RU2409575C2 - IMIDAZO[1,2-a]PYRIDINE DERIVATIVES USED AS PEPTIDE DEFORMYLASE INHIBITORS - Google Patents

Abstract

FIELD: chemistry. ^ SUBSTANCE: invention relates to imidazo[1,2-a]pyridine derivatives of formula in which radicals R1, R2, R3 and R4 independently denote a hydrogen atom, a halogen atom, a hydroxyl group, an amino group, a nitro group, a (C1-C12)alkyl radical which can be substituted with one or more halogen atoms or OH, and a O-(C1-C12)alkyl radicalwhich is substituted with phenyl, or two of radicals R1, R2, R3 and R4 can denote part of a phenyl ring; R5 denotes a (C1-C12)alkyl radical which can be substituted with one or more OH, methanesulphanyl, COOH or a halogen atom, (C2-C12)alkenyl radical, (C2-C12)alkynyl radical, (C6-C10)aryl radical, heteroaryl radical, which is an aromatic groupcontaining 5-10 ring members and 1-2 nitrogen or oxygen ring atoms, (C3-C10)cycloalkyl radical, (C1-C12)alkyl(C3-C10)cycloalkyl radical, (C6-C10)aryl(C1-C12)alkyl radical; radicals R6 and R7 independently denote a hydrogen atom or a (C1-C12)alkyl radical, which can be substituted with COOH, (C6-C10)aryl radical; and X denotes a group of formula - CO-NHOH or formula where U denotes a bond, CH2, V denotes O, S, W denotes NH, and Y denotes OH, or pharmaceutically acceptable salts thereof, solvates, hydrates. The invention also relates to the pharmaceutical composition based on the formula I compound and use of the formula I compound. ^ EFFECT: novel derivatives have peptide deformylase inhibiting activity. ^ 16 cl

Description

The present invention relates to new peptide deformylase inhibitors (PDPs). These compounds are of great interest, especially as antibiotics.

Peptide deformylase is a bacterial metal enzyme that contains iron. Its presence is determined in all bacteria; it plays a vital role in the metabolism of bacteria. In the process of protein synthesis, peptide deformylase catalyzes the removal of the formyl group at the N-ends of bacterial proteins. In the absence of an enzyme, the bacterium is not capable of producing any active proteins. Peptide deformylase is the subject of a new class of antibiotics called peptide deformylase inhibitors.

The present invention was based on the task of obtaining new peptide deformylase inhibitors, which can be obtained synthetically in a simple way.

The present invention provides compounds of formula (I),

in which the radicals R ¹ , R ² , R ³ and R ⁴ , independently from each other, represent a hydrogen atom, a halogen atom, a hydroxyl, amino, nitro or thiol group, an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl , cycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heterocycloalkyl, aralkyl or heteroalkyl radical, whereby each of these radicals, independently of one another, may be substituted, or two of the radicals R ¹ , R ² , R ³ and R ⁴ together may be part cycloalkyl a heterocycloalkyl, aryl or heteroaryl ring, whereby each of these rings may optionally be substituted;

R ⁵ represents a hydrogen atom, a halogen atom, a hydroxyl, amino, nitro or thiol group, an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heterocycloalkyl, aralkyl or heteroalkyl radical, each of these radicals may optionally be substituted;

the radicals R ⁶ and R ⁷ , independently of one another, represent a hydrogen atom, or an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heterocycloalkyl, aralkyl or heteroalkyl radical, whereby each of these radicals, independently of one another, may optionally be substituted; and

X represents a group of the formula —CS — NHOH, —CH ₂ —CO — CH ₂ —OH, —CO — CH ₂ —OH, —CO — NHOH, —CNH — NHOH, —CH ₂ —NOH — CHS, —NOH— CHS, —NOH — CHO, —CH ₂ —NOH — CHO, —CH ₂ —CHOH — CHO, —CHOH — CHO, —CHON — COOH, —CH (CH ₂ —OH) —COOH, —COOH, or —CH ₂ COOH, or it is selected from the following formulas:

in which U represents a bond, CH ₂ , NH, O or S, V represents O, S, NH or CH ₂ , W represents O, S, NH or CH ₂ , Y represents OH or NH ₂ , E represents is a bond, CH ₂ , NH, O, or S, and the groups D, G, and M, independently of one another, are N or CH, or a pharmacologically acceptable salt, solvate, hydrate, or a pharmaceutically acceptable mixture of the above.

The term "alkyl" means a saturated linear or branched hydrocarbon group that contains specifically from 1 to 20 carbon atoms, preferably from 1 to 12 carbon atoms, most preferably from 1 to 6 carbon atoms, for example methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, n-hexyl, 2,2-dimethylbutyl or n-octyl group.

The terms "alkenyl" and "alkynyl" mean at least partially unsaturated linear or branched hydrocarbon groups which contain specifically from 2 to 20 carbon atoms, preferably from 2 to 12 carbon atoms, most preferably from 2 to 6 carbon atoms, for example, an ethenyl, allyl, acetylenyl, propargyl, isoprenyl or hex-2-enyl group. Alkenyl groups preferably contain one or two (most preferably one) double bond (s), and the alkynyl group contains one or two (most preferably one) triple bond (s).

In addition, the terms “alkyl”, “alkenyl” and “alkynyl” mean groups in which, for example, one or more hydrogen atoms are replaced by a halogen atom (preferably F or Cl), —COOH, —OH, —SH, —NH ₂ , -NO ₂ , = O, = S, = NH, for example, a 2,2,2-trichloroethyl or trifluoromethyl group.

The term "heteroalkyl" means an alkyl, alkenyl or alkynyl group in which one or more (preferably 1, 2 or 3) carbon atoms are replaced by an oxygen, nitrogen, phosphorus, boron, selenium, silicon or sulfur atom (preferably an oxygen, sulfur or nitrogen). The term “heteroalkyl” further means a carboxylic acid or a group that is a derivative of a carboxylic acid, for example, acyl, acylalkyl, alkoxycarbonyl, acyloxy, acyloxyalkyl, carboxyalkylamide or alkoxycarbonyloxy.

Examples of heteroalkyl groups are groups of the formulas R ^a -OY ^a -, R ^a -SY ^a -, R ^a -N (R ^b ) -Y ^a -, R ^a -CO-Y ^a -, R ^a -O-CO-Y ^a -, R ^a -CO-OY ^a -, R ^a -CO-N (R ^b ) -Y ^a -, R ^a -N (R ^b ) -CO-Y ^a -, R ^a -O-CO-N (R ^b ) -Y ^a -, R ^a -N (R ^b ) -CO-OY ^a -, R ^a -N (R ^b ) -CO-N (R ^c ) -Y ^a -, R ^a -O- CO-OY ^a -, R ^a -N (R ^b ) -C (= NR ^d ) -N (R ^c ) -Y ^a -, R ^a -CS-Y ^a -, R ^a -O-CS-Y ^a -, R ^a -CS-OY ^a -, R ^a -CS-N (R ^b ) -Y ^a -, R ^a -N (R ^b ) -CS-Y ^a -, R ^a -O-CS-N ( R ^b ) -Y ^a -, R ^a -N (R ^b ) -CS-OY ^a -, R ^a -N (R ^b ) -CS-N (R ^c ) -Y ^a -, R ^a -O-CS -OY ^a -, R ^a -S-CO-Y ^a -, R ^a -CO-SY ^a -, R ^a -S-CO-N (R ^b ) -Y ^a -, R ^a -N (R ^b ) -CO-SY ^a -, R ^a -S-CO-OY ^a -, R ^a -O-CO-SY ^a -, R ^a -S-CO-SY ^a -, R ^a -S-CS-Y ^a - , R ^a- CS-SY ^a -, R ^a -S-CS-N (R ^b ) -Y ^a -, R ^a -N (R ^b ) -CS-SY ^a -, R ^a -S-CS-OY ^{a -, R a -O-CS} -SY a -, in which R ^a represents a hydrogen atom, C ₁ -C ₆ -alkyl, C ₂ -C ₆ alkenyl, or C ₂ -C ₆ -a kinilnuyu group; R ^b represents a hydrogen atom, a C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl group; R ^c represents a hydrogen atom, a C ₁ -C ₆ alkyl-, C ₂ -C ₆ alkenyl- or C ₂ -C ₆ alkynyl group; R ^d represents a hydrogen atom, a C ₁ -C ₆ alkyl, a C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl group, and Y ^a represents a direct bond, a C ₁ -C ₆ alkylene, C _{A 2} -C ₆ alkenylene or C ₂ -C ₆ alkynylene group, whereby each heteroalkyl group contains at least one carbon atom, and one or more hydrogen atoms may be substituted with fluorine or chlorine atoms. Specific examples of heteroalkyl groups are methoxyl, trifluoromethoxyl, ethoxyl, n-propyloxy, isopropyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, methoxyethyl, methylamino, ethylamino, dimethylamino, diethylamino, isopropylamino , di-isopropylaminoethyl, enol ether, dimethylaminomethyl, dimethylaminoethyl, acetyl, propionyl, butyryloxy, acetyloxy, methoxycarbonyl, ethoxycarbonyl, N-ethyl-N-methylcarbamoyl or N-methylcarbamoyl. Further examples of heteroalkyl groups are nitrile, isonitrile, cyanate, thiocyanate, isocyanate, isothiocyanate and alkylnitrile groups.

The term “cycloalkyl” means a saturated or partially unsaturated (eg, cycloalkenyl) cyclic group that contains one or more rings (preferably 1 or 2) containing specifically from 3 to 14 carbon atoms in the ring, preferably from 3 to 10 (specifically 3 4, 5, 6 or 7) carbon atoms in the ring. The term “cycloalkyl” also refers to groups in which one or more hydrogen atoms are replaced by fluorine, chlorine, bromine or iodine atoms, or —COOH, —OH, = O, —SH, = S, —NH ₂ , = NH or —NO ₂ , i.e., for example, to cyclic ketones, for example, cyclohexanone, 2-cyclohexenone or cyclopentanone. Other specific examples of cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, Spiro [4,5] decanyl, norbornyl, cyclohexyl, cyclopentenyl, cyclohexadienyl, decalinyl, cubanyl, bicyclo [4.3.0] nonyl, tetraline, cyclopentylcyclohexyl, or 2-enyl group.

By the term “heterocycloalkyl” is meant a cycloalkyl group as defined above, in which one or more (preferably 1, 2 or 3) ring carbon atoms is replaced by an oxygen, nitrogen, silicon, selenium, phosphorus or sulfur atom (preferably oxygen, sulfur or nitrogen) ) The heterocycloalkyl group preferably contains one or two rings that contain from 3 to 10 (specifically 3, 4, 5, 6 or 7) atoms in the ring. The expression “heterocycloalkyl” also refers to groups in which one or more hydrogen atoms are replaced by fluorine, chlorine, bromine or iodine atoms, or —COOH, —OH, = O, —SH, = S, —NH ₂ , = NH or —NO ₂ . Examples are the piperidyl, morpholinyl, urotropinyl, pyrrolidinyl, tetrahydrothiophenyl, tetrahydropyranyl, tetrahydrofuryl, oxacyclopropyl, azacyclopropyl or 2-pyrazolinyl groups, as well as lactams, lactones, cyclic imides and cyclic anhydrides.

The term “alkylcycloalkyl” means a group which, as defined above, contains both cycloalkyl and alkyl, alkenyl or alkynyl groups, for example, alkylcycloalkyl, alkylcycloalkenyl, alkenylcycloalkyl and alkynylcycloalkyl groups. The alkylcycloalkyl group preferably contains a cycloalkyl group that contains one or two rings comprising from 3 to 10 (specifically 3, 4, 5, 6 or 7) ring carbon atoms, and one or two alkyl, alkenyl or alkynyl groups containing one or more 2 to 6 carbon atoms.

The term “heteroalkylcycloalkyl” means alkylcycloalkyl groups as defined above, in which one or more (preferably 1, 2 or 3) ring carbon atoms and / or other carbon atoms are replaced by an oxygen, nitrogen, silicon, selenium, phosphorus or sulfur atom ( preferably oxygen, sulfur or nitrogen). The heteroalkylcycloalkyl group preferably contains 1 or 2 rings comprising from 3 to 10 (specifically 3, 4, 5, 6 or 7) ring atoms, and one or two alkyl, alkenyl, alkynyl or heteroalkyl groups comprising 1 or 2 to 6 atoms carbon. Examples of such groups are alkyl heterocycloalkyl, alkyl heterocycloalkenyl, alkenyl heterocycloalkyl, alkynyl heterocycloalkyl, heteroalkylcycloalkyl, heteroalkylheterocycloalkyl and heteroalkylheterocycloalkenyl, respectively, are cyclic or di-saturated groups.

By the term “aryl” or Ar is meant an aromatic group that contains one or more rings that contain specifically from 6 to 14 carbon atoms, preferably from 6 to 10 (specifically 6) ring carbon atoms. The term “aryl” (or Ar) additionally refers to groups in which one or more hydrogen atoms is replaced by fluorine, chlorine, bromine, or iodine atoms, or groups

—COOH, —OH, —SH, —NH ₂ , or —NO ₂ . Examples are the phenyl, naphthyl, biphenyl, 2-fluorophenyl, anilinyl, 3-nitrophenyl or 4-hydroxyphenyl groups.

The term "heteroaryl" means an aromatic group that contains one or more rings, including specifically from 5 to 14 ring atoms, preferably from 5 to 10 (specifically 5 or 6) ring atoms, and one or more (preferably 1, 2, 3 or 4) ring atoms of oxygen, nitrogen, phosphorus or sulfur (preferably oxygen, sulfur or nitrogen). The term “heteroaryl” further refers to groups in which one or more hydrogen atoms is substituted by fluorine, chlorine, bromine or iodine atoms, or —COOH, —OH, —SH, —NH ₂ , or —NO ₂ groups. Examples are 4-pyridyl, 2-imidazolyl, 3-phenylpyrrolyl, thiazolyl, oxazolyl, triazolyl, tetrazolyl, isoxazolyl, indazolyl, indolyl, benziimidazolyl, pyridazinyl, quinolinyl, 2,3-pyridyl, bridyl, aridi -pyrazolyl and isoquinolinyl groups.

The term "aralkyl" refers to groups which, in accordance with the above definitions, contain both aryl and alkyl, alkenyl, alkynyl and / or cycloalkyl groups, for example, arylalkyl, alkylaryl, arylalkenyl, arylalkynyl, arylcycloalkyl, arylcycloalkylalkyl, alkylarylcycloalkenyl groups. Specific examples of aralkyls are toluene, xylene, mesitylene, styrene, benzyl chloride, o-fluorotoluene, 1H-indole, tetraline, dihydronaphthalene, indanone, phenylcyclopentyl, cumene, cyclohexylphenyl, fluorene and indane. The aralkyl group preferably contains one or two aromatic rings containing from 6 to 10 ring carbon atoms, and one or two alkyl, alkenyl and / or alkynyl groups comprising 1 or 2 to 6 carbon atoms and / or a cycloalkyl group comprising 5 or 6 carbon atoms.

The term “heteroaralkyl” means an aralkyl group, as defined above, in which one or more (preferably 1, 2, 3 or 4) ring carbon atoms and / or other carbon atoms are replaced by an oxygen, nitrogen, silicon, selenium, phosphorus, boron atom or sulfur (preferably oxygen, sulfur or nitrogen), that is, this term refers to groups which, in accordance with the above definitions, contain both aryl or heteroaryl and alkyl, alkenyl, alkynyl, and / or heteroalkyl, and / or cycloalkyl , and / or heterocycle loalkyl groups. A heteroalkyl group preferably contains one or two aromatic rings comprising 5 or 6 to 10 ring carbon atoms, and one or two alkyl, alkenyl and / or alkynyl groups comprising one or 2 to 6 carbon atoms and / or a cycloalkyl group including 5 or 6 ring carbon atoms, whereby 1, 2, 3 or 4 of these carbon atoms are replaced by oxygen, sulfur or nitrogen atoms.

Examples are arilgeteroalkilnye, arilgeterotsikloalkilnye, arilgeterotsikloalkenilnye, arilalkilgeterotsikloalkilnye, arilalkenilgeterotsikloalkilnye, arilalkinilgeterotsikloalkilnye, arilalkilgeterotsikloalkenilnye, heteroarylalkyl, geteroarilalkenilnye, geteroarilalkinilnye, geteroarilgeteroalkilnye, geteroariltsikloalkilnye, geteroariltsikloalkenilnye, geteroarilgeterotsikloalkilnye, geteroarilgeterotsikloalkenilnye, geteroarilalkiltsikloalkilnye, geteroarilalkilgeterotsikloalkenilnye, geteroarilge teroalkylcycloalkyl, heteroaryl heteroalkylcycloalkenyl and heteroaryl heteroalkylheterocycloalkyl groups, whereby the cyclic groups are saturated or mono-, di- or tri-unsaturated. Specific examples are tetrahydroisoquinolinyl, benzoyl, 2- or 3-ethylindolyl, 4-methylpyridine group, 2-, 3- or 4-methoxyphenyl, 4-ethoxyphenyl, 2-, 3- or 4-carboxyphenylalkyl group.

The terms cycloalkyl, heterocycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl and heteroalkyl also refer to groups in which one or more hydrogen atoms are replaced by fluorine, chlorine, bromine or iodine, or OH groups, = O, SH, = S, NH ₂ , —NH or NO ₂ .

By the term “optionally substituted” is meant groups in which one or more hydrogen atoms are substituted, for example, with fluorine, chlorine, bromine or iodine atoms, or with OH, = O, SH, = S, NH ₂ , = NH or NO ₂ groups. This expression also refers to groups which are substituted with unsubstituted C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ heteroalkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₉ heterocycloalkyl, C ₆ -C ₁₀ aryl, C ₁ -C ₉ heteroaryl, C ₇ -C ₁₂ aralkyl or C ₂ -C ₁₁ heteroalkyl groups.

The compounds of formula (I) may contain one or more centers of chirality, depending on the substituents. The present invention therefore includes both all pure enantiomers and all pure diastereomers, as well as mixtures thereof in any respect. In addition, the present invention includes all cis / trans isomers of the compounds of general formula (I), as well as all mixtures thereof. In addition, the present invention includes all tautomeric forms of the compounds of formula (I).

Compounds of formula (I) in which W is NH and V is O, S or NH are preferred.

Compounds of formula (I) in which one, two or three groups D, G and M are nitrogen atoms are preferred.

Particularly preferred are compounds of formula (I) in which X is a group of the formula —CH ₂ —CO — NHOH, —CO — NHOH, —CH ₂ —NOH — CHS, —NOH — CHS, —CH ₂ —NOH — CHO, - NOH-CHO, —CH ₂ —CO — CH ₂ OH, —CO — CH ₂ OH, —CH ₂ —CHOH — CHO, —CHON — CHO, or a group having one of the following formulas:

Most preferably, substituent X has the formula —CO — NHOH.

In addition, R ¹ preferably represents a hydrogen atom, a chlorine atom, a bromine atom, an amino group, a methyl group or an ethyl group; specifically a hydrogen atom or an amino group.

R ² more preferably represents a hydrogen atom, a chlorine atom, a bromine atom, a methyl group or an ethyl group; specifically a hydrogen atom.

Further, R ³ and R ^{4 are} preferably not simultaneously hydrogen atoms.

R ³ represents, more preferably, a hydrogen atom, a chlorine atom, a bromine atom, an amino group, a methyl group, an ethyl group or a propyl group, specifically a chlorine atom, a bromine atom or an amino group.

R ⁴ , in turn, preferably represents a chlorine atom, a bromine atom, a methyl group, an ethyl group or a propyl group; specifically a chlorine atom or a bromine atom.

Compounds of formula (I) in which R ³ represents a bromine atom and R ⁴ represents a methyl group, or in which R ³ represents a hydrogen atom and R ⁴ represents a chlorine atom or a bromine atom, are particularly preferred.

More preferably, two of the radicals R ¹ , R ² , R ³ and R ⁴ together are part of a cycloalkyl, heterocycloalkyl, aryl or heteroaryl ring, whereby these rings may optionally be substituted.

R ⁵ , in turn, is preferably a tert-butyl group, an isopropyl group, a neopentyl group or an n-hexyl group; specifically a tert-butyl, neopentyl or n-hexyl group.

More preferably, the groups R ⁶ and R ⁷ , independently of one another, are hydrogen atoms, hydroxymethyl or methyl groups.

Examples of pharmacologically acceptable salts of the compounds of formula (I) are salts of physiologically acceptable mineral acids, for example hydrochloric acid, sulfuric acid and phosphoric acid; or salts of organic acids, for example methanesulfonic acid, para-toluenesulfonic acid, lactic acid, formic acid, acetic acid, trifluoroacetic acid, citric acid, succinic acid, fumaric acid, maleic acid and salicylic acid. The compounds of formula (I) may be solvated, specifically hydrated. Girdration can occur, for example, during the preparation process or as a result of hygroscopicity of the initially anhydrous compounds of formula (I).

The drug compositions of the present invention contain at least one compound of formula (I) as an active substance and optionally carriers and / or auxiliary components.

Drug precursors (for definitions and examples, see, for example, R. B. Silverman, Medizinische Chemie, VCH Weinheim, 1995, chap. 8, p. 361ff), which are likewise an object of the present invention, contain a compound of formula (I) and at least one pharmacologically acceptable protective group that cleaves under physiological conditions, for example, a hydroxyl, alkoxyl, aralkyloxy, acyl or acyloxy group, for example a methoxy, ethoxyl, benzyloxy, acetyl or acetyloxy group.

The therapeutic use of the compounds of formula (I), their pharmacologically acceptable salts or solvates and hydrates, as well as compositions and pharmaceutical compositions, are likewise an object of the present invention.

The compounds of formula (I) are of great interest especially as inhibitors of metalloproteinases (especially PDP). The use of these active ingredients in the manufacture of drugs that prevent and / or treat diseases, especially those that are tolerated by PDF, is also an object of the present invention. In general, the compounds of formula (I) are used using known acceptable methods, alone or in combination with any other therapeutic agent. Taking medications is possible, for example, in one of the following ways: orally, for example, in the form of dragees, coated tablets, pills, semisolid, soft or hard capsules, solutions, emulsions or suspensions; parenterally, for example, as an injection; rectally, in the form of suppositories; by inhalation, for example, in the form of a medicinal powder or aerosol, through the skin or through the nose. To prepare such tablets, pills, semisolid, coated tablets, dragees, and hard gelatine capsules, a therapeutically acceptable product may be mixed with pharmacologically inert inorganic or organic drug carriers, for example, lactose, sucrose, glucose, gelatin, malt, silica gel, starch or its derivatives, talc, stearic acid or its salts, skimmed milk powder and the like. In order to prepare soft capsules, drug carriers can be used, for example, vegetable oils, petroleum, animal or synthetic oils, paraffin, fat, polyols. To obtain liquid solutions and syrups, drug carriers such as water, alcohols, an aqueous solution of salt, an aqueous solution of dextrose, polyols, glycerin, vegetable oils, petroleum, animal or synthetic oils can be used. To obtain suppositories, drug carriers such as vegetable oils, petroleum, animal or synthetic oils, paraffin, fat and polyols can be used. To produce aerosols, compressed gases that are suitable for this purpose, for example, oxygen, nitrogen and carbon dioxide, can be used. Pharmaceutically acceptable constituents may also contain preservative and stabilizing additives, emulsifiers, sweeteners, aromatic substances, salts to modify the osmotic pressure, buffering agents, coating additives and antioxidants.

Compounds of formula (I) in which X = —COOCH ₃ can be prepared by the reaction of compounds of formulas (II), (III) and (IV).

Compounds of formula (I) in which X = —CO — NHOH can be prepared by reacting the product of this reaction with hydroxylamine in methanol.

Examples

General methodology:

50 μl of a 0.2 M solution of amine (II) in methanol is dispersed in a 96-well plate (methanol-insoluble amines are dispersed manually). 50 μl of a 0.2 M solution of aldehyde (III) in methanol are added. The tablet is shaken for 2 hours at room temperature. Then distribute 50 μl of a 0.2 M solution of isocyanide (IV) in methanol and 50 μl of a 0.4 M solution of acetic acid in methanol. The plate was shaken overnight at room temperature, the solvent was evaporated, and the residue was dissolved in 150 μl of a 0.5 M solution of NH ₂ OH in methanol. The tablet is shaken again overnight at room temperature.

The following compounds were prepared according to the general procedure using suitable starting materials and identified by mass spectrometry. All compounds were tested for activity as PDF inhibitors (for test methods see D.Chen et al. Antimicrobial Agents and Chemotherapy, Jan. 2004, C.250-261), IC ₅₀ values are in the range from 1 nmol to 50 μmol .

Examples Calc., [M + H] found [M + H] 2- (6-fluorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 225.09 225.08 2- (6-bromo-8-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 299.03 299.04 2- (6-bromo-3,5-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 313.05 313.08 N-hydroxy-2- (6-iodo-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) acetamide 389.07 389.10 2- (6-bromo-3,5-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 327.07 327.10 2- (3-tert-butyl-6-iodimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 389.07 389.11 2- (6-bromo-3-ethyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 327.07 327.10 2- (6-chloro-3-cyclopropylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 295.12 295.14 2- (6-chloro-3-isopropylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 297.14 297.18

Examples Calc., [M + H] found [M + H] 2- (6-bromo-3-ethyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 341.09 341.12 2- (6-bromo-3-isopropyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 341.09 341.12 2- [6-bromo-5-methyl-3 - ((E) -propenyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 339.07 339.11 2- (6-chloro-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 297.14 297.17 2- (3-tert-butyl-6-chlorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 297.14 297.16 2- (3-tert-butyl-6-chlorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 311.16 311.23 2- (3-tert-butyl-6-fluorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 281.17 281.15 2- (6-fluoro-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 281.17 281.19 N-hydroxy-2- (3-isobutyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) acetamide 277.20 277.21 2- (6-bromo-5-methyl-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 341.09 341.12 2- (6-bromo-3-isobutyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 355.11 355.14 2- (3-tert-butyl-6-methyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxy-acetamide 277.20 277.20 N-hydroxy-2- (6-iodo-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) propionamide 403.09 403.12 2- (6-bromo-8-methyl-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 355.11 355.08 2- (6-bromo-3-tert-butyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 355.11 355.13 2- (6-chloro-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 297.14 297.16

Examples Calc., [M + H] found [M + H] 2- (3-tert-butyl-6-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 291.22 291.22 2- (6-chloro-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 311.16 311.17 2- (6-bromo-5-methyl-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 355.11 355.13 2- (6-bromo-3-tert-butyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 369.13 369.16 2- (6-bromo-3-isobutyl-8-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 369.13 369.15 2- (6-bromo-3-isobutyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 369.13 369.15 N-hydroxy-2- (3-hydroxymethyl-5-methyl-imidazo [1,2-a] pyridin-2-ylamino) acetamide 251.14 251.15 2- (5-ethyl-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 265.16 265.17 2- (5-ethyl-3-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 249.16 249.17 N-hydroxy-2- [3- (1H-imidazo1-2-yl) -5-methylimidazo [1,2-a] pyridin-2-ylamino] acetamide 287.15 287.16 2- (3,5-diethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 263.18 263.19 2- [5-ethyl-3- (1H-imidazol-2-yl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 301.16 301.18 2- (5-ethyl-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxypropionamide 279.17 279.26 2- [5-ethyl-3 - ((E) -propenyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 275.18 0.00 2- [7-ethyl-3- (1H-imidazol-2-yl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 301.16 301.18 2- (3-furan-2-yl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 287.13 287.15

Examples Calc., [M + H] found [M + H] N-hydroxy-2- [8-methyl-3- (1H-pyrazol-3-yl) imidazo [1,2-a] pyridin-2-ylamino] acetamide 287.15 287.16 2- (3-cyclopropyl-5-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 275.18 275.18 N-hydroxy-2- (8-hydroxy-3-methylimidazo [1,2-a] pyridin-2-ylamino) -3-phenylpropionamide 327.17 327.10 N-hydroxy-2- (5-methyl-3-phenylimidazo [1,2-a] pyridin-2-ylamino) acetamide 297.16 297.17 N-hydroxy-2- (7-methylimidazo [1,2-a] pyridin-2-ylamino) -3-phenylpropionamide 311.18 311.15 2- (3-butyl-5-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 305.24 305.22 2- (3-ethyl-5-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 277.20 277.19 N-hydroxy-2- (3-isobutyl-5-propylimidazo [1,2-a] pyridin-2-ylamino) acetamide 305.24 305.14 N-hydroxy-2- (3-hydroxymethyl-5-propylimidazo [1,2-a] pyridin-2-ylamino) acetamide 279.17 279.17 2- (3-benzyl-5-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 339.22 339.22 N-hydroxy-2- (3-pentyl-5-propylimidazo [1,2-a] pyridin-2-ylamino) acetamide 319.26 319.25 N-hydroxy-2- (3-methyl-5-propylimidazo [1,2-a] pyridin-2-ylamino) acetamide 263.18 263.17 3- [2- (hydroxycarbamoylmethylamino) -5-propyl-imidazo [1,2-a] pyridin-3-yl] propionic acid 321.19 321.18 2- (3,5-dipropylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 291.22 291.21 N-hydroxy-2- [3- (2-methylsulfanylethyl) -5-propylimidazo [1,2-a] pyridin-2-ylamino] acetamide 323.19 323.18 2- (3-tert-butyl-5-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 305.24 305.22

Examples Calc., [M + H] found [M + H] 2- [3- (2,2-dimethylpropyl) -5-propylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 319.26 319.25 2- (3-hept-1-ynyl-5-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 343.26 343.25 N-hydroxy-2- (3-pentyl-6-trifluoromethylimidazo [1,2-a] pyridin-2-ylamino) acetamide 345.18 345.20 2- [3- (2,2-dimethylpropyl) -6-trifluoromethylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 345.18 345.20 2- (3-hept-1-ynyl-6-trifluoromethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 369.18 369.11 2- (6-fluoro-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 295.19 295.20 2- [3- (2,2-dimethylpropyl) -6-fluoro-imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 295.19 295.19 2- (3-butyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 277.20 277.19 2- (3-benzyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 311.18 311.19 N-hydroxy-2- (5-methyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) acetamide 291.22 291.22 N-hydroxy-2- [5-methyl-3- (2-methylsulfanylethyl) imidazo [1,2-a] pyridin-2-ylamino] acetamide 295.15 295.09 2- (3-tert-butyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 277.20 277.21 2- [3- (2,2-dimethyl-propyl) -5-methylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 291.22 291.22 2- (3-hept-1-ynyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 315.22 315.23 2- (1-butylimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 313.20 313.21 2- (1-benzylimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 347.18 347.20

Examples Calc., [M + H] found [M + H] N-hydroxy-2- (1-pentylimidazo [1,2-a] quinolin-2-ylamino) acetamide 327.22 327.23 N-hydroxy-2- (1-propylimidazo [1,2-a] quinolin-2-ylamino) acetamide 299.18 299.21 N-hydroxy-2- [1- (2-methylsulfanylethyl) imidazo [1,2-a] quinolin-2-ylamino] acetamide .331.15 331.18 2- (1-tert-butylimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 313.20 313.21 2- [1- (2,2-dimethylpropyl) imidazo [1,2-a] quinolin-2-ylamino] -N-hydroxyacetamide 327.22 327.23 2- (1-hept-1-ynilimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 351.22 351.23 2- (6-bromo-3-isobutyl-8-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 355.11 355.03 2- [6-bromo-3- (2,2-dimethyl-propyl) -8-methylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 369.13 369.15 2- (6-bromo-3-hept-1-ynyl-8-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 393.13 393.14 2- (6-chloro-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 311.16 311.17 2- [6-chloro-3- (2,2-dimethylpropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 311.16 311.17 2- (6-chloro-3-hept-1-ynilimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 335.16 335.17 2- (3-butyl-6-nitroimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 308.16 308.15 N-hydroxy-2- (3-isobutyl-6-nitroimidazo [1,2-a] pyridin-2-ylamino) acetamide 308.16 308.11 2- (3-benzyl-6-nitroimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 342.14 342.17 N-hydroxy-2- (6-nitro-3-pentyl-imidazo [1,2-a] pyridin-2-ylamino) acetamide 322.18 322.19

Examples Calc., [M + H] found [M + H] 2- [3- (2,2-dimethylpropyl) -6-nitroimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 322.18 322,20 2- (3-hept-1-ynyl-6-nitroimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 346.18 346.20 2- (3-butyl-6-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 277.20 277.18 N-hydroxy-2- (6-methyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) acetamide 291.22 291.22 2- [3- (2,2-dimethylpropyl) -6-methyl-imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 291.22 291.22 2- (3-hept-1-ynyl-6-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 315.22 315.22 2- (3-butyl-5,7-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 291.22 291.23 N-hydroxy-2- (3-isobutyl-5,7-dimethylimidazo [1,2-a] pyridin-2-ylamino) acetamide 291.22 291.21 N-hydroxy-2- (3-hydroxymethyl-5,7-cimethylimidazo [1,2-a] pyridin-2-ylamino) acetamide 265.16 265.16 2- (3-benzyl-5,7-dimethyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 325,20 325.21 2- (5,7-dimethyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 305.24 305.24 3- [2- (hydroxycarbamoylmethylamino) -5,7-cimethylimidazo [1,2-a] pyridin-3-yl] propionic acid 307.17 307.10 2- (5,7-dimethyl-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 277.20 277.26 2- [5,7-dimethyl-3- (2-methylsulfanylethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 309.17 309.18 2- (3-tert-butyl-5,7-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 291.22 291.22

Examples Calc., [M + H] found [M + H] 2- [3- (2,2-dimethylpropyl) -5,7-dimethylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 305.24 305.24 2- (3-hept-1-ynyl-5,7-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 329.24 329.24 2- (6,8-dibromo-3-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 419.00 419.03 2- (6,8-dibromo-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 419.00 419.03 2- (6,8-dibromo-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 392.93 393.00 2- (3-benzyl-6,8-dibromimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 452.97 453.02 2- (6,8-dibromo-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 433.02 433.05 2- [6,8-dibromo-3- (2-methylsulfanylethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 436.95 436.97 2- [6,8-dibromo-3- (2,2-dimethylpropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 433.02 433.02 2- (6,8-dibromo-3-hept-1-ynilimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 457.01 457.03 2- (3-butyl-8-chloro-6-trifluoromethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 365,12 365.14 2- (8-chloro-3-hydroxymethyl-6-trifluoromethyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 339.06 339.03 2- (3-benzyl-8-chloro-6-trifluoromethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 399.10 399.15 2- (8-chloro-3-pentyl-6-trifluoromethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 379.14 379.15 2- [8-chloro-3- (2,2-dimethyl-propyl) -6-trifluoromethyl-imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 379.14 379.15

Examples Calc., [M + H] found [M + H] 2- (8-chloro-3-hept-1-ynyl-6-trifluoromethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 403.14 403.14 2- (6-bromo-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 341.09 341.09 2- (6-bromo-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 355.11 355.10 2- (6-bromo-3-tert-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 341.09 341.09 2- [6-bromo-3- (2,2-dimethyl-propyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 355.11 355.11 2- (6-bromo-3-hept-1-ynilimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 379.11 379.12 2- (1-butyl-9-hydroxyimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 329.19 329.19 2- (1-ethyl-9-hydroxyimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 301.15 301.16 N-hydroxy-2- (9-hydroxy-1-isobutylimidazo [1,2-a] quinolin-2-ylamino) acetamide 329.19 329.19 2- (1-benzyl-9-hydroxyimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 363.17 363.18 N-hydroxy-2- (9-hydroxy-1-pentylimidazo [1,2-a] quinolin-2-ylamino) acetamide 343.21 343.21 N-hydroxy-2- (9-hydroxy-1-propylimidazo [1,2-a] quinolin-2-ylamino) acetamide 315.17 315.17 N-hydroxy-2- [9-hydroxy-1- (2-methylsulfanylethyl-imidazo [1,2-a] quinolin-2-ylamino] acetamide 347.14 347.15 2- (1-tert-butyl-9-hydroxyimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 329.19 329.19 2- [1- (2,2-dimethyl-propyl) -9-hydroxy-imidazo [1,2-a] quinolin-2-ylamino] -N-hydroxyacetamide 343.21 343.21 2- (8-bromo-3-butyl-6-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 355.11 355.11

Examples Calc., [M + H] found [M + H] 2- (8-bromo-6-methyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 369.13 369.12 2- [8-bromo-3- (2,2-dimethylpropyl) -6-methylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 369.13 369.12 2- (8-bromo-3-hept-1-ynyl-6-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 393.13 393.13 2- (3-butyl-5-chlorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 297.14 297.14 2- (5-chloro-3-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 269.10 269.14 2- (5-chloro-3-isobutyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 297.14 297.14 2- (5-chloro-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 271.07 271.09 2- (3-benzyl-5-chlorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 331.12 331.13 2- (5-chloro-3-pentyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 311.16 311.16 2- (5-chloro-3-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 255.08 255.09 3- [5-chloro-2- (hydroxycarbamoylmethylamino) -imidazo [1,2-a] pyridin-3-yl] propionic acid 313.09 313.13 2- (5-chloro-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 283.12 283.18 2- [5-chloro-3- (2-methylsulfanyl-ethyl) -imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 315.09 315.10 2- (3-tert-butyl-5-chlorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 297.14 297.14 2- [5-chloro-3- (2,2-dimethylpropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 311.16 311.16 2- (5-chloro-3-hept-1-ynilimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 335.16 335.17

Examples Calc., [M + H] found [M + H] N-hydroxy-2- (5-methyl-6-nitro-3-propylimidazo [1,2-a] pyridin-2-ylamino) acetamide 308.16 308.14 2- [3- (2,2-dimethylpropyl) -5-methyl-6-nitroimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 336,20 336.25 2- (5-bromo-3-propylimidazo [1,2-b] isoquinolin-2-ylamino) -N-hydroxyacetamide 377.09 377.13 2- [5-bromo-3- (2-methylsulfanylethyl) imidazo [1,2-b] isoquinolin-2-ylamino] -N-hydroxyacetamide 409.06 409.08 2- (6,8-dibromo-3-butyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 433.02 433.05 2- (6,8-dibromo-3-ethyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 404.98 405.00 2- (6,8-dibromo-3-isobutyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 433.02 433.03 2- (6,8-dibromo-3-hydroxymethyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 406.95 406.98 2- (3-benzyl-6,8-dibromo-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 466,99 466.96 2- (6,8-dibromo-5-methyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 447.03 447.04 2- (6,8-dibromo-3,5-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 390.96 390.98 2- (6,8-dibromo-5-methyl-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 419.00 419.01 2- [6,8-dibromo-5-methyl-3- (2-methylsulfanylethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 450.97 451.02 2- [6,8-dibromo-3- (2,2-dimethylpropyl) -5-methylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 447.03 447.05 2- (6,8-dibromo-3-hept-1-ynyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 471.03 471.08

Examples Calc., [M + H] found [M + H] 2- (1-butyl-5-hydroxyimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 329.19 329,20 N-hydroxy-2- (5-hydroxy-1-isobutyl-imidazo [1,2-a] quinolin-2-ylamino) acetamide 329.19 329.20 2- (1-benzyl-5-hydroxyimidazo [1,2-a] quinolin-2-ylamino) -N-hydroxyacetamide 363.17 363.17 N-hydroxy-2- (5-hydroxy-1-pentylimidazo [1,2-a] quinolin-2-ylamino) acetamide 343.21 343.19 N-hydroxy-2- (5-hydroxy-1-propylimidazo [1,2-a] quinolin-2-ylamino) acetamide 315.17 315.23 N-hydroxy-2- [5-hydroxy-1- (2-methylsulfanylethyl) imidazo [1,2-a] quinolin-2-ylamino] acetamide 347.14 347.15 2- [1- (2,2-dimethyl-propyl) -5-hydroxyimidazo [1,2-a] quinolin-2-ylamino] -N-hydroxyacetamide 343.21 343.21 2- (3-butyl-6,8-difluorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 299.16 299.16 2- (6,8-difluoro-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 299.16 299.16 2- (6,8-difluoro-3-pentyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxy-acetamide 313.18 313.18 2- [6,8-difluoro-3- (2-methylsulfanylethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 317.11 317.12 2- [3- (2,2-dimethyl-propyl) -6,8-difluorimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 313.18 313.18 2- (6-bromo-3-isobutyl-7,8-dimethyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxy-acetamide 369.13 369.13 2- (6-bromo-7,8-dimethyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 383.15 383.14 2- [6-bromo-3- (2,2-dimethylpropyl) -7,8-cimethylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 383.15 383.14

Examples Calc., [M + H] found [M + H] 2- (6-bromo-3-hept-1-ynyl-7,8-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 407.15 407.15 2- [3- (2,2-dimethyl-propyl) -7-methyl-6-nitroimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 336,20 336.21 2- (5-bromo-3-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 341.09 341.09 2- (5-bromo-3-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 313.05 313.06 2- (5-bromo-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 341.09 341.10 2- (5-bromo-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 315.02 315.04 2- (3-benzyl-5-bromimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 375.07 374.98 2- (5-bromo-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 355.11 355.06 2- (5-bromo-3-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 299.03 299.04 3- [5-bromo-2- (hydroxycarbamoylmethylamino) -imidazo [1,2-a] pyridin-3-yl] propionic acid 357.04 357.06 2- (5-bromo-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 327.07 327.07 2- [5-bromo-3- (2-methylsulfanylethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 359.04 359.06 2- (5-bromo-3-tert-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 341.09 341.17 2- [5-bromo-3- (2,2-dimethylpropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 355.11 355.11 2- (5-bromo-3-hept-1-ynilimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 379.11 379.12

Examples Calc., [M + H] found [M + H] 2- (3-butyl-8-ethyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 305.24 305.23 2- (8-ethyl-3-hydroxymethyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 279.17 279.18 2- (3-benzyl-8-ethyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 339.22 339.22 2- (8-ethyl-5-methyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 319.26 319.25 2- [3- (2,2-dimethylpropyl) -8-ethyl-5-methylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 319.26 319.25 2- (8-ethyl-3-hept-1-ynyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 343.26 343.26 2- (6,8-dichloro-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 305.03 305.06 2- (6,8-dichloro-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 345.12 345.12 2- (6-bromo-3-isobutyl-7-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 355.11 355.11 2- [6-bromo-3- (2,2-dimethylpropyl) -7-methylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 369.13 369.12 2- (3-butyl-5-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 291.22 291.22 2- (5-ethyl-3-isobutylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 291.22 291.21 2- (5-ethyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 305.24 305.23 3- [5-ethyl-2- (hydroxycarbamoylmethylamino) -imidazo [1,2-a] pyridin-3-yl] propionic acid 307.17 307.17 2- (5-ethyl-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 277.20 277.19 2- [5-ethyl-3- (2-methylsulfanylethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 309.17 309.18

Examples Calc., [M + H] found [M + H] 2- (3-tert-butyl-5-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 291.22 291.22 2- [3- (2,2-dimethylpropyl) -5-ethylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 305.24 305.24 2- (5-ethyl-3-hept-1-ynilimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 329.24 329.24 2- (6-bromo-3-butyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 355.11 355.11 2- (3-benzyl-6-bromo-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 389.09 389.06 2- (6-bromo-5-methyl-3-pentyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxy-acetamide 369.13 369.13 3- [6-bromo-2- (hydroxycarbamoylmethylamino) -5-methyl-imidazo [1,2-a] pyridin-3-yl] propionic acid 371.06 371.10 2- [6-bromo-5-methyl-3- (2-methylsulfanylethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 373.06 373.08 2- [6-bromo-3- (2,2-dimethylpropyl) -5-methylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 369.13 369.14 2- (6-bromo-3-hept-1-ynyl-5-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 393.13 393.03 2- (3,7-bis-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 267.13 267.13 N-hydroxy-2- (7-hydroxymethyl-3-propylimidazo [1,2-a] pyridin-2-ylamino) acetamide 279.17 279.17 2- (3-tert-butyl-7-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxy-acetamide 293.19 293.18 2- (3-cyclohexyl-7-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 319.21 319.20 3-butyl-2- (hydroxycarbamoylmethylamino) -imidazo [1,2-a] pyridine-6-carboxylic acid amide 306.19 306.18

Examples Calc., [M + H] found [M + H] 2- (hydroxycarbamoylmethylamino) -3-hydroxymethylimidazo [1,2-a] pyridine-6-carboxylic acid amide 280.12 280.14 3-tert-butyl-2- (hydroxycarbamoylmethylamipo) -imidazo [1,2-a] pyridine-6-carboxylic acid amide 306.19 306.18 2- (hydroxycarbamoylmethylamino) -3- (3,3,3-grifluoropropyl) imidazo [1,2-a] pyridine-6-carboxylic acid amide 346.13 346.15 3-cyclohexyl-2- (hydroxycarbamoylmethyl-amino) -imidazo [1,2-a] pyridine-6-carboxylic acid amide 332.21 332,20 2- (6,8-dibromo-3-butyl-5,7-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 447.03 447.05 2- (6,8-dibromo-3-ethyl-5,7-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 419.00 419.02 2- (3-benzyl-b, 8-dibromo-5,7-dimethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 481.01 481.05 2- (6,8-dibromo-5,7-dimethyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 461.05 461.08 3- [6,8-dibromo-2- (hydroxycarbamoylmethylamino) -5,7-cimethylimidazo [1,2-a] pyridin-3-yl] propionic acid 462.98 463.01 2- [6,8-dibromo-3- (2,2-dimethylpropyl) -5,7-cimethylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 461.05 461.10 2- [6,8-dibromo-5,7-dimethyl-3- (3,3,3-grifluoropropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 486.98 487.04 2- (8-bromo-6-chloro-3-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 347.01 347.10 2- [8-bromo-6-chloro-3- (2,2-dimethylpropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 389.07 389.07 2- (8-bromo-6-chloro-3-cyclohexylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 401.07 401.08

Examples Calc., [M + H] found [M + H] 2- (8-amino-3-butyl-6-chlorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 312.15 312.16 2- (8-amino-6-chloro-3-ethylimidazo [1,2-a] pyridin-2-ylamino) -] - N-hydroxyacetamide 284.11 284.12 2- (8-amino-6-chloro-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 286.09 286.02 2- (8-amino-3-benzyl-6-chlorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 346.13 346.15 2- (8-amino-6-chloro-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 326.17 326.18 3- [8-amino-6-chloro-2- (hydroxycarbamoylmethylamino) -imidazo [1,2-a] pyridin-3-yl] propionic acid 328,10 328.12 2- (8-amino-6-chloro-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 298.13 298.06 2- (8-amino-3-tert-butyl-6-chlorimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 312.15 312.16 2- [8-amino-6-chloro-3- (2,2-dimethylpropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 326.17 326.18 2- [8-amino-6-chloro-3- (3,3,3-grifluoropropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 352.10 352.05 2- (8-amino-6-chloro-3-cyclohexylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 338.17 338.18 2- (8-amino-6-bromo-3-butyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 356.10 356.12 2- (8-amino-6-bromo-3-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 328.06 328.08 2- (8-amino-6-bromo-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 330.04 330.06 2- (8-amino-3-benzyl-6-bromimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 390.08 390.11

Examples Calc., [M + H] found [M + H] 2- (8-amino-6-bromo-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 370.12 370.13 2- (8-amino-6-bromo-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 342.08 342.10 2- (8-amino-6-bromo-3-tert-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 356.10 356.11 2- [8-amino-6-bromo-3- (2,2-dimethylpropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 370.12 370.13 2- [8-amino-6-bromo-3- (3,3,3-grifluoropropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 396.04 396.05 2- [8-amino-6-bromo-3- (2,2,2-trifluoroethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 382.03 382.06 2- (8-amino-6-bromo-3-cyclohexyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 382.12 382.13 2- (6-amino-3-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 278.19 278.19 2- (6-amino-3-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 250.15 250.15 2- (6-amino-3-benzylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 312.17 312.25 2- (6-amino-3-pentyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxy-acetamide 292.21 292.20 3- [6-amino-2- (hydroxycarbamoylmethylamino) -imidazo [1,2-a] pyridin-3-yl] propionic acid 294.14 294.15 2- (6-amino-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 264.17 264.27 2- (6-amino-3-tert-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 278.19 278.18 2- [6-amino-3- (2,2-dimethylpropyl) -imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 292.21 292.20

Examples Calc., [M + H] found [M + H] 2- [6-amino-3- (3,3,3-trifluoropropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 318.14 318.15 2- [6-amino-3- (2,2,2-trifluoroethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 304.12 304.11 2- (6-amino-3-cyclohexylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 304.21 304.20 2- (8-amino-3-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 278.19 278.19 2- (8-amino-3-benzylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 312.17 312.18 2- (8-amino-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 292.21 292.20 2- (8-amino-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 264.17 264.20 2- (8-amino-3-tert-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 278.19 278.19 2- [8-amino-3- (2,2-dimethyl-propyl) -imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 292.21 292.20 2- [8-amino-3- (3,3,3-trifluoropropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 318.14 318.15 2- (5-amino-3-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 278.19 278.25 2- (5-amino-3-benzyl-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxy-acetamide 312.17 312.19 2- (5-amino-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 292.21 292.20 2- (5-amino-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 264.17 264.17 2- (5-amino-3-tert-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 278.19 278.19 2- [5-amino-3- (3,3,3-trifluoropropyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 318.14 318.16

Examples Calc., [M + H] found [M + H] 2- [5-amino-3- (2,2,2-trifluoroethyl) imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 304.12 304.10 2- (5-amino-3-cyclohexylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 304.21 304.21 2- (3-butyl-8-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 277.20 277.22 N-hydroxy-2- (3-hydroxymethyl-8-methylimidazo [1,2-a] pyridin-2-ylamino) acetamide 251.14 251.13 2- (3-benzyl-8-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 311.18 311.11 N-hydroxy-2- (8-methyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) acetamide 291.22 291.21 2- [3- (2,2-dimethylpropyl) -8-methylimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 291.22 291.21 N-hydroxy-2- [8-methyl-3- (3,3,3-trifluoropropyl) -imidazo [1,2-a] pyridin-2-ylamino] acetamide 317.14 317.15 2- (3-cyclohexyl-8-methylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 303.22 303.21 2- (3-butyl-7-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 291.22 291.21 2- (7-ethyl-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 265.16 265.07 2- (3-benzyl-7-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 325,20 325,20 2- (7-ethyl-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 305.24 305.23 2- (3-cyclohexyl-7-ethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 317.24 317.23 2- (3-butyl-8-hydroxy-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxy-acetamide 279.17 279.20 2- (3-ethyl-8-hydroxyimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 251.14 251.14

Examples Calc., [M + H] found [M + H] N-hydroxy-2- (8-hydroxy-3-hydroxymethyl-imidazo [1,2-a] pyridin-2-ylamino) acetamide 253.11 253.12 2- (3-benzyl-8-hydroxyimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 313.15 313.17 N-hydroxy-2- (8-hydroxy-3-pentylimidazo [1,2-a] pyridin-2-ylamino) acetamide 293.19 293.19 N-hydroxy-2- (8-hydroxy-3-propylimidazo [1,2-a] pyridin-2-ylamino) acetamide 265.16 265.16 2- (3-tert-butyl-8-hydroxyimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 279.17 279.17 2- [3- (2,2-dimethylpropyl) -8-hydroxyimidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 293.19 293.19 N-hydroxy-2- [8-hydroxy-3- (3,3,3-trifluoropropyl) -imidazo [1,2-a] pyridin-2-ylamino] acetamide 319.12 319.13 2- (3-cyclohexyl-8-hydroxy-imidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 305.19 305.19 2- (3-butylimidazo [2,1-a] isoquinolin-2-ylamino) -N-hydroxyacetamide 313.20 313.20 2- (3-benzylimidazo [2,1-a] isoquinolin-2-ylamino) -N-hydroxyacetamide 347.18 347.19 N-hydroxy-2- (3-pentylimidazo [2,1-a] isoquinolin-2-ylamino) acetamide 327.22 327.22 2- [3- (2,2-dimethyl-propyl) imidazo [2,1-a] isoquinolin-2-ylamino] -N-hydroxyacetamide 327.22 327.22 2- (3-cyclohexylimidazo [2,1-a] isoquinolin-2-ylamino) -N-hydroxyacetamide 339.22 339.21 2- (8-benzyloxy-3-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 369.23 369.23 2- (8-benzyloxy-3-hydroxymethylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 343.17 343.18 2- (8-benzyloxy-3-pentylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 383.25 383.23

Examples Calc., [M + H] found [M + H] 2- (8-benzyloxy-3-propylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 355.21 355.22 2- (8-benzyloxy-3-tert-butylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 369.23 369.25 2- [8-benzyloxy-3- (2,2-dimethylpropyl) -imidazo [1,2-a] pyridin-2-ylamino] -N-hydroxyacetamide 383.25 383.25 2- (8-benzyloxy-3-cyclohexylimidazo [1,2-a] pyridin-2-ylamino) -N-hydroxyacetamide 395.25 395.25 2- (hydroxycarbamoylmethylamino) -3-pentyl-imidazo [1,2-a] pyridine-6-carboxylic acid 321.19 321.14 3-butyl-2- (hydroxycarbamoylmethylamino) -imidazo [1,2-a] pyridine-8-carboxylic acid 307.17 307.20 2- (hydroxycarbamoylmethylamino) -3-pentyl-imidazo [1,2-a] pyridine-8-carboxylic acid 321.19 321.17 3- (2,2-dimethylpropyl) -2- (hydroxycarbamoylmethyl-amino) imidazo [1,2-a] pyridine-8-carboxylic acid 321.19 321.19 3-cyclohexyl-2- (hydroxycarbamoylmethylamino) -imidazo [1,2-a] pyridine-8-carboxylic acid 333.19 333.20

Claims (16)

1. The compounds of formula (I)

in which the radicals R ¹ , R ² , R ³ and R ⁴ , independently from each other, represent a hydrogen atom, a halogen atom, a hydroxyl group, an amino group, a nitro group, a (C ₁ -C ₁₂ ) alkyl radical which may be substituted with one or more, a halogen atom or OH, and an O- (C ₁ -C ₁₂ ) alkyl radical substituted with phenyl,
or two of the radicals R ¹ , R ² , R ³ and R ⁴ together can be part of a phenyl ring;
R ⁵ represents a (C ₁ -C ₁₂ ) alkyl radical which may be substituted by one or more OH, methanesulfanyl, COOH or a halogen atom, (C ₂ -C ₁₂ ) alkenyl radical, (C ₂ -C ₁₂ ) alkynyl radical, (C ₆ -C ₁₀ ) aryl radical, heteroaryl radical, which is an aromatic group that contains from 5 to 10 ring members and 1-2 ring nitrogen or oxygen atoms, (C ₃ -C ₁₀ ) cycloalkyl radical, (C ₁ -C ₁₂ ) alkyl (C ₃ -C ₁₀ ) cycloalkyl radical, (C ₆ -C ₁₀ ) aryl (C ₁ -C ₁₂ ) alkyl radical;
the radicals R ⁶ and R ⁷ , independently of one another, represent a hydrogen atom or a (C ₁ -C ₁₂ ) alkyl radical which may be substituted by COOH, a (C ₆ -C ₁₀ ) aryl radical; and
X represents a group of the formula —CO — NHOH or the formula

where U is a bond, CH ₂ ,
V represents O, S,
W represents NH, and
Y represents OH,
or a pharmaceutically acceptable salt, solvate, hydrate. 2. The compounds according to claim 1, in which R ¹ represents a hydrogen atom, a chlorine atom, a bromine atom, an amino group, a methyl group or an ethyl group. 3. The compounds according to claim 1, in which R ² represents a hydrogen atom, a chlorine atom, a bromine atom, a methyl group or an ethyl group. 4. The compounds according to claim 1, in which R ³ and R ⁴ are not simultaneously hydrogen atoms. 5. The compounds according to claim 1, in which R ³ represents a hydrogen atom, a chlorine atom, a bromine atom, an amino group, a methyl group, an ethyl group or a propyl group. 6. The compounds according to claim 1, in which R ⁴ represents a chlorine atom, a bromine atom, a methyl group, an ethyl group or a propyl group. 7. The compounds according to claim 1, in which R ³ represents a bromine atom, and R ⁴ represents a methyl group, or in which R ³ represents a hydrogen atom and R ⁴ represents a chlorine atom or a bromine atom. 8. The compounds according to claim 1, in which R ⁵ represents a tert-butyl group, an isopropyl group, a neopentyl group or an n-hexyl group. 9. The compounds according to claim 1, in which the groups R ⁶ and R ⁷ , independently of each other, are hydrogen atoms or a methyl group. 10. The compounds according to claim 1, in which X represents a group of the formula -CO-NH-OH. 11. A pharmaceutical composition having an inhibitory effect against peptide deformylase (PDF), which contains the compound according to claim 1 and carriers and / or auxiliary components. 12. The use of the compounds according to claim 1 for the inhibition of metalloproteinases. 13. The use of the compounds according to claim 1 for the inhibition of peptide deformylase (PDF). 14. The use of the compounds according to claim 1 for the prevention and / or treatment of diseases caused by the action of metalloproteinases. 15. The use of the compounds according to claim 1 for the prevention and / or treatment of diseases caused by the action of peptide deformylase (PDF). 16. The use of the compounds according to claim 1 as an antibiotic.