Benzothiazine dioxide derivatives

Details Benzothiazine dioxide derivatives Benzothiazine dioxide derivatives

C - Chemistry, Metallurgy

07

D

167/212, 260/243

C07D 279/02 (2006.01) C07D 417/12 (2006.01) C07D 417/14 (2006.01)

Patent

CA 1277662

Abstract A series of novel oxyalkyl ether derivatives of various enolic oxicam compounds have been prepared, including certain novel enol oxyalkyl ethers of 4- hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine- 3-carboxamide 1,1-dioxide (piroxicam). These par- ticular compounds are useful in therapy as prodrug forms of the known anti-inflammatory and analgesic oxicams. Typical and preferred member compounds include 4-[3-(hydroxy)-n-propyloxy]-2-methyl-N-(2- pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1- dioxide, 4-[5-(hydroxy)-n-pentyloxy]-2-methyl-N-(2- pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1- dioxide, 4-[3-(methoxycarbonyloxy)-n-propyloxy]-2- methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3- carboxamide 1,1-dioxide, 4-[3-(ethoxycarbonyloxy)-n- propyloxy]-2-methyl-N-(2-pyridinyl)-2H-1,2-benzo thiazine-3-carboxamide 1,1-dioxide, 4-[4-(ethoxy carbonyloxy)-n-butyloxy]-2-methyl-N-(2-pyridinyl- 2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide and 2-methyl-4-[3-(n-octyloxycarbonyloxy)-n-propyloxy]-N-(- 2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1- dioxide. Methods for preparing these compounds from known starting material are provided.

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