Method for synthesizing tauroursodeoxycholic acid

A technology of tauroursodeoxycholic acid and tauroursodeoxycholic acid, which is applied in the field of synthesis of tauroursodeoxycholic acid, can solve the problems of expensive and unfavorable tauroursodeoxycholic acid, and achieve Low cost, environment friendly, high yield effect

Inactive Publication Date: 2016-06-22
四川新功生物科技集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the ursodeoxycholic acid that this method needs is a kind of raw material that clinical supply exceeds demand, and the ...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Take 100g of chenodeoxycholic acid and dissolve it in 250mL of acetone with stirring, add 39mL of triethylamine, cool in an ice bath until the temperature is 0-5°C, gradually add 24.2mL of ethyl chloroformate, after the dripping is completed, gradually raise the temperature to room temperature and stir After 2 hours, the precipitate was removed by filtration, and the filtrate was obtained as a mixed acid anhydride solution;

[0028] Stir the above mixed acid anhydride solution, drop into taurine solution, the taurine solution is to take 38.3g taurine and dissolve in 255mL1N sodium hydroxide solution; stir at room temperature for 2 hours, after the reaction is over, concentrate under reduced pressure to recover acetone , adding 250mL of water to the residual solution to adjust the pH of the solution to 2-4, and a large amount of white solid was precipitated by filtration; after drying, 114.5g of taurochenodeoxycholic acid was obtained. Two-step yield 90%

[0029] Take 5...

Embodiment 2

[0032] Take 100g of chenodeoxycholic acid and dissolve it in 250mL of acetone with stirring, add 39mL of triethylamine, cool in an ice bath until the temperature is 0-2°C, gradually add 27.4mL of propyl chloroformate dropwise, after the dropwise, gradually warm up to room temperature, After stirring for 2 hours, the precipitate was removed by filtration to obtain the filtrate, namely the mixed acid anhydride solution.

[0033] Stir the above mixed acid anhydride solution, drop into taurine solution, the taurine solution is to take 38.3g of taurine and dissolve in 255mL of 1N sodium hydroxide solution; stir at room temperature for 3 hours, after the reaction is over, concentrate under reduced pressure to recover acetone , adding 250mL of water to the residual solution to adjust the pH of the solution to 3-4, and a large amount of white solid was precipitated by filtration; after drying, 115.2g of taurochenodeoxycholic acid was obtained. Two-step yield 91%

[0034] Take 50 g of...

Embodiment 3

[0037] Take 100g of chenodeoxycholic acid and dissolve it in 250mL of acetone with stirring, add 39mL of triethylamine, cool in an ice bath until the temperature is 0-1°C, gradually drop in 34mL of butyl chloroformate, after the drop is completed, gradually warm up to room temperature, and stir After 2 hours, the precipitate was removed by filtration to obtain the filtrate, namely the mixed anhydride solution.

[0038] Stir the above mixed acid anhydride solution, drop into taurine solution, the taurine solution is to take 38.3g taurine and dissolve in 255mL1N sodium hydroxide solution; stir at room temperature for 2 hours, after the reaction is over, concentrate under reduced pressure to recover acetone , adding 250mL of water to the residual solution to adjust the pH of the solution to 3-4, and a large amount of white solid was precipitated by filtration; after drying, 113.9g of taurochenodeoxycholic acid was obtained. The two-step yield is about 90%;

[0039] Take 50g of t...

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PUM

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Abstract

The invention discloses a method for synthesizing tauroursodeoxycholic acid. The method comprises the steps that chenodeoxycholic acid is adopted as an initial raw material, reacting is carried out under the action of alkyl chloroformate to obtain mixed anhydride, then mixed anhydride and taurine react to obtain taurochenodeoxycholic acid, and taurochenodeoxycholic acid is sequentially subjected to an oxidation reaction and a hydrogenation reaction to obtain tauroursodeoxycholic acid. The method is low in cost, easy to operate, environmentally friendly and suitable for industrial production. Tauroursodeoxycholic acid prepared through the method is high in purity and yield.

Description

technical field [0001] The invention relates to the technical field of medicine manufacturing, in particular to a method for synthesizing tauroursodeoxycholic acid. Background technique [0002] Tauroursodeoxycholic acid, the chemical name is 3α, 7β-dihydroxycholanoyl-N-taurine (TUDCA), is a conjugated bile acid discovered from bear bile in 1902, and was discovered in 1991 by Italian Beth Developed by Dida Pharmaceutical Factory, and listed in Italy for the first time. Tauroursodeoxycholic acid has antispasmodic, anticonvulsant, anti-inflammatory and gallstone-dissolving effects, and is mainly used clinically for the treatment of gallbladder cholesterol stones, primary sclerosing cholangitis, primary biliary cirrhosis and chronic hepatitis C virus infection. hepatitis etc. Clinical studies have shown that compared with ursodeoxycholic acid, tauroursodeoxycholic acid has faster dissolution rate and higher total dissolution rate, and has no obvious adverse reactions. [000...

Claims

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Application Information

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IPC IPC(8): C07J41/00
CPCC07J41/0061
Inventor 占伟赖永新谢建张海林
Owner 四川新功生物科技集团有限公司
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