from about 0.01 mg / kg to 10 g / kg of body weight, preferably from 0.1 mg / kg to 1 g / kg and the dose is administered once or separately 2-4 times a day . When the dose is administered intravenously, the daily dose is accordingly from about 0.01 mg / kg to 1 g / kg of body weight, and it is administered once or separately several times a day. The dose is respectively determined in each case, taking into account the condition, age, gender, etc.

Pharmaceutical composition, Syk inhibitor, medicine for treating allergic diseases, medicine for treating bronchial asthma, medicine for treating allergic rhinitis, medicine for treating allergic dermatitis, medicine for treating allergic conjunctivitis, medicine for treating autoimmune diseases, medicine for the treatment of rheumatoid arthritis, a drug for the treatment of systemic lupus erythematosus, a drug A joint agent for treating multiple sclerosis, a medicine for treating a malignant tumor, a medicine for treating B-lymphoma, B-cell leukemia, containing a compound represented by the general formula (I) of the present invention, can be used in conjunction with other anti-allergic therapeutic and / or a prophylactic agent.

In this case, the drug of the present invention and another antiallergic drug can be produced in the form of a combined preparation or separate pharmaceutical preparations, respectively, containing a suitable amount of each dose or, if necessary, can be a kit. When they are produced as separate pharmaceutical preparations, each preparation can be administered at the same time or administered at a time interval.

As an antiallergic drug, a chemical mediator release inhibitor, a histamine antagonist, a thromboxane synthesis inhibitor, a TH2 cytokine inhibitor, a leukotriene antagonist, etc. are known, but an antiallergic drug that can be used in combination with the drug of the present invention is not limited. specific options and can be used in a suitable combination. For example, sodium cromoglycate, emedastine fumarate, suplatast tosilate, epinastine hydrochloride, etc. can be used as an inhibitor of the release of chemical mediators, clematastine fumarate, d-chloropheniramine maleate, cyproheptadine hydrochloride, hydrochloride hydrochloride, hydrochloride, hydrochloride may be used , mequitazine, diphenhydramine hydrochloride, ebastin, cetirizine hydrochloride, olopatadine hydrochloride, fexofenadine hydrochloride, etc., as an inhibitor of thromboxane synthesis hydrochloride chloride can be used, etc., pranlukast hydrate, zafirlukast, etc. can be used as an antagonist of leukotriene.

Further, a process for preparing a compound represented by the general formula (I) of the present invention is described in particular. However, the present invention cannot be limited in this way. The preparation of a compound of the present invention can be suitably carried out in a portion that is easy to carry out. In addition, when there is a reactive functional group, the installation of protection or deprotection can be respectively carried out at each stage, and accordingly, a reagent other than the illustrated reagents can be used to facilitate the development of the reaction.

Any compound obtained in each step can be isolated and purified in a conventional manner, but the compound may optionally be reacted in the next step without isolation and purification.

As a method of isolation and purification, when they are carried out, a conventional method, such as distillation, crystallization, recrystallization, silica gel column chromatography, thin layer chromatography, preparative HPLC, can be selected or carried out in combination.

In the case where a compound in which R ⁷ is a nucleophilic substituent is desired, it can be obtained using the following preparation method.

Obtaining the compound according to example 1 (the method is presented in scheme 1)

(where X represents a leaving group, such as a halogen atom, and R ⁷ 'represents a nucleophilic substituent from among R ⁷ , and each other symbol represents the value indicated above).

Stage 1

Compound (3) is prepared by subjecting compound (2) to halogenation using a halogenation agent such as thionyl chloride, oxalyl chloride in a solvent such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, acetonitrile, toluene or react, using the leaving group cleavage with a reagent such as methanesulfonyl chloride, p-toluenesulfonyl chloride, sulfonic acid trifluoromethane anhydride in the presence of a base such as triethylamine, N, N-diisopropylethylamine and pyridine.

Stage 2

Compound (5) is obtained by converting compound (4) to thiourea using 9-fluorenylmethoxycarbonyl isothiocyanate, piperidine in a solvent such as ethanol, isopropanol, ethyl acetate, tetrahydrofuran, N, N-dimethylformamide, dimethyl sulfoxide, chloroform, acetyl nitrile, 1-acetonitrile , 4-dioxane, followed by reaction with compound (3).

Stage 3

Compound (6) is obtained by reacting compound (5) in acetic anhydride as a solvent, in the presence of formic acid or a reaction using N, N-dimethylformamide dimethyl acetal, N, N-dimethylformamide diethyl acetal, etc., in a solvent such as methanol, ethanol, isopropanol, tetrahydrofuran, acetonitrile, toluene in the presence of a base such as triethylamine, N, N-diisopropylethylamine, pyridine.

Stage 4

The compound represented by the general formula [I-2] is obtained by reacting the compound (6) obtained in step 3 with the compound (8) in a solvent such as toluene, benzene, 1,4-dioxane, tetrahydrofuran, dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, ethylene glycol dimethyl ether, 1-methyl-2-pyrrolidinone, N, N-dimethylformamide, N, N-dimethylacetamide in the presence of a base such as 2,2'-bis (diphenylphosphino) -1, 1-binaphthyl, palladium acetate and cesium carbonate, potassium carbonate, potassium phosphate.

Obtaining the compound of example 2 (the method is presented in scheme 2)

(Each symbol in the diagram represents, respectively, the value indicated above)

Stage 5

Compound (10) is prepared by reacting nicotinic acid chloride (8) and a malonic acid derivative (9) in a solvent such as acetonitrile, tetrahydrofuran, 1,4-dioxane, N, N-dimethylformamide in the presence of magnesium chloride and a base such as triethylamine , N, N-diisopropylethylamine, following the procedure described in Organic Letters, 5 (18), 3233-3236, (2003), and then decarboxylating and deprotecting the tert-butoxycarbonyl group using simultaneously concentrated hydrochloric acid.

Stage 6

Compound (12) is obtained by reacting compound (10) with compound (11) in a solvent such as acetonitrile, tetrahydrofuran, 1,4-dioxane, N, N-dimethylformamide, dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride. Bases such as pyridine, triethylamine, N, N-diisopropylethylamine may be used in this reaction, depending on the procedure. When compound (11) is a carboxylic acid compound, compound (12) can be obtained by carrying out a reaction using a condensing agent such as dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, diisopropylcarbodiimide, diphenylphosphorylazide, 2-ethoxy -1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ).

Stage 7

Compound (13) is prepared by reacting compound (12) using Lawesson's reagent in a solvent such as tetrahydrofuran, 1,4-dioxane, dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride. The compound represented by the general formula [I] is obtained by then performing the process according to the procedure described in step 4 above.

Obtaining the compound of example 3 (the method is presented in scheme 3)

Stage 8

Compound (15) can be obtained by reacting compound (7) and compound (14) in accordance with the method presented in stage 4.

Stage 9

Compound [I] can be obtained by reacting compound (15) with compound (16) in a solvent such as dimethoxyethane, diethyl ether, acetone, butanone, dioxane, tetrahydrofuran in the presence of tetrakis (triphenylphosphine) palladium and a base such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate.

When a compound [I] having a “—CONH bond” in the substituent R ⁷ is desired, the desired compound [I] having a “—CONH bond” can be obtained by introducing a compound having a “—COOH group” and a compound having an “—NH ₂ group” in an amidation reaction.

In addition, when the compound [I] having “—N (- (substituted) C _1-6 alkyl) -” in the substituent R ⁷ is desired, a known alkylation reaction may be carried out using a compound having the group “—NH— ".

When the compound [I] having the group “—CH (OH) -” in the substituent R ⁷ is desired, the known Grignard reaction can be carried out with the compound containing the group “—CH”.

When an acid addition salt or a base addition salt of a compound represented by the general formula [I] is desired, a well-known method can be used. For example, a compound represented by the general formula [I] is dissolved in water, methanol, ethanol, n-propanol, isopropanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethyl acetate, dichloromethane, 1,2-dichloroethane or chloroform or in mixed solvent, and then the solvent mentioned above is added in which the desired acid or base is dissolved, and the precipitated crystal can be immediately separated by filtration or concentration under reduced pressure.

When a compound represented by the general formula [I] or an intermediate is a racemate and an optically active substance is required, it can be resolved in a well-known manner. As for the separation method, this method can be suitably selected or carried out in combination with a conventional method, such as salt crystallization separation using optically active 1-phenethylamine, optically active alkaloid, optically active campharosulfonic acid, optically active tartaric acid and their derivatives, recrystallization, chiral column chromatography, chiral preparative HPLC.

The resulting compound of the invention can be separated and purified, if necessary, using a conventional method, for example, recrystallization, reprecipitation or the traditional method generally used to separate and purify the organic compound, for example, using a synthetic adsorbing agent, such as adsorption chromatography. on a column, column chromatography, a method using ion exchange chromatography, a method in which I combine methods of column chromatography using a normal phase / reversed phase silica gel or alkylated silica gel and elution is carried out with a suitable eluent.

The compound represented by the general formula [I] of the present invention and the method for its preparation are described in more detail using the following examples. However, it is understood that the present invention is not limited to these examples.

Example 1

Preparation of 1-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-2-one (compound A-1) :

Stage 1. Obtaining 2-bromo-6-chloromethylpyridine

2-Bromo-6-hydroxymethylpyridine (5.00 g, 25.5 mmol) was dissolved in chloroform (30 ml) and thionyl chloride (2.8 ml, 38.3 mmol) was added, then the mixture was stirred at room temperature for 3 hours . After this, the reaction solution was concentrated, saturated aqueous sodium hydrogen carbonate was added to the precipitate, and the precipitate was filtered off. After this is washed with water, drying is carried out under vacuum and the title compound is obtained (5.20 g, 99%).

Stage 2. Obtaining the amide 3-oxopiperazine-1-carboxylic acid

Piperazin-2-one (1.43 g, 14.3 mmol) was dissolved in chloroform (30 ml) and 9-fluorenylmethoxycarbonyl isothiocyanate (4.02 g, 14.3 mmol) was added, and then the mixture was stirred at room temperature for 2 hours. After this, the reaction solution was concentrated, diethyl ether was added to the residue, and the precipitate was filtered off. The resulting precipitate was dissolved in N, N-dimethylformamide (10 ml), piperidine (10 ml) was added and the mixture was stirred at room temperature for 6 hours. After this, the reaction solution was concentrated again, diethyl ether was added to the residue, and the precipitate was filtered off and, after drying in vacuo, the title compound (2.22 g, 98%) was obtained.

Stage 3. Obtaining 6-bromopyridin-2-ylmethyl ester of 3-oxopiperazine-1-carboxyimidothionic acid

The 2-bromo-6-chloromethylpyridine (1.50 g, 7.26 mmol) obtained in step 1 was dissolved in ethanol (15 ml) and 3-oxopiperazine-1-carboxylic acid amide (1.16 g, 7, 29 mmol) obtained in step 2, and the mixture was heated to boiling point for 2 hours. After this, the reaction solution was cooled to room temperature, the solution obtained by concentration in vacuo was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and the precipitated solid was separated by filtration, washed with water, and the title compound was obtained (1.67 g, 70%).

Step 4. Preparation of 4- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperazin-2-one

Formic acid (5 ml) and acetic anhydride (10 ml) are added to 3-oxopiperazine-1-carboxyimidothionic acid 6-bromopyridin-2-ylmethyl ester obtained in step 3 (1.67 g, 5.08 mmol), mixture stirred at room temperature for 12 hours. The crystals precipitated at a concentration in vacuo of the reaction solution were separated by filtration, washed with water, and the title compound (1.37 g, 80%) was obtained.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 8.22 (1H, broad), 8.01 (1H, s), 7.83 (1H, d, J = 7.8 Hz), 7.69 (1H, t, J = 7.8 Hz), 7.38 (1H, d, J = 7.8 Hz), 4.04 (2H, s), 3.73-3.68 (2H , m), 3.38-3.34 (2H, m).

Step 5. Preparation of 4- [5- (6-bromopyridin-2-yl) thiazol-2-yl] -1-methylpiperazin-2-one

The 4- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperazin-2-one obtained in step 4 (200 mg, 0.59 mmol) is dissolved in tetrahydrofuran (2 ml) and N, N dimethylformamide (2 ml) and then sodium hydride (60% in oil, 26 mg, 0.65 mmol) is added, methyl iodide (39 μl, 0.62 mmol) is added and the mixture is stirred overnight at room temperature. Water was added to the reaction solution, and the residue obtained by concentration in vacuo was extracted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to give the title compound (188 mg, 90%).

Step 6. Preparation of 1-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-2-one

4- [5- (6-Bromopyridin-2-yl) thiazol-2-yl] -1-methylpiperazin-2-one obtained in step 5 (188 mg, 0.53 mmol) is dissolved in toluene (5 ml) and then 2-amino-4-methylpyridine (58 mg, 0.53 mmol), 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (66 mg, 0.11 mmol), palladium acetate (18 mg, 0.08 mmol) and cesium carbonate (260 mg, 0.80 mmol) and the mixture was stirred overnight at a temperature of 100 ° C. Water was added to the reaction solution, and extracted with ethyl acetate, and the organic layer was washed with brine. The organic layer was dried over sodium sulfate and, after concentration in vacuo, the residue was washed with methanol to give the title compound (77 mg, 38%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 8.09 (1H, d, J = 4.8 Hz), 7.92 (1H, broad), 7.89 (1H, s), 7.60 (1H, dd, J = 8.4, 7.6 Hz), 7.26 (1H, d, J = 8.4 Hz), 7.26 (1H, d, J = 7.6 Hz ), 6.75 (1H, broad d, J = 4.8 Hz), 4.07 (2H, s), 3.80-3.77 (2H, m), 3.52-3.50 ( 2H, m), 2.92 (3H, s), 2.34 (3H, s).

Example 2

Preparation of 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxylic acid (compound A-2) :

(1) Preparation of 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxylic acid ethyl ester:

Stage 1. Obtaining ethyl ester of 1-thiocarbamoylpiperidin-4-carboxylic acid

9-Fluorenylmethoxycarbonylisothiocyanate (5.90 g, 21.0 mmol) was dissolved in chloroform (20 ml), after which a solution of piperidine-4-carboxylic acid ethyl ester (3.30 g, 21.0 mmol) in chloroform (10 ml) was added. ) and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated in vacuo and the precipitate obtained by adding diethyl ether was separated by filtration. The resulting material was dissolved in N, N-dimethylformamide (20 ml) and piperidine (20 ml) was added and the mixture was stirred at room temperature for 1 hour. After this, the reaction solution was washed with ethyl acetate and the organic layer was washed with saturated brine and dried over sodium sulfate, the residue obtained by concentration in vacuo was purified by silica gel chromatography (n-hexane: ethyl acetate), and the title compound (4.34 g, one hundred%).

Stage 2. Obtaining ethyl ester of 1- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperidine-4-carboxylic acid

The 2-bromo-6-chloromethylpyridine obtained in step 1 of Example 1 (2.90 g, 14.0 mmol) was dissolved in ethanol (30 ml) and 1-thiocarbamoylpiperidin-4-carboxylic acid ethyl ester (3.00 g , 13.9 mmol) obtained in stage 1, the mixture is heated to boiling point for 2 hours. The reaction solution was cooled to room temperature, dimethylformamide dimethylacetal (2.8 ml, 21.1 mmol) and triethylamine (5.9 ml, 42.3 mmol) were added and the mixture was again heated to boiling point for 1 hour. After concentration, water was added and the reaction solution was extracted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, and the residue obtained by concentration in vacuo was purified by silica gel chromatography (n-hexane: ethyl acetate = 50:50 to 0: 100) to obtain the title compound (3.60 g, 65%) .

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 7.92 (1H, s), 7.77 (1H, d, J = 7.8 Hz), 7.64 (1H, t, J = 7.8 Hz), 7.32 (1H, d, J = 7.8 Hz), 4.05 (2H, q, J = 7.2 Hz), 3.94-3.85 (2H, m) 3.22-3.12 (2H, m), 2.67-2.57 (2H, m), 1.94-1.86 (1H, m), 1.65-1.53 (2H, m) 1.16 (3H, t, J = 7.2 Hz).

Stage 3. Obtaining ethyl 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxylate

rac-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (434 mg, 0.70 mmol) and palladium acetate (117 mg, 0.52 mmol) are dissolved in toluene (15 ml), then sequentially add 2-amino-4-picoline (395 mg, 3.65 mmol) and a solution of ethyl 1- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperidine-4-carboxylate in toluene (15 ml ) obtained in stage 2 (1.38 g, 3.48 mmol), then cesium carbonate (1.70 g, 5.22 mmol) is added and the mixture is stirred at 100 ° C overnight. Water was added to the reaction solution, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, and the residue obtained by concentration in vacuo was purified by silica gel chromatography (n-hexane: ethyl acetate = 1: 1 to 1:10) to obtain the title compound (817 mg, 55%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.53 (1H, s), 8.08 (1H, d, J = 5.2 Hz), 7.92 (1H, s), 7 83 (1H, s), 7.58 (1H, dd, J = 8.0, 7.6 Hz), 7.23 (2H, dd, J = 9.6, 7.6 Hz), 6, 75-6.74 (1H, m), 4.09 (2H, q, J = 6.9 Hz), 3.94-3.87 (2H, m), 3.24-3.164 (2H, m) 2.69-2.61 (1H, m), 2.33 (3H, s), 1.99-1.93 (2H, m), 1.71-1.60 (2H, m), 1 , 20 (3H, t, J = 7.2 Hz).

(2) Preparation of 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxylic acid (compound A-2) :

Ethyl 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxylate obtained in the above Example (1) (817 mg, 1, 93 mmol), dissolved in a mixed solvent of tetrahydrofuran (4 ml), methanol (4 ml) and water (2 ml), lithium hydroxide monohydrate (202 mg, 4.81 mmol) was added and then the mixture was stirred at 50 ° C in within 5 hours. The concentrate obtained by concentration in vacuo is neutralized with 0.1N. hydrochloric acid solution, the precipitated solid was separated by filtration, washed with water and the title compound (721 mg) was obtained.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 12.34 (1H, broad s), 9.53 (1H, s), 8.08 (1H, d, J = 5.2 Hz) 7.92 (1H, s), 7.83 (1H, s), 7.58 (1H, dd, J = 4.0, 8.0 Hz), 7.23 (2H, dd, J = 11 6, 8.0 Hz), 6.75-6.73 (1H, m), 3.92-3.86 (2H, m), 3.23-3.15 (2H, m), 2, 58-2.52 (1H, m), 2.33 (3H, s), 1.99-1.90 (2H, m), 1.69-1.58 (2H, m).

MS: 396.2 (M ⁺ +1).

Example 3

Preparation of 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide (compound A-3) :

1- {5- [6- (4-Methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxylic acid (100 mg, 0.25 mmol) obtained in example 2, dissolved in N, N-dimethylformamide (2 ml) and benzotriazolyl oxitripyrrolidinophosphonium hexafluorophosphate (263 mg, 0.50 mmol), diisopropylethylamine (0.18 ml, 1.03 mmol) and ammonium chloride (41 mg, 0.77 mmol) are added, after which the mixture was stirred at room temperature for 1 hour. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the precipitated solid was separated by filtration, washed with water, and the title compound (89 mg, 89%) was obtained.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.53 (1H, s), 8.08 (1H, d, J = 5.2 Hz), 7.93 (1H, s), 7 , 83 (1H, s), 7.58 (1H, t, J = 8.0 Hz), 7.32 (1H, broad s), 7.23 (2H, t, J = 8.0 Hz) 6.83 (1H, br s), 6.74 (1H, d, J = 5.2 Hz), 3.99-3.92 (2H, m), 3.17-3.08 (2H , m), 2.43-2.34 (1H, m), 2.33 (3H, s), 1.86-1.78 (2H, m), 1.67-1.57 (2H, m )

MS: 395.2 (M ⁺ +1).

Example 4

Preparation of N-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) methyl-1-pyridin-2-yl] thiazol-2-yl} piperidin-4-

carboxamide (compound A-4) :

1- {5- [6- (4-Methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxylic acid (200 mg, 0.51 mmol) obtained in example 2, dissolved in N, N-dimethylformamide (5 ml), methylamine hydrochloride (68 mg, 1.00 mmol), benzotriazolyl oxitripyrrolidinophosphonium hexafluorophosphate (520 mg, 1.00 mmol) and triethylamine (0.28 ml, 2.01 mmol) are added and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, and the precipitated solid was separated by filtration, washed with water to obtain the title compound (160 mg, 78%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.53 (1H, s), 8.08 (1H, d, J = 5.1 Hz), 7.93 (1H, s), 7 82 (1H, s), 7.79 (1H, q, J = 4.5 Hz), 7.58 (1H, t, J = 8.0 Hz), 7.23 (2H, t, J = 8.0 Hz), 6.74 (1H, d, J = 5.1 Hz), 4.01-3.92 (2H, m), 3.18-3.07 (2H, m), 2, 57 (3H, d, J = 4.5 Hz), 2.44-2.35 (1H, m), 2.32 (3H, s), 1.83-1.75 (2H, m), 1 70-1.57 (2H, m).

MC: 409.2 (M ⁺ +1).

Example 5

Preparation of N- (2-hydroxyethyl) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide (compound A-5) :

Prepared in accordance with a procedure analogous to the preparation of the compound of Example 4 using 2-hydroxyethylamine (61 mg, 1.00 mmol) instead of methylamine hydrochloride, the title compound (70 mg, 32%) was obtained from 1- {5- [ 6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxylic acid (200 mg, 0.50 mmol) obtained in Example 2.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.53 (1H, s), 8.08 (1H, d, J = 5.1 Hz), 7.93 (1H, s), 7 82-7.86 (2H, m), 7.58 (1H, t, J = 8.0 Hz), 7.23 (2H, t, J = 8.0 Hz), 6.74 (1H, d, J = 5.1 Hz), 4.64 (1H, t, J = 5.7 Hz), 4.01-3.92 (2H, m), 3.43-3.35 (2H, m ), 3.16-3.06 (4H, m), 2.47-2.38 (1H, m), 2.33 (3H, s), 1.83-1.58 (4H, m).

MS: 439.2 (M ⁺ +1).

Example 6

Preparation of Trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid methyl ester (compound A-6) :

Step 1. Preparation of 2-amino-1- (6-bromopyridin-2-yl) ethanone hydrochloride

Magnesium chloride (21.30 g, 224 mmol) and triethylamine (62 ml, 446 mmol) are successively added to a suspension in acetonitrile (300 ml) of 2-tert-butoxycarbonylamidomalomonic acid monoethyl ester (50.30 g, 203 mmol) in an Ar atmosphere under ice cooling and the mixture was stirred for 1 hour. Then, a solution of 6-bromopyridin-2-carbonyl chloride (37.40 g, 170 mmol) in acetonitrile (150 ml) was added dropwise at the same temperature for 3 hours, and the mixture was stirred for 1 hour. After this, the reaction solution was concentrated, ethyl acetate (300 ml) was added, and insoluble impurities were filtered off. The filtrate is washed with a 10% aqueous citric acid solution, saturated brine and dried over magnesium sulfate, and after concentration in vacuo, an oily substance is obtained. Concentrated hydrochloric acid (200 ml) was added to a solution of the obtained oily substance in ethanol (200 ml) and heated to boiling point for 6 hours. After it was concentrated to dryness under reduced pressure, the reaction solution was washed with a mixed solvent of ethanol-isopropyl ether (1: 3), separated by filtration, dried in vacuo to give the title compound (25.40 g, 50%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 8.42-8.31 (3H, m), 8.16 (1H, t, J = 7.8 Hz), 8.07 (1H, dd, J = 7.8, 1.2 Hz), 7.92 (1H, dd, J = 7.8, 1.2 Hz), 4.58 (2H, broad s).

Stage 2. Obtaining methyl trans-4- [2- (6-bromopyridin-2-yl) -2-oxoethylcarbamoyl] cyclohexanecarboxylic acid

To a suspension of 2-amino-1- (6-bromopyridin-2-yl) ethanone hydrochloride (10.00 g, 39.8 mmol) in acetonitrile (200 ml) obtained in stage 1, methyl ether is added dropwise under ice-cooling trans-4-chlorocarbonylcyclohexanecarboxylic acid (9.00 g, 44.0 mmol), a solution of triethylamine (13.9 ml, 100 mmol) in acetonitrile (60 ml) for 2 hours. After this, the reaction solution was concentrated, water was added and extracted with ethyl acetate. The organic layer was washed successively with 10% citric acid solution, saturated aqueous sodium hydrogen carbonate solution, saturated saline and dried over magnesium sulfate. After concentration, the residue was purified by flash chromatography on silica gel (n-hexane: ethyl acetate = 1: 2) to obtain the title compound (7.38 g, 48%).

Stage 3. Obtaining methyl trans-4- [5- (6-bromopyridin-2-yl) thiazol-2-yl] cyclohexanecarboxylic acid

A solution of trans-4- [2- (6-bromopyridin-2-yl) -2-oxoethylcarbamoyl] cyclohexanecarboxylic acid methyl ester (7.38 g, 19.3 mmol) in tetrahydrofuran (120 ml), obtained in stage 2, and Lawson reagent (Lavson) (8.20 g, 20.3 mmol) is heated to boiling point for 2 hours in a stream of Ar. After the reaction solution was concentrated, saturated aqueous sodium hydrogen carbonate was added and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and dried over magnesium sulfate, and after concentration, the residue was purified by flash chromatography on silica gel (n-hexane: ethyl acetate = 1: 1) to obtain the title compound (6.1 g).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 8.41 (1H, s), 7.96 (1H, dd, J = 7.6, 1.2 Hz), 7.92 (1H, t, J = 7.6 Hz), 7.43 (1H, dd, J = 7.6, 1.2 Hz), 3.62 (3H, s), 2.97-3.05 (1H, m ), 2.45-2.37 (1H, m), 2.19-2.12 (2H, m), 2.05-1.98 (2H, m), 1.63-1.46 (4H , m).

Step 4. Preparation of trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid methyl ester

A suspension of trans-4- [5- (6-bromopyridin-2-yl) thiazol-2-yl] cyclohexanecarboxylic acid methyl ester (1.80 g, 4.72 mmol) in toluene (100 ml), obtained in step 3, 2-amino-4-picoline (613 mg, 5.66 mmol), palladium acetate (159 mg, 0.71 mmol), rac-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (529 mg , 0.85 mmol), cesium carbonate (2.00 g, 6.14 mmol) is heated and stirred at a temperature of 90 ° C in a stream of Ar for 7 hours. Water was added to the reaction solution and extracted with a mixed solvent: ethyl acetate-tetrahydrofuran. The organic layer was washed with brine and dried over magnesium sulfate; the residue obtained by concentration in vacuo was purified by flash chromatography on silica gel (n-hexane: ethyl acetate = 1: 2) and then washed with a mixed solvent of n-hexane-ethyl acetate to obtain the title compound (1.60 g, 83%) .

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.67 (1H, broad s), 8.30 (1H, s), 8.10 (1H, dd, J = 5.2, 0 , 8 Hz), 7.92 (1H, broad), 7.68 (1H, dd, J = 8.0, 7.6 Hz), 7.40 (1H, broad d, J = 8.0 Hz), 7.40 (1H, broad d, J = 7.6 Hz), 6.78-6.76 (1H, m), 3.62 (3H, s), 3.05-2.97 (1H, m), 2.45-2.38 (1H, m), 2.35 (3H, s), 2.21-2.15 (2H, m), 2.05-1.99 (2H , m), 1.64-1.48 (4H, m).

Example 7

Preparation of trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid (compound A-7) :

A solution of trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid methyl ester (1.50 g, 3.67 mmol) obtained in Example 6 above, lithium hydroxide monohydrate (770 mg, 18.4 mmol) in a mixture of methanol (40 ml), tetrahydrofuran (40 ml) and water (20 ml) was stirred at room temperature for 15 hours. After this, the reaction solution was concentrated, then it was neutralized with 2N. hydrochloric acid solution (9.2 ml, 18.4 mmol) and the precipitate is filtered off and washed with water and ethyl acetate. Then it was dried in vacuo to give the title compound (1.41 g, 97%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 12.14 (1H, broad s), 9.67 (1H, broad s), 8.30 (1H, s), 8.10 (1H d, J = 4.8 Hz), 7.93 (1H, br), 7.68 (1H, t, J = 8.0 Hz), 7.41 (1H, d, J = 8.0 Hz), 7.39 (1H, d, J = 8.0 Hz), 6.77 (1H, broad d, J = 4.8 Hz), 3.04-1.95 (1H, m), 2.35 (3H, s), 2.33-2.25 (1H, m), 2.21-2.15 (2H, m), 2.05-1.99 (2H, m), 1, 62-1.45 (4H, m).

Example 8

Preparation of (hydroxypiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} cyclohexyl) methanone (compound A-8) :

To a suspension in dimethylformamide (4 ml) trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid (504 mg, 1.28 mmol) obtained in Example 7 and 4-hydroxypiperidine (130 mg, 1.29 mmol) were added successively at room temperature with triethylamine (4 ml, 2.88 mmol), benzotriazolyl oxitripyrrolidinophosphonium hexafluorophosphate (731 mg, 1.40 mmol) and the mixture was stirred in within 1 hour. After this, the reaction solution was concentrated, saturated sodium bicarbonate solution and water were added, the precipitate was filtered off and washed with water, it was dried under vacuum and the title compound (585 mg, 96%) was obtained.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.67 (1H, br s), 8.30 (1H, s), 8.10 (1H, d, J = 5.2 Hz) 7.92 (1H, broad), 7.69 (1H, dd, J = 8.4, 7.6 Hz), 7.41 (1H, d, J = 8.4 Hz), 7.39 (1H, d, J = 7.6 Hz), 6.77 (1H, broad d, J = 5.2 Hz), 4.73 (1H, d, J = 4.4 Hz), 3.98 -3.90 (1H, m), 3.82-3.74 (1H, m), 3.73-3.66 (1H, m), 3.25-3.16 (1H, m), 3 04-1.94 (2H, m), 2.746-2.66 (1H, m), 2.35 (3H, s), 2.20-2.13 (2H, m), 1.81-1 49 (8H, m), 1.39-1.16 (2H, m).

MC: 478.2 (M ⁺ +1).

Example 9

Preparation of N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} ethyl) amine (compound A-9) :

Step 1. Preparation of {(S) -1- [2- (6-bromopyridin-2-yl) -2-oxoethylcarbamoyl] ethyl} carbamic acid tert-butyl ester

To a suspension of 2-amino-1- (6-bromopyridin-2-yl) ethanone hydrochloride (500 mg, 1.99 mmol) in acetonitrile (11 ml) obtained in Step 1 of Example 6 was added dropwise under ice-cooling over 15 minutes (S) -N-tert-butylcarbonylalanine (376 mg, 1.99 mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (379 mg, 1.99 mmol), 1-hydroxybenzotriazole monohydrate (305 mg , 1.99 mmol), a solution of triethylamine (0.7 ml) in acetonitrile (4 ml). The mixture was then stirred at the same temperature for 1 hour, water was added and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, and the residue obtained by concentration in vacuo was purified by flash chromatography on silica gel (n-hexane: ethyl acetate = 2: 1) to obtain the title compound (456 mg, 59 %).

Step 2. Preparation of {(S) -1- [5- (6-bromopyridin-2-yl) thiazol-2-yl] ethyl} carbamic acid tert-butyl ester

The title compound (282 mg, 71%) was obtained according to a similar procedure to the compound described in Step 3 of Example 6 using {(S) -1- [2- (6-bromopyridin-2) tert-butyl ester -yl) -2-oxoethylcarbamoyl] ethyl} carbamic acid (400 mg, 1.04 mmol) and Lawesson's reagent (419 mg, 1.04 mmol).

Step 3. Preparation of ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} ethyl) carbamic acid tert-butyl ester

The title compound (234 mg, 87%) was obtained according to a similar procedure to the preparation of the compound described in step 4 of Example 7 using {(S) -1- [5- (6-bromopyridin-2) tert-butyl ester -yl) thiazol-2-yl] ethyl} carbamic acid (250 mg, 0.65 mmol) obtained in stage 2, 2-amino-4-picoline (92 mg, 0.85 mmol), palladium acetate (15 mg , 0.07 mmol), rac-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (49 mg, 0.08 mmol) and cesium carbonate (276 mg, 0.85 mmol).

Step 4. Preparation of Amine N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} ethyl)

To a solution of (S) -1 - ({5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} ethyl) carbamic acid tert-butyl ester (200 mg, 0, 49 mmol) in chloroform (5 ml) obtained in step 3, trifluoroacetic acid (5 ml) was added and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated and saturated sodium bicarbonate was added and extracted with a mixed solution of ethyl acetate-tetrahydrofuran. The organic layer was washed with brine and dried over magnesium sulfate. The resulting residue was washed with diisopropyl ether, dried in vacuo to give the title compound (102 mg, 67%).

Example 10

Preparation of N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide (compound A-10) :

Acetic anhydride (0.02 ml, 0.24 mmol) is added to a solution of N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2 -yl} ethyl) amine (50 mg, 0.16 mmol) in pyridine (3 ml) obtained in Example 9, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated and extracted with a mixed solution of ethyl acetate-tetrahydrofuran. The organic layer was washed with brine and dried over magnesium sulfate. The resulting residue was washed with diisopropyl ether, dried in vacuo to give the title compound (43 mg, 76%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.68 (1H, s), 8.71 (1H, d, J = 7.6 Hz), 8.30 (1H, s), 8 09 (1H, d, J = 4.8 Hz), 7.97 (1H, broad s), 7.67 (1H, dd, J = 8.4, 7.6 Hz), 7.40 ( 1H, d, J = 7.2 Hz), 7.34 (1H, d, J = 8.4 Hz), 6.77 (1H, d, J = 5.2 Hz), 5.19-5, 12 (1H, m), 2.35 (3H, s), 1.92 (3H, s), 1.51 (3H, d, J = 7.2 Hz).

MS: 354.1 (M ⁺ +1).

Example 11

Preparation of (S) -3-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one (compound A-11) :

Step 1. Preparation of (S) -4- [2- (6-bromopyridin-2-yl)] - 2-oxoethylcarbamoyl-2,2-dimethyloxazolidin-3-carboxylic acid tert-butyl ester

To a suspension of 3-tert-butyl ether-4-lithium salt (S) -2,2-dimethyloxazolidine-3,4-dicarboxylic acid (12.00 g, 47.7 mmol) in acetonitrile (150 ml) was added under ice-cooling 1-hydroxybenzotriazole monohydrate (7.30 g, 47.7 mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (9.20 g, 47.7 mmol), 2-amino-1- (6- bromopyridin-2-yl) ethanone (10.00 g, 39.7 mmol) obtained in step 1 of Example 6, and the mixture was stirred for 3 hours. After this, the reaction solution was concentrated, water was added and extracted with ethyl acetate. The organic layer was washed successively with 10% aqueous citric acid solution, saturated aqueous sodium hydrogencarbonate, brine and dried over magnesium sulfate and then concentrated, dried in vacuo to give the title compound (13.70 g, 78%).

Step 2. Preparation of (S) -4- [5- (6-bromopyridin-2-yl) -5-thiazol-2-yl] -2,2-dimethyloxazolidin-3-carboxylic acid tert-butyl ester

The title compound (10.50 g, 77%) was obtained according to a similar procedure to the compound described in Step 3 of Example 6 using (S) -4- [2- (6-bromopyridin- 2-yl) -2-oxoethylcarbamoyl-2,2-dimethyloxazolidine-3-carboxylic acid (13.70 g, 31.0 mmol) obtained in stage 1, Lawesson's reagent (12.50 g, 31.0 mmol).

Step 3. Preparation of (S) -2-amino-2- [5- (6-bromopyridin-2-yl) thiazol-2-yl] ethanol dihydrochloride

To a solution of (S) -4- [5- (6-bromopyridin-2-yl) thiazol-2-yl] -2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (5.00 g, 11.4 mmol) in tetrahydrofuran (30 ml) obtained in stage 2, add 4N. a solution of hydrogen chloride-ethyl acetate (30 ml) and heated to boiling point at a temperature of 90 ° C for 2 hours. After this, the reaction solution was cooled, then it was concentrated and washed with ethyl ether, dried, and the title compound (3.57 g) was obtained.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 8.91-8.77 (2H, m), 8.62 (1H, s), 8.07 (1H, d, J = 8.0 Hz), 7.98 (1H, t, J = 8.0 Hz), 7.50 (1H, d, J = 8.0 Hz), 6.12-5.85 (3H, m), 4, 82-4.74 (1H, m), 3.90 (2H, d, J = 5.6 Hz).

Step 4. Preparation of (S) -4- [5- (6-bromopyridin-2-yl) thiazol-2-yl] oxazolidin-2-one

To a solution of (S) -2-amino-2- [5- (6-bromopyridin-2-yl) thiazol-2-yl] ethanol dihydrochloride (1.00 g, 2.68 mmol) in chloroform (15 ml), obtained in step 3, triethylamine (3.7 ml, 2.68 mmol), a solution of triphosgene (278 mg, 0.94 mmol) in chloroform (5 ml) are added dropwise while cooling to -78 ° C, and the mixture is stirred at same temperature for 2 hours. The reaction solution was warmed to room temperature and water was added and then it was extracted with ethyl acetate. After washing with brine, the organic layer was dried over magnesium sulfate. After concentration, the residue was purified by flash chromatography on silica gel (chloroform: methanol: ethyl acetate = 15: 1: 1) and the title compound (712 mg, 82%) was obtained.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 8.66 (1H, broad s), 8.54 (1H, s), 8.03 (1H, dd, J = 8.0, 0 8 Hz), 7.96 (1H, t, J = 7.8 Hz), 7.48 (1H, dd, J = 8.0, 0.8 Hz), 5.31 (1H, ddd, J = 8.6, 4.8, 1.2 Hz), 4.74 (1H, t, J = 8.6 Hz), 4.36 (1H, dd, J = 8.6, 4.8 Hz) .

Step 5. Preparation of (S) -4- [5- (6-bromopyridin-2-yl) thiazol-2-yl] -3-methyloxazolidin-2-one

(S) -4- [5- (6-Bromopyridin-2-yl) thiazol-2-yl] oxazolidin-2-one (488 mg, 1.50 mmol) obtained in stage 4, and sodium hydride (60% in oil, 72 mg, 1.80 mmol) are suspended in tetrahydrofuran (5 ml) and dimethylformamide (5 ml) is added under a stream of Ar and methyl iodide (0.1 ml, 1.65 mmol) under ice cooling and the resulting solution is stirred at room temperature temperature for 12 hours. After this, the reaction solution was concentrated, water was added and then extracted with ethyl acetate. Then the organic layer was washed with brine and dried over magnesium sulfate, it was concentrated and the residue was purified by flash chromatography on silica gel (chloroform: methanol = 20: 1) to obtain the title compound (205 mg, 40%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 8.59 (1H, s), 8.05 (1H, d, J = 7.8 Hz), 7.97 (1H, t, J = 7.8 Hz), 7.49 (1H, d, J = 7.8 Hz), 5.29 (1H, dd, J = 9.0, 5.6 Hz), 4.68 (1H, t, J = 9.0 Hz), 4.32 (1H, dd, J = 9.0, 5.6 Hz), 2.76 (3H, s).

Step 6. Preparation of (S) -3-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one (compound A- eleven)

The title compound (132 mg, 60%) was obtained according to a similar procedure to the compound described in Step 4 of Example 7 using (S) -4- [5- (6-bromopyridin-2-yl) thiazole- 2-yl] -3-methyloxazolidin-2-one (205 mg, 0.60 mmol), obtained in step 5, 2-amino-4-picoline (72 mg, 0.66 mmol), palladium acetate (20 mg, 0.09 mmol), rac-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (75 mg, 0.12 mmol) and cesium carbonate (295 mg, 0.90 mmol).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.71 (1H, br s), 8.47 (1H, s), 8.11 (1H, d, J = 4.8 Hz) 7.90 (1H, br s), 7.73 (1H, t, J = 8.0 Hz), 7.48 (1H, d, J = 8.0 Hz), 7.44 (1H, d, J = 8.0 Hz), 6.78 (1H, d, J = 4.8 Hz), 5.28 (1H, dd, J = 8.8, 4.8 Hz), 4.69 ( 1H, t, J = 8.8 Hz), 4.33 (1H, dd, J = 8.8, 4.8 Hz), 2.79 (3H, s), 2.34 (3H, s).

MS: 368.1 (M ⁺ +1).

Example 12

Preparation of (S) -2,2-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidine-3-carboxylic acid tert-butyl ester (compound A-12) :

The title compound (1.91 g, 90%) was obtained according to a similar procedure to the compound described in Step 4 of Example 6 using (S) -4- [5- (6-bromopyridin- 2-yl) -5-thiazol-2-yl] -2,2-dimethyloxazolidin-3-carboxylic acid (2.00 g, 4.54 mmol) obtained in Step 2 of Example 11, 2-amino-4-picoline (540 mg, 5.00 mmol), palladium acetate (153 mg, 0.68 mmol), rac-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (565 mg, 0.91 mmol) and cesium carbonate (2.22 g, 6.80 mmol).

Example 13

Preparation of (S) -2-amino-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol (compound A-13) :

To a solution of (S) -2,2-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidine-3-carboxylic tert-butyl ester acid (1.90 g, 4.06 mmol) in tetrahydrofuran (10 ml) obtained in example 12, add 4N. a solution of hydrogen chloride-ethyl acetate (10 ml) and stirred at a temperature of 60 ° C for 5 hours with heating. After this, the reaction solution was concentrated, it was neutralized with a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate, concentrated and the residue was purified by flash chromatography on silica gel (chloroform: methanol = 20: 1) to obtain the title compound (588 mg, 44%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.65 (1H, broad s), 8.30 (1H, s), 8.10 (1H, d, J = 4.8 Hz) 7.98 (1H, br s), 7.67 (1H, t, J = 7.8 Hz), 7.39-7.37 (2H, m), 6.77 (1H, d, J = 4.8 Hz), 5.01 (1H, t, J = 5.8 Hz), 4.16 (1H, dd, J = 6.8, 4.4 Hz), 3.77-3.72 (1H, m), 3.56-3.50 (1H, m), 2.35 (3H, s).

MC: 328.1 (M ⁺ +1).

Example 14

Preparation of (S) -4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one (compound A-14) :

To a solution of (S) -2-amino-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol (220 mg, 0.67 mmol) in chloroform (5 ml) obtained in example 13 is added while cooling to a temperature of -78 ° C, triethylamine (0.93 ml, 0.67 mmol), triphosgene (70 mg, 0.24 mmol) and the mixture is stirred at the same temperature within 3 hours. The reaction solution was warmed to room temperature and water was added and then it was extracted with ethyl acetate. After washing with brine, the organic layer was dried over magnesium sulfate. After concentration, the residue was washed with ethanol to give the title compound (41 mg, 17%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.70 (1H, broad s), 8.66 (1H, broad), 8.43 (1H, s), 8.11 (1H d, J = 5.2 Hz), 7.89 (1H, br s), 7.72 (1H, t, J = 8.0 Hz), 7.46 (1H, d, J = 8, 0 Hz), 7.44 (1H, d, J = 8.0 Hz), 6.78 (1H, broad d, J = 5.2 Hz), 5.28 (1H, ddd, J = 8, 8, 4.4, 1.2 Hz), 4.73 (1H, t, J = 8.8 Hz), 4.35 (1H, dd, J = 8.8, 4.4 Hz), 2, 34 (3H, s.)

MS: 354.1 (M ⁺ +1).

Example 15

Preparation of (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid dihydrochloride (compound A-15) :

Stage 1. Obtaining tert-butyl ether (1-thiocarbamoylpiperidin-4-yl) acetic acid :

To a solution of piperidin-4-yl-acetic acid tert-butyl ester (10.72 g, 50.0 mmol) in chloroform (100 ml) is added a solution of 9-fluorenylmethoxycarbonylisothiocyanate (14.07 g, 50.0 mmol) in chloroform (100 ml ) and the mixture was stirred at room temperature for 1 hour. Then piperidine (80 ml) was added and the mixture was again stirred at room temperature for 30 minutes. Then the reaction solution was concentrated, water was added, it was extracted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, and the residue obtained by concentration in vacuo was washed with isopropyl ether to obtain the title compound (11.35 g, 98%).

Stage 2. Obtaining tert-butyl ether of 1- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperidin-4-yl} acetic acid :

(1-Thiocarbamoylpiperidin-4-yl) acetic acid tert-butyl ester (11.95 g, 46.3 mmol) obtained in step 1 is added to a solution of 2-bromo-6-chloromethylpyridine (9.55 g, 6, 3 mmol) in ethanol (100 ml) obtained in Step 1 of Example 1, and the mixture was heated to boiling overnight. The temperature of the reaction solution was brought to room temperature; dimethylformamide dimethylacetal (9.3 ml, 69.4 mmol) was added and triethylamine (19 ml, 139 mmol) was added and heated to boiling point for 2 hours. After this, the reaction solution was concentrated, water was added, and then it was extracted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, and the residue obtained by vacuum concentration was purified by silica gel chromatography (n-hexane: ethyl acetate = 50:50 to 0: 100) to obtain the title compound (13.09 g, 65%) .

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 7.95 (1H, s), 7.80 (1H, d, J = 7.8 Hz), 7.67 (1H, t, J = 7.8 Hz), 7.36 (1H, d, J = 7.8 Hz), 4.02-3.95 (2H, m), 3.14-3.08 (2H, m), 2, 20 (2H, d, J = 7.2 Hz), 2.00-1.89 (1H, m), 1.79-1.72 (2H, m), 1.42 (9H, s), 1 34-1.21 (2H, m).

Step 3. Preparation of (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid tert-butyl ester :

rac-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (1.85 g, 2.97 mmol) and palladium acetate (500 mg, 2.22 mmol) are suspended in toluene (30 ml), after of this, 2-amino-4-picoline (1.60 g, 14.8 mmol) and tert-butyl ether {1- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperidin-4 are successively added -yl} acetic acid (6.50 g, 14.8 mmol) obtained in Step 2, then cesium carbonate (7.25 g, 22.2 mmol) is added and the mixture is stirred overnight at 100 ° C. Water was added to the reaction solution, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, and the residue obtained by concentration in vacuo was purified by silica gel chromatography (n-hexane: ethyl acetate = 1: 1 to 1:10) to obtain the title compound (4.30 g, 62% )

Step 4. Preparation of (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} piperidin-4-yl) acetic acid dihydrochloride:

Trifluoroacetic acid (20 ml) is added to the solution of tert-butyl ether (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} piperidin-4-yl) acetic acid (4.30 g, 9.23 mmol) in chloroform (20 ml) obtained in step 3, and stirred overnight at room temperature. Then 4n. hydrochloric acid-ethyl acetate solution (20 ml) was added to the concentrate obtained by concentration of the reaction solution in vacuo, and the precipitated solid was separated by filtration, washed with ethyl acetate (20 ml) to obtain the title compound (4.46 g, 100% )

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 12.23 (1H, br s), 8.45 (1H, d, J = 6.4 Hz), 8.07 (1H, s) , 7.88 (1H, t, J = 7.9 Hz), 7.56 (1H, d, J = 7.7 Hz), 7.50 (1H, broad s), 7.21 (1H, d, J = 6.4 Hz), 7.10 (1H, d, J = 8.2 Hz), 4.07-4.04 (2H, m), 3.25-3.15 (2H, m ), 2.50 (3H, s), 2.23 (2H, d, J = 7.1 Hz), 2.05-1.92 (1H, m), 1.86-1.78 (2H, m) 1.37-1.24 (2H, m).

MS: 410.3 (M ⁺ +1).

Example 16

Preparation of trans-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid (compound A-16) :

Stage 1. Obtaining methyl ester of trans-4-aminomethylcyclohexanecarboxylic acid hydrochloride:

Thionyl chloride (7 ml, 96 mmol) was added to a solution of trans-4-aminomethylcyclohexanecarboxylic acid (5.00 g, 31.8 mmol) in methanol (50 ml) and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated and the resulting solid was washed with diethyl ether (50 ml). Trans-4-aminomethylcyclohexanecarboxylic acid methyl ester hydrochloride (6.49 g, 98%) was obtained by separation by filtration and drying in vacuo.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 8.11-7.78 (3H, m), 3.59 (3H, s), 2.69-2.59 (2H, m), 2.31-2.19 (1H, m), 1.96-1.88 (2H, m), 1.85-1.75 (2H, m), 1.59-1.47 (1H, m) ), 1.36-1.21 (2H, m), 1.05-0.90 (2H, m).

Stage 2. Obtaining methyl ester of trans-4-thiouridide methylcyclohexanecarboxylic acid :

Sodium bicarbonate (1.68 g, 20.0 mmol) is added to a solution of trans-4-aminomethylcyclohexanecarboxylic acid methyl ester hydrochloride (2.07 g, 10.0 mmol) in chloroform (40 ml) obtained in step 1, 9- fluorenylmethoxycarbonyl isothiocyanate (2.81 g, 10.0 mmol) under ice-cooling. The reaction solution was stirred at room temperature for 16 hours, then piperidine (5 ml, 50 mmol) was added and the mixture was stirred at room temperature for another 6 hours. Trans-4-thiouridide methylcyclohexanecarboxylic acid methyl ester (1.55 g, 67%) was obtained by concentration in vacuo of the reaction solution and the resulting solid was purified by silica gel column chromatography (ethyl acetate).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 7.64-7.52 (1H, m), 6.96-6.76 (2H, m), 3.58 (1H, s), 3.26-3.16 (2H, m), 2.29-2.16 (1H, m), 1.95-1.84 (2H, m), 1.78-1.68 (2H, m) ), 1.51-1.38 (1H, m), 1.34-1.19 (2H, m), 1.01-0.83 (2H, m).

Stage 3. Obtaining methyl ester of trans-4 - {[5- (6-bromopyridin-2-yl) thiazol-2-ylamino] methyl} cyclohexanecarboxylic acid :

A solution in ethanol (15 ml) of methyl trans-4-thiouridide methylcyclohexanecarboxylic acid (1.55 g, 6.73 mmol) obtained in step 2, 2-bromo-6-chloromethylpyridine (1.38 g, 6.73 mmol) obtained in stage 1 of example 1, is stirred by heating to boiling point for 4 hours. After this, the reaction solution was cooled to room temperature, N, N-dimethylacetal dimethylformamide (0.9 ml, 10 mmol), triethylamine (1.8 ml, 20 mmol) were added, and the mixture was stirred under reflux for 1 hours. The reaction solution was cooled to room temperature and the solid obtained by concentration in vacuo was separated by filtration.

Trans-4 - {[5- (6-bromopyridin-2-yl) thiazol-2-ylamino] methyl} cyclohexanecarboxylic acid methyl ester (2.02 g, 73%) was obtained by washing it successively with water (10 ml), diethyl ether (10 ml) and drying in vacuo.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 8.15 (1H, t, J = 5.7 Hz), 7.83 (1H, s), 7.74 (1H, d, J = 7.9 Hz), 7.63 (1H, t, J = 7.9 Hz), 7.31 (1H, d, J = 7.9 Hz), 3.15-3.06 (2H, m) 2.32-2.19 (1H, m), 1.97-1.87 (2H, m), 1.85-1.76 (2H, m), 1.63-1.49 (1H, m), 1.37-1.23 (2H, m), 1.06-0.93 (2H, m).

Stage 4. Obtaining methyl ester of trans-4 - ({[5- (6-bromopyridin-2-yl] thiazol-2-yl) methylamino} methyl) cyclohexanecarboxylic acid :

Sodium hydride (53.6 mg, 60% in oil, 1.34 mmol) is added to a solution of trans-4 - {[5- (6-bromopyridin-2-yl) thiazol-2-ylamino] methyl} cyclohexanecarboxylic acid methyl ester (500 mg, 1.22 mmol) in N, N-dimethylformamide (5 ml) obtained in step 3, and the mixture was stirred at room temperature for 15 minutes. Methyl iodide (84 μl, 1.34 mmol) was added to the reaction solution, the mixture was stirred at room temperature for 2 hours and extracted by adding ethyl acetate (40 ml) and saturated aqueous ammonium solution (20 ml). The organic layer was washed with brine (20 ml × 2) and dried over magnesium sulfate. Trans-4 - ({[[5- (6-bromopyridin-2-yl) thiazol-2-yl] methylamino} methyl) cyclohexanecarboxylic acid methyl ester is obtained as a crude substance by filtration and concentration in vacuo.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 7.92 (1H, s), 7.77 (1H, d, J = 7.9 Hz), 7.65 (1H, t, J = 7.9 Hz), 7.32 (1H, d, J = 7.9 Hz), 3.58 (3H, s), 3.39-3.33 (2H, m), 3.10 (3H, s), 2.33-2.21 (1H, m), 1.97-1.86 (2H, m), 1.74-1.65 (2H, m), 1.57-1.47 ( 1H, m), 1.39-1.22 (2H, m), 1.11-0.97 (2H, m).

Step 5. Preparation of Trans-4 - [(N-methyl-N- {5- [6- (4-methyl-pyridin-2-ylamino) -pyridin-2-yl] thiazol-2-yl} amino) methyl] methyl ester]

cyclohexanecarboxylic acid :

To a solution of trans-4 - ({[5- (6-bromopyridin-2-yl) thiazol-2-yl] methylamino} methyl) cyclohexanecarboxylic acid methyl ester in toluene (10 ml) obtained in step 4 was added under Ar atmosphere 2-amino-4-picoline (132 mg, 1.22 mmol), palladium acetate (27 mg, 0.12 mmol), 2,2'-bis (diphenylphosphino) -1,1'-binaphthalene (75 mg, 0 , 12 mmol), cesium carbonate (596 mg, 1.83 mmol) and the mixture was stirred at 100 ° C for 16 hours. After this, the reaction solution was cooled to room temperature, it was filtered off, concentrated and trans-4 - [(methyl- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl methyl ester } amino] methyl]

cyclohexanecarboxylic acid (217 mg, 39%) was obtained by purification of the residue by silica gel chromatography (n-hexane: ethyl acetate = 1: 1).

Step 6. Preparation of trans-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino] methyl]

cyclohexanecarboxylic acid :

Trans-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] methyl ester solution]

cyclohexanecarboxylic acid (217 mg, 0.48 mmol) obtained in step 5, 1N. an aqueous solution of sodium hydroxide (2 ml, 2 mmol) in methanol (2 ml) and tetrahydrofuran (2 ml) was stirred at room temperature for 16 hours. It is neutralized with 1N. hydrochloric acid solution and extracted with chloroform (50 ml × 2). The organic layer was washed with brine (20 ml) and dried over magnesium sulfate, filtered and concentrated in vacuo. The solid obtained by adding a mixture of chloroform-diethyl ether (1: 1) (10 ml) to the residue was separated by filtration, dried in vacuo and thus obtained trans-4 - [(N-methyl-N- {5- [6 - (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl]

cyclohexanecarboxylic acid (190 mg, 90%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 12.04 (1H, s), 9.54 (1H, s), 8.08 (1H, d, J = 5.1 Hz), 8 , 03 (1H, s), 7.79 (1H, s), 7.56 (1H, t, J = 7.9 Hz), 7.20 (1H, d, J = 7.9 Hz), 7 15 (1H, d, J = 7.9 Hz), 6.75 (1H, d, J = 5.1 Hz), 3.38-3.29 (2H, m), 3.11 (1H, s), 2.34 (1H, s), 2.19-2.08 (1H, m), 1.97-1.87 (2H, m), 1.77-1.66 (2H, m) 1.57-1.43 (1H, m), 1.36-1.20 (2H, m), 1.10-0.97 (2H, m).

MS: 438.2 (M + 1).

Example 17

Preparation of 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid (compound A-17) :

Stage 1. Obtaining methyl ester of 3- (1-thiocarbamoylpiperidin-4-yl) propionic acid :

To a solution of 9-fluorenylmethoxycarbonylisothiocyanate (4.26 g, 15.2 mmol) in chloroform (40 ml) was added a solution of methyl ether (3-piperidin-4-yl) methylpropionic acid (2.62 g, 12.6 mol) in chloroform (10 ml) and sodium bicarbonate (6.40 g, 75.8 mmol) and the mixture was stirred overnight at room temperature. After this, the reaction solution was filtered to remove insoluble impurities, chloroform (20 ml) and piperidine (20 ml) were added, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate, the residue obtained by concentration in vacuo was purified by silica gel chromatography (n-hexane: ethyl acetate) to obtain the title compound (2.10 g, 63%).

Step 2. Preparation of 3- {1- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperidin-4-yl} propionic acid methyl ester :

To a solution of 2-bromo-6-chloromethylpyridine (1.88 g, 12 mmol) in ethanol (20 ml), obtained in step 1 of Example 1, methyl 3- (1-thiocarbamoylpiperidin-4-yl) propionic acid (2 10 g, 9.12 mmol) obtained in step 1, and the mixture is heated to the boiling point under reflux overnight. The temperature of the reaction solution was brought to room temperature, dimethylformamide dimethylacetal (1.8 ml, 14 mmol) and triethylamine (3.8 ml, 27 mmol) were added, and the resulting solution was heated to reflux for 1 hour. After this, the reaction solution was concentrated, water was added, and then it was extracted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, and the residue obtained by concentration in vacuo was purified by silica gel chromatography (n-hexane: ethyl acetate = 50:50 to 0: 100) to give the title compound (748 mg, 20%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 7.95 (1H, s), 7.80 (1H, dd, J = 7.9, 0.7 Hz), 7.67 (1H, t, J = 7.8 Hz), 7.36 (1H, dd, J = 7.7, 0.7 Hz), 4.00-3.97 (2H, m), 3.61 (3H, s ), 3.11-3.02 (2H, m), 2.37 (2H, t, J = 7.4 Hz), 1.79-1.72 (2H, m), 1.57-1, 49 (3H, m), 1.26-1.13 (2H, m).

Step 3. Preparation of 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid methyl ester :

rac-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (91 mg, 0.15 mmol) and palladium acetate (25 mg, 0.11 mmol) are suspended in toluene (7 ml), then sequentially add 2-amino-4-picoline (79 mg, 0.73 mmol) and 3- {1- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperidin-4-yl} propionic methyl ester acid (300 mg, 0.73 mmol) obtained in step 2, then cesium carbonate (357 mg, 1.1 mmol) is added and the mixture is stirred overnight at 100 ° C. Water was added to the reaction solution, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, and the residue obtained by concentration in vacuo was purified by silica gel chromatography (n-hexane: ethyl acetate = 1: 1 to 1:10) to obtain the title compound (250 mg, 55%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.55 (1H, br s), 8.09 (1H, d, J = 5.1 Hz), 7.96-7.93 ( 1H, m), 7.83 (1H, s), 7.58 (1H, t, J = 8.0 Hz), 7.23 (2H, t, J = 7.3 Hz), 6.77- 6.74 (1H, m), 3.99-3.92 (2H, m), 3.61 (3H, s), 3.11-3.02 (2H, m), 2.38 (2H, t, J = 7.3 Hz), 2.34 (3H, s), 1.81-1.74 (2H, m), 1.57-1.49 (3H, m), 1.29-1 15 (2H, m).

Step 4. Preparation of 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid :

To a mixed solution of 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-) propionic acid methyl ester (250 mg, 0, 57 mmol) obtained in Step 3 in tetrahydrofuran (5 ml) and methanol (5 ml) add 4N. sodium hydroxide solution (1.5 ml, 6.0 mmol) and the mixture was stirred at room temperature for 12 hours. The concentrate obtained by concentration in vacuo of the reaction solution was neutralized with 0.1N. hydrochloric acid solution and the precipitated solid was separated by filtration, washed with water and the title compound (142 mg, 59%) was obtained.

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 12.07 (1H, br s), 8.24 (1H, d, J = 4.6 Hz), 7.91 (1H, s) 7.76-7.66 (2H, m), 7.35 (1H, d, J = 7.7 Hz), 7.16 (1H, d, J = 8.1 Hz), 6.96- 6.90 (1H, m), 4.00 (2H, d, J = 13.0 Hz), 3.13-3.03 (2H, m), 2.41 (3H, s), 2.28 (2H, t, J = 7.3 Hz), 1.82-1.75 (2H, m), 1.55-1.47 (3H, m), 1.29-1.16 (2H, m )

MS: 424.1 (M ⁺ +1).

Example 18

Preparation of 2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid (compound A-18 ) :

Step 1. Preparation of 2-methyl-2- (1-thiocarbamoylpiperidin-4-yl) propionic acid ethyl ester :

To a solution of 9-fluorenylmethoxycarbonyl isothiocyanate (2.62 g, 9.32 mmol) in chloroform (20 ml) was added a solution of 2-methyl-2-piperidin-4-yl-propionic acid ethyl ester hydrochloride (2.27 g, 9.61 mmol) ) in chloroform (10 ml) and sodium bicarbonate (4.03 g, 48.0 mmol) and the mixture was stirred at room temperature. Then piperidine (30 ml) was added and the mixture was stirred at room temperature for another 2 hours. The reaction solution was concentrated in vacuo and the solid obtained by adding diethyl ether was separated by filtration. It was dissolved in N, N-dimethylformamide (20 ml) and piperidine (20 ml) was added and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate, and the residue obtained by concentration in vacuo was purified by silica gel chromatography (n-hexane: ethyl acetate) to obtain the title compound (2.4 g, 98%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 7.30 (2H, br s), 4.72-4.57 (2H, m), 4.08 (2H, q, J = 7 , 1 Hz), 2.88-2.77 (2H, m), 1.83-1.72 (1H, m), 1.55-1.46 (2H, m), 1.20-1, 09 (2H, m), 1.19 (3H, t, J = 7.1 Hz), 1.06 (6H, s).

Step 2. Preparation of 2- {1- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperidin-4-yl} -2-methylpropionic acid ethyl ester :

To a solution of 2-bromo-6-chloromethylpyridine (2.14 g, 10.4 mmol) in ethanol (30 ml) obtained in Step 1 of Example 1, 2-methyl-2- (1-thiocarbamoylpiperidin-4- ethyl ester was added il) propionic acid (2.44 g, 9.43 mmol) obtained in step 1, and the mixture is heated to boiling point for 5 hours. The reaction solution was cooled to room temperature, dimethylformamide dimethyl acetal (1.9 ml, 14 mmol) and triethylamine (3.9 ml, 28 mmol) were added and heated to reflux for 1 hour. After this, the reaction solution was concentrated, water was added, and then it was extracted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, and the residue obtained by vacuum concentration was purified by silica gel chromatography (n-hexane: ethyl acetate = 2: 1 to 1: 1) to obtain the title compound (2.48 g, 60%) .

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 7.93 (1H, s), 7.78 (1H, d, J = 7.8 Hz), 7.66 (1H, t, J = 7.8 Hz), 7.34 (1H, d, J = 7.8 Hz), 4.08-4.02 (2H, m), 4.08 (2H, q, J = 7.1 Hz) 3.08-2.98 (2H, m), 1.86-1.75 (1H, m), 1.66-1.58 (2H, m), 1.37-1.24 (2H, m), 1.18 (3H, t, J = 7.1 Hz), 1.08 (6H, s).

Step 3. Preparation of 2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid ethyl ester :

rac-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (213 mg, 0.34 mmol) and palladium acetate (58 mg, 0.26 mmol) are suspended in toluene (10 ml), then sequentially add 2-amino-4-picoline (203 mg, 1.88 mmol) and ethyl 2- {1- [5- (6-bromopyridin-2-yl) thiazol-2-yl] piperidin-4-yl} - 2-methylpropionic acid (748 mg, 1.71 mmol) obtained in step 2, then cesium carbonate (1.11 g, 3.41 mmol) was added and the mixture was stirred overnight at 100 ° C. Water was added to the reaction solution, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, and the residue obtained by concentration in vacuo was purified by silica gel chromatography (n-hexane: ethyl acetate = 1: 1 to 1: 3) to obtain the title compound (697 mg, 88%).

¹ H-NMR (400 MHz, DMSO- d ₆ ) δ: 9.53 (1H, br s), 8.09 (1H, d, J = 5.1 Hz), 7.95-7.92 ( 1H, m), 7.82 (1H, s), 7.58 (1H, t, J = 8.0 Hz), 7.25 (1H, d, J = 8.3 Hz), 7.22 ( 1H, d, J = 7.4 Hz), 6.75 (1H, d, J = 5.1 Hz), 4.09 (2H, q, J = 7.0 Hz), 4.06-4, 01 (2H, m), 3.09-2.99 (2H, m), 2.34 (3H, s), 1.86-1.77 (1H, m), 1.68-1.60 ( 2H, m), 1.41-1.28 (2H, m), 1.19 (3H, t, J = 7.0 Hz), 1.10 (6H, s).

Stage 4. Obtaining 2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid :

To a mixed solution of 2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid ethyl ester ( 697 mg, 1.50 mmol) obtained in Step 3 in methanol (5 ml) and tetrahydrofuran (10 ml), 4N was added. sodium hydroxide (3.7 ml, 15 mmol) and the mixture was stirred for 15 hours while heating to reflux. After concentration, the reaction solution is neutralized with 1N. hydrochloric acid solution (15 ml, 15 mmol) and the precipitated solid is separated by filtration, washed with water, ethyl acetate, tetrahydrofuran. It was then dried in vacuo to give the title compound (438 mg, 67%).

¹ H-NMR (400 MHz, DMSO-d ₆ ) δ: 9.53 (1H, br s), 8.09 (1H, d, J = 5.1 Hz), 7.95-7.92 ( 1H, m), 7.82 (1H, s), 7.58 (1H, t, J = 8.0 Hz), 7.25 (1H, d, J = 8.0 Hz), 7.22 ( 1H, d, J = 8.0 Hz), 6.75 (1H, d, J = 5.1 Hz), 4.07-4.00 (2H, m), 3.09-2.99 (2H , m), 2.34 (3H, s), 1.85-1.75 (1H, m), 1.71-1.64 (2H, m), 1.42-1.28 (2H, m ), 1.06 (6H, s).

MS: 438.2 (M ⁺ +1).

The following other aminopyridine compounds having a thiazole ring are prepared according to a procedure analogous to the general procedures mentioned above and / or the above examples. The structures of these compounds are determined by NMR analysis.

These compounds are presented in the following tables with the value of their inhibitory activity.

In the present description, the symbol "+++" IC50 (· M) means less than 0.1 · M, and the symbol "++" means not less than 0.1 · M and less than 1.0 M, and the symbol " + ”Means not less than 1.0 · M.

In addition, preferred compounds of the present invention also include the following compounds:

In addition, the preparation of compounds of the present invention containing thiophene will be described in detail as examples.

Example 19

Preparation of 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone (compound B-1)

Stage 1. Obtaining (6-bromopyridin-2-yl) - (4-methylpyridin-2-yl) amine

Suspension in toluene (200 ml) of 2,6-dibromopyridine (12.5 g), 2-amino-4-picoline (32.8 g, 139 mmol), palladium acetate (2.59 g, 11.6 mmol), rac-2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (8.64 g, 13.9 mmol), sodium tert-butoxide (13.3 g, 139 mmol) are heated and stirred in a stream of Ar at temperature of 80 ° C for 12 hours. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, the residue obtained by concentration in vacuo was purified by flash chromatography on silica gel (n-hexane: ethyl acetate = 3: 1) and then washed with isopropyl ether to obtain the title compound ( 15.4 g, 51%).

Stage 2. Obtaining 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone

Suspension in a solvent mixture of dimethoxyethane-water (12 ml) (6-bromopyridin-2-yl) - (4-methylpyridin-2-yl) amine (1.00 g, 3.79 mmol), 5-acetylthiophen-2-boronic acids (644 mg, 3.79 mmol), triphenylphosphine palladium tetrakis (440 mg, 0.38 mmol), sodium bicarbonate (480 mg, 5.68 mmol) are heated and stirred in a stream of Ar at 130 ° C for 12 hours. Water was added to the reaction solution and extracted with ethyl acetate. Then the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, the residue obtained by concentration in vacuo was washed with tetrahydrofuran-ethyl acetate (1: 1) to obtain the title compound (426 mg, 36%).

¹ H-NMR (300 MHz, DMSO-d ₆ ): 9.76 (broad s, 1H, broad s), 8.12 (1H, d, J = 4.8 Hz), 8.07 (1H , broad), 7.96 (1H, d, J = 4.2 Hz), 7.86 (1H, d, J = 4.2 Hz), 7.73 (1H, dd, J = 8.1 , 7.5 Hz), 7.52 (1H, d, J = 7.5 Hz), 7.43 (1H, d, J = 8.1 Hz), 6.80 (1H, broad d, J = 4.8 Hz), 2.56 (3H, s), 2.36 (3H, s).

Example 20

Preparation of 5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxaldehyde (Compound B-2) :

The title compound (293 mg, 26%) was obtained according to a similar procedure to the compound described for Step 2 of Example 14 using (6-bromopyridin-2-yl) - (4-methylpyridin-2-yl) amine (1.00 g, 3.79 mmol), 5-formylthiophene-2-boronic acid (1.30 g, 8.33 mmol), palladium tetrakistriphenylphosphine (875 mg, 0.76 mmol), sodium bicarbonate (954 mg, 11.4 mmol).

¹ H-NMR (300 MHz, DMSO-d ₆ ): 9.95 (1H, s), 9.80 (1H, s), 8.13 (1H, d, J = 5.2 Hz), 8, 02-8.10 (2H, m), 7.96 (1H, d, J = 3.8 Hz), 7.76 (1H, t, J = 7.9 Hz), 7.57 (1H, d , J = 7.2 Hz), 7.46 (1H, d, J = 8.3 Hz), 6.80 (1H, dd, J = 5.2, 0.9 Hz), 2.37 (3H , from).

Example 21

Preparation of 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanol (compound B-3) :

An ether solution of 3M-methylmagnesium bromide (0.19 ml, 0.57 mmol) was added to an ice-cooled solution of 5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carbaldehyde (70 mg, 0.24 mmol) in tetrahydrofuran (4 ml), after which the mixture was stirred at room temperature for 3 hours in a stream of Ar. Water was added to the reaction solution and extracted with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Then, the residue obtained by concentration in vacuo was washed with isopropyl ether to obtain the title compound (46 mg, 62%).

¹ H-NMR (300 MHz, CDCl ₃ ): 8.11 (1H, d, J = 7.2 Hz), 7.89 (1H, s), 7.57 (1H, t, J = 10.6 Hz), 7.42 (1H, d, J = 4.8 Hz), 7.33 (1H, broad), 7.19 (1H, d, J = 9.2 Hz), 7.12 (1H d, J = 11.2 Hz), 6.9 (1H, dd, J = 0.8, 1.2 Hz), 6.73 (1H, d, J = 7.2 Hz), 5.15 (1H, q, J = 8.5 Hz), 2.41 (3H, s), 1.65 (3H, d, J = 8.8 Hz).

Example 22

Obtaining ethyl 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} -acetic acid ethyl ester (compound B-4)

Acetic anhydride (0.02 ml, 0.19 mmol) was added to a solution of 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanol (40 mg , 0.13 mmol) in pyridine (2 ml) and it is reheated and stirred at a temperature of 60 ° C for 9 hours. Water was added to the reaction solution and extracted with acetic acid. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, the residue obtained by concentration in vacuo was purified by flash chromatography on silica gel (n-hexane: ethyl acetate = 2: 1) to obtain the title compound (10 mg, 22% )

¹ H-NMR (400 MHz, DMSO-d ₆ ): 9.64 (1H, s), 7.61-8.11 (2H, m), 7.36 (1H, d, J = 10.0 Hz ), 7.29 (1H, d, J = 11.6 Hz), 7.14 (1H, d, J = 4.8 Hz), 6.77 (1H, d, J = 7.2 Hz), 6.05-6.11 (1H, m), 2.36 (3H, s), 2.05 (3H, s), 1.61 (3H, d, J = 8.4 Hz).

In the description below, other aminopyridine compounds having a thiophene ring are prepared according to the general procedures and / or examples described above. The structures of these compounds are determined by NMR analysis.

These compounds are presented in the following tables with the value of their inhibitory activity.

In the present description, the symbol “+++” IC50 (· M) means less than 0.1 · M, and the symbol “++” means not less than 0.1 · M and less than 1.0 · M, and the symbol “+” Means not less than 1.0 · M.

The inhibitory activity against the Syk kinase of the compounds of the above example was studied. The testing method was the same as described below, inhibitory activity, etc. presented in the above tables.

Example 23

Syk kinase inhibition test (HTRF method) :

After the compounds are successively diluted with dimethyl sulfoxide (DMSO), 10 μl of them are 10-fold diluted with kinase buffer (20 mm HEPES pH 7.0, 10 mm MgCl ₂ , 50 mm NaCl, 1 mm 2-ME, 0.05% BSA) add to the optical tablet HTRF-96 (Packard) (with a final concentration of DMSO 2%). Add 20 μl of the substrate solution (kinase buffer mentioned above containing Syk Specific-Peptide Substrate Biot-EDPDYEWPSA-NH ₂ (Peptide Laboratory) 625 nM, 250 μM ATP (SIGMA)) (final substrate concentration 250 nM, 100 μM ATP), then add 20 μl of the enzyme solution (the above kinase buffer containing GST-Syk Full Protein (human) 16 nm) (final concentration of 6.4 nm); the mixture is immediately shaken on a plate shaker to start the enzymatic reaction. After reaching room temperature (20-25 ° C) for 30 min, the enzymatic reaction is stopped by adding 100 μl / well of buffer to stop and detect the reaction (30 mm HEPES pH 7.0, 150 mm KF, 0.15% BSA, 0.075 % Tween-20, 75 mM EDTA) containing HTRF reagent (5 μg / ml XL665-Streptavidin (CIS bio), 170 ng / ml Eu (K) -anti-PhosphoTyrosin, PT-66 (CIS bio)) (in the final concentrations of 20 mM HEPES pH 7.0, 100 mM KF, 0.1% BSA, 0.05% Tween-20, 50 mM EDTA). After keeping the reaction mixture for 1 hour at room temperature, the inhibitory effect of the compound on Syk kinase enzymatic activity was evaluated by measuring the ratio of fluorescence 665/620 to light excitation at 337 nm using ARVO (Wallac).

Example 24

Human mast cell culture inhibition test for degranulation

(1) Isolation of hematopoietic stem cells

After 10-60 ml of umbilical blood taken with heparin is diluted with an equivalent amount of buffer (0.5% BSA, 2 mM EDTA / PBS-), they are combined on a ficoll pack (Amersham Pharmacia Biotech) (ficoll / blood ( 1: 2)) and the mononuclear leukocyte fraction was collected by centrifugation at 400 × g (1350 rpm), 4 ° C for 30 minutes. After centrifugal washing (1500 rpm, 5 min, 4 ° C × 3) with buffer, the number of cells is counted and 0.1 ml of CD34 Progenitor Cell Isolation Kit (Miltenyi Biotec), reagent A1 (Fc-blocking) is added for every 1 × 10 ⁸ cells . After stirring, add 0.1 ml of reagent A2 (CD34 antibody-hapten) (final volume 0.5 ml / 1 × 10 ⁸ cells) and incubate at 9 ° C for an additional 15 minutes after stirring. After centrifugal washing (1500 rpm, 5 min, 4 ° C × 3), the reaction was resuspended in buffer (0.4 ml) and 0.1 ml of reagent B (anti-hapten antibody-microspheres) was added, stirred (final volume 0.5 ml / 1 × 10 ⁸ cells) and incubated at 9 ° C for another 15 minutes. After centrifugal washing (1500 rpm, 5 min, 4 ° C × 2), the reaction was resuspended in buffer (0.5 ml) and loaded onto a CS column (Miltenyi Biotec) installed in the MACS (MAgnetic Cell Sorting system; Miltenyi Biotec, Daiichi Pure Chemicals), then washed with 30 ml of buffer to remove CD34 ^- cells. The column was separated from the MACS and 30 ml of buffer was eluted, and the CD34 ⁺ column bound cells were collected and used as a population of hepatopoietic stem cells.

(2) Obtaining human mast cells by prolonged cultivation of hematopoietic stem cells:

CD34 ⁺ cells isolated as described in (1) are resuspended in Dulbecco's medium modified with Iscove (IMDM, Gibco) containing human (rh) SCF (1 μg / ml, Peprotech), rhIL-6 (0.5 μg / ml, Peprotech), rhIL-3 (10 ng / ml, Peprotech), 1% Insulin-Transferrin (Gibco), 5 × 10 ^-5 M 2-ME (Gibco), 0.1% BSA (Sigma) with a density 1 × 10 ⁶ cells / ml and dispensed on a 24-well cell plate in an amount of 0.1 ml / well, 0.9 ml IMDM (Methocult SF ^BIT StemCell technology) containing 0.9% methylcellulose was added and cultivation started. The described culture medium (excluding methyl cellulose) is added a week later and thereafter, 100 μl / well of said culture medium (also excluding IL-3) is added at weekly intervals so that these cells are diluted to maintain 10 ⁵ cells / ml / well and cultured for more than 8 weeks, and thus a human mast cell culture is obtained.

(3) Enhanced FcεRI Expression and Test for Inhibition of Degranulation-Stimulating IgE Cross-Binding

rhIL-4 (at a final concentration of 1 ng / ml, R & D) and Homo sapiens (h) IgE (at a final concentration of 0.5 μg / ml, CHEMICON) are added to obtain a culture of human mast cells and collected for 5 days for enhancing expression of FcεRI. After incubation, the cells are harvested and, after centrifugal washing (IMDM), are distributed on a 96-well culture plate in 5 × 10 ⁴ cells / 80 μl / well.

Add 10 μl of the compound, 10-fold diluted with IMDM, after dilution in DMSO (final concentration of DMSO 0.1%) and carry out the reaction for 10 minutes at 37 ° C. Then add 10 μl of anti-hIgE Ab (CHEMICON), adjusted to 100 μg / ml (final concentration of 10 μg / ml), and cause degranulation by stimulation at 37 ° C for 30 minutes. After centrifugation, 50 μl / well supernatant was collected and stored at −40 ° C. until degranulation volume was measured. Measurement of the volume of degranulation is performed using, as an indicator, the enzymatic activity of β-hexosaminidase contained in the granules. That is, an equivalent amount of p-nitrophenyl-N-acetyl-β-D-glucosaminide (1 mM) (containing 0.1% Triton X-100), which is a substrate of β-hexosaminidase, is added to 50 μl of the culture filtrate and then incubated with 37 ° C for 2 hours, the reaction is stopped by applying 100 μl of carbonate buffer (0.1 M, pH 10). The absorbance is measured at a wavelength of 405 nm and the amount (ratio) of degranulation is calculated relative to the level (Total) when the cells are destroyed by water. The effect of the test compound on the degranulation reaction is studied using this enzymatic activity as an indicator (IC ₅₀ value (μM)).

Example 25

Zap-70 kinase inhibition test (HTRF method)

After the compounds are sequentially diluted with DMSO, 10 μl of them, 10-fold diluted with kinase buffer (20 mm HEPES pH 7.0, 10 mm MgCl ₂ , 50 mm NaCl, 1 mm 2-ME, 0.05% BSA), add to the optical tablet HTRF-96 (Packard) (final concentration of DMSO 2%).

Add 20 μl of the substrate solution (the kinase buffer mentioned above containing Zap-70 specific peptide substrate Biot-EELQQDDYEMMEENLKKK-NH ₂ (Peptide Laboratory) 625 nm, ATP (SIGMA) 25 μM) (final substrate concentration of 250 nm, ATP 10 μM) and then add 20 μl of the enzyme solution (the above kinase buffer containing active Zap-70, UBI) 16 nM) (final concentration 6.4 nM), the mixture is immediately shaken on a plate shaker to start the enzymatic reaction. After incubation at room temperature for 90 minutes, the enzymatic reaction is stopped by adding 100 μl / well of buffer to stop and determine the reaction (30 mm HEPES pH 7.0, 150 mm KF, 0.15% BSA, 0.075% Tween-20, 75 mM EDTA) containing HTRF reagent (5 μg / ml XL665-Streptavidin (CIS bio), 170 ng / ml Eu (K) -anti-PhosphoTyrosin, PT-66 (CIS bio)) (with a final concentration of 20 mM HEPES pH 7 , 0, 100 mM KF, 0.1% BSA, 0.05% Tween-20, 50 mM EDTA). After the reaction mixture was kept at room temperature for 1 hour, the inhibitory effect of the compound against Zap-70 kinase enzymatic activity was evaluated by measuring the ratio of fluorescence 665/620 to light excitation at 337 nm using ARVO (Wallac).

Industrial applicability

The compound of the present invention is useful as an active ingredient in a pharmaceutical preparation. Since it has an inhibitory effect on Syk, the compound is particularly useful as a prophylactic / therapeutic agent in diseases in which an allergy or inflammatory reaction mediated by Syk is the main etiological cause (asthma, catarrhal rhinitis, atopic dermatitis, contact dermatitis, urticaria, food allergies, conjunctivitis, spring catarrh, etc.), for diseases in which ADCC is involved (autoimmune hemolytic anemia, malignant myasthenia, etc.), and for thrombosis in which thrombocyte aggregation is involved, etc.

Claims (24)

1. Aminopyridine compound represented by the following general formula (I)

where X ¹ represents
(1) —C (R ² ) = or
(2) a nitrogen atom;
X ² represents
(1) —C (R ³ ) = or
(2) a nitrogen atom;
X ³ represents
(1) —C (R ⁴ ) = or
(2) a nitrogen atom;
Z represents
(1) a nitrogen atom or
(2) -C (R ⁶ ') =;
Y ¹ represents
(1) -CH = or
Y ² represents
(1) -CH = or
(2) a nitrogen atom;
R represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group or
(3) an acyl group;
R ¹ represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group or
(3) a halogen atom;
R ² represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group or
(3) a halogen atom;
R ³ represents
(1) a hydrogen atom,
(2) a halogen atom,
(3) -N (R ³¹ ) (R ³² ),
where R ³¹ and R ³² represent a hydrogen atom or a C _1-6 alkyl group,
(4) a hydroxyl group,
(5) a C _1-6 alkoxy group, where a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a substituent selected from the following group Aa:
[Group Aa]
but. hydroxyl group
from. -N (R ³¹ ) (R ³² ),
where R ³¹ and R ³² have the meanings indicated above,
e. -CO-N (R ³¹ ) (R ³² ),
where R ³¹ and R ³² have the meanings indicated above, and
f. halogen atom
(6) an aralkoxy group,
(7) an acyl group,
(8) a saturated heterocyclic group, wherein the heterocyclic group may be substituted with a C _1-6 alkyl group, and the saturated heterocyclic group may partially have a double bond,
(9) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a substituent selected from the following Ab group:
[group ab]
but. hydroxyl group
b. -COOR ³³ , where R ³³ has the meaning indicated above,
from. —CO — N (R ³¹ ) (R ³² ), wherein R ³¹ and R ³² are as defined above, and
d. halogen atom
(10) -COOR ³³ ,
where R ³³ has the meaning indicated above,
(11) -CO-N (R ³¹ ) (R ³² ), where R ³¹ and R ³² are as defined above, or
(12) a cyano group,
R ³ together with R ² can form a group —C═C — C═C—;
R ⁴ represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group or
(3) a nitro group;
R ⁵ represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group, or
(3) -COOR ⁵¹ ,
where R ⁵¹ represents a C _1-6 alkyl group,
R ⁶ and R ^{6 '} may be the same or different, and each represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group,
(3) -COOR ⁶¹ ,
where R ⁶¹ represents a hydrogen atom or a C _1-6 alkyl group,
(4) -N (R ⁶² ) (R ⁶³ ),
where R ⁶² and R ⁶³ may be the same or different and each represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy group or an acyl group,
(5) -CO-N (R ⁶² ) (R ⁶³ ),
where R ⁶² and R ⁶³ have the meanings indicated above, or
(6) an acyl group;
R ⁷ represents a hydrogen atom, a halogen atom, a nitro group, a cyano group or the following R ^a , R ^b , R ^c , R ^d , R ^e , R ^f , R ^g or R ^h ;
R ^a is —C _p H _{2 (p-1)} (R ^a1 ) (R ^a2 ) —OR ^a3 ,
where (1) p is an integer from 1 to 6,
(2) R ^a1 represents a hydrogen atom or a C _1-6 alkyl group,
(3) R ^a2 represents a hydrogen atom, a C _1-6 alkyl group, an aralkyl group or an aryl group, where the C _1-6 alkyl group, an aralkyl group and an aryl group may be substituted with a substituent respectively selected from the following Ba group:
[Ba group]
but. hydroxyl group
b. carboxy group
from. C _1-6 alkoxycarbonyl group,
d. amino group
f. di-C _1-6 alkylamino group,
g. acyloxy group,
(4) R ^a3 represents a hydrogen atom, an acyl group, —CON (R ^a31 ) (R ^a32 ) or a C _1-6 alkyl group, where the alkyl group may be substituted with a C _1-6 alkoxycarbonyl group or —CON (R ^a31 ) (R ^a32 ),
where R ^a31 and R ^a32 may be the same or different and each represents
hydrogen atom
C _1-6 alkyl group,
R ^a31 and R ^a32 together with an adjacent nitrogen atom can form a 5- or 6-membered saturated heterocyclic group that has one or more nitrogen atoms, where the saturated heterocyclic group can be substituted with a hydroxyl group, oxo group, aralkylamino group or acylamino group;
R ^b represents-C _p H _{2 (p-1)} (R ^b1 ) (R ^b2 ) -N- (R ^b3 ) (R ^b4 ), where
(1) p is an integer from 1 to 6,
(2) R ^b1 represents a hydrogen atom or a C _1-6 alkyl group,
(3) R ^b2 represents
but. hydrogen atom
b. an aralkyl group, wherein the aralkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group which may be substituted with a hydroxyl group, an aralkyloxy group or —N (R ^b21 ) (R ^b22 ),
where R ^b21 and R ^b22 may be the same or different, and each represents a hydrogen atom, a C _1-6 alkyl group, an acyl group, a carbonyl group, a C _1-6 alkoxycarbonyl group or an aralkoxycarbonyl group,
from. an aryl group, wherein the aryl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group or an aralkoxy group, or
d. C _1-6 alkyl group, where C _1-6 alkyl group may be substituted with a substituent selected from the following Ca group:
[Group Ca]
hydroxyl group
aralkoxy group,
-COOR ^b23 ,
where R ^b23 represents a hydrogen atom, a C _1-6 alkyl group or an aralkyl group,
-N (R ^b21 ) (R ^b22 ), where R ^b21 and R ^b22 are as defined above, and
(4) R ^b3 and R ^b4 may be the same or different and each represents
but. hydrogen atom
b. C _1-6 alkyl group wherein C _1-6 alkyl group may be substituted with a substituent selected from hydroxy, carboxy, C _1-6 alkoxycarbonyl group, a carbamoyl group, C _1-6 alkylcarbamoyl group and a di-C _1-6 alkylcarbamoyl groups
from. -COOR ^b41 ,
where R ^b41 represents a hydrogen atom, a C _1-6 alkyl group or an aralkyl group,
d. -COR ^b42 ,
where R ^b42 represents
C _1-6 alkyl group, where C _1-6 alkyl group may be substituted with a substituent selected from
hydroxyl group
carboxy groups
C _1-6 alkoxycarbonyl group,
acyl group
acyloxy groups,
amino groups and
acylamino groups,
A C _3-8 cycloalkyl group, wherein a C _3-8 cycloalkyl group may be substituted with a hydroxyl group,
A 5- or 6-membered aromatic heterocyclic group having from 1 to 4 heteroatoms, where the heterocyclic group may be substituted with a C _1-6 alkyl group, or
an aryl group, wherein the aryl group may be substituted with a hydroxyl group,
e. -CO-N (R ^b43 ) (R ^b44 ), where R ^b43 and R ^b44 may be the same or different and each represents a hydrogen atom, a C _1-6 alkyl group or an acyl group, or
f. —SO ₂ —R ^b45 , where R ^b45 represents a C _1-6 alkyl group;
R ^c represents —C (= NR ^c1 ) —R ^c2 ,
where (1) R ^c1 represents
but. hydroxyl group
b. A C _1-6 alkoxy group, wherein a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a hydroxyl group or a C _1-6 alkoxy group, or
from. an acyloxy group, and
(2) R ^c2 represents a C _1-6 alkyl group or an amino group;
R ^d is —C (═O) —R ^d1 ,
where R ^d1 represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group or a C _1-6 alkoxycarbonyl group,
(3) a hydroxyl group,
(4) a C _1-6 alkoxy group and
(5) -N (R ^d11 ) (R ^d12 ),
where R ^d11 and R ^d12 may be the same or different and each represents a substituent selected from the following group Da:
[Da group]
but. hydrogen atom
b. C _1-6 alkoxy group,
from. C _3-8 cycloalkyl group, where the cycloalkyl group may be substituted by a hydroxyl group, and
d. A C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group or an amino group, or
R ^d11 and R ^d12 together with an adjacent nitrogen atom can form a 5- or 6-membered saturated heterocyclic group, which has one or more nitrogen atoms, where the saturated heterocyclic group can be substituted with C _1-6 alkyl groups, where the alkyl group can be substituted a carboxy group, or a carboxy group;
R ^e represents the following ring A:

where ring A represents
A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms,
A 5- or 6-membered aromatic heterocyclic group having from 1 to 4 heteroatoms,
A 9-12 membered fused aromatic heterocyclic group having 1 or 2 heteroatoms which may be partially saturated,
C _3-8 cycloalkyl group or
C _7-11 spiroheterocycloalkyl group having 1 or 2 heteroatoms; which may be substituted with a substituent respectively selected from the following group Ea:
[Group Ea]
a. -OR ^e1 where R ^e1 represents
hydrogen atom
A C _1-6 alkyl group, a C _1-6 alkyl group may be substituted with a carboxy group or —CON (R ^e11 ) (R ^e12 ),
where R ^e11 and R ^e12 may be the same or different and each represents a hydrogen atom or a C _1-6 alkyl group,
acyl group
carbamoyl group or
an aralkyl group,
b. -COOR ^e2 ,
where R ^e2 represents a hydrogen atom or a C _1-6 alkyl group,
from. -CO-N (R ^e41 ) (R ^e42 ),
where R ^e41 and R ^e42 may be the same or different and each represents
hydrogen atom
C _1-6 alkyl group, wherein the _C1-6 alkyl group may be substituted with a substituent selected from hydroxy, C _1-6 alkoxy, amino, C _1-6 alkylamino, di-C _1-6 alkylamino group, halogen atom, carboxyl group a carbamoyl group, a C _1-6 alkylcarbamoyl group, a di-C _1-6 alkylcarbamoyl group or a 5- or 6-membered saturated heterocyclic group or an aromatic heterocyclic group having 1 or 2 heteroatoms,
hydroxyl group
C _1-6 alkoxy,
A C _5-6 cycloalkyl group, wherein a C _5-6 cycloalkyl group may be substituted by a hydroxyl group or a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted by a hydroxyl group, or
C _1-6 alkylsulfonyl group,
d. -COR ^e3 ,
where R ^e3 represents
hydrogen atom
A C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a carboxy group, and a C _1-6 alkylsulfonyl group,
A 5- or 6-membered saturated heterocyclic group or an aromatic heterocyclic group having 1 or 2 heteroatoms, where the saturated heterocyclic group or aromatic heterocyclic group may be substituted by a hydroxyl group, an oxo group, a carboxy group, a C _1-6 alkoxy group, an acyl group, an amino group, an acylamino group di-C _1-6 alkylamino group, and C _1-6 alkyl group, where C _1-6 alkyl group may be substituted by a hydroxyl group, or
A C _5-6 cycloalkyl group or an aryl group, wherein a C _5-6 cycloalkyl group or an aryl group may be substituted with a hydroxyl group,
e. oxo group,
f. -N (R ^e51 ) (R ^e52 ),
where R ^e51 and R ^e52 may be the same or different, and each represents
hydrogen atom
C _1-6 alkylsulfonyl group,
A C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C _1-6 alkoxy group and a carbamoyl group,
an acyl group, where the acyl group may be substituted by a hydroxyl group or a C _1-6 alkoxy group,
-COR ^e511 ,
where R ^e511 represents a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted by a hydroxyl group or a C _5-6 cycloalkyl group, where the cycloalkyl group may be substituted by a hydroxyl group,
g. C _1-6 alkyl group, where C _1-6 alkyl group may be substituted with a substituent selected from the following group Eb:
[Group Eb]
hydroxyl group
A C _1-6 alkoxy group, wherein a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a carboxy group or —CO — N (R ^e11 ) (R ^e12 ), where R ^e11 and R ^e12 are as defined above,
-COOR ^e2 ,
where R ^e2 has the meaning indicated above,
-N (R ^e51 ) (R ^e52 ),
where R ^e51 and R ^e52 have the meanings indicated above,
-CO-N (R ^e51 ) (R ^e52 ),
where R ^e51 and R ^e52 have the meanings indicated above,
halogen atom and
A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, wherein the saturated heterocyclic group may be substituted with a hydroxyl group,
h. - (CH ₂ ) _n -N (R ^e61 ) - (CH ₂ ) _m -CO (R ^e62 ),
where n and m are an integer equal to 0 or from 1 to 4, and n + m are from 1 to 6, R ^e61 represents a hydrogen atom or a C _1-6 alkyl group and R ^e62 represents C _1-6 alkyl group, wherein the _C1-6 alkyl group may be substituted with a hydroxyl group, C _1-6 alkoxy, amino, C _1-6 alkylamino or di-C _1-6 alkylamino group,
i. hydroxyimino group,
j. C _1-6 alkylsulfonyl group,
k. cyano group
l. A 5- or 6-membered saturated heterocyclic group (which may be partially unsaturated) containing 1 or 2 heteroatoms selected from a nitrogen atom and an oxygen atom, or a 5- or 6-membered aromatic heterocyclic group containing from 1 to 4 heteroatoms, selected from a nitrogen atom and from an oxygen atom, where a saturated heterocyclic group and an aromatic heterocyclic group may be substituted by an oxo group or a C _1-6 alkyl group,
m. aminosulfonyl group and
n A C _1-6 alkylidene group, wherein a C _1-6 alkylidene group may be substituted with a halogen atom or a carboxy group;
R ^f represents a C _1-6 alkyl group or a C _2-6 alkenyl group, wherein said C _1-6 alkyl group and a C _2-6 alkenyl group may be substituted with a substituent selected from the following Fa group:
[Fa group]
but. A C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the alkoxy group may be substituted with a carboxy group, a C _1-6 alkoxycarbonyl group or —CON (R ^f21 ) (R ^f22 ),
where R ^f21 and R ^f22 may be the same or different and each represents
hydrogen atom
an acyl group, where the acyl group may be substituted by a hydroxyl group or a carboxy group,
C _1-6 alkoxycarbonyl group,
-O-COOR ^f1 ,
where R ^f1 represents a hydrogen atom or a C _1-6 alkyl group,
C _1-6 alkyl group,
where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group, a carbamoyl group,
C _1-6 alkylsulfonyl group or
carbamoyl group
b. -COOR ^f1 ,
where R ^f1 represents a hydrogen atom or a C _1-6 alkyl group,
from. -N (R ^f21 ) (R ^f22 ),
where R ^f21 and R ^f22 have the meanings indicated above,
d. -CON (R ^f21 ) (R ^f22 ),
where R ^f21 and R ^f22 have the meanings indicated above,
e. -N (R ^f23 ) CON (R ^f21 ) (R ^f22 ),
where R ^f23 represents a hydrogen atom or a C _1-6 alkyl group, and R ^f21 and R ^f22 have the meanings indicated above,
f. acyl group and
g. halogen atom;
R ^g is a substituent having ring B represented by the following formula (II):

where a is a linker selected from the following group Ga:
[Group Ga]
- (CH ₂ ) _k -,
- (CH ₂ ) _k -NR ^g1 - (CH ₂ ) _j -,
- (CH ₂ ) _k -O- (CO) NR ^g1 - (CH ₂ ) _j -,
- (CH ₂ ) _k -NR ^g1 (CO) - (CH ₂ ) _j -,
- (CH ₂ ) _k - (CO) - (CH ₂ ) _j -,
- (CO) -,
- (CH ₂ ) _k -O- (CH ₂ ) _j -,
- (CH ₂ ) _k -S- (CH ₂ ) _j -,
- (CH ₂ ) _k -O- (CO) - (CH ₂ ) _j -,
- (CO) NR ^g1 - and
- (CH ₂ ) _k -O- (CH ₂ ) _j (CO) - (CH ₂ ) _g -,
where k, j and g can be the same or different and represent an integer from 0 to 4, but k and j, or k and g cannot be equal to 0 at the same time,
R ^g1 represents
hydrogen atom
hydroxyl group
C _1-6 alkoxy,
an acyl group, where the acyl group may be substituted by a hydroxyl group or a carboxy group,
A C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group,
an aralkyl group or
C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group, —N (R ^g41 ) (R ^g42 ) or —CON (R ^g41 ) (R ^g42 ),
where R ^g41 and R ^g42 may be the same or different and represent
hydrogen atom
an acyl group, where the acyl group may be substituted by a hydroxyl group,
an aralkyl group,
C _1-6 alkylsulfonyl group or
C _1-6 alkyl group,
wherein the C _1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group, —N (R ^g51 ) (R ^g52 ) or —CO — N (R ^g51 ) (R ^g52 ),
where R ^g51 and R ^g52 may be the same or different and represent
hydrogen atom
an acyl group, where the acyl group may be substituted by a hydroxyl group,
C _1-6 alkyl group,
where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, an acylamino group, a C _1-6 alkoxycarbonyl group or a halogen atom,
C _1-6 alkoxycarbonyl group,
C _1-6 alkylsulfonyl group or
A C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group, or
R ^g51 and R ^g52 together with an adjacent nitrogen atom can form a 5- or 6-membered saturated heterocyclic group that has one or more nitrogen atoms, where the saturated heterocyclic group can be substituted with a hydroxyl group or a C _1-6 alkoxy group,
ring B is a ring selected from the following group On:
[Group On]
aryl group
C _3-8 cycloalkyl group,
5-7 membered saturated heterocyclic group containing one or more nitrogen atoms,
A 5-6 membered aromatic heterocyclic group containing at least one heteroatom, and
ring B may be substituted with a substituent selected from the following group Ia:
[Group Ia]
a. -OR ^g2 ,
where R ^g2 represents
hydrogen atom
C _1-6 alkyl group or
an aralkyl group,
b. -COOR ^g3 ,
where R ^g3 represents
hydrogen atom
C _1-6 alkyl group or
an aralkyl group, wherein the alkyl group may be substituted with a hydroxyl group,
from. -N (R ^g41 ) (R ^g42 ),
where R ^g41 and R ^g42 have the meanings indicated above,
d. —CO — R ^g53 , where R ^g53 is
C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group, a carboxy group or an acylamino group,
A C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group or an oxo group,
A 5- or 6-membered saturated heterocyclic group containing at least one heteroatom, wherein the saturated heterocyclic group may be substituted with a hydroxyl group, a C _1-6 alkyl group or an oxo group,
an aryl group, wherein the aryl may be substituted with a hydroxyl group,
A 5- or 6-membered aromatic heterocyclic group containing at least one heteroatom, or
an aralkyl group;
e. C _1-6 alkyl group, where C _1-6 alkyl group which may be substituted by hydroxyl group, C _1-6 alkoxy group, aralkoxy group, carboxy group, C _1-6 alkoxycarbonyl group, -CO-R ^g53 , where R ^g53 has the meaning indicated above, —N (R ^g51 ) (R ^g52 ) or —CO-N (R ^g51 ) (R ^g52 ),
where R ^g51 and R ^g52 have the meanings indicated above,
f. -CO-N (R ^g51 ) (R ^g52 ),
where R ^g51 and R ^g52 have the meanings indicated above,
g. C _1-6 alkylsulfonyl group,
h. oxo group
i. an aryl group, wherein the aryl group may be substituted with a hydroxyl group,
j. aralkyl group and
k. halogen atom; and
R ^h represents —N (R ^h1 ) (R ^h2 ),
where R ^hl represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group, —N (R ^g51 ) (R ^g52 ), —CO-N (R ^g51 ) (R ^g52 ), where R ^g51 and R ^g52 are as defined above, a C _1-6 alkylsulfonyl group or a halogen atom,
(3) a C _2-6 alkenyl group,
(4) a C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group, or
(5) an aralkyl group,
R ^h2 represents
(1) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a substituent selected from the following group Ja:
[Group Ja]
hydroxyl group
C _1-6 alkoxy group,
carboxy group
aromatic carbocyclic group, where the aromatic carbocyclic group may be substituted by a hydroxyl group, a C _1-6 alkyl group, where the alkyl group may be substituted by a carboxy group, a halogen atom, a C _1-6 alkoxy group, a carboxy group, a C _1-6 alkoxycarbonyl group, C _{2- 6 by an} alkenyl group, wherein the C _2-6 alkenyl group may be substituted with a carboxy group,
C _3-8 cycloalkyl group, where the cycloalkyl group may be substituted by a carboxy group or an aralkoxy group,
A 5- or 6-membered aromatic heterocyclic group containing 1 or 2 heteroatoms, where the aromatic heterocyclic group may be substituted with a carboxy group,
A 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms,
-N (R ^g51 ) (R ^g52 ),
where R ^g51 and R ^g52 have the meanings indicated above,
-CON (R ^g51 ) (R ^g52 ),
where R ^g51 and R ^g52 have the meanings indicated above,
-COR ^g53 , where R ^g53 has the meaning indicated above, and
-COOR ^g3 , where R ^g3 has the meaning indicated above,
(2) an acyl group, where the acyl group may be substituted by a hydroxyl group,
(3) C _1-6 alkoxycarbonyl group,
(4) a C _2-6 alkenyl group, wherein the alkenyl group may be substituted with a carboxy group or a halogen atom,
(5) a C _3-8 cycloalkyl group where the cycloalkyl group may be substituted with a hydroxyl group, —COOR ^g3 , where R ^g3 is as defined above, —COR ^g53 , where R ^g53 is as defined above, ^{—CONR g51} R ^g52 where R ^g51 and R ^g52 each have the meaning indicated above, or a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group,
(6) a 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted with —COR ^g53 , where R ^g53 is as defined above, —COOR ^g3 , where R ^g3 is as indicated above, ^{—CONR g51} R ^g52 , where R ^g51 and R ^g52 each, is as defined above, or a C _1-6 alkylsulfonyl group, or
(7) an aromatic carbocyclic group, where the aromatic carbocyclic group may be substituted by a carboxy group, a C _1-6 alkyl group, where the alkyl group may be substituted by a carboxy group or a C _2-6 alkenyl group, where the alkenyl group may be substituted by a carboxy group, or a pharmaceutically acceptable group thereof salt. 2. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein Z represents a nitrogen atom. 3. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 2, wherein the aminopyridine compound according to claim 1 is an aminopyridine compound represented by the following general formula (Ia-1):

where X ¹ represents
(1) —C (R ² ) =;
X ² represents
(1) —C (R ³ ) = or
(2) a nitrogen atom;
X ³ represents
(1) —C (R ⁴ ) = or
(2) a nitrogen atom;
Y ¹ represents
(1) -CH =;
R ¹ represents
(1) a hydrogen atom or
(2) a C _1-6 alkyl group;
R ² represents
(1) a hydrogen atom,
(2) a halogen atom or
(3) a C _1-6 alkyl group;
R ³ represents
(1) a hydrogen atom,
(2) a halogen atom,
(3) a C _1-6 alkoxy group, wherein a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a substituent selected from the following group Aa-1:
[Group Aa-1]
but. hydroxyl group
from. -N (R ³¹ ) (R ³² ),
where R ³¹ and R ³² represent a hydrogen atom or a C _1-6 alkyl group,
d. halogen atom
(4) an aralkoxy group,
(5) an acyl group,
(6) a saturated heterocyclic group, wherein the heterocyclic group may be substituted with a C _1-6 alkyl group, and the saturated heterocyclic group may partially have a double bond,
(7) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a substituent selected from the following Ab-1 group:
[Group Ab-1]
but. hydroxyl group
b. -COOR ³³ , where R ³³ represents a hydrogen atom or a C _1-6 alkyl group,
from. —CO — N (R ³¹ ) (R ³² ), wherein R ³¹ and R ³² are as defined above, and
d. a halogen atom, or
(8) a cyano group, or
R ³ together with R ² can form a group —C═C — C═C—;
R ⁴ represents
(1) a hydrogen atom or
(2) a C _1-6 alkyl group;
R ⁶ represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group, wherein a C _1-6 alkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group,
(3) -COOR ⁶¹ ,
where R ⁶¹ represents a hydrogen atom or a C _1-6 alkyl group,
(4) -N (R ⁶² ) (R ⁶³ ),
where R ⁶² and R ⁶³ may be the same or different and each represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy group or an acyl group,
(5) —CO — N (R ⁶² ) (R ⁶³ ), wherein R ⁶² and R ⁶³ are as defined above, or
(6) an acyl group; and
R ⁷ is the same as indicated in claim 1. 4. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claims 1-3, wherein the aminopyridine compound according to claims 1-3 is an aminopyridine compound represented by the following general formula (Ia-2):

where X ² represents
(1) = C (R ³ ) - or
(2) a nitrogen atom;
R ² represents
(1) a hydrogen atom or
(2) a halogen atom;
R ³ represents
(1) a hydrogen atom,
(2) a halogen atom,
(3) With _1-6 alkoxygroup,
where a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a substituent selected from the following Aa-2 group:
[Group Aa-2]
but. hydroxyl group and
b. halogen atom
(4) an acyl group,
(5) a saturated heterocyclic group, wherein the heterocyclic group may be substituted with a C _1-6 alkyl group, and the saturated heterocyclic group may partially have a double bond,
(6) A C _1-6 alkyl group which may be substituted with a substituent selected from the following Ab-2 group:
[Group Ab-2]
but. hydroxyl group and
b. halogen atom or
(7) a cyano group, or
R ³ together with R ² can form a group —C═C — C═C—;
R ⁶ represents
(1) a hydrogen atom or
(2) a C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group;
R ⁷ represents a hydrogen atom or the following R ^a , R ^b , R ^c , R ^d , R ^e , R ^f , R ^g or R ^h ;
R ^a represents —C _p H _{2 (p-1)} (R ^al ) (R ^a2 ) —OR ^a3 ,
where (1) p is an integer from 1 to 6,
(2) R ^a1 represents a hydrogen atom,
(3) R ^a2 represents
A C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group, an acyloxy group, or a di-C _1-6 alkylamino group,
an aralkyl group, wherein the aralkyl group may be substituted with a hydroxyl group, a carboxy group or an acyloxy group, or
aryl group
(4) R ^a3 represents a hydrogen atom, an acyl group or - (CO) N (R ^a31 ) (R ^a32 ),
where R ^a31 and R ^a32 may be the same or different and represent a hydrogen atom or a C _1-6 alkyl group;
R ^b represents —C _p H _{2 (p-1)} (R ^bl ) (R ^b2 ) -N- (R ^b3 ) (R ^b4 ), where
(1) p is an integer from 1 to 6,
(2) R ^b1 represents a hydrogen atom,
(3) R ^b2 represents
but. an aralkyl group, wherein the aralkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group which may be substituted with a hydroxyl group, an aralkyloxy group or —N (R ^b21 ) (R ^b22 ),
where R ^b21 and R ^b22 represent a hydrogen atom, a C _1-6 alkyl group, an acyl group or an aralkoxycarbonyl group,
b. an aryl group, wherein the aryl group may be substituted with a hydroxyl group or an aralkoxy group, or
from. A C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group, an aralkoxy group, an aralkoxycarbonyl group, an amino group,
(4) R ^b3 represents a hydrogen atom or a C _1-6 alkyl group,
(5) R ^b4 represents
but. hydrogen atom
b. A C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a carboxy group or a C _1-6 alkoxycarbonyl group,
from. -COR ^b32 ,
where R ^b32 represents a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group, an acyl group, a carboxy group, a C _1-6 alkoxycarbonyl group or an acyloxy group,
or
d. -CON (R ^b321 ) (R ^b322 ),
where R ^b321 and R ^b322 represent a hydrogen atom or a C _1-6 alkyl group;
R ^c represents —C (= NR ^c1 ) —R ^c2 ,
where (1) R ^c1 represents
but. hydroxyl group
b. A C _1-6 alkoxy group, wherein a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a hydroxyl group, or
from. acyloxy group
(2) R ^c2 represents a C _1-6 alkyl group
R ^d is —C (═O) —R ^d1 ,
where R ^d1 represents
(1) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group or a C _1-6 alkoxycarbonyl group,
(2) With _1-6 alkoxygroup,
(4) -N (R ^d11 ) (R ^d12 ),
where R ^d11 and R ^d12 may be the same or different and each represents
hydrogen atom
C _1-6 alkoxy or
A C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a hydroxyl group, a carboxy group or a C _1-6 alkoxycarbonyl group;
R ^e represents
A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms,
A 5- or 6-membered aromatic heterocyclic group having from 1 to 4 heteroatoms,
A 9-12 membered fused aromatic heterocyclic group, which may be partially saturated, having 1 or 2 heteroatoms,
C _3-8 cycloalkyl group or
C _7-11 spiroheterocycloalkyl group having 1 or 2 heteroatoms, and each may be substituted with a substituent selected from the following group Ea-1:
[Group EA-1]
a. -OR ^e1 where R ^e1 represents
hydrogen atom
A C _1-6 alkyl group, wherein a C _1-6 alkyl group may be substituted with a carboxy group or —CON (R ^e11 ) (R ^e12 ),
where R ^e11 and R ^e12 may be the same or different and each represents a hydrogen atom or a C _1-6 alkyl group,
acyl group
carbamoyl group or
an aralkyl group,
b. -COOR ^e2 ,
where R ^e2 represents a hydrogen atom or a C _1-6 alkyl group,
from. -CO-N (R ^e41 ) (R ^e42 ),
where R ^e41 and R ^e42 may be the same or different and each represents
hydrogen atom
A C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a substituent selected from a hydroxyl group, a C _1-6 alkoxy group, a di C _1-6 alkylamino group, a carboxy group, a halogen atom, a C _1-6 alkylcarbamoyl group, and A 5- or 6-membered saturated heterocyclic group or an aromatic heterocyclic group having 1 or 2 heteroatoms,
hydroxyl group
C _1-6 alkoxy,
A C _5-6 cycloalkyl group, wherein a C _5-6 cycloalkyl group may be substituted with a hydroxyl group, or,
C _1-6 alkylsulfonyl group,
d. -COR ^e3 ,
where R ^e3 represents a hydrogen atom, a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxy group, a carboxy group or a C _1-6 alkylsulfonyl group, a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted with a hydroxyl group, a carboxy group, a C _1-6 alkyl group, an acyl group, a C _1-6 alkoxy group, an amino group, an alkylamino group, a diC _1-6 alkylamino group, an alkylsulfonylamino group, an acylamino group or an oxo group A C _5-6 cycloalkyl group, wherein the C _5-6 cycloalkyl group may be substituted with a hydroxyl group, an aryl group where the aryl group may be substituted with a hydroxyl group,
e. oxo group,
f. -N (R ^e51 ) (R ^e52 ),
where R ^e51 and R ^e52 may be the same or different and each represents
hydrogen atom
C _1-6 alkylsulfonyl group,
C _1-6 alkyl group, where C _1-6 alkyl group may be substituted by a hydroxyl group,
an acyl group, where the acyl group may be substituted by a hydroxyl group, or
-COR ^e511 ,
where R ^e511 represents a C _5-6 cycloalkyl group, where the C _5-6 cycloalkyl group may be substituted by a hydroxyl group,
g. C _1-6 alkyl group, where C _1-6 alkyl group may be substituted with a substituent selected from the following group Eb-1:
[Group Eb-1]
hydroxyl group
A C _1-6 alkoxy group, wherein a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a carboxy group or —CO — N (R ^e11 ) (R ^e12 ), where R ^e11 and R ^e12 are as defined above,
-COOR ^e2 ,
where R ^e2 has the meaning indicated above,
-N (R ^e51 ) (R ^e52 ),
where R ^e51 and R ^e52 have the meanings indicated above,
-CO-N (R ^e51 ) (R ^e52 ),
where R ^e51 and R ^e52 have the meanings indicated above,
halogen atom and
A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms,
h. hydroxyimino group,
i. C _1-6 alkylsulfonyl group,
j. cyano group
k. A 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms selected from a nitrogen atom and an oxygen atom (which may be partially unsaturated and may be substituted by an oxo group or a C _1-6 alkyl group) or an aromatic heterocyclic group containing from 1 to 4 heteroatoms selected from a nitrogen atom and from an oxygen atom,
l. aminosulfonyl group and
m. A C _1-6 alkylidene group, wherein a C _1-6 alkylidene group may be substituted with a halogen atom or a carboxy group;
R ^f represents a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from the following Fa-1 group:
[Group Fa-1]
but. A C _1-6 alkoxy group, wherein the C _1-6 alkyl group in the alkoxy group may be substituted with a carboxy group, a C _1-6 alkoxycarbonyl group or —CON (R ^f21 ) (R ^f22 ),
where R ^f21 and R ^f22 may be the same or different and each represents
hydrogen atom
an acyl group, where the acyl group may be substituted by a hydroxyl group or a carboxy group,
C _1-6 alkoxycarbonyl group,
-O-COOR ^f1 ,
where R ^f1 represents a hydrogen atom or a C _1-6 alkyl group,
C _1-6 alkyl group,
where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, a C _1-6 alkoxycarbonyl group or a carbamoyl group,
C _1-6 alkylsulfonyl group or
carbamoyl group
b. -COOR ^f1 ,
where R ^f1 has the meaning indicated above,
from. -N (R ^f21 ) (R ^f22 ),
where R ^f21 and R ^f22 have the meanings indicated above,
d. -CON (R ^f21 ) (R ^f22 ),
where R ^f21 and R ^f22 have the meanings indicated above,
e. acyl group and
f. halogen atom;
R ^g is a substituent having ring B ′ represented by the following formula (IIa):

where A 'is a linker selected from the following group Ga-1:
[Group Ga-1]
- (CH ₂ ) _k ,
- (CH ₂ ) _k -NR ^g1 - (CH ₂ ) _j -,
- (CH ₂ ) _k -O- (CO) NR ^g1 - (CH ₂ ) _j -,
- (CH ₂ ) _k -NR ^g1 (CO) - (CH ₂ ) _j -,
- (CH ₂ ) _k - (CO) - (CH ₂ ) _j -,
- (CO) -,
- (CH ₂ ) _k -O- (CH ₂ ) _j -,
- (CH ₂ ) _k -S- (CH ₂ ) _j -,
- (CH ₂ ) _k -O- (CO) - (CH ₂ ) _j - and
- (CH ₂ ) _k -O- (CH ₂ ) _j (CO) - (CH ₂ ) _g -,
where k, j and g can be the same or different and represent an integer from 0 to 4, but k and j, or k and g cannot be equal to 0 at the same time,
R ^g1 represents
hydrogen atom
an acyl group, where the acyl group may be substituted by a carboxy group or a hydroxyl group, or
C _1-6 alkyl group,
ring B 'is a ring selected from the following Na-1 group:
[Group At-1]
aryl group
C _3-8 cycloalkyl group,
A 5-7 membered saturated heterocyclic group having at least one nitrogen atom, and
A 5- or 6-membered aromatic heterocyclic group containing 1 or 2 heteroatoms, and
ring B 'may be substituted with a substituent selected from the following group Ia-1:
[Group Ia-1]
a. -OR ^g2 ,
where R ^g2 represents
hydrogen atom
C _1-6 alkyl group or
aralkyl group,
b. -COOR ^g3 ,
where R ^g3 represents
hydrogen atom or
C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group,
c. -N (R ^g41 ) (R ^g42 ),
where R ^g41 and R ^g42 have the meanings indicated above,
d. —CO — R ^g53 , where R ^g53 is
C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group, a carboxy group or an acylamino group,
A C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group or an oxo group,
an aryl group, wherein the aryl group may be substituted with a hydroxyl group,
A 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted with a hydroxyl group, a C _1-6 alkyl group or an oxo group,
an aralkyl group or
A 5- or 6-membered aromatic heterocyclic group containing 1 or 2 heteroatoms,
e. A C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group or —CO — R ^g53 , where R ^g53 are as defined above,
f. -CO-N (R ^g51 ) (R ^g52 ),
where R ^g51 and R ^g52 may be the same or different and represent
hydrogen atom
an acyl group, where the acyl group may be substituted by a hydroxyl group,
C _1-6 alkyl group,
where the C _1-6 alkyl group may be substituted by a hydroxyl group, a carboxy group, an acylamino group, a C _1-6 alkoxycarbonyl group or a halogen atom,
C _1-6 alkylsulfonyl group,
C _1-6 alkoxycarbonyl group,
or
A C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group,
g. C _1-6 alkylsulfonyl group,
h. oxo group and
i. halogen atom; and
R ^h represents —N (R ^h1 ) (R ^h2 ),
where R ^h1 represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a hydroxyl group, a C _1-6 alkoxy group, —N (R ^g51 ) (R ^g52 ), —CO-N (R ^g51 ) (R ^g52 ), C _1-6 alkylsulfonyl or a halogen atom,
where R ^g51 and R ^g52 have the meanings indicated above,
(3) a C _2-6 alkenyl group,
(4) a C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group or a C _1-6 alkoxy group, or
(5) an aralkyl group,
R ^h2 represents
(1) a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted with a substituent selected from the following group Ja-1:
[Group Ja-1]
hydroxyl group
C _1-6 alkoxy group,
carboxy group
aromatic carbocyclic group, where the aromatic carbocyclic group may be substituted by a hydroxyl group, a C _1-6 alkyl group, where the alkyl group may be substituted by a carboxy group, a halogen atom, a C _1-6 alkoxy group, a carboxy group, a C _1-6 alkoxycarbonyl group, C _{2- 6 by an} alkenyl group, wherein the C _2-6 alkenyl group may be substituted with a carboxy group,
C _3-8 cycloalkyl group, where the cycloalkyl group may be substituted by a carboxy group or an aralkoxy group,
A 5- or 6-membered aromatic heterocyclic group containing 1 or 2 heteroatoms, where the aromatic heterocyclic group may be substituted with a carboxy group,
A 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms,
-N (R ^g51 ) (R ^g52 ) and
-CON (R ^g51 ) (R ^g52 ),
where R ^g51 and R ^g52 have the meanings indicated above,
(2) an acyl group, where the acyl group may be substituted by a hydroxyl group,
(3) a C _2-6 alkenyl group, wherein the alkenyl group may be substituted with a carboxy group or a halogen atom,
(4) a C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a hydroxyl group, —COOR ^g3 , where R ^g3 is as defined above, —COR ^g53 , where R ^g53 is as defined above, ^{—CONR g51} R ^g52 where R ^g51 and R ^g52 each have the meaning indicated above, or a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group,
(5) a 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted with —COR ^g53 , where R ^g53 is as defined above, —COOR ^g3 , where R ^g3 is as indicated above, ^{—CONR g51} R ^g52 , where R ^g51 and R ^g52 each, has the meaning indicated above, or a C _1-6 alkylsulfonyl group, or
(6) an aromatic carbocyclic group, wherein the aromatic carbocyclic group may be substituted with a carboxy group, a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group or a C _2-6 alkenyl group, where the alkenyl group may be substituted with a carboxy group. 5. The aminopyridine compound or its pharmaceutically acceptable salt according to claim 4, where
R ² represents a hydrogen atom,
R ³ represents a C _1-6 alkyl group, where the C _1-6 alkyl group may be substituted by a hydroxyl group or a halogen atom,
R ⁶ represents a hydrogen atom, and
R ⁷ represents R ^e , R ^g or R ^h . 6. The aminopyridine compound or its pharmaceutically acceptable salt according to claim 5, where
R ⁷ represents R ^e , and
R ^e represents
(1) a 5- or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms, where the saturated heterocyclic group may be substituted with a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group, -COR ^e3 , where R ^e3 represents A 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, where a 5- or 6-membered saturated heterocyclic group may be substituted with a hydroxyl group or —CO — N (R ^e41 ) (R ^e42 ), where R ^e41 and R ^e42 may be the same or different and each represents a hydrogen atom ode, or a C _1-6 alkyl group, or
(2) a C _3-8 cycloalkyl group, wherein the cycloalkyl group may be substituted with a C _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group, -COR ^e3 , where R ^e3 is a 5- or 6-membered saturated heterocyclic group, having 1 or 2 heteroatoms, where the 5- or 6-membered saturated heterocyclic group may be substituted by a hydroxyl group or —CO-N (R ^e41 ) (R ^e42 ), where R ^e41 and R ^e42 may be the same or different and each is a hydrogen atom or a C _1-6 alkyl group. 7. The aminopyridine compound or its pharmaceutically acceptable salt according to claim 6, where
R ^e represents
(1) a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms represented by the following ring L, where the saturated heterocyclic group may be substituted with 1 or 2 identical or different substituents selected from a C _1-6 alkyl group, where alkyl the group may be substituted with a carboxy group, -COR ^e3 , where R ^e3 is a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, where the 5- or 6-membered saturated heterocyclic group may be substituted with a hydroxyl group, or -CO -N (R ^e41 ) (R ^e42 ), where R ^e41 and R ^e42 may be the same or different and each represents a hydrogen atom or a C _1-6 alkyl group,

where the ring L represents a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, or (2) a 5- or 6-membered cycloalkyl group, where the cycloalkyl group may be substituted with 1 or 2 identical or different substituents selected from With a _1-6 alkyl group, where the alkyl group may be substituted with a carboxy group, -COR ^e3 , where R ^e3 is a 5- or 6-membered saturated heterocyclic group having 1 or 2 heteroatoms, where a 5- or 6-membered saturated heterocyclic group hydroxyl may be substituted hydrochloric group, or ^{-CO-N (R e41) (} R e42), wherein R ^e41 and R ^e42 are the same or different and each represents a hydrogen atom or a C _1-6 alkyl group. 8. The aminopyridine compound or its pharmaceutically acceptable salt according to claim 5, where
R ^h represents —N (R ^h1 ) (R ^h2 ) and R ^h1 represents a C _1-6 alkyl group, R ^h2 represents a C _3-8 cycloalkyl group, where the cycloalkyl group may be substituted with —COOR ^g3 , where R ^g3 represents a hydrogen atom or a C _1-6 alkyl group, where the alkyl group may be substituted by a hydroxyl group. 9. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein the aminopyridine compound is selected from the following group of compounds:
(001) 1-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-2-one,
(002) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxylic acid,
(003) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(004) N-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(005) N- (2-hydroxyethyl) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide,
(006) methyl trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid methyl ester,
(007) trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid,
(008) (4-hydroxypiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone,
(009) N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) amine,
(010) N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,
(011) (S) -3-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one,
(012) (S) -2,2-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-3- tert-butyl ester carboxylic acid
(013) (S) -2-amino-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,
(014) (S) -4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one,
(015) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(016) trans-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] cyclohexanecarboxylic acid,
(017) 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,
(018) 2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,
(019) N- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} propionamide,
(020) N- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} acetamide,
(021) N- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyrazin-2-yl] thiazol-2-yl} acetamide,
(022) ethyl ester (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} acetic acid,
(023) (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,
(024) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanone,
(025) 5- [6- (4-methyl-pyridin-2-ylamino) pyridin-2-yl] thiazole-2-carboxylic acid ethyl ester,
(026) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanone,
(027) (S) -5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} dihydrofuran-2-one,
(028) O- (2-hydroxyethyl) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanone,
(029) N-methoxy-N-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carboxamide,
(030) N-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carboxamide,
(031) N-methyl-N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,
(032) (S) -5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-one,
(033) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentanoic acid,
(034) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentan-1-ol,
(035) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentanamide,
(036) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanol,
(037) oxime 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanone,
(038) N- {6- [2 - ((S) -1-aminoethyl) thiazol-5-yl] pyridin-2-yl} -N - ([4,4 '] bipyridinyl-2-yl) amine,
(039) N - ((S) -1- {5- [6 - ([4,4 '] bipyridinyl-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,
(040) N - ((S) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,
(041) (S) -2-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} propan-1-ol,
(042) N - ((S) -1- {5- [6- (isoquinolin-3-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,
(043) (4-methylpyridin-2-yl) - [6- (2-piperidin-4-ylthiazol-5-yl) pyridin-2-yl] amine,
(044) trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,
(045) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pentylamine,
(046) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} butan-1-ol,
(047) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenol,
(048) 2-hydroxy-N - ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,
(049) 3 - ({5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazole-2-carbonyl} amino) propionic acid,
(050) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) benzoic acid,
(051) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperidin-4-ol,
(052) 3,3-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} butan-1-ol,
(053) [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenyl] methanol,
(054) N - ((R) - (4-hydroxyphenyl) - {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} methyl) acetamide,
(055) N- (2-hydroxyethyl) -4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) benzamide,
(056) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) cyclohexanone,
(057) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) cyclohexanol,
(058) ((3R, 4S) -3,4-dihydroxypyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2 -yl} cyclohexyl) methanone,
(059) (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) - (piperazin-1-yl) methanone,
(060) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-1-carboxamide,
(061) 2-hydroxy-1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-1-yl) ethanone,
(062) trans-4- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid,
(063) 3- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-1-yl) -3-oxopropionic acid,
(064) N- (4-methylpyridin-2-yl) -N- {6- [2- (piperazin-1-ylmethyl) thiazol-5-yl] pyridin-2-yl} amine,
(065) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperidin-4-ylamine,
(066) N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} methanesulfonamide,
(067) N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) acetamide,
(068) trans-4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid,
(069) 2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,
(070) (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanol,
(071) trans-4- {5- [6- (isoquinolin-3-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxylic acid,
(072) trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethylamine,
(073) ((3R, 4S) -3,4-dihydroxypyrrolidin-1-yl) - [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol- 2-yl} ethyl) phenyl] methanone,
(074) N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) acetamide,
(075) N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) methanesulfonamide,
(076) 2-hydroxy-N- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) acetamide,
(077) 2-hydroxy-N- [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenyl] acetamide,
(078) ((3R, 4S) -3,4-dihydroxypiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2 -yl} cyclohexyl) methanone,
(079) ((R) -3-hydroxypyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl ) methanone
(080) (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} phenyl) methanol,
(081) N- (4-methylpyridin-2-yl) -N- [6- (2-pyridin-3-ylmethylthiazol-5-yl) pyridin-2-yl] amine,
(082) N- (4-methylpyridin-2-yl) -N- {6- [2- (2-piperidin-4-yl-ethyl) thiazol-5-yl] pyridin-2-yl} -amine,
(083) N- (6- {2- [2- (1-methanesulfonylpiperidin-4-yl) ethyl] thiazol-5-yl} pyridin-2-yl) -N- (4-methylpyridin-2-yl) amine ,
(084) 2-hydroxy-1- [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) piperidin-1-yl] ethanone
(085) N- (2-hydroxyethyl) -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,
(086) N- (2-morpholin-4-yl-ethyl) -trans-4- {5- [6- (4-methyl-pyridin-2-ylamino) -pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,
(087) [3- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenyl] methanol,
(088) (3-hydroxypyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone,
(089) 4- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonyl) piperazin-2-one,
(090) ((R) -2-hydroxymethylpyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl ) methanone
(091) (4-aminopiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone,
(092) [4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) piperidin-1-yl] - (piperidin-4- sludge) methanone,
(093) (trans-4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) - (4-hydroxypiperidin-1-yl) methanone,
(094) N- (4-hydroxypiperidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,
(095) N - [(R) -2-hydroxy-1- (3H-imidazol-4-ylmethyl) ethyl] -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2 -yl] thiazol-2-yl} cyclohexanecarboxamide,
(096) N - [(S) -2-hydroxy-1- (3H-imidazol-4-ylmethyl) ethyl] -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2 -yl] thiazol-2-yl} cyclohexanecarboxamide,
(097) N- (2-dimethylaminoethyl) -trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,
(098) (3-aminopyrrolidin-1-yl) - (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) methanone,
(099) N- [1- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonyl) pyrrolidin-3-yl] methanesulfonamide,
(100) (3R, 4S) -1- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexylmethyl) pyrrolidin-3,4 diol
(101) trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonitrile,
(102) cis-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarbonitrile,
(103) (S) -5- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-one,
(104) (S) -1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,
(105) (S) -1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) ethanol,
(106) (S) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethanol,
(107) (S) -5- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-one,
(108) 3- (trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) -4H- [1,2,4] oxazole -5-he
(109) N- (4-methylpyridin-2-yl) -N- (6- {2- [4- (1H-tetrazol-5-yl) cyclohexyl] thiazol-5-yl} pyridin-2-yl) amine ,
(110) (S) -5- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidin-2-one,
(111) N- (1,1-dimethyl-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) acetamide,
(112) (S) -1- (5- {6- [4- (2-methyl- [1,3] dioxalan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2- sludge) ethanol,
(113) N-methyl-trans-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,
(114) N- (1,1-dimethyl-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) methanesulfonamide,
(115) trans-4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,
(116) trans-4- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexanecarboxamide,
(117) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} cyclohexanol,
(118) (S) -1- (5- {6- [4- (2-hydroxyethoxy) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) ethanol,
(119) dimethylcarbamic acid (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl ether,
(120) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperazin-2-one,
(121) 4- (2-hydroxy-2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) phenol,
(122) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethoxy} acetyl) piperazin-2-one,
(123) N - ((R) - (4-hydroxyphenyl) - {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} methyl) -N-methylacetamide,
(124) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperazin-2,6-dione,
(125) (S) -5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} oxazolidin-2-one,
(126) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperazin-2-one,
(127) N- (4-methylpyridin-2-yl) -N- [6- (2-morpholin-4-ylthiazol-5-yl) pyridin-2-yl] amine,
(128) 1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone,
(129) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-sulfonamide,
(130) N- (4-methoxypyridin-2-yl) -N- {6- [2- (morpholin-4-yl) thiazol-5-yl] pyridin-2-yl} amine,
(131) (3R, 4S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3,4-diol,
(132) N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} acetamide,
(133) N- [6- (4-methyl-2-morpholin-4-ylthiazol-5-yl) pyridin-2-yl] -N- (4-methylpyridin-2-yl) amine,
(134) N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,
(135) N-methyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-1-carboxamide,
(136) 1- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(137) N- {6- [2- (4-methoxypiperidin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine,
(138) N- {6- [2- (4-methylpiperazin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine,
(139) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ol,
(140) N-methyl-1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(141) 4- {4-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-1-carbaldehyde,
(142) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-4-carboxylic acid methyl ester,
(143) 2-hydroxy-1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone,
(144) 1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) propan-1-one,
(145) N, N-dimethyl-4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazine-1-carboxamide,
(146) 1- (4- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone,
(147) 1- (4- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) ethanone,
(148) 4- (methyl- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid,
(149) 4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxamide,
(150) 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) -4H- [1,2,4 ] oxadiazol-5-one,
(151) N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-piperidin-4-ylamine,
(152) 4- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carbonyl) piperazin-2-one,
(153) N- (2,2-dimethoxyethyl) -N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,
(154) 1- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] ethanone
(155) 2-hydroxy-1- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine- 1-yl] ethanone,
(156) N-methyl-4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1 carboxamide
(157) N- {2- [4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine -1-yl] -2-oxoethyl} acetamide,
(158) (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetic acid,
(159) 2- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetamide,
(160) N-methyl-2- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1-yl) acetamide,
(161) N- (2-hydroxyethyl) -2- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -2-oxopiperazin-1- il) acetamide,
(162) N-methyl-N-methylcarbamoylmethyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(163) N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-tetrahydropyran-4-ylamine,
(164) 4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] phenol,
(165) N - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) acetamide,
(166) (R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ylamine,
(167) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxylic acid,
(168) 2-hydroxy-N - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) acetamide ,
(169) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxamide,
(170) N-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxamide,
(171) N- (2-hydroxyethyl) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxamide,
(172) (R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ol,
(173) trans-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanol,
(174) N- {6- [2- (3-methoxymethylpiperidin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine,
(175) 2-hydroxy-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide,
(176) 2-hydroxy-N-methyl-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide ,
(177) N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) methanesulfonamide,
(178) N-methyl-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) methanesulfonamide,
(179) 2-hydroxy-N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ylmethyl) acetamide,
(180) N- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ylmethyl) acetamide,
(181) N-methyl- (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,
(182) N - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) methanesulfonamide,
(183) N- {6- [2 - ((R) -3-methoxypyrrolidin-1-yl) thiazol-5-yl] pyridin-2-yl} -N- (4-methylpyridin-2-yl) amine,
(184) N-methyl-4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxamide,
(185) N- (2-hydroxyethyl) -4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino ) cyclohexanecarboxamide,
(186) N- (2-acetylaminoethyl) -4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino ) cyclohexanecarboxamide,
(187) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-ylmethoxy) acetic acid,
(188) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) methanol,
(189) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-ylmethoxy) acetamide,
(190) 4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(191) N-methyl-4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxamide,
(192) N-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-ylmethoxy) acetamide,
(193) N- (2-hydroxyethyl) -4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(194) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide,
(195) N-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide,
(196) N- (2-hydroxyethyl) -2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetamide ,
(197) N, N-diallyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,
(198) N, N- [2- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] acetamide
(199) 2-hydroxy-N- [2- (N'-methyl- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] acetamide ,
(200) N- (4-methanesulfonylpiperidin-1-yl) -N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,
(201) N, N-dimethyl-4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine -1-carboxamide
(202) (4-hydroxyphenyl) - [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine- 1-yl] methanone,
(203) 1- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylamino} piperidin-1-yl) ethanone,
(204) 1- [4- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] ethanone
(205) N-methyl-2 - ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yloxy) acetamide ,
(206) 1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(207) 1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(208) 2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethanol,
(209) N- (2-methoxyethyl) -N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,
(210) N- [2- (N '- (1-acetylpiperidin-4-yl) -N' - {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2- il} amino) ethyl] methanesulfonamide,
(211) 1- [4- (N- (2-hydroxyethyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine- 1-yl] ethanone,
(212) 1- [4- (N- (2-methoxyethyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidine- 1-yl] ethanone,
(213) (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,
(214) N-methyl- (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,
(215) N- (2,2,2-trifluoroethyl) - (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin- 2-carboxamide
(216) (R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxylic acid,
(217) ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) methanol,
(218) (R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-carboxamide,
(219) 1- [4- (N-ethyl-N- {5- [6- (4-methylpyridin-2-ylamino),
(220) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] ethanone,
(221) 1- {4- [N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N- (2,2,2-trifluoroethyl) amino] piperidin-1-yl} ethanone,
(222) 1- [4- (N- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-methylamino) piperidin-1-yl] ethanone ,
(223) 1- [4- (N- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N-methylamino) piperidin-1-yl] - 2-hydroxyethanone,
(224) (R) -1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ol,
(225) (R) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-ol,
(226) 4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-4-carboxylic acid,
(227) (S) -1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,
(228) (S) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,
(229) 1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-carboxamide,
(230) 2- (N- (2-hydroxyethyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethanol,
(231) 2- [N- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N- (2-hydroxyethyl) amino] ethanol,
(232) (R) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxylic acid,
(233) 1- (5- {6- [4- (1-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-carboxamide,
(234) (R) -1- (5- {6- [4- (2-methyl- [1,3] dioxolan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2- il) pyrrolidin-3-ol,
(235) 1- (2- {6- [2 - ((R) -3-hydroxypyrrolidin-1-yl) thiazol-5-yl] pyridin-2-ylamino} pyridin-4-yl) ethanone,
(236) 4- (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) -4-oxo-butyric acid,
(237) N-hydroxy- (R) -1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxamide,
(238) 4- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) piperidin-1-yl] -4-hydroxybutyric acid,
(239) (R) -1- (5- {6- [4- (1-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidin-3-ol,
(240) 2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetamide,
(241) (R) -1- (5- {6- [4- (2-methyl- [1,3] dioxolan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2- il) piperidine-3-carboxylic acid,
(242) (R) -1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine-3-carboxylic acid,
(243) (S) -1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,
(244) (1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) methanol,
(245) 1 - [(R) -3- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pyrrolidin- 1-yl] ethanone,
(246) (S) -1- {5- [6- (4-acetylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxylic acid,
(247) (R) -1- (5- {6- [4- (2-methyl- [1,3] dioxolan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2- il) piperidine-3-carboxamide,
(248) ((S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) acetic acid,
(249) (S) -3-methyl-2- [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetylamino] butyric acid,
(250) 3- [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetylamino] propionic acid,
(251) [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetylamino] acetic acid,
(252) [1- (5- {6- [4- (2-methyl- [1,3] dioxolan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidine -4-yl] acetic acid,
(253) (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(254) 4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid,
(255) ((R) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yloxy) acetic acid,
(256) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-carboxylic acid,
(257) (R) -1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) pyrrolidin-3-ol,
(258) 4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) benzoic acid,
(259) (2S, 4R) -4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pyrrolidin-2 -carboxylic acid
(260) {N-methyl-N- [2- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino ) acetyl] amino} acetic acid,
(261) 2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid,
(262) 3 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid,
(263) {4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] phenyl} acetic acid,
(264) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-3-yl) acetic acid,
(265) (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperazin-1-yl) acetic acid,
(266) N- (4-methylpyridin-2-yl) -N- (6- {2 - [(R) -3- (1H-tetrazol-5-yl) piperidin-1-yl] thiazol-5-yl } pyridin-2-yl) amine,
(267) cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid,
(268) trans-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid,
(269) 4- [2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] benzoic acid,
(270) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yloxy) acetic acid,
(271) (4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} cyclohexyl) acetic acid,
(272) 4 - {[N-methyl-N- (5- {6- [4- (2-methyl- [1,3] dioxalan-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) amino] methyl} benzoic acid,
(273) 4 - [(N-dimethylcarbamoylmethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid,
(274) cis-4- (N-carbamoylmethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid,
(275) trans-4 - [(N-carbamoylmethyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] cyclohexanecarboxylic acid,
(276) 5 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] thiophen-2-carboxylic acid ,
(277) 3-chloro-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid ,
(278) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethoxy} benzoic acid,
(279) 3-methoxy-4 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] benzoic acid ,
(280) 2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,
(281) 2 - [(N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] thiazole-4-carboxylic acid ,
(282) [trans-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexyl] acetic acid,
(283) [cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexyl] acetic acid,
(284) 4- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} ethyl) cyclohexanecarboxylic acid,
(285) (4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(286) 4- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -3,4-dihydro-2H-benzo [1,4] oxazin-8 -carboxylic acid
(287) {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethoxy} acetic acid,
(288) 4- [1-methyl-1- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] benzoic acid,
(289) [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) phenyl] acetic acid,
(290) (1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(291) trans-4 - [(N-benzyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] cyclohexanecarboxylic acid,
(292) [trans-4- (N-benzyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexyl] acetic acid,
(293) trans-4 - [(N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] cyclohexanecarboxylic acid,
(294) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroquinoline-5-carboxylic acid,
(295) fluoro- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-ylidene) acetic acid,
(296) 5- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pentanoic acid,
(297) N- [2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetyl] methanesulfonamide,
(298) 4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) butyric acid,
(299) (1- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(300) (1- {5- [6- (5-chloropyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(301) (1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(302) trans-4- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) cyclohexanecarboxylic acid,
(303) 3- [4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) phenyl] propionic acid,
(304) (E) -6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-ena acid,
(305) (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinolin-6-yl) acetic acid ,
(306) 3- (2- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -1,2,3,4-tetrahydroisoquinolin-5-yl) propionic acid
(307) 5- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pentanoic acid,
(308) 5- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-
ilamino} pentanoic acid,
(309) 6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hexanoic acid,
(310) (Z) -2-fluoro-6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex -2-enoic acid
(311) (8- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -8-azabicyclo [3.2.1] oct-3-yl) acetic acid ,
(312) (8- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -8-azabicyclo [3.2.1] oct-3-yl) acetic acid ,
(313) (1- {5- [6- (4-cyanopyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(314) {4 - [(N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] phenyl} acetic acid,
(315) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,
(316) (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(317) 4- [1-methyl-1- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) ethyl] benzoic acid,
(318) 3-methyl-6- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-ena acid,
(319) 3-methyl-6- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-ena acid,
(320) (E) -6- (N-methyl-N- {5- [6- (4-trifluoromethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) hex-2-eno acid,
(321) N- (2-hydroxyethyl) - (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,
(322) 2- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) acetamide,
(323) 3-methyl-2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) butylamide,
(324) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) ethanol,
(325) 5- (N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) pentan-1-ol,
(326) (1- {5- [6- (pyrazin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(327) [1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl] acetic acid,
(328) fluoro- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(329) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} piperidine-4-carboxamide,
(330) (1- {5- [6- (4-ethylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(331) N-isopropyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amine,
(332) N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} -N- (2-morpholin-4-yl-ethyl) amine,
(333) 2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} amino) acetamide,
(334) 2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) butyric acid,
(335) trans-4 - [(N-methyl-N- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) methyl] cyclohexanecarboxylic acid,
(336) [1- (5- {6- [4- (2,2,2-trifluoroethoxy) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl] acetic acid ,
(337) 2-methyl-1- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino) propan-2-ol ,
(338) 3- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) propionic acid,
(339) N- (2-hydroxyethyl) -4- (N'-methyl-N '- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} amino ) piperidine-1-carboxamide,
(340) 2-methyl-2- (1- {5- [6- (pyrazin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,
(341) 4 - [(N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} amino) methyl] benzoic acid,
(342) (1- {5- [6- (4-tert-butylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(343) (1- {5- [6- (4-isopropylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(344) 2-ylamino) pyridin-2-yl] thiazol-2-yl} -6-azaspiro [2.5] octane-1-carboxylic acid,
(345) 2- [1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl] -2-methylpropionic acid,
(346) 2-methyl-2- (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,
(347) fluoro- (1- {5- [6- (pyrazin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(348) fluoro- (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid,
(349) [1- (5- {6- [4- (1-hydroxy-1-methylethyl) pyridin-2-ylamino] pyridin-2-yl} thiazol-2-yl) piperidin-4-yl] acetic acid ,
(350) 2-methyl-2- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) propionic acid,
(351) 5- (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-3-yl) pentanoic acid and
(352) 2-methyl-2- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-ylmethyl} amino) propionamide. 10. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 9, wherein the aminopyridine compound is selected from the following group of compounds:
(01) (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} pyrrolidin-2-carboxamide,
(02) cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} amino) cyclohexanecarboxylic acid,
(03) (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl) thiazol-2-yl} piperidin-4-yl) acetic acid and
(04) (4-methyl-1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4-yl) acetic acid. 11. The aminopyridine compound or a pharmaceutically acceptable salt thereof of claim 10, wherein the aminopyridine compound is (S) -1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2- il} pyrrolidine-2-carboxamide. 12. The aminopyridine compound or a pharmaceutically acceptable salt thereof of claim 10, wherein the aminopyridine compound is (1- {5- [6- (pyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidin-4 -yl) acetic acid. 13. The aminopyridine compound or a pharmaceutically acceptable salt thereof of claim 10, wherein the aminopyridine compound is (1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiazol-2-yl} piperidine -4-yl) acetic acid. 14. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein the aminopyridine compound is cis-4- (N-methyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl ) thiazol-2-yl} amino) cyclohexanecarboxylic acid. 15. The aminopyridine compound or its pharmaceutically acceptable salt according to claim 1, where Z represents a carbon atom. 16. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 15, wherein the aminopyridine compound according to claim 1 is an aminopyridine compound represented by the following general formula (Ib-1):

where X ¹ represents
(1) -CH = or
(2) a nitrogen atom;
Y ² represents
(1) -CH = or
(2) a nitrogen atom;
R represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group or
(3) an acyl group;
R ¹ represents
(1) a hydrogen atom or
(2) a halogen atom;
R ³ represents
(1) a hydrogen atom,
(2) a halogen atom,
(3) -N (R ³¹ ) (R ³² ),
where R ³¹ and R ³² represent a hydrogen atom or a C _1-6 alkyl group,
(4) a C _1-6 alkoxy group, wherein a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a substituent selected from the following Aa-3 group:
[Group Aa-3]
but. hydroxyl group and
b. -N (R ³¹ ) (R ³² ),
where R ³¹ and R ³² have the meanings indicated above,
(5) an acyl group,
(6) a saturated heterocyclic group, wherein the heterocyclic group may be substituted with a C _1-6 alkyl group, and the saturated heterocyclic group may partially have a double bond,
(7) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted with a substituent selected from the following Ab-3 group:
[Group Ab-3]
but. hydroxyl group
b. -COOR ³³ , where R ³³ represents a hydrogen atom or a C _1-6 alkyl group, and
from. —CO — N (R ³¹ ) (R ³² ), wherein R ³¹ and R ³² are as defined above, or
(8) —COOR ³³ , wherein R ³³ is as defined above;
R ⁵ represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group or
(3) -COOR ⁵¹ ,
where R ⁵¹ represents a C _1-6 alkyl group;
R ⁶ and R ⁶ 'may be the same or different and each represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group or
(3) an acyl group; and
R ⁷ has the meanings indicated in claim 1. 17. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 16, wherein the aminopyridine compound is an aminopyridine compound represented by the following general formula (Ib-2):

where R ³ represents
(1) a halogen atom,
(2) -N (R ³¹ ) (R ³² ),
where R ³¹ and R ³² represent a hydrogen atom or C _1-6 alkyl groups,
(3) With _1-6 alkoxygroup,
where a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted
a substituent selected from the following group Aa-4:
[Group Aa-4]
but. hydroxyl group and
b. -N (R ³¹ ) (R ³² ),
where R ³¹ and R ³² have the meanings indicated above,
(4) an acyl group,
(5) a saturated heterocyclic group, where the heterocyclic group partially has a double bond and may be substituted with a C _1-6 alkyl group,
(6) A C _1-6 alkyl group which may be substituted with a substituent selected from the following Ab-4 group:
[Group Ab-4]
but. hydroxyl group
b. -COOR ³³ , where R ³³ represents a hydrogen atom or a C _1-6 alkyl group, and
from. —CO — N (R ³¹ ) (R ³² ), wherein R ³¹ and R ³² are as defined above, or
(7) -COOR ³³ ,
where R ³³ has the meaning indicated above;
R ⁵ represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group or
(3) -COOR ⁵¹ ,
where R ⁵¹ represents a C _1-6 alkyl group;
R ⁶ and R ^{6 '} may be the same or different and each represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group, or
(3) an acyl group;
R ⁷ represents a hydrogen atom, a halogen atom, a nitro group, a cyano group or the following R ^a , R ^b , R ^c , R ^d , R ^e , R ^f , R ^g or R ^h ;
R ^a is —C _p H _{2 (p-1)} (R ^al ) (R ^a2 ) —OR ^a3 , where
(1) p is an integer from 1 to 6,
(2) R ^a1 represents a hydrogen atom,
(3) R ^a2 represents a C _1-6 alkyl group, wherein the C _1-6 alkyl group may be substituted with a hydroxyl group, a halogen atom, a carboxy group, and
(4) R ^a3 represents a hydrogen atom or an acyl group;
R ^b represents —C _p H _{2 (p-1)} (R ^b1 ) (R ^b2 ) -N- (R ^b3 ) (R ^b4 ), where
(1) p is an integer from 1 to 6,
(2) R ^b1 represents a hydrogen atom,
(3) R ^b2 represents a C _1-6 alkyl group,
(4) R ^b3 represents a hydrogen atom or a C _1-6 alkyl group and
(5) R ^b4 represents
but. hydrogen atom or
b. -COR ^b42 ,
where R ^b42 represents a C _1-6 alkyl group;
R ^c represents —C (= NR ^c1 ) —R ^c2 ,
Where
(1) R ^c1 represents
but. hydroxyl group
b. A C _1-6 alkoxy group, wherein a C _1-6 alkyl group in a C _1-6 alkoxy group may be substituted with a hydroxyl group or a C _1-6 alkoxy group, or
from. an acyloxy group, and
(2) R ^c2 represents a C _1-6 alkyl group or an amino group;
R ^d is —C (═O) —R ^d1 ,
where R ^d1 represents
(1) a hydrogen atom,
(2) a C _1-6 alkyl group, where a C _1-6 alkyl group may be substituted by a hydroxyl group,
(3) a hydroxyl group,
(4) With _1-6 alkoxygroup,
(5) -N (R ^d11 ) (R ^d12 ),
where R ^d11 and R ^d12 may be the same or different and represent
hydrogen atom or
C _1-6 alkyl group, where C _1-6 alkyl group may be substituted
an amino group, a carboxy group or a hydroxyl group, or
R ^d11 and R ^d12 together with an adjacent nitrogen atom can form a 5- or 6-membered saturated heterocyclic ring, or
(6) C _1-6 alkoxy;
R ^e is a 5- or 6-membered aromatic heterocyclic group having 1-4 heteroatoms, where the aromatic heterocyclic group may be substituted with a C _1-6 alkyl group or oxo group;
R ^f represents a C _1-6 alkyl group or a C _2-6 alkenyl group, wherein said C _1-6 alkyl group and a C _2-6 alkenyl group may be substituted with a substituent selected from the following Fa-2 group:
[Group Fa-2]
but. -COOH,
b. -N (R ^f21 ) (R ^f22 ),
where R ^f21 and R ^f22 may be the same or different and represent
hydrogen atom
acyl group or
C _1-6 alkyl group,
where the C _1-6 alkyl group may be substituted by a carboxy group, and
from. halogen atom
R ^g is a substituent having ring B ″ represented by
the following formula (IIb);

where A "refers to a linker selected from the following Ga-2 group:
[Group Ga-2]
- (CH ₂ ) _k -,
- (CH ₂ ) _k -NR ^g1 (CO) -,
- (CH ₂ ) _k -NR ^g1 - (CH ₂ ) _j -,
- (CH ₂ ) _k -O- (CO) -,
- (CH ₂ ) _k -O-,
- (CO) - and
- (CO) -NR ^g1 -,
where k and j can be the same or different and represent an integer from 1 to 4,
R ^g1 represents
hydrogen atom
an acyl group, where the acyl group may be substituted by a hydroxyl group or a carboxy group, or
- a C _1-6 alkyl group, where the alkyl group may be substituted with —CON (R ^g41 ) (R ^g42 ),
Ring B '' is a ring selected from the following Na-2 group:
[Group At-2]
aryl group
C _3-8 cycloalkyl group and
A 5-7 membered saturated heterocyclic group containing at least one nitrogen atom, and
ring B ″ may be substituted with a substituent selected from the following group Ia-2:
[Group Ia-2]
a. -OR ^g2 ,
where R ^g2 represents
hydrogen atom
C _1-6 alkyl group or
an aralkyl group, and
b. -COOR ^g3 ,
where R ^g3 represents
hydrogen atom or
A C _1-6 alkyl group, wherein the alkyl group may be substituted with a hydroxyl group; and
R ^h represents —N (R ^h1 ) (R ^h2 ),
where R ^h1 represents a hydrogen atom and R ^h2 represents an acyl group, where the acyl group may be substituted by a hydroxyl group or a C _1-6 alkoxycarbonyl group. 18. The aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein the aminopyridine compound is selected from the following group of compounds:
(01) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,
(02) 5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-carbaldehyde,
(03) 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanol,
(04) ethyl 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} acetic acid,
(05) N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} acetamide,
(06) N-methyl-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxamide,
(07) {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} methanol,
(08) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,
(09) 1- {5- [6- (4-methoxypyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,
(10) 5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxamide,
(11) 1- {5- [6- (6-isopropoxypyrimidin-4-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,
(12) N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} acetamide,
(13) O- (2-hydroxyethyl) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,
(14) N- (2-aminoethyl) -5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxamide,
(15) oxime 1- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} propan-1-one,
(16) {2- [6- (5-Acetylthiophen-2-yl) pyridin-2-ylamino] pyridin-4-yl} -acetic acid ethyl ester,
(17) 2- [6- (5-Acetylthiophen-2-yl) pyridin-2-ylamino] isonicotinic acid methyl ester,
(18) 1- (5- {6- [4- (2-hydroxyethyl) pyridin-2-ylamino] pyridin-2-yl} thiophen-2-yl) ethanol,
(19) N-hydroxy-5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophene-2-carboxyamidine,
(20) 1- (5- {6- [4- (2-hydroxyethoxy) pyridin-2-ylamino] pyridin-2-yl} thiophen-2-yl) ethanone,
(21) 1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,
(22) oxime 1- {5- [6- (4-chloropyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} ethanone,
(23) {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} piperazin-1-ylmethanone,
(24) 1- (5- {6- [4- (4,4-dimethyl-4,5-dihydrooxazol-2-yl) pyridin-2-ylamino] pyridin-2-yl} thiophen-2-yl) ethanone ,
(25) 2,2-difluoro-3-hydroxy-3- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-yl} propionic acid,
(26) 4 - [({5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid,
(27) 4 - [(N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid,
(28) trans-4 - [(N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] cyclohexanecarboxylic acid,
(29) 3- (N-acetyl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) propionic acid,
(30) 4 - [(N-isobutyryl-N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid and
(31) 4 - [(N- (2-hydroxyacetyl) -N- {5- [6- (4-methylpyridin-2-ylamino) pyridin-2-yl] thiophen-2-ylmethyl} amino) methyl] benzoic acid . 19. A pharmaceutical composition for treating or preventing allergic diseases, an autoimmune disease or a malignant tumor, containing as an active ingredient the aminopyridine compound or a pharmaceutically acceptable salt thereof according to claim 1. 20. Syk inhibitor containing as an active ingredient the aminopyridine compound or its pharmaceutically acceptable salt according to claim 1. 21. A therapeutic and / or prophylactic agent for the treatment of allergic diseases, autoimmune diseases or malignant tumors containing as an active ingredient the aminopyridine compound or its pharmaceutically acceptable salt according to claim 1. 22. The therapeutic and / or prophylactic agent of claim 21, wherein the allergic disease is bronchial asthma, allergic rhinitis, allergic dermatitis, or allergic conjunctivitis. 23. The therapeutic and / or prophylactic agent of claim 21, wherein the autoimmune disease is rheumatoid arthritis, systemic lupus erythematosus, multiple sclerosis. 24. The therapeutic or prophylactic agent of claim 21, wherein the cancer is B-lymphoma or B-cell leukemia.