Verfahren zur Herstellung von neuen Amino-dihalogen-phenylaethylaminen

摘要

1,178,191. Phenethylamine derivatives. KARL THOMAE G.m.b.H. 22 Sept., 1967 [22 Sept., 1966; 1 Feb., 1967; 15 Feb., 1967; 2 June, 1967; 5 Sept., 1967], No. 43327/67. Heading C2C. Novel phenethylamine derivatives of the general formula wherein each Hal is a bromine or chlorine atom; R 1 is a hydrogen atom or a hydroxyl group; R 2 and R 3 are each hydrogen atoms or C 1-4 alkyl radicals; and R 4 and R 5 are each hydrogen atoms or C 1-6 alkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl, dialkylaminoalkyl, cycloalkyl, phenyl, benzyl or adamantyl radicals, or R 4 and R 5 , together with the nitrogen atom to which they are attached, form a pyrrolidine, piperidine, piperazine, morpholine, hexamethyleneimine or camphidine ring, any of which rings may be substituted by C 1-3 alkyl radicals, and acid addition salts thereof are prepared (a) when R 4 and R 5 are not alkenyl or alkynyl radicals, by bromination or chlorination of the benzene ring of phenethylamines of the general formula wherein R is a hydrogen, chlorine, or bromine atom and R 4 and R 5 are as above defined, with the exception of alkenyl and alkynyl radicals; (b) when R 1 is a hydroxyl group, by reduction of ketones of the general formula with complex metal hydrides; (c) when R 1 is a hydrogen atom, by reduction of ketones of the third general formula above with hydrazine; (d) by reaction of phenethyl halides of the general formula wherein Hal1 is a chlorine, bromine or iodine atom, with amines of the general formula R 4 R 5 NH; (e) by reduction of nitro-substituted phenethylamines of the general formula (f) by deacylation of acylarnino-substituted phenethylamines of the general formula wherein Ac is an acyl radical; (g) when R 1 is a hydroxyl group and R 2 and R 3 are hydrogen atoms and the H 2 N group is in the 2-position, by reduction of diketones of the general formula with complex metal hydrides; and (h) when R 1 is a hydroxyl group and R 2 and R 3 are hydrogen atoms and the H 2 N group is in the 2- position, by reduction of hydroxyketones of the general formula with complex metal hydrides; followed optionally by conversion of the product to an acid addition salt thereof. Pharmaceutical compositions having circulatory, analgesic, sedative, antipyretic, antiphlogistic, anti-tussive and/or broncholytic activity comprise, as active ingredient, at least one phenethylamine derivative of the first general formula above or non-toxic acid addition salt thereof, together with a pharmaceutical carrier or excipient, and may be administered orally, parenterally or rectally.