MXPA99011261A - Phenylalkyl derivatives with thrombin-inhibiting effect - Google Patents

Abstract

The invention relates to phenylalkyl derivatives of general formula (I) in which A, B,W, Y and Ra to Rd are as defined in claim 1, their tautomers, their stereoisomers, their mixtures and their salts with valuable properties. The compounds of general formula (I), in which Rb is a hydrogen atom, a nitro group or a cyano group, are valuable intermediates for producing the other compounds of general formula (I). Furthermore, the compounds having general formula (I), in which Rb is one of the optionally substituted aminomethyl or amidino groups mentioned in claim 1, as well as their tautomers and stereoisomers, have valuable pharmacological properties, in particular as thrombin inhibitors and in extending the thrombin time.

Description

DERIVATIVES OF FENILALQUILO, PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS? PROCESSES TO PREPARE THEM DESCRIPTION OF THE INVENTION The present invention relates to phenylalkyl derivatives of the general formula their tautomers, their stereoisomers and mixtures thereof, and their salts, in particular their physiologically acceptable salts with organic and inorganic acids or bases, which have valuable properties The compounds of the general formula I above, in the that Rb denotes a hydrogen atom, a nitro or cyano group, are valuable intermediate products for producing the other compounds of the general formula I, and the compounds of the above general formula I in which Rb denotes one of the aminomethyl or amidino groups optionally substituted compounds mentioned below, and their tautomers and stereoisomers, possess valuable pharmacological properties, in particular an inhibitory activity of thrombin, the effect of prolonging the thrombin interval and an inhibitory effect of thrombocyte aggregation. Accordingly, the present invention relates to novel compounds of the above general formula I and their preparation, with pharmaceutical compositions containing the pharmacologically active compounds, and with their use. and * In the general formula I above Ra denotes a hydrogen atom, a carboxy group, C? _3-alkoxycarbonyl, benzoyl, phenylsulfonyl, nitro, R? NR2, R? NR2-X-, or (R3X) NR? - in which - Ri denotes a hydrogen atom, a C1-5-alkyl group which may be substituted with a group _ phenyl, carboxy, C? -4-alkoxycarbonyl or aminocarbonyl, 71as the amino group of the aminocarbonyl group - it may be additionally mono- or disubstituted with C groups - alkyl, phenyl-C? -3-alkyl, phenyl, carboxy-C? _3-alkyl or C? -3-alkoxycarbonyl-C? _3-alkyl, * ^^ - and the substituents may "be identical or different, .. or a linear chain C2-3-alkyl group that is "terminally substituted with amino group, C? _3-alkylamino, di- (C? -3-alkyl) amino, C? _-alkanoylamino, phenylamino, N-benzyloxycarbonyl-1-phenylamino, pyrrolidino, piperidino or" morpholino, R 2 denotes a hydrogen atom, a dealkyl group optionally substituted with one or two phenyl groups or with a naphthyl group, or a phenyl group which "may be substituted with a fluorine, chlorine or bromine atom, or with a group C2_3-straight-chain alkyl which is terminally substituted with an amino group, C1-3-alkylamino, C? _3-alkanoylamino, di- (C? -3-alkyl) amino, pyrrolidino, piperidino or morpholino Ri and R2 together with A nitrogen atom therebetween denote a pyrrolidino or piperidino group optionally substituted with a C? -3-alkyl, carboxy or C? -3-alkoxycarbonyl group, a pyrrolidino or piperidino group substituted with two C? -3-alkyl groups or a morpholino group R.sup.3 denotes a straight or branched chain C? _7-alkyl group which may be substituted at the 1, 2 or 3 position with a phenyl group, or at the 2 to 7 position with a fluorine, chlorine or bromine atom , with a carboxy or C? -3-alkoxycarbonyl group, a trifluoromethyl group, a phenyl, naphthyl or chromanil group or that in each case it can be substituted with a fluorine, chlorine or bromine atom, with a trifluoromethyl group, -C? _3-alkyl, C? _3-alkoxy, amino, C? _3-alkylamino, di- (C? -3"-alkyl) amino or aminocarbonyl, while the phenyl, naphthyl or chromanyl groups above The compounds mentioned can be further substituted with one to three methyl groups, a phenyl group or Taminophenyl substituted with two chlorine atoms or - bromine, a thienyl group optionally substituted with a chlorine or bromine atom or with a methyl group, a -C3-8-cycloalkyl group, Cs-12-bicycloalkane, quinolyl, ^ "isoquinolyl or benzimidazolyl, or -i * 1 = 5z?" -__ Ri and R3 together denote an n-alkylene group with 3 at 5 carbon atoms, where an ethylene group linked to the group S02- or CO- can be substituted with a 1, 2-phenylene group, and * X denotes a carbonyl or sulfonyl group, * or Ra can also be substituted represent a C2-3-α-alkanoyl group which on the alkyl moiety is substituted with a carboxy-C? -3-alkyl group or C1.-3-alkoxycarbonyl-C1- .3-alkyl and a benzoyl group, naphthoyl, phenylsulfonyl or - naphthylsulfonyl, -_ R denotes an amidino group optionally ^ substituted with a C? _? o-alkoxycarbonyl or phenyl- a cyano or aminomethyl group, Rc and d which may be identical or different, ^ denote each one a hydrogen atom, fluorine, chlorine, ? bromine or iodine, a methyl, methoxy, nitro, amino or aminocarbonyl group, or an amino group optionally substituted with a straight chain C2-alkanoyl group Note that the alkanoyl moiety may be terminally substituted with a carboxy or C? -3-alkoxycarbonyl group, - A denotes an ethylene, ethenylene, n-propylene or n-butylene group, optionally substituted with one or two C? -3-alkyl groups, while a methylene group of an ethylene group or "n-propylene optionally substituted with one or two C? _3-alkyl groups, linked - (i) the nitrogen atom can be substituted with a carbonyl group, or (ii) the phenyl nucleus can be substituted with an oxygen or sulfur atom, with a sulfinyl or sulfonyl group, or with an optionally substituted imino group ^ substituted with a group C? _3-alkyl, _B denotes a bond, a methylene group, ethylene, Eethylene or n-propylene, optionally substituted with one or two C1-.3-alkyl groups, while (iii) if the previously mentioned methylene, ethylene, ethenylene or n-propylene groups denote a carbonyl group or thiocarbonyl, a methylene group can be substituted with an oxygen atom or with an imino group optionally substituted by a 2-C-3-alkyl group, or 7_. { iv) if in the above-mentioned ethylene or n-propylene groups Y denotes a methylene group, a methylene group in the 3 or 4 position In relation to the nitrogen atom it can be substituted with an oxygen atom or with an imino group optionally substituted by a C1-3-alkyl group, which denotes a methino group or a nitrogen atom, and FY denotes a group methylene, carbonyl or thiocarbonyl. However, the preferred compounds of the above general formula I are those in which RaRa, Rc, Rd, A, B, W and Y are co or defined in the above, and den denotes an amidino group optionally ^ substituted with a C *? -? 0-alkoxycarbonyl or phenyl- ^ C? -3-alkoxycarbonyl group, their optical antipodes and their asbestos. ~ However, the compounds in particular - Preferred s of the above general formula I are * = £ to which those in which 'XR denotes a group R? NR2, Rx' NR2? -X- or (R3X) NR? ~ in which '~ Ri denotes uh hydrogen atom, a C? _- ^ alkyl group which may be substituted with a group ^ phenyl, carboxy, C? _2-alkoxycarbonyl or aminocarbonyl, -as the amino group of the aminocarbonyl group It may be additionally mono- or disubstituted with groups C? _- alkyl, phenel, benzyl, carboxy-C? _2- R 2 alkyl or C 2 -2-alkoxycarbonyl-C 2 -alkyl, and the substituents may be identical or different, or an ethyl group which is terminally substituted by amino group, acetylamino morpholino phenylamino or N-benzyloxycarbonyl phenylamino, R 2 denotes a hydrogen atom, a C? _3-f7alkyl group optionally substituted with one or two phenyl groups or with a naphthyl group, a cyclohexyl group, or a phenyl group optionally substituted with a chlorine atom, with a 2- group aminoethyl or 2-acetylamino, Ri? and R2 x have the meanings that were given t. above for Ri and R2 or together with the nitrogen atom they denote a pyrrolidino or piperidino group optionally substituted with a jmethyl, carboxy or C? -2-alkoxycarbonyl group, a -pyrrolidino or piperidino group substituted with two methyl groups , or a morpholino group, R3 denotes a straight or branched chain C? -5-alkyl group which may be substituted at the position 1, 2 or 3 with a phenyl, carboxy or C1-3-alkoxycarbonyl group, or in the 2 or 3 position with a chlorine atom, a trifluoromethyl group, a phenyl or tnaphthyl group which in each case can be substituted with a 'fluorine, chlorine atom' or bromine, with a trifluoromethyl group, C? -3-alkyl, C? -3-alkoxy, amino, C1-3- Alkylamino, di- (C? -3-alkyl) amino or aminocarbonyl, insofar as the aforementioned phenyl groups can be further substituted with one to three methyl groups, a phenyl or aminophenyl group substituted with two chlorine atoms or bromine, a thienyl group substituted with a "bromine or bromine atom, a C3_-cycloalkyl, quinolyl, isoquinolyl or benzimidazolyl group, or-Ri and 3 together denote an n-alkylene group with 3" to 5 carbon atoms , wherein an ethylene group linked to the group S02 or CO- can be substituted with a 1, 2-phenylene group, and X denotes a carbonyl or sulfonyl group, or Ra also denotes "a C2-3-alkanoyl group. which is substituted with a carboxy-C? -3-alkyl or Ci- 3-alkoxycarbonyl-C? _3-alkyl group and a benzoyl,? Tnaphthoyl, phenylsulfonyl or naphthylsulfonyl group, Rb denotes an amidino group optionally "substituted with a C group ? _? 0-alkoxycarbonyl or phenyl-C? -3-alkoxycarbonyl, Rc denotes a hydrogen atom, fluorine, chlorine, bromide or iodine, a methyl, methoxy, aminocarbonyl, amino or nitro group, or an optionally substituted amino group with a straight chain C2 alkanoyl group wherein the alkanoyl moiety may be terminally substituted with a caTrboxi or C? _3-alkoxycarbonyl group, Rd denotes a hydrogen atom A denotes an ethylene, n-propylene or n- ± butylene group, optionally substituted with one or two methyl groups, while a methylene group of an ethylene or n-propylene group optionally substituted with one or two methyl groups, which is * (i) bonded to the nitrogen atom can be substituted with a carbonyl group, B denotes a bond, a methylene group, ethylene, ethenylene or n-propylene optionally substituted with one or two methyl groups, while T ^ (iii) if in the previously mentioned methylene, ethylene or n-propylene groups Y denotes a carbonyl or thiocarbonyl group, a methylene group can be substituted with an oxygen atom or with an imino group optionally substituted with an methyl group, or (iv) if in the previously mentioned ethylene or n-propylene groups Y denotes a ^ methylene group, a methylene group in the 3 or 4 position relative to the nitrogen atom can be substituted with an oxygen atom or with an imino group optionally substituted with a methyl group, .sw denotes a methino group, and denotes a methylene, carbonyl or thiocarbonyl group, particularly the compounds mentioned above in which "Ra denotes a group (R3S02) ÑR ?, its optical antipodes or its salts. particularly preferred are those in which Ra denotes a group (R3S02) NR ?, while Ri and R3 are as defined above, Rb denotes an amidino group optionally substituted with a group C? -? 0- alkoxycarbonyl or phenyl-C? -3-alkoxycarbonyl,? Rc and Rd each denote a hydrogen atom, A denotes a n-propylene group optionally -substituted with a methyl group, B denotes an ethylene group, denotes a methino group, and Y denotes a carbonyl group, its optical antipodes and its salts.

The following particularly preferred compounds are mentioned by way of example: (a) l- [3- (4-amidino-phenyl) propionyl] -6- (4-fluoro-phenylsulfonamido) -1, 2, 3, 4-tetrahydro-quinoline, (b) l- [3- (4-amidino-phenyl) propionyl] -6-butyl-, sulfonamido-1,2,3,4-tetrahydro-quinoline, (c) l- [3- (4-amidino- phenyl) propionyl] -5-phenyl-1-sulfonamido-1,2,3,4-tetrahydro-quinoline, (d) "l- [3- (4-amidino-phenyl) -propionyl] -3-methyl-6- phenyl-sulfonamido-1,2,3,4-tetrahydro-quinoline, (e) l- [3- (4-amidino-phenyl) propionyl] -6- (5-chloro-thien-J2-ylsulfonamido) -1, 2,3,4-tetrahydro-quinoline, (f) l- [3- (4-amidino-phenyl) propionyl] -6-phenyl-sulfonamido-1,2,3,4-tetrahydro-quinoline, (g) l - [3- (4-amidino-phenyl ") propionyl] -6- (N-methyl-phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline, (h) l- [3- (4- amidino-phenyl) propionyl] -6- (N-ethoxy-carbonylmethyl-phenylsulfonamido) -1,2,3,4-tetrahydro- "" quinoline, (i) l- [3- (4-amidino-phenyl) propionyl] ] -6- (N-carboxymethyl-phenylsulfonamido) -1, ~ 2, 3, 4-tetrahydro-quinoline, (j) l- [3- (4-aminomethyl-phenyl) -propionyl] -6-phenylsulfonamido-1, 2,3,4-tetrahydro-quinoline, (k) l - [3- (4-amidino-phenyl) propyl] -6-phenylsulfonamido-, 1,2,3,4-tetrahydro-quinoline, (1) l- [3- (4-methyloxycarbonyl-amidino-phenyl) propionyl] - = 6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline, (m) ~ 1 - [3- (4-amidino-phenyl) -propionyl] -6- (N-phenyl- "methyl-aminocarbonyl) -1,2,3, 4-tetrahydro-quinoline, (n) l- [3- (4-amidino-phenoxy) -acetyl] -6- [N- (1-naphthyl-sulfonyl) -hydroxycarbonylmethylamino] -!, 2,3,4-tetra-; hydroquinoline, (o) l- [3- (4-amidino-phenyl) -propionyl] -β-diethylamino- "carbonylphenyl-1,2,3,4-tetrahydro-quinoline, (p) l- [3- (4-amidino-phenyl) -propionyl] -6- (N-benzoyl-J methylamino) -1, 2, 3, 4-tetrahydro-quinoline, (q) l- [3- (4-amidino-phenyl) - propionyl] -6- (N-benzoyl-methylamino) -1, 2, 3, 4-tetrahydro-quinoline, (r) l- [3- (4-amidino-phenyl) -propionyl] -6- [N- ( naphth-l-yl- ^ sulfonyl) -hydroxycarbonylmethylamino] -l, 2,3,4-tetrahydroquinoline, (s) _ l- [3- (4-amidino-fenif] -propionyl] -6- [N- (1-naphthyl) -hydroxycarbonylmethylamino] -!, 2,3,4-tetrahydroquinoline, (t) l- [3- (4-amidino-phenyl) -propionyl] -6- (N-benzoyl-hydroxycarbonylmethylamino) -1,2,3,4-tetrahydroxyquinoline, (u) __ 1 - [3- (4-amidino-pheny?) -propionyl] -6- [N- (quinolin-? 8-sulfonyl) -hydroxycarbonylmethylamino] -l, 2, 3, 4-tetra-, hydroquinoline, and (v) l- [3- (4-amidino-phenyl) -propionyl] -6- [ N- (n-butyl- sulfonyl) -hydroxycarbonylmethylamino] -l, 2,3,4-tetrahydroquinoline, * -its antipodes opt icos and their salts.

According to the invention, the novel compounds of the general formula I can be obtained by the following processes, for example: a) To prepare a compound of the general formula I in which Rb denotes a cyano group and Y denotes a methylene group: reaction of a compound of the general formula in which A and Ra are as defined in the preceding, with a compound of the general formula_ where B,, Rc and Rd are as defined in the preceding, and 'denotes a methylene group Zi denotes a lost group, such as a halogen atom, a sulfonic acid group, for example a chlorine, bromine or iodine atom, a methanesulfonyloxy or p-toluenesulfonyloxy group. Conveniently the reaction is carried out in a solvent or mixture of solvents, such as methylene chloride, chloroform, ether, tetrahydrofuran, dioxane or dimethylformamide, optionally in the presence of an inorganic or organic base, such as sodium hydroxide, potassium carbonate , triethylamine or pyridine, these latter two can simultaneously serve as a solvent, at temperatures between -25 and 100 ° C, but preferably at temperatures between -10 and 80 ° C. b) To prepare a compound of the general formula I wherein "Rb denotes a cyano group and Y denotes a carbonyl group:" * - reaction of a compound of the general formula in which _A and Ra are as defined in the preceding, with a compound of the general formula wherein _B, w .Rc and are as defined in the foregoing, Y '' denotes a carbonyl group, and Z2 denotes a hydroxy group or a lost group, such as a halogen atom, for example Jan. chlorine or bromine. Conveniently the reaction is carried out in a solvent or mixture of solvents, such as methylene chloride, chloroform, carbon tetrachloride, ether, tetrahydrofuran, dioxane benzene, toluene, acetonitrile or dimethylformamide, optionally in the presence of acid activating agent or an agent dehydrating, for example in the presence of ethyl chloroformate, thionyl chloride, phosphorus trichloride, phosphorus pentoxide, N, N'-dicyclohexylcarbodiimide, N, N '-dicyclohexylcarbodiimide / N-hydroxy-succinimide, N, N'-carbonyldiimidazole or N, N'-phenyldiimidazole or triphenylphosphine / carbon tetrachloride, and optionally in the presence of an inorganic base, such as sodium carbonate, or an organic base, such as triethylamine or pyridine which can serve simultaneously as a solvent, at temperatures between -25 'and 250 ° C, but preferably at temperatures between -10 ° C and the boiling temperature of the solvent that is used. c) _ To prepare a compound of the general formula I in which Ra denotes a group R? N (XR3) and Rb denotes a cyano group: reaction of a compound of the general formula wherein A, B, W, Y, Rc, Rd and Ri are as defined in the preceding, with a compound of the formula Z3-X-R3", (VI) in the T that X and R3 are as defined in the foregoing, and Z3 denotes a hydroxy group or a lost group, such as a halogen atom, for example a chlorine or bromine atom. "Conveniently the reaction is carried out in a solvent or mixture of solvents, such as water , methylene chloride, chloroform, ether, tetrahydrofuran, dioxane or dimethylformamide, optionally in the presence of a base inorganic or organic, such as sodium hydroxide, potassium carbonate, triethylamine or pyridine, these latter two can simultaneously serve as a solvent, at temperatures between -25 and 100 ° C, but preferably at temperatures "between -10 and 80 C. If Z3 denotes a hydroxy group and X denotes a carbonyl group, the reaction is preferably carried out in the presence of an acid activating agent or a dehydrating agent, for example in the presence of ethyl chloroformate, thionyl chloride, phosphorus trichloride, phosphorus pentoxide, N, N'-dicyclohexylcarbodiimide, N, N'-dicyclohexylcarbodiimide / N-hydroxysuccinimide, N, N'-carbonyldiimidazole or N, N'-tionildiimidazol or triphenylphosphine / carbon tetrachloride, and optionally in the presence of an inorganic base, such as sodium carbonate, or of an organic base, such as triethylamine or pyridine which can simultaneously serve as a solvent, at temperatures between -25 and 150 ° C, but preferably at eratures between -10 ° C and the boiling temperature of the solvent used. d) To prepare a compound of the general formula I in which Ra denotes a group R? NR2 or R? N (XR3) in which Ri is as defined above with the exception of the hydrogen atom, and Rb denotes a cyano group or an amidino group substituted with a C? -? or -alkoxycarbonyl or phenyl-C? _3- group alkoxycarbonyl,: reaction of a compound of the general formula where A, B, W, Y, Rc, and Rd are as defined in the preceding, R4 has the meanings given in the above for R2, or denotes a group R3-X, where R3 and X they are as defined in the foregoing, and Rb denotes a cyano group or an amidino group substituted with a Ci-io alkoxycarbonyl or phenyl-C? _3-alkoxycarbonyl with a compound of the formula ~~ Z4-R1 group ', (VIII) wherein Ri denotes a group C? -5-alkyl which may be substituted with a phenyl, carboxy, C? _4 alkoxycarbonyl or aminocarbonyl, while the amino group "of the aminocarbonyl group may be mono- adicinalmente or disubstituted with C? _4-alkyl, phenyl-C? _3-alkyl, phenyl, carboxy-C? _3-alkyl or C? -3-alkoxycarbonyl-C? -3-alkyl groups, and the substituents may be identical or different, or C2_3-alkyl group is straight chain terminally substituted __ group di- (C? _3-alkyl) amino, pyrrolidino, piperidino or morpholino, and Z4 denotes a lost group such as a halogen atom, by example a chlorine or bromine atom. Conveniently the reaction is carried out in a solvent or solvent mixture, such as water, methylene chloride, chloroform, ether, tetrahydrofuran, dioxane or dimethylformamide, optionally in the presence of an inorganic or organic base, such as sodium carbonate of potassium, triethylamine or pyridine, these latter two can simultaneously serve as a solvent, at temperatures between -25 and 100 ° C, but preferably at temperatures between -10 and 80 ° C. e) To prepare a compound of the general formula I in which Ra denotes a nitro group and Rb denotes a cyano group: nitration of a compound of the general formula in which A, B, W, Y, Rc and Rd are as defined in -precedent. Nitration is preferably carried out in a solvent such as glacial acetic acid or tetrahydrofuran in the presence of a nitrating agent such as nitric acid or nitric acid / sulfuric acid diluted or concentrated, at temperatures between 0 and 50 ° C, preferably at room temperature. The nitration can also be done without solvent. Furthermore, if a mixture of positional isomers is obtained it can be separated to obtain the individual isomers by conventional methods, for example by chromatography. F) To prepare a compound of the general formula I in which Ra denotes an amino group and Rb denotes a cyano group: reduction of a compound of the general formula where A, B,, Y, Rc and Rd are as defined in the preceding. The preference reduction is carried out in a solvent such as water, water / ethanol, methanol, acetic acid glacial, ethyl acetate or dimethylformamide, advantageously with hydrogen in the presence of a hydrogenation catalyst such as Raney nickel, platinum or palladium / carbon, with metals such as iron, tin or zinc in the presence of an acid, with salts such as sulfate of iron (II), tin (II) chloride, sodium sulphide, sodium hydrosulfite, sodium dithionite, or with hydrazine in the presence of Raney nickel, at temperes between 0 and 80 ° C, but preferably at temperes between 20 and 40 ° C ~. g) To prepare a compound of the general formula I in which Rb denotes an amidino group: reaction of a compound of the general formula optionally formed in the reaction mixture, wherein A, B, W, Y, Ra, Rc and Rd are as defined in the foregoing, and Z5 denotes an alkoxy or aralkoxy group such as methoxy, ethoxy, n- propoxy, isopropoxy or benzyloxy, or a thioalkyl or thioaralkyl group, such as the thiomethyl, thioethyl, n-propylthio or thiobenzyl group, with ammonium or with addition salts of ammonium. Conveniently the reaction is carried out in a solvent such as methanol, ethanol, n-propanol, water, methanol / water, tetrahydrofuran or dioxane at temperes between -10 and 120 ° C, with a corresponding free amine or with a corresponding salt of addition of acid, such as, for example, the corresponding carbonates, acetates or ammonium chlorides A compound of the general formula IX is obtained, for example, by reacting a corresponding nitrile with a corresponding alcohol, such as methanol, ethanol, n-paopanol , isopropanol or benzyl alcohol in the presence of an acid, such as hydrochloric acid, or by reacting a corresponding amide with a trialkyloxonium salt, such as triethyloxonium tetrafluorobo in a solvent such as methylene chloride, tetrahydrofuran or diaxane, at temperes between - 10 and 50 ° C, but preferably at temperes between 0 and 30 ° C, or a corresponding nitrile with hydrogen sulfide, conveniently in a solvent l as pyridine or dimethylformamide and in the presence of a base such as triethylamine, and subsequent alkylation of the thioamide formed with a corresponding alkyl or aralkyl halide, or by reacting a corresponding nitrile with an alkoxide, such as sodium methoxide in a solvent such as "dioxane or tetrahydrofuran, but" preferably in the corresponding alcohol. During reactions with an alcohol, any ester group present can be transesterified. h) To prepare a compound of the general formula I in which Rb denotes an amidino group substituted with a C? -? or -alkoxycarbonyl or phenyl-C? 3- alkoxycarbonyl group,: reaction of a compound of the general formula wherein A, B, W, Y, Ra, Rc and Rd are as defined in the preceding, with a compound of the general formula __ Z6-C0-0R4, (XIII) wherein R4 denotes a group C? _? 0-alkyl or phenyl-C? -3-alkyl, and Z6 denotes lost group, such as a halogen atom, for example a chlorine or bromine atom. Conveniently the reaction is carried out in a "solvent, such as tetrahydrofuran, methylene, chloroform, dimethylformamide, water or mixtures of these solvents, optionally in the presence of a base, such as a solution of sodium carbonate, potassium carbonate or soaio hydroxide, or in the presence of an organic base, such as triethylamine , N-ethyl-diisopropilamma, N-methyl-morpholine or pipdma, which can simultaneously serve as a solvent, at temperes between -30 and 100 ° C, but preferably at temperes between -10 ° C and 60 ° C. ~ i) ~~ To prepare a compound of the general formula I in which Rb denotes an aminomethyl group: reduction of a compound of the general formula where - A, B, ~ W, Y, Ra, Rc and Rd are as defined in the preceding. The reduction of preference is carried out in a suitable solvent, such as methanol, methanol / water, methanol / water / ammon, ethanol, ether, tetrahydrofuran, dioxane or dimethylformamide, optionally with the addition of an acid such as hydrochloric acid in the presence of catalytically activated hydrogen, for example hydrogen in the presence of Raney nickel, platinum or palladium / carbon, Or the presence of a metal hydride, such as sodium borohydride, lithium borohydride or lithium aluminum hydride, at temperatures between 0 and 100 ° C, preferably at temperatures between 20 and 80 ° C. j) To prepare a compound of the general formula 1 in which Ra denotes a group R? NR2, in which Ri is co or defined in the foregoing with the exception of the hydrogen atom, and Rb denotes a cyano group or an amidino group substituted with "a group C? _? 0- alkoxycarbonyl or fenii-C? _3-alkoxycarbonyl,: reaction of a compound of the general formula wherein A, B, W, Y, R2, Rc, and Rd are as defined in the foregoing, and Rb denotes a cyano group or an amidino group substituted with a C? _? o_ ^ alkoxycarbonyl or phenyl-C group -3-alkoxycarbonyl with a compound of the general formula Z7-R? ' , (XVI) in which Ri is as defined in the above, and Z7 denotes a lost group, such as a halogen atom, for example a chlorine or bromine atom, or together with a hydrogen atom of the carbon atom adjacent denotes an oxygen atom. Suitably the reaction is carried out in a solvent or mixture of solvents, such as water, methylene chloride, chloroform, ether, tetrahydrofuran, dioxane or dimethylformamide, optionally in the presence of an inorganic or organic base, such as sodium hydroxide, potassium carbonate, triethylamine or pyridine, these latter two can simultaneously serve as a solvent, at temperatures between -25 and 100 ° C, but preferably at temperatures between -10 and 80 ° C. The reaction with a carbonyl compound of the general formula XVI is preferably carried out in a suitable solvent, such as methanol, methanol / water, methanol / water / ammonium, ethanol, ether, tetrahydrofuran, dioxane or dimethylformamide, optionally with the addition of an acid such as hydrochloric acid in the presence of catalytically activated hydrogen, for example hydrogen in the presence of Raney nickel, platinum or palladium / carbon, or in the presence of a metal hydride, such as sodium borohydride, lithium borohydride- or lithium aluminum hydride, at temperatures between 0 and 100 ° C, preferably at temperatures between 20 and 80 ° C. k) To prepare a compound of the general formula I in which Rb denotes a cyano group and Y denotes a carbonyl group: reaction of a compound of the general formula wherein A and Ra are as defined in the foregoing, and Z8 denotes a lost group, such as a halogen atom, for example a chlorine or bromine atom, with a compound of the general formula - (XVIII) where B,, Rc and Rd are co or defined in the preceding, and Rs denotes an amino group optionally substituted with a C? _3-alkyl group. Conveniently the reaction is carried out in a solvent or mixture of solvents, such as water, methylene chloride, chloroform, ether, "tetrahydrofuran, dioxane or dimethylformamide, optionally in the presence of an inorganic or organic base, such as sodium hydroxide, potassium carbonate, triethylamine or pyridine, these two * can serve simultaneously as a solvent, at temperatures between -25 and 100 ° C, but preferably at temperatures "between -10 and 80 ° C. If, according to the invention, a compound of the general formula I is obtained in which X denotes a carbonyl group, this can be converted into a corresponding thiocarbonyl compound by means of a sulfating agent, or if a compound of the invention is obtained according to the invention. general formula I in which Ra contains an acyl group, this can be converted by hydrolysis into a compound of the general formula I in which Ra denotes a RiNH group, or in which Ra contains a carboxy group, or if according to the invention obtains a compound of the general formula I in which Ra denotes or contains a carboxylic or sulfonic acid group, which can be converted by amidation into a compound of the general formula I. The reaction is carried out with a sulfatizing agent, such as phosphorus pentasulfide or 2,4-disulfide 2,4-bis (4-methoxypheni?) -l-3-di-thia-2, 4- diphosphenone conveniently in a solvent such as toluene or xylene, at temperatures between 50 and 150 ° C, for example at the boiling temperature of the reaction mixture. The subsequent hydrolysis is preferably carried out hydrolytically in an aqueous solvent, for example in water, iso-propanol / water, tetrahydrofuran / water or dioxand / water, in the presence of an acid, such as hydrochloric acid or sulfuric acid, or in the presence of an alkali metal base, such as sodium hydroxide or potassium hydroxide, at temperatures between 0 and 100 ° C, preferably at the boiling temperature of the reaction mixture. optionally in a solvent or mixture of solvents, such as methylene chloride, dimethylformamide, benzene, toluene, chlorobenzene, tetrahydrofuran, benzene / tetrahydrofuran or dioxane with a corresponding amine, optionally in the presence of a dehydrating agent, for example in the presence of isobutyl chloroformate, tetraethyl orthocarbonate, trimethyl orthoacetate, 2,2-dimethoxypropane, tetramethoxysilane, thionyl chloride, trimethylchlorosilane, phosphorus trichloride, phosphorus pentoxide, N, N '-dicyclohexylcarbodiimide, N, N' -dicyclohexyl-carbodiimide / N-hydroxysuccinimide, N, N '-dicyclohexylcarbo-diimide / 1-hydroxy-benzotriazole, tetrafluoroborate 2- ( lH-benzotriazol-1-yl) -1, 1, 3, 3-tetramethyluronium, 2- (lH-benzotriazol-1-yl) -1, 1,3,3-tetramethyluronium / 1-hydroxy-benzotriazole tetrafluoroborate, N , N'-carbonyldiimidazole or triphenyl phosphine / carbon tetrachloride, and optionally with the addition of a base such as pyridine, 4-dimethylaminopyridine, N-methyl-morpholine or triethiamine, conveniently at temperatures between 0 and 150 ° C, preferably at temperatures between 0 and 100 ° C. The reaction with a corresponding amine of the corresponding carboxylic or sulfonic reactive acids, such as their esters, imidazolides or halides, is preferably carried out in a corresponding amine as solvent, optionally in the presence of another solvent, such as chloride * of methylene or ether, and preferably in the presence of a tertiary organic base, such as triethylamine, N-ethyl-diisopropylamine or N-methyl-morpholine, at temperatures between 0 and 150 ° C, preferably at temperatures between 50 and 100 ° C. In the above-described reactions, any reactive groups that are present, such as hydroxy, carboxy, amino, alkylamino or imino can be protected during the reaction by conventional protecting groups, which are re-split after the reaction. For example, a protecting group for a hydroxy group can be a trimethylsilyl, acetyl, benzoyl, tert-butyl, trityl, benzyl or tetrahydropyranyl group, the protecting groups for a carboxy group can be a trimethylsilyl, methyl, ethyl, tert-butyl group , benzyl or tetrahydropyranyl, and the protecting groups for an amino, alkylamino or imino group can be an acetyl, trifluoroacetyl, benzoyl, ethoxycarbonyl, tert-butoxycarbonyl, benzyloxycarbonyl, benzyl, methoxybenzyl, or 2,4-dimethoxybenzyl group and, additionally for the amino group, a phthalyl group. Any optionally used protective group is subsequently cleaved, for example by hydrolysis 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 alkali metal base, such as lithium hydroxide, sodium hydroxide or potassium hydroxide, or by ether cleavage, for example in the presence of iodotrimethylsilane, at temperatures between 0 and 100 ° C, preferably at temperatures between 10 and 50 ° C. ^ However, a benzyl group, methoxybenzyl or benzyloxycarbonyl is split, for example, in hydrogenolytic form, 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 1 to 7 bar, but preferably 3 to 5 bar. A tert-butyl or tert-butyloxycarbonyl group is preferably split by treatment with an acid, such as trifluoroacetic acid or hydrochloric acid, optionally using a solvent such as methylene chloride, dioxane or ether. In addition, the compounds of the general formula I obtained can be separated into their enantiomers and / or diastereomers. "Thus, for example, compounds obtained from general formula I that occur as racemates can be separated by methods known per se (compare Allihger N.L. and Eliel E.L. in" Topics in Stereochemistry ", Vol. 6, Wiley Interscience, 1971) in their optical antipodes, and the compounds of the general formula I with at least two asymmetric carbon atoms can be separated into their diastereomers based on their physico-chemical differences using methods known per se, example by chromatography and / or fractional crystallization and, if these compounds are obtained in the racemic form, they can be subsequently separated into the enantiomers as mentioned above. The enantiomers are preferably separated by column separation on chiral phases, or by recrystallization from an optically active solvent, or by reaction with an optically active substance which forms salts or derivatives such as, for example, esters or amides with the racemic compound, in particular acids and their derivatives or their activated alcohols, and separating the diastereomeric mixture from the salts or derivatives thus obtained, for example on the basis of their differences in solubility, while the free antipodes can be liberated from the pure diastereomeric salts or derivatives by the action of appropriate agents. Commonly used optically active acids are, for example, the D and L forms of tartaric or dibenzoyltartaric acid, di-o-tolyltartaric acid, maleic acid, mandelic acid, camphorsulfonic acid, acid glutamic acid, aspartic acid or quinine acid. An optically active alcohol can be, for example, menthol (+) or (-) and an optically active acyl group in amides can be, for example, a menthyloxycarbonyl (+) or (-), In addition, the compounds of the formula I they can be converted into their salts, particularly for pharmaceutical use in their physiologically acceptable salts with inorganic or organic acids. Acids that can be used for this purpose include, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, fumaric acid, succinic acid, lactic acid, citric acid, acid tartaric acid, maleic acid or methanesulfonic acid. In addition, if the new compounds of the formula I contain a carboxy group, if desired they can be subsequently converted into the salts thereof, with inorganic or organic bases, particularly for pharmaceutical use in their physiologically acceptable salts. Suitable bases for this purpose include, for example, sodium hydroxide, potassium hydroxide, arginine, cyclohexylamine, ethanolamine, diethanolamine and triethanolamine. The compounds of the general formulas II to XVIIi used as starting materials are obtained by methods known from the literature or known through the literature. Thus, for example, a compound of the general formula II can be obtained by the hydrogenation of a corresponding unsaturated compound, and a starting material of the general formulas V, VII, IX, X, XI and XIV by alkylation or acylation of a composed of the general formula II. As already mentioned above, the novel compounds of the general formula I and their salts have valuable properties. Accordingly, the compounds of the general formula I in which Rb denotes a hydrogen atom, a nitro or cyano group, are valuable intermediate products for producing the other compounds of the general formula I, and the compounds of the general formula I in which Rb denotes one of the above-mentioned optionally substituted aminomethyl or amidino groups, and their physiologically acceptable salts possess valuable pharmacological properties, in particular a thrombin inhibiting activity and an inhibiting effect of thrombocyte aggregation, an activity that prolongs the range of thrombin and an inhibitory effect of related serine proteases, such as trypsin, plasmin, factor Vlla, factor Xa, factor IX, factor Xi and factor XII of urokinase.

For example, the compounds A = l- [3- (4-amidino-phenyl) propionyl] -6-butyl-sulfonamido-1,2,3,4-tetrahydro-quinoline, the hydrochloride, B = l- [3- (4-Amidinophenyl) propionyl] -1,3,3,4-tetrahydro-quinoline-6-carboxylic acid methyl-N-phenyl-amide, l-diethylamide [3- (4-amidino-phenyl) -propionyl] -l, 2, 3, 4-tetrahydro-quinoline-6-carboxylic acid, D = N-benzyl-N-. { l- [3- (4-Amidino-phenyl) -propionyl] -1,2,3,4-tetrahydro-quinolin-6-yl} -acetami a, E = acid ( { l- [3- (4-amidino-phenyl) -propionyl] -l, 2, 3, 4- ratetrahydro-quinolin-β-carbonyl.}. -phenyl-amino) -acetic = l- [3- (4-amidino-phenyl) propionyl] -6-phenyl-sulfonamido-1,2,3,4-tetrahydro-quinoline, the hydrochloride, = (i) l- [3- (4-amidino-phenyl) propionyl] -β- (N-carboxymethyl-phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline, H "= acid [ { L- [3- (4-amidino-phenyl) -propionyl] -l, 2,3,4- ^ rtetrahydro-quinolin-6-yl.} - (naphthalene-1-sulfonyl) ) -amino] - -acetic - = [ { l- [3- (4-amidino-phenyl) -propionyl] -l, 2, 3, 4- * "tetrahydro-quinolin-6-yl acid} - (quinilin-8-sulfonyl) -amino] - acetic were investigated in relation to their effect on the thrombin interval, as follows: Material: Plasma, citrated human blood Thrombin test (bovine), 30 U / ml, Behring Werke, Marburg, Germany, 7 Diethybarbituric acetate regulator ORWH 60/61, Behring Werke, Marburg, Biomatic BIO coagulometer, Sarstedt Method: Thrombin interval was determined using a Biomatic BIO coagulometer made by the company Sarstedt. The test substance was filled into the test tubes prescribed by the manufacturer, with 0.1 ml of encrypted human plasma and 0.1 ml of the diethylbarbituric regulator (DBA regulator). The mixture was incubated for one minute at 37 ° C. The coagulation reaction was initiated by the addition of 0.3 U of the test thrombin in 0.1 ml of DBA regulator. Due to the design of the apparatus, the time interval that elapsed for the mixture to coagulate was measured at the time the thrombin was added. The mixtures to which 0.1 ml of the DBA regulator had been added were used as controls. According to the definition, the effective concentration of the substance at which the thrombin interval was twice that of the control was determined by a dosage / activity curve.

The following table contains the values found: In addition, no toxic side effects could be detected in rats when the preceding compounds were administered in a dose of 20 mg / kg i.v. or 100 mg / kg p.o. Accordingly, the compounds are well tolerated. In view of their pharmacological properties, the new compounds and their physiologically acceptable salts are? suitable for the prevention and treatment of venereal and arterial thrombotic diseases, such as for example the treatment of thromboangiitis of the lower leg veins, for the prevention of reocclusions after bypass operations or angioplasties (PT (C) A), and occlusion in peripheral arterial diseases such as pulmonary embolism, disseminated intravascular coagulation, for the prevention of coronary thrombosis, infarction, and lead occlusion (anastomosis) Additionally, the compounds according to the invention are suitable for antithrombotic support in thrombolytic treatments, such as for example with rt-PA (recombinant tissue-type plasminogen activator) or ~ streptokinase, for the prevention of long-term restenosis after (PT (C) A), for the prevention of metastasis and tumor growth in function of coagulation and inflammatory processes in function of fibrin. The dosage required to achieve an effect of this kind is appropriately from 0.1 to 50 mg / kg, preferably from 0.5 to 30 mg / kg by the intravenous route, and from 1 to 100 mg / kg, preferably from 0.5 to 50 mg / kg. orally, in each case administered 1 to 4 times a day. For this purpose, the compounds of the formula I prepared according to the invention can be formulated, optionally together with other active substances, with one or more conventional inert carriers and / or diluents, for example with corn starch, lactose, glucose, microcrystalline cellulose, magnesium stearate, polyvinylpyrrolidone, citric acid, tartaric acid, water, water / ethanol, water / glycerin, water / sorbitol, water / polyethylene glycol, propylene glycol, cetyl stearyl alcohol, carboxymethylcellulose or fatty substances such as solid fat or suitable mixtures thereof, to produce conventional galenic preparations as simple or coated tablets, capsules, powders, suspensions or suppositories. The following examples should illustrate the invention: Preparation of the starting compounds: ~ Example I 3- (4-Cyano-phenyl) propionic acid 100.1 g (0.578 mol) of 4-cyano-cinnamic acid are absorbed in 1400 ml of a potassium carbonate solution IN and hydrogenated on palladium / carbon at 5 bar for 2.5 hours. The solution is then acidified slightly, and the precipitate is filtered by suction and then dried in the circulating air dryer. Yield: 90.8 g (89.6% of theory), Melting point: 137-139 ° C - Example II 6-phenylsulfonamido-quinoline 61.5 g (0.426 mol) of 6-amino-quinoline are dissolved in 210 ml of pyridine and combine with 82.8 g (0.469 mol) of benzenesulfonic acid chloride at the time of cooling with ice. The solution is then heated to 100 ° C, and after 20 minutes it is slowly cooled to 45 ° C. Then 85 ml of a 6N sodium hydroxide solution are added, and the mixture is evaporated to dryness. The remaining precipitate is washed first with water, then with ethanol and then dried Yield: 106.6 g (87.9% of theory), Melting point: 219-221 ° C The following are prepared analogously: (1) ) 6- (2-naphthylsulfonamido) -quinoline Melting point: 152 ° C (2) 6- (1-naphthylsulfonamido) -quinoline Melting point: 248 ° C (3) 6- (4-fluoride) phenylsulfonamido) -quinoline Melting point: 220-221 ° C (4) 6-Butylsulfonamido-quinoline Melting point: 82-84 ° C (5) 5-phenylsulfonamido-quinoline Melting point: 112 ° C (6) 7- phenylsulfonamido-quinoline Melting point: 185-187 ° C (7) 7-benzylsulfonamido-quinoline JValue Rf: 0.73 (silica gel; methylene chloride / methanol = 9: 1) (8) 6-benzylcarboxamido-quinoline Melting point: 146-149 ° C (9) 6-phenylsulfonamido-2-methyl-quinoline '-Value Rf: 0.61 (silica gel; ethyl acetate) (10) 6-benzylsulfonamido -quinoline Melting point: 179-181 ° C (11) 6-benzoylamino-quinoline Melting point: 155-158 ° C (12) 6- (4-chloro-phenylsulfonamido) -quinoline (13) 6- (4- bromo-phenylsulfonamido) -quinoline (14) 6- (3-chloro-phenylsulfonamido) -quinoline (15) 6- (3-bromo-phenylsulfonamido) -quinoline (16) .6- (4-methyl-phenylsulfonamido) -quinoline - Example III 6- (N-methyl-phenylsulfonamido) -quinoline 4.0 g of 6-phenylsulfonamido-quinoline are dissolved in 50 ml of dimethyl sulfoxide and combined at room temperature with 1.83 g of potassium tert-butoxide.

Then 2.13 g of methyl iodide are added dropwise and the mixture is stirred overnight. It is then poured onto 300 ml of water / ice and extracted with ethyl acetate. The organic phase is dried and concentrated by evaporation. Yield: 3.0 g (71.8% of theory), Melting point: 101-103 ° C The following are prepared analogously: (1) 6- [N- (2-phenylethyl) -phenylsulfonamido] quinoline (2) 6- [N- (ethoxycarbonylmethyl) -phenylsulfonamido] quinoline Example IV 6-phenylsulfonamido-1, 2, 3, 4-tetrahydro-quinoline 106.6 g (0.375 mol) of 6-phenylsulfonamido-quinoline are dissolved in 1400 ml of glacial acetic acid and hydrogenated on 17 g of platinum oxide at 3 bar for 70 minutes. The catalyst is then removed by suction filtration, concentrated by evaporation, and the residue is washed with a little ethanol and dried. Yield: 98.4 g (91.0% of theory), Melting point: 160-162 ° C The following are prepared analogously (1) 6- (2-naphthylsulfonamido) -1,2,3,4-tetrahydro-quinoline Melting point: 152-154 ° C (2) 6- (1-naphthylsulfonamido) -1,2, 3, 4-tetrahydro-quinoline Melting point: 175-176 ° C (3) 6- (4-Fluorophenylsulfonamido) -1, 2, 3, 4-tetrahydroquinoline Melting point: 85 ° C (4) 6-Butylsulfonamido-1,2,4,4-tetrahydro-quinoline C? 3H2oN202S (268.36) Calculated: C 58. 18 H 7. 51"N 10. 43 Found: 57.95 ^ 7.70 10.22 (5) 6- (N-methyl-phenylsulfonamido) -l, 2, 3, 4-tetrahydro-7-quinoline (6) 7-benzylsulfonamido-1,2,4,4-tetrahydro-quinoline " Rf value: 0.72 (silica gel; ethyl acetate) (7) 5-phenylsulfonamido-1, 2,3,4-tetrahydroquinoline rTValor Rf: 0.82 (silica gel; ethyl acetate) (8) _7-phenylsulfonamido -1, 2,3, 4-tetrahydro-quinoline -Value Rf: 0.83 (silica gel, ethyl acetate) (9) 6-phenylacetylamino-1,2,4,4-tetrahydro-quinoline Melting point: 116- 118 ° C (10) 2-methyl-6-phenylsulfonamido-1,2,3,4-tetrahydroquinoline Rf value: 0.66 (silica gel; toluene / ethyl acetate = 6: 4) (ll) __ 6- benzylsulfonamido-l, 2, 3, 4-tetrahydro-quinoline (12) 6-benzoylamino-l, 2,3, 4-tetrahydro-quinoline Melting point: 150-153 ° C (13) 6- (4-fluoride- phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline Melting point: 85 ° C (14)) 6-n-Butylsulfonamido-1,2,4,4-tetrahydro-quinoline c C13H20N2O2S (268.38) Calculated : C 58. 18 H 7 57 N 10. 43 Found: 57. 95 7. 7 Ó "10.22 (15) ~ 6- [N- (2-phenylethyl) -phenylsulfonamido] -l, 2, 3,4-tetrahydroquinoline Rf value: 0.60 (silica gel; ethyl acetate / petroleum ether = 1: 1) ( 16) 6- [N- (ethoxycarbonylmethyl) -phenylsulfonamido] -l, 2, 3, 4-tetrahydro-quinoline (17) 6- (4-chloro-phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline _ (18) 6- (4-bromo-phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline (19) 6- (3-chloro-phenylsulfonamido) -1,2,4,4-tetrahydro-quinoline (20) ) 6- (3-bromo-phenylsulfonamido) -1,2,3,4-tetrahydroquinoline (21) 6- (4-methyl-phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline (22) 6 -morpholinocarbonyl-1, 2,3,4-tetrahydroquinoline Prepared from the compound prepared according to _ to example VII (6) Yield: 96% of the theory Rf value: 0.64 (silica gel; ethyl acetate) (23) 6-piperidinocarbonyl-l, 2,3,4-tetrahydroquinoline 'Prepared from the compound prepared according to example VII Performance: 36% of the theory Rf value: 0.57 (silica gel, ethyl acetate) (24) 6-benzylaminocarbonyl-l, 2,3, 4-tetrahydroquinoline Prepared from the compound prepared according to "to Example VII (1) Yield: 50% of theory Rf Value: 0.89 (silica gel; ethyl acetate) (25) 6- (N-methyl-phenylaminocarbonyl) -1,2,3,4-tetrahydro- quinoline Prepared from the compound prepared according to example VII (2) Yield: 62% of the theory Rf Value: 0.84 (silica gel; ethyl acetate) (26) 6-diethylaminocarbonyl-l, 2,3,4- tetrahydroquinoline Yield: 98% of the theory Prepared from the compound prepared according to example VII (3) Rf value: 0.60 (silica gel; ethyl acetate) (27) 6- (3 ', 5' -dimethyl- piperidinocarbonyl-1,2,3,4-tetrahydroquinoline ~ Prepared from the compound prepared according to example VII (4). 'Yield: 97% of the theory Rf Value: 0.67 (silica gel; ethyl) (28) 6-methoxycarbonyl-l, 2,3,4-tetrahydroquinoline 'Prepared from quinoline methyl-6-carboxylate (prepared analogously to J.Amer.Chem: Soc. 68, 2721 (1946)) Yield: 60% of theory (29) 6- (4'-methylpiperidinocarbonyl-1,2,3,4-tetrahydroquinoline) Prepared from the compound prepared according to Example VII (5) Yield: 96% of theory Rf Value: 0.67 (silica gel; ethyl acetate) Example V 6-trifluoroacetylamino-quinoline 7.2 g (0.05 mol) of 6- amino-quinoline and 14.2 g (0.11 mol) of N, N-diisopropyl-ethylamine are dissolved in 100 ml of methylene chloride. Then 11.55 g (0.055 mol) of trifluoroacetic acid anhydride are added dropwise at about 0 ° C, and the mixture is stirred at this temperature for 1 hour. The precipitate that forms is filtered by suction, washed with methylene chloride and water and then dried. The mother liquor is extracted three times with methylene chloride, then the organic phase is separated, dried over sodium sulphate, concentrated by rotary evaporation and combined with the precipitate obtained above. Yield: 10.69 g (89.0% of theory) Melting point: 183-185 ° C EXAMPLE VI 6-Trifluoroacetylamino-1,2,3,4-tetrahydro-quinoline 2.4 g (0.01 mol) of 6-trifluoroacetylamino-quinoline are dissolved in 20 ml of glacial acetic acid and hydrogenated for 1 hour with 0.6 g of sodium oxide. platinum at 3 ^ bars. The catalyst is then removed by suction filtration and the solution is concentrated by evaporation. The residue is washed with a little sodium hydrocarbonate solution and dried. Yield: 1.79 g (74% of theory), Melting point: 95-97 ° C ~ Example VII 6-piperidinocarbonyl-quinoline 3.0 g of quinolin-6-carboxylic acid chloride (prepared analogously to J. Med. Chem. 38, 3094-3105 (1995)) are combined with 4.25 ml of piperidine in 70 ml of pyridine at room temperature, and stirred for 20 minutes. The mixture is then concentrated by evaporation, the residue is taken up in a little water and extracted with methylene chloride. The organic phase is concentrated by evaporation and filtered on a column of silica gel with ethylene acetate. Yield: 2.1 g (52% of the theory), Rf value: 0.24 (silica gel, ethyl acetate) The following are prepared analogously: (1) 6-benzylaminocarbonyl-quinoline Yield: 73% of theory, Rf value: 0.45 (silica gel; ethyl acetate) (2) 6- (N-methyl-phenylaminocarbonyl) -quinoline Yield: 83% of theory , _Value Rf: 0.49 (silica gel, ethyl acetate) (3) 6-diethylaminocarbonyl-quinoline Yield: 72% of the theory, -Value Rf: 0.24 (silica gel, ethyl acetate) (4) 6- ( 3 ', 5'-dimethyl-piperidinocarbonyl) -quinoline Yield: 33% of theory, Rf value: 0.25 (silica gel; ethyl acetate) (5) 6- (4'-methylpiperidinocarbonyl) -quinoline Yield: 50% from the theory, 'Rf Value: 0.21 (silica gel; ethyl acetate) (6) 6-morpholinocarbonyl-quinoline = _ Yield: 69% of theory,, Rf Value: 0.22 (silica gel; ethyl acetate) Preparation of the compounds of the general formula I Example 1 l- [3- (4-cyano-phenyl) propionyl] -5-nitro-2,3-dihydro-indole 1.6 g of 5-nitro-2,3-dihydro- indole are dissolved in 40 ml of methylene chloride, then combined with 1.5 ml of triethylamine and then with 1.93 g of 3- (4-cyano-phenyl) propionic acid chloride in 4 ml of methylene chloride. After stirring overnight, the mixture is concentrated to dryness by evaporation. The product (3 g, 93% of theory) is processed without further purification. The following are prepared analogously: (1) l- [3- (4-cyano-phenyl) propionyl] -3-methyl-6-phenylsulfon- "amido-1,2,3,4-tetrahydro-quinoline-yield : 94% of theory, Rf value: 0.67 (silica gel; toluene / ethyl acetate = 6: 4) (2) l- [3- (4-cyano-phenyl) propionyl] -2, 3, 4, 5-tetrahydrobenzo [b] azepine-Yield: 82% of theory, Rf value: 0.55 (silica gel; toluene / ethyl acetate = 7: 3) (3) "l- [3- (4-cyano phenyl) propionyl] -4-methyl-6-nitro-tetrahydroquinoline, prepared from 3- (4-cyano-phenyl) propionyl chloride and 4-methyl-6-nitro-tetrahydroquinoline - ~ lina Yield: 55% of theory, Rf Value: 0.45 (silica gel, toluene / ethyl acetate = 9: 1) Example 2 5-amino-1- [3- (4-cyano-phenyl) propionyl] -2,3-dihydro-indole 2 g of l- [3- (4-cyano-phenyl) propionyl] -5-nitro- 2,3-dihydro-indole is dissolved in 100 ml of methanol / methylene chloride and hydrogenated at 3 bar on palladium / carbon. Then the mixture is concentrated by evaporation. Yield: 2 g (74% of the theory) Rf value: 0.20 (silica gel, toluene / ethyl acetate = 6: 4) "The following are prepared analogously: (1) 6-amino-1- [3 - (4-cyano-phenyl) propionyl] -3-methyl-1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 3 (1) Yield: 60% of the theory Rf Value: 0.35 (silica gel; toluene / ethyl acetate = 8: 2) (2) 7-amino-1- [3- (4-cyano-phenyl) propionyl] -2, 3, 4, 5-tetrahydro -! H-benzo [b] azepine Prepared from the compound prepared according to example 3 Yield: 74% of theory Rf value: 0.13 (silica gel; toluene / ethyl acetate = 7: 3) (3) _6-amino-l- [3- (4-cyano-phenyl) propionyl] -4-methyl-1, 2, 3, 4- 5-tetrahydroquinoline Yield: 75% of the theory Melting point: sintered from 80 ° C (4) l- [3- (2-amino-4-cyanophenyl) propionyl] -6-phenylsulfonyl-amino-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared from agreement "to example 9 (28) Yield: 67% of theory Rf value: 0.58 (silica gel; methylene chloride / methanol = 4: 1) Example 3 l- [3- (4-cyano-phenyl) propionyl ] -7-nitro-2, 3,4, 5-tetra- - hydro-lH-benzo [b] azepine 3 g of [3- (4-cyano-phenyl) propionyl] -2, 3, 4, 5- tetrahydro-lH-benzo [b] azepine (see example 1 (2)) are dissolved in 17 ml of glacial acetic acid and stirred with 1 ml of nitric acid in 3 ml of glacial acetic acid overnight at The mixture is then concentrated by evaporation and the residue is taken up in water and extracted 3 times with methylene chloride.The organic phase is dried, concentrated by evaporation The residue is chromatographed on a column of silica gel with toluene / ethyl acetate = 8: 2.

Yield: 1.2 g (35% of theory) Melting point: from 127 ° C The following is prepared analogously l- [3- (4-cyano-phenyl) propionyl] -3-methyl-6-nitro-l , 2, 3, 4 - tetrahydroquinoline Yield: 85% of the theory Rf Value: 0.72 (silica gel, toluene / ethyl acetate = 8: 2) Example 4 _ l- [3- (4-cyano- phenyl) propionyl] -6-trifluoroacetylamino-1,2,3,4-tetrahydro-quinoline 10 g (0.057 mol) of 3- (4-cyano-phenyl) propionic acid and 6.6 g (0.065 mol) of N-methyl- morpholine are dissolved in 250 ml of tetrahydrofuran and cooled to minus 20 ° C. Then 8.2 g are added dropwise. (0.057 mol) of isobutyl chloroformate. Then 13.9 g (0.057 mol) of 6- (trifluoroacetylamino) -1,2,3,4-tetrahydro-quinoline in 200 ml of tetrahydrofuran are added and the solution is allowed to warm overnight at room temperature. It is then diluted with 200 ml of ethyl acetate and washed with 2 x 80 ml of 0.5 N hydrochloric acid and then with 100 ml of a sodium hydrocarbonate solution. The organic phase is dried over sodium sulfate and concentrated by evaporation in vacuo. "Performance: 16 g (70% of theory) Melting point: 151-152 ° C C2? H? 8F3 3? 2 (401.39) Calculated: C 62.83 H 4.51 N 10.46 Found: 62.45 4.55 10.44 Example 5 6-amino-l- [3- (4-cyano-phenyl) propionyl] -1, 2,3, 4-tetrahydroquinoline, 16 g of l- [3- (4-cyano-phenyl) propionyl] -6-tri-fluoroacetylamino-1, 2, 3, 4-tetrahydro -quinoline are dissolved in 70 ml of methanol and 50 ml of dioxane, and stirred with 200 ml of IN sodium hydroxide solution for 2 hours at 40 ° C. After the mixture is extracted with methylene chloride, the organic phase is dried over sodium sulfate and concentrated by evaporation. Yield: 10.7 g (88% of theory) Melting point: 180-200 ° C C19H19.3O '(305.38) Calculated: C 74.72 H 6.27 N 13.75 - Found: 74.41 6.37 13.56 Example 6 6 (N-ethoxycarbonylmethyl-amino ) -l- [3- (4-cyano-phenyl) -propionyl] -l, 2,3,4-tetrahydroquinoline 10.7 g (35 mmoles) of 6-amino-1- [3- (4- cyano-phenyl) propionyl] -l, 2, 3, 4-tetrahydroquinoline are dissolved with 9.2 ml (53 mmoles) of N-ethyl-diisopropylamine in 70 ml of dimethylformamide, and 9 g (42 mmol) of ethyl iodoacetate are added at the time of cooling with ice. The solution is stirred overnight and then poured into water, extracted with ethyl acetate, and the organic phase is concentrated by rotary evaporation. Yield: 12.7 g (92% of theory) Melting point: 117-119 ° C The following are prepared analogously: (1) 6 (N-ethoxycarbonylmethyl-benzylamino) -l- [3- (4-cyano- ^ phenyl) -propionyl] -l, 2,3,4-tetrahydro-quinoline Prepared from 6-benzylamino-l- [3- (4-cyano-phenyl) -propionyl] -l, 2,3,4- tetrahydro-quinoline (see example 14) and ethyl iodoacetate Yield: 91% of theory Rf value: 0.36 (silica gel; methylene chloride / ethyl acetate = 19: 1) (2) 6- [N-ethoxycarbonylmethyl] - (naphthalimin-2-ylmethyl) -amino] -l- [3- (4-cyano-phenyl) -propionyl] -!, 2,3,4-tetrahydroquinoline Prepared from 6- (naphthalene-2- ylmethyl) -amino-1- [3- (4-cyano-phenyl) -propionyl] -l, 2, 3, 4-tetrahydroquinoline (see example 14 (2)) and ethyl iodoacetate Melting point: oil Performance: 93% of the theory (3) 6- [N-ethoxycarbonylmethyl- (naphthalin-1-ylmethyl) -amino] -l- "[3- (4-cyano-phenyl) -propionyl] -!, 2,3,4-tetrahydroquinoline Prepared from 6 - [(naphthalin-1-ylmethyl) -amino] -l- [3- (4-cyano-phenyl) -propionyl] -1,2,4,4-tetrahydroquinoline (see example 14 ( 1)) and ethyl iodoacetate Melting point: 80 ° C Yield: 96% of the theory (4) l- [3- (4-cyano-phenyl) -propionyl] -6- (N-ethoxycarbonyl- methyl- 2, 2-diphenyl-ethylamino) -1,2, 3,4-tetrahydroquinoline Prepared from l- [3- (4-cyano-phenyl) -propionyl] - ^ 6- (2,2-diphenyl- ethylamino) -l, 2, 3, 4-tetrahydro-quinoline _, (see example 14 (4)) and ethyl iodoacetate Yield: 93% of the theory Melting point: 156-158 ° C Example 7 l- [ 3- (4-cyano-phenyl) -propionyl] -6- [N-ethoxycarbonylmethyl- (isoquinoline-5-sulfonyl) -amino] -l, 2,3,4-tetrahydroquinoline 2.8 g of l - [3- (4-cyano-phenyl) -propionyl] -6- (isoquinoline-5-sulfonamido) -l, 2,3,4-tetrahydroquinoline (see Example 10 (14)) are dissolved in 4 0 ml of dimethyl sulfoxide, combine with 670 mg of tert-butoxide potassium and stir for 1 hour at room temperature. Then 1.0 g of ethyl bromoacetate is added and the solution is stirred overnight. It is then poured onto water / ice, 3 x is extracted with ethyl acetate, and the organic phase is dried and concentrated by rotary evaporation. Yield: 2.1 g (64% of theory) Melting point: 116-117 ° C The following are prepared analogously: (1) l- [3- (4-cyano-phenyl) -propionyl] -6- ( N-ethoxycarbonyl-methyl-n-butylsulfanolamino) -1,2,3,4-tetrahydro-quinoline - Prepared from the compound prepared according to example 9 (4) Yield: 77% of the theory Melting point: oil (2) l - [(4-cyano-phenoxy) -acetyl] -6- (N-ethoxycarbonylmethyl-1-naphthalenesulfonylamido) -1,2,3,4-tetrahydroquinoline Prepared from the compound prepared according to the example 9 (27) Yield: 77% of the theory C32H29N306S (583.61) Calculated: C 65. 85 H 5. 00 N 7. 19 Found: 65. 31 5. 15 7. 02 (3) 6- [N-methoxycarbonylpropyl) -naphth-l-yl-sulfonyl-amido] -l- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] -1,2,3,4-tetrahydro-quinoline Prepared from 6- (naphth-1-yl-sulfonylamido) -1- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] -1,2,3,4-tetrahydro-quinoline (see example 32) and 4 methyl-bromobutyrate Yield: 79% of the theory (4) 6- [N- (2-ethoxycarbonyl) -naphth-l-yl-sulfonylamido] -l- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl ] - 1,2,3,4-tetrahydro-quinoline Prepared from 6- (naphth-1-yl-sulfonylamido) -1- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] - 1, 2, 3 , 4-tetrahydro-quinoline (see example 32) and ethyl 2-bromopropionate Yield: 72% of theory Rf value: 0.24 (silica gel; methylene chloride / ethyl acetate = 8: 2) (5) 6 - [N-Methyl- (naphth-l-yl-sulfonyl) -amido] -l- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] -l, 2, 3, 4-tetrahydro-quinoline Prepared from 6 - [(naft-l-yl-sulfonyl) -amid or] -l- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] - 1, 2, 3, 4-tetrahydro-quinoline and methyl iodide Yield: 68% of theory Rf value: 0.57 (silica gel_, methylene chloride / ethyl acetate = 7: 3) (6) 6- [N-benzyl- (naphth-1-yl-sulfonyl) -amido] -1- [3- ( 4- benzyloxycarbonylamino-phenyl) -propionyl] -l, 2,3,4-tetrahydro-quinoline Prepared from 6- [(naphth-1-yl-sulfonyl) -amido] -l- [3- (4-benzyloxycarbonylamido -phenyl) -propionyl] - 1, 2, 3, 4-tetrahydro-quinoline and benzyl bromide Yield: 72% of theory Rf Value: 0.44 (silica gel; methylene chloride / ethyl acetate = 7: 3) (7) 6- [N-ethoxycarbonylmethyl- (naphth-1-yl-sulfonyl) -amido] -l- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] -1,2,3,4-tetrahydro-quinoline Prepared from 6 - [(naphth-l-yl-sulfonyl) -amido] -! - [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] - 1,2,3,4-tetrahydro-quinoline and bromine acetate of ethyl Yield: 83% of the theory (8) l- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] -6- [N- (naphth-1-yl-sulfonyl) -N, N-di (methoxycarbonylmethyl) - aminocarbonylmethyl) -amino] -l, 2,3,4-tetrahydroquinoline Prepared from the compound prepared according to example 32 and methyl bromoacetylmethoxycarbonylmethylamino acetate Yield: 59% of theory .. Rf value: 0.27 (silica gel; ethyl acetate / petroleum ether = 4: 1) Example 8: l- [3- (4-cyanophenyl) -propionyl] -6-methylamino- 1, 2, 3, 4-tetrahydro-quinoline 10.5 g (34 mmoles) of 1- (3-cyanophenyl-propionyl) -6-amino-1,2,4,4-tetrahydro-quinoline are boiled with 40 ml of triethyl orthoformate and 1 ml of trifluoroacetic acid for 6 hours, and then concentrated by rotary evaporation. The residue is absorbed in 50 ml of ethanol and at 0 ° C is added by so many 1. 45 g of sodium cyanoborohydride. This solution is stirred overnight at room temperature and then refluxed for 4 hours. Finally it is diluted with water / ice and acidified with hydrochloric acid. It is then neutralized with ammonium, extracted with methylene chloride, the organic phase is dried and concentrated by evaporation. The residue is column chromatographed on silica gel with methylene chloride / ethyl acetate 8: 2. Yield: 5. 4 g (49% of theory) Melting point: 120 ° C C20H21N3O (319.40) Calculated: C 75.20 H 6. 62 N 13. 15 Found: 75.02 _ 6.73 12.98 Example 9 l- [3- (4-Cyano-phenyl) -propionyl] -6-phenylsulfonamido- 1,2,3,4-tetrahydro-quinoline 4.6 g of 3- (4-cyano- phenyl) -propionic are dissolved with and 2.8 g of N-methyl-morpholine in 120 ml of tetrahydrofuran and cooled to -35 ° C. To this solution 3.6 ml of isobutyl chloroformate are added, stirring is continued for half an hour and then 7.2 g of 6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline are added at -40 ° C (see example IV) ). After 2 hours the solution is allowed to return slowly to room temperature, and stirring is continued overnight. It is then concentrated by evaporation and the residue is taken up in ethyl acetate and water. The organic phase is washed again with water, dried and concentrated by evaporation. The remaining oil is subjected to column chromatography on silica gel with ethyl acetate / petroleum ether (7: 3). Yield: 10.3 g (92.4% of theory) Melting point: 87-89 ° C Calculated: C 67.40 H 5.20 N 9.43 S 7.20 Found: 67.47 5.61 9.09 S 7.38 The following are prepared analogously: (1) l- [3- (4-Cyano-phenyl) -propionyl] -6- (2-naphthylsulfonamido) -1, 2, 3, 4-tetrahydroquinoline Prepared from the compound prepared in accordance with Example IV (1) Yield: 68% of the theory Melting point: 70 ° C C29H25 3? 3S (495.60) Calculated: C 70.28 H 5.08 N 8.48 Found: 70.42. 5.30 8.21 (2) l- [3- (4-Cyano-phenyl) -propionyl] -6- (1-naphthylsulfonamido) -1,2,3,4-tetrahydroquinoline Prepared from the compound prepared in accordance with with example IV (2) "Yield: 14% of theory Rf value: 0.56 (silica gel; toluene / ethyl acetate = 1: 1) (3) l- [3- (4-cyano-phenyl) -propionyl] -6- (4-fluoro-phenyl- - * sulfonamido) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (3) Yield: 64% of the theory "Melting point: 62-64 ° C C25H22F 3? 3S (463.53)." Calculated: C 64.78 H 4.78 N 9.07"Found: 65.00 5.16 8.73 (4) 6- (n-butyl-sulfonamido) -l- [3- (4-cyano-phenyl) -propionyl] -l, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared in accordance with Example IV (4) Yield: 53% of the theory Melting point: 138-140 ° C (5) l- [3- (4-cyano-phenyl) -propionyl] -5-phenyl-sulfonamido- 1,2, 3, 4-tetrahydro-quinoline. Prepared from the compound prepared according to example IV (7) Rf value: 0.32 (silica gel; toluene / ethyl acetate = 6: 4) (6) l- [3- (4-cyano-phenyl) - propionyl] -7-phenyl-sulfonamido-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (8) _7 Point, melting: 74-76 ° C _ (7) 7 -benzylsulfonamido-l- [3- (4-cyano-phenyl) -propionyl] -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (6) Melting point: 177 -180 ° C (8) l- [3- (4-cyano-phenyl) -propionyl] -6- (N-methyl-phenyl-sulfonamido) -1,2,3,4-tetrahydro-quinoline Prepared from of the compound prepared Conformance to Example IV (5) Yield: 74% of theory Melting point: 114-116 ° C C26H25 3O3S (459.57) Calculated: C 67.95 H 5.48 N 9.14 S 6.98 Found: 68.02 5.56 9.25 S 7.04 (9) l- [3- (4-Cyano-phenyl) -propionyl] -6-phenyl-acetylamino-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (9 ) Yield: 81% of theory (10) l- [3- (4-cyano-phenyl) -propionyl] -6- [N- (ethoxycarbonylmethyl) -phenylsulfonamido] -l, 2, 3, 4-tetrahydro -quinoline Prepared from the compound prepared according to example 6 Melting point: 148-150 ° C C29H29 305S (531.65) Calculated: C 65.52 H 5.50 N 7.90 S 6.03 Found: 65.34 5.54 7.86 S 6.03 (11) l- [3- (4-cyano-phenyl) -propionyl] -6- [N- (2-phenylethyl) - - "7-phenylsulfonamido] -l, 2,3,4-tetrahydro-quinoline" Prepared from the compound prepared in accordance with the example IV (15) (12) 6-benzylsulfonamido-l- [3- (4-cyano-phenyl) -propionyl] -1,2,3,4-tetrahydro-quinoline "Prepared from the compound prepared according to example IV (ll) Melting point: 161-163 ° C C26H25N3O3S (459.57) Calculated: C 67.95 H 5.48 N 9.14 Found: 67.93 5.56 9.07 (13) 6-benzoylamino-l - [3- (4-cyano-phenyl) -propionyl] -l, 2, 3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (12) • Yield: 83% of theory C26H23N303 (409.49) Calculated: C 76.26 H 5.66 N 10.26 Found: 76.17 5.85 10.19 (14) l- [3- (4-Cyano-phenyl) -propibnyl] -2-methyl-6-phenyl-sulfonamido-1,2, 3,4-tetrahydroquinoline Prepared from the compound prepared according to example IV (10) Yield: 41% of the theory (15) l- [3- (4-cyano-phenyl) -propionyl] -6- (4-Chloro-phenyl-1-sulfonamido-1, 2,3,4-tetrahydro-quinoline: Prepared from the compound prepared from - conformity with example IV (17) (16) l- [3- (4-cyano-phenyl) -propionyl] -6- (4-bromo-phenyl-1-sulfonamido-1,2,3,4-tetrahydro- quinoline - Prepared from the compound prepared according to example IV (18) (17) l- [3- (4-cyano-phenyl) -propionyl] -6- (3-chloro-phenylsulfonamido-1, 2, 3,4-tetrahydroquinoline Prepared from the compound prepared according to example IV (19) (18) l- [3- (4-cyano-phenyl) -propionyl] -6- (3-bromo-phenylsulfonamido- 1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (20) (19) l- [3- (4-cyano-phenyl) -propionyl] -6- (4- methi1-pheny1-sulfonamido-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (21) (20) l- [3- (4-cyano-phenyl) -propionyl] -6- (4-methoxy-phenylsulfonamido-1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (22) (21) l- [3- (4-cyano-phenyl) ) -? ropionyl] -6- [N- (2-phenylethyl) -phenylsulfonamido] -l, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (11) Yield: 69% of the theory (22) l- [3- (4-cyano-phenyl) -propionyl] -6- (4-methyl-piperidino-carbonyl) -1,2,3, 4-tetrahydro -quinoline Prepared from the compound prepared according to Example IV (29) Yield: 67% of the theory Rf Value: 0.73 (silica gel; methylene chloride / ethyl acetate = 8: 2) (23) l- [3 - (4-cyano-phenyl) -propionyl] -6- (morpholinocarbonyl) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (22) Yield: 37% of the Theory Rf value: 0.73 (silica gel_ "methylene / ethyl acetate = 8: 2") (24) l- [3- (3-cyano-phenyl) -propionyl] -6-phenylsulfonamido- 1,2, 3,4-tetrahydro-quinoline Prepared from the compound prepared according to Example IV - Yield: 78% of the theory Melting point: 130-133 ° C (25) l- [2- (4-cyano- phenyloxy) -acetyl] -6-phenylsulfonamido- 1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV and 4-cyanophenoxyacetic acid - Yield: 68% of the theory Melting point: 76-78 ° C l- [2- (4-cyano-phenyloxy) -acetyl] -6-phenylsulfonamido-1, 2, 3, 4- - Melting point: 76-78 ° C (26) _ l- [2- ((4 -cyano-phenyl) -methylamino) -acetyl] -6-benzole-sulfonamido-1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV Yield: 82% of the theory Fusion: 193-194 ° C (27) l- [2- (4-Cyano-phenyloxy) -acetyl] -6- (1-naphthylsulfonamido-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared in accordance with Example IV (2) Yield: 41% of the theory (28) l- [3- (4-cyano-2-nitro-phenyl) -propionyl] -6-phenyl-sulfonamido-1, 2, 3, 4-tetrahydro-quinoline ~ Rf value: 0.56 (silica gel; methylene chloride / methanol = 9: 1) (29) 1- (4-cyano-benzoyl) -6-phenyl-sulfonamido-1, 2, 3,4- tetrahydro-quinoline Prepared from the compound prepared according to example IV and 4-cyanobenzoic acid Yield: 71% of the theory Melting point: 132-134 ° C (30) l- [3- (4 -cyano-3-methyl-phenyl ) -propionyl] -6-phenyl- * sulfonamido-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to Example IV and 4-cyano-3-methyl-phenylpropionic acid Rf value: 0.40 (silica gel; methylene chloride / ethanol = 40: 1) (31) l- [3- (4-cyano-3-fluoro-phenyl) -propionyl] -6-phenyl-sulfonamido-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to Example IV and 4-cyano- 3-fluorophenylpropionic Yield: 36% of theory Melting point: 138-140 ° C (32) l- [3- (2-cyano-pyridin-5-yl) -propionyl] -6-phenylsulfonamido- 1, 2,3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example IV Yield: 73% of the theory Rf value: 0.35 (silica gel; methylene chloride / methanol = 40: 1) (33) l- [3- (4-Cyano-phenyl) -acyloyl] -6-phenyl-sulfonamido-1,2,3,4-tetrahydro-quinoline Yield: 74% of theory Melting point: 175-180 ° C (34) l- [3- (4-cyano-phenyl) -propionyl] -6-piperidinocarbonyl- 1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (23) Yield: 97% of the theory Value 'Rf: 0.38 (silica gel; ethyl acetate) (35) l- [3- (4-cyano-phenyl) ) -propionyl] -β-benzylamidocarbonyl-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to Example IV (24) Yield: 60% of the theory Rf Value: 0.38 (silica gel toluene / ethyl acetate = -4: 6) (36) l- [3- (4-cyano-phenyl) -propionyl] -6- (N-methyl-phenyl-aminocarbonyl-1, 2, 3, 4- tetrahydro-quinoline Prepared from the compound prepared according to example IV (25) - Yield: 82% of the theory Rf value: 0.72 (silica gel; ethyl acetate) (37) l- [3- (4- cyano-phenyl) -propionyl] -6- (diethylaminocarbonyl) -1,2,3,4-tetrahydro-quinoline ~ Prepared from the compound prepared according to example IV (26) Yield: 55% of theory Rf value: 0.21 (silica gel; methylene chloride / ethyl acetate = 8: 2) (38) l- [3- (4-cyano-phenyl) -propionyl] -6- (3, 5-dimethyl- piperidinocarbonyl-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example IV (27) Yield: 96% of the theory Rf value: 0.38 (silica gel; methylene chloride / ethyl acetate) ethyl = 8: 2) (39) l- [3- (4-cyano-phenyl) -propionyl] -6-methoxycarbonyl-1,2,3,4-tetrahydroquinoline Prepared from methyl 1, 2, 3,4-tetrahydroquinoline-6-carboxylate Yield: 65% of theory Example 10 l- [3- (4-cyano-phenyl) -propionyl] -6- (4-amino-3,5-dichlorophenyl) -sulfonamido) -1,2,3, 4-tetrahydro-quinoline _ 1.0 g of 6-amino l- [3- (4-cyano-phenyl) -propionyl] -1,2,3,4-tetrahydro-quinoline ( see example 5) is dissolved in 8 ml of pyridine, combined with 1 g of 4-amino-3,5-dichloro-phenylsulfonic acid chloride in so many, and then heated for 40 minutes at 100 ° C. The solvent is then removed, the residue is triturated with IN hydrochloric acid and extracted with methylene chloride. The organic phase is dried over sodium sulfate and concentrated by evaporation. Yield: 1.5 g (86% of theory) Melting point: 183-184 ° C C2sH22N4Cl2? 3S (529.45) Calculated: C 56.72 H 4.19 N 10.58 Found: 56.54. 4.25 10.44 The following are prepared analogously: (1) l- [3- (4-cyano-phenyl) -propionyl] -6- (5-dimethylamino-naphth-1-yl-sulfonamido) -1,2,3 , 4-tetrahydro-quinoline Prepared from the compound prepared according to example 5 Yield: 95% of the theory Melting point: 78-80 ° C C3? H3oN403S (538.67) Calculated: C 69.12 H 5.61 N 10.43 ncontrado: 70.11 5.82 9.79 (2) l- [3- (4-Cyano-phenyl) -propionyl] -6-propyl-sulfonamido- * 1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared in accordance with example 5 Yield: 95% of theory * Melting point: 152-153 ° C C22H25N3? 3S (411.52) Calculated: C 64.21 H 6.12 N 10.21 Found: 64.05 6.10 10.02 (3) 6- (5-chloro-thien) 2-yl-sulfonamido) -l- [3- (4-cyano-phenyl) -pro-ionyl] -l, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared from according to example 5 Yield: 69% of the theory Melting point: 153-154 ° C C23H2oClN3? 3S2 (486.01) Calculated: C 56.84 H 4.14 N 8.64 Cl 7.29 Found: 56.88 4.24 8.24 7.08 l- [3- (4 -cyano-f-enyl) -propionyl] -6-isopropyl-sulfonamido-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 5 Yield: 37% of the theory Melting point: 151-152 ° C C22H25N3O3S (411.52) Calculated: C 64.21 H 6.12 N 10.21 Found: 64.70 6.25 9.89 .5) 6- (3-Chloro-propylsulfonamido) -l- [3- (4-cyano-phenyl) -propionyl] -l, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 5 Yield: 55% of theory C22H2.CIN3O3S (445.97) Calculated: C 59.25 H 5.42 N 9.42 Cl 7.95 Found: 58.68 5.44 9.26 8.32 (6) l- [3- (4-Cyano-phenyl) -propionyl] -5-f-enyl-sulfonamido-2,3-dihydro-indole Prepared from the compound prepared from. according to example 2 Yield: 78% of the theory Rf value: 0.46 (silica gel; toluene / ethyl acetate = 6: 4) (7) l- [3- (4-cyano-phenyl) -propionyl] - 7-phenylsulfonamido-2,3,4,5-tetrahydro-lH-benzo [b] azepine Prepared from the compound prepared according to example 2 (2) Yield: 57% of the theory Rf Value: 0.30 (gel silica; toluene / ethyl acetate = 13: 7) (8) l- [3- (4-cyano-phenyl) -propionyl] -3-methyl-1-6-phenylsulfonamido-1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 2 (1) Yield: 79% of the theory Rf Value: 0.35 (silica gel; toluene / ethyl acetate = 7: 3) (9) l- [3- ( 4-cyano-phenyl) -propionyl] -4-methyl-6-phenyl-sulfonamido-1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 2 (3) Yield: 89% of the theory Rf Value: 0.21 (silica gel; toluene / acetate) ethyl = 7: 3) (10) l- [3- (4-cyano-phenyl) -propionyl] -6- (3-trifluoromethyl-phenylsulfonamido) -1, 2, 3, 4-tetrahydro-quinoline Prepared from compound prepared according to example 5 Yield: 72% of theory Rf value: 0.55 (silica gel; methylene chloride / ethanol = 4: 1) (11) l- [3- (4-cyano-phenyl) - propionyl] -6- (2, 5-dichloro-phenylsulfonamido) -1, 2, 3, 4-tetrahydro-quinoline Yield: 89% of the theory Melting point: 219-220 ° C "C25H2? Cl2N303S (514.43 ) Calculated: C 58.37 H 4.11 N 8.17 ~~ Found: 58.10 '4.33 8.05 (12) l- [3- (4-cyano-phenyl) -propionyl] -6- (2,3,5,6-tetramethylphenyl) -sulfonamido) -1,2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared from < _ conformance to example 5 Yield: 89% of the theory Melting point: 228 ° C (13) l- [3- (4-cyano-phenyl) -propionyl] -6- (2,4,6-trimethyl-) phenylsulfonamido) -1,2,3,4-tetrahydroquinoline Prepared from the compound prepared according to example 5 Yield: 86% of the theory Melting point: 182 ° C C28H29 3O3S (501.65) Calculated: C 68.97 H 5.99 N 8.62 Found: 68.91 6.08 8.68 (14) l- [3- (4-cyano-phenyl) -prop? onyl] -6- (isoquinolin-5-yl- - * sulfonamido) -1, 2, 3, 4-tetrahydroquinoline - Prepared from the compound. prepared from? conformance to example 5 Yield: 89% of the theory Melting point: 210-211 ° C Rf value: 0.46 (silica gel '; methylene chloride / ethanol = 20: 1) (15) l- [3- (4-cyano-phenyl) -propionyl] -6- (cyclopropyl-sulfonamido) -1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 5 Yield: 74% of the theory Melting point: 138-139 ° C (16) l- [3- (4-cyano-phenyl) -propionyl] -6- (benzimidazole -5-yl-sulfonamido) -1,2,3,4-tetrahydro-quinoline * "Prepared from the compound prepared according to example 5 Yield: 36% of the theory" Rf value: 0.29 (silica gel chloride , methylene / ethanol = 20: 1) (17) l- [3- (4-cyano-phenyl) -propionyl] -6- (cyclohexyl-sulfonamido) -1,2,3,4-tetrahydro-quinoline Prepared from of the compound prepared according to example 5 Yield: 57% of the theory Melting point: 159-163 ° C (18) l- [3- (4-cyano-phenyl) -propionyl] -6- (3-tolylsulfonamido) ) - 1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 5 Yield: 78% of the theory Melting point: 130 ° C - C26H25 303S (459.57) Calculated: C 67.95 H 5.48 N 9.14 Found: 67.68 5.54 8.89 (19) l- [3- (4-Cyano-phenyl) -propionyl] -6- (4-methoxy-benzolesulfonamido) -1,2,3, 4-tetrahydro-quinoline • Prepared from the compound prepared according to example 5 Yield: 87% of the theory Melting point: decomposition from 65 ° C C26H25N304S (475.57) Calculated: C 65.66 H 5.29 N 8.83 Found: 65.75 5.61 8.64 (20) l- [3- (4-Cyano-phenyl) -propionyl] -6- (N-ethoxycarbonyl-methyl-quinoline-8-sulfonylamido) -1,2,3,4-tetrahydroquinoline Prepared from l- [3- (4-Cyano-phenyl) -propionyl] -6- (N-ethoxycarbonylmethylamino) -1,2,3,4-tetrahydroquinoline (see example 6) and quinolinesulfonic acid chloride. Yield: 57% of theory (21) l- [3- (4-cyano-phenyl) -propionyl] -6- [N-ethoxycarbonyl-methyl-2-naphthylsulfonylamido] -l, 2,3,4-tetrahydro- quinoline Prepared from l- [3- (4-cyano-phenyl) -propionyl] -6-ethoxy-carbonylamino-l, 2,3,4-tetrahydro-quinoline (see example 6) and naphthalene-chloride 2- sulfonic. Yield: 69% of the theory (22) l- [3- (4-cyano-phenyl) -propionyl] -6- [N-benzyl-methanesulfonamido] -l, 2,3,4-tetrahydro-quinoline - Prepared from the compound prepared according to example 14 and methanesulfonic acid chloride - Yield: 51% of the theory - Rf value: 0.34 (silica gel; toluene / acetate) ethyl = 1: 1) (23) l- [3- (4-cyano-phenyl) -propionyl] -6- [N- (ethoxycarbonyl- methylamino) -phenylmethanesulfonamido] -l, 2,3,4-tetrahydro-quinoline. Prepared from the compound prepared according to Example 6 and phenylmethanesulfonic acid chloride Yield: 78% of the theory Example 11 l- [3- (4-cyano-phenyl) -propionyl] -6- (N-benzoyl-ethoxy) - carbonylmethylamino) -1, 2,3,4-tetrahydro-quinoline "1.57 g of l- [3- (4-cyano-phenyl) -propionyl] -6- (N- (ethoxycarbonylmethyl-amino) -1,2, 3,4-tetrahydro-quinoline (see example 6) and 1 g of triethylamine are dissolved in 20 ml of methylene chloride and 0.7 g of benzoyl chloride are slowly added dropwise while cooling with ice. the solution is stirred overnight at room temperature, then the solution is concentrated by evaporation, the residue is taken up in water and extracted with ethyl acetate.The organic phase is dried and concentrated by rotary evaporation. filter on a column on silica gel Yield: 1.7 g (85% of theory) The following are prepared analogously: (1) l - [3- (4-cyano-phenyl) -propionyl] -6- [N-ethoxycarbonyl-methyl- (naphth-1-yl) -amino] -l, 2,3,4-tetrahydro-quinoline Yield: 82% of the theory (2) l- [3- (4-Cyano-phenyl) -propionyl] -6- (N-benzoyl-methyl-amino) -1, 2,3,4-tetrahydroquinoline Prepared from the compound prepared in accordance with example 8 and benzoyl chloride Yield: 83% of the theory Value Rf 0.37 (silica gel; toluene / ethyl acetate = 1: 1) (3) l- [3- (4-cyano-phenyl) -propionyl ] -6- [N- (4-chlorobenzoyl) - __ methyl-amino] -l, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to Example 8 and 4-chlorobenzoyl chloride Yield: 91% of theory C27H24N302S (475.57) Calculated: C 70.81 H 5.28 N 9.17 Found: 71.52 5.51 8.50 (4) l- [3- (4-cyano-phenyl) -propionyl] -6- (N-naphthi-1- il-methyl-amino) -1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 8 and naphthalene-1-carboxylic acid chloride Yield: 94% of theory C3iH27N302 (473.57) J Calculated: C 78.62 H 5.74 N 8.87 Found: 78.30 6.03 8.52 (5) l- [3- (4-Cyano-phenyl) -propionyl] -6- (N-naphth-2-yl-methyl-amino) -1,2,3,4-tetrahydro-quinoline Prepared from compound prepared according to example 8 and naphthalene-2-carboxylic acid chloride Yield: 93% of theory C3? H27N302 (473.57) Calculated: C 78.62 H 5.74 N 8..87 J Found: 78.62 5.88 8.19 (6) l- [3- (4-Cyano-phenyl) -propionyl] -6- (N-butyryl-methyl-amino) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to the example 8 and butyric acid chloride Yield: 98% of theory C24H2.N3? 2 (389.49) Calculated: C 74.00 H 6.98 N 10.78 Found: 74.09 7.01 10.43 (7) l- [3- (4-cyano-2- acetylamino-phenyl) -propionyl] -6- phenylsulfonylamido-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 2 (4) and acetyl chloride Yield: 90% of theory ~~ Rf value: 0.58 (silica gel; methylene chloride / methanol = 9: 1) (8) l- [3- (4-Cyano-2- (2-ethoxycarbonylethylcarbonylamino) -propionyl] -6-phenylsulfonamido-1,3,4,4-tetrahydroquinoline Prepared from the compound prepared according to the example 2 (4) and ethyl succinate chloride - Rf value: 0.63 (silica gel; methylene chloride / methanol = 9: 1) (9) l- [3- (4-cyano-phenyl) -propionyl] -6 - (N-benzyl-acetylamino) -1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 14 and acetyl chloride Yield: 91% of the theory Rf Value: 0.27 (gel silica; toluene / ethyl acetate = 1: 1) (10) l- [3- (4-cyano-phenyl) -propionyl] -6- (N-benzyl-N- .- pentanoylamino) -1,2 , 3,4-tetrahydroquinoline Prepared from the compound prepared according to Example 14 and valerylchloride Yield: 83% of theory - Rf value: 0.57 (silica gel; toluene / ethyl acetate = 1: 1) (11) l- [3- (4-Cyano-phenyl) -propionyl] -6- [N-benzyl-N- (2-ethoxycarbonylethylcarbonyl) -amino] -l, 2, 3, 4-tetrahydroquinoline Prepared from the compound prepared according to Example 14 and ethyl succinate chloride Yield: 86% of the theory Value R £: 0.19 (silica gel; methylene chloride / ethyl acetate = 8: 2) (12) * l- [3- (4-cyano-phenyl) -propionyl] -6- (2-oxo-pyrrolidino) -1,2, 3,4-tetrahydro-quinoline Prepared from 6-amino l- [3- (4-cyano-phenyl) -propionyl] -l, 2, 3, 4-tetrahydro-quinoline and 4-chlorobutyric acid chloride Yield: 77% of the theory Rf Value: 0.40 (silica gel, ethyl acetate) ( 13) l- [3- (4-cyano-phenyl) -propionyl] -6- (2-oxo-piperidino) -1,2,3,4-tetrahydro-quinoline Prepared from 6-amino l- [3 - (4-cyano-phenyl) -propionyl] -l, 2, 3, 4-tetrahydro-quinoline and 5-chloropentanoic acid chloride Yield: 69% of the theory Rf Value: 0.11 (silica gel, ethyl acetate) Example 12 l- [3- (4-Cyano-phenyl) -propionyl] -6- (N-phenyl-butylaminocarbonyl) -1,2,3,4-tetrahydro-quinoline 0.9 g (4 mmoles) of l- [3- (4-cyano-phenyl) ) -propionyl] -6-methoxycarbonyl-l, 2, 3, 4-tetrahydro-quinoline (see example 9 (39)) are dissolved in 10 ml of dioxane and stirred with 10 ml of a 1 N sodium hydroxide solution at 40 ° C for 4 hours. The solution is then neutralized with hydrochloric acid, concentrated by evaporation, and the precipitate formed is filtered off with suction and dried. The product is suspended in 10 ml of thionyl chloride and refluxed for 3 hours. It is then concentrated by evaporation and the residue is taken up in 10 ml of methylene chloride, and combined with 0.93 ml of triethylamine and 0.6 g of N-phenylbutylamine in a little methylene chloride. The reaction is terminated after 20 minutes, and the mixture is added with 10 ml of a 1 N sodium hydroxide solution followed by 10 ml of water. The solution is then dried and concentrated by rotary evaporation, and the residue is column chromatographed on silica gel with toluene / ethyl acetate (8: 2). "Yield: 1.35 g (70% of theory) Rf value: 0.29 (silica gel; toluene / ethyl acetate = 7: 3) The following are prepared analogously: (1)" l- [3- (4-cyano-phenyl) -propionyl] -6- [N- (4-chloro-phenyl) -methylaminocarbonyl] -l, 2, 3, 4-tetrahydro-quinoline Yield: 75% of the theory Rf Value: 0.19 ( silica gel; toluene / acetate ethyl = 7: 3) (2) l- [3- (4-cyano-enyl) -propionyl] -6- (N-phenyl-ethylamino-carbonyl) -1,2,3,4-tetrahydro-quinoline Yield : 71% of the theory Rf Value: 0.16 (silica gel; toluene / ethyl acetate = 7: 3) (3) l- [3- (4-cyano-phenyl) -propionyl] -6- (diphenylamino-carbonyl ) -1,2,3, 4-tetrahydro-quinoline Yield: 34% of theory Rf Value: 0.37 (silica gel; toluene / ethyl acetate = 7: 3) (4) l- [3- (4- cyano-phenyl) -propionyl] -6- (N-phenyl-benzylaminocarbonyl) -1, 2, 3, 4-tetrahydroquinoline Yield: 29% of the theory Rf Value: 0.31 (silica gel: toluene / ethyl acetate = 7: 3) (5) l- [3- (4-cyano-phenyl) -propionyl] -6- (N-methoxycarbonyl-methyl-phenylaminocarbonyl) -1,2,3,4-tetrahydro-quinoline Yield: 66% of the theory _ Rf value: 0.18 (silica gel, toluene / ethyl acetate = 7: 3) (6) l- [3- (4-cyano-phenyl) -propionyl] -6- (N -cyclohexyl-methyl-aminocarbonyl) -1,2,3,4-tetrahydroquinoline Yield: 88% of the theory Rf Value: 0. 20 (silica gel; toluene / acetate ethyl = 7: 3) (7) l- [3- (4-cyano-phenyl) -propionyl] -6- (N-ethoxycarbonyl-methyl-cyclohexylaminocarbonyl) -1,2,3,4-tetrahydroquinoline Yield: 34% of theory Rf value: 0.13 (silica gel; toluene / ethyl acetate = 7: 3) (8) l- [3- (4-cyano-phenyl) -propibnyl] -6- (2-methoxycarbonyl- pyrrolidinocarbonyl) -1,2,3,4-tetrahydroquinoline Yield: 62% of theory Rf Value: 0.12 (silica gel; toluene / ethyl acetate = 1: 1) (9) l- [3- ( 4-cyano-phenyl) -propionyl] -6- (2-methoxycarbonyl-piperidinocarbonyl) -1,2,3,4-tetrahydroquinoline Yield: 64% of the theory "Rf value: 0.22 (silica gel; toluene / ethyl acetate = 1: 1) (10) 1-. { 1- [3- (4-cyano-phenyl) -propionyl]} -6- (3-ethoxycarbonyl-piperidinocarbonyl) -1,2,3,4-tetrahydroquinoline Yield: 75% of the theory ~ Rf value: 0.18 (silica gel; toluene: ethyl acetate = 1: 1) ( 11) l- [3- (4-cyano-phenyl) -propionyl] -6- [N- (2-acetylamino-ethyl) -phenylamidocarbonyl] -l, 2,3,4-tetrahydro-quinoline Yield: 67% of the theory Rf value: 0.27 (silica gel; ethyl acetate: ethanol = 19: 1) (12) l- [3- (4-cyano-phenyl) -propionyl] -6- [N- (N-benzyloxycarbonyl- N-phenyl-2-aminoethyl) -aminocarbonyl] -l, 2,3,4-tetrahydro-quinoline Yield: 73% of the theory Rf Value: 0.31 (silica gel; toluene / ethyl acetate = 1: 1) Example 13 l- [3- (4-Cyano-phenyl) -propionyl] -6- [N- (N-phenyl-2-amino-ethyl) -amidocarbonyl] -l, 2,3,4-tetrahydro-quinoline is prepared from l- [3- (4-cyano-phenyl) -propionyl] -6- [N- (N-benzyloxycarbonyl-N-phenyl-2-aminoethyl) -aminocarbonyl] -l, 2, 3, 4-tetrahydro -quinoline (see example 12 (12) by catalytic reduction in analogous manner to Example 25. Yield: 75% of the theory Example 14 l- [3- (4-cyano-phenyl) -propionyl] -6-benzylamino-1 , 2, 3, 4-tetrahydro-quinoline 2.9 g (9.5 mmol) of 6-amino-l- [3- (4-cyano-phenyl) -propionyl] -l, 2, 3, 4-tetrahydro-quinoline are dissolved in 80 ml of methanol and 0.6 ml of acetic acid, combine with 1.06 g (10 mmol) of benzaldehyde and they are stirred for 20 minutes at 0 ° C. Next, 0.63 g of sodium cyanoborohydride in small amounts, stirring is continued for half an hour, and then the mixture is allowed to warm to room temperature. The solution is then concentrated by rotary evaporation, and the residue is absorbed in a little water / ice. The solution is then acidified and sodium hydroxide solution is added until an alkaline reaction is obtained, and then the mixture is extracted with methylene chloride. The dried solution is concentrated by rotary evaporation, and the residue is column chromatographed on silica gel with toluene / ethyl acetate (1: 1). Yield: 3.7 g (98% of theory) C26H25N30 (395.51) Calculated: C 78.95 H 6.37 N 10.62 Found: 79.08 6.54 9.76 The following are prepared analogously: (1) l- [3- (4-cyano-phenyl ) -propionyl] -6 - [(naft-1-yl-methyl) -amino] -1, 2,3, 4-tetrahydro-quinoline Yield: 78% of theory C30H27N3O (445.57) Calculated: C 80.87 H 6.10 N 9.43 Found: 80.33 6.36 8.98 (2) l- [3- (4-Cyano-phenyl) -propionyl] -6 - [(naphth-2-yl-methyl) -amino] -1, 2, 3, 4-tetrahydro -quinoline Yield: 90% of theory C3oH27N30 (445.57) Calculated: C 80.87 H 6.10 N 9.43 Found: 80.66 6.30 8.89 (3) l- [3- (4-cyano-phenyl) -propionyl] -6- (N-methyl- benzyl-amino) -1,2,3,4-tetrahydro-quinoline Prepared from 6-benzylamino-l- [3- (4-cyano-phenyl) -propionyl] -l, 2, 3, 4-tetrahydro -quinoline (see example 14) and formaldehyde Rf value: 0.42 (silica gel; methylene chloride / ethyl acetate = 19: 1) (4) l- [3- (4-cyano-phenyl) -propionyl] - 6- (2, 2-diphenyl-ethyl-amino) -1,2,3,4-tetrahydro-quinoline Prepared from 6-amino-1- [3- (4-cyano-phenyl) -propionyl] -! , 2, 3, 4-tetrahydro-quinoline and diphenyl-acetyldehyde Yield: 80% of the theory Value Rf: 0.49 (silica gel; methylene chloride / ethyl acetate = 9: 1) Example 15 l- [3- (4-Cyano-phenyl) -propionyl] -6- (N-ethylaminocarbonyl-methyl-benzylamino) -1,2,3,4-tetrahydro-quinoline To a solution of 1.2 g of l- [3- (4-cyano-phenyl) -propionyl] -6- [N-hydroxycarbonylmethyl-N-benzyl-amino] - 1, 2, 3,4-tetrahydro-quinoline (prepared in a manner analogous to Example 32 from l- [3- (4-cyano-phenyl) -propionyl] -6- [N-ethoxycarbonylmethyl-N-benzyl-amino] ] -l, 2, 3, 4-tetrahydro-quinoline (see example 6 (1)) in 15 ml of dimethylformamide is added 0.8 g of dicyclohexyl carbodiimide, and the mixture is stirred for 10 minutes at 40 ° C. The mixture is cooled to 0 ° C and 0.22 g of ethylamine in 5 ml of diethylformamide are added and the mixture is stirred overnight, then the solution is concentrated by evaporation and the residue is chromatographed on a silica gel column with methylene chloride. ethyl acetate (8: 2) Yield: 94% of the theory Rf Value: 0.29 (silica gel, methylene chloride / ethyl acetate = 8: 2) The following are prepared analogously: (1) l - [3- (4-cyano-phenyl) -propionyl] -6- [N- (N, N-dipropyl-amino-carbonylmethyl) -benzylamino] -l, 2, 3, 4-tetrahydroquinoline Yield: 51% of the Rf value theory: 0.43 (silica gel; methylene oxide / ethyl acetate = 9: 1) (2) l- [3- (4-cyano-phenyl) -propionyl] -6- [N- (benzylamino-carbonylmethyl) -benzylamino] -l, 2,3 , 4-tetrahydroquinoline Yield: 92% of the theory Rf Value: 0.38 (silica gel; methylene chloride / ethyl acetate = 8: 2) (3) l- [3- (4-cyano-phenyl) -propionyl] -6- [ N- (phenylaminocarbonylmethyl) -benzylamino] -l, 2,3,4-tetrahydroquinoline Yield: 60% of theory Rf Value: 0.58 (silica gel; methylene chloride / ethyl acetate = 9: 1 Example 16 l- [3- (4-Cyano-phenyl) -propionyl] -6-phenylaminosulfonyl-1,2,3,4-tetrahydro-quinoline (a) l- [3- (4-cyano-phenyl) - propionyl] -l, 2, 3, 4-tetrahydroquinoline-6-sulfonyl-chloride (0.04 mol) of l- [3- (4-cyano-phenyl) -propionyl] - 1, 2, 3, 4-tetrahydro -quinoline are dissolved in 16 ml of chlorosulfonic acid at 0 ° C. The thick liquid mass is heated to 60 ° C and hydrochloric acid develops. The mixture is then carefully added to the ice and extracted with methylene chloride, dried and concentrated by rotary evaporation. Yield: 5.9 g (38% of theory) (b) l- [3- (4-cyano-phenyl) -propionyl] -6-phenylaminosulfonyl-1,2,3,4-tetrahydro-quinoline To a solution of 0.56 g of aniline in 15 ml of pyridine is added dropwise 2.33 g (6 mmol) of 1- [3- (4-cyano-phenyl) -propionyl] -! 2, 3, 4-tetrahydroquinoline-6-sulfonylchloride, insofar as ~ that cools with ice. The mixture is then heated for 30 minutes at 100 ° C and evaporated to dryness. The residue is column chromatographed on silica gel with methylene chloride: ethyl acetate. Yield: 0.5 g (18% of theory) The following are prepared analogously: (1) l- [3- (4-cyano-phenyl) -propionyl] -6-benzylaminosulfonyl- 1,2,3, 4- tetrahydro-quinoline Yield: 12% of the theory (2) l- [3- (4-cyano-phenyl) -propionyl] -6-phenylsulfonyl-1,2,3,4-tetrahydro-quinoline Prepared from l- [3- (4-cyano-phenyl) -propionyl] -1,2,3,4-tetrahydro-quinoline with benzenesulfonic acid chloride and aluminum chloride in dimethylformamide. Yield: 38% of the theory Rf Value: 0.19 (toluene / ethyl acetate = 8: 2) (3) l- [3- (4-cyano-phenyl) -propionyl] -6-benzoyl-l, 2, 3 4-tetrahydro-quinoline - Prepared from l- [3- (4-cyano-phenyl) -propionyl] -1,2,3,4-tetrahydro-quinoline with benzoic acid chloride and aluminum chloride in dimethylformamide.

Yield: 10% of the theory Rf Value: 0.61 (toluene / ethyl acetate = 7: 3) Example 17-1- [N- (4-cyano-benzyl) -methylaminocarbonyl] -6-phenyl-sulfonyl-amino-1 , 2, 3, 4-tetrahydro-quinoline A suspension of 0.87 g (3 mmoles) of 6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline in 8 ml of toluene and 1.55 ml of a 20% solution of Phosgene in toluene is stirred for 3 hours at room temperature, then combined with 0.44 g of p-cyano-N-methyl-benzylamine and refluxed for 3 hours. The reaction mixture is then concentrated by rotary evaporation and the residue is column chromatographed on silica gel with methylene chloride / methanol (39: 1). Yield: 0.81 g (58% of theory), Rf value: 0.32 (silica gel, methylene chloride / ethyl acetate = 4: 1) The following is prepared analogously (1) 1- [N- (4 -cyano-benzyl) -aminocarbonyl] -6-phenylsulfonyl- "amino-1,2,3,4-tetrahydro-quinoline. Yield: 64% of the theory, .Value Rf: 0.18 (silica gel; methylene chloride / ethyl acetate = 4: 1) Example 18 l- [3- (4-Cyano-phenyl) -propyl] -6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline 1.73 g of 6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline Dissolve with 0.7 g of triethylamine in 10 ml of dimethylformamide and combine with 1.62 g of 3- (4-cyano-phenyl) propyiolide in 15 ml of dimethylformamide, and stir for 5 hours at 40-50 ° C. The mixture is then concentrated by evaporation, the residue is dissolved in ethyl acetate / water, the organic phase is dried and concentrated by evaporation in vacuo. The product is column chromatographed on silica gel with methylene chloride / ethyl acetate (19: 1). Yield: 600 mg (23% of theory) Melting point: 131-132 ° C Example 19 l- [3- (4-cyano-phenyl) -thiopropionyl] -6-phenylsulfonamido- 1,2,3, 4- tetrahydro-quinoline 4.9 g of l- [3- (4-cyano-phenyl) -propionyl] -6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline are dissolved in 110 ml of toluene and boiled with 110 ml of Lawesson's reagent [2,4-bis (4-methoxy-phenyl) -1,3-dithia-2,4-diphosphetane-2,4-disulfide] for 1 hour at 110-120 ° C. The mixture is then evaporated to dryness and the residue is column chromatographed on silica gel with methylene chloride / ethyl acetate == 19: 1.

Yield: 3.5 g (69% of theory) C25H23N3O2S2 (461.61) Calculated: C 65.08 H 5.02 N 9.10 S 13.89 Found: 64.84 5.09 9.02 13.71 Example 20 l- [3- (4-cyano-phenyl) propionyl] -2, 3,4,5-tetrahydro-lH-benzo [b] azepine Prepared in a manner analogous to Example 1 by the reaction of 2, 3, 4, 5-tetrahydro-lH-benzo [b] azepine and 3- (3-chloride) 4-cyano-phenyl) propionic. Yield: 3.0 g (82% of theory) Rf value 0.54 (silica gel, toluene / ethyl acetate = 7: 3) Example 21 l- [3- (4-cyano-phenyl) propyl] -dihydrocarbostyril 1.47 g of Dihydrocarbostyril are dissolved in 10 ml of dimethyl sulfoxide and combined with 0.49 g of sodium hydride in oil at room temperature. Then 2.71 g of 3- (4-cyano-phenyl) -propyl iodide in 5 ml of dimethylsulfoxide are added and the mixture is stirred for 1 1/2 hours at room temperature. The solution is then added to 20 ml of water and extracted three times with ethyl acetate. The combined organic phases are dried and concentrated by evaporation in vacuo. The oil obtained is chromatographed on a gel silica with toluene / ethyl acetate (8: 2). Yield: 2.5 g (86% of theory) Rf value: 0.63 (silica gel; toluene / ethyl acetate = 8: 2) Example 22 l- [3- (4-cyano-phenyl) propyl] -6-nitro -dihydrocarbon-styryl is prepared analogously to Example 3 by nitration of l- [3- (4-cyano-phenyl) propyl] -dihydrocarbostyril. - Yield: 70% of the theory Rf Value: 0.30 (silica gel, toluene / ethyl acetate = 8: 2) Example 23 l- [3- (4-cyano-phenyl) propyl] -6-amino-dihydrocarbon- styryl Prepare analogously to Example 2 by reducing JL- [3- (4-cyano-phenyl) propyl] -6-nitro-dihydrocarbostyril. Yield: 86% of theory "Rf Value: 0.45 (silica gel; ethyl acetate) Example 24 l- [3- (4-Amidino-phenyl) propionyl] -6-phenyl-sulfonamido-1,2-hydrochloride 3, 4-tetrahydro-quinoline At 10 ° C 1.3 g of l- [3- (4-cyano-phenyl) - are added. propionyl] -6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline (see example 9) to 25 ml of ethanol saturated with hydrogen chloride, and at -5 ° C a weak stream of hydrogen chloride through the solution. The mixture is then allowed to warm to room temperature and is stirred overnight. It is then concentrated by evaporation, and the residue is washed with ethanol. The residue is then suspended in 50 ml of methanol, 2.25 g of ammonium carbonate is added, and the mixture is allowed to stand overnight. The mixture is then concentrated by evaporation and the residue is column chromatographed on silica gel with methylene chloride / methanol = 8: 2. Yield: 1.15 g (77% of theory) "Melting point: from 140 ° C (decomp) C25H26N403S x HCl x H20 (517.06) Calculated: C 58.08 H 5.65 N 10.84 S 6.20 Found: 58.39 5.73 10.54 6.07 The following are prepared analogously: (1) L- [3- (4-amidino-phenyl) propionyl] -6- (2-naphthylsulfonamido) -1,2,3,4-tetrahydroquinoline hydrochloride Prepared from compound prepared according to example 9 (1) Yield: 83% of the theory Melting point: from 115 ° C (decomp) ,.

- C29H2_N03S x 1.25 HCl (558.50) Calculated: C 62.41 H 5.30 N 10.03 Found: 61.94 -5.65 9.82 (2) L- [3- (4-amidino-phenyl) propionyl] -6- (1-) naphthyl- hydrochloride sulfonamido) -1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (2) Yield: 55% of the theory Melting point: 100 ° C (decomp) "C29H28N.1O3S x HCl x H20 (585.13) Calculated: C 59.50 H 5.68 N 9.75 Found: 59.66 5.84 10.03 (3) ~~ l- [3- (4-Amidino-phenyl) propionyl] -6- (4- fluoride- phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (3) Yield: 86% of the theory Melting point: 135 ° C (decomp) • - 'C25H25FN .1O3S x 1.25 HCl (526.14) 7 Calculated: C 57.08 H 5.03 N 10.65 'Found: 57.08 5.39 10.72 (4) L- [3- (4-amidino-phenyl) propionyl] -6-butyl • "-sulfonamido-1, 2,3,4-tetrahydro-quinoline 7 Hydrochloride Prepared from the compound prepared from ^ Conformance to Example 9 (4) Yield: 76% of theory "Melting point: 122 ° C (decomp) C23H3oN403S x HCl x 0.5 H20 (488.06) Calculated: C 56.60 H 6.60 N 11.48 Found: 56.56 6.60 11.50 ( 5) L- [3- (4-amidino-phenyl) -propionyl] -5- phenylsulfonamido-1, 2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to example 9 (5). Yield: 56% of theory Melting point: from 116 ° C (sinter from 95 ° C C25H26N403S x HCl x H20 (517.05) Calculated: C 58.07 H 5.65 N 10.84 Found: 58.53 5.80 10.94 (6) L- [3- (4-amidino-phenyl) propionyl] -7-phenylsulfonamido-1 hydrochloride, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (6) Yield: 67% of the theory Melting point: from 105 ° C C25H26 403S X HCl X H20 (517.05) "" Calculated: C 58.08 H 5.65 N 10.84 Found: 58.25 5.72 10.44 (7) l- [3- (4-Amidino-phenyl) propionyl] -7-benzylsulfonamido-1,2,3,4-tetrahydro-quinoline hydrochloride. Prepared from the compound prepared according to example 9 (7). ) Yield: 51% of the theory Melting point: from 108 ° C (decomp) C26H28N403S x HCl x 0.5 H20 (522.07) Calculated: C 59.82 H 5.79 N 10.73 Found: 59.66 5.87 10.45 (8) L- [3] Hydrochloride - (4-amidino-phenyl) propionyl] -6- (4-amino-3,5-dichloro-phenylsulfonamido) -1,2,3,4-tetrahydroquinoline Prepared from the compound prepared in accordance with Example 10 Performance: 73% of the theory Melting point: 115 ° C (decomp) C25H25Cl2N5? 3S x HCl (582.44) Calculated: C 51.51 H 4.50 N 12.01 ~ Found: 51.52 4.71 11.94 (9) Hydrochloride l- [ 3- (4-amidino-phenyl) propionyl] -6-propylsulfonamido-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 10 (2) - Yield: 46% of theory Melting point: 123 ° C (decomp) C22H28N403S x HCl (462.05). Calculated: C 56.82 H 6.29 N 12.05 Found: 57.19 6.52 11.77 (10) l- [3- (4-Amidino-phenyl) propionyl] -6- (5-chloro-thien-2-ylsulfonamido) -1,2-hydrochloride , 3,4-tetrahydroquinoline Prepared from the compound prepared according to example 10 (3) Yield: 96% of the theory Melting point: 100 ° C (decomp) C23H23C1N403S2 x HCl x 0.5 H20 (548.51) Calculated : C 50.36 H 4.50 N 10.21 - Found: 50.66. 4.70 10.01 (11) L- [3- (4-amidino-phenyl) propionyl] -6-isopropylsulfonamido-1, 2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to example 10 (4) "" "Yield: 62% of the theory Melting point: 110 ° C (decomp) _C22H28N403S X HCl x 0.5 H20 (472.04) Calculated: C 55.74 H 6.26 N 11.82 Found: 55.62 6.62 11.07 (12) Hydrochloride l- [3- (4-amidino-phenyl) propionyl] -6- (3-chloropropylsulfonamido) -1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared from Conformance to Example 10 (5) Yield: 100% of theory Melting point: 85 ° C (decomp) • C22H2-7C1N403S x HCl x C2H50H (545.53) Calculated: C 52.84 H 6.28 N 10.27 Found: 54.01 6.41 9.98 ( 13) l- [3- (4-Amidino-phenyl) -propionyl] -6-benzylsulfonamido-1,2,3,4-tetrahydro-quinoline hydrochloride Yield: 62% of > the theory Melting point: from 80 ° C C26H28N403S x HCl x H20 (531.08) Calculated: C 58.80 H 5.88 N 10. 55 S 6. 04 Found: 58.75 5.90 10. 61 5. 95 (14) l- [3- (4-Amidino-phenyl) -propionyl] -6-phenylacetylamino-1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to example 9 (9) Yield: 53% of the theory Melting point: from 150 ° C C27H28N402 x HCl x H20 (495.03) Calculated: C 65.51 H 6.31 N 11. 32 Found: 65.58 6.38 11. 13 (15) L- [3- (4-amidino-phenyl) propionyl] -6-benzoylamino-1, 2,3,4-tetrahydro-quinoline Hydrochloride Yield: 75% of theory Melting point: from 170 ° C _ C26H26N402 x HCl x H20 (487.00) Calculated: C 64.93 H 6.08 N 11.65 Found: 65.02 6.22 11.66 (16) L- [3- (4-amidino-f-enyl) propyl] hydrochloride] -6-f-enylsulfonamido-1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 18 Yield: 26% of the theory Melting point: from 140 ° C "C25H28N402S x HCl x H20 (503.07) Calculated: C 59.69 H 6.21 N 11.14 S 6.37 Found: 59.72 6.08 10.97 6.38 (17) l- [3- (4-Amidino-phenyl) thiopropionyl] -6-f-enylsulfonamido-1, 2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to example 19. : 14% of the theory Melting point: from 140 ° C (decomposed) C25H26N..O2S2 x HCl x H20 (533.12) Calculated: C 56.33 H 5.48 N 10.51 S 12.03 Cl 6.65 Found: 56.45 5.52 10.28 11.87 6.93 (18) l- [3- (4-Amidino-phenyl) -propionyl] -5-f-enylsulfonamido-2,3-dihydro-indole hydrochloride Prepared from the compound prepared from conformance to example 10 (6) Melting point: from 128 ° C (decomposed) C24H24N03S x HCl x 1.5 H20"(512.01) Calculated: C 56.14 H 5.31 N 10.96 Found: 56.30 5.51 10.96 (19) Hydrochloride l- [3- (4-amidino-phenyl) propionyl] -7- phenylsulfonamido-2,3,4,5-tetrahydro-lH-benzo [b] azepine Prepared from the compound prepared according to example 10 (7) Melting: from 207 ° C (decomp.) C26H28N03S x HCl x C2H5OH (559.07) -Calculated: C 60.16 H 6.31 N 10.02 Found: 60.44 6.42 9.41 (20) L- [3- (4-amidino-phenyl) hydrochloride propionyl] -3-methyl-6-phenylsulfonamido-I, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 10 (8) Yield: 55% of theory - Melting point: from 140 ° C C26H28N403S x HCl (513.07) Calculated: C 60.86 H 5.70 N 10.92 Found: 61.09"6.05 10.21 (21) l- [3- (4-Amidino-phenyl) -propionyl] -4-methyl-6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared from conformance to example 10 (9) Yield: 68% of theory Melting point: from 133 ° C (decomposed) C26H28N403S x HCl (513.07) Calculated: C 60.86 H 5.70 N 10.92 Found: 59.82 5.79 20.73 (22) Hydrochloride of l- [3- (4-amidino-phenyl) -propionyl] -2-methyl-6-phenylsulfonamido-1,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (14) Yield: 37% of the theory Melting point: from 112 ° C (decomposed) C26H29C1N403S x HCl x 2 H20 (549.07) Calculated: C 56.87 H 6.06 N 10.02 Found: 56.43 5.98 9.90 (23) I- [3] Hydrochloride - (4-amidino-phenyl) propionyl] -6 - [(5-dimethylamino-naphthi-1-yl) -sulfonamido] -l, 2,3,4-tetrahydroquinoline Prepared from the compound prepared in accordance with example 10 (1) Yield: 52% of the theory C31H33N5O3S x 1.25 HCl (601.03) Calculated: C 61.98. H 5.87 N 11.65 Found: 61.64 6.43 10.38 (24) 1- [N- (4-amidino-benzyl) -aminocarbonyl] - hydrochloride 6-phenylsulfonylamino-1,2,3,4-tetrahydro-quinoline Yield: 64% of theory C24H25N503S (463.57) Mass spectrum: FAB-MS: (M + H) + = 464 (25) Hydrochloride l- [ 3- (4-amidino-phenyl) propyl] -6- phenylsulfonamido-dihydrocarbostyril Melting point: from 136 ° C C25H26 403S x HCl x 2 H20 (535.07) Calculated: C 56.22 H 5.85 N 10.49 Found: 55.15 5.58 10.58 (26 L- [3- (4-amidino-phenyl) -propionyl] -6- (3-trifluoromethyl-benzenesulfonylamino) -1,2,3,4-tetrahydroquinoline-hydrochloride Prepared from the compound prepared in accordance with Example 10 (10) Yield: 72% of the theory Melting point: 146-147 ° C C26H25F3 403S X HCl x C2H50H (613.14) Calculated: C 54.85 H 5.26 N 9.14 Cl 5.78 Found: 54.71 5.23 9.10 6.00 (27) L- [3- (4-amidino-phenyl) propionyl] -6- (2,5-dichlorobenzenesulfonylamino) -1,2,3,4-tetrahydroquinoline-hydrochloride Prepared from the compound prepared from according to example 10 (11) Yield: 77% of the theory Melting point: 239 ° C C25H24C12N403S x HCl (567.93) Calculated: C 52.67 H 4.44 N 9.87 Found: 50.33 4.86 10.39 (28) L- [3- (4-amidino-phenyl) hydrochloride propionyl] -6- (2,3,5,6-tetramethylbenzenesulfonylamino) -1,2,3,4-tetrahydroquinoline _ Prepared from the compound prepared according to example 10 (12) Yield: 12% of the theory Melting point: 224-225 ° C - "Rf value: 0.28 (silica gel; methylene chloride / ethanol = 4: 1) (29) L- [3- (4-amidino-phenyl) hydrochloride propionyl] -6- (5-isoquinolinylsulfonylamino) -1,2,3,4-tetrahydroquinoline Prepared from the compound prepared according to example 10 (14) Yield: 66% of the theory Melting point: 195 ° C C28H27N503S x HCl x H20 (568.1) - Calculated: C 58.45 H 5.24 N 12.17 Found: 57.49 5.64 11.97 (30) L- [3- (4-amidino-phenyl) propionyl] -6- hydrochloride (cyclopropylsulfonylamino) -1,2, 3,4-tetrahydroquinoline Prepared from the compound prepared according to example 10 (15) Yield: 87% of the theory Melting point: from 85 ° C C22H26N403S x HCl (463.0) Calculated : C 57.07 H 5.88 N 12.10 - Found: 56.35 6.55 11.33 (31) l- [3- (4-Amidino-phenyl) propionyl] -6- (benzimidazol-5-ylsulfonylamino) -1,2,3,4-hydrochloride -tetrahydroquinoline Prepared from the compound prepared according to example 10 (16) Yield: 66% of the theory Melting point: from 220 ° C C26H26N603S x HCl x H20 (557.08) Calculated: C 56.06 H 5.25 N 15.09 Found: 55.76 5.37 14.74 (32) l- [3- (3-Amidino-phenyl) propionyl] -6-phenylsulfonylamino-1, 2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared in accordance with Example 9 (24) Yield: 17% of the theory Melting point: from 134-139 ° C C2sH26N403S x HCl x H20 (517.05) Calculated: C 58.08 H 5.65 N 10.84 Found: 57.52 5.83 10.04 (33) L - [(4-amidino-phenyloxy) acetyl] -6-phenylsulfonylamino-1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from compound prepared according to example 9 (25) Yield: 44% of theory Melting point: 137-143 ° C C24H24N40S x HCl x H20 (519.02) Calculated: C 55.54 H 5.24 N 10.79 Found: 54.57 5.31 10.50 (34 ) L- [2- ((4-Amidino-phenyl) -methyl-amino) -acetyl] -6-phenylsulfonylamino-l hydrochloride, 2, 3, 4-tetrahydroquinoline Prepared from the compound prepared according to example 9 (26) "Yield: 77% of the theory Melting point: sinter from 180 ° C" C25H27N503S x HCl x H20 (532.07) Calculated: C 56.44 H 5.68 N 13.16 S 6.03 Found: 55.71 5.53 13.03 5.87 (35) l- [3- (4-Amidino-phenyl) -propionyl] -6- (cyclohexylsulfonylamino) -1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to Example 10 ( 17) Yield: 62% of the theory Melting point: decomposition from 125 ° C C25H32N03S x HCl x H20 (523.10) Calculated: C 57.40 H 6.74 N 10.71 S 6.13 Found: 57.22 6.56 10.58 6.07 (36) L- [3- (4-amidino-phenyl) propionyl] -6- (3-tolylsulfonylamino) -1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared in accordance with example 10 (18) Yield: 69% of the theory Melting point: from 260 ° C C26H28N403S X HCl x H20 (531.08) Calculated: C 58.80 H 5.88 N 10.54 Found: 58.97 5.84 10.40 (37) Hydrochloride l- [3- (4-amidino-phenyl) propionyl] -6- (4-methoxybenzenesulfonylamino) -1,2,3,4-tetrahydroquinoline Prepared from the compound prepared according to example 10 (19) Yield: 80% of theory ^ C26H28N404S x HCl x H20 (547.08) Calculated: C 57.08 H 5.71 N 10.24 Found: 56.89 6.19 9.27 ; 38) L- [3- (4-amidino-phenyl) propionyl] -6- (3-) hydrochloride aminocarbonylbenzenesulfonylamino) -1,2,3,4-tetrahydroquinoline-Yield: 32% of the theory C26H27N504S x HCl x H20 (560.08) Calculated: C 55.76 H 5.40 N 12.50 Found: 54.15 5.74 10.75 (39) Hydrochloride of l- [3- (4-amidino-phenyl) propionyl] -6- (N-benzoyl-methylamino) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example_ 11 (2) Yield : 65% of theory Melting point: 90-92 ° C C27H28N02 x HCl x 2H20 (512.03) Calculated: C 63.34 H 6.30 N 10.94 Found: 63.21 6.48 10.92 (40) L- [3- (4-amidinohydrochloride phenyl) propionyl] -6- [N- (4-chlorobenzoyl) -methylamino] -!, 2,3,4-tetrahydroquinoline Prepared from the compound prepared according to example 11 (3) Yield: 76% of the theory C2H27N402C1 x HCl x H20 (529.47) Calculated: C 61.24 H 5.71 N 10.58 _. Found: 61.70 5.88 10.37 (41) L- [3- (4-amidino-phenyl) propionyl] -6- [N-] hydrochloride - (1-naphthoyl) -methylamino] -l, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 11 (4) Yield: 71% of theory C3? H30N402 x HCl x 1.5 H20 (554.09) Calculated: C 67.19 H 6.18 N 10.11 Found: 67.22 6.12 10.19 (42) L- [3- (4-amidino-phenyl) propionyl] -6- [N- (2-naphthoyl) -methylamino] hydrochloride] -1, 2,3, 4-tetrahydro-quinoline Prepared from the compound prepared from - conformance to example 11 (5) Yield: 72% of the theory C3iH3oN402 x HCl x H20 (545.09) Calculated: C 68.30 H 6.10 N 10.27 Found: 68.03 6.28 10.27 (43) l- [3- (4- Hydrochloride amidino-phenyl) propionyl] -6- (N-butyryl-methylamino) -1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared from -conformity with example 11 (6) Performance: 59% of theory C2H30N4O2 x HCl x H20 (461 01) "Calculated: C 62.52 H 7.21 N 12.15 -'Found: 62.66 7.28 11.84 [44) L- [3- (4-amidino-nitro-phenyl) propionyl] hydrochloride] - 6-phenyl-sulfonylamino-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (28) Yield: 35% of the theory Rf Value: 0.44 (silica gel; methylene / methanol = 4: 1)) (45) l- [3- (4-Amidino-amino-phenyl) propionyl] -6-phenyl-sulfonylamino-1,2,3,4-tetrahydro-quinoline Hydrochloride Yield: 53% of theory C25H2N503 x 2 HCl (514.65) Calculated: C 54.49 H 5.30 N 12.70 Found: 54.60 75.61 12.47 (46) L- [3- (4-amidino-acetylamino-phenyl) -propionyl] -6- hydrochloride phenyl-sulfonylamino-1,2,3,4-tetrahydroquinoline Prepared from the compound prepared according to example 11 (7) Yield: 59% of theory C2 H29N504S x HCl (556.08) Calculated: C 53.32 H 5.44 S 5.76 Found: 52.93 5.87 5.50 (47) l- [3- (4-Amidino-2- (2-ethoxycarbonyl-ethylcarbonylamino) -phenyl) -propionyl] -6-phenyl-sulfonyl-amino-1,2-hydrochloride 3, 4-tetrahydro-quinoline Prepared from the prep compound plow of according to example 11 (8). Yield: 35% of theory C3? H35N3506S x HCl (642.18) "Calculated: C 57.98 H 5.49 N 10.90 Found: 55.39 5.91 10.43 (48) 1- (4-Amidino-benzoyl) -6-phenylsulfonyl-amino- 1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (29) Yield: 62% of theory C23H22N403S x HCl x H20 (489.00) Calculated: C 56.49 H 5.15 N 11.46 Found: 55.80 5.04 11.15 (49) L- [3- (4-amidino-3-fluorophenyl) propionyl] -6-phenylsulfonylamino-1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared in accordance with with example 9 (31) Yield: 55% of theory C25H25FN403S x HCl (517.03) ~ Calculated: C 58.08 H 5.07 N 10.84 'Found: 57.63 5.18 10.75 (50) l- [3- (2-amidino- pyridin-5-yl) ropionyl] -6-phenylsulfonylamino) -1,2, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (32) Yield: 68% of theory C24H25N503S x HCl x H20 (518.04) Calculated: C 55.65 H 5.45 N 13.52 - Found: 55.23 5.54 12.75 (51) _ L- [3- (4-amidino-phenyl) -acroyl] - hydrochloride 6- f-enylsulfonylamine-1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (33) Yield: 18% of theory C25H24N403S x HCl x H20 (515.04) Calculated: C 58.30 H 5.28 N 10.88 S 6.23 Found: 56.82 5.29 10.84 6.29 (52) L- [3- (4-amidino-phenyl) propionyl] -6-piperidinocarbonyl-1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to example 9 (34) Yield: 65% of the theory _C25H3oN402 x HCl x 1.5 H20 (481 99) Calculated: C 62.29 H 7.11 N 11.62 Found: 61.78 6.94 11.40 (53) L- [3- (4-amidino-phenyl) propionyl] - hydrochloride 6- benzylaminocarbonyl-1, 2, 3, 4-tetrahydro-quinoline Yield: 3% of the theory C27H28N402 (440 55) Mass spectrum: (M + H) 442 (54) L- [3- (4-amidino-phenyl) propionyl] -6- (N- • methyl-phenyl-aminocarbonyl) -1,2, 3,4-tetrahydroquinoline hydrochloride Prepared from the compound prepared according to example 9 (36) Yield: 5% of the theory C27H28N402 x HCl x H20 (494 99) Calculated: C 65.51 H 6.31 N 11.32 Found: 65.60 6.26 11.23 (55) L- [3- (4) Hydrochloride -amidino-phenyl) propionyl] -6- diethylamino-carbonyl-1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (37) _ Yield: 7% of theory C24H30N402 x HCl x 2.5 H20 ("487 98) Calculated: C 59.07 H 7.44 N 11.48 Found: 59.05 7.06 11.12 (56) L- [3- (4-amidino-phenyl) propionyl] -6- (3, 5-) hydrochloride. dimethyl-piperidinocarbonyl) -1,2,3,4-tetrahydroquinoline Prepared from the compound prepared according to example 9 (38) * Yield: 7% of theory C2H34N402 x HCl x 2 H20 (519 04) Calculated : C 61.41 H 7.63 N 10.61 Found: 60.76 7.36 10.35 (57) L- [3- (4-amidino-phenyl) propionyl] -6- (N-phenylbutylamino-carbonyl) -1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to example 12 Yield: 15% of the theory C30H34N4O2 x HCl x H20 (537 07) Calculated: C 67.08 H 6.94 N 10.43 Found: 67.07 6.85 10.23 (58) I- [3] Hydrochloride - (4-amidino-phenyl) propionyl] -6- [N- (4-chlorophenyl) -methylaminocarbonyl] -l, 2,3,4-tetrahydro-quinoline _ Prepared from the compound prepared according to example 12 ( 1) Yield: 33% of theory C27H27N402 x HCl x H20 (529 43) Calculated: C 61.25 H 5.71 10.58 Found: 60.74 5.70 10.24 (59) L- [3- (4-amidino-phenyl) propionyl] - hydrochloride 6- (N-phenylethylaminocarbonyl) -1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 12 (2) Yield: 64% of theory C28H30N 02 x HCl x H20 (509. 02) Calculated: C 66. 06 H 6. 53 N 11. 01 Found: 66.55 6.49 10.82 (60) L- [3- (4-amidino-phenyl) -propionyl] -6-diphenylamino-carbonyl-1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared in accordance with with example 12 (3) Yield: 41% of the theory C32H30N4O2 x 2 HCl x 2 H20 (611.57) Calculated: C 62.85 H 5.94 N 9.17 Found: 61.57 5.99 8.61 (61) l- [3- (4- Hydrochloride amidino-phenyl) propionyl] -6- (N-phenylbenzylaminocarbonyl) -1,2,3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 12 (4) Yield: 33% of the theory Melting point: Decomposition from 130 ° C (62) l- [3- (4-Amidino-phenyl) propionyl] -6- (N-ethoxycarbonyl-methyl-phenylaminocarbonyl) -1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared from conformance to example 12 (5) Yield: 64% of the theory C30H32N4O2 x HCl (549.05) Calculated: C 65.62 H 6.06 N 10.20 Found: 66.23 6.29 10.12 (63) L- [3- (4-amidino-phenyl) hydrochloride ) propionyl] -6- (N- cyclohexyl-methylaminocarbonyl) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 12 (6) Yield: 30% of theory C2H3N402 x HCl x 0.5 H20 (492.04) Calculated : C 65.90 H 7.38 N 11.39 Found: 65.88 7.41 11.14 (64) L- [3- (4-amidino-phenyl) propionyl] -6- (4-methyl-piperidinocarbonyl) -1,2,3,4-hydrochloride tetrahydroquinoline Prepared from the compound prepared according to example 9 (22) Yield: 38% of theory C2H32N4? 2 x HCl x 2.5 H20 (514.02) Calculated: C 60.75 H 7.45 N 10.90 Found: 60.51 7.14 10.70 (65) L- [3- (4-amidino-phenyl) -propionyl] -6-morpholinocarbonyl) -1, 2, 3, 4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to example 9 (23) - Yield : 70% of theory C24H28N403 x HCl x 2.5 H20 (501.96) Calculated: C 57.42 H 6.83 N 11.16 Found: 57.86 6.63 10.73 (66) L- [3- (4-amidino-phenyl) propionyl] -6- hydrochloride (N- ethoxycarbonyl-cyclohexylaminocarbonyl) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 12 (7) Yield: 77% of theory C3oH38N404 x HCl x 0.5 H20 (564.10) Calculated: C 63.87 H 7.15 N 9.93 Found: 63.43 _7.18 9.43 (67) l- [3- (4-Amidino-phenyl) propionyl] -6- (2-ethoxycarbonyl-pyrrolidinocarbonyl) -1,2,3, 4- hydrochloride tetrahydroquinoline Prepared from the compound prepared according to example 12 (8) Yield: 61% of the theory C2H32N404 x HCl x H20 (531.02) C: calculated: C 61.06 H 6.64 N 10.55 Found: 60.50 6.57 10.50 (68) L- [3- (4-amidino-phenyl) propionyl] -6- (2-ethoxycarbonyl-piperidinocarbonyl) -1,2,3,4-tetrahydroquinoline hydrochloride Prepared from the compound prepared according to example 12 (9) Yield: 63% of theory C28H34N404 x HCl x H20 (545.05) Calculated: C 61.69 H 6.84 N 10.28 Found: 61.45 6.67 9.96 (69) l- [3- (4-Amidino-phenyl) -propionyl] -6- (3-ethoxycarbonyl-piperidinocarbonyl) -1,2,3,4-tetrahydro-quinoline _ Hydrochloride Prepared from of the compound prepared according to example 12 (10) Yield: 70% of theory C28H3N404 x HCl x H20 (545705) Calculated: C 61.69 H 6.84 N 10.28 Found: 61.69 6.82 10.21 (70) l- [3- Hydrochloride (4-amidino-phenyl) propionyl] -6- [N- (2-acetylaminoethyl) -phenylaminocarbonyl] -! 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 12 (11) Yield: 22% of theory C30H33N5O3 x HCl x 1.5 H20 (575.1) "Calculated: C 62.61 H 6.44 12.18 Found: 62.76 -6.35 12.04 (71) L- [3- (4-amidino-phenyl) propionyl] - hydrochloride 6- [N- (2-aminoethyl) -phenylaminocarbonyl] -l, 2, 3, 4-tetrahydroquinoline Prepared from the compound prepared according to example 13 Yield: 36% of theory Mass spectrum: FAB-MS: (M + H) + = 470 (72) _ l- [3- (4-Amidino-phenyl) propionyl] -6-benzylamino-1,2,3,4-tetrahydrochloride quinoline Prepared from the compound prepared according to example 14 Yield: 66% of the theory C26H28N40 x HCl x 1.5 H20 (476.04) Calculated: C 65.60 H 6.77 11.77 Found: 65.17 6.81 11.36 (73) Hydrochloride l- [3 - (4-amidino-phenyl) propionyl] -6- • _ (naphth-1-yl-methylamino) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 14 (1 ) Yield: 45% of the theory 'c3oH30N40 x HCl x 2 H20 (535.1) Calculated: C 67.33 H 6.59 N 10.47 Found: 66.07 6.85 9.42 (74) L- [3- (4-amidino-phenyl) propionyl] hydrochloride] -6- (naphthalin-2-yl-methyl-amino) -1, 2,3,4-tetrahydroquinoline Prepared from the compound prepared according to example 14 (2) Yield: 72% of theory C30H30N4O x HCl x 2 H20 (535.1) Calculated: C 67.33 H 6.59 N 10.47 Found: 66.21 6.64 10.05 (75) L- [3- (4-amidino-phenyl) propionyl] -6- (N-methyl-benzyl-amino) -1,2,3,4-tetrahydro-quinoline hydrochloride Prepared to from the compound prepared according to example 14 (3) Yield: 59% of the theory C27H30N4O x HCl x H20 (481.06) Calculated: C 67.41 H 6.91 N 11.64 Found: 67.44 - 7.03 11.28 (76) Hydrochloride l- [ 3- (4-amidino-phenyl) propionyl] -6- (N-ethoxycarbonyl-methylbenzylamino) -1,2,4,4-tetrahydroquinoline Prepared from the compound prepared according to example 6 (1) Yield: 52% of theory C30H34N4O3 x HCl x H20 (553.13) Calculated: C 64.10 H 6.81 N 9.96 Found: 64.17 6.76 10.04 (77) L- [3- (4-amidino-phenyl) propionyl] -6- [N] hydrochloride - (ethoxycarbonylmethyl) -N- (naphth-2-yl-methyl) -amino] -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 6 (2) Yield: 84% of the theory C34H36N403 x HCl x 1.5 H20 (612.19) Calculated: C 66.70 H 6.58 9.15 Found: 66.81 6.40 9.46 (78) L- [3- (4-amidino-phenyl) propionyl] -6- [N- (ethoxycarbonylmethyl) -N- (naft-1-yl- methyl) -amino] - 1, 2, 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 6 (3) Yield: 69% of the theory C34H36N403 x HCl x 1.5 H20 (612.19) Calculated: C 66.70 H 6.58 9.15 Found: 66.83 6.44 9.14 (79) L- [3- (4-amidino-phenyl) propionyl] -6- (N-acetyl-N-benzylamino) -1,2,3, 4- hydrochloride tetrahydroquinoline Prepared from the compound prepared according to example 11 (9) Yield: 46% of the theory C28H30N4O2 x HCl x 2 H20 (527.07) Calculated: C 63.80 H 6.69 N 10.63 Found: 63.69 6.86 10.21 (80) L- [3- (4-amidino-phenyl) propionyl] -6- (N-pentanoyl-N-benzylamino) -1, 2, 3, 4-tetrahydro-quinoline hydrochloride Yield: 63% of theory Prepared from the compound prepared according to example 11 (10) C3? H36N402 X HCl X H20 (551.15) - Calculated: C 67.55 H 7.13 N 10.16 Found: 66.99 7.30 10.08 (81) L- [3- (4-amidino-phenyl) -propionyl] -6- [N- (2-ethoxycarbonylethylcarbonyl) -benzylamino] -! , 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 11 (11) - Yield: 66% of theory C32H36N404 x HCl x 0.5 H20 (586.16) "Calculated: C 65.57 H 6.53 9.55 I Found: 65.07 6.34 9.79 (82) L- [3- (4-amidino-phenyl) propionyl] -6- (N-methanesulfonylbenzylamino) -1,2,3, 4-tetrahydro-chiholine hydrochloride Prepared from the compound prepared according to example 10 (22) Yield: 60% of the theory C2.H30N4O3 x HCl (527.12) "Calculated: C 61.52 H 5.92 10.62 Found: 61.18 6.26 10.45 (83) L- [3- (4-Hydrochloride -amidino-phenyl) propionyl] -6- [N- (ethylaminocarbonylmethyl) -benzylamino] -!, 2,3,4-tetrahydro-quinoline - Prepared from the compound. prepared in accordance with example 14.

Yield: 57% of theory C3oH35N5? 2 x HCl x 2 H20 (570.14) Calculated: C 63.20 H 7.00 N 12.28 Found: 63.06 7.00 11.61 (84) L- [3- (4-amidino-phenyl) -propionyl hydrochloride ] -6- [N- (N, N-dipropylaminocarbonylmethyl) -benzylamino] -l, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 14 (1) Yield: 62% of theory C34H3N502 x HCl x H20 (608.25) Calculated: C 67.14 H 7.62 N 11.51 Found: 67.72 7.67 11.17 (85) L- [3- (4-amidino-phenyl) -propionyl] -6- [N- (benzylaminocarbonylmethyl) hydrochloride] -benzylamino] - !, 2, 3, 4- tetrahydro-quinoline Prepared from the compound prepared according to the example 15 (2) Yield: 50% of the theory C35H37N502 x HCl x 2 H20 (632.21) Calculated: C 66.49 H 6.69 N 11.07 Found: 66.65"6.78 10.56 (86r 1- [3- (4-amidino-phenyl) -propionyl] -6- [N- (phenylaminocarbonylmethyl) -benzylamino] -l, 2,3,4- hydrochloride tetrahydroquinoline Prepared from the compound prepared according to example 15 (3) Yield: 78% of theory C3H35N502 x HCl x H20 (600.19) Calculated: C 68.04 H 6.38 N 11.66 Found: 67.92 6.58 11.37 (87) Hydrochloride l- [ 3- (4-amidino-phenyl) -propionyl] -6-phenyl-aminosulfonyl-1, 2,3, 4-tetrahydroquinoline Prepared from the compound prepared according to example 16b) - Yield: 21% of theory C25H26N03S x HCl x H20 (553.51) Calculated: C 54.25 H 5.46 N 10.12 Found: 54.52 5.54 10.16 (88) l- [3- (4-Amidino-phenyl) -propionyl] -6-benzyl-aminosulfonyl-1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to example 16 (1) Yield: 28% of theory C26H28N403S x HCl x 2 H20 (549.09) Calculated: C 56.87 H 6.06 N 10.20 - Found: 57.40 5.74 9.94 (89) L- [3- (4-amidino-phenyl) hydrochloride -propionyl] -6- p-phenylsulfonyl-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared in accordance - Example 16 (2) Yield: 48% of the theory 'C25H25N303S x HCl x H20 (502.01) Calculated: C 59.81 H 5.62 N 8.37 Found: 59.94 5.59 8.26 (90) L- [3- (4-amidinohydrochloride -phenyl) -propionyl] -6- benzoyl-1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 16 (3) Yield: 56% of the theory ~ C26H25N302 x HCl x 1.5 H20 (474.95) Calculated: C 65.75 H 6.15 N 8.85 Found: 66.12 5.93 9.05 (91) L- [3- (4-amidino-phenyl) -propionyl] -6- (2,2-diphenyl-ethyl-amino] hydrochloride ) -1,2,3, 4-tetrahydro-quinoline Prepared from the compound prepared according to Example 14 (4) Yield: 82% of theory C33H34N40 x HCl x 2 H20 (575.16) Calculated: C 68.91 H 6.81 N 9.74 Found: 67.62 6.82 9.26 (92) Hydrochloride of l- [3- (4-amidino-phenyl) -propionyl] -6- (N-ethoxycarbonylmethyl-2, 2-diphenylethylamino) -1, 2, 3, 4- "tetrahydro-quinoline Prepared from the compound prepared in accordance to Example 6 (4) Yield: 84% of theory _C37H40N4O3 x HCl x H20 (643.25) Calculated: C 68.62 H 6.73 N 8.71 Found: 69.13 6.75 8.83 (93) L- [3- (4-amidino-phenyl) hydrochloride ) -propionyl] -6- (2-oxo-pyrrolidino) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 11 (12) 'Yield: 59% of theory C23H26N402 x HCl x 1.5 H20 (453.98) Calculated: C 60.84 H 6.66 N 12.34 Found: 60.86 6.88 11.45 (94) L- [3- (4-amidino-phenyl) -propionyl] -6- (2-oxo-piperidino) hydrochloride -1,2,3, 4-tetrahydro-quinoline Prepared from the compound prepared according to "Example 11 (13) - Yield: 59% of theory C24H28 02 x HCl x 1.5 H20 (468.01) Calculated: 'C 61.59 H 6.90 N 11.97 Found: 61.78 7.02 11.46 (95) 1- [N- (4-amidino-phenyl) -methylaminocarbonyl] -6-phenylsulfonylamino-l, 2,3,4-tetrahydro-quinoline Hydrochloride Prepared from the compound prepared according to to Example 17 Yield: 59% of theory C25H27N503S (477.60) Mass spectrum: FAB-MS: (M + H) + = 478 Example 25 l- [3- (4-Amidino-phenyl) -propionyl] - hydrochloride 6- [(3-methoxycarbonylpropyl) -naphth-1-yl-sulfonylamino] -1,2,3,4-tetrahydro-quinoline 0.89 g of l- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] -6- [N- (3-methoxycarbonylpropyl) -naphth-1-yl-sulfonyl-amino] -l, 2,3,4-tetrahydro-quinoline (see example 7 (3)) are dissolved in 30 ml of methanol and 1.1 ml of 1N hydrochloric acid, and hydrogenated on palladium / carbon at room temperature for 3 hours with 3 bar of hydrogen. The catalyst is then removed by filtration, the solution is concentrated by evaporation and the residue is column chromatographed on silica gel with methylene chloride / methanol (8.5: 1.5). The main fraction is concentrated by rotary evaporation and the material obtained is dried. Yield: 0.39 g (53% of theory) C34H36N405S x HCl x H20 (667.23) Calculated: C 61.21 H 5.89 N 8.40 Found: 61.50 5.98 8.52 The following are prepared in an analogous way: (1) L- [3- (4-amidino-phenyl) -propionyl] -6- [N- (1-ethoxycarbonylethyl) -napht-1- i 1-sulfonylamino] -1,2,3-hydrochloride 4-tetrahydroquinoline Yield: 63% of the theory C34H36N405S x HCl x H20 (667.23) Calculated: C 61.21 H 5.89 N 8.40 ^. Found: 60.46"5.71 8.18 (2) L- [3- (4-amidinohydrochloride -phenyl) -propionyl] -6- [N- (naphth-1-yl-sulfonyl) -met i-lamino] -1,3,3,4-tetrahydroquinoline Yield: 70% of theory C3oH3oN03S x HCl x 1.5 H20 (590.15) Calculated: C 61.06 H 5.81 N 9.49 Found: 60.73 5.74 9.51 (3) L- [3- (4-amidino-phenyl) -propionyl] - 6- [N- (naft-1-yl- sulfonyl) -benzylamino] -l, 2,3,4-tetrahydroquinoline Yield: 81% of theory C36H34N403S x HCl x 1.5 H20 (666.25) Calculated: C 64.90 H 5.75 N 8.41 Found: 65.09 5.78 8.44 (4) Hydrochloride from l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (naphth-1-yl-sulfonyl) -N- (2-morpholinoethyl) -amino] -1,2,3,4 -tetrahydro-quinoline Prepared from l- [3- (4-benzyloxycarbonyl- amidino-phenyl) -propionyl] -6- [N- (naphth-1-yl-sulfonyl) -N- (2-morpholinoethyl) -amino] -l, 2, 3, 4-tetrahydro-quinoline Yield: 40% theory C35H37N505S x HCl x 2.5 H20 (721.28) "Calculated: C 58.28 H 6.01 N 9.71 - Found: 58.21 _ 5.88 9.48 (5). l- [3- (4-amidino-phenyl) -propionyl] -6 hydrochloride - [N- (naphth-1-ylsulfonyl) -N- (ethoxycarbonylmethyl) -amino] -1,2,3,4-tetrahydro-quinoline Yield: 70% of theory C33H34N405S X HCl x H20 (653.20) Calculated : C 60.68 H 5.71 N 8.58-Found: 60.01 5.69 8.54 (6) l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (naphth-1-ylsulfonyl) -N, N - (di (methoxycarbonylmethyl-aminocarbonylmethyl) -amino] -l, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 7 (8) Yield: 67% of the theory _ C3H39N508S X HCl X H20 (768.29) - Calculated: C 57.84 H 5.51 N 9.12 Found: 57.49 5.52 9.07 Example 26 L- [3- (4-amidino-phenyl) -propionyl] -6- (2,4,6-trimethyl-) hydroiodide benzenesulfonylamino) - 1,2,3,4- tetrahydroquinoline 1.32 g (2.7 mmol) of l- [3- (4-cyano-phenyl) -propionyl] -6- (2,4,6-trimethyl-benzenesulfonylamino) -1,2,3,4-tetrahydro- quinoline (see example 10 (13) are dissolved in 20 ml of pyridine and combined with 2 ml of triethylamine, then 3.6 g of hydrogen sulphide is pipetted at the time of cooling with ice, and the solution is The mixture is stirred overnight, nitrogen is then blown through the solution for 2 hours and the solution is concentrated by evaporation, the residue is taken up in 3 ml of concentrated hydrochloric acid and extracted 3 times with ethyl acetate. The organic is dried and concentrated by rotary evaporation.The crude thioamide derivative is dissolved in 50 ml of acetone and stirred for 2.5 hours with 8 ml of methyl iodide at 45 ° C, and finally it is concentrated by rotary evaporation. The residue is then dissolved in 50 ml of methanol or ethanol, combined with 3 g of ammonium acetate and stirred for 6 hours at 45 ° C and then concentrated by evaporation. The amidine formed is purified in a column on silica gel. Yield: 46% of theory Melting point: starting at 124 ° C C28H32N403S X Hl (632.57) Calculated: C 53.17 H 5.26 N 8.86 Found: 51.05 5.44 8.57 The following are prepared analogously: (1) L- [3- (4-amidino-phenyl) -propionyl] -6- [N- (quinoline-8-sulfonyl) -N-Jetoxycarbonylmethyl hydroiodide] ) -amino] - 1, 2, 3, 4-tetrahydro-quinoline Prepared from l- [3- (4-cyano-phenyl) -propionyl] -6- [N- (quinolino-8-sulfonyl) -N - (ethoxycarbonylmethyl) -amino] -1,2,3,4-tetrahydro-quinoline (see example 10 (20)). Yield: 48% of theory C32H33JN505S x Hl x 0.5 H20 (736.63) Calculated: C 52.18 ñ_ 4.79 N 9.51 Found: 52.13 4.90 9.39 (2) L- [3- (4-amidino-phenyl) -propionyl] - hydroiodide 6- [N- (isoquinoline-5-sulfonyl) -N- (ethoxycarbonylmethyl) -amino] -l, 2,3,4-tetrahydroquinoline Prepared from l- [3- (4-cyano-phenyl) - propionyl] -6- [N- (isoquinoline-5-sulfonyl) -N- (ethoxycarbonylmethyl) -amino] -l, 2, 3, 4-tetrahydro-quinoline (see example 7). Yield: 17% of theory C32H33N505S x Hl x H20 (745.63) -Calculated: C 51.55 H 4.87 N 9.39 Found: 51.30 4.96 8.87 (3) L- [3- (4-amidino-phenyl) -propionyl] - hydroiodide 6- [N- (phenyl ethanesulfonyl) -N- (ethoxycarbonylmethyl) -amino] -1,2,3,4-tetrahydroquinoline Prepared from l- [3- (4-cyano-phenyl) -propionyl] -6- [ N- (quinoline-8-sulfonyl-N- (ethoxycarbonylmethyl) -amino] -l, 2, 3, 4-tetrahydro-quinoline (see example) (24)). Yield: 57% of theory C30H34N405S x Hl x 0.5 H20 (699.61) Calculated: C 51.50 H 5.19 N 8.01 Found: 51.52 5.27 7.79 (4) L- [3- (4-amidino-phenyl) -propionyl] - hydroiodide 6- [N- (n-butyl-sulfonyl) -N- (ethoxycarbonylmethyl) -amino] -1,2,3,4-tetrahydro-quinoline Prepared from the compound according to example 7 (1) Yield: 56 % of theory, C2H36N405S x Hl (656.59) Calculated: C 49.39 H 5.68 N 8.53 Found: 48.88 5.77 8.38 (5) L- [3- (4-amidino-phenyl) -pro-ionyl] -6- [ N- (1-naphthylsulfonyl) -ethoxycarbonylmethylamino] -l, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (27). Performance: 48% of the theory "-C32H3N406S x Hl (728 59) - Calculated: C 52.75 H 4.56 N 7.69 Found: 52.33 4.79 '7.52 (6) L- [3- (4-amidino-phenyl) -propionyl] -6- (N-) hydroiodide benzoyl-ethoxy-carbonylmethylamino) -1,2,3,4-tetrahydro- "quinoline z. Prepared from the compound prepared according to example 11. Yield: 35% of the theory Melting point: 130 ° C with decomposition C30H32N4O x Hl x H20 (658.54) Calculated: C 54.72 H 5.36 N 8.51 Found: 55.04 5.45 8.41 (7) L- [3- (4-amidino-phenyl) -propionyl] -6- [N (l-naphtho-1-yl) -ethoxy-carbonylmethylamino] -l, 2,3,4-tetrahydroxy-hydroiodide quinoline Prepared from the compound prepared according to example 11 (1). Yield: 60% of the theory C34H34N404 x Hl x H20 (708.60). Calculated: C 57.63 H 5.26 Ñ 17.81 Found: 57.59"5.33 18.87 (8) L- [3- (4-amidino-phenyl) -propionyl] hydroiodide] -6- [N (2- naphthyl-sulfonyl) -ethoxycarbonylmethylamino] -l, 2,3,4- ~ tetrahydro-quinoline Prepared from the compound prepared according to example 10 (21). Yield: 51% of the theory Melting point: decomposition from 120 ° C C33H34N405S x Hl (726.64) Calculated: C 54.55 H 4.86 N 7.71 Found: 53.63 4.97 7.63 (9) l- [3- (4- amidino-3-methyl-phenyl) -propionyl] -6-phenylsulfonylamino-1,2,4,4-tetrahydroquinoline Prepared from the compound prepared according to example 9 (30). Yield: 10% of the theory Rf Value: 0.48 (silica gel; methylene chloride / ethanol = 9: 1) Example 27 l- [3- [4- (N-methoxycarbonyl-amidino) -phenyl] -propionyl] - 6- phenylsulfonamido-1,2,3,4-tetrahydro-quinoline 630 mg of l- [3- (4-amidino-phenyl) -propionyl] -6-phenylsulfonamido-1,2,3,4-tetrahydrochloride hydrochloride quinoline are dissolved in 10 ml of tetrahydrofuran and 1 ml of water, then 260 mg of sodium carbonate are added. Finally, 120 mg of methyl chloroformate in 1.5 ml of tetrahydrofuran are added dropwise and the stirring is continued for 4 hours. Then the mixture is combine with 20 ml of water and 30 ml of ethyl acetate. The organic phase is then separated, washed with water, dried and concentrated by evaporation. The residue is column chromatographed on silica gel with a mixture of ethyl acetate / methylene chloride (7: 3). Yield: 350 mg (56% of theory) Melting point: foam C27H29N05S (560.21) Calculated: C 62.29 H 5.42 N 10.76 S 6.16 Found: 61.85 5.61 10.00 6.40 Example 28 L- [3-4-amidino-phenyl] hydrochloride ) -propionyl] -6- methylamino-1, 2,3, 4-tetrahydro-quinoline and. L- [3- (4-amidino-phenyl) -pro-ionyl] -6- (N-methyl-phenyl-sulfonamido) -1,2,3,4-tetrahydro-quinoline hydrochloride Prepared in a manner analogous to Example 24 from l- [3- (4-cyano-phenyl) -propionyl] -6- (N-methyl-phenyl-sulfonamido) -1,2,3,4-tetrahydro-quinoline (see example 9 (8) ) and subsequent column chromatographic separation on silica gel using methylene chloride / methanol (8: 2). a) l- [3- (4-Amidino-phenyl) -propionyl] -6-methylamino-1,2,3,4-tetrahydro-quinoline hydrochloride Yield: 25% of the theory Melting point: sintered from 130 ° C C2oH2_N403 (390.92) x HCl (390.92) Calculated: C 61.45 H 6.96 N 14.73 Found: 61.27 _ 6.91 14.05 b) L- [3- (4-amidino-phenyl) -propionyl] -6- (N-methyl-) benzenesulfonate phenyl sulfonamido) -1,2,3, 4-tetrahydroquinoline-Yield: 6% of the theory Melting point: sinter from 90 ° C C26H28N403S x C6H5S03H x H20 (652.79) Calculated: C 58.88 H 5.56 N 8.58 Found: 58.53 5.37 7.94 The following are prepared analogously: (the) l- [3- (4-Amidino-phenyl) -propionyl] -6- (2-phenylethylamino) -1,2,3,4-hydrochloride -tetrahydro-quinoline Prepared from the compound prepared according to example 9 (11). Yield: 22% of theory Melting point: from 90 ° C C27H30N4O x 2.5 HCl x 2 H20 (553.76) Calculated: C 58.56 H 6.64 N 10.12 Found: 56.69 6.30 9.64 (Ib) l- [3- Hydrochloride (4-amidino-phenyl) -propionyl] -6- [N- (2-phenylethyl) -phenylsulfonamidoj-l, 2, 3, 4-tetrahydroquinoline Yield: 41% of theory Melting point: from 105 ° C C33H39N403S x HCl x 0.5 H20 (612.20) Calculated: C 64.75 H 5.93 N 9.15 S 5.24 Found: 64.66 6.04 9.01 5.51 (2a) L- [3- (4-amidino-) hydrochloride phenyl) -propionyl] -6 - "(N- -ethoxycarbonyl-methylamino) -1,2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 9 (10) Yield: 13.0% of the theory Melting point: from 135 ° C (decomp.) - C23H28 403 x HCl x 7.5 H20 (471.99). Calculated: C 58.53 H 6.83 N 11.87 Found: 58.44 6.44 11.58 (2b) Benzenesulfonate of l- [3 ~ - (4-amidino-phenyl) -propionyl] -6- (N-ethoxycarbonylmethyl-phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline Yield: 21% of theory Melting point: from 105 ° C C29H32N405S x 0.5 C6H5S03H x H20 x 0.5 HCl (664.00) Calculated: G 57.83 H 5.69 N 8.44 - Found: 56.96"5.60 8.47 Example 29 l- [3- (4-amidino-phenyl) -propionyl] -6- (N -carboxymethyl-phenyl-sulfonamido) -1,2,3,4-tetrahydro-quinoline 370 mg of l- [3- (4-amidino-phenyl) -propionyl] -6- (N- ethoxycarbonylmethyl-phenylsulfonamido) -1, 2, 3, 4-tetrahydro-quinoline are dissolved in 5 ml of ethanol and stirred overnight with 1.6 ml of a 1 N solution of sodium hydroxide. The mixture is then neutralized with hydrochloric acid, concentrated by evaporation and the residue chromatographed with methanol in a column on silica gel. Yield: 190 mg (65% of theory) C27H28N405S (520.61) Calculated: C 62.29 H 5.42 N 10.76 Found: 61.13 5.59 10.48 Example 30 l- [3- (4-aminomethyl-phenyl) -propionyl] -6-phenyl- sulfonamido-1, 2,3,4-tetrahydro-quinoline _ 900 mg of l- [3- (4-cyano-phenyl) -propionyl] -6-phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline hydrogenate in 20 ml of a methanolic ammonium solution at 3 bar for 17 hours on Raney nickel. The catalyst is then removed by suction filtration, the mixture is concentrated by evaporation, the residue obtained is dissolved in water and made alkaline. It is extracted with methylene chloride, the organic phase is separated, dried and concentrated by evaporation in vacuo. Yield: 0.6 g (67% of theory) Melting point: 130-132 ° C C25H27N3? 3S (449.58) Calculated: C 66.79 H 6.05 N 9.35 S 7.13 Found: 66.73 6.16 9.44 7.12 The following are prepared analogously: (1) l- [3- (4-aminomethyl-phenyl) -propionyl] -6 - (1-naphthylsulfonamido) -1,2,3,4-tetrahydro-quinoline (2) l- [3- (4-aminomethyl-phenyl) -propionyl] -6- (4-fluoro-phenylsulfonamido) -1, 2,3,4-tetrahydro-quinoline (3) l- [3- (4-aminomethyl-phenyl) -propionyl] -6-butyl-sulfonamido-1,2,3,4-tetrahydro-quinoline (4 ) l- [3- (4-aminomethyl-phenyl) -propionyl] -6- (N-methyl-phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline (5) ~ 1 - [3- (4- aminomethyl-phenyl) -propionyl] -6-benzyl-sulfonamido-1, 2,3,4-tetrahydro-quinoline (6) l- [3- (4-aminomethyl-phenyl) -propionyl] -6-benzoylamino-1, 2,3,4-tetrahydro-quinoline Example 31 l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (quinoline-8-sulfonyl) -hydroxycarbonylmethylamino] -! 2,3,4 - tetrahydro-quinoline 590 mg of l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (quinolino-8-sulfonyl) -N- (ethoxycarbonylmethyl) -amino] - 1,2,3 , 4-tetrahydro-quinoline (see example 26 (1) *) is dissolved in 15 ml of ethanol and 2.4 ml of a 1 N sodium hydroxide solution, and stirred -During 2.5 hours at room temperature. The mixture is then neutralized with 0.1N hydrochloric acid and concentrated by evaporation. The residue is stirred with water and ethanol and dried. Yield: 200 mg (41% of theory) Melting point: 215-217 ° C with decomposition C30H29N5O5S x 1.5 H20 (598.68) Calculated: C 60.19 H 5.39 N 1.1.70 Found: 59.70 5.45 11.34 The following are prepared in a manner Analogous: (1) "l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (isoquinolino-5-sulfonyl) -hydroxycarbonylmethylamino] -l, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 26 (2) Yield: 45% of the theory Melting point: 213-215 ° C with decomposition C30H29N5O5S x 1.5 H20 (598.68) Calculated: C 60.19 H 5.39 N 11.70 Found: 60.20 5.39 11.37 (2) l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (phenyl-methanesulfonyl) -hydroxycarbonylmethylamino] -l, 2, 3, 4-tetrahydro-quinoline Prepared to from the compound prepared according to example 26 (3) Yield: 81% of the theory C2sH30N4O5S x H20 (552.64) Calculated: C 60.85 H 5.84 N 10.14 Found: 61.25 5.94 10.16 (3) l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (n-butyl-sulfonyl) -hydroxycarbonylmethylamino] -l, 2,3,4- tetrahydroquinoline Prepared from the compound prepared according to example 26 (4) Yield: 68% of theory C25H32N405S x 0.5 H20 ( 509.63) Calculated: C 58.92 H 6.53 N 10.99 Found: 58.82 6.61 10.96 (4) L- [(4-amldino-phenoxy) -acetyl] -6- [N- (1-naphthylsulfonyl) -hydroxycarbonylmethylamino] -l hydrochloride 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 26 (5) Yield: 59% of theory C30H28NO6S x HCl x 0.5 H20 (618.14) Calculated: C 57.17 H 5.18 N 8.51 Found: 57.45 4.82 8.93 (5) l- [3- (4-amidino-phenyl) -propionyl] -6- [N-benzoyl-hydroxycarbonylmethylamino] -l, 2, 3, 4-tetrahydroquinoline Prepared from the compound prepared according to example 26 (6) Yield: 31% of the theory C28H28N404 x H20 (658.54) Calculated: C 66.92 H 6.02 N 11.15 Found: 66.23 6.18 10.98 (6) l- [3- ( 4-amidino-phenyl) -propionyl] -6- [N- (1-naphthoyl) -hydroxycarbonylmethylamino] -l, 2, 3, 4-tetrahydroquinoline Prepared from the compound prepared according to example 26 (7) C32H3oN404 x H20 (552.63) .. Calculated: C 69.55 H 5.84 N 10.14 Found: 68.84 5.84 9.93 (7) L- [3- (4-amidino-2-hydroxycarbonyl-ethylcarbonylamino) -phenyl) -propionyl] -6 hydrochloride] phenylsulfonylamino) -1, 2,3,4-tetrahydroquinoline Prepared from the compound prepared according to example 24 (47) (8) l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (naphth-2-yl-sulfonyl) -ethoxycarbonylmethylamino] -!, 2,3,4-tetrahydroquinoline Yield: 82% of theory C3iH30N4O5S x 1. 5 H20 (597.70) Calculated: C 62. 30 H 5. 57 N 9. 37 Found: 62.15 ^ 5.47 9.39 (9) l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (naphth-1-yl-sulfonyl) -N- (hydroxycarbonylpropyl) -amino] -l , 2,3, 4-. Tetrahydroquinoline Prepared from the compound prepared according to example 25 Yield: 48% of the theory - C33H3N405S (598.72) Mass spectrum: FAS-MS: '(M + H) + = 599 (10) l- [3- (4-Amidino-phenyl) -propionyl] -6- [N- (naphth-1-ylsulfonyl) -N- (1-hydroxycarbonylethyl) -amino] -1] hydrochloride , 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 25 (1) Yield: 80% of theory C32H32N405S X HCl X 1.5 H20 (611.72) Calculated: C 62.83 H 5.77 N 9.16 Found: 62.97 5.73 9.16 (11) l- [3- (4-Amidino-phenyl) -pro-ionyl] -6- [N- (naphth-1-ylsulfonyl) -hydroxycarbonylmethylamino] - - 1, 2-hydrochloride , 3,4-tetrahydroquinoline Prepared from the compound prepared according to example 25 (2) Yield: 77% of the theory _ C3? H30N4O5S x HCl x H0 (625.15 ) Calculated: C 63.25 H 5.48 N 9.52 Found: 63.45 5.83 9.76 (12) l- [3- (4-Amidino-phenyl) -propionyl] -6- [N- (naphth-1-ylsulfonyl) -N hydrochloride] - (N, N-di (hydroxycarbonylmethyl) -aminocarbonyl) -amino] -1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 25 (6) Yield: 91% of theory C3sH35N508S x H20 (703.78) Calculated: C 59.73 H 5.30 N 9.95 Found: 59.92 5.25 9.97 (13) L- [3- (4-amidino-phenyl) -propionyl] -6- (N-hydroxycarbonyl-methyl-phenylamino] hydrochloride ) -1,2,3, 4-tetrahydroquinoline Prepared from the compound prepared according to Example 24 (62) Yield: 26% of theory C28H28N404 X HCl x 1.5 H20 (548.02) Calculated: C 61.36 H 5.89 N 10.12 Found: 61.34 5.67 9.85 (14) L- [3- (4-amidino-phenyl) -propionyl] -6- (N-hydroxycarbonylmethyl-cyldhexylaminocarbonyl) -1,2,3,4-tetrahydro-quinoline hydrochloride Prepared from the compound prepared according to the example 24 (66) Yield: 58% of theory C28H34N404 x HCl x 0.5 H20 (536.05) Calculated: C 62.74 H 6.77 N 10.45 Found: 63.24 6.78 9.76 (15) L- [3- (4-amidino-phenyl) -propionyl] - hydrochloride 6- (2- hydroxycarbonylpyrrolidino) -l, 2, 3, 4-tetrahydroquinoline Prepared from the compound prepared according to example 24 (67) Yield: 35% of theory C25H28N404 x HCl x H20 (502.96) Calculated: C 59.70 H 6.21 N 11.16 Found: 60.02 6.31 10.17 (16) L- [3- (4-amidino-phenyl) -propionyl] -6- (2-hydroxycarbonylpiperidino) -1,2,3,4-tetrahydroquinoline hydrochloride Prepared from the compound prepared from conformance to example 24 (68) Yield: 46% of the theory C26H30N4O4 x HCl X H20 (517.03) Calculated: C 60.40 H 6.43 N 10.84 Found: 60.73 6.35 9.94 (17) L- [3- (4-amidinohydrochloride phenyl) -propionyl] -6- (3-hydroxycarbonylpiperidino) -1, 2, 3, 4-tetrahydroquinoline Prepared from the compound prepared according to Example 24 (69) Yield: 47% of the theory C26H3o 404 x HCl x H20 (517.03) Calculated: C 60.40 H 6.43 N 10.84 Found: 61.28 6.50 10.39 (18) Hydrochloride of l - [3- (4-amidino-phenyl) -propionyl] -6- [N- (naphthalin-2-ylmethyl) -hydroxycarbonylmethylamino] -1,2,3,4-tetrahydroquinoline Prepared from the compound prepared in accordance with example 24 (77) Yield: 70% of the theory C32H32N403 x HCl (557.13) Calculated: C 66.98 H 5.96 N 10.05 Found: 67.81 _ 6.45 8.86 (19) L- [3- (4-amidino-phenyl) hydrochloride ) -propionyl] -6- [N- (naphth-1-yl-methyl) -hydroxycarbonylmethyl-amino] -l, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to Example 24 (78 ) Yield: 69% of theory C32H32N403 x HCl x H20 (575.13) Calculated: C 66.82 H 6.13 N 9.74 Found: 67.43 6.75 8.46 (20) L- [3- (4-amidino-phenyl) -propionyl] - hydrochloride 6- [N- . (2-hydroxycarbonylethylcarbonyl) -benzylamino] -1, 2, 3, 4- "tetrahydro-quinoline, Prepared from the compound prepared according to the example" 24 (81) Yield: 98% of theory C30H32N4O4 x HCl x H20 (567.11) Calculated: C 63.53 H 6.22 N 9.87 Found: 63.53 6.38 9.11 (21) L- [3- (4-amidino-phenyl) -propionyl] -6- (N-hydroxycarbonylmethyl-benzylamino) -1.2 hydrochloride , 3,4-tetrahydro-quinoline Prepared from the compound prepared according to Example 24 (76) Yield: 79% of theory C28H30N4O3 x HCl x 1.5 H20 (534.07) Calculated: C 62.97 H 6.41 N 10.49 Found: 63.17 6.83 8.67 (22) l- [3- (4-Amidino-phenyl) -propionyl] -6- [N-hydroxycarbonylmethyl-N- (2, 2-diphenyl-ethyl) -amino] -1,2-hydrochloride 3, 4-tetrahydro-quinoline Prepared from the compound prepared according to example 24 (92) Yield: 90% of the theory: C35H36N403 x HCl (597.20) Calculated: C 69.79 H 6.04 N 8.46 "Found: 70.39 6.24 9.38 Example 32 l- [3- (4-Benzyloxycarbonylamino-phenyl) -propionyl] -6- (1-naphthylsulfonamido) -1, 2, 3, 4-tetrahydro-quinoline 15.5 g of hydrochloride 1- [3- (4-amidino-phenyl) -propionyl] -6- (1-naphthylsulfonamido) -1,2,3,4-tetrahydro-quinoline are dissolved in 250 ml of tetrahydrofuran and 25 ml of water, and combine with 6.9 g of sodium carbonate, then 5.8 g (0.032 mol) of benzyl chloroformate are added dropwise at room temperature over 30 minutes, and the solution is stirred overnight. the precipitate is decanted, the solution is concentrated to approximately 50 ml by evaporation, and extracted three times with ethyl acetate.The organic phase is dried, concentrated by rotary evaporation and the residue is filtered on a column on silica gel with chloride. of methylene / ethyl acetate (7: 3) Yield: 14.0 g (77% of theory) Melting point: 172-174 ° C The following are prepared in a manner Analogous: (1) l- [3- (4-benzyloxycarbonylamino-phenyl) -propionyl] -6-phenyl-sulfonylamino-1, 2,3,4-tetrahydro-quinoline Prepared from the compound prepared according to example 22 Performance: 75% of the theory Melting point: 172-174 ° C C33H32 405S x 0.5 H20 (605.72) Calculated: C 65.44 H 5.49 N 9.25 Found: 65.48 5.60 8.93 (2) l- [3- (4-methoxycarbonylamino-phenyl) -propionyl] -6 - [N- (quinolino-8-sulfonyl) -N-ethoxycarbonylmethyl-amino] -1,2,3,4-tetrahydro-quinoline (3) l- [3- (4-octyloxycarbonylamino-phenyl) -propionyl] -6 - [N- (quinoline-8-sulfonyl) -N-ethoxycarbonylmethyl-amino] -1,2,4,4-tetrahydro-quinoline (4) l- [3- (4-hexyloxycarbonylamino-phenyl) -propionyl] -6 - phenylsulfonylamino-1,2,3,4-tetrahydro-quinoline (5) l- [3- (4-ethyloxycarbonylamino-phenyl) -propionyl] -6- phenylsulfonylamino-1, 2,3,4-tetrahydro-quinoline (6 ) l- [3- (4-heptyloxycarbonylamino-phenyl) -propionyl] -6- [N- (naphth-1-ylsulfonyl) -N-ethoxycarbonylmethyl-amino] -l, 2, 3, 4-ethyl acetate -tetrahydro-quinoline (7) l- [3- (4-ethyloxycarbonylamino-phenyl) -propionyl] -6- [N- (aft-1-yl-sulfonyl) -N-ethoxycarbonylmethyl-amino] - 1, 2, 3, 4-tetrahydro -quinoline (8) l- [3- (4-octyloxycarbonylamine-phenyl) -propionyl] -6- (N-phenyl-sulfonyl-N-ethoxycarbonylmethyl-amino) -1,2,3,4-tetrahydro-quinoline (9 ) l- [3- (4-methyloxycarbonylamino-phenyl) -propionyl] -6- (N- * "phenyl-sulfonyl-N-ethoxycarbonylmethyl-amino) -1,2,3, 4- tetrahydro-quinoline (10) l- [3- (4-ethyloxycarbonylamino-phenyl) -propionyl] -6- (N- _ benzoyl-N-ethoxycarbonylmethyl-amino) -1,2,3,4-tetrahydro-quinoline (11) ) l- [3- (4-octyloxycarbonylamino-phenyl) -propionyl] -6- (N-ethoxycarbonylmethyl-phenylamino) -1,2,3,4-tetrahydroquinoline __ (12) l- [3- (4- methyloxycarbonylamino-phenyl) -propionyl] -6- (N-ethoxycarbonylmethyl-phenylamino) -1,2,3,4-tetrahydroquinoline Example 33 Dry ampoule containing 75 mg of active substance per 10 ml Composition Active substance 75.0 mg Mannitol 50.0 mg Water for injection cbp 10.0 ml Preparation: The active substance and mannitol dissolve in water. After being packed, the solution is lyophilized. To produce the ready-to-use solution, the product dissolves in water for injection. Example 34 Dry ampoule containing 35 mg of active substance per 2 ml Composition Active substance 35.0 mg Mannitol 100.0 mg Water for injection c.b.p. 2.0 ml Preparation: The active substance and mannitol dissolve in water. After being packed, the solution is lyophilized. To produce the ready-to-use solution, the product dissolves in water for injection. Example 35 Tablet containing 50 mg of active substance Composition (1) Active substance 50.0 mg (2) Lactose "98.0 mg (3) Corn starch 50.0 mg (4) Polyvinyl pyrrolidone * 15.0 mg (5) Magnesium stearate 2.0 mg 215.0 mg Preparation _ (1), (2) and (3) are mixed with each other and granulated with an aqueous solution of (4). (5) is added to the dry granulated material. , with facets on both sides and with a notch on one of the sides Diameter of the tablets: 9 mm.

Example '36 Tablet containing 350 mg of active substance Preparation: (1) Active substance 350.0 mg (2) Lactose "136.0 mg (3) Corn starch 80.0 mg (4) Polyvinyl pyrrolidone 30.0 mg (5) Magnesium stearate 4.0 mg 600.0 mg (1), (2) and (3) are mixed with each other and granulated with an aqueous solution of (4). (5) is added to the dry granulated material. Compressed tablets, biplanar, with facets on both sides and with a notch on one of the sides Diameter of the tablets: 12 mm Example 37 Capsules containing 50_ mg of active substance Composition: (1) Active substance 50.0 mg (2) Anhydrous corn starch 58.0 mg (3) Lactose powder 50.0 mg (4) Magnesium stearate 2.0 mg 160.0 mg Preparation: (1) Crush with (3). to the mixture of (2) and (4) mixing vigorously. This powder mixture is packed into number 3 hard gelatin capsules in a capsule filling machine. Example 38 Capsules containing 350 mg of active substance Composition: (1) Active substance 350.0 mg (2) Anhydrous corn starch 46.0 mg (3) Lactose powder 30.0 mg (4) Magnesium stearate 4.0 mg 430.0 mg Preparation: (1) ) is crushed with "(3)." Crushing is added to the mixture of (2) and (4) by mixing vigorously.This powder mixture is packed in number 0 hard gelatin capsules in a capsule filling machine.

Example 39 Suppositories containing 100 mg of active substance 1 suppository contains Active substance 100.0 mg Polyethylene glycol (P.M. 1500) 600.0 mg Polyethylene glycol (P.M. 6000) 460.0 mg Polyethylenesorbitol monostearate 840.0 mg 2,000.0 mg Method: Polyethylene glycol is fused together with polyethylene sorbitol monostearate. At 40 ° C the milled active substance is dispersed homogeneously in the melt. It is cooled to 38 ° C and poured into slightly cooled suppository molds

Claims (11)

1. CLAIMS Phenylalkyl derivatives of the general formula wherein Ra "denotes a hydrogen atom, a carboxy group, C? _3-alkoxycarbonyl, benzoyl, phenylsulfonyl, nitro, R? NR2, R? NR2-X-, or (R3X) NR? - where Ri denotes a hydrogen atom, a C 1-5 alkyl group which may be substituted with a phenyl, carboxy, C 4 -4 alkoxycarbonyl or aminocarbonyl group, while the amino group of the aminocarbonyl group may be additionally mono- or disubstituted with C groups ? - alkyl, phenyl-C? -3-alkyl, phenyl, carboxy-C? _3-alkyl or C? _3-alkoxycarbonyl-C? -3-alkyl, ~ "and the substituents may be identical or different, or a C2_3-straight chain alkyl group which is terminally substituted by an amino group, C? _3-alkylamino, di- (C? _3-alkyl) amino, C? -4-alkanoylamino, phenylamino, N-benzyloxycarbonyl-1-phenylamino, pyrrolidino, piperidino or morpholino, R2 denotes a hydrogen atom, a C? _3-alkyl group optionally substituted with one or two phenyl groups or with a naphthyl group, or a phenyl group which may be substituted with a fluorine, chlorine or bromine atom, "or with a C2-3-straight chain alkyl group which is terminally substituted by an amino group, C? _3-alkylamino, C? _3-alkanoylamino, di- (C? _3-alkyl) amino, pyrrolidino, piperidino or morpholino Ri and R2 together with the nitrogen atom therebetween denotes a pyrrolidino or piperidino group optionally substituted with a C? -3-alkyl, carboxy or C? _3-alkoxycarbonyl group, a pyrrolidino or piperidino group substituted with two C? _3-alkyl groups or a morpholino group R3 denotes a straight or branched chain C? -7-alkyl group which may be substituted at the 1, 2 or 3 position with a phenyl group, or at the 2 to 7 position with a fluorine atom, chlorine or bromine, with a carboxy or C? _3-alkoxycarbonyl group, a trifluoromethyl group, a phenyl, naphthyl or chroman group ilo which in each case can be substituted with a fluorine, chlorine or bromine atom, with a trifluoromethyl group, C? -3-alkyl, C? _3-alkoxy, amino, C? -3-alkylamino, di- (C? _3-alkyl) amino or aminocarbonyl, while the phenyl, naphthyl or chromanyl groups above mentioned may be further substituted with one to three methyl groups, a phenyl or aminophenyl group substituted with two chlorine or bromine atoms, a thienyl group optionally substituted with a chlorine or bromine atom or with a methyl group, a C3-8 group -cycloalkyl, C8_? 2-bicycloalkyl, quinolyl, isoquinolyl or benzimidazolyl, or Ri and R3 together denote an n-alkylene group with 3 to 5 carbon atoms, wherein an ethylene group linked to the group S02- or _CO- can be replaced with a 1, 2-phenylene group, and X denotes a carbonyl or sulfonyl group, or Ra can also represent a C2_3-alkanoyl group which on the alkyl moiety is substituted with a carboxy-C? -3-alkyl or C? _3 group -alkoxycarbonyl-C? _3-alkyl and a benzoyl, naphthoyl, phenylsulfonyl or naphsulfonyl group, Rb denotes an amidino group optionally substituted with a C? _? or -alkoxycarbonyl or phenyl-C? _3-alkoxycarbonyl group, a cyano group or aminomethyl, Rc and R, which may be identical or different, from they each note a hydrogen atom, fluorine, chlorine, bromine or iodine, a methyl, methoxy, nitro, amino or aminocarbonyl group, or an amino group optionally substituted with a straight chain C2_-alkanoyl group wherein the alkanoyl moiety can be terminally substituted with a carboxy or C? -3-alkoxycarbonyl group, A denotes an ethylene, ethenylene, n-propylene or n-butylene group, optionally substituted with one or two C? _3-alkyl groups, while a methylene group of an ethylene or n-propylene group optionally substituted with one or two C.sub.3-alkyl groups, linked (i) to the nitrogen atom can be substituted with a carbonyl group, or (ii) the phenyl nucleus can be substituted with an oxygen or sulfur atom, with a sulfinyl or sulfonyl group, or with an imino group optionally substituted with a C? _3-alkyl group, B denotes a bondTin, methylene, ethylene, ethenylene or n-propylene group, optionally substituted with one or two C? _3-alkyl groups, while (iii) if the previously mentioned methylene, ethylene, or n-propylene groups denote a group carbonyl or thiocarbonyl, a methylene group can be substituted with an oxygen atom or with an imino group optionally substituted with a C? _3-alkyl group, or (iv) if in the previously mentioned ethylene or n-propylene groups Y denotes a group methylene, a methylene group in the 3 or 4 position in relation to the nitrogen atom it can be substituted with an oxygen atom or with a group, imino optionally substituted by a C? _3-alkyl group, - W denotes a methino group or a nitrogen atom, and Y denotes a methylene group, carbonyl or thiocarbonyl their tautomers, their stereoisomers and their mixtures and their salts.
2. 2. Phenylalkyl derivatives of the general formula I according to claim 1, wherein Ra, Rc, Rd, A, B, W and Y are defined as in claim 1, and Rb denotes an amidino group optionally substituted with a C? -? o-alkoxycarbonyl or phenyl-C? -3-alkoxycarbonyl group, their optical antipodes and their salts.
3. 3. Phenylalkyl derivatives of the general formula I according to claim 1, wherein Ra denotes a group R? NR2, R? 'NR2, -X- or (R3X) NR? - where Ri denotes a hydrogen atom , a C? _4-alkyl group which may be substituted with a phenyl, carboxy, C? _2-alkoxycarbonyl or aminocarbonyl group, while the amino group of the aminocarbonyl group may be additionally mono- or disubstituted with C? _4-alkyl, phenyl, benzyl, carboxy-C-2-alkyl or • C? -2-alkoxycarbonyl-C? -2-alkyl groups, and the substituents may be. identical or different, or an ethyl group that is terminally substituted with an amino, acetylamino morpholino phenylamino or N-benzyloxycarbonyl-phenylamino group, R2 denotes a hydrogen atom, a C? -3-alkyl group optionally substituted with one or two phenyl groups or with a naphthyl group, a cyclohexyl group, or a phenyl group optionally substituted with a chlorine atom, with a 2-aminoethyl or 2-acetylamino group, Ri? and R 2 x have the meanings given above for R 1 and R 2 or together with the nitrogen atom they denote a pyrrolidino or piperidino group optionally substituted with a methyl, carboxy or C 2 -alkoxycarbonyl group, a pyrrolidino or piperidino group substituted with two methyl groups, or a morpholino group, R3 denotes a straight or branched chain C? -5-alkyl group which may be substituted at the 1, 2 or 3 position with a phenyl, carboxy or C? _3-alkoxycarbonyl group , or in the 2 or 3 position with a chlorine atom, a trifluoromethyl group, a phenyl or naphthyl group which in each case "may be substituted with one atom" of fluorine, chlorine or bromine, with a group trifluoromethyl, C? _3-alkyl, C? _3-alkoxy, amino, C? _3-alkylamino, di- (C? _3-alkyl) amino or aminocarbonyl, while the aforementioned phenyl groups can be further substituted with each other three methyl groups, a phenyl or aminophenyl group substituted with two chlorine or bromine atoms, a thienyl group substituted with a chlorine or bromine atom, a C3_7-cycloalkyl, quinolyl, isoquinolyl or benzimidazolyl group, or Ri Y3 together denote a n-alkylene group having 3 to 5 carbon atoms, wherein an ethylene group linked to the group S02 or CO- can be substituted with a 1,2-phenylene group, and X denotes a carbonyl or sulfonyl group, or Ra also denotes a C2-3-alkanoyl group which is substituted with a carboxy-C? _3-alkyl or Cx-3-alkoxycarbonyl-C? _3-alkyl group and a benzoyl, naphthoyl, phenylsulfonyl- or naphthylsulfonyl group, Rb denotes an optionally substituted amidino group with a C? -? or -alkoxycarbonyl or phenyl-C? _3-alkoxycarbonyl group, Rc denotes a a hydrogen atom, fluorine, chlorine, bromine or iodine, a methyl, methoxy, aminocarbonyl, amino or nitro group, or an amino group optionally substituted with a straight-chain C2_4-alkanoyl group wherein the alkanoyl moiety can be terminally substituted with a carboxy or C? _3-alkoxycarbonyl group, Rd denotes a hydrogen atom A denotes an ethylene, n-propylene or n-butylene group, optionally substituted with one or two methyl groups , while a methylene group of an ethylene or n-propylene group optionally substituted with one or two methyl groups, which is (i) bound to the nitrogen atom, can be substituted with a carbonyl group, B denotes a bond, a methylene group, ethylene, ethenylene or n-propylene optionally substituted with one or two methyl groups, while (iii) if in the methylene, ethylene or n-propylene groups previously mentioned Y denotes a carbonyl or thiocarbonyl group, a methylene group can be substituted with an oxygen atom or with an imino group optionally substituted with a methyl group, or (iv) if in the previously mentioned ethylene or n-propylene groups Y denotes a methylene group, a methylene group in the 3 or 4 position with respect to the Nitrogen atom can be substituted with an oxygen atom or with an imino group optionally substituted with a group methyl, W denotes a methino group, and Y denotes a methylene, carbonyl or thiocarbonyl group, their optical antipodes and their salts. .
4. Phenylalkyl derivatives of the general formula I according to claim 1, wherein Ra denotes a group (R3S02) NR ?, its optical antipodes or its salts.
5. 5. Phenylalkyl derivatives of the general formula I according to claim 1, wherein Ra denotes a group (R3S02) NR ?, while Ri and R3 are as defined in claim 4, Rb denotes an amidino group optionally substituted with a C? -? or -alkoxycarbonyl or phenyl-C? -3-alkoxycarbonyl group, Rc and Rd each denote a hydrogen atom, A denotes an optionally-substituted n-propylene group with a methyl group, B denotes an ethylene group, W denotes a methino group, and Y denotes a carbonyl group, its optical antipodes and its salts.
6. 6. The following phenylalkyl derivatives of the general formula I according to claim 1: (a) l- [3- (4-amidino-phenyl) propionyl] -6- (4-fluoro-phenylsulfonamido) -1, 2, 3, 4-tetrahydro-quinoline, (b) l- [3- (4 -amidino-phenyl) propionyl] -6-butyl-sulfonamido-1,2,3,4-tetrahydro-quinoline, (c) l- [3- (4-amidino-pheny?) propionyl] -5-phenylsulfonamido-1 , 2,3, 4-tetrahydro-quinoline, (d) l- [3- (4-amidino-phenyl) propionyl] -3-methyl-6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline, ( e) l- [3- (4-amidino-phenyl) propionyl] -6- (5-chloro-thien-2-ylsulfonamido) -1,2,3,4-tetrahydro-quinoline, (f) l- [3 - (4-amidino-phenyl) propionyl] -6-phenyl-sulfonamido-1,2,3,4-tetrahydro-quinoline, (g) l- [3- (4-amidino-phenyl) propionyl] -6- ( N-methyl-phenylsulfonamido) -1,2,3,4-tetrahydro-quinoline, (h) l- [3- (4-amidino-phenyl) propionyl] -6- (N-ethoxycarbonylmethyl-phenylsulfonamido) -1,2, 3, 4-tetrahydroquinoline, (i) l- [3- (4-amidino-phenyl) propionyl] -6- (N-carboxymethyl-phenylsulfonamido) -1,2,3,4 -tetrahydro-quinoline, (j) l- [3- (4-aminomethyl-phenyl) propionyl] -6-phenylsulfonamido-1, 2, 3, 4-tetra hydroquinoline, (k) l- [3- (4-amidino-phenyl) propyl] -6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline, (1) l- [3- (4-methyloxycarbonyl -amidino-phenyl) propionyl] -6-phenylsulfonamido-1,2,3,4-tetrahydro-quinoline, (m) l- [3- (4-amidino-phenyl) -propionyl] -6- (N-phenyl-methyl-aminocarbonyl) -1,2, 3,4-tetrahydro-quinoline, (n) l- [3 - (4-amidino-phenoxy) -acetyl] -6- [N- (1-naphthylsulfonyl) -hydroxycarbonylmethylamino] -l, 2,3,4-tetrahydroquinoline, (o) l- [3- (4-amidino-phenyl) -propionyl] -6-diethylamino-carbonyl-phenyl-1,2,3,4-tetrahydro-quinoline, (p) l- [3- (4-amidino-phenyl) -propionyl] -6- (N-benzoyl-methylamino) -1,2,3, 4-tetrahydro-quinoline, (q) l- [3- (4-amidino-phenyl) -propionyl] -6- (N-benzoyl-methylamino) -1 , 2,3, 4-tetrahydro-quinoline, (r) _ l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (naphth-1-yl-sulfonyl) -hydroxycarbonylmethylamino] -! , 2,3, 4-tetrahydroquinoline, (s) _ l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (1-naphthyl) -hydroxycarbonylmethylamino] -l , 2, 3, 4-tetrahydroquinoline, (t) l- [3- (4-amidino-phenyl) -propionyl] -6- (N-benzoyl-hydroxycarbonylmethylamino) -1,2,3, 4- tetrahydroquinoline, (u) l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (quinolin-8-sulfonyl) -hydroxycarbonylmethylamino] - 1, 2, 3, 4-tetrahydroquinoline, and (v) l- [3- (4-amidino-phenyl) -propionyl] -6- [N- (n-butyl-sulfonyl) -hydroxycarbonylmethylamino] - !, 2, 3, 4-tetra hydroquinoline, its optical antipodes and its salts.
7. 7. Physiologically acceptable salts of the compounds according to claims 1 to 6.
8. 8. Pharmaceutical compositions containing a compound according to at least one of claims 1 to 6, wherein Rb is as defined in claims 1 to 6 with the exception of the hydrogen atom, the nitro group and cyano, or a salt according to claim 7, optionally together with one or more carriers and / or inert diluents.
9. 9. Use of a compound according to at least one of claims 1 to 6, wherein Rb is as defined in claims 1 to 6 with the exception of the hydrogen atom, the nitro and cyano group, or a salt according to claim 7, for preparing a pharmaceutical composition having the effect of prolonging the thrombin range, which has a thrombin inhibitory effect and an inhibitory effect on the proteases of the related serine.
10. Process for preparing a pharmaceutical composition according to claim 8, characterized in that the compound according to at least one of claims 1 to 6, wherein Rb is - as defined in claims 1 to 6 with the Except for the hydrogen atom, the nitro and cyano group, or a salt according to claim 7, it is incorporated in one or more vehicles and / or inert diluents by a non-chemical method.
11. 11. Process for preparing the compounds according to claims 1 to 7, characterized in that a) to prepare a compound of the general formula I wherein Rb denotes a cyano group and Y denotes a methylene group: it is reacted "of a compound of the general formula wherein A and Ra are as defined in claims 1 to 6, with a compound of the general formula B - (III) wherein B, W, Rc and Rd are as defined in claims 1 to 6, Y 'denotes a methylene group Zi denotes a leaving group, or b) to prepare a compound of the general formula I wherein Rb denotes a cyano group and Y denotes a carbonyl group: a compound of the general formula is reacted wherein A and Ra are as defined in claims 1 to 6, with a compound of the general formula wherein B, W, Rc and Rd are as defined in claims 1 to 6, Y '' denotes a carbonyl group, and Z2 denotes a hydroxy group or a leaving group, or c) to prepare a compound of the general formula I where Ra denotes a group R? N (XR3) and Rb denotes a cyano group: a compound of the general formula is reacted wherein A, B, W, Y, Rc, Rd and Ri are as defined in claims 1 to 6, with a compound of the formula Z3-X-R3, (VI) wherein X and R3 are as defined in claims 1 to 6, and Z3"denotes a hydroxy group or a leaving group, od) to prepare a compound of the general formula I e that Ra denotes a group RXNR2 or RXN ( XR3) in which Ri is as defined in claims 1 to 6 with the exception of the hydrogen atom, and Rb denotes a group. cyano or an amidino group substituted with a C? _? 0-alkoxycarbonyl or phenyl-C? _3-alkoxycarbonyl group: a compound of the general formula is reacted wherein A, B, W, Y, Rc, and Rd. are as defined in claims 1 to 6, R4 has the meanings given in claims 1 to 6 for R2, or denotes a group R3-X , wherein R3 and X are as defined in claims 1 to 6, and Rb denotes a cyano group or an amidino group substituted with a C? -? 0 -alkoxycarbonyl or phenyl-C? -3-alkoxycarbonyl group with a compound of the general formula __ Z4-R1 ', (VIII) in which Ri denotes a C? -5-alkyl group which may be substituted with a phenyl, carboxy, C? _4-alkoxycarbonyl or aminocarbonyl group, while the group The amino group of the aminocarbonyl group can be additionally mono- or disubstituted with C ?4-alkyl, phenyl-C ?3-alkyl, phenyl, carboxy-C?-3-alkyl or C ?3-alkoxycarbonyl-C?-3-alkyl groups , and the substituents may be identical or different, or a straight chain C2_3-alkyl group which is terminally substituted with di- (C3_3-alkyl) amino, pyrrolidino, piperidino or morpholino group, and Z4 denotes a leaving group, oe ) to prepare a compound of the general formula I in which Ra denotes a nitro group and Rb denotes a cyano group: nitration of a compound of the general formula wherein A, B, W, Y, Rc and R are as defined in claims 1 to 6, or f) ~~ to prepare a compound of the general formula I in which Ra denotes an amino group and Rb denotes a cyano group: "reduction of a compound of the general formula wherein A, B, W, Y, Rc and Rd are as defined in claims 1 to 6, or g) to prepare a compound of the general formula I wherein Rb denotes an amidino group: a compound of the general formula "" is reacted optionally formed in the reaction mixture, wherein A, "B, W, Y, Ra, Rc and Rd are as defined in claims 1 to 6, and Z5 denotes an alkoxy or aralkoxy group such as the methoxy group, ethoxy, n-propoxy, isopropoxy or benzyloxy, or a thioalkyl group or thioaralkyl, such as the thiomethyl group, thioethyl, n-propylthio or thiobenzyl, with ammonium or with the ammonium aion salts, oh) to prepare a compound of the general formula I in which Rb denotes an amidino group substituted with a C group ? -? o -alkoxycarbonyl or phenyl-C? -3-alkoxycarbonyl,: is reacted from a compound of the general formula wherein '~~ A, B, W, Y, Ra, Rc and R are as defined in claims 1 to 6, with a compound of the general formula Z6-CO-OR4, (XIII) wherein R4 denotes a C? -? or-alkyl or phenyl-C? _3-alkyl group and Z6 denotes leaving group, or i) to prepare a compound of the general formula I wherein Rb denotes an aminomethyl group: it is reduced from a compound of the general formula wherein A, B, W, Y, Ra, Rc and Rd are as defined in claims 1 to 6, or j) to prepare a compound of the general formula I in which Ra denotes a group R? NR2, in which Ri is as defined in claims 1 to 6 with the exception of the hydrogen atom, and Rb denotes a cyano group or an amidino group substituted with a group C? _? 0 -alkoxycarbonyl or phenyl-C? _3-alkoxycarbonyl,: is reacted of a compound of the general formula in which A, B, W, Y, R2, Rc, and Rd are as defined in claims 1 to 6, and Rb? denotes a cyano group or an amidino group substituted with a C? -? 0-alkoxylcarbonyl or phenyl-C? -3-alkoxycarbonyl group with a compound of the general formula - -Ri ',:? V? : wherein Ri is as defined in the above, and Z7 denotes a leaving group or together with a hydrogen atom of the adjacent carbon atom denotes an oxygen atom, ok) to prepare a compound of the general formula I where Rb denotes a cyano group and Y denotes a carbonyl group: a compound of the general formula is reacted wherein A and Ra are as defined in claims 1 to 6, and Z8 denotes a leaving group, with a compound of the formula general Rc - B, (XVIII) wherein B, W, Rc and Rd are as defined in claims 1 to 6, and ~~ R5 denotes an amino group optionally substituted by a C? -3-alkyl group and if necessary, any used protective group is unfolded during the reactions to protect reactive groups and / or subsequently, if desired, a compound of the general formula I thus obtained wherein X denotes a carbonyl group can be converted to a corresponding thiocarbonyl compound by a sulfating agent, and / or a compound of the general formula I thus obtained in that Ra contains an acyl group can be converted by hydrolysis into a compound of the general formula I in which Ra denotes a group RiNH, or in which Ra contains a carboxy group, and / or a compound of the general formula I thus obtained wherein Ra denotes or contains a carboxylic or sulfonic acid group can be converted by amidation to a compound of the general formula I, and / or if desired, a compound of the formula I thus obtained is separated into its stereoisomers and / or - a group of formula I thus obtained is transformed into its salts, particularly for pharmaceutical use in its physiologically acceptable salts, with an inorganic or organic acid or base.