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Synthetic method of glycyrrhetinic acid ester derivative

A technology of glycyrrhetinic acid ester and glycyrrhizic acid, which is applied in the field of synthesis of glycyrrhetinic acid ester derivatives, can solve the problems of high equipment requirements, long reaction time, and unsuitability for industrial production, and achieve high drug efficacy and reduce waste of resources Effect

Inactive Publication Date: 2012-10-10
CHIA TAI TIANQING PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

), but this method needs to be carried out under high temperature and high pressure, the reaction time is long, the equipment requirements are high, and it is not suitable for industrial production

Method used

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  • Synthetic method of glycyrrhetinic acid ester derivative
  • Synthetic method of glycyrrhetinic acid ester derivative
  • Synthetic method of glycyrrhetinic acid ester derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 118

[0043] The synthesis of embodiment 118β-methyl glycyrrhetinate

[0044] Method 1. Add 10 g of 18β-glycyrrhizic acid to 100 ml of anhydrous methanol, add 5 ml of acetyl chloride, heat to reflux for 2 hours, add 100 ml of water, cool, crystallize a solid, filter, refine with ethanol / water, and dry to obtain the title compound.

[0045] Method 2. Add 20g of 18β-glycyrrhizic acid monoammonium salt into 100ml of anhydrous methanol, add 10ml of acetyl chloride, heat and reflux for 2 hours, the color turns brown, add 200ml of water, cool, crystallize a solid, filter, and refine with ethanol / water , dried to obtain the title compound in a yield of 79%.

[0046] IR: v as (-OH)3387cm -1 , v as (-COOCH 3 )1725cm -1 , v as (=O)1657, 1621cm -1 , v as (A district) 1387, 1361cm -1 , v as (Area B) 1322, 1278, 1246cm -1 .

Embodiment 218

[0047] The synthesis of embodiment 218α-ethyl glycyrrhetinate

[0048] Method 1. Add 10 g of 18α-glycyrrhizic acid into 100 ml of absolute ethanol, add 5 ml of acetyl chloride, heat to reflux for 2 hours, add 100 ml of water, cool, crystallize a solid, filter, refine with 80% ethanol, and dry to obtain the title compound. Yield 85%.

[0049] 1 H-NMR: 0.72(s, 3H), 0.81(s, 3H), 1.00(s, 3H), 1.14(s, 3H), 1.20(s, 3H), 1.22(s, 3H), 1.26(t, 3H), 1.35(s, 3H), 4.14(q, 2H), 5.57(s, 1H)

[0050] 13 C-NMR (ppm): 14.13, 15.62, 15.94, 16.47, 17.54, 18.49, 20.65, 20.75, 26.65, 27.22, 28.07, 28.40, 31.70, 33.75, 35.45, 35.97, 36.84, 37.60, 39.0792, 40.39. , 43.80, 44.89, 54.99, 60.42, 60.66, 78.70, 124.08, 165.64, 178.20, 199.74

[0051] Method 2. Add 10g of 18α-glycyrrhizic acid into 100ml of absolute ethanol, add 1ml of concentrated sulfuric acid, heat and reflux for 8 hours, add 100ml of water, cool, crystallize a solid, filter, refine with ethanol / water, and dry to obtain the title ...

Embodiment 7

[0076] Embodiment 7 Anti-inflammatory effect of the compound of the present invention

[0077] The anti-inflammatory effect of the drug was observed by injecting carrageenan into the paws of rats to induce swelling.

[0078] in:

[0079] (1) Experimental materials

[0080] Animals: male SD rats, 150-180g;

[0081] Inflammator: carrageenan;

[0082] Test substance: use 1% CMC-Na to make 11-deoxy-18α ethyl glycyrrhetinate to the required concentration;

[0083] Positive drug: indomethacin, prepared to the required concentration with 1% CMC-Na;

[0084] (2) Experimental method

[0085] 50 rats were randomly divided into 5 groups with 10 rats in each group, which were model group, positive group (administered indomethacin 10 mg / kg), and test drug dosage groups (30, 60, 120 mg / kg). Animals in each group were administered continuously for 3 days, and before the last administration, the volume of the left hind paw of the rats before administration was measured by micropipette mea...

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PUM

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Abstract

The present invention belongs to the field of biomedicine, and relates to a synthetic method of a glycyrrhetinic acid ester derivative, especially a preparation method of a glycyrrhetinic acid ester derivative shown as a formula I. Specifically, a raw material of R2H contacts with glycyrrhizic acid, glycyrrhizic acid salt or glycyrrhizic acid derivative to generate the glycyrrhetinic acid ester derivative shown as the formula I in the presence of a dehydrating agent of chloride or concentrated sulfuric acid.

Description

[0001] This application is a divisional application of a Chinese patent application titled "Synthetic Method of Glycyrrhetinic Acid Derivatives and Deoxyglycyrrhetinic Acid Compound" (application number: 200910027345.5) with a filing date of May 31, 2009. technical field [0002] The invention relates to a method for directly synthesizing glycyrrhetinate by using glycyrrhizic acid, and relates to 11-deoxy-18α glycyrrhetinate compound, its preparation method and its application in the fields of treating liver injury and anti-inflammation. Background technique [0003] Glycyrrhizae is the root and stem of the leguminous plant Glycyrrhizae, and its main pharmacological active substances are glycyrrhizic acid and its aglycone glycyrrhetinic acid. Modern studies have shown that glycyrrhetinic acid has anti-inflammatory, anti-ulcer, anti-viral (hepatitis virus, HIV, etc.), lowering blood lipids, and preventing and treating tumors. [0004] Glycyrrhetinic acid is structurally simil...

Claims

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Application Information

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IPC IPC(8): C07J63/00C07J75/00
Inventor 张爱明张喜全夏春光徐宏江王衡奇
Owner CHIA TAI TIANQING PHARMA GRP
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