Synthesizing process of fluorine propionate ticasone

A technology for fluticasone propionate and crude fluticasone propionate, which is applied in the field of synthesis of fluticasone propionate, can solve the problems of high production cost, limited product quality and price, etc., and achieve high yield of finished product, short reaction route and high yield. high rate effect

Inactive Publication Date: 2007-07-18
江苏新海康制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing products rely on imports, so that the product qual

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment one production steps:

[0041] 1. Preparation of 6α, 9α-difluoro-11β, 17α-dihydroxy-16α-methyl-3-oxoandrost-1,4-diene-17β-carboxylic acid (code: compound I):

[0042] In a reaction bottle at 30-40°C, flumetasone (6α,9α-difluoro-11β,17α-21-trihydroxy-16α-methyl-3-pregna-1,4-diene-3, 20-diketone) 4.590g (11mmol) was dissolved in a mixed solvent of tetrahydrofuran (50ml) and methanol (50ml), and sodium periodate solution (9.58g, 44.8mol dissolved in 40ml of water) was added under stirring. Stir at 30-40°C for 6 hours, and track the completion of the reaction by thin-layer chromatography. After the reaction was completed, the organic solvent was recovered under reduced pressure, and the reaction solution was cooled and filtered to obtain a white crystalline solid, which was washed with water and dried under reduced pressure. 4.39 g of white crystalline solid, 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxandrost-1,4-diene-17β-carboxylic acid, yield 99% was ob...

Embodiment 2

[0051] Embodiment two production steps:

[0052] 1. Preparation of 6α, 9α-difluoro-11β, 17α-dihydroxy-16α-methyl-3-oxoandrost-1,4-diene-17β-carboxylic acid (code: compound I):

[0053] In a reaction bottle at 30-40°C, flumetasone (6α,9α-difluoro-11β,17α-21-trihydroxy-16α-methyl-3-pregna-1,4-diene-3, 20-diketone) 3.53g (8.6mmol) was dissolved in tetrahydrofuran (50ml) and methanol (50ml) mixed solvent, and periodic acid solution (6.60g, 34.4mmol dissolved in 60ml water) was added under stirring. Stir at 30-40°C for 6 hours, and track the completion of the reaction by thin-layer chromatography. After the reaction was completed, the organic solvent was recovered under reduced pressure, and the reaction solution was cooled and filtered to obtain a white crystalline solid, which was washed with water and dried under reduced pressure. 3.34 g of a white crystalline solid, namely 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxandrost-1,4-diene-17β-carboxylic acid, were obtained. Y...

Embodiment 3

[0062] Embodiment three production steps:

[0063] 1. Preparation of 6α, 9α-difluoro-11β, 17α-dihydroxy-16α-methyl-3-oxoandrost-1,4-diene-17β-carboxylic acid (code: compound I):

[0064] In a reaction bottle at 30-40°C, flumetasone (6α,9α-difluoro-11β,17α-21-trihydroxy-16α-methyl-3-pregna-1,4-diene-3, 20-diketone) 3.98g (9.7mmol) was dissolved in a mixed solvent of tetrahydrofuran (50ml) and methanol (50ml), added catalyst base, exposed to the air, stirred at 30-40°C for 3-4 days, and used a thin layer Chromatography followed the reaction to completion. After the reaction was completed, the organic solvent was recovered under reduced pressure, and the reaction solution was cooled and filtered to obtain a white crystalline solid, which was washed with water and dried under reduced pressure. 3.78 g of a white crystalline solid, namely 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxandrost-1,4-diene-17β-carboxylic acid, were obtained. Yield 98.6%. [[α] D 20 +64.0° (c=0.01 ...

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Abstract

The present invention relates to new technological process of converting carboxylic acid into thiocarboxylic acid, and is especially synthesis process of fluticasone acetate. The present invention prepares fluticasone acetate with medicinal level flumethasone as initial material and through one of six technological paths, and has the advantages of short reaction path, high yield, simple reaction condition, high product purity, low cost, etc.

Description

technical field [0001] The invention discloses a process route for preparing fluticasone propionate from cheap flumetasone, and relates to a new process for converting carboxylic acid into thiocarboxylic acid. Background technique [0002] Fluticasone propionate is used to treat mild, moderate and severe chronic asthma. It can prevent and treat seasonal allergic rhinitis (including hay fever) and perennial allergic rhinitis. It is the drug of choice for the treatment of chronic asthma. Existing products rely on imports, so that the product quality and price are limited, and the production cost remains high. Contents of the invention [0003] The object of the present invention is to invent the synthetic method of the fluticasone propionate that takes flumetasone as starting material. [0004] The present invention scheme has six kinds: [0005] One includes the following steps: [0006] 1) Dissolve flumetasone in tetrahydrofuran and methanol solvent, and react with sodi...

Claims

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Application Information

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IPC IPC(8): C07J3/00C07J75/00
Inventor 秦国儒
Owner 江苏新海康制药有限公司
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