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Preparation and medical application of cholic acid berberine conjugate

A technology of berberine hydrochloride and conjugates, applied in the field of bile acid berberine conjugates, which can solve the problems of limited drug efficacy, malabsorption, and low water solubility

Inactive Publication Date: 2016-06-22
HEFEI HUAFANG PHARMA SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, due to the poor water solubility of bile acids, the oral bioavailability is low, which limits the full play of their efficacy.
However, berberine hydrochloride has very little water solubility, even less fat solubility, and poor absorption in the gastrointestinal tract, resulting in low oral bioavailability, which affects its systemic therapeutic effect.
Although bile acid drugs and berberine have many similar pharmacological activities, they all limit their clinical use to a certain extent due to their low bioavailability. The method of utilizing the degree and exerting the synergistic effect of the two will have very important clinical significance

Method used

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  • Preparation and medical application of cholic acid berberine conjugate
  • Preparation and medical application of cholic acid berberine conjugate
  • Preparation and medical application of cholic acid berberine conjugate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of Cholic Acid Berberine Conjugates

[0021] Take 3.7g of berberine hydrochloride, put it into a 500ml three-necked flask, add 100ml of ethanol, adjust the pH to 7-8 with 3mol / l sodium hydroxide, heat up to 60-70°C, stir to dissolve, then add 4.1g of cholic acid, Keep stirring at this temperature for 1-5 hours, cool down to room temperature, crystallize, filter, and dry to obtain 6.0 g of cholic acid berberine conjugate with a yield of 81%.

Embodiment 2

[0023] Synthesis of Cholic Acid Berberine Conjugates

[0024] Take 3.7g of berberine hydrochloride, put it into a 500ml three-necked flask, add 100ml of ethanol, adjust the pH to 7-8 with 3mol / l potassium hydroxide, heat up to 60-70°C, stir to dissolve, then add 4.3g of cholic acid, Keep stirring at this temperature for 1-5 hours, cool down to room temperature, crystallize, filter, and dry to obtain 6.6 g of cholic acid berberine conjugate with a yield of 89%. ESI-MS (M + +H)m / zcalcdforC 20 h 18 NO 4 + 337.12found337.16; ESI-MS (M + +H)m / zcalcdforC 24 h 39 o 5 408.28 found 408.30.

Embodiment 3

[0026] Synthesis of hyodeoxycholic acid berberine conjugate

[0027] Take 3.7g of berberine hydrochloride, put it into a 500ml three-necked flask, add 100ml of ethanol, adjust the pH to 7-8 with 3mol / l sodium hydroxide, raise the temperature to 60-70°C, stir to dissolve, then add 4.1g of hyodeoxychol acid, kept at this temperature and stirred for 1-3 hours, cooled to room temperature, crystallized, filtered, and dried to obtain 6.3 g of hyodeoxycholic acid berberine conjugate with a yield of 87%. ESI-MS (M + +H)m / zcalcdforC 20 h 18 NO 4 + 337.12found337.17; ESI-MS (M + +H)m / zcalcdforC 24 h 39 o 4 392.29 found 392.30.

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PUM

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Abstract

The invention provides a preparation method of a conjugate in the formula (I) and application thereof as medicine preventing or treating liver cirrhosis, adiposis hepatica, hyperlipidemia, hyperglycemia, obesity and hepatic fibrosis. Pharmacological experiments find that the conjugate has drug activity with various value. Specifically, the conjugate shows the functions of reducing blood sugar and low-density lipoprotein and improving the transaminase level in animal experiments. Besides, the invention further relates to a preparation, a preparation method and application of the conjugate.

Description

technical field [0001] The invention relates to the technical field of food and pharmaceuticals, in particular to the application of bile acid berberine conjugates in the treatment of liver cirrhosis, fatty liver, hyperlipidemia, hyperglycemia, obesity and liver fibrosis. Background technique [0002] Berberine BBR (Berberine, BBR) is the main active ingredient of Coptis chinensis, and the content of BBR in Coptis chinensis is the highest, accounting for 5.2-7.69%. Coptis chinensis is bitter in taste and has the effects of clearing heat, detoxifying, purging fire and curing diabetes. In the past, it was believed that it was not easy to absorb after oral administration, and it was effective for intestinal infections caused by Shigella, Escherichia coli, Staphylococcus aureus, conjunctivitis, suppurative otitis media, etc. It is mainly used for the treatment of intestinal infections in clinical practice. With the deepening of research, in recent years, it has been found that ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00C07D455/03A61K31/575A61K31/4375A61P9/12A61P1/16A61P3/06A61P3/10A61P3/04
CPCC07D455/03C07J9/00
Inventor 高永好何勇吴宗好封保龙
Owner HEFEI HUAFANG PHARMA SCI & TECH
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