Method for respectively recovering ursodesoxycholic acid and chenodeoxycholic acid from ursodesoxycholic acid waste mother liquor

A technology for ursodeoxycholic acid and chenodeoxycholic acid, which is applied in the field of recovering ursodeoxycholic acid and chenodeoxycholic acid respectively, can solve the problem of low yield of ursodeoxycholic acid, waste of active ingredients, and refining cost Advanced problems, to achieve the effect of easy large-scale industrial production, high recovery efficiency, and good product purity

Active Publication Date: 2012-11-07
苏州天绿生物制药有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the chemical synthesis method can only obtain the crude product of ursodeoxycholic acid after the reaction, which contains a variety of newly produced impurities. In order to obtain ursodeoxycholic acid with a single composition and meet the requirements of the Pharmacopoeia, the crude product must be refined, so After obtaining the fine ursodeoxycholic acid, a lot of waste mother liquor was produced. After analysis, it was found that the waste

Method used

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  • Method for respectively recovering ursodesoxycholic acid and chenodeoxycholic acid from ursodesoxycholic acid waste mother liquor
  • Method for respectively recovering ursodesoxycholic acid and chenodeoxycholic acid from ursodesoxycholic acid waste mother liquor

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Take 100g of the waste mother liquor refined by ursodeoxycholic acid, add 2L of pure water and 10g of sodium hydroxide, heat to 65°C and stir until dissolved, then add dilute hydrochloric acid with a concentration of 50% by mass to adjust the pH value to 8.0, The temperature was lowered to 25°C, and the solution was passed through ultrafiltration and nanofiltration membranes with a molecular weight cut-off of 10K to remove a large amount of impurities and color to obtain a clarified filtrate.

[0035] Add dilute hydrochloric acid with a mass percent concentration of 50% to the obtained filtrate, acidify to pH 3.0, continue stirring for 30 minutes, filter and dry to obtain total cholic acid solids including ursodeoxycholic acid and chenodeoxycholic acid.

[0036] Add 10 times the weight of total bile acid into sec-butanol and 20% of its weight into triethylamine, heat and reflux for 2 hours, then slowly cool down to about 20°C to obtain white ammonium ursodeoxycholic acid...

Embodiment 2

[0041] Take 200g of the waste mother liquor refined by ursodeoxycholic acid, add 2L of pure water and 20g of sodium hydroxide, heat to 65°C and stir until dissolved, add dilute hydrochloric acid with a concentration of 40% by mass to adjust the pH value to 7.0, and cool down to 25 ℃, the solution was passed through the ultrafiltration membrane and the nanofiltration membrane with a molecular weight cut-off of 3K to remove a large amount of impurities and color, and a clear filtrate was obtained.

[0042]Dilute hydrochloric acid with a concentration of 50% by mass was added to the obtained filtrate, acidified to a pH value of 2, filtered and dried to obtain total cholic acid solids including ursodeoxycholic acid and chenodeoxycholic acid.

[0043] The total bile acid was added into acetone and 20wt% diisopropylethylamine according to 15 times its weight, and after heating and refluxing for 3 hours, it began to slowly cool down to about 20°C, and a white ammonium ursodeoxycholic ...

Embodiment 3

[0048] Take 200g of the waste mother liquor refined by ursodeoxycholic acid, add 4L of pure water and 10g of sodium hydroxide, heat to 65°C and stir until dissolved, add dilute hydrochloric acid with a concentration of 60% by mass, adjust the pH value to 7.0, and cool down to At 25°C, pass the solution through an ultrafiltration membrane and a nanofiltration membrane with a molecular weight cut-off of 1K to remove a large amount of impurities and color to obtain a clear filtrate.

[0049] Dilute hydrochloric acid with a concentration of 50% by mass was added to the obtained filtrate, acidified to a pH value of 3.0, filtered and dried to obtain total cholic acid solids including ursodeoxycholic acid and chenodeoxycholic acid.

[0050] Add the total bile acid to ethyl acetate and 20wt% ethylenediamine according to 10 times its weight, heat and reflux for 2.5 hours, then slowly cool down to about 20°C to obtain white ammonium ursodeoxycholic acid precipitate, filter, The filter c...

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Abstract

The invention relates to a method for respectively recovering ursodesoxycholic acid and chenodeoxycholic acid from ursodesoxycholic acid waste mother liquor. Firstly waste mother liquor is dissolved in an inorganic base solution, and inorganic acid is added to form mixed sediment containing the ursodesoxycholic acid and the chenodeoxycholic acid; secondly, an organic solvent and an organic amine are added to separate ursodesoxycholic acid ammonium salt; and thirdly the ursodesoxycholic acid ammonium salt is acidized to recover the ursodesoxycholic acid, chenodeoxycholic acid ammonium salt left in the organic solvent is acidized and filtered to recover the chenodeoxycholic acid. The recovering method can effectively utilize the ursodesoxycholic acid waste mother liquor, recovers the ursodesoxycholic acid and the chenodeoxycholic acid contained in the ursodesoxycholic acid waste mother liquor, and is high in recover efficiency and product purity. The recovering method is simple to operate and mild in reaction conditions, used reagent is low in cost and wide in source, and the method is suitable for large-scale industrialized production.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a method for separately recovering ursodeoxycholic acid and chenodeoxycholic acid from ursodeoxycholic acid waste mother liquor. Background technique [0002] Ursodeoxycholic acid (3α, 7β-dihydroxy-5β-cholesteric acid), English name: Ursodeoxycholic Acid (UDCA for short), was first discovered from bear bile in 1902, until 1927, the Japanese Masada from bear bile Crystalline UDCA was isolated from China, and its chemical structure was clarified in 1937. It is the 7-position isomer of chenodeoxycholic acid, and its chemical structure is as follows. Bear bile is a rare and precious traditional Chinese medicine, so the separation of ursodeoxycholic acid from bear bile cannot meet the large market demand, so scholars finally synthesized it successfully in 1955 after hard research. [0003] [0004] Studies have found that ursodeoxycholic acid is more effective than chenodeoxy...

Claims

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Application Information

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IPC IPC(8): C07J9/00
Inventor 陆其华周大海
Owner 苏州天绿生物制药有限公司
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