CHINOLINE DERIVATIVES AND PROCESS FOR THE MANUFACTURE THEREOF

摘要

1280203 Quinoline derivatives F HOFFMANN-LA ROCHE & CO AG 2 July 1969 [2 July 1968] 57018/71 Divided out of 1280201 Heading C2C Novel quinoline derivatives of the Formulae Ia and Ib wherein R 1 is H, OH, halogen, C 1-7 alkyl, C 1-7 alkoxy or methylenedioxy, R 2 is vinyl or C 1-7 alkyl, R 4 is H or acyl, and m is 1 or 2, with the proviso that when R 1 is methylenedioxy m is 1, their antipodes and racemates and acid addition salts thereof are prepared by condensing the corresponding 4-methylquinolines with compounds of the Formulµ IIIa and IIIb wherein R 3 is C 1-7 alkyl, and, if desired, converting the bases so obtained into acid addition salts. The following starting materials and intermediates are prepared: 2-benzoyl-octahydro- 6(2H) - isoquinoline 2SP1/SP - benzoyl - 4,5 - dimethyl- 1SP1/SP,2SP1/SP,3SP1/SP,4SP1/SP,4SP1/SPa,7SP1/SP,8SP1/SP,8SP1/SPa - octahydrospiro- [1,3- dioxolane - 2,6SP1/SP(5SP1/SPH) - isoquinoline 7 - benzoyldecahydro - 2H - pyrido[3,4 - d]azepine - 2 - one, 2 - benzoyl - 1,2,3,4,7,8,9,9a - octahydro - 6H- pyrido[3,4 - d]azepine - 6 - one, 1 - benzoyl - 3- (2 - aminoethyl) - 4 - piperidineacetic acid ethyl ester, 1 - benzoyl - 3 - vinyl - 4 - piperidineacetic acid ethyl ester, 1 - benzoyl - 3 - (2 - dimethylaminoethyl)-4-piperidineacetic acid ethyl ester and its N-oxide, 7-benzoyl-3-nitroso-decahydro- 2H - pyrido[3,4 - d]azepin - 2 - one, 1 benzoyl. 3 - vinyl - 4 - piperidineacetic acid and its methyl ester, 3 - ( - benzyloxycarbonylcyanomethyl)glutaric acid diethyl ester, 3-(1- benzyloxycarbonyl - 1 - cyanopropyl)glutaric acid diethyl ester, 3- (1 .cyanopropyl)glutaric acid diethyl ester, 4-ethoxycarbonylmethyl-S-ethyl- 2 - piperdone, 3 - ethyl - 4 - piperidineacetic acid ethyl ester and 3-ethyl-4-ethoxycarbonyl- 6-ethoxy-1,2,3,4-tetrahydropyridine. Pharmaceutical compositions, having antiarrhythmic activity and suitable for oral or parenteral administration, contain the above novel quinoline derivatives, their antipodes or racemates or acid addition salts thereof, in association with suitable carriers or diluents.