Tauroursodeoxycholic acid synthesis method

A technology of tauroursodeoxycholic acid and tauroursodeoxycholic acid, which is applied in the field of synthesis of tauroursodeoxycholic acid, can solve the problems of high cost of raw materials and troublesome separation methods, and achieve low cost and easy Simple and controllable effect of industrialization and purification process

Inactive Publication Date: 2015-08-19
GUANGZHOU YINGYU PHARMA TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above method has the problems of troublesome separation method and high cost of raw materials.

Method used

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  • Tauroursodeoxycholic acid synthesis method

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preparation example Construction

[0022] A kind of synthetic method of tauroursodeoxycholic acid, the concrete processing step that it comprises is as follows:

[0023] (1) Dissolve chenodeoxycholic acid in an organic solvent, control the reaction temperature between 2-6°C, add N-hydroxybutanediimide or N-hydroxyphthalimide, stir, and then add Condensing agent and catalyst 4-dimethylaminopyridine, stirring for 0.5-2h, adding 3% sodium taurate aqueous solution and triethylamine to the reaction solution, continuing to stir the solution for 3-4h, adding HCl to adjust the pH of the reaction solution For 1-2, stir the reaction solution for 1-2h, concentrate the solvent, filter the precipitate with suction, wash with water until neutral, and dry at 70°C to obtain the crude taurochenodeoxycholic acid. Dissolve the crude taurochenodeoxycholic acid in acetone In a mixed solvent with water, heat until completely dissolved, cool to -3-3°C, stand for crystallization for 24-48h, filter, wash the filter cake with ice water,...

Embodiment 1

[0029] A kind of synthetic method of tauroursodeoxycholic acid, its concrete processing step is as follows:

[0030](1) Dissolve 19.6g (0.05mol) of chenodeoxycholic acid in 50ml of dioxane, control the reaction temperature between 0-5°C, add 6.9g (0.06mol) of N-hydroxybutanediimine 12.38 g (0.06 mol) of dicyclohexylcarbodiimide and 0.06 g of catalyst 4-dimethylaminopyridine (1% of the raw material) were added, stirred at 10°C for 2 hours, and then added to the reaction solution. Sodium sulfonate aqueous solution (250ml, 3%) was added dropwise to triethylamine (17ml, 0.06mol), and the solution was stirred for 2h, and HCl was added to adjust the pH of the reaction solution to 1-2, the reaction solution was stirred for 1h, the solvent was concentrated, and the The precipitate was filtered, washed with water until neutral, and dried at 70°C to obtain 19.5 g of crude taurochenodeoxycholic acid, with a yield of 78%. Taurochenodeoxycholic acid crude product 18g was dissolved in 20ml...

Embodiment 2

[0034] A kind of synthetic method of tauroursodeoxycholic acid, its concrete processing step is as follows:

[0035] (1) Dissolve 19.6g (0.05mol) of chenodeoxycholic acid in 50ml of dioxane, control the reaction temperature between 0-5°C, add 10.6g (0.06 mol), stir, then add 7.56g (0.06mol) of diisopropylcarbodiimide and 0.06g (1% of raw material) of catalyst 4-dimethylaminopyridine, maintain 10 ℃ and stir for 2h, in the reaction solution Add sodium taurate aqueous solution (250ml, 3%), then drop triethylamine (17ml, 0.06mol), continue to stir the solution for 2h, add HCl to adjust the pH of the reaction solution to 1-2, stir the reaction solution for 1h, concentrate Solvent, filter the precipitate with suction, wash with water until neutral, and dry at 70°C to obtain 19.0 g of crude taurochenodeoxycholic acid, with a yield of 76%;

[0036] (2) Add 12g (0.024mol) of taurochenodeoxycholic acid into 360ml of dioxane to dissolve, stir to dissolve, add 7.5g (0.048mol) of m-chloro...

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Abstract

The present invention discloses a tauroursodeoxycholic acid synthesis method, which comprises that chenodeoxycholic acid is adopted as a raw material, the chenodeoxycholic acid and N-hydroxy succinimide or N-hydroxyphthalimide are subjected to condensation under effects of a condensation agent and a catalyst to obtain an active ester, the active ester reacts with sodium taurocholate to obtain taurochenodeoxycholic acid, and further an oxidation reaction and a reduction reaction are performed to synthesize the tauroursodeoxycholic acid. The synthesis method of the present invention adopts the chenodeoxycholic acid as the raw material, and has characteristics of low cost, simple and controllable purification process, high target product purity, and easy industrialization.

Description

technical field [0001] The invention relates to the field of pharmaceutical raw materials, 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. [0003] T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
CPCC07J41/0066
Inventor 康健黄金昆邵敏陈新颖周树佳李心花汪晨霞
Owner GUANGZHOU YINGYU PHARMA TECH CO LTD
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