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18alpha- liquorice acid derivatives and preparation thereof

A technology of derivatives and glycyrrhizic acid esters, applied in the field of glycyrrhizic acid derivatives and their preparation, can solve the problems of low oral bioavailability and inconvenience to patients, and achieve good oral resistance to liver damage, excellent lipophilicity, and excellent bioavailability. degree of effect

Active Publication Date: 2007-10-31
CHIA TAI TIANQING PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since both 18β-glycyrrhizinate and 18α-glycyrrhizinate have the problem of low oral bioavailability, they must be injected intravenously to achieve good curative effect. Since liver disease requires long-term treatment, this brings great inconvenience and inconvenience to patients. great pain
How to solve the problem of low oral bioavailability of licorice preparations has become one of the urgent problems in clinical practice

Method used

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  • 18alpha- liquorice acid derivatives and preparation thereof
  • 18alpha- liquorice acid derivatives and preparation thereof
  • 18alpha- liquorice acid derivatives and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: Preparation of 18α-glycyrrhizic acid

[0044] Add 500 g of glycyrrhizic acid to 5 liters of 1M NaOH aqueous solution, heat to 70°C and stir for 5 hours, adjust the pH value to 2-4 after cooling, filter, wash with water, and dry to obtain 382 g of 18α-glycyrrhizic acid with a yield of 76.4%.

Embodiment 2

[0045] Example 2: 18α, 20β-methoxyacyl-11-oxo-n-oleanane-12-en-3β-yl-2-O-β-D-glucopyranuronalcarboxyl-α-D-glucopyranosyl Preparation of furanuronic acid

[0046]

[0047] Dissolve 10g of 18α-glycyrrhizic acid in 100ml of methanol, slowly add 3ml of acetyl chloride dropwise at room temperature (about 0.5h), continue to stir for 1h after addition, filter, and dry in vacuo to obtain the target compound, namely methyl 18α-glycyrrhizinate 6.0 grams, with a melting point of 244-247°C.

Embodiment 3

[0048] Example 3: 18α, 20β-ethoxyacyl-11-oxo-n-oleanane-12-en-3β-yl-2-O-β-D-glucopyranuronalcarboxyl-α-D-glucopyranosyl Preparation of furanuronic acid

[0049]

[0050] Dissolve 10g of 18α-glycyrrhizic acid in 100ml of ethanol, slowly add 3ml of acetyl chloride dropwise at room temperature (about 1h), continue stirring for 5h after addition, filter, and dry in vacuo to obtain the target compound, 7.3g of ethyl 18α-glycyrrhizinate , melting point 235 ~ 238 ℃.

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Abstract

The invention relates to a preparing method of glycyrrhizic acid derivant and usage.

Description

technical field [0001] The invention relates to glycyrrhizic acid derivatives and their preparation methods and uses, in particular to 18α-glycyrrhizic acid ester derivatives and their preparation methods and uses. Background technique [0002] Glycyrrhizin (Glycyrrhizin, GC) is an effective active ingredient extracted from licorice. Its biological activity has been extensively studied at home and abroad and has been used clinically for many years. It has anti-inflammatory, anti-allergic, anti-biological oxidation, immune function regulation, block Ca 2+ Influx, dissociation of adrenal cortex hormone and stabilization of lysosomal membrane and other pharmacological effects, among which anti-inflammatory effect is the main mechanism of glycyrrhizic acid against liver injury. [0003] Glycyrrhizic acid is a pentacyclic triterpene saponin, and the D / E ring in the glycyrrhizic acid triterpene component changes the direction of the C(17)-C(18) bond due to the obstruction of the ...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/704A61P1/16
Inventor 张喜全夏春光丁琴罗徐宏江耿文军于飞
Owner CHIA TAI TIANQING PHARMA GRP CO LTD
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