Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A chemical-enzymatic method for preparing ursodeoxycholic acid

A technology for the preparation of ursodeoxycholic acid by enzymatic method, which is applied in the field of chemical-enzymatic preparation of ursodeoxycholic acid, which can solve the problems of low yield and high pollution, and achieve the effect of high purity, good activity and wide application

Active Publication Date: 2021-11-16
BONTAC BIO ENG SHENZHEN
View PDF9 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, the synthesis of UDCA from HDCA is a chemical method, and the synthesis steps require about 7 steps, and the yield is low; in addition, chemical methods often use highly polluting reagents, such as pyridinium dichromate

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A chemical-enzymatic method for preparing ursodeoxycholic acid
  • A chemical-enzymatic method for preparing ursodeoxycholic acid
  • A chemical-enzymatic method for preparing ursodeoxycholic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1 A method for preparing ursodeoxycholic acid by chemical-enzymatic method, comprising:

[0050] (1) Dissolve 10 g of hyodeoxycholic acid in 200 mL of dichloromethane, continue to add 60 mL of DMSO, stir until dissolved, add 7.50 g of 2-iodoxybenzoic acid and stir for 4 hours at room temperature, then filter, and concentrate the filtrate to about 40 mL under reduced pressure. Slowly add 200 mL of deionized water dropwise to obtain 6-oxo-lithocholic acid, which is then dried. The above product was further recrystallized, including dissolving the 6-oxo-lithocholic acid obtained in the above process in 50 mL of methanol and filtering, slowly dripping 100 mL of deionized water into the filtrate, filtering, and drying to obtain 9.18 g of the product 6-oxo-lithocholic acid after recrystallization.

[0051] (2) Dissolve the above 9.18g 6-oxo-lithocholic acid and 8.50g p-toluenesulfonyl hydrazide in a mixed solution of 200mL methanol and 2mL acetic acid, stir at roo...

Embodiment 2

[0055] Embodiment 2 A chemical-enzymatic method for preparing ursodeoxycholic acid, comprising:

[0056] (1) Dissolve 10g of hyodeoxycholic acid in 200mL of dichloromethane, continue to add 40mL of DMSO, stir until dissolved, add 8.2g of 2-iodoxybenzoic acid and stir for 3 hours at room temperature, then filter, and concentrate the filtrate to about 40mL under reduced pressure. Slowly add 200 mL of deionized water dropwise to obtain 6-oxo-lithocholic acid, which is then dried. The above product was further recrystallized, including dissolving the 6-oxo-lithocholic acid obtained in the above process in 50 mL of methanol and filtering, slowly dripping 100 mL of deionized water into the filtrate, filtering, and drying to obtain 9.05 g of the product 6-oxo-lithocholic acid after recrystallization.

[0057] (2) Dissolve the above-mentioned 9.05g 6-oxo-lithocholic acid and 8.2g p-toluenesulfonylhydrazide in 200mL ethanol and 2mL acetic acid solution, stir at room temperature, then ...

Embodiment 3

[0061] Embodiment three A chemical-enzymatic method for preparing ursodeoxycholic acid, comprising:

[0062] (1) Dissolve 10g of hyodeoxycholic acid in 150mL of acetone, stir with 50mL of DMSO until dissolved, add 7.50g of 2-iodoxybenzoic acid and stir for 3 hours at room temperature, then filter, concentrate the filtrate under reduced pressure to about 40mL, slowly drop into 150mL of deionized Water, precipitated to obtain 6-oxo-lithocholic acid, and dried. The above product was further recrystallized, including dissolving the 6-oxo-lithocholic acid obtained in the above process in 50 mL of methanol and filtering, slowly dripping 100 mL of deionized water into the filtrate, filtering, and drying to obtain 9.25 g of the product 6-oxo-lithocholic acid after recrystallization.

[0063] (2) Dissolve the above 9.25g 6-oxo-lithocholic acid and 10.0g p-toluenesulfonylhydrazide in a mixed solution of 200mL ethanol and 4mL acetic acid, stir at room temperature, then add 100mL 80% sod...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

A chemical-enzymatic method for preparing ursodeoxycholic acid, comprising adding hyodeoxycholic acid into the first organic solvent, and oxidizing under the action of an oxidizing agent to obtain 6-oxo-lithocholic acid to obtain 6-oxo- Lithocholic acid; the 6-oxo-lithocholic acid and the sulfonyl hydrazide derivative are added to the second organic solvent to make the 6-oxo-lithocholic acid and the sulfonyl hydrazide derivative generate affinity Nucleoaddition-elimination reaction to obtain hydrazone compounds; in an inert gas environment, use a reducing agent to reduce the hydrazone compounds to obtain lithocholic acid; carry out the lithocholic acid under the catalysis of hydroxylase and coenzyme Hydroxylation reaction to obtain ursodeoxycholic acid. The method uses hyodeoxycholic acid as the initial raw material, and obtains ursodeoxycholic acid through a three-step chemical method and a one-step biological enzymatic method. The whole synthesis process has few steps, simple operation, high yield and low cost, and can be widely applied on an industrial scale Production.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a chemical-enzymatic method for preparing ursodeoxycholic acid. Background technique [0002] Ursodeoxycholic acid (UDCA), the molecular formula is C 24 h 40 o 4 , is the main component of traditional Chinese medicine bear bile, its chemical name is (3α, 7β)-dihydroxy-5β-cholanic acid, which is the 7β-hydroxyl epimer of chenodeoxycholic acid (Chenodeoxycholic acid, CDCA). UDCA has been mainly used in the treatment of gallstone disease. In recent years, foreign countries have reported the application of UDCA in the treatment of various acute and chronic liver diseases. New research shows that UDCA not only has a good curative effect on the treatment of primary biliary cirrhosis, primary sclerosing cholangitis, and chronic active hepatitis, but also can be used to treat chronic hepatitis and rejection after liver transplantation. Therefore, with the deepening of research, ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C12P33/06C07J9/00
CPCC07J9/005C12P33/06C07J9/00
Inventor 傅荣昭刘立辉江名刘玉凤
Owner BONTAC BIO ENG SHENZHEN
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com