Method for preparing Parecoxib

A technology of parecoxib and valdecoxib, applied in the field of prodrugs of valdecoxib, can solve problems such as unfavorable safe production, increased difficulty in industrialized operation and the like

Inactive Publication Date: 2012-01-25
海南霞迪药业有限公司 +1
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  • Abstract
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  • Application Information

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Problems solved by technology

The disadvantage of this route is that butyllithium is used as the reaction reagent, because its reaction system requires absolute anhydrous and oxygen-free, the reaction tempera

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  • Method for preparing Parecoxib
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  • Method for preparing Parecoxib

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Embodiment Construction

[0025] The present invention will be further described below in conjunction with preferred embodiment, but the present invention is by no means limited to following embodiment.

[0026] The 1,2-benzophenone used in the present invention is purchased from ACROS Company of the United States, and other raw materials are analytically pure or chemically pure provided by Sinopharm Group.

[0027] 1. Preparation of 1-phenyl-2-(4-sulfophenyl)ethanone (5)

[0028] 19.6 g (0.1 mol) of 1,2-benzophenone was dissolved in 200 mL of acetone, and 11.6 g (0.1 mol) of chlorosulfonic acid was slowly added dropwise at 0°C. After the dropwise addition, the temperature was naturally raised to 25° C., and the reaction was continued for 5 h. After the reaction is complete, distill off the acetone, add 100mL of water to the residue and continue to reflux for 12h, after cooling, add 50mL of ethyl acetate for extraction, combine the ester layer, dry the ester layer with anhydrous sodium sulfate, filter...

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Abstract

The invention discloses a method for preparing Parecoxib. The method for preparing the Parecoxib comprises the following steps of: performing sulfonation reaction on 1,2-diphenyl butanone serving as a raw material to obtain 1-phenyl-2-(4-sulfo phenyl)butanone; in the presence of alkali, performing condensation on the 1-phenyl-2-(4-sulfo phenyl)butanone and acetylchloride to prepare 1-phenyl-2-(4-sulfo phenyl)-2-acetyl butanone; performing cyclization on the 1-phenyl-2-(4-sulfo phenyl)-2-acetyl butanone and hydroxylamine hydrochloride to obtain 4-(5-methyl-3-phenyl-4-isoxazole)benzenesulfonic acid; performing chlorination and ammonolysis reaction to prepare Bextra; and reacting the Bextra with propionic anhydride to synthesize the Parecoxib. In the method, the raw materials are readily available and reaction conditions are not rigorous. The method is easy and convenient to operate and has certain industrialized value.

Description

technical field [0001] The invention relates to a method for preparing parecoxib. The product is a prodrug of valdecoxib, and its sodium salt is used clinically. It is mainly used for the short-term treatment of postoperative pain and the treatment of moderate or severe postoperative acute pain. Background technique [0002] There are currently three main methods for the preparation of parecoxib. [0003] Method 1: Letendre et al. (WO2005123701, 2005-12-29) used 1,2-benzophenone as the starting material, condensed with tetrahydropyrrole, and then chloroacetylated. Subsequent cyclization and dehydration under sodium acetate and hydroxylamine hydrochloride give 3,4-diphenyl-5-methylisoxazole. Finally, chlorosulfonation reaction and ammonolysis are carried out. Finally, the final product parecoxib was obtained after propionylation. In this route, expensive reaction reagents, such as 2,6-lutidine, are used as an acidic agent, which increases the cost. At the same time, the ...

Claims

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Application Information

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IPC IPC(8): C07D261/08
Inventor 王凯陈长潭易安茂
Owner 海南霞迪药业有限公司
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