Analogifremgangsmåte for fremstilling av terapeutisk aktive 2-fenylaminoimidazolin (2)-forbindelser

1455624 2 - Phenylaminoimidazolines - (2) BOEHRINGER INGELHEIM GmbH 22 Feb 1974 [23 Feb 1973] 8202/74 Heading C2C Novel 2 - phenylaminoimidazolines - (2) of the general formula wherein each of R 1 , R 2 and R 3 is a hydrogen, fluorine, chlorine or bromine atom or a methyl, ethyl, methoxy, trifluoromethyl or cyano group and each of R 4 and R 5 , which must be different, is a hydrogen atom or a group of formula in which R 6 is a hydrogen atom or a methyl or ethyl group, with the proviso that one of R 4 and R 5 is a hydrogen atom, and acid addition salts thereof are prepared (a) when R 5 is a hydrogen atom, by reacting the corresponding compound in which R 4 is a hydrogen atom with a compound of the general formula wherein Hal is a chlorine, bromine or iodine atom; (b) when R 5 is a hydrogen atom, by reacting a compound of the general formula wherein A is a cyano or -C(=NH)Y group, in which Y is an atom or group removable as an anion, with ethylene diamine or an acid addition salt thereof; (c) when R 4 is a hydrogen atom, by reacting a compound of the general formula wherein X is as Y above, with a compound of the general formula and (d) by reacting a compound of the general formula wherein M is a metal and n represents the charge on the cation, with a compound of the second general formula above; and, if desired, converting a resulting free base into an acid addition salt thereof. Pharmaceutical compositions having analgesic and blood pressure-reducing activity comprise, as active ingredient, at least one 2-phenylaminoimidazoline-(2) or physiologically compatible acid addition salt thereof, in association with a pharmaceutical carrier or excipient.