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Crystal form alpha of vonoprazan fumarate and the preparation method thereof

A technology for vornorazan fumarate and crystal form, which is applied in the preparation of the new crystal form, in the field of vornorazan fumarate crystal form α, can solve the problem of difficult to remove impurities, difficult to take into account yield and purity, Problems such as the purification method of vonoprazan fumarate are not provided to achieve the effects of high purity, easy industrial preparation and good controllability

Inactive Publication Date: 2017-01-11
YICHANG HUMANWELL PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because there are many impurities in vonoprazan fumarate that are difficult to remove, and the prior art does not provide an efficient purification method for vonoprazan fumarate, it is difficult to balance yield and purity

Method used

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  • Crystal form alpha of vonoprazan fumarate and the preparation method thereof
  • Crystal form alpha of vonoprazan fumarate and the preparation method thereof
  • Crystal form alpha of vonoprazan fumarate and the preparation method thereof

Examples

Experimental program
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Effect test

reference example

[0025] Refer to the method of CN201080018114.9 Example 5 to prepare the crude product of vonoprazan fumarate

[0026] To a nitrogen purged flask were added N,N-dimethylacetamide (108 ml) and sodium borohydride (3.06 g, 81.74 mmol), and the mixture was dissolved (Solution A). Into another nitrogen-purged flask was added 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (60.0 g, 181.64 mmol) and methanol ( 300ml), then a 40% solution of methylamine in methanol (18.34g, 236.13mmol) was added dropwise at room temperature. The mixture was further stirred for 30 minutes at an internal temperature of 20-30°C. The internal temperature was cooled to -10°C, and then the previously prepared solution A was added dropwise at the internal temperature not exceeding 0°C. N,N-Dimethylacetamide (12 ml) was added, and the mixture was stirred at an internal temperature of -10-0°C for 1 hour. 1N HCl (360 ml) was added dropwise at an internal temperature not exceeding 20°C, a...

Embodiment 1

[0028] Preparation of Vonorazan Fumarate Form α

[0029] Add 10 g of vonoprazan fumaric acid crude product to 100 g of ethylene glycol monomethyl ether, heat to 60 ° C to dissolve, then add 300 g of purified water, stir and react at room temperature for 1 hour, filter, wash the filter cake with purified water, and dry to obtain White solid crystal 9.2g, yield 92%, HPLC purity 99.92%; After determination, its X-RPD spectrum is as follows figure 1 As shown, its DSC-TGA spectrum is as figure 2 shown.

Embodiment 2

[0031] Preparation of Vonorazan Fumarate Form α

[0032] Add 10 g of vonoprazan fumaric acid crude product to 30 g of ethylene glycol monomethyl ether, heat to reflux to dissolve, then add 90 g of purified water, stir and react at room temperature for 1 hour, filter, wash the filter cake with purified water, and dry to obtain white 9.3 g of solid crystals, yield 93%, HPLC purity 99.89%.

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Abstract

The invention belongs to the technical field of pharmaceutical chemistry, in particular to a crystal form alpha of vonoprazan fumarate and the preparation method of the new crystal form. The crystal form has high purity as well as favorable chemical stability and crystal form stability; the crystal form can be prepared through mass production, of which the process is simple and the cost is low, so the potential applications are fantastic.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a crystal form α of vonoprazan fumarate and a method for preparing the new crystal form. Background technique [0002] Vonoprazan fumarate, chemical name 1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylformazan Amine fumarate has a chemical structure as shown in formula I. Vonoprazan fumarate is a new type of proton pump inhibitor, which can be used as a therapeutic drug for acid secretion inhibitors, tumor diseases or autoimmune diseases. As proton pump inhibitors such as omeprazole can effectively inhibit gastric acid secretion, but the instability in acidic conditions and the effect caused by metabolic enzyme polymorphisms and drug interactions are scattered. Excellent stability under certain conditions, so as to show more excellent therapeutic effects on peptic ulcer, reflux esophagitis, etc. [0003] [0004] I [0005] P...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12C07B2200/13
Inventor 不公告发明人
Owner YICHANG HUMANWELL PHARMA
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