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Preparation method of ursodeoxycholic acid

A technology for ursodeoxycholic acid and oxidation reaction, which is applied in the field of preparation of ursodeoxycholic acid, can solve the problems of high price of ursodeoxycholic acid and high requirements on preparation technology, and achieves low cost, stable quality and product purity. high effect

Inactive Publication Date: 2013-09-25
EAST CHINA UNIV OF SCI & TECH
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Problems solved by technology

The price of ursodeoxycholic acid is expensive, it can be seen that its industrial production has higher requirements on the preparation process

Method used

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  • Preparation method of ursodeoxycholic acid
  • Preparation method of ursodeoxycholic acid

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preparation example Construction

[0015] The preparation of ursodeoxycholic acid among the present invention is realized through the following steps:

[0016] The specific steps are:

[0017] (1) N-bromosuccinimide (NBS) was used to selectively oxidize the hydroxyl group at the C-7 position of chenodeoxycholic acid.

[0018] (2) Methyl monooxide was catalyzed by concentrated hydrochloric acid in methanol solution.

[0019] (3) Using NaBH 4 / CeCl 3 The system reduces the carbonyl group to increase the α / β selectivity.

[0020] (4) The hydrolysis reaction is carried out in a sodium hydroxide methanol solution with a concentration of 1 mol / L.

[0021] The organic solvent described in the step (1) of the present invention is a mixed solvent of acetone and water, the molar ratio of the oxidizing agent and chenodeoxycholic acid is optimally 1:1.6, the reaction temperature is 25° C., and the reaction time is 2 hours.

[0022] The organic solvent described in the step (2) of the present invention is methanol, whi...

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Abstract

The invention provides a preparation method of ursodeoxycholic acid. Commercial available chenodeoxycholic acid is taken as raw materials, the ursodeoxycholic acid is obtained by four steps including selective oxidation, esterification, deoxidation and hydrolyzation, and the total yield is 85.7%. In a mixture of acetone and water, NBS is used for selective oxidation of hydroxy at C- 7 bit of the chenodeoxycholic acid, and the selective oxidation possesses excellent selectivity and high yield. NaBH14 / CeC13 may be used to deoxidize carbonyl at C-7 bit into hydroxy, and the ratio of alpha / beta is as high as 5 / 95.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis. Specifically relates to a preparation method of ursodeoxycholic acid. Background technique [0002] Since the news that Fujian Guizhentang Pharmaceutical Co., Ltd. (hereinafter referred to as Fujian Guizhentang) intends to list on the GEM, the technology of bear bile powder has come into people's attention. The main component of bear bile is tauroursodeoxycholic acid, which is formed by combining ursodeoxycholic acid and taurine. [0003] Ursodeoxycholic acid is the only drug approved by the FDA for the treatment of primary biliary cirrhosis. Ursodeoxycholic acid (UDCA) is a hydrophilic cholic acid that exists in normal human bile, accounting for 3% of the total cholic acid in the human body. Initial studies have shown that ursodeoxycholic acid has the functions of changing the composition of bile acid pool, protecting liver cell membrane, regulating immunity, anti-oxidation, and in...

Claims

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Application Information

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IPC IPC(8): C07J9/00
Inventor 杨先金张晓奇
Owner EAST CHINA UNIV OF SCI & TECH
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