IE34859B1 - Isoquinoline derivatives - Google Patents

Abstract

1335261 Isoquinolines HOFFMANN-LA ROCHE & CO AG 5 Jan 1971 [6 Jan 1970] 454/71 Heading C2C Compounds of the general formula (R = OH, C 1-4 alkoxy; R 1 = H, OH, C 1-4 alkoxy or R + R 1 = OCH 2 O; R 2 = H, C 1-4 alkyl; R 3 = C 1-4 alkyl, Ph(C 1-4 alkyl); R 4 = halogen, NO 2 NH 2 , C 1-4 alkylamino, di-(C 1-4 alkyl)amino; n = 1,2) and their acid addition salts are prepared by (a) cyclizing a compound of the formula (X = OH, acyloxy, halogen), (b) alkylating or aralkylating a compound of the formula (R 40 = halogen, NO 2 , dialkylamino), (c) reducing a compound of the formula (R 0 = C 1-4 alkoxy; R 10 = H, C 1-4 alkoxy or R 0 + R 10 = OCH 2 O; R 30 = C 1-4 alkyl, Ph(C 2-4 alkyl); R 41 = halogen, dialkylamino) under acidic conditions or reducing a compound of the formula (d) reducing a compound of the formula (R 11 = OH, C 1-4 alkoxy or R + R 11 = OCH 2 O; Y = anion), (e) reducing a compound of the formula (f) when R and/or R 1 = OH, subjecting a corresponding compound in which R and/or R 1 = alkoxy to acidic ether-cleavage, (g) when R 4 = NH 2 (R 3 not PhCH 2 ), reducing a corresponding compound in which R 4 = NO 2 , (h) when R 4 = alkylamino or dialkylamino, monoalkylating a corresponding compound in which R 4 = NH 2 or alkylamino, (i) when R and/or R 1 = OH (R 3 not PhCH 2 , R 4 not NO 2 ), hydrolytically debenzylating a corresponding compound but in which R and/or R 1 = PhCH 2 O, (j) when the product is optically active, resolving the racemate or using an optically active starting material or (k) when the product contains at least two asymmetric carbon atoms, separating an individual racemate from the diastereomer mixture, optionally followed in each case by salt formation. The starting materials are prepared by the following routes The above compounds are antidepressants, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier. [GB1335261A]