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Preparation method for ursodesoxycholic acid

A technology of ursodeoxycholic acid and ketodeoxycholic acid, which is applied in the field of preparation of ursodeoxycholic acid, can solve the problems of poor stereoselectivity, low product yield, poor product quality, etc., and achieves easy operation control, Reduced purification steps, mild reaction conditions

Inactive Publication Date: 2016-03-23
CHANGDE YUNGANG BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most of the preparation process of ursodeoxycholic acid now uses alcohol + metal sodium system for hydrogenation reduction reaction. This system has poor stereoselectivity during hydrogenation reduction reaction, only about 80% of 7-ketodeoxycholic acid It is reduced to ursodeoxycholic acid, and the other 20% is reduced to chenodeoxycholic acid. After the reaction is completed, it needs to be separated and purified. The final ursodeoxycholic acid product is only about 60% of chenodeoxycholic acid. The product yield The rate is not high; and the product quality is poor

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Replace the air in the hydrogenation reactor with nitrogen, add 100L of methanol, stir and dissolve, add 10Kg of 7-ketodeoxycholic acid, 4Kg of potassium ethoxide, and 0.2 grams of 1# catalyst. After replacing the nitrogen in the reactor with hydrogen, keep the hydrogen pressure in the reactor at 15Mpa, and react at room temperature for 5 hours. Distill to remove the solvent in the reaction kettle, add 200L purified water, stir to dissolve, adjust PH4 with 1:1 hydrochloric acid, centrifuge, wash the filter cake with purified water until the pH of the washing water is greater than 5. Vacuum dry at 75°C until the water content is less than 0.5%, and obtain Xiongqu Oxycholic acid 9.5Kg.

Embodiment 2

[0028] Replace the air in the hydrogenation reactor with nitrogen, add 100L of ethanol, stir and dissolve, then add 10Kg of 7-ketodeoxycholic acid, 4Kg of sodium bicarbonate, and 0.5g of 2# catalyst. After replacing the nitrogen in the reactor with hydrogen, keep the hydrogen pressure in the reactor at 10Mpa, and react at room temperature for 3 hours. Distill to remove the solvent in the reaction kettle, add 150L purified water, stir to dissolve, adjust PH3 with 1:2 sulfuric acid, centrifuge, wash the filter cake with purified water until the pH of the washing water is greater than 5. Vacuum dry at 75°C until the water content is less than 0.5%, and get Xiongqu Oxycholic acid 9.4Kg.

Embodiment 3

[0030] Replace the air in the hydrogenation reactor with nitrogen, add 200L of tert-butanol, stir and dissolve, then add 10Kg of 7-ketodeoxycholic acid, 4Kg of sodium carbonate, and 1g of 3# catalyst. After replacing the nitrogen in the reactor with hydrogen, keep the hydrogen pressure in the reactor at 5Mpa, and react at room temperature for 4 hours. Distill to remove the solvent in the reaction kettle, add 300L purified water, stir to dissolve, adjust PH3 with 1:3 hydrochloric acid, centrifuge, wash the filter cake with purified water until the pH of the washing water is greater than 5. Vacuum dry at 75°C until the water content is less than 0.5%, and obtain Xiongqu Oxycholic acid 9.6Kg.

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PUM

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Abstract

The invention discloses a preparation method for ursodesoxycholic acid, and relates to the field of biochemical pharmacy. A preparation method for ursodesoxycholic acid in the prior art is relatively poor in stereoselectivity during a hydrogenation reduction reaction, and the method is relatively long in production line, not high in product yield and relatively poor in production quality. The preparation method comprises the following steps: dissolving 7-ketodesoxycholic acid in a solvent, adding a chiral catalyst, under an alkaline condition, maintaining the pressure to be 0-20 MPa, introducing hydrogen at 15-81 DEG C to carry out a hydrogenation reduction reaction, and performing distillation to remove the solvent after the reaction is completed; adding 13-95 times of purified water, and then adding acid liquor, so that a product after the hydrogenation reduction reaction is crystallized; separating solid and liquid, washing and drying the solid to obtain solid powder, namely the ursodesoxycholic acid. The preparation method is short in product line, high in product yield and good in product quality.

Description

technical field [0001] The invention relates to the field of biochemical pharmacy, in particular to a preparation method of ursodeoxycholic acid. Background technique [0002] At present, the starting materials for the synthesis of ursodeoxycholic acid at home and abroad are chenodeoxycholic acid and bovine cholic acid, and no matter what kind of raw material is used to synthesize ursodeoxycholic acid, it is necessary to prepare 7-ketodeoxycholic acid first. acid, and then undergo hydrogenation reduction to obtain ursodeoxycholic acid. [0003] Most of the preparation process of ursodeoxycholic acid now uses alcohol + metal sodium system for hydrogenation reduction reaction. This system has poor stereoselectivity in hydrogenation reduction reaction, only about 80% of 7-ketodeoxycholic acid It is reduced to ursodeoxycholic acid, and the other 20% is reduced to chenodeoxycholic acid. After the reaction is completed, it needs to be separated and purified. The final ursodeoxych...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
Inventor 邓家国
Owner CHANGDE YUNGANG BIOTECHNOLOGY CO LTD
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