MXPA06008978A - Novel carboxamides for use as xa inhibitors - Google Patents

Abstract

The invention relates to the novel substituted carboxamides of general formula (I), wherein A, B and R1 to R5 are defined as in claim 1, the tautomers, enantiomers, diastereomers, mixtures and salts thereof, especially the physiologically salts thereof with inorganic or organic acids or bases, which have valuable properties. The inventive compounds have an antithrombotic effect and are factor Xa inhibitors.

Description

NEW AMIDES OF CARBOXYLIC ACIDS AS INHIBITORS OF THE XA FACTOR The subject of the present invention are novel substituted carboxylic acid amides of the general formula its tautomers, its enantiomers, its diastereomers, its mixtures and its salts, especially its physiologically compatible salts with inorganic or organic acids or bases which have valuable properties. The compounds of general formula I above, as well as their tautomers, their enantiomers, their diastereomers, their mixtures and their salts, especially their physiologically compatible salts with inorganic or organic acids or bases, and their stereoisomers have valuable pharmacological properties, especially an antithrombotic activity and an inhibiting activity of factor Xa. Thus, the object of the present application is the new compounds of general formula I above, their preparation, the medicaments containing pharmacologically active compounds, their preparation and use.

In the above general formula, in a first embodiment, A means a group of general formula wherein m represents the number 1 or 2, R6a independently represents a hydrogen, fluorine, chlorine or bromine atom or a C ?3 alkyl, hydroxy, amino, C ?3-amino alkyl, di (C C alkyl? -3) amino, aminocarbonyl, Ci_3-aminocarbonyl alkyl, di (C3-alkyl) aminocarbonyl or C? -3-carbonylamino alkyl and R6b can be independently a hydrogen atom, a C? -4 alkyl group, alkyl C ? 4-carbonyl, alkyl C? -oxycarbonyl or C? _3-sulfonyl alkyl, with the proviso that the heteroatoms optionally introduced as substituents in the above-mentioned 5 to 7-membered substituted groups A are not exactly separated by an carbon of another heteroatom, or a group of general formula wherein m represents the number 1 or 2, X1 represents an oxygen atom or a methylene group, -NR6b, carbonyl or sulfonyl, X2 represents an oxygen atom or a group -NR6b, X3 represents a methylene, carbonyl or sulfonyl, X4 represents an oxygen or sulfur atom, -NR6b or a carbonyl group, X5 represents a carbonyl or sulfonyl group, X6 represents an oxygen atom, -NR6b or a methylene group, X7 represents an oxygen or sulfur atom or a group -NR6b, X8 represents a methyl or carbonyl group, X9 represents -NR6b or a carbonyl group, X10 represents a sulfinyl or sulfonyl group and R6a independently represents a hydrogen, fluorine, chlorine or bromine atom or a C? alkyl group? _3, hydroxy, amino, alkyl C? _3-amino,. di (C C_3 alkyl) amino, aminocarbonyl, C C-3-aminocarbonyl alkyl, di (C C alkyl) 3) aminocarbonyl or C3_3-carbonylamino alkyl and R6b can independently be a hydrogen atom, a C? _ Alkyl group, C! _4-carbonyl alkyl, C?-Carbonyl alkoxy or C?-3-sulfonyl alkyl , with the proviso that the heteroatoms optionally introduced as substituents in the above-mentioned 5 to 7-membered substituted groups A are not exactly separated by a carbon atom of another heteroatom, R1 represents a hydrogen, fluorine, chlorine or bromine atom, a C? _3 alkyl group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, a C2_3 alkenyl group, C2_3 alkynyl, nitro, amino, C?-3 alkoxy, mono-, di- or trifluoromethoxy, R 2 represents a hydrogen atom, fluorine, chlorine or bromine, or a C 1 - alkyl group, R 3 represents a hydrogen atom, a C 2 - 3 alkenyl group or C 2 - 3 alkynyl or a straight or branched chain C 1 - 6 alkyl group in which Hydrogen atoms can they are totally or partially replaced by fluorine atoms, and that it is eventually substituted by a nitrile, hydroxy, C1-5 alkoxy group in which the hydrogen atoms can be totally or partially substituted by fluorine atoms, an allyloxy group, propargyloxy, benzyloxy, alkyl C? _5-carbonyloxy, alkyl C? -5-oxycarbonyloxy, carboxyalkyl C? _3-oxy, alkyl C? _5-oxycarbonylalkyl C? _3-oxy, alkyl C? _8-oxycarbonylamino, mercapto, C? -3-sulfa? nyl alkyl, C? _3-sulfinyl alkyl, C? -3 alkyl? sulfonyl, C C -3-carbonylamino alkyl, C ?3-sulphanyl alkyl, C? -3-carbonylaminoalkyl C?-3-sulfinyl alkyl, C 1-3 alkylcarbonylaminoalkyl C 3 -sulfonyl, carboxy, C alkyl; 3-oxycarbonyl, allyloxycarbonyl, propargyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, C 1 -C 3 -aminocarbonyl alkyl, di (C 1-3 alkyl) aminocarbonyl, C 3-6 cycloalkylene iminocarbonyl, aminosulfonyl, C 1 -C 3 alkyl aminosulfonyl, di (C 1 alkyl) _ 3) aminosulfonyl, C3_6-iminosulfonyl cycloalkylene, amino, C3_3-amino alkyl, di (C3_3 alkyl) amino, C1-5 alkylcarbonylamino, C3_3_sulfonylamino alkyl, N- (C1_3 alkyl) -3-sulfonyl) C alqu-3-amino alkyl, C3_6-carbonylamino cycloalkyl, aminocarbonylamino, C C _3-aminocarbonylamino alkyl, di (C 1-3 alkyl) aminocarbonylamino, a 4 to 7 membered cycloalkyleneiminocarbonylamino group, benzyloxycarbonylamino, phenylcarbonylamino or guanidino, a carboxy group, aminocarbonyl, C ?4-aminocarbonyl alkyl, C3_6-aminocarbonyl cycloalkyl, di (C ?_3 alkyl) aminocarbonyl, C ?4-carbonyl alkoxy, C4_5-iminocarbonyl cycloalkylene, a phenyl or heteroaryl group, phenylcarbonylalkyl C3_3, phenylalkyl C1-3 or heteroarylalkyl C3_3, which on the phenyl or heteroaryl radical is optionally substituted once or several times with fluorine, chlorine or bromine atoms, C1-3 alkyl, amino, alkyl C? 3-amino, di (C C_3 alkyl) amino, hydroxy, C?-4-oxy alkyl, mono-, di- or trifluoromethoxy, benzyloxy, carboxyalkyl C?-3-oxy, alkyl C ?3-oxycarbonylalkyl C ?- 3-oxy, aminocarbonylalkyl-C3-oxy, alkylC? _-AminocarbonylalkylC? 3-oxy, di (alkylC3-) aminocarbonylalkyl • C? -3-oxy, cycloalkyleneiminocarbonylalkoxyC? _3 from 4 to 7 members, carboxy, alkyl C? -3-oxycarbonyl or C? _3-oxycarbonylamino alkyl, a cycloalkyl, cycloalkyleneimino, cycloalkylalkyl C1-3 alkyl or cycloalkyleneiminoalkyl C? _3 group from 3 to 7 members, wherein in the cyclic part a methylene group may be substituted by an -NH group optionally substituted by a C3_3 alkyl group or C3_3_carbonyl alkyl or by an oxygen atom, and in which additionally one of the methylene groups contiguous to a group -NH, -N (C 1 -C 3 alkylcarbonyl) or -N (C 1-3 alkyl) can be respectively substituted with a carbonyl or sulfonyl group, with the proviso that a cycloalkyleneimino group is excluded as defined above in which two nitrogen atoms are separated from each other exactly by a -CH2- group, R4 represents a hydrogen atom or a C3_3 or R3 alkyl group and R4 together with the The carbon to which they are attached represent a C3_7 cycloalkyl group in which one of the methylene groups of the C3_ cycloalkyl group can be substituted by an imino group, C3_3-imino alkyl, acylimino or sulfonylimino, R5 represents a hydrogen atom or a C1-3 alkyl group, B represents a group of formula wherein n represents the number 1 or 2, R7 represents a hydrogen atom or a C? _3 alkyl group, hydroxy, C?-5-oxycarbonyl alkyl, C?-3 carboxyalkyl, C C-alkyl-3-oxycarbonylalkyl C1- alkyl 3, amino or C1-3alkylamino and R8 independently represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a C? Alquilo alkyl group in which the hydrogen atoms may be totally or partially substituted by atoms fluorine, a C2-3 alkenyl group or C2-3 alkynyl, hydroxy, C1-3 alkoxy, trifluoromethoxy, amino, nitro or nitrile, wherein, unless otherwise indicated, by the term "heteroaryl group" recited previously in the definitions is to be understood a 5- or 6-membered monocyclic heteroaryl group, wherein the 6-membered heteroaryl group contains one, two or three nitrogen atoms and the 5-membered heteroaryl group contains an imino group optionally substituted with a alkyl group C? _3, phenyl or phenylalkyl C1-3, an atom d oxygen or sulfur or an imino group optionally substituted with a C1-3 alkyl group, phenyl, C2_3 aminoalkyl, C3_3-aminoalkyl alkyl C2_3, di (C1-3 alkyl) C2_3 aminoalkyl, cycloalkyleneiminoalkyl C1-3 of 4 to 7 members or C3_3 phenyloalkyl, or an oxygen or sulfur atom and additionally a nitrogen atom or an imino group optionally substituted with a C1-3 alkyl group or C1-3 phenylalkyl and two or three atoms of nitrogen, and furthermore, in the above-mentioned monocyclic heteroaryl groups, a phenyl ring optionally substituted with a fluorine, chlorine or bromine atom, a C?-3 alkyl group, hydroxy, alkyl Ci may be condensed by two adjacent carbon atoms. -3-oxy, amino, alkyl C? -3-amino, di (C? _3 alkyl) amino or C3-6-imino cycloalkylene, and the bonding is carried out by a nitrogen atom or by a carbon atom of the part heterocyclic or a fused phenyl ring, in which the alkyl and alkoxy groups contained in the above-mentioned definitions having more than two carbon atoms, unless otherwise indicated, can be straight or branched chain, and the groups alkyl in the dialquila residues two previously mentioned, for example the dialkylamino groups, may be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups contained in the aforementioned definitions may be totally or partially substituted by fluorine atoms, their tautomers, its enantiomers, its diastereomers, its mixtures and its salts. Examples of monocyclic heteroaryl groups are pyridyl, N-oxypyridyl, pyrazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, [1, 2, 3] triazinyl, [1, 3, 5] triazinyl, [1, 2, 4] triazinyl, pyrrolyl, imidazolyl, [1, 2, 4] triazolyl, [1,2,3] triazolyl, tetrazolyl, furanyl, isoxazolyl, oxazolyl, [1, 2, 3] oxadiazolyl, [1, 2, 4] oxadiazolyl, furanyl, thiophenyl, thiazolyl, isothiazolyl / [1, 2, 3] thiadiazolyl, [1,2,4] thiadiazolyl or [1, 2, 5] thiadiazolyl. Examples of bicyclic heteroaryl groups are benzimidazolyl, benzofuranyl, benzo [c] furanyl, benzothiophenyl, benzo [c] thiophenyl, benzothiazolyl, benzo [c] -isothiazolyl, benzo [d] isothiazolyl, benzooxazolyl, benzo [c] isoxazolyl, benzo groups. [d] isoxazolyl, benzo [1,2,5] oxadiazolyl, benzo [1,2,5] thiadiazolyl, benzo [1,2,3] thia-diazolyl, benzo [] [1,2,3-triazinyl, benzo [1] , 2,4] triazinyl, benzotriazolyl, cinolinyl, quinolinyl, N-oxyquinolinyl, isoquinolinyl, quinazolinyl, N-oxyquinazolinyl, quinoxalinyl, phthalazinyl, indolyl, isoindolyl or l-oxa-2,3-diazaindenyl. Examples of the Ci-g alkyl groups mentioned above in the definitions are methyl, ethyl, 1-propyl, 2-propyl, n-butyl, sec-butyl, tert-butyl, 1-pentyl, 2-pentyl, 3- pentyl, neopentyl, 1-hexyl, 2-hexyl, 3-hexyl, 1-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, 1-octyl, 2-octyl, 3-octyl or 4-octyl. Examples of the C 8 -oxi alkyl groups mentioned above in the definitions are methyloxy groups, ethyloxy, 1-propyloxy, 2-propyloxy, n-butyloxy, sec-butyloxy, tert-butyloxy, 1-pentyloxy, 2-pentyloxy, 3-pentyloxy, neopentyloxy, 1-hexyloxy, 2-hexyloxy, 3-hexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, 4-heptyloxy, 1-octyloxy, 2-octyloxy, 3-octyloxy or 4-octyloxy. For a group transformable in vivo e? a carboxy group is to be understood as, for example, a carboxy group esterified with an alcohol, which in the alcoholic part is preferably a C? _6 alkanol, a C? _3 phenylalcanol, a C3-g cycloalkanol, a C5_7 cycloalkenol, a C3-5 alkenol , a C3-5 phenylalkenol, a C3-5 alkynol or a C5 phenylalquinolone, with the proviso that no bond to the oxygen atom of a carbon atom carrying a double or triple bond, a C3_8 alkanol cycloalkyl ? _3 or an alcohol of formula R9-C0-0- (R10CR1: L) -OH, wherein R9 represents a C? -8 alkyl group, C5-cycloalkyl, phenyl or phenyl-C1-3 alkyl, R10 represents a hydrogen, a C? -3 alkyl group, Cs- or phenyl cycloalkyl and R11 represents a hydrogen atom or a C? _3 alkyl group. Preferred in vivo cleavable residues of a carboxy group are a C6_6 alkoxy group such as the methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, n-pentyloxy, n-hexyloxy or cyclohexyloxy groups or a phenylalkoxy group C1-3 as the benzyloxy group. Those compounds of general formula I in which R3 contains a group transformable in vivo in a carboxy group represent prodrugs for those compounds of general formula I in which R3 contains a carboxy group. A second embodiment of the present invention comprises those compounds of general formula I in which A represents a group of general formula wherein m represents the number 1 or 2, R6a independently represents a hydrogen or fluorine atom, a C1-3 alkyl group, hydroxy, amino, C C -3-amino alkyl, di (C C3 alkyl) amino , aminocarbonyl, C C3-aminocarbonyl alkyl, di (C3-3 alkyl) aminocarbonyl or C1-3 alkylcarbonylamino and R6b may independently be a hydrogen atom, a C? alkyl group, C alqu alkyl alqu carbonyl, C4-4alkoxycarbonyl or C3-3alkylsulfonylcarbonyl, with the proviso that the heteroatoms optionally introduced as substituents in the substituted groups A of 5 to 7 members mentioned above are not exactly separated by one carbon atom of another heteroatom, or a group of general formula wherein m represents the number 1 or 2, X1 represents a methylene group, -NR6b, carbonyl or sulfonyl, X2 represents an oxygen atom or a group -NR6, X3 represents a methylene, carbonyl or sulfonyl group, X4 represents an atom of oxygen or sulfur, a group -NR6b or carbonyl, X5 represents a carbonyl or sulfonyl group, X8 represents a carbonyl group, X9 represents a carbonyl group, R6a independently represents a hydrogen or fluorine atom, a C3_3 alkyl group , hydroxy, amino, alkyl C3-amino, di (C3_3 alkyl) amino, aminocarbonyl, C3_3-aminocarbonyl alkyl, di (C3_3 alkyl) aminocarbonyl or C3_3-carbonylamino alkyl and R6b may independently be a carbon atom. hydrogen, a C? _ _4 alkyl, C? -4-carbonyl, C alco-carbonyl or C?-3-sulfonyl alkoxy, with the proviso that heteroatoms optionally introduced as substituents on the substituted cyclic A groups from 5 to 7 members mentioned above are not separated by exactly one carbon atom of another heteroatom, R1 represents a hydrogen, fluorine, chlorine or bromine atom, a C3_3 alkyl group in which the hydrogen atoms may be total or partially substituted with fluorine atoms, a C2-3 alkenyl group, C2_3 alkynyl, nitro, amino, C1-3 alkoxy, mono-, di- or trifluoromethoxy, R2 represents a hydrogen, fluorine, chlorine or bromine atom or an alkyl group C? _3, R3 represents a C2_3 alkenyl or C2_3 alkynyl group or a group straight or branched chain C? _6alkyl in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, and which is optionally substituted with a nitrile, hydroxy, a C 1-5 -alkyl group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, an allyloxy, propargyloxy, benzyloxy, - C 1 -C 5 alkylcarbonyloxy, C 3 -5-oxycarbonyloxy, carboxyalkyl C 3 -oxi, alkyl C alkyl group; -5-oxycarbonylalkyl C? _3-oxy, alkyl C? -8-oxycarbonylamino, mercapto, alkyl C? _3-sulfañilo, alkyl C? _3-sulfinilo, alquil C? -3-sulfonyl, C? -3-alkylcarbonylaminoalkylC? -3-sulfanyl alkyl, C? -3-carbonylaminoalkylC? _3-sulfinyl alkyl, C1-3alkylcarbonylaminoalkylC? -3-sulfonyl, carboxy, alkyl C1-3-oxycarbonyl, allyloxycarbonyl, propargyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, C, -C3-aminocarbonyl alkyl, di (C1-3 alkyl) aminocarbonyl, C3-6-iminocarbonyl cycloalkylene, aminosulfonyl, C3_3-aminosulfonyl alkyl, di (alkyl) C? _ 3) aminosulfonyl, C3-6-iminosulfonyl cycloalkylene, amino, C? -3-amino alkyl, di (C1-3 alkyl) amino, C1-5 alkylcarbonylamino, C? -3-sulfonylamino alkyl, N- (C 1-3 alkylsulfonyl) alkyl C 3 -amino, C 3-6 -carbonylamino cycloalkyl, aminocarbonylamino, C 1 -C 3 -aminocarbonylamino alkyl, di (C 3 -C 3 alkyl) aminocarbonylamino, a 4 to 7 membered cycloalkyleneiminocarbonylamino group, benzyloxycarbonylamino, phenylcarbonylamino or guanidino, a carboxy group, aminocarbonyl, C 1 _4-aminocarbonyl alkyl, C 3-6 cycloalkyl-aminocarbonyl, di (C 1 -C 3 alkyl) aminocarbonyl, C 4 alkoxy -carbonyl, C4-6-cycloalkylene iminocarbonyl, a phenyl or heteroaryl group, phenylcarbonylalkyl C1-3 alkyl, phenylalkyl C1-3 or heteroarylalkylC3_3, which in the phenyl or heteroaryl part is optionally substituted once or several times with fluorine atoms, chlorine or bromine or C? _3 / amino alkyl, C ?3-amino alkyl, di (C1-3 alkyl) amino, hydroxy, C! _-4-oxy, mono-, di- or trifluoromethoxy, benzyloxy, carboxyalkyl C grupos alkyl groups 3-or i-, C 1 -C 3 alkylcarbonylalkyl C 3 -oxi, C 1 -3-oxy aminocarbonylalkyl, C 1 -C 3 alkylaminocarbonyalkyl 3-oxy, di (C 1-3 alkyl) aminocarbonylalkyl C 1 alkyl 3-Oxy, 3- to 7-membered C1-3-cycloalkyleneiminocarbonylalkoxy, carboxy, C?-3-oxycarbonyl or C?-3-oxycarbonylamino, a cycloalkyl group chyl, cycloalkyleneimino, cycloalkylalkylC1-3alkyl or cycloalkyleneiminoalkylC3-3 of 3 to 7 members, wherein in the cyclic part a methylene group can optionally be substituted by an -NH group substituted with a C1-3alkyl group or alkylC? -3-carbonyl or by an oxygen atom, and in which additionally a methylene group contiguous to a group -NH, -N (C 1 -C 3 alkylcarbonyl) or -N (C 1-3 alkyl) can be respectively substituted with a carbonyl or sulfonyl group, with the proviso that a cycloalkyleneimino group defined as above is excluded in which two nitrogen atoms are separated from each other exactly by a group -CH 2 -, R 4 represents a hydrogen atom or an alkyl group C ? _3, R5 represents a hydrogen atom or a C1-3 alkyl group, B represents a group of formula wherein n represents the number 1 or 2, R7 represents a hydrogen atom, a C3_3 alkyl group, hydroxy, C5_5-oxycarbonyl alkyl, C3_3 carboxyalkyl, C3_3 alkylcarbonylalkyl_3alkyl , amino or C C3-amino alkyl and R8 independently represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a C ?3 alkyl group in which the hydrogen atoms can be totally or partially substituted by carbon atoms. fluorine, a C2-3 alkenyl group or C2_3 alkynyl, a hydroxy group, C3_3 alkoxy, trifluoromethoxy, amino, nitro or nitrile, wherein, unless otherwise indicated, by the term cited in the above definitions " "heteroaryl group", is to be understood a 5- or 6-membered monocyclic heteroaryl group, in which the 6-membered heteroaryl group contains one, two or three nitrogen atoms and the 5-membered heteroaryl group contains an imino group optionally substituted with a alkyl group C? _3, phenyl or phenylalkyl C? _3, a oxygen atom or a sulfur atom or an imino group optionally substituted with an alkyl group Ca-3 / phenyl, aminoalkyl C2_3, alkyl C? _3 ~ aminoalkyl C2_3, di (C1-3alkyl) aminoalkyl C2_3, a cycloalkyleneiminoalkyl group C1-3 of 4 to 7 members or phenylalkyl C? -3 or an oxygen atom or sulfur atom, and additionally a nitrogen atom, or an imino group optionally substituted with a C1-3 alkyl group or phenylalkyl C1-3 and two or three nitrogen atoms, and furthermore, in the monocyclic heteroaryl groups mentioned above, a phenyl ring optionally substituted with one atom may be condensed by two adjacent carbon atoms of fluorine, chlorine or bromine, a C1-3 alkyl group, hydroxy, C C-3-oxy, amino, C?-3-amino alkyl, di (C1-3 alkyl) amino or C3_6-imino cycloalkylene, and the The connection is carried out by means of a nitrogen atom or by a carbon atom of the heterocyclic part or of a fused phenyl ring, in which the alkyl and alkoxy groups contained in the aforementioned definitions having more than two carbon atoms, unless what else is indicated , they can be straight or branched chain, and the alkyl groups in the above-mentioned dialkylated radicals, for example the dialkylamino groups, can be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups contained in the definitions cited above may be fully or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.

A third embodiment of the present invention encompasses those compounds of general formula I in which A means a group of general formula wherein m means the number 1 or 2, R6 independently represents a hydrogen or fluorine atom, a C? _3 alkyl, hydroxy, amino, alkyl group C3-amino, di (C1-3alkyl) amino, aminocarbonyl, C3_3-aminocarbonyl alkyl, di (C3-alkyl) aminocarbonyl or C3_3-carbonylamino alkyl, and R6b can be independently an atom of hydrogen, a C? _ alkyl, C alqu-4-alkylcarbonyl, C? _4-carbonyl or C?-3-sulfonyl alkoxy group, with the proviso that the heteroatoms optionally introduced as substituents in the substituted A groups of 5 to 7 members mentioned above are not exactly linked by a carbon atom with another heteroatom, or a group of general formula wherein m means the number 1 or 2, X 1 means a methylene group, -NR 6b, carbonyl or sulfonyl, X 2 means an oxygen group or -NR 6b, X 3 means a methylene, carbonyl or sulfonyl group, X 4 means an oxygen atom or sulfur or a group -NR6b, X5 means a carbonyl or sulfonyl group, R6a independently represents a hydrogen or fluorine atom, a C3_3 / hydroxy, amino, C3_3-amino alkyl, di (C1- alkyl) alkyl group 3) amino, aminocarbonyl, C1-3alkylaminocarbonyl, di (C1_3alkylamino) aminocarbonyl or C1-3alkylaminocarbonyland R6b can be independently of one another a hydrogen atom, a C? _4 alkyl group, C C _4 carbonyl alkyl, C_-carbonyl alkoxy or C?-3-sulfonyl alkyl, with the proviso that heteroatoms possibly introduced as substituents in the above-mentioned 5 to 7 membered substituted cyclic groups are not exactly separated by a carbon atom of another heteroatom, R1 may be a fluorine, chlorine or bromine atom, a C1-3 alkyl group in which the Hydrogen can be totally or partially substituted by fluorine atoms, a nitro group, C? _3 alkoxy, a mono-, di- or trifluoromethoxy group, R2 represents a hydrogen atom, R3 represents a straight chain C? _6 alkyl group or in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, and which is optionally substituted with a nitrile, hydroxy, benzyloxy, alkyl C5-5-oxy group in which the hydrogen atoms they can not be totally or partially replaced by fluorine atoms, an allyloxy group, C5_5-carbonyloxy alkyl, C5_5-oxycarbonyloxy alkyl, C3_3-oxy carboxyalkyl, C5_5 alkyl-oxycarbonylalkyl C3_3-oxy, alkyl Ci-s-oxycarboniTamino, C?-3-sulfañilo alkyl, C ?3-sulfonyl alkyl, carboxy, C C _3-oxycarbonyl alkyl, C?-3-aminocarbonyl alkyl, di (C 1-3 alkyl) aminocarbonyl, C3 cycloalkylene 6-iminocarbonyl, aminocarbonylamino, C3_3-aminocarbonylamino alkyl or di (C3_3) aminocarbonylamino alkyl, an aminocarbonyl group, C4_4-aminocarbonyl alkyl, C3_6-aminocarbonyl cycloalkyl or di (C1-3 alkyl) aminocarbonyl, a phenyl group or heteroaryl, phenylalkyl C1-3 or heteroarylalkyl C3_3 which is optionally substituted on the phenyl or heteroaryl part one or more times with fluorine, chlorine or bromine atoms, C?--3 alkyl, amino, C C1-.3- alkyl groups to ino, di (C3_3 alkyl) amino, hydroxy, C4_4-oxy, alkyl, mono-, di- or trifluoromethoxy, carboxy or C3_3-oxycarbonyl alkyl, a group C 3 to 7-membered icloalkyl in which a methylene group can be substituted in the cyclic part with an -NH group optionally substituted by a C 1-3 alkyl group or C 1 -C 3 alkylcarbonyl or an oxygen atom, R 4 represents a hydrogen atom, R5 represents a hydrogen atom, B represents a group of formula wherein n represents the number 1, R7 represents a hydrogen atom, and R8 represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a methyl group, C2_3 alkynyl or methoxy, in which the hydrogen atoms may be totally or partially substituted by fluorine atoms, in which, unless otherwise indicated, by the term quoted above in the definitions "heteroaryl group", it is to be understood a 5- or 6-membered monocyclic heterocyclic group in which the 6-membered heterocyclic group contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C? _3 alkyl group / an oxygen atom or a sulfur atom, or an imino group optionally substituted with a C1-3 alkyl group, or an oxygen atom or a sulfur atom, and additionally a nitrogen atom, or an imino group optionally substituted with a C3_3 alkyl group and two or three atom s of nitrogen, and the bonding is carried out by a nitrogen atom or by a carbon atom, in which the alkyl and alkoxy groups contained in the aforementioned definitions having more than two carbon atoms, unless otherwise indicated they can be straight or branched chain and the alkyl groups in the dialkylated moieties mentioned above, for example the dialkylamino groups, can be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups contained in the The aforementioned definitions can be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts. A fourth embodiment of the present invention encompasses those compounds of general formula I in which A, R1, R2, R4, R5 and B are defined as described in the third embodiment, and R3 represents a C6-chain alkyl group linear or branched in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, which is optionally substituted with a nitrile, hydroxy, benzyloxy group, a C 5 5 -oxi alkyl group in which the hydrogen atoms may be to be totally or partially substituted by fluorine atoms, an allyloxy group, C ?5-carbonyloxy alkyl, C ?s-oxycarbonyloxy alkyl, C?-3-oxy carboxyalkyl, C C _5alkyloxycarbonylalkyl C ?3-oxy, alkyl C ? 8-oxycarbonylamino, C 1 _ 3 -sulfanyl alkyl, C 3 _ -sulfonyl alkyl, carboxy, C 1-3 alkyloxycarbonyl, C 1 -3-aminocarbonyl alkyl, di (C 1 -C 3 alkyl) aminocarbonyl, C 3 6 -cyclohexylene iminocarbonyl, aminocarbonylamino , alkyl C? -3-aminocarbonylamino or di (C? -3) aminocarbonylamino, a aminocarbonyl group, C 1 -4-aminocarbonyl alkyl, C 3-6 cycloalkyl-aminocarbonyl or di (C 1 -C 3 alkyl) aminocarbonyl group, wherein the alkyl and alkoxy groups contained in the above-mentioned definitions having more than two carbon atoms, unless indicated otherwise, they may be straight or branched chain, and wherein the alkyl groups in the dialkylated moieties mentioned above, for example the dialkylamino groups, may be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions can be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts. A fifth embodiment of the present invention encompasses those compounds of general formula I in which. A, R1, R2, R4, R5 and B are defined as described in the third embodiment, and R3 represents a phenyl or heteroaryl group, phenylalkyl C3_3 or heteroarylalkyl C3_3 which in the phenyl or heteroaryl part is optionally substituted or several times with fluorine, chlorine or bromine atoms, C? _3 alkyl, amino, C alqu-3-amino alkyl, di (C C _3) alkyl amino, hydroxy, C C ~-oxy-, mono-, di- or trifluoromethoxy, carboxy or C3_3-oxycarbonyl alkyl, a cycloalkyl group of 3 to 7 members, wherein a methylene group in the cyclic part can be substituted by an -NH group optionally substituted with a C1-3 alkyl group or C3_3-carbonyl alkyl, or by an oxygen atom, in which, unless to be indicated otherwise, by the term cited in the above definitions "heteroaryl group", is meant a 5- or 6-membered monocyclic heteroaryl group in which the 6-membered heteroaryl group contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C? -3 alkyl group, an oxygen atom or a sulfur atom, or an imino group optionally substituted with a C? _3 alkyl group or an oxygen atom or a sulfur atom and additionally a nitrogen atom, or an imino group optionally substituted with a C? _3 alkyl group and two or three nitrogen atoms, and the bonding is carried out by a nitrogen atom or a carbon atom, in the that the Alkyl and alkoxy groups contained in the aforementioned definitions having more than two carbon atoms, unless otherwise indicated, may be straight or branched chain, and the alkyl groups in the dialkylated moieties mentioned above, for example the groups dialkylamino, can be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions can be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and its salts. A sixth embodiment of the present invention encompasses those compounds of general formula I in which wherein m represents the number 1 or 2, R6a independently represents a hydrogen or fluorine atom or a C? -3 alkyl group, and R6b can be a hydrogen atom or an alkyl group C? -3, with the proviso that the heteroatoms optionally introduced as substituents in the above-mentioned 5 to 7-membered substituted groups A are not exactly separated by a carbon atom of another heteroatom, or wherein m represents the number 1 or 2, X1 represents a methylene group, -NR6b, carbonyl or sulfonyl, X2 represents an oxygen atom or a group -NR6b, X3 represents a methylene, carbonyl or sulfonyl group, X4 represents an atom of oxygen or a sulfur atom or a group -NR5b, X5 represents a carbonyl group or a sulfonyl group, R6a independently represents a hydrogen or fluorine atom or a C1-3 alkyl group, and R6b may independently be a hydrogen atom or a C? _3 alkyl group, with the proviso that the heteroatoms introduced as substituents in the 5- to 7-membered cyclic A groups mentioned above are not exactly separated by a carbon atom of another hetero atom, R 1 represents an atom of chlorine or bromine, a methyl or methoxy group in which the hydrogen atoms may be totally or partially substituted by fluorine atoms, or a nitro group, R2 represents a hydrogen atom or, R3 represents a straight or branched chain C?-alkyl group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, and which is optionally substituted with a hydroxy group, an alkyl C C -4 group -oxi in which the hydrogen atoms may be fully or partially substituted with fluorine atoms, a C alqu-3-sulfañyl alkyl group, C?-3-sulfonyl alkyl, carboxy or C 1-3 alkyl-oxycarbonyl, a phenyl group or heteroaryl, phenylalkyl C3_3 or heteroarylalkyl C3_3, which in the phenyl or heteroaryl part is optionally substituted once or several times with fluorine, chlorine or bromine atoms, C1-3 alkyl groups, C3-4alkyloxy, mono-, di- or trifluoromethoxy, carboxy or C 1 -3-oxycarbonyl alkyl, R 4 represents a hydrogen atom, R 5 represents a hydrogen atom, and B represents a group of formula wherein n represents the number 1, R7 represents a hydrogen atom, and R8 represents a chlorine or bromine atom or the ethynyl group, wherein, unless otherwise indicated, by the term cited in the definitions above "heteroaryl group", is to be understood a 5- or 6-membered monocyclic heteroaryl group, wherein the 6-membered heteroaryl group contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C ?_3 alkyl group, or an oxygen atom or a sulfur atom, or an imino group optionally substituted with a C ?_3 alkyl group or an oxygen atom or a sulfur atom and additionally a nitrogen atom, or an imino group optionally substituted by a C3_3 alkyl group and two or three nitrogen atoms, and the bonding is carried out by a nitrogen atom or by a carbon atom, in which the alkyl and alkoxy groups contained in the above-cited definitions having more than two carbon atoms, unless otherwise indicated, may be straight or branched chain, and wherein the alkyl groups in the dialkylated moieties mentioned above, for example the dialkylamino groups, may they are the same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions can be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts. A seventh embodiment of the present invention encompasses those compounds of general formula I wherein A, R1, R2, R4, R5 and B are defined as described in the sixth embodiment, and R3 is a straight or branched chain C? ~ 4 alkyl group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, and which is optionally substituted by a hydroxy group, a C alqu _4 alkyl group -oxi in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, a C alqu _3-sulfanyl alkyl group, C? _3-sulfonyl alkyl, carboxy or C? _3-oxycarbonyl alkyl, in which the groups alkyl and alkoxy contained in the aforementioned definitions having more than two carbon atoms, unless otherwise indicated, may be straight or branched chain, and wherein the alkyl groups in the dialkylated moieties mentioned above, for example the dialkylamino groups can be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions can be totally or partially substituted by fluorine atoms, their taut monomers, their enantiomers, their diastereomers, their mixtures and their salts. An eighth embodiment of the present invention encompasses those compounds of general formula I wherein A, R1, R2, R4, R5 and B are defined as described in the sixth embodiment and R3 is a phenyl or heteroaryl group, phenylalkyl C? _3 or heteroaryl which on the phenyl or heteroaryl part is optionally substituted once or several times with fluorine, chlorine or bromine atoms, C? _3 alkyl groups, C C _4-oxy, ono-, di- or trifluoromethoxy-, carboxy-, alkyl-, or C C-3-oxycarbonyl alkyl, a 3- to 7-membered cycloalkyl group in which in the cyclic part a methylene group can be substituted by a group, NH optionally substituted with a C? _3 alkyl group or C C _ alkyl carbonyl, or by an oxygen atom, in which, unless otherwise indicated, by the term cited in the above definitions "heteroaryl group", it is to be understood a 5 or 6 membered monocyclic heteroaryl group, wherein the 6-membered heteroaryl group contains one, two or three nitrite atoms Oxygen, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C 1 -C 3 alkyl group, an oxygen atom or a sulfur atom or an imino group optionally substituted with a C 1 -C 3 alkyl group or an oxygen atom or sulfur and additionally a nitrogen atom or an imino group optionally substituted with a C? _3 alkyl group and two or three nitrogen atoms, and the bonding is carried out by a nitrogen atom or by a carbon atom, in which the groups alkyl contained in the aforementioned definitions having more than two carbon atoms, unless otherwise indicated, can be straight or branched chain, and wherein the alkyl groups in the dialkylated moieties mentioned above, for example the groups dialkylamino, they may be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions may be wholly or partly substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts. A ninth embodiment of the present invention encompasses those compounds of general formula I in which A represents a group of formula where m means the number 1 or 2, R6a independently represents a hydrogen atom or a fluorine atom or a C3_3 alkyl group, with the proviso that the fluorine atoms introduced as substituents in the cyclic groups A substituted from 5 to 7 members mentioned above are not separated directly by a carbon atom of another heteroatom, R1 means a chlorine or bromine atom, a methyl or methoxy group in which the hydrogen atoms may be fully or partially substituted, or a nitro group, R 2 signifies a hydrogen atom, R 3 signifies a straight or branched chain C 1 _ 4 alkyl group in which the hydrogen atoms may be totally or partially substituted by fluorine atoms, and which is optionally substituted with a group hydroxy, C C _-4-oxy alkyl in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, a C alqu-3-sulfanyl alkyl group, alkyl C 3 -sulfonyl, carboxy or C 1 3 -carbonyl alkoxy, a furanyl, thiophenyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridinyl C 1 -C 2 or imidazolylalkyl C 2 -2 group, which may be optionally substituted on the heteroaryl part with one or two C? _3 alkyl, C C-3-oxy, carboxy or C?-3-oxycarbonyl alkyl groups, and R 4 represents a hydrogen atom, R 5 represents a hydrogen atom, hydrogen and B represents a group of formula wherein n represents the number 1, R7 represents a hydrogen atom and R8 represents a chlorine or bromine atom or an ethynyl group, in which, unless otherwise indicated, by the term quoted in the above definitions " "heteroaryl group", is to be understood a 5- or 6-membered monocyclic heteroaryl group, in which the 6-membered heteroaryl group contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C? _3 alkyl group, an oxygen atom or a sulfur atom or an imino group optionally substituted with a C? _3 alkyl group or an oxygen or sulfur atom and additionally a nitrogen atom, or an imino group optionally substituted with a C? _3 alkyl group and two or three nitrogen atoms, and the bonding is carried out by a nitrogen atom or by a carbon atom, in which the alkyl groups contained in the above definitions Cited entities having more than two carbon atoms, unless otherwise indicated, may be straight or branched chain, and wherein the alkyl groups in the dialkylated moieties mentioned above, for example dialkylamino groups, may be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions can be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts. A tenth embodiment of the present invention encompasses those compounds of general formula I wherein A, R 1, R 2, R 4, R 5 and B are defined as described in the ninth embodiment, and R 3 is a straight chain C 1 -C alkyl group or branched in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, and which is optionally substituted with a hydroxy group, C 1 _ 4 -oxi alkyl in which the hydrogen atoms may be totally or partially substituted by fluorine atoms, a C alqu-3-sulfanyl alkyl group, C ^-sulphonyl alkyl, carboxy or C ?3-oxycarbonyl alkyl, in which the alkyl and alkoxy groups contained in the aforementioned definitions having more than two carbon atoms carbon, unless otherwise indicated, may be straight or branched chain, and wherein the alkyl groups in the dialkylated moieties mentioned above, for example the dialkylamino groups, may be the same or different, and wherein the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions may be fully or partially substituted by fluorine atoms, its tautomers, its enantiomers, its diastereomers, its mixtures and its salts. An eleventh embodiment of the present invention encompasses those compounds of general formula I wherein A, R1, R2, R4, R5 and B are defined as described in the ninth embodiment and a furanyl, thiophenyl, pyrrolyl, pyrazolyl, imidazolyl group, oxazolyl, isoxazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridinylalkyl C? _2 or imidazolylalkyl C? _2, which optionally in the heteroaryl part can be substituted with one or two C? _3 alkyl groups in which the hydrogen atoms can be total or partially substituted by fluorine atoms, C? _3-oxy groups in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, carboxy groups or Ci-3-oxycarbonyl alkyl, and in which, unless to be indicated otherwise, by the term cited in the above definitions "heteroaryl group", is meant a 5- or 6-membered monocyclic heteroaryl group, wherein the 6-membered heteroaryl group It has one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C? _3 alkyl group, an oxygen atom or a sulfur atom, or an imino group optionally substituted with a group C 1-3 alkyl or an oxygen atom or a sulfur atom and additionally a nitrogen atom, or an imino group optionally substituted with a C 1-3 alkyl group and two or three nitrogen atoms, and the bonding is carried out by an atom of nitrogen or by a carbon atom, in which the alkyl groups contained in the aforementioned definitions having more than two carbon atoms, unless otherwise indicated, may be straight or branched chain, and wherein the alkyl groups in the dialkylated radicals mentioned above, for example the dialkylamino groups, can be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in Previous definitions may be totally or partially replaced by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts. A twelfth embodiment of the present invention encompasses those compounds of general formula I corresponding to embodiments 1, 2, 3, 4, 5, 6, 7 and 8, in which the group X 1 represents a methylene group. A thirteenth embodiment of the present invention encompasses those compounds of formula "• general I corresponding to embodiments 1, 2, 3, 4, 5, 6, 7 and 8, in which the group X1 represents a carbonyl group. of the present invention encompasses those compounds of general formula I corresponding to embodiments 1, 2, 3, 4, 5, 6, 7, 8, 12 and 13, in which the group X3 represents a methylene group. A fifteenth embodiment of the present invention encompasses those compounds of general formula I corresponding to modalities 1, 2, 3, 4, 5, 6, 7, 8, 12 and 13 in which the group X3 represents a carbonyl group. A sixteenth embodiment of the present invention encompasses those compounds of general formula I corresponding to embodiments 1, 2, 3, 4, 5, 6, 7, 8, 12, 13, 14 and 15, in which group X4 represents a oxygen atom. A seventeenth embodiment of the present invention encompasses those compounds of general formula I corresponding to modalities 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 and 16, in which the rest B means the group A eighteenth embodiment of the present invention encompasses those compounds of general formula I corresponding to modalities 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 and 16, where the rest B means the group A nineteenth embodiment of the present invention encompasses those compounds of general formula I corresponding to modalities 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 and 16, in which the rest B means the group A twentieth embodiment of the present invention encompasses those compounds of general formula I corresponding to modalities 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19, in which the radical R8 represents a chlorine atom. A twenty-first embodiment of the present invention encompasses those compounds of general formula I corresponding to the modalities .1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19, in which the radical R8 represents a bromine atom. A twenty-second embodiment of the present invention encompasses those compounds of general formula I corresponding to modalities 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16 , 17, 18 and 19, in which # the rest R8 represents an ethynyl group. A twenty-third embodiment of the present invention encompasses those compounds of general formula I corresponding to modalities 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16 , 17, 18, 19, 20, 21 and 22, corresponding to the general formula (la) The following preferred compounds of general formula I are mentioned, for example: (1) 3-Chloro-N- [(lS) -l- (5-chloro-lH-benzimidazol-2-yl) ethyl] -4- ([1,4] diazepan-1-yl) benzamide, (2) 4- (4-N-Boc-piperazin-1-yl) -N- [(1S) -1- (5-chloro-1-ji-benzimidazole -2-yl) ethyl] -3-trifluoromethylbenzamide, (3) N- [(SS) -1- (5-Chloro-lH-benzimidazol-2-yl) ethyl] -4- (piperazin-1-yl) - 3-trifluoro-methylbenzamide, (4) N- [(IR) -1- (5-Chloro-1H-benzimidazol-2-yl) -2-methoxyethyl) -4- (piperazin-1-yl) -3-trifluoromethylbenzamide , (5) 4- (4-N-Acetylpiperazin-1-yl) -N- [(15) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -3-trifluoromethylbenzamide, (6) 4- (Azepan-2-on-l-yl) -N- [(1S) -1- (5-chloro-lff-benzimidazol-2-yl) ethyl] -3-methylbenzamide, (7) 4- (Azepan -2-on-l-il) -N- [(1)) -l- (5-chloro-l, l -benzimidazol-2-yl) -2-methoxyethyl] -3-methylbenzamide, (8) 4- ( Azepan-2-on-1-yl) -N- [(li?) -1- (5-chloro-lH-benzimidazol-2-yl) -2-hydroxyethyl] -3-methylbenzamide, (9) N- [ (ÍS) -1- (5-Chloro-lH-benzimid azol-2-yl) ethyl] -4- (pyrrolidin-2-on-l-yl) benzamide, (10) N- [(SS) -1- (5-Chloro-lH-benzimidazol-2-yl) ethyl) ] -3-methyl-4- (pyrrolidin-2-on-l-yl) benzamide, (11) N- [(SS) -1- (5-Chloro-lH-benzimidazol-2-yl) -3-methylsulfanylpropyl ] -3-methyl-4- (pyrrolidin-2-on-l-yl) benzamide, (12) 3-Chloro-N- [(SS) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -4- (4-N-methyl [1,4] diazepan-1-yl) benzamide, (13) 3-Chloro-N- [(SS) -1- (5-chloro-li? -benzimidazole- 2-yl) ethyl] -4- (2-methylpyrrolidin-1-yl) benzamide, (14) N- [(15) -1- (5-Chloro-1-benzimidazol-2-yl) ethyl] -3- chloro-4- (morpholin-1-yl) benzamide, (15) N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) ethyl] -3,5-difluoro-4- ( morpholin-1-yl) benzamide, (16) N- [(IR) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -3-trifluoromethyl-4- (morpholin-1 -il) benzamide(17) 4- (Azepan-1-yl) -N- [(SS) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -3-trifluoromethylbenzamide, (18) 4- (Azepan -1-yl) -3-chloro-N- [(15) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] benzamide, (19) 3-Chloro-N- [(SS) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -4- (piperidin-1-yl) benzamide, (20) 3-Chloro-N- [(1S) -1- (5-chloro -lB-benzimidazol-2-yl) ethyl] -4- ([1,4] oxazepan-4-yl) benzamide, (21) N- [(IR) -1- (5-Chloro-li? -benzimidazole- 2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4-yl) -3-trifluoromethylbenzamide, (22) N- [(li?) - l- (5-chloro-li-benzimidazole- 2-yl) -2-methoxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (23) N- [(1S) -1- (5-Chloro-l, 7-benzimidazole- 2-yl) -3-methylsulfanylpropyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (24) N- [(li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-hydroxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide,. (25) 4- (Azepan-2-on-1-yl) -3-chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] benzamide , (26) 4- (Azepan-2-on-l-yl) -N- [(li?) -1- (5-chloro-lif-benzimidazol-2-yl) -2-methoxyethyl] -3-trifluoromethylbenzamide , (27) N- [(lS) -l ~ (5-Chloro-l-benzimidazol-2-yl) ethyl] -4- (morpholin-3-on-4-yl) benzamide, (28) N- [(1S) -1- (5-Chloro-l-benzimidazol-2-yl) ethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (29) N- [(Í) ) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -4- (morpholin-3-on-4-yl) benzamide, (30) N- [(15) -1- (5 Chloro-lH-benzimidazol-2-yl) ethyl] -3-methyl-4- (piperazin-1-yl) benzamide, (31) N- [(SS) -1- (5-chloro-L-benzimidazole- 2-yl) ethyl] -3-methyl-4- (piperazin-2-on-l-yl) benzamide, (32) N- [(lS) -l- (5-Chloro-lH-benzimidazol-2-yl ) ethyl] -3-methyl-4- (piperidin-2-on-l-yl) benzamide, (33) N- [(1S) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl) ] -4- (N-Methylpiperazin-1-yl) -3-trifluoromethylbenzamide, (34) N- [(lS) -l- (5-Chloro-l-benzimidazol-2-yl) -3-methylsulfonylpropyl il] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (35) N- [(15) -1- (5-chloro-li-benzimidazol-2-yl) -3- methylsulfanylpropyl] -4- (pyrrolidin-2-on-l-yl) benzamide, (36) N- [1- (5-Chloro-lE-benzimidazol-2-yl) -1-phenylmethyl] -4- (pyrrolidin- 2-on-1-yl) benzamide, (37) N- [(15) -l- (5-Chloro-1-benzimidazol-2-yl) ethyl] -4- (3, 5-dimethylpiperidin-1-yl) ) benzamide, (38) 3-Chloro-N- [(SS) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- (3,4-dideshydropiperidin-1-yl) benzamide , (39) N- [(SS) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -3-methyl-4- ([1, 3] oxazepan-2-on-3- il) benzamide (40) N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) -3-methylsulfanylpropyl) -4- (piperazin-1-yl) -3-trifluoromethylbenzamide, (41 ) N- [(SS) -1- (5-Chloro-1-benzimidazol-2-yl) -3-methylsulfanylpropyl] -4- (morpholin-3-on-4-yl) -3-nitrobenzamide, (42) 3-Chloro-N- [(SS) -1- (5-chloro-li-benzimidazol-2-yl) ethyl] -4- (tetrahydro-pyrimidin-2-on-l-yl) benzamide, ( 43) N- [(li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- ([1,3] oxazepan-2-on- 3-yl) benzamide, (44) 3-Chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- ([1,4] oxazepan-5-on-4-yl) benzamide, (45) 3-Chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- ([1,4] oxazepan-3-on-4-yl) benzamide, (46) 3-Chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2 -methoxyethyl] -4- (piperidin-2-on-l-yl) benzamide, (47) N- [(li?) - l- (5-Bromo-lH-benzimidazol-2-yl) -2-hydroxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (48) N- [(1S) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -4 - (1,1-dioxoisothiazolidin-2-yl) -3-methylbenzamide, (49) N- [1- (5-Chloro-1-yl-indol-2-yl) ethyl] -3-methyl-4- (morpholino- 3-on-4-yl) benzamide, (50) 3-Chloro-N- [(15) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -4- [2- (4- methylpiperazin-l-ylmethyl) pip eridin-1-yl) benzamide, (51) N- [(lS) -l- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -3-methyl-4- (oxazolidin-2-on- 3-yl) benzamide, (52) 3-Chloro-N- [(SS) -1- (5-chloro-lff-benzimidazol-2-yl) ethyl] -4- (morpholin-3-on-4-yl) ) benzamide, (53) N- [(li, 2S) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxypropyl] -3-methyl-4- (morpholine-3-on- 4-yl) benzamide, (54) N- [(SS) -1- (5-Chloro-l-benzimidazol-2-yl) ethyl] -4- (3,5-dimethylpiperidin-1-yl) benzamide, ( 55) N- [(SS) -1- (5-Chloro-1-benzimidazol-2-yl) ethyl] -3-methyl-4- (thiomorpholin-3-on-4-yl) benzamide, (56) N - [(li?) - l- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (piperidin-2-on-l-yl) benzamide, (57 ) N- [(15) -1- (5-Chloro-l # -benzimidazol-2-yl) ethyl] -3-methyl-4- ([1, 3] oxazinan-2-on-3-yl) benzamide , (58) N- [(li?) - l- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- ([1,3] -oxazinan-2 -on-3-yl) benzamide, (59) N- [(li?) -1- (5-Chloro-l-2-benzimidazol-2-yl) -2-methoxyethyl] -4- (piperidin-2-on- l-il) -3-trifluoromethyl lbenzamide, (60) N- [(li?) - l- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (1, 1-dioxo [1,2] thiazinan-2-yl) -3-methylbenzamide, (61) N- [(lS) -l- (5-Chloro-l-benzimidazol-2-yl) -ethyl] -3 -methyl-4- (5,6-didehydro-azepan-2-on-l-yl) benzamide, (62) 4- (Azepan-2-on-l-yl) -N- [(1S) -1- (5-Chloro-6-fluoro-lH-benzimidazol-2-yl) ethyl] -3-methylbenzamide, (63) N- [(SS) -1- (5-Chloro-li'-benzimidazol-2-yl) ethyl) ] -4- (1, 3-dioxothiomorpholin-4-yl) -3-methylbenzamide, (64) N- [(15) -1- (5-Chloro-li-benzimidazol-2-yl) ethyl] -3- methyl-4- (1,1, 3-trioxothiomorpholin-4-yl) benzamide, (65) N- (li?) - l- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl ] -3-methyl-4- (piperazin-1-yl) benzamide, (66) N- [(li?) - l- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] - 3-methyl-4- (piperazin-2-on-1-yl) benzamide, (67) N- [(SS) -1- (5-Chloro-1-benzimidazol-2-yl) butyl] -3-methyl -4- (morpholin-3-on-4-yl) benzamide, (68) N- [(li?) - l- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4 - ([1,3] oxazepan-2-on-3-yl) -3-trifluoromethylbenzamide, (69) N- [(15) -1- (5-chloro-li-benzimidazol-2-yl) e tl] -3-methoxy-4- (piperidin-2-on-l-yl) benzamide, (70) N- [(li?) -1- (5-chloro-li-benzimidazol-2-yl) -2 -methoxyethyl] -3-methoxy-4- (piperidin-2-on-l-yl) benzamide, (71) N- [(li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (1, 1-dioxo [1,2,6] thiadiazin-2-yl) -3-methylbenzamide, (72) N- [(1S) -1- (5-Chloro-1H -benzimidazol-2-yl) ethyl] -4- (1,1-dioxo [1,2,6] thia-diazinan-2-yl) -3-methylbenzamide, (73) N- [(lS) -l- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -4- (1, l-dioxo-6-methyl [1, 2, 6] thiadiazin-2-yl) -3-methylbenzamide, (74) N- [(li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (1, l-dioxo-3-methyl [1,2,6] thiadiazin -2-yl) -3-methylbenzamide, (75) N-l (IR) -1- (5-Bromo-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholino- 3-on-4-yl) benzamide, (76) N- [(SS) -1- (5-Chloro-l-benzimidazol-2-yl) -3- (li-tetrazol-5-yl) propyl] - 3-methyl-4- (morpholin-3-on-4-yl) benzamide, (77) N- [(lS) -l- (5-Chloro-li? -benzimidazol-2-yl) -3-methoxypropyl] -3-methyl-4- (mo rfolin-3-on-4-yl) benzamide, (78) N- [1- (5-Chloro-1'-benzimidazol-2-yl) thiophen-3-ylmethyl] -3-methyl-4- (morpholin-3 ~ on-4-yl) benzamide, (79) N- [(li?) -1- (5-Chloro-l-benzimidazol-2-yl) -2-methylsulfanylethyl] -3-methyl-4- (morpholino- 3-on-4-yl) benzamide, (80) N- [(li?) -1- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (thiomorpholine) -3-on-4-yl) benzamide, (81) 3-Chloro-N- [(li?) -1- (5-chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4-yl) benzamide, (82) 3-Chloro-N- [(SS) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- (3 , 6-dihydro [1,2] oxazin-2-yl) benzamide, (83) 3-Chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2- methoxyethyl] -4- (1, 1-dioxo [1,2] thiazinan-2-yl) benzamide, (84) N- [(li?) - l- (5-Chloro-li? -benzimidazole-2-yl ) -2-methoxyethyl] -4- (1,1-dioxo [1,2] thiazepan-2-yl) -3-methylbenzamide, (85) N- [(1S) -l- (5-Chloro-1-benzimidazol-2-yl) ethyl] -4- (piperidin-2-on-1-yl) -3-trifluoromethoxybenzamide, (86) 3 -Bromo-N- [(SS) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- (piperidin-2-on-l-yl) benzamide, (87) 3-Bromo -N- [(li?) -1- (5-chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (piperidin-2-on-l-yl) benzamide, (88) N - [l- (5-Chloro-l-benzimidazol-2-yl) -l- (furan-2-yl) methyl] -3-methyl-4- (piperidin-2-on-l-yl) benzamide, ( 89) 3-Chloro-N- [(15) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -4- ([1,2] oxazinan-2-yl) benzamide, (90 ) N- [(li?) -1- (5-Chloro-li-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (5-oxo [1,4] oxazepan-4-yl) ) benzamide, (91) N- [(1S) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -4- (4,4-dimethyl-2-oxo-imidazolidin-1-yl) ) -3-methylbenzamide, (92) N- [(li?) - l- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (4, 4-dimethyl-2- oxoimidazolidin-1-yl) -3-methylbenzamide, (93) 3-Chloro-N- [(15) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -4- (4-methyl- 2-oxo-oxazo lidin-3-yl) benzamide, (94) 3-Chloro-N- [(li?) - l- (5-chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (4- methyl-2-oxooxazolidin-3-yl) benzamide, (95) N- [l- (5-Chloro-lH-benzimidazol-2-yl) -l-phenylmethyl] -3-methyl-4- (morpholin-3-) on-4-yl) benzamide, (96) N- [(1S) -1- (5-Chloro-li? -benzimidazol-2-yl) propyl] -3-methyl-4- (morpholine-3-on- 4-yl) benzamide, (97) 3-Bromo-N- [(li?) -1- (5-chloro-li-benzimidazol-2-yl) -2-methoxyethyl] -4- (morpholine-3-on -4-yl) benzamide, (98) N- [(15) -l- (5-Chloro-l-benzimidazol-2-yl) ethyl] -3-methyl-4- (7-oxo [1,4] diazepan-1-yl) benzamide, (99) N- [(li?) - l- (5-Chloro-lH-benzimidazol-2-yl) -l- (thiophen-2-yl) methyl] -3-methyl -4- (morpholin-3-on-4-yl) benzamide, (100) N- [(li?) -1- (5-Bromo-li? -benzimidazol-2-yl) -2-hydroxyethyl] -4 - (1,1-dioxo [1,2] thiazinan-2-yl) -3-methylbenzamide, (101) N- [(li?) -1- (5-Bromo-li-benzimidazol-2-yl) -2-hydroxyethyl] -3-methyl-4- ([1,3] oxazepan-2-on- 3-yl) benzamide, (102) N- [(li?) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (4- (45) -methyl-2-oxooxazolidin-3-yl) benzamide, (103) 3-Chloro-N- [(li?) -1- (5-chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] - 4- (4,4-dimethyl-2-oxooxazolidin-3-yl) benzamide, (104) N- [(li?) - l- (5-Chloro-li? -benzimid.azol-2-yl) -2 -methoxyethyl] -3-methyl-4- (4- (4R) -methyl-2-oxooxazolidin-3-yl) benzamide, (105) 3-Chloro-N- [(li?) -1- (5-chloro -li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (4- (4i?) -ethyl-2-oxooxazolidin-3-yl) benzamide, (106) N- [(li?) -1 - (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-fluoro-4- (morpholin-3-on-4-yl) benzamide, (107) N- [l- (5- Chloro-lH-benzimidazol-2-yl) -l- (li? -pyrazol-3-yl) methyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (108) N- [1- (1S) - (5-Chloro-lH-benzimidazol-2-yl) -2-cyanoethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (109) N- [1 - (5-Chloro-li? -benzimidazol-2-yl) -1-pyridin-3-ylmethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (110) N- [ 1- (5-Chloro-1H-benzimidazol-2-yl) -1- (1-methyl-3-yl) methyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide , (111) 3-Chloro-N- [(li?) -1- (5-chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (5-methylmorphino-3-on- 4-yl) benzamide, (112) 3-Chloro-N- [(1S) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -4- (3-dimethylamino-? Irrolidin-l- il) benzamide, (113) N- [(SS) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -4- (pyrazolidin-3-on-l-yl) -3-trifluoromethylbenzamide , (114) 3-Chloro-N- [(li?) -1- (5-chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (tetrahydropyrimidin-2-on-l-yl) benzamide, (115) N- [(li?) -1- (5-Chloro-li-J-benzimidazol-2-yl) -2-methoxyethyl] -3-chloro-4- ([1,4] diazepan-1-yl) benzamide, (116) 3-Chloro-N- [1- (5-chloro-l-indol-2-yl) -2-methoxyethyl] -4- ([1,4] diazepan-1-yl) benzamide, ( 117) N- [1- (5-Chloro-li? -indol-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (118) 3 -Bromo-N- [1- (5-chloro-l # -indol-2-yl) -1- (furan-2-yl) methyl] -4- ([1,4] oxazepan-5-on-4 -yl) -benzamide, (119) N- [1- (5-Bromo-l-indol-2-yl) -l- (l-methyl-li? -pyrazol-3-yl) methyl] -3-methyl -4- ([1, 3] oxazepan-2-on-3-yl) benzamide, (120) N- [1- (5-Chloro-l-indol-2-yl) -3- (methylsulfonyl) propyl] -3-methyl-4- (tetrahydro-pyrimidin-2-on-l-yl) benzamide, (121). N- [l- (5-Chloro-li? -indol-2-yl) -2-hydroxyethyl] -3-methyl-4- (5-methylpyrrolidin-2-on-l-yl) benzamide, (122) N- [l- (5-Chloro-li? -indol-2-yl) -l-phenylmethyl] -4- (piperazin-1-yl) -3-trifluoromethyl-benzamide, (123) 4- ( Azepan-2-on-l-yl) -3-chloro-N- [l- (5-chloro-lF-indol-2-yl) -3- (l-tetrazol-5-yl) propyl] benzamide, ( 124) N- [1- (5-Bromo-1-yl-indol-2-yl) -2-hydroxyethyl] -4- (1,1-dioxo [1, 2] thiazepan-2-yl) -3-methylbenzamide, (125) 3-Chloro-N- [1- (7-chloroimidazo [1, 2-a] pyridin-2-yl) -2-methoxyethyl] -4- (diazepan-1-yl) benzamide, (126) 3 -Chloro-N- [1- (7-chloroimidazo [1,2- a] pyridin-2-yl) ethyl] -4- ([1,4] oxazepan-5-on-4-yl) benzamide, (127 ) N- [(lS) -l- (7-Chloroimidazo [1,2-a] pyridin-2-yl) -3-methylbutyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (128) N- [l- (7-Chloroimidazo [1,2- a] pyridin-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (129) 3-Bromo-N- [1- (7-chloroimidazo [1, 2-a] pyridin-2-yl) -1- (li? -pyrazol-3-yl) methyl] -4- ( [1,4] oxazepan-5-on-4-yl) benzamide, (130) N- [1- (7-Bromoimidazo [1,2- a] pyridin-2-yl) -2-hydroxyethyl] -3- Chloro-4- (4-methylpiperazin-1-yl) benzamide, (131) N- [1- (7-Chloroimidazo [1,2- a] pyridin-2-yl) -2-hydroxyethyl] -3-methyl- 4- (morpholin-3-on-4-yl) benzamide, (132) N- [1- (7-Chloroimidazo [1,2- a] pyridin-2-yl) -1- (furan-2-yl) methyl] -4- (diazepan-1-yl) -3-trifluoromethylbenzamide, (133) N- [1- (7-Chloroimidazo [1,2-a] pyridin-2-yl) -1-phenylmethyl] -3- methyl-4- (1, 1-dio) xo [1, 2] thiazepan-2-yl) benzamide, (134) 3-Chloro-N- [1- (7-chloroimidazo [1, 2-a] pyridin-2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4-yl) benzamide, (135) 3-Bromo-N- [1- (7-chloroimidazo [1, 2-a] pyridin-2-yl) -3- (methylsulfanyl) propyl] -4- ([1,4] oxazepan-3-) on-4-yl) benzamide, (136) 3-Chloro-N- [1- (7-chloroimidazo [1,2- a] pyridin-2-yl) -2-hydroxyethyl] -4- (piperazin-2-) on-l-yl) benzamide, (137) N- [l- (7-Chloroimidazo [l, 2-a] pyridin-2-yl) -2-methoxyethyl] -3-methyl-4- (piperidin-2- on-l-yl) benzamide, (138) N- [1- (7-Bromoimidazo [1, 2-a] pyridin-2-yl) -3-methoxypropyl] -3-chloro-4- (1, 1- dioxo [1,2] thiazinan-2-yl) -benzamide, (139) N- [1- (7-Chloroimidazo [1,2- a] pyridin-2-yl) -2-trifluoromethoxyethyl] -3-methyl- 4- ([1,4] oxazepan-5-on-4-yl) benzamide, (140) N- [1- (5-Chloro-l-benzimidazol-2-yl) -3-methylbutyl] -3-methyl -4- (morpholin-3-on-4-yl) benzamide, (141) N- [(li?) - l- (5 ~ Chloro-l-1-benzimidazol-2-yl) -2-benzyloxyethyl] -3- methyl-4- (morpholin-3-on-4-yl) enzamide, (142) N- [1- (5-Chloro-li? -benzimidazol-2-yl) -3-benzyloxycarbonylpropyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (143) N- [l- (5-Chloro-lH-benzimidazol-2-yl) -3-hydroxycarbonylpropyl] -3-methyl -4- (morpholin-3-on-4-yl) benzamide, (144) N- [1- (5-Chloro-li? -benzimidazol-2-yl) -1- (pyrazin-2-yl) methyl] -3-methyl-4- (morpholin-3-on-4-) il) benzamide, (145) N- [1- (5-Chloro-lH-benzimidazol-2-yl) -1- (oxazol-2-yl) methyl] -3-methyl-4- (morpholin-3-on -4-yl) benzamide, (146) N- [1- (5-Chloro-li? -benzimidazol-2-yl) -1- (lff-imidazol-4-yl) methyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (147) N- [1- (5-Bromo-li? -benzimidazol-2-yl) -2-methoxyethyl] -3-difluoromethoxy-4- (morpholine- 3-on-4-yl) benzamide, (148) N- [l- (5-Chloro-li? -benzimidazol-2-yl) -l-methylethyl] -3-methyl-4- (morpholine-3-on -4-yl) benzamide, (149) N- [3- (5-Chloro-li? -benzimidazol-2-yl) tetrahydrofuran-3-yl] -3-methyl-4- (morpholin-3-on-4) -yl) benzamide, (150) N- [l- (5-Chloro-li? -benzimidazol-2-yl) -3- (pyrrolidin-1-ylcarbonyl) propyl] -3-methyl-4- (morpholin-3) -on-4-yl) benzamide, (151) N- [1- (5-Ethynyl-li? -benzimidazol-2-yl) ethyl] -3-methyl-4- (morpholin-3-on-4-yl) ) benzamide, (152) N- [l- (5-Ethynyl-li-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholine) -3-on-4-yl) benzamide, (153) N- [1- (5-Ethynyl-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (piperidin-2-on -l-yl) benzamide, (154) 3-Bromo-N- [1- (5-ethynyl-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4-) il) benzamide, (155) N- [1- (5-Ethynyl-lH-benzyl-idazol-2-yl) -2-methoxyethyl] -3-methyl-4- (4-methyloxazolidin-2-on-3-yl) ) benzamide, (156) N- [1- (5-Ethynyl-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- ([1,4] oxazepan-5-on-4-) il) benzamide, (157) N- [(lS) -l ~ (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (2-methyltetrahydropyridazin-1-yl) benzamide, its tautomers, its enantiomers, its diastereomers, its mixtures and its salts, with the compounds (1) 4- (Azepan-2-on-l-yl) -N- [(li?) -1- (5 -chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-methylbenzamide, (2) 4- (Azepan-2-on-l-yl) -N- [(li?) -1- (5 -chloro-lff-benzimidazol-2-yl) -2-hydroxyethyl] -3-methylbenzamide, (3) N- [(lS) -l- (5-Chloro-li-benzimidazol-2-yl) -3-methylsulfanylpropyl ] -3-methyl-4- (pyrrolidin-2-on-l-yl) benzamide, (4) N- [(li?) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4-yl) -3-trifluoromethylbenzamide, (5) N- [(li?) -1- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide , (6) N- [(lS) -l- (5-Chloro-li? -benzimidazol-2-yl) -3-methylsulfanylpropyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (7) N- [(li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-hydroxyethyl] -3-methyl-4- (morpholin-3-on-4-) il) benzamide, (8) 4- (Azepan-2-on-l-yl) -3-chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2 -methoxyethyl] benzamide, (9) 4- (Azepan-2-on-l-yl) -N- [(li?) -1- (5-chloro-lff-benzimidazol-2-yl) -2-methoxyethyl] -3-trifluoromethylbenzamide, (10) N- [(15) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -3-methyl-4- ([1,3] oxazepan-2- on-3-yl) benzamide, (11) N- [(SS) -1- (5-Chloro-li? -benzimidazol-2-yl) -3-methylsulfanylpropyl] -4- (morpholin-3-on-4) -yl) -3-nitrobenzamide, (12) N- [(li?) -1- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- ([1 , 3] oxazepan-2-on-3-yl) benzamide, (13) 3-Chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- ([1,4] oxazepan-5-on-4-yl) benzamide, (14) 3-Chloro-N- [(li?) -1- (5-chloro-1-yl-benzimidazol-2-yl ) -2-methoxyethyl] -4- (piperidin-2-on-l-yl) benzamide, (15) N- [(li?) -1- (5-Bromo-li? -benzimidazol-2-yl) - 2-hydroxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (16) N- [(li, 2S) -1- (5-Chloro-li? -benzimidazole-2 -yl) -2-methoxypropyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (17) N- [(SS) -1- (5-Chloro-li? -benzimidazole- 2-yl) ethyl] -3-methyl-4- (thiomorpholin-3-on-4-yl) benzamide, (18) N- [(li?) - l- (5-Chloro-lH-benzimidazole-2- il) -2-methoxyethyl] -3-methyl-4- (piperidin-2-on-l-yl) benzamide, (19) N- [(li?) -1- (5-Chloro-1-pyr-benzimidazole-2) -yl) -2-methoxyethyl] -3-methyl-4- ([1,3] oxazinan-2-on-3-yl) benzamide, (20) N- [(li?) -1- (5-Chloro -lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (piperidin-2-on-l-yl) -3-trifluoromethylbenzamide, (21) N- [(IR) -1- (5-chloro- liT-benzimidazole -2-yl) -2-methoxyethyl] -4- (1,1-dioxo [1,2] thiazinan-2-yl) -3-methylbenzamide, (22) N- [(SS) -1- (5-Chloro-lH-benzimidazol-2-yl) butyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (23) N- l (li?) - l ~ (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- ([1,3] oxazepan ~ 2-on-3-yl) -3 -trifluoromethylbenzamide, (24) N- [(li?) - l- (5-Chloro-li-benzimidazol-2-yl) -2-methoxyethyl] -4- (1, l-dioxo [1, 2, 6] thiadiazin-2-yl) -3-methylbenzamide, (25) N-l (li?) -1- (5-Bromo-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- ( morpholin-3-on-4-yl) benzamide, (26) N- [(15) -1- (5-Chloro-l-benzimidazol-2-yl) -3- (1H-tetrazol-5-yl) propyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (27) N- l (lS) -l- (5-Chloro-li? -benzimidazol-2-yl) -3 -methoxypropyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (28) N- l (li?) - l- (5-Gloro-li? -benzimidazol-2-yl) -2-methylsulfanylethyl] -3-methyl-4 ~ (morpholin-3-on-4-yl) benzamide, (29) N- [(li?) -1- (5-Chloro-lH-benzimidazol-2-yl ) -2-methoxyethyl] -3-methyl-4- (thiomorpholin-3-on-4-yl) benzamide, (30) 3-Chloro-N- [(li?) -1- (5-chloro-li- benzimidazol-2-yl) -2-methoxy ethyl] -4- (morpholin-3-on-4-yl) benzamide, (31) 3-Chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2 -methoxyethyl] -4- (1,1-dioxo [1,2] thiazinan-2-yl) benzamide, (32) N- [(li?) - l- (5-Chloro-lH-benzimidazole-2-yl ) -2-methoxyethyl] -4- (1,1-dioxo [1,2] thiazepan-2-yl) -3-methylbenzamide, (33) 3-Bromo-N- [(SS) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- (piperidin-2-on-l-yl) benzamide, (34) ) 3-Bromo-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- (piperidin-2-on-l-yl) benzamide, ( 35) N- [1- (5-Chloro-1-yl-benzimidazol-2-yl) -1- (furan-2-yl) methyl] -3-methyl-4- (piperidin-2-on-l-yl) benzamide, (36) N- [(li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (5-oxo [1,4] oxazepan-4-yl) benzamide, (37) 3-Chloro-N- [(li?) -1- (5-chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (4- methyl-2-oxooxazolidin-3-yl) benzamide, (38) N- [1- (5-Chloro-lH-benzimidazol-2-yl) -1-phenylmethyl] -3-methyl-4- (morpholin-3-) on-4-yl) benzamide, (39) 3-Bromo-N- [(li?) -1- (5-chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4-yl) ) benzamide, (40) N- [(li?) ~ l- (5-Chloro-l-benzimidazol-2-yl) -l- (thiophen-2-yl) ethyl] -3-methyl-4- (morpholine) -3-on-4-yl) benzamide, (41) N- [(li?) -1- (5-Bromo-l-benzimidazol-2-yl) -2-hydroxyethyl] -4- (1, 1- dioxo [1,2] thiazin-2-yl) -3-methylbenzamide, (42) N-l (li?) - l- (5-Bromo-l-benzimidazol-2-yl) -2-hydroxyethyl] -3 -methyl-4- ([1,3] oxazepan-2-on-3-yl) benzamide, (43) N- [(li?) -1- (5-Chloro-lH-benzimidazole-2-yl) - 2-methoxyethyl] -3-methyl-4- (4- (4S) -methyl-2-oxooxazolidin-3-yl) benzamide, (44) 3-Chloro-N- [(li?) -1- (5- chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (4,4-dimethyl-2-oxooxazolidin-3-yl) benzamide, (45) N- [(li?) -1- ( 5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (4- (4i?) -methyl-2-oxooxazolidin-3-yl) benzamide, (46) 3-Chloro -N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- (4- (4i?) -ethyl-2-oxooxazolidin-3-yl) benzamide, (47) N- l (li?) - l- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -3-fluoro-4- (morpholin-3-on-4-yl) benzamide, (48) N- [1- (5-Chloro-lif-benzimidazol-2-yl) -l- (lH-pyrazol-3-yl) methyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, (49) N- [1- (5-Chloro-lH-benzimidazol-2-yl) -1- (l, l-methyl-pyrazol-3-yl) methyl] -3-methyl-4- (morpholin-3-on -4-yl) benzamide, (50) 3-Chloro-N- [(li?) -1- (5-chloro-l, -benzimidazol-2-yl) -2-methoxyethyl] -4- (5-methylmorpholin- 3-on-4-yl) benzamide, (51) 3-Chloro-N- [(ljR) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- (tetrahydropyrimidin- 2-on-l-yl) benzamide, (52) N- [l- (5-Chloro-l-benzimidazol-2-yl) thiophen-3-ylmethyl] -3-methyl-4- (morpholin-3-) on-4-yl) benzamide, (53) N- [(1S) -1- (5-Chloro-l-benzimidazol-2-yl) ethyl] -3-methyl-4- ([1,3] oxazepan- 2-on-3-yl) benzamide, (54) N- l (15) -l- (5-Chloro-li? -benzimidazol-2-yl) -3-methylsulfanylpropyl) -4- (piperazin-1-yl) ) -3-trifluoromethylbenzamide, (55) N- [(1S) -1- (5-Chloro-lH-benzimidazol-2-yl) -3-methylsulfanylpropyl ] -4- (morpholin-3-on-4-yl) -3-nitrobenzamide, (56) N- [(li?) -1- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl ] -3-methyl-4- (piperazin-1-yl) benzamide, (57) N- l (15) -l- (7-Chloroimidazo [1,2- a] pyridin-2-yl) -3-methylbutyl ] -3-methyl-4- (morpholin-3-on-4-yl) benzamide, its tautomers, its enantiomers, its diastereomers, its mixtures and its salts. In the context of the present application, if present, by the term "isomer", "stereoisomer", "diastereomer", "enantiomer", "chiral", "racemate" or "racemic mixture" is to be understood as follows . "Compounds" are denominated compounds of the same additive formula that differ in the type or arrangement of the link of their atoms or their connectivity or the special arrangement of the atoms in the molecule. The isomers that are differentiated by the spatial arrangement of the atoms in the molecule with the same type of connectivity of their atoms and that are not superimposable are called "stereoisomers". Stereoisomers that do not behave as an object and mirror image each other are called "diastereomers", and the stereoisomers that behave as an object and mirror image each other are called "enantiomers". In the presence of an asymmetric center or atom (also called stereocenter or center of chirality), for example on a carbon atom substituted with four. different substituents, the molecule has the property of "chiral", and a pair of enantiomers is possible. An enantiomer can be characterized by the absolute configuration of its stereocenter. The description of the absolute configuration is made by the descriptors (R) and (S), which are determined by using the sequence rules of Cahn, Ingold and Prelog, or by describing the rotation of the plane of polarized light in the interaction with the molecule, which is designated as dextrorotatory or levorotatory (also corresponding to (+) or (-) as a descriptor). A chiral compound can be presented both as an individual enantiomer and as a mixture of the corresponding enantiomers. A mixture containing the same proportions of both enantiomers of a compound is called "racemate" or "racemic mixture". According to the invention, the compounds of general formula I are obtained by a known method, for example by the following methods: (a) For the preparation of compounds of general formula , (II) wherein R3 to R5 are defined as cited above and Z1 means a hydrogen atom or a protecting group and B 'represents a group of formula , (IH) in which R7 R ° are defined as mentioned above: cyclization of a compound optionally formed in the reaction mixture of the general formula , (IV) in which R3 to R5, R7 and R8 are defined as mentioned above and Z1 means a hydrogen atom or a protective group, then a protective group optionally present is cleaved. The cyclization is carried out for convenience in a solvent or mixture of solvents such as ethanol, isopropanol, glacial acetic acid, benzene, chlorobenzene, toluene, xylene, glycol, glycol monomethyl ether, diethylene glycol dimethyl ether, sulfolane, dimethylformamide or tetralin, dimethyl sulfoxide, methylene chloride, chloroform, tetrachloromethane, for example at temperatures between 0 and 250 ° C, but preferably between 20 and 100 ° C, optionally in the presence of a condensing agent such as phosphorus oxychloride, thionyl chloride, sulfuryl chloride, sulfuric acid, p toluenesulfonic acid, methanesulfonic acid, hydrochloric acid, phosphoric acid, polyphosphoric acid, acetic acid, acetic acid anhydride, N, N'-dicyclohexylcarbodiimide or optionally also in the presence of a base such as potassium ethylate or potassium tert-butylate. But the cyclization can also be carried out without solvent and / or condensation agent. The compounds of the general formula (IV) can be prepared by the acylation of compounds of the general formula (XXIV), wherein n, R7 and R8 are defined as quoted above, with compounds of general formula (XXV), wherein R3, R4 and R5 are defined as quoted above, Q means a halogen atom or a hydroxy group, C 1 - or C 1 4 -alkoxy acyl, and Z 1 a protecting group, according to the process described in (e). (b) For the preparation of a compound of general formula , (II) in which R3 to R5 are defined as recited above, Z1 means a hydrogen atom or a protecting group, for example a C5_5alkylcarbonyl or benzyloxycarbonyl group, and B 'represents a group of formula , (V) in which R7 and R8 are defined as mentioned above: i) Transition metal catalyzed coupling and cyclization of a compound of general formula , (vi) wherein R3 signifies a phenyl or heteroaryl group and R4 a hydrogen atom, and R5 is defined as recited above, with a compound of general formula wherein R8 is defined as cited above and Z1 means a protecting group, for example an acetyl or methylsulfonyl group, this protecting group is then cleaved. The reaction sequence is carried out for convenience in a solvent or mixture of solvents such as ethanol, isopropanol, glacial acetic acid, benzene, chlorobenzene, toluene, xylene, glycol, glycol monomethyl ether, diethylene glycol dimethyl ether, sulfolane, dimethylformamide, N-methylpyrrolidinone, tetralin, dimethisulfoxide, methylene chloride, chloroform or tetrachloromethane, for example at temperatures between 0 and 250 ° C, but preferably between 20 and 120 ° C, for convenience in the presence of transition metal catalysts such as bis (triphenylphosphino) palladium (II) chloride , bis (tricyclohexylphosphino) palladium (II) chloride, bis (triethylphosphino) palladium (II) chloride or bis (tri-o-tolylphosphino) palladium (II) chloride, and optionally in the presence of a transition metal catalyst such as iodide of copper (I), copper (I) bromide or copper (I) acetate, and for convenience in the presence of a base such as tetramethylguanidine, tetramethylethylenediamine or N, N'-dimethylethylenediamine, as well as eventually using an inert gas atmosphere (for example nitrogen or argon). ii) Alkylation and subsequent reductive amination of a compound of general formula wherein R7 and R8 are defined as recited above and Y signifies a C4-4 alkoxy group, C4-4 amino alkoxy or N-alkoxy C? _ -N-C? -4-amino alkyl, with a compound of general formula R4-M, (IX) wherein R4 is defined as quoted above and M is a metal, such as for example lithium, sodium or potassium, or a metal such as for example magnesium, cadmium, copper or tin, with a suitable counterion, such as, for example, chloride, bromide or iodide, or also a combination of two metals, such as magnesium and copper, lithium and copper or tin and copper, with suitable counterions such as, for example, cyanide, chloride, bromide or iodide , as well as its grouping containing combinations, and subsequent reductive amination of the compounds thus obtained. The alkylation is carried out for convenience in a solvent or mixture of solvents such as benzene, chlorobenzene, toluene, xylene, glycol dimethyl ether, diethylene glycol dimethyl ether, sulfolane, dimethylformamide, N-methylpyrrolidinone, tetralin, dimethyl sulfoxide, methylene chloride, chloroform, tetrachloromethane, diethyl ether, tert-butyl methyl ether or tetrahydrofuran, for example at temperatures between -100 and +100 ° C, but preferably between -100 and 30 ° C, with alkylation reagents such as Grignard reagents, organolytic reagents, Gilman or Knochel cuprates that can be achieved by known procedures in the literature, possibly using an atmosphere of inert gas (nitrogen or argon). The subsequent reductive amination of the ketones formed after the alkylation is carried out by reaction, for example, with ammonia, hydroxylamine, alkoxylamines, primary amines, hydroxylalkyl amines or alkoxyalkylamines followed or accompanied by reduction, for example, with hydride donors such as sodium borohydride, hydride lithium and aluminum, sodium cyanoborohydride, sodium triacetoxyborohydride or diisobutylaluminum hydride in a solvent or mixture of solvents such as ethanol, isopropanol, benzene, toluene, pyridine, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, N-alkylmorpholine, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, hexane or cyclohexane, or by hydrogenation optionally under pressure and for convenience in the presence of a catalyst such as Raney nickel, palladium, palladium on carbon, platinum or platinum oxide, in a solvent or mixture of solvents such as ethyl acetate, ethanol, isopropanol, benzene , toluene, pyridine, ethylene glycol ethers, diethylene glycol dimethyl ether, N-alkyl C? -5-morpholine, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, hexane or cyclohexane. (c) For the preparation of a compound of general formula (II) in which R to R5 are defined as quoted, Z1 means a hydrogen atom or a protective group, for example a C alqu5-oxycarbonyl or benzyloxycarbonyl alkyl group, and B 'represents a group of formula , (X) wherein R8 is defined as cited above: Coupling and subsequent cyclization of a compound of general formula , (XI) wherein n and Rb are defined as mentioned above, with a compound of general formula , (XII) in which R3 to R5 are defined as recited above, Z1 means a protecting group, for example a C alqu-5-oxycarbonyl or benzyloxycarbonyl alkyl group, and Z4 means a nucleofugic leaving group, for example an chlorine, bromine or iodine, a tosylate, triflate or mesylate group, the protecting group Z1 then being cleaved according to procedures known from the literature. The sequence of reactions is carried out for convenience in a solvent or mixture of solvents such as water, ethanol, isopropanol, benzene, chlorobenzene, toluene, xylene, glycol, glycol dimethyl ether, diethylene glycol dimethyl ether, dimethylformamide, N-methylpyrrolidinone, tetralin, dimethisulfoxide, sulfolane, methylene chloride, chloroform, tetrachloromethane or N-ethyldiisopropylamine, N-alkyl C 5 -orpholine, N-alkyl C 5 -piperidine, N-alkyl C 5 -pyrrolidine, triethylamine, pyridine, for example at temperatures between -30 and 250 ° C, but preferably between 0 and 150 ° C, optionally for convenience in the presence of bases such as potassium carbonate, sodium carbonate, sodium acid carbonate, potassium tert-butylate, sodium ethanolate, potassium hexamethyldisilazane, hydride of sodium or lithium diisopropylamide. (d) For the preparation of a compound of general formula , (xiii) wherein A, R1 and R2 are defined as quoted above and Q represents a halogen atom or a hydroxy, C alco - alkoxy or acyl C?-oxy group: i) Nucleophilic substitution of a compound of general formula A '- H, (XIV) in which A' represents a cycloalkyleneimino group of 5 to 7 members as mentioned above in the definition of A, with aromatic compounds of general formula wherein R1 and R2 are defined as recited above and Z2 represents a nitrile group or a C5-C5-alkoxy group, and subsequent saponification of the nitrile or C5-5 alkoxy group of Z2 and optional further reaction of the carboxyl group resulting, giving a reactive carboxylic acid derivative of general formula XIII. Nucleophilic substitution is carried out for convenience in a solvent or mixture of solvents such as ethanol, isopropanol, benzene, chlorobenzene, toluene, xylene, glycol, glycol dimethyl ether, diethylene glycol dimethyl ether, dimethylformamide, N-methylpyrrolidinone, tetralin, dimethisulfoxide, sulfolane, methylene chloride , chloroform, tetrachloromethane or N-ethyldiisopropylamine, N-alkyl C? -5-morpholine, N-alkyl C? -5-piperidine, N-alkyl C? -5-pyrrolidine, triethylamine, pyridine, for example at temperatures between -30 and 250 ° C, but preferably between 0 and 150 ° C, optionally for convenience in the presence of bases such as potassium carbonate, sodium carbonate, potassium tert-butylate, sodium ethanolate, potassium hexamethyldisilazane, sodium hydride or diisopropylamide. lithium. ii) Transition metal catalyzed coupling reaction of a compound of general formula A '- H, (XIV) wherein A' represents a 5- to 7-membered cycloalkyleneimino group as recited above in the definition of A, with compounds aromatics of general formula , (xvi) in which R1 and R2 are defined as recited above and Z2 represents a nitrile group or a C5-5 carbonyl alkoxy group and Z3 represents a chlorine, bromine or iodine atom or a triflate group, and subsequent saponification of the nitrile or C?-5-carbonyl alkoxy group of Z 2 and eventual subsequent reaction of the resulting carboxyl group thus giving a reactive carboxylic acid derivative of general formula XIII. The reaction is carried out for convenience in a solvent or mixture of solvents such as benzene, toluene, xylene, tetrahydrofuran, dioxane, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, sulfolane, dimethylformamide, N-methylpyrrolidinone, tetralin, dimethyl sulfoxide, methylene, chloroform or tetrachloromethane, for example at temperatures between -30 and 250 ° C, but preferably between 0 and 150 ° C, for convenience in the presence of transition metal catalysts such as nickel on active carbon, palladium on carbon, tetrakis (triphenylphosphine) ) palladium (0), tris (dibenzylidene ketone) dipalladium (0), palladium (II) acetate, palladium chloride (11) / bis (triphenylphosphine) palladium (II) chloride, bis (tricyclohexylphosphine) palladium (II) chloride , bis (triethylphosphine) palladium (II) chloride, bis (tri-o-tolylphosphine) palladium (II) chloride, optionally in the presence of ligands such as triphenylphosphine, tri-o-tolylphosphine, tri-tert. -butylphosphine, 1,3-bis (diphenylphosphino) propane, 2,2'-bis (diphenylphosphino) -1,1'-dinaphthyl, 1,1'-bis (diphenylphosphino) ferrocene, xantphos, and for convenience in the presence of a base such as sodium methanolate, sodium ethanolate, sodium tert-butylate, potassium tert-butylate, sodium terebutyldimethylsilanoate, potassium hexamethyldisilazane, lithium diisopropylamide, potassium carbonate, rubidium carbonate, cesium carbonate, phosphate potassium, sodium hydride, optionally in the presence of a complex former such as 18-crown-6-ether, as well as using for convenience an inert gas atmosphere (eg nitrogen or argon) and optionally under pressure. iii) Selective oxidation of a cycloalkyleneimino group in compounds of general formula , (XVII) wherein A 'represents a 5-to-7-membered 2-oxocycloalkyleneimino group optionally substituted also as cited above in the definition of A, R1 and R2 are defined as cited above and Z2 represents a carboxyl group, and optional additional reaction giving a reactive carboxylic acid derivative - of general formula XIII. The reaction of a compound of general formula XIII, obtained for example according to the processes described above, in which A 'signifies a cycloalkyleneimino group and Q signifies a hydroxy group, giving the corresponding lactam by oxidation of a methylene group contiguous with nitrogen, it is carried out, for example, with oxidation agents such as potassium permanganate, potassium chromate, potassium dichromate, chromium (VI) oxide, mercury (II) chloride, selenium (IV) oxide, lead (IV) oxide. , lead oxide (II, IV), potassium peroxomonosulfate, hydrogen peroxide, sodium hypochlorite, optionally in the presence of a suitable catalyst such as nickel (II) chloride, cobalt (II) chloride, ruthenium chloride (III) , osmium oxide (VIII), vanadium (IV) oxide and / or in the presence of a crown ether such as 18-crown-6, in a solvent or mixture of solvents such as water, formic acid, acetic acid, ethyl acetate, benzene, pyridine, dicl oromethane, chloroform, tetrachloromethane, optionally under biphasic conditions in the presence of a suitable phase transfer catalyst such as for example tetrabutylammonium chloride, tetrabutylammonium bromide, benzyltriethylammonium chloride or methyltrioctylammonium chloride, optionally in the presence of an acid such as acetic acid, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, sodium acid sulfate, sodium dihydrogen phosphate and / or a base such as sodium hydroxide, potassium hydroxide, ammonia, pyridine, potassium phosphate, dipotassium hydrogen phosphate or sodium acetate at temperatures between -30 and 250 ° C, but preferably between 0 and 150 ° C. For example, this reaction can be carried out as described in J. H. Markgraf, C. A. Stickney, J. Heterocycl. Chem. 2000, 37 (1), 109. iv) Transition metal catalyzed coupling reaction of a compound of general formula A '- H, (XIV) wherein A' represents a 5-to-7-membered 2-oxocycloalkyleneimino group optionally substituted as mentioned above in the definition of A, with aromatic compounds of general formula wherein R1 and R2 are defined as recited above, Z2 represents a nitrile group or a C5-C5-alkoxy group and Z3 represents a chlorine, bromine or iodine atom or a triflate group, and subsequent saponification of the nitrile group or C 2 -5-carbonyl alkoxy of Z 2 and optional further reaction of the carboxyl group thus resulting to give a reactive carboxylic acid derivative of general formula XII. The reaction is carried out for convenience in a solvent or mixture of solvents such as benzene, toluene, xylene, tetrahydrofuran, dioxane, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, sulfolane, dimethylformamide, N-methylpyrrolidinone, tetralin, dimethyl sulfoxide, methylene, chloroform or tetrachloromethane, for example at temperatures between -30 and 250 ° C, but preferably between 0 and 200 ° C, for convenience in the presence of transition metal catalysts such as tetrakis (triphenylphosphine) palladium (0), tris (dibenzylidenacetone) dipalladium (0), palladium (II) acetate, palladium (II) chloride, bis (triphenylphosphino) palladium (II) chloride, bis (tricyclohexylphosphino) palladium (II) chloride, bis (triethylphosphine) palladium (II) chloride ), bis (tri-o-tolylphosphino) palladium (II) chloride, optionally in the presence of ligands such as triphenylphosphine, tri-o-tolylphosphine, tri-tert-butylphosphine, 1,3-bis (diphenylphosphino) propane, 2,2 '- bis (diphenylphosphino) -1,1'-dinaphthyl, 1,1 '-bis (diphenylphosphino) ferrocene, Xantphos, or for example in the presence of a transition metal catalyst such as copper iodide (I), copper bromide (I) or copper (I) acetate, and for convenience in the presence of a base such as tetramethylguanidine, tetramethylethylenediamine or N, N'-dimethylethylenediamine, and for convenience in the presence of a base such as sodium methanolate, sodium ethanolate, sodium tert-butylate , potassium tert-butylate, sodium tert-butyldimethylsilanoate, potassium hexamethyldisilazane, lithium diisopropylamide, potassium carbonate, rubidium carbonate, cesium carbonate, potassium phosphate, sodium hydride, optionally in the presence of a complexing agent such as 18-crown-6-ether, as well as using for convenience an inert gas atmosphere (for example nitrogen or argon) and optionally under pressure. v) Acylation / sulphonylation and alkylation of a compound of general formula , (XVIII) wherein R1 and R2 are defined as recited above and Z2 represents a nitrile group or a C5.5-carbonyl alkoxy group, with a compound of general formula , (XIX) in which E represents a carbonyl, oxycarbonyl, sulfonyl or sulfamoyl group as recited above, G represents a chlorine, bromine or iodine atom or an anhydride group, C? _5 alkoxy or benzotriazoloxy or E and G represent together an isocyano group and Z4 represents a nucleofugic leaving group, for example a chlorine, bromine or iodine atom, a tosylate, triflate or mesylate group, and n is a number between 3 and 5, in which individual methylene groups according to the aforementioned description they may be further substituted or exchanged by heteroatoms, and then intramolecular cyclization by alkylation of the anuine nitrogen by cleavage of the nucleophilic leaving group Z4, followed by saponification of the nitrile or C ?5-carbonyl group of Z2 and optional further reaction of the carboxyl group thus resulting in giving a reactive carboxylic acid derivative of general formula XIII. The acylation / sulfonylation is carried out for convenience in a solvent or mixture of solvents such as benzene, chlorobenzene, toluene, xylene, glycol dimethyl ether, diethylene glycol dimethyl ether, dimethylformamide, N-methylpyrrolidinone, tetralin, dimethyl sulfoxide, sulfolane, methylene chloride, chloroform, tetrachloromethane, N-ethyldiisopropylamine, N-alkyl C? 5-morpholine, N-C 1-5 alkyl-piperidine, N-alkyl C? -5-pyrrolidine, triethylamine, pyridine, for example at temperatures between -30 and 250 ° C, but preferably between 0 and 150 ° C, for convenience in the presence of bases such as pyridine, triethylamine, p-dimethylaminopyridine, potassium carbonate, sodium carbonate, potassium tert-butylate, sodium methanolate, sodium ethanolate or basic ion exchangers. The subsequent intramolecular alkylation is carried out for convenience in an organic solvent or mixture of organic solvents such as benzene, chlorobenzene, toluene, xylene, glycol dimethyl ether, diethylene glycol dimethyl ether, dimethylformamide, dimethisulfoxide, sulfolane, methylene chloride, tetrachloromethane, N-ethyldiisopropylamine, N- alkyl C? -5-morpholine, N-alkyl C? 5-piperidine, N-alkyl C? 5-pyrrolidine, triethylamine, pyridine, for example at temperatures between -30 and 250 ° C, but preferably between 0 and 150 ° C , for convenience in the presence of bases such as pyridine, triethylamine, potassium carbonate, sodium carbonate, potassium tert-butylate, sodium methanolate, sodium ethanolate, sodium hydride, potassium hexamethyldisilazane or lithium diisopropylamide. vi) Carbamoylation / urea formation with a compound of general formula , (XX) in which R1 and R2 are defined as cited above and Z2 represents a nitrile group or a C5-C5-alkoxy group, and which can be obtained by methods known in the literature from compounds of general formula XVIII, for example by reaction with phosgene in toluene, with a compound of general formula (XD in which Z4 represents a nucleofugic leaving group, for example a chlorine, bromine or iodine atom, a tosylate, triflate or mesylate group, and E represents a hydroxyl, amino or C? _3-amino alkyl function, and n is a number between 2 and 4, in which individual methylene groups can be further substituted according to the aforementioned description, and then intramolecular cyclization by alkylation of the anuid nitrogen by cleavage of the nucleophilic leaving group Z4, followed by saponification of the nitrile or alkoxy C group The carbonyl of Z2 and any further reaction of the carboxyl group thus resulting in a reactive carboxylic acid derivative of general formula XIII Carbamoylation is carried out for convenience in a solvent or mixture of solvents such as benzene, chlorobenzene, toluene, xylene , glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dimethylformamide, N-methylpyrrolidinone, tetralin, d imethisulfoxide, sulfolane, methylene chloride, chloroform, tetrachloromethane, N-ethyldiisopropylamine, N-C 1-5 alkylmorpholine, N-alkyl C 5 -piperidine, N-alkyl C 5 -pyrrolidine, triethylamine, pyridine, for example temperatures between -30 and 250 ° C, but preferably between 0 and 150 ° C.

The subsequent intramolecular alkylation is carried out for example analogously to that described in v). vii) Ring closure metathesis of a compound of general formula , (XXII) wherein R1 and R2 are defined as described above, Z2 represents a nitrile group, C1-5 alkoxycarbonyl or carboxyl, E represents an aminocarbonyl, aminosulfonyl or optionally substituted amino group corresponding to the aforementioned description or a carbonyl or sulfonyl group or an oxygen or sulfur atom or a bond, in which m or o represent independently identical or different numbers between 1 and 3, which can be obtained by an alkylation and acylation / sulphonylation / carbamoylation / sulfamoylation sequence with the corresponding reagents according to processes already described herein or known in the literature, followed by saponification of the nitrile or C ?5-carbonyl group of Z2 and optional further reaction of the carboxyl group thus resulting in a reactive carboxylic acid derivative of general formula XIII. Ring closure by the metathesis reaction is carried out for convenience in a solvent or mixture of solvents such as benzene, chlorobenzene, toluene, xylene, methanol, ethanol, propanol, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether, diethylene glycol dimethyl ether. , dimethylformamide, N-methylpyrrolidinone, tetralin, dimethisulfoxide, sulfolane, methylene chloride, chloroform, tetrachloromethane, pyridine in the presence of a catalyst such as benzylidenebis (tricyclohexylphosphine) dichlororuthenium (first generation Grubbs catalyst) or benzylidene- [1,3-bis] (2,4,6-trimethylphenyl) -2-imidazolidinylidene] dichloro (tricyclohexylphosphine) ruthenium (second generation Grubbs catalyst) for example at temperatures between -30 and 250 ° C, but preferably between 0 and 150 ° C, for convenience in an inert gas atmosphere, for example argon. (e) For the preparation of a compound of general formula , (XXIII) in which A, B and R1 to R5 are defined as mentioned above: acylation of a compound of general formula , di) wherein B and R3 to R5 are defined as recited above and Z1 means a hydrogen atom, with a carboxylic acid or a reactive carboxylic acid derivative of the general formula wherein A, R1 and R2 are defined as cited above and Q represents a hydroxy or alkoxy group C? _4, a halogen atom or an acyloxy group. The acylation is carried out for convenience with the corresponding halide or anhydride in a solvent such as methylene chloride, chloroform, carbon tetrachloride, ether, tetrahydrofuran, dioxane, benzene, toluene, acetonitrile, dimethylformamide, sodium hydroxide or sulfolane, optionally in presence of an inorganic or organic base at temperatures between -20 and 200 ° C, but preferably at temperatures between -10 and 160 ° C. However, the acylation can also be carried out with the free acids, optionally in the presence of an acid activating agent or a dehydrating agent, for example in the presence of isobutyl ester of chloroformic acid, thionyl chloride, trimethylchlorosilane, hydrochloric acid, sulfuric acid , methanesulfonic acid, p-toluenesulfonic acid, phosphorus trichloride, phosphorus pentoxide, N, N1-dicyclohexylcarbodiimide, N, N '-dicyclohexylcarbodiimide / N-hydroxysuccinimide or 1-hydroxybenzotriazole, N, N1-carbonyldiimidazole, O- (benzotriazole tetrafluoroborate) -1-yl) -N, N, N ', N 1 -tetramethyluronium / N-methylmorpholine, O- (benzotriazol-1-yl) -N, N, N', N '-tetramet-illuronium / N-ethyldiisopropylamine tetrafluoroborate, O-pentafluorophenyl-N, N, N ', N'-tetramethyluronium / triethylamine hexafluorophosphate, N, N'-cytyldiimidazole or triphenylphosphine / carbon tetrachloride, at temperatures between -20 and 200 ° C, but preferably at temperatures between -10 and 160 ° C. Other methods for amide coupling are described, for example in P.D. Bailey, I.D. Collier, K.M. Morgan in "Comprehensive Functional Group Interconversions", Vol. 5, pages 257 et seq., Pergamon 1995. (f) For the preparation of a compound of general formula (II), (XXIV), (VII), (VIII), ( XI) or (XXIII), wherein A, B and R1 to R7 are defined as cited above and R8 signifies a C2_3 alkynyl group that is linked by the carbon atom with the aromatic compound which carries at the same time the triple linkage, from the corresponding compound wherein R8 means a bromine or iodine atom or a triflate group, boric acid or boric acid ester: transition metal catalyzed coupling reaction of a compound of general formula (XXVI), in which Z5 means a hydrogen atom, a methyl group or a protective group such as, for example, a trimethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl or triisopropyl group, which can then be cleaved, with a compound of the general formula (II), (XXIV), (VII), (VIII), (XI) or (XXIII), wherein A, B and R1 to R7 are defined as quoted above and R8 means a bromine or iodine atom or a triflate, boric acid or ester group of boric acid. The reaction is preferably carried out in a solvent or mixture of solvents such as acetonitrile, diethyl ether, tetrahydrofuran, dioxane, water or dimethylformamide or a mixture of solvents in the presence of a palladium catalyst such as for example bis (triphenylphosphino) palladium chloride.

(II), [1, 1 '-bis (diphenylphosphino) ferrocene] palladium chloride (II) or tetrakis (triphenylphosphino) palladium (0) in the presence of a base such as triethylamine, N-isopropyldiethylamine, N, N-diisopropylethylamine, potassium tert-butylate, sodium carbonate or cesium carbonate, optionally in the presence of ligands such as triphenylphosphine, tri-s-tolylphosphine, tri-tert-butylphosphine, 1,3-bis (diphenylphosphino) propane, 2,2'-bis (diphenylphosphino) -1,1'-dinaphthyl, 1,1'-bis (diphenylphosphino) ferrocene, Xantphos, and optionally in the presence of a transition metal compound such as a copper halide such as copper (I) iodide and at temperatures between 20 and 120 ° C, preferably at temperatures between 20 and 90 ° C under an argon atmosphere or nitrogen (see also K. Sonogashira, "Comprehensive Organic Synthesis", Vol. 3, page 52 et seq., Pergamon Press, Oxford 1991). The cleavage of an optional silyl protecting group present, for example trimethylsilyl, is preferably carried out in a solvent or mixture of solvents such as water, methanol, ethanol, isopropanol, acetone, dioxane, tetrahydrofuran or dimethylformamide in the presence of a base such as lithium hydroxide. , sodium hydroxide, potassium carbonate or sodium methylate. For cleavage in organic solvents such as diethyl ether, tetrahydrofuran or dichloromethane, fluoride reagents, such as, for example, tetrabutylammonium fluoride, lithium fluoride or potassium fluoride, optionally with addition of a complex former such as 18-crown-ether, are also suitable. . In the reactions described above, reactive groups optionally present as hydroxy, carboxy, amino, alkylamino or imino groups can be protected during the reaction by conventional protecting groups which are cleaved again after the reaction. For example, the methoxy, -benzyloxy, trimethylsilyl, acetyl, benzoyl, tert-butyl, trityl, benzyl or tetrahydropyranyl groups, as protective moieties for a carboxyl group, the trimethylsilyl, methyl, ethyl groups are taken into account as protective moieties for a hydroxy group. , tert-butyl, benzyl or tetrahydropyranyl and as protective moiety for an amino, alkylamino or imino group the acetyl, trifluoroacetyl, benzoyl, ethoxycarbonyl tert-butoxycarbonyl, benzyloxycarbonyl, benzyl, methoxybenzyl groups. or 2, 4-dimethoxybenzyl or 2,4-dimethoxybenzyl, and for the amino group additionally the phthalyl group. Other protecting groups are described and their cleavage in T.W. Greene, P.G.M. Wuts, "Protective Groups in Organic Synthesis", Wiley, 1991 and 1999. The optionally subsequent cleavage of a protective moiety used is carried out, for example, hydrolytically in an aqueous solvent, for example in water, isopropanol / water, tetrahydrofuran / water or dioxane / water, in the presence of an acid such as trifluoroacetic acid, hydrochloric acid or sulfuric acid or in the presence of an alkaline base such as lithium hydroxide, sodium hydroxide or potassium hydroxide or by cleavage of ether, for example in the presence of iodotrimethylsilane, at temperatures between 0 and 100 ° C, preferably at temperatures between 10 and 50 ° C. The cleavage of a benzyl, methoxybenzyl or benzyloxycarbonyl radical is, however, carried out, for example, by hydrogenolytically, for example with hydrogen in the presence of a catalyst such as palladium / carbon in a solvent such as methanol, ethanol, ethyl acetate, dimethylformamide, dimethylformamide / acetone or glacial acetic acid, optionally with the addition of an acid such as hydrochloric acid at temperatures between 0 and 50 ° C, but preferably at room temperature, and at a hydrogen pressure of 100 to 700 kPa, but preferably 100 to 500 kPa. The cleavage of a methoxybenzyl group can also be carried out in the presence of an oxidation agent such as cerium (IV) nitrate and ammonium in a solvent such as methylene chloride, acetonitrile, or acetonitrile / water at temperatures between 0 and 50 ° C, but preferably at room temperature. The cleavage of a methoxy group is carried out for convenience in the presence of boron tribromide in a solvent such as methylene chloride at temperatures between -35 and -25 ° C. The cleavage of a 2,4-dimethoxybenzyl radical is, however, preferably carried out in trifluoroacetic acid in the presence of anisole. The cleavage of a tert-butyl or tert-butoxycarbonyl residue is preferably carried out by treatment with an acid such as trifluoroacetic acid or hydrochloric acid, optionally using a solvent such as methylene chloride, dioxane or ether. The cleavage of a phthalyl moiety is preferably carried out in the presence of hydrazine or a primary amine such as methylamine, ethylamine or n-butylamine in a solvent such as methanol, ethanol, isopropanol, toluene / water or dioxane at temperatures between 20 and 50 ° C. The cleavage of an allyloxycarbonyl moiety is carried out by treatment with a catalytic amount of tetrakis (triphenylphosphine) palladium (0), preferably in a solvent such as tetrahydrofuran, and preferably in the presence of an excess of a base such as morpholine or 1,3-dimedone a temperatures between 0 and 100 ° C, preferably at room temperature and under an inert gas atmosphere, or by treatment with a catalytic amount of tris (triphenylphosphine) rhodium chloride (I) in a solvent such as aqueous ethanol, and optionally in the presence of a base as 1,4-diazabicyclo [2.2.2] octane at temperatures between 20 and 70 ° C. The preparation of compounds of general formula (II), in which the group B 'is transferred by a radical of general formula (III) and (IV), can be carried out analogously to K. Maekawa, J. Ohtani, Agr. Biol. Chem. 1976, 40, 791-799. In addition, the compounds of general formula I obtained can be separated into their enantiomers and / or diastereomers. Thus, for example, the compounds of general formula I obtained which appear as racemates can be separated according to known procedures (see Allinger N. L. and Eliel E. L. in "Topics in Stereochemistry", Vol. 6, Wiley Interscience, 1971) in their optical antipodes.; and compounds of general formula I with at least two asymmetric carbon atoms can be separated, on account of their chemical-physical differences, according to known methods, for example by chromatography and / or fractional crystallization, in their diastereomers which, in the case of produced in racemic form, they can be separated into the enantiomers as mentioned above. The separation of enantiomers is preferably carried out by column separation in chiral phase or by crystallization from an optically active solvent or by reaction with an optically active substance which forms salts or derivatives with the racemic compound, such as, for example, esters or amides, especially acids and their activated derivatives or alcohols; and separation of the salt mixtures or diastereoisomeric derivatives obtained in this way, for example because of different solubilities, the free antipodes can be liberated from the diastereomeric-pure salts or derivatives by the action of a suitable agent. Particularly optically active acids are, for example, the D and L forms of tartaric acid or dibenzoyltartaric acid, di-o-tolyltartaric acid, malic acid, mandelic acid, camphor sulfonic acid, glutamic acid, aspartic acid or quinic acid. Suitable optically active alcohols are, for example, (+) - or (-) -mentol and, as the optically active acyl residue, amides, for example, the (+) - or (-) - menthyloxycarbonyl radical. In addition, the compounds of formula I obtained in the form of their salts, especially for pharmaceutical use and their physiologically compatible salts, can be transformed with inorganic or organic acids. Suitable acids are, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, phosphoric acid, fumaric acid, succinic acid, lactic acid, citric acid, tartaric acid or maleic acid. In addition, the novel compounds of formula I thus obtained, if they contain a carboxyl group, can optionally be converted subsequently into their salt form with inorganic or organic bases, especially for pharmaceutical use in their physiologically compatible salts. As bases, for example, sodium hydroxide, potassium hydroxide, cyclohexylamine, ethanolamine, diethanolamine and triethanolamine can be taken into account. As already mentioned above, the compounds of general formula I as well as their tautomers, their enantiomers, their diastereomers and their physiologically compatible salts have pharmacologically valuable properties, especially an antithrombotic activity which is preferably based on an activity with influence on thrombin or factor. Xa, for example a thrombin inhibitory or factor Xa inhibitory activity, an aPTT time-elongation activity and / or an inhibitory activity of related serine proteases, such as for example urokinase, Vlla factor, factor IXa, factor Xla and factor Xlla. In the compounds mentioned in the experimental part, their activity on the inhibition of factor Xa was investigated as follows: Methodology: Enzymatic measurement with chromogenic substrate. The amount of p-nitroaniline (pNA) released by the human factor Xa from the colorless chromogenic substrate is determined photometrically at 405 nm. It is provides the activity of the enzyme used. The inhibition of the enzymatic activity by the test substance (referred to the control of solvent) is reported at different concentrations of test substance, and IC50 is calculated with it as that concentration which inhibits 50% factor Xa used.

Material: Tris (hydroxymethyl) aminomethane buffer (100 mMol) and sodium chloride (150 mMol), pH 8.0 plus fraction V of human albumin 1 mg / ml, free of protease. Factor Xa (Calbiochem), specific activity: 217 IU / mg, final concentration: 7 IU / ml per reaction mixture. Substrate S 2765 (Chromogenix), final concentration: 0.3 mM / 1 (1 KM) per reaction mixture. Test substance: final concentration 100, 30, 10, 3, 1, 0.3, 0.1, 0.03, 0.01, 0.003, 0.001 μMol / 1 Embodiment: 10 μl of a concentrated starting solution 23.5 times of test substance or solvent (control), 175 μl of TRIS / HSA buffer and 25 μl of factor Xa use solution of 65.8 are incubated for 10 minutes at 37 ° C. U / L. After the addition of 25 μl of S 2765 use solution (2.82 mMol / L), the sample is measured in a photometer (SpectraMax 250) at 405 nm for 600 seconds at 37 ° C.

Valuation: 1. Determination of the maximum increase (deltaDO / minute) in 21 measurement points. 2. Determination of% inhibition referred to solvent control. 3. Elaboration of an activity-dose curve (% inhibition versus substance concentration). 4. Determination of the CI5o by interpolation of the value of X (substance concentration) of the activity-dose curve at Y = 50% inhibition. All compounds tested showed IC 50 values less than 100 μmol / 1. The compounds prepared according to the invention are generally well compatible. Because of their pharmacological properties, the new compounds and their physiologically compatible salts are suitable for the prevention and treatment of venous and arterial thrombotic diseases, such as for example the prevention and treatment of deep vein thrombosis of the legs, the reduction of reocclusions after bypass or angioplasty operations (PT (C) A), as well as occlusion in peripheral arterial diseases, as well as the prevention and treatment of pulmonary emboli, disseminated intravascular coagulation and severe sepsis, reduction and prophylaxis of DVT in patients with exacerbation of COPD, treatment of ulcerative colitis, prophylaxis and treatment of coronary thrombosis, stroke prophylaxis and reduction of lead occlusion. Additionally, the compounds according to the invention are suitable as an antithrombotic support in a thrombolytic treatment, such as for example with alteplase, reteplase, tenecteplase, staphylokinase or streptokinase, for the reduction of long-term restenosis after PT (C) A, for prophylaxis and the treatment of ischemic events in patients with all forms of coronary heart disease, for the reduction of metastatization and the growth of tumors and inflammatory processes, for example in the treatment of pulmonary fibrosis, for the prophylaxis and treatment of arthritis rheumatoid, for the prophylaxis or reduction of tissue adhesions dependent on fibrin and / or tissue healing, as well as for the enhancement of wound healing processes. The new compounds and their physiologically compatible salts can be used therapeutically in combination with acetylsalicylic acid, with inhibitors of platelet aggregation as fibrinogen receptor antagonists (for example abciximab, eptifibatide, tirofiban, roxifiban), with activators and physiological inhibitors of the coagulation and its recombinant analogues (for example protein C, TFPI, antithrombin), with inhibitors-from ADP-induced aggregation (eg clopidogrel, ticlopidine), with P2T receptor antagonists (eg cangrelor) or with combined thromboxane receptor antagonists / synthetase inhibitors (eg terbogrel) . The dosage necessary for obtaining the corresponding activity is for convenience in intravenous administration of 0.01 to 3 mg / kg, preferably 0.03 to 1.0 mg / kg, and oral administration of 0.03 to 30 mg / kg, preferably 0.1 to 10. mg / kg, respectively 1 to 4 times a day. For this, the compounds of formula I prepared according to the invention, optionally in combination with other active substances, together with one or more conventional inert diluents and / or diluents, for example with corn starch, milk sugar, sugar of cane, microcrystalline cellulose, magnesium stearate, poly (vinyl pyrrolidone), citric acid, tartaric acid, water, water / ethanol, water / glycerin, water / sorbitol, water / polyethylene glycol, propylene glycol, cetylstearyl alcohol, carboxymethylcellulose or substances containing fats as Hard fat or its suitable mixtures, can be processed in conventional galenic preparations such as tablets, dragees, capsules, powders, suspensions or suppositories. The following examples should illustrate the invention in detail, but without limiting its scope: Experimental part For the prepared compounds, melting points, IR, UV, 1H-NMR and / or mass spectra are generally presented. If - not otherwise stated, the Rf values were determined using TLC plates prepared with silica gel 60 F25 (E. Merck, Darmstadt, item no. 1.05714) without chamber saturation. The Rf values reported in the Alox reference were determined using TLC plates prepared with 60 F25 aluminum oxide (E. Merck, Darmstadt, item # 1.05713) without chamber saturation. The Rf values reported in the reverse phase reference 8 were determined using TLC plates prepared with RP-8 F254s (E. Merck, Darmstadt, article number 1.15684) without camera saturation. The ratios given in the liquid media refer to volume units of the corresponding solvent. For chromatographic purifications, silica gel from the company Millipore (MATREX ™, 35-70 μm) was used. In the case of missing more detailed configuration data, it remains open if it is pure stereoisomers or mixtures of enantiomers / diastereoisomers. The following abbreviations are used in the test descriptions: Boc tert-butoxycarbonyl DIPEA N-Ethyldiisopropylamine DMSO Dimethylsulfoxide DMF N, N-dimethylformamide sat. saturated h hour (s) a. v. to empty conc. concentrate? N-methylmorpholine MM? MP N-Methylpyrrolidin-2-one or ortho PfTU O-pentafluorophenyl-N, N, N, N'-tetramethyluronium hexafluorophosphate PPA cycloanhydride of propanophosphonic acid quant. quantitative Rf retention factor Rt retention time rae. racemic TBTU tetrafluoroborate O- (benzotriazol-1-yl) -N, N, N ", N '-tetramethyluronium TEA triethylamine TFA trifluoroacetic acid THF tetrahydrofuran tere tertiary - performance throughout all the described steps carried out analogously HPLC / MS for examples 35 to 38 were obtained under the following conditions: (a) Waters ZMD HPLC, Alliance 2690, Waters 2700 autosampler, Waters 996 diode row detector. Mobile phase was used as: A: water with 0.1% of TFA B: acetonitrile with 0.1% TFA Time in min% A% B Flow in ml / min 0.0 95 5 1.00 0.1 95 5 1.00 5.1 2 98 1.00 6.5 2 98 1.00 7.0 95 5 1.00 As a stationary phase, a Waters X column served -Terra ™ MS C? 8 of 3.5 μm, 4.6 mm x 50 mm (column temperature: constant at 25 ° C) Detection of row of diodes was performed in a wavelength range of 210-500 nm. of mass spectrometric detection: m / z 120 am / z 950. (b) HPLC / E data M for the conventional examples, unless otherwise indicated, were obtained under the following conditions: HP 1100 with quaternary pump, Gilson G215 autosampler, HP diode row detector. The following was used as mobile phase: A: water with 0.1% TFA B: acetonitrile with 0.08% TFA Time in min% A% B Flow in ml / min 0.0 95 5 0.4 0.15 95 5 0.4 4.65 2 98 0. 4 6.0 2 98 0.4 6.5 95 5 0.4. A Waters X-Terra ™ MS C 18 column of 2.5 um, 2.1 mm x 50 mm (constant column temperature at 25 ° C) was used as the stationary phase. The row detection of diodes was performed in the wavelength range of 210-550 nm. Range of mass spectrometric detection: m / z 120 to m / z 1000.

Example 1 3-Chloro-N- [(15) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- ([1,4] diazepan-1-yl) benzamide (a) 4- (4-N-Acetyl [1,4] diazepan-1-yl) -3-chlorobenzonitrile 4.67 g (30 mmol) of 3-chloro-4-fluorobenzonitrile and 4.27 g (30 mmol) of Nl-acetyl [1,4] diazepane in 5.0 ml of DIPEA for 6 hours at 90 ° C. Next, concentrate a.v. and the residue is dissolved in dichloromethane. The organic phase is washed twice with water, dried over sodium sulfate and concentrated a.v. The residue is reacted again without further purification. Yield: 7.50 g (90%) Rf value: 0.20 (silica gel, dichloromethane / ethanol = 50: 1). (b) 3-Chloro-4- ([1,4] diazepan-1-yl) benzoic acid. The residue obtained in Example 7 (7.50 g, 27.0 mmol) in 50 ml of sodium hydroxide solution is refluxed for 8 h. 25% potassium hydroxide. Then, adjust to pH 5 with conc. Hydrochloric acid. The precipitated solid is filtered off, dried and reacted again without further purification. Yield: 5.60 g (81%). Rf value: 0 0 (silica gel; dichloromethane / ethanol = 9: 1). (c) 3-Chloro-4- ([1,4] diazepan-1-yl) benzoic acid methyl ester The residue obtained in Example Ib is suspended (3.00 g, 11.8 mmol) in 100 ml of methanol and hydrogen chloride is conducted through it for 1 hour with stirring and heating under reflux. Then concentrate a.v., mix the residue with a 5% sodium hydrogencarbonate solution and extract three times with dichloromethane. The combined organic phases are dried over sodium sulfate. The remaining residue is reacted again after concentrating a.v. without additional purification. Yield: 2.25 g (71%). Rf value: 0.10 (silica gel, dichloromethane / ethanol = 4: 1 + 2% ammonia). C13H? 7ClN202 (268.75). Mass spectrum: (M + H) + = 269/271 (chlorinated isotope). (d) 4- (4-N-Boc- [1,4] diazepan-1-yl) -3-chlorobenzoic acid methyl ester The residue obtained in example le (1.00 g, 3.72 mmol) is mixed in 10 ml. of dichloromethane with 0.53 g (3.80 mmol) of potassium carbonate and then 0.83 g (3.80 mmol) of pyrocarbonic acid di-tert-butyl ester are added dropwise. Then, it is stirred for 16 hours at room temperature. It is then diluted with dichloromethane, washed twice with water, dried over sodium sulfate and concentrated a.v. The purification is then carried out by chromatography on silica gel (eluent: methylene chloride / ethanol 99: 1). Yield: 1.34 g (98%).

Rf value # 0.50 (silica gel, dichloromethane / ethanol = 50: 1). Ca8H25ClN204 (368.86). Mass spectrum: (M + H) + = 369/371 (chlorinated isotope). (e) 4- (4-N-Boc- [1,4] diazepan-1-yl) -3-chlorobenzoic acid 0.60 g (1.63 mmol) of 4- (4-N-Boc) methyl ester are dissolved. [1,4] diazepan-1-yl) -3-chlorobenzoic acid in 10 ml of methanol, mixed with 4 ml of 2M potassium hydroxide solution and stirred for 3 hours at 40 ° C. Then concentrate a.v., dilute the residue with distilled water, acidify with a saturated solution of potassium hydrogen sulfate and extract three times with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated. The residue is reacted again without further purification. Yield: 0.50 g (87%). Rf value: 0.05 (silica gel, dichloromethane / ethanol = 50: 1). C? 7H23Cl? 204 (354.84). (f) 4- (4-N-Boc- [1,4] Diazepan-1-yl) -3-chloro-N- [(15) -1- (5-chloro-li? -benzimidazol-2-yl) ) ethyl] benzamide 532 mg (1.50 mmol) of 4 ~ (4-N-Boc [1,4] diazepan-1-yl) -3-chlorobenzoic acid are suspended in 15 ml of THF and, after the addition of 546 mg (1.70 mmol) of TBTU and 646 mg (5.0 mmol) of DIPEA is stirred for 30 minutes at room temperature. Then, 403 mg (1.50 mmol) of (15) -1- (5-chloro-li? -benzimidazol-2-yl) ethylamine dihydrochloride is added and stirred for another 16 hours at room temperature. After concentrating a.v., the residue is dissolved in ethyl acetate, the organic phase is washed with a 5% sodium hydrogen carbonate solution and water and dried over sodium sulfate. After concentrating a.v., the remaining residue is purified by chromatography on silica gel (gradient eluent: petroleum ether / ethyl acetate: 90:10 -> 60:40). Yield: 630 mg (79%). Rf value: 0.50 (silica gel, dichloromethane / ethanol = 19: 1). C26H3? Cl2N503 (532.48). Mass spectrum: (M + H) + = 532/534/536 (chlorinated isotope). (g) 3-Chloro-N- [(15) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -4- ([1,4] diazepan-1-yl) benzamide. solution of 610 mg (1.15 mmol) of 4- (4-N-Boc [1,4] diazepan-1-yl) -3-chloro-N- [(1S) -1- (5-chloro-1H-benzimidazole -2-yl) ethyl] -benzamide in 30 ml of dichloromethane with 3 ml of TFA and stirred for 3 hours at room temperature. Then concentrate a.v., collect the residue in ethyl acetate, wash with a 5% sodium hydrogen carbonate solution and water and dry over sodium sulfate. After concentrating a.v., the residue is purified by chromatography on silica gel (gradient eluent: petroleum ether / ethyl acetate 80:20 -> 50:50). Yield: 380 mg (77%). Rf value: 0.10 (silica gel, dichloromethane / ethanol = 9: 1). C2? H23Cl2N50 (432.36). Mass spectrum: (M + H) + = 432/434/436 (chlorinated isotope). The following compound was prepared analogously: EXAMPLE 2 4- (4-N-Boc-Piperazin-1-yl) -N- [(1S) -1- (5-chloro-1-yl-benzimidazol-2-yl) ethyl] -3-trifluoromethyl-benzamide (a) 4- (Piperazin-1-yl) -3-trifluoromethylbenzoic acid 37.9 g (195 mmol) of piperazine hexahydrate are suspended with 12.4 g (66 mmol) of 4-fluoro-3-trifluoromethylbenzonitrile in 40 ml of ethanol for 2 hours. reflux hours. Then, 13.7 ml (261 mmol) of 50% sodium hydroxide solution and 13.7 ml of water are added, the mixture is heated at reflux for a further 3.5 hours and maintained at room temperature for a further 15 hours. Then, 43.5 ml of conc. Hydrochloric acid are added. and it is cooled at 10 ° C for 30 minutes with stirring. The precipitate obtained is filtered off with suction, washed with little water and dried for 24 hours at 40 ° C in a drying chamber with air recirculation. Yield: 20.8 g (quantitative). (b) 4- (Piperazin-1-yl) -3-trifluoromethylbenzoic acid methyl ester 5.00 g (18.2 mmol) of 4- (piperazin-1-yl) -3-trifluoromethylbenzoic acid in 50 ml of methanolic hydrochloric acid are stirred. for 16 hours. After concentrating the reaction mixture a.v., the residue is stirred with isopropanol. The solid is filtered off, washed with diethyl ether and dried at 60 ° C in a drying chamber with air recirculation. Yield: 5.00 g (76%). C? 3H? 5F3N202 * 2 HCl (288.27 / 361.19). Mass spectrum: (M + H) + = 289. Rf value: 0.58 (silica gel; cyclohexane / dichloromethane / methanol = 70:15:15 + 2% conc. Ammonia solution). (c) 4- (4-N-Boc-piperazin-1-yl) -3-trifluoro-methylbenzoic acid methyl ester 5.77 g (11.78 mmol) of 4- (piperazin-1-yl) methyl ester are available. -3-trifluoromethylbenzoic acid in 100 ml of THF and mixed with 4.47 g (20.5 mmol) of di-tert-butyl ester of pyrocarbonic acid. After 40 hours at room temperature under a nitrogen atmosphere, the reaction mixture is concentrated a.v., the residue is mixed with water and a sat. of sodium chloride and extracted with ethyl acetate. The combined organic phases are washed with water, a semi-saturated solution and a saturated sodium chloride solution, dried over magnesium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (eluent gradient: petroleum ether / ethyl acetate 9: 1 -> 8: 1). Yield: 2.60 g (34%). Rf value: 0.52 (silica gel, petroleum ether / ethyl acetate 7: 3 + 1% conc. Ammonia solution). C? 8H23F3N204 (388.39). Mass spectrum: (M + H) + = 389. (d) 4- (4-N-Boc-piperazin-1-yl) -3-trifluoromethylbenzoic acid 2.60 g (6.69 mmol) of 4- (4-N-tert-butyloxycarbonylpiperazin-1-yl) methyl ester are dissolved. ) -3-trifluoromethylbenzoic acid in 10 ml of methanol and mixed with 12. 3 ml (12.3 mmol) of 1 M sodium hydroxide solution. After 15 minutes, another 10 ml of methanol are added and the reaction mixture is stirred for 42 hours at room temperature. Then, concentrate a.v., mix the residue with ice and acidify with acetic acid. The precipitate obtained is filtered off with suction, washed with water and dried in a drying chamber with recirculation of air at 50 ° C, as well as with a drying gun at 40 ° C on KOH and Si02. Yield: 2.40 g (96%). Rf value: 0.41 (silica gel; petroleum ether / ethyl acetate = 1: 1 + 1% acetic acid). C? 7H2? F3? 204 (374.36).

Mass spectrum: (M-H) = 373. (e) 4- (4-N-Boc-Piperazin-1-yl) -N- [(SS) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -3-trifluoromethylbenzamide Prepared analogously to example lf from 4- (4-N-Boc-piperazin-1-yl) -3-trifluoromethylbenzoic acid, TBTU,? MM and (1S) -1- (5-chloro-l-benzimidazol-2-yl) ethylamine in? MP and subsequent purification by chromatography on silica gel (eluent: petroleum ether / ethyl acetate = 50:50). Yield: 57%. Rf value: 0.20 (silica gel; petroleum ether / ethyl acetate = 1: 1). C26H29C1F3? 503 (552.00). Mass spectrum: (M + H) + = 552/554 (chlorinated isotope).

Example 3 N- [(SS) -1- (5-Chloro-1-benzimidazol-2-yl) ethyl] -4- (piperazin-1-yl) -3-trifluoromethyl-benzamide Prepared analogously to the example Ig from 4- (4-N-Boc-piperazin-1-yl) -N- [(SS) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -3 -trifluoromethyl'-benzamide and TFA in dichloromethane. Yield: 73% Rf value: 0.28 (silica gel, dichloromethane / methanol = 90:10 + ammonia solution). C21H2? ClF3N50 * 2 CF3COOH (679.93 / 451.88). Mass spectrum: (M + H) + = 452/454 (chlorinated isotope). Analogously to the sequence described in example 2 and 3 were prepared: Example 5 4- (4-N-Acetylpiperazin-1-yl) -N- [(15) -1- (5-chloro-1 H -benzimidazol-2-yl) ethyl] -3-trifluoromethylbenzamide 220 mg (0.32 mmol) of N- [(1S) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- (piperazin-1-yl) -3-trifluoromethylbenzamide ditrifluoroacetate are mixed. in 5 ml of THF with 0.23 ml (1.65 mmol) of TEA, 50 μl (0.70 mmol) of acetyl chloride are added dropwise with stirring and cooling in an ice bath and stirred for 2 hours at room temperature. The reaction mixture is poured into ice water and then extracted with ethyl acetate. The organic phase is washed with water and a sat. of sodium chloride, dried over sodium sulfate and concentrated a.v. The residue is triturated with a solvent mixture of ethyl acetate and diethylether, filtered off, washed with diethyl ether and dried with a drying gun at 50 ° C. Yield: 0.13 g (81%). Rf value: 0.55 (silica gel, dichloromethane / ethanol = 9: 1 + ammonia solution).

C23H23C1F3 502 (493.92). Mass spectrum: (M + H) + 494/496 (chlorinated isotope).

Example 6 4- (Azepan-2-on-l-il) -N- [(15) -1- (5-chloro-lff-benzimidazol-2-yl) ethyl] -3-methylbenzamide (a) 4- (6-Bromohexanoylamino) -3-methylbenzoic acid methyl ester A solution of 2.14 g (10 mmol) of 6-bromohexanoyl chloride in 5.0 ml of THF at 1.65 g (10 mmol) is slowly added dropwise. ) of 4-amino-3-methylbenzoic acid methyl ester in 50 ml of THF with 2 ml of DIPEA with stirring at room temperature.After 16 hours of stirring at room temperature, concentrate to v, dissolve the residue in dichloromethane, wash twice with water and dry over sodium sulfate The remaining residue after concentrating ak is reacted again without further purification Yield: 3.30 g (96%) Rf value: 0.40 (silica gel; ethyl acetate = 4: 1) .Ci5H2oBr 03 (342.24). (b) 4- (Azepan-2-on-l-yl) -3-methylbenzoic acid methyl ester 3.20 g (9.35 mmol) of the product obtained in example 5a in a freshly prepared solution of 1.00 g (43.5 mmol) of sodium in 80 ml of methanol for 4 hours Then concentrate a.v., acidify the residue with 2 M acetic acid and extract with ethyl acetate. The combined organic phases are washed with water and dried over sodium sulfate. The residue obtained a.v. after concentrating it is reacted again without further purification. Yield: 1.90 g (unpurified product). Rf value: 0.30 (silica gel, dichloromethane / ethanol = 50: 1). C? 5H19N03 (261.32). Mass spectrum: (M + H) + = 262. (c) 4- (Azepane-2-on-l-yl) -3-methylbenzoic acid 1.90 g of the product obtained in the example are mixed 5b in 30 ml of methanol with 10 ml of 2 M sodium hydroxide solution and stirred for 16 hours at room temperature. After a.v. concentration, the residue is mixed with water and acidified with conc. Hydrochloric acid. The precipitate that appeared is filtered off with suction and dried. After dissolution in methanol and extraction on silica gel, purification is carried out by chromatography on silica gel (gradient eluent: petroleum ether / ethyl acetate 70:30 -> 50:50). Yield: 0.23 g (10% in 2 stages). Rf value: 0.10 (silica gel; petroleum ether / ethyl acetate = 1: 2). C? 4H? 7N03 (247.30). Mass spectrum: (M + H) + = 248. (d) 4- (Azepan-2-on-l-yl) -N- [(SS) -1- (5-chloro-lff-benzimidazole-2- il) ethyl] -3-methylbenzamide Prepared analogously to example lf from 4- (azepan-2-on-l-yl) -3-methylbenzoic acid, TBTU, DIPEA and (1S) -1- (5-chloro- li? -benzimidazol-2-yl) ethylamine in THF and further purification by chromatography on silica gel (gradient eluent: ethyl acetate / ethanol 95: 5 - >; 90:10). Yield: 61%. Rf value: 0.30 (silica gel, ethyl acetate). C23H25C1? 02 (424.93). Mass spectrum: (M + H) + = 425/427 (chlorinated isotope). Analogously, the following compounds were prepared: Example 9 N- [(1S) -1- (5-Chloro-1-benzimidazol-2-yl) ethyl] (pyrrolidin-2-on-l-yl) benzamide (a) 4- (Pyrrolidin-2-on-1-yl) benzoic acid. 19.2 g (140 mmol) of 4-aminobenzoic acid are heated to reflux together with 25.8 ml (180 mmol) of 4-bromobutyric acid ethyl ester in 100 ml of DMF for 20 hours. After a.v. concentration, the residue is mixed with 100 ml of water and 50 ml of petroleum ether and stirred vigorously for 50 minutes. The precipitate is filtered off, crystallized from ethanol and dried at 80 ° C. Yield: 9.36 g (33%). C11H11? O3 (205.22) .. Mass spectrum: (M + H) + = 206. (b) N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) ethyl] -4- (pyrrolidin-2-on-l-yl) benzamide Prepared analogously to example lf from 4- (pyrrolidin-2-on-l-yl) benzoic acid, TBTU, DIPEA and (1S) -1- (5-chloro-lH-benzimidazol-2-yl) ethylamine in THF and subsequent purification by washing the solution of the residue in ethyl acetate with water, dilute sodium carbonate solution, water and sat. of sodium chloride, dried over sodium sulfate and removal of the solvent a.v. Yield: 61%. Rf value: 0.50 (silica gel, dichloromethane / ethanol = 9: 1). C20H19C1N402 (382.85). Mass spectrum: (M + H) + = 383/385 (chlorinated isotope).

Example 12 3-Chloro-N- [(15) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -4- (4-N-methyl [1,4] diazepan-1-yl) benzamide (a) 3-Chloro-4- (4-N-methyl [1,4] diazepan-1-yl) benzonitrile Prepared analogously to the example from 3-chloro-4-fluorobenzonitrile and 1-methyl [1,4 ] diazepane in DIPEA with subsequent purification by chromatography on silica gel (eluent gradient: dichloromethane / ethanol 98: 2 -> 94: 6). Performance: 71%.

Rf value: 0.20 (silica gel; methylene chloride / ethanol = 19: 1). C13H? 6ClN3 (249.75). Mass spectrum: (M + H) + = 250/252 (chlorinated isotope). (b) 3-Chloro-4- (4-N-methyl [1,4] diazepan-1-yl) benzoic acid Prepared analogously to Example Ib from 3-chloro-4- (4-methyl [1,4]) ] diazepan-1-yl) benzonitrile in a 25% aqueous potassium hydroxide solution. Performance: 99%. C13H1C1? 202 * HCl (268.74 / 305.21). Mass spectrum: (M + H) + = 269/271 (chlorinated isotope). (c) 3-Chloro-N- [(SS) -1- (5-chloro-li-benzimidazol-2-yl) ethyl] -4- (4-N-methyl [1,4] diazepan-1-yl) ) Benzamide Prepared analogously to the If example from 3-chloro-4- (4-methyl [1,4] diazepan-1-yl) benzoic acid, (S) -l- (5-chloro-lH-benzimidazole-2) -yl) ethylamine, TBTU and DIPEA in THF with subsequent purification by chromatography on silica gel (eluent gradient: petroleum ether / ethyl acetate 50:50 - > 20:80). Yield: 34%.

Rf value: 0.30 (silica gel, dichloromethane / ethanol = 9: 1 + 1% ammonia solution). C22H25C12N50 (446.38). Mass spectrum: (M + H) + = 446/448/450 (chlorinated isotope).

Example 13 3-Chloro-N- [(15) -1- (5-chloro-1-yl-benzimidazol-2-yl) ethyl] -4- (2-methylpyrrolidin-1-yl) benzamide (a) 3-Chloro-4- (2-methylpyrrolidin-1-yl) benzonitrile 5.90 g (37.9 mmol) of 3-chloro-4-fluorobenzonitrile are dissolved under nitrogen in 65 ml of DMF and mixed with 5.45 g. (39.5 mmol) of potassium carbonate and 4.2 ml (3.5 g, 39.5 mmol) of 2-methylpyrrolidine. After stirring for 2.5 days at 90 ° C, the reaction mixture is poured into 400 ml of water and extracted with ethyl acetate. The combined organic phases are washed several times with a dilute solution and sat. of sodium chloride, dried over magnesium sulfate and concentrated a.v. The remaining residue is further reacted without further purification.

Yield: 7.90 g (94%). Rf value: 0.40 (silica gel, petroleum ether / ethyl acetate - 9: 1 + 0.5% ammonia solution). C 2 H 3 ClN 2 (220.70). Mass spectrum: (M + H) + = 221/223 (chlorinated isotope). (b) 3-Chloro-4- (2-methylpyrrolidin-1-yl) benzoic acid 8.0 g (40 mmol) of the product obtained in example 13a are stirred in a mixture of 65 ml of 10 M sodium hydroxide solution and 65 ml of ethanol for 2.75 hours at 90 ° C. After, pour the reaction mixture into ice water, mix with conc. hydrochloric acid. and they concentrate a.v. the volatile organic components. The remaining aqueous phase is extracted with dichloromethane, mixed with ice and adjusted to pH 4.5 with half-concentrated hydrochloric acid and a 2 N potassium hydrogen sulfate solution. The precipitate which is created is stirred for another 10 minutes, then it is separated by filtration, Wash with water and dry at 55 ° C. Yield: 8.30 g (87%). Rf value: 0.55 (silica gel; petroleum ether / ethyl acetate = 6: 4 + 1% acetic acid). C? 2H? 4ClN02 (238.72). Mass spectrum: (M + H) + = 240/242 (chlorinated isotope). (c) 3-Chloro-N- [(15) -1- (5-chloro-lff-benzimidazol-2-yl) ethyl) -4- (2-methylpyrrolidin-1-yl) benzamide Prepared analogously to example lf a from 3-chloro-4- (2-methylpyrrolidin-1-yl) benzoic acid, (1S) -l- (5-chloro-1-benzimidazol-2-yl) ethylamine, TBTU and TEA in DMF, then precipitation by poured into a dilute sodium hydrogen carbonate solution, separation by filtration and washing with water. It is then dried at 55 ° C. Yield: 92%. Rf value: 0.66 (silica gel, dichloromethane / ethanol = 9: 1). C2? H22Cl2? 40 (417.34). Mass Spectrum: (M-H) "= 415/417/419 (chlorinated isotope) The following compounds were analogously prepared: Example 21 N- [(IR) -1- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4-yl) -3-trifluoromethylbenzamide (a) 4- (Morpholin-3-on-4-yl) -3-trifluoromethylbenzoic acid 1.00 g (3.63 mmol) of 4- (morpholin-4-yl) -3-trifluoromethylbenzoic acid (prepared by a sequence) is suspended. of synthesis analogous to example 13a and 13b) in 40 ml of water, and 150 mg (3.75 mmol) of sodium hydroxide are added. Then, 1.73 g (10.92 mmol) of potassium permanganate are added and the mixture is stirred for 1.5 hours at 45 ° C. Then, the reaction mixture is cooled in an ice bath and sodium thiosulfate is added until complete decolorization. After 3 extractions with ethyl acetate, the organic phases are dried over sodium sulfate and concentrated a.v. After placing the residue on silica gel, this is purified by chromatography on silica gel (eluent: dichloromethane / methanol 95: 5). Yield: 340 mg (32%). C12H? 0F3? O (289.21).

Mass spectrum: (M + H) + = 290. (b) N'- (2-Amino-4-chlorophenyl) -N-Boc- (S) -Q-methylserinamide and N'- (2-amino-5-chlorophenyl) '-N-Boc- (5) - 0-methylserinamide 30.0 g (137 mmol) of N-Boc- (S) -0-methylserine are dissolved together with 21.9 g (154 mmol) of 4-chloro-l, 2-phenylenediamine in 658 ml of THF and added with ice bath stirring 43.9 ml (316 mmol) of triethylamine as well as 103 ml (173 mmol) of a 50% PPA solution in ethyl acetate. After 15 minutes of stirring in an ice bath, the reaction mixture is warmed to room temperature, poured into water and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with a sat. of sodium carbonate and water, dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (eluent gradient: dichloromethane / methanol = 30: 1 -> 9: 1). Yield: 33.47 g (72%) of mixture of both regioisomers. C? 5H22Cl? 304 (343.81). Mass spectrum: (M-H) "= 342/344 (chlorinated isotope), Rf value: 0.80 (silica gel, dichloromethane / methanol = 9: 1). (c) (l £) -N-Boc-l- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethylamine 26.01 g (75.65 mmol) of the mixture obtained in Example 21b are dissolved in 1500 ml of toluene and 20.8 ml (364.mmol) of acetic acid are added as well as 10.0 g of molecular sieves of 4Á. The reaction mixture is stirred for 5 hours at 60 ° C. The reaction mixture is filtered, washed with ethyl acetate and the organic phases are washed with a semisat solution. of sodium hydrogen carbonate, dried over sodium sulfate and concentrated a.v. The residue is stirred with diethyl ether and the crystals created are filtered off with suction. The a.v. filtrate is concentrated. and the residue was purified by triple chromatography on silica gel (gradient eluent: dichloromethane / methanol 80: 1 -> 50: 1). Yield: 13.85 g (56%). C15H2oCl? 3? 3 (325.79). Mass spectrum: (M + H) + = 326/328 (chlorinated isotope). Rf value: 0.29 (silica gel, dichloromethanol / methanol = 30: 1). (d) (IR) -1- (5-Chloro-l-benzimidazol-1-yl) -2-methoxyethylamine 0.50 g (1.54 mmol) of (IR) -N-Boc-1- (5-chloro) is mixed. -lH-benzimidazol-2-yl) -2-methoxyethylamine in 1.5 ml of dichloromethane with 1.54 ml (20.0 mmol) of TFA, and stirred at room temperature for 2 h. Then, pour the mixture into a sat solution. of sodium hydrogen carbonate and the aqueous phase is extracted after mixing well with dichloromethane and ethyl acetate. The combined organic phases are dried over sodium sulfate and purified by chromatography on silica gel (eluent: dichloromethane / methanol = 9: 1 + 1% conc. Ammonia solution). Yield: 0.35 g (quant.). C? 0H12ClN3O (225.68). Mass spectrum: (M-H) "= 224/226 (chlorinated isotope) Rf value: 0.40 (silica gel, dichloromethane / methanol 9: 1 + 1% conc. Ammonia solution). (e) N- [(IR) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4-yl) -3-trifluoromethylbenzamide Prepared analogously to the If example from 4- (morpholin-3-on-4-yl) -3-trifluoromethylbenzoic acid, (li?) - l- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethylamine, TBTU and? MM in DMF, then precipitation by pouring in water, separation by filtration and drying Performance: 63%. Rf value: 0 57 (silica gel, dichloromethane / methane = 9: 1). C22H20ClF3? 4O4 (496.88).

Mass spectrum: (M + H) + = 497/499 (chlorinated isotope). The following compounds were prepared analogously: EXAMPLE 22 N- [(L1?) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholin-3-) on-4-yl) benzamide Prepared analogously to Example 1f from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid (prepared by a synthesis sequence analogous to example 30a, 2d and 21a), (IR) -1- (5-chloro-li? -benzimidazol-2-yl) -2-methoxyethylamine, TBTU and NMM in DMF, then poured into water, extraction with ethyl acetate, drying over sodium sulfate, concentration and purification by chromatography on silica gel (eluent gradient: ethyl acetate / isopropanol / ethanol 9: 1: 0 -> 9: 0: 1). Performance: 99%. Rf value: 0.13 (silica gel, dichloromethane / isopropanol = 19: 1). C22H23C1N04 (442.91). Mass spectrum: (M + H) + = 443/445 (chlorinated isotope). The following examples were similarly prepared: Example 27 N- [(15) -1- (5-Chloro-l-benzimidazol-2-yl) ethyl] (morpholin-3-on-4-yl) benzamide 254 mg (1.15 mmol) of 4- (morpholin-3-on-4-yl) benzoic acid (prepared by a synthetic sequence analogous to example 30a, 2d and 21a) are placed in 5 ml of DMF and 428 mg are added (1.0 mmol) of PfTU as well as 514 μl (3.0 mmol) of DIPEA. After stirring at room temperature for 10 minutes, 232 mg (1.0 mmol) of (15) -1- (5-chloro-l-benzimidazol-2-yl) ethylamine hydrochloride is added and stirred at room temperature for 16 hours. . Then, the reaction mixture is filtered through basic aluminum oxide and concentrated a.v. The residue is purified by chromatography on silica gel (gradient eluent: dichloromethane / methanol 100: 0 -> 90:10), the corresponding a.v. fractions are concentrated, the residue is dissolved in acetonitrile / water and lyophilized. Performance: 77%. C20H? 9ClN4O3 (398.85). Mass spectrum: (M + H) + = 399/401 (chlorinated isotope). The following compound was prepared analogously: Example 29 N- [(SS) -1- (5-Chloro-1 H -benzimidazol-2-yl) ethyl] -3-methyl-4- (4-N-methyl [1,4] diazepan-1-yl) benzamide (a) 4-Fluoro-3-methylbenzoic acid chloride 14.00 g (90.8 mmol) of 4-fluoro-3-methylbenzoic acid are heated at reflux together with 50 ml of thionyl chloride for 1 hour, and then concentrated a.v. The residue is reacted again without further purification. Yield: 15.70 g (quantitative). C8H6C1F0 (172.59). (b) 4-Fluoro-3-methylbenzamide 15.70 g (91.0 mmol) of 4-fluoro-3-methylbenzoic acid chloride dissolved in 30 ml of THF are added dropwise to 300 ml of conc. of ammonia, and then stirred for 2 hours at room temperature. The precipitate created is filtered off, washed with water and dried. Yield: 10.00 g (72%). C8H8FNO (153.16). Rf value: 0.31 (aluminum oxide, dichloromethane / methanol = 50: 1). (c) 4-Fluoro-3-methylbenzonitrile 10.00 g (65.29 mmol) of 4-fluoro-3-methylbenzoic acid amide are stirred together with 50 ml of phosphorus oxychloride for 4 hours at 60 ° C, and then concentrated a.v. The residue is poured into ice water, the created precipitate is filtered off and washed with water. After collecting in ethyl acetate, the organic phase is washed with a sat. of potassium carbonate, dried over sodium sulfate and completely concentrated a.v. Yield: 8.00 g (91%). C8H6FN (135.14). Rf value: 0.84 (silica gel, dichloromethane). (d) 3-Methyl-4- (4-N-methyl [1,4] diazepan-1-yl) benzonitrile 7.00 g (51.8 mmol) of 4-fluoro-3-methylbenzonitrile are heated together with 1-N-methyl [1, 4] diazepane for 1 week with shaking at 110 ° C. After concentrating a.v., the residue is separated off in aluminum oxide (eluent: dichloromethane) and the corresponding fractions are again purified on silica gel (gradient eluent: dichloromethane / methanol 100: 1 -> 9: 1). Yield: 1.70 g (14%). C? 4H19? 3 (229.33). Mass spectrum: (M + H) + = 230. Rf value: 0.25 (silica gel; dichloromethane / methanol = 9: 1). (e) 3-Methyl-4- (4-N-methyl [1,4] diazepan-1-yl) benzoic acid Prepared analogously to Example Ib from 3-methyl-4- (4-N-methyl) [1] , 4] diazepan-1-yl) benzonitrile with a 25% potassium hydroxide solution by refluxing for 36 hours. After a.v. concentration, the residue is separated off in aluminum oxide (eluent: dichloromethane) and the corresponding fractions are again purified on silica gel (gradient eluent: dichloromethane / methanol 100: 1 -> 9: 1). Yield: 14%. C? 4H? 9? 202 (248.33). Mass spectrum: (M + H) + = 249. Rf value: 0.30 (RP-18, methanol / 5% sodium chloride aqueous solution = 6: 4). (f) 3-Methyl-4- (4-N-methyl [1,] diazepan-1-yl) benzoic acid chloride Prepared analogously to Example 29a from 3-methyl-4- (4-N-methyl) acid [1,4] diazepan-1-yl) benzoic acid and thionyl chloride. Performance: quantitative. C? 4H? 9Cl? 20 * HCl (266.77 / 303.23). (g) N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) ethyl] -3-methyl-4- (4-N-methyl [1,4] diazepan-1-yl) ) benzamide 489 mg (1.61 mmol) of 3-methyl-4- (4-N-methyl [1,] diazepan-1-yl) benzoic acid chloride together with 400 mg (3.96 mmol) of TEA in 10 ml are prepared. of THF at room temperature, and a solution of 433 mg (1.61 mmol) of (1S) -1- (5-chloro-li? -benzimidazol-2-yl) ethylamine is added dropwise with stirring. After 16 hours of stirring at ambient temperature, the mixture is concentrated a.v., the residue is mixed with water and extracted with ethyl acetate. The combined organic phases are washed with a sat. of sodium chloride, dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on aluminum oxide (eluent: dichloromethane / methanol 100: 1). The concentrated fractions are treated with hydrochloric acid in ether, after the total concentration, the mixture is evaporated twice with ethyl acetate and diethyl ether and dried a.v. at 70 ° C. Yield: 120 mg (16%). C23H28C1? 50 * HCl (462.43 / 425.96). Mass spectrum: (M + H) + = 426/428 (chlorinated isotope). Rf value: 0.47 (aluminum oxide, dichloromethane / methanol 19: 1) EXAMPLE 30 N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) -ethyl] -3-methyl-4- (piperazin-1-yl) benzamide (a) 4- (N-Boc-piperazin-1-yl) -3-methylbenzoic acid methyl ester 4.00 g (17.5 mmol) of 4-bromo-3-methylbenzoic acid methyl ester are suspended together with 3.92 g (21.0) mmol) of N-Boc-piperazine, 39.2 mg (175 μmol) of palladium (II) acetate, 50.7 mg (175 μmol) of tri-tert-butylphosphonium tetrafluoroborate and 11.12 g (52.4 mmol) of potassium phosphate in 35 g. ml of toluene, and heated under an argon atmosphere in a microwave oven for 10 minutes at 150 ° C. The reaction mixture is then poured into water, stirred vigorously and extracted 3 times with ethyl acetate. The combined organic phases are dried over sodium sulfate, placed on silica gel and purified by chromatography on silica gel (eluent: dichloromethane / methanol 80: 1). Yield: 1.42 g (24%). C? 8H26? 204 (334.42). Mass spectrum: (M + H) + = 335. Rf value: 0.52 (silica gel; dichloromethane / methanol = 50: 1). (b) 4- (N-Boc-piperazin-1-yl) -3-methylbenzoic acid 1.42 g (4.24 mmol) of 4- (N-Boc-piperazin-1-yl) -3- methyl ester are dissolved. methylbenzoic acid in 7 ml of THF and 9.25 ml of water and 893 mg (21.3 mmol) of lithium hydroxide monohydrate are added. After stirring for 16 hours at room temperature, it is heated for 2 hours at 45 ° C. Then, 893 mg (21.3 mmol) of lithium hydroxide monohydrate is added again and stirred at room temperature for 4 days. Then, it is neutralized with 1 M hydrochloric acid and the reaction mixture is extracted with ethyl acetate. Dry the combined organic phases over sodium sulfate and concentrate completely a.v. Yield: 1.29 g (95%). C? 7H24? 204 (320.39). Mass spectrum: (M + H) + = 321. Rf value: 0.29 (silica gel; dichloromethane / methanol = 15: 1). (c) 4- (N-Boc-Piperazin-1-yl) -N- [(15) -1- (5-chloro-lff-benzimidazol-2-yl) ethyl) -3-methylbenzamide Prepared analogously to example lf from 4- (N-Boc-piperazin-1-yl) -3-methylbenzoic acid, (lS) -l- (5-chloro-li? -benzimidazol-2-yl) ethylamine, TBTU and? MM in DMF , then stirring in a conc. of sodium hydrogen carbonate, extraction with ethyl acetate, drying over sodium sulfate, a.v. and purification of the residue by chromatography on silica gel (gradient eluent: dichloromethane / methanol 50: 1 -> 15: 1). Performance: 85%. Rf value: 0.15 (silica gel, dichloromethane / methanol = 30: 1). C26H32C1N503 (498.03). Mass spectrum: (M + H) + = 498/500 (chlorinated isotope). (d) N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) ethyl] -3-methyl-4- (piperazin-1-yl) benzamide Prepared analogously to the example Ig from 4- (N-Boc-piperazin-1-yl) -N- [(15) -1- (5-chloro-l-benzimidazol-2-yl) ethyl) -3-methylbenzamide and TFA in dichloromethane. Performance: quantitative. C2? H24Cl? 50 (397.91). Mass spectrum: (M + H) + = 398/400 (chlorinated isotope). Rf value: 0.14 (silica gel, dichloromethane / methanol = 9: 1). The following compound was prepared analogously: Example 31 N- [(1S) -1- (5-Chloro-1-phenyl-benzimidazol-2-yl) ethyl] -3-methyl-4- (piperazin-2-on-1-yl) benzamide (a) 4- (N-Boc-piperazin-2-on-l-yl) -3-methylbenzoic acid methyl ester 758 mg (3.31 mmol) of 4-bromo-3-methylbenzoic acid methyl ester are suspended together with 796 mg (21.0 mmol) of 4-N-Boc-piperazin-2-one, 31.8 mg (167 μmol) of copper iodide (I), 35.1 μl (330 μmol) of N ^ N'-dimethylethylenediamine and 0.92 g (6.62 mmol) of potassium carbonate in 6.6 ml of toluene and heated under an argon atmosphere in a microwave oven with stirring for 1.5 hours at 140 ° C. The reaction mixture is then poured into water, stirred vigorously and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate, placed on silica gel and purified by chromatography on silica gel (eluent: dichloromethane / methanol 50: 1). Yield: 679 mg (59%). C18H24N205 (348.40). Mass spectrum: (M + H) + = 349. Rf value: 0.25 (silica gel, dichloromethane / methanol = 50: 1). (b) 4- (N-Boc-piperazin-2-on-l-yl) -3-methylbenzoic acid 775 mg (2.22 mmol) of 4- (N-Boc-piperazin-2-on) methyl ester are dissolved. -l-yl) -3-methylbenzoic acid in 3.7 ml of THF and 4.9 ml of water are added as well as 468 mg (11.2 mmol) of lithium hydroxide monohydrate. After stirring for 16 hours at room temperature, it is neutralized with 1 M hydrochloric acid and the reaction mixture is extracted with ethyl acetate. Dry the combined organic phases over sodium sulfate and concentrate completely a.v. Yield: 664 mg (89%). C? 7H22? 205 (334.38).

Mass spectrum: (M + H) + = 335. Rf value: 0.31 (silica gel, dichloromethane: methanol = 15: 1). (c) 4- (N-Boc-Piperazin-2-on-l-yl) -N- [(15) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl) -3-methylbenzamide Prepared analogously to the If example from 4- (N-Boc-piperazin-1-yl) -3-methylbenzoic acid, (15) -1- (5-chloro-li? -benzimidazol-2-yl) ethylamine, TBTU and ? MM in DMF, then stirring in a conc. of sodium hydrogen carbonate, extraction with ethyl acetate, drying over sodium sulfate, a.v. and purification of the residue by chromatography on silica gel (eluent: dichloromethane / methanol 30: 1). Performance: 71%. Rf value: 0.30 (silica gel, dichloromethane / methanol = 15: 1). C 26 H 30 Cl 5 O 4 (512.01). Mass spectrum: (M + H) + = 512/514 (chlorinated isotope). (d) N- [(SS) -1- (5-Chloro-1-benzimidazol-2-yl) ethyl] -3-methyl-4- (piperazin-2-on-1-yl) benzamide Prepared analogously to the example Ig from 4- (N-Boc-piperazin-1-yl) -N- [(15) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -3-methylbenzamide and TFA in dichloromethane . Performance: 36%. C21H22C1N502 (411.90). Mass spectrum: (M + H) + = 412/414 (chlorinated isotope). Rf value: 0.42 (silica gel, dichloromethane / methanol = 9: 1). Analogously, the following compounds were prepared: For example 32 N- [(ÍS) -1- (5-Chloro-lH-benzimidazol-2-yl) ethyl] -3-methyl-4- (piperidin-2-on-l-yl) benzamide (a) 3-Methyl-4- (piperidin-2-on-1-yl) benzoic acid methyl ester Prepared analogously to Example 31a from 4-bromo-3-methylbenzoic acid methyl ester and piperidin-2-one in the presence of copper iodide (I), N, N'-dimethylethylenediamine and potassium carbonate in toluene and dioxane under argon. Yield: 34%. C? 4H? 7? 03 (247.30). Mass spectrum: (M + H) + = 248. Rf value: 0.21 (silica gel, petroleum ether / ethyl acetate = 1: 1). (b) 3-Methyl-4- (piperidin-2-on-1-yl) benzoic acid Prepared analogously to Example 2d from 3-methyl-4- (piperidin-2-on-1-yl) methyl ester ) benzoic acid and 1 M sodium hydroxide solution in methanol. Performance: 83%.

C13H15 O3 (233.27). Mass spectrum: (M + H) + = 234. Rf value: 0.51 (silica gel; ethyl acetate / ethanol = 9: 1 + 1% conc. Ammonia solution). (c) N- [(15) -1- (5-Chloro-lff-benzimidazol-2-yl) ethyl) -3-methyl-4- (piperidin-2-on-l-yl) benzamide Prepared analogously to the example lf from 3-methyl-4- (piperidin-1-yl) benzoic acid, (15) -1- (5-chloro-l-benzimidazol-2-yl) ethylamine, TBTU and? MM in DMF, and after stirring in ice water, mixed with an ammonia solution, filtered, collected in dichloromethane, concentration and purification of the residue by chromatography on silica gel (gradient eluent: ethyl acetate / (methanol / conc. solution of ammonia 19: 1) 1: 0 -> 9: 1). Performance: 32%. Rf value: 0.30 (silica gel; ethyl acetate / ethanol = 9: 1 + 1% acetic acid). C22H23C1? 402 (410.91). Mass spectrum: (M + H) + = 411/413 (chlorinated isotope). The following compounds were prepared analogously: Example 33 N- [(SS) -1- (5-Chloro-1-benzimidazol-2-yl) ethyl] -4- (N-methyl-piperazin-1-yl) -3-trifluoromethyl-benzamide 170 mg (0.24 mmol) of N- [(15) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -4- (piperazin-1-yl) -3-trifluoromethylbenzamide in 2 ml are suspended. of 1,2-dichloroethane and mixed under nitrogen with 20 mg (0.67 mmol) of paraformaldehyde and 76 mg (0.36 mmol) of sodium triacetoxyborohydride. After adding 5 ml of THF, the reaction mixture is stirred for 6 hours at room temperature, then 100 mg (3.33 mmol) of paraformaldehyde and 100 mg (0.47 mmol) of sodium triacetoxyborohydride are added and stirred for another 22 hours. hours at room temperature. Then, it is mixed with a sat solution. of sodium hydrogen carbonate and extracted with ethyl acetate. Dry the combined organic phases over magnesium sulfate, concentrate a.v. and purified by silica gel chromatography (eluent gradient: dichloromethane / (methanol / conc. ammonia solution 19: 1) 100: 0 -> 92: 8). Yield: 70 mg (59%). C23H25C1F3? 502 (495.94).

Mass spectrum: (M + H) + = 496/498 (chlorinated isotope). Rf value: 0.25 (silica gel, dichloromethane / methanol = 9: 1 + 1% conc. Ammonia solution).

EXAMPLE 34 N- [(SS) -1- (5-Chloro-l-benzimidazol-2-yl) -3-methylsulfonylpropyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide 150 mg (0.32 mmol) of N- [(1S) -1- (5-chloro-lF-benzimidazol-2-yl) -3-methylsulfanylprop-1-yl] -3-methyl-4- (morpholino) are placed. 3-on-4-yl) benzamide dissolved in a mixture of 10 ml of dichloromethane and 1 ml of acetic acid at -15 ° C, and mixed with 204 mg (0.89 mmol) of 3-chloroperbenzoic acid. Then, the mixture is stirred for 30 minutes at -15 ° C - -10 ° C, warmed to room temperature and stirred another 16 hours. The reaction mixture is then washed twice with a 5% sodium hydrogen carbonate solution, dried over sodium sulfate, concentrated by evaporation and purified by chromatography on silica gel (eluent: dichloromethane / ethanol 95: 5) . Yield: 80 mg (50%). C23H25C1N40SS (505.00). Mass spectrum: (M + H) + = 505/507 (chlorinated isotope). Rf value: 0.45 (silica gel, dichloromethane / ethanol = 9: 1).

Example 35 N- [(1S) -1- (5-Chloro-1 H -benzimidazol-2-yl) -3-methylsulfanylpropyl] -4- (pyrrolidin-2-on-1-yl) benzamide Prepared analogously to Example 27 from 4- (pyrrolidin-2-on-1-yl) benzoic acid, (1S) -1- (5-chloro-l-benzimidazol-2-yl) -3-methylsulfanyl-propylamine, PfTU and TEA in DMSO at room temperature and subsequent cleavage of Boc with TFA analogously to the example Ig. HPLC-MS Results: Retention time: 3.69 min. C22H23C1? 402S (442.97). Mass spectrum: (M + H) + = 443/445 (chlorinated isotope).

The following compound was prepared analogously: Example 39 N- [(15) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -3-methyl-4- ([1,3] oxazepan-2-on-3-yl) benzamide (a) 4-Isocyanato-3-methylbenzoic acid methyl ester 1.50 g (9.08 mmol) of 4-amino-3-methylbenzoic acid methyl ester dissolved in 250 ml of dioxane are mixed with 1.3 ml (10.7 mmol) of chloroformate. trichloromethyl, and heated to reflux with stirring for 5.5 hours. Next, concentrate a.v. and the residue is reacted again without further purification. Yield: 1.74 g (quantitative). C? 0H9NO3 (191.1.). (b) 4- (N- [4-chlorobutoxycarbonyl] amino) -3-methylbenzoic acid methyl ester 1.74 g (9.08 mmol) of 4-isocyanato-3-methylbenzoic acid methyl ester dissolved in 100 ml of toluene are mixed with 1.07 ml (9.11 mmol) of 85% 4-chlorobutan-l-ol. The mixture is refluxed for 17 hours with stirring. After concentrating a.v., the residue is purified by chromatography on silica gel (gradient eluent: petroleum ether / ethyl acetate 17: 3 -> 17: 4). Yield: 1.19 g (44%). C? 4H? 8Cl? 04 (299.76). Mass spectrum: (M-H) ~ = 298/300 (chlorinated isotope). Rf value: 0.45 (silica gel; petroleum ether / ethyl acetate = 80:20). (c) 3-Methyl-4- ([1,3] oxazepan-2-on-3-yl) benzoic acid methyl ester 300 mg (1.00 mmol) of 4- (N- [4-methyl] methyl ester are mixed. -chlorobutoxycarbonyl] amino) -3-methylbenzoic acid dissolved in 10 ml of DMF with 168 mg (1.50 mmol) of potassium tert-butylate, and stirred for 3 hours at 60 ° C. Water is added to the reaction mixture and extracted 3 times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated a.v. The residue is then purified by chromatography on silica gel (eluent: petroleum ether / ethyl acetate 3: 2). Yield: 160 mg (61%). Rf value: 0.26 (silica gel; petroleum ether / ethyl acetate 3: 2). C? H? 7? 04 (263.30). Mass spectrum: (M + H) + = 264. (d) 3-Methyl-4- ([1,3] oxazepan-2-on-3-yl) benzoic acid 150 mg (0.57 mmol) of methyl 3-methyl-4- ([1, 3] oxazepan-2-on-3-yl) benzoic acid in 1 ml of ethanol and mixed with 0.26 ml (0.87 mmol) of 8% aqueous lithium hydroxide solution. It is stirred for 3 hours at room temperature and then concentrated a.v. The aqueous residue is extracted 2 times with ethyl acetate, then acidified and extracted again 2 times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated a.v. Yield: 122 mg (86%).

C13H15N04 '(249.27). Mass spectrum: (M + H) + = 250. Rf value: 0.14 (silica gel, dichloromethane / methanol = 95: 5). (e) N- [(SS) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -3-methyl-4- ([1,3] oxazepan-2-on-3-yl) ) benzamide Prepared analogously to Example 1f from 3-methyl-4- ([1, 3] oxazepan-2-on-3-yl) benzoic acid, (lS) -l- (5-chloro-li? -benzimidazole) -2-yl) ethylamine, TBTU and? MM in DMF, then acidification with TFA and purification of the residue by chromatography (preparative HPLC). Yield: 54%. C22H23C1? 03 * 2 CF3COOH (654, 96/426, 90). Mass spectrum: (M + H) + = 427/429 (chlorinated isotope) Rt: 2. 42 min. Analogously, the following compounds were prepared: Example 41 N- l (15) -1- (5-Chloro-li-benzimidazol-2-yl) -3-methylsulfanylpropyl] -4- (morpholin-3-on-4-yl) -3-nitrobenzamide (a) 4- (Morpholin-3-on-4-yl) -3-nitrobenzoic acid methyl ester 1.00 g (3.85 mmol) of 4-bromo-3-nitrobenzoic acid methyl ester is dissolved with 389 mg (3.85 mmol) ) of morpholin-3-one under a nitrogen atmosphere in 6 ml of dioxane and 36.6 mg (40 μmol) of tris (dibenzylideneacetone) dipalladium (0), 67.1 mg (116 μmol) of Xantphos and 1.75 g (5.38 mmol) are added. of cesium carbonate. The reaction mixture is heated at 95 ° C under a nitrogen atmosphere and with stirring for 16 hours. It is then filtered, the solution is concentrated a.v. and evaporate with ether. The residue is reacted again without further purification. Yield: 1.31 g (quantitative). C? 2H? 2N206 (280.24). Mass spectrum: (M + H) + = 281. Rf value: 0.47 (reverse phase 8, methanol / 5% sodium chloride solution = 6: 4). (b) 4- (2-Carboxymethoxyethylamino) -3-nitrobenzoic acid 400 mg (1.43 mmol) of 4- (morpholin-3-on-4-yl) -3-nitrobenzoic acid methyl ester dissolved in 15 ml of methanol with 4.5 ml (4.5 mmol) of a 1 M lithium hydroxide solution. The mixture is stirred for 2 hours at room temperature. The mixture is then concentrated, the residue is diluted with water, cooled in an ice bath and acidified with 2 M hydrochloric acid. After cooling for 10 minutes in an ice bath, the precipitate formed is filtered off, washed with water until neutral and dried in a drying chamber at 50 ° C.

Yield: 290 mg (72%). CnH? 2N207 (284.23). Mass spectrum: M + = 284. Rf value: 0.59 (reverse phase 8, methanol / 5% sodium chloride solution = 6: 4). (c) 4- (Morpholin-3-on-4-yl) -3-nitrobenzoic acid chloride 290 mg (1.02 mmol) of 4- (2-carboxymethoxyethylamino) -3-nitrobenzoic acid in 100 ml of dichloromethane are mixed with 0.186 ml (2.55 mmol) of thionyl chloride and 2 drops of DMF, and heated at reflux for one day. After the a.v. solution is concentrated, it is evaporated with toluene and the residue is reacted again without further purification. Yield: 290 mg (quant.). C11H9CIN2O5 (284.66). (d) N- [(15) -1- (5-Chloro-1-benzimidazol-2-yl) -3-methylsulfanylpropyl] -4- (morpholin-3-on-4-yl) -3-nitrobenzamide Dissolve 237 mg (0.93 mmol) of (15) -1- (5-chloro-l-l-benzimidazol-2-yl) -3-methylsulfanylpropylamine with 0.257 ml of TEA in 10 ml of THF and a solution of 290 is added dropwise. mg (1.02 mmol) of 4- (morpholin-3-on-4-yl) -3-nitrobenzoic acid chloride in 10 ml of THF. The reaction mixture is stirred for 16 hours at room temperature and then concentrated a.v. The residue is purified by chromatography on silica gel (eluent gradient: dichloromethane / ethanol 100: 0 -> 95: 5). Yield: 34%. C22H22C1N505S (503.97). Mass spectrum: (M-H) ~ = 502/504 (chlorinated isotope). Rf value: 0.46 (silica gel, dichloromethane / ethanol = 9: 1).

Example 42 3-Chloro-N- [(15) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -4- (tetrahydropyrimidin-2-on-l-yl) benzamide (a) 4- (3-Boc-Aminopropylamino) -3-chlorobenzonitrile 3.49 g (20 mmol) of 3-Boc-aminopropylamine in 5 ml of DMF are mixed with 2.75 ml (25 mmol) of? MM. After adding 3.11 g (20 mmol) of 3-chloro-4-fluorobenzonitrile, it is stirred for 3.5 hours at room temperature under a nitrogen atmosphere, heated at 105 ° C for 20 minutes and extracted with ethyl acetate. The combined organic phases are washed with water and a sat. of sodium chloride, dried over magnesium sulfate and concentrated a.v. The residue is reacted again without further purification. Yield: 5.50 g (89%). C15H2oN3? 2 (309.80). Mass spectrum: (M + H) + = 310/312 (chlorinated isotope). Rf value: 0.40 (silica gel; petroleum ether / ethyl acetate = 2: 1). (b) 4- (3-Aminopropylamino) -3-chlorobenzonitrile 4.50 g (14.5 mmol) of 4- (3-Boc-aminopropylamino) -3-chlorobenzonitrile dissolved in 50 ml of dioxane are mixed with 200 ml of 6 M hydrochloric acid. The mixture is stirred for 2 hours at room temperature, then washed with ether and the aqueous phase was poured into 125 ml of a conc. of ammonia cooled with ice. It is then extracted with ethyl acetate, the combined organic phases are washed with water and a sat. of sodium chloride, dried over magnesium sulfate and concentrated a.v. The residue is reacted again without further purification. Yield: 1.40 g (46%). C? 0H12ClN3 (209.68). Mass spectrum: (M + H) + = 210/212 (chlorinated isotope). Rf value: 0.30 (silica gel); dichloromethane / methanol = 9: 1 + 1% conc. of ammonia). (c) 3-Chloro- (tetrahydropyrimidin-2-on-1-yl) benzonitrile A solution of 349 mg (2.15 mmol) of N, N'-carbonyldiimidazole in 3 ml of? MP is mixed with stirring at room temperature with 450 mg (2.15 mmol) of 4- (3-aminopropylamino) -3-chlorobenzonitrile and after dissolving completely is heated for 1 hour at 145 ° C and for 1.5 hours at 155 ° C. The reaction mixture is washed with water and extracted with ethyl acetate.

The combined organic phases are washed with water and a sat. of sodium chloride, dried over magnesium sulfate and concentrated a.v. The residue is then purified by chromatography on silica gel (eluent gradient: ethyl acetate / (methanol / conc. Ammonia solution 19: 1) = 100: 0 → 95: 5). Yield: 260 mg (51%). Rf value: 0.40 (silica gel; ethyl acetate / ethanol 9: 1 + 1% conc. Ammonia solution). C11H10Cl 3O (235.68). Mass spectrum: (M + H) + = 236/238 (chlorinated isotope). (d) 3-Chloro-4- (tetrahydropyrimidin-2-on-1-yl) benzoic acid 350 mg (1.49 mmol) of 3-chloro-4- (tetrahydropyrimidin-2-on-1-yl) benzonitrile are suspended in 5 ml of ethanol and mixed with 2.0 ml of an aqueous solution of 10 M sodium hydroxide. Stir for 1 hour at 100 ° C and then concentrate by The aqueous residue is mixed with ice, acidified with acetic acid and extracted with ethyl acetate. The combined organic phases are washed with water and a sat. of sodium chloride, dried over magnesium sulfate and concentrated a.v. The aqueous phase is acidified with 6 M hydrochloric acid, extracted with ethyl acetate 5 times, the combined organic phases are washed with a sat. of sodium chloride, dried over magnesium sulfate and concentrated a.v. Yield: 340 mg (90%). C HNClN203 (254.68). Mass spectrum: (M + H) + = 255/257 (chlorinated isotope). Rf value: 0.35 (silica gel, dichloromethane / methanol = 9: 1 + 1% acetic acid). (e) 3-Chloro-N- [(15) -1- (5-chloro-lff-benzimidazol-2-yl) ethyl] -4- (tetrahydro-pyrimidin-2-on-l-yl) benzamide Prepared analogously to Example 1f from 3-chloro-4- (tetrahydropyrimidin-2-on-1-yl) benzoic acid, (1S) -1- (5-chloro-1-yl-benzimidazol-2-yl) ethylamine, TBTU and? MM in DMF, then poured into ice water, adding a conc. of ammonia, separation by filtration, washing with water and purification by chromatography on silica gel (gradient eluent of ethyl acetate / (methanol / conc. solution of ammonia 19: 1) = 98: 2 -> 90:10) with subsequent filtration on activated carbon, trituration with ether and drying with a drying gun at 70 ° C. Yield: 32% C20H? 9Cl2N5O2 (432.31). Mass spectrum: (M + H) + = 432/434/436 (chlorinated isotope). Rf value: 0.40 (silica gel, dichloromethane / methanol = 9: 1 + 1% acetic acid). The following compound was prepared analogously: Example 46: 3-Chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- (piperidin-2-on-l-yl) benzamide (a) 3-Chloro-4- (5-chloropentanoylamino) benzoic acid methyl ester A solution of 696 μl (0.84 g, 5.39 mmol) of 5-chloropentanoyl chloride in 10 ml of THF at 1.00 g is slowly added dropwise. (5.39 mmol) of 4-amino-3-chlorobenzoic acid methyl ester in 20 ml of THF with 1 ml of TEA with stirring in an ice bath. After 16 hours of stirring at room temperature, 3 hours at 50 ° C and 3 hours under reflux, it is poured into water and extracted with ethyl acetate. After drying the organic phases over sodium sulfate, concentrate a.v. and the remaining residue is purified by chromatography on silica gel (eluent: petroleum ether / ethyl acetate 85:15). Yield: 300 mg (14.6%) of 80% product. C13Hi5Cl2N03 (304.18). Mass spectrum: (M + H) + = 304/306/308 (chlorinated isotope). Rt value: 3.29 min. (b) 3-Chloro-4- (piperidin-2-on-1-yl) benzoic acid methyl ester 300 mg (0.79 mmol) of the product obtained in Example 46a are dissolved in 10 ml of DMF with 180 mg ( 1.60 mmol) of potassium tert-butylate, and heated at 60 ° C for 3 hours. Then, the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, concentrated a.v. and the residue obtained is purified by chromatography on silica gel '(eluent: dichloromethane / isopropanol 98: 2). Yield: 159 mg (75%). C? 3H? 4ClN03 (267.71). Mass spectrum: (M + H) + = 268/270 (chlorinated isotope). Rf value: 0.18 (silica gel; dichloromethane / isopropanol = 49: 1). (c) 3-Chloro-4- (piperidin-2-on-1-yl) benzoic acid Prepared analogo to Example 39d from 3-chloro-4- (piperidin-2-on-1-yl) methyl ester ) benzoic acid and a solution of 8% lithium hydroxide in ethanol. Performance: 36%. C12H2ClN03 (247.30).

Mass spectrum: (M + H) + = 252/254 (chlorinated isotope). Rf value: 0.27 (silica gel, dichloromethane / ethanol = 9: 1). (d) 3-Chloro-N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- (piperidin-2-on-l-yl) benzamide Prepared analogo to example 1f from 3-chloro-4- (piperidin-2-on-1-yl) benzoic acid, TBTU, αMM and (li?) -1- (5-chloro-1-yl-benzimidazole-2) -yl) -2-methoxyethylamine in DMF and subsequent purification by chromatography on silica gel (gradient eluent: ethyl acetate / ethanol 95: 5 -> 90:10). Yield: 70%. C22H22C12? 403 (461.35). Mass spectrum: (M-H) ~ = 459/461/463 (chlorinated isotope). Rf value: 0.19 (silica gel, dichloromethane / ethanol = 19: 1).

The following compound was prepared analogo: Example 47 N- l (li?) -1- (5-Bromo-lH-benzimidazol-2-yl) -2-hydroxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide (a) N - (2-Amino-4-bromophenyl) -N-Boc- (5) -serinamide and Nf- (2-amino-5-bromophenyl) -N-Boc- (5) -serinamide 5.49 g are dissolved (26.7 mmol) of (S) -N-Boc-serine with 5.00 g (26.7 mmol) of 4-bromo-1,2-phenylenediamine in 125 ml of THF, and a solution of 5.52 g is added dropwise. (26.7 mmol) of N, N'-dicyclohexylcarbodiimide in 20 ml of THF with ice-cooling. The reaction mixture is stirred for 16 hours at room temperature. After concentrating a.v., the residue is purified by chromatography on silica gel (eluent: dichloromethane / methanol 98: 2). Yield: 4.76 g (48%) of mixture of both regioisomers. C? H20BrN304 (374.24). Mass spectrum: (M + H) + = 374/376 (brominated isotope). (b) (Ji?) -N-Boc-1- (5-Bromo-l-benzimidazol-2-yl) -2-hydroxyethylamine 3.00 g (8.02 mmol) of the mixture obtained in 47a are dissolved in 30 ml of acetic acid and stirred for 2 hours at 50 ° C. The reaction mixture is added dropwise to a 10% sodium hydroxide solution and extracted three times with ethyl acetate. Dry the combined organic phases over magnesium sulfate, concentrate a.v. and the residue is crystallized with methanol. Yield: 1.96 g (69%). C? 4H18Br? 303 (356.22). Rf value: 0.59 (silica gel; petroleum ether / ethyl acetate = 1: 1). (c) (IR) -1- (5-Bromo-lH-benzimidazol-2-yl) -2-hydroxyethylamine 2.00 g (5.62 mmol) of (IR) -N-Boc-1- (5-bromo- l-benzimidazol-2-yl) -2-hydroxyethylamine in 40 ml of ethyl acetate with ice bath cooling with 8.0 ml of 4 M hydrochloric acid in dioxane, and stirred for 16 hours at room temperature. The reaction mixture is concentrated and the created precipitate is filtered off. Yield: 1.11 g (67%). C9H10BrN3O * HCl (292.57 / 256.10). Mass spectrum: (M + H) + = 256/258 (brominated isotope). (d) N- [(li?) -1- (5-Bromo-lH-benzimidazol-2-yl) -2-hydroxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide Prepared analogo to the If example from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid, (li?) -1- (5-bromo-l-benzimidazol-2-yl) -2 -hydroxyethylamine, TBTU and? MM in DMF with subsequent purification by preparative HPLC. Yield: 52%. C2? H2? Br? 0 * CF3COOH (587.35 / 473.32). Mass spectrum: (M + H) + = 473/475 (brominated isotope) Rf value: 0.33 (silica gel, dichloromethane / methanol = 19: 1). Analogo, the following compounds were prepared: Example 48 N- [(SS) -1- (5-Chloro-1 H -benzimidazol-2-yl) ethyl] -4- (1,1-dioxoisothiazolidin-2-yl) -3-methylbenzamide (a) 4- (3-Chloropropylsulfonylamino) -3-methylbenzeic acid methyl ester 100 mg (0.61 mmol) of 4-amino-3-methylbenzoic acid methyl ester are dissolved in 3 ml of pyridine, mixed with 82 μl (0.67 mmol) of 3-chloropropanesulfonic acid chloride and stir for 16 hours at room temperature. The reaction solution is mixed with water and ethyl acetate and then the aqueous phase is extracted again with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated a.v. The residue is reacted again without further purification. Yield: 170 mg (92%). C12H? 6ClN0S (305.78). Mass spectrum: (M + H) + = 306/308 (chlorinated isotope). Rf value: 0.10 (silica gel; petroleum ether / ethyl acetate = 8: 2). (b) 4- (1,1-Dioxoisothiazolidin-2-yl) -3-methylbenzoic acid methyl ester 370 mg (0.85 mmol) of methyl 4- (3-chloropropanesulfonylamino) -3-methylbenzoic acid methyl ester are dissolved % in 26 ml of DMF, are mixed with 275 mg (2.45 mmol) of potassium tert-butylate and stirred for 16 hours at room temperature. The reaction mixture is mixed with water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, concentrated a.v. and the residue is purified by chromatography on silica gel (eluent: dichloromethane / isopropanol 98: 2). Yield: 177 mg (47%). C? 2H15N04S (269.32). Mass spectrum: (M + H) + = 270.

Rf value: 0.10 (silica gel; petroleum ether / ethyl acetate = 7: 3). (c) 4- (1, l-dioxoisothiazolidin-2-yl) -3-methylbenzoic acid. 170 mg (0.63 mmol) of 4- (1,1-dioxoisothiazolidin-2-yl) -3- methyl ester are stirred. methylbenzoic acid in 2 ml of ethanol at room temperature for 3 hours with 0.6 ml of 2 M sodium hydroxide solution. The reaction solution is then concentrated, mixed with water and 0.6 ml of 2 M hydrochloric acid and extracted with acetate. of ethyl. The combined organic phases are dried over sodium sulfate, concentrated a.v. and the residue is reacted again without further purification. Yield: 148 mg (92%). CnH? 3N04S (255.30). Mass spectrum: (M-H) "= 254. Retention time: 2.23 min. (d) N- [(1S) -1- (5-Chloro-l-benzimidazol-2-yl) ethyl] -4- (1, l-dioxoisothiazolidin-2-yl) -3-methylbenzamide Prepared analogously to example If from 4- (1, l-dioxoisothiazolidin-2-yl) -3-methylbenzoic acid, (1S) -1- (5-chloro-li? -benzimidazol-2-yl) ethylamine, TBTU and? MM in DMF with subsequent extraction with ethyl acetate, drying over magnesium sulfate, activated carbon and silica gel, with subsequent purification on silica gel (eluent: dichloromethane / isopropanol 95: 5). Yield: 37%. C20H21C1N403S (432.93). Mass spectrum: (M + H) + = 433/435 (chlorinated isotope). Rf value: 0.32 (silica gel, dichloromethane / isopropanol = 19: 1). The following compounds were prepared analogously: Example 54 3-Amino-N- [(15) -1- (5-chloro-li? -benzimidazol-2-yl) -3-methylsulfanylpropyl] -4- (morpholin-3-on-4-yl) benzamide 65 mg (0.13 mmol) of N- [(SS) -1- (5-chloro-l-benzimidazol-2-yl) -3-methylsulfanylpropyl] -4- (morpholin-3-on-4-yl) are mixed. 3-nitrobenzamide dissolved in 2 ml of ethyl acetate with 143 mg (0.63 mmol) of tin (II) chloride dihydrate and 130 mg (1.55 mmol) of sodium hydrogen carbonate, and heated at reflux for 2 hours. The reaction solution is mixed with ice water, stirred for 10 minutes and then the precipitate formed is filtered off. After drying for 3 days, the residue is purified by chromatography on silica gel (gradient eluent: dichloromethane / ethanol 100: 0 -> 91: 9). Yield: 5 mg (8.2%). C22H24C1? 503S (473.99). Mass spectrum: (M + H) + = 474/476 (chlorinated isotope). Rf value: 0.48 (silica gel, dichloromethane / ethanol = 9: 1).

Example 61 N- [(15) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -3-methyl-4- (5,6-dideshydroazepan-2-on-l-yl) benzamide (a) 3-Methyl-4- (pent-4-en-1-ylamino) benzoic acid methyl ester Prepared analogously to Example 46a from 4-amino-3-methylbenzoic acid methyl ester and 4-amino acid chloride penten-l-oico in THF with ASD. Yield: 46%. C? H? 7N03 (247.30). Mass spectrum: (M + H) + = 248. Rt value: 2.88 min. (b) 4- (Allylpent-4-en-l-oylamino) -3-methylbenzoic acid methyl ester 1.00 g (4.04 mmol) of 3-methyl-4- (pent-4-en-3-methyl) methyl ester is mixed. l-oylamino) benzoic acid dissolved in 5 ml of DMF with 500 mg (4.7 mmol) of potassium tert-butylate, and 350 μl (489 mg, 4.04 mmol) of allyl bromide are added slowly with stirring at 40 ° C. Then, it is heated for 3 hours at 70 ° C. Then, the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, concentrated a.v., the residue is placed on silica gel and purified by chromatography on silica gel (eluent: petroleum ether / ethyl acetate 9: 1). Yield: 58%. C? 7H2? N03 (287.36).

Mass spectrum: (M + H) + = 288. Rf value: 0.46 (petroleum ether / ethyl acetate = 9: 1). (c) 4- (4,5-dideshydroazepan-2-on-1-yl) -3-methylbenzoic acid methyl ester 150 mg (0.52 mmol) of 4- (alilpent) methyl ester are purged with argon for 30 minutes. -4-en-l-oylamino) -3-methylbenzoic acid dissolved in 110 ml of degassed dichloromethane. Next, 88 mg (104 μmol) of benzylidene- [1,3-bis (2,4,6-trimethylphenyl) -2-imidazolidinylidene] dichloro- (tricyclohexylphosphino) ruthenium (second-generation Grubbs catalyst) are added and heat at reflux for 4.5 hours. Then concentrate a.v., place the residue on silica gel and purify by chromatography on silica gel (eluent: petroleum ether / ethyl acetate 3: 2). Yield: 83 mg (61%). Rf value: 0.22 (silica gel, petroleum ether / ethyl acetate 3: 2). C15H17N03 (259.31). Mass spectrum: (M + H) + = 260. (d) 4- (4,5-dideshydroazepan-2-on-1-yl) -3-methylbenzoic acid Prepared analogously to Example 39d from 4- (4,5-dideshydroazepan-2-on-) methyl ester 1-yl) -3-methylbenzoic acid and an 8% solution of lithium hydroxide in ethanol. Yield: 51%. Rf value: 0.05 (silica gel, dichloromethane / methanol = 19: 1). C? 4H15N03 (245.28). Mass spectrum: (M + H) + = 246. (e) N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) ethyl] -4- (4,5-dideshydroazepan-2-on-l-yl) -3-methylbenzamide Prepared analogously to the If example from 4- (4,5-dideshydroazepan-2-on-1-yl) -3-methylbenzoic acid, TBTU,? MM and (15) -1- (5-chloro-l-benzimidazole- 2-yl) ethylamine in DMF and subsequent purification by preparative HPLC. '' Yield: 32%. Rf value: 0.44 (silica gel, dichloromethane / methanol = 19: 1). C23H23C1? 02 * CF3COOH (536.94 / 422.91). Mass spectrum: (M + H) + = 423/425 (chlorinated isotope).

Example 63 N- [(15) -1- (5-Chloro-l-benzimidazol-2-yl) ethyl] -4- (1,3-dioxothiomorpholin-4-yl) -3-methylbenzamide 204 mg (0.48 mmol) of N- [(SS) -1- (5-chloro-li-benzimidazol-2-yl) ethyl] -3-methyl-4- (thiomorpholin-3-on-4-yl are available. ) benzamide dissolved in a mixture of 12 ml of dichloromethane and 1.2 ml of acetic acid at -15 ° C and mixed with 110 mg (0.48 mmol) of 3-chloroperbenzoic acid. Then, the mixture is stirred for 1 hour at -15 to -10 ° C, warmed to room temperature and stirred for another 3 hours. The reaction mixture is then mixed with a half-concentrated solution of sodium hydrogen carbonate and extracted with a solvent mixture of dichloromethane / methanol 19: 1. The combined organic phases are washed with water, dried over magnesium sulfate, concentrated a.v. and purified by chromatography on silica gel (eluent gradient: ethyl acetate / (ethanol / conc. solution of ammonia 19: 1) = 1: 0 -> 4: 1). Yield: 100 mg (47%). C2? H2? Cl? 403S (444.94). Mass spectrum: (M + H) + = 445/447 (chlorinated isotope). Rf value: 0.15 (silica gel; ethyl acetate / ethanol = 4: 1 + 1% conc. Ammonia solution). The following compound was prepared analogously: Example 69 N- l (1S) -1- (5-Chloro-l-benzimidazol-2-yl) ethyl] -3-methoxy-4- (piperidin-2-on-l-yl) benzamide (a) 4- (5-Chloropentanoylamino) -3-methoxybenzoic acid methyl ester Prepared analogously to Example 6a from 4-amino-3-methoxybenzoic acid methyl ester and 5-chloropentanoic acid chloride in THF with TEA. Yield: 99% C? 4H? 8ClN04 (299.76). Mass spectrum: (M + H) + = 300/302 (chlorinated isotope). Rt value: 3.14 min. (b) 3-Methoxy-4- (piperidin-2-on-1-yl) benzoic acid methyl ester 2.25 g (7.51 mmol) of 4- (5-chloropentanoylamino) -3-methoxybenzoic acid methyl ester dissolved in 60 ml of DMF with 1.26 g (11.2 mmol) of potassium tert-butylate and stir for 2.5 hours at 60 ° C. Then concentrate a.v., mix the residue with water and extract with ethyl acetate. The combined organic phases are dried over sodium sulfate, concentrated a.v. and the residue obtained is purified by chromatography on silica gel (eluent gradient: petroleum ether / ethyl acetate 3: 2 -> 0.:1). Yield: 0.99 g (50%). Rt value: 2.56 min. C? 4H17N04 (263.30). Mass spectrum: (M + H) + = 264. (c) 3-Methoxy-4- (piperidin-2-on-1-yl) benzoic acid Prepared analogously to Example 39d from 3-methoxy-4- (piperidin-2-on-1-yl) methyl ester ) benzoic acid and lithium hydroxide in ethanol.

Yield: 95%. Rf value: 0.10 (silica gel; petroleum ether / ethyl acetate = 1: 2). C? 3H? 5N04 (249.27). Mass spectrum: (M + H) + = 250. (d) N- [(15) -1- (5-Chloro-7-benzimidazol-2-yl) ethyl] -3-methoxy-4- (piperidin-2-on-1-yl) benzamide Prepared analogously to the example lf from - 3-methoxy-4- (piperidin-2-on-l-yl) benzoic acid, 'TBTU,? MM and (ÍS) -1- (5-chloro-l-benzimidazol-2-yl) ethylamine in DMF and subsequent purification by preparative HPLC. Performance: 75%. Rt value: 2.35 min. C22H23C1? 403 * CF3COOH (540.93 / 426.90). Mass spectrum: (M + H) + = 427/429 (chlorinated isotope). The following compounds are analogously prepared: Example 73 N- [(SS) -1- (5-Chloro-1-benzimidazol-2-yl) ethyl] -4- (1,1-dioxo-6-methyl [1, 2, 6] -thiadiazinan-2 -yl) -3-methylbenzamide (a) 4- (1, l-Dioxo-6-methyl [1,2,6] thiadiazinan-2-yl) -3-methylbenzoic acid methyl ester 400 mg (1.41 mmol) of methyl 4-methyl ester are dissolved. - (1,1-dioxo [1, 2, 6] thiadiazin-2-yl) -3-methylbenzoic acid in 4 ml of DMF at 40 ° C, are mixed with 240 mg (2.14 mmol) of potassium tert-butylate and 96 μl (1.54 mmol) of methyl iodide and stir for 5 hours at 40 ° C. The reaction solution is concentrated a.v., mixed with water and the aqueous phase is extracted with ethyl acetate. Dry the organic phases, combined over sodium sulfate and concentrate a.v. Yield: 220 mg (52%). C13H? 8? 204S (298.36). Mass spectrum: (M + H) + = 299. Rf value: 0.44 (silica gel, petroleum ether / ethyl acetate - 3: 2). (b) 4- (1, l-Dioxo-6-methyl [1,2,6] thiadiazin-2-yl) -3-methylbenzoic acid Prepared analogously to Example 39d from methyl ester of 4- (1, l-dioxo-3-methyl [1,2,6] thiadiazinan-2-yl) -3-methylbenzoic acid and lithium hydroxide in ethanol. Performance: (81%). C? 2H? 6N20S (284.34). Mass spectrum: (M + H) + = 285. Rf value: 0.07 (silica gel, dichloromethane / methanol = 19: 1). (c) N- [(15) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -4- (1, l-dioxo-6-methyl [1,2,6] -thiadiazinan -2-yl) -3-methylbenzamide Prepared analogously to example lf from 4- (1, l-dioxo-3-methyl [1, 2, 6] thiadiazin-2-yl) -3-methylbenzoic acid, (1S ) -1- (5-chloro-li? -benzimidazol-2-yl) ethylamine, TBTU and? MM in DMF with subsequent purification by preparative HPLC. Performance: 55%. C2? H24Cl? 503S * CF3COOH (576. 00/461.97). Mass spectrum: (M + H) + = 462/464 (chlorinated isotope). Rt value: 2. 50 min The following compound was prepared analogously: Example 75 N- (li?) -1- (5-Bromy-li? -benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholine-3-on -4-yl) benzamide (a) N '- (2-Amino-4-bromophenyl) -N-Boc- (S) -O-Methylserinamide and N'- (2-amino-5-bromophenyl) -N-Boc- (S) -O -methylserinamide 2.50 g (6.24 mmol) of the dicyclohexylammonium salt of N-Boc- (5) -O-Methylserine are dissolved in 20 ml of 5% citric acid, the 2x aqueous phase is extracted with 20 ml of ethyl acetate each time, the combined organic phases are dried over sodium sulfate and freed from solvent av The residue is dissolved together with 1.23 g (6.55 mmol) of 4-bromo-1,2-phenylenediamine in 30 ml of THF and 1.42 ml (14.0 mmol) of triethylamine as well as 4.97 ml (7.80 ml) are added with stirring in an ice bath. mmol) of a 50% solution of PPA in ethyl acetate. After stirring for 5 minutes in an ice bath, the reaction mixture is warmed up to room temperature and stirred for 23 hours at room temperature. The reaction mixture is poured into 100 ml of water and the aqueous phase is extracted with ethyl acetate. The combined organic phases are stirred with a sat solution. of sodium carbonate and water, dried over sodium sulfate and concentrated a.v. Yield: 2.38 g (98%) of mixture of both regioisomers. C? 5H22BrN304 (388.26). Mass spectrum: (M + H) + = 388/390 (brominated isotope). Rf value: 0.63 / 0.68 (silica gel; dichloromethane / ethanol = 9: 1). (b) (IR) -N-Boc-1- (5-Bromo-lH-benzimidazol-2-yl) -2-methoxyethylamine 2.38 g (6.13 mmol) of the mixture obtained in 75a are dissolved in 150 ml of toluene and 1.84 ml (30.7 mmol) of acetic acid as well as 4.00 g of 3Á molecular sieves are added. The reaction mixture is stirred for 3 hours at 55 ° C and then cooled in an ice bath for 15 minutes. The reaction mixture is filtered and poured into a mixture of 500 ml of water and ethyl acetate each. After vigorous mixing, the organic phase is separated, washed with a sat. of sodium chloride, dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (gradient eluent: dichloromethane / ethanol 100: 0 -> 97: 3). Yield: 1.40 g (62%). C? 5H20BrN3? 3 (370.24). Mass spectrum: (M + H) + = 370/372 (brominated isotope). Rf value: 0.81 (silica gel, dichloromethane / ethanol = 9: 1). (c) (li?) -1- (5-Bromo-lff-benzimidazol-l-yl) -2-methoxyethylamine Prepared analogously to example lg from (li?) -N-Boc-1- (5-bromo) -li? -benzimidazol-2-yl) -2-methoxyethylamine and TFA in dichloromethane. Yield: 51%. C? 0H12Br? 3O (270.13). Mass spectrum: (M + H) + = 270/272 (brominated isotope). Rf value: 0.20 (silica gel, dichloromethane / ethanol 9: 1). (d) N- [(li?) -1- (5-Bromo-l-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide Prepared analogously to the If example from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid, (li?) -1- (5-bromo-lH-benzimidazol-2-yl) -2 -methoxyethylamine, TBTU and DLPEA in THF with subsequent purification by chromatography on silica gel. Performance: quant. C22H23BrN404 (487.35). Mass spectrum: (M + H) + = 487/489 (brominated isotope). Rf value: 0.56 (silica gel, dichloromethane / ethanol = 9: 1).

EXAMPLE 76 N- [(SS) -1- (5-Chloro-l-benzimidazol-2-yl) -3- (1 H -tetrazol-5-yl) propyl] -3-methyl-4- (morpholin-3-) on-4-yl) benzamide (a) (2S) -2- (Benzyloxycarbonylamino) -4-cyanobutyric acid ethyl ester 5.00 g (11.3 mmol) of (2S) -2- (benzyloxycarbonylamino) -4-cyanobutanoate of diclohexylammonium in 100 ml of a solution are stirred. of 5% citric acid and then extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed by distillation a.v. The residue is dissolved in 70 ml THF, 4.35 g (13.5 mmol) of TBTU and 6.35 ml (33.8 mmol) of DIPEA are added and the mixture is stirred at room temperature for 10 minutes. Then, 50 ml of ethanol are added and the mixture is heated at reflux for 16 hours. The reaction mixture is then concentrated a.v., taken up in ethyl acetate, washed with a half-saturated solution of sodium hydrogencarbonate and water, dried over sodium sulfate and concentrated a.v. Yield: 3.20 g (98%). Ci5H? 8N204 (290.32). Mass spectrum: (M + NH4) + = 308. Rf value: 0.80 (silica gel, dichloromethane / ethanol = 9: 1). (b) (25) -2- (Benzyloxycarbonylamino) -4- (l, 2-tetrazol-5-yl) butyric acid ethyl ester 3.20 g (11.0 mmol) of (2S) -2- (benzyloxycarboniland) ethyl ester are dissolved. .no) -4-cyanobutyric acid in 40 ml of toluene and 1.08 g (16.5 mmol) of sodium azide and 2.28 g (16.5 mmol) of triethylamine hydrochloride are added. The reaction mixture is heated at 85 ° C for 24 hours, cooled to room temperature and extracted with water. The combined aqueous phases are acidified to pH 2 with half-concentrated hydrochloric acid, the created precipitate is filtered off with suction, washed with water and dried at 50 ° C. Yield: 2.90 g (79%). C? 5H? 9N50 (333.34). Mass spectrum: (M + H) + = 334. Rf value: 0.50 (silica gel, dichloromethane / ethanol = 9: 1). (c) (25) -2- (Benzyloxycarbonylamino) -4- (1H-tetrazol-5-yl) butyric acid Prepared analogously to example 30b-- from (2S) -2- (benzyloxycarbonylamino) ethyl ester - 4- (1H-tetrazol-5-yl) butyric acid and lithium hydroxide in a mixed solvent of water and THF. Performance: quant. C? 3H? 5N504 (305.29). Mass spectrum: (M + H) + = 306. Rf value: 0.30 (silica gel, dichloromethane / ethanol = 4: 1). (d) N- (2-amino-4-chlorophenyl) - (25) -2- (benzyloxy-carbonylamino) -4- (l-tetrazol-5-yl) butyric acid amide and N- (2-amino) acid -amino-5-chlorophenyl) - (25) -2- (benzyloxycarbonylamino) -4- (l, 2-tetrazol-5-yl) butyric Prepared analogously to example 47a from (2S) -2- (benzyloxycarbonylamino) acid -4- (1, 4-tetrazol-5-yl) butyric acid and 4-chloro-l, 2-phenylenediamine with DCC in THF. Yield: quant., Mixture of both regioisomers, slightly unpurified. C19H20C1N703 (429.86). Rf value: 0.20 (silica gel, dichloromethane / ethanol = 9: 1). (e) (15) -N- (Benzyloxycarbonyl) -1- (5-chloro-lff-benzimidazol-2-yl) -3- (lij-tetrazol-5-yl) propylamine Prepared analogously to example 47b from the product obtained in Example 76d and acetic acid. Performance: quant. C? 9H? 8Cl? 702 * CH3COOH (471.90 / 411.85). Rf value: 0.25 (silica gel, dichloromethane / ethanol / conc. Ammonia = 4: 1: 0.1). (f) (15) -1- (5-Chloro-lH-benzimidazol-2-yl) -3- (lff-tetrazol-5-yl) propylamine 2.10 g (4.45 mmol) of (1S) -N- are mixed. (benzyloxycarbonyl) -1- (5-chloro-lH-benzimidazol-2-yl) -3- (li? -tetrazol-5-yl) propylamine in 30 ml of dichloromethane with 1.9 ml (13.4 mmol) of iodotrimethylsilane and stirred for 16 hours at room temperature. Then, 20 ml of methanol are added, stirring is carried out for a further 30 minutes at room temperature and the reaction mixture is completely concentrated a.v. The residue is purified by chromatography on silica gel (eluent gradient: dichloromethane / (ethanol / ammonia conc.95: 5) = 70/30 -> 60:40). Yield: 690 mg (56%). CnH12ClN7 (277.71). Mass spectrum: (M + H) + = 278/280 (chlorinated isotope). Rf value: 0.15 (silica gel, dichloromethane / ethanol = 3: 2 + 1% conc. Ammonia). (g) N- [(15) -1- (5-Chloro-l-benzimidazol-2-yl) -3- (lff-tetrazol-5-yl) propyl] -3-methyl-4- (morpholine- 3-on-4-yl) benzamide Prepared analogously to the If example from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid, (15) -1- (5-chloro-l- benzimidazol-2-yl) -3- (li? -tetrazol-5-yl) propylamine, TBTU and DIPEA in THF with subsequent purification by chromatography on silica gel. Performance: 33%. C23H23C1? 803 (494.93). Mass spectrum: (M + H) + = 495/497 (chlorinated isotope). Rf value: 0.20 (silica gel, dichloromethane / ethanol = 4: 1).

Example 77 N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) -3-methoxypropyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide (a) N '- (2-amino-4-chlorophenyl) - (2S) -2- (Boc-amino) -3-methoxypropionic acid amide and Nf- (2-amino-5-chlorophenyl) - amide (25) -2- (Boc-amino) -3-methoxypropionic 4.90 g (21.0 mmol) of (25) -2- (Boc-amino) -3-methoxypropionic acid dissolved in 20 ml of THF are mixed with 13.57 g ( 42.0 mmol) of TBTU and 5.76 ml (52.5 mmol) of triethylamine and stir for 30 minutes at room temperature •, Then, 3.00 g (21.0 mmol) of 4-chloro-l, 2-phenylenediamine in 20 ml of THF are added. and the mixture is stirred for 16 hours at room temperature. Next, concentrate a.v. The reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are washed with a sat. of sodium hydrogen carbonate, dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (eluent: dichloromethane / methanol 99: 1). Yield: 5.60 g (75%) of the mixture of both regioisomers.

C? 6H2ClN303 (357.83). Mass spectrum: (M + H) + = 358/360 (chlorinated isotope). Rf value: 0.26 (silica gel, dichloromethane / methanol = 99: 1). (b) (SS) -N-Boc-1- (5-Chloro-1-benzimidazol-2-yl) -3-methoxypropylamine Prepared analogously to Example 47b from the product obtained in example 77a and acetic acid. Yield: 96%. C16H22C1? 303 (339.82). Mass spectrum: (M + H) + = 340/342 (chlorinated isotope). Rf value: 0.80 (silica gel, dichloromethane / methanol: 19: 1). (c) (SS) -1- (5-Chloro-l-1-benzimidazol-2-yl) -3-methoxypropylamine Prepared analogously to example lg from (SS) -N-Boc-1- (5-chloro-li β-benzimidazol-2-yl) -3-methoxypropylamine and TFA in dichloromethane. Performance: 31%. CnH? 4Cl? 30 (239.70). Mass spectrum: (M + H) + = 240/242 (chlorinated isotope). Rf value: 0.10 (silica gel, dichloromethane / ethanol = 9: 1). (d) N- [(15) -1- (5-Chloro-1-yl-benzimidazol-2-yl) -3-methoxypropyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide Prepared analogously to example lf from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid, (SS) -1- (5-chloro-lH-benzimidazol-2-yl) -3-methoxy -propylamine, TBTU and DIPEA in THF with subsequent purification by chromatography on silica gel. Yield: 59%. C23H25C1? 404 (456.92). Mass spectrum: (M + H) + = 457/459 (chlorinated isotope). Rf value: 0.51 (silica gel, dichloromethane / ethanol = 9: 1). The following compound was prepared analogously: Example 82 3-Chloro-N- [(SS) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- (3,6-dihydro [1,2] oxazin-2-yl) benzamide (a) 3-Chloro-4-nitrosobenzoic acid methyl ester 8.00 g (29.6 mmol) of potassium peroxodisulfate are added with stirring to 6.0 ml of sulfuric acid, stirred for 30 minutes at room temperature under nitrogen, stirred Mix in 50 g of ice and neutralize with 14 g of cesium carbonate. The solution obtained is mixed with a suspension of 2.78 g (15.0 mmol) of 4-amino-3-chlorobenzoic acid methyl ester in 300 ml of water and stirred for 16 hours at room temperature. The reaction mixture is filtered off with suction, the filter cake is washed with water, dried with air and purified by chromatography on silica gel (eluent: petroleum ether / ethyl acetate 9: 1). Yield: 1.00 g (33%). C8H6C1N03 (199.59). Mass spectrum: (M + H) + = 199/201 (chlorinated isotope). Rf value: 0.55 (silica gel; petroleum ether / ethyl acetate = 4: 1). (b) 3-Chloro-4- (3,6-dihydro [1,2] oxazin-2-yl) benzoic acid methyl ester 1.00 g (5.01 mmol) of 3-chloro-4- methyl ester Nitrosobenzoic acid in 10 ml of chloroform and a freshly prepared solution of 1.10 g (20.3 mmol) of butadiene in 6 ml of chloroform is added dropwise at 0 ° C with stirring. The reaction mixture is stirred for 30 minutes at 0-10 ° C and for 16 hours at room temperature, concentrated a.v. and purified by chromatography on silica gel (eluent: petroleum ether / ethyl acetate = 19: 1). Yield: 1.00 g (79%). C? 2H? 2ClN03 (253.68). Mass spectrum: (M + H) + = 254/256 (chlorinated isotope).

Rf value: 0.50 (silica gel; petroleum ether / ethyl acetate = 4: 1). (c) 3-Chloro-4- (3,6-dihydro [1,2] oxazin-2-yl) benzoic acid Prepared analogously to Example 2d from 3-chloro-4- (3,6) methyl ester -dihydro [1,2] oxazin-2-yl) benzoic acid and sodium hydroxide in a mixture of water and ethanol solvents. Performance: 90%. C11H10CINO3 (239.66). Mass spectrum: (M-H) ~ = 238/240. Rf value: 0.20 (silica gel; petroleum ether / ethyl acetate = 4: 1). (d) 3-Chloro-N- [(15) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -4- (3,6-dihydro [1,2] oxazin-2-yl) ) benzamide Prepared analogously to example lf from 3-chloro-4- (3,6-dihydro [1,2] oxazin-2-yl) benzoic acid, (15) -1- (5-chloro-lH-benzimidazole) -2-yl) ethylamine, TBTU and? MM in DMF .. Yield: 88%. C20H18C12? 402 (417.29). Mass spectrum: (M + H) + = 417/419/421 (chlorinated isotope). Rf value: 0.35 (silica gel; petroleum ether / ethyl acetate = 1: 1).

Example 83 3-Chloro-N- [(li?) -1- (5-chloro-lB-benzimidazol-2-yl) -2-methoxyethyl] -4- (1,1-dioxo [1,2] -thiazinan -2-il) benzamide (a) 2-Chloro-N- (4-chlorobutylsulfonyl) -4-methylaniline 1.30 ml (10.7 mmol) of 2-chloro-4-methylaniline in 30 ml of pyridine are mixed with 2.67 g (10.5 mmol) of 75% 4-chlorobutylsulfonic acid chloride for 16 hours at room temperature. The reaction mixture is poured into water and extracted with ethyl acetate ... The combined organic phases are washed with 6 M hydrochloric acid, dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (eluent gradient: petroleum ether / ethyl acetate = 9: 1 -> 7: 3). Yield: 1.27 g (40%). CuH15Cl2? 02S (296.21). Mass spectrum: (M + H) + = 296/298/300 (chlorinated isotope). Rf value: 0.42 (silica gel; petroleum ether / ethyl acetate = 4: 1). (b) 3-Chloro-4- (1,1-dioxo [1,2] thiazinan-2-yl) toluene 1.27 g (4.29 mmol) of 2-chloro-N- (4-chlorobutylsulfonyl) -4- are stirred. methylaniline together with 722 mg (6.43 mmol) of potassium tert-butylate in 50 ml of DMF for 16 hours at 60 ° C. Then, the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (eluent: petroleum ether / ethyl acetate = 3: 2). Yield: 850 mg (76%). CnH14Cl? 02S (259.75). Mass spectrum: (M + H) + = 260/262 (chlorinated isotope). Rf value: 0.27 (silica gel; petroleum ether / ethyl acetate = 4: 1). (c) 3-Chloro-4- (1, 1-dioxo [1,2] thiazinan-2-yl) benzoic acid. 250 mg (0.96 mmol) of 3-chloro-4- (1,1-dioxo [ 1, 2] thiazolin-2-yl) toluene in 10 ml of water with 456 mg (2.89 mmol) of potassium permanganate and 39 mg (0.98 mmol) of sodium hydroxide. The reaction mixture is refluxed for 4 hours. After cooling to room temperature, sodium thiosulfate is added until decolorized and then extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (eluent: dichloromethane / methanol = 19: 1). Yield: 50 mg (18%). C11H12CINO4S (289.74). Mass spectrum: (M + H) + = 290/292. Rt value: 2.50 min. (d) 3-Chloro-N- [(li?) -1- (5-chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (1,1-dioxo [1,2] thiazine -2-yl) benzamide Prepared analogously to example lf from 3-chloro-4- (1, 2-dioxo [1,2] thiazinan-2-yl) benzoic acid, (li?) - l- (5- chloro-li? -benzimidazol-2-yl) -2-methoxyethylamine, TBTU and? MM in DMF with subsequent purification by preparative HPLC. Yield: 34%. C2? H22Cl2? 404S (497.40). Mass spectrum: (M + H) + = 497/499/501 (chlorinated isotope). Rt value: 2.53 min.

Example 84 N- [(li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (1, 1-dioxo [1,2] thiazepan-2-yl) ) -3-methylbenzamide (a) 4- (5-Chloropentylsulfonylamino) -3-methylbenzoic acid methyl ester Prepared analogously to Example 83a from 4-amino-3-methylbenzoic acid methyl ester and 5-chloropentylsulfonic acid chloride in pyridine. Performance: 43%. C? H20ClNO4S (333.83). Mass spectrum: (M + H) + = 334/336 (chlorinated isotope). Rf value: 0.72 (silica gel; petroleum ether / ethyl acetate = 7: 3). (b) 4- (1,1-Dioxo [1,2] thiazepan-2-yl) -3-methylbenzoic acid methyl ester Prepared analogously to Example 83b from 4- (5-chloropentylsulfonylamino) -methyl ester - 3-methylbenzoic and potassium tert-butylate in DMF. Performance: 19%. C14H? 9N0S (297.37). Mass spectrum: (M + H) + = 298. Rt value: 0.30 (silica gel, petroleum ether / ethyl acetate = 4: 1). (c) 4- (1,1-Dioxo [1,2] thiazepan-2-yl) -3-methylbenzoic acid Prepared analogously to Example 39d from 4- (1,1-dioxo-methyl) methylester 1, 2] thiazepan-2-yl) -3-methylbenzoic acid and lithium hydroxide in a mixture of water and ethanol solvents. Yield: 60%. C? 3H? 7N04S (283.34). Mass spectrum: (M + H) + = 284. Rt value: 2.60 min. (d) N- [(li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (1, 1-dioxo [1,2] thiazepane-2-) il) -3-methylbenzamide Prepared analogously to the If example from 4- (1, 2-dioxo [1, 2] thiazepan-2-yl) -3-methylbenzoic acid, (li?) - l- (5-chloro) -li? -benzimidazol-2-yl) -2-methoxyethylamine, TBTU and? MM in DMF with subsequent purification by silica gel chromatography. Performance: 75%. C23H27C1? 404S (491.00). Mass spectrum: (M + H) + = 491/493 (chlorinated isotope). Rt value: 2.60 min.

Example 89 3-Chloro-N- [(SS) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -4- ([1, 2] oxazinan-2-yl) benzamide 209 mg (0.50 mmol) of 3-chloro-N- [(1S) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- (3,6-dihydro [1] are hydrogenated. 2] oxazin-2-yl) benzamide together with 100 mg of 10% palladium on charcoal in 5 ml of ethyl acetate for 7 minutes at room temperature under a hydrogen atmosphere of 500 kPa. It is then filtered off with suction, the a.v. filtrate is concentrated. and evaporate with ether. Yield: 200 mg (95%). C20H20Cl2? 4O2 (419.30). Mass spectrum: (M + H) + = 419/421/423 (chlorinated isotope). Rf value: 0.40 (silica gel; petroleum ether / ethyl acetate = 1: 1).

EXAMPLE 90 N- [(li?) -1- (5-Chloro-liH-enoimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (5-oxo [1,4] oxazepan-4-yl) benzamide (a) 3- (2-Benzyloxyethoxy) propionic acid ethyl ester 8.53 ml (60.0 mmol) of benzyloxyethanol are mixed in 40 ml of THF with 13 mg (0.57 mmol) of sodiumAfter dissolution, 5.95 ml (54.7 mmol) of ethyl acrylate is added under argon and stirred for 20 hours at room temperature. After neutralizing with 0.6 ml of 1 M hydrochloric acid, the reaction mixture is concentrated a.v., the residue is taken up in a sat. of sodium chloride and extracted with ethyl acetate. The combined organic phases are washed with a sat. of sodium chloride, dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (eluent: petroleum ether / ethyl acetate = 4: 1). Yield: 3.73 g (25%). C? 4H20O4 (252.31). Mass spectrum: (M + H) + = 253. Rf value: 0.48 (silica gel; petroleum ether / ethyl acetate = 4: 1). (b) 3- (2-Hydroxyethoxy) propionic acid ethyl ester 3.73 g (14.8 mmol) of 3- (2-benzyloxyethoxy) propionic acid ethyl ester are hydrogenated together with 665 mg of 10% palladium on charcoal in 70 ml of ethanol for 44 minutes at room temperature under hydrogen atmosphere at 300 kPa. It is then filtered off with suction and the a.v. filtrate is concentrated. Yield: 2.26 g (94%). C7H? 40 (162.18). Mass spectrum: (M + H) + = 163. (c) 3- (2-Chloroethoxy) propionic acid ethyl ester 2.26 g (13.9 mmol) of 3- (2-hydroxyethoxy) propionic acid ethyl ester in 5 ml (68.5 mmol) of thionyl chloride are suspended and added 20 μl (0.27 mmol) of DMF. The reaction mixture is refluxed for 4 hours and then concentrated a.v. The product is reacted again without further purification. Performance: quant. C7H? 303 (180.63). Mass spectrum: (M + H) + = 181/183 (chlorinated isotope). (d) 3- (2-Chloroethoxy) propionic acid 2.00 g (11.1 mmol) of 3- (2-chloroethoxy) propionic acid ethyl ester are suspended in 8 ml of ethanol and 4.96 ml (16.6 mmol) of ethanol solution are added. 8% lithium hydroxide. The mixture is stirred for 4 hours at room temperature, then concentrated a.v., acidified with 2M hydrochloric acid, mixed with diethyl ether and dried over sodium sulfate. It is then filtered off and concentrated a.v. Yield: 1.51 g (89%). Mass spectrum: (M-H) ~ = 151/153 (chlorinated isotope). (e) 3- (2-Chloroethoxy) propionic acid chloride Prepared analogously to Example 90c from 3- (2-chloroethoxy) propionic acid and thionyl chloride with DMF. Yield: 91%. C5H8C1202 (171.02). (f) 4- [3- (2-Chloroethoxy) propionylamino] -3-methylbenzoic acid methyl ester 1.70 g (10.3 mmol) of 4-amino-3-methylbenzoic acid methyl ester in 10 ml of THF are mixed with 2.84 g. ml (20.6 mmol) of triethylamine and stir for 20 minutes at room temperature. Then, a solution of 1.78 g (10.4 mmol) of 3- (2-chloroethoxy) propionic acid chloride in 25 ml of THF is added dropwise and stirred for another 2.5 hours at room temperature. Then water is added and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and fully concentrated a.v. The residue is purified by silica gel chromatography (eluent gradient: petroleum ether / ethyl acetate = 7: 3 -> 6: 4). Yield: 1.25 g (41%). C? 4 H 18 ClN04 (299.75). Mass spectrum: (M + H) + = 300/302 (chlorinated isotope). Rf value: 0.15 (silica gel; petroleum ether / ethyl acetate = 7: 3). (g) 3-Methyl-4- (5-oxo [1,4] oxazepan-4-yl) benzoic acid methyl ester 900 mg (3.00 mmol) of 4- [3- (2- (2- (2-methyl)] methyl ester is stirred. chloroethoxy) propionylamino] -3-methylbenzoic acid in 40 ml of DMF together with 520 mg (4.63 mmol) of potassium tert-butylate and 12 mg (80 μmol) of sodium iodide for 3 hours at 60 ° C. After concentrating a.v., the residue is mixed with water, extracted with ethyl acetate, the combined organic phases are dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (eluent: petroleum ether / ethyl acetate = 11: 9). Yield: 310 mg (39%).

C? 4H? 7N04 (263.29). Mass spectrum: (M + H) + = 264. (h) 3-Methyl-4- (5-oxo [1,4] oxazepan-4-yl) benzoic acid Prepared analogously to Example 39d from 3-methyl-4- (5-oxo) methyl ester [1] , 4] oxazepan-4-yl) benzoic acid and lithium hydroxide in a mixture of water and ethanol solvents. Performance: 69%. C? 3H15N04 (249.26). Mass spectrum: (M + H) + = 250. Rt value: 2.06 min. (i) N- [(li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (5-oxo [1,4] oxazepan- 4-yl) benzamide Prepared analogously to example lf from 3-methyl-4- (5-oxo [1,4] oxazepan-4-yl) benzoic acid, (li?) - l- (5-chloro-lii) -benzimidazol-2-yl) -2-methoxyethylamine, TBTU and? MM in DMF with subsequent purification by preparative HPLC. Performance: 83%. C23H25C1? 404 (456.92). Mass spectrum: (M + H) + = 457/459 (chlorinated isotope). Rt value: 2.23 min.

Example 91 N- [(1S) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -4- (4,4-dimethyl-2-oxoimidazolidin-1-yl) -3-methylbenzamide (a) 4- (3- [1,1-Dimethyl-2-hydroxyethyl] ureido) -3-methylbenzoic acid methyl ester 5.70 g (29.8 mmol) of 4-isocyanato-3-methylbenzoic acid methyl ester dissolved in 100 ml of THF and a solution of 2.86 ml (30.0 mmol) of 2-amino-2-methylpropan-1-ol in 25 ml of THF is added dropwise. The mixture is stirred for 2 hours at room temperature and then concentrated a.v. The residue is reacted again without further purification. Yield: 8.40 g (quant.). C? 4H20? 204 (280.32). Mass spectrum: (M-H) ~ = 279. Rf value: 0.20 (silica gel, dichloromethane / ethanol = 19: 1). (b) 4- (4, -Dimethyl-2-oxoimidazolidin-1-yl) -3-methylbenzoic acid methyl ester 7.00 g (25.0 mmol) of 4- (3- [1-, 1--] methyl ester are mixed. dimethyl-2-hydroxyethyl] ureido) -3-methylbenzoic acid dissolved in 400 ml of THF at 0 ° C with 6.73 g (60.0 mmol) of potassium tert-butylate. After stirring for 15 minutes at 0 ° C, a solution of 5.72 g (30.0 mmol) of p-toluenesulfonic acid in 50 ml of THF is added dropwise. After a further 10 minutes of stirring at 0 ° C, 300 ml of water are added, neutralized with 1 M hydrochloric acid and the THF a.v. The residue is extracted with dichloromethane. The combined organic phases are dried over sodium sulfate and concentrated a.v. The residue is then purified by chromatography on silica gel (eluent gradient: dichloromethane / ethanol = 100: 0 -> 97: 3). Yield: 2.50 g (38%). C? 4H? 8N203 (262.30). Mass spectrum: (M + H) + = 263. Rf value: 0.30 (silica gel, dichloromethane / ethanol = 19: 1). (c) 4- (4, -Dimethyl-2-oxoimidazolidin-1-yl) -3-methylbenzoic acid 2.70 g (10.3 mmol) of 4- (4,4-dimethyl-2-oxoimidazolidin-) methyl ester are suspended. 1-yl) -3-methylbenzoic acid in 75 ml of methanol and mixed with a solution of 1.68 g (30.0 mmol) of potassium hydroxide in 10 ml of water. It is stirred for 3 hours at room temperature and then concentrated a.v. The aqueous residue is diluted with water, acidified with 1 M hydrochloric acid and the precipitate obtained is filtered off with suction, washed with water and dried. Yield: 2.30 g (90%). C? 3 H 16 N 203 (248.28). Mass spectrum: (M + H) + = 249. Rf value: 0.50 (silica gel, dichloromethane / methanol = 9: 1). (d) N- (l5) -l- (5-Chloro-l # -benzimidazol-2-yl) ethyl] -3-methyl-4- ([1,3] oxazepan-2-on-3-yl) benzamide Prepared analogously to the If example from 4- (4,4-dimethyl-2-oxoimidazolidin-1-yl) -3-methylbenzoic acid, (ÍS) -1- (5-chloro-lH-benzimidazol-2-yl) ethylamine, TBTU and DIPEA in THF and purification of the residue by chromatography on silica gel. Yield: 59%. C22H2C1N502 (425.91). Mass spectrum: (M + H) + = 426/428 (chlorinated isotope). Rf value: 0.40 (silica gel, dichloromethane / methanol = 9: 1).

The following compound was prepared analogously: Example 93 3-Chloro-N- [(1S) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -4- (4-methyl-2-oxooxazolidin-3-yl) benzamide (a) 3-Chloro-4- (2-hydroxy-l-methylethylamino) benzonitrile 4.00 g (25.7 mmol) of 3-chloro-4-fluorobenzonitrile in 20 ml of DMSO are heated with 8.00 g (106.5 mmol) of 2- amino-1-propanol with stirring for 2 hours at 60 ° C. Then, the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are washed with water and a sat. of sodium chloride, dried over sodium sulfate and concentrated a.v. Yield: 5.20 g (96%). C? 0H ?? ClN2O (210.66). Mass spectrum: (M + H) + = 211/213 (chlorinated isotope). Rf value: 0.27 (silica gel, dichloromethane / methanol = 19: 1). (b) Acid. 3-Chloro-4- (2-hydroxy-l-methylethylamino) benzoic 5.20 g (24.7 mmol) of 3-chloro-4- (2-hydroxy-l-methylethylamino) benzonitrile in 50 ml of concentrated hydrochloric acid is heated to reflux. . for 6 hours. Next, concentrate a.v., alkalize with a conc. of ammonia and stirred with ethyl acetate. After acidifying the aqueous phase with acetic acid, it is extracted with ethyl acetate, the combined organic phases are washed with water and a sat. of sodium chloride, dried over sodium sulfate and concentrated a.v. Yield: 5.00 g (88%). C? 0H? 2ClNO3 (229.66). Mass spectrum: (M + H) + = 230/232 (chlorinated isotope). Rf value: 0.44 (silica gel; dichloromethane / methanol = 9: 1). (c) 3-Chloro-4- (2-hydroxy-1-methylethylamino) benzoic acid ethyl ester 5.00 g (21.8 mmol) of 3-chloro-4- (2-hydroxy-1-methylethylamino) benzoic acid are stirred in 100 ml satin ethanolic hydrochloric acid. for 16 hours at room temperature and then concentrated a.v. The residue is mixed with water and a conc. of ammonia and extracted with ethyl acetate. The combined organic phases are washed with water and a sat. of sodium chloride, dried over sodium sulfate and concentrated a.v. The residue is purified by chromatography on silica gel (eluent: dichloromethane / methanol = 50: 1). Yield: 3.40 g (61%). C? 2H? 6ClN03 (257.71). Mass spectrum: (M + H) + = 258/260 (chlorinated isotope). Rf value: 0.34 (silica gel, dichloromethane / methanol = 19: 1). (d) 3-Chloro-4- (4-methyl-2-oxooxazolidin-3-yl) benzoic acid ethyl ester 0.50 g (1.94 mmol) of 3-chloro-4- (2-hydroxy) ethyl ester -l-methylethylamino) benzoic together with 0. 22 g (2.20 mmol) of triethylamine in 30 ml of THF, and 1.10 ml (2.08 mmol) of 20% phosgene solution in toluene are added with stirring at room temperature. The mixture is stirred for 1 hour at room temperature, then 1 ml of water is added and the mixture is stirred for another 10 minutes. The a.v. mixture is then concentrated, mixed with water and extracted with ethyl acetate. The combined organic phases are washed with water and a sat. of sodium chloride, dried over sodium sulfate and concentrated a.v. Yield: 0.54 g (98%). C? 3H? 4ClN04 (283.71). Mass spectrum: (M + H) + = 284/286 (chlorinated isotope). Rf value: 0.71 (silica gel, dichloromethane / methanol = 19: 1). (e) 3-Chloro-4- (4-methyl-2-oxooxazolidin-3-yl) benzoic acid 0.90 g (3.17 mmol) of 3-chloro-4- (4-methyl-2-ethyl) ethyl ester are stirred. oxooxazolidin-3-yl) benzoic acid in 50 ml of methanol with 10 ml of 1 M aqueous lithium hydroxide solution at room temperature for 1 hour. Then, the mixture a.v. up to 20 ml, acidified with conc. hydrochloric acid. and extracted with ethyl acetate. The combined organic phases are washed with a sat. of sodium chloride, dried over sodium sulfate and concentrated a.v. The residue is crystallized with little diethyl ether and filtered off with suction. Yield: 0.45 g (56%).

C? H? 0ClNO4 (255.65). Mass spectrum: (M + H) + = 256/258 (chlorinated isotope) Rf value: 0.26 (silica gel, dichloromethane / methanol = 9: 1). (f) 3-Chloro-N- [(15) -1- (5-chloro-lH-benzimidazol-2-yl) ethyl] -4- (4-methyl-2-oxooxazolidin-3-yl) benzamide Prepared analogously to the If example from 3-chloro- (4-methyl-2-oxooxazolidin-3-yl) benzoic acid, (1S) -1- (5-chloro-l-benzimidazol-2-yl) ethylamine, TBTU and DIPEA in THF and purification of the residue by chromatography on aluminum oxide. Performance: 45%. C20H18Cl2? 4O3 (433.29). Mass spectrum: (M + H) + = 433/435/437 (chlorinated isotope). Rf value: 0.65 (silica gel, dichloromethane / methanol = 9: 1).

Analogously, the following compounds were prepared: Example 95 N- [1- (5-Chloro-l-benzimidazol-2-yl) -1-phenylmethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide (a) Nr - (2-Amino-4-chlorophenyl) -N-Boc-phenylglycinamide and N "- (2-amino-5-chlorophenyl) -N-Boc-phenylglycinamide Prepared analogously to Example 47 from N-Boc - phenylglycine, 4-chloro-l, 2-phenylenediamine and DCC - in THF Yield: quant Mixture of both regioisomers.

C19H22C1N303 (375.85). Mass spectrum: (M + H) + = 376/378 (chlorinated isotope). Rf value: 0.41 (silica gel, dichloromethane / ethanol = 19: 1). (b) N-Acetyl-1- (5-chloro-lg-benzimidazol-2-yl) -1-phenylmethylamine 3.65 g (9.71 mmol) of the mixture obtained in 95a are dissolved in 8 ml of acetic acid and heated to reflux for 6 hours with shaking. The reaction mixture is concentrated a.v. and the residue is purified by silica gel chromatography (eluent gradient: dichloromethane / ethanol = 100: 0 -> 94: 6). Yield: 1.34 g (46%). C 16 H 4 Cl 30 (299.76). Mass spectrum: (M + H) + = 300/302 (chlorinated isotope). Rf value: 0.19 (silica gel, dichloromethane / ethanol = 19: 1). (c) 1- (5-Chloro-l-benzimidazol-2-yl) -1-phenylmethylamine 1.34 g (4.47 mmol) of N-acetyl-1- (5-chloro-l-benzimidazol-2-yl are mixed. ) -1-phenylmethylamine in 9 ml of ethanol with 18 ml of conc. Hydrochloric acid. and it is heated for 2 days at 50 ° C. The reaction mixture is concentrated a.v. and it is collected twice in ethanol and concentrated again. Yield: 1.26 g (96%). C? H? 2ClN3 * HCl (294.18 / 257.72). Mass spectrum: (M + H) + = 258/260 (chlorinated isotope). (d) N- [1- (5-Chloro-l-1-benzimidazol-2-yl) -1-phenylmethyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide Prepared analogously to example lf from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid, 1- (5-chloro-l-benzimidazol-2-yl) -l-phenylmethylamine, TBTU and DIPEA in THF. Performance: 89%. C26H23C1? 403 (474.94). Mass spectrum: (M + H) + = 475/477 (chlorinated isotope). Rf value: 0.68 (silica gel, dichloromethane / ethanol = 9: 1). The following compound was prepared analogously: Example 96 N- [(SS) -1- (5-Chloro-l-benzimidazol-2-yl) propyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide (a) Nf - (2-amino-4-chlorophenyl) acid amide - (25) 2- (Boc-amino) butyric acid amide of N'- (2-amino-5-chlorophenyl) - (25) -2- (Boc-amino) butyric Prepared analogously to example 47a from acid (25) -2 - (Boc-amino) butyric, 4-chloro-l, 2-phenylenediamine and DCC in THF.

Yield: 89% mixture of both regioisomers. Ci5H22ClN303 (327.81). Mass spectrum: (M + H) + = 328/330 (chlorinated isotope). Rf value: 0.63 (silica gel, dichloromethane / ethanol = 19: 1). (b) (15) -N-Boc-1- (S-Chloro-li-J-benzimidazol-S-yl) propylamine Prepared analogously to Example 47b from the mixture obtained in 95a and acetic acid and purification of the residue by chromatography on Silica gel. Yield: 94%. C 5 H 20 Cl 3 O 2 (309.79). Mass spectrum: (M + H) + = 310/312 (chlorinated isotope). Rf value: 0.63 (silica gel, dichloromethane / ethanol = 19: 1). (c) (15) -1- (5-Chloro-lH-benzimidazol-2-yl) -1-phenylmethylamine Prepared analogously to Example 75c from (SS) -N-Boc-1- (5-chloro-l-benzimidazol-2-yl) propylamine and trifluoroacetic acid in dichloromethane. Performance: quant. C? QH? 2Cl? 3 * 2 CF3COOH (437.72 / 209.68). Mass spectrum: (M + H) + = 210/212 (chlorinated isotope). (d) N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) propyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide Prepared analogously to the example If from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid, (1S) -1- (5-chloro-li? -benzimidazol-2-yl) propylamine, TBTU and DIPEA in THF Yield: 17%. C22H23C1? 403 (426.90). Mass spectrum: (M + H) + = 427/429 (chlorinated isotope). Rf value: 0.45 (silica gel; dichloromethane / ethanol = 9: 1! The following examples were similarly prepared Example 106 N- l (IR) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-fluoro-4- (morpholin-3-on-4-yl) benzamide (a) 4- [(2-Chloroethoxy) acetylamino] -3-fluorobenzoic acid ethyl ester Prepared analogously to Example 46a from (2-chloroethoxy) acetyl chloride and 4-amino-3-fluorobenzoic acid ethyl ester with TEA in THF. Performance: 44%. C13H15C1FN04 (303.71). Mass spectrum: (M + H) + = 304/306 (chlorinated isotope). Rf value: 0.29 (silica gel, dichloromethane). (b) 4- (2-Carboxymethoxyethylamino) -3-fluorobenzoic acid 580 mg (1.91 mmol) of 4- [(2-chloroethoxy) acetylamino] -3-fluorobenzoic acid ethyl ester in 6 ml of dioxane is mixed with 3.82 ml. (7.64 mmol) of 2 M potassium hydroxide solution and 2 ml of water. It is then heated for 2 h at 70 ° C, then diluted with water and acidified with 6 M hydrochloric acid. After adding dichloromethane, the precipitate obtained is filtered off with suction and dried in a 50 ° drying chamber. C. Yield: 390 mg (79%). CnH? 2FN05 (257.22). Mass spectrum: (M + H) + = 258. Rf value: 0.66 (RP-8 in reverse phase, methanol / 5% NaCl solution = 6: 4). (c) 3-Fluoro-4- (morpholin-3-on-4-yl) benzoic acid chloride Prepared analogously to Example 41c from 4- (2-carboxymethoxyethylamino) -3-fluorobenzoic acid and thionyl chloride in dichloromethane with DMF. Performance: quant. CnH9ClFN03 (257.65). (d) N- [(li?) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -3-fluoro-4- (morpholin-3-on-4-yl) benzamide Prepared analogously to example 4Id from 3-fluoro-4- (morpholin-3-on-4-yl) benzoic acid chloride yi (li?) -1- (5-chloro-li? -benzimidazol-2-yl) ) -2-methoxyethylamine with TEA in THF. Yield: 47%. C2? H20ClF? 4O (446.86). Mass spectrum: (M + H) + = 447/449 (chlorinated isotope). Rf value: 0.40 (silica gel, dichloromethane / ethanol = 9: 1).

Example 109 N- [1- (5-Chloro-l-benzimidazol-2-yl) -1- (pyridin-3-yl) methyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide (a) N '- (2-amino-4-chlorophenyl) -2- (Boc-amino) -2- (pyridin-3-yl) acetic acid amide and Nr- (2-amino-5-) acid amide chlorophenyl) -2- (Boc-amino) -2- (pyridin-3-yl) -acetic acid 1.00 g (3.96 mmol) of N-Boc-amino-2- (pyridin-3-yl) acetic acid together with 0.59 g (4.16 mmol) of 4-chloro-1,2-phenylenediamine at 0 ° C in 20 ml of THF and 2.92 ml are added. (4.96 mmol) of 50% PPA solution in ethyl acetate, as well as 1.24 ml (8.92 mmol) of TEA. After stirring for 30 min at 0 ° C, it is stirred for 5 hours at room temperature and then fully concentrated a.v. The residue is purified by silica gel chromatography (eluent gradient: dichloromethane / ethanol = 10: 0 -> 9: 1). Yield: 1.32 g (88%) of a mixture of both regioisomers. C? 8H21Cl? 403 (376.84). Mass spectrum: (M + H) + = 377/379 (chlorinated isotope). Rf value: 0.40 (silica gel, dichloromethane / ethanol = 9: 1). (b) N-Boc-1- (5-Chloro-lH-benzimidazol-2-yl) -1- (pyridin-3-yl) methylamine Prepared analogously to example 47b "from the product obtained in the example Illa and acid acetic Yield: 81% C? 8H? 9ClN402 (358.82) Mass spectrum: (M + H) + = 359/361 (chlorinated isotope) Rf value: 0.51 (silica gel; dichloromethane / ethanol = 9 :1). (c) 1- (5-Chloro-li? -benzimidazol-2-yl) -1- (pyridin-3-yl) methylamine Prepared analogously to the example Ig from N-Boc-1- (5-chloro-li β-benzimidazol-2-yl) -1- (pyridin-3-yl) methylamine and trifluoroacetic acid in dichloromethane. Yield: 66%. C? 3 HnCl? 4 (258.71). Mass spectrum: (M + H) + = 259/261 (chlorinated isotope). Rf value: 0.62 (silica gel, dichloromethane / ethanol = 9: 1). (d) N- [1- (5-Chloro-1-yl-benzimidazol-2-yl) -1- (pyridin-3-yl) methyl] -3-methyl-4- (morpholin-3-on-4-yl) ) Benzamide Prepared analogously to the If example from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid and 1- (5-chloro-li? -benzimidazol-2-yl) -1- ( pyridin-3-yl) methylamine with TBTU and DIPEA in THF. Yield: 84%. C25H22CIN5O3 (475.93). Mass spectrum: (M + H) + = 476/478 (chlorinated isotope). Rf value: 0.31 (silica gel, dichloromethane / ethanol = 9: 1).

EXAMPLE 110 N- [1- (5-Chloro-li? -benzimidazol-2-yl) -1- (1-methylpyrazol-3-yl) methyl] -3-methyl-4- (morpholin-3-on-4) -il) benzamide (a) Ethoxycarbonylmethoxyimino- (1-methylpyrazol-3-yl) acetic acid methyl ester 5.00 g (20.7 mmol) of ethoxycarbonylmethoxyimino (pyrazol-3-yl) acetic acid together with 5.73 g. (41.5 mmol) of potassium carbonate at room temperature in ml of DMF, stir until the gas evolution has ended, then add 2.58 ml (41.5 mmol) of methyl iodide and stir for 2 h at 50 ° C. After concentrating the a.v. reaction mixture, the residue is mixed with water and ethyl acetate, the organic phase is washed with water, dried over magnesium sulfate and completely concentrated a.v. The residue is purified by silica gel chromatography (eluent gradient: petroleum ether / ethyl acetate = 80:20 -> 65:35). Yield: 2.61 g (26%) of a mixture of regioisomers. C11H15N3O5 (269.25). Mass spectrum: (M + H) + = 270. Rf value: 0.25 (silica gel, petroleum ether / ethyl acetate = 1: 1). (b) 2-Amino-2- (1-methylpyrazol-3-yl) acetic acid methyl ester 2.61 g (9.6.9 mmol) of ethoxycarbonylmethoxyimino- (1-methylpyrazol-3-yl) acetic acid methyl ester are hydrogenated. in 60 ml of ethanol with 1.1 g of 5% palladium on charcoal for 16 h at 50 ° C at 3400 kPa of pressure under a hydrogen atmosphere. It is then filtered off with suction and the filtrate is concentrated a.v. Yield: 1.90 g (quant.), Slightly unpurified. C7HuN302 (169.18).

Mass spectrum: (M + H) + = 170. Rf value: 0.30 (silica gel, dichloromethane / ethanol = 9: 1). (c) Methyl ester of N-Boc-2-amino-2- (1-methylpyrazol-3-yl) acetic acid Prepared analogously to example 1d from 2-amino-2- (1-methylpyrazole- 3-yl) acetic acid and di-tert-butyl ester of pyrocarbonic acid with TEA in dichloromethane. Performance: 81%. C? 2H19? 304 (269.30). Mass spectrum: (M + H) + = 270. (d) N-Boc-2-amino-2- (l-methylpyrazol-3-yl) acetic acid 1.16 g (4.31 mmol) of N-Boc-2-amino-2- (1-) methyl ester are mixed. methylpyrazol-3-yl) acetic acid in 16 ml of THF with 10 ml of water and add 10 ml of a 1 M lithium hydroxide solution. After stirring at room temperature for 2 hours, concentrate to v, mix the residue with water, it is filtered and the filtrate is brought to pH 5 with a solution of potassium hydrogen sulphate. After completely concentrating a.v., the residue is treated with dichloromethane and a little ethanol, filtered off with suction and the filtrate a.v. Yield: 0.92 g (84%). CnH? 7N304 (255.27). Mass spectrum: (M + H) + = 256. Rf value: 0.15 (silica gel, dichloromethane / etariol = 8: 2). (e) Nf- (2-amino-4-chlorophenyl) -2- (Boc-amino) -2- (l-methylpyrazol-3-yl) acetic acid amide and N'- (2-amino-) -amide 5-chlorophenyl) -2- (Boc-amino) -2- (l-methylpyrazol-3-yl) acetic acid Prepared analogously to example Illa from N-Boc-2-amino-2- (l-methylpyrazole-3) acid -yl) acetic acid and 4-chloro-1,2-phenylenediamine with PPA in ethyl acetate and? MM in dichloromethane. Yield: 55% mixture of both regioisomers. C? 7H22Cl? 503 (379.84). Rf value: 0.61 (silica gel, dichloromethane / ethanol = 9: 1). (f) N-Boc-1- (5-Chloro-lH-benzimidazol-2-yl) -1- (1-methylpyrazol-3-yl) methylamine Prepared analogously to Example 47b from the product obtained in example 112e and acetic acid. Performance: 81%. .

C 7 H 20 ClN 5 O 2 (361.83). Mass spectrum: (M + H) + = 362/364 (chlorinated isotope). Rf value: 0.60 (silica gel, dichloromethane / ethanol = 9: 1). (g) 1- (5-Chloro-li? -benzimidazol-2-yl) -1- (1-methylpyrazol-3-yl) methylamine Prepared analogously to example lg from N-Boc-1- (5-chloro -lif-benzimidazol-2-yl) -1- (l-methylpyrazol-3-yl) methylamine and trifluoroacetic acid in dichloromethane. Performance: 77%. C 2 H 2 Cl 5 (261.71). Mass spectrum: (M-? H3 + H) + = 245/247 (chlorinated isotope). Rf value: 0.30 (silica gel, dichloromethane / ethanol / conc. Ammonia solution = 9: 1: 0.1). (h) N- [1- (5-Chloro-lH-benzimidazol-2-yl) -1- (1-methylpyrazol-3-yl) methyl] -3-methyl-4- (morpholin-3-on-4 -yl) benzamide Prepared analogously to the If example from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid and 1- (5-chloro-li? -benzimidazol-2-yl) -1 - (1-methylpyrazol-3-yl) methylamine with TBTU and DIPEA in THF. Performance: 38%.

C24H23C1N603 (478.93). Mass spectrum: (M + H) + = 479/481 (chlorinated isotope). Rf value: 0.50 (silica gel, dichloromethane / ethanol = 9: 1).

Example 111 3-Chloro-N- [(li?) -1- (5-chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (5-methylmorpholin-3-on-4-yl benzamide (a) 4- [2- (tert-Butoxycarbonylmethoxy) -1-methylethylamino] -3-chlorobenzoic acid ethyl ester 1.12 g (4.35 mmol) of 3-chloro-4- (2-hydroxyethyl) ethyl ester are mixed. l-methylethylamino) benzoic acid in 10 ml of DMF with 0.21 g (4.78 mmol) of a 55% sodium hydride dispersion, and stirred for 5 min at room temperature. Then, 0.67 ml of bromoacetic acid tert-butyl ester are added and the mixture is stirred for another 16 hours at room temperature. Then, the reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are washed with water and a sat. of sodium chloride and dried thoroughly a.v. The residue is purified by chromatography on silica gel (eluent gradient: petroleum ether / ethyl acetate = 95: 5 -> 80:20). Yield: 230 mg (14%). C18H26C1N05 (371.86). Mass spectrum: (M + H) + = 372/374 (chlorinated isotope). Rf value: 0.65 (silica gel; petroleum ether / ethyl acetate = 7: 3). (b) 3-Chloro-4- [2- (hydroxycarbonylmethroxy) -1-methylethylamino] benzoic acid ethyl ester Prepared analogously to example lg from 4- [2- (tert-butoxycarbonylmethoxy) -1- ethyl ester methylethylamino] -3-chlorobenzoic acid and trifluoroacetic acid in dichloromethane. Performance: 87%. C? 4H? 8ClN05 (315.75). Mass spectrum: (M + H) + = 316/318. Rf value: 0.40 (silica gel, dichloromethane / ethanol = 9: 1). (c) 3-Chloro-4- (5-methylmorpholin-3-on-4-yl) benzoic acid ethyl ester Prepared analogously to Example 41c from 3-chloro-4- [2- (hydroxycarbonylmethoxy) ethyl ester ) -1-methylethylamino] benzoic acid and thionyl chloride with DMF in dichloromethane. Yield: 69% (without purification). C? 4H? 6ClN04 (297.73). Mass spectrum: (M + H) + = 298/300 (chlorinated isotope). Rf value: 0.40 (silica gel, dichloromethane / ethanol = 19: 1). (d) 3-Chloro-4- (5-methylmorpholin-3-on-4-yl) benzoic acid Prepared analogously to Example 31b from 3-chloro-4- (5-methylmorpholin-3-on) ethyl ester -4-yl) benzoic acid with lithium hydroxide in THF and water. ... Performance: 91%. C12H12C1N04 (269.68). Rf value: 0.30 (silica gel, dichloromethane / ethanol = 9: 1). (e) 3-Chloro-N- [(li?) -1- (5-chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (5-methylmorpholin-3-on-4-yl) ) benzamide Prepared analogously to example 1f from 3-chloro-4- (5-methylmorpholin-3-on-4-yl) benzoic acid and (li?) -l- (5-chloro-1-benzimidazole-2-acid) il) -2-methoxyethylamine with TBTU and TEA in DMF. Yield: 28%. C22H22C12? 404 (477.34).

Mass spectrum: (M-H) = 475/477/479 (chlorinated isotope). Rf value: 0.50 (silica gel, dichloromethane / ethanol = 9: 1).

Example 112 3-Chloro-N- [(15) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- (3-dimethylaminopyrrolidin-1-yl) benzamide (a) 3-Chloro-4- (3-dimethylaminopyrrolidin-1-yl) benzonitrile 0.75 g (4.82 mmol) of 3-chloro-4-fluorobenzonitrile are mixed together with 0.65 ml (0.58 g, 5.06 mmol) of 3-dimethylaminopyrrolidine. in 12 ml of DMF at room temperature with stirring and under an argon atmosphere with 231 mg (5.30 mmol) of 55% sodium hydride dispersion. After stirring at room temperature for 3.5 h, the reaction mixture is poured into water and after vigorous mixing is extracted with ethyl acetate. The combined organic phases are washed with a sat. of sodium chloride, dried over magnesium sulfate and completely concentrated a.v.

Yield: 1.11 g (92%). C? 3H? 6ClN3 (249.74). Mass spectrum: (M + H) + = 250/252 (chlorinated isotope). Rf value: 0.42 (silica gel; petroleum ether / ethyl acetate = 1: 1). (b) 3-Chloro-4- (3-dimethylaminopyrrolidin-1-yl) benzoic acid Prepared analogously to Example 13b from 3-chloro-4- (3-dimethylaminopyrrolidin-1-yl) benzonitrile with 10 M sodium hydroxide solution and ethanol. Yield: 27%. C? 3 H17ClN202 (268.74). Mass spectrum: (M + H) + = 269/271 (chlorinated isotope). (c) 3-Chloro-N- [(15) -1- (5-chloro-l-benzimidazol-2-yl) ethyl] -4- (3-dimethylaminopyrrolidin-1-yl) benzamide Prepared analogously to example lf a from 3-chloro-4- (3-dimethylaminopyrrolidin-1-yl) benzoic acid and (1S) -1- (5-chloro-1 H -benzimidazol-2-yl) ethylamine with TBTU and TEA in DMF. Yield: 74%, slightly unpurified. C22H25C12? 50 (446.37). Mass spectrum: (M + H) + = 446/448/450 (chlorinated isotope).

Rf value: 0.65 (silica gel, dichloromethane / methanol = 8: 2 + 0.5% conc. Ammonia solution).

Example 113 N- [(1S) -1- (5-Chloro-li? -benzimidazol-2-yl) ethyl] -4- (pyrazolidin-3-on-l-yl) -3-trifluoro-methylbenzamide (a) 4- (Pyrazolidin-3-on-1-yl) -3-trifluoromethylbenzonitrile 1.00 g (5.29 mmol) of 4-fluoro-3-trifluoromethylbenzonitrile are stirred together with 1.35 g (1.2.0 mmol) of tert-butylate of potassium in 4 ml of DMSO at room temperature under argon for 35 min, and then 1.00 g is added (8.16 mmol) of pyrazolidin-3-one hydrochloride in 3 ml of DMSO. After stirring at room temperature for 68 h, the reaction mixture is poured into a semisat solution. of sodium chloride and extracted with ethyl acetate. Dry the combined organic phases over magnesium sulfate and concentrate completely a.v. Performance: 0 58 g (43%). C? H8F3? 30 (255.20).

Mass spectrum: (M + H) + = 256. Rf value: 0.15 (silica gel, dichloromethane + 0.5% conc. Ammonia solution). (b) 4- (Pyrazolidin-3-on-1-yl) -3-trifluoromethylbenzoic acid Prepared analogously to Example 13b from 3-chloro-4- (3-dimethylaminopyrrolidin-1-yl) benzonitrile-or with bleach. 10 M soda and ethanol. Yield: 56%. CnH9F3N203 (274.20). Rf value: 0.60 (silica gel, dichloromethane / ethanol = 8: 2 + 0.5% acetic acid). (c) N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) ethyl] -4- (pyrazolidin-3-on-l-yl) -3-trifluoromethylbenzamide Prepared analogously to the example If from 4- (pyrazolidin-3-on-1-yl) -3-trifluoromethylbenzoic acid and (1S) -1- (5-chloro-1 H -benzimidazol-2-yl) ethylamine with TBTU and TEA in DMF. Yield: 12%, without purification. C2oH17ClF3? 5? 2 * 2 CF3COOH (679.88 / 451.83). Mass spectrum: (M + H) + = 452/454 (chlorinated isotope). Rf value: 0.58 (silica gel, dichloromethane / methanol = 8: 2 + 0.5% conc. Ammonia solution).

Example 127 N- [(SS) -1- (7-Chloroimidazo [1,2- a] pyridin-2-yl) -3-methylbutyl] -3-methyl-4- (morpholin-3-on-4-yl) benzamide (a) (15) -N-Boc-1- (7-Chloroimidazo [1,2-a] pyridin-2-yl) -3-methylbutylamine 1.68 g (6.37 mmol) of tert-butyl acid ester are mixed [ 1- (2-Chloroacetyl) -3-methylbutyl] carbamic acid in 15 ml of methanol at room temperature with stirring with 819 mg (6.37 mmol) of 2-amino-4-chloropyridine, and the mixture is refluxed for 3 days. After concentrating a.v., the residue is mixed with a 5% sodium hydrogen carbonate solution and stirred for 20 h at room temperature. It is then extracted with dichloromethane, the combined organic phases are dried over sodium sulfate and fully concentrated a.v. The residue is purified by chromatography on silica gel (gradient eluent: dichloromethane / ethanol = 100: 0 -> 94: 6). Yield: 180 mg (8%). C? 7H24Cl? 302 (337.85).

Mass spectrum: (M + H) A 338/340 (chlorinated isotope). Rf value: 0.61 (silica gel, dichloromethane / ethanol = 9: 1). (b) (15) -1- (7-Chloroimidazo [1,2-a] pyridin-2-yl) -3-methylbutylamine Prepared analogously to example lg from (1S) -N-Boc-1- (7 -chloroimidazo [1,2-a] pyridin-2-yl) -3-methylbutylamine with trifluoroacetic acid in dichloromethane. Performance: quant. C? 2H16Cl? 3 * 2 CF3C02H (465.78 / 237.73). Mass spectrum: (M + H) + = 238/240 (chlorinated isotope). (c) N- [(15) -1- (5-Chloroimidazo [1, 2-a] pyridin-2-yl) -3-methylbutyl] -3-methyl-4- (morpholin-3-on-4-) il) benzamide Prepared analogously to the example If. from 3-methyl-4- (morpholin-3-on-4-yl) benzoic acid and (15) -1- (5-chloroimidazo [1, 2-a] pyridin-2-yl) -3-methylbutylamine with TBTU and DIPEA in THF. Performance: quant. C24H27C1? 403 (454.95). Mass spectrum: (M + H) + = 455/457 (chlorinated isotope). Rf value: 0.54 (silica gel, dichloromethane / ethanol = 9: 1).

The following examples describe the preparation of pharmaceutical forms of use containing as active ingredient any compound of general formula I: EXAMPLE I Dry ampule with 75 mg of active ingredient per 10 ml Composition: Active ingredient 75.0 mg Mannitol 50.0 mg Water for injections up to 10.0 ml Preparation: The active principle and mannitol are dissolved in water. After filling, it is lyophilized. The solution is made for a solution ready for use with water for injections.

Example II Dry ampule with 35 mg of active ingredient per 2 ml Composition: Active ingredient 35.0 mg Mannitol 100.0 mg Water for injections up to 2.0 ml Preparation: The active principle and mannitol are dissolved in water. After filling, it is lyophilized. The solution is made for a solution prepared for use - with water for injections.

Example III Tablet with 50 mg of active ingredient Composition: (1) Active ingredient 50.0 mg (2) Milk sugar 98.0 mg (3) Corn starch 50.0 mg (4) Poly (vinylpyrrolidone) 15.0 mg (5) Magnesium stearate 2.0 mg 215.0 mg Preparation: Mix (1), (2) and (3) and granulate with an aqueous solution of (4). Mix (5) with the dried granulate. With this mixture compressed biplanes tablets with facets or both sides and a dividing notch on one side. Diameter of the tablets: 9 mm.

Example IV Compressed with 350 mg of active ingredient Composition: (1) Active ingredient 350.0 mg (2) Milk sugar 136.0 mg (3) Corn starch 80.0 mg (4) Poly (vinylpyrrolidone) 30.0 mg (5) Stearate magnesium 4.0 mg 600.0 mg Preparation: Mix (1), (2) and (3) and granulate with an aqueous solution of (4). Mix (5) with the dried granulate. With this mixture compressed biplanes with facets on both sides and a dividing notch on one side. Diameter of the tablets: 12 mm.

Example V Capsules with 50 mg of active ingredient Composition: (1) Active ingredient 50.0 mg (2) Dried corn starch 58.0 mg (3) Powdered milk sugar 50.0 mg (4) Magnesium stearate 2.0 mg 160.0 mg Preparation: crush (1) with (3). The mixture of (2) and (4) is added to this comminution with intensive mixing. Hollow gelatin capsules of size 3 are filled with this pulverized mixture in a capsule filling machine.

Example VI Capsules with 350 mg of active ingredient Composition: (1) Active ingredient 350.0 mg (2) Dried corn starch 46.0 mg (3) Powdered milk sugar 30.0 mg (4) Magnesium stearate 4.0 mg 4.30.0 mg Preparation : It is crushed (1) with (3). This trituration is added to the mixture of (2) and (4) with intensive mixing. Hollow gelatin capsules of size 0 are filled with this pulverized mixture in a capsule filling machine.

Example VII Suppositories with 100 mg of active ingredient 1 suppository contains: Active ingredient 100.0 mg Polyethylene glycol (MW 1500) 600.0 mg Polyethylene glycol (MW 6000) 460.0 mg Polyethylene sorbitan monostearate 840.0 mg 2000.0 mg Preparation: Polyethylene glycol is melted together with polyethylene sorbitan monostearate . The milled active substance is dispersed homogeneously at 40 ° C in the molten mixture. It is cooled to 38 ° C and poured into suppository molds gently pre-cooled

Claims (28)

1. CLAIMS 1. Substituted carboxylic acid amides of the general formula characterized because A means a group of formula gene in which; m represents the number 1 or 2, R 6'a independently represents a hydrogen, fluorine, chlorine or bromine atom or a C?-3 alkyl, hydroxy, amino, alkyl Ca_3-amino, di (C C alkyl- 3) amino, aminocarbonyl, C 1 -C 3 -aminocarbonyl alkyl, di (C 1 -C 3 alkyl) aminocarbonyl or C 1 -C 3 alkylcarbonylamino and R 6b can independently be a hydrogen atom, a C 1 alkyl group, alkyl C ??? - carbonyl, alkyl C? -oxycarbonyl or C? _3-sulfonyl alkyl, with the proviso that the heteroatoms optionally introduced as substituents in the above-mentioned 5 to 7-membered substituted groups A are not exactly separated by a carbon atom. carbon of another heteroatom, or a group of general formula ,. wherein m represents the number 1 or 2, X1 represents an oxygen atom or a methylene group, -NR, carbonyl or sulfonyl, X2 represents an oxygen atom or a group -NR6b, X3 represents a methylene, carbonyl or sulfonyl group , X4 represents an oxygen or sulfur atom, -NR6b or a carbonyl group, X5 represents a carbonyl or sulfonyl group, X6 represents an oxygen atom, -NR6b or a methylene group, X7 represents an oxygen or sulfur atom or a group -NR6b, X8 represents a methyl or carbonyl group, X9 represents -NR6b or a carbonyl group, X10 represents a sulfinyl or sulfonyl group and R6a independently represents a hydrogen, fluorine, chlorine or bromine atom or a C1-3 alkyl group , hydroxy, amino, C C _3-amino alkyl, di (C 1-3 alkyl) amino, aminocarbonyl, C alqu-3-aminocarbonyl alkyl, di (C Ci-3 alkyl) aminocarbonyl or C C-3-carbonylamino alkyl and R 6b can be independently of one another a hydrogen atom, a C1-4 alkyl group, alkyl C? _4- carbonyl, C?-4-carbonyl alkoxy or C?-3-sulfonyl alkyl, with the proviso that the heteroatoms optionally introduced as substituents in the above-mentioned 5 to 7-membered substituted groups A are not exactly separated by a carbon atom of another hetero atom, R1 represents a hydrogen, fluorine, chlorine or bromine atom, a C3_3 alkyl group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, a C2_3 alkenyl group, C2_3 alkynyl , nitro, amino, C1-3 alkoxy, mono-, di- or trifluoromethoxy, R2 represents a hydrogen, fluorine, chlorine or bromine atom, or a C1-3 alkyl group, R3 represents a hydrogen atom, a C2_ alkenyl group 3 or C2_3 alkynyl or a straight or branched chain C6-6 alkyl group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, and which is optionally substituted by a nitrile, hydroxy, alkoxy C group? _5 where the hydrogen atoms may be fully or partially substituted by fluorine atoms, an allyloxy, propargyloxy, benzyloxy, alkyl C 5 -carbonyloxy, alkyl C 5 -oxycarbonyloxy, carboxyalkyl C 3 -oxi, C 1 -5 alkyl group -oxocarbonylalkylC? -3-oxy, alkylC?-8-oxycarbonylamino, mercapto, C ?3-sulfañyl alkyl, C? -3-sulfinyl alkyl, C ?3-sulfonyl alkyl, C C3 alkylcarbonylamino-Ci-alkyl 3-sulphanyl, C 1 -C 3 alkylcarbonylamino-C 1 -3-sulfinyl alkyl, C 1-3 alkyl-carbonylamino-C 1 -3-sulfonyl alkyl, carboxy, C 1-3 alkyloxycarbonyl, allyloxycarbonyl, propargyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, C C3-aminocarbonyl alkyl, di (C ?3) alkyl aminocarbonyl, C3_6-iminocarbonyl cycloalkylene, aminosulfonyl, C C ~3-aminosulfonyl alkyl, di (C? _3 alkyl) aminosulfonyl, C3_6-iminosulfonyl cycloalkylene, amino, C?-3-amino alkyl, di (C 1-3 alkyl) amino, C 1-5 alkylcarbonylamino, C?-3-sulfonylamino alkyl, N- (C 1-3 alkyl) sulfonyl) C alqu-3-amino alkyl, cycloalkyl C 3-6-carbonylamino, aminocarbonylamino, alkyl C] _3-aminocarbonylamino, di (C 1-3 alkyl) aminocarbonylamino, a cycloalkyleneiminocarbonylamino group of 4 to 7 members, benzyloxycarbonylamino, phenylcarbonylamino or guanidino, a carboxy group, aminocarbonyl, C C4-aminocarbonyl alkyl, C3-6-aminocarbonyl cycloalkyl, di (C ?3 alkyl) aminocarbonyl, C?-carbonyl alkoxy, C4_6-iminocarbonyl cycloalkylene, a group phenyl or heteroaryl, phenylcarbonylalkyl C 1-3, phenylalkyl C 3-3 or heteroarylalkyl C 1-3, which in the phenyl or heteroaryl radical is optionally substituted once or several times with fluorine, chlorine or bromine atoms, C 1-3 alkyl, amino groups , alkyl C? _3-amino, di (C-3 alkyl) amino, hydroxy, C? _4-oxy alkyl, mono-, di- or trifluoromethoxy, benzyloxy, carboxyalkyl C? -3-oxy, alkyl C? _3-oxycarbonylalkyl C3-oxy, aminocarbonylalkylC3-oxy, alkylC3-aminocarbonylalkylC3-3-oxy, di (C1-3alkyl) aminocarbonylalkylC3-3-oxy, cycloalkyleneiminocarbonylalkoxyC3-7 from 4 to 7 members, carboxy, C C _-3-oxycarbonyl alkyl or C? _-3-oxycarbonylamino alkyl, a cycloalkyl, cycloalkyleneimino, cycloalkylalkyl 1-3 alkyl or cycloalkylene group C3_3 alkyl of 3 to 7 members, wherein in the cyclic part a methylene group can be substituted by a group -? H optionally substituted by a C3_3 alkyl group or C3_3_carbonyl alkyl or by an atom of oxygen, and in which additionally one of the methylene groups contiguous to a group -NH, -N (alkyl C? -3-carbonyl) or -N (alkyl C? -3) can be respectively substituted with a carbonyl group or sulfonyl, with the proviso that a cycloalkyleneimino group is excluded as defined above in which two nitrogen atoms are separated from each other exactly by a group -CH2, R4 represents a hydrogen atom or a C-3 or R3 alkyl group and R4 together with the carbon atom to which they are attached represent a C3- cycloalkyl group, in which one of the methylene groups of the C3- cycloalkyl group may be substituted by an imino group, C3_3-imino alkyl, acylimino or sulfonylimino , R5 represents a hydrogen atom or a C1-3 alkyl group, B re presents a formula group wherein n represents the number 1 or 2, R7 represents a hydrogen atom or a C! _3 alkyl, hydroxy, C?-5-oxycarbonyl, carboxy-C 1-3 alkyl, C C-alkyl 3-3-oxycarbonylalkyl 1-3 alkyl group , amino or C C -3-amino alkyl and R8 independently represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a C ?3 alkyl group in which the hydrogen atoms can be totally or partially substituted by atoms fluorine, a C2_3 alkenyl group or C2_3 alkynyl, hydroxy, C1-3 alkoxy, trifluoromethoxy, amino, nitro or nitrile, wherein, unless otherwise indicated, by the term "heteroaryl group" recited above in the definitions is to be understood a 5- or 6-membered monocyclic heteroaryl group, wherein the 6-membered heteroaryl group contains one, two or three nitrogen atoms and the 5-membered heteroaryl group contains an imino group optionally substituted with a C1- alkyl group .3, phenyl or phenylalkyl C? _3, an ox atom or sulfur or an imino group optionally substituted by a C3_3 alkyl group, phenyl, C2_3 aminoalkyl, C3_3alkylamino_C2-3alkyl, di (C3_3alkyl) C2_3 aminoalkyl, cycloalkyleneimino_alkyl C? _3 from 4 to 7 members or C1-3 phenyloalkyl, or an oxygen or sulfur atom and additionally a nitrogen atom or an imino group optionally substituted with an? -3 alkyl or phenyl? C3 alkyl group and two or three nitrogen atoms and, in addition, in the aforementioned monocyclic heteroaryl groups, a phenyl ring optionally substituted with a fluorine, chlorine or bromine atom, a C? _3 alkyl group, hydroxy, C C _3 alkyl can be condensed by two adjacent carbon atoms. -oxi, amino, alkyl C? _3-amino, di (C? _3 alkyl) amino or C3-6? imino cycloalkylene, and the bonding is carried out by a nitrogen atom or by a carbon atom of the heterocyclic part or by a fused phenyl ring, in which the alkyl and alkoxy groups contained in the s above-cited definitions having more than two carbon atoms, unless otherwise indicated, may be straight or branched chain, and the alkyl groups in the above-mentioned dialkylated moieties, for example the dialkylamino groups, may be the same or and in which the hydrogen atoms of methyl or ethyl groups contained in the aforementioned definitions may be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
2. 2. Amides of substituted carboxylic acids of general formula I according to claim 1, characterized in that A represents a group of general formula wherein m represents the number 1 or 2, R6a independently represents a hydrogen or fluorine atom, a C1-3 alkyl group, hydroxy, amino, C? -3-amino alkyl, di (C? -3 alkyl) amino, aminocarbonyl, C 1 -C 3 -aminocarbonyl alkyl, di (C 1 -C 3 alkyl) aminocarbonyl or C 1 -C 3 alkylcarbonylamino and R 6b may independently be a hydrogen atom, a C 4 alkyl group, alkyl C 4-carbonyl, C 1 -4 -alkoxycarbonyl or C 1 -C 3 -sulfonyl alkyl, with the proviso that the heteroatoms optionally introduced as substituents in the substituted groups A of 5 to 7 members mentioned above are not exactly separated by a carbon atom of another hetero atom, or a group of general formula wherein m represents the number 1 2, X 1 represents a methylene group, -NR 6b, carbonyl or sulfonyl, X represents an oxygen atom or a group -NR 6b, X 3 represents a methylene, carbonyl or sulfonyl group, X 4 represents an atom of oxygen or sulfur, a group -NR6b or carbonyl, X5 represents a carbonyl or sulfonyl group, X8 represents a carbonyl group, X9 represents a carbonyl group, R6a independently represents a hydrogen or fluorine atom, a C3_3 alkyl group , hydroxy, amino, alkyl C? _3-amino, di (C3-alkyl) amino, aminocarbonyl, C 1 3 3-aminocarbonyl alkyl, di (C 1-3 alkyl) aminocarbonyl or C C-3-carbonylamino alkyl and R 6b can independently be a hydrogen atom, a C? _4 alkyl group, C C-carbonyl alkyl, C 1 -C-carbonyl alkoxy or C 3 -3-sulfonyl alkyl, with the proviso that the heteroatoms optionally introduced as substituents in the above-mentioned 5 to 7-membered substituted cyclic groups A are not separated by exactly one carbon atom of another heteroatom , R1 represents a hydrogen, fluorine, chlorine or bromine atom, a C3_3 alkyl group in which the hydrogen atoms may be fully or partially substituted with fluorine atoms, a C2_3 alkenyl group / C2_3 alkynyl, nitro, amino, C.sub.1-3 alkoxy, mono-, di- or trifluoromethoxy, R.sub.2 represents a hydrogen, fluorine, chlorine or bromine atom or a C.sub.1-3 alkyl group, R.sub.3 represents a C.sub.2-3 alkenyl group or C.sub.2-3 alkynyl or an alkyl group C? _6 of straight or branched chain in which the át Hydrogen atoms may be completely or partially substituted by fluorine atoms, and is optionally substituted with a nitrile group, hydroxy, a C?-5-oxy group in which the hydrogen atoms may be totally or partially substituted by atoms fluorine, an allyloxy, propargyloxy, benzyloxy, C?-5-carbonyloxy alkyl, C 1 -5-oxycarbonyloxy, carboxyalkyl C 3 -oxi, C 1 -5 alkyl-oxycarbonylalkyl C 1 -3-oxy, C 1 alkyl group 8-oxycarbonylamino, mercapto, C C-3-sulfanyl alkyl, C? _3-sulfinyl alkyl, C?-3-sulfonyl alkyl, C? -3-carbonylaminoalkyl C?-3-sulfañyl alkyl, C?-3-alkylcarbonylaminoalkyl C 3 -sulfinyl, C 1-3 alkylcarbonylaminoalkyl C 3 -sulfonyl, carboxy, C 1-3 alkyloxycarbonyl, allyloxycarbonyl, propargyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, C 1 -C 3 -aminocarbonyl alkyl, di (C 1 -C 3 alkyl) aminocarbonyl, C3_6-iminocarbonyl cycloalkylene, aminosulfonyl, C3_3-aminosulfonyl alkyl, di (C3_3 alkyl) aminosulfonyl, cycloalkylene C3-6-iminosulfonyl, amino, C?-3-amino alkyl, di (C 1-3 alkyl) amino, alkyl β-5-carbonylamino, C 1 -C 3 -sulfonylamino alkyl, N- (C 1-3 alkylsulfonyl) C3_3-amino alkyl, C3_6-carbonylamino cycloalkyl, aminocarbonylamino, C3_3-aminocarbonylamino alkyl, di (C3_3) aminocarbonylamino, a 4 to 7 membered cycloalkyleneiminocarbonylamino group, benzyloxycarbonylamino, phenylcarbonylamino or guanidino, a carboxy group, aminocarbonyl, C C4-aminocarbonyl alkyl, C3-6-aminocarbonylcycloalkyl, di (C ?3 alkyl) aminocarbonyl, C? -4-carbonyl alkoxy, C4_6-iminocarbonyl cycloalkylene, a phenyl or heteroaryl group, phenylcarbonylalkylC1-3 alkyl, phenylalkyl C1-3 or heteroarylalkyl C1-3, which in the phenyl or heteroaryl part is optionally substituted once or several times with fluorine, chlorine or bromine atoms or C1-3 alkyl, amino, C3-amino-alkyl, di ( alkyl C? _3) amino, hydroxy, alkyl C? -oxy, mono-, di- or trifluoromethoxy, benzyloxy, carboxyalkyl C? _3-oxy-, alkyl C? _3-oxy carbonylalkyl C? -3-oxy, aminocarbonylalkyl C? -3-oxy, alkyl C? -3-aminocarbonyalkyl C1-3-oxy, di (C3_3 alkyl) aminocarbonylalkyl C? -3-oxy, cycloalkyleneiminocarbonylalkoxy C? _3 of 4 to 7 members, carboxy, C 1 3 3-oxycarbonyl or C?-3-oxycarbonylamino alkyl, a cycloalkyl, cycloalkyleneimino, cycloalkylalkyl C? _3 or cycloalkyleneiminoalkyl 3-3 membered, wherein in the cyclic part a methylene group is optionally substituted by an -NH group substituted with a C1-3 alkyl group or C3-alkylcarbonyl group or with an oxygen atom, and in which, additionally, a methylene group contiguous with a group -NH, - N (C 1 -C 3 alkylcarbonyl) or -N (C 1 -C 3 alkyl) can be respectively substituted with a carbonyl or sulfonyl group, with the proviso that a cycloalkyleneimino group defined as above in which two nitrogen atoms are excluded they are separated from each other exactly by a group ~ CH2, R4 represents a hydrogen atom or a graph upo alkyl C? _3, R5 represents a hydrogen atom or a C1-3 alkyl group, B represents a group of formula in which n represents the number 1 or 2, R 'represents a hydrogen atom, a C? _3 alkyl group, hydroxy, C? -5-oxycarbonyl alkyl, C? -3 carboxyalkyl, alkyl C] _3-oxycarbonylalkyl C 1-3, amino or C 1 -C 3 -alkylamino and R 8 independently represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a C?-3 alkyl group in which the Hydrogen can be totally or partially substituted by fluorine atoms, a C2-3 alkenyl group or C2_3 alkynyl, a hydroxy group, C? -3 alkoxy, trifluoromethoxy, amino, nitro or nitrile, in which, unless otherwise indicated by the term cited in the above definitions "heteroaryl group", is meant a 5- or 6-membered monocyclic heteroaryl group, wherein the 6-membered heteroaryl group contains one, two or three nitrogen atoms and the heteroaryl group of 5 members contains an imino group optionally substituted with a C? _3 alkyl group, phenyl or phenylalkyl C? -3, an oxygen atom or a sulfur atom or an imino group optionally substituted by a C? _3 alkyl group, phenyl, C2-3 aminoalkyl, C? -3-aminoalkyl C2_3 alkyl, di (alkyl) C? _3) C2_3 aminoalkyl, a C? -3 cycloalkyleneiminoalkyl group of 4 to 7 membered or phenylalkyl C? _3 or an oxygen atom or sulfur atom, and additionally a nitrogen atom, or an imino group optionally substituted with a group C? -3 alkyl or C? _3 phenylalkyl and two or three nitrogen atoms, and furthermore, in the monocyclic heteroaryl groups mentioned above, a phenyl ring optionally substituted with a fluorine atom, chlorine, can be condensed by two adjacent carbon atoms or bromine, a C? _3 alkyl, hydroxy, C? _3-oxy, amino, C? -3-amino alkyl, di (C? -3) amino or C3-6-imino cycloalkylene group, and the bond is carried out by means of a nitrogen atom or by means of a carbon atom of the heterocyclic part or of a ring -fe condensed nyl, wherein the alkyl and alkoxy groups contained in the above-cited definitions having more than two carbon atoms, unless otherwise indicated, can be straight or branched chain, and the alkyl groups on the dialkylated moieties above mentioned, for example the dialkylamino groups, may be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups contained in the definitions cited above may be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
3. 3. Substituted carboxylic acid amides of general formula I according to claim 1, characterized in that A represents a group of the general formula in which m denotes the number 1 or 2, R6a independently represents a hydrogen or fluorine atom, a C? _3 alkyl, hydroxy, amino, C? -3-amino alkyl, di (C? _3) amino, aminocarbonyl, C? -3-aminocarbonyl, di (C1-3 alkyl) aminocarbonyl or alkyl C? _3-carbonylamino, and R6b can independently be a hydrogen atom, a C? -4 alkyl group, C alqu ~4 alkylcarbonyl, C? -4-carbonyl alkoxy or C?-3-sulfonyl alkyl, with the condition that the heteroatoms optionally introduced as substituents in the above-mentioned 5 to 7 membered substituted groups A are not exactly linked by a carbon atom with another heteroatom, or a group of general formula wherein m means the number 1 or 2, X 1 means a methylene group, -NR 6b, carbonyl or sulfonyl, X 2 means an oxygen group or -NR 6b, X 3 means a methylene, carbonyl or sulfonyl group, X 4 means an oxygen atom or sulfur or a group -NR6b, X5 means a carbonyl or sulfonyl group, R6a independently represents a hydrogen or fluorine atom, a C3_3 alkyl group, hydroxy, amino, C3_3-amino alkyl, di (alkyl C? _3) amino, aminocarbonyl, C3_3-aminocarbonyl alkyl, di (C3_3 alkyl) aminocarbonyl or C3_3-carbonylamino alkyl, and R6b can be independently from each other a hydrogen atom, a C1_4 alkyl group, C 4 alkylcarbonyl, C 1 carbonyl alkoxy or C 1 3 -sulfonyl alkyl, with the proviso that heteroatoms optionally introduced as substituents in the aforementioned 5 to 7 membered substituted cyclic groups are not exactly separated by an atom of carbon from another hetero atom, R1 can be an atom or of fluorine, chlorine or bromine, a C3-alkyl group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, a nitro group, C3_3 alkoxy, a mono-, di- or trifluoromethoxy group , R 2 represents a hydrogen atom, R 3 represents a straight or branched chain C 6 -alkyl group in which the hydrogen atoms can be totally or partially substituted by fluorine atoms, and which is optionally substituted with a nitrile group, hydroxy, benzyloxy, C C-5-oxy alkyl in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, an allyloxy group, C ?5-carbonyloxy alkyl, C?-5-oxycarbonyloxy, carboxyalkyl C ? 3-oxy, alkyl C? -5-oxycarbonylalkyl C? _3-oxy, alkyl C? -8-oxycarbonylamino, C? -3-sulfañyl alkyl, C? _3-sulfonyl alkyl, carboxy, C3-oxycarbonyl alkyl, alkyl C ? 3-aminocarbonyl, di (C? _3 alkyl) aminocarbonyl, C3_6-iminocarbonyl cycloalkylene, aminocarbonylamino, alkyl l C3-aminocarbonylamino or di (C3_3 alkyl) aminocarbonylamino, an aminocarbonyl group, C C-aminocarbonyl alkyl, C3_6-aminocarbonyl cycloalkyl or di (C ?_3 alkyl) aminocarbonyl, a phenyl or heteroaryl group, phenylalkyl C? -3 or heteroarylalkyl C? _3 which is optionally substituted on the phenyl or heteroaryl part one or more times with fluorine, chlorine or bromine atoms, C? _3 alkyl, amino, C? _3-amino alkyl, di (alkyl) groups C? _3) amino, hydroxy, C4_4-oxy, alkyl, mono-, di- or trifluoromethoxy, carboxy or C3_3-oxycarbonyl alkyl, a 3- to 7-membered cycloalkyl group in which it may be substituted in the cyclic a methylene group by a group -NH optionally substituted by a C -3 alkyl group or C? -3-carbonyl alkyl or an oxygen atom, R4 represents a hydrogen atom, R5 represents a hydrogen atom, B represents a formula group wherein n represents the number 1, R7 represents a hydrogen atom, and R8 represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a methyl group, C2_3 alkynyl or methoxy, in which the hydrogen atoms may be completely or partially substituted by fluorine atoms, in which, unless otherwise indicated, by the expression mentioned above in the definitions "heteroaryl group", it is to be understood a 5- or 6-membered monocyclic heterocyclic group in which the 6-membered heterocyclic group contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C?-3 alkyl group, an oxygen atom or a sulfur atom, or a group imino optionally substituted with a C? -3 alkyl group, or an oxygen atom or a sulfur atom, and additionally a nitrogen atom, or an imino group optionally substituted with a C? -3 alkyl group and two or three carbon atoms? nitro and the connection is carried out by a nitrogen atom or by a carbon atom, in which the alkyl and alkoxy groups contained in the aforementioned definitions have more than two carbon atomsunless otherwise indicated, they may be straight or branched chain and the alkyl groups in the dialkylated radicals mentioned above, for example the dialkylamino groups, may be the same or different, and in which the hydrogen atoms of the groups methyl or ethyl contained in the above-mentioned definitions can be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
4. 4. Substituted carboxylic acid amides of general formula I according to claim 3, characterized in that A, R1, R2, R4, R5 and B are defined as described in claim 3 and R3 represents a straight-chain C6 alkyl group or branched in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, which is optionally substituted with a nitrile, hydroxy, benzyloxy group, a C 5 5 -oxy alkyl group in which the hydrogen atoms may be total or partially substituted by fluorine atoms, an allyloxy group, C 1 ~ 5 alkylcarbonyloxy, alkyl C 5 -oxycarbonyloxy, carboxyalkyl C 3 -oxy, alkyl C 5 -oxycarbonylalkyl C 3 -oxi, alkyl C ? -8-oxycarbonylamino, C? -3-sulfanyl alkyl, C? _3-sulfonyl alkyl, carboxy, C? -3-oxycarbonyl alkyl, C? -3-aminocarbonyl alkyl, di (C? _3) aminocarbonyl alkyl, C3 cycloalkylene -6-iminocarbonyl, aminocarbonylamino, alkyl C? -3-aminocarbonylamino or di (C? -3 alkyl) amino carbonylamino, an aminocarbonyl group, C 1 - aminocarbonyl alkyl, C 3-6 cycloalkyl aminocarbonyl or di (C 1 3 alkyl) aminocarbonyl group, in which the alkyl and alkoxy groups contained in the aforementioned definitions have more than two atoms of carbon, unless otherwise indicated, can be straight or branched chain, and in which the alkyl groups in the dialkylated moieties mentioned above, for example dialkylamino groups, can be the same or different, and in which Hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions may be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
5. 5. Substituted carboxylic acid amides of general formula I according to claim 3, characterized in that A, R1, R2, R4, R5 are defined as described in claim 3, and R3 represents a phenyl or heteroaryl group, phenylalkyl C ? -3 or heteroarylalkyl C? _ Which on the phenyl or heteroaryl moiety is substituted once or several times with fluorine, chlorine or bromine atoms, C? -3 alkyl groups, amino, C? -3-amino alkyl, di (C C_3 alkyl) amino, hydroxy, C?-oxy-, mono-, di- or trifluoromethoxy, carboxy or C C-3-oxycarbonyl alkyl, a 3- to 7-membered cycloalkyl group, in which a methylene group in the cyclic part it may be substituted by an -NH group optionally substituted with a C3_3 alkyl or C3_3-carbonyl group, or by an oxygen atom, in which, unless otherwise indicated, the expression cited in the above definitions "heteroaryl group", is to be understood a monocyclic heteroaryl group of 5 or 6 members in which the 6-membered heteroaryl group contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C ?3 alkyl group, an oxygen atom or a sulfur atom , or an imino group optionally substituted with a C? -3 alkyl group or an oxygen atom or a sulfur atom and additionally a nitrogen atom, or an imino group optionally substituted with a C? _3 alkyl group and two or three atoms of nitrogen, and the bonding is carried out by a nitrogen atom or a carbon atom, in which the alkyl and alkoxy groups contained in the aforementioned definitions having more than two carbon atoms, unless otherwise indicated, can be straight or branched chainand the alkyl groups in the dialkylated radicals mentioned above, for example the dialkylamino groups, can be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions can be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
6. 6. Amides of substituted carboxylic acids of general formula I according to claim 1, characterized in that A represents a group of general formula wherein m represents the number 1 or 2, R6a independently represents a hydrogen or fluorine atom or a C ?3 alkyl group, and R6b can be a hydrogen atom or a C? -3 alkyl group, with the proviso that the heteroatoms optionally introduced as substituents in the above-mentioned 5 to 7-membered substituted groups A are not exactly separated by a carbon atom of another heteroatom, or a group of general formula wherein m represents the number 1 or 2, X1 represents a methylene group, -NR6b, carbonyl or sulfonyl, X2 represents an oxygen atom or a group -NR6b, X3 represents a methylene, carbonyl or sulfonyl group, X4 represents an atom of oxygen or a sulfur atom or a group -NR6b, X5 represents a carbonyl group or a sulfonyl group, R6a independently represents a hydrogen or fluorine atom or a C3_3 alkyl group, and R6b may independently be a hydrogen atom or a C? _3 alkyl group, with the proviso that the heteroatoms introduced as substituents in the 5- to 7-membered cyclic A groups mentioned above are not exactly separated by a carbon atom of another hetero atom, R 1 represents an atom of chlorine or bromine, a methyl or methoxy group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, or a nitro group, R2 represents a hydrogen atom, R3 represents a is a straight or branched chain C? -4 alquilo alkyl group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, and which is optionally substituted with a hydroxy group, an alkyl C?-4-oxy group; wherein the hydrogen atoms may be fully or partially substituted with fluorine atoms, a C? _3-sulfañyl alkyl group, C? ~3-sulfonyl alkyl, carboxy or C? _3-oxycarbonyl alkyl, a phenyl or heteroaryl group, phenylalkyl C? -3 or heteroarylalkyl C? _3, which in the phenyl or heteroaryl part is optionally substituted once or several times with fluorine, chlorine or bromine atoms, C? _3 alkyl groups, C? -4-oxy, mono- , di- or trifluoromethoxy, carboxy or C 1 ~ 3-oxycarbonyl alkyl, R 4 represents a hydrogen atom, R 5 represents a hydrogen atom, and B represents a group of formula wherein n represents the number 1, R7 represents a hydrogen atom, and R8 represents a chlorine or bromine atom or the ethynyl group, wherein, unless otherwise indicated, by the term cited in the above definitions "heteroaryl group" is to be understood as a 5- or 6-membered monocyclic heteroaryl group, in which the 6-membered heteroaryl group contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an optionally substituted imino group with a C? _3 alkyl group, or an oxygen atom or a sulfur atom, or an imino group optionally substituted with a C? -3 alkyl group or an oxygen atom or a sulfur atom and additionally a nitrogen atom, or an imino group optionally substituted with a C? -3 alkyl group and two or three nitrogen atoms, and the bonding is carried out by a nitrogen atom or by a carbon atom, in which the alkyl and alkoxy groups contained in the definition is previously cited having more than two carbon atoms, unless otherwise indicated, they can be straight or branched chain, and wherein the alkyl groups in the dialkylated moieties mentioned above, for example the dialkylamino groups, can be same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions may be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
7. 7. Substituted carboxylic acid amides of general formula I according to claim 6, characterized in that A, R1, R2, R4, R5 and B are defined as described in claim 6 and R3 is a C? _4 alkyl group of straight or branched chain in which the hydrogen atoms may be fully or partially replaced by fluorine atoms, and which is optionally substituted with a hydroxy group, a C 4 -4 -oxi alkyl group in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, a C 3 -sulfanyl alkyl group, C 3 -sulfonyl alkyl, carboxy or C C-3-oxycarbonyl alkyl, wherein the alkyl and alkoxy groups contained in the above-cited definitions having more than two carbon atoms, unless otherwise indicated, may be straight or branched chain, and wherein the alkyl groups in the dialkylated radicals mentioned above, for example the dialkylamino groups, can be the same or different, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions can be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
8. 8. Substituted carboxylic acid amides of general formula I according to claim 6, characterized in that A, R1, R2, R4, R5 and B are defined as described in claim 6 and R3 is a phenyl or heteroaryl group, phenylalkyl C? _3 or heteroaryl which in the phenyl or heteroaryl part is optionally substituted once or several times with fluorine, chlorine or bromine atoms, C3 alkyl groups, C? _4-oxy alky, mono-, di- or trifluoromethoxy-, carboxy- or C3_3-oxycarbonyl alkyl, a 3- to 7-membered cycloalkyl group in which in the cyclic part a methylene group may be substituted by a group, NH optionally substituted with a C3_3 alkyl group or C3_3 alkyl carbonyl, or by an oxygen atom, in which, unless otherwise indicated, by the term cited in the above definitions "heteroaryl group", it is to be understood a 5 or 6 membered monocyclic heteroaryl group, wherein The 6-membered heteroaryl group contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C? _3 alkyl group, an oxygen atom or a sulfur atom or an imino group optionally substituted with a C?-3 alkyl group or an oxygen or sulfur atom and additionally a nitrogen atom or an imino group optionally substituted with a C? -3 alkyl group and two or three nitrogen atoms, and the bonding is carried out by a nitrogen atom or by a nitrogen atom. carbon, wherein the alkyl groups contained in the aforementioned definitions having more than two carbon atoms, unless otherwise indicated, can be straight or branched chain, and wherein the alkyl groups on the dialkylated moieties cited above, for example the dialkylamino groups, may be the same or different, and wherein the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions may be tot to or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
9. 9. Substituted carboxylic acid amides of general formula 1 according to claim 1, characterized in that A represents a group of formula where m means the number 1 or 2, R6a independently represents a hydrogen atom or a fluorine atom or a C3_3 alkyl group, with the proviso that the fluorine atoms introduced as substituents in the cyclic groups A substituted from 5 to 7 members mentioned above are not separated directly by a carbon atom of another heteroatom, R 1 signifies a chlorine or bromine atom, a methyl or methoxy group in which the hydrogen atoms may be totally or partially substituted, or a nitro group, R 2 signifies a hydrogen atom, R 3 signifies a straight or branched chain C 1 _ 4 alkyl group in which the hydrogen atoms may be totally or partially substituted by fluorine atoms, and which is optionally substituted with a hydroxy group, C C _-4-oxy alkyl, in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, a C alqu-3-sulfanyl alkyl group, C C _3-s alkyl ulphonyl, carboxy or C3-3-carbonyl alkoxy, a furanyl, thiophenyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridinyl-C6-2 or imidazolylalkyl-C2-2 group, which may be optionally substituted in the heteroaryl part with one or two C? _3 alkyl groups, C? -3-oxy, carboxy or C? -3-oxycarbonyl alkyl, and R4 represents a hydrogen atom, R5 represents a hydrogen atom and B represents a group of formula in which n represents the number 1, R7 represents a hydrogen atom and R8 represents a chlorine or bromine atom or an ethynyl group, in which, unless otherwise indicated, by the expression quoted in above definitions "heteroaryl group", is to be understood a 5- or 6-membered monocyclic heteroaryl group, wherein the 6-membered heteroaryl group contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group eventualme is substituted with a C? -3 alkyl group, an oxygen atom or a sulfur atom or an imino group optionally substituted with a C? _3 alkyl group or an oxygen or sulfur atom and additionally a nitrogen atom, or a group imino optionally substituted with a C? -3 alkyl group and two or three nitrogen atoms, and the bonding is carried out by a nitrogen atom or by a carbon atom, in which the alkyl groups contained in the aforementioned definitions have more than two carbon atoms, unless otherwise indicated, can be straight or branched chain, and in which the alkyl groups in the dialkylated moieties mentioned above, for example the dialkylamino groups, can be the same or different, and wherein the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions may be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastere monomers, their mixtures and their salts.
10. 10. Substituted carboxylic acid amides of general formula I according to claim 9, characterized in that A, R1, R2, R4, R5 and B are defined as described in claim 9 and R3 is a C? _4 alkyl group of linear or branched chain in which the hydrogen atoms may be totally or partially substituted by fluorine atoms, and which is optionally substituted with a hydroxy group, C alqu -4-4-oxy alkyl in which the hydrogen atoms may be total or partially substituted by fluorine atoms, a C? _3-sulfañyl alkyl, C?-3-sulfonyl, carboxy or C?-3-oxycarbonyl alkyl group, in which the alkyl and alkoxy groups contained in the aforementioned definitions have more than two carbon atoms, unless otherwise indicated, can be straight or branched chain, and in which the alkyl groups in the dialkylated moieties mentioned above, for example the dialkylamino groups, can be the same or different. stintos, and in which the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions may be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
11. 11. Amides of substituted carboxylic acids of general formula I according to claim 9, characterized in that A, R1, R2, R4, R5 and B are defined as described in claim 9 and a furanyl, thiophenyl, pyrrolyl, pyrazolyl, imidazolyl group , oxazolyl, isoxazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyridinyl, pyridinyl-C 1 -2 or imidazolylalkyl-C 2 -2, which optionally in the heteroaryl part may be substituted with one or two C 1 -3 alkyl groups in which the hydrogen atoms they may be wholly or partly substituted by fluorine atoms, C ?_3-oxy oxy groups in which the hydrogen atoms may be fully or partially substituted by fluorine atoms, carboxy groups or C ?3-oxycarbonyl alkyl, and in which , unless otherwise indicated, by the term cited in the above definitions "heteroaryl group", is meant a 5- or 6-membered monocyclic heteroaryl group, wherein the heteroaryl group of 6 members contains one, two or three nitrogen atoms, and the 5-membered heteroaryl group contains an imino group optionally substituted with a C? -3 alkyl group, an oxygen atom or a sulfur atom, or an optionally substituted imino group with a C? -3 alkyl group or an oxygen atom or a sulfur atom and additionally a nitrogen atom, or an imino group optionally substituted with a C? _3 alkyl group and two or three nitrogen atoms, and the bond is it is carried out by means of a nitrogen atom or by a carbon atom, in which the alkyl groups contained in the aforementioned definitions having more than two carbon atoms, unless otherwise indicated, can be straight or branched chain, and wherein the alkyl groups in the dialkylated moieties mentioned above, for example the dialkylamino groups, can be the same or different, and wherein the hydrogen atoms of the methyl or ethyl groups mentioned in the above definitions can be totally or partially substituted by fluorine atoms, their tautomers, their enantiomers, their diastereomers, their mixtures and their salts.
12. 12. Substituted carboxylic acid amides of general formula I according to one of claims 1 to 7 or 8, characterized in that the group X1 represents a methylene group.
13. 13. Substituted carboxylic acid amides of general formula I according to one of claims 1 to 8, characterized in that the group X1 represents a carbonyl group.
14. 14. Amides of substituted carboxylic acids of general formula I according to one of claims 1 to 8, 12 or 13, characterized in that the group X3 represents a methylene group.
15. 15. Substituted carboxylic acid amides of general formula I according to one of claims 1 to 8, 12 or 13, characterized in that the group X3 represents a carbonyl group.
16. 16. Amides of substituted carboxylic acids of general formula I according to one of claims 1 to 8, or 12 to 15, characterized in that the group X4 represents an oxygen atom.
17. 17. Amides of substituted carboxylic acids of general formula I according to one of claims 1 to 16, characterized in that the rest B means the group
18. 18. Amides of carboxylic acids of general formula I according to one of claims 1 to 16, characterized in that the rest B means the group
19. 19. Amides of substituted carboxylic acids of general formula I according to one of claims 1 to 16, characterized in that the rest B means the group
20. 20. Amides of carboxylic acids of general formula I according to one of claims 1 to 19, characterized in that the residue B represents a chlorine atom.
21. 21. Amides of carboxylic acids of general formula I according to one of claims 1 to 19, characterized in that the radical R8 represents a bromine atom.
22. 22. Substituted carboxylic acid amides of general formula I according to one of claims 1 to 19, characterized in that the radical R8 represents an ethynyl group
23. 23. Substituted carboxylic acid amides of general formula I according to one of claims 1 to 22, characterized because the general formula corresponds to (la)
24. 24. The following compounds of general formula I according to claim 1: 4- (Azepan-2-on-1-yl) -N- [(IR) -1- (5-chloro-1H-benzimidazole -2-yl) -2-methoxyethyl] -3-methylbenzamide, 4- (Azepan-2-on-l-yl) -N- [(li?) -1- (5-chloro-li? -benzimidazole-2 -yl) -2-hydroxyethyl] -3-methylbenzamide, N- [(SS) -1- (5-Chloro-lH-benzimidazol-2-yl) -3-methylsulfanylpropyl] -3-methyl-4- (pyrrolidin- 2-on-l-yl) -benzamide, N- [(li?) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4 -yl) -3-trifluoromethyl-benzamide, N- [(li?) -1- (5-Chloro-l, -benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholin-3-) on-4-yl) -benzamide, N- [(SS) -1- (5-Chloro-1-benzimidazol-2-yl) -3-methylsulfanyl-propyl] -3-methyl-4- (morpholin-3-) on-4-yl) -benzamide, N- [(li?) -1- (5-Chloro-1-yl-benzimidazol-2-yl) -2-hydroxyethyl] -3-methyl-4- (morpholin-3-on -4-yl) -benzamide, 4- (Azepan-2-on-l-yl) -3-chloro-N- [(li?) -1- (5-chloro-1-yl-benzimidazol-2-yl) - 2-methoxy-ethyl] -benzamide, 4- (Azepan-2-on-li l) -N- [(li?) -1- (5-chloro-lH-benzimidazol-2-yl) -2-methoxy-ethyl] -3-trifluoromethyl-benzamide, N- [(SS) -1- ( 5-Chloro-l-benzimidazol-2-yl) ethyl] -3-methyl-4- ([1, 3] oxazepan-2-on-3-yl) -benzamide, N- [(SS) -1- ( 5-Chloro-li-benzimidazol-2-yl) -3-methylsulfanyl-propyl] -4- (morpholin-3-on-4-yl) -3-nitro-benzamide, N- [(li?) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxy-ethyl] -3-methyl-4- ([1,3] oxazepan-2-on-3-yl) -benzamide, 3-Chloro- N- [(li?) -1- (5-chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- ([1,4] oxazepan-5-on-4-yl) -benzamide, 3-Chloro-N- [(li?) -1- (5-chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (piperidin-2-on-l-yl) -benzamide, N - [(li?) -1- (5-Bromo-lH-benzimidazol-2-yl) -2-hydroxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) -benzamide, N- [(li ?, 2S) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxypropyl] -3-methyl-4- (morpholin-3-on-4-yl) -benzamide, N - [(SS) -1- (5-Chloro-1-benzimidazol-2-yl) ethyl] -3-methyl-4- (thiomorpholin-3-on-4-yl) -benzamide, N- [(li? ) -1- (5-Chloro-l) i? -benzimidazol-2-yl) -2-methoxy-ethyl] -3-methyl-4- (piperidin-2-on-l-yl) -benzamide, N- [(11?) -1- (5- Chloro-li? -benzimidazol-2-yl) -2-methoxy-ethyl] -3-methyl-4- ([1,3] oxazinan-2-on-3-yl) -benzamide, N- [(li? ) -1- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- (piperidin-2-on-l-yl) -3-trifluoromethyl-benzamide, N- [(li?) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (1,1-dioxo [1,2] thiazinan-2-yl) -3-methyl-benzamide, N- [(1S) -1- (5-Chloro-lH-benzimidazol-2-yl) butyl] -3-methyl-4- (morpholin-3-on-4-yl) -benzamide, N- [(li?) -1- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -4- ([1,3] oxazepan-2-on-3-yl) -3-trifluoromethyl-benzamide, N- [ (li?) -1- (5-Chloro-li? -benzimidazol-2-yl) -2-methoxyethyl] -4- (1,1-dioxo [1,2,6] thiadiazin-2-yl) -3 -methyl-benzamide, N- [(li?) -1- (5-Bromo-li-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (morpholin-3-on-4-yl) ) -benzamide, N- [(15) -1- (5-Chloro-lH-benzimidazol-2-yl) -3- (1, 4-tetrazol-5-yl) propyl] -3-methyl-4- (morpholino- 3-on-4-il) -b Enzyme, N- [(15) -1- (5-Chloro-li? -benzimidazol-2-yl) -3-methoxypropyl] -3-methyl-4- (morpholin-3-on-4-yl) -benzamide , N- [(li?) -1- (5-Chloro-lE-benzimidazol-2-yl) -2-methylsulfanylethyl] -3-methyl-4- (morpholin-3-on-4-yl) -benzamide, N- [(li?) -1- (5-Chloro-l-benzimidazol-2-yl) -2-methoxyethyl] -3-methyl-4- (thiomorpholin-3-on-4-yl) -benzamide, 3 -Cloro-N- [(li?) -1- (5-chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (morpholin-3-on-4-yl) -benzamide, 3 ~ Chloro-N- [(li?) -1- (5-chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (1,1-dioxo [1,2] thiazinan-2-yl) -benzamide, N- [(li?) -1- (5-Chloro-lH-benzimidazol-2-yl) -2-methoxyethyl] -4- (1,1-dioxo [1, 2] thiazepan-2-yl) ) -3-methyl-benzamide, 3-Bromo-N- [(SS) -1- (5-chloro-li? -benzimidazol-2-yl) ethyl] -4- (piperidin-2-on-l-yl) ) -benzamide, 3-Bromo-N- [(li?) -1- (5-chloro-l-l-benzimidazol-2-yl) -2-methoxyethyl] -4- (piperidin-2-on-l-yl) -benzamide, N- [1- (5-Chloro-l-benzimidazol-2-yl) -1- (furan-2-yl) methyl] -3-methyl-4- (piperidin-2-on-l-yl) ) -benzamide, its tautomers, its enantiomers, their diastereomers, their mixtures and their salts are especially preferred.
25. 25. Physiologically compatible salts of the compounds according to claims 1 to 24.
26. 26. A medicament containing a compound according to at least one of claims 1 to 24 or a physiologically compatible salt according to claim 25, further characterized by optionally one or several vehicles and / or inert diluents.
27. 27. Use of a compound according to at least one of claims 1 to 24 or of a physiologically compatible salt according to claim 25 characterized by the preparation of a medicament with an inhibitory effect on factor Xa and / or an inhibitory effect on Related serine protease.
28. 28. Process for the preparation of a medicament according to claim 26, characterized in that a compound according to at least one of claims 1 to 24 or a physiologically compatible salt according to claim 25 is processed non-chemically in one or more vehicles and / or inert diluents.