Synthetic method of glycyrrhetinic acid ester derivative and deoxyglycyrrhetinic acid ester compound

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

Active Publication Date: 2010-12-01
CHIA TAI TIANQING PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 and deoxyglycyrrhetinic acid ester compound
  • Synthetic method of glycyrrhetinic acid ester derivative and deoxyglycyrrhetinic acid ester compound
  • Synthetic method of glycyrrhetinic acid ester derivative and deoxyglycyrrhetinic acid ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Synthesis of 18β-methyl glycyrrhetinate

[0043] 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.

[0044] 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%.

[0045] 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 2

[0046] Example 2 Synthesis of 18α-ethyl glycyrrhetinate

[0047] 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%.

[0048] 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)

[0049] 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

[0050] 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 compou...

Embodiment 4

[0051] Example 4 Synthesis of ethyl 11-deoxy-18α glycyrrhetinate

[0052] Add 11 g of ethyl 18α-glycyrrhetinate and 6 g of zinc powder into 150 ml of 1,4-dioxane, add a little water, pass in hydrogen chloride gas, and stir for 5 hours. Filter, evaporate the solvent from the mother liquor, add 50ml of water and 100ml of ethyl acetate, stir, separate layers, wash the organic layer with water, evaporate to dryness, and refine with ethanol / water to obtain 8.6g of white crystals.

[0053] IR: v as (-OH)3374cm -1 , v as (-COOCH 3 )1727cm -1 , v as (A district) 1382cm -1 , v as (Area B) 1300, 1278cm -1 .

[0054] 1 H-NMR: 0.66(s, 3H), 0.79(s, 3H), 0.96(s, 3H), 0.99(s, 3H), 1.00(s, 3H), 1.15(s, 3H), 1.22(s, 3H), 1.25(t, 3H), 4.12(q, 2H), 5.18(t, 1H)

[0055] 13 C-NMR (ppm): 14.19, 15.24, 15.69, 15.83, 17.44, 18.30, 20.93, 23.17, 23.17, 26.28, 27.27, 28.14, 28.73, 32.38, 34.15, 34.96, 36.07, 36.86, 38.661, 38.8 , 39.55, 42.70, 43.67, 47.24, 55.31, 60.20, 79.02, 117.55, 14...

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Abstract

The invention relates to a compound 11-deoxy-18 alpha glycyrrhetinic acid derivative in a formula II, and application thereof in the fields of hepatic injury treatment, anti-inflammatory and the like. The invention relates to a preparation method of the glycyrrhetinic acid ester derivative.

Description

technical field [0001] 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 [0002] 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. [0003] Glycyrrhetinic acid is structurally similar to hydrocortisone, and many clinical trials have demonstrated the anti-inflammatory effectiveness of glycyrrhetinic acid. Zakirov found that 3-amino-11-deoxyglycyrrhetinic acid exhibited obvious anti-inflammatory activity on aseptic arthritis in various ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07J75/00A61K31/56A61P29/00A61P1/16
CPCA61K31/56C07J63/008A61P1/16A61P29/00A61P39/02
Inventor 张爱明张喜全夏春光徐宏江王衡奇
Owner CHIA TAI TIANQING PHARMA GRP CO LTD
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