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Method for preparing fluticasone propionate

A kind of technology of fluticasone propionate, equation

Active Publication Date: 2008-02-20
湖南玉新药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The route of this method is relatively cumbersome, and at the same time, silver fluoride is used in the exchange of fluorine and iodine, which is expensive, easy to deliquesce, easy to decompose when exposed to light, and the final product yield is low and difficult to purify, which limits its use in indust

Method used

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  • Method for preparing fluticasone propionate
  • Method for preparing fluticasone propionate
  • Method for preparing fluticasone propionate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] S-(chloromethyl)-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-ketoandrost-1,4-diene-17β-thiocarboxylic acid Preparation of esters:

[0032] Add 6α, 9α-difluoro-11β-hydroxyl-16α-methyl-17α-propionyloxy-3-ketoandrost-1,4-diene-17β-thiocarboxylic acid in a 250mL three-neck flask (Fw: 468.55, 10.0g, 21.3mmol), DMF100mL, sodium bicarbonate (Fw: 84.01, 7.2g, 85.2mmol), then chlorobromomethane (Fw: 129.38, 11.0g, 85.2mmol) was added dropwise to the system at room temperature In 30min, the dropwise addition was completed, and then the system continued to stir and react at room temperature for 2h. After the reaction, the mixture in the system was poured into 500mL of water, a large amount of white solid was precipitated, filtered, the filter cake was fully washed with distilled water, and dried to obtain S-(chloromethyl)-6α,9α-difluoro-11β-hydroxyl-16α- Methyl-17α-propionyloxy-3-ketoandrost-1,4-diene-17β-thiocarboxylate (Fw: 517.03, 10.5 g, yield: 95%). HPLC conte...

Embodiment 2

[0034] S-(bromomethyl)-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-ketoandrost-1,4-diene-17β-thiocarboxylic acid Preparation of esters:

[0035] In a 250 mL three-necked flask, 100 mL of acetone and potassium carbonate (Fw: 138.21, 8.8 g, 63.9 mmol) were sequentially added, and then dibromomethane (Fw: 173.83, 14.8 g, 85.2 mmol) was added to the system. 6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-ketoandrost-1,4-diene-17β-thiocarboxylic acid (Fw: 468.55, 10.0g, 21.3mmol) was dissolved in 50mL of acetone, and was added dropwise to the system at room temperature, and the dropwise addition was completed in about 30min, and then the system was stirred and reacted at room temperature for 4h. Warming to reflux for 1h. After the reaction was completed, the system was cooled to room temperature, most of the solvent was evaporated under reduced pressure, the mixture was poured into 300mL water, a large amount of white solid was precipitated, filtered, the fi...

Embodiment 3

[0037] S-(fluoromethyl)-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-ketoandrost-1,4-diene-17β-thiocarboxylic acid Preparation of esters:

[0038] Anhydrous tetrabutylammonium fluoride (Fw: 261.46; 5.07g; 19.4mmol) was successively added into a 100mL dry three-necked flask, followed by [Bmim][BF 4] 20.0mL was added to the system and stirred for 5min. The S-(chloromethyl)-6α,9α-difluoro-11β-hydroxyl-16α-methyl-17α-propionyloxy-3-ketoandrost-1,4-diene- 17β-thiocarboxylic acid (Fw: 517.03, 5.0 g, 9.7 mmol) was added to the system, and then 50 mL of anhydrous acetonitrile was added to the system. The system was heated to reflux for 15h. After the reaction was completed, the system was cooled to room temperature, most of the solvent was evaporated under reduced pressure, the mixture was poured into 150mL water, a large amount of white solid was precipitated, filtered, the filter cake was washed with distilled water, dried, and then recrystallized from acetone to obta...

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Abstract

The invention discloses a preparation method of fluticasone propionate, 6 Alpha, 9 Alpha- difluoro-ll Beta-hydroxide radical-16 Alpha-methyl-17 Alpha- propionyloxy-3-androsterone-1, 4-diene-17 Beta- thiocarboxylic acid is put into solvent to be reacted with monobromomethane when alkali exists, then the products from the reaction are reacted with tetraalkyl fluorizate ammonium salt or M+F- when ion liquid and solvent exist, finally the target products are collected from the reaction products. The method of the invention has simple operation, high yield, low cost and easy disposal after reaction, thereby having good industrial production prospect.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a novel synthesis method for preparing fluticasone propionate. Background technique [0002] English common name of fluticasone propionate: Fluticasone Propionate; chemical name: S-(fluoromethyl)-6α, 9α-difluoro-11β-hydroxyl-16α-methyl-17α-propionyloxy-3-ketone Androst-1,4-diene-17β-thiocarboxylate. [0003] Fluticasone propionate is a topically acting corticosteroid with potent anti-inflammatory activity. When it acts locally on the nasal mucosa, no systemic effects have been detected, implying minimal hypothalamic-pituitary-adrenal inhibition. It is mainly used to treat bronchial stenosis and inflammation. [0004] At present, existing technology, such as U.S. Patent US4335121, provides a kind of method for preparing fluticasone propionate, [0005] The route of this method is relatively cumbersome, and at the same time, silver fluoride is used in the exchange of fluorine an...

Claims

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Application Information

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IPC IPC(8): C07J3/00
Inventor 申玉良刘喜荣谢来宾何辉贤
Owner 湖南玉新药业有限公司
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