Celecoxib preparation process

Abstract

The invention provides a process for simply and efficiently preparing a selective cyclooxygenase-2 (COX-2) inhibitor 4-[3-trifluoromethyl-5-(4-methylphenyl)-1H-pyrazolyl]benzenesulfonamide (celecoxib, I). The process comprises the following steps: reacting an alkyl trifluoroacetate and 4-methylacetophenone which are initial raw materials under the action of an organic alkali solution, directly adding a dilute acid, an organic solvent and 4-aminosulfonylhydrazinobenzene or its acid salt to the resulting system, and heating to prepare the celecoxib. Above reaction adopts one kettle way, so the process has the advantages of mild condition, simple operation, high product yield and high product purity, and is suitable for industrialized production.

Description

technical field

[0001] The invention belongs to the technical field of medicine, in particular to a simple and efficient preparation of selective cyclooxygenase-2 (COX-2) inhibitor 4-[3-trifluoromethyl-5-(4-methylphenyl)- 1H-pyrazolyl]benzenesulfonamide (celecoxib, Celecoxib, I) method.

[0002] Background technique

[0003] Non-steroidal anti-inflammatory drugs (NSAIDs) have antipyretic, analgesic, anti-inflammatory, anti-rheumatic and anti-coagulant effects, and are widely used clinically in the treatment of osteoarthritis, rheumatoid arthritis and various pain and fever Relief of symptoms. Traditional NSAIDs play a therapeutic role by inhibiting COX, but inevitably bring about adverse reactions in the gastrointestinal tract (GI). Selective COX-2 inhibitors only reduce the synthesis of inducible COX-2 without affecting the synthesis of physiological COX-1, which not only has significant anti-inflammatory activity, but also reduces gastrointestinal damage. Celecoxib, ...

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