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Synthesis method of chenodeoxycholic acid

A technology of chenodeoxycholic acid and synthesis method, which is applied in the synthesis field of chenodeoxycholic acid, can solve the problems of incompatibility, low yield, complicated extraction and preparation process and the like

Inactive Publication Date: 2006-11-29
SHENYANG SUNSHINE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] Chenodeoxycholic acid is mainly extracted from poultry or animal bile. The traditional extraction and preparation process is complicated, the yield is low, and a large amount of unsafe organic solvents are used (Pharmaceutical Industry, 1987, 18 (9), 416; Applied Technology, 1998 , 4:9-10; US Patent, 4,331,607; US Patent, 4,163,017) cannot adapt to the requirements of modern industry

Method used

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  • Synthesis method of chenodeoxycholic acid

Examples

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Embodiment Construction

[0025] (1) Preparation of cholic acid ester

[0026] 50 grams of cholic acid was weighed, dissolved in 150 ml of anhydrous methanol, added with 5 ml of concentrated hydrochloric acid, refluxed for 30 minutes, slowly cooled and placed in a freezer, the yield of methyl cholic acid was 95%.

[0027] (2) Preparation of methyl diacetyl-12α-hydroxy-cholate

[0028] Weigh 50 grams of methyl cholic acid, dissolve it in 100 ml of refined pyridine, make it completely dissolved, add 100 ml of acetic anhydride under stirring, react at room temperature for 3 to 4 hours, pour it into 500 ml of water, there is a white precipitate, put it in. Put it in the refrigerator and filter the next day to obtain methyl diacetyl-12α-hydroxy-cholate with a yield of 40%.

[0029] (3) Preparation of 3α,7α-diacetoxy-12-oxo-methylcholanoic acid

[0030] Weigh 25 g of the crude product obtained above, dissolve it in 250 ml of acetone, filter to remove insoluble matter, slowly add Jones reagent under stirrin...

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Abstract

A process for synthesizing chenodeoxycholic acid includes such steps as preparing the ester used for cholic acid, preparing diacetyl-12a-hydroxy-methyl cholate, preparing 3a, 7a-diacetyloxy-12-oxy-methyl cholanic acid, preparing 12-oxy- chenodeoxycholic acid, preparing chenodeoxycholic acid, and purifying.

Description

technical field [0001] The invention relates to a method for synthesizing chenodeoxycholic acid (3α, 7α-dihydroxy-5β-cholanoic acid), in particular to a method for synthesizing chenodeoxycholic acid by chemical methods. Background technique [0002] Chenodeoxycholic acid (3α, 7α-dihydroxy-5β-cholanoic acid) ChenodeoxycholioAcid (CDCA) is a drug for the treatment of gallstones. It was first discovered in goose bile in 1848 and named chenodeoxycholic acid in 1924. [0003] Chenodeoxycholic acid has the functions of relieving asthma, reducing phlegm, antitussive and anti-inflammatory, and its choleretic effect is particularly significant. It reduces cholesterol absorption and synthesis, and reduces cholesterol in bile, thereby inhibiting the formation of cholesterol stones and promoting It dissolves and can effectively reduce cholesterol saturation. [0004] Chenodeoxycholic acid can also be used as an intermediate for the preparation of ursodeoxycholic acid (3α, 7β-dihydroxy...

Claims

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Application Information

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IPC IPC(8): C07J9/00
Inventor 孟艳秋张力
Owner SHENYANG SUNSHINE PHARMA
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