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Synthesis method of esomeprazole sodium

A technology for esomeprazole sodium and omeprazole sodium is applied in the field of esomeprazole sodium synthesis, and can solve the problems of many impurities, high synthesis cost, low esomeprazole content, and the like, To achieve the effect of simple synthesis process, low cost and lower synthesis cost

Pending Publication Date: 2021-10-19
SICHUAN ZIREN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, esomeprazole is easy to obtain impurities during the preparation process, the impurities are many and high, the content of esomeprazole is low, and the synthesis cost is high

Method used

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  • Synthesis method of esomeprazole sodium
  • Synthesis method of esomeprazole sodium
  • Synthesis method of esomeprazole sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A kind of synthetic method of esomeprazole sodium, synthetic steps are as follows:

[0032] (1) preparation of omeprazole sulfide

[0033] 12kg of 5-methoxy-2-mercaptobenzimidazole was stirred in a mixed solution of ethanol (density 0.81g / ml, addition 46.8kg), sodium hydroxide solution (5.33kg sodium hydroxide, 14.4kg purified water) until Dissolve, add 14.79kg of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride after dissolving 5-methoxy-2-mercaptobenzimidazole, heat, stir and reflux until the end of the reaction, The reaction solution was obtained, wherein during the process of feeding and stirring, the temperature was controlled at 35° C., the reflux reaction time was 0.5 h, and after the reaction was completed, it was purified by crystallization of the organic phase.

[0034] Wherein, the organic phase is crystallized to be purified by adding the reaction liquid to the organic phase of ethyl acetate, adjusting the pH to 10 through sodium hydroxide soluti...

Embodiment 2

[0048] A kind of synthetic method of esomeprazole sodium, synthetic steps are as follows:

[0049] (1) preparation of omeprazole sulfide

[0050] 12kg of 5-methoxy-2-mercaptobenzimidazole was stirred in a mixed solution of ethanol (density 0.81g / ml, addition 46.8kg), sodium hydroxide solution (5.33kg sodium hydroxide, 14.4kg purified water) until Dissolve, add 14.79kg of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride after dissolving 5-methoxy-2-mercaptobenzimidazole, heat, stir and reflux until the end of the reaction, The reaction solution was obtained, wherein during the process of feeding and stirring, the temperature was controlled at 35° C., the reflux reaction time was 1.5 h, and after the reaction was completed, it was purified by crystallization of the organic phase.

[0051] Wherein, the organic phase is crystallized to be purified by adding the reaction solution to the organic phase of ethyl acetate, adjusting the pH to 11 through sodium hydroxide solu...

Embodiment 3

[0065] A kind of synthetic method of esomeprazole sodium, synthetic steps are as follows:

[0066] (1) preparation of omeprazole sulfide

[0067] 12kg of 5-methoxy-2-mercaptobenzimidazole was stirred in a mixed solution of ethanol (density 0.81g / ml, addition 46.8kg), sodium hydroxide solution (5.33kg sodium hydroxide, 14.4kg purified water) until Dissolve, add 14.79kg of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride after dissolving 5-methoxy-2-mercaptobenzimidazole, heat, stir and reflux until the end of the reaction, A reaction liquid was obtained, wherein during the process of feeding and stirring, the temperature was controlled at 35° C., the reaction time of reflux was 1 h, and after the reaction was completed, it was purified by crystallization of the organic phase.

[0068] Wherein, the organic phase is crystallized to be purified by adding the reaction liquid to the organic phase of ethyl acetate, adjusting the pH to 10 through sodium hydroxide solution ...

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Abstract

The invention discloses a synthesis method of esomeprazole sodium, and belongs to the field of organic synthesis. The method comprises the following steps: carrying out a heating reaction on 5-methoxy-2-mercaptobenzimidazole and 2-chloromethyl-3, 5-dimethyl-4-methoxypyridine hydrochloride in the presence of an ethanol-sodium hydroxide solution to obtain omeprazole thioether, adding alkali and carrying out a symmetric oxidation reaction to obtain a methyl isobutyl ketone solution of esomeprazole, and reacting with sodium hydroxide to obtain the esomeprazole sodium. According to the synthesis method, the raw material utilization rate is high, the content and variety of impurities are reduced, the extraction rate of the esomeprazole sodium is greatly increased, the yield can reach 75%, the purity is larger than 99%, the synthesis route is short, and the synthesis cost is greatly reduced.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing esomeprazole sodium. Background technique [0002] The main component of omeprazole sodium is esomeprazole, which can be specifically distributed on gastric mucosal cells after oral administration, specifically blocking gastric acid secretion, and has strong and long-lasting effects on excessive gastric acid secretion caused by various reasons. inhibitory effect. [0003] The main indications for esomeprazole are: (1) Peptic ulcer. Esomeprazole has a strong acid-suppressing effect, which can effectively reduce the erosion of gastric acid on the erosive surface of ulcers and protect the gastric mucosa. (2) Helicobacter pylori infection. Helicobacter pylori is the pathogenic factor of duodenal ulcer and gastric ulcer, and is the main cause of ulcer recurrence. Esomeprazole inhibits the activity of Helicobacter pylori. (3) Reflux esophagitis and gastro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 李昌华
Owner SICHUAN ZIREN PHARMA
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