Processes for preparing piroxicam and intermediates leading ther

Details Processes for preparing piroxicam and intermediates leading ther Processes for preparing piroxicam and intermediates leading ther

1984-04-05

1984-11-20

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

548210, C07D27902

Patent

active

044839820

ABSTRACT:
Processes for the preparation of the antiinflammatory agent piroxicam and intermediates leading thereto, the first of which comprises reacting N-methylsaccharin with (N-2-pyridyl)haloacetamides and alkyl haloacetates in the presence of an appropriate base to give, respectively, piroxicam and alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides, intermediates which can be converted into piroxicam; and the second of which comprises reacting a novel alkyl 2-(2-methyl-3-hydroxy-2,3-dihydro-1,2-benzisosulfonazol-3-yl)-2-haloacetat e with a metal hydride to give alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides, intermediates leading to piroxicam.

REFERENCES:
patent: 3591584 (1971-07-01), Lombardino
patent: 3853862 (1974-12-01), Lombardino
patent: 3891637 (1975-06-01), Lombardino
patent: 4116964 (1978-09-01), Zinnes et al.
patent: 4376204 (1983-03-01), Weeks
Barton and Ollis, Comprehensive Organic Chemistry, vol. 4, Pergamon, New York, (1979), pp. 1093-1095.
Lombardino et al., "Synthesis . . . 2H-1,2-Benzothiazine 1,1 Dioxide," J. Med. Chem. 14, pp. 1171-1175, (1971).

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