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A kind of synthetic method of Erecoxib

A synthesis method and compound technology, applied in the field of erecoxib synthesis, can solve the problems of low yield, high bromine and bromine toxicity, and great harm to the environment and human body, and achieve simple reaction steps, easy industrial production, and environmental reduction. and the effects of harm to the human body

Active Publication Date: 2016-08-24
SHANDONG BOYUAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It solves the problem that the existing Erecoxib synthesis route is long, the yield is too low, and bromine is used in the production process, which is highly toxic and harmful to the environment and human body

Method used

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  • A kind of synthetic method of Erecoxib
  • A kind of synthetic method of Erecoxib
  • A kind of synthetic method of Erecoxib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Take 50g of p-methylphenylacetyl chloride and 19.3g of n-propylamine into a 500ml three-necked flask, add 200ml of toluene, heat and reflux for 4 hours, cool down to room temperature, wash twice with 100ml of drinking water, and distill the toluene under reduced pressure to obtain an oily substance 54g, yield 95%.

[0031] Add 200ml of methanol to the oil, stir to dissolve the oil, add 32g of sodium methoxide, continue to stir and dissolve, add 66.8g of methylsulfonylphenyl chloroethanone, heat and reflux for 6 hours, evaporate the solvent under reduced pressure, add drinking water 300ml was beaten for 1 hour, filtered, and the filter cake was washed with 30ml of drinking water, and dried to obtain 90.8g of white solid, with a yield of 87%.

Embodiment 2

[0033] Take 50g of p-methylphenylacetyl chloride and 19.3g of n-propylamine and put them into a 500ml three-necked flask, add 200ml of dichloromethane, heat and reflux for 6 hours, cool down to room temperature, wash twice with 100ml of drinking water, and distill off the dichloromethane under reduced pressure , to obtain 53 g of oily matter, yield 93%.

[0034] Add 200ml of methanol to the oil, stir to dissolve the oil, add 30g of sodium methoxide, continue to stir and dissolve, add 78.1g of methylsulfonylphenylbromoethanone, heat and reflux for 6 hours, evaporate the solvent under reduced pressure, add drinking water 300ml was beaten for 1 hour, filtered, and the filter cake was washed with 30ml of drinking water, and dried to obtain 92.1g of white solid, with a yield of 90%.

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PUM

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Abstract

The invention discloses a synthesis method of imrecoxib and belongs to the field of drug synthesis. The method comprises the following steps: reacting p-toluene acetyl halide with propylamine to produce a compound III p-toluene levulinic amine; reacting the compound III with p-methylsulfonyl chloroacetophenone under an alkaline condition to produce a compound V; and then cyclizing to obtain a compound VII, namely n-propyl-3-(4-methyl phenyl)-4-(4-methylsulfonyl phenyl)-2,5-dihydro-1H-2-pyrrolidone. The method disclosed by the invention comprises simple reaction steps and can be put into industrial production easily.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a synthesis method of Erecoxib. Background technique [0002] Erecoxib is a highly selective COX-2 inhibitor. It mainly inhibits COX-2, thereby inhibiting the production of inflammatory prostaglandins and suppressing inflammation. It less inhibits COX-1 and therefore has little effect on physiological protective functions. Based on this mechanism of action, Erecoxib can produce good anti-inflammatory and analgesic effects, causing only few side effects. Erecoxib is a non-steroidal anti-inflammatory analgesic drug used to relieve the pain symptoms of osteoarthritis. [0003] The prior art of Erecoxib has (CN 102206178 B), and its synthetic route is as follows: [0004] [0005] The synthetic route is long, the yield is too low, and bromine is used in the production process, which is highly toxic and harmful to the environment and human body. Contents of the invention [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/38
CPCC07D207/38
Inventor 赵孝杰刘远慧梁辉吕红超王超
Owner SHANDONG BOYUAN PHARM CO LTD
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