MXPA06011067A - Imidazole derivatives used as tafia inhibitors - Google Patents

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.

Description

DERIVATIVES OF IMIDAZOL USED AS TAFIa INHIBITORS The invention relates to novel compounds of formula I which inhibit the enzyme TAFIa (inhibitor of activatable fibrinolysis by activated thrombin), to processes for their preparation and to their use as medicaments.

The enzyme TAFIa is produced, for example, through the activation of thrombin from the zymogen, an inhibitor of thrombin-activated fibrinolysis (TAFI). The enzyme TAFI is also called plasma procarboxypeptidase B, procarboxypeptidase U or procarboxypeptidase R, and is a proenzyme similar to carboxypeptidase B (L. Bajzar, Arterioscler, Thromb. Vasc. Biol., 2000, pp. 2511-2518).

During the formation of a clot, thrombin is generated as the final product of the coagulation cascade, and induces the conversion of soluble plasma fibrinogen into an insoluble fibrin matrix. At the same time, thrombin activates the inhibitor of endogenous fibrinolysis TAFI. Therefore, activated TAFI (TAFIa) occurs during the formation of thrombi and the lysis of the TAFI zymogen by the action of thrombin; thrombomodulin, in a complex with thrombin, increases this effect approximately 1250 times. TAFIa cleaves basic amino acids at the carboxy terminus of fibrin fragments. The loss of carboxy-terminal plants as binding sites for plasminogen leads, then, to the inhibition of fibrinolysis. Effective inhibitors of TAFIa prevent the loss of these high-affinity lysine binding sites for plasminogen and, thus, help endogenous fibrinolysis by plasmin: TAFIa inhibitors have profibrinolytic effects.

To maintain hemostasis in blood, mechanisms have been developed that lead to blood clotting and clot breakage; these are in balance. If an altered balance favors coagulation, fibrin is produced in greater quantities, so that the pathological processes of thrombus formation can lead to serious pathological conditions in humans.

Just as excessive coagulation can lead to serious pathological conditions caused by thrombosis, an antithrombotic treatment involves the risk of unwanted bleeding through the alteration of the formation of a necessary hemostatic plug. The inhibition of TAFIa increases the endogenous fibrinolysis (without influencing coagulation and platelet aggregation), that is, the altered equilibrium shifts in favor of fibrinolysis. Therefore, it is possible to counteract the formation of a clinically important thrombus and increase the lysis of a preexisting clot. On the other hand, the construction of a hemostatic plug is not difficult, so that probably a hemorrhagic diathesis is not expected (Bouma et al., J. Thrombosis and Haemostasis, 1, 2003, pp. 1566-1574).

TAFIa inhibitors have already been described in international applications WO03 / 013526 and WO03 / 061653.

The TAFIa inhibitors of the invention are suitable for prophylactic and therapeutic use in humans suffering from disorders associated with thrombosis, embolisms, hypercoagulability or fibrotic changes. They are suitable for acute and long-term therapy.

The invention, therefore, relates to a compound of formula I and / or all stereoisomeric forms of the compound of formula I and / or mixtures of these forms in any proportion, and / or the physiologically tolerated salt of the compound of formula I, wherein U is 1) a hydrogen atom, ) -alkyl (C <? -C6) -, 3) -cycloalkyl (C3-C5) -, 4) fluorine, 5) -O-CF3 or 6) -CF3, X is the radical of formula II - (A1) m-A2 (II) where m is the integer zero or 1, A1 is 1) - (CH2) rr. where n is the integer 1, 2 or 3, or 2) -O- (CH2) rr. wherein n is the integer zero, 1, 2 or 3, A2 is 1) a Het ring of 4 to 15 members comprising at least one N atom, and is substituted with an amino group and may also be independently substituted one, two or three times with an -alkyl (C? -C3) -, halogen, -CF3 0 -O-CF3, 2) -alkyl (C? -C6) -NH2 or 3) -cycloalkyl (C3-) C8) -NH2, Y is 1) the radical of formula III A3- (A4) 0- (A5) p (III) wherein a) A3 is -cycloalkyl (C3-C8) - or -alkynylene (C2) -C6) -, in which the cycloalkyl or alkynylene are not substituted or are independently substituted one, two or three times with -O-R10 or R1, A4 is -N (R2) 2-, where R2 is as defined below, and the two radicals R2 are independently defined, A5 is absent, or is the integer zero or 1, and R10 is hydrogen, -alkyl (C? -Cg) - or -aryl (C6-C- | 4) -, b) A3 is -cloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted yes one, two or three times with -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, or is the integer 1, and p is the integer 1, c) A3 is a cyclic amine having from 3 to 8 atoms in the ring, in which the cyclic amine is unsubstituted or is independently substituted one, two or three times with R1, A4 and A5 are as defined in b), that A5 is attached to the N atom of A3, or is the integer zero, and p is the integer zero or 1, od) A3 is - (CH2) q-aryl (Cg-Ci4) -, in which the aryl is not replaced or is replaced inde each other one, two or three times with R1, A4 and A5 are as defined in b), or 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) j-Het, in which Het is a Het ring of 4 to 15 members, and the Het ring is unsubstituted or is independently substituted one, two or three times with = O or R1, A4 and A5 are as defined in b), or 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-aryl (C6-C? 4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -O-, A5 is -aryl (C6-Ci4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, oyp is the integer 1 and q is the integer zero, 1, 2 or 3, g) -CH (- aryl (C6-C14)) - aryl (C6-C14) -, wherein R1 is a) -aryl (C6-Ci4) -, wherein the aryl is unsubstituted or is independently substituted one, two or three times with -alkyl (CrC6) -, -alkyl (C0-C4) ) -cycloalkyl (C3-C8) -, -CF3, = O, -O-CF3 or halogen, b) a Het ring of 4 to 15 members, c) -alkyl (C? -C6) -, d) -alkyl (Co-C4) -cycloalkyl (C3-C8) -, e) -CF3, f) -O-CF3 0 g) halogen, wherein R2 is a) -aryl (C6-C- | 4) ) -, wherein the aryl is unsubstituted or is independently substituted one, two or three times with R1, b) -alkyl (C? -C6) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, c) -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, d) -CF3 or e) a hydrogen atom, wherein R3, R6 and R7 are identical or different and are, independently of each other a) -alkyl (C? -C6) -, in which the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) -ari! or (C5-Ci4) - , wherein the aryl is unsubstituted or is independently substituted one, two or three times with R1, c) a Het ring of 4 to 15 members, wherein the Het ring is unsubstituted or is independently substituted one, two or three times with R1, d) -cycloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, oe) a hydrogen atom, in which R4 and R5 are identical or different and are, independently of each other a) -alkyl (C? -C6) - or -alkenylene (C2-C? Rj) -, in the that the alkyl or alkenylene are unsubstituted or are independently substituted one, two or three times with R1, b) -aryl (Ci-Ci4) -, in which the aryl is unsubstituted or substituted independently of one another, two or three times with R1, c) a Het ring of 4 to 15 members, in which the Het ring is unsubstituted or is independently substituted one, two or three times with R1, d) -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, or R4 and R5 form, together with the atom of nitrogen to which they are attached, a ring having from 3 to 8 ring atoms, which may also comprise, in addition to the nitrogen atom, one or two further heteroatoms of the oxygen, sulfur or nitrogen series, and Y is 2) the radical of formula IV, wherein R8 is a) -alkyl (C- | -C6) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) -aryl (C6-Ci4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, c) a Het ring of 4 to 15 members, in which the Het ring is unsubstituted or is independently substituted yes one, two or three times with R1, d) -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, and is 3) the radical of formula V wherein, in case a) R12 is 1) -alkyl (C? -C6) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, 2) -alkyl (Cn-C3) -cycloalkyl (C3-C6) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, 3) -alkyl (Co-C3) -aryl (C6-C-j4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, or 4) -alkyl (Crj-C3) -Het, in which Het does not is substituted or independently substituted one, two or three times with R1, and R13 is 1) -alkyl (Co-C3) -aryl (C6-C- | 4) -, wherein the alkyl and aryl are unsubstituted or are independently substituted each other one, two or three times with R1, or 2) -alkyl (Co-C3) -Het, wherein the alkyl and Het each is unsubstituted or substituted independently of each other one, two or three times with R1, wherein, in case b) R12 is 1) a hydrogen atom, 2) -alkyl (C? -Cβ) -, wherein the alkyl is unsubstituted or substituted independently one, two or three times with R1, 3) -alkyl (Co-C3) -aryl (C6-Ci4) -, wherein the aryl is unsubstituted or is independently substituted one, two or three times with R1, or 4) -alkyl (Crj-C3) -Het, in which Het is unsubstituted or independently substituted one, two or three times with R1, and R13 is -CH (R8) -R9, wherein R8 and R9 are independently from each other -aryl (C6-C-j4) - or Het, wherein Het and the aryl are each unsubstituted or substituted independently substituted one, two or three times with -O-alkyl (d-C4) - or R1, and R16, R17, R18 and R19 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -acyl (C-? -Ce) -, in which the alkyl is unsubstituted or is substituted once or twice with R 1, 3) halogen, 4) -OH, 5) -NH 2, 6) -alkyl ( Co-C3) -aryl (C6-C-j4) -, wherein the alkyl and aryl are each unsubstituted or independently substituted one, two or three times with R1, or 7) -alkyl (Cn- C3) -Het, wherein the alkyl and Het each is unsubstituted or is independently substituted one, two or three times with R1, or R16 and R17, or R18 and R19 form, together with the carbon atom at the which are respectively attached, a ring having from 3 to 6 ring atoms, or Y is 4) the radical of formula VI, where R24 and R25 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C? -Cβ) -, in which the alkyl is unsubstituted or is substituted once or twice with R1, 3) -alkyl (Crj-C3) -ary (C6-Ci4) -, wherein the alkyl and aryl are each unsubstituted or independently substituted one, two or three times with R1, 4) -alkyl (Crj-C3) -Het, wherein the alkyl and Het are each unsubstituted or independently substituted one, two or three times with R1, or 5) -a! Qui! (Cn-C3) -cycloalkyl (C3-C5) -, or R24 and R25 form, together with the nitrogen atom to which they are attached, a ring having from 3 to 8 ring atoms, which may also comprise, in addition to the atom of nitrogen, one or two more heteroatoms of the oxygen, sulfur or nitrogen series, R26, R27, R28 and R29 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkullo (C? -C6 ) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) halogen, 4) -OH, 5) -NH2, 6) -alkyl (Co-C3) -aryl (Cg-C-i4) -. wherein the alkyl and aryl each is unsubstituted or is independently substituted one, two or three times with R1, or 7) -a! quil (Co-C3) -Het, wherein the alkyl and Het each one is unsubstituted or is independently substituted one, two or three times with R1, or R26 and R27, or R28 and R29 form, together with the carbon atom to which they are respectively attached, a ring having from 3 to 6 ring atoms, Z is 1) a hydrogen atom, 2) -alkyl-Ce) -, 3) alkyl (C < / - C6) -OH, 4) -alkyl (C0-C4) -c chloralkyl (C3-C6) -, 5) -alkyl (dC? o) -OC (O) -O-R1, 6) - (CH2) raryl (C6-C-j4) -, wherein the aryl is unsubstituted or is independently substituted one, two or three times with R1, and r is the integer zero, 1, 2 or 3, or 7) - (CH2) S-Het, in which Het is unsubstituted or is independently substituted one, two or three times with R1, and s is the integer zero, 1, 2 or 3.

The invention also relates to the compound of formula U is 1) a hydrogen atom, 2) -alkyl (C? -C6) -, 3) - cycloalkyl (C3-C6) -, 4) fluorine, 5) -O-CF3 or 6 ) -CF3, X is the radical of formula II, where m is the integer zero or 1, A1 is 1) - (CH2) rr. where n is the integer 1, 2 or 3, or 2) -O- (CH2) m where n is the integer zero, 1, 2 or 3, A2 is 1) a ring Het of 4 to 15 members, wherein the 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, isoindolyl, isoindolyl, soquinolinyl (benzimidazolyl), isothiazolidinyl, 2- isothiazolinyl, isothiazolyl, isoxazolyl, isoxazolidinyl, 2-isoxazolinyl, morpholinyl, naphthyridinyl, octahydroisoquinolinyl, oxadiazolium, 1,3-oxadiazolyl, 1,4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1,3,4 -oxadiazolyl, oxazolidinyl, oxazolyl, pyrimidinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, fenoxatünilo, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, piroazolidinilo, pyrazolinyl, pyrazolyl, pyridazinyl, piridooxazolilo, pyridoimidazolyl, piridotiazolilo, piridotiofenilo , pyridinyl, pyridyl, pyrimidinyl, pyrrolidinium, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrahydropyridinyl, 6H-1, 2,5-thiazinyl, 1,4-thiadiazolyl, 1, 2,5-thiadiazolyl 1, 3,4-tladiazoyl, thianthrenyl, thiazolyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiomorpholinyl, triazinyl, 1,2,3-triazolyl, 1,4-triazolyl, 1,2,5-triazolyl, 1,3 , 4-triazolyl and xa ntenyl, and wherein the Het ring is substituted with an amino group, and can also be independently substituted one, two or three times with an alkyl (Cj-C3) -, halogen, -CF3 0 -O-CF3 , 2) -alkyl (C? -C6) -NH2 or 3) -cycloalkyl (C3-C8) -NH2, Y is 1) the radical of formula III, wherein a) A3 is -cycloalkyl (C3-C8) - or -alkynylene (C2-C6) -, in which the cycloalkyl or alkynylene are not substituted or are independently substituted one, two or three times with R1, A4 is -N (R2) 2-, wherein R2 is as defined below, and the two radicals R2 are independently defined from each other, A5 is absent is the integer zero or 1, b) A3 is -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with 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, or is the integer 1, and p is the integer 1, c) A3 is a cyclic amine of the group of propylamine, azetidine, pyrrolidine, piperidine, azepanes or azoanes, wherein the cyclic amine is not substituted or is independently substituted one, two or three times with R1, A4 and A5 are as defined in b), wherein A5 is attached to the N atom of A3, or is the integer zero, and p is the integer zero or 1, od) A3 is - (CH2) q-aryl (C6-C <i4) -, wherein the aryl is selected from the group of phenyl, naphthyl, anthryl or fluorenyl, and is unsubstituted or substituted independently one, two or three times with R1, A4 and A5 are as defined in b) or is the integer zero or 1, and p is the integer number 1, and • q is the integer zero, 1, 2 or 3, e) A3 is - (CH2) r-Het, where Het is as defined above, and is not substituted or independently substituted one, two or three times with = 0 or R1, A4 and A5 are as defined in b), or is the integer zero or 1, p is the integer 1, and r is the integer zero, 1, 2 or 3, f) A3 is -aryl (CH2) q- (C6-C? 4) -, wherein the aryl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -O-, A5 is -ar Iio (C6-Ci4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, oyp is the integer 1 and 5 is the integer zero , 1, 2 or 3, g) -CH (phenyl) -phenyl, wherein R1 is a) -aryl (C6-C-14) -, wherein aryl is as defined above, and wherein the aryl is unsubstituted or is independently substituted one, two or three times with -alkyl (CrC6) -, -alkyl (C0-C4) -cycloalkyl (C3-C8) -, -CF3, = O, -O- CF3 or halogen, b) a 4 to 15 membered Het ring, in which Het is as defined above, 15 c) -acyl (C? -C6) -, d) -cycloalkyl (C3-C8) -, and ) -CF3, f) -O-CF3 og) halogen, wherein R2 is a) -aryl (C6-C-i4) -, wherein aryl is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, b) -alkyl (C? -C6) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, c) -alkanoic acid (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, d) -CF3 or 10 e) a hydrogen atom, in which R3, R6 and R7 are identical or different and are, independently of each other a) -alkyl (C? -C6) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) -aryl (C6-C-i4) -, in which aryl is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, 20 c) a ring Het of 4 to 15 members, wherein the Het ring is as defined above, and is unsubstituted or substituted independently of one, two or three times with R1, d) -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, in which R4 and R5 are identical or different and are, independently of each other a) -alkullo (C- | -Cg) - or -alkenyl (C2-C? o) - > wherein the alkyl or alkenyl are unsubstituted or are independently substituted with one, two or three times with R1, b) -aryl (C6-Ci4) -, in which aryl is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, 15 c) a Het ring of 4 to 15 members, wherein the Het ring is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, d) -cycloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, or R4 and R5 form, together with the nitrogen atom to which are attached, a ring having from 3 to 8 ring atoms selected from the group of propylamine, azetidine, pyrrolidine, piperidine, azepanes, azoanes, azepine, dioxazole, dioxazine, 1,4-diazepane, 1,2-diazepine, 1, 3- diazepine, 1,4-diazepine, imidazole, imidazoline, imidazolidine, isothiazole, isothiazolidine, isothiazoline, soxazole, isoxazoline, isoxazolidine, 2-isoxazoline, cetopiperazine, morpholine, [1,4] oxazepane, oxazole, piperazine, pyrazine, pyrazole, pyrazoline, pyrazolidine, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolidinone, pyrroline, tetrahydropyridine, thiazole, thiazole, thiazolidine, thiazoline, thiomorpholine, 1,2,3-triazine, 1,4-triazine, 1, 3, 5- triazine, 1,2,3-triazole or 1,2,4-triazole, and Y is 2) the radical of formula IV, wherein formula IV is a compound of the group of azetidin-2. one, pyrrolidin-2-one, piperidin-2-one, azepane-2-one and azocan-2-one, and is substituted at the nitrogen atom in each case with R8, wherein R8 is a) -alkyl or (C -? - Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) -aryl (C6-C- | 4) -, wherein aryl is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, c) a Het ring of 4 to 15 members, wherein the Het ring is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, d) -cycloalkyl (C3-C8) ) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, and is 3) the radical of formula V, in which, in the case a) R12 is 1) -alkyloylC-j-Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, 2) -alkyl (Crj-C3) - cycloalkyl (C3-C6) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, 3) -alkyl (Co-C3) -aryl (C6-C- | 4) -, in which aryl is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, or 4) -alkyl (C () - C3) -Het, in which Het is as defined above, and is not substituted or independently substituted one, two or three times with R1, and R13 is 1) -alkyl (Co-C3) -aryl (Ce-C-] 4) -, wherein alkyl and aryl are as defined above, and each is unsubstituted or substituted independently of each other one, two or three times with R1, or 2) -alkyl (Co-C3) -Het, wherein alkyl and Het are as defined above, and each is unsubstituted or substituted independently of one another , two or three times with R1, or in case b) R12 is 1) a hydrogen atom, 2) -alkyl (C? -C5) -, wherein the alkyl is unsubstituted or is independently substituted with one another , two or three times with R1, 3) -alkyl (Co-C3) -aryl (C6-C- | 4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, or 4) -alkyl (Crj-C3) -Het, in which Het is unsubstituted or is independently substituted one, two or three times with R1, and R13 is -CH (R8) -R9, wherein R8 and R9 are independently between yes -aryl (Cß-Ci4) - or Het, in which Het and aryl is each as defined above and is unsubstituted or substituted independently of one another once, twice or three times by -O-alquiIo (CRC4) - or R1, and R16, R17, R18 and R19 are identical or different and are independently from each other 1) a hydrogen atom, 2) -alkyloylCi-Cg) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) halogen, 4) -OH, 5) -NH2 , 6) -alkyl (Co-C3) -aryl (C6-Ci4) -, wherein alkyl and aryl are as defined above, and each is unsubstituted or is independently substituted one, two or three times with R1, or 7) -alkyl (Crj-C3) -Het, wherein alkyl and Het are as defined above, and each is unsubstituted or is independently substituted one, two or three times with R1, or R16 and R17, or R18 and R19 form, together with the carbon atom to which they are respectively attached, a ring having from 3 to 6 ring atoms of the cyclopropyl group, cyclobutyl, cyclopentyl or cyclohexyl, or Y is 4) the radical of formula VI, in which R24 and R25 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C? -C6) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) -alkyl (Co-C3) -aryl (C6-Ci4) -, wherein alkyl and aryl are as defined above, and each is unsubstituted or substituted is independently substituted one, two or three times with R1, 4) -alkyl (Co-C3) -Het, wherein alkyl and Het are as defined above, and each is unsubstituted or substituted independently from each other one, two or three times with R1, or 5) -alkyl (Co-C3) -cycloalkyl (C3-C6) -, or R24 and R25 form, together with the nitrogen atom to which they are attached, a ring that It has 3 to 8 ring atoms of the group of propylamine, azetidine, pyrrolidine, piperidine, azepanos, azócanos, 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, R26, R27, R28 and R29 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C -? - Cß) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) halogen, 4) -OH, 5) -NH2, 6) -alkyl (Cn-C3) -aryl (C6-C < i4) -, wherein alkyl and aryl are as defined above, and each is unsubstituted or is independently substituted one, two or three times with R1, or 7) -alkyl (Co-C3) -Het, wherein alkyl and Het are as defined above, and each is unsubstituted or is independently substituted one, two or three times with R1, or R26 and R27, or R28 and R29 form, together with the carbon atom to which are attached respectively, a ring that It has 3 to 6 ring atoms of the cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group, Z is 1) a hydrogen atom, 2) -alkyl (C- | -C6) -, 3) cycloalkyl (C3-Cg) -, 4) alkyl (C? -C0) -OC (O) -O-R1.5) - (CH2) r -aryl (Cg-Ci4) -, wherein aryl is as defined above, and is unsubstituted or substituted independently one, two or three times with 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 not substituted or independently substituted one, two or three times with R1, and s is the integer zero, 1, 2 or 3. The invention also relates to the compound of formula la, wherein U is a hydrogen atom, -CF3, fluorine or -CH3, X is the radical of formula II, wherein m is the integer 1 , A1 is 1) - (CH2) -, 2) -O- (CH2) n-. wherein n is the integer zero or 1, or 3) a covalent bond, A2 is 1) aminopyridyl, wherein aminopyridyl is unsubstituted or independently substituted with one another once, twice or three times with -a! chyle ( C? -C3) -, halogen or -CH3, 2) amlnothiazolyl, in which aminothiazolyl is unsubstituted or is independently substituted one, two or three times with -alkyl (C- | -C3) -, halogen or -CH3, 3) -alkyl (C? -C3) -NH2 or 4) -cycloalkyl (C3-C8) -NH2, Y is 1) the radical of formula III, wherein a) A3 is -cycloalkyl (C3-C8) - or -alkynylene (C2-Cg) -, in which the cycloalkyl or alkynylene are not substituted or are independently substituted one, two or three times with -O-R10 or R1, A4 is -N (R2) 2-, wherein R2 is as defined below, and the two radicals R2 are independently defined from each other, A5 is absent, or is the integer zero or 1, and R10 is hydrogen, -alkyl (C -? - Cg) - or phenyl, b) A3 is -cycloalkyl (C3-Cg) -, wherein the cycloalkyl is not is substituted or independently substituted one, two or three times with -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, or is the integer 1, and p is the integer 1, c) A3 is a cyclic amine having from 3 to 8 atoms in the ring, in which the cyclic amine is unsubstituted or substituted independently of one another, two or three times with R1, A4 and A5 are as defined in b), where R5 is attached to the N atom of A3, or is the integer zero, and p is the integer zero or 1, od) A3 is - (CH2) q-aryl (Cg-C-i4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, A4 and A5 are as defined in b), or 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, where Het is pyrrolidine, benzothiophene or piperidine, which are not substituted or are independently substituted one, two or three times with = O or R1, A4 and A5 are as defined in b), or is the integer zero or 1, p is the integer 1, and r is the integer zero, 1, 2 or 3, f) A3 is -phenyl (CH2) q-, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -O-, A5 is phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, and p and p are the integer 1 and p is the integer 1 or 2, wherein R1 is a) phenyl, wherein phenyl is unsubstituted or is independently substituted one, two or three times with -alkyl (CrC4) -, b) triazolyl or pyridinyl, c) -alkyl (C- | -C4) -, d) -cycloalkyl (C3-Cg) -, e) -CF3, f) -O-CF3, g) fluorine or chloro, wherein R2 is a) phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, b) -alkyl (Cj-C3) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, c) -cycloalkyl (C3-Cg) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, d) -CF30 e ) a hydrogen atom, in which R3, R6 and R7 are identical or different and are, independently of each other a) -alkyl (C- | -Cg) -, wherein the alkyl is unsubstituted or is independently substituted yes one, two or three times with R1, b) -aryl (Cg-Ci4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, c) a Het ring of 4 to 15 members, in which the Het ring is unsubstituted or is independently substituted one, two or three times with R1, d) -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, wherein R4 and R5 are identical or different and are, independently of each other a) -alkyl (C? -Cg) - or -alkenyl (C2-Cg) -, wherein the alkyl or alkenyl are unsubstituted or are independently substituted each other or three times with R1, b) -aryl (Cg-C ^ 4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, c) a Het ring of 4 to 15 members, wherein the Het ring is unsubstituted or is independently substituted one, two or three times with R1, d) -cycloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted each other one, two or three times with R1, oe) a hydrogen atom, or R4 and R5 form together with the nitrogen atom to which they are attached, a ring derived from azetidine, pyrrolidine, piperidine, azepanos, azócanos, azepine, dioxazole, dioxazine, 1, 4-diazepane, 1, 2-diazepine, 1, 3-diazepine, 1, 4-diazepine, imidazole, imidazoline, midazolidina, isothiazole, isothiazolidine, isothiazoline, soxazol, isoxazoline, soxazolidina, 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-triazoi or 1, 2,4-triazole, Y is 2) the radical of formula IV selected from the group of azetidin-2-one, pyrrolidin-2-one or piperidin-2-one, wherein the radical is substituted on the nitrogen atom in each case R8, wherein R8 is a) -alquüo ( C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) phenyl, wherein the phenyl is unsubstituted or is independently substituted by one, two or three times with R1, c) a hydrogen atom, or d) -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, Y is 3) the radical of formula V, wherein, in case a) R12 is 1) -alkyl (C- | -Cg) -, wherein the alkyl is not substituted or substituted independently of one another once, twice or three times by R1, 2) -C (Crj-C3) -cicloaIqu¡lo (C3-Cg) -, wherein the cycloalkyl is unsubstituted or substituted independently one, two or three times with R1, or 3) -alkyl (Co-C3) -phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, and R13 is 1) -alkyl (Co-C3) -phenyl, wherein the alkyl and phenyl are each unsubstituted or independently substituted one, two or three times with R1, or 2) -alkyl (Co-C3) -pyridyl, wherein the alkyl and pyridyl are each unsubstituted or independently substituted one, two or three times with R1, or in case b) R12 is 1) a hydrogen atom, 2) -alkyl (C? Cg) -, in which the alkyl is not substituted or independently substituted one, two or three times with R1, 3) -alkyl (Crj-C3) -phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, or 4) -alkyl (Crj-C3) -pyridyl, wherein the alkyl and pyridyl are each unsubstituted or independently substituted one, two or three times with R1, and R13 is -CH (R8) -R9 wherein R8 and R9 are each independently phenyl or pyridinyl, wherein the phenyl or pyridyl each is unsubstituted or is substituted independently one, two or three sometimes with -O-alkyl (CrC4) - or R1, and R16, R17, R18 and R19 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C <? -C3) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) fluoro, 4) -OH, 5) -NH2 or 6) -alkyl (Crj-C3) -phenyl, wherein alkyl and phenyl each is unsubstituted or is independently substituted one, two or three times with R1, or Y is 4) the radical of formula VI, wherein R24 and R25 are identical or different and are, independently of each other 1) an atom of hydrogen, 2) -alkyl (C- | -Cg) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) -alkyl (Crj-C3) -phenyl, wherein the alkyl and phenyl each is unsubstituted or is independently substituted one, two or three times with R1, or 4) -alkyl (Co-C3) -cycloalkyl (C3-C6) -, or R26, R27, R28 and R29 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C? -C3) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1 , 3) fluorine, 4) -OH, 5) -NH2 or 6) -alkyl (Co-C3) -phenyl, wherein the alkyl and phenyl are each unsubstituted or substituted independently of one, two or three times with R1, and Z is a hydrogen atom or allyl (d-C4) -. The invention also relates to the compound of formula la, wherein U is a hydrogen atom, X is the radical of formula II, wherein m is the integer 1, A1 is - (CH2) -, A2 is aminopyridyl , in the aminopyridyl is unsubstituted or is independently substituted one, two or three times with halogen or -CH3, Y is 1) the radical of formula III, wherein a) A3 is -cycloalkyl (C3-C8) ) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, b) A3 is -alkynylene (C3-C8) -, wherein the Alkynylene is unsubstituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, c) A3 is a cyclic amine having from 3 to 8 ring atoms, wherein the cyclic amine is not substituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, d) A3 is -phenyl ( CH2) q-, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -N (R2) -, wherein 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, or 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, where Het is pyrrolidine or piperidine , which are not substituted or are independently substituted one, two or three times with R1, A4 is absent and A5 is as defined in d), where A5 is attached to the nitrogen atom of A3, p is the number integer 1, and r is the integer zero, 1, 2 or 3, f) A3 is -CH2-phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -O-, A5 is phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, wherein R1 is a) phenyl, wherein phenyl is unsubstituted or is independently substituted one, two or three times with -alkyl (d-C4) -, b) triazolyl or pyridinyl, c) -alkyl (CrC4) -, d) -cycloalkyl (C3-C6) -, e) -CF3, g) fluorine or i) chloro, wherein R2 is a hydrogen atom or -alkylCrd) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, wherein R3, R6 and R7 are identical or different and are, independently of each other a) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, c) a hydrogen atom, or d) -cycloalkyl (C3-C6) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, where R4 and R5 are identical or different and are, independently of each other a) -alkyl (Cj-Cg) -, wherein the alkyl is unsubstituted or is independently replaced each other one, two or three times with R1, b) phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, c) a hydrogen atom, or d) -cycloalkyl (C3-Cg) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R 1, Y is 2) the radical of a pyrrolidin-2-one, in which the radical is each substituted with R 8 on the nitrogen, wherein R8 is a) -alkyl (Cj-Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) phenyl, wherein the phenyl is unsubstituted or substituted I, independently of one another, two or three times with R1, c) -cycloalkyl (C3-C6) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, Y is 3) the radical of formula V, wherein R12 is a hydrogen atom or -alkyl (CrC6) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, and R13 is -CH (R8) -R9, wherein R8 and R9 are, independently of each other, phenyl or pyridyl, wherein the pyridyl and phenyl each is unsubstituted or is independently substituted one, two or three times with R1, and R16, R17, R18 and R19 are identical or different and are, independently of each other 1) a hydrogen atom, • 2) -alkyl (C? -C3) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, or 3) -alkyl (Co-C3) -phenyl, wherein the alkyl and phenyl each is unsubstituted or is independently substituted one, two or three times with R1, and Z is 1) a hydrogen atom, 2) -alkyl (C < -GC) -, 3) -alkyl (C- | -Cg) -OH, 4) -alkyl (Cn-C4) -cycloalkyl (C3-Cg) -, 5) -alkyl (C? -C? o) -0-C (O) -O-cycloalkyl (C3-Cg) -. The invention also relates to a compound of formula la, wherein U is a hydrogen atom, X is the radical of formula II, wherein m is the integer 1, A1 is - (CH2) -, A2 is the radical which is unsubstituted or is independently substituted one, two or three times with F, Cl, Br, I or -CH3, Y is 1) the radical of formula III, wherein a) A3 is -cycloalkyl (C3-) C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, b) A3 is -alkynylene (C2-C4) -, wherein the alkynylene is unsubstituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, c) A3 is a cyclic amine having from 3 to 6 ring atoms, wherein the amine cyclic is unsubstituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, d) A3 is -phenyl (CH2) q-, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -N (R2) -, where R2 is as defined below, A5 is a) 1) -C (O) -R3, a) 2) - CO)- N (R4) -R5, a) 3) - (SO2) -R6 or a) 4) -C (O) -O-R7, or is the integer 1, p is the integer number 1, and q is the integer zero, 1 or 2, e) A3 is - (CH2)? ~ Het, where Het is pyrrolidine or piperidine, which are unsubstituted or substituted independently of one another , two or three times with R1, A4 is absent and A5 is as defined in d), where A5 is attached 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, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -O-, A5 is phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, wherein R1 is a) phenyl, wherein phenyl is not substituted or independently substituted one, two or three times with -a (C4-4) alkyl, (b) pyridyl or tetrazolyl, c) -alkyl (CrC4) -, d) -cycloalkyl (C3-C6) - , e) -CF3, g) fluorine or i) chloro, wherein R2 is a hydrogen atom or -alkylCrd) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, wherein R3, R6 and R7 are identical or different and are, independently of each other a) -alkyl (Cj-Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) phenyl , wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R 1, c) cycloalkyl (C 3 -C 6) -, wherein the cycloalkyl is unsubstituted or is independently substituted with one another , two or three times with R1, wherein R4 and R5 are identical or different and are, independently of each other a) -alkyl (C? -Cg) - or -alkenylene (C2-C4) -, wherein the alkyl or alkenylene are unsubstituted or substituted independently of one another, two or three times with R 1, b) phenyl, wherein The phenyl is unsubstituted or is independently substituted one, two or three times with R1, c) a hydrogen atom, or d) -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1 Y is 2) the radical of a pyrrolidin-2-one, wherein the radical is substituted in each case with R8 on the nitrogen atom, wherein R8 is phenyl, wherein the phenyl is unsubstituted or substituted independently of each other one, two or three times with R1, Y is 3) the radical of formula V, wherein R12 is a hydrogen atom or -alkyl (CrC6) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, and R13 is -CH (R8) -R9, wherein R8 and R9 are, independently of each other, phenyl or pyridyl, wherein the pyridyl and phenyl each is unsubstituted or substituted independently of one another, two or three times with R1, R16, R17, R18 and R19 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C < C3) -, wherein the alkyl is not is substituted or is substituted once or twice with R1, or 3) -alkyl (Crj-C3) -phenyl, wherein the alkyl and phenyl are each unsubstituted or substituted independently of one another, two or three times with R1, and Z is a hydrogen atom. The invention also relates to compounds of the formula of the series 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazol-4-yl) propionic acid, 3- (6-Aminopyridin-3-yl) -2- (1-cyclohexyl-1H-imidazole-4-yl) propionate methyl; 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazol-4-yl) isopropyl propionate, 3- (6-Aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazole-4-y!) Propionate of cyclopropylmethyl, 3- (6-aminopyridin-3-yl) -2 2-hydroxyethyl (1-cyclohexyl-1 H-imidazol-4-yl) propionate, 3- (6-aminopyridn-3-yl) -2- (1-cyclohexyl-1 H-imidazole) 4-yl) 1-cyclohexyloxycarbonyloxyethyl propionate, 3- (6-aminopyridin-3-yl) -2- (1-cyclopentyl-1 H-imidazol-4-yl) propionic acid, - (6-aminopyridin-3-yl) -2- (1-piperidin-4-yl-1 H-imidazol-4-yl) propionic acid, 3- (6-aminopyridin-3-yl) - 2- [1 - (2-OXO-1-phenylpyrrolidin-3-yl) -1 H-imidazol-4-yl-propionic acid, 3- (6-aminopyridin-3-yl) -2-. { 1 - [(benzylcarbamoyl) methyl] -1 H-imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2-. { 1 - [(benzhydrilcarbamoyl) metl] -1 H -amdazol-4-yl} isopropyl propionate, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [4- (3-phenylureido) phenyl] -1 H-imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [2- (1-diphenylacetylpiperidin-4-yl) ethyl] -1 H- imidazol-4-iI} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [2- (1-benzoylpiperidn-4-yl) ethyl] -1 H-imidazol-4-yl} propionic, 3- (6-aminopyridn-3-yl) -2- [1- (1-benzoylpperidin-2-ylmethyl) -1H-methyldazole-4-yl] -propionic acid 3- (6-aminopyridin-3-yl) -2- (1- { 2- [1- (3-phenylpropionyl) pperiod-3-yl] etl.) -1 H- mida-zol-4-yl) propionic acid, 3- (6-aminopyridine-3-yl) -2- [1- ( 1-diphenylacetylpyridin-3-ylmethyl) -1H-methyldazole-4-yl] -propionic acid, 3- (6-aminonol-3-yl) -2 - (1- { 2- [1- (3-phenylpropionl) p¡per¡din-4-1] etl.} -1 H- mida-zol-4-il ) propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [2- (1-phenylacetylpperidin-3-yl) etl) -1 H-imidazole-4-yl} -proponic, 3- (6-aminopyrid-3-yl) -2- acid. { 1- [2- (1-phenylacetylpiperidin-4-yl) etl) -1H-ylamdazol-4-yl} -propionic, 3- (6-aminopyrin-3-yl) -2- acid. { 1 - [1 - (4'-methyl-phenyl-3-carbonyl) piperidn-4-ylmethyl] -1H-imidazole-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- [1 - (1-benzoylpiperidin-4-ylmethyl) -1 H-imidazol-4-??] - propionic acid, 3- acid (6-aminopyridin-3-yl) -2- (1-benzhydryl-1 H-imidazol-4-yl) propionic acid, 3- (6-aminopyridin-3-yl) -2- [1- (4- [ 1, 2,4] triazol-1-ylbenzyl) -1 H-imidazol-4-yl] -pro-pionic acid, 3- (6-aminopyridin-3-yl) -2- [1 - (4 -trifluoromethoxybenzyl) -1 H -amidazo-4-yl] pro pionic, 3- (6-aminopyridin-3-yl) -2- [1- (1,1-d-oxo-1H-1, 6-benzo [b] tofen-2-acid] Lmethyl) -1 H-imi-dazol-4-yl] propionic acid, 3- (6-aminopyridin-3-yl) -2- [1 - (5-chlorobenzo [b] thiophen-3] -ylmethyl) -1 H-imidazol-4-yl] propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [3- (4-fluorophenoxy) benzyl] -1H-imidazol-4-yl} propionic, 3- (6-amynopyridin-3-yl) -2- [1 - (2-phenoxybenzyl) -1 H-imidazol-4-yl] propionic acid, 3- (6-aminonyr) acid d-n-3-yl) -2- [1- (4-phenoxybenzyl) -1H-imidazol-4-yl] propionic acid, 3- (6-aminopyridin-3-yl) -2- (1-prop) -2-inyl-1 H-imidazole-4-yl) propionic acid, 3- (6-aminopyridin-3-yl) -2- (1-but-2-ynyl-1 H-imidazole-4) -yl) propionic acid, 3- (6-aminopyridin-3-yl) -2- [1- (4,4-dimethylcyclohexyl) -1H-imidazol-4-ylpropionic acid, 3- ( 6-aminopyridin-3-yl) -2-. { 1 - [(benzhydrylmethylcarbamoyl) methyl] -1 H -imidazol-4-yl} propionic acid, 3- (6-aminopyrid-3-yl) -2- [1 - ( { [(4-chlorophenyl) phenylmethyl] carbamoyl} methyl) -1 H- my-dazol-4-yl] propionic acid, 3- (6-aminopyridin-3-yl) -2- [1 - ( { [Bis- (4-methoxyphenyl) methyl] carbamoyl.} Methyl. ) -1 H-imi-dazol-4-yl] propionic acid, 3- (6-aminopyridn-3-yl) -2-. { 1- [4- (3-propylalidido) pheny] -1 H-imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [4- (Toluene-4-sulfonylamino) phenyl] -1H-imidazole-4-yl} -propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [3- (3-propylureido) benzyl] -1 H-imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [3- (3-phenyl-uretide) -benzyl] -1H-imidazol-4-ylpro-pionic acid, 3- (6-aminopyridin-3-yl) -2-. { 1- [3- (3-benzylurethane) benzyl] -1H-imidazol-4-ylpro-pionic acid, 3- (6-aminopyridin-3-yl) -2-. { 1 - [3- (3-vinylidene) benzyl] -1H-imidazol-4-yl} pro-pionic, 3- (2-aminothiazol-4-yl) -2- acid. { 1 - [(benzhydrylcarbamoyl) methyl] -1H-imidazol-4-yl} propionic acid, 3- (2-aminothiazol-4-yl) -2- [1 - ( { [(4-chlorophenyl) phenylmethyl] carbamoyl.} methyl) -1 H-imida-zol-4- il] propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [4- (3-tert-butylureido) phenyl] -1H-imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1- [4- (3-benzylureido) benzyl] -1 H-imidazol-4-yl} propionic, or ethyl 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazol-4-yl) propionate. The term "alkyl (C? -Cg) -" or "(C? -C-) n" - "alkyl means hydrocarbon radicals whose carbon chain is linear or branched, and comprises from 1 to 6 carbon atoms, or from 1 to 10 carbon atoms, for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, pentyl, isopentyl, neopentyl, hexyl, 2,3-dimethylbutane, neohexyl, heptyl, octanyl, nonanyl or decanyl.

The term "-alkylene (Crj-C4) -" means hydrocarbon radicals whose carbon chain is linear or branched, and comprises from 1 to 4 carbon atoms, for example methylene, ethylene, propylene, isopropylene, isobutylene, butylene or tertiary butylene. "Alkylene-CQ-" is a covalent bond. The term "(C- | -C?) -" alkyl also means hydrocarbon radicals such as "-alkenylene (C2-C? O) -", whose carbon chain is straight or branched, and comprises from 2 to 10 carbon atoms and having, depending on the length of the chain, 1, 2 or 3 double bonds, for example ethenylene, propenylene, isopropenylene, isobutenylene or butenlene; the substitutenes in the double bond can, if the possibility exists in principle, be arranged in the E or Z configuration. The expression "alkyl (C? -C-? o) -" also means hydrocarbon radicals such as "-aikinylene" ( C2-C- | n) - ", which means hydrocarbon radicals whose carbon chain is linear or branched, and comprises 2 to 10 carbon atoms and which, depending on the length of the chain, has 1, 2 or 3 triple bonds , for example ethynylene, propenylene, isopropynylene, isobutylinylene, butynylene, pentynylene or the isomers of pentinylene or hexinylene, or the isomers of hexinylene. The term "(C3-C8) cycloalkyl-" means radicals such as compounds derived from 3- to 8-membered monocycles such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctanyl.

The term "cyclic amine having from 3 to 8 ring atoms" means radicals derived from propylamine, azetidine, pyrrolidine, piperidine, azepanes or azoanes. The expression "- (CH2) rr. - (CH2) q-, - (CH2) r., In which n, q or r is the integer zero, 1, 2 or 3" means radicals such as methylene, ethylene or propylene. In the case where n, q or r is the integer zero, the radical has the meaning of a covalent bond. The expression "R16 and R17, or R18 and R19 form, together with the carbon atom to which they are respectively attached, a ring having from 3 to 6 ring atoms" means radicals derived from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. The expressions "R4 and R5 form, together with the nitrogen atom to which they are attached, a ring having from 3 to 8 ring atoms which may also comprise, in addition to the nitrogen atom, one or two additional heteroatoms of the oxygen series, sulfur or nitrogen "or" R24 and R25 form, together with the nitrogen atom to which they are attached, a ring having from 3 to 8 ring atoms which may also comprise, in addition to the nitrogen atom, one or two further heteroatoms of the oxygen, sulfur or nitrogen series "means radicals derived from propylamine, azetidine, pyrrolidine, piperidine, azepanes, azoanes, azepine, dioxazine, 1,4-diazepane, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine , imidazole, imidazoline, imidazolidine, isothiazolidine, isothiazoline, isoxazoline, isoxazolidine, 2-isoxazoline, cetopiperazine, morpholine, [1,4] oxazepane, piperazine, pyrazine, pyrazoline, pyrazolidine, pyridazine, pyrrolidinone, pyrroline, tetrahydropyridine, thiazolidine, thiazoline, thiomorpholine. The "radicals of formula IV" mean substituents derived from azetidin-2-one, pyrrolidin-2-one, piperidin-2-one, azepane-2-one and azocan-2-one and, in each case, are substituted in the Nitrogen atom with R8. -y The partial formula "R18 19" of formula V means, in the case where the branching point is present one, two or three times, radicals such as methylene, ethylene or propylene which, in each case, are substituted with the radicals R18 and R19. In the case where the branching point is present zero times, the result is a covalent bond.

The partial formula " "of formula VI means, in the case where the branching point is present one, two or three times, radicals such as methylene, ethylene or propylene which, in each case, are substituted with the radicals R28 and R29. in which the branching point is present zero times, the result is a covalent bond.It should be noted that in partial formula III, the binding to 1 H-imidazole is carried out through A3, and not through A5. "- aryl (Cg-C- | 4) -" means aromatic hydrocarbon radicals having from 6 to 14 ring carbon atoms Examples of aryl radicals (Cg-C- | 4) - are phenyl, naphthyl , for example, 1-naphthyl, 2-naphthyl, anthryl or fluorenyl, the naphthyl radicals and, in In particular, phenyl radicals are preferred aryl radicals. The term "4 to 15 member Het ring" or "Het" means ring systems having from 4 to 15 carbon atoms, which are present in one, two or three mutually connected ring systems, and which comprise one, two , three or four heteroatoms identical or different from the oxygen, nitrogen or sulfur series. Examples of these ring systems are acridinyl, azepinyl, azetidinyl, aziridinyl, benzimidazolinyl, benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzthiazolyl, benztriazolyl, benztetrazolyl, benzisoxazolyl, benzisothiazolyl, carbazolyl, 4aH-carbazolyl, carbolinyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, chromanyl, chromenyl, cinnolinyl, deca-hydroquinolinyl, dibenzofuranyl, dibenzothiophenyl, dihydrofuran [2,3-b] -tetrahydrofuranyl, dihydrofuranyl, dioxolyl, dioxanyl, 2H, 6H-1, 5.2 -dithiazinium, furanyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl (benzimidazolyl), isothiazolidinyl, 2-isothiazolinyl, isothiazolyl, isoxazolyl, isoxazolidinyl, 2-isoxazolinyl, morpholiniol, naphthyridinyl, octahydroisoquinolinyl or, oxadiazolyl, 1,2,3-oxadiazolyl, 1,4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1,4-oxadiazolyl, oxazolidinyl, oxazolyl, oxothiolanyl, pyrimidinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxythinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, piroazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridooxazolyl, pyridoimidazolyl, pyridothiazolyl, pyridothiophenyl, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrahydropyridinyl, 6H-1, 2,5-thiazinyl, 1,2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 2,5-thiadiazolyl, 1,3-thiadiazolyl, thianthenyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiomorpholinyl, thiophenyl, triazinyl, 1,2,3-triazolyl, 1, 2,4-triazolyl, 1, 2,5-triazolyl, 1,4-triazolyl and xanthenyl. Preferred Het rings are the benzofuranyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzothiophenyl, 1,3-benzodioxolyl, quinazolinyl, quinolinyl, quinoxalinyl, chromanyl, cinnolinyl, furanyl, such as 2-furanyl and 3-furanyl radicals; imidazolyl, indolyl, indazolyl, isoquinolinyl, isochromanyl, isoindolyl, isothiazolyl, isoxazolyl, oxazolyl, phthalazinyl, pteridinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridoimidazolyl, pyridopyridinyl, pyridapyrimidinyl, pyridyl, such as 2-pyridyl, 3-pyridyl or 4-pyridyl; pyrimidinyl, pyrrolyl, such as 2-pyrrolyl and 3-pyrrolyl; purinyl, thiazolyl, tetrazolyl or thienyl, such as 2-thienyl and 3-thienyl. The term "halogen" means fluorine, chlorine, bromine or iodine. The term "= O" means an oxo radical or a carbonyl radical (-C (O) -) or nitroso (-N = O). The compounds of the invention can be prepared by well known processes or by processes described herein. The functional groups in the intermediates used, for example amino or carboxyl groups, can, in this respect, be masked by adequate protective groups. Examples of suitable protecting groups for the amino functions are the t-butoxycarbonyl, benzyloxycarbonyl or phthaloyl group, and the trityl or tosyl protecting group. Examples of suitable protecting groups for the carboxyl function are alkyl, aryl or arylalkyl esters. Protective groups can be introduced and eliminated by techniques that are well known or described herein (see Green, TW, Wutz, PGM, Protective Groups in Organic Synthesis (1991), 2nd ed., Wiley-lnterscience, or Kocienski, P ., Protecting Groups (1994), Thieme). The term "protecting group" may also include the corresponding protective groups attached to polymers. Compounds of formula (la) which are masked in this manner, and in which the functional groups of the radical X, when appropriate, can be masked in a similar manner, can be converted, although they are not themselves pharmacologically active, when it results. appropriate, after administration to mammals, in the pharmacologically active compounds of the invention by metabolism. The invention further relates to a process for preparing the compound of formula I and / or a stereoisomeric form of the compound of formula I and / or the physiologically tolerated salt of the compound of formula I, comprising a) preparing the compound of formula I as shown in scheme 1, wherein X and Y have, in each case, the meanings indicated above: Scheme 1 J (C) (F) The compounds according to (Vil) can be obtained by conventional methods, for example from the hydrochloride of 4-imidazole acetic acid, by reaction in lower alcohols in the presence of thionyl chloride, in which PG1 is a suitable carboxyl protecting group. A suitable protecting group PG2 is introduced by conventional processes in step (A) of the process. The resulting compounds (VIII) are reacted in step (B) of the process in the presence of a base in an inert solvent at temperatures between -90 ° C and 50 ° C with a compound of formula to produce the compounds (IX), in which PG1 'is a suitable carboxyl protecting group. The reaction of the compounds (IX) in step (C) of the process in the presence of a strong base in an inert solvent at temperatures between -90 ° C and + 50 ° C with the compounds of formula X-LG (XIV) produces the compounds (X), in which the functional groups present in X can be masked by suitable protecting groups, and LG is a suitable activating group such as, for example, chlorine, bromine, iodine, mesylate, tosylate or triflate. In step (D) of the process, the compounds (X) are converted to the compounds (XI) by removing the protecting groups PG1, PG1 'and PG2 and, where appropriate, the protective group present in X, by conventional processes and, when appropriate, treating under acid-aqueous conditions at temperatures between room temperature and 100 ° C. The compounds (XII) can be obtained from the compounds (XI) in step (E) by introducing a suitable carboxyl protecting group PG1"under conventional conditions The compounds according to (Ia) can be obtained in step (F). ) by reacting the compounds (XII) in the presence of a base at temperatures between -90 ° C and + 60 ° C in an inert solvent, with compounds of formula Y-LG (XV), in which LG is a suitable activating group such as chlorine, bromine, iodine, mesylate, tosylate or triflate, and Y has the meanings indicated above. The compounds (la) can be obtained, alternatively, by reacting the compounds (XII) under the conditions of Mitsonobu with the compounds of the formula Y-OH (XVI), in which Y has the meanings indicated above. Compounds (la) can be obtained, alternatively, by reacting the compounds (XII) in the presence of a base at temperatures between -90 ° C and + 60 ° C in an inert solvent, with six-fluoronitroaromatic compounds of six members or 4-fluoronitroaromatic compounds with six members. The nitro group is subsequently reduced to produce the amino group by conventional processes, eg at room temperature in lower alcohols with hydrogen in the presence of a transition metal catalyst, or in inert solvents in the presence of tin chloride (II). dihydrate, and acylated by conventional processes. The compounds according to (Ib) are obtained in step (G) by removing the protecting group PG1"and, when appropriate, the protective group present in X under conventional conditions. Compounds (XIII), (XIV), (XV) and (XVI) are available in the market, are known in the literature, or can be prepared by known processes in the bibliography. The reactions can be carried out under atmospheric pressure, elevated or reduced. In general they are carried out under atmospheric pressure. Suitable solvents for steps (B), (C) and (F) of the process are inert organic solvents. These include, for example, ethers such as dioxane, THF or 1,2-dimethoxyethane, hydrocarbons such as cyclohexane, benzene, toluene or xylene, nitroaromatic compounds such as nitrobenzene, carboxamides such as dimethylformamide or dimethylacetamide, alkyl sulfoxides such as dimethyl sulfoxide, aliphatic nitriles as acetonitrile, or other solvents such as N-methylpyrrolidinone. Similarly, it is also possible to use mixtures of the solvents mentioned. Suitable bases for stages (B), (C) and (F) of the process are the usual Inorganic and organic bases. These include, preferably, alkali metal and alkaline earth metal carbonates such as sodium, potassium or calcium carbonate, alkali metal hydrides such as sodium hydride, amides such as lithium bis (trimethylsilyl) amide or lithium diisopropylamide, organic amines. such as pyridine, 4-N, N-dimethylaminopyridine, triethylamine, ethyldiisopropylamine, N-methylmorpholine, N-methylpiperidine, 1,5-diazabicyclo (4.3.0) non-5-ene (DBN) or 1,8-diazabicyclo ( 5.4.0) undec-7-ene (DBU), or organometallic compounds such as butyl lithium or phenyl-lithium. Particularly preferred are sodium hydride, lithium b.s (tr ymethylsilyl) amide and triethylamine. The conditions of Mitsonobu mean, in general, the use of inert solvents in the presence of an azodicarboxylate, when appropriate in the presence of another reagent, preferably in a temperature range from 0 ° C to room temperature under atmospheric pressure. Examples of inert solvents are halohydrocarbons such as methylene chloride, ethers such as dioxane, THF or 1,2-dimethoxyethane, hydrocarbons such as benzene, toluene or xylene, nitroaromatic compounds such as nitrobenzene, carboxamides such as dimethylformamide or dimethylacetamide, alkyl sulfoxides such as dimethyl sulfoxide. , aliphatic nitriles such as acetonitrile, esters such as ethyl benzoate or other solvents such as N-methylpyrrolidinone. Similarly, it is also possible to use mixtures of the solvents mentioned. Examples of other common reagents for the Mitsonobu reaction are triphenylphosphine, diphenyl (2-pyridyl) phosphine or (4-dimethylamino-phenyl) diphenylphosphine. Examples of azodicarboxylates are diethyl azodicarboxylate, dimethyl azodicarboxylate, diisopropyl azodicarboxylate or di-tert-butyl azodicarboxylate. A compound of formula I prepared as shown in scheme 1, or a suitable precursor of formula I, which is produced due to its chemical structure in enantiomeric forms, by saline formation with enantiopure acids or bases, a chromatography in chiral stationary phases , or a derivatization using chiral enantiopure compounds as amino acids, a separation of the diastereomers obtained from this Thus, an elimination of the chiral auxiliary groups fractionates the pure enantiomers (process b), or the compound of formula I prepared as shown in scheme 1 is isolated in the free form or, in the case where groups are present. acid or basic, it becomes the physiologically tolerated salts (process c). In step b) of the process, the compound of formula I, if it appears as a mixture of diastereomers or enantiomers or is produced as its mixtures in the chosen synthesis, is separated into the pure stereoisomers by chromatography on an optionally chiral support material or , if the racemic compound of formula I is capable of forming salts, by fractional crystallization of the diastereomeric salts formed with a base or optically active acid as an adjuvant. The chiral stationary phases suitable for thin layer or column chromatography to separate the enantiomers are, for example, modified silica gel supports (the so-called Pirkle phases) and high molecular weight carbohydrates, such as triacetylcellulose. It is also possible to use, for analytical purposes, gas chromatographic methods on chiral stationary phases after appropriate derivatization, known to those skilled in the art. To separate the enantiomers from the racemic carboxylic acids, diastereomeric salts with different solubility will be formed using an optically active base, which is usually commercially available, such as (-) - nicotine, (+) - and (-) - phenylethylamine, bases of quinine, L-lysine or L- and D-arginine, the less soluble component is isolated as a solid, the more soluble diastereomer is deposited from the mother liquor, and the pure enantiomers are obtained from the diastereomeric salts obtained in this manner. In the same way it is possible, in principle, to convert the racemic compounds of formula I containing a basic group, such as an amino group, with optically active acids, such as acid (+) - camphor-10-sulfonic acid, D- and L-tartaric acid, D- and L-lactic acid and (+) and (-) - mandelic acid, to produce the pure enantiomers. Chiral compounds containing alcohol or amine functions can also be converted with appropriately activated enantiopure amino acids or, where appropriate, N-protected to produce the corresponding esters or amides, or conversely, chiral carboxylic acids can be converted, with enantiopure amino acids carboxyl-protected, in the amides, or with enantiopure hydroxycarboxylic acids, such as lactic acid, to produce the corresponding chiral esters. The chirality of the amino acid or alcohol moiety introduced in the enantiopure form can then be used to separate the isomers by the mode of a separation of the diastereomers which are now present by crystallization or chromatography on suitable stationary phases and then removing the included chiral moiety by suitable methods . Another possibility with some of the compounds of the invention is to employ diastereomeric or enantiomerically pure starting materials to prepare framework structures. Therefore, it is possible, when appropriate, to also use other simplified processes or processes to purify the final products. These starting materials have been previously prepared in an enatiomeric or diastereomerically pure form by processes known in the literature. This may mean, in particular, that enantioselective processes are used in the synthesis of the basic structures, or a separation of enantiomers (or diastereomers) can also be carried out at an early stage of the synthesis and not at the stage of the final products. Similarly, a simplification of these separations can be achieved by acting in two or more stages. The acidic or basic products of the compound of formula I can be in the form of their salts or in the free form. Preferred are pharmacologically acceptable salts, for example, alkali metal salts or alkaline earth metal salts or hydrochlorides, hydrobromides, sulfates, hemisulfates, all possible phosphates, and salts of amino acids, natural bases or carboxylic acids. Physiologically tolerated salts are prepared from compounds of formula I capable of forming salts, including their stereoisomeric forms, in step c) of the process in a manner known per se. The compounds of formula I form alkali metal, alkaline earth metal salts or, when appropriate, stable substituted ammonium salts with basic reagents such as hydroxides, carbonates, bicarbonates, alcoholates and ammonia or organic bases, for example trimethyl- or triethylamine, ethanolamine, diethanolamine or triethanolamine, trometamol or also with basic amino acids, for example lysine, ornithine or arginine. If the compounds of formula I have basic groups, it is also It is possible to prepare stable acid addition salts with strong acids. Suitable for this purpose are inorganic and organic acids such as hydrochloric, hydrobromic, sulfuric, hemsulfuric, phosphoric, methanesulphonic, benesulphonic, p-toluenesulphonic, 4-bromobenzenesulphonic, cyclohexylamido-sulphonic, trfluoromethylsulphonic, 2-hydroxyethanesulphonic, acetic, oxalic, tartaric, succinic, glycerolophosphoric, lactic, malic, adipic, citric, fumaric, maleic, gluconic, glucuronic, palmitic or trifluoroacetic. The invention also relates to medicaments characterized by an effective content of at least one compound of formula I and / or of a physiologically tolerated salt of the compound of formula I and / or an optionally stereoisomeric form of the compound of formula I, together with a vehicle, additive and / or other pharmaceutically suitable and physiologically tolerated ingredients and excipients. Because of the pharmacological properties, the compounds of the invention are suitable for the prophylaxis and therapy of all disorders that can be treated by the inhibition of TAFla. Therefore, TAFla inhibitors are suitable for prophylactic use and for therapeutic use in humans. They are suitable for acute treatment and long-term therapy. TAFla inhibitors can be used in patients who suffer deterioration of their well-being or diseases associated with thrombosis, embolism, hypercoagulability or fibrotic changes. These include myocardial infarction, angina pectoris and all other types of acute coronary syndrome, cerebrovascular accidents, peripheral vascular disorders, deep vein thrombosis, pulmonary embolism, embolic or thrombotic events caused by cardiac arrhythmias, cardiovascular events such as restenosis after revascularization, angioplasty and similar procedures such as stent implants and bypass operations. TAFla inhibitors can also be used in all procedures that lead to contact of blood with foreign surfaces, such as for dialysis patients and patients with internal catheters. TAFla inhibitors can be used to reduce the risk of thrombosis after surgical procedures such as knee and hip joint operations. TAFla inhibitors are suitable for the treatment of patients with disseminated intravascular coagulation, sepsis and other intravascular events associated with inflammation. TAFla inhibitors are also suitable for the prophylaxis and treatment of patients with atherosclerosis, diabetes and the metabolic syndrome and its sequelae. Impairments of the hemotic system (eg, fibrin deposits) have been implicated in the mechanisms that lead to the growth of tumors and tumor metastasis; TAFla inhibitors are adequate to slow or prevent these processes. Other indications for the use of TAFla inhibitors are fibrotic changes in the lung, such as obstructive pulmonary disease. chronic, adult respiratory distress syndrome (ARDS), and the eye, such as fibrin deposits after eye operations. TAFla inhibitors are also suitable for the prevention and / or treatment of bedsores. The medicaments of the invention can be administered orally, inhalationally, rectally or transdermally, or by subcutaneous, intra-articular, intraperitoneal or intravenous injection. Oral administration is preferred. Stents and other surfaces that come in contact with blood in the body may be coated with TAFla inhibitors. The invention also relates to a process for producing a medicament, which comprises preparing a suitable dosage form of at least one compound of formula I with a pharmaceutically suitable and physiologically tolerated carrier and, when appropriate, more active ingredients, additives or excipients. adequate. Suitable pharmaceutical or solid formulations are, for example, granules, powders, coated tablets, tablets, (micro) capsules, suppositories, syrups, solutions, suspensions, emulsions, drops or injectable solutions, and products with delayed release of the active ingredient, in the production of which uses normal physiologically suitable adjuvants, such as vehicles, disintegrants, binders, coating agents, swelling agents, glidants or lubricants, flavors, sweeteners and solubilizers. The excipients that are used with frequency and that can be mentioned are magnesium carbonate, titanium dioxide, lactose, mannitol and other sugars, talc, milk protein, gelatin, starch, cellulose and its derivatives, animal and vegetable oils such as fish liver oil, oil of sunflower, peanut or sesame, polyethylene glycol, and solvents such as, for example, sterile water and monohydric and polyhydric alcohols, such as glycerol. The pharmaceutical products are preferably produced and administered in dosage units, in which each unit comprises, as an active ingredient, a specific dose of the compound of the invention of formula I. In the case of solid dosage units such as tablets, capsules, tablets coated or suspensions, this dose may be up to about 1000 mg, but preferably from about 50 to 300 mg and, in the case of injectable solutions in the form of ampoules, up to about 300 mg but preferably from about 10 to 100 mg. The daily doses indicated for the treatment of an adult patient weighing approximately 70 kg are, depending on the activity of the compound of formula I, from about 2 mg to 1000 mg of the active ingredient, preferably from about 50 mg to 500 mg. However, in some circumstances, higher or lower daily doses may also be appropriate. The daily dose can be administered by a single administration in the form of a unit dosage unit, or also a plurality of smaller dosage units, or by multiple administration of divided doses at specific intervals. TAFla inhibitors can be administered as monotherapy and together with all antithrombotics (anticoagulants and inhibitors of platelet aggregation), thrombolytics (plasminogen activators of any type), other substances that have profibrinolytic activity, antihypertensive agents, blood glucose regulators, agents that decrease lipids and antiarrhythmics.

Examples The final products are usually determined by mass spectroscopy methods (FAB-, ESI-MS) and 1H NMR; the main peak or the two main peaks are indicated in each case. The temperatures are indicated in degrees Celsius, TA means room temperature (21 ° C to 24 ° C). The abbreviations used are explained or correspond to the usual conventions. Unless otherwise indicated, LC-MS analyzes are performed under the following conditions: Method A: Column: YMC Jsphere 33 x 2.1 mm, 4 μm loading material, mobile phase: CH3CN + trifluoroacetic acid (TFA) 0.05%: H2O + 0.05% TFA, gradient: 5:95 (0 min) to 95: 5 (3.4 min), flow rate: 1 ml / min, temperature: 30 ° C; Method B: Column: YMC Jsphere 20 x 2.1 mm, material from charge 4 μm, mobile phase: CH3CN + 0.05% trifluoroacetic acid (TFA): H2O + 0.05% TFA, gradient: 4:96 (0 min) to 95: 5 (2.0 min), flow rate : 1 ml / min, temperature: 30 ° C; Method C: Column: YMC Jsphere 33 x 2.1 mm, loading material 4 μm, mobile phase: CH3CN + 0.05% trifluoroacetic acid (TFA): H2O + 0.05% TFA, gradient: 5:95 (0 min) to 95: 5 (2.5 min), flow rate: 1.3 ml / min, temperature: 30 ° C. Unless otherwise indicated, the chromatographic separations were performed on silica gel with ethyl acetate / heptane mixtures as the mobile phase, and the preparative separations on reverse phase silica gel (RP) (HPLC) with water mixtures. containing trifluoroacetic acid / acetonitrile as the mobile phase. The solvents were removed by evaporation usually under reduced pressure from 35 ° C to 45 ° C.

EXAMPLE 1 3- (6-Aminopyridin-3-yl) -2- (1-cethexyl-1 H-imidazol-4-yl) propionic acid Example 1a (tert-butyl) 5-methylpyridin-2-yl carbamate A solution of 60.54 g (277 mmol) of di-tert-butyl dicarbonate in 50 ml of CH2Cl2 was added dropwise to a solution of 30.00 g (177 mmol) of 5-methy1pyridin-2-ylamine and 3.39 g (28 mmol) of 4-dimethylaminopyridine in 150 ml of CH2Cl2. The resulting solution was stirred for 16 h (h) at room temperature and then concentrated to dryness. Purification by chromatography on silica gel yielded 15.4 g of the product as a colorless solid. MS (ES +) = 209 [M + H] + Example 1b A solution of 14.9 g (72 mmol) of the compound of example 1a was introduced into 700 ml of CCI and heated until it boiled. Addition of a mixture of 12.8 g (72 mmol) of N-bromosuccinimide and 1.2 g (7 mmol) of 2,2'-azobis (isobutyronitrile) was followed by heating at reflux for 2.5 h. The reaction mixture was filtered in a quench, the filter residue was washed with CCI4, and the solvent was removed from the combined filtrates. The residue was recrystallized from acetonitrile, removed by suction filtration, washed with acetonitrile and acetonitrile / methyl tert-butyl ether (1: 1) and dried under reduced pressure. 6.94 g of the desired compound were obtained as a cream-colored solid. 1 H-NMR (500 MHz, DMSO-d 6): d = 1.48 (s, 9 H), 4.71 (s, 2 H), 7.78 (d, 1 H), 7.82 (d, 1 H) ), 8.32 (s, 1 H). Example 1c Methyl 4-imidazoleacetate hydrochloride 5.0 g (30.75 mmol) of 4-imidazoleacetic acid was dissolved in 50 ml of methanol and then 5.6 ml (76.87 mmol) of thionyl chloride was added. The resulting solution was heated to reflux for 4 h and, after cool, evaporated to dryness. Drying under reduced pressure yielded 5.3 g of the desired product as a pale yellow solid. MS (ES +) = 141 [M + H] + Example 1d [1- (tolyl-4-sulfonyl) -1H-imidazol-4-yl] methyl acetate A solution of 5.0 g (28.31 mmol) of the Compound of Example 1c and 9.8 mL of triethylamine (70.72 mmol) in 350 mL of CH2Cl2 was cooled to 0 ° C, and then 7.04 g (36.90 mmol) of p-toluenesulfonyl chloride was added. The solution was stirred at 0 ° C for 15 minutes (min) and at room temperature for 15 min, concentrated and then washed with a solution of ammonium chloride and water. The organic phase was dried over Na 2 SO 4 and, after filtration, evaporated to dryness. Purification by chromatography on silica gel yielded 7.2 g of the desired product. T.r. (method A) = 1.71 min MS (ES +) = 295 [M + Hf Example 1e • 2- [1- (tolyl-4-sulfonyl) -1 H-imidazol-4-yl] dimethyl malonate A solution of 3.0 g (10.19 mmol) of the compound of Example 1d in 50 ml of absolute tetrahydrofuran (THF) was cooled to 0 ° C and 9.3 ml (11.1 mmol) of a solution was slowly added dropwise. to the % lithium bis (trimethylsilyl) amide in THF. After stirring at 0 ° C for 30 min, 0.89 ml of methyl cyanoformate was added, and the resulting solution was slowly heated to room temperature throughout the course of the reaction. a period of 1, 5 h. The reaction solution was then poured into about 300 ml of a saturated ammonium chloride solution. It was extracted several times with ethyl acetate (EA) and the combined EA extracts were washed with water and dried over Na 2 SO 4 and then evaporated to dryness. Purification by chromatography on silica gel yielded 2.2 g of the title compound. T.r. (method A) = 1.89 min MS (ES +) = 353 [M + H] + Example 1f 2- (6-tert-Butyloxycarbonylaminopyridin-3-ylmethyl) -2- [1- (tolyl-4-sulfonyl-1 Dimethyl H-imidazol-4-yl] malonate A solution of 2.2 g (6.24 mmol) of the compound of Example 1e in 40 ml of absolute N, N'-dimethylformamide (DMF) was cooled to 0 ° C and 150 mg (6.26 mmol) of NaH (50%) were added, and the mixture was stirred at room temperature for 1 h After cooling to 0 ° C, 1.8 g (6.24 mmol) was added. of 2- (6-tert-butyloxycarbonylaminopyridin-3-yl) methyl bromide, and the resulting solution was stirred at 0 ° C for 30 min, then 50 ml of water was added, and the mixture was extracted several times with EA. The combined EA extracts were dried over Na 2 S 4, filtered and evaporated to dryness Purification of the residue by chromatography on silica gel yielded 2.9 g of the desired compound Tr (method A) = 2.10 min MS (ES +) = 559 [M + H] + Example 1g Ethyl 3- (6-aminopyridin-3-yl) -2- (1 H-imidazol-4-yl) propionate 400.0 mg (0.72 mmol) of the compound of Example 1f were suspended in a solution of 5 ml of concentrated hydroiodic acid at 37% and ml of water. The resulting suspension was heated in a microwave oven at 180 ° C for 20 min. The reaction solution was then concentrated, and the resulting residue was suspended in 50 ml of ethanol and again concentrated. The remaining residue was dissolved in 50 ml of ethanol and, after the addition of 40 ml of an ethereal solution saturated with gaseous HCl, the solution was stirred for 3 h. Evaporated to dryness, the residue was suspended in 20 ml of a mixture of EA and a saturated solution of NaHCO 3, and the reaction solution was extracted several times with EA. The combined EA extracts were dried over Na 2 SO 4, filtered and concentrated. Purification of the residue by chromatography on silica gel yielded 134 mg of the desired compound. T.r. (method A) = 0.20 min MS (ES +) = 261 [M + H] + Example 1h 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1H-imidazole-4) -yl) effile propionate Method 1: A solution of 60.1 mg (0.23 mmol) of the compound of example 1g, 37.7 mg (0.23 mmol) of bromocyclohexane and 100 μl of triethylamine in 1 ml of THF absolute was treated in a microwave oven at 170 ° C for 40 min The reaction solution was then suspended in a little EA / water (1: 1), and the phases were separated, dried over Na 2 SO 4, filtered and evaporated to dryness. Purification by chromatography on RP silica gel with CH3CN / water / TFA 0, 1% as mobile phase, and lyophilization of the pooled product fractions yielded 18.0 mg of the desired compound as the bistrifluoroacetate as an amorphous solid. As an alternative to method 1, the title compound was also prepared by method 2 described below. Method 2: A solution of 200.0 mg (0.77 mmol) of the compound of Example 1e and 39.0 mg (0.77 mmol, 60%) of NaH in 5 mL of absolute DMF was stirred at room temperature for 1 h and then 123.7 mg (0.77 mmol) of 3-bromocyclohexene were added. The resulting solution was stirred at room temperature for 1 h. After the addition of 2 ml of water, extraction with EA was carried out several times and drying of the extracts of AE collected over MgSO. A concentration, a purification of the residue by chromatography on RP silica gel with water / acetonitrile (5:95) and a concentration of the required fractions yielded 152 mg of 3- (6-aminopyridin-3-yl) -2. - ethyl (1-cyclohex-2-en-1 H-imidazol-4-yl) propionate. This compound was then hydrogenated in 15 ml of methanol in the presence of Pd / activated carbon (10%) at room temperature for 2 h. Concentration and drying under reduced pressure yielded 127 mg of the desired title compound as an amorphous solid.

T.r. (method A) = 0.89 min MS (ES +) = 343 [M + H] + 1 H-NMR (500 MHz, DMSO-d 6): d = 1.12 (t, 3 H), 1.18 (m, 1 H), 1.38 (m, 2 H), 1.68 (m, 3 H), 1.80 (m, 2H), 2.03 (m, 2H), 3.08 (dd, 1 H), 3.15 (dd, 1 H), 3.42 (q, 2H), 4.10 (dt, 1 H), 4.24 (m, 1H), 6.95 (d, 1H), 7.75 (m, 3H), 8.10 (s, 2H). Example 1 i 3- (6-Aminopyridin-3-yl) -2- (1-cyclohexyl-1H-imidazol-4-yl) propionic acid hydrochloride A solution of 13.7 mg (0.03 mmol) of the Example 1h in 0.5 ml of water and 0.5 ml of concentrated hydrochloric acid at 37% was treated in a microwave oven at 180 ° C for 5 min. It was then evaporated to dryness under reduced pressure, the residue was suspended in a little water, and the solution was lyophilized. This produced 8.0 mg of the title compound as the bishydrochloride in the form of an amorphous solid. T.r. (method A) = 0.80 MS (ES +) = 315 [M + H] + 1 H NMR (400 MHz, DMSO-d6): d = 0.86 (m, 1H), 1.28 (m, 5H ), 1.60 (m, 3H), 1.78 (m, 2H), 1.92 (m, 2H), 2.77 (dd, 1H), 2.95 (dd, 1H), 3.55 (dt, 1 H), 3.95 (m, 1 H), 5.60 (s, 2H), 6.34 (d, 1 H), 7.00 (s, 1 H), 7.14 ( dd, 1 H), 7.58 (s, 1 H), 7.68 (s, 1 H). The two enantiomers of the compound of Example 1g were separated by preparative chiral phase chromatography; phase: Chiralpak ADH40, column dimensions: 250 x 4 mm, mobile phase: heptane: ethanol: methanol 8: 1: 1 plus 0.1% ammonium acetate (isocratic), Flow rate: 1 ml / min, temperature 30 ° C: Enantiomer 1: T.r. = 6.13 min Enantiomer 2: T.r. 46.32 min.

Example 2 Methyl 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazol-4-yl) propionate 3 ml of a saturated ethereal solution of HCl was added to a solution of 50, 0 mg (0.16 mmol) of the compound of example 1i in 8 ml of methanol and stirred at room temperature for 6 h. The solution was then concentrated to dryness, and the resulting residue was dried at high vacuum. 51 mg of the title compound was produced as the bishydrochloride in the form of an amorphous solid. T.r. (method A) = 0.90 min MS (ES +) = 329 [M + Hf 1 H NMR (500 MHz, DMSO-d6): d = 1.20 (m, 1 H), 1.37 (m, 2H), 1.65 (m, 3H), 1.82 (m, 2H), 2.0 (m, 2H), 3.10 (dd, 1 H), 3.18 (dd, 1H), 3 , 65 (s, 3H), 4.22 (m, 2H), 6.95 (d, 1H), 7.72 (m, 3H), 8.05 (s, 2H) The two enantiomers of the compound were separated by preparative chiral phase chromatography; phase: Chiracel OD / H-61, mobile phase: heptane: propanol: methanol 15: 1: 1 plus 0.1% diethylamine (Socratic), flow rate: 1 ml / min, temperature: 30 ° C: Enantiomer 1: T.r. = 14.05 min. Enantiomer 2: T.r. = 17,15 min.

EXAMPLE 3 Impopropyl 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1H-imidazoI-4-yl) propionate. 2 ml of a saturated ethereal HCl solution was added. to a solution of 38.0 mg (0.12 mmol) of the compound of example 1i in 5 ml of isopropanol and stirred at room temperature for 4 h. The solution was then concentrated to dryness, and the resulting residue was dried under high vacuum. 25 mg of the title compound was produced as the bishydrochloride in the form of an amorphous solid. T.r. (method A) = 0.92 min MS (ES +) = 357 [M + Hf 1 H NMR (500 MHz, DMSO-d6): d = 1.02 (d, 6H), 1.15 (m, 3H) , 1.38 (m, 2H), 1.68 (m, 3H), 1.85 (m, 1 H), 2.03 (m, 1 H), 3.05 (dd, 1 H), 3 , 14 (dd, 1 H), 3.78 (dt, 1 H), 4.20 (m, 2H), 4.90 (m, 1 H), 6.90 (m, 1 H), 7, 74 (m, 3H), 8.00 (m, 1 H) EXAMPLE 4 Cyclopropylmethyl 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1H-imidazol-4-yl) propionate 1 ml of a saturated ethereal solution of HCl was added to a solution of 50.0 mg (0.16 mmol) of the compound of example 1i in 2 ml of cyclopropylcarbinol and stirred at room temperature for 12 h. The solution was then concentrated to dryness, and the resulting residue was dried at high vacuum. A purification by chromatography on gel of silica with CH2Cl2 / methane as mobile phase yielded 29 mg of the title compound as an amorphous solid. T.r. (method A) = 0.91 min MS (ES +) = 369 [M + H] + 1 H-NMR (500 MHz, DMSO-d 6): d = 0.18 (m, 2 H), 0.42 (m, 2 H), 0.98 (m, 1 H), 1.18 (m, 1 H ), 1, 34 (m, 2H), 1, 60 (m, 3H), 1.75 (d, 2H), 1, 94 (d, 2H), 2.90 (m, 2H), 3.70 (m, 1H), 3.78 (d, 2H), 3.97 (m, 1H), 5.70 (s, 2H) , 6.34 (d, 1 H), 7.05 (s, 1 H), 7.13 (d, 1 H), 7.55 (s, 1 H), 7.70 (s, 1 H) EXAMPLE 5 2-Hydroxyethyl 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H -methazol-4-yl) propionate 0.4 ml of a saturated ethereal solution of HCl was added to a solution of 50.0 mg (0.16 mmol) of the compound of example 1i in 1 ml of ethylene glycol and stirred at room temperature for 1 h. The solution was then concentrated to dryness, and the residue was suspended in a saturated solution of NaHCO3 and extracted with EA several times. The combined EA extracts were dried, filtered and concentrated. The resulting residue was dried under high vacuum, resulting in 33 mg of the title compound as a pale yellow oil. T.r. (method A) = 0.85 min MS (ES +) = 359 [M + H] + 1 H NMR (500 MHz, DMSO-d6): d = 0.85 (m, 1 H), 1, 15-1 , 35 (m, 5H), 1, 60 (m, 3H), 1.78 (d, 1 H), 1.95 (m, 1H), 2.90 (m, 1H), 3.48 (m , 1 H), 4.00 (m, 2H), 5.68 (s, 2H), 6.32 (d, 1 H), 7.05 (s, 1 H), 7.13 (d, 1 H), 7.55 (s, 1 H), 7.65 (d, 1H) EXAMPLE 6 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazol-4-yl) 1-cyclohexyloxycarbonyloxyethyl propionate A solution of 50.0 mg. , 16 mmol) of the compound of Example 1i and 39 mg (0.19 mmol) of 1-cyclohexyloxycarbonyloxy-1-ethyl chloride, 13 mg (0.08 mmol) of Kl and 26 mg (0, 19 mmol) of K2CO3 in 2 ml of DMF was stirred at 60 ° C for 12 h. Then 5 ml of water was added and the reaction solution was extracted several times with EA. The combined EA extracts were dried, filtered and concentrated to dryness. The resulting residue was purified on silica gel with CH2Cl2 / methanol as mobile phase, resulting in 32 mg of the title compound as an amorphous solid. T.r. (method A) = 0.81 min MS (ES +) = 485 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): d = 0.86 (m, 4H), 1, 20-1, 40 (m, 8H), 1.63 (m, 2H), 1.70 (m , 2H), 1.95 (m, 1 H), 2.90 (m, 1 H), 3.45 (m, 1 H), 3.52 (s, 3H), 3.70 (m, 1 H), 3.94 (m, 1 H), 4.13 (m, 2H), 4.52 (m, 1 H), 5.68 (d, 1 H), 6.30 (t, 1 H) ), 6.55 (m, 1 H), 7.00 (s, 1 H), 7.13 (m, 1 H), 7.72 (m, 2H).

Example 7 3- (6-Aminopyridin-3-yl) -2- (1-cyclopentyl-1 H-imidazol-4-yl) pro-pionic acid Example 7a (cyclopentyl 1-cyclopentyl-1 H-lmidazol-4-yl) acetate. Midazole-4-acetic acid hydrochloride (5.30 g, 32.60 mmol) and cesium carbonate (31) were introduced. , 90 g, 97.80 mmol) in absolute DMF. Cyclopentyl bromide (10.5 ml, 97.80 mmol) was added. The mixture was stirred at 110 ° C for 3 h and then filtered through a lightening layer, the residue was washed with CH 2 Cl 2 and the filtrate was concentrated under reduced pressure. The residue was suspended in EA, and the solution was washed with water and 0.5N HCl. The organic phase was dried over Na2SO4 and the solvent was then removed under reduced pressure. A purification of the raw product through a cartridge (70 g of silica gel) yielded 2.65 g of cyclopentyl (1-cyclopentyl-1 H-imidazol-4-yl) acetate. Tr: (method B) = 0.89 min MS (ES +) = 263 [M + Hf Example 7b Cyclopentylmethyl 2- (1-cyclopentyl-1 H-imidazol-4-yl) malonate) (1-cyclopentyl-1 was dissolved Clclopentyl H-imidazol-4-yl) acetate (2.00 g, 7.60 mmol) in tetrahydrofuran (THF, 45 mL). The reaction solution was cooled to 0 ° C and then lithium hexamethyldisilazane (20% in THF, 6.33 mL, 7.60 mmol) was added dropwise. The mixture was stirred at 0 ° C for another hour. Then methyl cyanoformate (0.66 ml, 8.36 mmol) was added. The mixture was stirred at 0 ° C for 10 min and then at room temperature for 7 h. The reaction solution was then added to a saturated solution of NH CI. It was extracted with AE, and the organic phase was washed with H2O and dried over Na2SO4. The solvent was removed under reduced pressure. Purification of the crude product by column chromatography (120 g of silica gel, EtOAc / n-heptane-2/1) yielded 0.46 g of 2- (1-cyclopentyl-1H-ylamdazole-4-). L) Cyclopen tilthyl malonate. T.r. (method B) = 1, 01 min MS (ES +) = 321 [M + H] + Example 7c Cyclopentylmethyl 2- (6-aminopyridin-3-ylmethyl) -2- (1-cyclopentyl-1H-imidazol-4-yl) malonate 2- (1-cyclopentyl-1H-imidazole-4- was dissolved il) Cyclopentylmethyl malonate (0.46 g, 1.44 mmol) in absolute DMF (5 mL). Sodium hydride (50%, 0.07 g, 1.44 mmol) was added at 0 ° C. The mixture was stirred at room temperature for 1 h and then cooled again to 0 ° C. Then tert-butyl (5-bromomethylpyridin-2-yl) carbamate (0.41 g, 1.44 mmol) was added, and the mixture was stirred at room temperature for 2 h.

While cooling on ice, the mixture was quenched with H2O and then extracted twice with EA. The organic phase was separated and dried over Na2SO4 and the solvent was then removed under reduced pressure. Purification of the crude product through a cartridge (50 g of silica gel) yielded 0.31 g of 2- (6-aminopyridin-3-methylmethyl) -2- (1-cyclopentyl-1 H-imidazole). -4-yl) cyclopentylmethyl malonate. T.r. (method C) = 1.47 min MS (ES +) = 527 [M + Hf Example 7d 3- (6-Aminopyridin-3-yl) -2- (1 -cidopentyl-1 H -amidazol-4-yl) propionic acid 2- (6-aminopyridin-3-ylmethyl) -2- was dissolved Cyclopentylmethyl (1-cyclopentyl-1 H-imidazol-4-yl) malonate (0.30 g, 0.57 mmol) in absolute ethanol (5 mL). Ethanolic HCl was added at 0 ° C. The reaction solution was allowed to stand at 10 ° C for 48 h. It was then concentrated under reduced pressure, and the residue was suspended in 2N HCl. It was heated in a microwave oven (3 x 4 min, 180 ° C). It was then washed with EA, and the aqueous phase was neutralized with 1 N NaOH and then lyophilized. The residue was suspended in methanol and filtered twice through a cartridge (C18). Concentration of the filtrate under reduced pressure yielded 0.10 g of 3- (6-aminopyridin-3-yl) -2- (1-cyclopentyl-1 H -amidazol-4-yl) propionic acid. T.r. (method C) = 0.64 min MS (ES +) = 301 [M + H] + NMR of H (d6-DMSO): 1.60 (m, 2H), 1.73 (m, 4H), 2.18 (m, 2H), 2.87 (ddd, 1H), 3.58 (t , 1 H), 3.78 (qt, 2H), 4.45 (t, 1H), 5.52 (s, 2H), 6.29 (d, 1H), 6.95 (s, 1 H), 7.11 (dd, 1H), 7.55 (s, 1H), 7.658 (s, 1H).

EXAMPLE 8 3- (6-Aminopyridin-3-yl) -2- (1-piperidn-4-yl-1 H-imidazol-4-yl) propionic acid Example 8a 3- ( 6-aminopyridin-3-yl) -2- (1- (benzylloxycarbonyl) piperidin-4-yl-1 H-imidazol-4-yl) ethyl propionate A solution of 60.1 mg (0.23 mmol) of the compound of Example 1g, 68.9 mg (0.23 mol) of 4-bromo-1-benzyloxycarbonylpiperidine, 97 μl (0.69 mmol) of triethylamine in 1 ml of absolute THF was treated in a microwave oven at 180 ° C for 2 h. The reaction solution was then mixed with 2 ml of EA / water (1: 1), and the EA phase was separated and dried over Na2S? 4. Filtration, separation of the solvent and purification of the remaining residue by chromatography on RP silica gel with CH3CN / water / 0.1% TFA as the mobile phase yielded 33 mg of the title compound as the bistrifluoroacetate. T.r. (method A) = 1.18 min MS (ES +) = 478 [M + H] + Example 8b 3- (6-aminopyridin-3-yl) -2- (1-piperidin-4-yl) acid thiazide -1H-imidazol-4-yl) propionic A solution of 17.7 mg (0.03 mmol) of the compound of example 2a in 0.5 ml of water and 0.5 ml of concentrated hydrochloric acid 37% was treated in a microwave oven at 180 ° C for 5 min. It was then evaporated to dryness under reduced pressure, the residue dissolved in a little water, and the solution was lyophilized. This produced 11.0 mg of the title compound as an amorphous solid. T.r. (method A) = 0.18 min MS (ES +) = 316 [M + H] + 1 H NMR (500 MHz, DMSO-d6): d = 1.27 (m, 2H), 2.20 (m, 4H), 2.28 (m, 2H), 3.08 (dd, 1H), 3.17 (dd, 1H), 4.15 (m, 2H), 4.52 (m, 1H), 6, 85 (d, 1 H), 7.52 (d, 1 H), 7.75 (m, 2H).

Example 9 3- (6-Aminopyridin-3-yl) -2- [1- (2-OXO-1-phenylpyrrolidin-3-yl) -1 H- midazol-4-yl] pro-pionic acid Example 9a 3 - (6-aminopyridin-3-yl) -2- [1 - (2-oxo-1-phenylpyrrolidin-3-yl) -1 H-imida-zol-4-yl] ethyl propionate A solution of 60.1 mg (0.23 mmol) of the compound of example 1g in 1 ml of absolute DMF was mixed with 11 mg (0.23 mmol) of sodium hydride (50% strength) and stirred at room temperature for 1 h.

Then 55.5 mg (0.23 mmol) of (+/-) - 3-bromo-1-phenyl-2-pyrrolidinone was added, and the mixture was stirred at room temperature for 45 min. The reaction solution was mixed with 1 ml of water and extracted several times with EA. The combined EA extracts were dried over Na 2 SO 4, filtered and concentrated. Purification of the resulting residue by chromatography on silica gel with CH2Cl2 / methanol (92: 8 to 85:15 eh min) as mobile phase produced 52.2 mg of the title compound. T.r. (method A) = 0.93 min MS (ES +) = 420 [M + H Example 9b 3- (6-aminopyridin-3-yl) -2- [1- (2-oxo-1-phenylpyrrolidin-) acid bis-hydrochloride 3-yl) -1 H -methazol-4-yl] propionic A solution of 23.1 mg (0.06 mmol) of the compound of example 9a in 0.5 ml of water and 0.5 ml of concentrated hydrochloric acid to the 37% was treated in a microwave oven at 180 ° C for 3 min. The reaction solution was suspended in ethanol and concentrated under reduced pressure several times. Lyophilization of the residue suspended in water afforded 19.0 mg of the desired compound as an amorphous solid. T.r. (method A) = 0.73 min MS (ES +) = 392 [M + H] + 1 H-NMR (500 MHz, DMSO-d 6): d = 2.74 (m, 1 H), 3.00 (dd, 1 H), 3.12 (dd, 1 H), 4.91 (m, 1 H), 4.02 (m, 3H), 5.48 (dd, 1 H), 6.85 (d, 1 H), 7.20 (t, 1H), 7.38 (m, 2H), 7.70 (m, 5H), 7.95 (broad s, 2H).

EXAMPLE 10 3- (6-Aminopyridin-3-yl) -2- acid. { 1 - [(benzhydrylcarbamoyl) methyl] -1H-imidazol-4-iI} propionic Example 10a N-benzhydryl-2-bromoacetamide A solution of 2.91 g (14.39 mmol) of bromoacetyl bromide in 40 ml was cooled to 0 ° C and 2.1 ml (14.39 mmol) were successively added. of triethylamine and 2.64 g (14.39 mmol) of benzhydrylamine. The reaction solution was then evaporated to dryness under reduced pressure, and the resulting residue was purified on silica gel with EA as the mobile phase. The product crystallized from the product fractions was filtered with suction, washed with a little cold diethyl ether and dried under reduced pressure, yielding 0.85 g of the title compound. MS (ES +) = 305 [M + Hf Example 10b 3- (6-aminopyridin-3-yl) -2-. { 1 - [(benzhydrocarbamoyl) methyl] -1 H- midazol-4-yl} ethyl propionate A solution of 60.1 mg (0.23 mmol) of the compound of example 1g in 1 ml of absolute DMF was mixed with 11 mg (0.23 mmol) of sodium hydride (50%) and it was stirred at room temperature for 1 h. Then 70.3 mg (0.23 mmol) of the compound of Example 10a were added, and the mixture was stirred at room temperature for 1 h. The reaction solution was mixed with 1 ml of water and extracted several times with EA. The combined EA extracts were dried over Na 2 SO 4, filtered and concentrated. Purification of the resulting residue by chromatography on silica gel with CH2Cl2 / methanol (9: 1) as mobile phase yielded 71.4 mg of the title compound. T.r. (method A) = 1.24 min MS (ES +) = 484 [M + Hf Example 10c 3- (6-aminopyridin-3-yl) -2- acid bistrifluoroacetate. { 1 - [(benzhydricarbamoyl) methyl] -1H-imidazol-4-yl} propionic A solution of 14 mg (0.03 mmol) of the compound of example 10b in 1 ml of THF was mixed with 147 μl of a 1 N lithium hydroxide solution and stirred at room temperature for 30 min. After another addition of 100 μl of a 1 N lithium hydroxide solution, it was stirred at room temperature overnight. The pH of the solution was then adjusted to neutrality by adding 1 N hydrochloric acid, and this solution evaporated to dryness under reduced pressure. Purification of the resulting residue by preparative HPLC chromatography with 0.1% TFA / CH3CN (5: 100) as mobile phase yielded 16 mg of the desired compound. T.r. (method A) = 1.13 min MS (ES +) = 456 [M + H] + 1 H NMR (500 MHz, DMSO-d6): d = 2.98 (dd, 1H), 3.14 (dd, 1 H), 4.08 (dd, 1H), 5.00 (s, 2H), 6.08 (d, 1 H), 6.87 (d, 1 H), 7.27 (m, 6H), 7 , 35 (m, 4H), 7.50 (broad s, 1H), 7.72 (m, 2H), 7.95 (broad s, 2H), 9.38 (d, 1 H).

The two enantiomers of the compound of Example 10c were separated by preparative chiral phase chromatography; Phase: Chiralpak ADH40, column dimensions: 250 x 4 mm, mobile phase: heptane: ethanol: methanol 1: 1: 1 plus 0.1% ammonium acetate (isocratic), flow: 1 ml / min, temperature: 30 ° C : Enantiomer 1: Tr = 3.42 min Enantiomer 2: T.r. = 12.35 min.

Example 11 3- (6-aminopyridin-3-yl) -2-. { 1 - [(benzhydricarbamoyl) methyl] -1H-imida-zol-4-yl} proprotyl propionate 3 ml of a saturated ethereal solution of HCl was added to a solution of 50 mg (87.8 μmol) of the compound of example 10c in 5 ml of isopropanol and stirred at room temperature for 12 h. The solution was then concentrated to dryness, and the resulting residue was dried under high vacuum. 39 mg of the title compound was produced as the bishydrochloride in the form of an amorphous solid. T.r. (method A) = 1, 31 min MS (ES +) = 498 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): d = 1.15 (d, 6H), 3.13 (m, 2H), 4.25 (dd, 1 H), 4.92 (dt, 1 H ), 5.10 (s, 2H), 6.15 (d, 1H), 6.94 (d, 1 H), 7.28 (m, 2H), 7.33 (m, 8H), 7, 53 (s, 1 H), 7.75 (m, 2H), 8.05 (broad s, 1 H), 9.50 (d, 1 H).

Example 12: 3- (6-Aminopyridn-3-yl) -2- acid. { 1 - [4- (3-Phenylimide) phenyl] -1 H-imidazol-4-yl} Example 12a (methyl 1-trityl-1 H-methyldazole-4-yl) acetate A solution of 2.78 g (19.80 mmol) of the compound of Example 1c, 5.52 g (19.80 mmol) of triphenylmethyl chloride and 2.00 g (19.80 mmol) of triethylamine in 5 ml of DMF were stirred at room temperature overnight, then poured into 200 ml of water and stirred at room temperature. environment for one hour. The precipitate that separated was removed by suction filtration. The filtrate was extracted three times with EA. The combined organic phases were dried over Na 2 SO 4, filtered and concentrated. The yellow oil resulting from this and the precipitate were combined and chromatographed on silica gel. 4.2 g of the desired compound were produced. 1 H-NMR (400 MHz, CDCl 3): d = 3.62 (s, 2H), 3.69 (s, 3H), 6.78 (s, 1H), 7.10-7.18 (m, 6H) ), 7.30-7.36 (m, 9H), 7.38 (s, 1H).

Example 12b dimethyl 2- (1-trityl-1H-imidazol-4-yl) malonate 3.50 g (9.15 mmol) of the compound of the example was dissolved. 12a in 50 ml of dry THF and cooled to 0 C. 1.67 g (9.96 mmol) of lithium bis (trimethylsilyl) amide was added as a concentrated solution at room temperature. % in THF drop by drop to this solution while stirring. The resulting mixture was stirred at 0 ° C for 30 min and then 0.86 g was added. (10.07 mol) of methyl cyanoformate. The reaction mixture was warmed to room temperature and stirred for a further 2 h, then poured into 400 ml of a saturated aqueous solution of NH Cl and extracted twice with EA. The combined organic phases were washed with water, dried over Na 2 SO 4, filtered and concentrated. Chromatography of the residue on silica gel yielded 1.92 g of the title compound. Another chromatography of the resulting mixed fraction yielded an additional 40 mg of the desired compound. T.r. (method C) = 2.17 min MS (ES +) = 498 [M + H] + 1 H NMR (400 MHz, CDCl 3): 8 = 3.76 (s, 6H), 4.78 (s, 1H), 6.98 (s, 1 H) 7.10-7.18 (m, 6H) ), 7.28-7.33 (, 9H), 7.38 (s, 1H). Example 12c Dimethyl 2- (6-tert-butoxycarbonylaminopyridin-3-ylmethyl) -2- (1-trityl-1H-imidazol-4-yl) malonate 0.12 g (5.12 mmol, 50%) of sodium hydride to a solution of 2.25 g (5.11 mmol) of the compound of example 12b in 40 ml of dry DMF at 0 ° C and stirred at this temperature for 5 min. Mix then it was allowed to reach room temperature, stirred for 1 h, again cooled to 0 ° C and then 1.47 g (5.11 mmol) of the compound of example 1b were added in one portion. Stirring was continued at this temperature for 30 min, then 50 ml of water was added while cooling on ice, and the mixture was extracted three times with CH 2 Cl 2. The combined organic phases were dried over Na 2 SO 4, filtered and concentrated. The residue was purified by chromatography on silica gel. 3.15 g of the title compound were obtained. 1 H NMR (400 MHz, CDCl 3): d = 1.53 (s, 9H), 3.63 (s, 2H), 3.72 (s, 6H), 7.01-7.05 (m, 2H) ), 7.06-7.11 (m, 6H), 7.28-7.37 (m, 10H), 7.42. (s, 1 H), 7.70-7.77 (m, 2H). Example 12d Dime-tyl 2- (6-tert-butoxycarbonylaminopyridin-3-ylmethyl) -2- (1 H-imidazol-4-yl) malonate 0.20 g (1.70 mmol, 272 μl) was added of triethylsilane and 1.76 g (15.46 mmol, 1.19 ml) of trifluoroacetic acid to a solution of 1.00 g (1.55 mmol) of the compound of example 12c in 15 ml of CH2Cl2 while cooling on ice and stirring, and stirring it continued at 0 ° C. After 5 h, while cooling on ice, 10 ml of water was added and the pH was adjusted to 9 with 2 N NaOH. The resulting precipitate was removed by suction filtration, triturated in about 20 ml of CH2Cl2, removed by filtration with suction and dried. 0.55 g of the desired compound were obtained. 1 H NMR (400 MHz, CDCl 3): d = 1.49 (s, 9H), 3.58 (s, 2H), 3.77 (s, 6H), 6.99 (d, 1H), 7.06 (s, 1 H), 7.21 (s, 1 H), 7.60-7.69 (m, 3H) . Example 12e Dimethyl 2- (6-tert-butoxycarbonyllamine-pyridin-3-ylmethyl) -2- [1- (4-nitrophenyl) -1H-lmidazol-4-yl] malonate A solution of 404 mg (1.00 mmol) of the compound of Example 12d in 10 ml of DMF was cooled to 0 ° C and, while stirring, 80 mg (2.00 mmol, 60%) of sodium hydride was added in portions. . The mixture was stirred at 0 ° C for 1 h and then 423 mg (3 mmol) of 4-fluoronitrobenzene was added and stirred at room temperature until the conversion was complete. A saturated aqueous solution of NaHCO3 to the mixture, which was extracted with EA. The organic phase was dried over Na2SO, filtered and concentrated. The residue was purified by chromatography on silica gel. 394 mg of the title compound were obtained. T.r. (method B) = 1, 30 min MS (ES +) = 526 [M + H] + Example 12f 2- [1- (4-aminophenyl) -1H-imidazol-4-yl] -2- (6-tert- dimethyl butoxycarbonylami-nopyridin-3-methylmethyl) malonate. 824 mg (3.66 mmol) of tin (II) chloride dihydrate was added to a solution of 384 mg (0.73 mmol) of the compound of example 12e in 10 ml. of DMF and stirred at room temperature overnight. The solvent was then removed by evaporation, and the residue was partitioned between EA and a saturated aqueous solution of NaHCO3. The aqueous phase was extracted twice with EA. The combined organic phases are dried over Na2SO, filtered and concentrated. 103 mg of the title compound were obtained. T.r. (method B) = 0.93 min MS (ES +) = 496 [M + H] + Example 12g 2- (6-tert-butoxycarbonylaminopyridin-3-ylmethyl) -2-. { 1 - [4- (3-phenylureido) phenyl] -1H-imydazoI-4-yl} dimethyl malonate 50 mg (0.10 mmol) of the compound of Example 12f were dissolved in 10 ml of acetonitrile. The resulting solution was cooled to 0 ° C, and 14 mg (0.12 mmol, 13.2 μl) of phenyl isocyanate and 20 mg (0.20 mmol, 28 μl) of triethylamine were added. The mixture was warmed to room temperature and the tip of a spatula of 4-dimethylaminopyridine was added. The reaction mixture was allowed to stand overnight and then evaporated, and the residue was chromatographed on silica gel. 47 mg of the title compound were obtained. T.r. (method B) = 1, 28 min MS (ES +) = 615 [M + H] + Example 12h: 3- (6-aminonyridin-3-yl) -2- acid. { 1 - [4- (3-phenylimide) phenyl] -1 H -imide-zol-4-yl} propanoic 47 mg (75 μmol) of the compound of example 12g were heated in 4 ml of 50% concentrated hydrochloric acid to 100 ° C. After 1.5 h, the mixture was diluted with water, and the reaction mixture was lyophilized. A Preparative HPLC of the residue afforded 19 mg of the title compound as the bistrifluoroacetate.

T.r. (method B) = 0.85 min MS (ES +) = 443 [M + H] + 1 H NMR (400 MHz, DMSO-d6): d = 3.07 (dd, 1H), 3.20 (dd, 1 H), 4.00 (, 1H), 6.90 (d, 1 H), 6.98 (t, 1 H), 7.30 (t, 2H), 7.43 (d, 2H), 7.61 (m, 4H), 7.78 (s, 1 H), 7.80 (dd, 2H), 7.90 (s, 2H, broad), 8.82 (s, 1H, broad), 8.98 (s, 1 H), 9.16 (s, 1 H).

Example 13 3- (6-aminopyridine-3-iI) -2- acid. { 1- [2- (1-Diphenyl-acetylpperidin-4-yl) ethyl] -1H-imidazol-4-yl} Propionic Example 13a 1- [4- (2-Hydroxyethyl) piperidin-1-yl] -2,2-d-phenylene tanone 2-piperidin-4-ylethanol (1, 12 g 8.65 mmol) in dimethylformamide (DMF, 10 ml). Then, in this sequence, hydroxybenzotriazole (HOBT, 1.46 g, 9.51 mmol), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC-HCl, 1.83 g, 9.51) was added. mmol) and diphenylacetic acid (2.02 g, 9.51 mmol). Then N, N-diisopropylethylamine (DIEA, 1.67 ml, 9.51 mmol) was added to the reaction mixture, which was stirred at room temperature for 16 h. The reaction solution was concentrated under reduced pressure. The residue was suspended in EA, and the organic solution was washed successively with a saturated solution of NaHCOs, 2 N HCl and a saturated solution of NaCl. The organic phase was separated, dried over Na2SO, filtered and concentrated. 1- [4- (2-Hydroxyethyl) piperidin-1-yl] -2,2-diphenyletanone (2.39 g, 8.11 mmol) obtained from this mode was reacted afterwards without further purification. T.r. (method B) = 1, 33 min MS (ES +) = 324 [M + H] + Example 13b 1 - [4- (2-Bromoethyl) piperidin-1 -I] -2,2-diphenylethaneone 1- [4- (2-hydroxyethyl) piperidin-1-yl] -2,2-diphenyletanone (2 , 39 g, 8.11 mmol) was dissolved in dichloromethane (20 ml). Phosphorus tribromide (1.6 ml, 8.92 mmol) was slowly added dropwise at room temperature. The reaction mixture was heated to reflux for 4 h. After cooling, it was washed with a saturated solution of NaHCO3, 2N HCl and a saturated solution of NaCl, and the organic phase was separated and dried over Na2SO. The solvent was removed under reduced pressure. Purification of the residue through a cartridge (silica gel) yielded 1- [4- (2-bromoethyl) piperidin-1-yl] -2,2-diphenyl-ethanone (0.75 g, 2.13 mmol). T.r. (method B) = 1.79 min MS (ES +) = 386 [M + Hf Example 13c 3- (6-aminopyridin-3-yl) -2-. { 1- [2- (1-D-phenylacetylpiperidin-4-yl) ethyl] -1 H -imidazol-4-yl} ethyl propionate Ethyl 3- (6-aminopyridin-3-yl) -2- (1 H-imidazol-4-yl) propionate (100 mg, 0.38 mmol) was dissolved in absolute DMF (2 ml). Sodium hydride (50%, 19 mg, 0.38 mmol) was added, and the reaction mixture was stirred at room temperature for 1 h. Then 1- [4- (2-bromoetyl) p-peridin-1-yl] -2,2-d-phenyletanone (148 mg, 0.38 mmol) dissolved in absolute DMF (1 ml). The reaction mixture was stirred at room temperature for 1 h and then concentrated under reduced pressure. The residue was suspended in 1 N HCl and washed with dichloromethane (CH2Cl2, 2?). The aqueous phase was made basic with 1N NaOH and extracted with CH2Cl2 (3?). The combined organic phases were dried over Na2SO4. Removal of the solvent under reduced pressure yielded 3- (6-aminopyridin-3-yl) -2-. { 1- [2- (1-diphenylacetylpi-peridin-4-yl) etiI] -1 H -imidazol-4-yl} ethyl propionate (71 mg, 0.12 mmol). T.r. (method B) = 0.98 min MS (ES +) = 566 [M + H] + Example 13d 3- (6-Aminopyridin-3-yl) -2- acid. { 1- [2- (1-diphenylacetylpiperidin-4-yl) ethyl] -1H-imidazol-4-yl} propionic 3- (6-aminopyridin-3-yl) -2- was dissolved. { 1- [2- (1-diphenylacetylpperidin-4-yl) ethyl] -1H-lmidazole-4-ll} Ethyl propionate (71 mg, 0.12 mmol) in absolute ethanol (600 μl). 1 N NaOH (128 μl, 0.12 mmol) was added. The reaction mixture was stirred at room temperature for 16 h. It was then neutralized with 1 N HCl (128 μL, 0.12 mmol) and concentrated under reduced pressure. The residue was suspended in methanol and filtered through a C-18 cartridge. The methanol was removed and acetonitrile was added and decanted from the residue (2 x).

Then the residue was triturated with diethyl ether. The precipitate was removed by filtration and dried under high vacuum at 40 ° C. 3- (6-Aminopyridin-3-yl) -2- acid was obtained. { 1 - [2- (1-D-phenylacetylpiperidin-4-yl) ethyl] -1H-imidazol-4-yl} propionic (50 mg, 0.09 mmol) as a colorless solid. T.r. (method C) = 1, 20 min MS (ES +) = 538 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 0.90 (m, 1 H), 1.02 -1.51 (m, 5H), 1.61 (m, 2H), 2.67 (m, 2H), 2.94 (m, 1H), 3.11 (m, 1H), 3.18- 3.56 (m, 3H) ), 3.65 (m, 1 H), 3.90 (m, 1 H), 4.09 (t, 1 H), 5.54 (m, 2H), 6.29 (d, 1 H) , 6.89 (s, 1 H), 7.23 (m, 12H), 7.65 (m, 1 H), Example 14 3- (6-Aminopyridn-3-yl) -2- acid. { 1- [2- (1-benzoylpiperidn-4-yl) ethyl] -1 H -imidazol-4-yl} -propionic The title compound (54 mg, 0.12 mmol) was synthesized in analogy to Example 13. T.r. (method C) = 0.88 min MS (ES +) = 448 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 1.10 (m, 2H), 1.41 (m, 1 H), 1. 60 (m, 3H), 1.72 (m, 1 H), 2.71 (m, 2H), 2.95 (m, 2H), 3.48 (m, 3H), 3.92 (t, 2H), 4.45 (m, 1H), 5.57 (s, 2H), 6.28 (d, 1H), 6.90 (s, 1 H), 7.11 (d, 1 H), 7.32 (m, 2H), 7.43 (m, 3H), 7.49 (s, 1H), 7.61 (s, 1H).

EXAMPLE 15 3- (6-Aminopyridin-3-yl) -2- [1- (1-benzoy-piperidin-2-ylmethyl) -1 H -imidazol-4-yl] -propionic acid The title compound (41 mg, 0.09 mmol) was synthesized in analogy to example 13. Tr (method C) = 0.81 min MS (ES +) = 434 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 1.12 (m, 2H), 1.39 (m, 1H), 1. 61 (m, 1 H), 1, 92 (m, 1 H), 2.80 (m, 4H), 3.48 (m, 5H), 4.20 (m, 1 H), 5.60 ( s, 2H), 6.28 (d, 1H), 6.90 (m, 1 H), 7.10 (d, 1H), 7.35 (m, 6H), 7.61 (s, 1H).

EXAMPLE 16 3- (6-Aminopyridin-3-yl) -2- (1 -. {2- [1- (3-phenylpropionyl) piperidin-3-yl] ethyl} -1 H-imide-zol acid -4-μl) propionic The title compound (15 mg, 0.03 mmol) was synthesized in analogy to example 13. Tr (method C) = 1, 04 min MS (ES +) = 476 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 1.15 (m, 3 H), 1.55 (m, 3 H), 1.75 (m, 1 H), 2.59 (m, 2 H), 2 , 77 (m, 2H), 2.92 (m, 2H), 3.40 (m, 4H), 3.65 (m, 1 H), 3.89 (t, 2H), 4.15 (m, 1 H), 5.55 (s, 2H), 6.28 (d, 1 H), 6.89 (m, 1 H) ), 7.13 (m, 2H), 7.22 (m, 4H), 7.45 (s, 1H), 7.63 (m, 1H).

Example 17 3- (6-Aminopyridin-3-yl) -2- [1- (1-diphenylacetyl-piperidin-3-ylmethyl) -1H-imidazol-4-yl] -propionic acid The title compound (19 mg, , 03 mmol) was synthesized in analogy to example 13. Tr (method C) = 1.13 min MS (ES +) = 524 [M + H] + 1 H NMR (500 MHz, DMSO-d6): 0.85-1.75 (m, 5H), 2.55- 3.07 (m, 4H), 3.07-3.83 (m, 6H), 4.09 (m, 1 H), 5.62 (m, 2H), 6.29 (m, 1H), 6.89 (m, 1H), 7.23 (m, 12H), 7.65 (m, 1 H), EXAMPLE 18 3- (6-aminopyridin-3-yl) -2- (1 -. {2- 2- [1 - (3-phenylpropionyl) piperidin-4-yl] etl. H-imida-zol-4-yl) propionic The title compound (81 mg, 0.17 mmol) was synthesized in analogy to Example 13. Tr (method C) = 1.00 min MS (ES +) = 476 [M + Hf 1 H NMR (500 MHz, DMSO-d 6): 0.92 (m, 2 H), 1.32 (m, 1 H), 1.55 (m, 4 H), 2.55 (m, 2 H), 2 , 85 (m, 4H), 3.40 (m, 4H), 3.79 (m, 1H), 3.88 (t, 2H), 4.33 (d, 1 H), 5.65 (s) , 2H), 6.29 (d, 1 H), 6.89 (s, 1 H), 7.13 (m, 2H), 7.22 (m, 4H), 7.45 (s, 1 H) ), 7.63 (m, 1 H).

EXAMPLE 19 3- (6-Aminopyridin-3-yl) -2- acid. { 1- [2- (1-Phenylacetylpiperidin-3-yl) etiI] -1 H -imidazol-4-yl} -propionic The title compound (28 mg, 0.06 mmol) was synthesized in analogy to example 13. T.r. (method C) = 0.93 min MS (ES +) = 462 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 0.90 (m, 2H), 1.35 (m, 1 H), 1.58 (m, 4H), 2.80 (m, 2H), 2 , 95 (m, 2H), 3.40 (m, 4H), 3.69 (s, 1H), 3.85 (t, 2H), 4.33 (d, 1H), 5.60 (s, 2H), 6.29 (d, 1 H), 6.90 (s, 1 H), 7.10 (dd, 1 H), 7.19 (m, 3H), 7.27 (m, 2H), 7.48 (s, 1 H), 7.61 (m, 1 H).

Example 20 3- (6-aminonopyridin-3-yl) -2- acid. { 1- [2- (1-phenylacetyl) pyridin-4-yl) ethyl] -1 H-imydazoI-4-yl} -propionic The title compound (41 mg, 0.08 mmol) was synthesized in analogy to Example 13. T.r. (method C) = 0.91 min MS (ES +) = 462 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 0.92 (m, 2 H), 1.25 (m, 1 H), 1.58 (m, 4 H), 2.65 - 4.20 (m, 12H), 5.65 (m, 2H), 6.29 (m, 1H), 6.90 (m, 1H), 7.20 (6H), 7.60 (m, 2H).

Example 21: 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [1 - (4'-Methylbiphenyl-3-carbonyl) pi-peridin-4-ylmethyl] -1 H -amidazol-4-yl} propionic The title compound (33 mg, 0.06 mmol) was synthesized in analogy to Example 13. T.r. (method C) = 1, 21 min MS (ES +) = 524 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 1.12 (m, 2 H), 1.45 (m, 2 H), 1.95 (m, 1 H), 2.36 (s, 3 H), 2 , 80-3.60 (m, 6H), 3.71 (t, 1H), 3.85 (d, 2H), 4.45 (m, 1 H), 6.49 (d, 1H), 6 , 60 (m, 2H), 6.87 (s, 1 H), 7.29 (m, 4H), 7.58 (m, 4H), 7.65 (m, 1 H), 7.72 ( m, 2H).

Example 22 3- (6-Aminopyridin-3-yl) -2- [1- (1-benzoylpiperidin-4-ylmethyl) -1 H-imidazol-4-yl] pro-pylonic acid The title compound (46 mg, 0.10 mmol) was synthesized in analogy to Example 13. T.r. (method C) = 0.81 min MS (ES +) = 434 [M + H NMR of 1H (500 MHz, DMSO-d6): 1.10 (m, 2H), 1.45 (m, 2H), 1 , 95 (m, 1 H), 2.80 - 3.10 (m, 4H), 3.50 (m, 2H) 3.62 (t, 1H), 3.82 (d, 2H), 4, 48 (m, 1 H), 6.03 (m, 2H), 6.48 (d, 1H), 6.90 (d, 1 H), 7.19 (d, 1 H), 7.35 (m , 2H), 7.42 (m, 3H), 7.55 (s, 1 H), 7.61 (s, 1 H). Example 23 3- (6-Aminopyridin-3-yl) -2- (1-benzhydryl-1 H-imidazol-4-yl) pro-pionic acid 11 mg (0.23 mmol, 50%) of hydride was added of sodium to a solution of 50 mg (0.19 mmol) of 3- (6-aminopyridin-3-yl) -2- (1 H-imidazol-4-yl) ethyl propionate (example 1g) at 0, 5 ml of DMF at room temperature and stirred for 1 h. Then 48 mg (0, 19 mmol) of bromodiphenylmethane, and the mixture was stirred at room temperature for 3.5 h. It was then heated at 60 ° C for 2 h and, after cooling, 1 ml of water was added, the mixture was extracted with EA, and the organic phase was dried over Na 2 SO 4, filtered and concentrated. Chromatography on silica gel afforded ethyl 3- (6-aminopyridin-3-yl) -2- (1-benzhydryl-1H-imidazol-4-yl) propionate. The product obtained in this manner was suspended in 0.4 ml of 50% concentrated hydrochloric acid and treated in a microwave oven at 180 ° C for 3 min. A lyophilization after cooling of the reaction mixture afforded 5 mg of the title compound as the bismhydrochloride.

T.r. (method A) = 1, 04 min MS (ES +) = 399 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 3.05 (dd, 1H), 3.11 (dd, 1H), 3.70 (m, 1 H), 4.12 (m, 1H), 6 , 38 (dd, 1 H), 7.02 (s, 1H), 7.12 (dd, 1 H), 7.23-7.51 (m, 6H), 7.67 (d, 1H), 7.72 (m, 1H), 8.02 (s, a, 2H), 9.03 (s, 1H).

Example 24: 3- (6-Aminopyridin-3-yl) -2- [1 - (4- [1, 2,4] triazol-1-ylbenzyl) -1 H-imidazol-4-yl] pro-pionic acid added 11 mg (0.23 mmol, 50%) of sodium hydride to a solution of 60 mg (0.23 mmol) of 3- (6-aminopyridin-3-yl) -2- (1H-imidazole). ethyl) propionate (example 1g) in 0.5 ml of DMF at room temperature, and stirred for 1 h. Then 55 mg (0.23 mmol) of 1- [4- (bromomethyl) pheny1] -1H-1,2,4-triazole was added, and the mixture was stirred at room temperature for 3 h. After this, 1 ml of water was added, the mixture was extracted with EA, and the organic phase was dried over Na2SO, filtered and concentrated. Chromatography on silica gel yielded 3- (6-aminopyridin-3-yl) -2- [1 - (4- [1, 2,4] triazol-1-ylbenzyl) -1H-imidazole ethyl ester. -4-iljpropionic. The product obtained in this manner was suspended in 0.4 ml of 50% concentrated hydrochloric acid and treated in a microwave oven at 180 ° C for 3 min. A lyophilization after cooling of the reaction mixture afforded 5 mg of the title compound as the bishydrochloride. T.r. (method A) = 0.16 min MS (ES +) = 390 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 3.03 (dd, 1 H), 3.21 (dd, 1 H), 4.21 (m, 1 H), 5.45 (s, 2H) , 6.91 (d, 1 H), 7.50 (d, 2H), 7.60 (s, 1 H), 7.70-7.78 (m, 2H), 7.86 (d, 1 H), 7.95 (d, 2H), 8.08 (s, a, 2H), 8.26 (s, 1 H), 9.28 (s, 1H), 9.38 (s, 1H) .

Example 25 3- (6-Aminopyridin-3-yl) -2- [1- (4-trifluoromethoxybenzyl) -1 H -imidazol-4-yl] propionic acid The title compound was prepared in analogy to example 24. Tr (method A) = 1, 04 min MS (ES +) = 407 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 2.98 (dd, 1 H), 3.12 (dd, 1 H), 4.02 (m, 1 H), 5.33 (s, 2 H), 6.84 (d, 1 H), 7.30 (dd, 1H), 7.35-7.46 (m, 4H), 7.68 (m, 2H), 7.93 (s, a, 2H) ), 8.75 (s, a, 1H).

EXAMPLE 26 3- (6-Aminopyridin-3-yl) -2- [1- (1,1-dioxo-1 H-1,6-benzo [b] thio-phen-2-ylmethyl) -1 H-imi acid -dazol-4-yl] propionic The title compound was prepared in analogy to Example 24. Tr (method A) = 0.88 min MS (ES +) = 411 [M + Hf 1 H NMR (500 MHz, DMSO-d6): 2.10 (s, 2H), 3.06 (dd, 1H), 3.18 (dd, 1 H), 3.99 (m, 1 H), 7.40 (d, 1H), 7.22 (d, 1 H), 7.60 (s, 1 H), 7 , 70-7.82 (m, 5H), 7.98 (s, a, 2H), 7.99 (s, 1 H), 8.46 (s, 1 H), EXAMPLE 27 3- (6-Aminopyridin-3-yl) -2- [1- (5-chlorobenzo [b] thiophen-3-ylmethyl) -1 H-lmidazole-4-yl] -proponone The compound of The title was prepared in analogy to Example 24 and was obtained as the bistrifluoroacetate after a preparative HPLC. T.r. (method A) = 0.98 min MS (ES +) = 413 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 2.98 (dd, 1H), 3.13 (dd, 1H), 4.06 (m, 1 H), 5.61 (s, 2H), 6 , 78 (d, 1 H), 7.42-7.53 (m, 2H), 7.63 (d, 1 H), 7.70 (s, 1 H), 7.84-7.98 ( m, 3H), 8.02 (s, 1H), 8.09 (d, 1 H), 8.92 (s, a, 1H), EXAMPLE 28 3- (6-Aminopyridin-3-yl) -2- acid. { 1 - [3- (4-fluorophenoxy) benzyl] -1H-imidazol-4-yl} Propionic The title compound was prepared in analogy to Example 24 and was obtained as the bistrifluoroacetate after a preparative HPLC. T.r. (method A) = 1, 09 min MS (ES +) = 433 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 2.98 (dd, 1 H), 3.13 (dd, 1 H), 4.08 (m, 1 H), 5.30 (s, 2H) , 6.81 (d, 1H), 6.95 (dd, 2H), 7.07 (m, 3H), 7.23 (dd, 2H), 7.40 (dd, 1 H), 7.44 (m, 1H), 7.69 (m, 2H), 7.93 (s, a, 2H), 8.87 (s, a, 1H), EXAMPLE 29 3- (6-Aminopyridin-3-yl) -2- [1- (2-phenoxybenzyl) -1 H-imidazol-4-ylpropionic acid The title compound was prepared in analogy to Example 24 and was obtained as the bistrifluoroacetate after a preparative HPLC. T.r. (method A) = 1, 05 min MS (ES +) = 415 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 2.97 (dd, 1 H), 3.13 (dd, 1 H), 4.03 (m, 1 H), 5.37 (s, 2 H), 6.82 (m, 2H), 6.90 (d, 2H), 7.17 (m, 2H), 7.30 (d, 1 H), 7.32-7.43 (m, 4H), 7.69 (m, 2H), 7.92 (s, a, 2H), 8.82 (s, a, 1H), EXAMPLE 30 3- (6-Aminopyridin-3-yl) -2- [1- (4-phenoxybenzyl) -1 H -imidazole-4-ylpropionic acid The title compound was prepared in analogy to Example 24 and was obtained as the bistrifluoroacetate after a preparative HPLC. T.r. (method A) = 1, 08 min MS (ES +) = 415 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): 2.99 (dd, 1 H), 3.13 (dd, 1H), 4.07 (m, 1H), 5.28 (s, 2H), 6 , 84 (d, 1H), 7.01 (m, 3H), 7.17 (dd, 1H), 7.32 (d, 2H), 7.40 (m, 3H), 7.48 (m, 1 H), 7.68 (m, 2H), 7.90 (s, a, 2H), 8.88 (s, a, 1 HOUR), Example 31 3- (6-Aminopyridin-3-yl) -2- (1-prop-2-ynyl-1 H-imidazol-4-yl) pro-pionic acid Example 31a 2- (6-tert-butoxycarbonylaminopyridin-3) -ethylmet.I) -2- (1-prop-2-ynyl-1H-imidazol-4-yl) dimethyl malonate 322 mg (0.99 mmol) of cesium carbonate and 20 μl (0.27 mmol, 80% pure in toluene) of propargyl bromide were successively added to a solution of 100 mg (0.25 mmol) 2- ( Dimethyl dimethyl-6-tert-butoxycarbonylaminopyridin-3-ylmethyl) -2- (1 H-imidazol-4-yl) (example 12d) in 2 ml of DMF. The mixture was stirred at room temperature for 3 h and then poured into water and extracted with EA. Purification by chromatography on silica gel yielded 27 mg of the title compound. 1 H NMR (400 MHz, CDCl 3): 1.49 (s, 9H), 1.52 (d, 1 H), 2.52 (m, 1 H), 3.60 (s, 2H), 4, 67 (d, 2H), 6.98 (d, 1 H), 7.12 (s, 1 H), 7.21 (s, 1 H), 7.60 (s, 1 H), 7.68 (d, 1H). Example 31b 3- (6-Aminopyridin-3-yl) -2- (1-prop-2-ynyl-1 H-imidazol-4-yl) pro-pionic acid A solution of 40 mg (0.09 mmol) of the composed of the example 31a in 1, 4 ml of 50% concentrated hydrochloric acid was heated at 95 ° C for 9 h. Freeze drying after cooling produced 21 mg of the title compound such as bishydrochloride. 1 H NMR (500 MHz, DMSO-d 6): 3.11 (dd, 1H), 3.20 (dd, 1H), 3.78 (s, 1H), 4.21 (t, 1H), 5, 12 (d, 2H), 6.92 (d, 1H), 7.54 (s, 1H), 7.75 (m, 2H), 8.04 (s, a, 2H), 9.03 (s, 1H).

Example 32 3- (6-aminopyridin-3-yl) -2- (1-but-2-yn-1 H-imidazole-4-yl) propionic acid Example 32a 3- (6-aminopyridin-3) ethyl) -2- (1-but-2-ynyl-1H-imidazol-4-yl) propionate 11 mg (0.23 mmol, 50%) of sodium hydride were added to a solution of 60 mg (0.23 mmol) of ethyl 3- (6-aminopyridin-3-yl) -2- (1H-imidazol-4-yl) propionate (example 1g) in 0.5 ml of DMF at room temperature and stirred for 1 h. Then 31 mg (37 μL, 0.23 mmol) of 1-bromo-2-butyne were added, and the mixture was stirred at room temperature for 1 h. Then 1 ml of water was added and the mixture was extracted with EA. The organic phase was dried over Na2SO4, filtered and concentrated. Chromatography of the residue on silica gel afforded 28 mg of the title compound. T.r. (method A) = 0.69 min MS (ES +) = 313 [M + Hf Example 32b 3- (6-aminopyridin-3-yl) -2- (1-but-2-ynyl-1 H-imidazole- 4-yl) pro-pionic A solution of 25 mg (0.08 mmol) of the compound of example 32a in 2 ml of THF was mixed with 88 μl of 1 N NaOH and stirred at room temperature for 4 h. Then, and again after stirring overnight, 40 μl of NaOH was added. After stirring for a further 24 h, the reaction mixture was neutralized with 2 N HCl and lyophilized. An HPLC Preparation afforded 5 mg of the title compound as the bistrifluoroacetate. T.r. (method A) = 0.23 min MS (ES +) = 285 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): d = 1.88 (s, 3 H), 3.12 (m, 2 H), 4.18 (m, 1 H), 5.02 (s, 2 H) , 6.93 (d, 1 H), 7.56 (s, 1H), 7.78 (m, 2H), 8.04 (s, a, 2H), 8.97 (s, a, 1 H) ). The following compounds were prepared in analogy to Example 1: EXAMPLE 33 3- (6-Aminopyridin-3-yl) -2- [1- (4,4-dlmethylcyclohexyl) -1 H-imida-zol-4-ylpropionic acid such as bishydrochloride T.r. (method C) = 0.93 min MS (ES +) = 343 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): d = 0.93 (s, 3 H), 1.00 (s, 3 H), 1.33 (m, 2 H), 1.48 (m, 2 H), 1.85 (m, 4H), 3.04 (dd, 1 H), 3.20 (dd, 1 H), 4.11 (t, 1 H), 4.16 (m, 1 H), 6 , 90 (d, 1 H), 7.73 (d, 2H), 7.81 (s, 1H), 8.02 (s, 2H, a), 9.14 (s, 1 H). The following compounds were prepared in analogy to Example 10: Examples 34-36 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [(benzhydrylmethylcarbamoyl) methyl] -1 H -amidazol-4-yl} propionic such as bistrifluoroacetate T.r. (method C) = 1, 18 min MS (ES +) = 470 [M + H] + 3- (6-aminopyridin-3-yl) -2- [1- ( { [(4-chlorophen L) phenylmethyl] carbamoyl] methyl) -1H-imidazol-4-yl] propionic as the bistrifluoroacetate T.r. (method C) = 1, 22 min MS (ES +) = 490 [M + H] + or 3- (6-aminopyridin-3-yl) -2- [1- ( { [bis- (4- methoxyphenyl) methyl] carbamoyl.] methyl) -1 H-imidazoi-4-yl] propionic such as bistrifluoroacetate Tr (method B) = 0.92 min MS (ES +) = 516 [M + H] + Example 37 3- (6-Aminopyridin-3-yl) -2- acid. { 1- [4- (3-propyl) phenyl] -1H-imi-dazol-4-yl} propionic Example 37a Methyl 3- (6-tert-butoxycarbonylaminopyridin-3-yl) -2- [1- (toluene-4-sulfonyl) -1 H-imidazol-4-yl] propionate A solution of 1.00 g ( 3.39 mmol) of methyl (1-benzenesulfonyl-1H-imidazol-4-yl) acetate (example 1d) in 100 ml of THF was cooled to -78 ° C and 3.74 ml (3.74 ml) was added. mmol, 1 M in THF) of lithium bis (trimethylsilyl) amide in three portions over 3 min. The mixture was stirred at this temperature for 5 min and then 0.65 g (2.26 mmol) of tert-butyl (5-bromomethylpyridin-2-yl) carbamate (Example 1b) was added in one portion. The mixture was stirred at -78 ° C for 1 h and then allowed to reach room temperature. The mixture was poured into a mixture of EA and a saturated solution of NaHCO3. After stirring, the organic phase was separated, dried over Na2SO4, filtered and concentrated to dryness. The residue was recrystallized from EA / heptane. The resulting crystals they were removed by suction filtration, washed with a little EA and heptane, and dried. 0.66 g of the title compound were obtained. T.r. (method B) = 1, 30 min MS (ES +) = 501 [M + H] + Example 37b Methyl 3- (6-tert-butoxycarbonlaminopyridin-3-yl) -2- (1 H-imidazol-4-yl) propionate 0.80 g (5.24 mmol) of hydrated 1-hydroxybenzotriazole was added. to a solution of 0.65 g (1.29 mmol) of 3- (6-tert-butoxycarbonyl-lane-pyridin-3-yl) -2- [1- (toluene-4-sulfonyl) -1 H-imidazole 4-yl] methyl propionate (example 37a) in 25 ml of methanol, and the mixture was stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure, and the residue was purified on silica gel, the mobile phase being a mixture of CH2Cl2 and 10% concentrated ammonia / methanol. A second column chromatography on silica gel yielded 341 mg of the title compound. T.r. (method B) = 0.78 min MS (ES +) = 347 [M + H NMR of 1H (400 MHz, d6-DMSO): 1.46 (s, 9H), 3.08 (m, 2H), 3 , 52 (s, 3H), 3.87 (t, 1 H), 6.92 (s, 1 H), 6.98 (d, 1 H), 7.55 (s, 1H), 7.63 (d, 1 H), 7.98 (s, 1 H). Example 37c 3- (6-Aminopyridin-3-yl) -2- acid. { 1 - [4- (3-propylureido) phenyl] -1 H -imi-dazol-4-yl} propionic The title compound was obtained by reacting the compound of example 37b in analogy to examples 12e-12g and subsequently removing the protecting group in the usual manner in the literature in CH2Cl2 / TFA (1: 1). The substitution was then carried out as in example 10c. A preparative HPLC yielded 8 mg of the title compound as the bistrifluoroacetate. T.r. (method B) = 0.73 min MS (ES +) = 409 [M + H] + 1 H NMR (400 MHz, d6-DMSO): 0.88 (t, 3H), 1.45 (dt, 2H), 3.07 (m, 3H), 3.18 (m, 1H), 3, 97 (t, 1 H), 6.28 (t, 1H), 6.89 (d, 1 H), 7.51 (m, 4H), 7.21 (d, 2H), 7.31 (d) , 1 H), 7.86 (s, 2H, a), 8.19 (s, 1 H).

EXAMPLE 38 3- (6-Aminopyridin-3-yl) -2- acid. { 1- [4- (toluene-4-sulfonylamino) phenyl] -1H-imidazol-4-yl} propionic Example 38a 3- (6-tert-butoxycarbonylaminopyridin-3-yl) -2-. { 1 - [bis- (4- (to! Uen-4-sulfonyl) amino) phenyl] -1H-imidazol-4-yl} methyl propionate A solution of 115 mg (0.26 mmol) of 2- [1- (4-aminophenyl) -1 H -imidazol-4-yl] -3- (6-tert-butoxycarbonylaminopyridin-3-yl) propionate of methyl (obtained from example 37b) was dissolved in 20 ml of CH3CN. The solution was cooled to 0 ° C and 60 mg (0.32 mmol) of p-toluenesulfonyl chloride, 73 μL (53 mg, 0.53 mmol) of triethylamine and 0.3 mg (2.6 μmol) were added. of 4-dimethylaminopyridine. The mixture was warmed to room temperature and allowed to stand overnight. A Column chromatography on silica gel yielded 112 mg of the title compound. T.r. (method B) = 1.45 mln MS (ES +) = 746 [M + H] + Example 38b 3- (6-Aminopyridin-3-yl) -2- acid. { 1 - [4- (Toluene-4-sulphonyl) phenyl] -1 H-imidazol-4-yl} Propionic A solution of 109 mg (0.146 mmol) of the compound according to Example 38a in 1 mL of THF was mixed with 190 μL (0.190 mmol) of a 1 N aqueous LiOH solution. The mixture was heated to 40 °. C and stirred for 2 days at this temperature. After heating at 60 ° C for several hours, the solution was cooled to room temperature, neutralized with 1 N HCl and the THF was removed under reduced pressure. The resulting aqueous solution was purified by preparative HPLC and 3- (6-tert-butoxycarbonylaminopyridin-3-yl) -2- acid was obtained. { 1- [4- (Toluene-4-sulfonylamino) phenyl] -1H-imidazole-4-N} pure propionic The compound was dissolved in 1 ml of TFA and stirred at room temperature. After 30 min, the TFA was removed under reduced pressure and the residue was dissolved in water and lyophilized. 24 mg of the title compound were obtained as the bistrifluoroacetate. T.r. (method B) = 0.84 min MS (ES +) = 487 [M + H] + 1 H NMR (400 MHz, d6-DMSO): 1.22 (s, 3 H), 3.02 (dd, 1 H), 3.13 (dd, 1 H), 3.92 (t, 1 H), 6.87 (d, 1 H), 7.21 (d, 2H), 7.88 (d, 2H), 7.53 (d, H), 7.62 (s, 1 H), 7.68 (d, 2H), 7.72 (s, 1 H), 7.77 (d, 1H), 7.88 (s, 2H, a), 8.44 (s, 1 H, a).

Example 39 3- (6-Aminopyridin-3-yl) -2- acid. { 1 - [3- (3-propylureido) benzyl] -1 H- midazole-4-yl} Propionic The title compound was prepared in analogy to Example 38. Only the hydrolysis of the intermediate carboxylic ester was different: 3- (6-aminopyridin-3-yl) -2- was dissolved. { 1 - [3- (3-propylureido) benzyl] -1 H-imidazol-4-yl} Methyl propionate (120 mg, 0.275 mmol) in THF. An aqueous solution of LiOH (1 N, 275 μL) and an aqueous solution of hydrogen peroxide (30%, 27 μL) were added. The solution was stirred overnight at room temperature and then at 50 ° C for 4 h. The reaction solution was neutralized with aqueous HCl (1 N) and then the solvents were removed. The residue was suspended in a little methanol and the solution was filtered through a column (500 mg). The methanol was removed, and the resulting product (100 mg, 0.237 mmol) was crystallized from diethyl ether. T.r. (method C) = 0.93 min MS (ES +) = 423 [M + H] + 1 H NMR (500 MHz, DMSO-d6): d = 0.85 (t, 3H), 1.42 (q, 2H), 2.65 (m, 1 H), 2.92 (m, 1 H), 3.02 (m, 2H), 3.45 (m, 2H), 5.00 (s, 2H), 5.50 (s, 2H), 6.25 (d, 1H), 6.60 (d, 1 H), 6.73 (s, 1H), 7.05 (d, 1H), 7.21 (d. t, 1H), 7.23 (s, 1 H), 7.33 (d, 1H), 7.50 (m, 1 H), 7.62 (s, 1 H), 9.12 (s, 1 H).

Example 40 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [3- (3-phenethylureido) benzyl] -1 H- imidazol-4-yl} pro-pionic The compound was prepared in analogy to example 39. T.r. (method B) = 0.86 min MS (ES +) = 485 [M + Hf 1 H NMR (500 MHz, DMSO-d6): d = 2.72 (m, 2H), 2.85 (m, 1 H ), 2.95 (m, 1 H), 3.25 (m, 2H), 3.50 (s, 2H), 4.95 (s, 1 H), 5.05 (s, 1 H), 5, 45 (s, 1 H), 5.55 (s, 1 H), 6.28 (dd, 1 H), 6.65 (t, 1 H), 6.92 (s, 1 H), 7, 08-7.31 (m, 9H), 7.62 (m, 2H), 9.15 (s, 1 H).

Example 41 3- (6-Aminopyridin-3-yl) -2- acid. { 1- [3- (3-benzylureido) benzyl] -1 H-imidazol-4-ll} pro-pionic The compound was prepared in analogy to example 39. T.r. (method B) = 0.84 min MS (ES +) = 471 [M + H] + 1 H NMR (500 MHz, DMSO-d6): d = 2.65 (m, 1 H), 2.92 (m , 1 HOUR), 3.45 (m, 2H), 3.75 (m, 1 H), 4.25 (d, 2H), 5.00 (s, 2H), 5.50 (s, 2H), 6.25 (m, 1 H), 6.65 (m, 1 H), 6.78 (s, 1 H), 7.08-7.40 (m, 9H), 7.62 (m, 2H), 9 , 45 (s, 1 H).

Example 42: 3- (6-Aminopyridin-3-yl) -2- acid. { 1- [3- (3-vinylurethane) benzyl] -1 H -imi-dazol-4-yl} propionic The compound was prepared in analogy to example 39. T.r. (method B) = 0.60 min MS (ES +) = 407 [M + H] + 1 H NMR (500 MHz, DMSO-d 6): d = 2.68 (m, 1 H), 2.92 (m, 1 H), 3.45 (m, 2 H), 3.82 (m, 1 H), 4.18 (m, 2H), 5.00 (s, 2H), 5.50 (s, 2H), 6.25 (d, 1 H), 6.62-6.77 (m, 3H), 7.09 (m, 1 H), 7.25 (m, 2H), 7.45 (m, 1 H), 7.62 (m, 2H).

Example 43 3- (2-aminothiazol-4-yl) -2- acid. { 1 - [(benzhydrilcarbamoyl) methyl] -1 H -imidazoI-4-yl} pro-pionic The compound was prepared in analogy to examples 37a-37b and 10b. The removal of the protecting group took place as described above. T.r. (method C) = 1.13 min MS (ES +) = 462 [M + H] + 1 H NMR (500 MHz, DMSO-d6): d = 2.75 (m, 1 H), 3.10 (m , 1 H), 3.50 (s, 2H), 3.75 (m, 1H), 3.98 (d, 2H), 6.07 (s, 1 H), 6.10 (d, 1 H) ), 6.65 (s, 1 H), 7.20-7.35 (m, 9H), 7.39 (s, 1 H), 7.40 (t, 1 H), 8.78 (d) , 1 HOUR).

EXAMPLE 44 3- (2-Aminothiazol-4-yl) -2- [1- ( { [(4-chlorophenyl) phenylmethyl] carbamoyl} methyl) -1H-imidazol-4-yl] propionic acid The compound was prepared in analogy to examples 37a-37b and 10b. The removal of the protecting group took place as described above. T.r. (method C) = 1, 26 min MS (ES +) = 496 [M + H] + 1 H-NMR (500 MHz, DMSO-d 6): d = 2.78 (m, 1 H), 3.10 (m, 1 H), 3.50 (s, 2 H), 3.75 (m, 1 H), 3.95 (d, 2H), 6.08 (s, 1H), 6.11 (d, 1H), 6.65 (s, 1H), 7.20-7.41 (m, 9H), 7 , 60 (t, 1H), 8.85 (d, 1H). Examples 45 and 46 were prepared in analogy to the previous description.

Example 45 3- (6-Aminopyridin-3-yl) -2- acid. { 1 - [4- (3-tert-butylureido) phenyl] -1H-imidazol-4-yl} propà ³ nico like the bistrfl uoroacetato T.r. (method B) = 0.75 min MS (ES +) = 423 [M + H] + 1 H NMR (400 MHz, DMSO-d6): d = 1.29 (s, 9H), 3.10 (dd, 1H), 3.28 (dd, 1H), 4.09 (t, 1H), 6.71 (d, 2H), 7.28 (d, 1H), 7.33 (d, 2H), 7, 56 (d, 1H), 7.85 (s, 1H), 7.92 (s, 1H), 7.99 (s, 1H), 9.03 (s, 1H), 9.28 (s, 1H) ).

Example 46 3- (6-aminopyridin-3-yl) -2- acid. { 1- [4- (3-benzylureido) phenyl] -1H-imi-dazol-4-II} Propionic like bistrifluoroacetate T.r. (method B) = 0.81 mln MS (ES +) = 457 [M + H] + 1 H NMR (400 MHz, DMSO-d6): d = 3.03 (dd, 1H), 3.18 (dd, 1 H), 3.99 (t, 1 H), 4.32 (d, 2H), 6.79 (t, 1 H), 6.90 (d, 1 H), 7.22 (m, 1 H), 7.32 (m, 4H), 7.49 (d, 2H), 7.53 (d, 2H), 7.72 (s, 2H), 7.28 (d, 1H), 7.88 (s, 2H, a), 8.71 (s, 1H, a), 8.86 (s, 1H).

Example 47 Ethyl 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1H-imidazoI-4-yl) propionate The title compound was synthesized as the hydrochloride in analogy to example 2. T.r. (method C) = 0.87 min MS (ES +) = 343 [M + H] + 1 H-NMR (500 MHz, DMSO-d 6): 1.12 (t, 3 H), 1, 13-1, 27 (m, 1 H), 1.31-1.41 (m, 2 H), 1.61 -1, 73 (m, 3H), 1.80-1.86 (m, 2H), 1.98-2.05 (m, 2H), 3.12 (dd, 1 H), 3.18 ( dd, 1 H), 4.12 (m, 2H), 4.21-4.27 (m, 2H), 6.93 (d, 1 H), 7.72-7.78 (m, 3H) , 8.08 (s, 2H), 9.12 (s, 1H).

Pharmacological examples The prepared substances were tested for inhibition of TAFla using the American Diagnostica Actichrome plasma TAFI activity kit (product no. 874). This involved adding 29 μl of assay buffer (20 mM Hepes, 150 mM NaCl, pH 7.4) and 10 μl of TAFla (American Diagnostica product no. 874TAFIA; 2.5 / ml) to 1 μl of a solution of 5 mM DMSO of the substance and incubate in a microtiter plate of 96 wells media at room temperature for 15 minutes. The enzymatic reaction began by adding 10 μl of the TAFla (predilulted to 1: 2 with water). The reaction time course was monitored at 420 nm in a microtiter plate reader (SpectraMax plus 384, Molecular Devices) for 15 minutes.

The C150 was calculated from the mean of the values (determination in duplicate) of serial dilutions of the substance, with the help of the Grafit 4 computer program (Erithacus Software, United Kingdom). Table 1 shows the results.

Table 1 :

Claims (10)

1. A compound of formula and / or all stereoisomeric forms of the compound of formula I and / or mixtures of these forms in any proportion, and / or the physiologically tolerated salt of the compound of formula I, wherein U is 1) a hydrogen atom, ) -alkyl (C? -Cg) -, 3) -cycloalkyl (C3-Cg) -, 4) fluorine, 5) -O-CF3 0 6) -CF3, X is the radical of formula II - (A1) m -A2 (II) where m is the integer zero or 1, A1 is 1) - (CH2) n- > where n is the integer 1, 2 or 3, or 2) -O- (CH2) m where n is the integer zero, 1, 2 or 3,
2. A2 is 1) a 4 to 15 membered Het ring comprising at least one N atom, and is substituted with an amino group and may also be independently substituted one, two or three times with an -alkyl (C? - C3) -, halogen, -CF3 or -O-CF3, 2) -alkyl (C1-Cg) -NH2 or 3) -cycloalkyl (C3-C8) -NH2, Y-is 1) the radical of formula III A3- (A4) 0- (A5) p (III) wherein a) A3 is -cycloalkyl (C3-C8) - or -alkynylene (C2-Cg) -, in which the cycloalkyl or alkynylene are unsubstituted or are independently substituted one, two or three times with -O-R10 or R1, A4 is -N (R2) 2-, wherein R2 is as defined below, and the two radicals R2 are independently defined from each other , A5 is absent, or is the integer zero or 1, and R10 is a hydrogen atom, -alkyl (C? -Cg) - o -aryl (Cg-C < / 4) -, b) A3 is - cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted yes one, two or three times with -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, or is the integer 1, and p is the integer 1, c) A3 is a cyclic amine having from 3 to 8 atoms in the ring, in which the cyclic amine is unsubstituted or is independently substituted one, two or three times with R1, A4 and A5 are as defined in b), that A5 is attached to the N atom of A3, or is the integer zero, and p is the integer zero or 1, od) A3 is - (CH2) q-aryl (Cg-C-j4) -, where the aryl is unsubstituted or is independently substituted one, two or three times with R1, A4 and A5 are as defined in b), or is the integer zero or 1, and p is the integer 1, and q is the whole number zero, 1, 2 or 3, e) A3 is - (CH2) r-Het, where Het is a Het ring of 4 to 15 members, and the Het ring is unsubstituted or is independently substituted one, two or three times with = O or R1, A4 and A5 are as defined in b), or is the integer zero or 1, p is the integer 1, and r is the integer zero, 1, 2 or 3, f) A3 is -aryl (CH2) q- (C6-C?) -, in which the aryl is unsubstituted or is independently substituted among if one, two or three times with R1, A4 is -O-, A5 is -Ri (Cg-C- | 4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, o and p are the integer 1 and q is the integer zero, 1, 2 or 3, wherein R1 is a) -aryl (Cg-Ci4) -, wherein the aryl is unsubstituted or is independently substituted one, two or three times with -alkyl (d-C6) -, -alkyl (C0-C4) - cycloalkyl (C3-C8) -, -CF3, = O, -O-CF3 or halogen, b) a Het ring of 4 to 15 members, c) -alkyl (C? -Cg) -, d) -acyl (Cn-C4) -cycloalkyl (C3-C8) -, e) -CF3, f) -O-CF3 og) halogen, wherein R2 is a) -aryl (Cg-C-j4) -, wherein the aryl is unsubstituted or is independently substituted one, two or three times with R1, b ) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, c) -cycloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, d) -CF3 or e) a hydrogen atom, wherein R3, R6 and R7 are identical or different and are, independently of each other a) - alkyl (C? -Cg) -, wherein the alkyl is not substituted or independently substituted one, two or three times with R1, b) -aryl (Cg-Ci4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, c) a Het ring of 4 to 15 members, in which the Het ring is unsubstituted or is independently substituted one, two or three times with R1, d) -cycloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R 1, or e) a hydrogen atom, in which R 4 and R 5 are identical or different and are, independently of each other a) -alkyl (C- | -Cg) - or wherein the alkyl or alkenyl are unsubstituted or are independently substituted one, two or three times with R 1, b) -aryl (Cg-Ci 4) -, wherein the aryl is unsubstituted or substituted independently of one another one, two or three times with R1, c) a Het ring of 4 to 15 members, in which the Het ring is unsubstituted or is independently substituted one, two or three times with R1, d) -cycloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, or R4 and R5 form, together with the nitrogen atom to which they are attached, a ring having from 3 to 8 ring atoms, which may also comprise, in addition to the nitrogen atom, one or two more heteroatoms of the oxygen, sulfur or nitrogen series, Y is 2) the radical of formula IV, wherein R8 is a) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) -aryl (Cg-C < i4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, c) a Het ring of 4 to 15 members, wherein the Het ring is unsubstituted or is independently substituted one, two or three times with R1, d) -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, and is 3) the radical of formula V wherein, in case a) R12 is 1) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, 2) -alkyl (Cn-C3) -cycloalkyl (C3-Cg) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1,
3. 3) -alkyl (Co-C3) -aryl (Cg-Ci4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, or 4) -alkyl (Co-C3 ) -Het, in which Het is unsubstituted or independently substituted one, two or three times with R1, and R13 is 1) -alkyl (Co-C3) -aryl (Cg-C-) 4) -, wherein the alkyl and aryl are unsubstituted or are independently substituted each other one, two or three times with R1, or 2) -alkyl (Crj-C3) -Het, wherein the alkyl and Het each do not is substituted or independently substituted one, two or three times with R1, wherein, in case b) R12 is 1) a hydrogen atom, 2) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, 3) -alk (Crj-C3) -ary (Cg-Ci4) -, in the that the aryl is unsubstituted or is independently substituted one, two or three times with R1, or 4) -alkyl (Co-C3) -Het, in which Het is unsubstituted or is independently substituted one, two or three times with R1, and R13 is -CH (R8) -R9, wherein R8 and R9 are independently of each other -aryl (Cg-C- | 4) - or Het, wherein Het and the aryl each is unsubstituted or is independently substituted one, two or three times with -O-alkyl (Crd) - or R1, and R16, R17, R18 and R19 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C- | -Cg) -, wherein the alkyl is unsubstituted or is substituted once or twice with R 1, 3) halogen, 4) -OH, 5) -NH 2, 6 ) -alkyl (Co-C3) -aryl (Cg-C- | 4) -, wherein the alkyl and aryl are each unsubstituted or substituted independently one, two or three times with R1, or 7) -alqui (Crj-C3) -Het, wherein the alkyl and Het each is unsubstituted or is independently substituted one, two or three sometimes with R1, or R16 and R17, or R18 and R19 form, together with the carbon atom to which they are respectively attached, a ring having from 3 to 6 ring atoms, or Y is 4) the radical of formula VI, wherein R24 and R25 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) -alkyl (Co-C3) -aryl (Cg-Ci4) -, wherein the alkyl and aryl each is unsubstituted or is independently substituted one, two or three times with R1, 4) -alkyl (Crj-C3) -Het, wherein the alkyl and Het are each unsubstituted or independently substituted one, two or three times with R1, or 5) -alkyl (Co-C3) - cycloalkyl (C3-Cg) -, or 'R24 and R25 form, together with the nitrogen atom to which they are attached, a ring having from 3 to 8 ring atoms, which may also comprise, in addition to the nitrogen atom, one or two further heteroatoms of the oxygen, sulfur or nitrogen series, R26, R27, R28 and R29 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C- | -Cg) -, in that the alkyl is unsubstituted or is substituted once or twice with R1, 3) halogen, 4) -OH, 5). -NH2, 6) -alkyl (Co-C3) -aryl (Cg-C- | 4) -, wherein the alkyl and aryl are each unsubstituted or independently substituted one, two or three times with R1 , or 7) -alkyl (Co-C3) -Het, wherein the alkyl and Het each is unsubstituted or is independently substituted one, two or three times with R1, or R26 and R27, or R28 and R29 form, together with the carbon atom to which they are respectively attached, a ring having from 3 to 6 ring atoms, Z is 1) a hydrogen atom, 2) -alkylofC-i- Cg) -, 3) -alkyl (C? -Cg) -OH, 4) -alkyl (Co-C) -cycloalkyl (C3-C6) -, 5) -alkyl (d-C10) -OC (O) - O-R1, 6) - (CH2) rarl1 (C6-Ci4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, and r is the integer zero , 1, 2 or 3, or 7) - (CH2) s_Het, in which Het is not substituted or independently substituted one, two or three times with R1, and s is the integer zero, 1, 2 or 3 . A compound of the formula according to claim 1, wherein U is 1) a hydrogen atom, 2) -alkyl (C? -Cg) -, 3) -cycloalkyl (C3-Cg) -, 4) fluorine, 5) -O-CF3 or 6) -CF3, X is the radical of formula II, wherein m is the integer zero or 1, A1 is 1) - (CH2) n-, wherein n is the integer 1, 2 or 3, or 2) -O- (CH2) m where n is the integer zero, 1, 2 or 3, A2 is 1) a Het ring of 4 to 15 members, wherein the Het ring is selected from the group of acridinyl, azepinyl, azetidinyl, aziridinyl, benzimidazalinyl, benzimidazolyl, carbolinyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, chromanyl, chromenyl, cinnolinyl, decahydroquinolinyl, imidazolidinyl, imidazolinyl , imidazolyl, 1H-indazolyl, indolinyl, indolizinyl, indolyl, indolyl, 3H-indolyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl (benzimidazolyl), isothiazolidyl, 2- isothiazolinyl, isothiazolyl, isoxazolyl, isoxazolidinyl, 2-isoxazolinyl, morpholinyl , naphthyridinyl, octahydroisoquinolinyl, oxadiazolium, 1,2,3-oxadiazoliol, 1,2,4-oxadiazolyl, 1 , 2,5-oxadiazolyl, 1,4-oxadiazolyl, oxazolidinyl, oxazolyl, pyrimidinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxyntinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, piroazolidinyl, pyrazolinyl , pyrazolyl, pyridazinyl, pyridooxazolyl, pyridoimidazolyl, pyridothiazolylpyridothiophenyl, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrahydropyridinyl, 6H-1,2,5-thiazinyl, 1,2,3-thiadiazolyl, 1,4-thiadiazolium 1,2,5-thiadiazolyl, 1,4-thiadiazolyl, thiantrenyl, thiazolyl, thienothiazolyl, thienooxazolyl, thienoimidazole, thiomorpholinyl, triazinyl, 1,2,3-triazolyl, 1,4-triazole, 1,2 , 5-triazolyl, 1, 3,4-triazoly and xanthenyl, and wherein the Het ring is substituted with an amino group, and can also be independently substituted one, two or three times with an -alkyl (C-) | -C3) -, halogen, -CF3 0 -O-CF3, 2) -alk (C? -Cg) -NH2 or 3) -cycloalkyl (C3-C8) -NH2, Y is 1) the radical of formula III, wherein A3 is -cycloalkyl (C3-C8) - or -alkyne (C2-C6) -, in which the cycloalkyl or alkynylene are unsubstituted or substituted independently one, two or three times with -O-R10 or R1, A4 is -N (R2) 2-, wherein R2 is as defined below, and the two radicals R2 are independently defined, A5 is absent, I is the integer zero or 1, and R10 is a hydrogen atom, -alkyl (CrC6) - or phenyl, b) A3 is -cycloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or substituted independently of one, two or three sometimes with -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, or is the integer 1, and p is the integer 1, c) A3 is a cyclic amine of the propylamine group , azetidine, pyrrolidine, piperidine, azepanes or azoanes, in which the cyclic amine is unsubstituted or is independently substituted one, two or three times with R1, A4 and A5 are as defined in b), where A5 is attached to the N atom of A3, or is the integer zero, and p is the integer zero or 1, od) A3 is - (CH2) q-aryl (Cg-C'j4) -, wherein the aryl is selected from the group of phenyl, naphthyl, anthryl or fluorenyl, and is unsubstituted or substituted each other one, two or three times with R1, A4 and A5 are as defined in b) or 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, where Het is as defined above, and is unsubstituted or substituted independently one, two or three times with = O or R1, A4 and A5 are as define in b), or is the integer zero or 1, p is the integer 1, and r is the integer zero, 1, 2 or 3, f) A3 is -aril (CH2) q- (C6-C? ) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -O-, A5 is -aryl (Cg-Ci4) -, in which the aryl is not substituted or independently substituted one, two or three times with R1, o and p are the integer 1 and q is the integer zero, 1, 2 or 3, g) -CH (phenyl) -phenyl, wherein R1 is a) -aryl (Cg-Ci4) -, wherein aryl is as defined above, and wherein the aryl is unsubstituted or substituted, independently of one, two or three times with - alkyl (CrC6) -, -alkyl (C0-C) -cycloalkyl (C3-C8) -, -CF3, = O, -O-CF3 or halogen, b) a Het ring of 4 to 15 members, in which Het is as defined above, c) -alkyl (C? -Cg) -, d) -cycloalkyl (C3-C8) -, e) -CF3, f) -O-CF3 or g) halogen, wherein R2 is a ) -aryl (Cg-C? 4) -, in which aryl is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, b) -alkyl (C? -Cg ) -, in which the alkyl is unsubstituted or is independently substituted one, two or three times with R1, c) -cycloalkyl (C3-C8) -, in which the cycloalkyl is not is substituted or independently substituted one, two or three times with R1, d) -CF3 or e) a hydrogen atom, wherein R3, R6 and R7 are identical or different and are. independently from each other a) -alkyl (C- | -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) -aryl (Cg-Ci4) -, wherein aryl is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, c) a 4 to 15 membered Het ring, wherein the ring Het is as defined above, and is unsubstituted or substituted independently of one another, two or three times by R 1, d) -cycloalkyl (C 3 -C 8) -, wherein the cycloalkyl is unsubstituted or substituted independently from yes one, two or three times with R1, oe) a hydrogen atom, in which R4 and R5 are identical or different and are, independently of each other a) -alkyl (C-j-Cg) - or -alkenyl (C2-C-jo) -. wherein the alkyl or alkenyl are unsubstituted or are independently substituted one, two or three times with R 1, b) -aryl (Cg-C- | 4) -, wherein aryl is as defined above, and is unsubstituted or is independently substituted one, two or three times with R1, c) a Het ring of 4 to 15 members, in which the ring Het is as defined above, and is unsubstituted or substituted independently of one another, two or three times by R 1, d) -cycloalkyl (C 3 -C 8) -, wherein the cycloalkyl is unsubstituted or is independently substituted among yes one, two or three times with R1, oe) a hydrogen atom, or R4 and R5 form, together with the nitrogen atom to which they are attached, a ring having from 3 to 8 ring atoms selected from the propylamine group , azetidine, pyrrolidine, piperidine, azepanes, azoanes, azepine, dioxazole, dioxazine, 1,4-diazepane, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, imidazole, imidazoline, imidazolidine, isothiazole, isothiazolidine , isothiazoline, isoxazole, isoxazolin, isoxazolidine, 2-isoxazoline, cetopiperazine, 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 1,4-triazole, and is 2) the radical of formula IV, in which formula IV is a compound of the group of azetidin-2-one, pyrrolidin-2-one, piperidin-2-one, azepan-2-one and azocan-2-one , and is substituted at the nitrogen atom in each case with R8, wherein R8 is a) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) -aryl (Cg-C- | 4) -, in which aryl is as defined above, and is unsubstituted or is independently substituted one, two or three times with R1, c) a ring Het of 4 to 15 members, wherein the Het ring is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, d) -cycloalkyl (C3-C8) -, wherein the cycloalkyl no is substituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, and is 3) the radical of formula V, wherein, in case a) R12 is 1) -alkyl ( C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, 2) -alkyl (Co-C3) -cycloalkyl (C3-Cg) -, that the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, 3) -alkyl (Crj-C3) -arylo (Cg-C-i4) -, wherein aryl is as defined above, and is unsubstituted or substituted independently one, two or three times with R1, or 4) -alkyl (Co-C3) -Het, in which Het is as defined above, and is not substituted or independently substituted one, two or three times with R1, and R13 is 1) -alkyl (Co-C3) -aryl (Cg-Ci4) -, wherein alkyl and aryl are as defined above, and everyone does not is replaced or is substituted independently of each other one, two or three times with R1, or 2) -alkyl (Co-C3) -Het, wherein alkyl and Het are as defined above, and each is unsubstituted or substituted independently of one another , two or three times with R1, or in case b) R12 is 1) a hydrogen atom, 2) -alkyl (Cj-Cg) -, wherein the alkyl is unsubstituted or substituted independently of one another, two or three times with R1, 3) -alkyl (Crj-C3) -aryl (Cg-C-j4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, or 4) -alkyl (Cn-C3) -Het, wherein Het is unsubstituted or is independently substituted one, two or three times with R1, and R13 is -CH (R8) -R9, wherein R8 and R9 are independently each other -aryl (Cg-C-j4) - or Het, wherein Het and aryl is each as defined above, and is unsubstituted or substituted independently of one, two or tr is times with -O-alkyl (d-d) - or R1, and R16, R17, R18 and R19 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -a? Qullo (C -? - Cg) -, wherein the alkyl is unsubstituted or substituted once or twice with R1, 3) halogen, 4) -OH, 5) -NH2, 6) -alkyl (Co-C3) -ariIo (Cg-Ci4) -, wherein alkyl and aryl are as defined above , and each is unsubstituted or substituted independently one, two or three times with R1, or 7) -alkyI (Crj-C3) -Het, wherein alkyl and Het are as defined above, and each is unsubstituted or is independently substituted one, two or three times with R1, or R16 and R17, or R18 and R19 form, together with the carbon atom to which they are respectively attached, a ring having from 3 to 6 ring atoms of the cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group, or Y is 4) the radical of formula VI, in which R 24 and R 25 are identical or different and are independently from each other 1) a hydrogen atom, 2) -alkyl (Cj-Cg) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) -alkyl (Co-C3) -aryl (Cg-) Ci4) -, wherein alkyl and aryl are as defined above, and each is unsubstituted or is independently substituted one, two or three times with R1, 4) -alkyl (Crj-C3) -Het, in alkyl and Het are as defined above, and each is unsubstituted or is independently substituted one, two or three times with R1, or 5) -alkyl (Crj-C3) -cycloalkyl (C3-Cg) - , or R24 and R25 form, together with the nitrogen atom to which they are attached, a ring having from 3 to 8 ring atoms of the group of propylamine, azetidine, pyrrolidine, piperidine, azepanes, azoanes, azepine, dioxazole, dioxazine, 1,4-diazepane, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, imidazole, imidazoline, imidazolidine, isothiazole, isothiazolidine, isothiazoline, isoxazole, isoxazoline, soxazolidin a, 2-isoxazoline, cetopiperazine, morpholine, [1,4] oxazepane, oxazole, piperazine, pyrazine, pyrazole, pyrazoline, pyrazolidine, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolidinone, pyrroline, tetrahydropyridine, thiazole, thiazole, thiazolidine, thiazoline , thiomorpholine, 1,2,3-triazine, 1,2,4-triazine, 1, 3,5-triazine, 1,2,3-triazole or 1,4-triazole, R26, R27, R28 and R29 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or substituted or twice with R1, 3) halogen, 4) -OH, 5) -NH2, 6) -alkyloCo-Csy-aryl ^ -C ^) -, wherein alkyl and aryl are as defined above, and each is unsubstituted or is independently substituted one, two or three times with R1, or 7) -alkyl (Co-C3) -Het, wherein alkyl and Het are as defined above, and each is unsubstituted or substituted is independently substituted one, two or three times with R1, or R26 and R27, or R28 and R29 form, together with the carbon atom to which they are respectively attached, a ring having from 3 to 6 ring atoms of the group of cyclopropyl, cidobutyl, cyclopentyl or cyclohexyl, Z is 1) a hydrogen atom, 2) -alkyl (C? -Cg) -, 3) cycloalkyl (C3-Cg) -,
4. 4) alkyl (C? -C10) -OC (O) -O-R1,
5. 5) - (CH2) radical (Cg-Ci4) -, wherein aryl is as defined above, and is unsubstituted or is independently substituted one, two or three times with R1, and r is the integer zero, 1, 2 or 3, or
6. 6) - (CH2) S-Het, in which Het is as defined above, and not is substituted or independently substituted one, two or three times with R1, and s is the integer zero, 1, 2 or 3. 3. - A compound of the formula according to claim 1 or 2, wherein U is a hydrogen atom, -CF3, fluorine or -CH3, X is the radical of formula II, wherein m is the integer 1, A1 is 1) - (CH2) -, 2) -O- (CH2) m wherein n is the integer zero or 1, or 3) a covalent bond, A2 is 1) aminopyridyl, wherein aminopyridyl is unsubstituted or is independently substituted one, two or three times with -alkyl (Cj-C3) -, halogen or -CH3, 2) aminothiazole, in which amnotol-azolyl is unsubstituted or is independently substituted one, two or three times with -alkyl (C? -C3) -, halogen or -CH3, 3) -alkyl (C -? - C3) -NH2 or 4) -cycloalkyl (C3-C8) -NH2, Y is 1) the radical of formula III, in which a) A3 is -cycloalkyl (C3-C8) - or -alkynylene (C2-Cg) -, in which the cycloalkyl or alkynylene are not substituted or are independently substituted one, two or three times with R1, A4 is -N (R2) 2-, wherein R2 is as defined below, and the two radicals R2 are independently defined from each other, A5 is absent and or the integer zero or 1, b) A3 is -cycloalkyl (C3-Cg) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with 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, or is the integer 1, and p is the integer 1, c) A3 is a cyclic amine having from 3 to 8 atoms in the ring, in which the cyclic amine is unsubstituted or substituted independently of one another, two or three times with R1, A4 and A5 are as defined in b), where A5 is attached to the N atom of A3, or is the integer zero, and p is the integer zero or 1, od) A3 is - (CH2) q-aryl (Cg-C-j4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, A4 and A5 are as defined in b), or 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, where Het is pyrrolidine, benzothiophene or piperidine, which are not substituted or are independently substituted one, two or three times with = O or R1, A4 and A5 are as defined in b), or is the integer zero or 1, p is the integer 1, and r is the integer zero, 1, 2 or 3, f) A3 is -phenyl (CH2) q-, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -O-, A5 is phenyl, in which the phenyl is unsubstituted or is independently substituted one, two or three times with R1, oyp is the integer 1 and q is the integer 1 or 2, wherein R1 is a) phenyl, wherein phenyl is unsubstituted or is independently substituted one, two or three times with -alkyl (CrC4) -, b) triazolyl or pyridinyl, c) -alkyl ( C? -C4) -, d) -cycloalkyl (C3-Cg) -, e) -CF3, f) -O-CF3, g) fluorine or chlorine, in which R2 is a) phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, b) -alkyl (C? -C3) ~, wherein the alkyl is unsubstituted or substituted independently of one another, two or three times with R1, c) -cycloalkyl (C3-Cg) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, d) -CF3 E) a hydrogen atom, wherein R3, R6 and R7 are identical or different and are, independently of each other a) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted each other one, two or three times with R1, b) -ariIo (Cg-C- | 4) -, in which the aryl is unsubstituted or is independently substituted one, two or three times with R1, c) a ring Het of 4 to 15 members, in which the ring Het is not substituted or is independently substituted one, two or three times with R1, d) -cycloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, wherein R4 and R5 are identical or different and are, independently of each other a) -alkyl (C- | -Cg) - or -alkenyl (C2-Cg) -, wherein the alkyl or alkenyl are unsubstituted or substituted independently of one, two or three times with R1, b) -aryl (Cg-Ci4) -, wherein the aryl is unsubstituted or is independently substituted with one another, two or three times with R1, c) a Het ring of 4 to 15 members, in which the Het ring is unsubstituted or is independently substituted one, two or three times with R1, d) -cycloalkyl (C3-) C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or e) a hydrogen atom, or R4 and R5 form, together with the nitrogen atom to which are bound, a ring derived from azetidine, pyrrolidine, piperidine, azepanes, azoanes, azepine, dioxazole, dioxazine, 1,4-diazepane, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, imidazole, imidazoline, imidazolidine, isothiazole, isothiazolidine, siazoline, isoxazole, isoxazoline , isoxazolidine, 2-oxazoline, cetopiperazine, morpholine, [1,4] oxazepane, oxazole, piperazine, pyrazine, pyrazole, pyrazoline, pyrazolidine, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolidinone, pyrroline, tetrahydropyridine, thiazole, thiazolide, thiazolidine , thiazoline, thiomorpholine, 1,2,3-triazine, 1, 2,4-triazine, 1, 3,5-triazine, 1,2,3-triazole or 1,4-triazole, Y is 2) radical of formula IV selected from the group of azetidin-2-one, pyrrolidin-2-one or piperidin-2-one, wherein the radical is substituted at the nitrogen atom in each case with R8, wherein R8 is a ) -alkyl (Cj-Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, c) a hydrogen atom, or d) -cycloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted with one, two or three times with R1, Y is 3) the radical of formula V, in which, in case a) R12 is 1) -alkyl (Cj-Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, 2) -alkyl (Co-C3) -cycloalkyl (C3-Cg) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, or 3) -alkyl (Crj-C3) -phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, and R13 is 1) -alkyl (Cr- C3) -phenium, wherein the alkyl and phenyl are each unsubstituted or independently substituted one, two or three times with R1, or 2) -alkyl (Cn-C3) -pyridyl, wherein the alkyl and pyridyl each is unsubstituted or is independently substituted one, two or three times with R1, or in case b) R12 is 1) a hydrogen atom, 2) -alkyl (C -? - Cg) -, wherein the alkyl is unsubstituted or substituted independently of one another one, two or three times with R1, 3) -alkyl (Co-C3) -phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, or 4) -alkyl (Cfj-C3) -pyridyl, wherein the alkyl and pyridyl are each unsubstituted or substituted independently one, two or three times with R1, and R13 is -CH (R8) -R9, wherein R8 and R9 are independently phenyl or pyridinyl, wherein the phenyl or pyridyl each is unsubstituted or substituted independently of one, two or three sometimes with -O-alkyl (C C4) - or R1, and R16, R17, R18 and R19 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (Cj-C3) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) fluoro, 4) -OH, 5) -NH2 or 6) -alkyl (Crj-C3) -phenyl, wherein the alkyl and phenyl each is not substituted or is independently substituted each one one, two or three times with R1, or Y is 4) the radical of formula VI, wherein R24 and R25 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl ( C -? - Cg) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) -alkyl (Cn-C3) -phenyl, wherein the alkyl and phenyl each do not is substituted or independently substituted one, two or three times with R1, or 4) -acyl (C0-C3) -cycloalkyl (C3-C6) -, or R26, R27, R28 and R29 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (Cj-C3) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, 3) fluorine, 4) -OH, 5) -NH2 or 6) -alkyl (Co-C3) -phenyl, wherein the alkyl and phenyl are each unsubstituted or independently substituted one, two or three times with R1, and Z is a hydrogen atom or alkyl (CrC) -. 4. - A compound of the formula according to claim 2, wherein U is a hydrogen atom, X is the radical of formula II, wherein m is the integer 1, A1 is - (CH2) -, A2 is amlnopyridyl, in the aminopyridyl is unsubstituted or is independently substituted one, two or three times with halogen or -CH3, Y is 1) the radical of formula III, wherein a) A3 is -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, b) A3 is -alkynylene (C2-C) -, in which the alkylene is unsubstituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, c) A3 is a cyclic amine having from 3 to 8 ring atoms, wherein the cyclic amine is not is substituted or independently substituted one, two or three times with R1, and A4 and A5 are absent, d) A3 is -phen (CH2) q-, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -N (R2) -, wherein 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, or is the integer 1, and p is the integer 1, and q is the integer zero, 1 or 2, and ) A3 is - (CH2) [- Het, where Het is pyrrolidine or piperidine, which are unsubstituted or substituted independently one, two or three times with R1, A4 is absent and A5 is as defined in d ), wherein A5 is attached 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, wherein the phenyl is not is substituted or independently substituted one, two or three times with R1, A4 is -O-, A5 is phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, wherein R1 is a) phenyl, wherein phenyl is unsubstituted or substituted independently of one, two or three vec it's with -alkyl (CrC4) -, b) triazolyl or pyridinyl, c) -alkyloid-d) -, d) -cycloalkyl (C3-C6) -, e) -CF3, f) -O-CF3, g ) fluorine or i) chlorine, wherein R2 is a hydrogen atom or -alkyl (CrC3) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, wherein R3 , R6 and R7 are identical or different and are, independently of one another a) -alkyl (C- | -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, c) a hydrogen atom, or d) -cycloalkyl (C3-C6) -, wherein the cycloalkyl it is unsubstituted or substituted independently of one another, two or three times with R1, in which R4 and R5 are identical or different and are, independently of each other a) -alkyl (C? -Cg) - or -alkenyl (C2-Cg) -, wherein the alkyl or alkenyl are unsubstituted or are independently substituted one, two or three times with R1, b) phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, c) a hydrogen atom, or d) -cycloalkyl (C3-C6) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, Y is 2) the radical of a pyrrolidin-2-one, in which the radical is each substituted with R8 on the nitrogen atom, in which R8 is a) -alkyl (C- | -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R 1, b) phenyl, wherein the phenol is unsubstituted or is independently substituted one, two or three times with R1, c) -cycloalkyl (C3-C6) -, wherein the cycloalkyl is unsubstituted or substituted independently one, two or three times with R1, Y is 3) the radical of formula V, wherein R12 is a hydrogen atom or -alkyl (CrC6) -, wherein the alkyl is unsubstituted or substituted independently one, two or three times with R1, and R13 is -CH (R8) -R9, wherein R8 and R9 are, independently of each other, phenyl or pyridyl, wherein the pyridyl and phenyl each is unsubstituted or is independently substituted one, two or three times with R1, and R16, R17, R18 and R19 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C? -C3) -, wherein the alkyl is unsubstituted or is substituted once or twice with R1, or 3) -alkyl (Co-C3) -phenyl, wherein the alkyl and phenyl are each unsubstituted or substituted independently from each other yes one, two or three times with R1, and Z is 1) a hydrogen atom, 2) -alkyl (C -? - Cg) -, 3) -alqull (C- | -Cg) -OH, 4) - alkyl (Co-C4) -cycloalkyl (C3-Cg) -, or 5) -alkyl (C? -C? o) -0-C (O) -O-cycloalkyl (C3-Cg) -. 5. - A compound of the formula according to one or more of claims 1 to 4, wherein U is a hydrogen atom, X is the radical of formula II, wherein m is the integer 1, A1 is A2 is not replaced or is substituted independently one, two or three times with F, Cl, Br, I or -CH3, Y is 1) the radical of formula III, wherein a) A3 is -cloalkyl (C3-C8) -, wherein the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, b) A3 is -alkynylene (C2-C) -, in which the alkynylene is unsubstituted or is independently substituted one, two or three times with R1, and A4 and A5 are absent, c) A3 is a cyclic amine having from 3 to 6 ring atoms, in which the cyclic amine is unsubstituted or substituted independently one, two or three times with R1, and A4 and A5 are absent, d) A3 is -phenyl (CH2) q-, wherein the phenyl is unsubstituted or is independently substituted one, two or three sometimes with R1, A4 is -N (R2) -, wherein 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, or is the integer 1, p is the integer 1, and q is the integer zero, 1 or 2, e) A3 is - (CH2) r-Het, where Het is pyrrolidin or piperidine, which are not substituted or are independently substituted one, two or three times with R1, A4 is absent and A5 is as defined in d), wherein A5 is attached 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-phenol, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, A4 is -O-, A5 is phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R1, wherein R1 is a) phenyl, wherein phenyl is not substituted or independently substituted one, two or three times with -alkyl (d-C4) -, b) pyridyl or tetrazolyl, c) -alkyl (CrC4) -, d) -cycloalkyl (C3-C6) -, e) -CF3, g) fluorine or i) chloro, wherein R2 is a hydrogen atom or -alkyl (CrC3) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, wherein R3, R6 and R7 are identical or different and are, independently of each other a) -alkyl (C? -Cg) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, b) phenyl, wherein the phenol is unsubstituted or is independently substituted one, two or three times with R 1, c) cycloalkyl (C 3 -C 6) -, wherein the cycloalkyl is unsubstituted or is independently replaced each other one, two or three times with R1, wherein R4 and R5 are identical or different and are, independently of each other a) -alkyl (C? -Cg) - or -alkenyl (C2-C4) -, wherein the alkyl or alkenyl are unsubstituted or are independently substituted one, two or three times with R 1, b) phenyl, wherein the phenyl is unsubstituted or is independently substituted one, two or three times with R 1, c) a hydrogen atom, or d) -cycloalkyl (C3-C8) -, in which the cycloalkyl is unsubstituted or is independently substituted one, two or three times with R1, Y is 2) the radical of a pyrrolidin-2-one, in which the radical is in each case substituted with R8 on the nitrogen atom, wherein R8 is phenyl, wherein the phenyl is unsubstituted or is independently replaced one, two or three times with R1, Y is 3) the radical of formula V, wherein R12 is a hydrogen atom or -alkyl (CrC6) -, wherein the alkyl is unsubstituted or is independently substituted one, two or three times with R1, and R13 is -CH (R8) -R9, wherein R8 and R9 are, independently of each other, phenyl or pyridyl, wherein the pyridyl and phenyl each is unsubstituted or substituted independently of one another, two or three times with R1, R16, R17, R18 and R19 are identical or different and are, independently of each other 1) a hydrogen atom, 2) -alkyl (C- | -C3) -, wherein the alkyl is not substituted or is substituted once or twice with R1, or 3) -alkyl (CQ-C3) -phenium, in which the alkyl and phenyl each do not is substituted or independently substituted one, two or three times with R1, and Z is a hydrogen atom. 6. A compound of the formula according to one or more of claims 1 to 5, which is the compound 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazol-4-yl) acid propionic, 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazol-4-yl) methyl propionate, 3- (6-aminopyridin-3-yl) -2- (1-cyclohexy) -1 H-imidazole-4-yl) isopropyl propionate, cyclopropylmethyl 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazoI-4-yl) propionate, 3- (6 2-hydroxyethyl, -aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazol-4-yl) propionate, 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1) H-imidazole-4-yl) 1-cyclohexyloxycarbonyloxyethyl 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-1 H-imidazole-4-II) propionic, 3- (6-aminopyridin-3-yl) -2- [1 - (2-Oxo-1-phenylpyrrolidin-3-yl) -1 H -imidazol-4-yl] propionic acid, 3- (6-aminopyridin-3-yl) -2-. { 1 - [(benzhydrocarbamoyl) methyl] -1 H- imidazole-4-H} proplónico, 3- (6-aminopiridin-3-iI) -2-. { 1 - [(benzhydriIcarbamoll) methyl] -1 H -imidazol-4-yl} isopropyl propionate, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [4- (3-phenyl] -ureido) phenyl] -1H-imidazol-4-yl} pro-pionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1- [2- (1-diphenylacetylpiperidin-4-yl) ethyl] -1H-imidazoI-4-yl} propionic acid 3- (6-aminopyridin-3-yl) -2-. { 1- [2- (1-benzoylpiperidin-4-yl) ethyl] -1H-imi-dazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- [1 - (1-benzoylpiperidin-2-ylmethyl) -1 H-imidazol-4-yl] propionic acid, 3- (6-aminopyridin-3) -l) -2- (1 - {2- [1 - (3-phenylpropionyl) piperidin-3-yl] ethyl} - 1 H-imidazol-4-yl) propionic acid, 3- (6 -aminopyridin-3-yl) -2- [1 - (1-diphenylacetylpiperidin-3-ylmethyl) -1 H -amido-zol-4-ll] propionic acid, 3- (6-aminopyridin-3-yl) ) -2- (1 - { 2- [1 - (3-phenyipropionyl) piperidin-4-yl] ethyl.} - 1 H-imidazol-4-yl) propionic acid, 3- (6-aminopyridine) 3-il) -2-. { 1 - [2- (1-phenylacetylpiperidin-3-yl) ethyl] -1 H -imi-dazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1- [2- (1-phenylacetylpperidin-4-yl) etl] -1H-imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [1 - ^ '- Methylblphenyl-S-carboni piperidin-4-ylmethyl] -1H-imldazol-4-iI} proponic, 3- (6-aminopyridin-3-yl) -2- [1- (1-benzoyl-pyridin-4-ylmethyl) -1H-imidazol-4-yl] propionic acid, 3- (3- (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-ylbenzyl) -1H-imidazol-4-yl] propionic acid, 3- (6-aminopyridin-3-yl) -2- [1- (4-trifluoromethoxybenzyl) -1 H-imidazol-4-ylpropionic acid, 3- (6-aminopyridin-3-yl) -2- [1- (1,1-dioxo-1 H-1,6-benzo [b] thiophen-2-ylmethyl) -1 H-lmidazol-4-yl] propionic acid, 3- (6-aminopyridin-3-yl) -2- [1 - (5-cyclobenzo [b] thiophen-3-ylmethyl) -1 H-imidazole -4-il] propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [3- (4-fluorophenoxy) benzyl] -1 H -imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- [1- (2-phenoxybenzyl) -1 H -imidazol-4-ylpropionic acid, 3- (6-aminopyridin-3-yl) - 2- [1- (4-phenoxybenzyl) -1 H-imidazol-4-ylpropionic acid, 3- (6-aminopyridin-3-yl) -2- (1-prop-2-ynyl-1 H-imidazole-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) -1 H -imidazol-4-ylproproionic acid, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [(benzhydrylmethylcarbamoyl) methyl] -1 H -imi-dazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- [1- ( { [(4-chlorophenol) phenylmethyl] carbamoyl} -ethyl) -1 H-imidazole-4- il] propionic acid, 3- (6-aminopyridin-3-yl) -2- [1- ( { [b.s- (4-methoxy-phenyl) -methyl] -carbamoyl} -methyl. ) -1H-imidazol-4-yl] propionic acid, 3- (6-aminopyridin-3-yl) -2-. { 1- [4- (3-propylureldo) phenyl] -1 H-imidazol-4-yl} -propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [4- (Toluene-4-sulfonylamino) phenyl] -1H-imide-zol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1- [3- (3-propylurethane) benzyl] -1 H -imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [3- (3-phenethylureido) benzyl] -1 H-imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1 - [3- (3-benzylureido) benzyl] -1 H-imidazol-4-yl} propionic, 3- (6-aminopyridin-3-yl) -2- acid. { 1- [3- (3-vinyluretho) benzyl] -1 H-lmidazol-4-ylpropionic acid, 3- (2-aminothiazol-4-yl) -2- acid. { 1 - [(benzhydrilcarbamoyl) methyl] -1H-imidazol-4-yl} propionic, 3- (2-aminothiazol-4-yl) -2- [1- ( { [(4-chlorophenyl) phenylmethyl] carbamoyl] methyl) - "1 H -imidazol-4-yl] propionic acid, 3- (6-aminopyridin-3-yl) -2- { 1 - [4- (3-tert-butylureido) phenyl] -1H-imide-zol -4-yl.} Propionic, 3- (6-aminopyridin-3-yl) -2- { 1 - [4- (3-benzylureido) benzyl] -1 H-imidazole- 4-l} propionic, or ethyl 3- (6-aminopyridin-3-yl) -2- (1-cyclohexyl-1 H-imidazol-4-yl) propionate.
7. 7. - A process for preparing the compound of formula I according to one or more of claims 1 to 6, comprising a) a compound of formula VII wherein PG1 is a carboxyl protecting group, which is converted into a compound of formula I, according to claim 1, b) a compound of formula I that has been prepared by process a) or a suitable precursor of formula I , which is produced due to its chemical structure in enantiomeric forms, which is fractionated by saline formation with enantiopure acids or bases, a chromatography in chiral stationary phases, or a derivatization using chiral enantiopure compounds as amino acids, a separation of the diastereomers obtained from this and the elimination of the chiral auxiliary groups to produce the pure enantiomers, or c) the compound of formula I prepared by processes a) or b) which is isolated in the free form or, in the case where acid groups are present or basic, it becomes the salts physiologically tolerated
8. 8. A medicament having an effective content in at least one compound of formula I according to one or more of claims 1 to 6, together with a pharmaceutically suitable and physiologically tolerated vehicle, additive and / or other active ingredients and excipients.
9. 9. The use of the compound of formula I according to one or more of claims 1 to 6, to produce a medicament for the prophylaxis and therapy of all disorders associated with thrombosis, embolisms, hypercoagulability or fibrotic changes.
10. 10. The use according to claim 9, which is applied to myocardial infarction, angina pectoris and other types of acute coronary syndrome, cerebrovascular accidents, peripheral vascular disorders, deep vein thrombosis, pulmonary embolism, embolic or thrombotic events caused by cardiac arrhythmias , cardiovascular events such as restenosis after revascularization, and angioplasty and similar procedures such as stent implants and bypass operations, or reducing the risk of thrombosis after surgical procedures such as in knee and hip joint operations, or disseminated intravascular coagulation , sepsis and other intravascular events that are associated with a inflammation, atherosclerosis, diabetes and the metabolic syndrome and its sequelae, tumor growth and tumor metastasis, haemostatic system deteriorations such as fibrin deposits, fibrotic changes of the lung such as chronic obstructive pulmonary disease, adult respiratory distress syndrome or fibrin deposits in the eye after ocular operations, or the prevention and / or treatment of the formation of eschar.