Berberine glycyrrhetinic acid enantiomeric salts and preparation method and application thereof

A technology of glycyrrhetinic acid and berberine, which is applied in pharmaceutical formulations, medical preparations containing active ingredients, digestive system, etc., can solve the problems of berberine's clinical curative effect and insufficient therapeutic range.

Inactive Publication Date: 2011-01-05
HANGHZOU HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to solve the deficiency of existing single compound berberine in clinical curative effect and therapeutic range, and to provide a kind of berberine glycyrrhetinic acid enantiomer whose therapeutic effect on tumor, diabetes and chronic inflammatory disease is better than single compound Salt

Method used

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  • Berberine glycyrrhetinic acid enantiomeric salts and preparation method and application thereof
  • Berberine glycyrrhetinic acid enantiomeric salts and preparation method and application thereof
  • Berberine glycyrrhetinic acid enantiomeric salts and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The 5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolane[5,6-a]quinazine·18β,3β-hydroxy -11-Oxooleanane-12-ene-30-carboxylate: Its preparation method is:

[0026] Take 84g of berberine and dissolve with 80% ethanol, and dissolve 117.5g of 18β-glycyrrhetinic acid with 80% ethanol, add the above solution and mix and stir for 2 hours, remove the solvent under reduced pressure, grind the residue with a small amount of ethyl acetate, precipitate, filter, reduce Press and dry to obtain 104.3 g of light yellow powder with a yield of 51.7%.

[0027] mp: 316~321℃

[0028] [C] D20+170.0° (c=1, chloroform)

[0029]

Embodiment 2

[0031] The 5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolane[5,6-a]quinazine·18a,3β-hydroxy The preparation method of -11-oxooleanane-12-ene-30-formate is:

[0032] Take 84g of berberine and dissolve with 80% ethanol, dissolve 117.5g of 18a-glycyrrhetinic acid with absolute ethanol, add the above solution and mix and stir for 2 hours, remove the solvent under reduced pressure, grind the residue with a small amount of ethyl acetate, precipitate, filter, reduce Press and dry to obtain 112.6 g of light yellow powder with a yield of 55.9%.

[0033] mp: 346~351℃

[0034] [C] D20+98° (c=1, chloroform)

[0035]

[0036]

Embodiment 3

[0038] This embodiment describes the effect of the compounds of the present invention on the blood sugar of alloxan diabetic mice:

[0039]Alloxan was used to create a hyperglycemia model in mice, and the mice with blood glucose>11mmol / l were randomly divided into model control group, 18β-glycyrrhetinic acid berberine salt, 18a-glycyrrhetinic acid berberine salt, positive control group, Give normal saline, 18β-glycyrrhetinic acid berberine salt, 18a-glycyrrhetinic acid berberine salt, and berberine, once a day, for 14 consecutive days, fasting for 12 hours after the last administration, without water, and testing for fasting Blood sugar, observe changes in blood sugar before and after medication.

[0040] Table 1:

[0041] Blood glucose before and after alloxan administration in mice

[0042]

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Abstract

The invention discloses novel organic berberine glycyrrhetinic acid enantiomeric salts used for medicines and a production method and application thereof. The chemical name of the organic berberine glycyrrhetinic acid enantiomeric salts is: 5,6-dihydrogen-9,10-dimethoxybenzo[g]-1,3-benzodioxolane[5,6-a]quinolizidine.18a(beta),3beta-hydroxyl-11-oxooleanane-12-olefine-30-formate. The production method comprises the following steps of: respectively dissolving berberine and a glycyrrhetinic acid enantiomer in 80 percent ethanol according to a medicament eutecticum principle, mixing the two liquids, stirring for 2 hours, removing the ethanol under reduced pressure, and treating by using ethyl acetate to prepare the berberine glycyrrhetinic acid enantiomeric salts. The organic salts with dual parent nuclei have positive practical significance for resisting diseases such as tumors, diabetes, chronic inflammatory diseases such as rheumatoid arthritis, hepatitis, Alzheimer disease and the like of human and developing medicines.

Description

technical field [0001] The present invention relates to a new compound that can be used for the treatment of diseases such as tumors and diabetes, specifically a compound salt formed by combining berberine and glycyrrhetinic acid, which is the different enantiomer 18a-glycyrrhetinic acid of berberine and glycyrrhetinic acid Or 18β-glycyrrhetinic acid combined salt. Background technique [0002] Berberine is an isoquinoline alkaloid extracted from Coptis chinensis of the family Ranunculaceae, and is the main component of Chinese medicine Coptis chinensis. In the past, it was often believed that it was not easy to absorb after oral administration, and because it is effective against intestinal infections caused by Shigella, Escherichia coli, and Staphylococcus aureus, conjunctivitis, suppurative otitis media, etc., it is mainly used clinically for the treatment of intestinal infections. With the deepening of research, in recent years, it has been found that it has pharmacolog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07D455/03A61K31/56A61K31/4375A61P35/00A61P3/10A61P29/00A61P19/02A61P1/16A61P25/28
Inventor 王佩吴锡铭
Owner HANGHZOU HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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