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Vonoprazan fumarate single crystal, preparation method and uses thereof

A vonoprazan fumaric acid single crystal technology, applied in organic chemistry methods, digestive system, organic chemistry, etc., can solve the problems of high impurity content and difficult separation, and achieve good reproducibility, good shape, and guaranteed The effect of accuracy

Inactive Publication Date: 2017-03-08
WATERSTONE PHARMA WUHAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the vonoprazan fumarate at this stage has high impurity content and is not easy to separate

Method used

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  • Vonoprazan fumarate single crystal, preparation method and uses thereof
  • Vonoprazan fumarate single crystal, preparation method and uses thereof
  • Vonoprazan fumarate single crystal, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Synthesis of Crude Vonorazan Fumarate

[0030] According to the following two steps to synthesize the crude product of vonoprazan fumarate, the specific synthesis method is as follows:

[0031] Step 1 Synthesis of 5-(2-fluorophenyl)-1-[(pyridin-3-yl)sulfonyl]-1H-pyrrole-3-carbaldehyde, the specific method is as follows:

[0032] Add acetonitrile (50ml), 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (10g), 4-dimethylaminopyridine (1.3g) and N,N-diisopropyl to the reaction flask at room temperature Ethylamine (13 g), stirred at 40° C. to 50° C. for 2 hours, followed by TLC to complete the reaction. Add 1 mol / L hydrochloric acid solution to the reaction system to adjust the pH=4-5, then add water (60ml) and stir. Filtration and drying gave 5-(2-fluorophenyl)-1-[(pyridin-3-yl)sulfonyl]-1H-pyrrole-3-carbaldehyde (15.5 g, yellow solid).

[0033] Step 2 Synthesize the crude product of vonoprazan fumarate, the specific method is as follows:

[0034] Methanol (40ml)...

Embodiment 2

[0036] Example 2 Preparation of Vonoprazan Fumarate Single Crystal

[0037] Weigh 1.0 g of the vonoprazan fumaric acid crude product obtained in Example 1, add the crystallization solvent methanol / water (5 ml / 5 ml) mixed solution, raise the temperature to 60 ° C ~ 70 ° C, and wait until the product is completely dissolved. In the evaporation method, the temperature was set at 25° C., and cultured for 5 days, colorless crystals were precipitated, and observed under a microscope, the crystals were vonoprazan fumaric acid single crystals, and the HPLC purity was 99.5%.

Embodiment 3

[0038] Example 3 Preparation of Vonoprazan Fumarate Single Crystal

[0039] Weigh 1.0 g of the vonoprazan fumaric acid crude product obtained in Example 1, add the crystallization solvent methanol / water (4 ml / 16 ml) mixed solution, raise the temperature to 60° C. to 70° C., and wait until the product is completely dissolved. In the evaporation method, the temperature was set at 30° C., and cultured for 10 days, a colorless crystal was precipitated, and observed under a microscope, the crystal was vonoprazan fumaric acid single crystal, and the HPLC purity was 99.6%.

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Abstract

The present invention relates to a vonoprazan fumarate single crystal, a preparation method and uses thereof. According to the present invention, the X-ray powder diffraction results show that the characteristic peaks are showed at the 2[theta] of 11.4, 12.3, 13.5, 15.1, 15.3, 16.9, 18.6, 20.4, 20.7, 22.4 and 25.1, the obtained single crystal is not reported, and other determination results show that the crystal structure belongs to a monoclinic system, the space group is P2(1) / c, the intracellular molecular number Z is 4m the single crystal is a colorless orthorhombic crystal at a room temperature, the morphology is good, and the HPLC purity is up to more than 99.5%; and with the preparation method, the vonoprazan fumarate and other impurities are well separated, and the good reproducibility is good.

Description

technical field [0001] The invention belongs to the field of chemical synthesis. Specifically, the invention relates to a single crystal of vonoprazan fumarate and its preparation method and application. Background technique [0002] Oral anti-gastric acid new drug developed by Takeda Pharmaceutical Co., Ltd.—Vonoprazan fumarate (compound shown in formula I) belongs to potassium ion (K + ) A new class of gastric acid secretion inhibitors, competitive acid blockers (P-CAB), can inhibit the last step of gastric acid secretion in parietal cells by inhibiting K + to H + -K + - The combination of ATPase (proton pump) terminates the secretion of gastric acid in advance, and has a strong and long-lasting inhibitory effect on gastric acid secretion. [0003] [0004] Takeda Pharmaceutical has submitted a new drug application (NDA) for vonoprazan fumarate to the Japanese Ministry of Labor, Health and Welfare (MHLW) on February 28, 2014, and obtained vonoprazan fumarate in Japan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A61P1/04A61P31/04
CPCC07B2200/13C07D401/12
Inventor 陈继伟秦志平孟源崔健钱丽娜
Owner WATERSTONE PHARMA WUHAN
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