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Preparation method of esomeprazole sodium

A technology of esomeprazole sodium and benzimidazole is applied in the field of preparation of optically pure esomeprazole and can solve problems such as lack of

Inactive Publication Date: 2020-09-08
SUZHOU SIXTH PHARMA PLANT OF JIANGSU WUZHONG PHARMA GROUP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In summary, this area still lacks a kind of productive rate high, the preparation method of esomeprazole sodium with good optical selectivity

Method used

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  • Preparation method of esomeprazole sodium
  • Preparation method of esomeprazole sodium
  • Preparation method of esomeprazole sodium

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of embodiment 1S-omeprazole sodium

[0030] The basic process is as follows:

[0031]

[0032] Step 1 Preparation of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfur]-1H-benzimidazole

[0033] Add 2-mercapto-5-methoxy-1H-benzimidazole (62 g, 0.34 mol) and methanol (210 mL) into the reaction tank, and stir to dissolve. Add a 100ml aqueous solution of sodium hydroxide (28g, 0.7mol), and then dissolve 210ml of 2-chloromethyl-4-methoxyl-3,5-lutidine hydrochloride (70g, 0.32mol) within 10min The methanol solution was added dropwise to the reaction tank. After the dropwise addition, the stirring reaction was continued at 0-30° C. for 3-5 hours.

[0034] After the reaction is completed, the temperature of the reaction liquid is controlled at 89-92° C. and distilled to dryness. After the distillation is complete, add 200 mL of dichloromethane and stir to dissolve, then add 100 mL of purified water for washing. The dichloromethane layer was d...

Embodiment 2

[0039] The preparation of embodiment 2S-omeprazole sodium

[0040] The basic process is as follows:

[0041]

[0042] Step 1 Preparation of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfur]-1H-benzimidazole

[0043] Add 2-mercapto-5-methoxy-1H-benzimidazole (62 g, 0.34 mol) and methanol (210 mL) into the reaction tank, and stir to dissolve. Add a 100ml aqueous solution of sodium hydroxide (28g, 0.7mol), and then dissolve 210ml of 2-chloromethyl-4-methoxyl-3,5-lutidine hydrochloride (70g, 0.39mol) within 10min The methanol solution was added dropwise to the reaction tank. After the dropwise addition, the stirring reaction was continued at 0-30° C. for 3-5 hours.

[0044] After the reaction is completed, the temperature of the reaction liquid is controlled at 89-92° C. and distilled to dryness. After the distillation is complete, add 200 mL of dichloromethane and stir to dissolve, then add 100 mL of purified water for washing. The dichloromethane layer was d...

Embodiment 3

[0049] The preparation of embodiment 3 S-omeprazole sodium

[0050] The basic process is as follows:

[0051]

[0052] Step 1 Preparation of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfur]-1H-benzimidazole

[0053] Add 2-mercapto-5-methoxy-1H-benzimidazole (62 g, 0.34 mol) and methanol (210 mL) into the reaction tank, and stir to dissolve. Add a 100ml aqueous solution of sodium hydroxide (28g, 0.7mol), and then dissolve 210ml of 2-chloromethyl-4-methoxyl-3,5-lutidine hydrochloride (70g, 0.39mol) within 10min The methanol solution was added dropwise to the reaction tank. After the dropwise addition, the stirring reaction was continued at 0-30° C. for 3-5 hours.

[0054] After the reaction is completed, the temperature of the reaction liquid is controlled at 89-92° C. and distilled to dryness. After the distillation is complete, add 200 mL of dichloromethane and stir to dissolve, then add 100 mL of purified water for washing. The dichloromethane layer was ...

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Abstract

The invention provides a preparation method of esomeprazole sodium, specifically a preparation method of optically pure esomeprazole sodium. The preparation method comprises the step of preparing esomeprazole sodium by taking 2-mercapto-5-methoxy-1H-benzimidazole and 2-chloromethyl-4-methoxy-3,5-dimethyl pyridine hydrochloride as starting raw materials. The method provided by the invention has good selectivity, can obtain almost optically pure products, and is suitable for industrial production of esomeprazole sodium.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular, the invention provides a method for preparing optically pure esomeprazole. Background technique [0002] Esomeprazole, the s-optical isomer of omeprazole, is the world's first isomer proton pump inhibitor, which reduces gastric acid secretion by specifically inhibiting the proton pump of gastric parietal cells. A large number of clinical experiments and drug studies have confirmed that it can maintain gastric pH > 4 for a longer period of time, and has higher acid suppression efficiency. The curative effect is better than the previous two generations of proton pump inhibitors, and the individual differences are small. As a new generation of proton pump inhibitors, it has been widely used in clinical treatment of many acid-related diseases. Therefore, how to obtain esomeprazole sodium through a simple and feasible method and ensure the safety of esomeprazole sodium through preci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07B53/00
CPCC07B53/00C07B2200/07C07D401/12
Inventor 刘宝硕李海军武卫袁双沈玲查丹丹
Owner SUZHOU SIXTH PHARMA PLANT OF JIANGSU WUZHONG PHARMA GROUP
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