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Preparation method of valdecoxib

A technology for valdecoxib and refined products, which is applied in the field of chemical pharmacy, can solve the problems of low purity and yield, unfavorable industrial production of valdecoxib, etc., and achieve the effect of improving purity and yield

Pending Publication Date: 2021-07-23
蚌埠丰原涂山制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

But the product that above-mentioned method obtains often has lower purity and yield, is unfavorable for the industrialized production of valdecoxib, and needs to be improved

Method used

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  • Preparation method of valdecoxib
  • Preparation method of valdecoxib

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Embodiment 1

[0046] The present embodiment provides a kind of preparation method of valdecoxib, comprising the following steps:

[0047] (1) Synthesis of 4-(5-methyl-3-phenyl-4-isoxazole) benzenesulfonyl chloride:

[0048] Weigh 19.2kg of dichloromethane and 4.0kg of 5-methyl-3,4-diphenylisoxazole into a 50L glass reactor. Weigh 18.9 kg of chlorosulfonic acid to be added dropwise at a high position. Turn on stirring, cool down in an ice bath, and cool down the temperature of the feed solution to 5°C. Start to add chlorosulfonic acid dropwise, and control the feed liquid temperature <10°C during the dropwise addition. After the addition of chlorosulfonic acid was completed, the temperature was slowly raised to 37° C., and the reaction was kept for 12 hours. Adopt TLC (thin-layer chromatography, developing agent is the mixed solution of ethyl acetate and sherwood oil volume ratio 1:6) monitors to after reaction is complete, the material liquid is left standstill layered, separates the low...

Embodiment 2

[0055] The present embodiment provides a kind of preparation method of valdecoxib, comprising the following steps:

[0056] (1) Synthesis of 4-(5-methyl-3-phenyl-4-isoxazole) benzenesulfonyl chloride:

[0057] Weigh 19kg of dichloromethane and 4.0kg of 5-methyl-3,4-diphenylisoxazole into a 50L glass reactor. Weigh 19kg of chlorosulfonic acid to be added dropwise at a high position. Start stirring, cool down in an ice bath, and cool down the feed solution to 0°C. Start to add chlorosulfonic acid dropwise, and control the feed liquid temperature <10°C during the dropwise addition. After the addition of chlorosulfonic acid was completed, the temperature was slowly raised to 33° C., and the reaction was kept for 14 hours. Adopt TLC (thin-layer chromatography, developing agent is the mixed solution of ethyl acetate and sherwood oil volume ratio 1:6) monitors to after reaction is complete, the material liquid is left standstill layered, separates the lower organic phase layer (4-...

Embodiment 3

[0064] The present embodiment provides a kind of preparation method of valdecoxib, comprising the following steps:

[0065] (1) Synthesis of 4-(5-methyl-3-phenyl-4-isoxazole) benzenesulfonyl chloride:

[0066] Weigh 19.5kg of dichloromethane and 4.0kg of 5-methyl-3,4-diphenylisoxazole into a 50L glass reactor. Weigh 19kg of chlorosulfonic acid to be added dropwise at a high position. Start stirring, cool down in an ice bath, and cool down the temperature of the feed solution to 3°C. Start to add chlorosulfonic acid dropwise, and control the feed liquid temperature <10°C during the dropwise addition. After the chlorosulfonic acid was added dropwise, the temperature was slowly raised to 35°C, and the reaction was kept for 13 hours. Adopt TLC (thin-layer chromatography, developing agent is the mixed solution of ethyl acetate and sherwood oil volume ratio 1:6) monitors to after reaction is complete, the material liquid is left standstill layered, separates the lower organic pha...

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Abstract

The invention provides a preparation method of valdecoxib. The preparation method comprises the following steps: dissolving 5-methyl-3,4-diphenylisoxazole in dichloromethane, adding chlorosulfonic acid, controlling the temperature of feed liquid to be less than or equal to 10 DEG C in the adding process, then carrying out heat preservation reaction at 30-40 DEG C, and after the reaction is finished, carrying out vacuum concentration on an organic phase to remove dichloromethane, so as to obtain 4-(5-methyl-3-phenyl-4-isoxazole)benzene sulfonyl chloride; and dissolving the obtained 4-(5-methyl-3-phenyl-4-isoxazole) benzene sulfonyl chloride in methylbenzene, and adding ammonia water for a reaction, so as to obtain valdecoxib. Compared with the prior art, the preparation method provided by the invention has the advantage that the purity and the yield of the valdecoxib product are effectively improved.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy, and in particular relates to a preparation method of valdecoxib. Background technique [0002] The chemical name of valdecoxib is: 4-(5-methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide. Molecular formula is C 16 h 14 N 2 o 3 S, the molecular weight is 314.36, the structural formula is as follows: [0003] [0004] Valdecoxib is a new generation of COX-2 inhibitors, which mainly exerts anti-inflammatory, analgesic and antipyretic effects by selectively inhibiting the synthesis of COX-2. It is often used clinically to treat osteoarthritis and rheumatoid arthritis and various acute pains. Valdecoxib is not only the key intermediate in the synthesis of parecoxib sodium, but also the main hydrolyzate of parecoxib sodium. The non-steroidal anti-inflammatory drug parecoxib sodium commonly used in the market is used as the precursor of valdecoxib The main therapeutic principle of the c...

Claims

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Application Information

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IPC IPC(8): C07D261/08
CPCC07D261/08
Inventor 张祖杨胡志国许祥雷
Owner 蚌埠丰原涂山制药有限公司
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