DE19548797A1 - New amino-imidazole substituted amino acid derivatives - Google Patents

Abstract

2-Amino-imidazol-4-yl N-(hetero)arylsulphonyl-amino acid amides (I), their stereoisomers, mixtures and salts are new: A = 1-6C alkylene; or 3-6C alkenylene with the double bond alpha to the imidazole ring; R1 = Ph optionally monosubstituted by alkyl, alkoxy, NMe2, NEt2, NO2, NH2, CN, CF3, F, Cl, Br or I; Ph disubstituted by alkyl or alkoxy; Ph substituted by 1 NH2 and 2 Cl or Br; 1- or 2-naphthyl optionally monosubstituted by alkyl, alkoxy, NMe2, NEt2 or Cl; 1- or 2-naphthyl disubstituted by alkyl or alkoxy; quinolin-8-yl or isoquinolin-5, -6- or -7-yl optionally monosubstituted by alkyl; isoindolin-5-yl-, 1,2,3,4-tetrahydroquinolin-8-yl, 1,2,3,4-tetrahydro-isoquinolin-5-, -6- or -7-yl or 2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl optionally monosubstituted by alkyl in the non-aromatic ring; 5,6,7,8-tetrahydro(1 or 2)naphthyl; anthracen-1-yl; anthraquinon-1-yl; 9H-fluoren-3-yl; dibenzofuran-2- or 4-yl; 9H-xanthen-2-yl; dibenzothiophen-2-yl; or phenoxathiin-2-yl; R2 = H; Me; or Y1-CO-1-3C alkyl; Y1 = OH; alkoxy; benzyloxy; NH2; NH(alkyl); or N(alkyl)2; R3 = H or Me; R4 = 1-6C alkyl; 3-6C alkenyl; 3-7C cycloalkyl; alkoxyalkyl; benzyl; tetrahydrofuran-2-ylmethyl; or tetrahydropyran-2-ylmethyl; R5 = H; 1-6C alkyl; 3-6C alkenyl; Y1-CO-1-3C alkyl; or (p-Y1-CO-C6H4)-1-3C alkyl; or NR4R5 = 4-6C alkyleneimino optionally monosubstituted by alkyl, alkoxy or W or disubstituted by alkyl and W; W = HOCH2-; alkoxy-CH2-; (alkyl or alkoxy)-CO-O-CH2-; H2N-CH2-; alkyl-NH-CH2-; benzyl-NH-CH2-; (alkyl, alkoxy or benzyloxy)-CO-NH-CH2-; (alkyl or benzyl)2N-CH2-; CN; 1H-tetrazol-5-yl; or Y2-CO-; Y2 = OH; alkoxy; NH2; NH(alkyl or benzyl); N(alkyl or benzyl)2; or (carboxyalkyl, alkoxycarbonyl or benzyloxycarbonylalkyl)amino; and unspecified alkyl and alkylene contain 1-4C.

Description

Thrombin cleaves into fibrinogen (Aα, Bβ, γ) ₂, the 376 Arg / Lys-Xaa Contains bonds, highly specific P1-P1 ′ to only four Arg (= P1). First and fastest is the splitting at Arg¹⁶ (with elimination of fibrinopeptide A). For the high spec fibrinopeptide recognition in thrombin Specificity pocket and the simultaneous fibrinogen-composite Detection blamed (M. T. Stubbs and W. Bode, Thrombosis Research 1993, 69, 1-58). The fact that at the Cleavage point P1 is always an arginine, illuminates the large Be interpretation of this rest for its specific interaction with Thrombin-Asp¹⁸⁹ in the specificity pocket.

Because of the central and diverse role of thrombin in Coagulation events are of great interest in ge suitable thrombin inhibitors to thrombin (with) induced throma to avoid evil or to influence it favorably. Known com petitive thrombin inhibitors either contain an arginine (such as Argatroban) or arginine mimetics. Among the latter are those which instead of the guanidino group of arginine cycli based guanidino groups, (benz) amidino or imidazole-4 (5) - have yl groups.

It has now been found that the new substituted 2-amino imidazoles of the general formula

their stereoisomers, their mixtures and their salts, in particular their physiologically compatible salts with inorganic or organic acids or bases, valuable pharmacological Have properties, in particular a thrombin-inhibiting and the thrombin time prolonging effect.

The present invention thus relates to the new sub substituted 2-amino-imidazoles of the above general formula (1), their stereoisomers, their mixtures and their salts, ins especially their physiologically tolerable salts with inorganic or organic acids or bases, these compounds containing medicinal products, their use and their manufacture lung.

In the above general formula, (1) means
A is an alkylene group with 1 to 6 carbon atoms or an alkenylene group with 3 to 6 carbon atoms, in each of which the double bond is in the α-position to the imidazole ring,
R₁ an optionally by an alkyl, alkoxy, dimethyl amino, diethylamino, nitro, amino, cyano or trifluoromethyl group or a fluorine, chlorine, bromine or iodine atom monosubstituted phenyl radical, an alkyl or Alkoxy groups disubstituted phenyl radical, where the substituents can be the same or different, or a phenyl radical trisubstituted by an amino group and two chlorine or bromine atoms,
a naphthyl or 2-naphthyl radical which is optionally monosubstituted by an alkyl, alkoxy, dimethylamino or diethylamino group or a chlorine atom or a 1-naphthyl or 2-naphthyl radical which is disubstituted by alkyl or alkoxy groups, the substituents being identical or can be different,
a quinolin-8-yl, isoquinolin-5-yl, isoquinolin-6-yl or isoquinolin-7-yl radical which is optionally substituted by an alkyl group,
an isoindolin-5-yl-, 1,2,3,4-tetrahydro-ohinolin-8-yl-, 1,2,3,4-tetrahydro-isoquinolin-5-yl- which is optionally substituted in the non-aromatic ring by an alkyl group, 1,2,3,4-tetrahydro-isoquinolin-6-y1-, 1,2,3,4-tetrahydro-isoquinolin-7-yl- or 2,3,4,5-tetrahydro-1H-3-benzazepine 7-yl residue,
a 5,6,7,8-tetrahydro-1-naphthyl-, 5,6,7,8-tetrahydro-2-naphthyl-, anthracen-1-yl-, anthraquinon-1-yl-, 9H-fluorene-3 -yl, dibenzofuran-2-yl, dibenzofuran-4-yl, 9H-xanthene-2-yl, dibenzothiophene-2-yl or phenoxathiin-2-yl radical,
R₂ is a hydrogen atom, a methyl group or a Y₁-CO- (C₁-C₃) alkyl group, wherein

Y₁ is a hydroxy, alkoxy, benzyloxy, amino, alkylami represents no or dialkylamino radical,

R₃ is a hydrogen atom or a methyl group,
R₄ is an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 3 to 6 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms, an alkoxyalkyl, benzyl, Te trahydrofuran-2-yl-methyl- or tetrahydropyran-2-yl-methyl - rest,
R₅ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a Y₁-CO- (C₁-C₃) alkyl or (p-Y₁-CO-C₆H₄) - (C₁-C₃) alkyl - Group, wherein Y₁ is defined as mentioned at the beginning, or
R₄ and R₅ together with the intermediate nitrogen atom, an alkyleneimino radical optionally monosubstituted by an alkyl or alkoxy group or by a radical W or an alkyleneimino radical disubstituted by an alkyl group and a radical W, the alkyleneimino radical containing 4 to 6 carbon atoms can and

W is a HOCH₂-, alkoxy-CH₂-, alkyl-CO-O-CH₂-, alkoxy-CO-O-CH₂-, H₂N-CH₂-, alkyl-NH-CH₂-, benzyl-NH-CH₂-, alkyl-CO -NH-CH₂-, alkoxy-CO-NH-CH₂-, benzyloxy-CO-NH-CH₂-, (alkyl) ₂N-CH₂-, (benzyl) ₂N-CH₂-, NC-, 1H-tetrazol-5-yl - or Y₂-CO group, wherein
Y₂ is a hydroxyl, alkoxy, amino, alkylamino, benzyl amino, dialkylamino, dibenzylamino, (carboxyalkyl) amino, (alkoxycarbonylalkyl) amino or (benzyloxycar bonylalkyl) amino radical ,

unless stated otherwise, the above he mentioned alkyl and alkylene parts each of 1 to 4 carbon can contain atoms.

Preferred compounds of the above general formula I are those in which
A is an alkylene group with 1 to 4 carbon atoms or an alkenylene group with 3 or 4 carbon atoms, in each of which the double bond is in the α-position to the imidazole ring,
R₁ is a phenyl radical monosubstituted by an alkyl, alkoxy, dimethylamino, diethyl amino, nitro or amino group in the 4-position, a phenyl radical disubstituted by two alkyl or two alkoxy groups in the 3,4-position or one by an amino group in the 4-position and by chlorine or bromine atoms in the 3,5- or 2,5-position trisubstituted phenyl radical,
a 1-naphthyl or 2-naphthyl radical which is optionally monosubstituted by an alkyl, alkoxy or dimethyl amino group or a 1-naphthyl or 2-naphthyl radical which is disubstituted by two alkyl or two alkoxy groups,
a quinolin-8-yl or isoquinolin-5-yl radical optionally substituted by an alkyl group,
an isoindolin-5-yl-, 1,2,3,4-tetrahydroquinolin-8-yl-, 1,2,3,4-tetrahydro-isoquinolin-5-yl- which is optionally substituted in the non-aromatic ring by an alkyl group , 1,2,3,4-tetrahydro-isoquinolin-6-yl-, 1,2,3,4-tetrahydro-isoquinolin-7-yl- or 2,3,4,5-tetrahydro-1H-3-benzazepine -7-yl residue,
R₂ is a hydrogen atom or a methyl group,
R₃ is a hydrogen atom,
R₄ is an alkyl group with 1 to 5 carbon atoms, a cyclo alkyl group with 3 to 6 carbon atoms or a benzyl group,
R₅ is a hydrogen atom, an alkyl group or a Y₁-CO-CH₂ group, wherein

Y₁ is a hydroxy, alkoxy, benzyloxy, amino, alkylami represents no or dialkylamino radical,

or R₄ and R₅ together with the nitrogen in between atom one optionally by an alkyl group or a W radical or substituted by an alkyl group and a W radical  ized alkyleneimino radical, the alkyleneimino radical being 4 to 6 May contain carbon atoms and

W represents a Y₂-CO group, wherein
Y₂ is a hydroxyl, alkoxy, benzyloxy, amino, alkyl amino, dialkylamino, (carboxyalkyl) amino, (alkoxy carbonylalkyl) amino or (benzyloxycarbonylalkyl) amino radical,

mean,
Unless otherwise stated, the alkyl and alkylene parts mentioned above may each contain 1 to 4 carbon atoms,
their stereoisomers, their mixtures and their salts, in particular their acid addition salts.

Particularly preferred compounds of the general formula I above are those in which
A is an alkylene group with 1 to 3 carbon atoms or a propenylene group in which the double bond is in the α-position to the imidazole ring,
R₁ is a phenyl radical trisubstituted by an amino group in the 4-position and by two chlorine atoms in the 3,5- or 2,5-position,
a 1-naphthyl or 2-naphthyl radical optionally substituted by a dimethylamino group,
a quinolin-8-yl or isoquinolin-5-yl radical optionally substituted by a methyl group,
a 1,2,3,4-tetrahydro-quinolin-8-yl-, 1,2,3,4-tetrahydro-isoquinolin-5-yl-, 1,2,3, which is optionally substituted in the non-aromatic ring by a methyl group, 4-tetrahydro-isoquinolin-6-yl or 1,2,3,4-tetrahydro-isoquinolin-7-yl radical,
R₂ is a hydrogen atom,
R₃ is a hydrogen atom,
R₄ and R₅ together with the intermediate nitrogen atom represent a piperidino radical optionally substituted by an alkyl group in the 4-position or a piperidino radical substituted by an alkyl group in the 4-position and by a radical W in the 2-position, where

W is a carboxy, alkoxycarbonyl, benzyloxycarbonyl, Aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbo nyl-, (carboxymethyl) aminocarbonyl-, (alkoxycarbonyl methyl) aminocarbonyl- or (benzyloxycarbonylmethyl) represents aminocarbonyl group,

mean,
in particular the compounds mentioned above which contain a (2R, 4R) -disubstituted piperidino radical,
unless otherwise mentioned, the alkyl parts mentioned above may each contain 1 to 4 carbon atoms,
their stereoisomers, their mixtures and their salts.

However, very particularly preferred compounds are those which are configured on the C * carbon atom (S), and their phy Siologically compatible salts, especially their acid additives tion salts.  

Examples of particularly preferred compounds are fol mentioned above:

• (a) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2- amino-imidazol-4-yl) -4- (Z) -pentene-oyl] -4-methyl-piperidine,
• (b) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2- amino-imidazol-4-yl) -4- (E) -pentene-oyl] -4-methyl-piperidine,
• (c) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2- amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine,
• (d) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -6- (2- amino-imidazol-4-yl) -5- (Z) -hexen-oyl] -4-methyl-piperidine,
• (e) 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl- 1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -4- (Z) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester,
• (f) 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl- 1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -4- (E) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester,
• (g) 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl- 1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -pentanoyl} - (2R, 4R) - 4-methyl-piperidine-2-carboxylic acid ethyl ester and
• (h) 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3R, S) -3-methyl- 1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -pentanoyl} - (2R, 4R) - 4-methyl-piperidine-2-carboxylic acid

as well as their salts.

According to the invention, the new compounds are obtained, for example wise according to the following procedures:  

a) implementation of an imidazo [1,2-a] pyrimidine of the general formula

in the
A and R₁ to R₅ are as defined in the beginning, with hydrazine of the formula

H₂N - NH₂ (3).

The reaction is advantageously carried out in a solvent such as methanol, ethanol, dioxane, tetrahydrofuran, diethyl ether, Benzene, toluene, acetonitrile or dimethylformamide, especially advantageous, however, with an excess of hydrazine, when he high temperatures, preferably at the boiling point of Reaction mixture carried out.

b) For the preparation of a compound of the general formula (1) in which A represents an alkylene group having 3 to 6 carbon atoms:
Hydrogenation of a substituted 2-amino-imidazole of the general formula

in the
R₁ to R₅ are as defined in the introduction and
A₁ represents an alkenylene group with 3 to 6 carbon atoms, in each of which the double bond is in the α-position to the imidazole ring.

The catalytic hydrogenation is carried out with hydrogen in counter were a catalyst, preferably palladium / carbon, in one Solvents such as methanol, ethanol, or ethyl acetate Glacial acetic acid, optionally with the addition of an acid such as hydrochloric acid at temperatures between 0 and 50 ° C, but preferably at Room temperature, and at a hydrogen pressure of 1 to 7 bar, but preferably from 3 to 5 bar.

c) separation of protective residues from a connection of the general my formula

in the
A and R₁ to R₅ are as defined in the introduction,
one of the radicals R₆ and R₇ a protective group for an amino or imino group and
the other of the radicals R₆ and R₇ represents a hydrogen atom or a protective group for an amino or imino group.

For example, come as protective residues for the amino and / or Imino group of a 2-amino-imidazol-4-yl group the acetyl, tert-butoxycarbonyl, benzyloxycarbonyl, benzyl, methoxy benzyl, 2,4-dimethoxybenzyl and triphenylmethyl group in Be dress.

A protective residue used is split off for the purpose moderately hydrolytically in an aqueous solvent, e.g. B. in water, isopropanol / water, tetrahydrofuran / water or dio xan / water, in the presence of an acid such as trifluoroacetic acid, Hydrochloric acid or sulfuric acid or in the presence of an alkali base such as sodium hydroxide or potassium hydroxide or aprotic, e.g. B. in Presence of iodotrimethylsilane, at temperatures between -10 and 100 ° C, preferably at temperatures between 0 and 60 ° C.

The splitting off of a benzyl, methoxybenzyl or benzyloxycar bonylrestes is advantageously carried out acidolytically with means of bromine or hydrogen chloride in glacial acetic acid or hydrogenolytically, z. B. with hydrogen in the presence of a catalyst such as palladium / carbon in a solvent such as methanol, Etha nol, ethyl acetate or glacial acetic acid, optionally with the addition of an acid such as hydrochloric acid at temperatures between 0 and 50 ° C, but preferably at room temperature, and at a hydrogen pressure of 1 to 7 bar, but preferably from 3 to 5 bar,
the cleavage of a 2,4-dimethoxybenzyl radical, however, preferably in trifluoroacetic acid in the presence of anisole,
however, the cleavage of a tert-butyl or tert-butyloxycarbonyl residue is preferably carried out by treatment with an acid such as trifluoroacetic acid or hydrochloric acid, optionally using a solvent such as methylene chloride, dioxane or ether, and
the cleavage of a triphenylmethyl radical, however, preferably acidolytically, for. B. with hydrogen chloride in acetone or in 80% acetic acid or with trifluoroacetic acid in methylene chloride / methanol, or by catalytic hydrogenolysis, for. B. on palladium black.

d) For the preparation of a compound of the general formula (1) in which A represents an alkylene group with 1 to 6 carbon atoms:
Implementation of an imidazole of the general formula

in the
R₁ to R₅ are as defined in the introduction and
A₂ represents an alkylene group with 1 to 6 carbon atoms,
with a diazonium salt of the general formula

in the
R₈ is a hydrogen or halogen atom, a methyl, nitro or alkoxycarbonyl group, preferably a methoxycarbonyl or ethoxycarbonyl group, and
X⁻ is a chloride or bromide anion,
and subsequent hydrogenative cleavage of the azo compound of the general formula obtained

in the
A₂, R₁ to R₅ and R₈ are as defined above.

The reaction is conveniently in a buffered aq solvent if necessary with the addition of Te trahydrofuran, dioxane, methanol or ethanol at temperatures between -10 and 40 ° C, preferably at temperatures between 0 and 10 ° C, and expediently at a pH of 9.0 to 9.5 carried out.

The subsequent catalytic hydrogenation is carried out with water substance in the presence of a catalyst, preferably on platinum dioxide, in a solvent such as methanol, ethanol or Ethyl acetate, optionally with the addition of an acid such as hydrochloric acid or acetic acid at temperatures between 0 and 50 ° C, but preferably at room temperature, and at one Hydrogen pressure from 1 to 7 bar, but preferably from 3 to 5 bar.  

e) implementation of a carboxylic acid of the general formula

in the
A, R₁ to R₃ are as defined in the introduction,
R₉ is a hydrogen atom or a protecting group for an amino group and
R₁₀ represent a hydrogen atom or a protective group for an imino group,
with an amine of the general formula

in the
R₄ and R₅ are as defined at the beginning,
or with their reactive derivatives optionally prepared in the reaction mixture,
and if necessary, subsequent splitting off of protective residues, if used.

As reactive derivatives of a compound of the general Formula (9) includes, for example, their esters such as methyl, Ethyl or benzyl esters, their thioesters such as the methylthio or Ethyl thioesters, their halides such as acid chloride, their anhydrides or imidazolides into consideration.  

The reaction is conveniently carried out in a solvent such as Methylene chloride, chloroform, carbon tetrachloride, ether, Te trahydrofuran, dioxane, benzene, toluene, acetonitrile or dime thylformamide, optionally in the presence of an acid tivatives or a dehydrating agent, e.g. B. in the presence of ethyl chloroformate, chloroformate rice butyl ester, thionyl chloride, phosphorus trichloride, phosphorus pentoxide, N, N'-dicyclohexylcarbodiimide, N, N'-dicyclohexylcarbo diimide / N-hydroxysuccinimide, O- (benzotriazol-1-yl) -N, N, N ′, N′-th tramethyl uronium tetrafluoroborate, O- (benzotriazol-1-yl) - N, N, N ′, N′-tetramethyl uronium tetrafluoroborate / N-hydroxy-1H- benzotriazole, N, N'-carbonyldiimidazole or N, N-thionyldiimida zole or triphenylphosphine / carbon tetrachloride, or one the amino group of (10) activating agents, e.g. B. phosphorus trichloride, and optionally in the presence of an inorganic Base such as sodium carbonate or a tertiary organic base such as triethylamine or pyridine, which at the same time as a solution can serve at temperatures between -25 and 250 ° C, but preferably at temperatures between -10 ° C and Boiling temperature of the solvent used. The reaction can also be carried out without a solvent, furthermore, water formed during the reaction can by azeotropic distillation, e.g. B. by heating with toluene on Water separator, or by adding a desiccant such as Magnesium sulfate or molecular sieve are separated.

f) implementation of an amino compound of the general formula

in the
A, R₂ to R₅, R₉ and R₁₀ are as defined in the introduction,
with a sulfonic acid halide of the general formula

R₁-SO₂-Y (12),

in the
R₁ is as defined in the introduction and
Y is a leaving group such as a halogen atom, e.g. B. a chlorine or bromine atom means
and, if necessary, subsequent splitting off of protective residues, if used.

The reaction is advantageously carried out in a solvent or solvent mixture such as tetrahydrofuran, methylene chloride, Chloroform, ethyl acetate or dimethylformamide conveniently in the presence of an inorganic base such as sodium carbonate, Ka lium carbonate or sodium hydroxide solution or in the presence of a tertiary organic base such as triethylamine, N-ethyl-diisopropylamine, N-methyl-morpholine or pyridine, which at the same time as Solvents can be used at temperatures between -30 ° C and 100 ° C, but preferably at temperatures between -10 ° C and 60 ° C.

g) For the preparation of a compound of the general formula (1) in which A represents an alkylene group with 1 to 6 carbon atoms:
Implementation of an aminoketone hydrochloride of the general formula

in the
R₁ to R₅ are as defined in the introduction and
A₂ represents an alkylene group with 1 to 6 carbon atoms,
with cyanamide of the formula

H₂N-CN (14).

The reaction is advantageously carried out in an aqueous solution means, e.g. B. in water, methanol / water, ethanol / water, Tetrahydrofuran / water, dioxane / water or dimethylformamide / Water at temperatures between 20 and 150 ° C, preferably at temperatures between 80 and 100 ° C. The order However, settlement can also be carried out without a solvent in the melt be performed.

If, according to the invention, a compound of the general formula (1) is obtained in which R 1 represents a quinolin-8-yl or isoquinolin-5-yl radical which is optionally substituted by an alkyl group having 1 to 4 carbon atoms, this can be obtained by reduction, preferably by catalytic hydrogenation, into a corresponding compound of the general formula (1) in which R₁ is a 1,2,3,4-tetrahydro-quinolin-8-yl- or 1, which is optionally substituted by an alkyl group having 1 to 4 carbon atoms, 2,3,4-Tetrahydro-isoquinolin-5-yl residue represents, are performed, or
a compound of the general formula (1) in which R₂ is an alkoxycarbonyl (C₁-C₃) alkyl radical, this can be by means of hydrolysis into a corresponding compound of the general formula (1) in which R₂ is a carboxy- (C₁ -C₃) alkyl group represents, transferred, or
a compound of the general formula (1) in which R₅ represents an alkoxycarbonyl- (C₁-C₃) alkyl or (p-alkoxycarbonyl-phenyl) - (C₁-C₃) alkyl radical, this can be hydrolysed into a corresponding compound of the general formula (1) in which R₅ represents a carboxy- (C₁-C₃) alkyl or (p-carboxy-phenyl) - (C₁-C₃) alkyl radical are converted, or
a compound of the general formula (1) in which the R₄R₅N group contains a substituted by a radical W alkyleneimino radical having 4 to 6 carbon atoms in the alkylene part, this can, if W represents an alkoxycarbonyl or benzyloxycarbo nylgruppe, by hydrolysis in a corresponding compound of the general formula (1) in which W represents a carboxy group, or,
if W represents a benzyloxycarbonyl group, be converted by hydrolysis into a corresponding compound of the general formula (1) in which W represents a carboxy group.

The subsequent hydrolysis is carried out hydrolytically in an aqueous solution Rigen solvent, for. B. in water, isopropanol / water, tetra hydrofuran / water or dioxane / water, in the presence of an acid such as trifluoroacetic acid, hydrochloric acid or sulfuric acid or in Presence of an alkali base such as sodium hydroxide or potassium hy hydroxide or aprotic, e.g. B. in the presence of iodotrimethylsilane, at temperatures between -10 and 100 ° C, preferably at tem temperatures between 0 and 60 ° C.  

The subsequent catalytic hydrogenation or hydrogenolysis takes place with hydrogen in the presence of a catalyst such as Palladium / carbon in a solvent such as methanol, ethanol, Ethyl acetate or glacial acetic acid, optionally with addition an acid such as hydrochloric acid at temperatures between 0 and 50 ° C, but preferably at room temperature and with water fabric pressure from 1 to 7 bar, but preferably from 3 to 5 bar.

In the implementations described above, there may be if reactive groups such as hydroxy, carboxy, Amino, alkylamino, imino or imidazolyl groups during the Implementation are protected by usual protection groups, which be split off after implementation.

For example, the trimethylsilyl, acetyl, benzoyl, tert-butyl, trityl, benzyl or tetrahydropyranyl group comes as a protective radical for a hydroxyl group,
as a protective radical for a carboxyl group, the trimethylsilyl, methyl, ethyl, tert-butyl, benzyl or tetrahydropyranyl group,
as a protective radical for an amino, alkylamino or imino group, the acetyl, tert-butoxycarbonyl, benzyloxycarbonyl, benzyl, methoxybenzyl or 2,4-dimethoxybenzyl group and for the amino group additionally the phthalyl group and
as protective residues for the amino and / or imino group of a 2-amino-imidazol-4-yl group, the acetyl, tert-butoxycarbonyl, benzyloxycarbonyl, benzyl, methoxybenzyl, 2,4-dimethoxy benzyl and triphenylmethyl Group considered.

The subsequent subsequent splitting off of one used Protective residue takes place, for example, hydrolytically in an aqueous solution Rigen solvent, for. B. in water, isopropanol / water, tetra  hydrofuran / water, dioxane / water or glacial acetic acid / water, in Ge presence of an acid such as trifluoroacetic acid, hydrochloric acid or Sulfuric acid or in the presence of an alkali base such as sodium hydroxide or potassium hydroxide or aprotic, e.g. B. in the present of iodotrimethylsilane, at temperatures between -10 and 100 ° C, preferably at temperatures between 0 and 60 ° C.

The splitting off of a benzyl, methoxybenzyl or benzyloxy car However, bonylrestes is carried out, for example, by acidolysis Hydrogen bromide or hydrogen chloride in glacial acetic acid or hydrogenolytic, e.g. B. with hydrogen in the presence of a catalyst such as Palla dium / coal in a solvent such as methanol, ethanol, vinegar acid ethyl ester or glacial acetic acid, optionally with the addition of a Acid such as hydrochloric acid at temperatures between 0 and 50 ° C but preferably at room temperature, and with a hydrogen pressure from 1 to 7 bar, but preferably from 3 to 5 bar.

However, a 2,4-dimethoxybenzyl radical is split off preferably in trifluoroacetic acid in the presence of anisole.

The cleavage of a tert-butyl or tert-butyloxycarbonyl the rest is preferably done by treatment with an acid such as trifluoroacetic acid or hydrochloric acid optionally under Use of a solvent such as methylene chloride, dioxane or ether.

A triphenylmethyl radical is preferably split off acidolytic, e.g. B. with hydrogen chloride in acetone or in 80% acetic acid or with trifluoroacetic acid in methylene chloride rid / methanol, or also by catalytic hydrogenolysis, e.g. B. to Palladium-Mohr.

A phthalyl radical is preferably split off in Ge presence of hydrazine or a primary amine such as methylamine, Ethylamine or n-butylamine in a solvent such as methanol,  Ethanol, isopropanol, toluene / water or dioxane at temperature ren between 20 and 80 ° C.

Furthermore, the compounds of general form mel (1), as already mentioned at the beginning, in their enantio mers and / or diastereomers are separated. So can for example connections with at least one optically ak tive carbon atom are separated into their enantiomers.

For example, the compounds obtained from general formula (1), which occur as racemates, according to known methods (see Allinger N. L. and Eliel E. L. in "Topics in Stereochemistry", Vol. 6, Wiley Interscience, 1971) in their optical antipodes, and compounds of gen my formula (1) with at least 2 asymmetric carbon atoms due to their physico-chemical differences according to known methods, e.g. B. by chromatography and / or fractional crystallization, in their diastereomers separate which, if they occur in racemic form, on finally be separated into the enantiomers as mentioned above can.

The separation of enantiomers is preferably carried out by column trenches on chiral phases, by recrystallization from an op table active solvent, or by reaction with an op table active substance with formation of diastereomeric salts or derivatives, separating the diasters thus obtained reomeric salts or derivatives, e.g. B. due to various Solubilities, being from the pure diastereomeric salts or Derivatives the antipodes by the action of suitable agents can be released.

Furthermore, the compounds of formula (1) obtained in their salts, especially for pharmaceutical use, in their physiologically compatible salts with inorganic or organic acids. Coming as acids  for this, for example hydrochloric acid, hydrobromic acid, Schwe rock acid, phosphoric acid, acetic acid, fumaric acid, amber acid, lactic acid, citric acid, tartaric acid or maleic acid Consideration.

In addition, the new compounds obtained in this way Formula (1), if they contain a carboxyl group, ge if desired, then in their salts with inorganic or organic bases, especially for pharmaceutical Use in their physiologically tolerated salts Ren. For example, sodium hydroxide, Potassium hydroxide, ammonia, cyclohexylamine, ethanolamine, dietha nolamine and triethanolamine.

The compounds used as starting materials are partial known from the literature or obtained from known literature Procedure (see examples).

For example, one obtains an output compound of general formula (2) as follows:

(i) For the preparation of a compound of the general formula (2) in which A represents an alkylene group with 3 to 6 carbon atoms or an alkenylene group with 3 to 6 carbon atoms, in each of which the double bond is in the α-position to the imidazole ring:
Implementation of an aldehyde of the general formula

in the
R₁ to R₅ are as defined in the introduction and
m represents the number 1, 2, 3 or 4,
with a phosphonium salt of the general formula

in the
X⁻ represents a chloride or bromide anion,
in the presence of a suitable organic or inorganic base
and optionally subsequent hydrogenation.

The aldehyde of the general formula (14) required for this is, for example, by oxidation of a corresponding alcohol hols or by reduction of an appropriate N-acylated Obtained N, O-dimethyl-hydroxylamine; the necessary for this Phosphonium salt of the general formula (15) is replaced by Um settlement of 2-chloromethyl- or 2-bromomethyl-imidazo [1,2-a] pyrimidine (Farmaco, Ed. Sci., 1976, 31, 731-737) in the usual Way with triphenylphosphine (CA 115: 71478r; Ukr. Khim. Zh. (Russ. Ed.) 1991, 57, 187-191).

(ii) For the preparation of a starting compound of the general formula (2) in which A represents an alkylene group having 3 to 6 carbon atoms:
Conversion of an amino acid of the general formula

in the
R₂ and R₃ are as defined in the introduction and
n means the numbers 1 to 6,
analogous to those in Rec. Trav. Chim. Pays-Bas 1975, 94, 182-185; Synth. Commun. 1989, 19, 2069-2076; or methods described in EP-A-0,399,556 (Examples O and S) with the aid of suitable protective groups,
into an ω-halogen ketone of the general formula

in the
R₂ to R₅ and n are as defined in the introduction,
R₁₁ is a protecting group for an amino group and
X represents a chlorine or bromine atom,
subsequent reaction with 2-amino-pyrimidine analogous to Bull. Soc. Chim. 1966, 2529-2531 and J. Het. Chem. 1971, 8, 643-650 to a corresponding 2-substituted imidazo [1,2-a] pyrimidine of the general formula

in the
R₂ to R₅, R₁₁ and n are as defined in the introduction,
Elimination of a protective radical used and reaction of a compound of the general formula thus obtained

in the
R₂ to R₅ and n are defined as above, with a corresponding sulfochloride to the desired compound.

(iii) reaction of a carboxylic acid of the general formula

in the
A and R₁ to R₃ are as defined in the introduction,
with an amine of the general formula

in the
R₄ and R₅ are as defined at the beginning,
and optionally subsequent hydrogenation.

The carboxylic acid of the general formula required for this (21) can, for example, from a corresponding carboxylic acid amide by acid hydrolysis or from a corresponding car bonic acid ester obtained by hydrogenolysis or hydrolysis the.

(iv) reaction of an amino compound of the general formula

in the
R₂ to R₅ and A are defined as above,
with a sulfonic acid halide of the general formula

R₁-SO₂-Y (12)

in the
R₁ and Y are as defined in the introduction,
and optionally subsequent hydrogenation.

A starting compound of the general formula (5) can be obtained from can be obtained for example as follows:

(i) For the preparation of a compound of the general formula (5) in which A represents an alkylene group with 3 to 6 carbon atoms or an alkenylene group with 3 to 6 carbon atoms, in each of which the double bond is in the α-position to the imidazole ring:
Reaction of an aldehyde of the general formula (15) with a phosphonium salt of the general formula

in the
R₆ and R₇ are as defined in the introduction and
X⁻ represents a chloride or bromide anion,
in the presence of a suitable organic or inorganic base
and optionally subsequent hydrogenation.

The preparation of the phosphonium salt required for this of the general formula (23) is advantageously carried out by man 1-Boc-4-formyl 2-tritylamino-1H-imidazole (FR-A-2,681,323; CA 119: 139229a) via the corresponding 4-hydroxymethyl verbin tion into the corresponding 4-chloromethyl compound and reacted this with triphenylphosphine.

(ii) For the preparation of a starting compound of the general formula (5) in which A denotes a methylene group:
Conversion of a 2'-amino-histidine with the aid of suitable protective groups (see, for example, Helv. Chim. Acta 1990, 73, 86-96) into a corresponding carboxylic acid, which is then reacted with an amine of the general formula (10) to give the desired amide ; if necessary, subsequent cleavage of a protective radical used and subsequent sulfonylation. [Racemic 2'-amino-histidine can be like 2'-amino-L-histidine (see J. Org. Chem. 1973, 38, 1971-1974) or by alkylation of acetamido-malonic ester with 2-chloromethyl-imidazo [1, 2-a] pyrimidine, reaction of the obtained 2-substituted imidazo [1,2-a] pyrimidine with hydrazine and subsequent hydrolysis.]

(iii) To prepare a starting compound of the general formula (5) in which A denotes an alkylene group having 1 to 6 carbon atoms:
Reaction of an ω-halogen ketone of the general formula (18)
with Formamidin analog Rec. Trav. Chim. Pays-Bas 1975, 94, 182-185 and Synth. Commun. 1989, 19, 2069-2076 to a corresponding imidazole, which is subsequently converted into a corresponding azo compound using a diazonium salt of the general formula (7) and then converted into a corresponding 2- by hydrogenative cleavage, removal of a protective radical used and sulfonylation Amino imidazole is converted
or with sodium formylamide (analog Synthesis 1990, 615-618), or with sodium azide and subsequent hydrogenation (analog J. Org. Chem. 1986, 51, 3374-3376), or with potassium phthalimide and subsequent hydrazinolysis or aminolysis to a corresponding ω-amino ketone of the general formula

in the
R₂ to R₅, R₁₁ and n are as defined in the introduction,
which is then converted into a corresponding 2-amino-imidazole by reaction with cyanamide, elimination of a protective radical used and sulfonylation.

As already mentioned at the beginning, the new connections of the general formula (1) valuable pharmacological properties on, in particular a thrombin-inhibiting effect. You inhibit Thrombin-induced or -induced physiological processes such as B. platelet aggregation and blood coagulation. There they have a thrombin-specific inhibitory effect; on their serine proteases, especially trypsin, are not or little inhibited.

The compounds of the invention were found, for example their effectiveness tested in the following tests:

1. Competitive inhibition of thrombin in vitro

Thrombin inhibition of a compound was detected in one Chromogenic assay at 37 ° C for 4 minutes at 0.29 U / ml Bovine thrombin (Behringwerke, Marburg) and 160 µM chromozyme TH (Boehringer Mannheim) as substrate in a 100 mM TRA buffer solution pH 7.4, which contained 200 mM NaCl.

An IC₅₀ was calculated as the concentration of the compound, which reduces the enzymatic activity of the control experiment by 50% inhibited.

2. Competitive inhibition of trypsin in vitro

The trypsin inhibition of a compound was detected in one Chromogenic assay at 25 ° C for 4 minutes at 0.073 U / ml Bovine trypsin (Boehringer Mannheim) and 213 µM chromozyme TRY (Boehringer Mannheim) as substrate in a 100 mM TRIS / HCl Buffer solution pH 8.0, which contained 150 mM NaCl.

An IC₅₀ was calculated as the concentration of the compound, which reduces the enzymatic activity of the control experiment by 50% inhibited.  

The following table contains the results found:

table

Due to the pharmacological properties mentioned above ten of the new compounds, especially by inhibiting them blood coagulation and the inhibition of the development of Thrombi in the arterial and venous vasculature can new compounds of general formula (1) and their physio logically acceptable salts are used for therapy or Prevention of diseases such as thrombosis, heart attack, brain stroke, inflammation or arteriosclerosis, as well as with and after clinical measures involving thrombotic complications can occur, e.g. B. bypass and hip surgery and angio plastic. You can use it alone or in combination with thromboly tables agents, such as tissue plasminogen activator (TPA), Strep tokinase, urokinase, and / or other antithrombotic agents like aspirin, thromboxane A₂ antagonists, thromboxane syn thetase inhibitors or fibrinogen receptor (GP IIb-IIIa) antago nesting can be used.

The necessary to achieve a corresponding effect Dosage is expedient for intravenous bolus administration 0.1 to 50 mg / kg, preferably 1 to 20 mg / kg, and oral  Administration 1 to 100 mg / kg, preferably 5 to 50 mg / kg, each 1 up to 3 times a day, and with intravenous infusion from 0.01 to 5.0 mg / kg / h, preferably 0.01 to 0.1 mg / kg / h. To do this the compounds of the formula prepared according to the invention (1), if necessary in combination with other active substances, together with one or more inert customary carriers and / or diluents, e.g. B. with corn starch, milk sugar, Cane sugar, microcrystalline cellulose, magnesium stearate Polyvinylpyrrolidone, citric acid, tartaric acid, water, water / Ethanol, water / glycerin, water / sorbitol, water / polyethylene gly kol, propylene glycol, cetylstearyl alcohol, carboxymethyl cellulo se or fatty substances such as hard fat or their suitable neten mixtures, in common galenical preparations such as Ta Bletten, coated tablets, capsules, wafers, powder, solutions, suspensions Work in sions, emulsions, syrups, suppositories, etc.

The following examples are intended to explain the invention in more detail tern:  

Preliminary remarks

The following abbreviations are used in the following examples:
Asp = L-aspartic acid
Boc = tert-butyloxycarbonyl
Bzl = benzyl
Celite = diatomaceous earth
DBU = 1,8-diazabicyclo [5.4.0] undec-7-ene
DC = thin layer chromatogram
DMSO = dimethyl sulfoxide
Eq. = Equivalent
EtOAc = ethyl acetate
EtOH = ethanol
Glu = L-glutamic acid
MeOH = methanol
THF = tetrahydrofuran
T _i = internal temperature
Z = benzyloxycarbonyl

example 1 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino- imidazol-4-yl) -4- (Z) -pentene-oyl] -4-methyl-piperidine × HCl × 0.5 H₂O × 0.28 diethyl ether a) 1- [Boc-Asp (OBzl)] - 4-methyl-piperidine

To a cooled (T _i = -30 ° C) and stirred solution of 36 g (111 mmol) of Boc-Asp (OBzl) -OH and 13.4 ml (122 mmol) of N-methyl morpholine in 400 ml of anhydrous THF are added dropwise, in each case within half a 10 minutes, 16.2 ml (125 mmol) isobutyl chloroformate and after 30 minutes at -30 ° C 14.4 ml (122 mmol) 4-methyl piperidine. The mixture is stirred for 2 hours at -30 ° C and then come to room temperature overnight. It is filtered and the filtrate is evaporated in vacuo. The evaporation residue was dissolved in EtOAc, washed with water and 1% aqueous citric acid, the organic solution was dried over sodium sulfate, filtered and evaporated in vacuo. The yellow oil obtained is crystallized by adding 200 ml of petroleum ether (30-60 ° C).
Yield: 39.3 g (87% of theory)
Melting point: 95-98 ° C; [α] = -58.4 ° (c = 0.25; MeOH);
C₂₂H₃₂N₂O₅:
Calc .: C 65.32; H 7.97; N 6.93.
Found: C 65.05; H 7.79; N 6.72.

b) 1- [H-Asp (OBzl)] - 4-methyl-piperidine

240 ml (3.13 mol) of trifluoroacetic acid are added to a stirred and ice-cooled solution of 39.3 g (97 mmol) of 1- [Boc-Asp (OBzl)] - 4-methyl-piperidine in 400 ml of methylene chloride and the mixture is stirred for 2 hours. It is evaporated in vacuo and the evaporated residue is distributed between methylene chloride and aqueous sodium bicarbonate solution. The organic phase is dried over sodium sulfate, filtered and evaporated in vacuo. The raw product obtained will be implemented as quickly as possible.
Crude yield: 29.1 g (98% of theory), yellow oil; [α] = -9.94 ° (c = 0.815; MeOH)

c) 1 - [(4-Amino-3,5-dichlorobenzenesulfonyl) Asp (OBzl)] - 4-methyl piperidine

To a stirred solution of 29 g (95 mmol) of 1- [H-Asp (OBzl)] - 4-methyl-piperidine and 16 ml (114 mmol) of triethylamine in 300 ml of anhydrous methylene chloride are added with cooling with cold water within 15 minutes the solution of 24.8 g (95 mmol) of 4-amino-3,5-dichlorobenzenesulfochloride in 150 ml of anhydrous methylene chloride and stirred for 2.5 days at room temperature. The reaction solution is washed three times with 250 ml of water each time, the organic phase is dried over sodium sulfate, filtered and evaporated in vacuo. The brown oily evaporation residue is purified by column chromatography on silica gel with petroleum ether / EtOAc (2: 1).
Yield: 43.7 g (86% of theory), yellow viscous oil; [α] = + 21.9 ° (c = 0.315; MeOH)

d) 1 - [(4-Amino-3,5-dichlorobenzenesulfonyl) Asp] -4-methyl-pi peridin

The solution of 43.6 g (80 mmol) of 1 - [(4-amino-3,5-di chlorobenzenesulfonyl) Asp (OBzl)] - 4-methyl-piperidine and 165 ml of 1N sodium hydroxide solution in 440 ml of EtOH is stirred 4 hours at 40 ° C, add a further 50 ml of 1N sodium hydroxide solution and stir for a further 2 hours at 40 ° C. 215 ml of 1N hydrochloric acid are added and the mixture is cooled in ice, with crystallization taking place. The crystals obtained are filtered off, washed with ice water and dried at 60 ° C. overnight.
Yield: 30.7 g (85% of theory);
Melting point 167-168.5 ° C; [α] = + 34.8 ° (c = 0.29; MeOH);
C₁₆H₂₁Cl₂N₃O₅S:
Calc .: C 43.84; H 4.83; N 9.59; Cl 16.18.
Found: C 43.53; H 4.79; N 9.45; Cl 16.57.

e) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -4-hydroxy butanoyl] -4-methyl-piperidine

To a cooled (T _i = -20 ° C) and stirred solution of 11 g (25 mmol) of 1 - [(4-amino-3,5-dichlorobenzenesulfonyl) Asp] -4-methyl piperidine and 2.89 ml (26.3 mmol) of N-methylmorpholine in 115 ml of anhydrous THF is added dropwise to 3.43 ml (26.3 mmol) of isobutyl chloroformate within 10 minutes. After 30 minutes, filter. The filtrate is then a solution of 2.36 g (62.5 mmol) of sodium borohydride in 20 ml of water at an internal temperature of max. + 5 ° C added dropwise. The mixture is stirred for 3 hours at room temperature and then neutralized by adding 2N hydrochloric acid with cooling in ice. 200 ml of saturated sodium chloride solution are added and the mixture is extracted twice with 200 ml of EtOAc. The combined organic phases are shaken with saturated sodium bicarbonate solution and then with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in vacuo. The evaporation residue is crystallized from EtOH.
Yield: 8.9 g (83% of theory);
Melting point: 188-192 ° C; [α] = + 99.2 ° (c = 0.265; MeOH);
C₁₆H₂₃Cl₂N₃O₄S:
Calc .: C 45.29; H 5.46; N 9.90; Cl 16.71.
Found: C 44.92; H 5.47; N 9.61; Cl 16.50.
Calc .: Molpeak M⁺ = 423/425/427 (Cl₂).
Found: Molpeak M⁺ = 423/425/427 (Cl₂).

f) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -4-oxo-bu tanoyl] -4-methyl-piperidine

To a stirred solution of 2.0 g (4.71 mmol) of 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -4-hydroxy-butanoyl] -4-methyl piperidine and of 2.0 ml (14.13 mmol) of triethylamine in 12 ml of anhydrous DMSO is dropped at T _i = + 15 ° C with ice cooling, the solution of 2.25 g (14.13 mmol) of sulfur trioxide-pyridine complex in 12 ml of anhydrous DMSO. After 10 minutes, pour on ice water and extract several times with methylene chloride. The organic phase is washed with 0.5 molar aqueous potassium hydrogen sulfate solution and with water, dried over sodium sulfate, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on aluminum oxide (activity level II / III) with EtOAc / EtOH (10: 1).
Yield: 1.4 g (70% of theory);
Melting point 135-137 ° C; [α] = + 89.1 ° (c = 1.01; EtOH);
C₁₆H₂₁Cl₂N₃O₄S:
Calc .: Molpeak M⁺ = 421/423/425 (Cl₂).
Found: Molpeak M⁺ = 421/423/425 (Cl₂).

The oxidation can also be carried out by adding 1.5 eq. Pyridinium chlorochromate to a solution of the alcohol in anhydrous methylene chloride, stirring for 5 hours at 20 ° C., filtration and evaporation in vacuo; the subsequent cleaning then takes place as described above.
Yield: 59% of theory;
C₁₆H₂₁Cl₂N₃O₄S:
Calc .: Molpeak M⁺ = 421/423/425 (Cl₂).
Found: Molpeak M⁺ = 421/423/425 (Cl₂).

g) 1 - [(2S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (imida zo [1,2-a] pyrimidin-2-yl) -4- (Z) -pentene-oyl] -4-methyl-piperidine and 1 - [(2S) -2- (4-amino-3,5-dichlorobenzene-sulfonamido) -5- (imidazo- [1.2-a] pyrimidin-2-yl) -4- (E) -pentene-oyl] -4-methyl-piperidine

To 6.6 g (15.4 mmol) (imidazo [1,2-a] pyrimidin-2-yl-methyl) -triphenylphosphonium chloride with a melting point of 275 ° C. [prepared from 2-chloromethyl-imidazo [1,2-a] pyrimidine and triphenylphosphine in acetonitrile] in 150 ml of anhydrous THF are added at T _i = -70 ° C. with stirring and under dry nitrogen, 4.0 g (35.5 mmol) of potassium tert-butoxide. The yellow-colored solution is stirred for 15 minutes at -70 ° C., then the solution of 5.0 g (11.84 mmol) of 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfone amido) - is rapidly dropped. 4-oxo-butanoyl] -4-methyl-piperidine in 50 ml of anhydrous THF, and is allowed to come to room temperature. After 4 hours, pour on ice water and extract several times with EtOAc. The organic phase is dried over sodium sulfate, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel first with EtOAc, then with EtOAc / EtOH (10: 1). First the (Z) -isomer (R _f = 0.53), then the (E) -isomer (R _f = 0.30; TLC system: EtOAc / EtOH (10: 1)) is eluted.
(Z) -isomer: Yield: 0.43 g (6.8% of theory);
Melting point: 192-195 ° C (from ether); [α] = + 17.8 ° (c = 0.40; MeOH);
400 MHz 1 H NMR (d₆ DMSO); Rotamers A (63%) and B (37%); olefinic protons H _α 6.47 (d; A) or 6.43 (d; B) and H _β 5.79 (dt; A) or 5.73 (dt; B) ppm; J = 11.7 Hz (= cis)
C₂₃H₂₆Cl₂N₆O₃S:
Calc .: C 51.39; H 4.88; N 15.64; Cl 13.19.
Found: C 51.32; H 4.83; N 15.28; Cl 13.03.
Calc .: Molpeak (M + H) ⁺ = 537/539/541 (Cl₂).
Found: Molpeak (M + H) ⁺ = 537/539/541 (Cl₂).
(E) -isomer: yield: 2.38 g (37.4% of theory);
Melting point: 100-104 ° C (from ether); [α] = + 105.2 ° (c = 0.27; MeOH);
400 MHz 1 H NMR (d₆ DMSO); Rotamers A (56%) and B (44%); olefinic protons: H _α 6.58 (d; A) or 6.52 (d; B) and H _β 6.68 (dt; A) bw. 6.62 (dt; B) ppm; J = 15.7 Hz (= trans).
C₂₃H₂₆Cl₂N₆O₃S:
Calc .: C 51.39; H 4.88; N 15.64; Cl 13.19.
Found: C 51.04; H 5.15; N 5.25; Cl 12.89.
Calc .: Molpeak (M + H) ⁺ = 537/539/541 (Cl₂).
Found: Molpeak (M + H) ⁺ = 537/539/541 (Cl₂).

h) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-ami no-imidazol-4-yl) -4- (Z) -pentene-oyl] -4-methyl-piperidine × HCl × 0.5 H₂O × 0.28 diethyl ether

0.33 g (0.614 mmol) of 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (imidazo [1,2-a] pyrimidin-2-yl) -4- is heated (Z) -pen ten-oyl] -4-methyl-piperidine together with 0.20 ml of 80% aqueous hydrazine hydrate in 5 ml of EtOH under reflux for 5.5 hours. In the TLC (silica gel; methylene chloride / MeOH / concentrated ammonia = 50: 10: 0.2), in addition to the main product (R _f = 0.44), there is also a starting product (R _f = 0.95; blue fluorescence). Evaporate in vacuo, dissolve the evaporation residue in toluene, evaporate again and repeat this procedure several times. The evaporation residue obtained is purified by column chromatography on silica gel (system as for DC). From the combined uniform fractions, 0.25 g (76% of theory) of the base is obtained by evaporation in vacuo, which is converted into the hydrochloride using ethereal hydrochloric acid.
Yield: 0.19 g (54.5% of theory);
Melting point: 140 ° C; [α] = + 15.8 ° (c = 0.26; MeOH);
C₂₀H₂₆Cl₂N₆O₃S × HCl × 0.5 H₂O × 0.28 Et₂O:
Calculated: C 44.67; H 5.50; N 14.80; Cl 18.73.
Found: C 44.31; H 5.55; N 14.88; Cl 18.23.
Calc .: Molpeak (M + H) ⁺ = 501/503/505 (Cl₂).
Found: Molpeak (M + H) ⁺ = 501/503/505 (Cl₂).

Example 2 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino- imidazol-4-yl) -4- (E) -pentene-oyl] -4-methyl-piperidine × HCl × H₂O

Prepared analogously to Example 1h from 1.40 g (2.6 mmol) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (imidazo [1,2-a] py rimidin-2- yl) -4- (E) -pentene-oyl] -4-methyl-piperidine (Example 1g) with 0.50 ml of 80% aqueous hydrazine hydrate in 30 ml of EtOH by heating under reflux for 8 hours.
Yield: 1.03 g (71% of theory);
TLC, silica gel, methylene chloride / MeOH / conc. Ammonia (5: 1: 0.02):
R _f = 0.33;
Melting point: 160 ° C (dec.); [Α] = + 87.2 ° (c = 0.25; MeOH)
C₂₀H₂₆Cl₂N₆O₃S × HCl × H₂O:
Calc .: C 43.21; H 5.26; N 15.11; Cl 19.13.
Found: C 43.16; H 5.41; N 14.95; Cl 19.06.
Calc .: Molpeak (M + H) ⁺ = 501/503/505 (Cl₂).
Found: Molpeak (M + H) ⁺ = 501/503/505 (Cl₂).

Example 3 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino- imidazol-4-yl) pentanoyl] -4-methyl-piperidine × HCl × 1.5 H₂O

0.50 g (0.93 mmol) of 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4- (E ) -pentene oyl] -4-methyl-piperidine × HCl × H₂O (Example 2; R _f = 0.65) in 25 ml EtOH over 50 mg palladium-carbon (10%) for 2.5 hours at 20 ° C and 3.4 bar (50 psi ). It is filtered through Celite and the filtrate is evaporated in vacuo. The evaporation residue is chromatographed on silica gel using EtOAc / EtOH / conc. Ammonia (5: 2: 0.02) cleaned. The base obtained (0.45 g; R _f = 0.29) is converted into the hydrochloride using ethereal hydrochloric acid.
Yield: 0.34 g (65% of theory);
Melting point: 150 ° C; [α] = + 73.2 ° (c = 0.265; MeOH);
C₂₀H₂₈Cl₂N₆O₃S × HCl × 1.5 H₂O:
Calc .: C 42.37; H 5.69; N 14.83; Cl 18.76.
Found: C 42.06; H 5.55; H 14.36; Cl 12/19
Calc .: Molpeak M⁺ = 502/504/506 (Cl₂).
Found: Molpeak M⁺ = 502/504/506 (Cl₂).

Example 4 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -6- (2-amino- imidazol-4-yl) -5- (Z) -hexen-oyl] -4-methyl-piperidine a) 1- [Z-Glu (OMe)] - 4-methyl-piperidine

Prepared analogously to Example 1a from Z-Glu (OMe) -OH and 4-methyl piperidine in THF.
Yield: 76.3% of theory, almost colorless oil;
TLC, silica gel, petroleum ether / EtOAc (1: 1): R _f = 0.39.

b) 1- [H-Glu (OMe)] - 4-methyl-piperidine

33 g (87.7 mmol) of 1- [Z-Glu (OMe)] - 4-methyl-piperidine are stirred in 100 ml of glacial acetic acid, 200 ml of 33% strength bromohydrogen / glacial acetic acid solution are added dropwise, and the mixture is stirred for 1.5 hours at room temperature temperature. It is evaporated in vacuo at a bath temperature of 35 ° C. and the evaporation residue is distributed between ether and a little water. Solid sodium bicarbonate is added to the acidic aqueous phase for neutralization and extracted several times with EtOAc. The organic phase is dried over sodium sulfate, filtered and evaporated in vacuo. The raw product obtained is reacted as quickly as possible.
Crude yield: 18.2 g (85.7% of theory), almost colorless oil;
TLC, silica gel, EtOAc / MeOH / conc. Ammonia (5: 1: 0.01): R _f = 0.36.

c) 1 - [(4-Amino-3,5-dichlorobenzenesulfonyl) -Glu (OMe)] - 4-methyl- piperidine

Prepared analogously to Example 1c from 18.0 g (74.3 mmol) of 1- [H-Glu (OMe)] - 4-methyl-piperidine and 21.3 g (81.7 mmol) of 4-amino-3,5-dichlorobenzenesulfochloride in methylene chloride in the presence of 12.5 ml (89.2 mmol) of triethylamine.
Yield: 23 g (66.4% of theory);
Melting point: 125-127 ° C;
TLC, silica gel, petroleum ether / EtOAc (1: 1): R _f = 0.41.

d) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5-hydroxy- pentanoyl] -4-methyl-piperidine

To the stirred solution of 8.0 g (17.1 mmol) of 1 - [(4-amino-3,5-di chlorobenzenesulfonyl) -Glu (OMe)] - 4-methyl-piperidine in 150 ml of ether, 50 ml of THF and 1.04 ml (25.65 mmol) MeOH, 0.65 g (25.65 mmol) lithium borohydride is added at room temperature under dry nitrogen (gas evolution; slightly exothermic). The mixture is stirred for 2.5 hours at room temperature and carefully hydrolyzed by dropwise addition of 1N hydrochloric acid. The organic phase is washed with water, dried over sodium sulfate, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with petroleum ether / EtOAc (1: 2).
Yield: 6.3 g (83.8% of theory), foam;
DC: R _f = 0.26;
C₁₇H₂₅Cl₂N₃O₄S:
Calc .: Molpeak M⁺ = 437/439/441 (Cl₂).
Found: Molpeak M⁺ = 437/439/441 (Cl₂).

e) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5-oxo-pen tanoyl] -4-methyl-piperidine

Prepared analogously to Example 1f from 6.0 g (13.69 mmol) 1 - [(2S) - 2- (4-amino-3,5-dichlorobenzenesulfonamido) -5-hydroxy-pentanoyl] - 4-methyl-piperidine in 35 ml DMSO and 5.8 ml (41.07 mmol) of triethylamine under nitrogen with 6.5 g (41.07 mmol) of sulfur tri-oxide-pyridine complex, dissolved in 35 ml of DMSO.
Yield: 2.9 g (48.6% of theory);
Melting point: 145-147 ° C (from ether);
TLC, silica gel, petroleum ether / EtOAc (1: 2): R _f = 0.52;
C₁₇H₂₃Cl₂N₃O₄S:
Calculated: C 46.79; H 5.31; N 9.63; Cl 16.25.
Found: C 46.75; H 5.32; N 9.62; Cl 16.02.
Calc .: Molpeak M⁺ = 435/437/439 (Cl₂).
Found: Molpeak M⁺ = 435/437/439 (Cl₂).

The oxidation can also be carried out by stirring a solution of the alcohol in anhydrous chloroform with a 20-fold excess excess of activated manganese dioxide at room temperature (24 hours), although a certain amount of alcohol remains, which can also be obtained by heating under reflux (2 hours ) is not oxidized.
Yield: 43.5% of theory;
Melting point: 142-145 ° C.

f) 1 - [(2S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -6- (imida zo [1,2-a] pyrimidin-2-yl) -5- (Z) -hexen-oyl] -4-methyl-piperidine and 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -6- (imidazo- [1.2-a] pyrimidin-2-yl) -5- (E) -hexen-oyl] -4-methyl-piperidine

2.9 g (6.65 mmol) of 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5-oxopentanoyl] -4-methyl-piperidine are placed in 40 ml of anhydrous THF dry nitrogen with stirring and first gives the solution of 3.43 g (7.98 mmol) (imidazo- [1,2-a] pyrimidin-2-yl-methyl) -triphenylphosphonium chloride in 40 ml of anhydrous EtOH and then at T _i = + 10 ° C 1.21 g (7.98 mmol) DBU. The mixture is stirred at room temperature for 24 hours, evaporated in vacuo, the evaporation residue is partitioned between water and EtOAc, dried and filtered, the organic phase is evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with EtOAc / EtOH (20: 1).
(Z) -isomer (R _f = 0.54):
Yield: 0.91 g (24.9% of theory);
Melting point: 100 ° C (from petroleum ether / ether); [α] = + 84.5 ° (c = 0.11; MeOH);
C₂₄H₂₈Cl₂N₆O₃S:
Calc .: Molpeak (M + H) ⁺ = 551/553/555 (Cl₂).
Found: Molpeak (M + H) ⁺ = 551/553/555 (Cl₂).
(E) -isomer (R _f = 0.42):
Yield: 1.44 g (39.3% of theory);
Melting point: 130 ° C (from ether); [α] = + 130.4 ° (c = 0.23; MeOH);
Calc .: Molpeak (M + H) ⁺ = 551/553/555 (Cl₂).
Found: Molpeak (M + H) ⁺ = 551/553/555 (Cl₂)

g) 1 - [(2S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -6- (2-ami no-imidazol-4-yl) -5- (Z) -hexen-oyl] -4-methyl-piperidine

Prepared analogously to Example 1h from 1 - [(2S) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -6- (imidazo [1,2-a] pyrimidin-2-yl) - 5- ( Z) -hexen-oyl] -4-methyl-piperidine and 80% aqueous hydrazine hydrate in EtOH. Around 50% rearrangement to the (E) isomer occurs (see Example 5).
Yield: 30.4% of theory, foam;
TLC, silica gel, EtOAc / EtOH / conc. Ammonia (5: 1: 0.01): R _f = 0.53; [α] = + 56.3 ° (c = 0.135; MeOH);
C₂₁H₂₈Cl₂N₆O₃S:
Calc .: Molpeak (M + H) ⁺ = 515/517/519 (Cl₂).
Found: Molpeak (M + H) ⁺ = 515/517/519 (Cl₂).

Example 5 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -6- (2-amino- imidazol-4-yl) -5- (E) -hexen-oyl] -4-methyl-piperidine

Prepared analogously to Example 1h from 1 - [(2S) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -6- (imidazo [1,2-a] pyrimidin-2-yl) - 5- ( E) -hexen-oyl] -4-methyl-piperidine (Example 4f) and 80% aqueous hydrazine hydrate in EtOH. Rearrangement to the (Z) isomer is not observed.
Yield: 23.4% of theory;
Melting point: 100 ° C (from ether);
TLC, silica gel, EtOAc / Etoll / conc. Ammonia (5: 1: 0.01): R _f = 0.42; [α] = + 97.6 ° (c = 0.21; MeOH);
C₂₁H₂₈Cl₂N₆0₃S:
Calc .: Molpeak (M + H) ⁺ = 515/517/519 (Cl₂).
Found: Molpeak (M + H) ⁺ = 515/517/519 (Cl₂).

If one tries to convert the base into the hydrochloride, it takes place partial cyclization (see example 6).

Example 6 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -6- (2-amino- imidazol-4-yl) -5- (E) -hexen-oyl] -4-methyl-piperidine (I) × HCl and 1 - {[(2S) -1- (4-amino-3,5-dichlorobenzenesulfonyl) -5- (2-amino- imidazol-4-yl) piperidin-2-yl] carbonyl} -4-methyl-piperidine (II) × HCl

1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) - 6- (2-amino-imidazol-4-yl) -5- (E) -hexen-oyl] - is dissolved. 4-methyl-piperidine (I) (Example 5) in EtOH, adds ethereal hydrochloric acid until an acid reaction and evaporates in vacuo. According to DC [silica gel, EtOAc / EtOH / conc. Ammonia (5: 1: 0.01)] a mixture with a melting point of 120 ° C, each consisting of approx. 50% (I) -hydrochloride (R _f = 0.42) and (II) -hydrochloride (R _f = 0.18) with the same Molpeaks.

Example 7 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -6- (2-amino- imidazol-4-yl) hexanoyl] -4-methyl-piperidine × HCl

0.22 g (0.43 mmol) of 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) -5- (E) is hydrogenated -hexen-oyl] - 4-methyl-piperidine (Example 5) in 20 ml EtOH with 30 mg palladium-carbon (10%) for a total of 5 hours at 20 ° C and 3.4 bar (50 psi) After 2.5 hours, the hydrogenation continues to add a further 50 mg of catalyst and after 4 hours 0.5 ml of 1N hydrochloric acid. It is filtered through Celite and the filtrate is evaporated in vacuo. The evaporation residue is determined by column chromatography on silica gel with methylene chloride / MeOH / conc. Ammonia (50: 10: 0.4) cleaned. The base obtained is converted into the hydrochloride using ethereal hydrochloric acid.
Yield: 0.14 g (59% of theory);
Melting point: 130 ° C; [α] = + 60.0 ° (c = 0.20; MeOH);
C₂₁H₃₀Cl₂N₆O₃S × HCl:
Calc .: Molpeak M⁺ = 516/518/520 (Cl₂).
Found: Molpeak M⁺ = 516/518/520 (Cl₂).

Example 8 1- [rac-5- (2-Amino-imidazol-4-yl) -2- (quinolin-8-sulfonamido) - 4- (E) -pentene-oyl] -4-methyl-piperidine × 2 HCl × 0.5 H₂O a) rac-N-Boc-2-amino-butyrolactone

107 ml (769 mmol) of triethylamine are added dropwise to a stirred solution of 70 g (384 mmol) of rac-α-amino-γ-butyrolactone hydrobromide in 1000 ml of dioxane / water (2: 1) while cooling with ice. After 10 minutes, the solution of 92.2 g (422 mmol) of di-tert-butyl pyrocarbonate in 30 ml of dioxane is added dropwise at T _i = 0 ° C., the mixture is stirred at 0 ° C. for 6 hours and at room temperature overnight.

It is evaporated in vacuo and the evaporation residue is stirred with ice-cold water. The precipitate is filtered off and dried.
Yield: 58 g (75% of theory);
Melting point: 115-118 ° C;
C₉H₁₅NO₅:
Calc .: C 53.72; H 7.51; N 6.96.
Found: C 53.81; H 7.52; N 6.93.

b) 1- [rac-N-Boc-2-amino-4-hydroxy-butanoyl] -4-methyl-piperidine

The solution of 45 g (223 mmol) of rac-N-Boc-2-amino butyrolactone and 145 ml (1230 mmol) of 4-methyl-piperidine in 450 ml of dioxane is refluxed for 2 hours. It is evaporated in vacuo and the residue is partitioned between ether and 0.5 M aqueous potassium hydrogen sulfate solution. The organic phase is dried over sodium sulfate, filtered and evaporated in vacuo. The evaporation residue is crystallized from petroleum ether.
Yield: 64.7 g (96% of theory);
Melting point: 87-90 ° C;
C₁₅H₂₈N₂O₄:
Calc .: C 59.98; H 9.40; N 9.33.
Found: C 60.30; H 9.50; N 9.22.

c) 1- [rac-N-Boc-2-amino-4-oxo-butanoyl] -4-methyl-piperidine

Dropwise to a stirred solution of 10 g (33.3 mmol) of 1- [rac-N-Boc-2-amino-4-hydroxy-butanoyl] -4-methyl-piperidine and 14 ml (99.9 mmol) of triethylamine in 67 ml of anhydrous DMSO at T _i = + 15 ° C the solution of 15.9 g (99.9 mmol) of sulfur tri oxide-pyridine complex in 80 ml of anhydrous DMSO. After 30 minutes, the reaction solution is poured onto ice. It is extracted with EtOAc, the combined organic phases are washed with saturated potassium hydrogen sulfate solution and with water, dried over sodium sulfate, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with petroleum ether / EtOAc (1: 1).
Yield: 7.5 g (75% of theory);
Melting point: 75-77 ° C (petroleum ether);
C₁₅H₂₆N₂O₄:
Calc .: C 60.38; H 8.78; N 9.39.
Found: C 60.36; H 8.83; N 9.36.

The oxidation can also be carried out with activated manganese dioxide (6-fold excess by weight) in anhydrous dioxane at 100-120 ° C. within 7 hours.
Yield: 23% of theory;
Calc .: Molpeak M⁺ = 298.
Found: Molpeak M⁺ = 298.

d) 1- [rac-N-Boc-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E) - pentene-oyl] -4-methyl-piperidine

To 5.61 g (13.07 mmol) (imidazo [1,2-a] pyrimidin-2-ylmethyl) triphenylphosphonium chloride in 30 ml of anhydrous THF are added at T _i = -65 ° C. with stirring and under dry nitrogen 3.83 g (30.15 mmol) potassium tert-butoxide. The yellow colored solution is stirred for 15 minutes at T _i = -65 ° C. and the solution of 3.0 g (10.05 mmol) of 1- [rac-N-Boc-2-amino-4-oxo-butanoyl] -4 is then quickly added dropwise -methyl-piperidine in 128 ml of anhydrous THF. The mixture is stirred for 30 minutes at -30 ° C. and overnight at room temperature. The red-brown colored reaction mixture is poured into ice-cold water, the aqueous phase is saturated with sodium chloride and extracted several times with EtOAc. The combined organic phases are dried, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with EtOAc / EtOH (10: 1).
Yield: 1.11 g (26.7% of theory);
Melting point: 182-184 ° C (ether);
C₂₂H₃₁N₅O₃:
Calc .: C 63.90; H 7.56; N 16.94.
Found: C 63.69; H 7.65; N 16.58.

e) 1- [rac-2-Amino-5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E) -pen ten-oyl] -4-methyl-piperidine × 2 CF₃COOH × 0.5 H₂O

To a solution of 1.11 g (2.66 mmol) of 1- [rac-N-Boc-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E ) - penten-oyl] -4-methyl-piperidine in 20 ml of methylene chloride, 6.5 ml of trifluoroacetic acid are added. After 2.5 hours at 20 ° C., the mixture is evaporated in vacuo.
Yield: 1.36 g (93% of theory), foam;
Melting point: 80 ° C;
C₁₇H₂₃N₅O × 2 CF₃COOH × 0.5 H₂O:
Calc .: C 45.82; H 4.76; N 12.72.
Found: C 45.91; H 4.87; N 12.48.

f) 1- [rac-2- (quinoline-8-sulfonamido) -5- (imidazo [1,2-a] pyrimi din-2-yl) -4- (E) -pentene-oyl] -4-methyl-piperidine

To a stirred solution of 0.31 g (0.725 mmol) of 1- [rac-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E) -pentene-oyl] -4 - Methyl-piperidine × 2 CF₃COOH × 0.5 H₂O and 0.4 ml (2.9 mmol) of triethylamine in 10 ml of methylene chloride are added at 20 ° C 0.165 g (0.725 mmol) of quinoline-8-sulfochloride. After 20 hours, shake out with water. The organic phase is dried, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with EtOAc / MeOH (5: 1).
Yield: 0.26 g (69% of theory), foam;
C₂₆H₂₈N₆O₃S:
Calc .: Molpeak M⁺ = 504.
Found: Molpeak M⁺ = 504.

g) 1- [rac-5- (2-amino-imidazol-4-yl) -2- (quinolin-8-sulfonamido) - 4- (E) -pentene-oyl] -4-methyl-piperidine × 2 HCl × 0.5 H₂O

Prepared analogously to Example 1h from 0.23 g (0.456 mmol) of 1- [rac- 2- (quinolin-8-sulfonamido) -5- (imidazo [1,2, a-pyrimidin-2-yl) -4- (E) - penten-oyl] -4-methyl-piperidine with 0.1 ml of 80% aqueous hydrazine hydrate by heating in 3.5 ml of EtOH under reflux for 8 hours.
Yield: 0.14 g (63% of theory);
Melting point: 160 ° C;
C₂₃H₂₈N₆O₃S × 2 HCl × 0.5 H₂O.
Calc .: C 50.18; H 5.68; N 15.26.
Found: C 50.49; H 6.08; N 14.81.
Calc .: Molpeak (M + H) ⁺ = 469.
Found: Molpeak (M + H) ⁺ = 469.

Example 9 1- {(2S) -5- (2-Amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4- tetrahydro-quinoline-8-sulfonamido] -4- (Z) -pentene-oyl} - (2R, 4R) - 4-methyl-piperidine-2-carboxylic acid ethyl ester × 1.3 HCl a) 1- [Boc-Asp (OBzl)] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid - ethyl ester

8.5 g (26 mmol) of Boc-Asp (OBzl) -OH, 5.0 g (29 mmol) of (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester [bp₆: 76-77 ° C .; [α] = -22.5 ° (c = 1.04; EtOH); GC-MS: 97.8% trans- (2R, 4R), 2.2% cis- (2R, 4S)], 6.4 g (31 mmol) N, N′-dicyclohexyl carbodiimide and a small spatula tip 1-hydroxy-1H-benzotriazole in 150 ml of toluene + 20 ml of THF and stirred for 18 hours at room temperature. It is filtered, the filtrate is evaporated in vacuo and the evaporation residue is purified by column chromatography on silica gel with petroleum ether / EtOAc (2: 1).
Yield: 12.4 g (100% of theory), oil; [α] = -28.6 ° (c = 1,015; EtOH);
C₂₅H₃₆N₂O₇:
Calc .: Molpeak M⁺ = 476.
Found: Molpeak M⁺ = 476.

b) 1- [H-Asp (OBzl)] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid - ethyl ester

Prepared analogously to Example 1b from 1- [Boc-Asp (OBzl)] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester and trifluoroacetic acid in methylene chloride, the evaporation in vacuo at max. + 30 ° C is carried out.
Yield: 100% of theory, oil.

c) 1 - [(3-Methyl-quinoline-8-sulfonyl) -Asp (OBzl)] - (2R, 4R) -4-me ethyl piperidine-2-carboxylic acid ethyl ester

To a stirred solution of 9.5 g (25 mmol) of 1- [H-Asp (OBzl)] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester and 4.2 ml (30 mmol) of triethylamine in 100 ml anhydrous methylene chloride, the solution of 6.1 g (25 mmol) of 3-methyl-quinoline-8-sulfochloride in 50 ml of anhydrous methylene chloride is added dropwise at 20 ° C. and the mixture is stirred for 24 hours. The reaction solution is washed with dilute potassium hydrogen sulfate solution and with water, dried over sodium sulfate, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with petroleum ether / EtOAc (2: 1).
Yield: 12.8 g (87% of theory), oil; [α] = + 27.7 ° (c = 1,075; EtOH);
C₃₀H₃₅N₃O₇S:
Calc .: Molpeak M⁺ = 581.
Found: Molpeak M⁺ = 581.

d) 1 - {[(3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinoline-8-sulfo nyl] -Asp} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester

10.9 g (18.7 mmol) of 1 - [(3-methyl-quinoline-8-sulfonyl) -Asp- (OBzl)] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester are dissolved in 180 ml of glacial acetic acid hydrogenated on 1.7 g of platinum dioxide for 40 minutes at 20 ° C. and 3.4 bar (50 psi). A TLC sample [silica gel, petroleum ether / EtOAc (1: 1)] shows the absence of the starting product (R _f = 0.59) and the presence of a new intermediate product (R _f = 0.84), which according to the mass spectrum 1 - [( (3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinoline-8-sulfonyl) -Asp (OBzl)] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid represents ethyl ester.
C₃₀H₃₉N₃0₇S:
Calc .: Molpeak M⁺ = 585;
Found: Molpeak M⁺ = 585.

The platinum dioxide is filtered off, 2.0 g of palladium-carbon (10%) are added and the mixture is hydrogenated at 20 ° C. and 3.4 bar for 60 minutes. A TLC sample [silica gel, EtOAc / MeOH / HOAc (10: 1: 0.01)] shows the absence of the intermediate (R _f = 0.88) and the presence of a new product (R _f = 0.49). It is filtered, the filtrate is evaporated in vacuo, the evaporation residue is dissolved several times in toluene, each time it is evaporated again and triturated with petroleum ether (30-60 ° C.).
Yield: 8.4 g (90% of theory), foam;
Melting point: 50 ° C; [α] = -12.5 ° (c = 0.255; EtOH);
C₂₃H₃₃N₃O₇S:
Calc .: C 55.74; H 6.71; N 8.48.
Found: C 56.04; H 7.11; N 8.19.
Calc .: Molpeak M⁺ = 495.
Found: Molpeak M⁺ = 495.

e) 1 - {(2S) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydroquinoline- 8-sulfonamido] -4-hydroxy-butanoyl} - (2R, 4R) -4-methyl-piperidine- 2-carboxylic acid ethyl ester

Prepared analogously to Example 1e from 1 - {[(3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinoline-8-sulfonyl] -Asp} - (2R, 4R) -4-methyl - Piperidine-2-carboxylic acid ethyl ester over the mixed anhydride by reduction with sodium borohydride and column chromatography purification on silica gel with petroleum ether / EtOAc (2: 1).
Yield: 77% of theory; Oil; [α] = + 133.8 ° (c = 0.305; EtOH);
C₂₃H₃₅N₃O₆S:
Calc .: Molpeak (M + H) ⁺ = 482.
Found: Molpeak (M + H) ⁺ = 482.

f) 1 - {(2S) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinoline- 8-sulfonamido] -4-oxo-butanoyl} - (2R, 4R) -4-methyl-piperidine- 2-carboxylic acid ethyl ester

Prepared analogously to Example 7c from 1 - {(2S) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -4-hydroxy-butanoyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester with sulfur trioxide-pyridine complex in DMSO in the presence of triethylamine.
Yield: 76% of theory, oil; [α] = + 35.3 ° (c = 0.405; EtOH);
C₂₃H₃₃N₃O₆S:
Calc .: Molpeak M⁺ = 479.
Found: Molpeak M⁺ = 479.

g) 1 - {(2S) -5- (imidazo [1,2-a] pyrimidin2-yl) -2 - [(3-R, S) -3-me thyl-1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -4- (Z) -pentene oyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester and 1 - {(2S) -5- (imidazo [1,2-a] pyrimidin-2-yl) -2 - [(3-R, S) -3-methyl- 1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -4- (E) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester

Prepared analogously to Example 4f from 1 - {(2S) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -4-oxo-butanoyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester with (imi dazo [1,2-a] pyrimidin-2-yl-methyl) -triphenylphosphonium chloride in THF / EtOH (1: 1) and DBU and by column chromatography on silica gel with EtOAc / EtOH (20: 1).
(Z) -isomer (TLC, silica gel, toluene / EtOAc / EtOH (4: 2: 0.5):
R _f = 0.29):
Yield: 24.1% of theory, foam; [α] = + 90.1 ° (c = 0.325; EtOH);
C₃₀H₃₈N₆O₅S:
Calc .: Molpeak (M + H) ⁺ = 595.
Found: Molpeak (M + H) ⁺ = 595.
(E) -isomer (R _f = 0.17):
Yield: 26.2% of theory, foam; [α] = + 37.0 ° (c = 0.300; EtOH);
Calc .: Molpeak M⁺ = 594.
Found: Molpeak M⁺ = 594.

h) 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl- 1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -4- (Z) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester × 1.3 HCl

0.70 g (1.18 mmol) of 1 - {(2S) -5- (imidazo [1,2-a] pyrimidin-2-yl) -2 - [(3-R, S) -3-methyl-1 are heated , 2,3,4-tetrahydro-quinoline-8-sulfonamido] -4- (Z) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester together with 0.070 ml (1.18 mmol) 80% aqueous hydrazine hydrate in 10 ml of anhydrous EtOH under reflux for 16 hours. It is evaporated in vacuo and the evaporation residue is purified by column chromatography on silica gel with methylene chloride / EtOH / conc. Ammonia (5: 1: 0.02). In addition to starting material (0.32 g, R _f = 0.96), the desired base (0.25 g, R _f = 0.50) is isolated, which is treated with ethereal hydrochloric acid.
Yield: 0.19 g (25% of theory);
Melting point: 100 ° C (foam); [α] = + 70.0 ° (c = 0.24; EtOH)
C₂₇H₃₈N₆O₅S × 1.3 HCl:
Calc .: C 53.50; H 6.53; N 13.87; Cl 7.61.
Found: C 56.39, H 6.78; N 13.98; Cl 7.74.
Calc .: Molpeak (M + H) ⁺ = 559.
Found: Molpeak (M + H) ⁺ = 559.

Example 10 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4- tetrahydro-quinoline-8-sulfonamido] -4- (E) -pentene-oyl} - (2R, 4R) - Ethyl 4-methyl-piperidine-2-carboxylate × 1.5 HCl

Prepared analogously to Example 9h from 0.75 g (1.26 mmol) 1 - {(2S) - 5- (imidazo [1,2-a] pyrimidin-2-yl) -2 - [(3-R, S) -3-methyl -1,2,3,4- tetrahydro-quinoline-8-sulfonamido] -4- (E) -pentene-oyl} - (2R, 4R) - 4-methyl-piperidine-2-carboxylic acid ethyl ester (Example 9g) by refluxing with 0.075 ml (1.26 mmol) of 80% aqueous hydrazine hydrate in 10 ml of anhydrous EtOH for 5 hours. In addition to 0.55 g of starting compound, 0.15 g of base is obtained, which is treated with ethereal hydrochloric acid.
Yield: 0.12 g (15% of theory);
Melting point: 150 ° C; [α] = + 63.4 ° (c = 0.235; EtOH);
C₂₇H₃₈N₆Q₅S × 1.5 HCl:
Calc .: C 52.86; H 6.49; N 13.70; Cl 8.67.
Found: C 52.51; H 6.73; N 13.48; Cl 8.16.
Calc .: Molpeak (M + H) ⁺ = 559.
Found: Molpeak (M + H) ⁺ = 559.

Example 11 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4- tetrahydro-quinoline-8-sulfonamido] -pentanoyl} - (2R, 4R) -4-methyl- ethyl piperidine-2-carboxylate × 1.3 HCl

0.127 g (0.21 mmol) of 1 - {(2S) -5- (2-aminoimidazole-4-l) -2 - [(3-R, S) -3-methyl-1,2,3, 4-tetrahydroquinoline-8-sulfone amido] -4- (Z) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carbonate, ethyl ester × 1.3 HCl (Example 9) in 15 ml EtOH on 20 g palladium-carbon (10%) for 2 hours at 20 ° C and 3.4 bar (50 psi). It is filtered and the filtrate is evaporated in vacuo.
Yield: 0.107 g (84% of theory);
Melting point: 120 ° C (dec.); [Α] = + 96.2 ° (c = 0.160; EtOH);
C₂₇H₄₀N₆O₅S × 1.3 HCl:
Calc .: Molpeak M⁺ = 560.
Found: Molpeak M⁺ = 560.

Example 12 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4- tetrahydro-quinoline-8-sulfonamido] -pentanoyl} - (2R, 4R) -4-methyl- piperidine-2-carboxylic acid × HCl

0.085 g (0.14 mmol) of 1 - {(2S) -5- (2-aminoimidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3, 4-tetrahydro-quinoline-8-sulfone amido] -pentanoyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester × 1.3 HCl (Example 11) together with 2.8 ml conc. Hydrochloric acid 7 days at 20 ° C. It is cooled to -70 ° C. and evaporated under freeze drying at 0.1 torr.
Yield: 0.061 g (76% of theory), foam; [α] = + 81.8 ° (c = 0.110; EtOH);
C₂₅H₃₆N₆O₅S × HCl:
Calc .: Molpeak (M + H) ⁺ = 533.
Found: Molpeak (M + H) ⁺ = 533.

Example 13 1 - [(2S) -3- (2-Amino-imidazol-4-yl) -2- (4-methyl-benzenesulfonami do) -propanoyl] -4-methyl-piperidine × HCl a) 1- [Boc-His (Bzl)] - 4-methyl-piperidine

Prepared analogously to Example 1a from Boc-His (Bzl) -OH and 4-methyl piperidine in THF and column chromatographic purification on silica gel with EtOAc / EtOH (10: 1).
Yield: 42% of theory, oil (R _f = 0.57).

b) 1- [H-His (Bzl)] - 4-methyl-piperidine 00200012000285919988800040 0002019548797 00004 99880ô CF₃COOH

Prepared analogously to Example 1b from 1- [Boc-His (Bzl)] - 4-methyl piperidine with trifluoroacetic acid in methylene chloride and evaporating the reaction solution in vacuo.
Crude yield: 100% of theory, oil;
TLC, silica gel, EtOAc / EtOH / conc. Ammonia (10: 1: 0.01): R _f = 0.12.

c) 1 - [(4-Methyl-benzenesulfonyl) -His (Bzl)] - 4-methyl-piperidine

Prepared analogously to Example 1c from crude 1- [H-His (Bzl)] - 4-methyl-piperidine × CF₃COOH with 4-methyl-benzenesulfonyl chloride in methylene chloride in the presence of 3 equivalents of triethylamine and by column chromatography purification on silica gel with EtOAc / EtOH ( 10: 1).
Yield: 72% of theory; Oil (R _f = 0.60).

d) 1 - [(4-methyl-benzenesulfonyl) -His] -4-methyl-piperidine × HCl × 0.8 H₂O

0.85 g (1.77 mmol) of 1 - [(4-methyl-benzenesulfonyl) - His (Bzl)] - 4-methyl-piperidine is hydrogenated in 50 ml of MeOH in the presence of 1.8 ml of 1N hydrochloric acid on 0.5 g of palladium-carbon (10 %) 18 hours at 50 ° C and 5 bar. It is filtered, evaporated in vacuo, and the evaporation residue is triturated with ether.
Yield: 0.67 g (86% of theory);
Melting point: 227-230 ° C;
C₁₉H₂₆N₄O₃5 × HCl × 0.8 H₂O:
Calc .: C 51.70; H 6.36; N 12.69; Cl 8.03.
Found: C 51.99; H 6.30; N 12.38; Cl 8.40.
Calc .: Molpeak M⁺ = 390.
Found: Molpeak M⁺ = 390.

e) 1 - {(2S) -3- [2- (4-methoxycarbonylphenyl) azo-imidazol-4-yl] - 2- (4-methyl-benzenesulfonamido) propanoyl} -4-methyl-piperidine

To 0:21 g (1:41 mmol) of 4-amino-benzoic acid methylester in 2.5 ml of 2N hydrochloric acid Chem added dropwise at T _i = 0 ° C, the solution 0.10 g Na triumnitrit in 1.6 ml H₂O (analogously to J. Org.. 1973 38, 1971-1974; J. Med. Chem. 1987, 30, 2222-2227). After stirring for 30 minutes, the cold (0 ° C.) diazonium salt solution is added dropwise to a cold (0 ° C.) stirred suspension of 0.60 g (1.40 mmol) 1 - [(4-methyl-benzenesulfonyl) -His] -4- methyl-piperidine × HCl × 0.8 H₂O in 47 ml of a 0.25M aqueous disodium tetraborate solution, which turns red. The pH is kept at 9.0 to 9.5; to this end, a little 2N sodium hydroxide solution is added at the end of the dropwise addition. The mixture is stirred at 0 ° C. for 2 hours, filtered, the precipitate is washed with water and dissolved in EtOAc. The EtOAc solution is dried over sodium sulfate, filtered and evaporated in vacuo. In the TLC [silica gel, methylene chloride / MeOH (10: 1)] of the reddish-brown evaporation residue (0.8 g) you can see a trace of the starting product (R _f = 0.33), a red substance (R _f = 0.58) and two yellow substances (R _f = 0.51 or 0.43). The yellow substances are the 4- or the 2-azo-imidazole derivative, the red colored substance is probably the 2,4-bis-azo-imidazole derivative. - The crude product is purified by column chromatography on silica gel with methylene chloride / MeOH (20: 1).
Yield: 0.15 g (19.2% of theory), red-brown foam;
R _f = 0.43;
200 MHz 1 H NMR (d6-DMSO / d-MeOH): doublet at 7.13 ppm for H-5 (4);
C₂₇H₃₂N₆O₅5:
Calc .: Molpeak (M + H) ⁺ = 553.
Found: Molpeak (M + H) ⁺ = 553.

f) 1 - [(25) -3- (2-Amino-imidazol-4-yl) -2- (4-methyl-benzenesulfone amido) propanoyl] -4-methyl-piperidine × HCl

0.15 g (0.271 mmol) of 1 - {(2S) -3- [2- (4-methoxycar bonylphenyl) azo) imidazol-4-yl] -2- (4-methyl-benzenesulfone amido) -propanoyl} -4-methyl-piperidine in 20 ml MeOH at 30 mg Platinum dioxide for 3 hours at 20 ° C and 5 bar (analogous to J. Org. Chem. 1973, 38, 1971-1974; J. Med. Chem. 1987, 30, 2222-2227). DC: little starting product, little target product and a lot of corresponding hydrazo compound.

A further 30 mg of platinum dioxide are added and the mixture is hydrogenated for a further 17 hours. TLC: a lot of 4-amino-benzoic acid methyl ester and a lot of target product. It is evaporated in a vacuum. The evaporation residue (0.13 g) is by column chromatography on silica gel with methylene chloride / MeOH / conc. Ammonia (10: 1: 0.01) cleaned. The base obtained (0.05 g) is mixed with ethereal hydrochloric acid.
Yield: 0.03 g (25% of theory), foam;
Melting point: 60 ° C;
TLC, silica gel, methylene chloride / MeOH / conc. Ammonia (5: 1: 0.02):
R _f = 0.29); [α] = + 59.2 ° (c = 0.125; EtOH);
C₁₉H₂₇N₅O₃S × HCl:
Calc .: Molpeak M⁺ = 405.
Found: Molpeak M⁺ = 405.

Example 14 1 - [(2S) -5- (2-Amino-imidazol-4-yl) -2- (4-methyl-benzenesulfonami do) -pentanoyl] -4-methyl-piperidine × HCl a) 1- [Z-Asp (OtBu)] - 4-methyl-piperidine

Prepared analogously to Example 1a from Z-Asp (OtBu) -OH and 4-methylpiperidine in THF and by column chromatography purification on silica gel with petroleum ether / EtOAc (2: 1).
Yield: 96% of theory, oil (R _f = 0.51).

b) 1- [Z-Asp] -4-methyl-piperidine

A stirred solution of 30 g (74.2 mmol) of 1- [Z-Asp (OtBu)] - 4-methyl piperidine in 300 ml of methylene chloride is mixed with 185 ml of trifluoroacetic acid while cooling with ice. The mixture is stirred at room temperature for 20 hours, evaporated in vacuo at a bath temperature of 30 ° C., the evaporation residue is dissolved in EtOAc and shaken out several times with water. The organic phase is dried, filtered and evaporated in vacuo.
Crude yield: 24.1 g (93% of theory), brown oil;
DC, silica gel; EtOAc / MeOH / AcOH (10: 1: 0.01): R _f = 0.44.

c) 1 - [(2S) -2-Z-Amino-4-hydroxy-butanoyl] -4-methyl-piperidine

Prepared analogously to Example 1e from 1- [Z-Asp] -4-methyl-piperidine via the mixed anhydride by reduction with sodium borohydride and purification by column chromatography on silica gel with EtOAc.
Yield: 54% of theory; Oil (R _f = 0.44).

d) 1 - [(2S) -2-Z-Amino-4-oxo-butanoyl] -4-methyl-piperidine

16.2 g (162 mmol) of chromium trioxide are added at T _i = 10 ° C. to a stirred solution of 29.4 ml of anhydrous pyridine in 200 ml of anhydrous methylene chloride, the mixture is stirred at room temperature for 20 minutes and the solution is then set at 8.9 g (27 mmol) 1 - [(2S) -2- Z-Amino-4-hydroxy-butanoyl] -4-methyl-piperidine in 40 ml of methylene chloride. After stirring for 30 minutes at 20 ° C., the solid fraction is extracted with methylene chloride and the combined methylene chloride phases are shaken out several times with saturated aqueous potassium hydrogen sulfate solution. The organic extract is dried, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel using EtOAc.
Yield: 61% of theory, colorless oil (R _f = 0.75).

e) 1 - [(2S) -2-Z-amino-5- (1-triphenylmethyl-imidazol-4-yl) -4- (Z) - penten-oyl] -4-methyl-piperidine and 1 - [(2S) -2-Z-Amino-5- (1-triphenylmethyl-imidazol-4-yl) -4- (E) - pentene-oyl] -4-methyl-piperidine

For the suspension of 12.1 g (19.53 mmol) (1-triphenylmethylimidazol-4-ylmethyl-triphenylphosphonium chloride) stirred at -70 ° C. and under dry nitrogen [see Examples 1.1 and 1.2 of EP-A-0,565,396; melting point 240-245 ° C; literature melting point: 210 ° C] in 120 ml of anhydrous THF, 12.7 ml (19.53 mmol) of a 1.6 Mn-butyllithium solution in n-hexane are added dropwise, and the mixture is stirred at -70 ° C for 10 minutes and then gives then the red-brown colored ylene solution rapidly to a solution of 5.4 g (16.24 mmol) of 1 - [(2S) - 2-Z-amino-4-oxo-butanoyl] -4 which was stirred at -70 ° C. and under dry nitrogen -methyl-piperidine in 50 ml of water-free THF. The mixture is stirred for 1 hour at -70 ° C., allowed to come to room temperature and stirred overnight. Saturated sodium chloride solution is added. The organic phase is separated off, dried, filtered and The evaporation residue is purified by column chromatography on silica gel using petroleum ether / EtOAc (1: 1) - TLC, silica gel, toluene / EtOAc / EtOH (40: 20: 10).
(Z) isomer (R _f = 0.76):
Yield: 1.3 g (12.5% of theory), yellow oil;
C₄₁H₄₂N₄O₃:
Calc .: Molpeak (M + H) ⁺ = 639.
Found: Molpeak (M + H) ⁺ = 639.
(E) -isomer (R _f = 0.62):
Yield: 5.6 g (53.9% of theory), yellow oil;
Calc .: Molpeak (M + H) ⁺ = 639.
Found: Molpeak (M + H) ⁺ = 639.

f) 1 - [(2S) -2-amino-5- (1-triphenylmethylimidazol-4-yl) pentane oyl] -4-methyl-piperidine

5.0 g (7.8 mmol) of 1 - [(2S) -2-Z-amino-5- (1-triphenylmethylimidazol-4-yl) -4- (E) -pentene-oyl] -4-methyl are hydrogenated -piperidine in 100 ml EtOH on 0.8 g palladium-carbon (10%) for 9 hours at 20 ° C and 3.4 bar (50 psi). It is filtered, evaporated in vacuo and the evaporation residue is purified by column chromatography on silica gel with methylene chloride / EtOH / conc. Ammonia (10: 1: 0.01).
Yield: 2.7 g (68% of theory), yellow oil;
TLC, silica gel, methylene chloride / EtOH / conc. Ammonia (5: 1: 0.01):
R _f = 0.49;
C₃₃H₃₈N₄O:
Calc .: Molpeak M⁺ = 506.
Found: Molpeak M⁺ = 506.

g) 1 - [(2S) -2- (4-methyl-benzenesulfonamido) -5- (1-triphenylmethyl- imidazol-4-yl) pentanoyl] -4-methyl-piperidine

To a solution of 0.95 g (1.88 mmol) 1 - [(2S) -2-amino-5- (1-triphenyl-methyl-imidazol-4-yl) -penta noyl] -4-methyl- stirred at 20 ° C. piperidine and 0.40 ml (2.82 mmol) of triethylamine in 30 ml of anhydrous methylene chloride are added dropwise to the solution of 0.39 g (2.07 mmol) of 4-methyl-benzenesulfonyl chloride in 10 ml of water-free methylene chloride. After 2 hours, the mixture is extracted with water. The organic phase is separated off, dried, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with EtOAc / EtOH (20: 1).
Yield: 2.7 g (68% of theory), colorless oil (R _f = 0.61);
C₄₀H₄₄N₄O₃S.

h) 1 - [(2S) -2- (4-methyl-benzenesulfonamido) -5- (1H-imidazole-4 (5) - yl) -pentanoyl] -4-methyl-piperidine × HCl

1.25 g (1.89 mmol) of 1 - [(2S) -2- (4-methyl-benzenesulfonamido) -5- (1-triphenylmethyl-imidazol-4-yl) -pentanoyl] -4-methyl-piperidine are heated in 10 ml 80% aqueous acetic acid 20 minutes on the steam bath, then cools in ice and provides by adding conc. Alkaline ammonia. It is extracted several times with EtOAc. The organic phase is dried, filtered and evaporated in vacuo. The evaporation residue is column chromatographically on silica gel with methylene chloride / EtOH / conc. Cleaned on moniak (5: 1: 0.01). The base obtained is treated with ethereal hydrochloric acid.
Yield: 0.59 g (68% of theory);
R _f = 0.50;
Melting point: 110-120 ° C;
C₂₁H₃₀N₄O₃S × HCl:
Calc .: C 55.43; H 6.87; N 12.31; Cl 7.79.
Found: C 55.09; H 7.13; N 11.93; Cl 7.60.
Calc .: Molpeak (M + H) ⁺ = 419.
Found: Molpeak (M + H) ⁺ = 419.

i) 1 - {(2S) -5- [2- (4-methoxycarbonylphenyl) azo-imidazol-4-yl] - 2- (4-methyl-benzenesulfonamido) pentanoyl} -4-methyl-piperidine

Prepared analogously to Example 13e from 1 - [(2S) -2- (4-methylbenzene sulfonamido) -5- (imidazol-4-yl) pentanoyl] -4-methylpiperidine × HCl. The crude product is purified by column chromatography on silica gel with methylene chloride / MeOH (10: 1). In addition to the title compound (R _f = 0.82), 4-azo compound (R _f = 0.51; 4.7% of theory) and starting material (R _f = 0.26; 70% of theory) are isolated.
Yield: 11% of theory, red-yellow foam;
C₂₉H₃₆N₆O₅S:
Calc .: Molpeak (M + H) ⁺ = 581.
Found: Molpeak (M + H) ⁺ = 581.

j) 1 - [(2S) -5- (2-Amino-imidazol-4-yl) -2- (4-methyl-benzenesulfone amido) -pentanoyl] -4-methyl-piperidine × HCl

Prepared analogously to Example 13f from 1 - {(2S) -5- [2- (4-methoxycarbonylphenyl) azo-imidazol-4-yl] -2- (4-methyl-benzenesulfone amido) -pentanoyl} -4- methyl piperidine.
Yield: 21% of theory, foam;
C₂₁H₃₁N₅O₃S × HCl:
Calc .: Molpeak (M + H) ⁺ = 434.
Found: Molpeak (M + H) ⁺ = 434.

Example 15 1 - [(2S) -5- (2-Amino-imidazol-4-yl) -2- (3-methyl-quinolin-8-sul fonamido) -pentanoyl] -4-methyl-piperidine × HCl a) 1 - [(2S) -2- (3-methyl-quinoline-8-sulfonamido) -5- (1-triphenyl methyl-imidazol-4-yl) pentanoyl] -4-methyl-piperidine

Prepared analogously to Example 14g from 1 - [(2S) -2-amino-5- (1-tri-phenylmethyl-imidazol-4-yl) pentanoyl] -4-methyl-piperidine (Example 14f) with 3-methyl-quinoline -8-sulfochloride.
Yield: 61% of theory, viscous oil;
TLC, silica gel, toluene / EtOAc / EtOH (6: 3: 1): R _f = 0.54;
C₄₃H₄₅N₅O₃S:
Calc .: Molpeak (M + H) ⁺ = 712.
Found: Molpeak (M + H) ⁺ = 712.

b) 1 - [(2S) -2- (3-methyl-quinoline-8-sulfonamido) -5- (imidazole- 4-yl) -pentanoyl] -4-methyl-piperidine × HCl

Prepared analogously to Example 14h from 1 - [(2S) -2- (3-methyl-quino lin-8-sulfonamido) -5- (1-triphenylmethyl-imidazol-4-yl) -pentanyl] -4-methyl-piperidine with 80% aqueous acetic acid.
Yield: 84% of theory, foam;
TLC, silica gel, toluene / EtOAc / EtOH / conc. Ammonia (30: 20: 10: 1): R _f = 0.34; [α] = + 116.7 ° (c = 0.21; MeOH);
C₂₄H₃₁N₅O₃5 × HCl:
Calc .: Molpeak M⁺ = 469.
Found: Molpeak M⁺ = 469.

c) 1 - {(2S) -5- [2- (4-methoxycarbonylphenyl) azo-imidazol-4-yl] - 2- (3-methyl-quinoline-8-sulfonamido) pentanoyl} -4-methyl-piperi din

Prepared analogously to Example 13e from 1 - [(2S) -2- (3-methyl-quino lin-8-sulfonamido) -5- (imidazol-4-yl) pentanoyl] -4-methyl-pipe ridin × HCl. The crude product is purified by column chromatography on silica gel with methylene chloride / MeOH (10: 1). In addition to the title compound (R _f = 0.52), 2,4-bis-azo compound (R _f = 0.58) and 4-azo compound (R _f = 0.46; 10% of theory) are isolated.
Yield: 15% of theory, foam;
200 MHz 1 H NMR (CDCl₃): signal at 7.15 ppm for H-5 (4);
C₃₂H₃₇N₇O₅5:
Calc .: Molpeak (M + H) ⁺ = 632.
Found: Molpeak (M + H) ⁺ = 632.

d) 1 - [(2S) -5- (2-amino-imidazol-4-yl) -2- (3-methyl-quinoline- 8-sulfonamido) pentanoyl] -4-methyl-piperidine × HCl

Prepared analogously to Example 13f from 1 - {(2S) -5- [2- (4-methoxycarbonyl-phenyl) azo-imidazol-4-yl] -2- (3-methyl-quinoline-8-sulfone amido) -pentanoyl } -4-methyl-piperidine.
Yield: 16% of theory, foam;
C₂₄H₃₂N₆O₃5 × HCl:
Calc .: Molpeak M⁺ = 484.
Found: Molpeak M⁺ = 484.

Example 16 1 {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4- tetrahydro-quinoline-8-sulfonamido] -pentanoyl} -4-methyl-pipe ridin × HCl a) 1 {(2S) -5- (imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetra hydro-quinoline-8-sulfonamido] -pentanoyl} -4-methyl-piperidine × HCl

0.34 g (0.67 mmol) of 1 - [(2S) -2- (3-methyl-quinoline-8-sulfonamido) -5- (imidazol-4-yl) -pentanoyl] -4-methyl-piperidine × HCl (HCl ( Example 15b; R _f = 0.34) in 10 ml MeOH over 0.35 g rhodium carbon (5%) for 2 hours at 20 ° C and 3.4 bar (50 psi). After adding 0.15 g of fresh catalyst, hydrogenation is continued for 4 hours. It is filtered and evaporated in vacuo. The evaporation residue is column chromatographed on silica gel with toluene / EtOAc / EtOH / conc. Ammonia (30: 20: 10: 1) cleaned. The base obtained is treated with ethereal hydrochloric acid.
Yield: 0.22 g (65% of theory);
R _f = 0.47;
Melting point: 86-89 ° C (dec.); [Α] = + 110.9 ° (c = 0.21; MeOH);
C₂₄H₃₅N₅O₃5 × HCl:
Calc .: Molpeak M⁺ = 473.
Found: Molpeak M⁺ = 473.

b) 1 - {(2S) -5- [2- (4-methoxycarbonylphenyl) azo-imidazol-4-yl] - 2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinoline-8-sulfonamido] - pentanoyl} -4-methyl-piperidine

Prepared analogously to Example 13e from 1 {(2S) -5- (imidazol-4-yl) - 2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinoline-8- sulfonamido] - pentanoyl} -4-methyl-piperidine × HCl.
Yield: 10% of theory, foam;
C₃₂H₄₁N₇O₅S:
Calc .: Molpeak (M + H) ⁺ = 636.
Found: Molpeak (M + H) ⁺ = 636.

c) 1 {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl- 1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -pentanoyl} -4-methyl- piperidine × HCl

Prepared analogously to Example 13f from 1 - {(2S) -5- [2- (4-methoxycarbonylphenyl) azo-imidazol-4-yl] -2 - [(3-R, 5) -3-methyl-1 , 2,3,4-tetrahydro-quinoline-8-sulfonamido] -pentanoyl} -4-methyl-piperidine.
Yield: 13% of theory, foam;
C₂₄H₃₆N₆O₃5 × HCl:
Calc .: Molpeak M⁺ = 488.
Found: Molpeak M⁺ = 488.

Example 17 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4- tetrahydro-quinoline-8-sulfonamido] -pentanoyl} -4-methyl-piperi din × HCl

Prepared analogously to Example 16a from 1 - [(2S) -5- (2-amino-imidazol-4-yl) -2- (3-methyl-quinoline-8-sulfonamido) pentanoyl] -4-methyl piperidine × HCl (Example 15d) by hydrogenation on rhodium carbon (5%) in MeOH.
Yield: 61% of theory;
C₂₄H₃₆N₆O₃5 × HCl.
Calc .: Molpeak M⁺ = 488.
Found: Molpeak M⁺ = 488.

Example 18 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino- imidazol-4-yl) pentanoyl] -4-methyl-piperidine × HCl a) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (1-tri phenylmethyl-imidazol-4-yl) -4-penten-oyl] -4-methyl-piperidine

Prepared analogously to Example 14e from 1 - [(2S) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -4-oxo-butanoyl] -4-methyl-piperidine (Example 1f) with (1-triphenylmethyl -imidazol-4-yl) methyl triphenylphosphonium chloride and n-butyllithium in anhydrous THF at -70 ° C and by column chromatography on silica gel with EtOAc.
Yield: 34% of theory, foam;
C₃₉H₃₉Cl₂N₅O₃S:
Calc .: Molpeak (M + H) ⁺ = 728/730/732 (Cl₂).
Found: Molpeak (M + H) ⁺ = 728/730/732 (Cl₂).

b) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (imida zol-4-yl) -4-pentenoyl] -4-methylpiperidine

Prepared analogously to Example 14h from 1 - [(2S) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -5- (1-triphenylmethyl-imidazol-4-yl) - 4-penten-oyl] - 4-methyl-piperidine with 80% aqueous acetic acid.
Yield: 69% of theory, foam;
Melting point: 70 ° C;
C₂₀H₂₅Cl₂N₅O₃S:
Calc .: Molpeak M⁺ = 485/487/489 (Cl₂).
Found: Molpeak M⁺ = 485/487/489 (Cl₂).

c) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (imida zol-4-yl) pentanoyl] -4-methyl-piperidine × HCl

Prepared analogously to Example 14f from 1 - [(2S) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -5- (imidazol-4-yl) -4-pentenoyl] -4-methyl -piperidine by hydrogenation on palladium-carbon (10%), by column chromatography purification on silica gel with methylene chloride / MeOH (5: 1) and treatment of the base with ethereal hydrochloric acid.
Yield: 53% of theory, foam; [α] = + 78.4 ° (c = 0.125; EtOH);
C₂₀H₂₇Cl₂N₅O₃S × HCl:
Calc .: Molpeak M⁺ = 487/489/491 (Cl₂).
Found: Molpeak M⁺ = 487/489/491 (Cl₂).

d) 1 - {(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- [2- (4- methoxycarbonyl-phenyl) azo-imidazol-4-yl] -pentanoyl} -4-methyl- piperidine

Prepared analogously to Example 13e from 1 - [(2S) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -5- (imidazol-4-yl) pentanoyl] -4-methylpiperidine × HCl.
Yield: 11% of theory, foam;
C₂₈H₃₃Cl₂N₇O₅S:
Calculated: Molpeak M⁺ = 649/651/653 (Cl₂).
Found: Molpeak M⁺ = 649/651/653 (Cl₂).

e) 1 - {(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- [2-ami no-imidazol-4-yl] -pentanoyl} -4-methyl-piperidine × HCl

Prepared analogously to Example 13f from 1- {(2S) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -5- [2- (4-methoxycarbonylphenyl) azo imidazol-4-yl] pentanoyl } -4-methyl-piperidine.
Yield: 21% of theory, foam;
C₂₀H₂₈Cl₂N₆O₃S × HCl:
Calc .: Molpeak M⁺ = 502/504/506 (Cl₂).
Found: Molpeak M⁺ = 502/504/506 (Cl₂).

Example 19 1- [rac-2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino- imidazol-4-yl) pentanoyl] -4-methyl-piperidine × HCl a) 3- (1H-Imidazol-4-yl) -2-propen-1-ol × HCl

Prepared analogously to Example 1e from 3- (1H-imidazol-4-yl) acrylic acid via the mixed anhydride by reduction with sodium borohydride, acidification of the reaction mixture with half-concentrated hydrochloric acid to pH 5 and shaking out the organic phase with 2N-HCl. The combined hydrochloric acid phases are evaporated in vacuo after extraction with ether. The evaporation residue was purified by column chromatography on silica gel with methylene chloride / MeOH (3: 1).
Yield: 19% of theory;
R _f = 0.32;
Melting point: 130-135 ° C;
C₆H₈N₂O × HCl:
Calculated: C 44.87; H 5.65; N 17.45.
Found: C 45.17; H 5.56; N 17.57.
Calc .: Molpeak M⁺ = 124.
Found: Molpeak M⁺ = 124.

b) 3- (1H-Imidazol-4-yl) -2-propenyl chloride x HCl

To 3.0 g (18.7 mmol) of 3- (1H-imidazol-4-yl) -2-propen-1-ol × HCl in 30 ml of anhydrous chloroform is added dropwise with stirring 20 ° C 20 ml of thionyl chloride, stirred for 3 hours, evaporated in vacuo , adds toluene to the evaporation residue and evaporates again in the Vacuum on. The crude product obtained continues immediately implemented.

c) 2-Acetylamino-2-ethoxycarbonyl-5- (1H-imidazol-4-yl) -4-pen ethyl tenate

A solution of 1.1 g (48 mmol) of sodium in 60 ml of anhydrous EtOH is added, 10.4 g (48 mmol) of acetamido-malonic acid diethyl ester are added and the mixture is heated under reflux for 2 hours. It is cooled in ice and this solution is added to 18.7 mmol of crude 3- (1H-imidazol-4-yl) -2-propenyl chloride × HCl. The reaction mixture is heated under reflux for 3 hours, cooled, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with methylene chloride / MeOH (10: 1).
Yield: 3.92 g (65% of theory), viscous oil;
C₁₅H₂₁N₃O₅:
Calc .: Molpeak M⁺ = 323.
Found: Molpeak M⁺ = 323.

d) (rac) -2-amino-5- (1H-imidazol-4-yl) -4-pentenoic acid × 2 HCl

3.8 g (11.8 mmol) of 2-acetylamino-2-ethoxycarbonyl-5- (1H-imidazol-4-yl) -4-pentenoic acid ethyl ester together with 70 ml of semi-concentrated hydrochloric acid are refluxed for 4 hours and evaporated in vacuo , dissolves the evaporation residue several times in EtOH and evaporates again. Finally, it is dried at 120 ° C / 0.1 Torr.
Crude yield: 3.0 g (100% of theory), foam;
TLC, silica gel, methylene chloride / MeOH / conc. Ammonia (3: 1: 0.2):
R _f = 0.13;
C₈H₁₁N₃O₂ × 2 HCl.

e) (rac) -2-Boc-amino-5- (1-Boc-imidazol-4 (5) -yl) -4-pentenoic acid

To the stirred solution of 3.7 g (14.6 mmol) of crude (rac) -2-amino-5- (1H-imidazol-4-yl) -4-pentenoic acid × 2 HCl in dioxane / water (2: 1) is added 4.4 ml (43.7 mmol) of triethylamine, cools to T _i = + 5 ° C., adds 8.26 g (37.9 mmol) of di-tert.butyl pyrocarbonate in portions and stirred overnight at room temperature. It is evaporated in vacuo, the evaporation residue is dissolved in 50 ml of water, the pH is adjusted to 2.5 with saturated aqueous potassium hydrogen sulfate solution and the mixture is extracted with EtOAc. The organic phase is dried, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with EtOAc / MeOH (3: 1 to 1: 1).
Yield: 3.0 g (54% of theory), foam;
TLC, silica gel, EtOAc / MeOH (3: 1): R _f = 0.39;
C₁₈H₂₇N₃O₆:
Calc .: Molpeak (MH) ⁻ = 380.
Found: Molpeak (MH) ⁻ = 380.

f) 1 - [(rac) -2-Boc-amino-5- (1-Boc-imidazol-4 (5) -yl) -4-pentene oyl] -4-methyl-piperidine

Prepared analogously to Example 1a from (rac) -2-Boc-amino-5- (1-Boc-imidazol-4 (5) -yl) -4-pentenoic acid over the mixed anhydride with 4-methyl-piperidine in THF and by column chromatography Purification on silica gel with methylene chloride / MeOH (15: 1).
Yield: 12.5% of theory, oil;
R _f = 0.51;
C₂₄H₃₈N₄O₅:
Calc .: Molpeak M⁺ = 462.
Found: Molpeak M⁺ = 462.

g) 1 - [(rac) -2-Amino-5- (1H-imidazol-4-yl) -4-pentenoyl] -4-me thyl-piperidine × 2 CF₃COOH

Prepared analogously to Example 1b from 1 - [(rac) -2-Boc-amino-5- (1-Boc-imidazol-4 (5) -yl) -4-penten-oyl] -4-methyl-piperidine with trifluoroacetic acid in Methylene chloride and evaporation of the reaction mixture in vacuo.
Crude yield: 100% of theory, oil;
TLC, silica gel, methylene chloride / MeOH / conc. Ammonia (100: 10: 1):
R _f = 0.24;
C₁₄H₂₂N₄O × 2 CF₃COOH:
Calc .: Molpeak (M + H) ⁺ = 263.
Found: Molpeak (M + H) ⁺ = 263.

h) 1 - {(rac) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- [1H- imidazole-4 (5) -yl] -4-pentene-oyl} -4-methyl-piperidine

Prepared analogously to Example 1c from 1 - [(rac) -2-amino-5- (1H-imi dazol-4-yl) -4-penten-oyl] -4-methyl-piperidine × 2 CF₃COOH and 4-amino-3 , 5-dichlorobenzenesulfonyl chloride with triethylamine in methylene chloride. The crude product obtained is treated at 20 ° C. in MeOH with 2N-NaOH, neutralized with 2N-HCl, evaporated in vacuo and the evaporation residue is distributed between EtOAc and water. The organic extract is dried, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel, starting with toluene / EtOAc (1: 1), then with methylene chloride / MeOH (10: 1).
Yield: 9% of theory, oil;
C₂₀H₂₅Cl₂N₅O₃S:
Calc .: Molpeak (M + H) ⁺ = 486/488/490 (Cl₂).
Found: Molpeak (M + H) ⁺ = 486/488/490 (Cl₂).

i) 1 - {(rac) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- [1H- imidazole-4 (5) -yl] -pentanoyl} -4-methyl-piperidine × HCl

Prepared analogously to Example 14f from 1 - {(rac) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -5- [1H-imidazole-4 (5) -yl] -4-penten-oyl} - 4-methyl-piperidine by hydrogenation on palladium-carbon (10%) in EtOH.
Yield: 64% of theory, foam;
C₂₀H₂₇Cl₂N₅O₃S:
Calc .: Molpeak M⁺ = 487/489/491 (Cl₂).
Found: Molpeak M⁺ = 487/489/491 (Cl₂).

j) 1- {rac-2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- [2- (4- methoxycarbonyl-phenyl) azo-imidazol-4-yl] -pentanoyl} -4-methyl- piperidine

Prepared analogously to Example 13e from 1- [rac-2- (4-amino-3,5-di chlorobenzenesulfonamido) -5- (imidazol-4-yl) pentanoyl] -4-methylpiperidine × HCl.
Yield: 13% of theory, foam;
C₂₈H₃₃Cl₂N₇O₅S:
Calculated: Molpeak M⁺ = 649/651/653 (Cl₂).
Found: Molpeak M⁺ = 649/651/653 (Cl₂).

k) 1- {rac-2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- [2-ami no-imidazol-4-yl] -pentanoyl} -4-methyl-piperidine × HCl

Prepared analogously to Example 13f from 1- {rac-2- (4-amino-3,5-di chlorobenzenesulfonamido) -5- [2- (4-methoxycarbonyl-phenyl) azo-imidazol-4-yl] pentanoyl} -4-methyl-piperidine.
Yield: 19% of theory, foam;
C₂₀H₂₈Cl₂N₆O₃5 × HCl:
Calc .: Molpeak M⁺ = 502/504/506 (Cl₂).
Found: Molpeak M⁺ = 502/504/506 (Cl₂).

Example 20 1 - [(2S) -2- (naphthalene-1-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] -4-methyl-piperidine × HCl a) 4-Methyl-1 - [(2S) -4-methylthio-2-phthalimido-butanoyl] pipe ridin

Prepared analogously to Example 9a from N-phthalyl-L-methionine (see Helv. Chim. Acta 1958, 41, 1852-1867) and 4-methyl-pi peridine in anhydrous toluene with N, N'-dicyclohexyl-carbodiimide and a small one Spatula tip 1-hydroxy-1H-benzotriazole and by column chromatography on silica gel with petroleum ether / EtOAc (1: 1).
Yield: 100% of theory, oil (R _f = 0.61);
C₁₉H₂₄N₂O₃S

b) 4-Methyl-1 - [(2S) -4-methylthio-4-oxo-2-phthalimido-butyl] -pi peridin

To 23 g (63.8 mmol) of 4-methyl-1 - [(2S) -4-methylthio-2-phthal imido-butanoyl] -piperidine in 400 ml of carbon tetrachloride was slowly added dropwise with stirring at T _i = 0 ° C 5.2 ml ( 63.8 mmol) sulfuryl chloride and stirred for 1 hour at 0 ° C and 1 hour at 20 ° C (analog Synthesis 1993, 1225-1226). Then 9.0 ml (63.8 mmol) of triethylamine are added dropwise with ice cooling, the mixture is stirred at T _i = -15 ° C. for 1 hour and filtered. The filtrate is evaporated in vacuo at a bath temperature of 30 ° C. The evaporation residue was stirred together with 400 ml of water at 20 ° C. for 6 days. It is extracted with ether, the ether phase is washed with saturated aqueous sodium bicarbonate solution, dried and filtered, and evaporated in vacuo. The evaporation residue (20 g) is purified by column chromatography on silica gel with petroleum ether / EtOAc (1: 1). 9.1 g of an oil are obtained, which partly crystallizes on addition of ether (K); the mother liquor is evaporated in a vacuum (oily, R). The 2,4-dinitro-phenylhydrazine sample is positive for -CH = O for both K and R. The rotation values indicate that K is apparently partially racemized.
Crystallizate K:
Yield: 2.1 g (10% of theory);
Melting point 140-143 ° C;
TLC, silica gel, petroleum ether / EtOAc (1: 2): R _f = 0.38; [α] = -8.5 ° (c = 1.02; MeOH)
C₁₈H₂₀N₂O₄:
Calc .: C 65.84; H 6.14; N 8.53.
Found: C 65.83; H 6.19; N 8.56.
Calc .: Molpeak M⁺ = 328.
Found: Molpeak M⁺ = 328.
Oily fraction R:
Yield: 7.0 g (33% of theory);
R _f = 0.38; [α] = -59.0 ° (c = 1.49; MeOH);
Calc .: Molpeak M⁺ = 328.
Found: Molpeak M⁺ = 328.

The reaction can also be carried out with N-chlorosuccinimide in the presence of a catalytic amount of α, α′-azo-isobutyronitrile in carbon tetrachloride and by subsequent hydrolysis.
Yield: 30% of theory, oil (R _f = 0.38).

c) 1 - [(2S) -2-phthalimido-5- (1-triphenylmethylimidazol-4-yl) - 4- (Z) -pentene-oyl] -4-methyl-piperidine and 1 - [(2S) -2-phthalimido-5- (1-triphenylmethyl-imidazol-4-yl) -4- (E) -pentene-oyl] -4-methyl-piperidine

Prepared analogously to Example 14e from 4-methyl-1 - [(2S) -4-methylthio-4-oxo-2-phthalimido-butyl] piperidine (oily portion, R) with (1-triphenylmethyl-imidazol-4-yl ) methyl triphenyl phosphonium chloride and n-butyllithium in anhydrous THF at -70 ° C and by column chromatography on silica gel with EtOAc.
(Z) isomer:
Yield: 12% of theory, foam;
TLC, silica gel, EtOAc / EtOH (100: 4): R _f = 0.87;
C₄₁H₃₈N₄O₃:
Calc .: Molpeak M⁺ = 634.
Found: Molpeak M⁺ = 634.
(E) isomer:
Yield: 22% of theory, foam; R _f = 0.76;
Calc .: Molpeak M⁺ = 634.
Found: Molpeak M⁺ = 634.

d) 1 - [(2S) -2-amino-5- (1-triphenylmethylimidazol-4-yl) -4- (E) - pentene-oyl] -4-methyl-piperidine

1.2 g (1.89 mmol) of 1 - [(2S) -2-phthalimido-5- (1-tri phenylmethylimidazol-4-yl) -4- (E) -pentene-oyl] -4-methyl pipe are heated ridine with 0.2 ml (2.84 mmol) of 80% aqueous hydrazine hydrate in 12 ml EtOH in a bath at 90 ° C. for 60 minutes and, after adding another 0.2 ml hydrazine hydrate, for a further 30 minutes. It is cooled, filtered and the filtrate evaporated in vacuo. The residue is evaporated by column chromatography on silica gel with methylene chloride / MeOH / conc. Ammonia (95: 5: 0.1) cleaned. Yield: 0.30 g (31.6% of theory), oil (R _f = 0.31);
C₃₃H₃₆N₄O:
Calc .: Molpeak (M + H) ⁺ = 505.
Found: Molpeak (M + H) ⁺ = 505.

e) 1 - [(2S) -2- (naphthalene-1-sulfonamido) -5- (1-triphenylmethyl- imidazol-4-yl) -4- (E) -pentene-oyl] -4-methyl-piperidine

Prepared analogously to Example 1c from 0.20 g (0.4 mmol) of 1 - [(2S) - 2-amino-5- (1-triphenylmethyl-imidazol-4-yl) -4- (E) -pentene-oyl] - 4-methyl -piperidine in methylene chloride, each with 1 eq. naphthalene-1-sulfochloride and triethylamine. The reaction mixture is evaporated and reacted without further purification.
TLC, silica gel, methylene chloride / MeOH / conc. Ammonia (10: 1: 0.01): R _f = 0.84.

f) 1 - [(2S) -2- (naphthalene-1-sulfonamido) -5- (1H-imidazole-4 (5) - yl) -4- (E) -pentene-oyl] -4-methyl-piperidine × HCl × H₂O

The crude mixture obtained in Example 20e is treated analogously to Example 14h with 80% aqueous acetic acid. Finally, the purification is carried out by column chromatography on silica gel with EtOAc / EtOH / conc. Ammonia (10: 1: 0.01). The base obtained is treated with ethereal hydrochloric acid.
Yield: 0.15 g (76% of theory), foam (R _f = 0.38);
C₂₄H₂₈N₄0₃5 × HCl × H₂O:
Calc .: C 56.84; H 6.16; N May 11
Found: C 57.09; H 6.40; N 10.61.
Calc .: Molpeak M⁺ = 452.
Found: Molpeak M⁺ = 452.

g) 1 - [(2S) -2- (naphthalene-1-sulfonamido) -5- (1H-imidazole-4 (5) - yl) -pentanoyl] -4-methyl-piperidine × HCl

Prepared analogously to Example 14f from 1 - [(2S) -2- (naphthalene-1-sulfonamido) -5- (1H-imidazole-4 (5) -yl) -4- (E) -pentene-oyl] - 4- methyl-piperidine × HCl × H₂O (R _f = 0.73) by hydrogenation on palladium-carbon (10%) in EtOH.
Yield: 83% of theory, foam;
TLC, silica gel, methylene chloride / MeOH (5: 1): R _f = 0.57;
C₂₄H₃₀N₄O₃S × HCl:
Calc .: Molpeak M⁺ = 454).
Found: Molpeak M⁺ = 454.

h) 1 - {(2S) -2- (naphthalene-1-sulfonamido) -5- [2- (4-methoxycarbo nyl-phenyl) azo-imidazol-4-yl] pentanoyl} -4-methyl-piperidine

Prepared analogously to Example 13e from 1 - [(2S) -2- (naphthalene-1-sulfonamido) -5- (1H-imidazole-4 (5) -yl) -pentanoyl] -4-methylpiperidine × HCl.
Yield: 11% of theory, foam;
C₃₂H₃₆N₆O₅S:
Calc .: Molpeak M⁺ = 616.
Found: Molpeak M⁺ = 616.

i) 1 - [(2S) -5- (2-amino-imidazole-4 (5) -yl) -2- (naphthalene-1-sul fonamido) -pentanoyl] -4-methyl-piperidine × HCl

Prepared analogously to Example 13f from 1 - {(2S) -2- (naphthalene-1-sulfonamido) -5- [2- (4-methoxycarbonyl-phenyl) azo-imidazol-4-yl] -pentanoyl} -4-methyl- piperidine.
Yield: 20% of theory, foam;
C₂₄H₃₁N₅O₃S × HCl:
Calc .: Molpeak M⁺ = 469.
Found: Molpeak M⁺ = 469.

Example 21 1 - [(2S) -2- (naphthalene-2-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] -4-methyl-piperidine × HCl a) 1 - [(2S) -2-amino-5- (1-triphenylmethyl-imidazol-4-yl) -4- (Z) - pentene-oyl] -4-methyl-piperidine

Prepared analogously to Example 20d from 1 - [(2S) -2-phthalimido-5- (1-triphenylmethylimidazol-4-yl) -4- (Z) -pentene-oyl] -4-methylpiperidine (Example 20c) by heating with 80% aqueous hydrazine hydrate in EtOH and by column chromatography cleaning on silica gel with methylene chloride / MeOH / conc. Ammonia (10: 1: 0.01).
Yield: 31.5% of theory, oil (R _f = 0.49; contains approx. 10% (E) isomer, R _f = 0.44);
C₃₃H₃₆N₄O:
Calc .: Molpeak (M + H) ⁺ = 505.
Found: Molpeak (M + H) ⁺ = 505.

b) 1 - [(2S) -2- (naphthalene-2-sulfonamido) -5- (1-triphenylmethyl- imidazol-4-yl) -4- (Z) -pentene-oyl] -4-methyl-piperidine

Prepared analogously to Example 1c from 1 - [(2S) -2-amino-5- (1-tri-phenylmethyl-imidazol-4-yl) -4- (Z) -pentene-oyl] -4-methyl-pipe ridine in methylene chloride with 1 eq. of naphthalene-2-sulfochloride and triethylamine as well as by column chromatography on silica gel with toluene / EtOAc / EtOH (4: 2: 0.5).
Yield: 75% of theory, oil (R _f = 0.63).

c) 1 - [(2S) -2- (naphthalene-2-sulfonamido) -5- (1H-imidazole-4 (5) - yl) -4- (Z) -pentene-oyl] -4-methyl-piperidine × HCl × 0.5 H₂O

Prepared analogously to Example 14h from 1 - [(2S) -2- (naphthalene-2-sulfonamido) -5- (1-triphenylmethylimidazol-4-yl) -4- (Z) -pentene-oyl] -4-methyl -piperidine with 80% aqueous acetic acid and by column chromatography on silica gel with EtOAc / EtOH / conc. Ammonia (90: 10: 0.2). The base obtained is treated with ethereal hydrochloric acid.
Yield: 64% of theory, foam; (R _f = 0.37; contains approx. 10% (E) -isomer, R _f = 0.28);
C₂₄H₂₈N₄O₃S × HCl × 0.5 H₂O.
Calc .: C 57.88; H 6.07; N 11.25.
Found: C 57.70; H 6.38; N 10.81.
Calc .: Molpeak M⁺ = 452.
Found: Molpeak M⁺ = 452.

d) 1 - [(2S) -2- (naphthalene-2-sulfonamido) -5- (1H-imidazole-4 (5) - yl) -pentanoyl] -4-methyl-piperidine × HCl

Prepared analogously to Example 14f from 1 - [(2S) -2- (naphthalene-2-sulfonamido) -5- (1H-imidazole-4 (5) -yl) -4- (Z) -pentene-oyl] -4- methyl piperidine × HCl × 0.5 H₂O (R _f = 0.49) by hydrogenation on palladium-carbon (10%) in EtOH.
Yield: 86% of theory, foam;
TLC, silica gel, EtOAc / EtOH / conc. Ammonia (10: 1: 0.01):
R _f = 0.33;
C₂₄H₃₀N₄O₃S × HCl:
Calc .: Molpeak M⁺ = 454.
Found: Molpeak M⁺ = 454.

e) 1 - {(2S) -2- (naphthalene-2-sulfonamido) -5- [2- (4-methoxycarbo nyl-phenyl) azo-imidazol-4-yl] pentanoyl} -4-methyl-piperidine

Prepared analogously to Example 13e from 1 - [(2S) -2- (naphthalene-2-sulfonamido) -5- (1H-imidazole-4 (5) -yl) -pentanoyl] -4-methylpiperidine × HCl.
Yield: 14% of theory, foam;
C₃₂H₃₆N₆O₅S:
Calc .: Molpeak M⁺ = 616.
Found: Molpeak M⁺ = 616.

f) 1 - [(2S) -5- (2-Amino-imidazole-4 (5) -yl) -2- (naphthalene-2-sulfone amido) -pentanoyl] -4-methyl-piperidine × HCl

Prepared analogously to Example 13f from 1 - {(2S) -2- (naphthalene-2-sulfonamido) -5- [2- (4-methoxycarbonyl-phenyl) azo-imidazol-4-yl] -pentanoyl} -4-methyl- piperidine.
Yield: 16% of theory, foam;
C₂₄H₃₁N₅O₃S × HCl:
Calc .: Molpeak M⁺ = 469.
Found: Molpeak M⁺ = 469.

Example 22 1- {5- (2-Amino-imidazol-4-yl) -1 - [(3-R, S) -3-methyl-1,2,3,4-tetra hydroquinoline-8-sulfonyl] -L-prolinyl} - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid × 1.5 HCl × H₂O

Prepared analogously to Example 12 from 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydro -quinoline-8-sulfone amido] -4- (E) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carbonic acid ethyl ester × 1.5 HCl (Example 10; R _f = 0.41) with conc. Hydrochloric acid 7 days at 20 ° C, with the intention of hydrolyzing only the ethyl ester to the corresponding carboxylic acid. However, cyclization to the title compound also occurs.
Yield: 95% of theory, foam;
Melting point 80 ° C;
TLC, Merck RP-8 F₂₅₄ plate, 5% aqueous sodium chloride solution / MeOH (3: 7): R _f = 0.54; [α] = + 36.8 ° (c = 0.25; EtOH);
C₂₅H₃₄N₆O₅S × 1.5 HCl × H₂O:
Calc .: C 50.55; H 6.17; N 13.71; Cl 8.68.
Found: C 50.36; H 6.41; N 3.50; Cl 3.29.
Calc .: Molpeak (M + H) ⁺ = 531.
Found: Molpeak (M + H) ⁺ = 531.

Example 23 1- [5- (2-Amino-imidazol-4-yl) -1- (4-amino-3,5-dichlorobenzenesul fonyl) -L-prolinyl] -4-methyl-piperidine

0.10 g (0.18 mmol) of 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4- (E) is stirred -pentene-oyl] - 4-methyl-piperidine × HCl × H₂O (Example 2; R _f = 0.54) in 2 ml methanesulfonic acid for 2 hours at 20 ° C, the reaction mixture is poured into cold (0 ° C) semi-concentrated ammonia and extra with EtOAc. The organic phase is dried, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with EtOAc / EtOH / conc. Ammonia (5: 2: 0.02) cleaned.
Yield: 0.05 g (56% of theory), foam;
Melting point: 60 ° C;
R _f = 0.38; [α] = + 51.4 ° (c = 0.36; EtOH);
C₂₀H₂₆Cl₂N₆O₃S:
Calc .: Molpeak M⁺ = 500/502/504 (Cl₂).
Found: Molpeak M⁺ = 500/502/504 (Cl₂).

The same cyclized compound can be obtained when in Based on Tetrahedron Letters 1994, 35, 351-354,  the connection of example 2 starting from 1 - [(2S) -2- (4- Amino-3,5-dichlorobenzenesulfonamido) -5-oxopentanoyl] -4-methyl- piperidine (Example 4e) with 1 eq. 2-amino-imidazole × 0.5 H₂SO₄ to synthesize in methanesulfonic acid (2.5 days at 20 ° C).

Example 24 1 - [(2S) -5- (2-Amino-imidazol-4-yl) -2- (quinolin-8-sulfonamido) - 4- (E) -pentene-oyl] -4-methyl-piperidine × 2 HCl a) 1- [Boc-Asp] -4-methyl-piperidine

Prepared analogously to Example 1d from 1- [Boc-Asp (OBzl)] - 4-methylpiperidine (Example 1d) with 1N sodium hydroxide solution in ethanol.
Yield: 77% of theory; Oil; [α] = 51.7 ° (c = 1,215; MeOH);
C₁₅H₂₆N₂O₅:
Calc .: Molpeak (MH) ⁻ = 313.
Found: Molpeak (MH) ⁻ = 313.

The benzyl radical can also be split off analogously to Example 9d by hydrogenation on palladium-carbon in glacial acetic acid or in ethanol respectively.

b) 1- (2S) -N-Boc-2-amino-4-hydroxy-butanoyl] -4-methyl-piperidine

Prepared analogously to Example 1e from 1- [Boc-Asp] -4-methyl-piperidine via the mixed anhydride by reduction with sodium borohydride.
Yield: 55% of theory; Oil; [α] = -21.3 ° (c = 1,415; MeOH);
C₁₅H₂₈N₂O₄:
Calc .: Molpeak M⁺ = 300.
Found: Molpeak M⁺ = 300.

c) 1 - [(2S) -N-Boc-2-amino-4-oxo-butanoyl] -4-methyl-piperidine

Prepared analogously to Example 8c from 1 - [(2S) -N-Boc-2-amino-4-hydroxy-butanoyl] -4-methyl-piperidine by oxidation with sulfur trioxide-pyridine complex in dimethyl sulfoxide.
Yield: 90% of theory; Oil; [α] = 16.4 ° (c = 0.225; chloroform)

d) 1 - [(2S) -N-Boc-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl] - 4- (Z) -pentene-oyl] -4-methyl-piperidine and 1 - [(2S) -N-Boc-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl] -4- (E) - pentene-oyl] -4-methyl-piperidine

Prepared analogously to Example 4f from 1 - [(2S) -N-Boc-2-amino-4-oxo-butanoyl] -4-methylpiperidine with (imidazo [1,2-a] pyrimidin-2-yl methyl) - triphenylphosphonium chloride in THF / EtOH (1: 1) and DBU. (Z) -isomer (TLC, silica gel, EtOAc / ethanol (10: 1): R _f = 0.53):
Yield: 29.7% of theory;
Melting point: 165-168 ° C; [α] = + 15.7 ° (c = 0.375; MeOH);
C₂₂H₃₁N₅O₃:
Calc .: C 63.90; H 7.56; N 16.94.
Found: C 63.86; H 7.70; N 16.77.
Calc .: Molpeak M⁺ = 413.
Found: Molpeak M⁺ = 413.
E isomer (R _f = 0.29):
Yield: 28.4% of theory;
Melting point: 163-165 ° C; [α] = + 7.2 ° (c = 0.25; MeOH);
Calc .: C 63.90; H 7.56; N 16.94.
Found: C 63.70; H 7.75; N 17.32.
Calc .: Molpeak M⁺ = 413.
Found: Molpeak M⁺ = 413.

e) 1 - [(2S) -2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl] -4- (E) - penten-oyl] -4-methyl-piperidine × 2 CF₃COOH

Prepared analogously to Example 8e from 1 - [(2S) -N-Boc-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl] -4- (E) -pentene-oyl] -4 -methyl piperidine with trifluoroacetic acid in methylene chloride.
Yield: 95% of theory, foam;
C₁₈H₂₃N₅O × 2 CF₃COOH

f) 1 - [(2S) -2- (quinoline-8-sulfonamido) -5- (imidazo [1,2-a] pyrimi din-2-yl] -4- (E) -pentene-oyl] -4-methyl-piperidine

Prepared analogously to Example 8f from 1 - [(2S) -2-amino-5- (imida zo [1,2-a] pyrimidin-2-yl] -4- (E) -pentene-oyl] -4-methyl- piperidine × 2 CF₃COOH with quinoline-8-sulfochloride and triethylamine in methylene chloride.
Yield: 65% of theory, foam;
C₂₆H₂₈N₆O₃S:
Calc .: Molpeak M⁺ = 504.
Found: Molpeak M⁺ = 504.

g) 1 - [(2S) -5- (2-Amino-imidazol-4-yl) -2- (quinolin-8-sulfonami do) -4- (E) -pentene-oyl] -4-methyl-piperidine × 2 HCl

Prepared analogously to Example 1h from 1 - [(2S) -2- (quinolin-8-sulfonamido) -5- (imidazo [1,2-a] pyrimidin-2-yl] -4- (E) -pentene oyl] - 4-methyl-piperidine with hydrazine hydrate in ethanol Yield: 60% of theory, foam;
C₂₃H₂₈N₆O₃5 × 2HCl:
Calc .: Molpeak (M + H) ⁺ = 469.
Found: Molpeak (M + H) ⁺ = 469.

Example 25 1 - [(2S) -5- (2-Amino-imidazol-4-yl) -2- (quinolin-8-sulfonamido) - 4- (E) -pentanoyl] -4-methyl-piperidine × 2 HCl a) 1 - [(2S) -N-Boc-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) - pentanoyl] -4-methyl-piperidine

Prepared analogously to Example 11 from 1 - [(2S) -N-Boc-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl] -4- (Z) -pentene-oyl] -4 -methyl piperidine by hydrogenation in ethanol over palladium-carbon (10%) for 3 hours at 20 ° C. and 3.4 bar (50 psi) and by column-chromatographic purification on silica gel with EtOAc / methanol (5: 1).
Yield: 58% of theory, foam (R _f = 0.62);
C₂₂H₃₃N₅O₃:
Calc .: Molpeak M⁺ = 415.
Found: Molpeak M⁺ = 415.

As a by-product (R _f = 0.40) 1 - [(2S) -N-Boc-2-amino-5- (4,5,6,7-tetrahydro-imidazo [1,2-a] pyrimidin-2-yl ) -penta noyl] -4-methyl-piperidine isolated.

The hydrogenation can also be carried out in ethanol on Raney nickel 3 Carry out hours at 40 ° C and 3.4 bar (50 psi); doing so practically no (tetrahydro) by-product observed.

b) 1 - [(2S) -2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoyl] - 4-methyl-piperidine × 2 CF₃COOH

Prepared analogously to Example 8e from 1 - [(2S) -N-Boc-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoyl] -4-methyl-piperidine with trifluoroacetic acid in methylene chloride .
Yield: 91% of theory, foam;
C₁₇H₂₅N₅O × 2 CF₃COOH

c) 1 - [(2S) -2- (quinoline-8-sulfonamido) -5- (imidazo [1,2-a] pyrimi din-2-yl) pentanoyl] -4-methyl-piperidine

Prepared analogously to Example 8f from 1 - [(2S) -2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoyl] -4-methyl-piperidine × 2 CF₃COOH with quinoline-8- sulfochloride and triethylamine in methylene chloride.
Yield: 71% of theory, foam;
C₂₆H₃₀N₆O₃S:
Calc .: Molpeak M⁺ = 506.
Found: Molpeak M⁺ = 506.

d) 1 - [(2S) -5- (2-amino-imidazol-4-yl) -2-quinolin-8-sulfonamido) - pentanoyl] -4-methyl-piperidine × 2 HCl

Prepared analogously to Example 1h from 1 - [(2S) -2- (quinolin-8-sul fonamido) -5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoyl] -4-methylpiperidine Hydrazine hydrate in ethanol.
Yield: 62% of theory, foam;
C₂₃H₃₀N₆O₃S × 2 HCl:
Calc .: Molpeak (M + H) ⁺ = 471.
Found: Molpeak (M + H) ⁺ = 471.

Example 26 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino- imidazol-4-yl) pentanoyl] -4-methyl-piperidine × HCl × 1.5 H₂O a) 1 - [(2S) -5- (2-amino-imidazol-4-yl) -2-N-Boc-aminopentanoyl] - 4-methyl-piperidine

Prepared analogously to Example 1h from 1 - [(2S) -N-Boc-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoyl] -4-methyl-piperidine with hydrazine hydrate in ethanol.
Yield: 58% of theory, foam;
C₁₉H₃₃N₅O₃:
Calc .: Molpeak (M + H) ⁺ = 380.
Found: Molpeak (M + H) ⁺ = 380.

b) 1 - [(2S) -2-amino-5- (2-amino-imidazol-4-yl) pentanoyl] -4- methyl-piperidine × 2 CF₃COOH

Prepared analogously to Example 8e from 1 - [(2S) -5- (2-amino-imidazol-4-yl) -2-N-Boc-amino-pentanoyl] -4-methyl-piperidine with trifluoroacetic acid in methylene chloride.
Yield: 95% of theory, foam;
C₁₄H₂₅N₅O × 2 CF₃COOH

c) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2- amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine × HCl × 1.5 H₂O

Prepared analogously to Example 8f with 4-amino-3,5-dichlorobenzenesulfochloride and triethylamine in methylene chloride.
Yield: 17% of theory;
Melting point: 148-150 ° C;
C₂₀H₂₈Cl₂N₆O₃S × HCl × 1.5 H₂O:
Calc .: Molpeak M⁺ = 502/504/506 (Cl₂).
Found: Molpeak M⁺ = 502/504/506 (Cl₂).

Example 27 1- {rac-5- (2-Amino-imidazol-4-yl) -2- [N- (quinolin-8-sulfonyl) -N- (ethoxycarbonyl-methyl) -amino] -4- (E) -pentene-oyl} -4-methyl- piperidine × 2 HCl a) 1- {rac-2- [N- (quinoline-8-sulfonyl) -N- (ethoxycarbonyl-methyl) - amino] -5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E) -pentene-oyl} -4- methyl piperidine

Made from 1- [rac-2- (quinoline-8-sulfonamido) -5- (imida zo [1,2-a] pyrimidin-2-yl) -4- (E) -pentene-oyl] -4-methyl -piperidine (R _f = 0.32) in DMSO at 20 ° C by reaction with 1 eq. of potassium tert-butoxide and - after stirring for 5 minutes - with 1 eq. of ethyl bromoacetic acid. After 30 minutes at 20 ° C., water is added and the mixture is extracted with EtOAc. The organic extract is dried, filtered and evaporated in vacuo. The evaporation residue is purified by column chromatography on silica gel with EtOAc / EtOH (5: 1).
Yield: 78% of theory, foam (R _f = 0.48);
C₃₀H₃₄N₆O₅S:
Calc .: Molpeak (M + H) ⁺ = 591.
Found: Molpeak (M + H) ⁺ = 591.

b) 1- {rac-5- (2-Amino-imidazol-4-yl) -2- [N- (quinolin-8-sulfonyl) - N- (ethoxycarbonyl-methyl) -amino] -4- (E) -pentene-oyl} -4-methyl- piperidine × 2 HCl

Prepared analogously to Example 1h from 1- {rac-2- [N- (quinolin-8-sulfonyl) -N- (ethoxycarbonyl-methyl) -amino] -5- (imidazo [1,2-a] pyrimidin-2-yl ) -4- (E) -pentene-oyl} -4-methyl-piperidine with hydrazine hydrate in EtOH.
Yield: 56% of theory, foam;
C₂₇H₃₄N₆O₅S × 2 HCl:
Calc .: Molpeak (M + H) ⁺ = 555.
Found: Molpeak (M + H) ⁺ = 555.

Example 28 1- {rac-5- (2-Amino-imidazol-4-yl) -2- [N- (quinolin-8-sulfonyl) - N- (ethoxycarbonyl-methyl) amino] pentanoyl} -4-methyl-piperidine × 2 HCl

Prepared analogously to Example 3 from 1- {rac-5- (2-amino-imidazol-4-yl) -2- [N- (quinolin-8-sulfonyl) -N- (ethoxycarbonyl-methyl) -amino] -4 - (E) -pentene-oyl} -4-methyl-piperidine × 2 HCl in EtOH by hydrogenation on palladium-carbon (10%).
Yield: 69% of theory, foam;
C₂₇H₃₆N₆O₅S × 2 HCl:
Calc .: Molpeak (M + H) ⁺ = 557.
Found: Molpeak (M + H) ⁺ = 557.

Example 29 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino- imidazol-4-yl) pentanoyl] -4-methyl-piperidine × HCl × 1.5 H₂O a) (2S) -N-Z-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (Z) -pen tert-butyl ten-acid and (2S) -N-Z-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E) -pentene- acid tert-butyl ester

Prepared analogously to Example 4f from (2S) -NZ-2-amino-4-oxobutyric acid tert-butyl ester (see Synthesis 1988, 786-791; can also be prepared in good yield from Z-Asp-OtBu via Z-Asp [N (Me) OMe] -OtBu by reduction with 1.5 eq. Diisobutylaluminum hydride in THF at -75 ° C) with (imidazo [1,2-a] pyrimidin-2-yl-methyl) -triphenylphosphonium chloride in THF / EtOH ( 1: 1) and DBU.
(Z) isomer:
Yield: 26% of theory, foam;
C₂₃H₂₆N₄O₄:
Calc .: Molpeak M⁺ = 422.
Found: Molpeak M⁺ = 422.
(E) isomer:
Yield: 27% of theory, foam;
Calc .: Molpeak M⁺ = 422.
Found: Molpeak M⁺ = 422.

b) (2S) -2-Amino-5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoic acid - tert-butyl ester

Prepared analogously to Example 14f from (2S) -NZ-2-amino-5- (imida zo [1,2-a] pyrimidin-2-yl) -4- (Z) -pentenoic acid tert-butyl ester in EtOH Hydrogenation on palladium-carbon (10%).
Yield: 45% of theory, foam;
C₁₅H₂₂N₄O₂
The same compound is obtained when (2S) -NZ-2-amino-5- (imidazo [1,2-a] pyridmidin-2-yl) -4- (E) -pentene acid tert.bu tylester is used becomes.

c) (2S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoic acid tert-butyl ester

Prepared analogously to Example 8f from (25) -2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoic acid tert-butyl ester with 4-amino-3,5-dichlorobenzosulfochloride and triethylamine in methylene chloride.
Yield: 63% of theory, foam;
C₂₁H₂₅Cl₂N₅O₄5

d) (2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (imidazo [1.2-a] pyrimidin-2-yl) pentanoic acid × CF₃COOH

Prepared analogously to Example 14b from (2S) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -5- (imidazo [1,2-a] pyrimidin-2-yl) - pentanoic acid tert-butyl ester with Trifluoroacetic acid in methylene chloride.
Yield: 95% of theory, foam;
C₁₇H₁₇Cl₂N₅O₄5 × CF₃COOH

e) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (imida zo [1,2-a] pyrimidin-2-yl) pentanoyl] -4-methyl-piperidine

Prepared analogously to Example 1a from (2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoic acid × CF₃COOH in THF at T _i = -30 ° C with 2.5 eq. N-methyl-morpholine and 1.2 eq. isobutyl chloroformate, reaction of the mixed anhydride with 4-methylpiperidine, and finally purification by column chromatography on silica gel with EtOAc / EtOH (10: 1).
Yield: 75% of theory, foam;
C₂₃H₂₈Cl₂N₆O₃5:
Calc .: Molpeak (M + H) ⁺ = 539/541/543 (Cl₂).
Found: Molpeak (M + H) ⁺ = 539/541/543 (Cl₂).

f) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-ami no-imidazol-4-yl) pentanoyl] -4-methyl-piperidine × HCl × 1.5 H₂O

Prepared analogously to Example 1h from 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoyl] -4 -methyl piperidine with hydrazine hydrate in EtOH.
Yield: 60% of theory;
Melting point: 147-149 ° C
C₂₀H₂₈Cl₂N₆O₃5 × HCl × 1.5 H₂O; Calc .: Molpeak M⁺ = 502/504/506 (Cl₂).
Found: Molpeak M⁺ = 502/504/506 (Cl₂).

Example 30 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino- imidazol-4-yl) pentanoyl] -4-methyl-piperidine × HCl × 1.5 H₂O a) (2S) -N-Z-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E) -pen ten-acid × CF₃COOH

Prepared analogously to Example 14b from (2S) -NZ-2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E) -pentene acid tert-butyl ester with trifluoroacetic acid in methylene chloride .
Yield: 93% of theory, foam;
C₁₉H₁₈N₄O₄ × CF₃COOH

b) 1 - [(2S) -2- (N-Z-amino) -5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E) -pentene-oyl] -4-methyl-piperidine

Prepared analogously to Example 1a from (2S) -NZ-2-amino-5- (imida zo [1,2-a] pyrimidin-2-yl) -4- (E) -pentene acid × CF₃COOH in THF at T _i = -30 ° C with 2.5 eq. N-methyl-morpholine and 1.2 eq. Isobutyl chloroformate, reaction of the mixed anhydride with 4-methyl-piperidine, and finally purification by column chromatography on silica gel with EtOAc / EtOH (10: 1) .
Yield: 69% of theory, foam;
C₂₅H₂₉N₅O₃

c) 1 - [(2S) -2-amino-5- (imidazo [1,2-a] pyrimidin-2-yl) pentanoyl] - 4-methyl-piperidine

Prepared analogously to Example 14f from 1 - [(2S) -2- (NZ-amino) -5- (imidazo [1,2-a] pyrimidin-2-yl) -4- (E) -pentene-oyl] -4 -methyl piperidine in EtOH by hydrogenation on palladium-carbon (10%).
Yield: 49% of theory, foam;
C₁₇H₂₅N₅O:
Calc .: Molpeak M⁺ = 315.
Found: Molpeak M⁺ = 315.

d) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (imi add [1,2-a] pyrimidin-2-yl) pentanoyl] -4-methyl-piperidine

Prepared analogously to Example 14g from 1 - [(2S) -2-amino-5- (imi dazo [1,2-a] pyrimidin-2-yl) pentanoyl] -4-methyl-piperidine in methylene chloride with 4-amino- 3,5-dichlorobenzenesufochloride and triethylamine.
Yield: 58% of theory;
C₂₃H₂₈Cl₂N₆O₃S:
Calc .: Molpeak (M + H) ⁺ = 539/541/543 (Cl₂).
Found: Molpeak (M + H) ⁺ = 539/541/543 (Cl₂).

e) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2- amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine × HCl × 1.5 H₂O

Prepared analogously to Example 1h from 1 - [(2S) -2- (4-amino-3,5-di chlorobenzenesulfonamido) -5- (imidazo [1,2-a] pyrimidin-2-yl) -pen tanoyl] -4-methyl-piperidine with hydrazine hydrate in EtOH.
Yield: 63% of theory;
Melting point: 148-50 ° C.
Calc .: Molpeak M⁺ = 502/504/506 (Cl₂).
Found: Molpeak M⁺ = 502/504/506 (Cl₂).

The following compounds can be prepared analogously to the examples above:
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] pyrrolidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] hexamethyleneimine
1 - [(S) -2- (4-Dimethylamino-benzo-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (4-Diethylamino-benzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (Naphth-1-ylamino-benzenesulfonamido) -5- (2-amino-imi dazol-4-yl) pentanoyl] piperidine
[(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (6,7-Dimethoxy-naphth-1-yl-sulfonamido) 5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (Naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] piperidine
1 - [(S) -2- (5-Dimethylamino-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (6, 7-Dimethoxy-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] piperidine
1 - [(S) -2- (2-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -piperidine
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -piperidine
1 - [(S) -2- (Isoquinolin-5-yl-sulfonamido) -5- (imidazol-2-yl) -aminopentanoyl] piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-5-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-6-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] - piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -piperidin-2- carboxylic acid
1 - [(S) -2- (4-A mino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -pyrrolidin-2 -carboxylic acid ethyl ester
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -pyrrolidin-2- carboxylic acid
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -hexamethyleneimin-2- carboxylic acid ethyl ester
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -hexamethyleneim in-2 -carboxylic acid
1 - [(S) -2- (4-amino-2,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2- (4-amino-2,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -piperidin-2- carboxylic acid
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -pyrrolidine-2-carboxylic acid, ethyl ester
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -pyrrolidin-2-carboxylic acid
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidine-2-carboxylic acid, ethyl ester
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -hexamethyleneimine-2-carboxylic acid, ethyl ester
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -hexamethyleneimine-2-carboxylic acid
1 - [(S) -2- (4-Diethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidine-2-carboxylic acid, ethyl ester
1 - [(S) -2- (4-Diethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -piperidin-2- carboxylic acid
1 - [(S) -2- (6,7-Dimethoxy-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -piperidine- 2-carboxylic acid ethyl ester
1 - [(S) -2- (6,7-Dimethoxy-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -piperidine- 2-carboxylic acid
1 - [(S) -2- (Naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] - (R, S) -piperidine-2-carboxylic acid, ethyl ester
1 - [(S) -2- (Naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (5-Dimethylamino-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2 - (5-dimethylamino-naphth-2-yl-sulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (R, S) -piperidin-2- carboxylic acid
1 - [(S) -2- (6,7-dimethoxy-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -piperidine- 2-carboxylic acid ethyl ester
1 - [(S) -2- (6,7-dimethoxy-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -piperidine- 2-carboxylic acid
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] - (R, S) -piperidine-2-carboxylic acid, ethyl ester
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (2-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidin-2 -carboxylic acid ethyl ester
1 - [(S) -2- (2-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidin-2 -carboxylic acid
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -pyrrolidin-2 -carboxylic acid ethyl ester
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -pyrrolidin-2 -carboxylic acid
1 - [(S) -2- (3-methyl-hinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidine- 2-carboxylic acid ethyl ester
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidin-2 -carboxylic acid
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -hexamethyleneimin-2 -carboxylic acid- ethyl ester
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -hexamethyleneimin-2 -carboxylic acid
1 - [(S) - 2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidin-2 -carboxylic acid ethyl ester
1 - [(S) -2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidin-2 -carboxylic acid
1 - [(S) -2- (Isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidine-2-carboxylic acid, ethyl ester
1 - [(S) - 2- (Isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S ) -piperidine-2-carbon acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S ) -piperidine-2-carbon acid
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S ) -piperidine-2-carbon acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (R, S ) -piperidine-2-carbon acid
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4yl) -pentanoyl] - (R, S) - piperidine-2-carbon acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S ) -piperidine-2-carbon acid
1 - [(S) -2- (2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -piperidine-2-carbonic acid ethyl ester
1 - [(S) -2- (2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -piperidine-2-carboxylic acid, ethyl ester
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (4-Amino-2,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -4-methylpiperidine
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (6,7-Dimethoxy-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (Isoquinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (2-methyl-isoquinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (4-Methylisoquinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl- piperidine
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (Isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl- piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-6-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl -piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] -4-methyl- piperidine
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] - 4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl- methyl piperidine-2-carbonate
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl- propyl piperidine-2-carbonate
1 - [(S) -2- (4Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-piperidine- 2-carbon acid tert-butyl ester
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl- benzyl piperidine-2-carbonate
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methylpiperidine-2-carboxylic acid, ethyl ester
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] - (2R, 4R) - 4-methyl-piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2- (naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] - (2R, 4R) -4-methyl-piperidin-2- carboxylic acid
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -penta noyl] - (2R, 4R) -4-methyl -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl- piperidine-2-carbon acid
1 - [(S) -2- (6,7-dimethoxy-naphth-1-yl-sulfonamido) -5 - (2-amino-imidazol-4-yl) -pentanoyl] - (2R, 4R) -4- methyl piperidine-2-carbon acid ethyl ester
1 - [(S) -2- (6,7-dimethoxy-naphth-1-yl-sulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (2R, 4R) -4- methyl piperidine-2-carbon acid
1 - [(S) -2- (quinolin-8yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid- ethyl ester
1 - [(S) -2- (quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] - (2R, 4R) -4-methyl-piperidin-2- carboxylic acid
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl -piperidine-2-carboxylic acid
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl -piperidine-2-carboxylic acid methyl ester
1 - [(S) -2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl -piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-Tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R ) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-Tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R ) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid methyl ester
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid propyl ester
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid tert-butyl ester
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid benzyl ester
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid ethyl ester
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid
1 - [(S) -2- (4-methyl-1, 2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid ethyl ester
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2 R, 4R) -4-methyl-pipe ridin-2-carboxylic acid
1 - [(S) -2- (isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (2,4R) -4-methyl-piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2- (isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (2R, 4R) -4-methyl-piperidin-2- carboxylic acid
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R ) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R ) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R ) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R ) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R ) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R ) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] - (2R, 4R) -4-methyl-piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2 (isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-cyano-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2- (1H-tetrazol-5-yl ) -4-methyl-piperi din
1 - [(S) -2- (2-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-cyano-4-methyl-piperidine
1 - [(S) -2- (2-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2- (1H-tetrazol-5- yl) -4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-cyano-4-methyl-piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2- (1H-tetrazol-5- yl) -4-methyl-piperidine
1 - [(S) -2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-cyano-4-methyl-piperidine
1 - [(S) -2- (4-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2- (1H-tetrazol-5- yl) -4-methyl-piperidine
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-cyano-4-methyl-pipe ridin
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2- (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-cyano-4-methyl-pipe ridin
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2- (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-cyano-4-methyl-pipe ridin
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2- (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5 - (2-amino-imidazol-4-yl) -pentanoyl] -2-cyano- 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2- (1H -tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-cyano- 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2- (1H -tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (1,2, 3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-cyano- 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2- (1H -tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] - 2-cyano-4-methyl-piperidine
1 - [(S) -2- (2,3,4,5-tetrahydro-1M-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] - 2- (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-cyano-4-methyl-piperidine
1 - [(S) -2- (isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2- (1H-tetrazol-5-yl) -4- methyl piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-hydroxymethyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-acetoxymethyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-propionyloxymethyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-ethoxymethyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-hydroxymethyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-acetoxymethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-hydroxymethyl-4-methyl piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-acetoxymethyl-4-methyl piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-propionyloxymethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxymethyl-4-methyl piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-aminomethyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-ethylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-dimethylaminomethyl-4-methylpipe ridine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-acetylaminomethyl-4-methylpiperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-ethoxycarbonylaminomethyl-4-methylpiperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-benzyloxycarbonylaminomethyl-4-methyl piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-hydroxycarbonylmethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-ethoxycarbonylmethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-benzyloxycarbonylmethylaminocar bonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4yl) pentanoyl] -2-ethylaminocarbonyl-4-methylpiperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -2-dimethylarmnocarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-aminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-dimethylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-acetylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) 5- (2-amino-imidazol-4-yl) -pentanoyl] -2-ethoxycarbonylaminomethyl-4-methyl-pipe ridin
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-benzyloxycarbonylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-hydroxycarbonylmethylaminocarbonyl-4-methyl piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-ethoxycarbonylmethylaminocarbonyl-4-methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-benzyloxycarbonylmethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (2-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-ethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-dimethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-aminomethyl-4-methyl piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-dimethylamino-methyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-acetylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl aminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-benzyloxycarbonyl aminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-hydroxycarbonylmethylaminocarbonyl-4-methylpiperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonylmethylaminocarbonyl-4-methylpiperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-benzyloxycarbonyl methylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-aminocarbonyl-4-methyl piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-aminocarbonyl-4-methyl piperidine
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-aminocarbonyl-4-methyl piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-dimethylamino-car bonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-hydroxycarbonylmethyl aminocarbonyl -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonylmethyl aminocarbonyl -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-benzyloxycarbonylmethyl aminocarbonyl -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-aminocarbonyl- 4-methyl-pi peridine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-ethylaminocarbonyl- 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-dimethylaminocarbonyl- 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-hydroxycarbonylmethyl aminocarbonyl -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonylmethyl aminocarbonyl -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-benzyloxycarbonylmethyl aminocarbonyl -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-aminocarbonyl- 4-methyl-pi peridine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethylaminocarbonyl- 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-dimethylaminocarbonyl- 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-hydroxycarbonylmethyl aminocarbonyl -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonylmethylamino carbonyl -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-benzyloxycarbonylmethyl aminocarbonyl -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-aminocarbonyl- 4-methyl-pi peridine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-ethylaminocarbonyl- 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -pentanoyl] -2-dimethylaminocarbonyl- 4-methyl-piperidine
1 - [(S) -2- (2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -pentanoyl] - 2-aminocarbonyl-4-methylpiperidine
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonylpiperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-carboxy-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl-4- methyl pipe ridin
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-carboxy-4- methyl piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-carboxy-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-carboxypiperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl-4- methyl pipe ridin
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-carboxy-4- methyl piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) pentanoyl] -2-carboxy-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -pentanoyl] -piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -pentanoyl] -4-methyl-pi peridine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -pentanoyl] -2-ethoxycar bonyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -pentanoyl] -2-carboxy-pi peridine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -pentanoyl] -2-ethoxycar bonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -pentanoyl] -2-carboxy-4-methyl-piperidine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] glycine
N - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [methyl] glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [methyl] glycine
N - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [ethyl] glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [ethyl] glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [2-methoxy-ethyl] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [2-methoxy-ethyl] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [tetrahydrofuran-2-yl-methyl ] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [tetrahydrofuran-2-yl-methyl ] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [tetrahydropyran-2-yl-methyl ] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [tetrahydropyran-2-yl-methyl ] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [cyclobutyl] glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [cyclobutyl] glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [cyclopentyl] glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [cyclopentyl] glycine
N - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [cyclohexyl] glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [cyclohexyl] glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [cycloheptyl] glycine ethyl ester
N - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [cycloheptyl] glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -N- [3-methylbutyl] - glycine
N - [(S) -2- (Quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] -glycine ethyl ester
N - [(S) -2- (quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - pentanoyl] -glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [methyl] glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [methyl] glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclopropyl] glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclopropyl] glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclobutyl] glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclobutyl] glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclopentyl] glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclopentyl] glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclohexyl] glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclohexyl] glycine
N - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] glycine ethyl ester
N - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [methyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [methyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [ethyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [ethyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [2-methoxy-ethyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [2-methoxy-ethyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [tetrahydrofuran-2-ylmethyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [tetrahydrofuran-2-yl-methyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [tetrahydro-2H-py ran-2-yl-methyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [tetrahydro-2M-py ran-2-yl-methyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclopropyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclopropyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclobutyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclobutyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2 amino-imidazole-4-yl) -pentanoyl] -N - [cyclopentyl] -gly cin-ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclopentyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclohexyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cyclohexyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cycloheptyl] gly cin ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [cycloheptyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [benzyl] glycine ethyl ester
M - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [benzyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [3-methylbutyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -N- [3-methylbutyl] glycine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-aminoimidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl- piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4- methyl-pi peridine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl -piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazol-4yl) pentanoyl] -4-methyl -piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl- piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidin-2- carboxylic acid
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl- 4-methylpiperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl- piperidine-2-carbon acid
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -2- ethoxycar bonyl-4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4- methyl-pi peridine-2-carboxylic acid
1 - [(S) -2- (4-amino- 59395 00070 552 001000280000000200012000285915928400040 0002019548797 00004 592763,5-dichlorobenzenesulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) - pentanoyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl -piperidine-2-carboxylic acid
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-benzyloxycar bonyl-methyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] - 2-ethoxy-carbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-benzyloxycar bonyl-methyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] - 4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (Quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl-4-methyl- piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) pentanoyl] piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl- piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4- methyl pipe ridin
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonyl methyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4- methyl-pi peridine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl -piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl- 4-methyl-pipe ridin
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl- piperidine-2-carbon acid
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl- (N-ethoxycarbonyl methyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -2- ethoxycar bonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl- (N-ethoxycarbonyl methyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4- methyl-pi peridine-2-carboxylic acid
1 - [(S) -2- (3Methyl-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonyl methyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycar bonyl -4-methyl-piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) -pentanoyl] -4- methyl piperidine-2-carboxylic acid
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -2-ethoxycarbonyl - 4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl -piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-Tetrahydro-quinolin-8-yl-sulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl ] piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-quinolin-8-yl-sulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl ] -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-quinolin-8-yl-sulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl ] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-quinolin-8-yl-sulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) pentanoyl ] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazole-4- yl) pentanoyl] piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazole-4- yl) -pentanoyl] -4-methyl-pi peridine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) -pen tanoyl] -4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) - pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazole-4 -yl) -pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazole-4- yl) -pentanoyl] -2-ethoxycar bonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methyl) amino) -5- (2-amino-imidazole-4- yl) -pentanoyl] -4-methyl-pi peridin-2-carboxylic acid
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) -pen tanoyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) -pen tanoyl] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) - pentanoyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) - pentanoyl] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazole-4 -yl) -pentanoyl] -2- ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazole-4 -yl) -pentanoyl] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (4-nitro-benzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] -4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (2R, 4R) -2-hydroxymethyl- 4-methyl-pi peridine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (2R, 4R) -2- (ethoxycarbonylmethyl aminocarbonyl) -4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) pentanoyl] - (2R, 4R) -2- (hydroxycarbonylmethyl aminocarbonyl) -4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] pyrrolidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] hexamethyleneimine
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (4-Diethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (Naphth-1-ylamino-benzenesulfonamido) -5- (2-amino-imi dazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (6,7-Dimethoxy-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (Naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentenoyl] piperidine
1 - [(S) -2- (5-Dimethylamino-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (6,7-Dimethoxy-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentenoyl] piperidine
1 - [(S) -2- (2-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) - 2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (1,2,3,4-Tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl ] piperidine
1 - [(S) -2- (2-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4 -pentene-oyl] -piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4 -pentene-oyl] -piperidine
1 - [(S) -2- (4-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4 -pentene-oyl] -piperidine
1 - [(S) -2- (Isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - piperidine
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (2,3,4,5-Tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentene -oyl] -piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (R, S) - piperidine-2-carboxylic acid
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (R, S) - pyrrolidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (R, S) - pyrrolidine-2-carboxylic acid
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (R, S) - hexamethyleneimine-2-carbon acid ethyl ester
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (R, S) - hexamethyleneimine-2-carbon acid
1 - [(S) -2- (4-amino-2,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (R, S) - piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (4-amino-2,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (R, S) - piperidine-2-carboxylic acid
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -pyrrolidine-2-carboxylic acid -ethyl ester
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -pyrrolidine-2-carboxylic acid
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid -ethyl ester
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentene-oyl] - (R, S) -hexamethyleneimine-2-carboxylic acid - ethyl ester
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentene-oyl] - (R, S) -hexamethyleneimine-2-carboxylic acid
1 - [(S) -2- (4-Diethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentene-oyl] - (R, S) -piperidine-2-carboxylic acid -ethyl ester
1 - [(S) -2- (4-Diethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) - piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) - piperidine-2-carboxylic acid
1 - [(S) -2- (6,7-Dimethoxy-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S ) -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (6,7-Dimethoxy-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S ) -piperidine-2-carboxylic acid
1 - [(S) -2- (naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentenoyl] - (R, S) -piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2- (naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentenoyl] - (R, S) -piperidin-2- carboxylic acid
1 - [(S) -2- (5-Dimethylamino-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) - piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (5-Dimethylamino-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) - piperidine-2-carboxylic acid
1 - [(S) -2- (6,7-Dimethoxy-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S ) -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (6,7-Dimethoxy-naphth-2-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S ) -piperidine-2-carboxylic acid
1 - [(S) -2- (quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentenoyl] - (R, S) -piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2- (quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentenoyl] - (R, S) -piperidin-2- carboxylic acid
1 - [(S) -2- (2-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (2-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -pyrrolidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -pyrrolidine-2-carboxylic acid
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -hexamethyleneimine-2-carboxylic acid ethyl ester
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -hexamethyleneimine-2-carboxylic acid
1 - [(S) -2- (4-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (4-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2- (isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidin-2- carboxylic acid
I - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidine-2-carboxylic acid
1 - [(S) -2- (2,3,4,5-Tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentene -oyl] - (R, S) -piperidin-2-car bonic acid ethyl ester
1 - [(S) -2- (2,3,4,5-Tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentene -oyl] - (R, S) -piperidin-2-car bonic acid
1 - [(S) -2- (isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidin-2- carboxylic acid ethyl ester
1 - [(S) -2- (isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (R, S) -piperidin-2- carboxylic acid
1 - [(S) -2- (4-Amino-2,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -4-methylpiperidine
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentene-oyl] -4-methyl-piperidine
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperidine
1 - [(S) -2- (6,7-dimethoxy-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl- piperidine
1 - [(S) -2- (Isoquinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperidine
1 - [(S) -2- (2-Methylisoquinolin-8-yl-sulfonamido) -5- (2-amino-i midazol-4-yl) -4-pentenoyl] -4-methylpiperidine
1 - [(S) -2- (4-Methyl-isoquinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 4-methyl-piperidine
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -4-methyl-piperidine
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -4-methyl-piperidine
1 - [(S) -2- (Isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 4-methyl-piperidine
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperidine
1 - [(S) -2- (2,3,4,5-Tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentene -oyl] -4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (2R, 4R) - 4-methyl-piperidin-2-car bonic acid methyl ester
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (2R, 4R) - 4-methyl-piperidin-2-car propyl ester
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (2R, 4R) - 4-methyl-piperidin-2-carbonic acid tert-butyl ester
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (2R, 4R) - 4-methyl-piperidin-2-car benzyl ester
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentene-oyl] - (2R, 4R) -4-methyl-piperidine -2-carbonic acid ethyl ester
1 - [(S) -2- (4-Dimethylamino-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine- 2-carboxylic acid
1 - [(S) -2- (Naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentenoyl] - (2R, 4R) -4-methyl- piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (Naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentenoyl] - (2R, 4R) -4-methyl- piperidine-2-carboxylic acid
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) - 4-methyl-piperidin-2-car bonic acid ethyl ester
1 - [(S) -2- (5-Dimethylamino-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) - 4-methyl-piperidin-2-car bonic acid
1 - [(S) -2- (6,7-dimethoxy-napth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidin-2-car bonic acid ethyl ester
1 - [(S) -2- (6,7-Dimethoxy-naphth-1-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R ) -4-methyl-piperidin-2-car bonic acid
1 - [(S) -2- (quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentenoyl] - (2R, 4R) -4-methyl- piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentenoyl] - (2R, 4R) -4-methyl- piperidine-2-carboxylic acid
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carbon acid
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) Methyl -4-methyl-piperidine-2-carbonate
1 - [(S) -2- (4-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carbon acid ethyl ester
1 - [(S) -2- (4-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carbon acid
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2 - (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonami do) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid, methyl ester
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid propyl ester
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid tert-butyl ester
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid benzyl ester
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl- piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl- piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl- piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2- (isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - (2R, 4R) -4-methyl- piperidine-2-carboxylic acid
1 - [(S) -2- (2,3,4,5-Tetrahydro-1M-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentene -oyl] - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid ethyl ester
1 - [(S) -2- (2,3,4,5-Tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentene -oyl] - (2R, 4R) -4-methyl-pipe ridin-2-carboxylic acid
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-cyano-4- methyl piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2- (1H-tetrazole -5-yl) -4-methyl-pi peridine
1 - [(S) -2- (2-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-cyano-4 -methyl piperidine
1 - [(S) -2- (2-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- (1H- tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-cyano-4 -methyl piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- (1H- tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-cyano-4 -methyl piperidine
1 - [(S) -2- (4-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- (1H- tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-cyano-4-methylpiperidine
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2- (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-cyano-4-methylpiperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2- (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-cyano-4-methylpiperidine
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2- (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-cyano-4-methyl-piperi din
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2- (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-cyano-4-methyl-piperi din
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2- (1H-tetrazol-5-yl) -4-methylpiperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-cyano-4-methyl-piperi din
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2 - (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (2,3,4,5-Tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentene -oyl] -2-cyano-4-methyl-pipe ridin
1 - [(S) -2- (2,3,4,5-Tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentene -oyl] -2- (1H-tetrazol-5-yl) -4-methyl-piperidine
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentene-oyl] -2-cyano-4-methyl-piperidine
1 - [(S) -2- (isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- (1H-tetrazol5-yl) - 4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-hydroxymethyl-4- methyl piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2acetoxymethyl-4-methyl- piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-propionyloxymethyl-4- methyl-pi peridine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-ethoxymethyl-4- methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-hydroxymethyl-4 -methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-acetoxymethyl-4 -methyl piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -2-hydroxymethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -2-acetoxymethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-propionyloxy methyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4 -pentene-oyl] -2-ethoxymethyl-4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-aminomethyl-4- methyl piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-ethylaminomethyl-4- methyl pipe ridin
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-dimethylaminomethyl-4- methyl-pi peridine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-acetylaminomethyl-4- methyl pipe ridin
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-ethoxycarbonylaminomethyl-4- methyl piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-benzyloxycarbonylaminomethyl-4- methyl piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-hydroxycarbonylmethylaminocar bonyl-4 -methyl piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-ethoxycarbonylmethylaminocar bonyl-4 -methyl piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-benzyloxycarbonylmethylaminocar bonyl-4 -methyl piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-aminocarbonyl-4- methyl piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-ethylaminocarbonyl-4- methyl-pi peridine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -2-dimethylaminocarbonyl-4- methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-aminomethyl-4 -methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-ethylaminomethyl-4 -methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-dimethylaminomethyl-4 -methyl-piperi din
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-acetylaminomethyl-4 -methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-ethoxycarbonylaminomethyl-4 -methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-benzyloxycarbonylaminomethyl-4 -me thyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-hydroxycarbonylmethylaminocarbonyl-4 - methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-ethoxycarbonylmethylaminocarbonyl-4 - methyl piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-benzyloxycarbonylmethylaminocarbonyl- 4 -methyl piperidine
1 - [(S) -2- (2-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-aminocarbonyl-4 -methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-aminocarbonyl-4 -methyl piperidine
1 - [(S) -2- (4-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-aminocarbonyl-4 -methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-ethylaminocarbonyl-4 -methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-dimethylaminocarbonyl-4 -methyl pipe ridin
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-aminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-ethylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-dimethylamino-methyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -2-acetylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-ethoxycarbonyl aminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-benzyloxycar bonylaminomethyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-hydroxycarbonylmethylaminocarbonyl-4-methylpiperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-ethoxycarbonyl methylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-benzyloxycar bonyl-methylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (2-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-ethylaminocar bonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -2-dimethylamino carbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-hydroxycarbonylmethyl aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-ethoxycarbonylmethyl aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-benzyloxycarbonyl methyl aminocarbonyl-4-methyl piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-aminocarbonyl-4-methylpiperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-ethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-dimethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-hydroxycarbonylmethyl aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-ethoxycarbonylmethyl aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-benzyloxycarbonyl methyl aminocarbonyl-4-methyl piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-aminocarbonyl-4-methylpiperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-ethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-6-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-dimethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-hydroxycarbonylmethyl aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-ethoxycarbonylmethyl amino-carbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-benzyloxycarbonyl methyl aminocarbonyl-4-methyl piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-aminocarbonyl-4-methylpiperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-ethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-isoquinolin-7-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-dimethylaminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (2,3,4,5-Tetrahydro-1H-3-benzazepin-7-yl-sulfonamido) - 5- (2-amino-imidazol-4-yl) -4-pentene -oyl] -2-aminocarbonyl-4-methyl piperidine
1 - [(S) -2- (Isoindolin-5-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-aminocarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4- methyl piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- ethoxycarbonyl piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- carboxy-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- ethoxycarbonyl-4-methylpiperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- carboxy-4-methyl-piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-ethoxycarbonyl-4methyl -piperidine
1 - [(S) -2- (Quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-carboxy-4 -methyl piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4- methyl piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- ethoxycarbonyl piperidine
1 [(S) -2- (3-Methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-carboxy -piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- ethoxycarbonyl-4-methylpiperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2- carboxy-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -2-carboxy-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -4-pentenoyl] piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -4-pentenoyl] -4-methylpiperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -4-pentenoyl] -2- ethoxycarbonylpiperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -4-pentene-oyl] -2-carboxy-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -4-pentenoyl] -2- ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -2-methyl-5- (2-amino-imidazol-4-yl ) -4-penten-oyl] -2-carboxy-4-methyl-piperidine
N - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [methyl] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [methyl] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [ethyl] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [ethyl] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [2-methoxy -ethyl] -glycine-ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [2-methoxy -ethyl] -glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [tetrahydrofuran-2 -yl-methyl] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [tetrahydrofuran-2 -yl-methyl] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [tetrahydropyran-2 -yl-methyl] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [tetrahydropyran-2 -yl-methyl] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [cyclobutyl] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [cyclobutyl] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N - [cyclopentyl] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [cyclopentyl] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [cyclohexyl] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [cyclohexyl] - glycine
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [cycloheptyl] - glycine ethyl ester
N - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [cycloheptyl] - glycine
N - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] -N- [3-methyl -butyl] -glycine
N - [(S) -2- (Quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentene-oyl] glycine ethyl ester
N - [(S) -2- (quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentenoyl] glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentene-oyl] glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [methyl] -glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [methyl] -glycine
N [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [cyclopropyl] - glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [cyclopropyl] -glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [cyclobutyl] -glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [cyclobutyl] -glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [cyclopentyl] -glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [cyclopentyl] -glycine
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [cyclohexyl] -glycine ethyl ester
N - [(S) -2- (3-methyl-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -N- [cyclohexyl] -glycine
N - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - glycine ethyl ester
N - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -N- [methyl] -glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-t etrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4 -pentene-oyl] -N- [methyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -N- [ethyl] -glycine ethyl ester
N - [(S) -2 (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4-pentene -oyl] -N- [ethyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [2-methoxy ethyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [2-methoxy ethyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -N- [tetrahydrofuran-2-yl-methyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -N- [tetrahydrofuran-2-yl-methyl] -glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -N- [tetrahydro-2H-pyran-2-yl-methyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -N- [tetrahydro-2H-pyran-2-yl-methyl] -glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cyclopropyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cyclopropyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cyclobutyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cyclobutyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cyclopentyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cyclopentyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cyclohexyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cyclohexyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cycloheptyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [cycloheptyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- penten-oyl] -N- [benzyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [benzyl] glycine
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [3-methylbutyl] glycine ethyl ester
N - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonamido) -5- (2-amino-imidazol-4-yl) -4- pentene-oyl] -N- [3-methylbutyl] glycine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-aminoimidazol-4-yl) -4-pentenoyl ] piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-aminoimidazol-4-yl) -4-pentenoyl ] -4-methylpiperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperi din
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl ] -4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-ethoxycarbonyl-piperi din
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - piperidine-2-carboxylic acid
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 4-methyl-piperidin-2-car bonic acid
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-aminoimidazol-4-yl) -4-pentenoyl ] -2- ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-aminoimidazol-4-yl) -4-pentenoyl ] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-ethoxycar bonyl-4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperi din-2-carboxylic acid
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-benzyloxycar bonyl-methyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentene -oyl] -2- ethoxy-carbonyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonyl- (N-benzyloxycar bonyl-methyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentene -oyl] -4- methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (Quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] piperidine
1 - [(S) -2- (quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl- piperidine
1 - [(S) -2- (quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-ethoxycarbonyl- 4-methyl-piperi din
1 - [(S) -2- (quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl- piperidine-2-carboxylic acid
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl ] -4-methylpiperidine
1 [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonyl methyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperi din
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 2-ethoxycarbonyl-4-methylpiperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] - 4-methyl-piperidine-2-carbon acid
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl ] -2- ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl ] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonyl methyl) amino) -5- (2-amino-imidazol-4-yl) -4-penten-oyl ] -2- ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl ] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -2-ethoxycar bonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazol-4-yl) -4-pentenoyl] -4-methyl-piperi din-2-carboxylic acid
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4 -pentene-oyl] -piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4 -pentene-oyl] -4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4 -pentene-oyl] -2-ethoxycar bonyl-4-methyl-piperidine
1 - [(S) -2- (1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methylamino) -5- (2-amino-imidazol-4-yl) -4 -pentene-oyl] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazole-4- yl) -4-pentenoyl] piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazole-4- yl) -4-pentenoyl] -4-methylpiperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) -4-pen en-oyl] -4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) -4-pentene-oyl] -4-methyl-piperidine
1- [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazole-4 -yl) -4-pentene-oyl] -4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methyl-amino) -5- (2-amino-imidazole-4- yl) -4-pentene-oyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl-N-methyl) amino) -5- (2-amino-imidazole-4- yl) -4-pentene-oyl] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) -4-pen ten-oyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-ethoxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) -4-pen ten-oyl] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) -4-pentene-oyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-benzyloxycarbonylmethyl) amino) -5- (2-amino-imidazole-4 -yl) -4-pentene-oyl] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazole-4 -yl) -4-pentene-oyl] -2-ethoxycarbonyl-4-methyl-piperidine
1 - [(S) -2- (3-Methyl-1,2,3,4-tetrahydro-quinolin-8-yl-sulfonyl- (N-carboxymethyl) amino) -5- (2-amino-imidazole-4 -yl) -4-pentene-oyl] -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- (4-nitro-benzenesulfonamido) -5- (2-amino-imidazol-4-yl) - 4-pentene-oyl] -4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamide o) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (2R, 4R) -2-hydroxymethyl-4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (2R, 4R) - 2- (ethoxycarbonylmethylaminocarbonyl) -4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -5- (2-aminoimidazol-4-yl) -4-pentenoyl] - (2R, 4R) - 2- (hydroxycarbonylmethyl aminocarbonyl) -4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -3- (2-aminoimidazol-4-yl) propanoyl] -4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -3- (2-aminoimidazol-4-yl) propanoyl] - (2R, 4R) -4-methyl- piperidine-2-carbon acid ethyl ester
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -3- (2-aminoimidazol-4-yl) propanoyl] - (2R, 4R) -4-methyl- piperidine-2-carbon acid
1 - [(S) -2- (3-methyl-quinolin-8-sulfonamido) -3- (2-amino-imidazol-4-yl) propanoyl] - (2R, 4R) -4-methyl-piperidine- 2-carboxylic acid ethyl ester
1 - [(S) -2- (3-methyl-quinolin-8-sulfonamido) -3- (2-amino-imidazol-4-yl) propanoyl] - (2R, 4R) -4-methyl-piperidine- 2-carboxylic acid
1 - [(S) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahyroquinoline-8-sulfone amido] -3- (2-amino-imidazole-4 -yl) -propanoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester
1 - [(S) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahyroquinoline-8-sulfone amido] -3- (2-amino-imidazole-4 -yl) -propanoyl] - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid
1 - [(S) -2- [N- [3-methyl-quinoline-8-sulfonyl] -N- [ethoxycarbonyl methyl] amino] -3- (2-amino-imidazol-4-yl) propanoyl] - 4-methyl-pi peridine
1 - [(S) -2- [N- [3-methyl-quinoline-8-sulfonyl] -N- [hydroxycarbonyl methyl] amino] -3- (2-amino-imidazol-4-yl) propanoyl] - 4-methyl-pi peridine
1 - [(S) -2- [N- [3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinolin-8-sulphonyl] -N- [ethoxycarbonyl-methyl] amino ] -3- (2-amino-imidazol-4-yl) propanoyl] -4-methyl-piperidine
1 - [(S) -2- [N- [3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinolin-8-sulphonyl] -N- [hydroxycarbonyl-methyl] amino ] -3- (2-amino-imidazol-4-yl) propanoyl] -4-methyl-piperidine
1 - [(S) -2- (4-Amino-3,5-dichlorobenzenesulfonamido) -4- (2-aminoimidazol-4-yl) butanoyl] -4-methyl-piperidine
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -4- (2-aminoimidazol-4-yl) butanoyl] - (2R, 4R) -4-methyl- piperidine-2-carbon acid ethyl ester
1 - [(S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -4- (2-aminoimidazol-4-yl) butanoyl] - (2R, 4R) -4-methyl- piperidine-2-carbon acid
1 - [(S) -2- (3-methyl-quinolin-8-sulfonamido) -4- (2-amino-imidazol-4-yl) butanoyl] - (2R, 4R) -4-methyl-piperidine- 2-carboxylic acid ethyl ester
1 - [(S) -2- (3-methyl-quinolin-8-sulfonamido) -4- (2-amino-imidazol-4-yl) butanoyl] - (2R, 4R) -4-methyl-piperidine- 2-carboxylic acid
1 - [(S) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahyroquinoline-8-sulfone amido] -4- (2-amino-imidazole-4 -yl) -butanoyl] - (2R, 4R) -4-methyl-pi peridin-2-carboxylic acid ethyl ester
1 - [(S) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahyroquinoline-8-sulfone amido] -4- (2-amino-imidazole-4 -yl) -butanoyl] - (2R, 4R) -4-methyl-pi peridin-2-carboxylic acid
1 - [(S) -2- [N- [3-methyl-quinoline-8-sulfonyl] -N- [ethoxycarbonyl methyl] amino] -4- (2-amino-imidazol-4-yl) butanoyl] - 4-methyl-pi peridine
1 - [(S) -2- [N- [3-methyl-quinoline-8-sulfonyl] -N- [hydroxycarbonyl methyl] amino] -4- (2-amino-imidazol-4-yl) butanoyl] - 4-methyl-pi peridine
1 - [(S) -2- [N- [3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinolin-8-sulphonyl] -N- [ethoxycarbonyl-methyl] amino ] -4- (2-amino-imidazol-4-yl) butanoyl] -4-methyl-piperidine
1 - [(S) -2- [N- [3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinolin-8-sulphonyl] -N- [hydroxycarbonyl-methyl] amino ] -3- (2-amino-imidazol-4-yl) butanoyl] -4-methyl-piperidine

Claims (14)

1. Substituted 2-amino-imidazoles in the
A is an alkylene group with 1 to 6 carbon atoms or an alkenylene group with 3 to 6 carbon atoms, in each of which the double bond is in the α-position to the imidazole ring,
R₁ an optionally by an alkyl, alkoxy, dimethyl amino, diethylamino, nitro, amino, cyano or trifluoromethyl group or a fluorine, chlorine, bromine or iodine atom monosubstituted phenyl radical, an alkyl or Alkoxy groups disubstituted phenyl radical, where the substituents can be the same or different, or a phenyl radical trisubstituted by an amino group and two chlorine or bromine atoms,
a 1-naphthyl or 2-naphthyl radical which is optionally monosubstituted by an alkyl, alkoxy, dimethylamino or diethylamino group or a chlorine atom or a 1-naphthyl or 2-naphthyl radical which is disubstituted by alkyl or alkoxy groups, the substituents may be the same or different,
a quinolin-8-yl, isoquinolin-5-yl, isoquinolin-6-yl or isoquinolin-7-yl radical which is optionally substituted by an alkyl group,
an isoindolin-5-yl-, 1,2,3,4-tetrahydroquinolin-8-yl-, 1,2,3,4-tetrahydro-isoquinolin-5-yl- which is optionally substituted in the non-aromatic ring by an alkyl group, 1,2,3,4-tetrahydro-isoquinolin-6-yl-, 1,2,3,4-tetrahydro-isoquinolin-7-yl- or 2,3,4,5-tetrahydro-1H-3-benzazepine 7-yl residue,
a 5,6,7,8-tetrahydro-1-naphthyl-, 5,6,7,8-tetrahydro-2-naphthyl-, anthracen-1-yl-, anthraquinon-1-yl-, 9H-fluorene-3 -yl, dibenzofuran-2-yl, dibenzofuran-4-yl, 9H-xanthene-2-yl, dibenzothiophene-2-yl or phenoxathiin-2-yl radical,
R₂ is a hydrogen atom, a methyl group or a Y₁-CO- (C₁-C₃) alkyl group, whereY₁ represents a hydroxyl, alkoxy, benzyloxy, amino, alkylamino or dialkylamino radical, R₃ is a hydrogen atom or a methyl group ,
R₄ is an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 3 to 6 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms, an alkoxyalkyl, benzyl, Te trahydrofuran-2-yl-methyl- or tetrahydropyran-2-yl-methyl - rest,
R₅ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a Y₁-CO- (C₁-C₃) alkyl or (p-Y₁-CO-C₆H₄) - (C₁-C₃) alkyl - Group, wherein Y₁ is defined as mentioned at the beginning, or
R₄ and R₅ together with the intermediate nitrogen atom, an alkyleneimino radical optionally monosubstituted by an alkyl or alkoxy group or by a radical W or a alkyleneimino radical disubstituted by an alkyl group and a radical W, the alkyleneimino radical containing 4 to 6 carbon atoms can andW a HOCH₂-, alkoxy-CH₂-, alkyl-CO-O-CH₂-, alkoxy-CO-O-CH₂-, H₂N-CH₂-, alkyl-NH-CH₂-, benzyl-NH-CH₂-, alkyl- CO-NH-CH₂-, alkoxy-CO-NH-CH₂-, benzyloxy-CO-NH-CH₂-, (alkyl) ₂N-CH₂-, (benzyl) ₂N-CH₂-, NC-, 1H-tetrazole-5- yl or Y₂-CO group, wherein
Y₂ is a hydroxyl, alkoxy, amino, alkylamino, benzyl amino, dialkylamino, dibenzylamino, (carboxyalkyl) amino, (alkoxycarbonylalkyl) amino or (benzyloxycar bonylalkyl) amino radical , mean, where, unless stated otherwise, the alkyl and alkylene parts mentioned above may each contain 1 to 4 carbon atoms,
their stereoisomers, their mixtures and their salts. 2. Substituted 2-amino-imidazoles of the general formula I according to claim 1, in which
A is an alkylene group with 1 to 4 carbon atoms or an alkenylene group with 3 or 4 carbon atoms, in each of which the double bond is in the α-position to the imidazole ring,
R₁ is a phenyl radical monosubstituted by an alkyl, alkoxy, dimethylamino, diethyl amino, nitro or amino group in the 4-position, a phenyl radical disubstituted by two alkyl or two alkoxy groups in the 3,4-position or one by an amino group in the 4-position and by chlorine or bromine atoms in the 3,5- or 2,5-position trisubstituted phenyl radical,
a 1-naphthyl or 2-naphthyl radical which is optionally monosubstituted by an alkyl, alkoxy or dimethyl amino group or a 1-naphthyl or 2-naphthyl radical which is disubstituted by two alkyl or two alkoxy groups,
a quinolin-8-yl or isoquinolin-5-yl radical optionally substituted by an alkyl group,
an isoindolin-5-yl-, 1,2,3,4-tetrahydroquinolin-8-yl-, 1,2,3,4-tetrahydro-isoquinolin-5-yl- which is optionally substituted in the non-aromatic ring by an alkyl group , 1,2,3,4-tetrahydro-isoquinolin-6-yl-, 1,2,3,4-tetrahydro-isoquinolin-7-yl- or 2,3,4,5-tetrahydro-1H-3-benzazepine -7-yl residue,
R₂ is a hydrogen atom or a methyl group,
R₃ is a hydrogen atom,
R₄ is an alkyl group with 1 to 5 carbon atoms, a cyclo alkyl group with 3 to 6 carbon atoms or a benzyl group,
R₅ is a hydrogen atom, an alkyl group or a Y₁-CO-CH₂ group, where Y₁ is a hydroxy, alkoxy, benzyloxy, amino, alkylamino or dialkylamino radical, or R₄ and R₅ together with the intermediate nitrogen atom an alkyleneimino radical optionally substituted by an alkyl group or a radical W or by an alkyl group and a radical W, where the alkyleneimino radical can contain 4 to 6 carbon atoms andW represents a Y₂-CO group, where
Y₂ represents a hydroxyl, alkoxy, benzyloxy, amino, alkyl amino, dialkylamino, (carboxyalkyl) amino, (alkoxy carbonylalkyl) amino or (benzyloxycarbonylalkyl) amino radical, unless otherwise mentioned, the alkyl and alkylene parts mentioned above may each contain 1 to 4 carbon atoms,
their stereoisomers, their mixtures and their salts. 3. Substituted 2-amino-imidazoles of the general formula I according to claim 1, in which
A is an alkylene group with 1 to 3 carbon atoms or a propenylene group in which the double bond is in the α-position to the imidazole ring,
R₁ is a phenyl radical trisubstituted by an amino group in the 4-position and by two chlorine atoms in the 3,5- or 2,5-position,
a 1-naphthyl or 2-naphthyl radical optionally substituted by a dimethylamino group,
a quinolin-8-yl or isoquinolin-5-yl radical optionally substituted by a methyl group,
a 1,2,3,4-tetrahydro-quinolin-8-yl-, 1,2,3,4-tetrahydro-isoquinolin-5-yl-, 1,2,3, which is optionally substituted in the non-aromatic ring by a methyl group, 4-tetrahydro-isoquinolin-6-yl or 1,2,3,4-tetrahydro-isoquinolin-7-yl radical,
R₂ is a hydrogen atom,
R₃ is a hydrogen atom,
R₄ and R₅ together with the intermediate nitrogen atom, a piperidino radical optionally substituted by an alkyl group in the 4-position or a piperidino radical substituted by an alkyl group in the 4-position and a radical W in the 2-position, where W is a carboxy -, Alkoxycarbonyl, benzyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, (carboxymethyl) aminocarbonyl, (alkoxycarbonylmethyl) aminocarbonyl or (benzyloxycarbonylmethyl) aminocarbonyl group, unless otherwise stated, means before alkyl parts mentioned above may each contain 1 to 4 carbon atoms,
their stereoisomers, their mixtures and their salts. 4. Substituted 2-amino-imidazoles of the general formula I according to claims 1 to 3, which contain a (2R, 4R) -disubstituted piperidino radical,
their stereoisomers, their mixtures and their salts. 5. Substituted 2-amino-imidazoles of the general formula I according to claims 1 to 4, which on the C * carbon atom (S) - are configured, and their salts. 6. The following substituted 2-amino-imidazoles of the general formula I:

• (a) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4- (Z) -pentene-oyl] -4-methyl-piperidine,
• (b) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) -4- (E) -pentene-oyl] -4-methyl-piperidine,
• (c) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -5- (2-amino-imidazol-4-yl) pentanoyl] -4-methyl-piperidine,
• (d) 1 - [(2S) -2- (4-amino-3,5-dichlorobenzenesulfonamido) -6- (2-amino-imidazol-4-yl) -5- (Z) -hexen-oyl] -4-methyl-piperidine,
• (e) 1 - {(2S) -5- (2-Amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydroquinoline -8-sulfonamido] -4- (Z) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid, ethyl ester,
• (f) 1 - {(2S) -5- (2-Amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydro-quinoline -8-sulfonamido] -4- (E) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid, ethyl ester,
• (g) 1 - {(2S) -5- (2-Amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydroquinoline -8-sulfonamido] -pentanoyl} - (2R, 4R) - 4-methyl-piperidine-2-carboxylic acid ethyl ester and
• (h) 1 - {(2S) -5- (2-Amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl-1,2,3,4-tetrahydroquinoline -8-sulfonamido] -pentanoyl} - (2R, 4R) - 4-methyl-piperidine-2-carboxylic acid

as well as their salts. 7. 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl- 1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -4- (E) -pentene-oyl} - (2R, 4R) -4-methyl-piperidine-2-carboxylic acid ethyl ester and its Salts. 8. 1 - {(2S) -5- (2-amino-imidazol-4-yl) -2 - [(3-R, S) -3-methyl- 1,2,3,4-tetrahydro-quinoline-8-sulfonamido] -pentanoyl} - (2R, 4R) - 4-methyl-piperidine-2-carboxylic acid ethyl ester and its salts.   9. Physiologically acceptable salts of the compounds according to Claims 1 to 8. 10. Medicament containing a compound according to the claims chen 1 to 8 or a physiologically acceptable salt according to Claim 9. 11. Process for the manufacture of a medicament according to An saying 10, characterized in that a connection according to claims 1 to 8 or a physiologically acceptable Salt according to claim 9 in one or more inert customary Carriers are incorporated. 12. Use of a compound according to claims 1 to 9 for Production of a drug with a thrombin-inhibiting and prolonging the thrombin time. 13. A process for the preparation of the compounds according to claims 1 to 9, characterized in that

• a) an imidazo [1,2-a] pyrimidine of the general formula in the
  A and R₁ to R₅ are as defined in claims 1 to 8,
  is reacted with hydrazine of the formula H₂N-NH₂ (3), or
• b) for the preparation of a compound of the general formula (1) in which A represents an alkylene group having 3 to 6 carbon atoms,
  a substituted 2-amino-imidazole of the general formula in the
  R₁ to R₅ are as defined in claims 1 to 8 and
  A₁ represents an alkenylene group with 3 to 6 carbon atoms, in each of which the double bond is in the α-position to the imidazole ring, is hydrogenated, or
• c) a compound of the general formula in the
  A and R₁ to R₅ are as defined in claims 1 to 8,
  one of the radicals R₆ and R₇ a protective group for an amino or imino group and
  the other of the radicals R₆ and R₇ represent a hydrogen atom or a protective group for an amino or imino group, protective radicals are split off, or
• d) for the preparation of a compound of the general formula (1) in which A represents an alkylene group having 1 to 6 carbon atoms,
  an imidazole of the general formula in the
  R₁ to R₅ are as defined in claims 1 to 8 and
  A₂ represents an alkylene group with 1 to 6 carbon atoms,
  with a diazonium salt of the general formula in the
  R₈ is a hydrogen or halogen atom, a methyl, nitro or alkoxycarbonyl group and
  X⁻ is a chloride or bromide anion,
  implemented and then a so obtained azo compound of the general formula in the
  A₂, R₁ to R₅ and R₈ are as defined in claims 1 to 8,
  is split hydrating, or
• e) a carboxylic acid of the general formula in the
  A, R₁ to R₃ are as defined in claims 1 to 8,
  R₉ is a hydrogen atom or a protecting group for an amino group and
  R₁₀ represent a hydrogen atom or a protective group for an imino group,
  with an amine of the general formula in the
  R₄ and R₅ are as defined in claims 1 to 8,
  or are reacted with their reactive derivatives, which may have been prepared in the reaction mixture, and, if necessary, subsequent protective residues are subsequently split off, or
• f) an amino compound of the general formula in the
  A, R₂ to R₅, R₉ and R₁₀ are defined as in claims 1 to 8,
  with a sulfonic acid halide of the general formula R₁-SO₂-Y (12) in which
  R₁ is as defined in claims 1 to 8 and
  Y represents a leaving group such as a halogen atom,
  implemented and, if necessary, subsequently split off any protective residues used, or
• g) for the preparation of a compound of the general formula (1) in which A represents an alkylene group having 1 to 6 carbon atoms,
  an aminoketone hydrochloride of the general formula in the
  R₁ to R₅ are as defined in claims 1 to 8 and
  A₂ represents an alkylene group with 1 to 6 carbon atoms,
  is reacted with cyanamide of the formula H₂N-CN (14) and
  if desired, a compound of the general formula (1) thus obtained, in which R 1 represents a quinolin-8-yl or isoquinolin-5-yl radical optionally substituted by an alkyl group having 1 to 4 carbon atoms, by reduction into a corresponding compound of general formula (1) in which R 1 is an 1,2,3,4-tetrahyro-quinolin-8-yl- or 1,2,3,4-tetrahydro-isoquinoline which is optionally substituted by an alkyl group having 1 to 4 carbon atoms -5-yl- represents residue, is transferred and / or
  a compound of the general formula (1) thus obtained, in which R₂ is an alkoxycarbonyl (C₁-C₃) alkyl radical, by hydrolysis into a corresponding compound of the general formula (1), in which R₂ is a carboxy- (C₁- C₃) alkyl group, is transferred and / or
  a compound of the general formula (1) thus obtained, in which R₅ represents an alkoxycarbonyl- (C₁-C₃) alkyl or (p-alkoxycarbonylphenyl) - (C₁-C₃) alkyl radical, by hydrolysis into a corresponding compound of the general Formula (1) in which R₅ represents a carboxy- (C₁-C₃) alkyl or (p-carboxy-phenyl) - (C₁-C₃) alkyl radical, is converted and / or
  a compound of the general formula (1) thus obtained, in which the R₄R₅N group contains an alkyleneimine radical with 4 to 6 carbon atoms in the alkylene part which is substituted by a radical W, by hydrolysis, if W represents an alkoxycarbonyl or benzyloxycarbonyl group, is converted into a corresponding compound of the general formula (1) in which W represents a carboxy group, or by means of hydrogenolysis, if W represents a benzyloxy carbonyl group, into a corresponding compound of the general formula (1) in which W represents a carboxy group and or
  if necessary, a protective residue used during the reactions to protect reactive groups is split off and / or
  if desired, a compound of the general formula I thus obtained is then separated into its stereoisomers and / or
  a compound of the general formula I thus obtained is converted into its salts, in particular into its physiologically tolerable salts with an organic or organic base.