Refining method of glycochenodeoxycholic acid sodium

A technology of sodium glycochenodeoxycholate and glycochenodeoxycholic acid, which is applied in the field of refining sodium glycochenodeoxycholate, can solve the problems of low HPLC purity, and achieve process stability, easy control, and process operability strong effect

Inactive Publication Date: 2019-04-19
YAOPU SHANGHAI PHARMA TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Sodium glycochenodeoxycholate is used in the research of the field of drug therapy, and its sample purity is required to be not less than 98%, and the impurities are controllable. Glycine obtained by the chemical synthesis preparation method of sodium glycochenodeoxycholate disclosed in the prior art The HPLC purity of sodium chenodeoxycholate, and sodium glycochenodeoxycholate sold in the market is less than 98%

Method used

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  • Refining method of glycochenodeoxycholic acid sodium
  • Refining method of glycochenodeoxycholic acid sodium
  • Refining method of glycochenodeoxycholic acid sodium

Examples

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Embodiment 1

[0039] Example 1 Sodium glycochenodeoxycholate refined

[0040] Such as figure 2 , take 1 kg of commercially available sodium glycochenodeoxycholate, HPLC purity 96.6%, add 6 kg of water and stir to dissolve completely, adjust the pH value to 5.5~6.0 with concentrated hydrochloric acid, and extract three times with ethyl acetate. The pH value of the water phase was adjusted to 1.5-2.0 with concentrated hydrochloric acid, stirred, filtered, the filter cake was rinsed with water, and dried to obtain 918 g of glycochenodeoxycholic acid.

[0041] Glycychenodeoxycholic acid and triethylamine were added to ethyl acetate at a molar ratio of 1:1.2, heated to 80 o C under stirring for 10 hours, cooled and filtered, washed with ethyl acetate, and dried to obtain 1.06 kg of triethylamine salt of glycochenodeoxycholic acid.

[0042] Suspend triethylamine salt of glycochenodeoxycholic acid in acetone and water, adjust the pH value to 1.5~2.0 with concentrated hydrochloric acid, stir, fi...

Embodiment 2

[0044] Example 2 Refining Sodium Glychenodeoxycholate

[0045] Such as image 3 , take 1 kg of commercially available sodium glycochenodeoxycholate, HPLC purity 95.2%, add 6 kg of water and stir to dissolve completely, adjust the pH value to 5.5~6.0 with acetic acid, and extract three times with ethyl acetate. The pH of the aqueous phase was adjusted to 1.5-2.0 with concentrated hydrochloric acid, stirred, filtered, the filter cake was rinsed with water, and dried to obtain 922 g of glycochenodeoxycholic acid.

[0046] Glycychenodeoxycholic acid and triethylamine were added to ethyl acetate at a molar ratio of 1:1.2, heated to 80 o C under stirring for 8 hours, cooled and filtered, washed with ethyl acetate, and dried to obtain 1.04 kg of triethylamine salt of glycochenodeoxycholic acid.

[0047] Dissolve triethylamine salt of glycochenodeoxycholic acid in water, adjust the pH value to 1.5~2.0 with concentrated hydrochloric acid, stir, filter, rinse the filter cake with water,...

Embodiment 3

[0049] Example 3 Refining Sodium Glycychenodeoxycholate

[0050] Such as Figure 4 , take 1 kg of commercially available sodium glycochenodeoxycholate, HPLC purity 97.2%, add 6 kg of water and stir to dissolve completely, adjust the pH value to 5.5~6.0 with concentrated hydrochloric acid, and extract three times with ethyl acetate. The pH of the aqueous phase was adjusted to 1.5-2.0 with concentrated hydrochloric acid, stirred, filtered, the filter cake was rinsed with water, and dried to obtain 932 g of glycochenodeoxycholic acid.

[0051] Glycychenodeoxycholic acid and triethylamine were added into acetone at a molar ratio of 1:1.2, heated to 60 o C under stirring for 12 hours, cooled and filtered, washed with ethyl acetate, and dried to obtain 1.1 kg of triethylamine salt of glycochenodeoxycholic acid.

[0052] Dissolve triethylamine salt of glycochenodeoxycholic acid in water, adjust the pH value to 1.5-2.0 with concentrated hydrochloric acid, stir, filter, rinse the fil...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a refining method of glycochenodeoxycholic acid sodium. The method includes the steps of S1, adding commercially-available glycochenodeoxycholic acid sodium to water, adjusting the pH value into the weak acid range with an acid water solution, conducting extracting through an organic solvent, adjusting the pH valueof the water phase into the strong acid range with the acid water solution, and conducting filtering to obtain glycochenodeoxycholic acid; S2, heating and stirring the glycochenodeoxycholic acid andorganic alkali in a solvent to form salt, and conducting cooling and filtering to obtain glycochenodeoxycholic acid organic alkali salt; S3, adjusting the pH value of the glycochenodeoxycholic acid organic alkali salt in the solvent into the strong acid range with an acid water solution, and conducting filtering, washing and drying to obtain a glycochenodeoxycholic acid refined product. The methodhas the advantages of being simple and easy to operate, stable in process, easy to control, beneficial for post-treatment, safe, friendly to the environment and the like, and can be continuously produced on a large scale.

Description

technical field [0001] The invention belongs to the technical field of product purification in fine chemical industry, and relates to a method for refining sodium glycochenodeoxycholate. Background technique [0002] Glycochenodeoxycholic acid sodium (GCDA) is a bile salt. In recent years, scientists have found that sodium glycochenodeoxycholate is not only a natural regulator involved in the absorption of dietary lipids and fat-soluble nutrients, but also an important signaling molecule in the human body, involved in multiple paracrine And endocrine functions, related to the balance of lipid and cholesterol levels, control of energy expenditure and regulation of the immune system. For example, sodium glycochenodeoxycholate has a strong apoptosis-inducing effect on liver cancer cells, can induce DNA clearance, and can be used in biochemical and therapeutic research on liver cancer. Therefore, sodium glycochenodeoxycholate has broad application prospects in the field of dru...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
CPCC07J41/0061
Inventor 何秀君柳惠
Owner YAOPU SHANGHAI PHARMA TECH CO LTD
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