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Preparation method of vonoprazan fumarate

A technology of vonoprazan fumarate and fluorophenyl, which is applied in the field of preparation of pharmaceutical compounds, can solve problems such as difficulty in removal, affecting product quality, and low purity of vonoprazan fumarate

Active Publication Date: 2015-08-26
ZHEJIANG CHENGYI PAHRMACEUTICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0027] The disadvantage of this preparation method is that the obtained vonoprazan fumarate has low purity, and the impurities include N,N-dimethylacetamide, 5-(2-fluorophenyl)-1-(pyridine-3 -ylsulfonyl)-1H-pyrrole-3-carbaldehyde and pyridine-3-sulfonyl chloride, especially 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3 - The content of formaldehyde and pyridine-3-sulfonyl chloride is relatively high, and it is difficult to remove. Although the content of vonoprazan fumarate obtained by the above-mentioned prior art can be greater than 98.5%, the content of the above-mentioned two related impurities is greater than 0.3% , affecting the quality of the product, in order to meet higher standard requirements, the present invention has carried out the improvement on the method

Method used

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  • Preparation method of vonoprazan fumarate
  • Preparation method of vonoprazan fumarate
  • Preparation method of vonoprazan fumarate

Examples

Experimental program
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Effect test

Embodiment 1

[0059] Preparation of Vonorazan Fumarate

[0060] step 1,

[0061] Add 10g of 5-(2-fluorophenyl)pyrrole-3-carbaldehyde, 1.3g of 4-dimethylaminopyridine, 7.5g of triethylamine and acetonitrile (40ml) into the reaction flask, stir at room temperature; 11.3g of pyridine-3-sulfonyl chloride Add acetonitrile (10ml) dropwise to the reaction flask; heat to 45°C for 1.5 hours; cool to 25°C, add water (30ml); adjust the pH of the system to 4-5 with concentrated hydrochloric acid, and stir at 25°C for half an hour; Cool to 0-5°C and stir for 1 hour; filter, rinse the filter cake with acetonitrile:water (1:2) 30ml, then rinse with water (20ml) twice, and dry under vacuum at 50°C to obtain 5-(2-fluorobenzene Base)-1-(pyridine-3-sulfonyl)pyrrole-3-carbaldehyde 15g;

[0062] step 2

[0063] Dissolve 10 g of 5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)pyrrole-3-carbaldehyde in methanol (70ml); under nitrogen protection and stirring at room temperature, methylamine methanol solution (15g, 30...

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Abstract

The invention relates to preparation of a medical compound, and in particular relates to a preparation method of a stomach-acid resistant medicine vonoprazan fumarate. A synthetic route of the compound is as shown in the specification.

Description

Technical field: [0001] The invention relates to the preparation of a pharmaceutical compound, in particular to a preparation method of an antigastric acid medicine vonoprazan fumarate. Background technique: [0002] Vonoprazan fumarate, the chemical structure is as follows: [0003] [0004] English name: Vonoprazan fumarate (TAK-438) [0005] Chemical name: 5-(2-fluorophenyl)-N-methyl-1-(3-pyridylsulfonyl)-1H-pyrrole-3-methylamine fumarate This drug belongs to potassium ion competitive acid inhibition It is a new class of inhibitors of Potassium-competitive acid blocker (P-CAB), which has a strong and long-lasting inhibitory effect on gastric acid secretion. The combination of ATPase (proton pump) also has an early termination effect on gastric acid secretion. [0006] The drug was developed by Takeda Corporation of Japan and is used for erosive esophagitis, gastric ulcer, duodenal ulcer, and Helicobacter pylori eradication. [0007] The Chinese patents related to t...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 茆利平
Owner ZHEJIANG CHENGYI PAHRMACEUTICAL
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