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Preparation method of R-budesonide

A single, isomer technology, applied in the field of preparation of adrenal cortex hormone drugs, can solve the problems of unfavorable target products, high production costs, and high toxicity of operators, and achieve good separation effect and high yield.

Inactive Publication Date: 2014-04-16
CHENGDU YILUKANG MEDICAL TECH & SERVICE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The method uses prednisone acetate as the starting material, undergoes esterification with trifluoroacetic anhydride, hydrogenation with sodium borohydride, heat elimination, oxidation of osmium tetroxide, condensation and hydrolysis with 75% hydrofluoric acid to obtain R-budesonide , its total yield is only about 5%; and in the reaction process, expensive trifluoroacetic anhydride is used to increase the production cost, and osmium tetroxide is more poisonous to operators; in the hydrogenation process with sodium borohydride, it may Produces 11-α or β hydroxyl groups, which is unfavorable to the target product of synthesis

Method used

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  • Preparation method of R-budesonide
  • Preparation method of R-budesonide
  • Preparation method of R-budesonide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Put 100 g of the prepared compound of formula VII (R / S=85 / 15) into a reaction flask with mechanical stirring, add 800 ml of methanol, and reflux to dissolve completely. Then it was cooled to room temperature and filtered to obtain 89.0 g of VII.

[0038] R isomer (VIIa): 95.2%; S isomer (VIIb): 4.8%.

Embodiment 2

[0040] Put 100 g of the purified compound of formula VII (R / S=95 / 5) into a reaction flask with mechanical stirring, add 800 ml of methanol, and reflux to dissolve completely. Then it was cooled to room temperature and filtered to obtain 92.0 g of VII.

[0041] R isomer (VIIa): 98.9%; S isomer (VIIb): 1.1%.

Embodiment 3

[0043] Put 100 g of the refined and purified compound of formula VII (R / S=99 / 1) into a reaction flask with mechanical stirring, add 800 ml of methanol, and reflux to dissolve completely. Then it was cooled to room temperature and filtered to obtain 93.6g of VII.

[0044] R isomer (VIIa): 99.6%; S isomer (VIIb): 0.4%.

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Abstract

The invention discloses a preparation method of an adrenal cortex hormone medicament and particularly relates to a preparation method of a high-purity R-budesonide isomer. According to the method disclosed by the invention, prednisolone is used as an original raw material and the budesonide acetic ester is prepared by cyclization, ring opening, esterification, elimination, oxidation, cyclization and hydrolysis. The method disclosed by the invention has a simple process and high yield and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of adrenocortical hormone drugs, in particular to a preparation method of high-purity budesonide R isomer. Background technique [0002] Budesonide is a glucocorticoid with highly effective local anti-inflammatory effect developed by AB Bofors in Sweden. Budesonide is a racemate composed of two isomers 22R and 22S at the C-22 position in a ratio of approximately 1:1. It is clinically used topically to treat skin or respiratory symptoms caused by inflammation and allergies (such as skin diseases, asthma and rhinitis), etc. [0003] Dexbudesonide (R isomer) belongs to adrenal corticosteroid drugs, and is a single isomer at the C-22 position of budesonide prepared by chemical synthesis. Its local anti-inflammatory activity (rat auricle swelling method) is 1.4 to 1.7 times that of budesonide, 1.6 to 2 times that of levobudesonide (S isomer), and 13 times that of dexamethasone; the local glucocorticoid effect ...

Claims

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Application Information

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IPC IPC(8): C07J71/00
Inventor 骆均勇陶长戈
Owner CHENGDU YILUKANG MEDICAL TECH & SERVICE
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