GB1414327A - Substituted imidates - Google Patents

Abstract

1414327 N-aryl-imidates SCHERICO Ltd 21 Dec 1972 [23 Dec 1971] 59163/72 Heading C2C Novel N-aryl-imidates of the general formula wherein R 1 is a C 1-6 alkyl, C 3-6 cycloalkyl, aralkyl or aryl group, X is a nitro or trifluoromethyl group or a halogen atom, Y is a hydrogen or halogen atom or a nitro, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkanoyl, polyfluoro-C 1-6 alkoxy, polyfluoro- C 1-6 alkyl or trifluoromethylthio group, A is -C(R 2 )(R 3 )-, in which each of R 2 and R 3 is a Z-substituted C 1-5 alkyl group or ZR 2 R 3 C is a Z-substituted C 3-5 cycloalkyl group, and Z is a hydrogen or halogen atom or a free, etherified or esterified hydroxyl group, with the proviso that when each of X and Y is a chlorine atom or X is a chlorine atom and Y is a methyl group, then R 1 is a C 1-6 alkyl, C 3-6 cycloalkyl or aralkyl group, and pharmaceutically acceptable acid addition salts thereof are prepared (a) when Z is a hydrogen or halogen atom or an etherified hydroxyl group, by reaction of an N-arylimidohalide of the general formula wherein Hal is a halogen atom, with a compound of the general formula R 1 OH or a salt thereof; (b) by condensation of a thioanilide of the general formula with a haloformate of the general formula R 1 OCOHal; and (c) when X is a nitro group, by condensation of a halobenzene of the general formula wherein X is a nitro group, -with an imidate of the general formula HN=C(OR 1 )AZ. N-Aryl-imidohalides of the second general formula above are prepared by condensation of an aniline of the general formula with a compound of the general formula Hal.CO.AZ and treatment of the resulting anilide of the general formula with a phosphorus pentahalide under anhydrous conditions. Thioanilides of the fourth general formula above are prepared by reaction of the corresponding anilide with P 2 S 5 . Pharmaceutical compositions having antiandrogenic activity comprise, as active ingredient, an N-aryl-imidate of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, in association with a suitable carrier, and may be administered orally, parenterally or rectally.