SUBSTITUTED 3-CHLORO-2-HYDRAZONOMETHYL-4-AZA-2, 4-PENTADIENENITRILES, A METHOD FOR PRODUCING THEM MEDICAMENTS CONTAINING THEM

摘要

1427849 3 - Chloro - 2 - hydrazonomethyl- 4 - aza - 2,4 - pentadienenitriles BYK GULDEN LOMBERG CHEMISCHE FABRIK GmbH 5 Sept 1973 [8 Sept 1972 (3)] 41666/73 Heading C2C Novel compounds I in which R1 and R2 are a C 1-7 alkyl, C 2-7 alkenyl or C 2-7 alkynyl group or together represent C 2-5 alkylene (in which one or more methylene groups may be replaced by O, S, or NR7) R3 is C(=X)R4, C(=X)-Y-R4 or [in which R4 is hydrogen, a C 1-14 alkyl, C 2-7 alkenyl or C 2-7 alkynyl group in which a methylene group may be replaced by oxygen and in which alkyl may be substituted by an NR5R6 group, C 3-6 cycloalkyl optionally substituted by an NR5R6 group or a phenyl or phenyl C 1-6 alkyl group (optionally substituted by C 1-4 alkyl, C 1-7 alkoxy, C 1-7 alkylthio, C 2-5 alkoxycarbonyl halogen, CF 3 , NO 2 and/or CN) R5 and R6 are hydrogen a C 1-7 alkyl, C 2-7 alkenyl or C 2-7 alkynyl group in which a methylene group may be replaced by oxygen, C 3-6 cycloalkyl or together represent C 2-5 alkylene in which one or more methylene groups may be replaced by O, S or NR7, X is O, S or NR7, Y is O, S or NH and R7 is hydrogen, C 1-7 alkyl C 2-7 alkenyl or C 2-7 alkynyl C 2-7 alkenyl or C 2-7 alkynyl] and their salts are prepared by reaction of a compound II R1R2N-CH=N-C(Cl)=C(CN)-CHO with R3-NH-NH 2 . Compounds I prepared are those in which R1 and R2 are methyl and R 3 is (in which R4 is hydrogen, C 1-14 alkyl in which a methylene group is optionally replaced by -O-, cyclohexyl, phenyl, p-methoxyphenyl, p-cyanophenyl or benzyl), -C(=Y)-NR5R6 (in which R 5 and R 6 are hydrogen, methyl or phenyl and Y is O, S or NH). Compounds II are prepared by hydrolysis of in which R8 and R9 are defined as for R1 and R2 and Z is an anion. Compounds I inhibit xanthineoxidase and may also be used for treating coronary insufficiency and arrhythmias. They form with a suitable vehicle a pharmaceutical composition, which may be administered orally or parenterally.