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Silybin rosmarinate and its preparation method and use

A technology of rosmarinic acid and silibinin, which is applied in pharmaceutical formulations, medical preparations containing active ingredients, digestive system, etc., can solve the problems of affecting clinical efficacy, low bioavailability, unstable absorption, etc.

Active Publication Date: 2017-12-26
TIANJIN TASLY PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because silibinin is insoluble in water and oil, the bioavailability is low and the absorption is unstable, thus affecting the clinical efficacy

Method used

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  • Silybin rosmarinate and its preparation method and use
  • Silybin rosmarinate and its preparation method and use
  • Silybin rosmarinate and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the preparation of silybin rosmarinate

[0054]

[0055] Under nitrogen protection, add rosmarinic acid (Sigma-Aldrich, 96%) (1.0g, 2.77mmol), silibinin (Jiangsu Tasly Diyi Pharmaceutical Co., Ltd., 98%), batch number: 20110502) [mixture of 10S, 11S+10R, 11R] (1.6g, 3.33mmol), EDCl (0.69g, 3.6mmol) and HOBt (0.49g, 3.6mmol), with 30ml of anhydrous N,N-dimethyl Formamide was dissolved, and triethylamine (0.8 g, 6.9 mmol) was slowly added dropwise, and stirred at room temperature for 48 hours. After stopping the reaction, the reaction solution was poured into 200ml of ice water, and a large amount of solids were separated out. After the solids were dried by suction filtration, they were purified by silica gel column chromatography (eluent: dichloromethane / methanol=20 / 1) to obtain silybin rosemary Carboxylate (I) (yellow solid, 0.45 g, 25% yield).

[0056] 1 H NMR (CD 3 OD,400MHz):δ7.57(1H,d,J=16.0Hz),7.10-6.94(6H,m),6.86-6.84(2H,m),6.81-6.78(2H,m),6.6...

Embodiment 2

[0059] Embodiment 2: the preparation of silybin rosmarinate

[0060] Under nitrogen protection, add 2.77mmol rosmarinic acid, 2.77mmol silibinin, 2.77mmol EDCl and 2.77mmol HOBt to the dry reaction flask, dissolve with 30ml of anhydrous N,N-dimethylformamide, drop slowly Add 4.16mmol triethylamine, stir at room temperature for 48 hours, stop the reaction, pour the reaction solution into ice water, and precipitate a large amount of solid, and the solid is filtered and dried by silica gel column chromatography (eluent is dichloromethane / methanol=50 / 1) purification to obtain silybin rosmarinate (I).

Embodiment 3

[0061] Embodiment 3: the preparation of silybin rosmarinate

[0062] Under the protection of nitrogen, add 2.77mmol rosmarinic acid, 5.54mmol silibinin, 4.16mmol EDCl and 4.16mmol HOBt to the dry reaction flask, dissolve with 30ml anhydrous N,N-dimethylformamide, drop slowly Add 13.85mmol triethylamine, stir at room temperature for 48 hours, stop the reaction, pour the reaction solution into ice water, and precipitate a large amount of solid, and the solid is filtered and dried by silica gel column chromatography (eluent is dichloromethane / methanol=10 / 1) purification to obtain silybin rosmarinate (I).

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Abstract

The invention relates to silibinin rosmarinate shown in a formula (I) specified in the description as well as pharmaceutical salts or solvates thereof. The invention further relates to a preparation method for a compound shown in the formula (I) as well as a medicine composition and medical application thereof. The compound shown in the formula (I) disclosed by the invention has a function of protecting liver cells, and can be used as a medicine for treating liver injuries and hepatic fibrosis diseases.

Description

technical field [0001] The present invention relates to silybin rosmarinate and its preparation method and application. The compound of the invention has the effect of protecting liver cells and can be used as a medicine for treating liver damage and liver fibrosis diseases. Background technique [0002] Liver fibrosis is a common pathological feature of most chronic liver diseases, and it is also an important intermediate link in the further development and deterioration of chronic hepatitis and cirrhosis. Alcoholism is the most common cause of liver fibrosis in foreign countries, especially in Europe and America, accounting for 50% to 80%. In China, the main cause of liver fibrosis is hepatitis virus infection. my country is a high prevalence area of ​​hepatitis B virus (HBV) infection, about 750 million people have been infected with HBV, and about 120 million people are chronic HBV carriers. HCV infection is more likely to cause chronicity, and 20% to 25% of chronic HC...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/04A61K31/357A61P1/16
CPCC07D407/04
Inventor 吴廼峰马晓慧韩民颜璐璐张莉华王晶褚扬曹晶靳元鹏周水平朱永宏
Owner TIANJIN TASLY PHARMA CO LTD
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