IMPROVEMENTS IN OR RELATING TO THIAZOLE DERIVATIVES

1293741 2 - Alkylimino - 3 - alkyl - 5 phenyl- 4-thiazoline derivatives SANDOZ Ltd 1 Jan 1970 [13 Jan 1969 19 June 1969] 71/70 Heading C2C Novel 2 - alkylimino - 3 - alkyl - 5 - phenyl - 4- thiazoline derivatives of the general formula wherein R and R o are each a fluorine or chlorine atom or a C 1-3 alkyl or trifluoromethyl group, R 1 and R 2 are each a straight chain C 1-3 alkyl group, R 1 and R 2 are each a straight chain C 1-3 alkyl group or R 1 and R 2 together signify (CH 2 ) n , where n is 2 or 3, A is a hydrogen atom and B is a hydroxyl group or A and B together signify a carbon to carbon bond, and acid addition salts thereof are prepared (a) when A is a hydrogen atom and B is a hydroxyl group, by reaction of an α-halo-phenylacetaldehyde of the general formula with a thiourea of the general formula or (b) when A and B together signify a carbon to carbon bond, by dehydration of the product of (a); followed optionally by salification of the product. α-Halo-phenylacetaldehydes of the second general formula above are prepared by chlorination or bromination of a phenylacetaldehyde of the general formula Phenylacetaldehydes of the fourth general formula above wherein R and R o are not both a halogen atom are prepared by treatment of a phenylacetonitrile of the general formula with aqueous formic acid in the presence of Raney nickel alloy. Pharmaceutical compositions having hypotensive activity comprise, as active ingredient, a 2 - alkylimino - 3 - alkyl - 5 - phenyl - 4 - thiazoline derivative of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutically acceptable carrier, and may be administered orally or parenterally.