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Synthesis method of parecoxib sodium

A technology of parecoxib sodium and its synthesis method, which is applied in the direction of organic chemistry, can solve the problems of increased reaction cycle, long reaction time, source limitation, etc., and achieves the effects of less environmental pollution, convenient operation, and low cost

Inactive Publication Date: 2015-05-06
CHENGDU CLIMB PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this route is that the starting material 1-phenylacetone is more expensive, and the source of benzonitrile N oxide is limited. At the same time, the first step reaction time is too long, which will increase the reaction cycle
Therefore, the scale of industrialization of this route has certain limitations

Method used

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  • Synthesis method of parecoxib sodium
  • Synthesis method of parecoxib sodium
  • Synthesis method of parecoxib sodium

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: a kind of synthetic method of parecoxib sodium, it comprises the following steps:

[0025] S1. Sulfonation reaction: Add 15kg of dichloromethane and 4.5kg of 5-methyl-3,4-diphenylisoxazole into the reaction kettle, control the reaction temperature below 30°C, add 13.5kg of chlorosulfonic acid dropwise, and add After completion, heat up to 40-50°C, reflux for 3 hours, take a sample every 0.5 hours and monitor it with TLC (EA:PE=1:3), and react until the TLC monitoring 5-methyl-3,4-diphenylisoxazole spot disappears , that is, the reaction of 5-methyl-3,4-diphenylisoxazole is complete, the reaction solution is cooled to room temperature, and added dropwise to 18kg of ice water, and the temperature is controlled below 20°C. After the dropwise addition, 15kg of dichloromethane Extraction and liquid separation, add 10kg of dichloromethane to the aqueous phase for extraction, and combine the organic phases to obtain the parecoxib sodium intermediate I dichloromet...

Embodiment 2

[0029] Embodiment 2: a kind of synthetic method of parecoxib sodium, it comprises the following steps:

[0030] S1. Sulfonation reaction: add 15kg of dichloromethane and 4.5kg of 5-methyl-3,4-diphenylisoxazole into the reaction kettle, control the reaction temperature below 30°C, add 22.5kg of chlorosulfonic acid dropwise, After the addition, raise the temperature to 40-50°C, reflux for 8 hours, take samples every 0.5 hours and monitor them with TLC (EA:PE=1:3), and monitor the spots of 5-methyl-3,4-diphenylisoxazole by TLC after reaction disappear, that is, the reaction of 5-methyl-3,4-diphenylisoxazole is complete, the reaction solution is cooled to room temperature, added dropwise to 18kg ice water, and the temperature is controlled below 20°C. After the dropwise addition, 15kg dichloro Methane extraction and liquid separation, adding 10 kg of dichloromethane to the aqueous phase for extraction, and combining the organic phases to obtain the parecoxib sodium intermediate I ...

Embodiment 3

[0034] Embodiment 3: a kind of synthetic method of parecoxib sodium, it comprises the following steps:

[0035] S1. Sulfonation reaction: Add 15kg of dichloromethane and 4.5kg of 5-methyl-3,4-diphenylisoxazole into the reaction kettle, control the reaction temperature below 30°C, add 18kg of chlorosulfonic acid dropwise, add dropwise After completion, heat up to 40-50°C, reflux for 5 hours, take a sample every 0.5 hours and monitor it once with TLC (EA:PE=1:3), and react until the TLC monitoring 5-methyl-3,4-diphenylisoxazole spot disappears , that is, the reaction of 5-methyl-3,4-diphenylisoxazole is complete, the reaction solution is cooled to room temperature, and added dropwise to 18kg of ice water, and the temperature is controlled below 20°C. After the dropwise addition, 15kg of dichloromethane Extraction and liquid separation, add 10kg of dichloromethane to the aqueous phase for extraction, and combine the organic phases to obtain the parecoxib sodium intermediate I dic...

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Abstract

The invention discloses a synthesis method of parecoxib sodium, and belongs to the technical field of medicines. The target product, namely parecoxib sodium, is synthesized from 5-methyl-3,4-diphenyl isoxazole which is taken as an initial raw material through sulfonation, amination, propionylation and salt forming reaction. The invention has the following beneficial effects: the method disclosed by the invention has the advantages of simple synthesis route, mild reaction conditions, convenient operation, low cost, low environmental pollution and high yield, and is applicable to large-scale factory production.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a method for synthesizing parecoxib sodium. Background technique [0002] The English name of Parecoxib sodium is Parecoxib Sodium, and its chemical name is N-[[4-(5-methyl-3-phenyl-4-isoxazolyl)phenyl]sulfonyl]propionamide sodium salt. Molecular formula is C 19 h 17 N 2 o 4 SNa, the molecular weight is 392.41, the CAS accession number is 198470-85-8, and the structural formula is as shown in formula I: [0003] [0004] Parecoxib Sodium (Parecoxib Na) is an analgesic, and it is the main component of Parecoxib Sodium Injection for the short-term treatment of pain after surgery. It is the first specific ring that can be injected intravenously and intramuscularly As an inhibitor of oxidase-2, parecoxib sodium has the characteristics of significant postoperative analgesic effect, wide range of medical treatment, small side effects, high market value, and easy storage. The ...

Claims

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Application Information

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IPC IPC(8): C07D261/08
CPCC07D261/08
Inventor 蒋明勇刘芍利叶丁林蓉莹
Owner CHENGDU CLIMB PHARMA TECH
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