GB1340720A — Benzomorphan derivatives processes for producing them and composi tions containing them

USPTO Abstract

1340720 Benzomorphans SUMITOMO CHEMICAL CO Ltd 12 Aug 1971 [14 Aug 1970 (2) 17 Sept 1970 (2) 20 Oct 1970 30 Oct 1970 8 Dec 1970 (2) 17 Dec 1970 24 Dec 1970 28 Dec 1970 (2) 29 Jan 1971 8 Feb 1971] 37975/71 Heading C2C Novel benzomorphan derivatives of Formula (I) where R is hydrogen, C 1 -C 3 alkoxy, acyloxy, hydroxyl, nitro, halogen, cyano, amino, carboxyl, carbamoyl or sulpho; R 1 is hydrogen, C 1 -C 3 alkyl or a group of formula (where m is 1 to 6, p is 1 to 2 and R q is hydroxyl or C 1 -C 3 alkoxy); R 2 is hydrogen or C 1 -C 3 alkyl, R 3 and R 4 are hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy C 1 -C 3 alkylthio, nitro, trifluoromethyl, amino or hydroxyl; R 5 is hydrogen or methyl; R 6 is hydrogen or C 1 -C 3 alkyl; R 7 is hydrogen C 1 -C 3 alkyl, phenyl or C 1 -C 3 alkoxy phenyl; R 8 is hydrogen or hydroxyl or R 7 with R 8 may form a C 1 -C 3 alkylidene group or an oxo group and n is 2 to 4 with the proviso that if n = 2, R 1 and R 2 are methyl, R is hydrogen or hydroxyl and R 4 , R 5 , R 6 , R 7 and R 8 are hydrogen then R 3 is halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 . alkylthio, nitro trifluoromethyl, amino or hydroxyl, or if R is hydrogen, hydroxyl or C 1 -C 3 alkoxy, R 1 is C 1 -C 3 alkyl, R 3 and R 4 are hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, nitro, trifluoro-methyl, amino or hydroxyl, R 5 , R 6 , R 7 and R 8 are hydrogen and n = 3 or 4 then R 2 is hydrogen are prepared by hydrolysing a novel ethylenedioxy derivative of Formula (II) preferably in water or alcohol with an acid catalyst. Compounds of Formula (I) may also be prepared by reacting a 6, 7 benzomorphen of Formula (III) with a halide of Formula IV where X is halogen and Y is oxygen or an ethylene dioxy group and when Y is ethylene dioxy, hydrolysing the derivative. The reaction is preferably carried out in the presence of a base and in an inert organic solvent. Compounds of Formula (I) in which R 2 is a C 1 -C 3 alkyl group have two stereo isomers (α,#) which may be separated by fractional crystallization, distillation or chromatography. Compounds of Formula (I) are analgesics and have tranquillizing and local anaesthetic properties. These compounds form a pharmaceutical preparation, with a suitable adjuvant, and are administered parenterally or orally.