Highly pure fluticasone propionate preparation method

A kind of fluticasone propionate, high-purity technology, applied in the field of organic chemical synthesis

Inactive Publication Date: 2014-08-27
WUHAN NUOAN PHARMACY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Patents such as US4335121, WO01 / 62722 (US2002 / 0133032), CN200610161627[1].0, CN200710044880[1].2 and other patents all describe the synthesis of fluticasone propionate, but none of the patents relates to the detailed description of the purification of each step of the intermediate Thereby obtain the method for high-purity fluticasone propionate, the purity of the crude product processed according to the present invention can reach more than 99%, a single main impurity is no more than 0.2%, and a single recrystallization can reach the limit requirement that a single main impurity is no more than 0.1%. The rate is 80% to 98%

Method used

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  • Highly pure fluticasone propionate preparation method
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  • Highly pure fluticasone propionate preparation method

Examples

Experimental program
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example 1

[0029] Add 5 g (12.61 mmol) of the first crude product solid oxidized with flumetasone into the flask, add 0.9 g of sodium hydroxide solution dissolved in 150 ml of water, stir at room temperature for 2 hours to dissolve, filter under reduced pressure, and use a small amount of Wash the filter cake and filter bottle with water, combine the filtrate and lotion, add 50ml of methanol to the flask, stir at room temperature for 20 minutes, add dropwise 2M hydrochloric acid to make the pH of the solution 2 to 4, stir for 2 hours, and filter under reduced pressure. The filter cake was washed with water until neutral, and dried at 70°C to obtain 4.9 g with an HPLC purity of 99.7%.

example 2

[0031] Put 5 grams (11.05 mmol) of the crude solid in the second step into the flask, add 0.8 grams of sodium hydroxide solution dissolved in 200 ml of water, stir at room temperature for 2 hours to dissolve, filter under reduced pressure, and wash the filter cake and Filter the flask, combine the filtrate and washing liquid, add 80ml of methanol to the flask, stir at room temperature for 20 minutes, add dropwise 2M hydrochloric acid to make the pH of the solution 2 to 4, stir for 2 hours, filter under reduced pressure, and wash the filter cake with water until Neutral, dried at 70°C to obtain 5.0 g of solid with HPLC purity of 99.6%.

example 3

[0033] Put 5 grams of the crude product in the third step into the reaction flask, add 150ml of ethyl acetate, stir at room temperature to dissolve, then extract with 5×50ml of 3% aqueous sodium hydroxide solution, then wash with 2×50ml of water, and wash with anhydrous sodium sulfate Dry, concentrate under reduced pressure to dryness, add water and stir at room temperature, disperse the solid, filter under reduced pressure, and dry at 75°C to obtain 4.8 g with an HPLC purity of 99.4%.

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Abstract

The invention discloses a highly pure S-fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-17alpha-propionooxo-3-androsterone-1,4-diene-17beta-benzothiodiazole (fluticasone propionate) preparation method. The method is characterized in that various highly-pure intermediates of fluticasone propionate are prepared in order to obtain highly pure fluticasone propionate; and post-treatment and purification of the intermediates obtained in each step are carried out in order to obtain the highly pure fluticasone propionate. The method has the advantages of simple operation, high purity and low quantity of impurities, common and cheap reagents, and suitableness for the large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to the high-purity preparation of intermediates in each step of fluticasone propionate, thereby preparing a method for high-purity fluticasone propionate. Background technique [0002] Patents such as US4335121, WO01 / 62722 (US2002 / 0133032), CN200610161627[1].0, CN200710044880[1].2 and other patents all describe the synthesis of fluticasone propionate, but none of the patents relates to the detailed description of the purification of each step of the intermediate Thereby obtain the method for high-purity fluticasone propionate, the purity of the crude product processed according to the present invention can reach more than 99%, a single main impurity is no more than 0.2%, and a single recrystallization can reach the limit requirement that a single main impurity is no more than 0.1%. The rate is between 80% and 98%. Contents of the invention [0003] The problem to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J31/00
Inventor 徐金喜
Owner WUHAN NUOAN PHARMACY
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