method for preparing thieno (2,3-c derivatives of (3.2), and (c) pyridines, new derivatives of thieno (2,3-c) pyridine obtained and their therapeutic application

摘要

This invention relates to a process for the preparation of antiinflammatory thieno [2,3-c]- and [3,2-c]pyridines having respectively the following formulae: IMAGE in which R1 and R2, which may be the same or different, represent each a hydrogen atom or an alkyl group, and their pharmaceutically acceptable acid addition salts, comprising: (a) condensing a compound of the following formulae (VII) or (VIII), respectively, IMAGE with a sulfonyl chloride having the formula ClSO2R3, in which R3 is a lower alkyl radical or a phenyl radical optionally substituted with a halogen atom or a lower alkyl group, within a two-phase solvent system and in the presence of sodium carbonate; (b) oxidizing in a solvent medium the resulting alcohols having respectively the following formula (V) or (VI): IMAGE (V) IMAGE (VI) (c) treating the resulting ketones, having the following formula (III) or (IV): IMAGE (III) IMAGE (IV) with a basic agent having the formula RO-M+ in which R is a branched- or straight-chain aliphatic alkyl radical and M+ is an alkali metal cation, within an alcohol solvent having the formula ROH, and at the reflux temperature of the reaction mixture, to give the compounds of the formula (I) or (II), respectively.