CA2563401A1

CA2563401A1 - Imidazole derivatives used as tafia inhibitors

Info

Publication number: CA2563401A1
Application number: CA002563401A
Authority: CA
Inventors: Christopher Kallus; Holger Heitsch; Andreas Lindenschmidt; Sven Grueneberg; Hauke Szillat
Original assignee: Sanofi-Aventis Deutschland Gmbh; Christopher Kallus; Holger Heitsch; Andreas Lindenschmidt; Sven Grueneberg; Hauke Szillat
Current assignee: Sanofi Aventis Deutschland GmbH
Priority date: 2004-04-22
Filing date: 2005-04-07
Publication date: 2005-11-10
Anticipated expiration: 2025-04-07
Also published as: AU2005238144A1; ATE386737T1; AR053302A1; PE20060172A1; DE502005002927D1; NZ550757A; UY28868A1; NI200600217A; DE102004020186A1; JP4939401B2; EP1740569A1; DK1740569T3; RS50553B; ECSP066941A; TW200602325A; ATE523505T1; PL1740569T3; KR20070007346A; IL178672A; BRPI0510159A

Abstract

The invention relates to compounds of formula (I), which are inhibitors of the activated thrombin-activatable fibrinolysis inhibitor. The compounds of formula (I) are suited for producing medicaments for the prevention and treatment of diseases accompanied by thromboses, embolisms, hypercoagulability or fibrotic changes.

Claims

1. A compound of the formula and/or all stereoisomeric forms of the compound of the formula I and/or mixtures of these forms in any ratio, and/or a physiologically tolerated salt of the compound of the formula I, where U is 1) hydrogen atom,

2) -(C1-C6)-alkyl,

3) -(C3-C6)-cycloalkyl,

4) fluorine,

5) -O-CF3 or

6) -CF3, X is the radical of the formula II
-(A1)m-A2 (II) in which m is the integer zero or 1, A1 is 1) -(CH2)n- in which n is the integer 1, 2 or 3, or 2) -O-(CH2)n- in which n is the integer zero, 1, 2 or 3, A2 is 1) 4- to 15-membered Het ring in which Het ring comprises at least one N atom and is substituted by an amino group and may additionally be substituted independently of one another once, twice or three times by a -(C1-C3)-alkyl, halogen, -CF3 or -O-CF3, 2) -(C1-C6)-alkyl-NH2 or 3) -(C3-C8)-cycloalkyl-NH2, Y is 1) the radical of the formula III
A3-(A4)o-(A5)p (III) where a) A3 is -(C3-C8)-cycloalkyl or -(C2-C6)-alkynylene, in which cycloalkyl or alkynylene is unsubstituted or substituted independently of one another once, twice or three times by -O-R10 or R1, A4 is -N(R2)2- in which R2 is as defined below, and the two R2 radicals are defined independently of one another, A5 is absent , o is the integer zero or 1, and R10 is a hydrogen atom, -(C1-C6)-alkyl or -(C6-C14)-aryl, b) A3 is -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by -O-R10 or R1, A4 is-N(R2)-, and A5 is a)1) -C(O)-R3, a)2) -C(O)-N(R4)-R5, a)3) -(SO2)-R6, or a)4) -C(O)-O-R7, o is the integer 1, and p is the integer 1, c) A3 is cyclic amine having 3 to 8 ring atoms in which cyclic amine is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 and A5 are as defined under b), where A5 is bonded to the N atom of A3, o is the integer zero, and p is the integer zero or 1, or d) A3 is -(CH2)q-(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 and A5 are as defined under b), o is the integer zero or 1, and p is the integer 1, and q is the integer zero, 1, 2 or 3, e) A3 is -(CH2)r-Het in which Het is a 4- to 15-membered Het ring, and Het ring is unsubstituted or substituted independently of one another once, twice or three times by =O or R1, A4 and A5 are as defined under b), o is the integer zero or 1, p is the integer 1 and r is the integer zero, 1, 2 or 3, f) A3 is -(CH2)q-(C6-C14)-aryl, in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 i s -O-, A5 is -(C6-C14)-aryl, in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, o and p are the integer 1 and q is the integer zero, 1, 2 or 3, g) -CH(-(C6-C14)-aryl)-(C6-C14)-aryl, where R1 is a) -(C6-C14)-aryl, where aryl is unsubstituted or substituted independently of one another once, twice or three times by -(C1-C6)-alkyl, -(C0-C4)-alkyl-(C3-C8)-cycloalkyl, -CF3, =O, -O-CF3 or halogen, b) 4- to 15-membered Het ring, c) -(C1-C6)-alkyl, d) -(C0-C4)-alkyl-(C3-C8)-cycloalkyl, e) -CF3, f) -O-CF3 or g) halogen, where R2 is a) -(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -CF3 or e) hydrogen atom, where R3, R6 and R7 are identical or different is independently of one another a) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) 4- to 15-membered Het ring in which Het ring is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or e) hydrogen atom, where R4 and R5 are identical or different is independently of one another a) -(C1-C6)-alkyl or -(C2-C10)-alkenyl, in which alkyl or alkenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) 4- to 15-membered Het ring in which Het ring is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or e) hydrogen atom, or R4 and R5 form together with the nitrogen atom to which they are bonded a ring having 3 to 8 ring atoms which may, in addition to the nitrogen atom, also comprise one to two additional heteroatoms from the series oxygen, sulfur or nitrogen, Y is 2) the radical of the formula IV, where R8 is a) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) 4- to 15-membered Het ring in which Het ring is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or e) hydrogen atom, Y is 3) the radical of the formula V

where in case a) R12 is 1) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, 2) -(C0-C3)-alkyl-(C3-C6)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, 3) -(C0-C3)-alkyl-(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, or 4) -(C0-C3)-alkyl-Het in which Het is unsubstituted or substituted independently of one another once, twice or three times by R1, and R13 is 1) -(C0-C3)-alkyl-(C6-C14)-aryl in which alkyl and aryl are each unsubstituted or substituted independently of one another once, twice or three times by R1, or 2) -(C0-C3)-alkyl-Het in which alkyl and Het are each unsubstituted or substituted independently of one another once, twice or three times by R1, where in case b) R12 is 1) hydrogen atom, 2) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, 3) -(C0-C3)-alkyl-(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, or 4) -(C0-C3)-alkyl-Het in which Het is unsubstituted or substituted independently of one another once, twice or three times by R1, and R13 is -CH(R8)-R9 where R8 and R9 are independently of one another -(C6-C14)-aryl or Het in which Het and aryl are each unsubstituted or substituted independently of one another once, twice or three times by -O-(C1-C4)-alkyl or R1, and R16, R17, R18 and R19 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted once or twice by R1, 3) halogen, 4) -OH, 5) -NH2, 6) -(C0-C3)-alkyl-(C6-C14)-aryl in which alkyl and aryl are each unsubstituted or substituted independently of one another once, twice or three times by R1, or

7) -(C0-C3)-alkyl-Het in which alkyl and Het are each unsubstituted or substituted independently of one another once, twice or three times by R1, or R16 and R17 or R18 and R19 form together with the carbon atom to which they are respectively bonded a ring having 3 to 6 ring atoms, or Y is 4) the radical of the formula VI, where R24 and R25 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, 3) -(C0-C3)-alkyl-(C6-C14)-aryl in which alkyl and aryl are each unsubstituted or substituted independently of one another once, twice or three times by R1, 4) -(C0-C3)-alkyl-Het in which alkyl and Het are each unsubstituted or substituted independently of one another once, twice or three times by R1, or 5) -(C0-C3)-alkyl-(C3-C6)-cycloalkyl, or R24 and R25 form together with the nitrogen atom to which they are bonded a ring having 3 to 8 ring atoms which may, in addition to the nitrogen atom, also comprise one to two additional heteroatoms from the series oxygen, sulfur or nitrogen, R26, R27, R28 and R29 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, 3) halogen, 4) -OH, 5) -NH2;
6) -(C0-C3)-alkyl-(C6-C14)-aryl in which alkyl and aryl are each unsubstituted or substituted independently of one another once, twice or three times by R1, or 7) -(C0-C3)-alkyl-Het in which alkyl and Het are each unsubstituted or substituted independently of one another once, twice or three times by R1, or R26 and R27 or R28 and R29 form together with the carbon atom to which they are respectively bonded a ring having 3 to 6 ring atoms, Z is 1) hydrogen atom, 2) -(C1-C6)-alkyl, 3) -(C1-C6)-alkyl-OH, 4) -(C0-C4)-alkyl-(C3-C6)-cycloalkyl, 5) -(C1-C10)-alkyl-O-C(O)-O-R1, 6) -(CH2)r(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, and r is the integer zero, 1, 2 or 3, or 7) -(CH2)s-Het in which Het is unsubstituted or substituted independently of one another once, twice or three times by R1, and s is the integer zero, 1, 2 or 3.

2. A compound of the formula Ia, as claimed in claim 1, where U is 1) hydrogen atom, 2) -(C1-C6)-alkyl, 3) -(C3-C6)-cycloalkyl, 4) fluorine, 5) -O-CF3 or 6) -CF3, X is the radical of the formula II in which m is the integer zero or 1, A1 is 1) -(CH2)n- in which n is the integer 1, 2 or 3, or 2) -O-(CH2)n- in which n is the integer zero, 1, 2 or 3, A2 is 1) 4- to 15-membered Het ring in which Het ring is selected from the group of acridinyl, azepinyl, azetidinyl, aziridinyl, benzimidazalinyl, benzimidazolyl, carbolinyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, chromanyl, chromenyl, cinnolinyl, deca-hydroquinolinyl, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl (benzimidazolyl), isothiazolidinyl, 2-isothiazolinyl, isothiazolyl, isoxazolyl, isoxazolidinyl, isoxazolinyl, morpholinyl, naphthyridinyl, octahydroisoquinolinyl, oxadiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolidinyl, oxazolyl, pyrimidinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxathiinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, purynyl, pyranyl, pyrazinyl, pyroazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pryidooxazolyl, pyridoimidazolyl, pyridothiazolyl, pyridothiophenyl, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrahydropyridinyl, 6H-1,2,5-thiadazinyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianthrenyl, thiazolyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiomorpholinyl, triazinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl and xanthenyl and in which the Het ring is substituted by an amino group and may additionally be substituted independently of one another once, twice or three times by a -(C1-C3)-alkyl, halogen, -CF3 or -O-CF3, 2) -(C1-C6)-alkyl-NH2 or 3) -(C3-C8)-cycloalkyl-NH2, Y is 1) the radical of the formula III where a) A3 is -(C3-C8)-cycloalkyl or -(C2-C6)-alkynylene in which cycloalkyl or alkylnylene is unsubstituted or substituted independently of one another once, twice or three times by -O-R10 or R1, A4 is-N(R2)2- in which R2 is as defined below, and the two R2 radicals are defined independently of one another, A5 is absent and o is the integer zero or 1, and R10 is hydrogen atom, -(C1-C6)-alkyl or phenyl, b) A3 is -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by -O-R10 or R1, A4 is-N(R2)-, and A5 is a)1) -C(O)-R3, a)2) -C(O)-N(R4)-R5, a)3) -(SO2)-R6, or a)4) -C(O)-O-R7, o is the integer 1, and p is the integer 1, c) A3 is cyclic amine from the group of propylamine, azetidine, pyrrolidine, piperidine, azepanes or azocanes, in which cyclic amine is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 and A5 are as defined under b), where A5 is bonded to the N atom of A3, o is the integer zero, and p is the integer zero or 1, or d) A3 is -(CH2)q-(C6-C14)-aryl in which aryl is selected from the group of phenyl, naphthyl, anthryl or fluorenyl and is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 and A5 are as defined under b) o is the integer zero or 1, and p is the integer 1, and q is the integer zero, 1, 2 or 3, e) A3 is -(CH2)r-Het in which Het is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by =O or R1, A4 and A5 are as defined under b), o is the integer zero or 1, p is the integer 1 and r is the integer zero, 1, 2 or 3, f) A3 is -(CH2)q-(C6-C14)-aryl in which is aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 i s -O-, A5 is -(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, o and p are the integer 1 and q is the integer zero, 1, 2 or 3, g) -CH(phenyl)-phenyl, where R1 is a) -(C6-C14)-aryl in which aryl is as defined above and where aryl is unsubstituted or is substituted independently of one another once, twice or three times by -(C1-C6)-alkyl, -(C0-C4)-alkyl-(C3-C8)-cycloalkyl, -CF3, =O, -O-CF3 or halogen b) 4- to 15-membered Het ring in which Het is as defined above, c) -(C1-C6)-alkyl, d) -(C3-C8)-cycloalkyl, e) -CF3, f) -O-CF3 or g) halogen, where R2 is a) -(C6-C14)-aryl in which aryl is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -CF3 or e) hydrogen atom, where R3, R6 and R7 are identical or different is independently of one another a) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C6-C14)-aryl in which aryl is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, c) 4- to 15-membered Het ring in which Het ring is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or e) hydrogen atom, where R4 and R5 are identical or different is independently of one another a) -(C1-C6)-alkyl or -(C2-C10)-alkenyl, in which alkyl or alkenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C6-C14)-aryl in which aryl is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, c) 4- to 15-membered Het ring in which Het ring is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or e) hydrogen atom, or R4 and R5 form together with the nitrogen atom to which they are bonded a ring having 3 to 8 ring atoms selected from the group of propylamine, azetidine, pyrrolidine, piperidine, azepanes, azocanes, azepine, dioxazole, dioxazine, 1,4-diazepane, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, imidazole, imidazoline, imidazolidine, isothiazole, isothiazolidine, isothiazoline, isoxazole, isoxazoline, isoxazolidine, 2-isoxazoline, ketopiperazine, morpholine, [1,4]oxazepane, oxazole, piperazine, pyrazine, pyrazole, pyrazoline, pyrazolidine, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolidinone, pyrroline, tetrahydropyridine, thiazole, thiadiazole, thiazolidine, thiazoline, thiomorpholine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, 1,2,3-triazole or 1,2,4-triazole, Y is 2) the radical of the formula IV where formula IV is a compound from the group of azetidin-2-one, pyrrolidin-2-one, piperidin-2-one, azepan-2-one and azocan-2-one and is substituted on the nitrogen atom in each case by R8, where R8 is a) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C6-C14)-aryl in which aryl is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, c) 4- to 15-membered Het ring in which Het ring is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or e) hydrogen atom, Y is 3) the radical of the formula V, where in case a) R12 is 1) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, 2) -(C0-C3)-alkyl-(C3-C6)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, 3) -(C0-C3)-alkyl-(C6-C14)-aryl in which aryl is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, or 4) -(C0-C3)-alkyl-Het in which Het is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, and R13 is 1) -(C0-C3)-alkyl-(C6-C14)-aryl in which alkyl and aryl is as defined above and are each unsubstituted or substituted independently of one another once, twice or three times by R1, or 2) -(C0-C3)-alkyl-Het, in which alkyl and Het are as defined above and are each unsubstituted or substituted independently of one another once, twice or three times by R1, or in case b) R12 is 1) hydrogen atom, 2) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, 3) -(C0-C3)-alkyl-(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, or 4) -(C0-C3)-alkyl-Het in which Het is unsubstituted or substituted independently of one another once, twice or three times by R1, and R13 is -CH(R8)-R9 where R8 and R9 are independently of one another -(C6-C14)-aryl or Het in which Het and aryl are each as defined above and are unsubstituted or substituted independently of one another once, twice or three times by -O-(C1-C4)-alkyl or R1, and R16, R17, R18 and R19 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, 3) halogen, 4) -OH, 5) -NH2, 6) -(C0-C3)-alkyl-(C6-C14)-aryl in which alkyl and aryl is as defined above and are each unsubstituted or substituted independently of one another once, twice or three times by R1, or 7) -(C0-C3)-alkyl-Het in which alkyl and Het is as defined above and are each unsubstituted or substituted independently of one another once, twice or three times by R1, or R16 and R17 or R18 and R19 form together with the carbon atom to which they are respectively bonded a ring having 3 to 6 ring atoms from the group of cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or Y is 4) the radical of the formula VI, where R24 and R25 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, 3) -(C0-C3)-alkyl-(C6-C14)-aryl in which alkyl and aryl is as defined above and are each unsubstituted or substituted independently of one another once, twice or three times by R1, 4) -(C0-C3)-alkyl-Het, in which alkyl and Het is as defined above and are each unsubstituted or substituted independently of one another once, twice or three times by R1, or 5) -(C0-C3)-alkyl-(C3-C6)-cycloalkyl, or R24 and R25 form together with the nitrogen atom to which they are bonded a ring having 3 to 8 ring atoms from the group of propylamine, azetidine, pyrrolidine, piperidine, azepanes, azocanes, azepine, dioxazole, dioxazine, 1,4-diazepane, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, imidazole, imidazoline, imidazolidine, isothiazole, isothiazolidine, isathiazoline, isoxazole, isoxazoline, isoxazolidine, 2-isoxazoline, ketopiperazine, morpholine, [1,4]oxazepane, oxazole, piperazine, pyrazine, pyrazole, pyrazoline, pyrazolidine, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolidinone, pyrroline, tetrahydropyridine, thiazole, thiadiazole, thiazolidine, thiazoline, thiomorpholine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, 1,2,3-triazole or 1,2,4-triazole, R26, R27, R28 and R29 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, 3) halogen, 4) -OH, 5) -NH2, 6) -(C0-C3)-alkyl-(C6-C14)-aryl in which alkyl and aryl is as defined above and are each unsubstituted or substituted independently of one another once, twice or three times by R1, or 7) -(C0-C3)-alkyl-Het in which alkyl and Het is as defined above and are each unsubstituted or substituted independently of one another once, twice or three times by R1, or R26 and R27 or R28 and R29 form together with the carbon atom to which they are respectively bonded a ring having 3 to 6 ring atoms from the group of cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, Z is 1) hydrogen atom, 2) -(C1-C6)-alkyl, 3) (C2-C6)-cycloalkyl, 4) (C1-C10)-alkyl-O-C(O)-O-R1, 5) -(CH2)r-(C6-C14)-aryl in which aryl is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, and r is the integer zero, 1, 2 or 3, or 6) -(CH2)s-Het in which Het is as defined above and is unsubstituted or substituted independently of one another once, twice or three times by R1, and s is the integer zero, 1, 2 or 3.

3. A compound of the formula la as claimed in claims 1 or 2, where U is hydrogen atom, -CF3, fluorine or -CH3, X is the radical of the formula II in which m is the integer 1, A1 is 1) -(CH2)-, 2) -O-(CH2)n- in which n is the integer zero or 1, or 3) covalent bond, A2 is 1) aminopyridyl in which aminopyridyl is unsubstituted or substituted independently of one another once, twice or three times by -(C1-C3)-alkyl, halogen or -CH3, 2) aminothiazolyl in which aminothiazolyl is unsubstituted or substituted independently of one another once, twice or three times by -(C1-C3)-alkyl, halogen or -CH3, 3) -(C1- C3)-alkyl-NH2 or 4) -(C3-C8)-cycloalkyl-NH2, Y is 1) the radical of the formula III where a) A3 is -(C3-C8)-cycloalkyl or (C2-C6)-alkynylene in which cycloalkyl or alkynylene is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 is -N(R2)2- in which R2 is as defined below, and the two R2 radicals are defined independently of one another, A5 is absent and o is the integer zero or 1, b) A3 is -(C3-C6)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 is-N(R2)- , and A5 is a)1) -C(O)-R3, a)2) -C(O)-N(R4)-R5, a)3) -(SO2)-R6 or a)4) -C(O)-O-R7, o is the integer 1, and p is the integer 1, c) A3 is cyclic amine having 3 to 8 ring atoms in which cyclic amine is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 and A5 are as defined under b), where A5 is bonded to the N atom of A3, o is the integer zero, and p is the integer zero or 1, or d) A3 is -(CH2)q-(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 and A5 are as defined under b), o is the integer zero or 1, and p is the integer 1, and q is the integer zero, 1, 2 or 3, e) A3 is -(CH2)r-Het in which Het is pyrrolidine, benzothiophene or piperidine, which is unsubstituted or substituted independently of one another once, twice or three times by =O or R1, A4 and A5 are as defined under b), o is the integer zero or 1, p is the integer 1 and r is the integer zero, 1, 2 or 3, f) A3 is -(CH2)q-phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 i s -O-, A5 is phenyl, in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, o and p are the integer 1 and q is the integer 1 or 2, where R1 is a) phenyl, where phenyl is unsubstituted or substituted independently of one another once, twice of three times by -(C1-C4)-alkyl, b) triazolyl or pyridinyl, c) -(C1-C4)-alkyl, d) -(C3- C6)-cycloalkyl, e) -CF3, f) -O-CF3, g) fluorine or h) chlorine, where R2 is a) phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C1- C3)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) -(C3-C6)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -CF3 or e) hydrogen atom, where R3, R6 and R7 are identical or different are independently of one another a) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) 4- to 15-membered Het ring in which Het ring is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or e) hydrogen atom, where R4 and R5 are identical or different are independently of one another a) -(C1-C6)-alkyl or (C2-C6)-alkenyl, in which alkyl or alkenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) -(C6-C14)-aryl in which aryl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) 4- to 15-membered Het ring in which Het ring is unsubstituted or substituted independently of one another once, twice or three times by R1, d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or e) hydrogen atom, or R4 and R5 form together with the nitrogen atom to which they are bonded a ring derived from azetidine, pyrrolidine, piperidine, azepanes, azocanes, azepine, dioxazole, dioxazine, 1,4-diazepane, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, imidazole, imidazoline, imidazolidine, isothiazole, isothiazolidine, isothiazoline, isoxazole, isoxazoline, isoxazolidine, 2-isoxazoline, ketopiperazine, morpholine, [1,4]oxazepane, oxazole, piperazine, pyrazine, pyrazole, pyrazoline, pyrazolidine, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolidinone, pyrroline, tetrahydropyridine, thiazole, thiadiazole, thiazolidine, thiazoline, thiomorpholine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, 1,2,3-triazole or 1,2,4-triazole, Y is 2) the radical of the formula IV selected from the group of azetidin-2-one, pyrrolidin-2-one or piperidin-2-one, where the radical is substituted on the nitrogen atom in each case by R8, where R8 is a) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) hydrogen atom or d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, Y is 3) the radical of the formula V where in the case a) R12 is 1) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, 2) -(C0-C3)-alkyl-(C3-C6)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or 3) -(C0-C3)-alkyl-phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, and R13 is 1) -(C0-C3)-alkyl-phenyl in which alkyl and phenyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, or 2) -(C0-C3)-alkyl-pyridyl in which alkyl and pyridyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, or in the case b) R12 is 1) hydrogen atom, 2) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, 3) -(C0-C3)-alkyl-phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or 4) -(C0-C3)-alkyl-pyridyl in which alkyl and pyridyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, and R13 is -CH(R8)-R9 where R8 and R9 are independently of one another phenyl or pyridyl in which phenyl or pyridyl are each unsubstituted or substituted independently of one another once, twice or three times by-O-(C1-C4)-alkyl or R1, and R16, R17, R18 and R19 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C3)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, 3) fluorine, 4) -OH, 5) -NH2 or 6) -(C0-C3)-alkyl-phenyl, in which alkyl and phenyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, or Y is 4) the radical of the formula VI, where R24 and R25 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, 3) -(C0-C3)-alkyl-phenyl in which alkyl and phenyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, or 4) -(C0-C3)-alkyl-(C3-C6)-cycloalkyl, or R26, R27, R28 and R29 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1- C3)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, 3) fluorine, 4) -OH, 5) -NH2 or 6) -(C0-C3)-alkyl-phenyl in which alkyl and phenyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, and Z is hydrogen atom or (C1-C4)-alkyl.

4. A compound of the formula la as claimed in claims 1 or 2, where U is hydrogen atom, X is the radical of the formula II in which m is the integer 1, A1 is -(CH2)-, A2 is aminopyridyl in which aminopyridyl is unsubstituted or substituted independently of one another once, twice or three times by halogen or -CH3, Y is 1) the radical of the formula III where a) A3 is -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, and A4 and A5 are absent, b) A3 is -(C2-C4)-alkynylene in which alkynylene is unsubstituted or substituted independently of one another once, twice or three times by R1, and A4 and A5 are absent, c) A3 is cyclic amine having 3 to 8 ring atoms in which cyclic amine is unsubstituted or substituted independently of one another once, twice or three times by R1, and A4 and A5 are absent, d) A3 is -(CH2)q-phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 is -N(R2)- in which R2 is as defined below A5 is a)1) -C(O)-R3, a)2) -C(O)-N(R4)-R5, a)3) -(SO2)-R6 or a)4) -C(O)-O-R7, o is the integer 1, and p is the integer 1, and q is the integer zero, 1, or 2, e) A3 is -(CH2)r-Het in which Het is a pyrrolidine or piperidine which is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 is absent and A5 is as defined under d), where A5 is bonded to the nitrogen atom of A3, p is the integer 1, and r is the integer zero, 1, 2 or 3, f) A3 is -CH2-phenyl, where phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 is -O-, A5 is phenyl, where phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, where R1 is a) phenyl where phenyl is unsubstituted or substituted independently of one another once, twice or three times by -(C1-C4)-alkyl, b) triazolyl or pyridinyl, c) -(C1-C4)-alkyl, d) -(C3-C6)-cycloalkyl, e) -CF3, f) -O-CF3, g) fluorine or i) chlorine, where R2 is hydrogen atom or -(C1-C3)-alkyl in which is alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, where R3, R6 and R7 are identical or different are independently of one another a) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) hydrogen atom, or d) -(C3-C6)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, where R4 and R5 are identical or different are independently of one another a) -(C1-C6)-alkyl or -(C2-C6)-alkenyl, in which alkyl or alkenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) hydrogen atom, or d) -(C3-C6)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, Y is 2) the radical of a pyrrolidin-2-one where the radical is substituted in each case by R8 on the nitrogen atom, where R8 is a) -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) -(C3-C6)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, Y is 3) the radical of the formula V where R12 is hydrogen atom or -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, and R13 is -CH(R8)-R9 where R8 and R9 are independently of one another phenyl or pyridyl in which pyridyl and phenyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, and R16, R17, R18 and R19 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C3)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, or 3) -(C0- C3)-alkyl-phenyl, in which alkyl and phenyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, and Z is 1) hydrogen atom, 2) -(C1-C6)-alkyl, 3) -(C1-C6)-alkyl-OH, 4) -(C0-C4)-alkyl -(C3-C6)-cycloalkyl, or 5) -(C1-C10)-alkyl-O-C(O)-O-(C3-C6)-cycloalkyl.

5. A compound of the formula la as claimed in one or more of claims 1 to 4, where U is hydrogen atom, X is the radical of the formula II in which m is the integer 1, A1 is -(CH2)-, A2 is the radical which is unsubstituted or substituted independently of one another once, twice or three times by F, Cl, Br, I or -CH3, Y is 1) the radical of the formula III where a) A3 is -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, and A4 and A5 are absent, b) A3 is -(C2-C4)-alkynylene in which alkynylene is unsubstituted or substituted independently of one another once, twice or three times by R1, and A4 and A5 are absent, c) A3 is cyclic amine having 3 to 6 ring atoms in which cyclic amine is unsubstituted or substituted independently of one another once, twice or three times by R1, and A4 and A5 are absent, d) A3 is -(CH2)q-phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 is -N(R2)- in which R2 is as defined below, A5 is a)1) -C(O)-R3, a)2) -C(O)-N(R4)-R5, a)3) -(SO2)-R6 or a)4) -C(O)-O-R7, o is the integer 1, p is the integer 1, and q is the integer zero, 1, or 2, e) A3 is -(CH2)r-Het in which Het is a pyrrolidine or piperidine which is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 is absent and A5 is as defined under d), where A5 is bonded to the nitrogen atom of A3, p is the integer 1, and r is the integer zero, 1, 2 or 3, f) A3 is -CH2-phenyl, where phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, A4 i s -O-, A5 is phenyl, where phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, where R1 is a) phenyl where phenyl is unsubstituted or substituted independently of one another once, twice or three times by -(C1-C4)-alkyl, b) pyridyl or tetrazolyl, c) -(C1-C4)-alkyl, d) -(C3-C6)-cycloalkyl, e) -CF3, f) -O-CF3, g) fluorine or i) chlorine, where R2 is hydrogen atom or -(C1-C3)-alkyl in which is alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, where R3, R6 and R7 are identical or different are independently of one another a) (C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, or c) -(C3-C6)-cycloalkyl, in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, where R4 and R5 are identical or different are independently of one another a) (C1-C6)-alkyl or -(C2-C6)-alkenyl, in which alkyl or -(C2-C6)-alkenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, b) phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, c) hydrogen atom, or d) -(C3-C8)-cycloalkyl in which cycloalkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, Y is 2) the radical of a pyrrolidin-2-one where the radical is substituted in each case by R8 on the nitrogen atom, where R8 is phenyl in which phenyl is unsubstituted or substituted independently of one another once, twice or three times by R1, Y is 3) the radical of the formula V where R12 is hydrogen atom or -(C1-C6)-alkyl in which alkyl is unsubstituted or substituted independently of one another once, twice or three times by R1, and R13 is -CH(R8)-R9 where R8 and R9 are independently of one another phenyl or pyridyl in which pyridyl and phenyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, R16, R17, R18 and R19 are identical or different and are independently of one another 1) hydrogen atom, 2) -(C1-C3)-alkyl in which alkyl is unsubstituted or substituted once or twice by R1, or 3) -(C0- C3)-alkyl-phenyl, in which alkyl and phenyl are each unsubstituted or substituted independently of one another once, twice or three times by R1, and Z is hydrogen atom.

6. A compound of the formula I as claimed in one or more of claims 1 to 5, which is the compound 3-(6-Aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionic acid, Methyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate, Isopropyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate, Cyclopropylmethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate, 2-Hydroxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate, 1-Cyclohexyloxycarbonyloxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)-propionate, 3-(6-Aminopyridin-3-yl)-2-(1-cyclopentyl-1H-imidazol-4-yl)propionic acid, 3-(6-Aminopyridin-3-yl)-2-(1-piperidin-4-yl-1H-imidazol-4-yl)propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(2-oxo-1-phenylpyrrolidin-3-yl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[(benzhydrylcarbamoyl)methyl]-1H-imidazol-4-yl}propionic acid, Isopropyl 3-(6-aminopyridin-3-yl)-2-{1-[(benzhydrylcarbamoyl)methyl]-1H-imidazol-4-yl}-propionate, 3-(6-Aminopyridin-3-yl)-2-{1-[4-(3-phenylureido)phenyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}-propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[2-(1-benzoylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(1-benzoylpiperidin-2-ylmethyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-(1-{2-[1-(3-phenylpropionyl)piperidin-3-yl]ethyl}-1H-imidazol-4-yl)propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(1-diphenylacetylpiperidin-3-ylmethyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-(1-{2-[1-(3-phenylpropionyl)piperidin-4-yl]ethyl}-1H-imidazol-4-yl)propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[2-(1-phenylacetylpiperidin-3-yl)ethyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[2-(1-phenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[1-(4'-methylbiphenyl-3-carbonyl)piperidin-4-ylmethyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(1-benzoylpiperidin-4-ylmethyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-(1-benzhydryl-1H-imidazol-4-yl)propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(4-[1,2,4]triazol-1-yl-benzyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(4-trifluoromethoxybenzyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(1,1-dioxo-1H-1,6-benzo[b]thiophen-2-ylmethyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(5-chlorobenzo[b]thiophen-3-ylmethyl)-1H-imidazol-4-yl]-propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[3-(4-fluorophenoxy)benzyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(2-phenoxybenzyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(4-phenoxybenzyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-(1-prop-2-ynyl-1H-imidazol-4-yl)propionic acid, 3-(6-Aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-(4,4-dimethylcyclohexyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[(benzhydrylmethylcarbamoyl)methyl]-1H-imidazol-4-yl}- propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-({[(4-chlorophenyl)phenylmethyl]carbamoyl}methyl)-1H- imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-[1-({[bis-(4-methoxyphenyl)methyl]carbamoyl}methyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[4-(3-propylureido)phenyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[4-(toluene-4-sulfonylamino)phenyl]-1H-imidazol-4-yl}-propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[3-(3-propylureido)benzyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[3-(3-phenethylureido)benzyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[3-(3-benzylureido)benzyl]-1H-imidazol-4-yl}propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[3-(3-vinylureido)benzyl]-1H-imidazol-4-yl}propionic acid, 3-(2-Aminothiazol-4-yl)-2-{1-[(benzhydrylcarbamoyl)methyl]-1H-imidazol-4-yl-propionic acid, 3-(2-Aminothiazol-4-yl)-2-[1-({[(4-chlorophenyl)phenylmethyl]carbamoyl}methyl)-1H-imidazol-4-yl]propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[4-(3-tert-butylureido)phenyl]-1H-imidazol-4-yl}-propionic acid, 3-(6-Aminopyridin-3-yl)-2-{1-[4-(3-benzylureido)phenyl]-1H-imidazol-4-yl}propionic acid or Ethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate.

7. A process for preparing the compound of the formula I as claimed in one or more of claims 1 to 6, which comprises a), a compound of the formula VII

where PG1 is a carboxyl protective group, being converted into a compound of the formula I as claimed in claim 1, b) a compound of the formula I which has been prepared by process a), or a suitable precursor of the formula I which occurs owing to its chemical structure in enantiomeric forms being fractionated by salt formation with enantiopure acids or bases, chromatography on chiral stationary phases or derivatization using chiral enantiopure compounds such as amino acids, separation of the diastereomers obtained in this way, and elimination of the chiral auxiliary groups into the pure enantiomers, or c) the compound of the formula I prepared by processes a) or b) being either isolated in free form or, in the case where acidic or basic groups are present, converted into physiologically tolerated salts.

8. A medicament having an effective content of at least one compound of the formula I as claimed in one or more of claims 1 to 6 together with a pharmaceutically suitable and physiologically tolerated carrier, additive and/or other active ingredients and excipients.

9. The use of the compound of the formula I as claimed in one or more of claims 1 to 6 for producing a medicament for the prophylaxis and therapy of all disorders associated with thromboses, embolisms, hypercoagulability or fibrotic changes.

10. The use as claimed in claim 9, which is applied to myocardial infarction, angina pectoris and other types of acute coronary syndrome, stroke, peripheral vascular disorders, deep vein thrombosis, pulmonary embolism, embolic or thrombotic events caused by cardiac arrhythmias, cardiovascular events such as restenosis following revascularization and angioplasty and similar procedures such as stent implantations and bypass operations, or reduction of the risk of thrombosis following surgical procedures as in knee and hip joint operations, or disseminated intravascular coagulation, sepsis and other intravascular events which are associated with an inflammation, atherosclerosis, diabetes and the metabolic syndrome and its sequelae, tumor growth and tumor metastasis, impairments of the hemostatic system such as fibrin deposits, fibrotic changes of the lung such as chronic obstructive lung disease, adult respiratory distress syndrome or fibrin deposits in the eye after eye operations or prevention and/or treatment of scar formation.