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Preparation method of high-purity etravirine

An ingavirine and high-purity technology is applied in the field of preparation of high-purity ingavirin, which can solve the problems of affecting product quality and low purity of ingavirin, and achieve the effects of ingenious conception and simple process

Active Publication Date: 2012-10-31
SICHUAN BAILI PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

We have found through experiments that the purity of ingaverine obtained by post-treatment of this method is not high, and it contains impurities such as triethylamine, histamine dihydrochloride, glutaric anhydride, glutaric acid, etc., which seriously affect the quality of its products

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Add 2.98g of crude ingaverine and 50mL of methanol into a flask, add 25mL of triethylamine dropwise with stirring until the solid dissolves, then slowly add 360mL of ethyl acetate, cool down to 0°C, stir and crystallize for 2h, filter , the filter cake was washed with 100 mL of ethyl acetate, the filter cake was collected, and dried under reduced pressure at 60° C. for 5 hours to obtain 1.94 g of a white solid.

[0031] Experimental results: The purity of HPLC is 99.91%, no histamine peak, single impurity is less than 0.1%, m.p.194.6~195.0℃.

Embodiment 2

[0032] Example 2: Add 2.98g of crude ingaverine and 50mL of DMSO into a flask, add 25mL of triethylamine dropwise with stirring until the solid dissolves, then slowly add 360mL of ethyl acetate, cool down to 0°C, stir and crystallize for 2h, filter, The filter cake was washed with 100 mL of ethyl acetate, the filter cake was collected, and dried under reduced pressure at 60° C. for 5 hours to obtain 1.82 g of a white solid.

[0033] Experimental results: HPLC detected its purity as 99.81%, no histamine peak, single impurity less than 0.1%, m.p.194.4~195.0℃

Embodiment 3

[0034] Example 3: Add 2.98g of crude ingaverine, 25mL of DMSO and 25mL of methanol into a flask, add 25mL of triethylamine dropwise under stirring until the solid dissolves, then slowly add 360mL of ethyl acetate, cool down to 0°C and stir for crystallization for 2h , filtered, the filter cake was washed with 100 mL of ethyl acetate, the filter cake was collected, and dried under reduced pressure at 60° C. for 5 hours to obtain 2.1 g of a white solid.

[0035] Experimental results: HPLC detected that its purity was 99.77%, without histamine peak, and a single impurity was less than 0.1%. m.p.194.5~195.0℃

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Abstract

The invention discloses a preparation method of high-purity etravirine, which comprises the following steps: A. dissolving a crude etravirine product in a solvent at -40-150 DEG C; B. adding a poor solvent into the mixture obtained in the step A at -40-150 DEG C; C. precipitating an etravirine solid from the mixture obtained in the step B at -80-150 DEG C; and D. separating the etravirine solid obtained in the step C to obtain the required high-purity etravirine. The preparation method disclosed by the invention has the advantages of ingenious concept and simple process; and the purity of the prepared etravirine is up to higher than 99.9%, and the prepared etravirine conforms to various medicine standards.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy and relates to a preparation method of high-purity ingavirin. Background technique [0002] Ingavirin (ingavirin, chemical name: 5-((2-(1 hydrogen-imidazol-4-yl) ethyl) amino)-5-oxopentanoic acid) is an effective drug against influenza virus and adenovirus infection. drug. [0003] Application No. WO9901103 first mentioned the compound 5-((2-(1 hydrogen-imidazol-4-yl) ethyl) amino)-5-oxopentanoic acid), i.e. Ingavirin, against virus Have better effect. The literature T. A. Kromova, G. A. Zheltukhina. Pharmaceutical Chemistry Journal. Vol. 39, No. 3, 2005 reported the synthesis method of ingaverine: using histamine dihydrochloride as raw material, DMF as solvent, reacting with glutaric anhydride to obtain Ingavelin. We have found through experiments that the ingaverine obtained by the post-treatment of this method is not high in purity, and contains impurities such as triethylamine, h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64
Inventor 吴勇朱义海俐刘威加余永国
Owner SICHUAN BAILI PHARM CO LTD
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