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Synthetic method and application of pantoprazole sodium

A technology of pantoprazole sodium and a synthesis method, applied in the field of pharmaceutical synthesis, can solve the problems of difficult purification of intermediates and products, short technological process, low solubility, etc., and achieves improved raw material utilization, shortened technological process, simplified Effects of Synthesis Steps

Pending Publication Date: 2021-07-27
HAINAN JINRUI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the process flow of this method is short, the raw materials used are salt substances, which have low solubility in organic solvents, and there are more three wastes produced in the post-treatment process, making it difficult to purify intermediates and products

Method used

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  • Synthetic method and application of pantoprazole sodium
  • Synthetic method and application of pantoprazole sodium
  • Synthetic method and application of pantoprazole sodium

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A kind of synthetic method of embodiment 1 pantoprazole sodium A1

[0028] The present embodiment provides a kind of synthetic method of pantoprazole sodium A1, and its synthetic method comprises the following steps:

[0029] 1) Weigh 21.6g of 5-difluoromethoxy-2-sulfanyl-1H-benzimidazole into 100ml of dichloromethane, add 38g of 40% peracetic acid, and keep stirring at room temperature for 1h to carry out the sulfnylation reaction , TLC monitors the reaction, and the disappearance of the raw material point is the end of the reaction. The reaction solution is concentrated to an oily state at 30°C under reduced pressure to obtain 21.3g of intermediate M1 (yield is 81%), and its reaction formula is:

[0030]

[0031] 2) Weigh 21.3g of intermediate M1 and 18.9g of ((3,4-dimethoxypyridin-2-yl)methyl)boronic acid dissolved in 150ml of tetrahydrofuran, stir to dissolve, continue stirring and add 12.7g of sodium carbonate, Replace the air in the reaction vessel with nitrog...

Embodiment 2

[0033] A kind of synthetic method of pantoprazole sodium A2 of embodiment 2

[0034] The present embodiment provides a kind of synthetic method of pantoprazole sodium A2, and its synthetic method comprises the following steps:

[0035] 1) Weigh 21.6g of 5-difluoromethoxy-2-sulfanyl-1H-benzimidazole into 100ml of dichloromethane, add 38g of 40% peracetic acid, and keep stirring at room temperature for 1h to carry out the sulfonylation reaction. TLC monitors the reaction, and the disappearance of the raw material point is the end of the reaction. The reaction solution is concentrated under reduced pressure at 30°C to an oily state to obtain 21g of intermediate M2 (yield is 80%), and its reaction formula is:

[0036]

[0037] 2) Dissolve 21g of intermediate M2 and 18.9g ((3,4-dimethoxypyridin-2-yl)methyl)boronic acid in 150ml 1,4-dioxane, stir to dissolve, keep stirring and Add 21.6g of potassium carbonate, replace the air in the reaction vessel with nitrogen for three times,...

Embodiment 3

[0039] A kind of synthetic method of pantoprazole sodium A3 of embodiment 3

[0040] The present embodiment provides a kind of synthetic method of pantoprazole sodium A3, and its synthetic method comprises the following steps:

[0041] 1) Weigh 21.6g of 5-difluoromethoxy-2-sulfanyl-1H-benzimidazole into 100ml of dichloromethane, add 38g of 40% peracetic acid, and keep stirring at room temperature for 1h to carry out the sulfonylation reaction. TLC monitors the reaction, and the disappearance of the raw material point is the end of the reaction. The reaction solution is concentrated under reduced pressure at 30°C to an oily state to obtain 20.4g of intermediate M3 (yield is 79%), and its reaction formula is:

[0042]

[0043] 2) Weigh 20.4g of intermediate M3 and 22.7g of ((3,4-dimethoxypyridin-2-yl)methyl)boronic acid and dissolve in 150ml of 1,4-dioxane, stir to dissolve, keep stirring and Add 37.5g of cesium carbonate, replace the air in the reaction vessel with nitrogen...

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Abstract

The invention belongs to the field of medicine synthesis, and discloses a synthesis method and application of pantoprazole sodium. The pantoprazole sodium is synthesized by the following steps: firstly carrying out sulfinylation on 5-difluoromethoxy-2-sulfenyl-1H-benzimidazole, and then carrying out Suzuki reaction on the 5-difluoromethoxy-2-sulfenyl-1H-benzimidazole and ((3, 4-dimethoxypyridine-2-yl) methyl) boric acid. According to the invention, the synthesis method of pantoprazole sodium provided by the invention can effectively improve the utilization rate of raw materials, improve the yield of intermediates and further reduce the production cost; the purification process of the synthesized intermediate and the final product in the synthesis method is simple, and the technological process is further shortened; and the synthesis method provided by the invention is suitable for synthesizing pantoprazole sodium, and the synthesized pantoprazole sodium is used for preparing a pantoprazole sodium injection.

Description

Technical field [0001] The invention belongs to the field of drug synthesis and relates to a drug synthesis method and application for gastrointestinal ulcers, specifically a synthesis method and application of pantoprazole sodium. Background technique [0002] Pantoprazole Sodium, chemical name: 5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridyl)-methyl]sulfinyl]-1H - Benzimidazole sodium monohydrate is a safe and effective drug for the treatment of peptic ulcers and bleeding caused by acute gastric mucosal lesions. It has a high cure rate for peptic ulcers and reflux esophagitis. Its powder for injection was first successfully developed by Byk Gulden Pharmaceuticals in Germany (now renamed Takeda Pharmaceuticals) and was first launched in South Africa in October 1994 under the trade name of Pantoprol. [0003] Chinese patent CN201310025427.2 describes a production method of a pharmaceutical composition of pantoprazole sodium. The pharmaceutical composition contains pantoprazo...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61K9/00
CPCC07D401/12A61K9/0019
Inventor 潘淑华王进宇王寿春
Owner HAINAN JINRUI PHARMA
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