4-(BENZOTHIAZOL-2-YL)FLUORO PHENYL-ACETIC ACIDS

1379526 Benzthiazole - 2 - yl - phenylacetic acids MERCK & CO Inc 12 Feb 1973 [17 Feb 1972] 6788/73 Heading C2C Novel compounds (I) in which R1α is a hydrogen atom or a C 1-5 alkyl radical and Rα is a hydrogen atom or R1α and Rα together represent a methylene or C 2-3 alkylidene radical; R 2 is a hydrogen or halogen atom or a hydroxy, C 1-5 alkoxy, mercapto, C 1-5 alkylthio, C 1-5 alkylsulphinyl, C 1-5 alkylsulphonyl, nitro, amino, di-(C 1-5 alkyl)amino, C 1-5 alkanoylamino, sulphamoyl, or sulpho radical; R 3 is a hydrogen or halogen atom or a C 1-5 alkoxy, nitro, hydroxy, or amino radical; X is a hydrogen or halogen atom or a di-(C 1-5 alkyl)amino, C 1-5 alkoxy, C 1-5 alkylthio, C 1-5 alkylsulphinyl, C 1-5 alkylsulphonyl, nitro, amino, or C 1-5 alkyl radical; Y is a hydrogen or halogen atom or a di-(C 1-5 alkyl)amino, C 1-5 alkylamino, or C 1-5 alkoxy radical; R 4 is a carboxy or hydroxymethyl radical or a radical of formula -COOR, COOM or where R is C 1-5 alkyl, C 3-5 alkenyl, C 3-7 cycloalkyl, phenyl, phenyl-(C 1-5 alkyl), (C 1-5 alkoxy)- (C 1-5 alkyl), C 1-5 hydroxyalkyl, or di-(C 1-5 alkyl)- amino-(C 1-5 alkyl) radical; M is an anion; R 5 is a hydrogen atom or a C 1-5 alkyl, phenyl-(C 1-5 alkyl), phenyl, or C 3-7 cycloalkyl radical and R 6 is a hydrogen atom or a C 1-5 alkyl radical, provided that R 4 is not -COOH or -CONH 2 when X, Y, R 2 , R 3 , Rα and R1α are all H, are made by standard methods, especially from the corresponding nitriles which are themselves obtained from the corresponding -CRαR1αBr compounds. The following compounds are also prepared: 2 - (4 - ethylphenyl) - benzothiazole, 2 - (3 - fluoro- 4 - methyl - phenyl) - benzothiazole, 4 - carboxy- α - hydroxyhydratropamide and 4 - carboxyatropamide. Pharmaceutical preparations showing antiinflammatory, analgesic and antipyretic actions contain (I) and/or 4-(benzothiazol-2-yl)-phenylacetic acid as active ingredient. Administration is orally, parenterally, rectally or topically.