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Synthesis method of etoricoxib

A technology of etoricoxib and a synthesis method, applied in the field of synthesizing etoricoxib, can solve the problems of easy deterioration of sodium methoxide, large loss, flammability and explosion, etc., and achieves simplified post-processing process, improved synthesis steps, simplified reaction operation Effect

Inactive Publication Date: 2015-06-10
JIANGSU TIANHE PHARMA CO LTD
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Problems solved by technology

[0007] There are following defects in the above-mentioned synthetic method of etoricoxib: in the fourth step cyanation reaction, because sodium cyanide is insoluble in general organic solvents, it is necessary to use solvents such as dimethyl sulfoxide to react
Although the reaction can be carried out completely in dimethyl sulfoxide, because dimethyl sulfoxide and water are miscible and have a relatively high boiling point, the loss in the post-treatment is relatively large, and the yield cannot be improved.
Sodium methoxide is used in the fifth step reaction. Sodium methoxide is easy to deteriorate. It needs to be prepared with metal sodium and methanol before use. The cost is high, and metal sodium is also dangerous, flammable and explosive.
In the first step of the last step, potassium tert-butoxide is used. Potassium tert-butoxide is very easy to deteriorate, and sometimes it needs to be prepared and used immediately. Similarly, potassium metal is also more dangerous.

Method used

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  • Synthesis method of etoricoxib
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Embodiment Construction

[0028] Chemical name of the following compound A: p-methylthiobenzaldehyde; chemical name of compound B: p-methylthiobenzyl alcohol; chemical name of compound C: p-methylthiobenzyl chloride; chemical name of compound D: p-methylthiobenzyl alcohol Benzyl cyanide; chemical name of compound E: 2-(4-methylthiophenyl)-3-(6-methylpyridinium)-3-yl-3-oxopropionitrile; chemical name of compound F: 3-p-methylthiophenylacetyl-6-picoline; Chemical name of compound G: 3-p-methylsulfonylphenylacetyl-6-picoline; Chemical name of compound G 2: (Z)-N -(2-Chloro-3-(dimethylimino)allylidene)-N-methylmethylamine; compound H is etoricoxib.

[0029] 1. Existing synthetic technology steps:

[0030] 1. Synthetic Compound A:

[0031] Raw materials: p-chlorobenzaldehyde: 14.6g; sodium methyl mercaptide: 50g (20% aqueous solution); tetrabutylammonium bromide: 3.5g; water: 7ml; toluene: 30ml.

[0032] Dissolve the starting material in toluene, add sodium methyl mercaptide, water, tetrabutylammonium br...

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Abstract

The invention provides a synthesis method of etoricoxib and relates to the technical field of synthesis of non-steroid anti-inflammatory drugs. According to the synthesis method, the synthesis steps of the non-steroid anti-inflammatory drug etoricoxib are improved by use of a phase-transfer catalytic reaction, and therefore, the cost is greatly reduced, the yield is improved and the safety is also improved.

Description

technical field [0001] The invention relates to the technical field of synthesis of non-steroidal anti-inflammatory drugs, especially etoricoxib. Background technique [0002] Etoricoxib (5-chloro-6-methyl-3[4-(methylsulfonyl)phenyl]-2,3-bipyridine), molecular formula: C 18 h 15 ClN 2 o 2 S. Etoricoxib is an important non-steroidal anti-inflammatory drug, a highly selective cyclooxygenase-2 inhibitor, and an important analgesic drug. Its performance is better than that of traditional non-steroidal anti-inflammatory drugs. It has been greatly improved, and it is the only proven coxib drug for the treatment of acute gout and arthritis, and it has become the first choice drug for the treatment of rheumatoid arthritis in my country, so the market potential is huge. [0003] The research on the synthesis of etoricoxib at home and abroad has never stopped. At present, there are many reports on the synthesis of etoricoxib, and one of the methods is currently the method with...

Claims

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Application Information

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IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 戴振亚赵云德王子昱张学艳许莎莎
Owner JIANGSU TIANHE PHARMA CO LTD
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