GB1359871A - Amino propanol - Google Patents

Abstract

1359871 Aminopropanols SANDOZ Ltd 27 Sept 1971 [30 Sept 1970 (2)] 44810/71 Heading C2C Compounds of the general formula (R 1 =H, C 3-7 cycloalkyl, C 1-8 alkyl, (C 3-7 cycloalkyl)-(C 1-6 alkyl) or phenyl-(C 1-6 alkyl) or diphenyl-(C 1-6 alkyl) in which the phenyl radicals may be substituted in the 3, 4 or 5 position(s) by 1-3 OH or OMe groups or in the 3,4-position by a methylenedioxy group) and salts thereof are prepared by (a) converting the ether groups into OH groups in a compound of the formula (R 2 =Me, Et, PhCH 2 ), (b) hydrogenolytically debenzylating a compound of the formula (R<SP>II</SP> 1 =H, C 3-7 cycloalkyl, C 1-8 alkyl, (C 3-7 cycloalkyl)-C 1-6 alkyl) or phenyl-(C 2-6 alkyl) or diphenyl-(C 2-6 alkyl) in which the phenyl radicals may be substituted in the 3, 4 or 5 position(s) by 1-3 OH or OMe groups or in the 3,4- position by a methylenedioxy group and are separated from the nitrogen atom by at least two carbon atoms; R 3 =H or PhCH 2 ; R<SP>I</SP> 3 = PhCH 2 or (R 3 =PhOH 2 )H, (c) reacting a compound of the formula with R 4 COR 5 (R 4 =H, C 1-7 alkyl, C 3-7 cycloalkyl, (C 3-7 cycloalkyl)-(C 1-5 alkyl) or phenyl- (C 1-5 alkyl) or diphenyl-(C 1-5 alkyl) in which the phenyl radicals may be substituted in the 3, 4 or 5 position(s) by 1-3 OH or OMe groups or in the 3,4-position by a methylenedioxy group and are separated from the oxygen atom by at least two carbon atoms; R 5 =H or C 1-7 alkyl, provided that when R 4 and R 5 =alkyl they together contain not more than 7 carbon atoms and when R 5 = alkyl and R 4 = cycloalkylalkyl, phenylalkyl or diphenylalkyl the total number of carbon atoms in R 5 and the alkylene residue of R 4 is not greater than 5) or a C 4-7 cycloalkanone under reductive alkylation conditions or (d) reducing a compound of the formula (R 6 , 7 = C 1-4 alkyl) and hydrolysing the product, optionally followed in each case by salt formation and/or resolution. The preparation of ethyl 2-(3,4-dimethoxyphenyl)-3-isopropylaminopropionate and its hydrochloride, 2 - (3,4 - dimethoxyphenyl) - 3 - isopropylaminopropanol and its hydrochloride, 3- amino - 2 - (3,4 - dimethoxyphenyl) propanol and its hydrochloride, ethyl 3-tert.-butylamino-2-(3,4- dimethoxyphenyl) propionate and its hydrochloride, 3 - tert. - butylamino - 2 - (3,4 - dimethoxyphenyl) propanol (resolved with di-p-toluoyltartaric acid), ethyl 2-(3,4-dibenzyloxyphenyl)-3- p - methoxyphenethylaminopropionate hydrochloride, 2 - (3,4 - dibenzyloxyphenyl) - 3 - (pmethoxyphenethylamino) propanol, ethyl 3-cyclopentylmethylamino - 2 - (3,4 - dimethoxyphenyl)- propionate and its hydrochloride, 3-cyclopentylmethylamino - 2 - (3,4 - dimethoxyphenyl) propanol, ethyl 3-(3-cyclopentylpropylamino)-2-(3,4- dimethoxyphenyl) propionate and its naphthalene- 1,5 - disulphonate, 3 - (3 - cyclopentylpropylamino) - 2 - (3,4 - dimethoxyphenyl) propanol and its hydrochloride, ethyl 3-cyclohexylmethylamino- 2-(3,4-dimethoxyphenyl) propionate and its hydrochloride and 3-cyclohexylmethylamino-2-(3,4-dimethoxyphenyl) propanol is described. The above compounds possess sympathomimetic activity, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.