A kind of method of synthesizing celecoxib

A technology for celecoxib and a compound is applied in the field of drug synthesis and preparation, and can solve the problems of being difficult to meet a large number of demands in the field of pharmaceutical synthesis, affecting large-scale production, and unsatisfactory product yield.

Inactive Publication Date: 2017-12-15
李文淏
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Nevertheless, these processes are still difficult to meet the large demand in the field of pharmaceutical synthesis, and due to the limited types of synthetic raw materials and unsatisfactory product yields, these affect the actual large-scale production to varying degrees.

Method used

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  • A kind of method of synthesizing celecoxib
  • A kind of method of synthesizing celecoxib
  • A kind of method of synthesizing celecoxib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of celecoxib

[0026]

[0027] Add 1mmol of the compound of formula (I) and 9g of solvent to the reactor, stir and mix at room temperature for 8min, then add 1.1mmol of the compound of formula (II), continue to stir and mix for 7min, then add 0.11mmol of the catalyst In(OAc) 3 , 0.12mmol ligand, 1.6mmol LiOH and 18mg additives Molecular sieves, stirred at room temperature and reacted for 5h. After the reaction was completed, the compound of formula (III) was obtained by filtration, vacuum concentration, and column chromatography (eluted with n-hexane / ethyl acetate), and the yield was 97.1%.

[0028] Wherein, the solvent is a mixture of ethylene glycol dimethyl ether and N-butylpyridine tetrafluoroborate with a mass ratio of 4:1; the ligand is 9-[2-(dicyclohexylphosphino)phenyl]- 9H-carbazole.

Embodiment 2

[0029] Embodiment 2: the synthesis of celecoxib

[0030]

[0031] Add 1mmol of the compound of formula (I) and 8g of solvent to the reaction kettle, stir and mix at room temperature for 5min, then add 1.1mmol of the compound of formula (II), continue to stir and mix for 10min, then add 0.1mmol of the catalyst In(OAc) 3 , 0.14mmol ligand, 1.7mmol LiOH and 15mg additives Molecular sieves, stirred at room temperature and reacted for 4h. After the reaction was completed, the compound of formula (III) was obtained by filtration, vacuum concentration, and column chromatography (eluted with n-hexane / ethyl acetate). The yield was 96.7%.

[0032] Wherein, the solvent is a mixture of ethylene glycol dimethyl ether and N-butylpyridine tetrafluoroborate with a mass ratio of 4:1; the ligand is 9-[2-(dicyclohexylphosphino)phenyl]- 9H-carbazole.

Embodiment 3

[0033] Embodiment 3: the synthesis of celecoxib

[0034]

[0035] Add 1mmol of the compound of formula (I) and 10g of solvent to the reactor, stir and mix at room temperature for 10min, then add 1.2mmol of the compound of formula (II), continue to stir and mix for 5min, then add 0.12mmol of the catalyst In(OAc) 3 , 0.13mmol ligand, 1.8mmol LiOH and 16mg additives Molecular sieves, stirred at room temperature and reacted for 6h. After the reaction was completed, the compound of formula (III) was obtained by filtration, vacuum concentration, and column chromatography (eluted with n-hexane / ethyl acetate). The yield was 97.3%.

[0036] Wherein, the solvent is a mixture of ethylene glycol dimethyl ether and N-butylpyridine tetrafluoroborate with a mass ratio of 4:1; the ligand is 9-[2-(dicyclohexylphosphino)phenyl]- 9H-carbazole.

[0037] Product Confirmation

[0038] After testing, the parameters of the celecoxib products prepared in all examples are consistent with those r...

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Abstract

The invention relates to a method for synthesizing celecoxib. According to the method, an oxo-phosphate compound is taken as a reaction raw material, a novel composite catalytic reaction system and a solvent environment are constructed, and reaction process parameters are optimized, so that high-yield preparation of celecoxib is achieved, and the celecoxib has wide market application prospects.

Description

technical field [0001] The invention relates to a preparation process of a nitrogen-containing heterocyclic compound, more specifically to a catalytic preparation process of celecoxib, which belongs to the field of drug synthesis and preparation. Background technique [0002] Celecoxib, English name Celebrex, and rofecoxib are specific inhibitors of two cyclooxygenase-2 (COX-2) commonly used in clinical practice, belonging to non-steroidal anti-inflammatory drugs, showing excellent Its anti-inflammatory and analgesic effects can be used to treat various acute and chronic arthritis and rheumatoid arthritis and other inflammatory diseases. Due to its wide application and high demand, the efficient preparation process of celecoxib drug has become one of the key issues concerned by many scientific researchers and medical workers. [0003] By reviewing the relevant reports so far, it is known that the prior art has successively disclosed various synthesis methods of the drug cel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/12
CPCC07D231/12
Inventor 李文淏
Owner 李文淏
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