Process for preparing tauroursodeoxycholic acid hydrate

A technology of deoxycholic acid and taurine, which is applied in the direction of steroids and organic chemistry, can solve the problems of waste of resources and energy consumption, impact on product quality, long reaction process, etc., and achieve the goal of producing less three wastes Effect

Inactive Publication Date: 2012-07-11
ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The process of producing taurine ursodeoxycholic acid hydrate product by the above-mentioned process is due to the long reaction process, resulting in a large increase in the use of organic solvents and the discharge of environmentally unfriendly waste, and the impact of chiral isomers due to side reactions Product quality, waste of resources and energy consumption caused by non-purpose products

Method used

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  • Process for preparing tauroursodeoxycholic acid hydrate
  • Process for preparing tauroursodeoxycholic acid hydrate
  • Process for preparing tauroursodeoxycholic acid hydrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Add 25.0 g of chenodeoxycholic acid and 150 ml of acetone into a 1000 ml three-necked reaction flask, and stir evenly at 15°C; then add 8.9 ml of triethylamine, and stir at high speed for 60 min to make it into a solid suspension. Cool down to -10°C, add 6.5ml of ethyl chloroformate to react for 2 hours; after the reaction is completed, remove the insoluble matter by filtration to obtain the mother liquor of chenodeoxy mixed anhydride.

[0037] (2) 10.4g of sodium taurine, 0.5g of sodium hydroxide and 18.6ml of pure water were stirred and dissolved; after being cooled to room temperature, they were put into the obtained chenodeoxy mixed anhydride mother liquor of step (1), and stirred at a high speed at room temperature for 2 ~5h; after the reaction, adjust the pH value to 1~2, stir at a medium speed for 30min; slowly add 500ml of acetone, drop the temperature to 0~5°C after the dropwise addition, stir at a low speed for 2~5h; filter it, and wash it with a small amou...

Embodiment 2

[0041] 1) Add 25.0 g of chenodeoxycholic acid and 400 ml of dioxane to a 1000 ml three-necked reaction flask and stir at 15°C until uniform, then add 8.2 g of 4-dimethylaminopyridine and stir at high speed for 60 min. Cool down to -5°C, add 8.2ml of isobutyl chloroformate and react for 2h. After the reaction was completed, the insolubles were removed by filtration to obtain the mixed acid anhydride mother liquor.

[0042]2) 11.4g of potassium taurine, 0.5g of potassium hydroxide, and 18.6ml of pure water were stirred and dissolved, cooled to room temperature, and put into the mixed acid anhydride solution, and reacted with high-speed stirring at room temperature for 2 to 5 hours. After the reaction, adjust the pH value to 2-3, stir for 60 minutes, slowly add 500ml of dioxane, drop the temperature to 0-5°C and stir at a low speed for 2-5 hours, filter, wash with a small amount of frozen dioxane, and dry to obtain cattle 30.1 g of chenodeoxycholic acid sulfonate product.

[00...

Embodiment 3

[0046] 1) Add 25.0 g of chenodeoxycholic acid and 200 ml of cyclohexanone to a 1000 ml three-necked reaction flask and stir evenly at 15°C, then add 8.9 ml of pyridine and stir at high speed for 60 min to form a solid suspension. Cool down to -15°C, add 8.7ml of isobutyl chloroformate to react for 2h. After the reaction was completed, the insolubles were removed by filtration to obtain the mixed acid anhydride mother liquor.

[0047] 2) 10.3g of sodium taurine, 0.5g of barium hydroxide, and 18.6ml of pure water were stirred and dissolved, cooled to room temperature and then put into the mixed acid anhydride solution, and reacted with high-speed stirring at room temperature for 2 to 5 hours. After the reaction, adjust the pH value to 0.5-1, stir for 60 minutes, slowly add 600ml of cyclohexanone, drop the temperature to 0-5°C and stir at a low speed for 2-5 hours, filter, wash with a small amount of frozen cyclohexanone, and dry to obtain goose taurine Deoxycholic acid product ...

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Abstract

The invention discloses a process for preparing a tauroursodeoxycholic acid hydrate, which comprises the steps of reacting chenodeoxycholic acid with acyl chloride compound to obtain chenodeoxycholic acid mixed anhydride in an anhydrous organic solvent with ketone groups and in presence of an acid scavenger; reacting the chenodeoxycholic acid mixed anhydride with igepon with water under an alkaling condition to obtain taurine chenodeoxycholic acid; reacting the taurine chenodeoxycholic acid with an oxidizing agent in presence of water under an alkaling condition to obtain taurine-7-ketone group gallstone acid; leading hydrogen into the taurine-7- ketone group gallstone acid under the condition of chiral catalyst and alkalinity and maintaining a certain pressure and temperature for a hydrogenation reduction reaction to obtain the tauroursodeoxycholic acid; mingling the tauroursodeoxycholic acid with the mixed organic solvent to obtain the tauroursodeoxycholic acid hydrate. The tauroursodeoxycholic acid hydrate has the advantages of being low in cost, safe in process, good in production quality, and applicable to industrialization.

Description

technical field [0001] The invention relates to a preparation method of taurine ursodeoxycholic acid hydrate. Background technique [0002] Tauroursodeoxycholic acid is mainly used clinically for the treatment of gallbladder cholesterol stones, primary sclerosing cholangitis, primary biliary cirrhosis and chronic hepatitis C virus. Clinical studies have shown that compared with ursodeoxycholic acid, taurine ursodeoxycholic acid has a faster rate of dissolving stones, a higher total dissolution rate, and no obvious adverse reactions. [0003] Compared with ursodeoxycholic acid, taurine ursodeoxycholic acid hydrate has the same medicinal effect, relatively stable thermodynamics, better hydrophilicity and less moisture absorption, and is suitable for the production of various formulations. [0004] The production of tauroursodeoxycholic acid hydrate by the existing process is mainly to obtain chenodeoxycholic acid from cholic acid or taurine chenodeoxycholic acid, and then obt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
Inventor 黄凌张和平秦和平沈惠冰黄文军刘遗松
Owner ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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