Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing parecoxib

A synthesis method, parecoxib technology, applied in the field of parecoxib synthesis, can solve the problems of low yield, complex synthesis process of parecoxib, difficulty in separation, etc., to reduce production cost, increase yield, The effect of less by-products

Inactive Publication Date: 2018-08-24
TAICANG YUNTONG BIOCHEM ENG
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] This process has an obvious disadvantage, that is, another isomer (9) will be produced when the key intermediate (5) is formed, namely , since the two structures are very similar, it is difficult to separate
[0008] Looking at the above prior art, the synthesis process of parecoxib is relatively complicated and the yield is low

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing parecoxib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] According to the ratio of raw materials, that is, the amount of trifluoromethanesulfonic acid is 0.08 (based on the molar number of benzophenone oxime as 1), and the amount of solvent used for acetonitrile and tetrahydrofuran (the volume ratio of the two is 1:1) is 3ml ( The molar dosage of benzophenone oxime is 1 mmol), and the dosage of p-sulfophenylpropyne is 0.5 (the molar dosage of benzophenone oxime is 1). Add magnetons into the three-necked flask, put in p-sulfophenylpropyne, benzophenone oxime, trifluoromethanesulfonic acid, acetonitrile and tetrahydrofuran, and turn on the magnetic stirrer. React at 60°C. Use TLC plate and GC-MS to monitor, after the reaction is complete, cool naturally, filter, and rotate to evaporate the solvent, and finally use n-hexane and ethyl acetate in an appropriate proportion as mobile phase, and purify and separate the pure product by column chromatography, which is 5-Methyl-3-phenyl-4-(4'-sulfo)phenylisoxazole.

[0030] Add 5-meth...

Embodiment 2

[0033] According to the ratio of raw materials, that is, the amount of trifluoromethanesulfonic acid is 0.12 (based on the molar number of benzophenone oxime as 1), and the amount of solvent used for acetonitrile and tetrahydrofuran (the volume ratio of the two is 2:1) is 7ml ( The molar dosage of benzophenone oxime is 1 mmol), and the dosage of p-sulfophenylpropyne is 0.9 (the molar dosage of benzophenone oxime is 1). Add magnetons into the three-necked flask, put in p-sulfophenylpropyne, benzophenone oxime, trifluoromethanesulfonic acid, acetonitrile and tetrahydrofuran, and turn on the magnetic stirrer. React at 80°C. Use TLC plate and GC-MS to monitor, after the reaction is complete, cool naturally, filter, and rotate to evaporate the solvent, and finally use n-hexane and ethyl acetate in an appropriate proportion as mobile phase, and purify and separate the pure product by column chromatography, which is 5-Methyl-3-phenyl-4-(4'-sulfo)phenylisoxazole.

[0034] Add 5-meth...

Embodiment 3

[0037] According to the ratio of raw materials, that is, the amount of trifluoromethanesulfonic acid is 0.12 (based on the molar number of benzophenone oxime as 1), and the amount of solvent used for acetonitrile and tetrahydrofuran (the volume ratio of the two is 2:1) is 3ml ( The molar dosage of benzophenone oxime is 1 mmol), and the dosage of p-sulfophenylpropyne is 0.5 (the molar dosage of benzophenone oxime is 1). Add magnetons into the three-necked flask, put in p-sulfophenylpropyne, benzophenone oxime, trifluoromethanesulfonic acid, acetonitrile and tetrahydrofuran, and turn on the magnetic stirrer. React at 70°C. Use TLC plate and GC-MS to monitor, after the reaction is complete, cool naturally, filter, and rotate to evaporate the solvent, and finally use n-hexane and ethyl acetate in an appropriate proportion as mobile phase, and purify and separate the pure product by column chromatography, which is 5-Methyl-3-phenyl-4-(4'-sulfo)phenylisoxazole.

[0038] Add 5-meth...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing parecoxib. Widely sourced adenosine is taken as an initial raw material and is subjected to cyclization, amination and amidation sequentially. Fewer steps are adopted, few by-products are obtained, the yield is increased, and the production cost is reduced.

Description

technical field [0001] The present invention relates to the technical field of parecoxib, in particular to a method for synthesizing parecoxib. Background technique [0002] Parecoxib is a cyclooxygenase-2 (COX-2) specific inhibitor. Coxib analgesics belonging to anti-arthritic drugs. Common English name: Parecoxib, trade name: Te Nai (Chinese pinyin of trade name: tenai), chemical name: N-[[4-(5-methyl-3-phenyl-4-isoxazolyl)phenyl ]sulfonyl]propionamide salt, (N-[[4-(5-methyl-3-phenyl-4-isoxazolyl)phenyl]sulfonyl]-), alias: Dynastat, SC-69124. Molecular formula: C19H18N2O4S, molecular weight: 370.43, molecular structure as follows: [0003] . [0004] Parecoxib is a prodrug of valdecoxib. Valdecoxib is a selective cyclooxygenase-2 (COX-2) inhibitor in the clinical dose range, which is involved in the synthesis of prostaglandins. There are two isomers of COX-1 and COX-2. Studies have shown that COX-2 is induced as a cyclooxygenase isoform by pro-inflammatory stimuli...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/08
CPCC07D261/08
Inventor 张卫东
Owner TAICANG YUNTONG BIOCHEM ENG
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com