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Large-scale preparation method for high-purity amide compound crystal form B

A large-scale preparation, high-purity technology, applied in organic chemistry methods, separation/purification of carboxylic acid amides, organic chemistry, etc.

Inactive Publication Date: 2017-11-10
NANJING KEFEI PINGSHENGHUI PHARMA CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is currently no suitable route to obtain high-purity, crystal form B 5-(2,5-dimethylphenoxy)- N The method of -(2-(4-hydroxyphenyl)-2-oxoethyl)-2,2-dimethylpentanamide objectively needs to find a method suitable for the industrial production of crystal form B drug substances

Method used

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  • Large-scale preparation method for high-purity amide compound crystal form B
  • Large-scale preparation method for high-purity amide compound crystal form B
  • Large-scale preparation method for high-purity amide compound crystal form B

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Experimental program
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Effect test

Embodiment 1

[0017] The formula I compound 5-(2,5-dimethylphenoxy)- N -(2-(4-Hydroxyphenyl)-2-oxoethyl)-2,2-dimethylpentanamide crude product (A+B mixed crystal, HPLC>99%, max. 0.1%~0.15% ) 395g and toluene 3L were added to a 5L three-necked flask, stirred, and heated to reflux. Divide the water, stir for 3 hours, cool down to 54°C naturally, add 0.1g of B seed crystals, continue to cool down to 0°C, keep warm for 0.5h, filter, and vacuum-dry the filter cake at 40°C to obtain 379g of crystal form B samples, HPLC: 99.83% , the maximum simple impurity <0.05%.

Embodiment 2

[0019] The formula I compound 5-(2,5-dimethylphenoxy)- N -(2-(4-Hydroxyphenyl)-2-oxoethyl)-2,2-dimethylpentanamide crude product (Mixed crystal A, HPLC>99%, maximum single hetero0.1%~0.15%) 98g 1. Add 500mL of toluene into a 1L three-necked flask, stir, and heat up to reflux. Divide the water, stir for 5 hours, cool down to 60°C naturally, add 0.1g of B seed crystals, continue to cool down to 0°C, keep warm for 3h, filter, and vacuum-dry the filter cake at 30°C to obtain 95g of crystal form B samples, HPLC: 99.78%, The maximum simple impurity <0.05%.

Embodiment 3

[0021] The formula I compound 5-(2,5-dimethylphenoxy)- N -(2-(4-Hydroxyphenyl)-2-oxoethyl)-2,2-dimethylpentanamide crude product (A+B mixed crystal, HPLC>99%, max. 0.1%~0.15% ) 87g and acetonitrile 1300mL were added to a 5L three-necked flask, stirred, and heated to 70°C. Stir for 4 hours, cool down to 60°C naturally, add 0.1g of B seed crystals, continue to cool down to 0°C, keep warm for 5h, filter, and vacuum-dry the filter cake at 40°C to obtain 69g of crystal form B samples, HPLC: 99.64%, maximum single hetero <0.05%.

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Abstract

The invention relates to a large-scale preparation method for a high-purity crystal form B, i.e., 5-(2,5-dimethylphenoxy)-N-(2-(4-hydroxylphenyl)-2-oxoethyl)-2,2-dimethyl valeramide (represented by a formula I shown in the description). According to the obtained sample, the HPLC purity is higher than 99%, and the maximum single impurity content is lower than 0.05%.

Description

technical field [0001] The invention relates to a large-scale preparation of high-purity 5-(2,5-dimethylphenoxy)-N-(2-(4-hydroxyphenyl)-2-oxoethyl)-2,2- A method for crystal form B of dimethylvaleramide. Background technique [0002] WO2012175049 reports an amide compound that regulates blood lipids and prevents gallstones in vivo. The compound can not only reduce the level of triglyceride in hyperlipidemic model animals, but also has a good effect of reducing cholesterol and low-density lipoprotein. On the golden hamster stone model, it has the effect of preventing and curing gallstones. Wherein the compound 5-(2,5-dimethylphenoxy)- N -(2-(4-hydroxyphenyl)-2-oxoethyl)-2,2-dimethylpentanamide (formula I) can reduce total cholesterol and triglyceride at the same time, with few side effects, and can treat Hyperlipidemia, atherosclerosis and other cardiovascular and cerebrovascular diseases and gallstones, and less toxic, has a good market development prospect. [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/24C07C235/18
CPCC07B2200/13C07C231/24C07C235/18
Inventor 秦引林年四昀苏梅
Owner NANJING KEFEI PINGSHENGHUI PHARMA CO LTD