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18 alpha-glycyrrhetinic o-phthalate, and preparation and use thereof

A technology of glycyrrhetic acid and phthalate, applied in pharmaceutical formulations, medical preparations containing active ingredients, digestive system, etc., can solve the problem of slow biotransformation, inability to produce inflammatory mediators, and inability to immediately exert curative effects, etc. problems, to achieve strong anti-inflammatory, reduce production costs, reduce tissue damage

Inactive Publication Date: 2009-07-22
HANGHZOU HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been confirmed by clinical trials that the use of 18β-glycyrrhizinic acid injection can inhibit the activity of phospholipase A2 and block the metabolism of arachidonic acid in the initial stage, so that prostaglandins, leukotrienes and other inflammatory mediators cannot be produced, playing a role Anti-inflammatory and strong protection of liver cells; it can also inhibit the binding activity of nuclear transcription factor-kB, block the production of various inflammatory factors, thereby reducing tissue damage; but due to the high polarity of 18β-glycyrrhizic acid, the The absorption is poor, and the biotransformation speed in the body is slow, so the curative effect cannot be exerted immediately

Method used

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  • 18 alpha-glycyrrhetinic o-phthalate, and preparation and use thereof
  • 18 alpha-glycyrrhetinic o-phthalate, and preparation and use thereof
  • 18 alpha-glycyrrhetinic o-phthalate, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 1. Weigh 823g (1.0mol) of 18β-glycyrrhizic acid produced by Xi'an Fujie Pharmaceutical Co., Ltd. and put it into a reaction tank, add 60L of 4mol / L sodium hydroxide, heat and reflux for 8 hours to obtain 576g of 18α-glycyrrhizic acid, The product yield is 69.99%.

[0036] [α] 20 =+18.0°(C=0.5 ethanol)

[0037] Elemental Analysis Results

[0038] Calculated value (%) Carbon: 61.30 Hydrogen: 7.59

[0039] Measured value (%) Carbon: 61.42 Hydrogen: 7.53

[0040] The 18α-glycyrrhizic acid that takes by weighing 823g (1.0mol) is put into reaction tank, first adds 80L water and stirs to dissolve, then adds hydrogen type sulfonic acid cationic resin catalytic hydrolysis, wherein the add-on of hydrogen type sulfonic acid cationic resin is 18α- 50 times the volume of glycyrrhizic acid. Then heat the reaction tank to 98°C, stir and reflux for 9 hours, filter to remove the resin, and concentrate the filtrate under reduced pressure; add ethanol until the alcohol content is 40%...

Embodiment 2

[0049] Weigh 823g (1.0mol) of 18β-glycyrrhizic acid produced by Xi'an Fujie Pharmaceutical Co., Ltd. and put it into a reaction tank, add 80L of 4mol / L sodium hydroxide, and heat and reflux for 10 hours to obtain 576g of 18α-glycyrrhizic acid. The rate is 69.99%.

[0050] Weigh 823g (1.0mol) of the prepared 18α-glycyrrhizic acid into a reaction tank, first add 80L of water and stir to dissolve, then add 8L of sulfuric acid with a concentration of 50%, and bathe in boiling water for 5 hours. Filter, wash the precipitate with distilled water until the pH is close to 7, and dry at 105°C to obtain 350 g of 18α-glycyrrhetinic acid with a yield of 74.4%.

[0051] Weigh 0.5g of the prepared 18α-glycyrrhetinic acid and put it into the reaction tank, first add phthalic anhydride, wherein the molar ratio of 18α-glycyrrhetinic acid to the added phthalic anhydride is 1:30; then add 7ml of pyridine to dissolve, boil water bath Reflux for 50 hours. After the reaction is complete, dilute hy...

Embodiment 3

[0055] Weigh 823g (1.0mol) of 18β-glycyrrhizic acid produced by Xi'an Fujie Pharmaceutical Co., Ltd. and put it into a reaction tank, add 80L of 4mol / L sodium hydroxide, and heat and reflux for 12 hours to obtain 576g of 18α-glycyrrhizic acid. The rate is 69.99%.

[0056] Weigh 823g (1.0mol) of the prepared 18α-glycyrrhizic acid into a reaction tank, first add 80L of water and stir to dissolve, then add 10L of 50% hydrochloric acid, and bathe in boiling water for 8 hours. Filter, wash the precipitate with distilled water until the pH is close to 7, and dry at 105° C. to obtain 330 g of 18α-glycyrrhetinic acid, with a product yield of 70.1%.

[0057] Weigh 0.5 g of the prepared 18α-glycyrrhetinic acid and put it into the reaction tank, first add phthalic anhydride, wherein the molar ratio of 18α-glycyrrhetinic acid to the added phthalic anhydride is 1:20; then add 7ml of N,N- Dimethylformamide was dissolved, and the boiling water bath was refluxed for 30 hours. After the react...

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Abstract

The invention relates to an 18Alpha-glycyrrhetinic acid o-phthalate, a method for preparing the 18Alpha-glycyrrhetinic acid o-phthalate and the application thereof in drugs. The invention aims at providing an 18Alpha-glycyrrhetinic acid o-phthalate which has safe use, strong pharmacological activity, and fast effect, and a method for preparing the 18Alpha-glycyrrhetinic acid o-phthalate; and the method has the advantages of simple process, and high product quality and yield. The technical proposal provided by the invention is as follows: the 18Alpha-glycyrrhetinic acid o-phthalate is characterized by being a pentacyclic triterpenoid derivative of o-phthalic acid which has the chemical name of 3-(1-carboxy-2-oxidation phenoxy)-11-O-18Alpha-oleanane-12-ene-29-formate, the molecular weight of 618.8, and the molecular formula of C38H 50O7 question mark R.

Description

technical field [0001] The invention relates to a 18α-glycyrrhetinic acid phthalate; at the same time, the invention also relates to a preparation method of the 18α-glycyrrhetinic acid phthalate and its application in medicine. Background technique [0002] Glycyrrhizic acid is the most important active ingredient in natural licorice. Since licorice is a well-known and widely used natural medicine, research on its active ingredient glycyrrhizic acid and its salts has been quite in-depth. At present, studies have shown that licorice contains two epimers, 18α and 18β, but most of the glycyrrhizic acid in licorice is in the 18β configuration, and the 18α epimer only exists in a small amount in licorice. middle. It has been confirmed by clinical trials that the use of 18β-glycyrrhizinic acid injection can inhibit the activity of phospholipase A2 and block the metabolism of arachidonic acid in the initial stage, so that prostaglandins, leukotrienes and other inflammatory mediato...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P29/00A61P37/08A61P37/02A61P13/12A61P1/16A61P19/04A61P35/00
Inventor 俞进吴锡铭
Owner HANGHZOU HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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