GB1338996A - Benzothiopyran derivatives - Google Patents

Abstract

1338996 Benzothiopyran WARNER-LAMBERT CO 14 July 1972 [15 July 1971 7 April 1972 8 May 1972] 33061/72 Heading C2C Novel benzothiopyran derivatives of the formula wherein R 1 is an optionally substituted aryl radical and R 2 is H, halogen, CN, NO 2 , CF 3 , alkyl, alkoxy, aryl or aralkyl; and salts thereof with bases are prepared by reacting the corresponding R 2 substituted thiochroman-4-one 1,1-dioxides with bases and thereafter with aryl isocyanates of the formula R 2 NCO, or by reacting the appropriate alkyl or aryl 4-hydroxy-2H- 1-benzothiopyran-3-carboxylates with amines of the formula R 1 NH 2 , or by reacting the corresponding thiochroman-4-one 1,1-dioxides with amines of the formula R 4 , R 5 , NH, wherein R 4 and R 5 are alkyl radicals or are joined together directly or via a heteroatom to form a herocyclic ring, treating the resulting enamines of the Formula V with phosgene and triethylamine, reacting the corresponding 4-(NR 4 R 5 )-2H-1-benzothiopyran- 3-carboxylic acid chloride 1,1-dioxides thus produced with amines of the formula R 1 NH 2 , and hydrolysing the resulting enamine amides with acids, or by reacting enamines of Formula V above with isocyanates of the formula R 1 NCO and hydrolysing the resulting enamine amides with acids. Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above novel compounds or salts thereof in admixture with solid or liquid pharmaceutical diluents or carriers. The compounds possess anti-inflammatory activity.