MXPA01006088A

MXPA01006088A - Substituted aryl and heteroaryl derivatives, their production and their use as medicines

Info

Publication number: MXPA01006088A
Application number: MXPA/A/2001/006088A
Authority: MX
Inventors: Uwe Ries; Norbert Hauel; Henning Priepke; Jean Marie Stassen; Wolfgang Wienen; Herbert Nar; Iris Kauffmann
Original assignee: Boehringer Ingelheim Pharma Kg; Norbert Hauel; Iris Kauffmann; Herbert Nar; Henning Priepke; Uwe Ries; Jean Marie Stassen; Wolfgang Wienen
Priority date: 1998-12-16
Filing date: 2001-06-15
Publication date: 2002-05-09

Abstract

The invention relates to new substituted aryl and heteroaryl derivatives of the general formula (I) Ar - A - HCR1 - X - Y, in which A, Ar, X, Y and R1 have the meanings given in claim 1, and to their tautomers, stereoisomers, mixtures and salts, notably physiologically compatible salts with inorganic or organic acids or bases, which present valuable properties. Accordingly, the compounds of the above general formula (I), in which Y does not contain a cyano group, notably have an antithrombotic action, and the compounds of the above general formula (I), in which Y does not contain a cyano group, are valuable intermediate products for the production of compounds of the general formula (I) in which R5 is a possibly substituted aminomethyl, amidino or guanidino group.

Description

DERIVATIVES OF SUBSTITUTE ARYL AND HETEROARYL, ITS PREPARATION AND ITS USE AS MEDICINES Description of the invention The object of the present invention are new substituted aryl and heteroaryl derivatives of the general formula Ar - A - (HCR - X - Y (I) their tautomers , its stereoisomers, its mixtures and its salts, in particular its physiologically compatible salts with inorganic or organic acids or bases, which have valuable properties The compounds of the above general formula I in which Y does not contain a cyano group have valuable properties pharmacological agents, in particular an antithrombotic effect, and the compounds of the above general formula I in which Y contains a cyano group constitute valuable intermediates for the preparation of compounds of the general formula I, in which R 5 represents an aminoalkyl group Cl- 3, amidino, guanidino or guanidin-Cl-3 alkyl, optionally substituted, are therefore the subject of this invention the new compounds of the general formula I and its preparation, the medicaments containing the pharmacologically active compounds and their use.

In the above general formula A means an ethynylene group, a vinylene or ethylene group optionally substituted by a Cl-3 alkyl or Cl-3 carboxyalkyl group or by a chlorine, bromine or iodine atom, R? a hydrogen atom, a Cl-3 alkyl group or Cl-3 carboxyalkyl, Ar a phenyl group substituted by the residues R2 to R4, wherein R2 represents a Cl-6 alkyl or C3-C7-cycloalkyl-Cl-3 alkyl group , which in each case in the alkyl part Cl-6 and Cl-3 can be substituted by a carboxy, phenyl, amino, alkyl-Cl-3-amino, carboxy-alkyl-Cl-3-amino, di (alkyl) group -Cl-3) -amino, N- (carboxy-alkyl-Cl-3) -alkyl-Cl-3-amino, C3-7-amino-cycloalkyl, phenylamino, N- (alkyl-Cl-3) -phenyl- amino, N- (alkanoyl-Cl-4) -phenylamino, heteroarylamino, N- (alkyl-Cl-3) -heteroarylamino, N- (carboxy-alkyl-Cl-3) -phenylamino or N- (carboxy-alkyl-Cl) -3) -heteroarylamino, a carboxy-alkyl-Cl-5 group which in the alkyl part is substituted with an alkyl-Cl-3-amino group, N, N-di (alkyl-Cl-3) -amino, pyrrolidino, piperidino or hexamethyleneimino, a carboxy-alkyl-Cl-5 group in which the hydrogen atoms of a methylene group are substituted by a n-alkylene-C2-5 bridge, or A phenyl, phenyloxy or phenylsulfonyl group, which in the phenyl part in each case may be substituted by a fluorine, chlorine, bromine or iodine atom, by an alkyl-Cl-3, carboxy-alkyl-Cl-3 or alkoxy group; Cl-3, an alkyl-Cl-5-amino group, carboxy-alkyl-Cl-3-amino, di (alkyl-Cl-5) -amino, N- (carboxy-alkyl-Cl-3) -alkyl-Cl -5-amino, C3-7-amino-cycloalkyl, N- (carboxy-alkyl-Cl-3) -3-amino-cycloalkyl, phenylamino, N- (alkyl-Cl-3) -phenylamino, N- ( carboxy-alkyl-Cl-3) -phenylamino, heteroarylamino, N- (alkyl-Cl-3) -heteroarylamino or N- (carboxy-alkyl-Cl-3) -heteroarylamino, an alkyl-Cl-5-carbonylamino group, cycloalkyl -C3-7-carbonylamino, arylcarbonylamino, heteroarylcarbonylamino, alkyl-Cl-5-sulphonylamino, arylsulfonylamino, heteroarylsulfonylamino, N- (alkyl-Cl-3) -alkyl-Cl-5-carbonylamino, N- (alkyl-Cl-3) -cycloalkyl-C3-7-carbonylamino, N- (alkyl-Cl-3) -arylcarbonylamino,, N- (alkyl-Cl-3) -heteroarylcarbonylamino, N- (alkyl-Cl-3) -alkyl-Cl-5- sulfonilam or N- (alkyl-Cl-3) -arylsulfonylamino or N- (alkyl-Cl-3) -heteroarylsulphonylamino, wherein the abovementioned N- (alkyl-Cl-3) moieties can be further substituted by a carboxy group, carboxy-alkyl-Cl-3-aminocarbonyl or N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-aminocarbonyl, or with the exception of the carbon atom a relative to the nitrogen atom, also by a hydroxy group, carboxy-alkoxy-Cl-3, amino, carboxy-alkyl-Cl-3-amino or N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino, a cycloalkyleneimino group of 5 to 7 members, a amino group, alkyl-Cl-5-amino, cycloalkyl-C3 -7-amino, anl-amino, aryl-alkyl-Cl-3-amino, heteroarylamino or heteroaryl-alkyl-Cl-3-amino, which in each case can be substituted at the amino nitrogen atom with an alkyl-Cl-3-carbonyl, carboxy-alkyl-Cl-3-carbonyl, carboxy- alkyl-Cl-3-aminocarbonyl, 2-oxo-pyrrolidinylcarbonyl or piperazinocarbonyl, wherein (i) the aforementioned amino group which is monosubstituted by an alkyl-Cl-3-carbonyl, carboxy-alkyl-Cl-3-carbonyl group or carboxy-alkyl-Cl-3-aminocarbonyl is substituted by a 5- to 7-membered cycloalkyleneimino group or by a N, N-di- (alkyl-Cl-5) -amino group, and (ii) the alkyl part of the group The aforementioned alkyl-Cl-3-carbonyl is substituted by a carboxy, amino, hydroxy, carboxy-alkoxy-Cl-3, carboxy-alkyl-Cl-3-aminocarbonyl, carboxy-alkyl-Cl-3-amino group, N- (alkyl-Cl-3) -carbox? -alkyl-Cl-3-amino or amino-alkyl-Cl-3-carbonylamino, or by a carboxy or hydroxy group and by an amino or trifluoroacetylamino group, a carbony substituted group at the nitrogen atom by a carboxy-alkoxy-Cl-3, amino, alkyl-Cl-3-amino, carboxy -alkyl-Cl-3-amino, di- (alkyl-Cl-3) -amino group or N- (carboxy-alkyl-Cl-3) -alkyl-Cl-3-amino, and at the carbon atom by an alkyl-Cl-5 group, by a femlo group optionally substituted by an alkyl-Cl-3 group or alkoxy? -Cl-3, or by a heteroaryl group optionally substituted by an alkyl-Cl-3 group, a heteroaryl or heteroaryl-alkyl-Cl-3 group, which in each case may additionally also be substituted on the heteroaryl part by a phenyl or heteroaryl group, or a phenyl or heteroaryl group and a carboxy-alkyl-Cl-3 or alkoxy-Cl-3-carbonyl-alkyl-Cl-3 group, a 5-oxo-4,5-dihydro group -pyrazolyl or 6-oxo-4,5-dihydro-pyridazinyl, optionally substituted by 1 to 3 alkyl-Cl-3 groups, wherein an alkyl substituent can simultaneously be substituted by a carboxy or alkoxy-Cl-3-carbonyl group , or a carbonyl group, which may be substituted by a hydrogen atom, a hydroxy group, alkoxy-Cl-5 or cycloalkoxy-C3-7, by an alkyl-Cl-5 or cycloalkyl-C3-7 group optionally substituted by a carboxy group, by an alkyl-Cl-3 group substituted by a piperazino group, by a phenyl group which may be substituted by a fluorine, chlorine, bromine or iodine atom, by an alkyl-Cl-3, carboxy-alkyl-Cl-3, alkoxy-Cl-3 or carboxy group , by an amino group, alkyl-Cl-5-amino, carboxyalkyl-Cl-3-amino, C3-7-amino-cycloalkyl, phenylamino or heteroarylamino, which in each case may additionally be substituted at the nitrogen atom by a group alkyl-Cl-5, cycloalkyl-C 3-7, phenyl-alkyl-Cl-3, carboxy-alkyl-Cl-3, 2- (di- (alkyl-Cl-3) -amino) -ethyl, 3- (di- - (alkyl-Cl-3) -amino) -propyl, di- (alkyl-Cl-3) -amino, 2- (N-carboxy-alkyl-Cl-3-alkyl-Cl-3-amino) -et. il, 3- (N-carboxy-alkyl-Cl-3-alkyl-Cl-3-amino) -propyl or N-carboxy-alkyl-Cl-3-alkyl-Cl-3-amino, phenyl, pyridyl, pyrrolidinyl or piperidinyl, for a pyrrolyl, thienyl, imidazolyl, pyrazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl group optionally substituted by one or two alkylene-Cl-3 groups, to which a phenyl ring may be condensed in each case through two atoms adjacent carbon atoms, by a C3-6-iminocycloalkylene-cycloalkylene-C5-8-imino group, morpholino, piperazino, dihydropyrazolo, tetrahydropyrazolo, tetrahydroisooxazole, tetrahydropyrazinyl or tetrahydropyridazinyl, optionally substituted by an alkyl-Cl- group 3 or carboxy-alkyl-Cl-3, or by a cycloalkylene-C3-6-imino group optionally substituted by an alkyl-Cl-3, carboxy-alkyl-Cl-3, hydroxy, hydroxy-alkyl-Cl-3 group, amino, carboxy, carboxy-alkoxy-Cl-3-alkyl-Cl-3, carboxy-alkyl-Cl-3-amino-alkyl-Cl-3, or carboxy-alkyl-Cl-3-amino-carbonyl-alkyl-Cl -3, by a bicycloalkylene-C5-8-imino group, morpholino, piperazino, dihydropyrazolo, tetrahydropyrazolo, tetrahydroisooxazole, tetrahydropylamide inyl or tetrahydropyridazinyloptionally substituted by an alkyl-Cl-3 or carboxy-alkyl-Cl-3 group, R3 represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a formyl or trifluoromethyl group, an alkoxy-Cl-3, amino group , alkyl-Cl-3-amino, di- (alkyl-Cl-3) -amino, alkanoyl-Cl-4-amino or N- (alkanoyl-Cl-4) -alkyl-Cl-3-amino an alkyl- Cl-3 optionally substituted by a hydroxy, alkoxy-Cl-3, carboxy, carboxy-alkoxy-Cl-3, carboxy-alkyl-Cl-3-amino, N- (alkyl-Cl-3) -carboxy-alkyl group Cl-3-amino or carboxy-alkyl-Cl-3-aminocarbonyl, a C2-3 alkenyl group substituted by a carboxy or carboxy-alkyl-Cl-3-aminocarbonyl group, or a carbimino group optionally substituted on the carbon atom by an alkyl-Cl-3 group, which at the imino nitrogen atom is substituted by a carboxy-alkoxy-Cl-3 or aminocarbonylamino group, or R2 and R3 together represent a group -CO-0-CH2- or -C0 -0-CH2CH2-, and R4 represents a hydrogen, fluorine, chlorine, bromine or iodine atom, an alkyl group -Cl-3, C3-7 cycloalkyl, trifluoromethyl or alkoxy-Cl-3, or Ar also means a heteroaryl group which may be substituted by the aforementioned residues R2 to R4, which are defined as mentioned above, X represents an oxygen or sulfur atom, a methylene group optionally substituted by one or two alkyl-Cl-3 groups, a carbonyl, sulfinyl, sulfonyl, imino, N- (alkyl-Cl-3) -imino or N- group ( carboxy-alkyl-Cl-3) -imino, where the alkyl part of the group N- (alkyl-Cl-3) -imino can be further substituted in the 2 or 3 position by an amino group, alkyl-Cl-3 - amino, di- (alkyl-Cl-3) -amino, alkanoyl-Cl-4-amino or N- (alkanoyl-Cl-4) -alkyl-Cl-3-amino, and Y represents a cyclohexyl group substituted by a group amino, or a phenyl or heteroaryl group substituted by the residue R5, wherein the aforementioned phenyl group may be substituted in each case by a fluorine, chlorine, bromine or iodine atom, or by a group alkyl-Cl-3 or alkoxy-Cl-3, as well as the heteroaryl group may be substituted by an alkyl-Cl-3 group, and R 5 represents a hydrogen atom, a cyano group or an amino, amino-alkyl-Cl group -3, amidino, guanidino or guanidino-alkyl-Cl-3 optionally substituted by a cleavable group in vivo. The aforementioned heteroaryl groups should be understood to mean a 5-membered heteroaromatic group optionally substituted by one or two alkyl-Cl-3 groups, containing an imino group optionally substituted by an alkyl-Cl-3 group, an oxygen or sulfur atom and one or two nitrogen atoms, as well as their partially hydrogenated derivatives, in particular dihydro derivatives, or a 6-membered heteroaromatic group containing one, two or three nitrogen atoms, wherein additionally a phenyl ring may be fused to the rings 5 and 6 member heteroaromatics previously mentioned through two adjacent carbon atoms. In addition, the carboxy groups previously mentioned in the definition of the residues may be substituted by a tetrazolo group or by a group which in vivo can be converted to a carboxy group, for example by a hydromethyl or formyl group, by an esterified carboxy group with an alcohol, in which the alcoholic portion is preferably an alkanol -Cl-6, a phenyl-alkanol-Cl-3, a cycloalkanol-C3-9, wherein a C5-8-cycloalkanol may additionally be substituted by one or two alkyl-Cl-3 groups, in which a methylene group in the 3 or 4 position is substituted by an oxygen atom or by an imino group optionally substituted by an alkyl-Cl-3, phenyl-alkyl-Cl-3 group , phenyl-alkoxy-Cl-3-carbonyl or alkoxy-C2-6-carbonyl or l-C2-6 alkane, and the cycloalkanoyl part may additionally be substituted by one or two alkyl-Cl-3 groups, a cycloalkenol-C4 -7 , an alkenol-C3-5, a phenyl-alkenol-C3-5, an alkynol-C3-5 or a phenyl-alkynol-C3-5, with the condition that there is no bond to the oxygen atom by a carbon atom carrying a double or triple bond, a C3-8-cycloalkyl-Cl-3 cycloalkyl, a bicycloalkanol with a total of 8 to 10 carbon atoms, which in the bicycloalkyl part is substituted by one or two C1-C3 alkyl groups, a 1,3- dihydro-oxo-1-isobenzofuranol or an alcohol of the formula RaC0-0- (RbCRc) -OH, in which Ra represents an alkyl-Cl-8, cycloalkyl-C5-7, phenyl or phenyl-alkyl-Cl- group 3, Rb represents a hydrogen atom, an alkyl-Cl-3, a C5-7 cycloalkyl or a phenyl group, and Rc represents a hydrogen atom or an alkyl-Cl-3 group, and the imino or amino groups mentioned in The definition of the residues can be replaced by a residue cleavable in vivo, for example by a hydroxy group, an acyl group such as the benzoyl or pyridinoyl group or an alkanoyl-Cl-16 group such as the formyl, acetyl, propionyl, butanoyl, pentanoyl group or hexanoyl, by an allyloxycarbonyl group, by an alkoxy-Cl-16-carbonyl group such as methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, isopropyloxycarbonyl , butyloxycarbonyl, tertiary butyloxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl or hexadecyloxycarbonyl, for a phenyl-alkoxy-Cl-16-carbonyl group such as the benzyloxycarbonyl group, phenylethyloxycarbonyl or phenylpropyl-oxycarbonyl, for an alkyl-Cl group -3-sulfonyl-C2-4-alkoxycarbonyl, alkoxy-Cl -3-alkoxyC2-4 -alkoxyC2-4 -carbonyl or RaCO-0- (RbCRc) -O-CO, wherein Ra a Rb are defined as mentioned in the above. In addition, the saturated alkyl and alkoxy moieties defined therein containing more than 2 carbon atoms, as well as the unsaturated alkanoyl and alkyl portions containing more than 3 carbon atoms also include their branched isomers, such as, for example, the groups isopropyl, terbutil, isobutyl, etc. Preferred compounds of the general formula I of the present invention are those in which A ethynylene group, a vinylene or ethylene group optionally substituted by a Cl-3 alkyl or Cl-3 carboxyalkyl group, or by a chlorine atom, bromine. or iodine, Rx a hydrogen atom, a Cl-3 alkyl group or Cl-3 carboxyalkyl, Ar a phenyl group substituted by residues R2 to R4, R2 representing a Cl-3 alkyl group which may be substituted by a group carboxy, phenyl, amino, alkyl-Cl-3-amino, carboxy-alkyl-Cl-3-amino, di (alkyl-Cl-3) -amino, N- (carboxy-alkyl-Cl-3) -alkyl -Cl -3-amino, phenylamino, N- (alkyl-Cl-3) -phenylamino, N- (alkanoyl-Cl-4) -phenylamino, heteroarylamino, N- (alkyl-Cl-3) -heteroarylamino, N- ( carboxy-alkyl-Cl-3) -phenylamino or N- (carboxy-alkyl-Cl-3) -heteroarylamino, a phenyl or phenylsulfonyl group, which in the phenyl part in each case can be substituted by a fluorine, chlorine atom, bromine or iodine, for a gru alkyl-Cl-3, carboxy-alkyl-Cl-3 or alkoxy-Cl-3, an alkyl-Cl-3-amino, carboxy-alkyl-Cl-3-amino, di (alkyl-Cl-3) group amino, N- (carboxy-alkyl-Cl-3) -alkyl-Cl-3-amino, phenylamino, N- (alkyl-Cl-3) -phenylamino, N- (carboxy-alkyl-Cl-3) -phenylamino, heteroarylamino, N- (alkyl-Cl-3) -heteroarylamino or N- (carboxy-alkyl-Cl-3) -heteroarylamino, an alkyl-Cl-5-carbonylamino, arylcarbonylamino, heteroarylcarbonylamino, alkyl-Cl-5-sulfonylamino group, arylsulfonylamino, heteroarylsulfonylamino, N- (alkyl-Cl-3) -alkyl-Cl-5-carbonylamino, N- (alkyl-Cl-3) -arylcarbonylamino, N- (alkyl-Cl-3) -heteroarylcarbonyl-a, N - (alkyl-Cl-3) -alkyl-Cl-5-sulfonylamino, N- (alkyl-Cl-3) -arylsulfonylamino or N- (alkyl-Cl-3) -heteroarylsulfonylamino, N- (carboxy-alkyl-Cl-) 3) -alkyl-Cl-5-carbonyl, N- (carboxy-alkyl-Cl-3) -arylcarbonyl-arnino, N- (carboxy-alkyl-Cl-3) -heteroarylcarbonyl, N- (carboxy-alkyl-Cl-) 3) -alkyl-Cl-5-sulfonylamino, N- (carboxy-alkyl-Cl-3) -arylsulfonyl amino or N- (carboxy-alkyl-Cl-3) -heteroarylsulfonylamino, a carbimino group substituted at the nitrogen atom by a carboxy-alkoxy-Cl-3, amino, alkyl-Cl-3-amino group, carboxy-alkyl-Cl-3-amino, di- (alkyl-Cl-3) -amino or 'N- (carboxy-alkyl-Cl-3) -alkyl-Cl-3-amino, and on the carbon atom by an alkyl-Cl-5 group, by a phenyl group optionally substituted by an alkyl-Cl-3 or alkoxy-Cl-3 group, or by a heteroaryl group optionally substituted by an alkyl-Cl-3 group, a heteroaryl group or heteroaryl-alkyl-Cl-3, which in each case can also be additionally substituted on the heteroaryl part by a phenyl or heteroaryl group, or by a phenyl or heteroaryl group and by a carboxy-alkyl-Cl-3 or alkoxy -Cl group -3-carbonyl-alkyl-Cl-3, or a carbonyl group which may be substituted by a hydrogen atom, a hydroxy group, alkoxy-Cl-5 or cycloalkoxy-C3-7, by an alkylene-Cl- group 5 or C3-7 cycloalkyl optionally substituted by a carboxy group, by a phenyl group which may be substituted by a fluorine, chlorine, bromine or iodine atom, by an alkyl-Cl-3, carboxy-alkyl-Cl- group 3, alkoxy? -Cl-3 or carboxy, p or an amino group, alkyl-Cl-5-amino, C3-7-amino-cycloalkyl, phenylamino or heteroarylamino, which in each case may additionally be substituted at the nitrogen atom by an alkyl-Cl-5, cycloalkyl-C5 group -7, phenyl-alkyl-Cl-3, carboxy-alkyl-Cl-3, 2- (di- (alkyl-Cl-3) -amino) -ethyl, 3- (di- (alkyl-Cl-3) - ammo) -propyl, di- (alkyl-Cl-3) -amino, 2- (N-carboxy-alkyl-Cl-3-alkyl-Cl-3-amino) -ethyl, 3- (N-carboxy-alkyl- Cl-3-alkyl-Cl-3-amino) -propyl or N-carboxy-alkyl-Cl-3-alkyl-Cl-3-amino, pyrrolidinyl or piperidinyl, by a pyrrolyl, thienyl, imidazolyl, pyrazolyl, thiazolyl group, pyridinyl, pyrimidinyl, pyrazinyl or pyridazomyl optionally substituted by an alkyl-Cl -3 group, to which a phenyl ring may be condensed in each case through two adjacent carbon atoms, by a C-C6-6alkylene group imino, bicyclo-alkylene-C5-8-? m? no, morpholino, piperazino, dihydro-pyrazolo, tetrahydropyrazolo, tetrahydroisooxazole, tetr ahydropyraziphenyl or tetrahydropyridazinyl, optionally substituted by an alkyl-Cl-3 or carboxy-alkylo-Cl-3 group, or by a pyrrolidino group, the previously mentioned pyrrolidino group being substituted by a hydroxy, hydroxy-alkyl-Cl-3 group , amino, carboxy, carboxy-alkyl-Cl-3, carboxy-alkoxy-Cl-3-alkyl-Cl-3, carboxy-alkyl-Cl-3-amino-alkyl-Cl-3 or carboxy-alkyl-Cl-3 -amino-carbonyl-alkyl-Cl-3, R3 represents a hydrogen atom, or a formyl group, an amino group, alkyl-Cl-3-amino, di- (alkyl-Cl-3) -amino, alkanoyl-Cl -4-amino or N- (alkanoyl-Cl-4) -alkyl-Cl-3-amino an alkyl-Cl-3 group optionally substituted by a hydroxy, alkoxy-Cl-3, carboxy, carboxy-alkoxy-Cl- group 3, carboxy-alkyl-Cl-3-amino, N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino or carboxy-alkyl-Cl-3-aminocarbonyl, a substituted C2-3 alkenyl group by a carboxy or carboxy-alkyl-Cl-3-aminocarbonyl group, or a possibly substituted carbimino group in the carbohydrate atom not by an alkyl-Cl-3 group, which at the imino nitrogen atom is substituted by a carboxyalkoxy-Cl-3 or aminocarbonylamino group, or R2 and R3 together represent a group -CO-0-CH2- or -C0- 0-CH2CH2-, and R4 represents a hydrogen atom, fluorine, chlorine, bromine or iodine, an alkyl-Cl-3, cycloalkyl-C3 -7, or alkoxy-Cl-3, or Ar also means a heteroaryl group which it may be substituted by the residues R2 to R4 mentioned above, X represents an oxygen or sulfur atom, a methylene group optionally substituted by one or two alkyl-Cl-3 groups, a carbonyl, sulfinyl, sulfonyl, imino, N- group ( alkyl-Cl-3) -imino or N- (carboxy-alkyl-Cl-3) -imino, wherein the alkyl part of the group N- (alkyl-Cl-3) -imino can be additionally substituted in the 2-position or 3 by an amino group, alkyl-Cl-3-amino, di- (alkyl-Cl-3) -amino, alkanoyl-Cl-4-amino or N- (alkanoyl-Cl-4) -alkyl-Cl-3- amino, and Y represents a cyclohexyl group substituted by an amino group, or a phenyl or heteroaryl group substituted by the residue R5, wherein the aforementioned phenyl group may be substituted in each case by a fluorine, chlorine, bromine or iodine atom, or by an alkyl-Cl-3 or alkoxy-Cl-3 group, as well as the heteroaryl group may be substituted by an alkyl-Cl-3 group, and R 5 represents a hydrogen atom, a cyano group or an amino group, amino-alkyl-Cl-3, amidino, guanidino or guanidino-alkyl-Cl-3 optionally substituted by a cleavable group in vivo, their pro-drugs, their tautomers, their stereoisomers, their mixtures and their salts, in particular those in which they mean A vinylene group optionally substituted by a chlorine, bromine or iodine atom, an ethylene or ethynylene group, Rj a hydrogen atom or an alkyl group Cl-3, Ar a pyridyl or thienyl group substituted by a benzoyl group, a bromofuranyl group substituted by a pyrrolidinocarbonyl group, a phenyl group substituted by the residues R2 to R4, R2 representing a phenyl or phenoxy group: a Cl-3 alkyl group which may be substituted by a phenyl, phenylamino, N- (alkyl-Cl-3) -phenylamino or N- (alkanoyl-Cl-4) -phenylamino group, a carboxy or alkoxy group -Cl-3-carbonyl, a benzoyl or phenylsulfonyl group, which in the phenyl part in each case may be substituted by a fluorine, chlorine or bromine atom, by a methyl, methoxy, carboxy or alkoxy-Cl-3-carbonyl group , being that in the previously mentioned benzoyl groups additionally the oxygen atom may be substituted by carboxy-alkoxy-Cl-3-imino or alkoxy-Cl-3 -carbonyl-alkoxy-Cl-3 -imino group, an alkyl -Cl group - 5-amino which in the alkyl part may be substituted by a phenyl, carboxy, alkoxy-Cl-3 group -carbonyl, carboxy-alkyl-Cl-3-aminocarbonyl, alkoxy-Cl-3-carbonyl-alkyl-Cl-3-aminocarbonyl, N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino-carbonyl , or N- (alkyl-Cl-3) -alkoxy-Cl-3-carbonyl-alkyl-Cl-3-aminocarbonyl, or a C3-7-cyanocarbonyl-cycloalkyl group, wherein the previously mentioned groups can be respectively further substituted in the nitrogen atom of the amine by a C3-7 cycloalkanoyl group, benzoyl or phenylsulfonyl, by a carboxy-alkyl-Cl-3-carbonyl or alkoxyl-Cl-3-carbonyl-alkyl-Cl-3 group -carbonyl, wherein the alkyl part of the alkylcarbonyl group in each case can be substituted by an amino group or trifluoroacet Llamino, by an alkanoyl-C 2-4 group, which in the alacanoyl part is substituted by an ammonium group , carboxy, alkoxy-Cl-3-carbonyl, carboxy-alkoxy-Cl-3, alkoxy? -Cl-3-carbon? l-alkoxy? -Cl-3, carboxy-alkyl-Cl-3-a mocarbonyl, alkoxy- Cl -3 -carbonyl -alkyl-Cl-3-apunocarbonyl, N- (alkyl-Cl-3) -carboxy-al which-Cl-3-apunocarbonyl or N- (alkyl-Cl-3) -alkoxy-Cl-3 -carbonyl-alkyl-Cl-3-ammocarbonyl, by a carboxy-alkyl-Cl-2 group -ammocarbonyl, alkoxy? -Cl-3-carbonyl-alky L-Cl-2-ammocarbonyl, carboxy-alkyl-Cl-3-ammocarbonyl-alkyl-Cl-2-ammocarbonyl or alkoxy-Cl-3 -carbonyl-alkyl -Cl -3-aminocarbonyl-alkyl-Cl-2-aminocarbonyl, a formyl, pyridylcarbonyl, thienylcarbonyl, imidazolylcarbonyl, 1-methyl-? M? Dazolecarbonyl, thiazolylcarbonyl or m-dylcarbonyl group, a benz. m? dazol-1-? l, benz? dazol-1-? -methyl 5-oxo-4, 5-d? h? dro-p? razol-3-? l eventually replaced by one or two methylene groups, a pyrolyl group substituted by a phenyl group, by a phenyl group and an alkylene group, or by one or two alkylene-Cl groups, in wherein an alkyl substituent may be simultaneously substituted by a carboxy or alkoxy-Cl-3-carbonyl group, or a carbonyl group which may be substituted by an alkyl-Cl-5 group optionally substituted by a carboxy or alkoxy-Cl-3 group -carbonyl, a C3-7 cycloalkyl group, by a ring group, alkyl-Cl-5-amino, which in each case may additionally be substituted on the nitrogen atom by an alkyl-Cl-5 group, which may be substituted by a C3-7 cycloalkyl group, phenyl, pyrrolidinyl or pyridinyl, or in the 2 or 3 position by a di- (alkyl-Cl-3) -amino group, or by a di- (alkyl-Cl-3) group -amino, by a carboxy-alkyl-Cl-3-amino or alkoxy-Cl-3-carbonyl-alkyl-Cl-3 group min, which in each case are substituted at the nitrogen atom of the amine by a pyrazole group optionally substituted by an alkyl-Cl-3 group, by a cycloalkyleneimino group of 3 to 7 members, which may be substituted by one or two groups alkyl-Cl-3, where the aforementioned pyrrolidino groups optionally substituted by a methyl group can be further substituted by a hydroxymethyl, carboxy, alkoxy-Cl-3-carbonyl, carboxy-alkyl-Cl-3, alkoxy-Cl- group 3-carbonyl-alkyl-Cl-3, carboxy-alkyloxy-Cl-3-alkyl-Cl-3, alkoxy-Cl-3-carbonyl-alkyloxy-Cl-3-alkyl-Cl-3, carboxy-alkyl-Cl-3-amino-alkyl-Cl-3 , N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino-alkyl-Cl-3, a1-coxy-Cl-3-carbonyl-alkyl-Cl-3-amino-alkyl-Cl-3, N - (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino-alkyl-Cl-3-amino-alkyl-Cl-3, by a morpholino group, piperazino, 4-methyl-piperazino, piperazine-alkyl- Cl-3, dihydropyrazole, tetrahydropyrazolo, tetrahydroisooxazolo, or 7- azabicycloheptyl, or by a group N- (alkyl-Cl-3) -phenyl or N- (alkyl-Cl-3) -pyridylamino optionally substituted on the alkyl part by a carboxy or alkoxy-Cl-3-carbonyl group, R3 represents a hydrogen, fluorine, chlorine or bromine atom, a hydroxy, alkoxy-Cl-3, trifluoromethyl, amino or alkanoyl-C2 -3-amino group, an alkyl- Cl-3, which may be substituted by a hydroxy, carboxy, alkoxy-Cl-3-carbonyl, carboxy-alkoxy-Cl-3, alkoxy-Cl-3-carbonyl-alkoxy-Cl-3, carboxyalkyl-Cl-3 group -aminocarbonyl, alkoxy-Cl-3 -carbonyl -alkyl-C1 -3-aminocarbonyl, N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-aminocarbonyl or N- (alkyl-Cl-3) -alkoxy -Cl-3-carbonyl-alkyl-Cl-3-aminocarbonyl, an alkyl-Cl-3 group substituted by a carboxyalkyl-Cl-3-amino group, alkoxy-Cl-3-carbonyl-alkyl-Cl-3-amino, N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino, or alkoxy-Cl-3-carbonyl-alkyl-Cl-3-aminocarbonyl, a C 2-3 alkenyl group substituted by a carboxy group or alkoxy-Cl-3-carbonyl, or a carbimino group optionally substituted on the carbon atom by an alkyl-Cl-3 group, which at the imino nitrogen atom is substituted by a carboxy-alkoxy-Cl-3, alkoxy group -Cl-3-carbonyl-alkoxy-Cl-3 or aminocarbonylamino, or R2 and R3 together represent a group -CO-0-CH2-, and R4 represents a hydrogen, fluorine, chlorine or bromine atom, an alkyl-Cl group -3 or trifluoromethyl, X represents an oxygen or sulfur atom, a NH group optionally substituted by an alkyl-Cl-3 group, and Y represents a cyclohexyl group substituted by an amino group, or a phenylene or pyridinylene group substituted by an amidino group which may be substituted by a benzoyl or alkoxy-Cl-8-carbonyl group, wherein the aforementioned phenylene group may be substituted by a methyl or methoxy group, and the pyridinylene pgroup previously mentioned by a methyl group, their tautomers, their stereoisomers, their mixtures and their salts. The especially preferred compounds of the present invention are the compounds of the general formula to. wherein A anethylene or ethynylene group, X an oxygen atom or an imino group optionally substituted by a methyl group, R2 an alkyl-Cl -4 -carbonylamino group or a C3-5-carbonylamino cycloalkyl group, each of which In the case of the nitrogen atom of the amine, they are substituted by a carboxy-alkyl-Cl-2, alkoxy-Cl-3-carbonyl-alkyl-Cl-2, carboxy-alkyl-Cl-2-aminocarbonyl-alkyl-Cl- group. 2, or alkoxy-Cl-3-carbonyl-alkyl-Cl-2-aminocarbonyl-alkyl-Cl-2, an alkyl-Cl-4-amino or C3-5-amino-cycloalkyl group, which in each case in the Nitrogen atom of the amine are substituted by a carboxy-alkyl-Cl-3-carbonyl, alkoxy-Cl-3-carbonyl-alkyl-Cl-3-carbonyl, carboxy-alkyl-Cl-2-aminocarbonyl-alkyl -Cl group -2-carbonyl, alkoxy-Cl-3-carbonyl-alkyl-Cl-2-aminocarbonyl-alkyl-Cl-2-carbonyl, carboxy-alkyl-Cl-2-aminocarbonyl, alkoxy-C-3-carbonyl-alkyl -Cl -2-aminocarbonyl, carboxyalkyl-Cl-2-aminocarbonyl-alkyl-Cl- 2-aminocarbonyl or alkoxy-Cl-3-carbonyl-alkyl-Cl-2-aminocarbonyl-alkyl-Cl-2-ammocarbonyl substituted by an amino group optionally substituted on the alkyl part, by a carboxymethyloxymethylcarbonyl group, alkoxy-Cl -3- carboni1 -methyloxymethylcarbonyl, carboxymethylaminomethylcarbonyl, alkoxy-Cl-3 -carbonylmethylaminomethylcarbonyl, N-methylcarboxymethylaminomethylcarbonyl, N-methyl-alkoxy-Cl-3 -carbonyl-1-carboxy-ethyl-1-amino-methylcarbonyl, aminomethylcarbonyl, 2-aminoethylcarbonyl, carboxy-alkyl-Cl-2- aminocarbonylmethyloxymethylcarbonyl, alkoxy-Cl-3-carbonyl-alkyl-Cl-2-aminocarbonylmethyloxymethylcarbonyl, carboxy-alkyl-Cl -2-aminocarbonylmethylaminomethylcarbonyl, alkoxy-Cl-3-carbonyl-alkyl-Cl-2-aminocarbonylmethylamino-methylcarbonyl, N-methyl-1-carboxy -alkyl-Cl-2-aminocarbonylmethylaminomethylcarbonyl, or N-methyl-alkoxy-Cl-3-carbonyl-alkyl-Cl-2-aminocarbonylmethylaminomethylcarbonyl, or a carbonyl group substituted by a cyclopentyl group, a group quilo-C3 -5, which may additionally be substituted by a carboxy or alkoxy-Cl-3-carbonyl group, an alkyl-Cl -4-amino, phenylamino or pyridylamino group substituted at the nitrogen atom of the amine by an alkyl group -Cl-4, carboxy-alkyl-Cl-3 or alkoxy-Cl-3-carbonyl-alkyl-Cl-3, by a pyrolidino group substituted by a methyl, hydroxymethyl, amino, carboxy, alkoxy-Cl-3-carbonyl group , carboxy-alkyl-Cl -2, a1-coxy-Cl -3-carbonyl-alkyl-Cl-2, carboxymethyloxymethyl, alkoxy-Cl-3-carbonylmethyloxymethyl, carboxymethylaminomethyl, a-coxy-Cl -3-carbonylmethylamino-methyl, carboxymethylaminocarbonylmethyloxymethyl or alkoxy -Cl-3-carbonylmethylaminocarbonylmethyloxymethyl, R3 a hydrogen, fluorine, chlorine or bromine atom or a trifluoromethyl group, an alkyl-Ci-2 group optionally substituted by a hydroxy, carboxy, alkoxy-Cl-3-carbonyl, carboxymethyloxy, alkoxy group -Cl-3-carbonylmethyloxy, carboxymethylamino, N-methyl-carboxymethylamino, alkoxy-Cl-3-carbonylmethylamino, N-methyl-alkoxy-Cl-3-carbonylmethylamino, carboxyethylaminocarbonyl or alkoxy-Cl-3-carbonyl-methylaminocarbonyl, a vinyl group substituted by a carboxy or alkoxy-Cl-3-carbonyl group, R4 a hydrogen, fluorine, chlorine or bromine atom, a methyl, ethyl or trifluoromethyl group, and Y an amidino group optionally substituted by an alkoxy-Cl-8-carbonyl or benzoyl group, their tautomers, their stereoisomers, their mixtures and their you go out . Very especially preferred compounds of the present invention are the compounds of the general formula la, in which A, an ethylene or ethynylene group, X an imino group, R2 an alkyl-Cl-4-aminocarbonyl group which in each case the nitrogen atom of the amine is substituted by a carboxy-alkyl-Cl-2 group, or alkoxy-Cl-3-carbonyl-alkyl-Cl-2, an alkyl-Cl-4-amino group substituted on the nitrogen atom of the amine by a carboxy-alkyl-Cl-3-carbonyl, alkoxy-Cl-3-carbonyl-alkyl-Cl-3-carbonyl, carboxy-alkichl-Cl-2-aminocarbonyl or alkoxy-Cl-3-carbonyl-alkyl -Cl-2-aminocarbonyl, or a carbonyl group which may be substituted by a C3-5 alkyl group which may additionally be substituted by a carboxy or alkoxy-Cl-3-carbonyl group, by an alkyl-Cl-4 amino or substituted pyridylamino group in the Nitrogen atom of the amine by a carboxy-alkyl-Cl-3 or alkoxy-Cl-3 carbonyl-alkyl-Cl-3 group, by a pyrolidine group optionally substituted by a methyl group, R3 an alkyl-Cl-2 group optionally substituted by a carboxy or alkoxy-Cl-3-carbonyl group, R4 a hydrogen atom or a methyl group, and Y an amidino group optionally substituted by an alkoxy-Cl-8-carbonyl or benzoyl group, its tautomers, its stereoisomers, its mixtures and its salts. As especially preferred compounds, the following are mentioned by way of example: (a) rac-4-. { 3- [5-Ethoxycarbonylmethyl-2-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} benzamidine, (b) rac-4-. { 3- [2,5-dimethyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} benzamidine, (c) 4- [3- (2, 5-dimethyl-4-isopropylcarbonyl-phenyl) -propargylaminobenzamidine, (d) 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-pyridin-2-yl-aminocarbonyl) -phenyl] -propargylamino} benzamidine, (e) 4 -. { 3 - [2,5-dimethyl-4- (N-methyl-N-pyridin-2-yl-aminocarbonyl) -phenyl] -prop-1-ylamino} benzamidine, (f) 4- [3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzamidine, (g) 4-. { 3- [2, 5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-ethyl-carbonylamino) -phenyl] -propargylamino} benzamidine, (h) 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-hydroxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylaminobenzamidine, e (i) 4 -. { 3 - [2,5-dimethyl-4- (N-isopropyl-N-hydroxycarbonyl-1-methylcarbonyl-amino) -phenyl] -propargylamino} benzamidine and its salts. According to the invention, the compounds of the general formula I are obtained according to known methods, for example according to the following procedures: a. Reaction of a compound of the general formula Ar - Z? (II) wherein Ar is defined as mentioned at the beginning and Z- represents a group lost as a halogen atom or a sulfonyloxy group, for example a chlorine, bromine or iodine atom or a trifluoromethylsulfonyloxy group, with a compound of general formula in which R-! and X are defined as mentioned at the beginning, Y 'has the meanings mentioned at the beginning for Y, with the proviso that an existing amno or imino group is protected by a usual protective residue, and A' represents an ethynyl group, and optional subsequent catalytic hydrogenation and / or cleavage of the protective residue used. The reaction is preferably carried out in a solvent such as acetonitrile, diethyl ether, tetrahydrofuran or dimethylformamide in the presence of a palladium catalyst such as bis- (triphenylphosphine) -palladium (II) chloride or tetrakis- (triphenylphosphine) -palladium (cf. ) in the presence of a tertiary or inorganic base such as triethylamine, N-isopropyl-diethylamine, potassium terbutylate, sodium carbonate or cesium carbonate, and in the presence of a reaction accelerator such as a copper halide, such as copper iodide ( I) and at temperatures between 20 and 120 ° C, preferably at temperatures between 40 and 100 ° C (see also K. Sonogashira, Comprehensive Organic Synthesis, Vol. 3, Seite 52ff., Pergamon Press, Oxford 1991). The protective residues eventually used and their cleavage will be described below (see also T. Greene, Protective Groups in Organic Synthesis, Wiley Interscience, New York 1981). b. For the preparation of a compound of the general formula I in which the residue Ar-A contains a carboxy group and R5 is defined as mentioned at the beginning or in which the residue Ar-A is defined as mentioned at the beginning and R5 represents an amino group, amino-Cl-3 alkyl, amidino or guanidino or the residue Ar-A contains a carboxy group and R5 represents an amino, amino-Cl-3 alkyl, amidino or guanidino group: The conversion of a compound of the general formula Ar '- A - HCR - X - Y' '(IV) in which A, R? and X are defined as mentioned at the beginning, Ar1 and Y'1 have the meanings mentioned at the beginning for Ar and Y, with the proviso that Ar 'contains a group that by hydrolysis, treatment with an acid or a base, thermolysis or hydrogenolysis can be converted to a carboxy group, and Y1 'has the meaning mentioned at the beginning, or Ar' has the meanings mentioned at the beginning for Ar and Y '' contains a group that by hydrolysis, treatment with an acid or base, thermolysis or hydrogenolysis can be converted to an amino group, aminoalkyl Cl-3, amidino or guanidino, or Ar 'contains a group which by hydrolysis, treatment with an acid or base, thermolysis or hydrogenolysis can be converted to a carboxy group and Y' 'contains a group which by hydrolysis, treatment with an acid or base, thermolysis or hydrogenolysis can be converted to an amino group, amino-Cl-3 alkyl, amidino or guanidino, by hydrolysis, treatment with an acid or base, thermolysis or hydrogenolysis to a compound of the general formula I, in which the residue Ar-A contains a carboxy group and R5 is defined as mentioned at the beginning, or the residue Ar-A is defined as mentioned at the beginning and R 5 represents an amino group, amino-alkyl Cl-3, amidino or guanidino or the residue Ar-A contains a carboxy group and R 5 represents a amino group, amino-Cl-3 alkyl, amidino or guanidino. As the group which can be converted to a carboxy group, for example, a carboxyl group protected by a protective residue, such as its functional derivatives, for example, its unsubstituted amides, esters, thioesters, trimethylsilyl esters, orthoesters or imino esters, are suitable. or substituted, which are conveniently converted to a carboxyl group by hydrolysis, their esters with tertiary alcohols, for example, the terbutyl ester, which are conveniently converted to a carboxyl group by treatment with an acid or thermolysis, and their esters with aralkanols , for example, benzyl ester which are converted to a carboxyl group conveniently by hydrogenolysis. The hydrolysis is conveniently carried out either in the presence of; an acid such as hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, trichloroacetic acid, trifluoroacetic acid or their mixtures, or in the presence of a base such as lithium hydroxide, sodium hydroxide or potassium hydroxide in a suitable solvent such as water, water / methanol, water / ethanol, -water / isopropanol, methanol, ethanol, water / tetrahydrofuran or water / dioxane, at temperatures between -10 and 120 ° C, for example, at temperatures between room temperature and the boiling temperature of the mixture of the reaction. If a compound of the general formula IV contains, for example, the terbutyl or tert-butyloxycarbonyl group, then these can also be cleaved by treatment with an acid such as trifluoroacetic acid, formic acid, p-toluenesulfonic acid, sulfuric acid, hydrochloric acid , phosphoric acid or polyphosphoric acid, optionally in an inert solvent such as methylene chloride, chloroform, benzene, toluene, diethyl ether, tetrahydrofuran or dioxane, preferably at temperatures between -10 and 120CC, for example at temperatures between 0 and 60 ° C, or also in thermal form, optionally in an inert solvent such as methylene chloride, chloroform, benzene, toluene, tetrahydrofuran or dioxane, and preferably in the presence of a catalytic amount of an acid such as p-toluenesulfonic acid, sulfuric acid, phosphoric acid or polyphosphoric acid, preferably at the boiling temperature of the solvent used, for example at temperatures Between 40 and 120 ° C. If a compound of the formula IV generates, for example, the benzyloxy or benzyloxycarbonyl group, then these can also be cleaved in a hydrogenating form in the presence of a hydrogenation catalyst such as palladium / carbon in a suitable solvent such as methanol, ethanol, ethanol / water, glacial acetic acid, ethyl acetate, dioxane or dimethylformamide, preferably at temperatures between 0 and 50 ° C, for example, at room temperature and a hydrogen pressure of 1 to 5 bar. c. For the preparation of a compound of the general formula I in which R 5 represents an amidino group: The reaction of a compound which is optionally formed in the reaction mixture, of the general formula wherein A, Ar, R-, and X are defined as mentioned at the beginning, and Y'1 means one of the residues mentioned at the beginning for Y, with the proviso that and R5 represents a group Za - (HN =) C, in which Zx represents an alkoxy group or aralkoxy such as the methoxy, ethoxy, n-propoxy, isopropoxy or benzyloxy group, or an alkylthio or aralkylthio group such as the methylthio, ethylthio, n-propylthio or benzylthio group with an ammonium salt such as diammonium carbonate or ammonium acetate.

The reaction is conveniently carried out in a solvent such as methanol, ethanol, n-propanol, tetrahydrofuran or dioxane at temperatures between 0 and 150 ° C, preferably at temperatures between 0 and 80 ° C. A compound of the general formula V is obtained, for example, by the reaction of a corresponding cyano compound with a corresponding alcohol such as methanol, ethanol, n-propanol, isopropanol or benzyl alcohol, in the presence of an acid such as hydrochloric acid, or by the reaction of a corresponding amide with a trialkyloxonium salt such as tiethyxonium tetrafluoroborate in a solvent such as methylene chloride, tetrahydrofuran or dioxane, at temperatures between 0 and 50 ° C, however, preferably at 20 ° C, or a corresponding nitrile with acid sulfhydryl, suitably in a solvent such as pyridine or dimethyl-fomamide and the presence of a base such as triethylamine, and the subsequent alkylation of the thioamide formed with a corresponding alkyl or aralkyl halide. In the previously described action, an addition of halogen acid to an electron-rich or electron-poor triple bond can be carried out simultaneously. d. For the preparation of a compound of the general formula I in which R 5 represents an amidino group substituted with a hydroxy group: The reaction of a compound which is optionally formed in the reaction mixture, of the general formula Ar - A - HCR - X - Y1 '(V) in which A, Ar, RL and X are defined as mentioned at the beginning, and Y1' means one of the residues mentioned at the beginning for Y, with the proviso that and R5 represents a group Z ? - (HN =) C, in which ZL represents an alkoxy or aralkoxy group such as the methoxy, ethoxy, n-propoxy, isopropoxy or benzyloxy group, or an alkylthio or aralkylthio group such as the methylthio, ethylthio, n-propyl or benzylthio group with hydroxylamine or its salts. The reaction is conveniently carried out in a solvent such as methanol, ethanol, n-propanol, water, tetrahydrofuran, tetrahydrofuran / water, dioxane or dioxane / water, at temperatures between 0 and 150 ° C, preferably at temperatures between 0 and 80 °. C. and. For the preparation of a compound of the general formula I in which X represents an oxygen or sulfur atom, a carbonyl, inmino or? - (C1.3 alkyl) -imino group: The reaction of a compound of the general formula I Ar - A - HCRX - Z2 (VI) wherein A, Ar, R? are defined as mentioned at the beginning, and Z2 represents a group lost as a halogen atom or a sulfonyloxy group, for example a bromine or iodine atom, a methanesulfonyloxy or p-toluenesulfonyloxy group, with a compound of the general formula U - Y (VII) wherein Y is defined as mentioned at the beginning, and U means a hydroxy, mercapto, hydroxycarbonyl, imino or N- (C 1 -) alkylimino group. The reaction is preferably carried out in a solvent such as methanol, ethanol, methylene chloride, tetrahydrofuran, toluene, dioxane, dimethylsulfoxide or dimethylformamide, optionally in the presence of an inorganic or tertiary organic base, preferably at temperatures between 20 ° C and 20 ° C. boiling temperature of the solvent used. F. For the preparation of a compound of the general formula I in which Ar and / or Y contain an in vivo cleavable residue: The reaction of a compound of the general formula Ar 1 1 - A - HCR, - X - Y '1' (VIII) where A, R? and X are defined as mentioned at the beginning, Ar "and Y '' 'have the meaning mentioned at the beginning for Ar and Y, with the proviso that Ar' 'contains a carboxy group and Y' '' has the meanings mentioned above. principle for Y, or Ar '' have the meanings mentioned at the beginning for Ar and Y '' 'contain an amino group, amino-C ^ alkyl, amidino or guanidmo, or Ar' 'contains a carboxy group and Y' '' a amino group, amino-C1-3alkyl, amidino or guanidino, with a compound of the general formula Z3-R7 (IX) in which R7 signifies an alkoxycarbonyl group, a RaCO-0- (RbCRc) group or the acyl residue of one of the in-vivo cleavable residues mentioned at the beginning, where Ra a Rc is defined as mentioned at the beginning, and Z3 means a nucleophilic lost group such as a halogen atom, for example a chlorine, bromine or iodine atom, or a p-nitrophenyl group, or else, if Ar '' contains a carboxy group, a hydroxy group. The reaction is preferably carried out in a solvent such as methanol, ethanol, methylene chloride, tetrahydrofuran, toluene, dioxane, dimethylsulfoxide or dimethylformamide, optionally in the presence of an acid activating agent or a dehydrating agent, and optionally in the presence of an inorganic or tertiary organic base, preferably at temperatures between 20 ° C and the boiling temperature of the solvent used. With a compound of the general formula IX in which Z3 represents a nucleophobic lost group, the reaction is preferably carried out in a solvent such as methylene chloride, acetonitrile, tetrahydrofuran, toluene, dimethylformamide or dimethyl sulfoxide, optionally in the presence of a base such as sodium hydride, potassium carbonate, potassium terbutylate or N-ethyldiisopropylamine, at temperatures between 0 and 60 ° C. With a compound of the general formula IX in which Z3 represents a hydroxy group, the reaction is optionally carried out in a solvent or mixture of solvents such as methylene chloride, dimethylformamide, benzene, toluene, chlorobenzene, tetrahydrofuran, benzene / tetrahydrofuran or dioxane in the presence of a dehydrating agent, for example in the presence of chloroformic isobutyl ester, orthocarbonic acid tetraethyl ester, orthoacetic acid trimethyl ester, 2,2-dimethoxypropane, tetramethoxysilane, thionyl chloride, trimethylchlorosilane, phosphorus trichloride , phosphorus pentoxide, N, N '-dicyclohexyl-carbodiimide, N, N' -dicyclohexylcarbodiimide / N-hydroxy-succinimide, N, N '-dicyclohexylcarbodiimide / 1-hydroxy-benzotriazole, 2- (lH-benzotriazole-1-tetrafluoroborate) -yl) -1, 1, 3, 3-tetramethyluronium, 2- (lH-benzotriazol-1-yl) -1, 1,3,3-tetramethyluronium / 1-hydroxy-benzotriazole, N, N'-carbonyldiimidazole tetrafluoroborate or trif enylphosphine / carbon tetrachloride, and optionally with the addition of a base such as pyridine, 4-dimethylaminopyridine, N-methylmorpholine or triethylamine, conveniently at temperatures between 0 and 150 CC, preferably at temperatures between 0 and 100 ° C. If in a compound of the general formula IX Z3 means a hydroxy group, then the reaction can also be carried out with one of its reactive derivatives such as its esters, imidazolides or halides, preferably in a solvent such as methylene chloride or ether, and preferably in the presence of a tertiary organic base such as triethylamine, N-ethyl-diisopropylamine or N-methylmorpholine at temperatures between 0 and 150 CC, preferably at temperatures between 50 and 100 ° C. If, according to the invention, a compound of the general formula I is obtained in which R 5 represents an amidino group, then it can be converted by alkylation into a halogenated acetic acid derivative, by subsequent hydrolysis and decarboxylation in a corresponding amidino compound substituted by one or two methyl groups, and / or a compound of the general formula I in which R 5 represents a hydroxyamidino group, then it can be transformed by catalytic hydrogenation into a corresponding amidino compound, and / or a compound of the general formula I containing a double or triple bond, then this can be transformed by catalytic hydrogenation into a corresponding saturated compound, and / or a compound of the general formula I in which X represents a sulfur atom, then it can be transformed by oxidation in a corresponding sulfinyl or sulfonyl compound, and / or a compound of the formula I, in which R2 represents a tetrahydropyrazolecarbonyl group, then it can be converted by oxidation into a corresponding 4,5-dihydropyrazolcarbonyl compound, and / or a compound of the general formula I containing a carbonyl group, then this can be transformed by a corresponding oxime into a corresponding oxime compound, and / or a compound of the general formula I containing a carboxy group, then this can be transformed by a corresponding amine into a corresponding amide.

The subsequent alkylation is conveniently carried out in a solvent such as methylene chloride, tetrahydrofuran, dioxane, dimethisulfoxide, dimethylformamide or acetone, optionally in the presence of a reaction accelerator such as sodium or potassium iodide, and preferably the presence of a base such as sodium carbonate or potassium carbonate or in the presence of a tertiary organic base such as N-ethyl-diisopropylamine or N-methyl-morpholine, which at the same time can also serve as solvents, or possibly in the presence of silver carbonate or silver oxide, at temperatures between -30 and 100 ° C, but nevertheless preferably at temperatures between -10 and 80 ° C. The subsequent hydrolysis is conveniently carried out either in the presence of an acid such as hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, trichloroacetic acid, trifluoroacetic acid or mixtures thereof, or in the presence of a base such as lithium hydroxide, hydroxide sodium or potassium hydroxide, in a suitable solvent such as water, water / methanol, water / ethanol, water / isopropanol, methanol, ethanol, water / tetrahydrofuran or water / dioxane. The subsequent decarboxylation is carried out in the presence of an acid as described above at temperatures between -10 and 120 ° C, for example at temperatures between room temperature and the boiling temperature of the reaction mixture. The subsequent catalytic hydrogenation is preferably carried out in the presence of a hydrogenation catalyst such as palladium / carbon and in a suitable solvent such as methanol, ethanol, ethanol / water, glacial acetic acid, ethyl acetate, dioxane or dimentylformamide, preferably a temperatures between 0 and 50 ° C, for example at room temperature and at a hydrogen pressure of 1 to 5 bar. The subsequent oxidation is preferably carried out in a solvent or mixture of solvents, for example in water, water / pyridine, acetone, methylene chloride, acetic acid, acetic acid / acetic anhydride, dilute sulfuric acid or trifluoroacetic acid according to oxidizing agent used, conveniently at temperatures between -80 and 100 ° C. For the preparation of a corresponding sulfinyl compound of the general formula I, the oxidation is conveniently carried out with an equivalent of the oxidation agent used, for example with hydrogen peroxide in glacial acetic acid, trifluoroacetic acid or formic acid from 0 to 20 ° C, or in acetone from 0 to 60 ° C, with a peracid such as perforic acid in glacial acetic acid or trifluoroacetic acid of 0 to 50 ° C or with m-chloro perbenzoic acid in methylene chloride, chloroform or dioxane. 20 to 80 ° C, with sodium metaperiodate in methanol or aqueous ethanol of -15 to 25 ° C, with bromine in glacial acetic acid or aqueous acetic acid, possibly in the presence of a weak base such as sodium acetate, with N-bromosuccinimide in ethanol, with terbutilhipochlorite in methanol from -80 to -30CC, with iodine benzodichloride in aqueous pyridine from 0 to 50CC, with nitric acid in glacial acetic acid from 0 to 20 ° C, with chromic acid in glacial acetic acid oe n acetone from 0 to 20 ° C, and with sulfuryl chloride in methylene chloride at -70 ° C, the thio-ether-chloro complex obtained therefrom is conveniently hydrolyzed with aqueous ethanol. For the preparation of a sulfonyl compound of the general formula I, oxidation from a corresponding sulfinyl compound is conveniently carried out with one or more equivalents of the oxidation agent used, or from a corresponding sulfenyl compound, conveniently with two or more equivalents of the oxidizing agent used, for example with hydrogen peroxide in glacial acetic acid / acetic anhydride, trifluoroacetic acid or in formic acid from 20 to 100 ° C, or in acetone from 0 to 60 ° C, with a peracid as acid perfromic acid or m-chloroperbenzoic acid in glacial acetic acid, trifluoroacetic acid, methylene chloride or chloroform, at temperatures between 0 and 60 ° C, with nitric acid in glacial acetic acid from 0 to 20 ° C, with chromic acid, sodium periodate or potassium permanganate - in acetic acid, water / sulfuric acid or in acetone from 0 to 20 ° C. For the preparation of a 4,5-dihydropyrazolocarbonyl compound of the general formula I the oxidation can also be carried out by the oxygen of the air at room temperature in one of the aforementioned solvents. The subsequent formation of the oxime is conveniently carried out in a solvent such as methanol / toluene, in the presence of a dehydrating agent such as a molecular filter, preferably at the boiling temperature of the solvent used. The subsequent formation of the amide is preferably carried out in a solvent or mixture of solvents such as methylene chloride, dimethylformamide, benzene, toluene, chlorobenzene, tetrahydrofuran, benzene / tetrahydrofuran or dioxane in the presence of a dehydrating agent, for example in the presence isobutyl ester of chloroformic acid, orthocarbonic acid tetraethyl ester, orthoacetic acid trimethyl ester, 2,2-dimethoxypropane, tetramethoxysilane, thionyl chloride, trimethylchlorosilane, phosphorus trichloride, phosphorus pentoxide, N, N'-dicyclohexylcarbodiimide, N, N '-dicyclohexylcarbodiimide / N-hydroxysuccinimide, N, N' -dicyclohexylcarbodiimide / 1-hydroxy-benzotriazole, 2- (lH-benzotriazol-1-yl) -, 1,3,3-tetramethyluronium tetrafluoroborate, 2-tetrafluoroborate - (1H-benzotriazol-1-yl) -1, 1, 3, 3-tetramethyluronium / 1-hydroxy-benzotriazole, N, N'-carbonyldiimidazole or triphenylphosphine / carbon tetrachloride, and optionally with the ad of a base such as pyridine, 4-dimethylaminopyridine, N-methyl-morpholine or triethylamine, conveniently at temperatures between 0 and 150 ° C, preferably at temperatures between 0 and 100 ° C. In the case of the reactions described above it is possible to protect the optionally existing reactive groups such as the hydroxy, carboxy, amino, alkylamino or imino groups with the usual protecting groups, which after the reaction are further cleaved (see also T. Greene , Protective Groups in Organic Synthesis, Wiley Interscience, New York 1981). As the protective residue for a hydroxy group, the trimethylsilyl, acetyl, benzoyl, tertiary butyl, trityl, benzyl or tetrahydropyranyl group can be used as protective residues for a carboxyl group, the trimethylsilyl group, methyl, ethyl, tert-butyl, benzyl or tetrahydropyranyl, and protective residue for an amino, alkylamino or imino group the acetyl group, trifluoroacetyl, benzoyl, ethoxycarbonyl, tert-butoxycarbonyl, benzyloxycarbonyl, benzyl, methoxybenzyl or 2,4-dimethoxybenzyl, and additionally for the amino group the phthalyl group. the eventual subsequent cleavage of a used protective residue is effected, for example, in hydrolytic form in an aqueous solvent, for example in water, isopropanol / water, tetrahydrofuran / water or dioxane / water, in the presence of an acid such as trifluoroacetic acid, hydrochloric acid or sulfuric acid, or in the presence of an alkaline base such as lithium hydroxide, sodium hydroxide or potassium hydroxide, or by cleavage of ether, for example in the presence of iodotrimethylsilane, at temperatures between 0 and 100 ° C, preferably at temperatures between 10 and 50 ° C. The cleavage of a benzylcarbonyl, methoxybenzylcarbonyl or benzyloxycarbonyl residue is carried out, 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, acetic acid ethyl ester, dimethylformamide , dimethylformamide / acetone or glacial acetic acid, optionally with the addition of an acid such as hydrochloric acid at temperatures between 0 and 50 CC, however preferably at room temperature, and with a hydrogen pressure of 1 to 7 bar, however preferably from 3 to 5 bar. The cleavage of a terbutyl or terbutyloxycarbonyl residue is preferably carried out by treatment with an acid such as trifluoroacetic acid or hydrochloric acid, possibly with the use of a solvent such as water, methylene chloride, diethyl ether, tetrahydrofuran or dioxane. The cleavage of an allyloxycarbonyl residue is carried out by treatment with a catalytic amount of tet ra- (triphenylphosphin) -palladium (0), preferably in a solvent such as tetrahydrofuran and preferably in the presence of an excess of a base such as morpholine or 1,3-dimedon, at temperatures between 0 and 100 ° C, preferably at room temperature and under an inert gas, or by treatment with a catalytic amount of tri- (triphenylphosphine) -rodium chloro (I) in a solvent such as aqueous ethanol and optionally in the presence of a base such as 1,4-diazabicyclo [2.2.2] -octane at temperatures between 20 and 70 ° C. The compounds of the general formulas II to IX which are used as starting substances, which are known in the literature in part, are obtained according to processes known from the literature and, for that matter, their preparation is described in the examples.

Thus, a compound of the general formula II is obtained, for example, by the reaction of a corresponding halogenated benzene substituted with a corresponding compound, a compound of the general formula III by the reaction of a corresponding aniline with a propargylhalogenide and the subsequent conversion of the substituted aniline obtained in this way to a compound of the general formula III according to known methods, for example by the reaction of Pinner, as well as the compounds of the general formulas IV, V, VI and VIII conveniently according to usual methods as described in the present invention. In addition, the compounds of the general formula 1 obtained can be separated into their obtained enantiomers and / or diastereomers, and the compounds of the general formula I obtained which contain a double bond can be separated into their cis / trans isomers. Thus, for example, compounds obtained from general formula I that appear as racemates can be separated according to methods known to them (see Allinger NL and Eliel EL in "Topics in Stereochemistry", Vol. 6, Wiley Interscience, 1971) in their optical antipodes and the compounds of the general formula I with at least 2 asymmetric carbon atoms can be separated into their diastereomers on the basis of their physicochemical differences according to methods known to them, for example by chromatography and / or fractional crystallization, which , if they are produced in racemic form, they are then separated into the enantiomers as mentioned above. The enantiomeric separation is preferably effected 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 activated as alcohols, and the separation of the mixture of salt or the diastereomer derivative obtained in this way, for example by virtue of different solubilities, being that from the salts or derivatives of pure diastereomeric form they can release the free antipodes by the effect of appropriate means. Particularly preferred optically active acids are, for example, the D and L forms of tartaric acid or dibenzoyl tartaric acid, di-o-tolyltartaric acid, malic acid, mandelic acid, camphorsulfonic acid, glutamic acid, asparaginic acid or quinic acid. Optically active alcohols include, for example, menthol (+) or (-) and as an optically active acyl residue in amides, for example, the methyloxycarbonyl residue (+) or (-). In addition, the novel compounds of the formula I thus obtained, if they contain a carboxy group, can then be converted, if desired, into their salts with inorganic or organic bases, in particular for pharmaceutical use in their physiologically acceptable salts. As a matter of fact, for example, they come under consideration, for example, hydrc > sodium oxide, potassium hydroxide, cyclohexylamine, ethanolamine, diethanolamine and triethanolamine. As already mentioned at the beginning, the new compounds of the general formula I and their salts have valuable properties. Thus, the compounds of the general formula I in which Y contains a cyano group have valuable pharmacological properties, in particular an antithrombotic effect, which is preferably based on an effect that influences thrombin or factor Xa, for example an effect inhibitor of thrombin or factor Xa, in an effect that prolongs the aPTT interval and in an effect of inhibition on similar serinoproteases, such as trypsin, urine kinase factor Vlla, factor IX, factor XI and factor XII, and the compounds of the general formula I in which Y contains a cyano group represent valuable intermediates for the preparation of the general formula I in which R 5 represents an aminomethyl group, amidino or guanidinomethyl optionally substituted. For example, the compounds A = rac-4-. { 3- [5-Ethoxycarbonylmethyl-2-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} benzamidine, B = rac-4-. { 3- [2,5-dimethyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargi lamino} benzamidine, C = 4- [3- (2, 5-d? met il -4 -isopropylcarbonyl-phenyl) -propargylamino] benzamidine, D = 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-pyridin-2-yl-aminocarbonyl) -phenyl] -propargylamino} benzamidine, E = 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-pyridin-2-yl-aminocarbonyl) -phenyl] prop-1-ylamino} benzamidine, F = 4- [3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzamidine, G = 4-. { 3- [2, 5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-ethyl-carbonylamino) -phenyl] -propargylamino} benzamidine, H = 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-hydroxycarbonyl-methyl-aminocarbonyl-amino) -phenyl] -propargylamino} benzamidine, and I = 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-hydroxycarbonylmethylcarbonyl-amino) -phenyl] -propargylamino} Benzamidine were investigated with respect to its effect on the prolongation of the aPTT interval as follows: Material: - human citrate blood plasma, - PTT reagent, Boehringer Mannheim (524298), calcium solution (0.025 mol / 1), Behring Werke, Marburg (ORH 056/57), - diethylbarbiturate acetate regulator, Behring Werke , Marburg (ORWH 60/61) - Biomatic BIO Coagulometer, Desaga, Wiesloch. Way of carrying out: The determination of the aPTT interval was carried out with a Biomatic BIO coagulometer from the company Desaga. The test substance is introduced into test containers prescribed by the manufacturer with 0.1 ml of human citrate-plasma and 0.1 ml of PTT reagent. The preparation is incubated for three minutes at 37 ° C. By adding 0.1 ml of calcium solution the coagulation reaction starts. Depending on the devices, the measurement of the time until the coagulation of the preparation begins with the introduction of the calcium solution. As controls serve preparations to which 0.1 ml of DBA regulator is added. According to the definition, the effective concentration of the substance is determined through a dose activity curve in which the aPTT interval is doubled compared to the control.

The following table contains the values found: By virtue of their pharmacological properties, the novel compounds and their physiologically acceptable salts are suitable for the prevention and treatment of thrombotic diseases of the veins and arteries, such as for the treatment of thrombosis of the deep veins of the legs, for avoid reocclusions after bypass operations or angioplasty (PTCA), as well as occlusion in the case of peripheral diseases of the arteries such as pulmonary embolism, disseminated intravascular coagulation, prophylaxis of coronary thrombosis, prophylaxis of stroke and avoid the occlusion of short circuits. Additionally, the compounds according to the invention are suitable for antithrombotic support in the case of a thrombolytic treatment, such as for example with rtPA or streptokinase, to avoid prolonged restenosis after PT (C) A, to avoid metastasis and growth of coagulation-dependent tumors and inflammatory processes dependent on fibrin. The dosage necessary to obtain a corresponding effect conveniently is 0.1 to 30 mg / kg, preferably 0.3 to 10 mg / kg in the case of intravenous administration, and 0.1 to 50 mg / kg, preferably 0.3 to 30 mg / kg in the case of oral administration, in each case from 1 to 4 x day. For this purpose it is possible to prepare the compounds of the formula 1 prepared according to the invention, optionally in combination with other active ingredients, with one or more usual inert carriers and / or diluents, for example corn starch, lactose, cane sugar, microcrystalline cellulose, magnesium stearate, polyvinylpyrrolidone, citric acid, tartaric acid, water, water / ethanol, water / glycerin, water / sorbitol, water / polyethylene glycol, propylene glycol, cetilestearyl alcohol, carboxymethylcellulose or substances containing fats such as solid fat or their appropriate mixtures in usual galenical preparations such as tablets, dragees, capsules, powders, suspensions or suppositories. The following examples will explain the invention in greater detail. Example 1 rac-N-terbutoxycarbonyl-4-. { 3- [5-Ethoxycarbonylmethyl-2-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine a. 4-Bromo-2, 5-dimethyl-benzoic acid At -78 ° C to a solution of 43.63 g (0.162 mol) of 2,5-dibromoxylene there is dropwise added 100 ml (0.16 mol) of a 1.6 molar solution of n-butyllithium in hexane, and stirring is continued for 1 hour. Then carbon dioxide is introduced for 4 hours in the solution. Heat slowly to room temperature and continue stirring for 16 hours. After the slow addition of 210 ml of 2N hydrochloric acid, the phases are separated, the aqueous phase is extracted 2 × with respectively 200 ml of etherThe combined organic phases are washed with a concentrated NaCl solution and dried with Na 2 SO 4. After removing the solvent in vacuo, the crude product is mixed with 200 ml of 2N NaOH and the obtained coffee solution is extracted 3 x with 100 ml of diethyl ether. The aqueous phase is acidified with concentrated HCl and the resulting precipitate is separated by suction, washed with water / ice and dried. Yield: 34.99 g (94% of theory), R £ Value: 0.55 (silica gel; ethyl acetate / petroleum ether = 2: 1). b. 4-Bromo-2-ethoxycarbonylmethyl-5-methyl benzoic acid To a solution prepared with 4.2 ml (30 mmol) of diisopropylamine and 19 ml of a 1.6 molar solution of n-butyllithium in hexane in 35 ml of tetrahydrofuran , cooled to -78 ° C, a solution of 1.7 ml (14 mmol) of diethyl ether of carbonic acid and 2.3 g (10 mmol) of 4-bromo-2 acid is added dropwise within a range of 2.5 hours, 5-dimethyl-benzoic acid in 15 ml of tetrahydrofuran. It is then heated to 0 ° C, poured into 200 ml of a solution of NH 4 Cl, brought to pH 6 with acetic acid and extracted by stirring with ethyl acetate. The acetic ester phase is washed with a 14% NaCl solution and dried with Na 2 SO 4. The solvent is lost by distillation and the remaining residue is digested several times in little diisopropyl ether / petroleum ether and then dried. Yield: 1.95 g (65% of the theory), Rf value: 0.35 (silica gel, ethyl acetate / petroleum ether = 3: 7 + 1 drop of glacial acetic acid). c. rac-N- (4-bromo-2-ethoxycarbonylmethyl-5-methyl-benzoyl) -2-methyl-pyrrolidine To a solution of 1.9 g (6.31 mmol) of 4-bromo-2-ethoxycarbonylmethyl-5-ethyl acid -benzoic acid in 660 ml of tetrahydrofuran / H: 0 (9: 1) 2.2 g (6.85 mmol) of O- (benzotriazol-1-yl) -N, N, N ', N'-tetra tetraf luorborate are added successively. eti Luromo, 2.41 ml (13.9 mmol) of N, N-diisopropyl-ethylamma and 0.27 g (2.0 mmol) of 1-hydroxy-1H-benzotriazole. After stirring for 10 minutes 0.59 g (6.94 mmol) of rac-2-methyl-pyrrolidine are added, stirring is continued for 19 hours and finally diluted with 200 ml of ethyl acetate. The obtained solution is washed with a 14% NaCl solution and 2 x extracted with ethyl acetate. The combined organic phases are washed with a 14% solution of NaCl and dried with Na 2 SO 4. After the solvent is distilled off and flash chromatography (silica gel, methylene chloride / ethanol = 98: 2), the desired compound is obtained. Yield: 2.00 g (86% of theory), Rf value: 0.3 (silica gel, ethyl acetate / petroleum ether = 3: 7 + 1 drop of glacial acetic acid). C17H22BrN03 (368.27) Mass spectrum: M + = 367/369 (isotopes of bromine) (M + H) + = 368/370 (isotopes of bromine) (M-H) - = 366/368 (isotopes of bromine) d. 4-propargylamino-benzonitrile A solution of 23.6 g (0.20 mol) of 4-amino-benzonitrile, 16.6 ml (0.22 mol) of propargyl bromide and 38.3 ml (0.22 mol) of diisopropyl-ethylamine are heated in 500 ml of toluene for 27 hours at 90 ° C. It is then diluted with ethyl acetate, washed 3 x with H20 and dried over MgSO4. After the solvent is distilled off, the crude product is purified by flash chromatography (silica gel, ethyl acetate / petroleum ether = 20:80 to 75:25). Yield: 22.9 g (73% of theory), Rf value: 0.38 (silica gel, ethyl acetate / petroleum ether = 3: 7). and. 4-propargylamino-benzamidine A solution of 5.0 g (32 mmol) of 4-propargylamino-benzonitrile is stirred in 150 ml of ethanol saturated with hydrogen chloride gas first for 3 hours at 0 ° C, then 21 hours at room temperature. The solvent is removed under vacuum at a maximum bath temperature of 30 ° C, and replaced by 250 ml of absolute ethanol. 10.7 g (0.11 mol) of ammonium carbonate are then added and the mixture is stirred for 36 hours. The solvent is removed by distillation, the residue is taken up in 200 ml of methylene chloride / ethanol (94: 6), the insoluble components are filtered off, concentrated and purified by flash chromatography (silica gel; methylene / ethanol = 90:10 to 75:25). Yield: 6.52 g (97% of theory), "R £ Value: 0.22 (silica gel; methylene chloride / ethanol = 80:20). f. N- (4-tert-butoxycarbonylamino-phenyl) -propargylamine A solution of 1.9 g (9.06 mmol) of 4-propargylamino-benzamidine and 2.35 g (10.8 mmol) of di-tert-butyl ester of pyrocarbonic acid in 50 ml of tetrahydrofuran is slowly mixed at 5 ° C with 45 ml of 0.2N NaOH and stirring is continued for 2.5 hours at room temperature. The solvent is removed by distillation, the solid residue is washed with H20 and dried. Yield: 2.2 g (88% of theory), Rf value: 0.41 (reversed-phase silica gel RP-8, methanol / 5% NaCl solution = 60:40). g. rac-N-terbutoxycarbonyl-4-. { 3- [5-Ethoxycarbonylmethyl-2-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine A solution of 1.00 g (2.72 mmol) of N- (4-bromo-2-ethoxycarbonylmethyl-5-methyl-benzoyl) -2-methyl-pyrrolidine, 1.11 g (4.07 mmol) of N-tert-butoxycarbonyl-4 -propargylamino-benzamidine and 10.4 ml (13.5 mmol) of triethylamine in 3.0 ml of acetonitrile is stirred for 15 minutes under nitrogen atmosphere, then mixed successively with 0.32 g (0.277 mmol) of tetra- (triphenylphosphine) -palladium (0) and 0.11 (0.578 mmol) of copper iodide (I), and stirred 1 hour at 90 ° C. The solvent is then removed by distillation and the crude product is purified by flash chromatography (silica gel, methylene chloride / ethanol = 99: 1 to 95: 5). Yield: 0.18 g (12% of theory), R £ Value: 0.3 (silica gel, methylene chloride / ethanol = 19: 1) C32H40N4O5 (560.69) Mass spectrum: (M + H) + = 561 ( MH) - = 559 Example 2 rac-4-. { 3- [5-Ethoxycarbonylmethyl-2-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine A solution of 0.36 g (0.642 mmol) of rac-N-terbutoxycarbonyl-4-. { 3- [5-ethoxycarbonylmethyl-2-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine in 20 ml of methylene chloride and 3 ml of trifluoroacetic acid is stirred for 4 hours. The solvent is then removed by distillation and the crude product is purified by flash chromatography (silica gel, methylene chloride / ethanol = 95: 5 to 80:20). Yield: 0.20 g (54% of theory), R £ Value: 0.3 (reversed-phase silica gel RP-8, methanol / 5% NaCl solution = 60:40). C27H32N403 (460.58 / 574.61) Mass spectrum: (M + H) * = 461 Example 3 rac-4-. { 3- [5-hydroxycarbonylmethyl-2-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine A mixture of rac-4 -. { 3 - [5-Ethoxycarbonylmethyl-2-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine, 3.5 ml of tetrahydrofuran, 2.5 ml of H20 and 1.3 ml of LiOH IN solution is stirred for 5 hours. Then 78 mg (1.45 mmol) of ammonium chloride are added, stirring is continued for another 16 hours and the solvent is distilled off. The residue is triturated with H20, separated by suction and washed with little H20. Yield: 35 mg (29% of theory), Rf value: 0.35 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C25H28N403 x HCl (432.53 / 468.99) Mass spectrum: (M + H) * = 433 (M-H) - = 431 Example 4 4 -. { 3-methyl -4 - [(thiazol-2-yl) carbonyl) -phenyl] -propargylamino} -benzamidine a. 2- (4-Bromo-2-methyl-benzoyl) -thiazole 2.0 g (13 mmol) of 2-trimethylsilylthiazole and 6.1 g (26 mmol) of 4-bromo-2-methyl-benzoic acid chloride are combined under cooling with Ice bath and heat for 3 hours at 80 ° C. The crude product is taken up in 30 ml of ethyl acetate, washed with H20, saturated NaHCO3 and H: 0 solution, dried and purified by flash chromatography (silica gel, methylene chloride). Yield: 1.4 g (40% theory), R £ Value: 0.65 (silica gel; ethyl acetate / petroleum ether = 20: 80). b. 4-. { 3- [3-met? L-4 - [(thiazol-2-yl) carbonyl] -phenyl] -propargylamino} -benzonityl is prepared analogously to the example lg from 2- (4-bromo-2-methyl-benzoyl) -thiazole, 4-propargyl-amino-benzonitrile, tetra (triphenylphosphine) palladium (0), copper iodide (I) and triethylamine in acetonitrile. Yield: 72% of the theory, Rf value: 0.43 (silica gel; ethyl acetate / petroleum ether = 20: 80). c. 4 -. { 3 - [3-methyl-4 - [(thiazol-2-yl) carbonyl] -phenyl] -propargylamino} -benzamidine 0.7 g (2 mmol) of 4-. { 3- [3-methyl-4- [(thiazol-2-yl) carbonyl] -phenyl] -propargylamino} -benzonitrile is stirred in 50 ml of ethanol saturated with hydrogen chloride gas first for 2 hours at 0CC, then 6 hours at room temperature. The solvent is removed under vacuum at a maximum bath temperature of 30 ° C, and replaced with 50 ml of absolute ethanol. Then add 1.4 g of ammonium carbonate, and stir during 16 hours. The solvent is then removed by distillation and the residue obtained is purified by flash chromatography (silica gel, methylene chloride / ethanol = 98: 2 to 80:20). Yield: 0.7 g (88% of the theory), R £ Value: 0.31 (silica gel, ethyl acetate / ethanol / ammonia = 90: 10: 1) C21H18N40S x HCl (374.47 / 410.93) Spectrum of mass: (M + H) + = 375 Example 5 4 - [3- (4-biphenyl) -propargylamino] -benzamidine a. 4- [3- (4-biphenyl) -propargylamino] -benzonitrile is prepared analogously to the example lg from 2- (4-bromobiphenyl, 4-propargyl-amino-benzonitrile, tetr (triphenylphosphine) palladium (0), copper iodide (I) and triethylamine in acetonitrile Yield: 29% of the theory, Rf value: 0.48 (silica gel; ethyl acetate / petroleum ether = 25:75) b. 4- [3- (4 -biphenyl) -propargylamino] -benzamidine To a solution of 0.50 g (1.6 mmol) of 4- [3- (4-biphenyl) -propargylamino] -benzamidine and 78 ml (5.6 mmol) of triethylamine in 25 ml of absolute pyridine were added. Hydrogen sulphide is introduced for a long time until it is no longer possible to check starting material according to thin layer chromatography, then the solvent is distilled off, the residue obtained is taken up in methylene chloride and washed with 2N HCl and H20. The organic phase is dried and the solvent is distilled off, the residue is taken up in 25 ml of acetone and mixed with 2.0 ml (32 mmol). of methylene iodide. After 20 hours the volatile components are distilled off, the crude product is taken up in 35 ml of ethanol and 15 ml of methylene chloride and mixed with 2.8 g (36 mmol) of ammonium acetate. The product of the reaction is stirred for 8 hours at 40 ° C and 60 hours at room temperature, concentrated in vacuo and purified by flash chromatography (silica gel; methylene chloride / ethanol = 98: 2 to 80:20 ). Yield: 0.57 g (78% of theory), R £ value: 0.21 (silica gel, methylene chloride / ethanol = 80:20). C22H19N3 x Hl (325.41 / 453.32) Mass spectrum: (M + H) + = 326 Example 6 4-. { 3- [3- (2-methyl-benzimidazol-l-methyl-4- (2-methyl) -phenyl] -propargylamino] -benzamidine a. 1- (3-bromobenzyl) -2-methylbenzimidazole To a solution of 1.32 g (10 mmol) of 2-methyl-benzimidazole in 10 ml of absolute dimethylsulfoxide is added 1.23 g of potassium terbutylate and after 45 minutes 2.62 g (10.5 mmol) of 3-bromo-benzylbromide, and is stirred for After 4 hours, the reaction mixture is diluted with ethyl acetate, washed 3 × with a 14% NaCl solution, dried, concentrated and purified by flash chromatography (silica gel, petroleum ester). ethyl acetate = 9: 1 to ethyl acetate) Yield: 2.4 g (80% theory), C15H13BrN2 (301.19) Mass spectrum: M + = 300/302 (bromine isotopes) b. 3- [3- (2-methylbenzimidazol-l-yl-methyl) -4-phenyl] -propargylamino] -benzamidine Prepared analogously to the example lg from 1- (3-bromobenzyl) -2-methyl -benzimidazole, N-tert-butoxycarbon il-4-propargylamino-benzamidine, tetra- (triphenylphosphine) palladium (0), copper iodide (I) and triethylamine in acetonitrile, and subsequent cleavage of the terbutoxycarbinyl residue by trifluoroacetic acid analogously to example 2.

Yield: 55% of theory, R £ Value: 0.13 (silica gel; methylene chloride / ethanol = 80:20). C25H23N5 x CF3C00H (393.49 / 507.51) Mass spectrum: (M + H) * = 394 (M + 2HX "= 197.6 Example 7 4- { 3- [3-methyl-4- (2-methyl-benzimidazole- 2-yl) -phenyl] -propargylamino.} - benzamidine a.N- (2-nitrophenyl) -4-bromo-2-methyl-aniline A mixture of 2.9 ml (27.5 mmol) of 2-fluoro-nitrobenzene, . 55 g (55 mmol) of 4-bromo-2-methyl-aniline and 1.60 (27.5 mmol) of spray-dried potassium fluoride are heated to 180 ° C. After cooling, the reaction mixture is taken up in methylene chloride, washed with H20, with 10% hydrochloric acid and again with H20, dried over Na2SO4, concentrated and purified by flash chromatography (silica gel, petroleum ether ethyl acetate = 75:25) Yield: 5.95 g (70% theory), R £ value: 0.69 (silica gel, petroleum ether / ethyl acetate = 75:25). b. N- (2-aminophenyl) -4-bromo-2-methyl-aniline A suspension of 5.34 g (17.4 mmol) of N- (2-nitrophenyl) -4-bromo-2-methyl-aniline and 1.7 g of platinum on The carbon is stirred for 1 hour in 100 ml of dichloromethane and 100 ml of methanol at a hydrogen pressure of 3 bar. The catalyst is then removed by filtration, and the filtrate is concentrated by evaporation. Yield: 4.8 g (100% theory), Rf value: 0.27 (silica gel, petroleum ether / ethyl acetate = 75:25). c. 1- (4-bromo-2-methyl-phenyl) -2-methyl-benzimidazole A mixture of 5.22 g (18.8 mmol) of N- (2-aminophenyl) -4-bromo-2-methyl-aniline and 7.1 ml (75.2 mmol) of acetic anhydride are heated to boiling for 30 hours. The reaction mixture is then concentrated and purified by flash chromatography (silica gel, mee-filled chloride). Rf value: 0.20 (silica gel, petroleum ether / ethyl acetate = 75:25). d. 4-. { 3- [3-methyl-4- (2-methyl-benzimidazol-2-yl) -phenyl] -propargylamino} -benzamidine Prepared analogously to the example lg from 1- (4-bromo-2-methyl-phenyl) -2-methyl-benzimidazole, N-tert-butoxycarbonyl-4-propargylamino-benzamidine, tetra- (triphenylphosphine) palladium (0), copper iodide (I) and triethylamine in acetonitrile, and subsequent cleavage of the terbutoxycarbonyl residue by trifluoroacetic acid, analogously to example 2.

Yield: 41% of theory, R £ Value: 0.13 (silica gel; methylene chloride / ethanol = 80:20). C2SH23NS x CF3C00H (393.49 / 507.51) Mass spectrum: (M + H) + = 394 (M + 2HX = 197.6 Example 8 4- { 3- [4- (3- (2-ethoxycarbonyl-ethyl) -5 phenyl-pyrazol-1-yl) -3-methyl-phenyl] -propargylamino) -benzamidine a. 1- (4-iodo-2-methyl-phenyl) -3- (2-hydroxycarbonyl-ethyl) -5-phenyl-pyrazole A mixture of 2.5 g (8.78 mmol) of 4-iodo-2-methyl-phenylhydrazine (prepared in a manner analogous to J. Am. Chem. Soc. 78, 5854-5857 (1956)), 1.93 g (8.78 mmol) of 4,6-dioxo-6-phenyl-hexanic acid (prepared analogously to Synthesis 1991, 18-20) and 1.22 ml (8.78 mmol) of triethylamine in 70 ml of methanol are stirred for 3 hours at room temperature. The volatile components are then distilled off, the crude product obtained is taken up in 100 ml of ether, washed with IN HCl and the aqueous phase is extracted with 50 ml of ether and 50 ml of methylene chloride. The combined organic phases are dried, concentrated and the crude product is purified by flash chromatography (silica gel, methylene chloride / ethanol = 98: 2).

Yield: 2.26 g (60% of theory), Rf value: 0.45 (silica gel, methylene chloride / ethanol = 95: 5). C19H17IN202 (432.26) Mass spectrum: (M + H) + = 433 (M + Na) * = 455 (M-H) - = 431 b. 3- (2-Ethoxycarbonylethyl) -1- (4-iodo-2-methyl-phenyl) -5- phenyl-pyrazole A mixture of 2.26 g (5.23 mmol) of l- (4-iodo-2-methyl-phenyl) -3- (2-hydroxycarbonyl-ethyl) -5-phenyl-pyrazole and 0.93 g (5.75 mmol) of N, N'-carbonyldiimidazole in 50 ml of ethanol is stirred for 1 hour, then mixed with 5.0 ml of absolute ethanol it is heated at boiling for 1 hour, concentrated and purified by flash chromatography (silica gel, methylene chloride to methylene chloride / ethanol 98: 2). Yield: 1.4 g (58% of the theory), Rf value: 0.35 (silica gel, methylene chloride / ethanol = 99: 1). C21H21IN202 (460.32) Mass spectrum: (M + H) + = 461 (2M + NaX = 943 d.4- {. 3- [4- (3- (2-ethoxycarbonyl-ethyl) -5-phenyl-pyrazole - 1-yl) -3-methyl-phenyl] -propargylamino.} - benzamidine Prepared analogously to the example lg from 3- (2-ethoxycarbonyl-ethyl) -1- (4-iodo-2-methyl) phenyl) -5-phenyl-pyrazole, N-terbutoxycarbonyl-4-propargyl-amino-benzamidine, tetra (triphenylphosphine) palladium (0), copper iodide (I) and triethylamine in acetonitrile, and subsequent cleavage of the terbutoxycarbonyl residue by acid trifluoroacetic acid, analogously to example 2. Yield: 71% of theory, R £ value: 0.13 (inverted phase RP-8 silica gel; methanol / 5% NaCl solution = 6: 4). C31H31N502 x CF3C00H (505.63 /619.65) Mass spectrum: (M + H) + = 506 Example 9 4 - [3- (3-methyl-4-morpholinocarbonyl-phenyl) -propargthio] -benzamidine a. 4- [3- (3-methyl-4-morpholinocarbonyl-phenyl) -propargylthio] -h > Enzyme is prepared analogously to the example lg from N- (4-bromo-2-methyl-benzoyl) -morpholine, propargylalcohol, tetra (triphenylphosphine) palladium (0), copper iodide (I) and triethylamine in acetonitrile. Yield: 46% of theory, Rf Value: 0.40 (silica gel; ethyl acetate / petroleum ether = 6: 4). b. N- [4- (3-methylsulfonyl-propin-1-yl) -2-methyl-benzoyl] -morpholine A mixture of 0.90 g (3.5 mmol) of N- [4- (3-hydroxy-propin-1-yl) ) -2-methyl-benzoyl] -morpholine, 0.45 g (3.9 mmol) of methanesulfonic acid chloride and 1.0 ml (7 mmol) of triethylamine in 20 ml of tetrahydrofuran are stirred for 1 hour at room temperature. Water / ice is then added, extracted with ethyl acetate, the organic phase is washed with water and concentrated. Yield: 2.0 g of brown oil (83% of theory), Rf value: 0.72 (silica gel, methylene chloride / ethanol / ammonia = 90: 10: 1). c. 4- [3- (3-methyl-4-morpholinocarbonyl-phenyl) -propargylthio] -benzonitrile A solution of 1.0 g (3 mmol) of N- [4- (3-methylsulfonyl-propin-1-yl) -2- methyl-benzoyl] -morpholine, 4-cyano-thiophenol and 5 ml of N, -diisopropyl-ethylamine in 10 ml of dimethylformamide is heated for 30 minutes at 100 ° C.

It is then diluted with 50 ml of ethyl acetate, washed 2 × with a 14% NaCl solution, dried, concentrated and purified by flash chromatography. (silica gel; elution with gradient: methylene chloride to methylene chloride / ethanol = 98: 2). Yield: 0.8 g (73% of the theory), Rf value: 0.62 (silica gel, methylene chloride / ethanol = 95: 5). d. 4- [3- (3-methyl-4-morpholinocarbonyl-phenyl) -propargylthio] -benzamidine is prepared analogously to Example 4c from 4- [3- (3-methyl-4-morpholinocarbonylphenyl) -propargylthio] -benzo-nitrile, with gaseous hydrogen chloride, saturated ethanol and love carbonate. go. Yield: 87% of theory, Rf value: 0.38 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C22H23N302S X HCl (393.53 / 429.99) Mass spectrum: (M + H) "= 394 Example 10 E-4- { 3- [3- (2-ethoxycarbon? I-vmil) -4-pyrrolidinocarbonyl- phenyl] -propargylamino-oenzamidine a.-5-bromo-l, 3-dihydro-isobenzofuran-1-on A solution of 0.43 g (2.0 mmol) of 4-bromo-2-methyl-benzoic acid, 0.34 g (1.9 mmol) ) of n-bromo-succinimide and 20 mg of azaisobutyric acid nitrile in 7 ml of propionic acid methyl ester is heated to boiling for 1 hour under a nitrogen atmosphere and is irradiated with a mercury lamp. it is concentrated, it is absorbed in methylene chloride, washed with H20, dried over Na2SO4 and purified by flash chromatography (silica gel, ethyl acetate / petroleum ether = 5:95 to 15:85).

Yield: 0.25 g (54% of theory), R £ value: 0.52 (silica gel, ethyl acetate / petroleum ether = 20:80) C8H5Br02 (213.03) Mass spectrum: M + = 212/214 (isotopes of bromine) b. N- (4-bromo-2-hydroxymethyl-benzoyl) -pyrrolidine A mixture of 2.55 g (11.9 mmol) of 5-bromo-1,3-dihydro-isofuran-1-one and 1.3 ml (15.5 mmol) of pyrrolidine in 15 ml of ethanol is heated to boiling for 8 hours: Then 1.3 ml of pyrrolidine are added again and the mixture is heated for a further 22 hours. The solvent is then removed, taken up in ethyl acetate, washed with H20, dried over Na2SO4 and purified by flash chromatography (silica gel, methylene chloride / ethanol = 99: 1 to 99: 2). 3.01 g (89% of the theory), R £ value: 0.45 (silica gel, methylene chloride / ethanol = 95: 5). c. N- (4-bromo-2-formyl-benzoyl) -pyrrolidine To a mixture of 4.0 g (14 mmol) of N- (4-bromo-2-hydroxymethyl-benzoyl) -pyrrolidine in 80 ml of methylene chloride is added per portions, distributed over several hours, a total of 25 g of manganese dioxide and stirred for a total of 30 hours. It is then filtered on infusoria soil and the solvent is distilled off. The crude product is reacted without further purification. Yield: 3.3 g (84% of theory), R £ Value: 0.31 (silica gel, methylene chloride / ethanol = 95: 5). d. EN- [4-Bromo-2- (2-ethoxycarbonyl-vinyl) -benzoyl] -pyrrolidine A solution of 1.27 g (4.5 mmol) of N-bromo-2-formyl-benzoyl) -pyrrolidine and 1.65 g (4.5 mmol) of carboethoxymethylenetriphenylphosphorane in 45 ml of toluene are heated for 4 hours at 80 ° C. After separating the solvent, it is purified by flash chromatography (silica gel); methylene chloride / ethanol = 99: 1 to 99: 2). Yield: 1.07 g (67% of theory), R £ Value: 0.33 (silica gel, petroleum ether / ethyl acetate = 1: 1). and. E-4-. { 3- [3- (2-ethoxycarbonyl-vinyl) -4-pyrrolidinocarbonyl-phenyl] -propargylamino} -benzamidine is prepared analogously to the example lg from EN- [4-bromo-2- (2-ethoxycarbonyl-vinyl) -benzoyl] -pyrrole idine, N-tert-butoxycarbonyl-4-propargylamino-benzamidine, tetra- (tri-phenylphosphine) palladium (0), copper (I) iodide and triethylamine in acetonitrile, and subsequent cleavage of the terbutoxycarbonyl residue by trifluoroacetic acid in analogous manner to Example 2. Yield: 56% of the theory, R £ Value: 0.17 (silica gel; methylene chloride / ethanol = 4: 1). C26H28N403 x CF3C00H (444.54 / 558.56) Mass Spectrum: (M + H) * = 445 Example 11 N-Terbutoxycarbonyl -4 - [3 - (2,5-dimethyl-4-isopropylcarbonyl-phenyl) propargylamino] benzamidine a. 4-bromo-2, 5-dimethyl-l-isopropylcarbonylbenzole To a solution cooled to -78 ° C of 13.5 g (50 mmol) of 2,5-dibromo-p-xylene in 100 ml of tetrahydrofuran is added dropwise. drop 31.2 ml (50 mmol) of a 1.6 molar n-butyllithium solution in hexane, stir for 30 minutes and then mix with. 4.5 ml (50 mmol) of isobutyronitrile. Allow the reaction mixture to warm slowly to room temperature, stir for 1 hour, then mix with 50 ml of 2N HCl and 70 ml of diethyl ether, and stir for another 16 hours. The aqueous phase is separated and extracted 2 × with diethyl ether. The combined organic phases are dried with Na 2 SO 4, concentrated and the residue is purified by flash chromatography (silica gel, petroleum ether / ethyl acetate = 9: 1). Yield: 6.08 g (48% of the theory), R £ Value: 0.58 (silica gel, petroleum ether / ethyl acetate = 9: 1). C12H15BrO (255.16) Mass spectrum: M * = 254/256 (isotopes of bromine) b. N-terbutoxycarbonyl-4- [3- (2, 5-dimethyl-4-isopropyl-carbonyl-phenyl) -propargylamino] benzamidine Prepared analogously to the example lg from 4-bromo-2,5-dimethyl- l-iso-propylcarbonyl-benzole, N-tert-butoxycarbonyl-4-propargylamino-benzamidine, tetra (triphenylphosphine) palladium (0), copper iodide (I) and triethylamine in acetonitrile. Yield: 57% of the theory, Rf value: 0.3 (silica gel, methylene chloride / ethanol = 98: 2). C27H33N303 (447.58) Mass spectrum: (M + H) * = 448 Example 12 4 - [3 - (2,5-dimethyl-4-isopropylcarbonyl-l-phenyl) -propargylamino] -benzamidine Prepared analogously to Example 2 from N-tert-butoxycarbonyl-4- [3 - (2,5-dimethyl-4-isopropyl-carbonyl-phenyl) -propargylamine] -benzamidine and trifluoroacetic acid. Yield: 34% of the theory, R £ Value: 0.30 (silica gel, methylene chloride / ethanol = 4: 1). C22H25N30 X CF3COOH (347.46 / 461.88) Mass spectrum: (M + H) '= 348 Example 13 4-. { 3- [4- [(1-methyl-β-rudazol-2-yl) carbonyl] -phenyl] -propargylamino} -benzamidine a. 2 - (4-Iodo-benzoyl) -1-methyl-imidazole 0.82 g (10 mmol) of 1-methylene imidazole and 2.7 g (10 mmol) of 4-iodobenzoic acid chloride are combined under water / ice bath 10 ml of acetonitrile, mix with 1.4 ml (10 mmcl) of triethylamine and then stir for 16 hours at room temperature. The crude product is taken up in 30 ml of ethyl acetate, washed with H20, dried and purified by flash chromatography (silica gel, methylene chloride). Yield: 1.9 g (51% of theory), R £ Value: 0.28 (silica gel, ethyl acetate / petroleum ether = 60: 40). c. 4-. { 3- [4- [(1-methyl-imidazol-2-yl) carbonyl] -phenyl] -propargyl-amino} -benzamidine Prepare analogously to example 4c from 4. { 3 - [4- [(1-methyl-imidazol-2-yl) carbonyl] -phenyl] -propargylamino} -benzonitirlo, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 77% of theory, Rf Value: 0.37 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C21H19NsO x HCl (357. 42/3 93.89) Mass spectrum: (M + H) + = 358 (M + 2H) "= 179.6 (M + HC1) * = 394/396 (chlorine isotopes) Example 14 4 -. { 3 - [3-methyl-4 - [(1-methyl-imidazol-2-yl) -carbonyl] -phenyl] -propargylamino} -benzamidine Prepare analogously to example 4c from 4. { 3- [3- [(1-methyl-imidazol-2-yl) carbonyl] -phenyl-propargylamino} -benzonitir (prepared analogously to example 13b) with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 62% of theory, R £ Value: 0.39 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C22H21N50 X HCl (371.45 / 407.191) Mass spectrum: (M + H) + = 372 Example 15 4 -. { 3 - [4- [(imidazol-2-yl) carbonyl] -phenyl] -propargylamino} -benzamidine, prepared analogously to example 4c from 4. { 3- [4- [(imidazol-2-yl) carbonyl] -phenyl] -propargylamino} -benzonitirlo, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 60% of theory, R £ Value: 0.35 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C22H21N50 x HCl (343.41 / 379.87) Mass spectrum: (M + H) * = 344 (M + 2H) ** = 172.7 Example 16 4-. { 3- [4- [(thiophen-2-yl) carboni1] -phenyl] -propargylamino} -benzamidine, prepared analogously to example 4c from 4. { 3 - [4- [(thiophen-2-yl) carbonyl] -phenyl] -propargylamino} -benzonitirlo, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 85% of theory, R £ Value: 0.45 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C22H21N30 x HCl (359. 45 / 395.91) Mass spectrum: (M + H) * = 360 Example 17 4-. { 3- [4- (2-methylphenylcarbonyl) -phenyl] -propargylamino} -benzamidine, prepared analogously to example 4c from 4. { 3- [4- (2-Methylphenylcarbonyl] -phenyl] -propargyl-amino} -benzonityryl, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate Yield: 80% of theory, R £ Value: 0.45 ( silica gel; methylene chloride / ethanol = 4: 1). C24H21N30 x HCl (367.45 / 403.91) Mass spectrum: (M + H) * = 368 Example 18 4-. { 3- [4- (4-methylphenylcarbonyl) -phenyl] -propargylamino} -benzamidine, prepared analogously to example 4c from 4. { 3 - [4- (4-Methylphenylcarbonyl] -phenyl] -propargyl-amino) -benzonityryl, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 65% of theory, R £ Value: 0.15 (silica gel; methylene chloride / ethanol = 4: 1). C24H21N30 x HCl (367.45 / 403.91) Mass spectrum: (M + H) * = 368 (2M + H) + * = 735 Example 19 4-. { 3- [4- (2-chlorophenylcarbonyl) -phenyl] -propargylamino} -benzamidine, is prepared analogously to example 2 from N-terbutoxycarbonyl 4-. { 3- [4- (2-Chlorophenylcarbonyl] -phenyl] -propargylamino] -benzamidine and trifluoroacetic acid.

Yield: 52% of theory, R £ Value: 0.29 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C23H18C1N30 x CF3COOH (387.87 / 501.90) Specimen of mass: (M + H) * = 388/390 (i chlorine sotopes) Example 20 4-. { 3- [4- (3-chlorophenylcarbonyl) -phenyl] -propargylamino} -benzamidine, is prepared analogously to example 4c from 4 -. { 3 - [4 - (3-chlorophenylcarbonyl] -phenyl] -propargyl-ammo.} .benzonityryl, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate Yield: 61% of theory, Rf value: 0.25 (gel silica, methylene chloride / ethanol = 4: 1) C23H18C1N30 x HCl (387.87 / 423.33) Mass spectrum: (M + H) * = 388/390 (chlorine isotopes) Example 21 4-. { 3- [4- (4-chlorophenylcarbonyl) -phenyl] -propargylamino} -benzamidine, is prepared analogously to example 2 from N-terbutoxycarbonyl 4-. { 3 - [4 - (2-Chlorophenylcarbonyl] -phen?] -propargylamino.} - benzamidine and trifluoroacetic acid.

Yield: 42% of the theory, R £ Value: 0.29 (silica gel, methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C23H18C1N30 X CF3COOH (387.87 / 501.90) Mass spectrum: (M + H) * = 388/390 (chlorine isotopes) Example 22 4-. { 3- [4- (pyrid-2-? L -carboni 1) -phenyl] -propargylamino} -benzamidine, prepared analogously to example 4c from 4. { 3 - [4 - (p? Pd-2-yl-carbonyl] -phenyl] -propargyl-amino} -benzonityr, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate Yield: 47% of theory, R £ value: 0.48 (silica gel; methylene chloride / ethanol / ammonia = 50: 45: 5). C22H18N40 x HCl (354.42 / 390.88) Mass spectrum: (M + H) * = 355 Example 23 4-. { 3- [4- (pyrid-3-yl-carbonyl) -f-enyl] -propargylamino} -benzamidine, is prepared analogously to example 2 from N-terbutoxycarbonyl 4 -. { 3 - [4- (pyrid-3-yl-carbonyl] -phenyl] -propargylamino] -benzamidine and trifluoroacetic acid Yield: 89% of theory, R £ value: 0.37 (silica gel; ethanol / ammonia = 50: 45: 5) C22H18N40 x CF3C00H (354.42 / 468.44) Mass spectrum: (M + H) * = 355 Example 24 4- { 3- [4- (pyrid-4-yl- carbonyl) -phenyl] -propargylamino.} - benzamidine, prepared analogously to Example 2 from N-terbutoxycarbonyl 4-. {3- [4- (pyrid-4-yl-carbonyl] -phenyl] - propargylamine.} - benzamidine and trifluoroacetic acid Yield: 84% of the theory, R £ value: 0.37 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5) C22H18N40 x CF3COOH (354.42 / 468.44 ) Mass spectrum: (M + H) * = 355 Example 25 4- [3- (2-Methyl-4-phenylcarbonyl) -phenyl] -propargylamino] -benzamidine, prepared analogously to Example 4c from 4- [3- (2-Methyl-4-phenylcarbonyl] -phenyl] -propargyl-amino} .benzonitrile, with hydrogen chloride gas, ethane l saturated and ammonium carbonate. Yield: 50% of theory, R £ value: 0.16 (silica gel, methylene chloride / ethanol = 4: 1). C24H21N30 X HCl (367.45 / 403.91) Mass spectrum: (M + H) * = 368 Example 26 4- [3- (3-Methyl-4-phenylcarbonyl) -phenyl] -propargylamino} -benzamidine, prepared analogously to Example 4c from 4- [3- (3-methyl-4-phenylcarbonyl] -phenyl] -propargyl-amino.}. -benzonitirole, with hydrogen chloride gas, ethanol. saturated and ammonium carbonate Yield: 50% of theory, R £ Value: 0.16 (silica gel; methylene chloride / ethanol = 4: 1). C24H21N30 x HCl (367.45 / 403.91) Mass spectrum: (M + H) * = 368 Example 27 4- [3- (4-phenylcarbonyl) -phenyl] -propargylamino} -benzamidine. Prepared analogously to example 4c from 4- [3 - (4-phenylcarbonyl] -phenyl] -propargyl-amino} -benzonitrile, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 78% of theory, R £ Value: 0.13 (silica gel; methylene chloride / ethanol = 4: 1). C23H19N30 x HCl (353.42 / 389.88) Mass spectrum: (M + H) * = 354 Example 28 4- [3- (2-amino-4-phenylcarbonyl) -phenyl) -propargylamino] -benzamidine, a . 4-iodo-3-nitro-benzophenone Under cooling with ice bath, 5.3 g (17 mmol) of 4-iodo-3-nitrobenzoic acid and 8.0 g (60 mmol) of aluminum trichloride in 70 ml of benzene are successively introduced. It is then stirred for 2 hours at room temperature, then poured into water, extracted with methylene chloride, dried over sodium sulfate and concentrated in vacuo. Yield: 5.4 g (90% of the theory) R £ value: 0.83 (silica gel, ethyl acetate / petroleum ether = 3: 7) b. 3-amino-4-iodo-benzophenone A mixture of 5.0 g (14 mmol) of 4-iodo-3-nitro-benzophenone, 7.5 g (42 mmol) of sodium dithionite, 40 ml of pyridine and 15 ml of water were added. heat 2 hours at 40 ° C. It is then concentrated in vacuo, mixed with water / ice and extracted with ethyl acetate. The organic phase is dried with sodium sulfate and the solvent is removed by vacuum distillation. Yield: 3.4 g (76% of theory) R £ Value: 0.60 (silica gel; ethyl acetate / petroleum ether = 3: 7) c. 4- [3- (2-amino-4-phenylcarbonyl-phenyl) -propargylamino} -benzamidine is prepared analogously to the example lg from 3-amino-4-iodo-benzophenone, N-terbutoxycarbonyl-4-propargylamino-benzamide, tetra (triphenylphosphine) -palladium (O), copper iodide (I) ) and triethylamine in acetonitrile, and subsequent cleavage of the terbutoxycarbonyl residue by trifluoroacetic acid analogously to Example 2. Yield: 54% of theory, R £ value: 0.60 (silica gel, ethyl acetate / ethanol / ammonia = 50: 45: 5) C23H20N4O x CF3COOH (368.46 / 482.48) Mass spectrum: (M + H) '= 369 Example 29 4- [3- (2-Acetamido-4-phenylcarbonyl-phenyl) -propargylamino} -benzamidine is prepared analogously to the example lg from 3-acetamido-4-iodo-benzophenone, N-terbutoxycarbonyl-4-propargylamino-benzamidine, tetra (triphenylphosphine) -palladium (0), copper iodide (I) and triethylamine in acetonitrile, and subsequent cleavage of the terbutoxycarbonyl residue by trifluoroacetic acid analogously to example 2. Yield: 61% of theory, R £ value: 0.30 (silica gel; ethyl acetate / ethanol / ammonia = 50:45: 5) C25H22N402 x CF3COOH (410.49 / 524.51) Mass spectrum: (M + H) * = 411 Example 30 4 - ¡3 - [4 - (2-methoxycarbonyl-phenylcarbonyl) -phenyl] -propargyl-amino } -benzamidine Prepare analogously to example 4c from 4 -. { 3 - [4 - > 2-methoxycarbonyl-phenylcarbonyl) -phenyl] -propargylamino} -benzonit rilo, with gaseous hydrogen chloride, saturated methanol and ammonium carbonate. Performance: 18% of 1 theory, Rf value: 0.1 (silica gel, methylene chloride / ethanol = 4: 1). C25H21N303 x HCl (411.46 / 44 ^ .92) Mass spectrum: (M + H) = 412 Example 31 4-. { 3- [4- (2-hydroxycarbonyl-phenylcarbonyl) -phenyl] -propargyl-amino} -benzamidma Prepared analogously to example 3 from 4. { 3- [4- (2-methoxycarbonyl-phenylcarbonyl) -phenyl] -propargylamino} -benzamidine and lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 41% of theory C24H19N303 x HCl (397.43 / 433.89) Mass spectrum: (M + H) * = 398 (M + Na) * = 420 (M + 2Na) ** = 221.6 Example 32 4- [1-methyl-3- (4-phenylcarbonyl-phenyl) -propargylamino] -benzamidine, is prepared analogously to Example 4c from 4- [1-methyl-3- (4-phenylcarbonyl-phenyl) - propargyl-amino] -benzonitirole, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 80% of theory, R £ Value: 0.52 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C24H21N30 x HCl (367.47 / 403.93) Mass spectrum: (M + H) * = 368 Example 33 3-methoxy-4- [3- (4-phenylcarbonyl-3-methyl-phenyl) -propargyl-amino ] -benzamidine, prepared analogously to Example 4c from 3-methoxy-4- [3- (4-phenylcarbonyl-3-methyl-phenyl) -propargylamino] -benzonityryl, with hydrogen chloride gas, saturated ethanol and ammonium carbonate. Yield: 29% of theory, R £ value: 0.24 (silica gel; methylene chloride / ethanol = 4: 1). C25H23N302 x HCl (397.48 / 433, 94) Mass spectrum: (M + H) * = 398 Example 34 4- [3- (5-Phenylcarbonyl-pyrid-2-yl) -propargylamino] -benzamidine, is prepared in a manner analogous to the example lg from 2-chloro-5-phenylcarbonyl-pyridine, N-terbutoxy-carbonyl-4-propargylamino-benzamidine, tetra (triphenylphosphine) -palladium (0), copper iodide (I) and triethylamine in acetonitrile, and subsequent cleavage of the terbutoxycarbonyl residue by trifluoroacetic acid analogously to example 2. Yield: 47% of theory, R £ value: 0.55 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5) C22H18N40 x CF3C00H (354.42 / 468.44) Mass spectrum: (M + H) * = 355 Example 35 4- [3- (5-phenylcarbonyl-thiophen-2-yl) -propargylamino] -benzamidine A solution 1.2 g (2.6 mmol) of N-terbutoxy-carbonyl-4- [3- (5-phenylcarbonyl-thiophen-2-yl) -propargylamino] -benzamidine and 4 ml of trimethylsilyliodide in 50 ml of methylene chloride are stirred for 3 hours, then d with 50 ml of methylene chloride and 25 ml of ethanol and washed with water. The organic phase is dried, concentrated and purified by flash chromatography (silica gel, methylene chloride / ethanol = 49: 1 to 9: 1).

Yield: 20% of theory, R £ Value: 0.28 (silica gel, ethyl acetate / ethanol / ammonia = 50: 45: 5) C21H17N3OS x Hl (359.46 / 487.37) Mass spectrum: (M + H) * = 360 Example 36 4- [3- (4-isopropylcarbonyl-phenyl) -propargylamino] -benzamidine Prepare analogously to example 4c from 4- [3- (4-isopropylcarbonyl-phenyl) - propargylamino] -benzonitirole, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 24% of theory, R £ Value: 0.13 (silica gel; methylene chloride / ethanol = 4: 1). C20H21N3O x HCl (319.41 / 355.87) Mass spectrum: (M + H) * = 320 (M + H + HC1) + = 356/358 (chlorine isotopes) Example 37 4- [3- (4-Cyclopentylcarbonyl-phenyl) -propargylamino] -benzamidine Prepared analogously to Example 4c from 4- [3- (4-cyclopentylcarbonyl-phenyl) -propargylamino] -benzonityl, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 53% of theory, R £ Value: 0.20 (silica gel; methylene chloride / ethanol = 4: 1). C22H23N30 x HCl (34 5.44 / 3 8 1. 90) Mass spectrum: (M + H) * = 346 Example 38 4- [3- (4-tert-butylcarbonyl-2, 5-dimethyl-phenyl) -propargylamino] -benzamidine is prepared from N-tert-butoxycarbonyl -4 - [3- (4-tert-butylcarbonyl-2, 5-dimethyl-phenyl) -propargylamino] -benzamidine and trifluoroacetic acid analogously to example 2. Yield: 18% of the Theory, Rf Value: 0.35 (silica gel; methylene chloride / ethanol = 4: 1 + 1 drop of acetic acid). C23H27N30 x CF3COOH (361.49 / 475.51) Mass spectrum: (M + H) * = 362 Example 39 4 -. { 3 - [4- (1,1-dimethyl-2-ethoxycarbonyl-ethylcarbonyl) -2,5-dimethyl-phenyl] -ropyrogylamino} -benzamidine a. 4- (4-Bromo-2, 5-dimethyl-phenyl) -3,3-dimethyl-4-oxo-botanical acid To a suspension of 1.44 g (approximately 30 mmol) of 50% sodium hydride in oil in 300 ml of tetrahydrofuran is added dropwise within 5 minutes a solution of 2.85 g (10 mmol) of 4- (4-bromo-2, 5-d? Methyl-phenyl) -4-oxo- Bury and heat for 2 hours at boiling. The mixture is then cooled to room temperature, 2.8 ml of methylodide are added dropwise and the mixture is reheated for a further 2.5 hours at boiling. Pour into 150 ml of water and the organic solvent is removed by distillation. The aqueous phase is washed 2 × with petroleum ether, acidified with hydrochloric acid and extracted with methylene chloride. The organic phase is dried with sodium sulfate and concentrated. Yield: 2.45 g (78% of theory), Rf value: 0.35 (gel of yes) ice, ethyl acetate / petroleum ether 30:70 + 1-acetic acid drop). C14H17Br03 (313.19) Mass spectrum: (M-H) * = 311/313 (bromine isotopes) b. Ethyl 4- (4-bromo-2,5-dimethyl-phenyl) -3,3-dimethyl-4-oxo-botanical acid A solution of 3.2 g (10 mmol) of 4- (4-bromo) acid -2,5-dimethyl-phenyl) -4-oxo-thanane in tetrahydrofuran is mixed with 3.60 g (11 mmol) of carbonyldiimidazole and stirred for one hour at room temperature. The solvent is replaced with 20 ml of ethanol and heated to boiling for 2 hours. The solvent is then distilled off, the crude product is taken up in methylene chloride, washed with water, dried over sodium sulfate, concentrated and purified by flash chromatography (silica gel, ethyl acetate / petroleum ether == 3:97). Yield: 2.95 g (87% of theory), Rf value: 0.55 (silica gel, ethyl acetate / petroleum ether 1: 9). C16H21Br03 (341.25) Mass spectrum: (M + H) * = 341/343 (isotopes of bromine) (M + Na) + = 363/365 (isotopes of bromine) c. 4-. { 3- [4- (1, 1-dimethyl-2-ethoxycarbonyl-ethylcarbonyl) -2,5-dimethyl-phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to the example lg from 4- (4-bromo-2,5-dimethyl-phenyl) -3,3-dimethyl-oxo-botanical acid ethyl ester, N-terbutoxycarbonyl- 4-propargylamino-benzamidine, tetra (triphenyl-phosphine) -palladium (O), copper iodide (I) and triethylamine in acetonitrile, and subsequent cleavage of the terbutoxycarbonyl residue by trifluoroacetic acid, analogously to example 2. Yield: 9% of the theory, Rf Value: 0.35 (silica gel; methylene chloride / ethanol = 4: 1) C26H31N303 x CF3COOH (433.46 / 547.58) Mass spectrum: (M + H) * = 434 Example 40 4-. { 3- [4- (1,1-dimethyl-2-hydroxycarbonyl-ethylcarbonyl) -2,5-dimethyl-phenyl] -propargi lamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [4- (1,1-dimethyl-2-ethoxycarbonyl-ethylcarbonyl) -2,5-dimethyl-phenyl] -propargylamino} -benzamidine and lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 50% of the theory Value R £: 0.3 (reversed-phase silica gel RP-8, methanol / 5% NaCl solution = 60:40). C24H27N303 x HCl (405.50 / 441.96) Mass spectrum: (M + H) * = 406 Example 41 4- [3- (4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4- [3- (4-pyrrolidinocarbonyl-phenyl) propargylamino] -benzamidine and trifluoroacetic acid.

Yield: 37% of theory, R £ Value: 0.29 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C21H22N40 x CF3COOH (346.44 / 460.46) Mass spectrum: (M + H) * = 347 Example 42 4- [3- (3-Methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzamidine Prepared analogously to the example 2 from N-ter-but-oxo-carbon? L-4- [3- (3-met? L-4-pyrrolidmo-carbonyl-phenyl) proparg? Lam? No] -benzam? Dma and trifluoroacetic acid. Yield: 52% of theory, R £ value: 0.27 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C22H24N40 x CF3COOH (3 60. 46 / 474.48) Mass spectrum: (M + H) * = 361 (M + 2H) * = 181 Example 43 4 - [3- (2, 5-d? Met? L -4-pyrrolidonecarbonyl-phenyl) -propargyl-amine] -benzamidem Prepared analogously to Example 2 from N-tert-butoxycarbonyl -4- [3 - (2, 5 -dimetll-4-pyrrolidone-carbonyl-phenyl) proparg? lammo] -benzamidena and trifluoroacetic acid. Performance: 20% of the theory, Rf value: 0.3 (silica gel, methylene chloride / ethanol = 4: 1). C23H26N40 x CF3COOH (374.49 / 488.51) Mass Spectrum: (M + H) * = 375 Example 44 4- [N-Met? L-3- (3-methyl-4-pyrrolidmocarbonyl-phenyl) -propargylamino] -benzamidma Se prepare analogously to example 4c from 4 - [N-methyl-3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzonityryl, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate.

Yield: 67% of theory, R £ Value: 0.19 (silica gel; methylene chloride / ethanol = 4: 1). C23H26N40 x HCl (374.49 / 410.95) Mass spectrum: (M + H) * = 375 Example 45 rac-4-. { 3- [4- (2-methyl-pyrrole-idinocarbonyl) -phenyl] -propargyl-amino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [4- (2-methyl-pyrrolidino-carbonyl) -phenyl] -propargyl-amino} -benzamidine and trifluoroacetic acid. Yield: 32% of theory, R £ Value: 0.34 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C22H24N40 x CF3C00H (360.48 / 474.48) Mass spectrum: (M + H) * = 361 (M + 2H) * '= 181 Example 46 rac-4-. { 3- [3-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [3-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenol] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 90% of theory, Rf Value: 0.31 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C23H26N40 X CF3COOH (374.49 / 488.51) Mass spectrum: (M + H) '= 375 Example 47 rac-4-. { 3- [2-met? L- - (2-methyl-1-pyrrids-linocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-ter-butcx? carbonyl-4-. { 3- [2-methyl-4- (2-methyl-pyrrolidinocarbonyl) -inyl] -propargylamino} -benzamidine and trifluoroacetic acid; co. Yield: 63% of theory, R £ Value: 0.2 (silica gel; methylene chloride / ethanol = 4: 1). C23H26N40 x CF3COOH (3 74. 49 / 488.51) Mass spectrum: (M + H) * = 375 Example 48 4- [3- (2-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzamidine prepare analogously to example 2 from N-tert-butoxycarbonyl -4 - [3- (2-methyl-4-pyrrolidinocarbonyl-phenyl) propargylamino] -benzamidine and trifluoroacetic acid. Yield: 86% of the theory, R £ Value: 0.25 (silica gel, methylene chloride / ethanol = 4: 1). C22H24N40 x CF3COOH (360.46 / 474.48) Mass spectrum: (M + H) * = 361 Example 49 rac ~ 2-methoxy-4-. { 3- [3-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 4c from rac-2-methoxy-4-. { 3 - [3-Methyl-4- (2-methyl-pyrrolidino-carbonyl) -phenyl] -propargylamino} -benzamidine, with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 23% of theory, R £ Value: 0.33 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C24H28N402 x HCl (404.54 / 440.98) Mass spectrum: (M + H) * = 405 (2M + H) * = 809 Example 50 4- [l-methyl-3- (3-methyl-4- pyrrolidinocarbonyl-phenyl) -propargylamino] -benzamidine Prepared in a manner analogous to example 4c from 4- [1-methyl-3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamide: no] -benzonityl, with chloride of gaseous hydrogen, saturated ethanol and ammonium carbonate.

Yield: 79% of theory, R £ Value: 0.43 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C23H26N402 x HCl (374.49 / 410.96) Mass spectrum: (M + H) * = 375 Example 51 rac-4-. { 3- [2,5-dimethyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamine} -benzamidine It is prepared analogously to Example 2 starting from rae-N-tert-butoxycarbonyl-4 -. { 3 - [2,5-dimethyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 4% of theory, R £ Value: 0.1 (silica gel; methylene chloride / ethanol = 4: 1). C24H28N40 x CF3C00H (388.51 / 502.54) Mass spectrum: (M + H) * = 389 Example 52 2- [3- (3-Methyl-4-pyrrolidinocarbonyl-f-enyl) -propargylamino] -5 -amidino-pyridine Prepared in a manner analogous to Example 4c from 2 - [3 - (3-methyl-4-pyrrolidinocarbonyl-f-enyl) -propargylamino] -5-cyano-pyridine, with hydrogen chloride gas, saturated ethanol and ammonium carbonate. Yield: 43% of the theory, R £ Value: 0.20 (silica gel; methylene chloride / ethanol = 4: 1). C21H23N50 X HCl (361.45 / 3 97.91) Mass spectrum: (M + H) * = 362 Example 53 4- [3- (3-methyl-4-tetrahydropyrazolocarbonyl-phenyl) -propargylamino] -benzamidine Prepared in a manner analogous to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [3-methyl-4- (2-butoxycarbonyl-tetrahydropyrazolocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 28% of the theory, R £ Value: 0.45 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C21H23N50 x 2 CF3COOH (361.46 / 589.50) Mass spectrum: (M + H) * = 362 Example 54 4 -. { 3 - [3-methyl-4- (4,5-dihydropyrazolocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 with N-tert-butoxycarbonyl-4-. { 3- [3-methyl-4- (tetrahydropyrazolocarbonyl) -phenyl] -propargylamino} -benzamidine old, oxidized with oxygen from the air and trifluoroacetic acid.

Yield: 5% of the theory, R £ Value: 0.49 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C21H21N50 x CF3COOH (359.46 / 473.46) Mass spectrum: (M + H) * = 360 Example 55 4 -. { 3 - [2,5-dimethyl-4- (7-azabicyclo [2,2,2] hept-7-yl -carbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [2, 5-dimethyl-4- (7-azabicyclo [2.2, 1] hept-7-yl -carbonyl) -phenyl] -propargyl ami no} -benzamidine and trifluoroacetic acid. Yield: 58% of theory, R £ Value: 0.49 (silica gel; methylene chloride / ethanol = 19: 1). C25H28N40 x CF3COOH (400.53 / 514.55) Mass spectrum: (M + H) * = 401 Example 56 rac-4-. { 3- [4- (3-amino-pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- (3- (terbutoxycarbonyl) amino-pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 100% of theory, R £ value: 0.60 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C22H25NsO x 2CF3COOH (375.48 / 603.52) Mass spectrum: (M + H) '= 376; M - 2 H) '= 188.5 Example 57 4 -. { 3 - [4- (indolin-1-ylcarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 starting from N-tert-butoxycarbonyl -4-. { 3- [4- (indolin-1-yl-carbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid.

Yield: 42% of the theory, Rf value: 0.30 (inverted phase RP-8 silica gel, methanol / solution at 5% NaCl 60:40). C25H22N40 x CF3COOH (394.48 / 508.50) Mass spectrum: (M + H) '= 395 Example 58 rac-4-. { 3- [4- (2-Hydroxymethyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- (2-Hydroxymethyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 51% of the theory, R £ Value: 0.26 (silica gel, methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C22H24N402 X CF3COOH (376.46 / 490.48) Mass spectrum: (M + H) * = 377 (M + 2H) ** = 189 (M + Na + H) ++ = 200 Example 59 rac-4-. { 3- [4- (2-ethoxycarbonylmethyl-pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- (2-ethoxycarbonylmethyl-pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 66% of theory, R £ Value: 0.27 (silica gel; chloride methylene / ethanol = 4: 1 and one drop of acetic acid). C26H30N4O3 x CF3COOH (446.55 / 560.57) Mass spectrum: (M + H) * = 447 (M + 2H) ++ = 224 (M + Na + H) * + = 235 Example 60 rac-4-. { 3- [4- (2- (2-ethoxycarbonyl-ethyl) -pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- (2- (2-ethoxycarbonyl-ethyl) -3-methyl-pyrrolidylcarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Performance: 56% of the theory, R £ Value: 0.28 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C27H32N403 x CF3COOH (460.58 / 574.61) Mass spectrum: (M + H) * = 461 (M + Na + H) ** = 242 Example 61 4-. { 3- [4- (2-methoxycarbonyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- (2-methoxycarbonyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 69% of theory, R £ Value: 0.26 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C23H24N403 X CF3COOH (404.47 / 518.49) Mass spectrum: (M + H) * = 405 (M + Na + H) ** = 214 (M + 2H) * '= 203 Example 62 rac-4-. { 3- [4- (2-ethoxycarbonylmethyloxymethyl-pyrrole idinocarbonyl) -phenyl] -3-methyl-propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- (2-Ethoxycarbonylmethyloxymethyl-1-pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid.

Yield: 76% of theory, R £ Value: 0.26 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C27H32N404 x CF3COOH (476.58 / 590.61) Mass spectrum: (M + H) * = 477 (M + Na + H) * + = 250 Example 63 rac-4-. { 3- [4- (2-ethoxycarbonylmethylaminocarbonylmethyl-pyrrolidinocarbonyl) -3-methyl phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- (2-ethoxycarbonylmethyl-aminocarbonylmethyl-pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} benzamidine and trifluoroacetic acid. Yield: 60% of the theory, R £ Value: 0.21 (silica gel, methylene chloride / ethanol = 4: 1 and one drop of acetic acid). C28H33N504 x CF3COOH (503.61 / 617.63) Mass spectrum: (M + H) * = 504 (M + Na + H) * + = 263.7 (M + 2H) ** = 252.7 Example 64 4-. { 3- [3- (2-ethoxycarbonyl-ethyl) -4-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [3- (2-ethoxycarbonyl-ethyl) -4-pyrrolidinocarbonyl) -phenyl] -propargylamino} benzamidine and trifluoroacetic acid. Yield: 30% of theory, R £ Value: 0.16 (silica gel; methylene chloride / ethanol = 4: 1). C 26 H 30 N 4 O 3 X CF 3 COOH (44 6 55/560 57) Mass spectrum: (M + H) * = 447 (M + 2 HX * = 224 (M + Na + H) ** = 235 Example 65 rac-4-. {3- [3- (N-ethoxycarbonylmethyl-N-methyl-aminomethyl) -4- (2-methyl-1-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepared analogously to Example 2 from rac -N-tert -butoxycarbonyl-4-. {3- [3- (N-ethoxycarbonylmethyl-N-methyl-aminomethyl) -4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine and acid Trifluoroacetic performance: 49% of theory, R £ value: 0.23 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40) C28H35N503 x CF3COOH (489.62 / 603.64) mass: (M + H) '= 490 (M + 2H) ** = 245.5 (M + Na + H) ** = 256.5 Example 66 4- [3- (3-ethoxycarbomethylmethoxymethyl-4-pyrrolidinocarbonyl-phenyl) -propargylaminobenzamidine Prepared analogously to example 2 from rac-N-tert-butoxycarbon? l-4- [3- (3-ethoxycarbonylmethyloxy-methyl-4-pyrrolidinocarbonyl-phenyl) -propargyl amino] -benzamidine and trifluoroacetic acid. Yield: 96% of theory, R £ Value: 0.23 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C26H30N4O4 X CF3COOH (462.55 / 576.57) Mass spectrum: (M + H) * = 463 (M + 2H) ** = 232 (M + Na + H) ** = 243 Example 67 4- [3- (3 - ethoxycarbonylmethyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] benzamidine Prepared analogously to example 2 from rac-N-tert-butoxycarbonyl-4- [3- (3-ethoxycarbonylmethyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] benzamidine and trifluoroacetic acid. Yield: 85% of theory, R £ Value: 0.45 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C2SH28N403 x CF3COOH (432.53 / 546.55) Mass spectrum: (M + H) * = 433 Example 68 4 - [3- (3-Ethoxycarbonylmethyl-aminocarbonylmethyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] benzamidine Prepared analogously to the example 2 from rac-N-tert-butoxycarbonyl-4- [3 - (3-ethoxycarbonylmethyl-aminocarbonylmethyl-4-pyrrolidinocarbonyl-phenyl) -propargyl-amino] benzamidine and trifluoroacetic acid. Yield: 91% of theory, R £ Value: 0.35 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C27H31N504 x CF3COOH (489.58 / 603.60) Mass spectrum: (M + H) * = 490 Example 69 4-. { 3- [4- [phenyl- (ethoxycarbonylmethyloxyimino) -methylene] -phenyl] -propargylamino} -benzamidine a. 4-. { 3- [4- [phenyl- (hydroxycarbonylmethyloxyimino) -methylene] -phenyl] -propargylamino} -benzonitrile A mixture of 0.50 g (1.5 mmol) of 4- [3- (4-phenylcarbonyl-phenyl) -propargylamino] -benzonitrile, 0.50 g (2.3 mmol) of carboxy-methoxylamine hydrochloride, 0.32 ml (2.3 mmol) of triethylamine, 3 g of molecular filter 3 Angstrom and 3 g of molecular filter 4 Angstrom in 45 ml of methanol / toluene (2: 1) is heated to boiling for a week. It is then filtered, concentrated and purified by flash chromatography (silica gel, petroleum ether / ethyl acetate = 2: 1 to ethyl acetate / acetic acid = 200: 1). Performance: 75% of the theory Value R £: < 0.1 (silica gel; ethyl acetate / petroleum ether = 1: 1) b. 4-. { 3- [4- [phenyl- (ethoxycarbonylmethyloxyimino) -methylene] -phenyl] -propargylamino} -benzamidine Prepare analogously to example 4c from 4. { 3- [4 - [phenyl- (hydroxycarbonylmethyloxyimino) -methylene] -phenyl] -propargylamino} -benzonitrile with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate.

Yield: 27% of theory, R £ Value: 0.23 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C27H26N403 X HCl (454.53 / 490.99) Mass spectrum: (M + H) * = 455 Example 70 4-. { 3- [4- [N- (2-ethoxycarbonyl-ethyl) -N-isopropyl-amino-carbonyl] -3-methyl-feryl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- [N- (2-ethoxycarbonyl-ethyl) -N-isopropyl-aminocarbonyl] -3-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 44% of the theory, R £ Value: 0.1 (silica gel, methylene chloride / ethanol = 4: 1). C26H32N403 x CF3COOH (448.56 / 562.59) Mass spectrum: (M + H) * = 449 Example 71 4-. { 3- [4- [N- (2-ethoxycarbonyl-ethyl) -N-methyl-aminocarbonyl] -3-methyl-phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- [N- (2-ethoxycarbonyl-ethyl) -N-isopropyl-aminocarbonyl] -3-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 16% of theory, R £ Value: 0.1 (silica gel; methylene chloride / ethanol = 4: 1). C24H28N403 x CF3COOH (420.52 / 534.54) Mass spectrum: (M + H) + = 421 Example 72 4-. { 3- [4- [N- (2-methoxycarbonyl-ethyl) -N-pyridin-2-yl-aminocarbonyl] -2,5-dimethyl-phenyl] -propargylamino} -benzamidine It is prepared analogously to Example 2 starting from rac-N-tert-butoxycarbonyl4-. { 3- [4- [N- (2-methoxycarbonyl-ethyl) -N-pyridin-2-yl-aminocarbonyl] -2,5-dimethyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 48% of the theory, R £ Value: 0.25 (silica gel, methylene chloride / ethanol = 4: 1). C28H29N503 x 2CF3COOH 1483.53 / 711.62) Mass spectrum: (M + H) '= 484 Example 73 rac-4-. { 3- [4- (2-Hydroxycarbonylmethyl-pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino. -benzamidine Prepared analogously to example 3 from rac-4-. { 3- [4- (2-ethoxycarbonylmethyl-pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 53% of the theory Value R £: 0.36 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C24H26N403 x HCl (418.50 / 454.96) Mass spectrum: (M + H) + = 419 (M + Na) + = 441 (M + Na + H) ++ = 232 Example 74 rac-4-. { 3- [4- (2- (2-Hydroxycarbonyl-ethyl) -pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine Prepared analogously to example 3 from rac-4-. { 3- [4- (2- (2-ethoxycarbonyl-ethyl) -pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 67% of the theory Value R £: 0.39 (silica gel RP-8 inverted phase; methanol / 5% NaCl solution = 60:40). C25H28N403 x HCl (432.52 / 468.98) Mass spectrum: (M + H) * = 433 (M + Na) + = 455 (M + 2Na) * + = 239 Example 75 rac-4-. { 3- [4- (2-hydroxycarbonyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepared analogously to example 3 from rac-4-. { 3- [4- (2-methoxycarbonyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 42% of the theory Value R £: 0.32 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C22H22N403 x HCl (390.45 / 426.91) Mass spectrum: (M + H) * = 391 (M + Na) * = 413 (M + 2Na) ** = 218 Example 76 rac-4-. { 3- [4- (2-Hydroxycarbonylmethyloxymethyl-1-pyrrolidinocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine Prepared analogously to example 3 from rac-4-. { 3- [4- (2-ethoxycarbonylmethyloxymethyl-pyrrolidino-carbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 30% of the theory Value R £: 0.4 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C2SH28N404 x HCl (448.53 / 484.99) Mass spectrum: (M + H) * = 449 (MH) "= 447 Example 77 rac-4- { 3- [4- (2-Hydroxycarbonylmethylaminocarbonylmethyl-pyrrolidinocarbonyl) -3- methyl-pheny1] -propargylamino.} - benzamidine Prepared analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. {3- [4- (2-ethoxycarbonylmethyl-aminocarbonylmethyl-pyrrolidinocarbonyl) - 3-methyl-phenyl] -propargylamino.} - benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride Yield: 80% of theory, R £ value: 0.38 (inverted phase RP-8 silica gel; methanol / 5% NaCl solution = 60:40). C26H29Ns04 x HCl (475.55 / 512.01) Mass spectrum: (M + H) * = 476 (M-H) '= 474 Example 78 4-. { 3- [3- (2-hydroxycarbonyl-ethyl) -4-pyrrolidinocarbonyl-phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [3- (2-ethoxycarbonyl-ethyl) -4-pyrrolidinocarbonyl-phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Performance: 84% of the theory Value R £: > 0.1 (silica gel; methylene chloride / ethanol 4: 1). C24H26N403 x HCl (418.50 / 454.96) Mass spectrum: (M + H) + = 419 (M + 2H) * '= 210 (M + Na + H) ** = 221 (M + 2Na) * + = 232 Example 79 4-. { 3- [3- (2-hydroxycarbonyl-vinyl) -4-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [3- (2-ethoxycarbonyl-vinyl) -4-pyrrolidinocarbonyl-phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Performance: 45% of the theory Value R £: > 0.1 (silica gel; methylene chloride / ethanol 4: 1). C24H24N403 X HCl (416.48 / 452.94) Mass spectrum: (M + H) * = 417 (M + Na) * = 439 (M + Na + H) ** = 220 (M + 2Na) ** = 231 Example 80 rac-4-. { 3- [3- (N-hydroxycarbonylmethyl-N-methyl-aminomethyl) -4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepared analogously to example 3 from rac-4-. { 3- [3- (N-ethoxycarbonylmethyl-N-methyl-aminomethyl) -4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 30% of the theory Value R £: 0.42 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C26H31N503 x HCl (461.57 / 498.03) Mass spectrum: (M + H) * = 462 (MH) * = 460 Example 81 4 - [3- (3-Hydroxycarbonylmethyloxymethyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] benzamidine Prepared from Analogously to example 3 from 4- [3- (3-ethoxycarbonylmethyloxymethyl-4-pyrrolidino-carbonyl-phenyl) -propargylamino] benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 21% of the theory Rf Value: 0.23 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C24H26N404 X HCl (434.50 / 470.96) Mass spectrum: (M + H) '= 435 (MH) = 433 Example 82 4- [3- (3-hydroxycarbonylmethyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] benzamidine Prepared in a manner analogous to Example 3 from 4- [3- (3-ethoxycarbonylmethyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 62% of the theory Value R £: 0.45 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C23H24N403 x HCl (404.47 / 440.93) Mass spectrum: (M + H) * = 405 (MH) "= 403 Example 83 4 - [3- (3-Hydroxycarbonylmethylaminocarbonylmethyl-4-pyrrolidinocarbonyl-phenyl) propargylamino] benzamidine Prepared in a manner analogous to Example 3 from 4- [3- (3-ethoxycarbonylmethylaminocarbonylmethyl-4-pyrroli-dinocarbonyl-phenyl) -propargylamino] benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride Yield: 42% of the theory Rf value: 0.45 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40) C25H27N504 x HCl (461.53 / 497.99) Mass spectrum: (M + H ) + = 462 (M + Na) + = 484 Example 84 4- {3- [3- (hydroxycarbonylmethyloxyimino) -methylene-4-pyrrolidinocarbonyl-phenyl] -propargylamino} -benzamidine Prepared analogously to the example 2 from rac-N-tert-butoxycarbonyl-4-. {3- [3- (hydroxycarbonylmethyloxyimino) methylene-4-pyrrolidinocarbonyl-phenyl] -propargyl-amino} -benzamidine and acid trifluoroacetic Yield: 42% of the theory, R £ Value: 0.4 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C24H25N504 x CF3C00H (447.50 / 561.52) Mass spectrum: (M + H) + = 448 (M + Na) * = 470 (M + 2H) ** = 224.5 (M + Na + H) ** = 235.7 (M + 2Na) ~ * = 246.6 Example 85 rac-4-. { 3- [2-methoxy-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [2-methoxy-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 90% of theory, R £ Value: 0.38 (silica gel; methylene chloride / ethanol = 4: 1 and one drop of acetic acid). C23H26N402 x CF3C00H (390.49 / 504.51) Mass spectrum: (M + H) * = 391 (M + 2H) + * = 196 Example 86 4- [3- (3-methoxy-4-pyrrolidinocarbonyl-phenyl) -propargyl- amino] benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4- [3- (3-methoxy-4-pyrrolidino-carbonyl-phenyl) -propargylamino] benzamidine and trifluoroacetic acid. Yield: 58% of the theory, Rf value: 0.20 (silica gel, methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C22H24N402 x CF3COOH (376.46 / 490.48) Mass spectrum: (M + H) + = 377 Example 87 4- [3- (3-hydroxy-4-pyrrolidinocarbonyl-phenyl) -propargyl-aminojbenzamidine Prepared analogously to example 2 from N-tert-butoxycarbonyl-4- [3- (3-hydroxy-4-pyrrolidinocarbonyl-phenyl) propargylamino] benzamidine and trifluoroacetic acid. Yield: 54% of the theory, R £ Value: 0.46 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C21H22N402 x CF3COOH (362.44 / 476.46) Mass spectrum: (M + H) + = 363 Example 88 rac-4-. { 3- [3-hydroxymethyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [3-hydroxymethyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 57% of the theory, Rf value: 0.54 (inverted phase RP-8 silica gel; methanol / 5% NaCl solution = 60:40). C23H26N402 X CF3COOH (390.49 / 504.51) Mass spectrum: (M + H) * = 391 Example 89 4 - [3- (3-Foryl-4-pyrrolidinocarbonyl-phenyl) -propargyl-amino] benzamidine Prepared analogously to Example 2 from N-tert-butoxycarbonyl-4- [3- (3-formyl-4-pyrrolidino-carbonyl-phenyl) -propargylamino] benzamidine and trifluoroacetic acid. Yield: 71% of the theory, R £ Value: 0.4 (reversed-phase silica gel RP-8, methanol / 5% NaCl solution = 60:40). C22H22N402 x CF3COOH (374.45 / 488.47) Mass spectrum: (M + H) * = 375 Example 90 4 - [3 - (3-aminocarbonylaminoiminomethylene-4-pyrrolidinocarbonyl-phenyl) propargylamino] benzamidine Prepared analogously to example 2 to Starting from N-tert-butoxycarbonyl -4 - [3- (3-aminocarbonylaminoimino-methylene-4-pyrrolidinocarbonyl-phenyl) propargylamino] -benzamidine and trifluoroacetic acid. Yield: 83% of theory, Rf value: 0.4 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40).

C23H25N702 x CF3COOH (43 1. 50 / .545.53) Mass spectrum: (M + H) * = 432 (M + Na + H) ** = 227. Example 91 4- [l-Methyl-3- (4-pyrrole idinocarbonyl-phenyl) -propargyl-amino] benzamidine Prepared analogously to example 4c from 4- | l-methyl-3- (4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzonityryl, with hydrogen chloride gas, saturated ethanol and ammonium carbonate. Yield: 78% of theory, Rf value: 0.57 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C22H24N40 x HCl (360.47 / 396.93) Mass spectrum: (M + H) * = 361 (M + Cl) "= 395/397 (M + C1 + HC1)" = 431/433 / 435N Example 92 4 - [3 - (4-piperidinocarbonyl-phenyl) propargylamino] benzamidine Prepared in a manner analogous to example 4c from 4- [3- (4-piperidinocarbonyl-phenyl) propargyl-amino] -benzonitrile, with hydrogen chloride gas, saturated ethanol and ammonium carbonate. Yield: 65% of the theory, R £ Value: 0.25 (inverted phase RP-8 silica gel; methanol / 5% NaCl solution = 60:40). C22H24N40 x HCl (360.47 / 396.93) Mass spectrum: (M + H) * = 360 Example 93 rac-4-. { 3- [4- (4-methylpiperidinocarbonyl) -phenyl] -propargyl-amino} -benzamidine Prepare analogously to example 2 from rac-N-tert-butoxycarbonyl-4-. { 3- [4- (4-methylpiperidino-carbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 70% of theory, R £ Value: 0.27 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C23H26N40 x CF3C00H (374.49 / 488.51) Mass spectrum: (M + H) * = 375 Example 94 4 - [3- (4-Acetidinocarbonyl-phenyl) -propargylamino] benzamidine Prepared analogously to Example 2 from N -ter-butoxycarbonyl-4- [3- (4-acetyldinocarbonyl-phenyl) -propargylamino] benzamidine and trifluoroacetic acid. Yield: 72% of theory, R £ Value: 0.21 (silica gel; methylene chloride / ethanol 4: 1 and a drop of acetic acid). C20H20N4O x CF3C00H (3 32.41 / 446.43) Mass spectrum: (M + H) * = 333 Example 95 4- [3- (3-methyl-4-morpholinocarbonyl-phenyl) -propargyl-amino] benzamidine prepare, a in a manner analogous to Example 2, starting with N-tert-butoxycarbonyl-4- [3- (3-methyl-4-morpholinocarbonyl-phenyl) -propargylamino] benzamidine and trifluoroacetic acid.

Yield: 90% of theory, R £ Value: 0.32 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C22H24N402 x CF3COOH (376.47 / 490.49) Mass spectrum: (M + H) + = 377 Example 96 4- [3- (2-methyl-4-morpholinocarbonyl-phenyl) propargyl-amino] benzamidine Prepared analogously to the example 2 from N-tert-butoxycarbonyl-4- [3- (2-methyl-4-morpholinocarbonyl-phenyl) -propargylamino] benzamidine and trifluoroacetic acid. Yield: 80% of theory, Rf Value: 0.38 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C22H24N402 X CF3COOH (376.47 / 490.49) Mass spectrum: (M + H) + = 377 Example 97 4 -. { 3 - [4 - (4-methylpiperazinocarbonyl) -phenyl] propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [4- (4-methyl-piperazine-carbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 87% of theory, Rf value: 0.59 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40) .. C22H25N50 X 2CF3COOH (375.48 / 603.52) Mass spectrum: (M + H) * = 376 Example 98 4- [3- (4-dimethylaminocarbonyl-phenyl) -propargylamino] -benzamidine Prepared analogously to Example 2 from N-tert-butoxycarbonyl-4- [3- (4-dimethylaminocarbonyl-phenyl) -propargylamino] benzamidine and trifluoroacetic acid.

Yield: 66% of theory, Rf Value: 0.21 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C19H20N4O x CF3COOH (320.40 / 434.42) Mass spectrum: (M + H) * = 321 Example 99 4- [3- (2, 5-dimethyl-4-dimethylaminocarbonyl-phenyl) -propargyl-amino] benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4- [3- (2, 5-dimethyl-4-dimethylamino-carbonyl-phenyl) propargylamino] benzamidine and trifluoroacetic acid. Yield: 54% of theory, R £ Value: 0.13 (silica gel; methylene chloride / ethanol = 4: 1). C21H24N40 X CF3COOH (348.46 / 462.49) Mass spectrum: (M + H) * = 349 Example 100 4 - [3 - (4-Diethylaminocarbonyl-3-methyl-phenyl) propargyl-amino] benzamidine Prepared analogously to the example 2 from N-tert-butoxycarbonyl-4 - [3-methyl- (4-diethylaminocarbonyl-3-methyl-phenyl] -propargylamine] -benzamidine and trifluoroacetic acid Yield: 80% of theory, R £ Value: 0.29 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C22H26N40 x CF3COOH (362.46 / 476.50) Mass spectrum: (M + H) + = 363 Example 101 4 -. { 3 - [4- (N-isopropyl-N-methyl-aminocarbonyl) -2,5-dimethyl-phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [4- (N-isopropyl-N-methyl-amino-carbonyl) 2,5-dimethyl-phenyl] -propargylamino} benzamidine and trifluoroacetic acid. Yield: 92% of theory, R £ Value: 0.15 (silica gel; methylene chloride / ethanol = 4: 1). C23H28N40 x CF3COOH (376.51 / 490.53) Mass spectrum: (M + H) "= 377 Example 102 4 - { 3 - [4- (N -tertbutyl-N-methyl-1-aminocarbonyl) -2,5-dimethyl phenyl] -propargylamino) -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. {3- [4- (N-tert-butyl-N-methyl-amino-carbonyl) -2 , 5-dimethyl-phene] propargylamino, benzamidine and trifluoroacetic acid Yield: 41% of theory, Rf value: 0.3 (silica gel; methylene chloride / ethanol = 4: 1). C24H30N4O x CF3COOH (390.54 / 504.56) Mass spectrum: (M + H) * = 391 Example 103 4- [3- (4-Trimethylhydrazinocarbonyl-3-methyl-phenyl) -propargyl-amino] benzamidine Prepared analogously to Example 2 is prepared from N-tert-butoxycarbonyl-4- [3- (4-trimethylhydrazinocarbonyl-3-methyl-phenyl] -propargylamino] benzamidine and trifluoroacetic acid.

Yield: 7% of theory, Rf value: 0.3 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 60:40). C21H25N50 x 2CF3COOH (363.47 / 591.61) Mass spectrum: (M + H) * = 364 Example 104 4-. { 3- [4- (N- (2-dimethylamino-ethyl) -N-methyl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [4- (N- (2-dimethylamino-ethyl) -N-methyl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 23% of the theory, R £ Value: 0.51 (inverted phase RP-8 silica gel); methanol / 5% NaCl solution = 60:40). C22H27N50 x 2CF3COOH (377.50 / 605.54) Mass spectrum: (M + H) + = 378 (M + 2H) ** = 189.7 Example 105 4-. { 3- [4- (N- (3-dimethylamino-propyl) -N-methyl-aminocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [4- (N- (3-dimethylamino-propyl) -N-methyl-aminocarbonyl) -3-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid.

Yield: 5% of the theory, R £ Value: 0.5 (silica gel RP-8 - inverted phase, methanol / 5% NaCl solution = 60:40). C24H31N50 x 2CF3COOH (405.56 / 633.60) Mass spectrum: (M + 2H) * "= 203.8 Example 106 4- { 3- [4- (N-cyclopentyl-N-methyl-aminocarbonyl) -3-methyl-phenyl ] -propargylamino.} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. {3- [4- (N-cyclopentyl-N-methyl-aminocarbonyl) -3-methyl) -phenyl] -propargylamino.} - benzamidine and trifluoroacetic acid Yield: 84% of theory, Rf value: 0.3 (silica gel; methylene chloride / ethanol = 4: 1) .C24H28N40 x CF3COOH (388.52 / 502.54) Mass spectrum: (M + H) * = 389 Example 107 4- {3- [4- (pyrrolidin-3-ylamino-carbonyl) -3-methylphenyl] -propargylamino} -benzamidine Prepared analogously to Example 2 from N-tert-butoxycarbonyl-4-. {3- [4- (1-tert-butoxycarbonyl-pyrrolidin-3-yl-aminocarbonyl) -3-methyl-phenyl] -propargylamino] -benzamidine and trifluoroacetic acid, subsequent absorption in ethanol and precipitation with etheric hydrochloric acid Yield: 33% of the t e, Rf Value: 0.41 (inverted phase RP-8 silica gel; methanol / 5% NaCl solution = 60:40). C22H25NsO X 2HC1 (375.49 / 448.41) Mass spectrum: (M + H) * = 376 (M + 2H) ** = 185.5 Example 108 4-. { 3- [5- (N-cyclopentyl-N-methyl-aminocarbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [5- (N-cyclopentyl-N-methyl-amino-carbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 70% of theory, Rf Value: 0.21 (silica gel; methylene chloride / ethanol = 4: 1). C24H28N40 x CF3COOH (388.52 / 502.54) Mass spectrum: (M + H) * = 389 Example 109 4-. { 3- [5- (N-methyl-N- (2-phenyl-ethyl) -aminocarbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [5- (N-methyl-N- (2-phenyl-ethyl) -aminocarbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 54% of theory, R £ Value: 0.22 (silica gel; methylene chloride / ethanol = 4: 1). C27H28N40 x CF3COOH (424.56 / 538.58) Mass spectrum: (M + H) * = 425 Example 110 4-. { 3- [5- (N-methyl-N-benzyl-aminocarbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [5- (N-methyl-N-benzyl-aminocarbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 55% of theory, R £ value: 0.25 (silica gel; methylene chloride / ethanol = 4: 1). C26H26N40 x CF3COOH (410.53 / 524.55) Mass spectrum: (M + H) * = 411 Example 111 4-. { 3- [5- (2-phenyl-ethylaminocarbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [5- (2-phenyl-ethylamino-carbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid.

Yield: 54% of theory, Rf Value: 0.13 (silica gel; methylene chloride / ethanol = 4: 1). C26H26N40 x CF3COOH (410.53 / 524.55) Mass spectrum: (M + H) * = 411 Example 112 4 -. { 3 - [4- (N-methyl-N-phenyl-ammocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 4c from 4 -. { 3 - [4 - (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} -benzon? trilo with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 97% of the theory, Rf value: 0.20 (silica gel, methylene chloride / ethanol = 4: 1 and one drop? Acetic acid). C24H22N40 x HCl (382.47 / 418.93) Mass spectrum: (M + H) * = 383 Example 113 4-. { 3 - [2,5-dimethyl -4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [2,5-dimethyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} Benzamidine and trifluoroacetic acid.

Yield: 30% of theory, R £ Value: 0.18 (silica gel; methylene chloride / ethanol = 4: 1). C26H2íN4Ox CF3C00H (410.53 / 524.55) Mass spectrum: (M + H) * = 411 Example 114 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -N-methyl-propargylamino} -benzamidine Prepare analogously to example 4c from 4. { 3- [2,5-dimethyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -N-methyl-propargylamine} -benzonitrile with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 54% of the theory, R £ Value: 0.2 (silica gel, methylene chloride / ethanol = 4: 1). C27H28N40 x HCl (424.55 / 461.01) Mass spectrum: (M + H) * = 425 Example 115 4-. { 3- [2-methyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [2-methyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} benzamidine and trifluoroacetic acid.

Yield: 71% of theory, R £ Value: 0.22 (silica gel; methylene chloride / ethanol = 4: 1). C25H24N40 x CF3COOH (396.50 / 510.52) Mass spectrum: (M + H) * = 397 Example 116 4 -. { 3 - [2,5-dimethyl-4- (N-methyl-1-N-pyridin-2-yl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [2,5-dimethyl-4- (N-methyl-N-pyridin-2-yl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 50% of the theory, Rf value: 0.18 (silica gel, methylene chloride / ethanol = 4: 1). C25H25N50 x 2CF3COOH (411.51 / 639.55) Mass spectrum: (M + H) * = 412 Example 117 4-. { 3- [2-methyl-5- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [2-methyl-5- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} benzamidine and trifluoroacetic acid. Yield: 75% of the theory, R £ Value: 0.13 (silica gel; methylene chloride / ethanol = 4: 1). C2eH24N40 x CF3COOH (396.50 / 510.52) Mass spectrum: (M + H) + = 397 Example 118 4-. { 3- [4- (N-methyl-N-phenyl-aminomethyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 4c from 4. { 3- [4- [N-methyl-N-phenyl-aminomethyl) -phenyl] -propargylamino} -benzonitrile with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 70% of theory, Rf value: 0.22 (silica gel; methylene chloride / ethanol = 4: 1 + 1 drop of acetic acid). C24H24N4 x HCl (368.49 / 404.95) Mass spectrum: (M + H) + = 369 Example 119 4-. { 3- [4- (N-acetyl-N-phenyl-aminomethyl) -phenyl] -propargyl-amino} -benzamidine Prepare analogously to example 4c from 4. { 3- [4- [N-acetyl-N-phenyl-aminomethyl) -phenyl] -propargylamino} -benzonitrile with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 48% of the theory, Rf value: 0.25 (silica gel, methylene chloride / ethanol = 4: 1 + 1 drop of acetic acid). C2SH24N40 x HCl (396.50 / 432.96) Mass spectrum: (M + H) * = 397 Example 120 4-. { 3- [3- (N-methyl-N-phenyl-a-ino) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 4c from 4. { 3 - [3 - [N-methyl-N-phenyl-amino) -phenyl] -propargyl-amino} -benzonitrile with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 61% of theory, R £ Value: 0.37 (silica gel; methylene chloride / ethanol = 4: 1 + 1 drop of acetic acid). C23H22N4 x HCl (354.45 / 390.92) Mass spectrum: (M + H) * = 354 Example 121 4 - [3- (4-Benzyl-phenyl) propargylamino] benzamidine Prepared in a manner analogous to Example 2 from N-tert-butoxycarbonyl-4- [3- (4-benzyl-phenyl) -propargyl-amino] benzamidine and trifluoroacetic acid. Yield: 38% of theory, Rf Value: 0.26 (silica gel; methylene chloride / ethanol = 4: 1 + 1 drop of acetic acid). C23H21N3 x CF3C00H (339.44 / 453.46) Mass spectrum: (M + H) * = 340 Example 122 4- [3- (4-phenylsulfonyl-phenyl) -propargylaminoj-benzamidine Prepared analogously to example 4c from 4 - [3- [4-phenylsulfonyl-phenyl] -propargylamino] -benzonitrile with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 64% of theory, Rf Value: 0.14 (silica gel; methylene chloride / ethanol = 4: 1) C22H19N3S02 X HCl (389.47 / 425.93) Mass spectrum: (M + K) * = 390 Example 123 4-. { 3- [4- (4-Methylphenylsulfonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to example 4c from 4-³ 3 - [4- [4-methylphenylsulfonyl) phenyl] -propargylamino} benzonitrile with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 88% of theory, R £ Value: 0.13 (silica gel; methylene chloride / ethanol = 4: 1). C23H._N.SO_ x HCl (403.50 / 439.96) Mass spectrum: (M + H) + = 404 Example 124 4- [3- (4-Methyl-phenyl) -propargylamino] -benzamidine and 4- [2-chloro- 3- (4-Methyl-phenyl) -propenylamino] -benzamidine as a 4: 6 mixture Prepare analogously to Example 4c from 4- [3- (4-methyl-phenyl) -propargylamino] -benzonitrile with hydrogen chloride gas , saturated ethanol and ammonium carbonate. Yield: 47% of the theory, R £ Value: 0.2 (silica gel, methylene chloride / ethanol = 4: 1). C17H17N3 x HCl (263.34 / 299.80) Mass spectrum: (M + H) * = 264 C17H18C1N3 x HCl (299.80 / 336.26) Mass spectrum: (M + H) * = 300/302 (chlorine isotopes) Example 125 4- [3- (3-Methyl-phenyl) -propargylamino] -benzamidine Prepare analogously to Example 4c from 4- [3- (3-methyl-phenyl) -propargylamino] -benzonitrile with hydrogen chloride gas , saturated ethanol and ammonium carbonate. Yield: 38% of theory, R £ Value: 0.28 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C17H17N3 x HCl (263.34 / 299.80) Mass spectrum: (M + H) * = 263 Example 126 4 - [3 - (3-biphenyl) propargylamino] -benzamidine Prepare analogously to example 4c from 4- [ 3- (3-biphenyl) propargylamino] -benzonitrile with gaseous hydrogen chloride, saturated ethanol and ammonium carbonate. Yield: 74% of theory, R £ Value: 0.29 (silica gel; methylene chloride / ethanol = 4: 1 and a drop of acetic acid). C22H19N3 x HCl (325.42 / 361.88) Mass spectrum: (M + H) + = 326 Example 127 4 - [3- (4-ethoxycarbonyl-3-methyl-phenyl) propargylamino] -benzamidine Prepared analogously to example 4c from 4- [3- (4-imidazol-1-yl-carbonyl-3-methyl-phenyl) -propargylamino-benzonitrile with hydrogen chloride gas, saturated ethanol and ammonium carbonate. Yield: 46% of theory, Rf Value: 0.37 (silica gel; ethyl acetate / ethanol / ammonia = 50: 45: 5). C20H21N3O2 x HCl (335.41 / 371.87) Mass spectrum: (M + H) * = 336 (2M + H) + = 671 Example 128 4-. { 3- [4- (3- (2-hydroxycarbonyl-ethyl) -5-f-enyl-pyrazol-1-yl) -3-methyl-phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [4- (3- (2-ethoxycarbonyl-ethyl) -5-phenyl-pyrazol-1-yl) -3-methyl-phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 58% of the theory Value R £: 0.24 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4). C29H27N502 x CF3COOH (477.58 / 591.60) Mass spectrum: (M + H) * = 478 (M-H) = 476 Example 129 4 -. { 3 - [4- (3, 5-diethyl-pyrazol-1-yl) -3-methyl-phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl -4 -. { 3 - [4- (3,5-Diethyl-pyrazol-1-yl) -3-methyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Performance: 40% of the theory Rf Value: 0.3 (silica gel; methylene chloride / ethanol = 4: 1). C24H27N5 x CF3COOH (385.52 / 499.54) Mass spectrum: (M + H) + = 386 M * = 385 (M-H) = 384 Example 130 4-. { 3- [2-methyl-5- (N-methyl-N-pyrid-2-yl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl-4-. { 3- [2-methyl-5- (N-methyl-N-pyrid-2-yl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 54% of the theory Value R £: 0.17 (silica gel, methylene chloride / ethanol = 4: 1). C24H23N50 x CF3COOH (397.49 / 511.51) Mass spectrum: (M + H) * = 398 (M-H) "= 396 (M + CF3COOH-H)" = 510 Example 131 4-. { 3- [4- [N- (2-hydroxycarbonyl-ethyl) -N-pyrid-2-yl-aminocarbonyl] -2,5-dimethyl-phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [4- [N- (2-methoxycarbonyl-ethyl) -N-pyridin-2-yl-amino-carbonyl] -2,5-dimethyl-phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with ammonium chloride. Yield: 13% of the theory R £ Value: 0.5 (inverted phase RP-8 silica gel; methanol / 5% NaCl solution = 6: 4). C27H27N503 x HCl (469.55 / 542.47) Mass spectrum: (M + H) * = 470 (M-H) = 468 Example 132 4-. { 3- [5-Ethoxycarboniimethyl-2-methyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-terbutoxycarbonyl-4-. { 3 - [5-Ethoxycarbonylmethyl-2-methyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 34% of the theory, R £ Value: 0.25 (inverted phase RP-8 silica gel; methanol / 5% NaCl solution = 6: 4). C29H30N4O3 x CF3COOH (482.59 / 596.61) Mass spectrum: (M + H) * = 483 Example 133 4 - [3- (1,3-Dihydro-isobenzofuran-1-on-5-yl) propargylamino] -benzamidine Prepared as secondary product in the treatment with trifluoroacetic acid of rac-N-tert-butoxycarbonyl -4 -. { 3 - [3-Hydroxymethyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -propargylamino} -benzamidine according to example 88. Yield: 7% of the theory, R £ value: 0.59 (inverted-phase silica gel RP-8, methanol / 5% NaCl solution = 60:40). C18H15N302 X CF3COOH (305.34 / 419.36) Mass spectrum: (M + H) * = 306 Example 134 4- [3- (3-Methyl-4-pyrrolidinocarbonyl-phenyl) -propargyl-amino] pyridine a. 4-propargylaminopyridine A solution of 1.9 g (20 mmol) of 4-aminopyridine in 40 ml of tetrahydrofuran is mixed dropwise with 10 ml (30 mmol) of a 3 molar ether solution of magnesium methyl bromide and stirred for 2 hours. Subsequently, 3.7 g (28 mmol) of propargylmethanesulfonate in 40 ml of toluene are added dropwise and heated slowly to 110 ° C, whereby the volatile components are removed by distillation. After 48 hours at 110 ° C it is mixed with 100 ml of ethyl acetate, washed with 100 ml of a 14% NaCl solution, filtered and dried with sodium sulfate. After distilling off the solvent, the crude product is purified by chromatography (aluminum oxide: methylene chloride / ethanol 97: 3). Yield: 0.60 g (22% of theory) R £ Value: 0.48 (aluminum oxide: methylene chloride / ethanol 19: 1). b. 4- [3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] -pyridine Prepared analogously to the example lg from N- (bromo-2-methyl-benzoyl) pyrrolidine, 4-propargylaminopyridine, tetra (triphenyl-phosphin) -palladium (0), copper iodide and triethylamine in acetonitrile. Yield: 31% of theory, R £ value: 0.35 (silica gel; ethyl acetate / ethanol / ammonia 80: 40: 2) C20H21N3O3 (319.41) Mass spectrum: (M + H) + = 319 Example 135 Trans -4- [3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargyl-amino] cyclohexamine a. 3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargyl bromide To a solution of 3.1 g (13 mmol) of 3- (3-methyl-pyrrolidino-carbonyl-phenyl) -propargylalcohol (prepared analogously to the example 9a) and 2.27 g (14 mmol) of 1,1'-carbonyldiimidazole in 90 ml of acetonitrile 7.71 g (64 mmol) of allylbromide are added dropwise and the mixture is then stirred for 30 minutes at room temperature, then for 4 hours at 80 ° C. After this it is diluted with 350 ml of ethyl acetate, washed with 100 ml of water and 100 ml of saturated NaCl solution, dried over sodium sulphate, concentrated and purified by flash chromatography (silica gel, methylene chloride to methylene chloride). / ethanol 49: 1). Yield: 1.75 g (45% of theory), R £ Value: 0.6 (silica gel, ethyl acetate) C15H16BrNO (306) Mass spectrum: M + = 305/307 (bromine isotopes) b. Trans-4- [3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] cyclohexylamine To a solution of 0.50 g (1.63 mmol) of 3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylbromide and 0.88 g (4.10 mmol) of trans-4-tert-butoxycarbonylamino-cyclohexyl amine in 50 ml of THF is added at 0.degree. C. 0.53 g (4.09 mmol) of N-ethyl-diisopropylamine, and then it is stirred for 2 hours at 0 ° C, 2 hours at 50 ° C and 15 hours at room temperature. It is then washed twice with respectively 50 ml of a saturated solution of sodium hydrocarbonate and with 50 ml of a sodium chloride solution, the aqueous phases are extracted with 50 ml of ethyl acetate and the combined organic phases are dried with water. Sodium sulfate and concentrate in vacuo. The crude product is transformed directly in a manner analogous to Example 2 with trifluoroacetic acid and methylene chloride in the title compound. Yield: 0.38 g (41% of theory), R £ Value: 0.3 (aluminum oxide; ethyl acetate / ethanol / ammonia = 50: 45: 5). C21H29N30 x CF3COOH (339.49 / 567.53) Mass spectrum: M * = 339 Example 136 4-. { 3- [5- (2-phenyl-ethylaminocarbonyl) -2-methyl-phenyl] -prop-1-ylamino} -benzamidine A suspension of 100 mg (0.19 mmol) of 4-. { 3- [5- (2-phenyl-ethylaminocarbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine and 40 mg of 10% palladium on carbon in 20 ml of ethanol was hydrogenated for 15 minutes at 3 bar of hydrogen pressure. The catalyst was then filtered off and the filtrate was concentrated by evaporation. Yield: 100% of the theory, R £ Value: 0.59 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4). C 26 H 30 N 4 O x CF 3 COOH (414.56 / 528.58) Density spectrum: (M + H) * = 415 Example 137 4 - [3 - (2,5-dimethyl-4-isopropylcarbonyl-phenyl) -prop-1-ylamino] -benzamidine Prepared in a manner analogous to Example 136 from 4- [3 - (2,5-dimethyl-4-isopropylcarbonyl-phenyl) -propargylamino] -benzamidine, with 10% palladium on carbon and hydrogen in ethanol. Yield: 100% of the theory Value R £: 0.13 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4). C22H29N30 x CF3COOH (351.50 / 465.52) Mass spectrum: (M + H) '= 352 Example 138 4 - [3- (2,5-dimethyl-4-pyrrolidinocarbonyl-phenyl) -prop-1-ylamino] -benzamidine Prepared in a manner analogous to Example 136 from 4 - [3 - (2,5-dimet ii-4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzamidine, with 10% palladium on carbon and hydrogen in ethanol. Yield: 69% of the theory Value R £: 0.21 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4). C23H30N4O x CF3COOH (378.53 / 492.55) Mass spectrum: (M + H) * = 379 Example 139 rac-4-. { 3- [3-methyl-4- (2-methyl-pyrrolidinocarbonyl) -phenyl] -prop-1-ylamino} -benzamidine Prepared analogously to example 136 from rac-4-. { 3- [3-methyl-4- (2-methyl-pyrrolidino-carbonyl) -phenyl] -propargylamino} -benzamidine with 10% palladium on carbon and hydrogen in ethanol.

Yield: 99% of the theory Value R £: 0.2 (silica gel, methylene chloride / ethanol 4: 1). C23H30N4O X CF3COOH (378.52 / 492.55) Mass spectrum: (M + H) * = 379 Example 140 4-. { 3- [3- (2-hydroxycarbonyl-ethyl) -4-pyrrolidinocarbonyl-phenyl] -prop-1-ylamino} -benzamidine Prepared analogously to example 136 starting from 4 -. { 3- [3- (2-Hydroxycarbonyl-ethyl) -4-pyrrolidino-carbonyl-phenyl] -propargylamino} -benzamidine with 10% palladium on carbon and hydrogen in ethanol. Yield: 100% of the theory Value R £: 0.1 (silica gel, methylene chloride / ethanol 4: 1). C24H30N4O3 x CF3COOH (422.54 / 536.56) Mass spectrum: (M + H) * = 423 Example 141 4- [3- (3-Methyl-4-phenylcarbonyl-phenyl) -prop-1-yl-amino] -benzamidine Prepared in a manner analogous to Example 136 from 4- [3- (3-methyl-4-phenylcarbonyl-phenyl) -propargyl-amino] -benzamidine, with 10% palladium on carbon and hydrogen in ethanol. R £ value: 0.18 (silica gel; methylene chloride / ethanol 4: 1). C24H25N30 x HCl (371.43 / 407.95) Mass spectrum: (M + H) * = 372 (M + HC1 + H) * = 406/408 (chlorine isotope) Example 142 4-. { 3- [4- (N- (3-dimethylamino-propyl) -N-methyl-aminocarbonyl) -3-methyl-phenyl] -prop-1-ylamino} -benzamidine Prepared in a manner analogous to example 136 starting from 4-. { 3- [4- (N- (3-dimethylamino-propyl) -N-methyl-aminocarbonyl) -3-methyl-phenyl] -} propargylamino] -benzamidine, with 10% palladium on carbon and hydrogen in ethanol. Yield: 100% of the theory R £ value: 0.52 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4). C24H35N50 x 2 CF3C00H (409.59 / 637.63) Mass spectrum: (M + H) + = 410 Example 143 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -prop-1-ylamino} -benzamidine Prepared in a manner analogous to example 136 starting from 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} -berry millidine, with 10% palladium on carbon and hydrogen in ethanol. Yield: 100% of the theory R £ Value: 0.34 (inverted phase RP-8 silica gel; methanol / 5% NaCl solution = 6: 4). C26H30N4O x CF3COOH (414.56 / 528.58) Mass spectrum: (M + H) * = 415 Example 144 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -N-methyl-prop-1-ylamino} -benzamidine Prepared in a manner analogous to example 136 starting from 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -N-methyl-propargylamino} -benzamidine, with 10% palladium on carbon and hydrogen in ethanol. Yield: 59% of the theory Value R £: 0.2 (silica gel, methylene chloride / ethanol = 4: 1). C27H32N40 x HCl (428.53 / 465.03) Mass spectrum: (M + H) * = 429 Example 145 4-. { 3- [5- (N-methyl-N- (2-phenyl-ethyl) -aminocarbonyl) -2-methyl-phenyl] -prop-1-ylamino} -benzamidine Prepared in a manner analogous to example 136 starting from 4-. { 3- [5- (N-methyl-N- (2-phenyl-ethyl) -amino-carbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine, with 10% palladium on carbon and hydrogen in ethanol. Yield: 97% of the theory Value R £: 0.20 (silica gel, methylene chloride / ethanol = 4: 1).

C27H32N40 x CF3COOH (4 28.59 / 542.61) Mass spectrum: (M + H) * = 429 Example 146 4-. { 3- [5- (2-phenyl-ethylaminocarbonyl) -2-methyl-phenyl] -prop-1-ylamino} -benzamidine Prepared in a manner analogous to example 136 starting from 4-. { 3 - [5- (2-phenyl-ethylaminocarbonyl) -2-methyl-phenyl] -propargylamino} -benzamidine, with 10% palladium on carbon and hydrogen in ethanol. Yield: 100% of the theory Value R £: 0.26 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4). C26H30N4O x CF3COOH (414.56 / 528.58) Mass spectrum: (M + H) * = 415 Example 147 4-. { 3- [2-methyl-5- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -prop-1-ylamino} -benzamidine Prepared in a manner analogous to example 136 starting from 4-. { 3- [2-methyl-5- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine, with 10% palladium on carbon and hydrogen in ethanol. Yield: 79% of the theory Value R £: 0.27 (silica gel RP-8 inverted phase; methanol / 5% NaCl solution = 6: 4). C25H28N40 x CF3COOH (400.52 / 514.54) Mass spectrum: (M + H) * = 401 Example 148 4-. { 3- [2, 5-dimethyl-4 - (N-methyl-N-pyridin-2-yl-aminocarbonyl) -phenyl] -prop-1-ylamino-benzamidine Prepared in a manner analogous to Example 136 from 4 - . { 3 - [2,5-dimethyl-4- (N-methyl-N-pyridin-2-yl-aminocarbonyl) -phenyl] -propargylamino} -benzamidine, with 10% palladium on carbon and hydrogen in ethanol. Yield: 60% of the theory Value R £: 0.12 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4). C25H29N50 x 2 CF3COOH (415.53 / 643.59) Mass spectrum: (M + KX = 416 Example 149 4- [2-iodo-l- (5-phenylcarbonyl-pyrid-2-yl) prop-1-en-3 il-amino] benzamidine Prepared from N-tert-butoxycarbonyl-4- [3 - (5-phenylcarbonyl-pyrid-2-yl) -propargylamino] benzamidine by successive treatment with trimethylsilyliodide in the form analogous to example 35 and acid trifluoroacetic in analogous form to example 2. Yield: 66% of the theory, Rf value: 0.28 (silica gel, ethyl acetate / ethanol / ammonia = 50: 45: 5) C22H19IN40 x CF3COOH (482.35 / 596.37) Spectrum of mass: (M + H) * = 483 Example 150 4 - [2-Chloro-1- (5-phenylcarbonyl-1-pyrid-2-yl) prop-1-en-3-yl-amyl] benzamidine Prepared analogously to Example 4c from 4- [3 - (5-enylcarbonyl-pyrid-2-yl) propargylamino] -benzonitrile with hydrogen chloride gas, saturated ethanol and ammonium carbonate Yield: 76% of the theory, R £ value: 0.3 (silica gel; ethyl acetate / ethanol / ammonia = 5 0: 45: 5) C22H19C1N40 x HCl (390.88 / 427.34) Mass spectrum: (M + H) * = 391/393 (chlorine isotopes) Example 151 E-4- [l-chloro-l- (4-phenyloxy-phenyl) prop-l-en-3-yl-amino] benzamidine and 2-4 - [i-doro-1- (4-phenyloxy- phenyl) prop-1-en-3-yl-amino] benzamidine Prepared analogously to example 4c from 4- [3- (4-phenyloxy-phenyl) -propargylamino] -benzonitrile with hydrogen chloride gas, saturated ethanol and ammonium carbonate. Yield: 26% of an E / Z isomeric mixture which is separated by preparative HPLC (reverse phase Lichrospher 250x8mm; Eluent: component A: methanol / acetonitrile = 5: 1, component B: ammonium formate regulator pH 4.6 at 1%, components A: B 65:35) 1. Isomer (Rt = 19.05 minutes, addition product HCl- cis): E-4- [l-chloro-1- (4-phenyloxy-phenyl) prop-1-en-3-yl-amino] -benzamidine 2. Isomer (Rt = 23.53 minutes, addition product HCl-trans ): Z-4- [l-chloro-l- (4-fesnyloxyphenyl) prop-l-en-3-yl-amino] -benzamidine C22H20ClN3O x HCl (377.87 / 414.33) Mass spectrum of the mixture: ( M + H) * = 378/380 (Chlorine isotopes) Analogously to the preceding examples, the following compounds are obtained: (1) 4 -. { 3 - [4- (isoxazole idin-2-ylcarbonyl) -2,5-dimethyl-phenyl] -propargylamino} -benzamidine, (2) 4-. { 3- [4- [N- (2-ethoxycarbonyl-ethyl) -N-pyrrolidino-amino-carbonyl] -2,5-dimethyl-phenyl] -propargylamino} -benzamidine, (3. 4-. { 3- [4- [N- (2-hydroxycarbonyl-ethyl) -N-pyrrolidino-amino-carbonyl] -2,5-dimethyl-phenyl] -propargylamino} -benzamidine, (4) 4 -. { 3 - [2,5-dimethyl-4- (N-methyl-N-phenyl-amino-carbonyl) -phenyl] -propargyloxy} -benzamidine, (5) 4- [3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzamidine (6) 4-. { 3- [2,5-dimethyl-4- (N-benzoyl-N- (2-hydroxycarbonyl-ethyl) -amino) -phenyl] -propargyloxy} -benzamidine, (7) 4-. { 3- [2,5-dimethyl-4- (N-benzoyl-N- (2-ethoxycarbonyl-ethyl) -amino) -phenyl] -propargyloxy} -benzamidine, (8) 4-. { 3- [2,5-dimethyl-4- (N-isopropylcarbonyl-N- (2-hydroxycarbonyl-ethyl) -amino) -phenyl] -propargyloxy} -benzamidine, (9) 4 -. { 3 - [2,5-dimethyl -4- (N-isopropylcarbonyl-N- (2-ethoxy-carbonyl-ethyl) -amino) -phenyl] -propargyloxy} -benzamidine, (10) 4-. { 3- [2,5-dimethyl-4- (N-phenylsulfonyl-N- (2-hydroxycarbonyl-ethyl) -amino) -phenyl] -propargyloxy} -benzamidine, (11) 4 -. { 3 - [2,5-dimethyl-4- (N-phenylsulfonol-N- (2-ethoxycarbonyl-ethyl) -amino) -phenyl] -propargyloxy} -benzamidine Example 152 4-. { 3- [5-hydroxycarbonylmethyl-2-methyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} benzamidine Prepared analogously to example 3 from 4. { 3- [5-Ethoxycarbonyl-methyl-2-methyl-4- (N-methyl-N-phenyl-aminocarbonyl) -phenyl] -propargylamino} benzamidine, lithium hydroxide and subsequent treatment with trifluoroacetic acid. Yield: 5% of the theory Value R £: 0.42 (reversed-phase silica gel RP-8, methanol / 5% solution of NaCl = 6: 4).

C27H26N403 x CF3COOH (454.53 / 568.45) Mass spectrum: (M + H) * = 455 (MH) "= 453 Example 153 4- { 3- [4- [N- (2-ethoxycarbonyl-ethyl) -N - (1-ethylpyrazol-5-yl) aminocarbonyl] -2,5-dimethyl-phenyl] -propargylamino] -benzamidine It is prepared analogously to Example 2 from N-tert-butoxycarbonyl-4. 3- [4- [N- (2-ethoxycarbonyl-ethyl) -N- (1-ethyl-pyrazol-5-yl) -aminocarbonyl] -2,5-dimethyl-phenyl] -propargyl-amino.} - benzamidine and trifluoroacetic acid Yield: 24% of theory, R £ value: 0.22 (silica gel; methylene chloride / ethanol = 4: 1). C29H34N603 X CF3COOH (514.63 / 628.65) Mass spectrum: (M + H) * = 515 Example 154 4-. { 3- [4- [N- (2-hydroxycarbonyl-ethyl) -N- (1-ethylpyrazol-5-yl) -aminocarbonyl] -2,5-dimethyl-1-pheny1] -propargylamino} -benzamidine Prepare analogously to Example 3 starting from 4-. { 3- [4- [N- (2-ethoxycarbonyl-ethyl) -N- (1-ethylpyrazol-5-yl) -aminocarbonyl] -2,5-dimethyl-phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with trifluoroacetic acid.

Yield: 6% of theory, C27H30N6O3 x CF3COOH (486.58 / 600.60) Mass spectrum: (M + H) * = 487 Example 155 4-. { 3- [4- (Isoxazolid-n-2-ylcarbonyl) -3-methyl-phenyl] -propargylaminobenzamidine. Prepared analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [4- (isoxazolidin-2-yl-carbonyl) -3-methyl-phenyl] -propargylamino} benzamidine and trifluoroacetic acid. Yield: 42% of theory, Rf Value: 0.09 (silica gel; methylene chloride / ethanol = 4: 1). C21H22N402 X CF3COOH (362.44 / 476.46) Mass spectrum: (M + H) * = 363 Example 156 4 -. { 3 - [4- (diethylaminocarbonyl) -2,5-dimethyl-phenyl] -propargylamino} -benzamidine Prepare analogously to Example 2 from N-tert-butoxycarbonyl-4-. { 3- [4- (diethylaminocarbonyl) -2,5-dimethyl-phenyl] -propargylamino} benzamidine and trifluoroacetic acid. Yield: 36% of the theory, R £ Value: 0.1 (silica gel, methylene chloride / ethanol = 4: 1).

C23H28N40 x CF3C00H (376. 51 / 490.53) Mass spectrum: (M + H) + = 377 Example 157 4-. { 3- [2,5-dimethyl -4- (N- (2-methoxycarbonyl-ethyl) -N-ethyl-carbonylamino) -phenyl] -propargylamino} -benzamidine a. 2, 5-dimethyl-4- (2-methoxycarbonyl-ethyl-amino) -1-iodo-benzene 15.0 g (0.061 mol) of 2,5-dimethyl-4-iodo-aniline, 55 ml (0.611 mol) of acrylic acid methyl ester, 6 ml of benzyltrimethylammonium hydroxide and 0.3 g (3 mmol) of hydroquinone are heated for 11 days under reflux. The excess acrylic ester is then distilled off and the residue is chromatographed on silica gel, eluting with methylene chloride. Yield: 11.7 g (58% of the theory), R £ value: 0.65 (silica gel, ethyl acetate / petroleum ether = 4: 6). b. 2, 5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-ethyl-carbonylamino) -1-iodo-benzene 0.5 ml (6 mmol) of propionic acid chloride are prepared in 30 ml of tetrahydrofuran, under ice-cooling, 2.0 g (6 mmol) of 2,5-dimethyl-4- (2-methoxycarbonyl-ethyl-amino) -1-iodo-benzene are added dropwise to the reaction mixture. ml of tetrahydrofuran and stirring is continued for 30 minutes under cooling with ice. During the night, they are stirred at room temperature, then diluted with a 14% NaCl solution and extracted with ethyl acetate. The combined organic extracts are dried over sodium sulfate and concentrated by evaporation. Residue is chromatographed on silica gel eluting with petroleum ether / ethyl acetate (3: 1). Yield: 2.08 g (89% of theory), R £ value: 0.38 (silica gel, dichloromethane / ethanol = 98: 2). c. N-tert-butoxycarbonyl-4-. { 3- [2,5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-ethylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared analogously to the example lg from 2, 5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-ethyl-carbonyl-amino) -iodo-benzene, N-tert-butoxycarbonyl -4 -propargylamino-benzamidine, tetra (triphenyl-phosph) -palladium (0), copper iodide (1) and triethylamine in acetonitrile. Yield: 0.4 g (20% of theory), C30H38N4O5 (534.66) Mass spectrum: (M + H) + = 535 (M + Na) + = 557 d. 4 -. { 3 - [2,5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-ylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl-4-. { 3- [2, 5-dimethyl-4- (N- (2-methoxy-carbonyl-ethyl) -N-ethylcarbonyl-amino) -phenyl] -propargyl-amino} -benzamidine and trifluoroacetic acid. Yield: 77% of theory C25H30N4O3 x CF3COOH (434.57 / 548.57) Mass spectrum: (M + H) * = 435 (MH) "= 433 Example 158 4- { 3- [2, 5-dimethyl-4 - (N- (3-ethoxycarbonyl-propioni1) -N-isopropyl-amino) -phenyl] -propargylamino} benzamidine a.2,5-dimethyl-4-iodo-aniline To a solution of 8.8 ml (70.8 mmol) of 2,5-dimethylaniline in 250 ml of methanol and 600 ml of dichloromethane is added 25.0 g (71.8 mmol) of benzyltrimethylammonium dichloroiodate and 12.8 g (92.5 mmol) of potassium carbonate and stirred for 1 hour at room temperature. Then the inorganic salts are removed by suction and the solvent is distilled off, the residue is mixed with a solution of 13.5 g (70.8 mmol) of sodium pyrosulfite in 640 ml of water and extracted with ether. they are dried over sodium sulphate and concentrated by evaporation, the crude product is triturated with petroleum ether, separated by suction and dried. g (76% of theory), R £ value: 0.65 (silica gel; ethyl acetate / petroleum ether = 3: 7). b. 2,5-dimethyl-4-iodo-N-isopropyl-aniline 4.1 g (0.017 mol) of 2, 5-dimethyl-4-iodo-aniline, 1.4 ml (0.019 mol) of acetone, 1.4 ml (0.024 mol) of Glacial acetic acid and 0.1 g (0.001 mol) of p-toluenesulfonic acid are dissolved in 30 ml of tetrahydrofuran and stirred for 30 minutes at room temperature. Subsequently, 4.7 g (0.022 mol) of sodium acetate oxy borohydride are added and stirring is continued for 20 hours at room temperature. After adding 150 ml of water, sodium carbonate is added until a development of C02 can no longer be seen. After this it is extracted with ethyl acetate, the combined organic extracts are dried over sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel eluting with ethyl acetate / petroleum ether. Yield: 4.4 g (91.3% of theory), R £ value: 0.50 (silica gel, ethyl acetate / petroleum ether = 3: 7). c. 2, 5-dimethyl-4- (N- (3-ethoxycarbonyl-propionyl) -N-isopropyl-4-iodo-aniline 2.0 g (6.9 mmol) of 2,5-dimethyl-4-iodo-N-isopropyl-aniline and 2.4 ml (13.8 mmol) of N-ethyl-diisopropylamine are dissolved in 30 ml of tetrahydrofuran and after adding 1.5 ml (10.5 mmol) of succinic acid ethyl chloride, the mixture is heated at reflux for 2 hours. Room temperature is diluted with ethyl acetate and washed successively with 1 molar hydrochloric acid and 1 molar sodium hydroxide.The organic phase is dried over sodium sulfate and concentrated by evaporation Yield: 2.9 g (100% theory), R £ value: 0.85 (silica gel, ethyl acetate / petroleum ether = 3: 7) d.N-tert-butoxycarbonyl -4 -. {3 - [2, 5-dimethyl -4- (N- (3 -ethoxy-carbonyl-propionyl) -N-isopropyl-amino) -phenyl] -propargyl-amino.} benzamidine is prepared analogously to the example lg from 2,5-dimethyl-4 - (N- (3 - ethoxycarbonyl-propionyl) -N-isopro pil-4-iodo-aniline, N-tert-butoxycarbonyl-4-propargyl-amino-benzamidine, tetra (triphenyl-phosphin) -palladium (0), copper iodide (I) and triethylamine in acetonitrile. Yield: 39% of theory, R £ Value: 0.38 (silica gel; dichloromethane / ethanol = 19: 1). C32H42N405 (562.72) Mass spectrum: (M + H) + = 563 (M + Na) * = 585 e. 4-. { 3- [2,5-dimethyl-4- (N- (3-ethoxy-carbonyl-propionyl) -N-isopropyl-amino) -phenyl] -propargylamino} benzamidine Prepared analogously to example 2 from N-terbutoxycarbonyl-4-. { 3- [2,5-dimethyl-4- (N- (3-ethoxy-carbonyl-propionyl) -N-isopropyl-amino) -phenyl] -propargyl-amino} benzamidine and trifluoroacetic acid. Yield: 47% of theory C27H34N403 X CF3COOH (462.62 / 576.62) Mass spectrum: (M + H) * = 463. (M-H) * = 461 Example 159 4-. { 3- [5- [N- (2-ethoxycarbonylethyl) -N- (2-pyridyl) -aminocarbonyl] -2-ethyl-phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl-4-. { 3- [5- [N- (2-ethoxycarbonylethyl) -N- (2-pyridyl) -aminocarbonyl] -2-ethyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 47% of the theory Value R £: 0.19 (silica gel, dichloromethane / ethanol = 4: 1). C29H31N503 x CF3COOH (497.60 / 611.62) Mass spectrum: (M + H) * = 498 Example 160 4 -. { 3 - [5 - [N- (2-Hydroxycarbonylethyl) -N- (2-pyridyl) -amino-carbonyl] -2-ethyl-phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [5- [N- (2-ethoxycarbonylethyl) -N- (2-pyridyl) -aminocarbonyl] -2-ethyl-phenyl] -propargylamino} -benzamidine, sodium hydroxide and subsequent treatment with trifluoroacetic acid. Yield: 55% of the theory Rf Value: 0.31 (silica gel; dichloromethane / ethanol = 4: 1). C27H27N503 x CF3COOH (469.54 / 583.57) Mass spectrum: (M + H) * = 470 (MH) "= 468 Example 161 4- { 3- [2, 5 -dimethyl-4- (N- (2 - methoxycarbonyl-ethyl) -N-benzoyl-amino) -phenyl] -propargylamino.} -benzamidine Prepared in a manner analogous to Example 2 from N-tert-butoxycarbonyl-4-. {3- [2, 5-dimethyl-4 - (N- (2-methoxy-carbonyl-ethyl) -N-benzoyl-ammo) -f-enyl] -propargylamino} -benzamidine and trifluoroacetic acid Yield: 29% of the theory C29H30N4O3 x CF3COOH (482.59 / 596.61 ) Mass spectrum: (M + H) * = 483 Example 162 4 -. {3 - [2,5-dimethyl-4- (N- (2-pyridyl) -N-methyl-aminocarbonyl) -phenyl] - N-methyl-propargylamino.} -benzamidine Prepared analogously to the example from 4. {3 - [2, 5-dimethyl-4 - (N- (2-pyridyl) -N-methyl-amino -carbonyl) -phenyl] -N-methyl-propargylamino.}. -benzonitrile and hydrochloric acid / ammonium carbonate in ethanol Yield: 6% of theory C26H27N50 x HCl (425.54 / 462.00) Mass spectrum: (M + H ) * = 42 6 Example 163 4 -. { 3 - [4- (3,5-Diethyl-pyrazol-1-yl) -2,5-dimethyl-phenyl] -propargylamino} -benzamidma Prepared analogously to example 2 from N-terbutoxycarbonyl -4 -. { 3 - [4- (3, 5-diethyl-pyrazol-1-yl) -2,5-dimethyl-phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 96% of theory C25H29N5 x CF3COOH (399. 55 / 513. 57) Mass spectrum: (M + H) + = 400 Example 164 4-. { 3- [2,5-dimethyl-4- (N-ethylcarbonyl-N- (2-hydroxycarbonyl-ethyl) -amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2,5-dimethyl -4- (N-ethylcarbonyl-N- (2-methoxycarbonyl-ethyl) -amino) -phenyl] -propargylamino} -benzamidine and sodium hydroxide. Yield: 59% of theory C24H28N403 (420.52) Mass spectrum: (M + H) * = 421 (M-Na) * = 443 Example 165 4 -. { 3 - [2,5-dimethyl-4- (N-phenylsulfonyl-N- (2-methoxycarbonyl-ethyl) -amino) -phenyl] -proparg-lamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl -4 -. { 3 - [2,5-dimethyl-4- (N-phenyl-sulfonyl-N- (2-methoxycarbonyl-ethyl) -amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 63% of theory C28H30N4O4S x CF3COOH (518.64 / 632.66) Mass spectrum: (M + H) * = 519 Example 166 4-. { 3- [2,5-dimethyl-4- (N-phenylsulfonyl-N- (2-hydroxycarbonyl-ethyl) -amino) -phenyl] -proparg-lamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4 -. { 3 - [2,5-dimethyl -4- (N-phenyl-sulfonyl-N- (2-methoxycarbonyl-ethyl) -amino) -phenyl] -propargylamino} -benzamidine, lithium hydroxide and glacial acetic acid. Yield: 37% of theory C27H28N404S (504.61) Mass spectrum: (M + H) * = 505 (M + Na) * = 527 Example 167 4-. { 3- [2,5-dimethyl-4- (N-phenylsulfonyl-N- (2-methoxycarbonyl-ethyl) -amino) -phenyl] -prop-1-ylamino} -benzamidine Prepared in a manner analogous to example 136 starting from 4-. { 3 - [2,5-Dimethyl-4- (N-phenyl-sulfonyl-N- (2-methoxy-carbonyl-ethyl) -amino) -phenyl] -propargylamino} -benzamidine, 10% palladium on active carbon and hydrogen in ethanol. Yield: 65% of theory C28H34N404S x CF3COOH (522.68 / 636.70) Mass spectrum: (M + H) '= 523 Example 168 4-. { 3- [2,5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-propylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonii-4-. { 3- [2,5-dimethyl -4- (N- (2-methoxycarbonyl-ethyl) -N-propy -carbonyl-amino) -phenyl] -propargyl-amino} -benzamidine and trifluoroacetic acid. Yield: 82% of theory C26H32N403 x CF3COOH (448.57 / 562.59) Mass spectrum: (M + H) * = 449 Example 169 4 -. { 3 - [2,5-dimethyl -4- (N- (2-methoxycarbonyl-ethyl) -N-cyclopropylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl -4 -. { 3 - [2,5-dimethyl -4- (N- (2-methoxycarbonyl-ethyl) -N-cyclopropyl-carbonyl-amino) -phenyl] -propargyl-amino} -benzamidine and trifluoroacetic acid.

Yield: 37% of the theory C26H30N4O3 x CF3COOH (446.56 / 560.58) Mass spectrum: (M + H) * = 447 (MH) "= 445 Example 170 4- { 3- [2, 5 -dimetil -4 - (N- (2-methoxycarbonyl-ethyl) -N-methylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 2 from N-terbutoxycarbonyl -4 -. {3 - [ 2,5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-methylcarbonyl-amino) -phenyl] -propargyl-amino} -benzamidine and trifluoroacetic acid Yield: 90% of theory C24H28N403 x CF3COOH (420.52 / 534.54) Mass spectrum: (M + H) * = 421 Example 171 4 -. {3 - [2,5-dimethyl-4- (N- (2-hydroxycarbonyl-ethyl) -N-methylcarbonyl -amino) -fen l] -propargylamino.}. -benzamidine Prepared in a manner analogous to Example 3 starting from 4 -. {3 - [2,5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-methyl -carbonyl-amino) -phenyl] -propargylamino.} - benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid Yield: 57% of a theory C23H26N403 (406.49) Mass spectrum: (M-H) * = 405 Example 172 4 -. { 3 - [2,5-dimethyl -4- (N- (2-hydroxycarbonyl-ethyl) -N-propylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2,5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-propyl-carbonyl-amino) -phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid. Yield: 65% of theory C25H30N4O3 (434.54) Mass spectrum: (MH) "= 433 (M + H) * = 433 Example 173 4 - {3 - [2, 5-dimethyl-4- (N- 2-hydroxycarbonyl-1-ethyl-N-cyclopropyl-carbonyl-amino) -phenyl] -propargylamino.} -benzamidine Prepared in a manner analogous to Example 3 starting from 4 -. {3 - [2,5-dimethyl- 4- (N- (2-methoxycarbonyl-ethyl) -N-cyclopropylcarbonyl-1-amino) -phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid Yield: 75% of theory C25H28N403 ( 432.53) Mass spectrum: (M + Na) + = 455 (M + H) * = -433 Example 174 4 - {3 - [2, 5 -dimethyl-4- (N- (3-hydroxycarbonyl-propionyl ) -N-isopropyl-amino) -phenyl] -propargylamino.} - benzamidine Prepared in a manner analogous to Example 3 starting from 4-. {3- [2, 5-dimethyl-4- (N- (3 - ethoxycarbonyl-propionyl) -N-iso-propyl-amino) -phenyl-propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid. Impulse: 73% of theory C25H30N4O3 (434.54) Mass spectrum: (M + H) + = 435 (M-H) = 433 Example 175 4-. { 3- [2,5-dimethyl-4- (N-ethylcarbonyl-N- (2-methoxycarbonylethyl) -amino) -phenyl] -prop-1-ylamino} -benzamidine Prepared in a manner analogous to example 136 starting from 4-. { 3 - [2,5-dimethyl-4- (N-ethylcarbonyl-N- (2-methoxy-carbonyl-ethyl) -amino) -phenyl] -propargylamino} -benzamidine, 10% palladium on active carbon and hydrogen in ethanol. Yield: 99% of theory C25H34N403 x CF3COOH (438.58 / 552.60) Mass spectrum: (M + H) * = 439 Example 176 4-. { 3- [2,5-dimethyl-4- (N- (3-hydroxycarbonyl-propionyl) -N-isopropyl-amino) -phenyl] -prop-1-ylamino} -benzamidine Prepared analogously to example 136 starting from 4 -. { 3 - [2,5-dimethyl-4- (N- (3-hydroxycarbonyl-propionyl) -N-iso-propyl-ammo) -phenyl] -propargylamino} -benzamidine, 10% palladium on active carbon and hydrogen in ethanol. Yield: 99% of theory C, 5H34N403 (438.58 / 552.60) Mass spectrum: (M + H) * = 439 (M-H) = 437 Example 177 4-. { 3- [2,5-dimethyl-4- (N- (3-ethoxycarbonyl-propionyl) -N-benzyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl -4 -. { 3 - [2,5-dimethyl-4- (N- (3-ethoxycarbonyl-propionyl) -N-benzyl-amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 64% of theory C31H34N403 x CF3COOH (510.66 / 624.67) Mass spectrum: (M + H) * = 511 Example 178 4-. { 3- [2,5-dimethyl-4- (N- (3-hydroxycarbonyl-propionyl) -N-benzyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2,5-dimethyl-4- (N- (3-hydroxycarbonyl-propionyl) -N-benzyl-amino) -phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid. Yield: 73% of the theory C29H30N4O3 x CF3COOH (4 82.59 / 596.61! Mass spectrum: (M + H) = 483 (MH) = 481 Example 179 4 - { 3- [2, 5 -Dimethyl-4 - (Ne il carbonyl-N-methoxycarbonylmethylamino) -phenyl] -propargy lamino.) -benzamidine Prepared in a manner analogous to Example 2 from N-terbutoxycarbonyl-4--, 2- [2,5-dimethyl] -4- (N-Ethylcarbonyl-methoxycarbonylmet i 1 -ammo) -phenyl] -propargylamino.} - benzamidine and trifluoroacetic acid Yield: 67% of theory C24H28N403 x CF3COOH (420.52 / 534.54) Mass spectrum: (M + CF3C00H-H) * = 533 Example 180 4 - {3 - [4- (4,4-dimethyl-5-oxo-4,5-dihydro-lH-pyrazol-3-yl) -2,5-dimethyl phenyl] -propargylamino.} benzamidine a) 4-bromo-2, 5-dimethylbenzoic acid chloride 10.3 g (45 mmol) of 4-bromo-2,5-dimethyl benzoic acid are dissolved in 250 ml of dichloromethane and then of adding 9.9 thousand (135 mmol) of thionyl chloride are heated for two hours under reflux. centers by evaporation to dryness. Yield: 3.2 g (100% of the theory) b. 3- (4-Bromo-2, 5-d? Meth? -phenyl) -2, 2-dimethyl-3-oxo-propionic acid methyl ester 5.4 g (0.022 mol) of 4-bromo-2 acid chloride , 5-d? Met? Lbenzyl? Co, 4.5 ml (0.022 mmol) of l-methox? -2-met? L-1- (trimethylsi Lyloxy) -1-propene and 8.2 ml (0.066 mol) of triforide etherate of boron are heated at reflux for 20 hours in 50 ml of diethyl ether under a nitrogen atmosphere. The mixture is then washed 2 × with 50 ml of sodium hydroxide IN and 1 × with 50 ml of water. The organic phase is dried with sodium sulfate and the solvent is distilled off. Yield: 3.6 g (53% of theory) R £ Value: 0.6 (silica gel; petroleum ether / ethyl acetate = 4: 1). c. 3- (4-bromo-2, 5-d? Met? L-phenyl) -4,4-d? Met? L-4, 5- d? H? Dro-lH-p? Razol-5-one 3.5 g (11.7 mmol) of the 3- (4-bromo-2,5-dimethyl-L-phenyl) -2,2-dimethyl-3-oxo-propionic acid methyl ester and 28 ml (28 mmol) of a 1 molar solution of hydrazma in tetrahydrofuran are heated in 50 ml of ethanol for 24 hours under reflux. The solvent is removed by distillation and the residue is recrystallized from ethanol. Yield: 2.1 g (64% of the theory) R £ Value: 0.9 (silica gel, petroleum ether / ethyl acetate = 7: 3). d. N-terbutoxycarbonyl-4-. { 3- [4- (4,4-dimethyl-5-oxo-4,5-dihydro-lH-pyrazol-3-yl) -2,5-dimethyl-phenyl] -propargylamino} benzamidine Prepared analogously to the example lg from 3- (4-bromo-2,5-dimethyl-phenyl) -4,4-dimethyl-4,5-dihydro-lH-pyrazol-5-one, N- ter-butoxycarbonyl-4-propargyl-amino-benzamidine, tetra (triphenyl-phosphin) -palladium (0), copper iodide (I) and triethylamine in acetonitrile. Yield: 19% of theory, R £ Value: 0.2 (silica gel, dichloromethane / ethanol = 19: 1). and. 4-. { 3- [4- (4,4-dimethyl-5-oxo-4, 5-dihydro-lH-pyrazol-3-yl) -2,5-dimethyl-phenyl] -propargylamino} benzamidine Prepared analogously to example 2 from N-terbutoxycarbonyl-4-. { 3- [4- (4,4-dimethyl-5-oxo-4,5-dihydro-lH-pyrazol-3-yl) -2,5-dimethyl-phenyl] -propargyl-amino} benzamidine and trifluoroacetic acid. Yield: 93% of theory C23H25NS0 x CF3C00H (387.49 / 501.51) Mass spectrum: (M + H) * = 388 Example 181 4-. { 3- [2,5-dimethyl-4- (N-ethylcarbonyl-N-hydroxycarbonylmethyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2,5-dimethyl-4- (N-ethylcarbonyl-N-methoxycarbonyl-methyl-amino) -phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid. Yield: 74% of theory C23H26N403 x (406. 49) Mass spectrum: (M + H) * = 407 (M + Na) * = 429 (MH) "= 405 Example 182 4- { 3- [ 2,5-dimethyl-4- (N-ethylcarbonyl-N-ethoxycarbonylmethyl-aminocarbonylmethyl-amino) -phenyl] -propargylamino.} - benzamidine Prepared in a manner analogous to Example 2 from N-terbutoxycarbonyl -4 -. 3 - [2,5-dimethyl-4- (N-ethylcarbonyl-N-ethoxycarbonylmethyl-aminocarbonylmethyl-amino) -phenyl] -propargylamino] -benzamidine and trifluoroacetic acid Yield: 61% of theory C27H33N504 x CF3COOH (491.60 / 605.62) Mass spectrum: (M + H) * = 492 Example 183 4- {3- [2, 5-dimethyl-4- (N-ethylcarbonyl-N-hydroxycarbonylmethyl-aminocarbonylmethyl-amino) -phenyl] - propargylamino.} - benzamidine Prepared in a manner analogous to Example 3 from 4-. {3- [2, 5-dimethyl-4- (N-ethylcarbonyl-N-ethoxycarbonyl-methyl-aminocarbonylmethyl-amino) -phenyl] -propargylamino.} -benzamidine, lithium hydroxide and subsequent treatment or with glacial acetic acid. Yield: 48% of theory C25H29N504 x [463.54 Mass spectrum: (M + H) * = 464 (M-H) = 462 Example 184 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-ethoxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl-4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-ethoxycarbonylmethyl -.aminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 67% of theory C26H33N503 x CF3COOH (463.59 / 577.61) Mass spectrum: (M + H) * = 464 Example 185 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-hydroxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-methoxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine, lithic hydroxide and subsequent treatment with glacial acetic acid. Yield: 68% of theory C24H29N503 (435.53) Mass spectrum: (M + H) * = 436 (MH) "= 434 Example 186 4- { 3- [2, 5 -dimethyl-4- ( N-isopropy1-N- (3-trifluoroacetylamino-3-methoxycarbonyl-propyoml) -amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 2 from N-terbutoxycarbonyl -4 - .3. - [2,5-dimethyl-4- (N- isopropyl-N- (3-trifluoroacetylamine-3-methoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino] -benzamidine and trifluoroacetic acid.

Yield: 65% of theory C28H32Ns04 x CF3COOH (559.59 / 673.61) Mass spectrum: (M + H) * = 560 (M-H) = 558 Example 187 4-. { 3 - [2,5-dimethyl-1-4 - (N-isopropyl-N-methoxycarbonylmethoxy-methylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl-4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-methoxycarbonylmethoxymethylcarbonyl-amino) -phenyl-propargyl-amino} -benzamidine and trifluoroacetic acid. Yield: 65% of theory C26H32N404 x CF3COOH (464.47 / 578.59) Mass spectrum: (M + H) * = 464 Example 188 4 -. { 3 - [2,5-Dimethyl-4- (N-isopropyl-N-hydroxycarbonylmethoxy-methylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-methoxycarbonylmethoxy-methylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid. Yield: 12% of theory C2SH30N4O4 (450.54) Mass spectrum: (M + H) * = 451 (MH) "= 449 Example 189 4- { 3- [2, 5-dimethyl-4- (N- isopropyl-N-methoxycarbonylmethylcarbonyl-amino) -phenyl] -propargylamino.} - benzamidine Prepared analogously to Example 2 from N-terbutoxycarbonyl -4 -. {3 - [2, 5-dimethyl -4- (N - isopropyl-N-methoxycarbonylmethylcarbonyl-amino) -phenyl] -propargylamino.} - benzamidine and trifluoroacetic acid Yield: 74% of theory C25H30N4O3 x CF3COOH (434.54 / 548.56) Mass spectrum: (M + H ) * = 435 (MH) "= 433 Example 190 4 -. { 3 - [2,5-dimethyl -4 - (N-isopropyl-N-hydroxycarbonyl-lime -carbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-methoxycarbonylmethyl-carbonyl-amino) -phenyl] -propargylamino} -benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid. Yield: 80% of theory C24H28N403 (420.51) Mass spectrum: (M + H) * = 421 (M-H) = 419 (M + Na) * = 443 Example 191 4-. { 3 - [2,5-dimethyl -4- (N-isopropyl-N-methoxycarbonylmethyl-aminocarbonylmethylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine 0.3 g (0.71 mol) of 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-hydroxycarbonylmethylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine and 0.1 g (0.71 mol) of glycine methyl ester are dissolved in 10 ml of dimethylformamide and after adding 0.2 g (0.78 mol) of N, N'-dicyclohexylcarbodiimide is stirred for 20 hours at room temperature. The precipitated seat is then separated by suction and the mother liquor is concentrated by evaporation to dryness. The residue is chromatographed on silica gel eluting with dichloromethane / 5-14% ethanol.

Yield: 88% of theory C27H33N504 x HCl (491.60 / 528.06) Mass spectrum: (M + H) * = 492 (M-H) * = 490 Example 192 4-. { 3- [2,5-dimethyl-4- (N-propyl-N- (3-ethoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} benzamidine Prepared analogously to example 2 from N-terbutoxycarbonyl-4-. { 3- [2,5-dimethyl-4- (N-propyl-N- (3-ethoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 58% of theory C27H34N403 x CF3COOH (462.59 / 576.62) Rf value: 0.2 (silica gel, dichloromethane / ethanol 4: 1). Mass spectrum: (M + H) * = 463 Example 193 4-. { 3- [2,5-dimethyl-4- (N-cyclobutyl-N- (3-ethoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} benzamidine Prepared in a manner analogous to example 2 from N-tert-butoxycarbonyl-4-. { 3- [2,5-dimethyl-4- (N-cyclobutyl-N- (3-ethoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 49% of theory C28H34N403 x CF3COOH (474.61 / 588.63) Mass spectrum: (M + H) * = 475 Example 194 4-. { 3- [2,5-dimethyl-4- (N-propyl-N- (3-hydroxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} benzamidine Prepared in a manner analogous to Example 3 starting from 4 -. { 3 - [2, 5-dimethyl-4- (N-propyl-N- (3-ethoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid. Yield: 63% of theory C25H30N4O3 x HCl (434.54 / 471.00) Mass spectrum: (M + H) * = 435 (M-H) = 433 Example 195 4-. { 3- [2,5-dimethyl -4- (N-ethyl-N- (3-ethoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl -4 -. { 3 - [2,5-Dimethyl-4- (N-ethyl-N- (3-ethoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 49% of theory C26H32N403 x CF3COOH (448.57 / 562.59) Mass spectrum: (M + H) * = 449 Example 196 4-. { 3 - [2,5-dimethyl-4- (N-ethyl-N- (3-hydroxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} -benzamidine 0.2 g (0.267 mol) of 4-. { 3- [2,5-dimethyl-4- (N-ethyl- N- (3-ethoxycarbonyl-propionyl) l) -amino) -phenyl] -propargyl-amino} -benzamidine are stirred, at room temperature for 19 hours in 30 ml of 6 molar hydrochloric acid. It is then concentrated by evaporation in vacuo, the residue is triturated cor. acetone and separated by suction. Yield: 98% of theory C24H28N403 x HCl (420.52 / 456.98) Mass spectrum: (M + H) * = 421 (M-H; = 419 Example 197 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N- (N '-ethoxycarbonylmethyl-N' -methyl-aminomethylcarbonyl) -amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 2 from N-tert-butoxycarbonyl-4- (3- [2, 5-dimethyl-4- (N-isopropyl-N- (ethoxycarbonylmethyl- (N-methyl-amino) methylcarbonyl) - amino) -phenyl] -propargylamino.} - benzamidine and trifluoroacetic acid Yield: 66% of theory C28H37N503 x 2 CF3COOH (491.64 / 719.68) Mass spectrum: (M + H) * = 492 (MH) = 490 Example 198 4 -. {3 - [2,5-dimethyl-4- (N-isopropyl-N- (3-ethoxycarbonyl-propionyl) -amino) -phenyl] -propargyloxy} -benzamidine Prepared in a manner analogous to the example The starting material was 4- {3- [2, 5-d} methyl-4- (N-isopropyl-N- (3-ethoxy-carbonyl-propionyl) -amino) -phenyl} -propargyloxy} - benzo-nitrile and hydrochloric acid / ammonium carbonate in ethanol Yield: 9% of the theory C27H33N304 x HCl (463.59 / 500.047) R £ value: 0.62 (reversed-phase silica gel RP-8; methanol / 6% solution NaCl = 4: 1). Mass spectrum: (M + H) * = 464 Example 199 4- { 3- [2, 5-dimethyl -4- (N-isopro pil-N- (3-hydroxycarbonyl-propionyl) -amino) -phenyl] -propargyloxy} -benzamidine Prepared in a manner analogous to the example from 4-. { 3- [2,5-d? Methyl-4- (N-isopropyl-N- (3-ethoxy-carbonyl-propionyl) -amino) -phenyl] -propargyloxy} -benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid. Yield: 65% of theory C25H29N304 (435.53) R £ value: 0.62 (inverted phase RP-8 silica gel, methanol / 6% NaCl solution = 4: 1). Mass spectrum: (M + H) * = 436 (MH) "= 434 Example 200 4- { 3- [2, 5-dimethyl-4- (N-isopropyl-N-hydroxycarbonylmethyl-aminocarbonylmethylcarbonyl-1-amino) - pheny1] -propargylamino.} - benzamidine Prepared in a manner analogous to Example 3 from 4-. {3- [2, 5-dimethyl-4- (N-isopropyl-N-methoxycarbonylmethyl-aminocarbonylmethylcarbonyl-amino) -phenyl) ] -propargylamino.} -benzamidine, lithium hydroxide and subsequent treatment with glacial acetic acid Yield: 3% of theory C26H31N504 (477.568) R £ value: 0.74 (inverted phase RP-8 silica gel; methanol / solution at 6% NaCl = 4: 1.) Mass spectrum: (M + H) * = 478 (M + Na) * = 500 (MH) "= 476 Example 201 4 -. { 3 - [2,5-dimethyl-4- (N-isopropyl-N- (3-amino-3-ethoxycarbonyl-propionyl-amino) -phenyl] -propargylamino] -benzamidine Prepared in a manner analogous to Example 2 starting from of N-terbutoxycarbonyl-4-. {3- [2, 5-dimethyl-4- (N-isopropyl-N- (3-tert-butoxycarbonyl-amino-3-ethoxycarbonyl-propionylamino) -phenyl] -propargylamino} - benzamidine and trifluoroacetic acid and subsequent treatment with ethanolic hydrochloric acid.

Yield: 86% of theory C27H._N.O_ 2 HCl (477.62 / 550.54) Rf value: 0.74 (inverted phase RP-8 silica gel, methanol / 6% solution of? ACl = 4: 1). Mass spectrum: (M + H) * = 478 Example 202 4 -. { 3 - [2,5-dimethyl-4- (γ-isopropyl-β- (3-amino-3-hydroxycarbonyl-propionyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from of 4 - { 3 - [2, 5-dimethyl-4 - (? - isopropyl-? - (3-amino-3-ethoxycarbonyl-propionyl-amino) -phenyl] -propargylamino.} - benzamidine and hydroxide of potassium and subsequent treatment with ethanolic hydrochloric acid Yield: 12% of theory C25H31? 503 x 2HC1 (449. 56 / 522.49) R £ value: 0.74 (inverted phase RP-8 silica gel; 6% de? ACl = 4: 1). Mass spectrum: (M + H) * = 450 (MH) "= 448 Example 203 4- { 3- [5-fluoro-2-methyl-4- ( β-isopropyl-β-ethoxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 2 from β-tert-butoxycarbonyl-4-. {3- [5-fluor-2 - methyl-4- (? -isopropyl-β-ethoxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylamino.} - benzamidine and trifluoroacetic acid and treats Subsequent treatment with ethanolic hydrochloric acid.

Yield: 43% of theory C25H30FN5O3 x HCl (467.55 / 504.01) R £ value: 0.2 (silica gel; dichloromethane / methanol = 3: 1). Mass spectrum: (M + H) * = 468 (MH) "= 466 Example 204 4 -. {3 - [5-f luor-2-methyl-4 - (N-isopropyl-N-hydroxycarbonyl-methylaminocarbonyl- amino) -phenyl] -propargylamino.} - benzamidine Prepared in a manner analogous to Example 3 from 4-. {3- [5-fluoro-2-methyl-4- (N-isopropyl-N-ethoxycarbonyl-methylaminocarbonyl -amino) -phenyl] -propargylamino.} - benzamidine, potassium hydroxide and subsequent treatment with glacial acetic acid Yield: 92% of theory C23H26FN503 (439.49) Mass spectrum: (M + H) * = 440 (M + Na) * = 462 (MH) "= 438 Example 205 4 -. { 3 - [2-methyl-4- (N-isopropyl-N-ethoxycarbonyl-methylaminocarbonyl-amino) -phenyl] -propargi lamino} -benzamidine Prepared in a manner analogous to Example 2 from N-terbutox? carbon? l-4- 3- [2-met? l-4- (N-isopropyl-N-ethoxy-carbonylmethylammocarbonyl-amino) -phen? ] -proparg? lammo} -benzamidma and acide tri-fluoroacetic acid. Yield: 56% of theory C25H31N503 x CF3C00H (449 55 / 563.58) Mass spectrum. (M + H) = 450 Example 206 4-. { 3- [2, 5-dimethyl-4 (N-cyclobutyl-N-methoxycarbonylmethyl-carbonyl-ammo) phen? I] -proparg? Lammo} -benzamidma Prepared in a manner analogous to example 2 from N-terbutox? carbon? l-4-! 3 - [2,5-dimethyl-4- (N-cyclobutyl-N-methoxycarbonylmethyl-carbonyl-amino) -phen? l] -proparg? lam? no} -benzamidma and trifluoroacetic acid. Yield: 65% of theory C26H30N4O3 x CF3COOH (446.55 / 560.56) Mass spectrum: (M + H) * = 447 Example 207 4 -. { 3 - [2,5-dimet II -4 - (N-isopropyl-N-ammomethylcarbonyl-ammo) -f in? L] -proparg? Lam? No} -benzam? d? na Prepared analogously to example 2 from N-terbutox? carbon? l -4 -. { 3 - [2, 5 -d? Met? L -4 - (N- isopropyl-N-terbutoxycarbonylammomethylcarbonyl-amino) -fenyl] -proparg? Lam? No} -benzam? d? na and tri luoracético acid. Yield: 61% of theory C23H29NsO x 2 CF3COOH (391.53 / 619.57) R £ value: 0.70 (inverted phase RP-8 silica gel, methanol / 6% NaCl solution = 4: 1). Mass spectrum: (M + H) * = 392 Example 208 4-. { 3- [2-methyl-4- (N-isopropyl-N-hydroxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2-methyl-4- (N-isopropyl-N-ethoxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine, sodium hydroxide and subsequent treatment with glacial acetic acid. Yield: 42% of theory C23H27Ne03 (421.50) Mass spectrum: (M + H) * = 422 (M + Na) * = 444 (MH) "= 420 Example 209 4 - { 3 - [2-chloro -5-methyl-1-4- (N-isopropyl-N-ethoxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylamino.) -benzamidine Prepared in a manner analogous to Example 2 from N-terbutoxycarbonyl-4-. {3 - [2-Chloro-5-methyl-4- (N-isopropyl-N-ethoxycarbonylmethylaminocarbonyl-amino) -phenyl] -propargylamino] -benzamidine and trifluoroacetic acid Yield: 38% of the theory C25H30ClN5O3 x CF3COOH ( 484.00 / 598.02) R £ value: 0. 4 (gel of yes l ice; dichloromethane / methanol = 4: 1). Mass spectrum: (M + H) * = 484/486 (chlorine isotopes) Example 210 4 -. { 3 - [2-Chloro-5-methyl-4- (N-isopropyl-N-hydroxycarbonyl-methylaminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2-Chloro-5-methyl-4- (N-isopropyl-N-ethoxycarbonyl-methylaminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine, sodium hydroxide and subsequent treatment with glacial acetic acid. Yield: 7% of theory C23H26C1N503 (455.94) Mass spectrum: (M + H) * = 456/458 (chlorine isotopes) (M + Na) * = 478/480 (chlorine isotopes) (MH) "= 454/456 (chlorine isotopes) Example 211 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N- (3-amino-3-propionyl) -ammo) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl -4 -. { 3 - [2,5-dimethyl -4- (N-isopropyl-N- (3-tert-butoxycarbonyl-amino-propionyl) -amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 71% of the theory R £ Value: 0.36 (silica gel, dichloromethane / ethanol = 4: 1) R £ Value: 0.36 (inverted phase RP-8 silica gel, methanol / 6% NaCl solution = 4: 1). C24H31N50 x 2 CF3C00H (405.55 / 633.59) Example 212 4 -. { 3 - [3-methyl-4- (N-isopropyl-N-ethoxycarbonylmethylaminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl-4-. { 3- [3-methyl-4- (N-isopropyl-N-ethoxycarbonylmethylaminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 46% of the theory Rf Value: 0.21 (silica gel, dichloromethane / ethanol = 4: 1) C25H31N503 x CF3COOH (449.56 / 563.58) Mass spectrum: (M + H) * = 450 (MH ) "= 448 Example 213 4-. {3- [3-Methyl-4- (N-isopropyl-N-hydroxycarbonylmethylamino-carbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared from 4-. {3- [3-Methyl-4- (N-isopropyl-N-ethoxycarbonylmethylamino-carbonyl-amino) -phenyl] -propargylamine] -benzamidine by the action of 18 hours of 20 ml of 6N HCl and subsequent elimination by distillation of volatile components Yield: 82% of the theory Value R £: 0.46 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4) C23H27N502 X HCl (421.50 / 457.96 ) Mass spectrum: (M + H) * = 422 (M + Na) * = 444 (MH) = 420 (M + HC1-HX = 456/458 (chlorine isotopes) Example 214 4-. [2-methyl-4- (N-isopropyl-N- (2-trifluoroacetylamino-3-methoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} -be nzamidine Prepared in a manner analogous to Example 2 from N-terbutoxycarbonyl-4-. { 3- [2-methyl-4- (N-isopropyl-N- (2-trifluoroacetylamino-3-methoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid. Yield: 100% of the theory Value R £: 0.17 (silica gel, dichloromethane / ethanol = 4: 1) C27H30N5O4 x CF3COOH (545.57 / 659.59) Mass spectrum: (M + H) * = 546 ( MH) "= 544 [M + CF3COOH-H) + = 658 Example 2 15 4- { 3- [2-methyl-4- (N-isopropyl-N- (2-trifluoroacetylamino-3-hydroxycarbonyl-propionyl ) -amino) -phenyl] -propargylamino.} -benzamidine Prepared in a manner analogous to Example 213 from 4-. {3 - [2-ene] -4- (N-isopropyl-N- (2-trifluoroacetyl) -amino-3-methoxycarboni 1 -propionyl) -amino) -phenyl] -propargylamino.} - benzamidine and 6N HCl Yield: 100% of the theory Rf Value: 0.46 (silica gel inverted phase RP-8; methanol / 5% solution of NaCl = 6: 4) C26H28N504 X HCl (531.540 / 568.00) Mass spectrum: (M + H) * = 532 (MH) = 530 (M + CF3COOH-H) + = 658 Example 216 4- {3- [2-methyl-4- (N-isopropyl-N- (2-amino-3-hydroxycarbonyl-propionyl-amino) -phenyl] -propargylamino} -benzamidine Prepared 0.160 g (0.282) mmol) of 4- { 3- [2 -methyl-4- (N-isopropyl-N- (2-trifluoroacetylamino-3-hydroxy-carbonyl-propionyl) -amino) -phenyl] -propargylamino} -benzamidine and 120 mg of sodium carbonate in 20 ml of methanol by stirring at room temperature for 5 days. After the subsequent heating for 1 day at 60 ° C, the volatile components are distilled off.

Yield: 98% of the theory Rf Value: 0.46 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4). C24H29N503 x HCl (435.53 / 471.99) Example 217 4 -. { 3 - [2,5-dimethyl-4- (N-isopropyl-N- (N '-hydroxycarbonyl-methyl-N' -methyl-aminomethylcarbonyl) -amino) -phenyl] -propargyl-amino} -benzamidine Prepared in a manner analogous to Example 3 starting from 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N- (N '-ethoxycarbonylmethyl-N' -methyl-aminomethylcarbonyl) -amino) -phenyl] -propargylamino} -benzamidine, sodium hydroxide, subsequent precipitation with glacial acetic acid and multiple chromatographic purification on HPLC column. Yield: 2% of theory C26H33N503 x HCl (463.58 / 500.04) Mass spectrum: (M + H) * = 464 Example 218 4-. { 3- [2-methyl-4- (N-isopropyl-N- (3-trifluoroacetylamino-3-methoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to example 2 from N-terbutoxycarbonyl-4-. { 3- [2-methyl-4- (N-isopropyl-N- (3-trifluoroacetylamino-3-methoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid.

Performance: 89% of the theory Rf Value: 0.21 (silica gel, dichloromethane / ethanol = 4: 1) C27H30F3N5O4 X CF3COOH (545.57 / 659.59) Mass spectrum: (M + H) * = 546 (MH) "= 544 Example 219 4- [3- (3-bromo-5- (2-methyl-pyrrolidinocarbonyl ) -furan-2-yl) -propargylamino] benzamidine Prepared in a manner analogous to the example lg from 2,3-dibromo-5- (2-methyl-pyrrolidinocarbonyl) -furan, N-tert-butoxycarbonyl -4- propargyl-amino-benzamidine, tetra (triphenyl-phosphin) -palladium (0), copper iodide (I) and triethylamine in acetonitrile, and subsequent cleavage of the terbutoxycarbonyl residue by trifluoroacetic acid in analogous manner to Example 2. Yield: 17% the theory, R £ Value: 0.28 (silica gel; dichloromethane / ethanol = 4: 1). C20H21BrN4O2 x CF3COOH (429.32 / 543.34) Mass spectrum: (M + H) * = 429/431 (bromine isotopes) Example 220 4-. { 3- [2-tnethyl-4- (N-isopropyl-N- (3-amino-3-methoxycarbonyl-propionyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 216 from 4 - { 3- [2-methyl-4- (N-isopropyl-N- (3-trifluoroacetylamino-3-methoxycarbonyl-propionyl) -amino) -phenyl] -propargylamino] -benzamidine and sodium carbonate in methanol Yield: 93% of the theory R £ Value: 0.45 (inverted phase RP-8 silica gel, methanol / 5% NaCl solution = 6: 4) C25H31N503 x CF3COOH (449.56 / 563.58) EXAMPLE 221 4- {3- [3-methyl-4- (N-isopropyl-N-methoxycarbonylmethylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 2 from N-terbutoxycarbonyl -4- {3- [3-methyl-4- (N-isopropyl-N-methoxycarbonylmethylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine and trifluoroacetic acid Yield: 55% of the theory Value R £ : 0.21 (silica gel; dichloromethane / ethanol = 4: 1) C24H28N403 x CF3COOH (420.52 / 534.54) Mass spectrum: (M + H) * = 421 (M + CF3C00H-H) "= 533 Example 222 4 - {3 - [3 - methyl -4- (N-cyclopenti1-N-methoxycarbonylmethylcarbonyl-amyl) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 2 from N-terbutoxycarbonyl-4-. {3- [3-methyl-4- (N-cyclopentyl-N-methoxycarbonylmethylcarbonyl-amino) -phenyl] -propargylamino] -benzamidine and trifluoroacetic acid Yield: 85% of the theory Value R £: xxxx (silica gel; dichloromethane / ethanol = 4: 1) C26H30N4O3 x CF3COOH (446.55 / 560.57) Mass spectrum: (M + H) * = 447 (M + CF3COOH-H) "= 559 Example 223 4 - {3 - [3 -methyl- 4- (N- i sopropy1-N-hydroxycarbonylmethylcarbonyl-amino) -phenyl] -propargylamino.} - benzamidine Prepared in a manner analogous to Example 213 from 4 -. {3- [3-methyl-4- (N-isopropyl -N-methoxycarbonyl-methylcarbonyl-amino) -phenyl] -propargylamino.} - benzamidine and 6N HCl. Yield: 100% of the theory Value R £: 0.40 (silica gel; dichloromethane / ethanol = 4: 1). C23H26N403 X HCl (4 06.48 / 442.94) Mass spectrum: (M + H) * = 407 (M-H) = 405 Example 224 4 -. { 3- [3-methyl-4- (N-cyclopentyl-N-hydroxycarbonylmethi-carbonyl-amino) -phenyl] -propargylamino} -benzamidine Prepared in a manner analogous to Example 213 from 4-. { 3 - [3-methyl-4 - (N-cyclopentyl-N-methoxycarbonyl-methylcarbonyl-amino) -phenyl] -propargylamino} -benzamidine and 6N HCl. Yield: 92% of the theory Value R £: 0.23 (silica gel; dichloromethane / ethanol = 4: 1). C25H28N403 x HCl (432.52 / 468.99) Mass spectrum: (M + H) * = 433 (M-H) = 431 Analogously to the preceding examples, the following compounds can be prepared: 4-. { 3- [2-Bromo-5-methyl-4- (N-isopropyl-N- (2-ethoxy-carbonyl-ethyl-carbonyl) -amino) -phenyl] -propargylamino} -benzamidine 4 -. { 3 - [2,5-dimethyl-4- (N-isopropyl-N- (2-ethoxycarbonyl-2-aminoacetylamino) -phenyl] -propargylamino] -benzamidine 4 -. {3 - [2,5-dimethyl] -4- (N-isopropyl-N- (2-hydroxycarbonyl-2-amino-acetylamino) -phenyl] -propargylamino}. -benzamidine 4-. {3- [2,5-Bis (trifluoromethyl) - 4- (N-isopropyl-N-ethoxycarbonylmethylaminocarbonyl-amino) -phenyl] -propargyl-amino.} - benzamidine 4 -. {3 - [2, 5-Bis (trifluoromethyl) -4- (N-isopropyl-N -hydroxycarbonylmethylaminocarbonyl-amino) -phenyl] -propargyl-amino.}. -benzamidine 4 -. {3 - [2-trifluoromethyl-5-methyl-4- (N- isopropyl-N-ethoxycarbonylmethylaminocarbonyl-amino) -phenyl] - propargi1-amino.}. -benzamidine 4 - { 3 - [2-trifluoromethyl-5-methyl-4- (N-isopropyl-N-hydroxycarbonylmethylaminocarbonyl-amino) -phenyl] -propargylamino.} - benzamidine 4 -. {3 - [2-trifluoromethyl-4- (N-isopropyl-N-ethoxycarbonylmethylaminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine 4 -. {3 - [2-trifluoromethyl-4 - (N-isopropyl -N-hid roxy -carbonylmethylaminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine 4 -. { 3 - [2,5-dimethyl-4- (N-isopropyl-N- (2-ethoxycarbonylethylaminocarbonyl) -amino) -phenyl] -propargylamino} -benzamidine 4-. { 3- [2,5-dimethyl -4- (N-isopropyl-N- (2-hydroxycarbonylethylaminocarbonyl) -amino) -phenyl] -propargylamino} -benzamidine 4-. { 3- [2,5-dimethyl -4- (N-isopropyl-N- (ethoxy-carbonylmethylaminomethylcarbonyl) -amino) -phenyl] -propargyl-amino} -benzamidine 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N- (hydroxycarbonylmethylaminomethylcarbonyl) -amino) -phenyl] -propargyl-amino} -benzamidine 4-. { 3- [2,5-dimethyl -4- (N-isopropyl-N- (4-amino-4-ethoxycarbonylbutanoyl) -amino) -phenyl] -propargylamino} -benzamidine 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N- (4-amino-4-hydroxycarbonylbutanoyl) -amino) -phenyl] -propargylamino} -benzamidine 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N- (2-amino-4-ethoxycarbonylbutanoyl) -amino) -phenyl] -propargylamino} -benzamidine 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N- (2-amino-4-hydroxycarbonylbutanoyl) -amino) -phenyl] -propargylamino} -benzamidine 4 -. { 3 - [2,5-Dimethyl-4- (N-isopropyl-N- (2-ethoxycarbonylethylaminocarbonyl) -amino) -phenol] -propargylamino} -benzamidine 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N- (2-hydroxycarbonylethylaminocarbonyl) -amino) -phenyl] -propargylamino} -benzamidine 4-. { 3- [2-methyl-4- (N- isopropyl-N- (3-amino-3-hydroxycarbonylpropionyl) -amino) -phenyl] -propargylamino} -benzamidine 4-. { 3- [2-methyl-4- (N-isopropyl-N- (2-amino-3-methoxy-carbonylpropionyl) -amino) -phenyl] -propargylamino} -benzamidine 4-. { 3 - [2,5-dimethyl-4 - (N-isopropyl-N-aminocarbonyl-1-amino) -phenyl] -propargylamino} -benzamidine 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-piperazin-1-yl -carbonyl) -amino) -Eenyl-J-propargylamino} -benzamidine 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-piperazin-1-yl-methylcarbonyl) -amino) -phenyl] -propargylamino} -benzamidine 4 -. { 3 - [2,5-dimethyl-4- (N-isopropyl-N- (2-pyrrolidon-5-yl-carbonyl) -amino) -phenyl] -propargylamino} -benzamidine 4 -. { 3 - [3-Bromo-5-pyrrolidinocarbonyl-furan-2-yl] -propargylamino} benzamidine Example 225 Dry ampoule with 75 mg of active substance per 10 ml Composition: Active substance 75.0 mg Mannitol 50.0 mg Water for injection purposes ad 10.0 ml Preparation: Active substance and mannitol are dissolved in water. After filling it is lyophilized. The solution to obtain the solution ready to be used is made with water for purposes of; injection. Example 226 Dry ampule with 35 mg of active substance per 2 ml Composition: Active substance 35.0 mg Mannitol 100.0 mg Water for purposes of: injection ad 2.0 ml Preparation: Active substance and mannitol are dissolved in water. After filling it is lyophilized. The solution to obtain the ready-to-use solution is made with water for injection purposes. Example 227 Tablet with 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 mq 215.0 mg Preparation: ( 1), (2) and (3) are mixed and granulated with an aqueous solution of; (4) . When the dry granulate is intermixed (5) . Compressed tablets, biplanes with facet on both sides and unilateral groove are compressed from this mixture. Diameter of the tablets: 9 mm Example 228 Tablet with 350 mg of active substance Composition (1) Active substance 350.0 mg (2) Lactose 136.0.0 mg (3) Corn starch 80.0 mg (4) Polyvinylpyrrolidone 30.0 mg (5) Magnesium stearate 4.0 mg 600.0 mg Preparation: (1), (2) and (3) are mixed and granulated with an aqueous solution of. (4) . The dry granulate is intermixed (5). Compressed tablets, biplanes with facet on both sides and unilateral groove are compressed from this mixture. Diameter of the tablets: 12 mm Example 229 Capsules with 50 mg of active substance (1) Active substance 50.0 mg (2) Dry corn starch 58.0 mg (3) Powdered lactose 50.0 mg (4) Magnesium stearate 2.0 mq 160.0 mg Preparation : (1) is crushed with (3). This grinding is added to the mixture of (2) and (4) by mixing intensively. This powder mixture is filled in a capsule filling machine in size 3 hard gelatin capsules. Example 230 Capsules with 350 mg of active substance (1) Active substance 350.0 mg (2) Dry corn starch 46.0 mg (3) Lactose powdered 30.0 mg (4) Magnesium stearate 4.0 mg, 430.0 mg Preparation: (1) is crushed with (3). This grinding is added to the mixture of (2) and (4) by mixing intensively. This powder mixture is filled in a capsule filling machine in size 0 hard gelatin capsules. Example 231 Suppositories with 100 mg of active substance 1 suppository contains Active substance 100.0 mg Polyethylene glycol (MG 1500) 600.0 mg Polyethylene glycol (MG 6000) 460.0 mg polyethylene sorbitol monostearate 840.0 mq 2000.0 mg Preparation Polyethylene glycol is fused together with polyethylene sorbitol monostearate. At 40 ° C the active substance is dispersed homogeneously inside the melt. It is cooled to 38 ° C and filled into slightly cooled suppository molds.

Claims

1. Substituted aryl and heteroaryl derivatives of the general formula Ar - A- (HCR - X - Y (I) wherein A ethynylene group, a vinylene or ethylene group optionally substituted by an alkyl group, Gl-3 or carboxyalkyl Cl-3 or by a chlorine, bromine or iodine atom, means A RL a hydrogen atom, a Cl-3 alkyl group or Cl-3 carboxyalkyl, Ar a phenyl group substituted by the residues R2 to R4, wherein R2 represents a Cl-6 alkyl or C3-7 cycloalkyl-C1-6 alkyl group 3, which in each case in the alkyl part Cl-6 and Cl-3 can be substituted by a carboxy, phenyl, amino, alkyl-Cl-3-amino, carboxy-alkyl-Cl-3-amino group, di ( alkyl-Cl-3) -amino, N- (carboxy-alkyl-Cl-3) -alkyl-Cl-3-amino, C3-7-amino-cycloalkyl, phenylamino, N- (alkyl-Cl-3) -phenyl -amino, N- (alkanoyl-Cl-4) -phenylamino, heteroarylamino, N- (alkyl-Cl-3) -heteroarylamino,, N- (carboxy-alkyl-CL-3) -phenylamino or N- (carboxy-alkyl) -Cl-3) -heteroarylamino, a carboxy-alkyl-Cl-5 group which in the alkyl part is substituted with an alkyl-Cl-3-amino group, N, -di (alkyl-Cl-3) -amino, pyrrolidino , piperidino or hexameti1enimino, a carboxy-alkyl-Cl-5 group in which the hydrogen atoms of a methylene group are substituted by a n-alkylene-C2-5 bridge , a phenyl, phenyloxy or phenylsulfonyl group, which in the phenyl part in each case may be substituted by a fluorine, chlorine, bromine or iodine atom, by an alkyl-Cl-3, carboxy-alkyl-Cl-3 or alkoxy group -Cl-3, an alkyl-Cl-5-amino group, carboxy-alkyl-Cl-3-amino, di (alkyl-Cl-5) -amino, N- (carboxy-alkyl-Cl-3) -alkyl- Cl-5-amino, C3-7-amino-cycloalkyl, N- (carboxy-alkyl-Cl-3) -3-C3-amino-cycloalkyl, phenylamino, N- (alkyl-Cl-3) -phenylamino, N- (carboxy-alkyl-Cl-3) -phenylamino, heteroarylamino, N- (alkyl-Cl-3) -heteroarylamino or N- (carboxy-alkyl-Cl-3) -heteroarylamino, an alkyl-Cl-5-carbonylamino group, C3-7-cycloalkylcarbonyl-amino, aryl-carbonylamino, heteroarylcarbonylamino, alkyl-Cl-5-sulfonylamino, arylsulfonylamino, heteroarylsulphonylamino, N- (alkyl-Cl-3) -alkyl-Cl-5-carbonylamino, N- (alkyl) -Cl-3) -cycloalkyl-C3-7-carbonylamino, N- (alkyl-Cl-3) -aryl-carbonylamino, N- (alkyl-Cl-3) -heteroarylcarbonylamino, N- (alkyl-Cl-3) - alkyl-Cl-5-sulfoni lamino,. N- (alkyl-Cl-3) -aryl-sulfonylamino or N- (alkyl-Cl-3) -heteroaryl-sulfonylamino, whereby the above-mentioned N- (alkyl-Cl-3) moieties can be further substituted by a group carboxy, carboxy-alkyl-Cl-3-aminocarbonyl or N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-aminocarbonyl, or with the exception of the carbon atom a relative to the nitrogen atom, also by a group hydroxy, carboxy-alkoxy-Cl-3, amino, carboxy-alkyl-Cl-3-amino or N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino, a cycloalkyleneimino group of 5 to 7 members , an amino group, alkyl-Cl-5-amino, C3-7-amino-cycloalkyl, aryl-amino, aryl-alkyl-Cl-3-amino, heteroarylamino or heteroaryl-alkyl-Cl-3-amino, which in each case may be substituted at the amino nitrogen atom with an alkyl-Cl-3-carbonyl, carboxy-alkyl-Cl-3-carbonyl, carboxy-alkyl-Cl-3-amino-carbonyl, 2-oxo-pyrrolidinylcarbonyl group or piperazino-carbonyl, being that in addition (i) the amino group precedes The above-mentioned monosubstituted by an alkyl-Cl-3-carbonyl, carboxy-alkyl-Cl-3-carbonyl or carboxy-alkyl-Cl-3-aminocarbonyl group is substituted by a 5- to 7-membered cycloalkyleneimino group or by a group N, N-di- (alkyl-Cl-5) -amino, and (ii) the alkyl part of the aforementioned alkyl-Cl-3-carbonyl group is substituted by a carboxy, amino, hydroxy, carboxy-alkoxy-Cl group -3, carboxy-alkyl-Cl-3-aminocarbonyl, carboxy-alkyl-Cl-3-amino, N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino or amino-alkyl-Cl-3 -carbonylamino, or by a carboxy or hydroxy group and by an amino or trifluoroacetylamino group, a carbimino group substituted on the nitrogen atom by a carboxy-alkoxy-Cl-3 group, amino, alkyl-Cl-3-amino, carboxy-alkyl-Cl-3-amino, di- (alkyl-Cl-3) -amino or N- (carboxy-alkyl-Cl-3) -alkyl-Cl-3 -amino, and at the carbon atom by an alkyl-Cl-5 group, by a phenyl group optionally substituted by an alkyl-Cl-3 or alkoxy-Cl-3 group, or by a heteroaryl group optionally substituted by an alkyl group -Cl-3, a heteroaryl or heteroaryl-alkyl-Cl-3 group, which in each case may also be additionally substituted in the. heteroaryl portion by a phenyl or heteroaryl group, or by a phenyl or heteroaryl group and by a carboxy-Cl-3 alkyl or alkoxy-Cl-3-carbonyl-Cl-3 alkyl group, a 5-oxo-4 group, 5-dihydro-pyrazolyl or 6-oxo-4,5-dihydro-pyridazinyl, optionally substituted by 1 to 3 alkyl-Cl-3 groups, wherein an alkyl substituent may simultaneously be substituted by a carboxy or alkoxy group? Cl-3-carbonyl, or a carbonyl group, which may be substituted by a hydrogen atom, a hydroxy group, alkoxy-Cl-5 or c?-Cloalcoxβ-C3-7, by an alkyl-Cl- group 5-C6-7alkyl-C3-7 optionally substituted by a carboxy group, by an alkylene-Cl-3 group substituted by a piperazm group, by a phenyl group which may be substituted by a fluorine, chlorine, bromine atom or iodine, by an alkyl-Cl-3, carboxy-alkyl-Cl-3, alkoxy-Cl-3 or carboxy group, by an ammo group, alkyl-Cl-5-ammo, carboxy alkyl -Cl - 3-amino, cycloaikyl-C3 -7-amine, phenylalamine or heteroaplammo, which in additionally, they may be substituted at the nitrogen atom with an alkylene-Cl-5, c-chloralkyl-C3-7, phenyl-alkylene-Cl-3, carboxy-alkyl-Cl -3 group, 2- (di- (alkyl-Cl-3) -amino) -ethyl, 3- (di- (alk-1-Cl-3) -amino) -propyl, di- (alk-1-Cl-3) - ammo, 2- (N-carbox? -alkyl-Cl-3-alkyl? -Cl-3-ammo) -ethyl, 3- (N-carbox? alkyl? -Cl-3 -alkyl) Cl-3 -ammo) -propyl or N-carboxy-alky1-Cl-3-alky1-Cl-3-ammo, phenyl, pipdyl, pyrrolidyl or piperidyl, by a pyrrolyl, thienyl, imidazolyl, pyrazolyl group, thiazolyl, pyridyl, pipmidyl, pyrazyl or pyridazinyl optionally substituted by one or two alkyl-Cl-3 groups, to which a phenyl ring may be condensed in each case through two adjacent carbon atoms, by a C3-cycloalkylene group 6-imino, bicyclo-alkylene-C5-8-imino, morpholino, piperazino, dihydro-pyrazolo, tetrahydropyrazolo, tetrahydroisooxazole, tetrahydropyrazinyl or tetrahydropyridazinyl, optionally substituted by an alkyl-C group l-3 or carboxy-alkyl-Cl-3, or by a cycloalkylene-C3-6-imino group optionally substituted by an alkyl-Cl-3, carboxy-alkyl-Cl-3, hydroxy, hydroxy-alkyl-Cl- group 3, amino, carboxy, carboxy-alkoxy-Cl-3-alkyl-Cl-3, carboxy-alkyl-Cl-3-amino-alkyl-Cl-3, or carboxy-alkyl-Cl-3-amino-carbonyl-alkyl -Cl-3, by a bicycloalkylene-C5-8-imino group, morpholino, piperazino, dihydropyrazolo, tetrahydropyrazolo, tetrahydroisooxazole, tetrahydropyrazinyl or tetra-hydropyridazinyl, optionally substituted by an alkyl-Cl-3 or carboxy-alkyl-Cl-3 group , R3 represents a hydrogen, fluorine, chlorine, bromine or iodine atom, a formyl or trifluoromethyl group, an alkoxy-Cl-3, amino, alkyl-Cl-3-amino group, di- (alkyl-Cl-3) - amino, alkanoyl-Cl-4-amino or N- (alkanoyl-Cl-4) -alkyl-Cl-3-amino an alkyl-Cl-3 group optionally substituted by a hydroxy group, alkoxy-Cl-3, carboxy, carboxy -alkoxy -Cl-3, carboxy-alkyl-Cl-3-amino, N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amin or carboxy? -alkyl-Cl-3-aminocarbonyl, a C2-3 alkenyl group substituted by a carboxy or carboxy-alkyl-Cl-3-aminocarbonyl group, or a carbimino group optionally substituted on the carbon atom by an alkyl group -Cl-3, which in the imino nitrogen atom is substituted by a carboxy-alkoxy-Cl-3 or aminocarbonylamino group, or R2 and R3 together represent a group -C0-0-CH2- or -CO-0-CH2CH2 -, and R4 represents a hydrogen atom, fluorine, chlorine, bromine or iodine, an alkyl-Cl-3, cycloalkyl-C3-7, trifluormetho or alkoxy-Cl-3 groupor Ar also means a heteroaryl group which may be substituted by the residues R2 to R4 mentioned above, which are defined as mentioned above, X represents an oxygen or sulfur atom, a methylene group optionally substituted by one or two C 1-3 alkyl groups, a carbonyl, sulfinyl, sulfonyl, imino, N- (alkyl-Cl-3) -imino or N- (carboxy-alkyl-Cl-3) -imino group, the alkyl part being of the group N- (alkyl-Cl-3) -imino can be further substituted in the 2 or 3 position by an amino group, alkyl-Cl-3-amino, di- (alkyl-Cl-3) -amino, alkanoyl- Cl-4-amino or N- (alkanoyl-Cl-4) -alkyl-Cl-3-amino, and Y represents a cyclohexyl group substituted by an amino group, or a phenyl or heteroaryl group substituted by the residue Rs, being that the aforementioned phenyl group may in each case be substituted by a fluorine, chlorine, bromine or iodine atom, or by an alkyl-Cl-3 or alkoxy-Cl-3 group, as well as the hetero group aryl may be substituted by an alkyl-Cl-3 group, and R 5 represents a hydrogen atom, a cyano group or an amino, amino-alkyl-Cl-3, amidino, guanidino or guanidino-alkyl-Cl-3 group optionally substituted by a cleavable group in vivo, whereby the above-mentioned heteroaryl groups should be understood to mean a 5-membered heteroaromatic group optionally substituted by one or two alkyl-Cl-3 groups, containing an imino group optionally substituted by an alkyl-Cl group -3, an oxygen or sulfur atom and one or two nitrogen atoms, as well as their partially hydrogenated derivatives, in particular dihydro derivatives, or a 6-membered heteroaromatic group containing one, two or three nitrogen atoms, being additionally a phenyl ring can be condensed to the aforementioned 5- and 6-membered heteroaromatic rings through two adjacent carbon atoms, which the carboxy groups previously mentioned two in the definition of the residues can be substituted by a tetrazolyl group or by a group that in vivo can be converted to a carboxy group, and that the imino or amino groups mentioned in the definition of the residues can be replaced by a scissile residue : in vivo, their tautomers, their stereoisomers, their mixtures and their salts,

2. Compounds of the general formula I, according to claim 1, in which they mean A a vinylene group optionally substituted by a chlorine, bromine or iodine atom, an ethylene or ethynylene group, Ri a hydrogen atom or a Cl-3 alkyl group, Ar a pyridyl or thienyl group substituted by a benzoyl group, a bromofuranyl group substituted by a pyrrolidinocarbonyl group, a phenyl group substituted by the residues R2 to R4, wherein R2 represents a phenyl or phenoxy group an alkyl Cl-3 group which may be substituted by a phenyl, phenylamino, N- (alkyl-Cl-3) -phenylamino or N- (alkane-1-Cl-4) -phenylamino group, a carboxy or alkoxy-Cl-3-carbonyl group, a benzoyl group or phenylsulfonyl, which in the phenyl part in each case may be substituted by a fluorine, chlorine or bromine atom, by a methyl, methoxy, carboxy or alkoxy-Cl-3-carbonyl group, wherein in the above-mentioned benzoyl groups additionally the Oxygen atom may be substituted by carboxy-alkoxy-Cl-3-imino or alkoxy-Cl-3-carbonyl-alkoxy-Cl-3 -imino group, an alkyl-Cl-5-amino group which in the alkyl part may be substituted by a phenyl, carboxy, alkoxy-Cl-3-carbonyl, carboxy-alkyl-Cl-3-amino-carbonyl group, coxi-Cl-3 -carbonyl-alkyl-Cl-3-aminocarbonyl, N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino-carbonyl, or N- (alkyl-Cl-3) -alkoxy -Cl-3-carbonyl-alkyl-Cl-3-aminocarbonyl, or a C3-7-aminocarbonyl cycloalkyl group, wherein the previously mentioned groups can be respectively respectively substituted on the nitrogen atom of the amine by a cycloalkanoyl group C3-7, benzoyl or phenylsulfonyl, by a carboxy-alkyl-Cl-3-carbonyl or alkoxy-Cl-3-carbonyl-alkyl-Cl-3-carbonyl group, in which the alkyl part of the alkylcarbonyl group in each case can to be substituted by an amino or trifluoroacetylamino group, by a C 2-4 alkanoyl group, which in the alacanoyl part is substituted by an amino, carboxy, alkoxy-Cl-3-carbonyl, carboxy-alkoxy-Cl-3, alkoxy- Cl -3 -carbony1-alkoxy-Cl -3, carboxy-alkyl-Cl-3-aminocarbonyl, alkoxy-Cl-3 -carbonyl-alkyl-Cl-3-aminocarbonyl, N- (alkyl-Cl-3) -carboxy- alkyl-Cl-3-aminocarbonyl or N- (alkyl-Cl-3) -alkoxy-C l-3-carbonyl-alkyl-Cl-3-aminocarbonyl, by a carboxyalkyl-Cl-2-aminocarbonyl group, alkoxy-Cl -3-carbonyl-alkyl-C1-2-aminocarbonyl, carboxy-alkyl-Cl-3-aminocarbonyl -alkyl-Cl-2-aminocarbonyl or alkoxy-Cl-3-carbonyl-alkyl-Cl-3-aminocarbonyl-alkyl-Cl-2-aminocarbonyl, a formyl, pyridylcarbonyl, thienylcarbonyl, imidazolylcarbonyl, 1-methyl-imidazolylcarbonyl, thiazolylcarbonyl group or indolylcarbonyl, a benzimidazol-1-yl, benzimidazol-1-ylmethyl or 5-OXO-4,5,5-dihydro-pyrazole-3-yl group optionally substituted by one or two methylene groups, a pyrazole-1 group -yl substituted by a phenyl group, by a phenyl group and an alkyl-Cl-4 group, or by one or two alkyl-Cl-4 groups, in which an alkyl substituent can be simultaneously substituted by a carboxy or alkoxy group; Cl -3-carbonyl, or a carbonyl group which may be substituted by an alkyl-Cl-5 group optionally substituted by a carboxy or alkoxy-Cl-3-carbonyl group, a cyclo group C 3 -C 7 -alkyl, for an amino group, alkyl-Cl-5-amino, which in each case may additionally be substituted at the nitrogen atom by an alkyl-Cl-5 group, which may be substituted by a cycloalkyl- C3 -7, phenyl, pyrrolidinyl or pyridinyl, or in the 2 or 3 position by a di- (alkyl-Cl-3) -amino group, or by a di- (alkyl-Cl-3) -amino group, for a carboxy-alkyl-Cl-3-amino or alkoxy-Cl-3-carbonyl-alkyl-Cl-3-amino group, which in each case are substituted on the nitrogen atom of the amine by a pyrazole group optionally substituted by a group alkyl-Cl-3, by a 3 to 7-membered cycloalkyleneimino group, which may be substituted by one or two alkyl-Cl-3 groups, where the aforementioned pyrrolidino groups optionally substituted by a methyl group may be further substituted by a hydroxymethyl, carboxy, alkoxy-Cl-3-carbonyl, carboxy-alkyl-Cl-3, alkoxy-Cl-3-carbonyl-alkyl-Cl-3, carboxy-alkyloxy group i -Cl-3 -alkyl-Cl-3, alkoxy-Cl-3-carbonyl-alkyloxy-Cl-3-alkyl-Cl-3, carboxy-alkyl-Cl-3-amino-alkyl-Cl-3, N- (alkyl-Cl-3) -carboxy-alkyl -Cl-3-amino-alkyl-Cl-3, alkoxy-Cl-3-carbonyl-alkyl-Cl-3-amino-alkyl-Cl-3, N- (alkyl-Cl-3) -carboxy-alkyl-Cl -3-amino-alkyl-Cl-3-amino-alkyl-Cl-3, by a morpholino, piperazino, 4-methyl-piperazino, piperazin-alkyl-Cl-3, dihydropyrazolo, tetrahydropyrazolo, tetrahydroisooxazole, or 7-azabicycloheptyl group , or by a group N- (alkyl-Cl-3) -phenyl or N- (alkyl-Cl-3) -pyridylamino optionally substituted on the alkyl part by a carboxy or alkoxy-Cl-3-carbonyl group, R3 represents a hydrogen atom, fluorine, chlorine or bromine, a hydroxy group, alkoxy-Cl-3, trifluoromethyl, amino or C2-3 alkanoyl-amino, an alkyl-Cl-3 group, which may be substituted by a hydroxy, carboxy group , alkoxy-Cl-3-carbonyl, carboxy-alkoxy-Cl-3, alkoxy-Cl-3-carbonyl-1-alkoxy-Cl-3, carboxy-alkyl-Cl-3-aminocarbonyl, alkoxy-Cl-3-carbonyl-alk il-Cl-3-aminocarbonyl, N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-aminocarbonyl or N- (alkyl-Cl-3) -alkoxy-Cl-3-carbonyl-alkyl-Cl- 3-aminocarbonyl, an alkyl-Cl-3 group substituted by a carboxy-alkyl-Cl-3-amino group, alkoxy-Cl-3-carbonyl-alkyl-Cl-3-amino, N- (alkyl-Cl-3) -carboxy-alkyl-Cl-3-amino, or alkoxy-Cl-3-carbonyl-alkyl-Cl-3-aminocarbonyl, a C 2-3 alkenyl group substituted by a carboxy or alkoxy-Cl-3-carbonyl group, or a carbimino group optionally substituted on the carbon atom by an alkyl-Cl-3 group, which at the imino nitrogen atom is substituted by a carboxy-alkoxy-Cl-3, alkoxy-Cl-3-carbonyl-alkoxy group; Cl-3 or amino-carbonylamino, or R2 and R3 together represent a group -CO-0-CH2-, and R4 represents a hydrogen, fluorine, chlorine or bromine atom, an alkyl-Cl-3 or trifluoromethyl group, X represents an oxygen or sulfur atom, a NH group optionally substituted by an alkyl-Cl-3 group, and Y represents a cyclohroup an exyl substituted by an amino group, or a phenylene or pyridinylene group substituted by an amide group which may be substituted by a benzoyl or alkoxy-Cl-8-carbonyl group, wherein the aforementioned phenylene group may be substituted by a methyl group or methoxy, and the pyridinylene pgroup previously mentioned by a methyl group, their tautomers, their stereoisomers, their mixtures and their salts.

3. Compounds of the general formula

3. wherein A anethylene or ethynylene group, X is an oxygen atom or an imino group optionally substituted by a methyl group, R2 an alkyl-Cl -4 -carbonylamino or a C3-5 -carbonylamino cycloalkyl group, which at each case in the nitrogen atom of the amine are substituted by a carboxy-alkyl-Cl-2, alkoxy-Cl-3-carbonyl-alkyl-Cl-2, carboxy-alkyl-Cl-2-ammocarbonyl-alkyl-Cl- group 2, or alkoxy-Cl-3-carbonyl-alkyl-Cl-2-ammocarbonyl-alkyl-Cl-2, an alkyl-Cl-4-amino group or C3-5-amino-cycloalkyl, which in each case in the Nitrogen atom of the amine are substituted by a carboxy-alkyl-Cl-3-carbonyl, alkoxy-Cl-3-carbon-1-alkyl-Cl-3-carbonyl, carboxy-alkyl-Cl-2-aminocarbonyl-alkyl group Cl-2 -carbonyl, alkoxy-Cl -3 -carbonyl-alkyl-Cl-2-aminocarbonyl-alkyl-Cl-2-carbonyl, carboxy-alkyl-Cl-2-aminocarbonyl, alkoxy-C-3-carbonyl-alkyl- Cl-2-aminocarbonyl, carboxyalkyl-Cl -2-aminocarbonyl-alkyl-C l-2-aminocarbonyl or alkoxy-Cl-3-carbonyl-alkyl-Cl-2-aminocarbonyl-alkyl-Cl-2-aminocarbonyl substituted by an amino group optionally substituted on the alkyl part by a carboxymethyloxymethylcarbonyl group, alkoxy-Cl- 3-carbonyl-1-methyloxymethylcarbonyl, carboxymethylaminomethylcarbonyl, alkoxy-Cl-3 -carbonylmethylaminomethylcarbonyl, N -methylcarboxymethylaminomethylcarbonyl, N-methyl-alkoxy-Cl-3-carbonylcarboxy -methylaminomethylcarbonyl, aminomethyl -carbonyl, 2-aminoethylcarbonyl, carboxy-alkyl -Cl-2-aminocarbonylmethyloxymethylcarbonyl, alkoxy-Cl-3-carbonyl-alkyl-Cl-2-aminocarbonylmethyloxymethylcarbonyl, carboxy-alkyl-Cl-2-aminocarbonylmethylaminomethylcarbonyl, alkoxy-Cl-3-carbonyl-alkyl-Cl -2-aminocarbonylmethylamino methyl- carbonyl, N-methyl-carboxy-alkyl-Cl-2-aminocarbonylmethyl -aminomethylcarbonyl, or N-methyl-alkoxy-Cl-3 -carbonyl-alkyl-Cl -2-aminocarbonylmethylaminomethylcarbonyl, or a carbonyl group substituted by a cyclopentyl group, a gr upo C3 -5 alkyl, which may additionally be substituted by a carboxy or alkoxy-Cl-3-carbonyl group, an alkyl-Cl-4-amino, phenylamino or pyridylamino group substituted on the nitrogen atom of the amine by a group alkyl-Cl-4, carboxy-alkyl-Cl-3 or alkoxy-Cl-3-carbonyl-alkyl-Cl-3, by a pyrolidino group substituted by a methyl, hydroxymethyl, amino, carboxy, alkoxy-Cl-3 group carbonyl, carboxy-alkyl-Cl-2, alkoxy-Cl-3-carbonyl-alkyl-Cl-2, carboxymethyloxymethyl, alkoxy-Cl-3-carbonylmethyloxymethyl, carboxymethylaminomethyl, alkoxy-Cl-3-carbonylmethylamino-methyl, carboxymethylaminocarbonyl- methyloxymethyl or alkoxy-Cl-3-carbonylmethylaminocarbonylmethyloxymethyl, R3 a hydrogen, fluorine, chlorine or bromine atom or a trifluoromethyl group, an alkyl-Cl-2 group optionally substituted by a hydroxy, carboxy, alkoxy-Cl-3- group carbonyl, carboxymethyloxy, alkoxy-Cl-3-carbonylmethyloxy, carboxymethylamino, N-methyl-carboxymethylamino, alkoxy-Cl-3-carbonylmethyl ilamino, N-methyl-alkoxy-Cl-3-carbonylmethylamino, carboxymethylaminocarbonyl or alkoxy-Cl-3-carbonyl-methyl-aminocarbonyl, a vinyl group substituted by a carboxy or alkoxy-Cl-3-carbonyl group, R4 a hydrogen atom , fluorine, chlorine or bromine, a methyl, ethyl or trifluoromethyl group, and Y an amidino group optionally substituted by an alkoxy-Cl-8-carbonyl or benzoyl group,. its tautomers, its stereoisomers, its mixtures and its salts. 4. Compounds of the general formula la, according to claim 3, in which A is an ethylene or ethynylene group, X is an imino group, R2 is an alkyl-Cl-4-aminocarbonyl group which in each case is on the nitrogen atom of the amine is substituted by a carboxy-alkyl-Cl-2, or alkoxy-Cl-3-carbonyl-alkyl-Cl-2, an alkyl-Cl-4-amino group substituted on the nitrogen atom of the amine by a carboxy-alkyl-Cl-3-carbonyl, alkoxy-Cl-3-carbonyl-alkyl-Cl-3-carbonyl. carboxy-alkyl-Cl-2-aminocarbonyl or alkoxy-Cl-3-carbonyl-alkyl-Cl-2-aminocarbonyl, or a carbonyl group which may be substituted by a C3-5 alkyl group which may additionally be substituted by a carboxy or alkoxy-Cl-3-carbonyl group, by an alkyl-Cl-4 amino or substituted pyridylamino group on the atom of nitrogen of the amine by a carboxy-alkyl-Cl-3 or alkoxy-Cl-3 carbonyl-alkyl-Cl-3 group, by a pyrrolidine group optionally substituted by a methyl group, R 3 an optionally substituted alkyl-Cl-2 group by a carboxy or alkoxy-Cl-3-carbonyl group, R4 a hydrogen atom or a methyl group, and Y an amidino group optionally substituted by an alkoxy-Cl-8-carbonyl or benzoyl group, its tautomers, its stereoisomers, its mixtures and their salts.

5. The following compounds of the general formula I according to claim 1, 3 or 4: (a) rac-4-. { 3- [5-Ethoxycarbonylmethyl-2-methyl-4- (2-meth i 1 -pyrrolidinocarbonyl) -phenyl] -propargi lamino} -benzamidine, (b) rae -4 -. { 3 - [2,5-dimethyl-4- (2-methyl-pyrrole idino-carbonyl) -phenyl] -propargylamino} benzamidine, (c) 4- [3- (2, 5-dimethyl-4-isopropylcarbonyl-phenyl) -propargylaminobenzamidine, (d) 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-pyridin-2-yl-aminocarbonyl) -phenyl] -propargi lamino} benzamidine, (e) 4-. { 3- [2,5-dimethyl-4- (N-methyl-N-pyridin-2-ylaminocarbonyl) -phenyl] -propyl-ylamino} benzamidine, (f) 4- [3- (3-methyl-4-pyrrolidinocarbonyl-phenyl) -propargylamino] -benzamidine, (g) 4-. { 3- [2,5-dimethyl-4- (N- (2-methoxycarbonyl-ethyl) -N-ethyl-carbonylamino) -phenyl] -propargylamino} -benzamidine, (h) 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-hydroxycarbonylmethyl-aminocarbonyl-amino) -phenyl] -propargylamino} -benzamidine, e (i) 4-. { 3- [2,5-dimethyl-4- (N-isopropyl-N-hydroxycarbonyl-methyl-carbonyl-amino) -phenyl] -propargylamino} -benzamidine and its salts.

6. Physiologically acceptable salts of the compounds according to claims 1 to 5, characterized in that Y does not trust a cyano group.

7. Medicament containing a compound according to at least one of claims 1 to 5, wherein Y does not contain a cyano group, or a salt according to claim 6, optionally in combination with one or more carriers and / or diluents.

8. Use of a compound according to at least one of claims 1 to 5 wherein Y does not contain a cyano group, or a salt according to claim 6 for the preparation of a medicament characterized by a prolongation activity of the range of thrombin, an inhibitory activity of thrombin and an inhibitory activity on related serine proteases. Process for the preparation of a medicament according to claim 7, characterized in that a compound according to at least one of claims 1 to 5 is incorporated by the non-chemical route in which Y does not contain a cyano group, or a salt according to claim 6 in one or more inhertes vehicles and / or diluents. 10. Method for the preparation of compounds according to claims 1 to 6, characterized in that a. a compound of the general formula Ar-Zx (II) is reacted wherein Ar is defined as mentioned in claims 1 to 5 and Z? constitutes a lost group, with a compound of general formula H-A '- UCR1 - X - Y' (III) in which R? and X is defined as mentioned in claims 1 to 5 and 'has the meanings as recited in claims 1 to 5, with the proviso that an existing amino or imino group is protected by a usual protective residue, and A' they constitute an ethynyl group, and that a compound thus obtained in the following is optionally hydrogenated catalytically and / or a protective residue is cleaved using a compound obtained in this way, or b. for the preparation of a compound of the general formula I in which the residue Ar-A contains a carboxy group and R5 is defined as mentioned in claims 1 to 5, or the residue Ar-A is defined as mentioned in claims 1 to 5 and R5 constitutes an amino group, amino-Cl-3 alkyl, amidino or guanidino or the residue Ar-A contains a carboxy group and R5 constitutes an amino, amino-Cl-3 alkyl, amidino or guanidino group, a composed of the general formula in which A, R? and X is defined as recited in claims 1 to 5, Ar 'and Y "has the meanings as recited in claims 1 to 5 for Ar and Y, with the proviso that Ar' contains a group that by hydrolysis , treatment with an acid or a base, thermolysis or hydrogenolysis can be converted into a carboxy group, and Y '' has the meaning mentioned in claims 1 to 5, or Ar 'has the meanings mentioned in claims 1 to 5 for Ar, and Y' 'contains a group which by hydrolysis, treatment with a. acid or base, thermolysis or hydrogenolysis can be converted to an amino group, amino-alkyl Cl-3, amidino or guanidino, or Ar 'contains a group that by hydrolysis, treatment with an acid or base, thermolysis or hydrogenolysis can be converted to a carboxy group and Y'1 contains a group which, by hydrolysis, treatment with an acid or base, thermolysis or hydrogenolysis, can be converted to an amino, amino-Cl-3 alkyl, amidino or guanidino group, converted by hydrolysis, treatment with an acid or base, thermolysis or hydrogenolysis to a compound of the general formula I, in which the residue Ar-A contains a carboxy group and R5 is defined as mentioned in claims 1 to 5, or the residue Ar-A is defined as mentioned, in Claims 1 to 5 and R5 represents an amino, amino-Cl-3 alkyl, amidino or guanidino group, or the residue Ar-A contains a carboxy group and R5 represents an amino, amino-alkyl Cl group. -3, amidino or guanidino, or c. for the preparation of a compound of the general formula I in which R5 represents an amidino group, a compound that is optionally formed in the reaction mixture, of the general formula wherein A, Ar, R1 and X are defined as mentioned in claims 1 to 5, and Y "means one of the residues mentioned in claims 1 to 5 for Y, with the proviso that y R5 represents a group Z - (HN =) C, wherein Z represents an alkoxy, alkylthio, aralkoxy or aralkylthio group is reacted with an ammonium salt, while simultaneously an electron-rich or electron-deficient triple bond can be added a halogen acid, or d. for the preparation of a compound of the general formula I in which R 5 represents an amidino group substituted with a hydroxy group, a compound which is optionally formed in the reaction mixture, of the general formula wherein A, Ar, RL and X is defined as mentioned in claims 1 to 5, and Y "means one of the residues mentioned in claims 1 to 5 for Y, with the proviso that R5 represents a group Zx - (HN =) C, in that Zx represents an alkoxy, alkylthio, aralkoxy or aralkylthio group is reacted with hydroxylamine or its salts, or e. for the preparation of a compound of the general formula I in which X constitutes an oxygen or sulfur atom, a carbonyl, inmino or N- (C 3 alkyl) -imino group, a compound of the general formula I in which A, Ar, Ri are defined as mentioned in claims 1 to 5, and Z2 represents a lost group, is reacted with a compound of the general formula UY (VII) wherein Y is defined as mentioned in Claims 1 to 5, and U means a hydroxy, mercapto, hydroxycarbonyl, imino or N- (C, alkyl) -imino group, or f. for the preparation of a compound of the general formula I in which Ar and / or Y contain an in vivo cleavable residue, a compound of the general formula Ar '' - A - HCR, - X - Y '' '( VIII) in which A, Rx and X are defined as mentioned in claims 1 to 5, Ar '' and Y '' 'have the meaning mentioned in claims 1 to 5 for Ar and Y, with the proviso that Ar '' contains a carboxy group and Y '' 'having the meanings mentioned in claims 1 to 5 for Y, or Ar "has the meanings mentioned in claims 1 to 5 for Ar and Y' '' contains an amino group , amino-C C-aminoalkyl, amidino or guanidino, or Ar "contains a carboxy group and Y '' 'an amino, amino-C C, amidino or guanidino alkyl group, is reacted with a compound of the general formula Z3 - R7 (IX) in which R7 signifies a C-carbonyl alkoxy group, a RaCO-0- (RbCRc) group or the acyl residue of one of the in vivo cleavable residues mentioned in claims 1 to 5, wherein Ra a Rc is defined as recited in claims 1 to 5, and Z3 means a nucleophilic lost group, or else, if Ar "contains a carboxy group., a hydroxy group, and then, if desired, a compound of the general formula I obtained in this manner in which Rs represents an amidino group can be transformed into a corresponding amidino compound substituted by one or two methyl groups by means of alkylation in a halogenated acetic acid derivative, and subsequent hydrolysis and decarboxylation, and / or a compound of the general formula I obtained in this manner in which R 5 represents a hydroxyamidino group, can be transformed into a corresponding amidino compound by catalytic hydrogenation, and / or a compound of the general formula I obtained in this manner which contains a double or triple bond, can be converted into a corresponding saturated compound by catalytic hydrogenation, and / or a compound of the general formula I obtained in this way, in the that X represents a sulfur atom, can be transformed into a corresponding sulfinyl or sulfonyl compound by oxidation n, and / or a compound of the general formula I obtained in this manner in which R 2 represents a tetrahydropyrazolecarbonyl group, can be converted to a corresponding 4,5-dihydropyrazolcarbonyl compound by oxidation, and / or a compound of the general formula I obtained in this way containing a carbonyl group, it can be transformed into a corresponding oxyme compound by a corresponding oxime, and / or a compound of the general formula I obtained in this manner containing a carboxy group, can be transformed into an amide a corresponding amine, and / or if necessary, a protecting group used during the reactions for the protection of the reactive groups is cleaved, and / or if desired a compound of the general formula I obtained in this way is separated into its stereoisomers, and / or a compound of the general formula I obtained in this manner containing a double bond is separated into its cis / trans isomers, and / or a compound of the general formula I obtained in this way is converted into its salts, in particular for pharmaceutical use, into its physiologically acceptable salts with an inorganic or organic acid or base.