Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1975-12-29
1977-08-09
Gallagher, R. J.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
C07D27506
Patent
active
040410420
ABSTRACT:
A novel process for preparing 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide (I), starting with 3-amino-5-methylisoxazole (II) is disclosed. Compound I exhibits anti-inflammatory properties and is useful for treating inflammation. In the process of the invention an intermediate obtained, 2,3-dihydro-N-(5-methyl-3-isoxazolyl)-3-oxo-1,2-benzisothiazole-2-acetamid e 1,1-dioxide (IV) undergoes rearrangement to provide 1-{[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl}eth anone S,S-dioxide (V), which is methylated, according to conventional procedures. The methylated intermediate VI, upon further treatment, undergoes a second rearrangement to obtain the desired anti-inflammatory compound I.
Fabian Arthur C.
Genzer Jerome D.
Kasulanis Charles Francis
Shavel, Jr. John
Zinnes Harold
Chow Frank S.
Gallagher R. J.
Graddis Albert H.
Kelly Anne M.
Warner-Lambert & Company
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