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Preparation method for celecoxib isomer

A technology of celecoxib and isomers, which is applied in the field of preparation of celecoxib isomers, can solve the problem of low content and achieve the effects of high yield, high selectivity and low cost

Inactive Publication Date: 2012-08-01
STONE LAKE PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During the synthesis of celecoxib, there will be by-products such as celecoxib isomers, but their content is low, and it is difficult for many pharmaceutical manufacturers to separate and obtain a small amount of celecoxib isomers

Method used

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  • Preparation method for celecoxib isomer
  • Preparation method for celecoxib isomer
  • Preparation method for celecoxib isomer

Examples

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Embodiment Construction

[0022] Participate in Figure 4 , the preparation method of celecoxib isomer of the present invention comprises the following steps:

[0023] Step (1): In a round bottom flask, dissolve 46.0 g of 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione in 300 mL of ethanol, and add 18.4 g of methoxylamine hydrochloride, and then heated to reflux for 8-10 h under stirring, followed by TLC spot plate. After the reaction was completed, the solvent was removed in vacuo, and 46.6 g of crude product 4,4,4-trifluoro-3-methoxyimino-1-(4-methylphenyl)-1-butanone was obtained by eluting with petroleum ether as a solvent. The yield is 90%.

[0024] Step (2): In a round bottom flask, add 46.6 g of crude product 4,4,4-trifluoro-3-methoxyimino-1-(4-methylphenyl)-1-butanone obtained in step (1) and 48.4 g of p-sulfamoylphenylhydrazine hydrochloride were dissolved in 300 mL of ethyl acetate (or petroleum ether) and 15 mL of acetic acid (also hydrochloric acid or sulfuric acid), then heated to re...

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Abstract

The invention discloses a preparation method for celecoxib isomer, which includes the steps: firstly, preparing a crude product of 4, 4, 4-trifluoro-3-methoxyimino-1-(4-cresyl)-1-butanone from 4, 4, 4-trifluoro-1-(4-cresyl)-1, 3-butanedione with methoxylamine hydrochloride serving as ammoniation protective reagent; and secondly, adding p-amino sulfonyl phenylhydrazine hydrochloride into the prepared crude product, dissolving with ethyl acetate and acetic acid, obtaining a crude product after heating and backflow, and recrystallizing to obtain a pure product of 4-[3-(4-methylphenyl)-5-(trifluoromethyl)-1H-pyrazolyl] benzene sulfonamide, namely, the celecoxib isomer, which is white or almost white crystalline powder in appearance. The preparation method has the advantages of low cost, simplicity in post-processing, high yield and high selectivity.

Description

[0001] technical field [0002] The invention relates to pharmaceutical preparations, in particular to a method for preparing celecoxib isomers. Background technique [0003] See attached figure 1 , Celecoxib (Celecoxib) is a new generation of compounds with a unique mechanism of action that specifically inhibits cyclooxygenase-2 (COX-2). Inflammatory stimulation can induce the production of COX-2, thus leading to the synthesis and accumulation of inflammatory prostaglandins, especially prostaglandin E2, causing inflammation, edema and pain. Celecoxib can prevent the production of inflammatory prostaglandins by inhibiting COX-2, and achieve anti-inflammatory, analgesic and antipyretic effects, such as the symptoms and signs of acute or chronic osteoarthritis and rheumatoid arthritis. [0004] Since celecoxib is widely used in the field of medicine, many scientists and pharmaceutical manufacturers are constantly researching and improving the synthesis process of celecoxib. ...

Claims

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Application Information

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IPC IPC(8): C07D231/12
Inventor 吕少波邱玲玲
Owner STONE LAKE PHARMA TECH
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