GB1264737A - - Google Patents

Abstract

1,264,737. Salicylic acid derivatives containing sulphur. MERCK & CO. Inc. 18 June, 1970 [25 June, 1969; 20 April, 1970], No. 29538/70. Heading C2C. Novel compounds I (including anhydrides and salts thereof) where R is OH, NH 2 , alkoxy, mono- or di-alkylamino, dialkylamino - alkyl - amino, phenylamino, dialkylaminoalkoxy, hydroxyalkoxy, polyhydroxyalkoxy, alkoxy-alkoxy, optionally substituted phenoxy, phenalkoxy, hydrazino, morpholino, piperidino, pyrrolidino, hydroxyalkylamino or a N-attached radical derived from an amino-acid, R 2 is H, acyl, alkyl or alkoxycarbonyl, R 3 is H, halogen, alkyl, haloalkyl, alkoxy or cycloalkyl, each X which may be the same or different is H, alkyl, halogen, OH, alkoxy, haloalkyl, acyloxy, amino, mono- or di-alkylamino, NO 2 , acylamino, SH, alkylmercapto, alkylsulphinyl, alkylsulphonyl, aminoalkyl, sulphamoyl, sulphinylamido, alkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, alkylthioalkyl, CN, CO 2 H, alkoxycarbonyl, CONH 2 , aryl, aralkyl or aryloxy and Y is S, SO or SO 2 are made by reacting a compound II (obtained, e.g. by demethylating the corresponding methoxy compound which is itself obtained, e.g. by interacting an appropriate benzenethiol sodium salt and a halophenol-ether in the presence of copper powder) with a carboxylating agent, e.g. CO 2 ; esters, amides and anhydrides are made according to standard methods and I in which Y is S can be oxidized to I in which Y is SO or SO 2 (the SO or SO 2 group can also be introduced at an intermediate stage of the synthesis, i.e. before the demethylation step). In general, compounds I may be converted one into the other if desired. p - Methylthio - benzotrifluoride, obtained by interacting p-methylthio-benzoic acid and sulphur tetra-fluoride, is demethylated in the presence of pyridine hydrochloride to afford p - mercaptobenzotrifluoride; 4- hydroxy - 4<SP>1</SP>- mercaptodiphenylsulphide, which is similarly obtained from p - (p - methylthiophenylthio)- anisole, is converted into p-(4-methylthiophenylthio)-phenol utilizing dimethylsulphate. Pharmaceutical preparations showing, in particular, anti-inflammatory action and also antipyretic, analgesic, diuretic, anti-fibrinolytic and hypoglycaemic action contain I as active ingredient; administration may be orally, rectally, parenterally or topically.