Patent EP-0257294-B1 (EP)
IPC: C07C255/64
Filed: 1987-07-20
Granted: 1990-09-12
Abstract: 1. Mixtures of E/Z isomers and pure Z isomers of N**alpha -(2-cyano-2-alkoximino-acetyl)-amino acid derivatives and peptides of the general formula (I)  see diagramm : EP0257294,P17,F1  in which R represents straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl or alkinyl in each case having 2 to 4 carbon atoms, cyanoalkyl having 1 to 4 carbon atoms, 1,2,4-triazol-1-ylalkyl and pyrazol-1-ylalkyl in each case having 1 to 6 carbon atoms in the alkyl part, phenylalkyl, having 1 to 4 carbon atoms in the alkyl part, which is optionally mono- to trisubstituted in the phenyl part by identical or different substituents, substituents which may preferably be mentioned being : halogen, cyano, nitro, hydroxyl, alkyl, alkoxy, alkylsulphinyl, alkylsulphonyl and alkylthio in each case having 1 to 4 carbon atoms, and phenyl which is optionally mono- to trisubstituted by identical or different halogen substituents ; or represents cycloalkyl, having 3 to 7 carbon atoms, which is optionally mono- to trisubstituted by identical or different substituents, substituents which may preferably be mentioned being halogen and alkyl having 1 to 4 carbon atoms ; R**1 represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, or phenyl or benzyl which is in each case optionally mono- to trisubstituted by identical or different substituents, suitable substituents preferably being the phenyl substituents already mentioned in the case of R ; R**2 represents hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms ; R**3 represents hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched hydroxyalkyl having 1 to 4 carbon atoms, alkoxycarbonylalkyl having 1 to 4 carbon atoms in both the alkoxy part and in the alkyl part, hydroxycarbonylalkyl and aminocarbonylalkyl in each case having 1 to 4 carbon atoms in the alkyl part, 1,2,4-triazol-1-ylalkyl, 1,2,4-triazol-4-ylalkyl, imidazol-4-ylalkyl and pyrazol-1-ylalkyl in each case having 1 to 6 carbon atoms in the alkyl part, cyanoalkyl having 1 to 4 carbon atoms, alkenyl or alkinyl in each case having 2 to 4 carbon atoms, cycloalkyl, having 3 to 7 carbon atoms, which is optionally mono- to trisubstituted by identical or different substituents, substituents which may preferably be mentioned being halogen and alkyl having 1 to 4 carbon atoms, furthermore represents phenyl or phenylalkyl, having 1 to 4 carbon atoms in the alkyl part, which is optionally mono- to trisubstituted in the phenyl part by identical or different substituents, suitable substituents in each case preferably being the phenyl substituents already mentioned in the case of R, or represents the R**4 -SOn -Z group, where R**4 represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, phenylalkyl, having 1 to 4 carbon atoms in the alkyl part, which is optionally mono- to trisubstituted in the phenyl part by identical or different substituents, suitable substituents being the phenyl substituents already mentioned in the case of R ; n represents the numbers 0, 1 or 2, and Z represents a straight-chain or branched alkylene chain having 1 to 4 carbon atoms ; R**1 and R**3 , together with the nitrogen atom and the carbon atom to which they are bound, represent a 5- or 6-membered heterocycle ; R**2 and R**3 , together with the carbon atom to which they are bound, represent cycloalkylidene having 3 to 6 carbon atoms ; X represents the -OR**I or -NR**II R**III groups, where R**1 represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, or alkenyl or alkinyl in each case having 2 to 4 carbon atoms ; R**II represents hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms ; R**III represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl in each case having 2 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxyalkyl having 1 to 4 carbon atoms in both the alkoxy part and in the alkyl part, dialkylaminoalkyl having up to 4 carbon atoms in the individual alkyl parts, alkoxycarbonylalkyl having 1 to 4 carbon atoms in both the alkoxy part and in the alkyl part, hydroxycarbonylalkyl having 1 to 4 carbon atoms in the alkyl part, aminocarbonylalkyl, alkylaminocarbonylalkyl or dialkylaminocarbonylalkyl in each case having 1 to 4 carbon atoms in each alkyl part cyanoalkyl having 1 to 4 carbon atoms in the alkyl part, phenylalkyl, having 1 to 4 carbon atoms in the alkyl part, which is optionally mono- to trisubstituted in the phenyl part by identical or different substituents, or phenyl which is mono- to trisubstituted by identical or different substituents, suitable substituents in each case being the phenyl substituents already mentioned in the case of R, and also represents cycloalkyl, having 3 to 7 carbon atoms, which is optionally substituted by identical or different substituents, suitable substituents preferably being halogen and alkyl having 1 to 4 carbon atoms ; or R**II and R**III , together with the nitrogen atom to which they are bound, represent a 5- or 6-membered heterocycle, which may optionally contain oxygen or nitrogen as further heteroatoms and may optionally be substituted by cyano, halogen, alkyl having 1 to 4 carbon atoms, hydroxycarbonyl, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part, aminocarbonyl, and alkylaminocarbonyl and dialkylaminocarbonyl in each case having 1 to 4 carbon atoms in the individual alkyl parts, with the exception of the compounds N-(methoxycarbonylmethyl)-(2-cyano-2-methoximino)-acetamide and N-(carbamoylmethyl)-(2-cyano-2-methoximino)-acetamide.