GB1180862A - 2-[(Halophenoxy)Methyl]-2-Imidazolines - Google Patents

Abstract

1,180,862. 2 - [Halophenoxy) - methyl] - 2 - imidazolines. DOW CHEMICAL CO. 3 April, 1968 [4 April, 1967 (3)], No. 16060/68. Heading C2C. Novel 2 - (substituted phenoxymethyl) - 2 - imidazoline compounds, and the physiologically acceptable salts thereof, the compounds corresponding to the Formula (I) wherein Z represents a radical corresponding to one of the Formulµ (II) to (V) inclusive wherein X, X 1 and X 2 each independently represent chlorine or bromine, X<SP>1</SP> represents chlorine, bromine or methyl and A represents acetamido or amino, R represents trifluoromethyl, chlorine or bromine and R<SP>1</SP> represents hydrogen, trifluoromethyl, chlorine or bromine are prepared by a process which comprises: (a) where Z is one of Formulµ (II) or (IV) wherein X, X 1 , X 2 and X<SP>1</SP> are as defined above and A represents acetamido, reacting a substituted phenoxyacetonitrile of the formula Z-O-CH 2 -C#N, where Z is as defined above or ethyl - 2,6 - dihalo - 3 - methylphenoxyacetimidate hydrochloride, with ethylenediamine monotoxylate, and thereafter hydrolysing the thus formed tosylate; (b) where Z is Formula (III) wherein X 1 and X 2 are as defined above, reacting an alkyl-2,6-dihalo-3- methyl-phenoxyacetimidate hydrochloride with ethylenediamine monotosylate and thereafter hydrolysing the thus formed tosylate; (c) where Z is Formula (V) where A is acetamido and R and R<SP>1</SP> are as defined above, mixing a substituted phenoxyacetonitrile with ethylenediamine p-toluene-sulphonate and thereafter hydrolysing the thus formed tosylate; (d) where Z is Formula (IV) or (V) as defined above, but having A as amino, hydrolysing the corresponding compounds where A is acetamido with 5N hydrochloric acid. 2 - (Substituted phenoxymethyl) - 2 - imidazoline tosylates, i.e. the tosylates of compounds of the general Formula (I) are prepared as above. 2,6 - Dichlorophenoxyacetonitriles are prepared by mixing the corresponding dichlorophenol with chloroacetonitrile, anhydrous K 2 CO 3 and dimethyl sulphoxide. Ethyl - 2,6 - dichloro - 3 - methyl - phenoxyacetimidate hydrochloride is prepared by mixing 2,6 - dichloro - 3 - methylphenoxy - acetonitrile, ethanol, diethyl ether and saturating the mixture with hydrochloric acid. Pharmaceutical compositions having use in studying the drug effects on the central and peripheral nervous system and having analgesic, duiretic and antidepressant activities and containing compounds of the Formula (I) defined above or a physiologically-acceptable salt thereof are administered by intraperitoneal injection in association with a pharmaceutically acceptable carrier.