Arylalkanes, arylalkenes and aryl-azaalkanes, pharmaceutical compositions containing these compounds and processes for preparing them

Abstract

The present invention relates to compounds of general formula R-Z 1 -Z 2 -Z 3 -R  (I), wherein R, R 1 and Z 1 to Z 3 are defined as in claim 1 , the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable pharmacological properties, particularly CGRP-antagonistic properties, pharmaceutical compositions containing these compounds, their use and processes for preparing them.

1 . Arylalkanes, arylalkenes and aryl-azaalkanes of general formula  
       R-Z 1 -Z 2 -Z 3 -R 1   (I),  wherein    R denotes the H 2 N group or the group of formula                          wherein 
 denotes the number 1 or, if Y does not denote a nitrogen atom, also denotes the number 0,  
 p denotes the number 1 or, if Y does not denote a nitrogen atom, also denotes the number 0,  
 Y denotes the carbon atom or, if Y is not linked to a heteroatom, may also denote the nitrogen atom,  
 R 2  denotes a pair of tree electrons, if Y denotes the nitrogen atom, or, if Y denotes the carbon atom, it denotes the hydrogen atom or an alkyl group with 1 to 3 carbon atoms,  
 R 3  and R 4  denote hydrogen atoms or together denote an alkylene bridge with 1 to 3 carbon atoms,  
 R 5  and R 6  denote hydrogen atoms or together denote a one-to three-membered unbranched alkylene bridge wherein a methylene group may be replaced by a methylimino group,  
 R N  denotes a saturated, mono- or diunsaturated 5- to 7-membered aza, diaza, triaza, oxaza, thiaza, thiadiaza or S,S-dioxido-thiadiaza heterocycle, 
 wherein the abovementioned heterocycles may be linked via a carbon or nitrogen atom and  
 may contain, adjacent to a nitrogen atom, a carbonyl, thioxo or iminocarbonyl group or two carbonyl groups or a carbonyl group and a thioxo or iminocarbonyl group, wherein the abovementioned iminocarbonyl groups may be substituted by a cyano group or by an alkoxycarbonyl group with 1 to 4 carbon atoms in the alkyl moiety,  
 may be substituted at one of the nitrogen atoms by an alkanoyl, hydroxycarbonylalkyl or alkoxycarbonylalkyl group,  
 may be substituted at one or two carbon atoms by a branched or unbranched alkyl group, by a phenyl, phenylmethyl, naphthyl, biphenylyl, pyridinyl, diazinyl, furyl, thienyl, pyrrolyl, 1,3-oxazolyl, 1,3-thiazolyl, isoxazolyl, pyrazolyl, 1-methylpyrazolyl, imidazolyl or 1-methylimidazolyl group, wherein the substituents may be identical or different,  
 wherein additionally an unbranched alkylene group with 3 to 6 carbon atoms may be attached to the abovementioned 5- to 7-membered heterocycles via two adjacent carbon atoms or the group ═CH—S—CH═ may be attached to the abovementioned 5- to 7-membered saturated heterocycles via two adjacent carbon atoms or  
 an olefinic double bond of one of the abovementioned unsaturated heterocycles may be fused to a benzene, pyridine, diazine, 1,3-oxazole, thiophene, furan, thiazole, pyrrole, N-methyl-pyrrole, quinoline, imidazole or N-methyl-imidazole ring,  
 
 or, if Y denotes the carbon atom, R N  denotes the hydroxy group, a benzoylaminocarbonylamino group, a phenylamino group optionally substituted at the aniline nitrogen by an aminocarbonyl group or a phenylmethylamino group optionally-substituted at the benzylamine nitrogen by an alkoxycarbonyl group, 
 wherein the phenyl, pyridinyl, diazinyl, furyl, thienyl, pyrrolyl, 1,3-oxazolyl, 1,3-thiazolyl, isoxazolyl, pyrazolyl, 1-methylpyrazolyl, imidazolyl or 1-methylimidazolyl groups contained in the groups mentioned under R N  as well as benzo-, thieno-, pyrido-, diazino- and quinolino-fused heterocycles in the carbon skeleton may additionally be mono-, di- or trisubstituted by fluorine, chlorine or bromine atoms, by alkyl groups, by cycloalkyl groups with 3 to 8 carbon atoms, nitro, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulphonylamino, phenyl, phenylalkoxy, trifluoromethyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxy, carboxyalkyl, dialkylaminoalkyl, hydroxy, amino, acetylamino, propionylamino, cycloalkanecarbonylamino, benzoyl, benzoylamino, benzoylmethylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxyalkylaminocarbonyl, (4-morpholinyl)carbonyl, (1-pyrrolidinyl)carbonyl, (1-piperidinyl)carbonyl, (hexahydro-1-azepinyl)carbonyl, (4-methyl-1-piperazinyl)carbonyl, [4-(1-piperidinyl)piperidinyl]carbonyl, [4-(1-piperidinyl)piperidinyl]carbonylamino, methylenedioxy, aminocarbonylamino, aminocarbonylaminoalkyl, alkylaminocarbonylamino, dialkylaminocarbonylamino, aminomethyl, alkanoyl, cyano, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl groups, wherein the substituents may be identical or different and the abovementioned benzoyl, benzoylamino, benzoylaminocarbonylamino and benzoylmethylamino groups may in turn additionally be substituted in the phenyl moiety by a fluorine, chlorine or bromine atom, an alkyl, trifluoromethyl, amino or acetylamino group,  
 and the alkyl groups contained in the abovementioned groups, unless otherwise stated, may contain 1 to 5 carbon atoms,  
 
   or, if Z 1 -Z 2 -Z 3  denotes the divalent group CO—CH 2 —CH 2 —CO, R may also denote the 4-[3,4-dihydro-2(1H)-oxoquinazolin-3-yl]-[1.4]bipiperidinyl-1′-yl group,    Z 1  denotes a methylene or carbonyl group or, if Z 2  denotes a divalent group of general formula III, may also denote a bond,    Z 2  denotes one of the groups —(CH 2 ) 2 — or —(CH 2 ) 3 —, 
 wherein a hydrogen atom may be replaced by a C 1-3 -alkyl or a hydroxy group,  
   one of the groups —NH—CH 2 , —CH 2 —NH, —NH—(CH 2 ) 2 — or —(CH 2 ) 2 —NH—, 
 wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group and the nitrogen atoms are each linked to a carbonyl group of the groups Z 1  or Z 3 ,  
   the group —CH═CH— or a divalent group of general formula                          wherein 
 m and n independently of one another denote one of the numbers 1, 2, 3 or 4 and the nitrogen atom is linked to a carbonyl group of the group Z 3 ,  
   Z 3  denotes the methylene or carbonyl group, 
 wherein at least one of the groups Z 1  and Z 3  denotes a carbonyl group, and  
   R 1  denotes a phenyl, 1-naphthyl, 2-naphthyl, benzimidazolyl, 1,3-dihydro-2-oxobenzimidazolyl, octahydro-9-phenanthryl or benzodioxolanyl group, 
 wherein the abovementioned aromatic and heteroaromatic groups in the carbon skeleton may additionally be mono-, di- or trisubstituted by fluorine, chlorine, bromine or iodine atoms, by alkyl groups, by cycloalkyl groups with 3 to 8 carbon atoms, phenylalkyl groups, hydroxy, alkoxy, phenyl, phenylalkoxy, trifluoromethyl, alkoxycarbonylalkyl, carboxyalkyl, alkoxycarbonyl, carboxy, dialkylaminoalkyl, amino, aminoalkyl, alkylamino, dialkylamino, acetylamino, propionylamino, benzoyl, benzoylamino, benzoylmethylamino, 4-(dialkylaminoalkyl)-1-piperazinyl, piperidinyl, 4-(1-piperidinyl)-1-piperidinyl, 4-(4-methyl-1-piperazinyl)-1-piperidinyl, 4-(4-dialkylaminoalkyl-1-piperazinyl)-1-piperidinyl, nitro, methanesulphonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkanoyl, cyano, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl groups and the substituents may be identical or different and the abovementioned benzoyl, benzoylamino and benzoylmethylamino groups may in turn additionally be substituted in the phenyl moiety by a fluorine, chlorine or bromine atom or by an alkyl, trifluoromethyl, amino or acetylamino group,  
   wherein the hydroxy, amino and imidazolyl groups contained in the abovementioned groups may be substituted with protecting groups well known from peptide chemistry, preferably with the acetyl, benzyloxycarbonyl or tert.butyloxycarbonyl group,    all the abovementioned alkyl and alkoxy groups and the alkyl or alkylene moieties present inside the other groups specified may contain 1 to 7 carbon atoms, unless otherwise stated, and    all the abovementioned cycloalkyl groups and the cycloalkyl groups present inside the other groups specified may contain 5 to 10 carbon atoms, unless otherwise stated,    the tautomers, the diastereomers, the enantiomers and the salts thereof.    
   
   
       2 . Compounds of the above general formula I according to  claim 1 , wherein 
 R denotes the H 2 N group, if Z 1  and Z 3  each denote the CO group and R 1  is at least disubstituted by the H 2 N group and an additional substituent or if Z 2  does not contain an imino group,    or the group of formula                          wherein 
 o, p, R 5 , R 6  and Y are as hereinbefore defined,  
 R 2  denotes a pair of free electrons, if Y denotes the nitrogen atom, or, if Y denotes the carbon atom, R 2  denotes the hydrogen atom or a methyl group,  
 R 3  and R 4  denote hydrogen atoms or together denote an alkylene bridge with 2 to 3 carbon atoms,  
 R N  denotes a monocyclic saturated, mono- or diunsaturated 5- to 7-membered aza, diaza, triaza, oxaza, thiaza, thiadiaza- or S,S-dioxido-thiadiaza heterocycle containing one to two imino groups, 
 wherein the abovementioned heterocycles are linked via a carbon or nitrogen atom and  
 adjacent to a nitrogen atom contain a carbonyl, thioxo or iminocarbonyl group or two carbonyl groups or a carbonyl group and a thioxo or iminocarbonyl group, wherein the abovementioned iminocarbonyl groups may be substituted by a cyano group or by an alkoxycarbonyl group with 1 to 4 carbon atoms in the alkyl moiety,  
 the abovementioned heterocycles containing two imino groups may be substituted at one of the imino-nitrogen atoms by an alkanoyl, hydroxycarbonylalkyl or alkoxycarbonylalkyl group with 1 to 3 carbon atoms in the alkyl moieties,  
 
 may be substituted at one or two carbon atoms by an unbranched alkyl group, by a phenyl, phenylmethyl, naphthyl, biphenylyl or thienyl group, wherein the substituents may be identical or different, 
 and wherein additionally an unbranched alkylene group with 3 to 4 carbon atoms may be attached to the abovementioned 5- to 7-membered heterocycles via two adjacent carbon atoms or the group ═CH—S—CH═ may be attached to the abovementioned 5- to 7-membered saturated heterocycles via two adjacent carbon atoms or an olefinic double bond of one of the abovementioned unsaturated heterocycles may be fused to a benzene, pyridine, diazine, thiophene or quinoline ring,  
 with the provisos that  
 (i) R N  does not take on the meaning of the 2,6-dioxo-3-phenyl-3,4,5,6-tetrahydro-1H-pyrimidin-3-yl group, the 2-oxo-1,3,4,5-tetrahydro-1-imidazolyl group optionally monosubstituted by an acyl group in the 3 position and the 2(1H)-oxo-3,4,5,6-tetrahydro-1-pyrimidinyl group and  
 (ii) R 1  does not denote a 2-alkoxy-4-amino-5-chlorophenyl, 2-alkoxy-4-amino-5-bromophenyl, 2-alkoxy-4-acetylamino-5-chlorophenyl or 2-alkoxy-4-acetylamino-5-bromophenyl group if R N  takes on the meaning of the 1,3-dihydro-2(2H)-oxobenzimidazol-1-yl, 1,3-dihydro-2(2H)-thioxobenzimidazol-1-yl, 2(1H)-oxoquinoxalin-1-yl, 3-oxo-2,3-dihydrobenzoxazin-4-yl, 3-oxo-2,3,4,5-tetrahydrobenz[f][1,4]oxazepin-4-yl or 22(1H)-oxoquinolin-3-yl group,  
 
 or, if Y denotes the carbon atom, with the proviso that 
 (i) R 1  does not denote a 2-alkoxy-4-amino-5-bromophenyl, 2-alkoxy-4-amino-5-chlorophenyl or naphthyl group or  
 (ii) Z 2  does not denote a group containing N or  
 (iii) Z 1  and Z 3  each denote the CO group,  
 
 R N  may also represent the hydroxy group  
 or, if Y denotes the carbon atom and Z 1  and Z 3  each denote the CO group, a benzoylaminocarbonylamino group, a phenylamino group optionally at least monosubstituted at the aniline nitrogen by an aminocarbonyl group and in the phenyl moiety,  
 or, if Y denotes the carbon atom, Z 1  and Z 3  each denote the CO group and in the group of general formula (II) o and p each assume the value 1, a phenylmethylamino group optionally at least monosubstituted at the benzylamine nitrogen by a C 1-4 -alkoxy-carbonyl group and in the phenyl moiety, 
 wherein the phenyl and thienyl groups contained in the groups mentioned under R N  as well as benzo-, thieno-, pyrido-, diazino- and quinolino-fused heterocycles may additionally be mono-, di- or trisubstituted in the carbon skeleton by fluorine, chlorine or bromine atoms, by methyl groups, by cycloalkyl groups with 5 to 6 carbon atoms, nitro, methoxy, methylthio, methylsulphinyl, methylsulphonyl, methanesulphonylamino, phenyl, trifluoromethyl, methoxycarbonyl, carboxy, hydroxy, amino, acetylamino, cyclohexanecarbonylamino, aminocarbonyl, hydroxyethylaminocarbonyl, (4-morpholinyl)carbonyl, (1-pyrrolidinyl)carbonyl, (1-piperidinyl)carbonyl, (hexahydro-1-azepinyl)carbonyl, (4-methyl-1-piperazinyl)carbonyl, [4-(1-piperidinyl)-piperidinyl]carbonyl, [4-(1-piperidinyl)piperidinyl]-carbonylamino, aminocarbonylamino, alkylaminocarbonylamino, dialkylaminocarbonylamino, aminomethyl, acetyl, cyano or trifluoromethoxy groups, wherein the substituents may be identical or different,  
 
   or, if Z 1 -Z 2 -Z 3  denotes the divalent group CO—CH 2 —CH 2 —CO, R may also denote the 4-[3,4-dihydro-2(1H)-oxoquinazolin-3-yl]-[1.4′]bipiperidinyl-1′-yl group,    Z 1  denotes the methylene or carbonyl group or, if Z 2  denotes a divalent group of general formula III, may also denote a bond,    Z 2  denotes one of the groups —(CH 2 ) 2 — or —(CH 2 ) 3 —, 
 wherein a hydrogen atom may be replaced by a C 1-3 -alkyl or a hydroxy group,  
   one of the groups    —NH—CH 2 , —CH 2 —NH, —NH—(CH 2 ) 2 — or —(CH 2 ) 2 —NH—, 
 wherein the nitrogen atoms are each linked to a carbonyl group of the groups Z 1  or Z 3  and the hydrogen atom of the imino group may in each case be replaced by a C 1-3 -alkyl group,  
   the group —CH═CH— or, if R 1  does not denote an aromatic or heteroaromatic group substituted by cycloalkyl or phenyl groups or R N  is not linked via an imino group bound in the adjacent position to a fused-on benzene ring, it also denotes a divalent group of general formula                          wherein 
 m and n independently of one another denote one of the numbers 1, 2 or 3 and  
 the nitrogen atom is linked to the group Z 3  with the meaning of a carbonyl group,  
   Z 3  denotes the carbonyl group or, if R N  is not linked via an imino group bound in the adjacent position to a fused-on aromatic or heteroaromatic ring, it also denotes the methylene group, 
 wherein at least one of the groups Z 1  and Z 3  denotes a carbonyl group and the sequence Z 1 -Z 2 -Z 3  is at least four-membered, and  
   R 1  denotes a mono-, di- or trisubstituted phenyl group, a benzimidazolyl, 1,3-dihydro-2-oxobenzimidazolyl, octahydro-9-phenanthryl or benzodioxolanyl group or, if Z 1  and Z 3  each denote the CO group, R 1  may also denote a 1-naphthyl or 2-naphthyl group, 
 wherein the abovementioned aromatic and heteroaromatic groups may be mono-, di- or trisubstituted in the carbon skeleton by fluorine, chlorine, bromine or iodine atoms, by alkyl groups with 1 to 4 carbon atoms, by cycloalkyl groups with 5 to 6 carbon atoms, hydroxy, alkoxy, phenyl, trifluoromethyl, methoxycarbonyl, ethoxycarbonyl, carboxy, amino, aminomethyl, methylamino, dimethylamino, acetylamino, 4-[3-(dimethylaminopropyl)]-1-piperazinyl, piperidinyl, 4-(1-piperidinyl)-1-piperidinyl, 4-(4-methyl-1-piperazinyl)-1-piperidinyl, 4-[4-(3-dimethylaminopropyl)-1-piperazinyl]-1-piperidinyl, nitro, methanesulphonyloxy, aminocarbonyl, acetyl, cyano or trifluoromethoxy groups and the substituents may be identical or different,  
   wherein all the abovementioned alkyl and alkoxy groups and the alkyl or alkylene moieties present inside the other groups specified may contain 1 to 5 carbon atoms unless otherwise stated,    the tautomers, diastereomers, enantiomers and salts thereof.    
   
   
       3 . Compounds of the above general formula I according to  claim 1 , wherein 
 R denotes the H 2 N group, if Z 1  and Z 3  each denote the CO group and R 1  is at least disubstituted by the H 2 N group and an additional substituent or if Z 2  does not contain an imino group, or the group of formula                          wherein 
 o, p and Y are as hereinbefore defined,  
 R 2  denotes a pair of free electrons, if Y denotes the nitrogen atom, or, if Y denotes the carbon atom, R 2  denotes the hydrogen atom or a methyl group,  
 R 3  and R 4  denote hydrogen atoms or together denote an alkylene bridge with 2 carbon atoms,  
 R 5  and R 6  denote hydrogen atoms or together denote an n-propylene bridge wherein the central methylene group may be replaced by a methylimino group,  
 R N  denotes a monocyclic saturated, mono- or diunsaturated 5- to 7-membered aza, diaza, triaza, thiadiaza or S,S-dioxido-thiadiaza heterocycle containing one to two imino groups, 
 wherein the abovementioned heterocycles are linked via a carbon or nitrogen atom and adjacent to a nitrogen atom contain a carbonyl, thioxo or iminocarbonyl group or two carbonyl groups or a carbonyl group and a thioxo or iminocarbonyl group,  
 wherein the abovementioned iminocarbonyl groups may be substituted by a cyano group or by a tert.butoxycarbonyl group,  
 the abovementioned heterocycles containing two imino groups may be substituted at one of the imino-nitrogen atoms by an acetyl, carboxymethyl or methoxycarbonyl-methyl group,  
 may be substituted at one or two carbon atoms by a methyl group, by a phenyl, phenylmethyl, naphthyl, biphenylyl or thienyl group, wherein the substituents may be identical or different,  
 and wherein additionally an unbranched alkylene group with 4 carbon atoms may be attached to the abovementioned 5- to 7-membered heterocycles via two adjacent carbon atoms or the group ═CH—S—CH═ may be attached to the abovementioned 5- to 7-membered saturated heterocycles via two adjacent carbon atoms or an olefinic double bond of one of the abovementioned unsaturated heterocycles may be fused to a benzene, pyridine, diazine, thiophene or quinoline ring,  
 with the provisos that  
 (i) R N  does not take on the meaning of the 2,6-dioxo-3-phenyl-3,4,5,6-tetrahydro-1H-pyrimidin-3-yl group, the 2-oxo-1,3,4,5-tetrahydro-1-imidazolyl group optionally monosubstituted in the 3 position by an acyl group and the 2(1H)-oxo-3,4,5,6-tetrahydro-1-pyrimidinyl group, and  
 (ii) R 1  does not denote a 2-alkoxy-4-amino-5-chlorophenyl, 2-alkoxy-4-amino-5-bromophenyl, 2-alkoxy-4-acetylamino-5-chlorophenyl or 2-alkoxy-4-acetylamino-5-bromophenyl group, if R N  takes on the meaning of the 1,3-dihydro-2(2H)-oxobenzimidazol-1-yl, 1,3-dihydro-2(2H)-thioxobenzimidazol-1-yl, 2(1H)oxoquinoxalin-1-yl, 3-oxo-2,3-dihydrobenzoxazin-4-yl, 3-oxo-2,3,4,5-tetrahydrobenz[f][1,4]oxazepin-4-yl or 2(1H)-oxoquinolin-3-yl group,  
 
 or, if Y denotes the carbon atom, with the proviso that 
 (i) R 1  does not denote a 2-alkoxy-4-amino-5-bromophenyl, 2-alkoxy-4-amino-5-chlorophenyl or naphthyl group or  
 (ii) Z 2  does not denote a group containing N, or  
 (iii) Z 1  and Z 3  each denote the CO group,  
 
 R N  may also denote the hydroxy group,  
 or, if Y denotes the carbon atom and Z 1  and Z 3  each denote the CO group, a benzoylaminocarbonylamino group, a phenylamino group optionally at least monosubstituted by an aminocarbonyl group at the aniline nitrogen and in the phenyl moiety,  
 or, if Y denotes the carbon atom, Z 1  and Z 3  each denote the CO group and in the group of general formula (II) o and p each assume the value 1, a phenylmethylamino group optionally at least monosubstituted by a tert. butoxycarbonyl group at the benzylamine nitrogen and in the phenyl moiety, 
 wherein the phenyl and thienyl groups contained in the groups mentioned under R N  as well as benzo-, thieno-, pyrido-, diazino- and quinolino-fused heterocycles may additionally be mono-, di- or trisubstituted in the carbon skeleton by fluorine, chlorine or bromine atoms, by methyl, nitro, methoxy, methanesulphonylamino, phenyl, trifluoromethyl, methoxycarbonyl, carboxy, hydroxy, amino, acetylamino, cyclohexanecarbonylamino, aminocarbonyl, hydroxyethylaminocarbonyl, (4-morpholinyl)carbonyl, (4-methyl-1-piperazinyl)-carbonyl, [4-(1-piperidinyl)-1-piperidinyl]carbonyl, [4-(1-piperidinyl)piperidinyl]carbonylamino, aminomethyl or aminocarbonylamino groups, wherein the substituents may be identical or different,  
 
   or, if Z 1 -Z 2 -Z 3  denotes the divalent group CO—CH 2 —CH 2 —CO, R may also denote the 4-[3,4-dihydro-2(1H)-oxoquinazolin-3-yl]-[1.4′]bipiperidinyl-1′-yl group,    Z 1  denotes methylene or carbonyl group or, if Z 2  denotes a divalent group of general formula III, may also denote a bond,    Z 2  denotes one of the groups —(CH 2 ) 2 — or —(CH 2 ) 3 —, 
 wherein a hydrogen atom may be replaced by a C 1-3 -alkyl or hydroxy group,  
   one of the groups    —NH—CH 2 , —CH 2 —NH— or —(CH 2 ) 2 —NH—, 
 wherein the nitrogen atoms are each linked to a carbonyl group of the groups Z 1  or Z 3  and the hydrogen atom of the imino group may be replaced by a C 1-3 -alkyl group in each case,  
   the group —CH═CH— or, if R 1  does not denote an aromatic or heteroaromatic group substituted by cycloalkyl or phenyl groups or R N  is not linked via an imino group bound in the adjacent position to a fused-on benzene ring, it may also denote a divalent group of general formula                          wherein 
 m denotes one of the numbers 1 or 2 and n denotes one of the numbers 1, 2 or 3 and the nitrogen atom is linked to the group Z 3  with the meaning of a carbonyl group,  
   Z 3  denotes the carbonyl group or, if R N  is not linked via an imino group bound in the adjacent position to a fused-on aromatic or heteroaromatic ring, it may also denote the methylene group, 
 wherein at least one of the groups Z 1  and Z 3  denotes a carbonyl group and the sequence Z 1 -Z 2 -Z 3  is at least four-membered, and  
   R 1  denotes a monosubstituted phenyl group, a 5-benzimidazolyl, 1,3-dihydro-2-oxobenzimidazol-5-yl, octahydro-9-phenanthryl or 5-benzodioxolanyl group or, if Z 1  and Z 3  each denote the CO group, it may also denote a 1-naphthyl or 2-naphthyl group,    wherein the abovementioned aromatic and heteroaromatic groups may additionally be mono-, di- or trisubstituted in the carbon skeleton by fluorine, chlorine, bromine or iodine atoms, by alkyl groups with 1 to 4 carbon atoms, by cyclohexyl, hydroxy, alkoxy groups with up to 3 carbon atoms in the alkyl moiety, phenyl, trifluoromethyl, methoxycarbonyl, ethoxycarbonyl, carboxy, amino, aminomethyl, methylamino, dimethylamino, acetylamino, 4-[3-(dimethylaminopropyl)-1-piperazinyl, piperidinyl, 4-(1-piperidinyl)-1-piperidinyl, 4-(4-methyl-1-piperazinyl)-1-piperidinyl, 4-[4-(3-dimethylaminopropyl)-1-piperazinyl)-1-piperidinyl, nitro, cyano or trifluoromethoxy groups and the substituents may be identical or different,    the tautomers, diastereomers, enantiomers and salts thereof.    
   
   
       4 . Compounds of the above general formula I according to  claim 1 , wherein 
 R denotes the H 2 N group, if Z 1  and Z 3  each denote the CO group and R 1  is at least disubstituted by the H 2 N group and an additional substituent or if Z 2  does not contain an imino group, or R denotes the group of formula                          wherein 
 Y denotes the carbon atom and o and p independently of one another denotes the numbers 1 or 0 or  
 Y denotes the nitrogen atom and o and p each represent the number 1,  
 R 2  denotes a pair of free electrons, if Y denotes the nitrogen atom, or, if Y denotes the carbon atom, R 2  denotes the hydrogen atom or the methyl group,  
 R 3  and R 4  denote hydrogen atoms or together denote a ethylene bridge,  
 R 5  and R 6  denote hydrogen atoms or together denote a —CH 2 —N(CH 3 )—CH 2 — bridge,  
 R N  denotes a 3,4-dihydro-2(1H)-oxoquinazolin-3-yl, 3,4-dihydro-2(1H)-oxoquinazolin-1-yl, 1,3-dihydro-4-phenyl-2H-2-oxoimidazol-1-yl, 3,4-dihydro-2(1H)-oxopyrido[2,3-d]pyrimidin-3-yl, 4-phenyl-1,3,4,5-tetrahydro-2H-2-oxoimidazol-1-yl, 1,3-dihydro-5-methyl-4-phenyl-2H-2-oxoimidazol-1-yl, 3,4-dihydro-2(1H)-oxothieno[3,4-d]pyrimidin-3-yl, 1,3-dihydro-4-(3-thienyl)-2H-2-oxoimidazol-1-yl, 2,4-dihydro-5-phenyl-3(3H)-oxo-1,2,4-triazol-2-yl, 3,4-dihydro-2(1H)-oxothieno[3,2-d]pyrimidin-3-yl, 3,4-dihydro-2(1H)-oxopyrido[3,4-d]pyrimidin-3-yl, 3,4-dihydro-2(1H)-oxopyrido[4,3-d]pyrimidin-3-yl, 3,4-dihydro-2(1H)-oxoquinolin-3-yl, 2(1H)-oxoquinoxalin-3-yl, 1,1-dioxido-3(4H)-oxo-1,2,4-benzothiadiazin-2-yl, 1,3-dihydro-2(2H)-oxoimidazo[4,5-d]pyrimidin-3-yl, 3,4,4a,5,6,7,8,8a-octahydro-2(1H)-oxoquinazolin-3-yl, 2,5-dioxo-4-(phenylmethyl)-imidazolidin-1-yl, 2,5-dioxo-4-phenyl-imidazolidin-1-yl, 3,4-dihydro-2,2-dioxido-2,1,3-benzothiadiazin-3-yl, 1,3-dihydro-4-(2-naphthyl)-2H-2-oxoimidazol-1-yl, 4-(4-biphenylyl)-1,3-dihydro-2H-2-oxoimidazol-1-yl, 1,3-dihydro-2(2H)-oxoimidazo[4,5-c]quinolin-3-yl, 2-(dimethylethoxycarbonylamino)-3,4-dihydroquinazolin-3-yl, 2-amino-3,4-dihydroquinazolin-3-yl, 3,4-dihydro-2(1H)-thioxoquinazolin-3-yl, 3,4-dihydro-2(1H)-cyanoiminoquinazolin-3-yl, 2,3,4,5-tetrahydro-2(1H)-oxo-1,3-benzodiazepin-3-yl or 2,4(1H, 3H)-dioxoquinazolin-3-yl group or,  
 if R 1  does not denote a 2-alkoxy-4-amino-5-chlorophenyl, 2-alkoxy-4-amino-5-bromophenyl, 2-alkoxy-4-acetylamino-5-chlorophenyl or 2-alkoxy-4-acetylamino-5-bromophenyl group, may also denote a 1,3-dihydro-2(2H)-oxobenzimidazol-1-yl or 2(1H)-oxoquinolin-3-yl group, 
 wherein the abovementioned mono- and bicyclic heterocycles containing two imino groups may be substituted at one of the imino-nitrogen atoms by an acetyl, carboxymethyl or methoxycarbonylmethyl group and/or  
 may additionally be mono-, di- or trisubstituted in the carbon skeleton and/or at the phenyl groups contained in these groups by fluorine, chlorine or bromine atoms, by methyl groups, nitro, methoxy, methanesulphonylamino, phenyl, trifluoromethyl, methoxycarbonyl, carboxy, hydroxy, amino, acetylamino, cyclohexanecarbonylamino, aminocarbonyl, hydroxyethylaminocarbonyl, (4-morpholinyl)carbonyl, (4-methyl-1-piperazinyl)carbonyl, [4-(1-piperidinyl)-1-piperidinyl]carbonyl, [4-(1-piperidinyl)piperidinyl]-carbonylamino or aminocarbonylamino groups, wherein the substituents may be identical or different and multiple substitution with the last six substituents is ruled out,  
 
 or, if Y denotes the carbon atom, with the proviso that 
 (i) R 1  does not denote a 2-alkoxy-4-amino-5-bromophenyl, 2-alkoxy-4-amino-5-chlorophenyl or naphthyl group or  
 (ii) Z 2  does not denote an N-containing group,  
 
 R N  may also denote the hydroxy group,  
 or, if Y denotes the carbon atom and Z 1  and Z 3  each denote the CO group, a benzoylaminocarbonylamino group, a phenylamino group optionally at least monosubstituted by an aminocarbonyl group at the aniline nitrogen and in the phenyl moiety  
 or, if Y denotes the carbon atom, Z 1  and Z 3  each denote the CO group and in the group of general formula (II) o and p each assume the value 1, a phenylmethylamino group optionally at least monosubstituted by a tert. butoxycarbonyl group at the benzylamine nitrogen and in the phenyl moiety,  
   or, if Z 1 -Z 2 -Z 3  denotes the divalent group CO—CH 2 —CH 2 —CO, R may also denote the 4-[3,4-dihydro-2(1H)-oxoquinazolin-3-yl]-(1.4′]bipiperidinyl-1′-yl group,    Z 1  denotes the methylene or carbonyl group or, if Z 2  denotes a divalent group of general formula III, may also denote a bond,    Z 2  denotes one of the groups —(CH 2 ) 2 — or —(CH 2 ) 3 —, 
 wherein a hydrogen atom may be replaced by a methyl or hydroxy group,  
   one of the groups    —NH—CH 2 , —CH 2 —NH— or —(CH 2 ) 2 —NH—, 
 wherein the nitrogen atoms are each linked to a carbonyl group of the groups Z 1  or Z 3  and the hydrogen atom of the imino group may be replaced in each case by the methyl group,  
   the group —CH═CH— or, if R 1  does not represent an aromatic or heteroaromatic group substituted by cycloalkyl or phenyl groups or R N  is not linked via an imino group bound in the adjacent position to a fused-on benzene ring, it also denotes a divalent group of general formula                          wherein 
 m denotes one of the numbers 1 or 2 and n denotes one of the numbers 1, 2 or 3 and the nitrogen atom is linked to the group Z 3  with the meaning of a carbonyl group,  
   Z 3  denotes the carbonyl group or, if R N  is not linked via an imino group bound in the adjacent position to a fused-on aromatic or heteroaromatic ring, it also denotes the methylene group,    wherein at least one of the groups Z 1  and Z 3  denotes the carbonyl group and the sequence Z 1 -Z 2 -Z 3  is at least four-membered, and    R 1  is defined as in  claim 3 ,    the tautomers, diastereomers, enantiomers and salts thereof.    
   
   
       5 . Compounds of the above general formula I according to  claims 1  to  4 , characterised in that they are described in Examples 1 to 16.  
   
   
       6 . The following compounds of general formula I: 
 1-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-1,3-dihydro-4-phenyl-2(2H)-imidazolone,    1-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-1,3-dihydro-4-(3-trifluoromethylphenyl)-2(2H)-imidazolone,    1-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-1,3-dihydro-4-(3-thienyl)-2(2H)-imidazolone,    3-[1′-(4-amino-3,5-dibromobenzoyl)-[1.4′]bipiperidinyl-4-yl]-3,4-dihydro-2(1H)-quinazolinone,    (E)-3-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxo-2-buten-1-yl]-4-piperidinyl}-3,4-dihydro-2(1H)-quinazolinone,    (E)-1-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxo-2-buten-1-yl]-4-piperidinyl}-1,3-dihydro-4-phenyl-2(2H)-imidazolone,    3-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-3,4-dihydro-2(1H)-quinazolinone,    methyl 3-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-3,4-dihydro-2(1H)-oxoquinazoline-7-carboxylate,    3-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-3,4-dihydro-2(1H)-oxoquinazoline-7-carboxamide,    3-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-3,4-dihydro-N-(2-hydroxyethyl)-2(1H)-oxoquinazolin-7-carboxamide,    3-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-1,3-dihydro-2(2H)-imidazo[4,5-c]quinolinone and 3-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-3,4-dihydro-2(1H)-quinazolinethione 
 and the salts thereof.  
   
   
   
       7 . Physiologically acceptable salts of the compounds according to at least one of  claims 1  to  6  with inorganic or organic acids or bases.  
   
   
       8 . Pharmaceutical compositions containing a compound according to at least one of  claims 1  to  6  or a physiologically acceptable salt according to  claim 7  optionally together with one or more inert carriers and/or diluents.  
   
   
       9 . Use of a compound according to at least one of claims-1 to 7 for preparing a pharmaceutical composition which has CGRP-antagonistic properties.  
   
   
       10 . Use of a compound according to at least one of  claims 1  to  7  for preparing a pharmaceutical composition which is suitable for the acute and prophylactic treatment of headaches, for treating non-insulin-dependent diabetes mellitus, cardiovascular diseases, skin diseases, inflammatory diseases, allergic rhinitis, asthma, diseases which are accompanied by excessive vasodilatation and consequent reductions in blood flow through the tissues, morphine tolerance or for controlling menopausal hot flushes.  
   
   
       11 . Process for preparing a pharmaceutical composition according to  claim 8 , characterised in that a compound according to at least one of  claims 1  to  7  is incorporated in one or more inert carriers and/or diluents by a non-chemical method.  
   
   
       12 . Process for preparing the compounds of general formula I according to  claims 1  to  7 , characterised in that 
 a) in order to prepare a compound of general formula I wherein Z 1  denotes the methylene group, Z 2  denotes one of the groups —(CH 2 ) 2 , —(CH 2 ) 3 — or —CH═CH— and Z 3  denotes the carbonyl group and    R has the meanings given in  claims 1  to  6  with the exception of a 4-[3,4-dihydro-2(1H)-oxoquinazolin-3-yl]-[1.4′]bipiperidinyl-1′-yl group,    a compound of general formula      R′—H  (IVa),    wherein    R′ has the meanings given for R in  claims 1  to  6  with the exception of a 4-[3,4-dihydro-2(1H)-oxoquinazolin-3-yl]-[1.4′]bipiperidinyl-1′-yl group,    is reacted with a compound of general formula      X—CH 2 -Z 2 -Z 3 -R 1   (V),    wherein    R 1  is defined as in  claims 1  to  6 ,    Z 2  denotes one of the groups —(CH 2 ) 2 , —(CH 2 ) 3 — or —CH═CH—,    Z 3  denotes the carbonyl group and    X denotes a leaving group, or    b) in order to prepare a compound of general formula I wherein    Z 1  denotes the carbonyl group,    Z 2  denotes one of the groups —(CH 2 ) 2 — or —(CH 2 ) 3 , wherein a hydrogen atom may be replaced by a C 1-3 -alkyl or a hydroxy group,    one of the groups —CH 2 —NH— or —(CH 2 ) 2 —NH, wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group, or the group —CH═CH— and    Z 3  denotes the methylene or carbonyl group,    a carboxylic acid of general formula      HOOC-Z 2 -Z 3 -R 1   (VI),    wherein    R 1  is defined as in  claims 1  to  6 ,    Z 2  denotes one of the groups —(CH 2 ) 2 — or —(CH 2 ) 3 , wherein a hydrogen atom may be replaced by a C 1-3 -alkyl or a hydroxy group,    one of the groups —CH 2 —NH— or —(CH 2 ) 2 —NH, wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group, or the group —CH═CH—, and    Z 3  denotes the methylene or carbonyl group,    is coupled with a compound of general formula      R—H  (IV),    wherein    R has the meanings given in  claims 1  to  6 , or    c) in order to prepare compounds of general formula I wherein    Z 1  denotes the carbonyl group,    Z 2  denotes one of the groups —(CH 2 ) 2 — or —(CH 2 ) 3 , wherein a hydrogen atom may be replaced by a C 1-3 -alkyl or hydroxy group, one of the groups —CH 2 —NH— or —(CH 2 ) 2 —NH, wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group, or the group —CH═CH— and    Z 3  denotes a methylene or carbonyl group,    a compound of general formula      Nu-CO-Z 2 -Z 3 -R 1   (VII),    wherein    R 1  is defined as in  claims 1  to  6 ,    Z 2  denotes one of the groups —(CH 2 ) 2 — or —(CH 2 ) 3 , wherein a hydrogen atom may be replaced by a C 1-3 -alkyl or a hydroxy group,    one of the groups —CH 2 —NH— or —(CH 2 ) 2 —NH, wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group, or the group —CH═CH—,    Z 3  denotes a methylene or carbonyl group and    Nu denotes a leaving group,    is coupled with a compound of general formula      R—H  (IV),    wherein    R is defined as in  claims 1  to  6 , or    d) in order to prepare a compound of general formula I wherein    Z 1  and Z 3  each denote the carbonyl group and    Z 2  denotes the group —(CH 2 ) 2 —:    a compound of general formula    R—CO—CH═CH—CO—R 1  (I′),    wherein    R and R 1  are defined as in  claims 1  to  6 , is catalytically hydrogenated, or    e) in order to prepare a compound of general formula I wherein    Z 1  denotes a methylene or carbonyl group or, if Z 2  denotes a divalent group of general formula III, may also denote a bond,    Z 2  denotes one of the groups —CH 2 —NH— or —(CH 2 ) 2 —NH, wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group, or a divalent group of general formula                          wherein    m and n independently of one another denote one of the numbers 1, 2, 3 or 4 and    Z 3  denotes the carbonyl group:    a carboxylic acid of general formula                          wherein    R 1  is defined as in  claims 1  to  6 ,    is coupled with a compound of general formula      R-Z 1 -Z 2 -H  (IX),    wherein    R is defined as in  claims 1  to  6 ,    Z 1  denotes a methylene or carbonyl group or, if Z 2  denotes a divalent group of general formula III, may also denote a bond,    Z 2  denotes one of the groups —CH 2 —NH— or —(CH 2 ) 2 —NH, wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group, or a divalent group of general formula                          wherein    m and n independently of one another denote one of the numbers 1, 2, 3 or 4 and    Z 3  denotes the carbonyl group, or    f) in order to prepare a compound of general formula I wherein    Z 1  denotes a methylene or carbonyl group or, if Z 2  denotes a divalent group of general formula III, Z 1  may also denote a bond,    Z 2  denotes one of the groups —CH 2 —NH— or —(CH 2 ) 2 —NH, wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group, or Z 1  denotes a divalent group of general formula                          wherein    m and n independently of one another denote one of the numbers 1, 2, 3 or 4 and    Z 3  denotes the carbonyl group,    a compound of general formula                          wherein    R 1  is defined as in  claims 1  to  6  and    Nu denotes a leaving group,    is coupled with a compound of general formula      R-Z 1 -Z 2 -H  (IX),    wherein    R 1  is defined as in  claims 1  to  6 ,    Z 1  denotes a methylene or carbonyl group or, if Z 2  denotes a divalent group of general formula III, may also denote a bond,    Z 2  denotes one of the groups —CH 2 —NH— or —(CH 2 ) 2 —NH wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group, or a divalent group of general formula                          wherein    m and n independently of one another denote one of the numbers 1, 2, 3 or 4 and    Z 3  denotes the carbonyl group, or    g) in order to prepare a compound of general formula I wherein R and R 1  are defined as in  claims 1  to  6 , with the proviso that they must not carry any free amino groups,    Z 1  denotes the carbonyl group,    Z 2  denotes one of the groups —NH—CH 2 — or —NH—(CH 2 ) 2 , wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group and    Z 3  denotes the methylene or carbonyl group,    an amine of general formula      R″—H  (XI),    wherein    R″ has the meanings given for R in  claims 1  to  6 , with the proviso that the group does not contain a free amino group,    is reacted with a carbonic acid derivative of general formula                          wherein    X 1  denotes a nucleofugic group and with a compound of general formula      H-Z 2 -Z 3 R 1′   (XIII),    wherein    the group R 1′  has the meanings given for R 1  in  claims 1  to  6 , with the proviso that the group does not contain a free amino group,    Z 2  denotes one of the groups —NH—CH 2 — or —NH—(CH 2 ) 2 , wherein a hydrogen atom bound to a carbon atom and/or the hydrogen atom of the imino group may each be replaced by a C 1-3 -alkyl group and    Z 3  denotes the methylene or carbonyl group, or    h) in order to prepare a compound of general formula I wherein at least one of the groups R and R 1  contains one or more carboxy groups:    a carboxylic acid ester of general formula      R a -Z 1 -Z 2 -Z 3 -R 1a   (Ia),    wherein    Z 1 , Z 2  and Z 3  are defined as in  claims 1  to  6  and    R a  and R 1a  have the meanings given for R and R 1 , respectively, in  claims 1  to  6 , with the proviso that at least one of these groups contains one or more alkoxycarbonyl groups,    is subjected to alkaline saponification and subsequently, if desired, the basic carboxylic acid is liberated by treatment with a dilute organic or inorganic acid, or    i) in order to prepare a compound of general formula I wherein at least one of the groups R and R 1  contains one or more amino groups,    an acylamine of general formula      R b -Z 1 -Z 2 -Z 3 -R 1b   (Ib),    wherein    Z 1 , z and Z 3  are defined as in  claims 1  to  6 ,    R b  and R 1b  have the meanings given in  claims 1  to  6  for R and    R 1 , respectively, with the proviso that R b  is substituted by an acetylamino, propionylamino, cycloalkanecarbonylamino or benzoylamino group and/or R 1b  is substituted by an acetylamino, propionylamino or benzoylamino group, is subjected to acid hydrolysis, or    j) in order to prepare a compound of general formula I wherein the group R contains one or two primary or secondary amino groups,    a compound of general formula      R c -Z 1 -Z 2 -Z 3 -R 1   (Ic),    wherein    R, Z 1 , Z 2  and Z 3  are defined as in  claims 1  to  6  and    R c  has the meanings given for R in  claims 1  to  6 , with the proviso that this group contains one or two primary or secondary amino groups which are substituted by a tert.alkoxy-carbonyl group, is subjected to acid hydrolysis, or    k) in order to prepare a compound of general formula I wherein    Z 1  and Z 3  each denote the carbonyl group,    Z 2  denotes the group —(CH 2 ) 2 — and    the group R 1  denotes a phenyl group which carries a tertiary amino group in the 4 position relative to the point of attachment but may otherwise be substituted as described in  claims 1  to  6 ,    a compound of general formula      R-Z 1 -Z 2 -Z 3 -R 1d   (Id),    wherein    R is defined as in  claims 1  to  6 ,    Z 1  and Z 3  each denote the carbonyl group,    Z 2  denotes the group —(CH 2 ) 2 — and    the group R 1d  denotes a phenyl group which carries a nucleophilically exchangeable function in the 4 position relative to the point of attachment, but may otherwise be substituted as described in  claims 1  to  6 ,    is nucleophilically substituted with a corresponding amine or    l) in order to prepare a compound of general formula I wherein the group R is uniformly mono-, di- or trisubstituted in the carbon skeleton by an aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group,    a compound of general formula      R e -Z 1 -Z 2 -Z 3 -R 1   (Ie),    wherein    the group R e  has the meanings given for R in  claims 1  to  6  with the proviso that it is mono-, di- or trisubstituted in the carbon skeleton by the carboxy group, and R 1 , Z 1 , Z 2  and Z 3  are defined as in  claims 1  to  6 ,    is coupled with ammonia or a corresponding alkylamine or dialkylamine, or    m) in order to prepare a compound of general formula I wherein the group R is substituted in the carbon skeleton by an acetylamino group or in the carbon skeleton by an acetylamino group and at the same time is substituted at one of the aza-nitrogen atoms by an acetyl group,    a compound of general formula      R f -Z 1 -Z 2 -Z 3 -R 1   (If),    wherein    R 1 , Z 1 , Z 2  and Z 3  are defined as in  claims 1  to  6  and    the group R f  has the meanings given for R in  claims 1  to  6 , with the proviso that it is substituted in the carbon skeleton by an amino group, is acylated or    n) in order to prepare a compound of general formula I wherein the group R is defined as in  claims 1  to  6 , with the proviso that it is substituted in the carbon skeleton by an acetylamino, propionylamino, cycloalkanecarbonylamino or benzoylamino group,    a compound of general formula                          wherein    R G  denotes a methyl, ethyl, cycloalkyl or phenyl group and    Nu denotes a leaving group    is coupled with a compound of general formula      R f -Z 1 -Z 2 -Z 3 -R 1   (If),    wherein    R 1 , Z 1 , Z 2  and Z 3  are defined as in  claims 1  to  6  and the group R f  has the meanings given for R in  claims 1  to  6 , with the proviso that it is substituted in the carbon skeleton by an amino group, or    o) in order to prepare a compound of general formula I wherein the group R is defined as in  claims 1  to  6 , with the proviso that it is substituted in the carbon skeleton by an aminocarbonylamino group,    a compound of general formula      R 1 -Z 1 -Z 2 -Z 3 -R 1   (If),    wherein    R 1 , Z 1 , Z 2  and Z 3  are defined as in  claims 1  to  6  and the group R f  has the meanings given for R in  claims 1  to  6 , with the proviso that it is substituted in the carbon skeleton by an amino group,    is reacted with cyanic acid, or    p) in order to prepare a compound of general formula I wherein the group R is defined as in  claims 1  to  6 , with the proviso that it is substituted by an aminomethyl group in the carbon skeleton, and    Z 2  has the meanings given in  claims 1  to  6  with the exception of the group —CH═CH—,    a compound of general formula      R g -Z 1 -Z 2 -Z 3 -R 1   (Ig),    wherein    R 1 , Z 1 , Z 2  and Z 3  are defined as in  claims 1  to  6  and the group R g  has the meanings given for R in  claims 1  to  6 , with the proviso that it is substituted in the carbon skeleton by a nitrile group,    is catalytically hydrogenated, or    q) in order to prepare a compound of general formula I wherein R is the 4-[3,4-dihydro-2(1H)-thioxoquinazolin-3-yl]-1-piperidinyl or 4-[3,4-dihydro-2(1H)-cyanoiminoquinazolin-3-yl]-1-piperidinyl group,    a diamine of general formula                          wherein    R 1 , Z 1 , Z 2  and Z 3  are defined as in  claims 1  to  6 ,    is reacted with N,N′-thiocarbonyldiimidazole or cyanoimino-diphenylcarbonate and    subsequently, if desired, a compound of general formula I thus obtained which contains a C═C double bond is resolved into the geometric isomers thereof, and/or    a racemate of general formula I thus obtained is resolved into its isomers and/or    a compound of general formula I thus obtained which contains an acid or basic function is converted into the salts thereof.