4',5,6-trimethoxy scutellarin as well as preparation method and pharmaceutical composition thereof

A scutellarin and trimethoxy technology, which is applied in the field of scutellarin derivatives, can solve the problems of poor solubility, low bioavailability, and unsatisfactory therapeutic effects of scutellarin or its derivatives. , to achieve the effect of low cost, easy operation and mild reaction conditions

Active Publication Date: 2009-11-25
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the existing scutellarin or its derivatives have poor s

Method used

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  • 4',5,6-trimethoxy scutellarin as well as preparation method and pharmaceutical composition thereof
  • 4',5,6-trimethoxy scutellarin as well as preparation method and pharmaceutical composition thereof
  • 4',5,6-trimethoxy scutellarin as well as preparation method and pharmaceutical composition thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 4

[0027] Preparation Example 4', 5, the preparation of 6-trimethoxy scutellarin (A1)

[0028] 5 grams (10.8mmol) scutellarin was dissolved in 100 milliliters of DMF and dichloromethane mixed solvent, added 4.6 gram iodomethane and 7.5 grams (54mmol) potassium carbonate, stirred at room temperature for 2 days, TLC (thin layer chromatography ) shows that the reaction raw materials are complete, add 50 milliliters of 1N hydrochloric acid, and extract 3 times with 50 milliliters of ethyl acetate, combine the organic phases, dry with colorless sodium sulfate, spin the organic solvent, and cross the column with silica gel (ethyl acetate: methanol = 10:1), to obtain 3.1 g of a light yellow solid with a yield of 60%. h 1 NMR (400MHz, CDCl 3 )δ7.78(d, 2H), 6.92(d, 2H), 6.60(s, 1H), 6.50(s, 1H), 4.94(d, 1H), 4.01(d, 1H), 3.83(s, 3H ), 3.81(s, 3H), 3.71(s, 3H), 3.47-3.67(m, 5H); C 13 NMR (100MHz, CDCl 3 )δ181.76,181.68,168.14,163.59,163.54,161.79,155.15,152.38,152.10,151.62,132.25,127...

experiment example 1

[0029] Experimental Example 1 Pharmacological study on the protective effect of A1 on cardiovascular and cerebrovascular ischemia

[0030] A large number of pharmacological studies have proved that breviscapine can dilate cerebral blood vessels, reduce cerebral vascular resistance, increase cerebral blood flow, improve microcirculation, improve blood-brain barrier permeability, enhance the phagocytic immune function of macrophages in the body, and resist pituitrin. The result is cerebral ischemia and hypoxia, and can resist platelet aggregation caused by adenosine diphosphate (ADP). Breviscapine is widely used clinically to treat paralysis caused by cerebral thrombosis, cerebral infarction and undetermined types of post-stroke paralysis, hypertension, cerebral embolism, multiple neuritis, chronic arachnoid and other cerebrovascular accidents, as well as coronary heart disease, angina pectoris, Treatment of gouty arthritis and other diseases.

[0031] The activity of compound ...

experiment example 2

[0100] Experimental example 2 Comparative study on the solubility of compound A1 of the present invention and scutellarin

[0101] Table 7 Solubility comparison of compound A1 of the present invention and scutellarin

[0102]

[0103] Note: According to the 2005CP regulations, the definitions of extremely soluble, easily soluble, soluble, slightly soluble, slightly soluble, very slightly soluble, almost insoluble and insoluble.

[0104] It can be seen from Table 7 that, compared with scutellarin, compound A1 of the present invention has significantly improved biophysical and chemical properties, that is, both water solubility and fat solubility have been significantly improved, and its bioavailability can be significantly improved, and its curative effect can be improved.

[0105] The application of the compounds of the present invention in the preparation of pharmaceutical preparations is illustrated by the following examples.

[0106] Formulation Preparation Example 1: P...

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Abstract

The invention discloses a 4',5,6-trimethoxy scutellarin as well as a preparation method and a pharmaceutical composition thereof. The compound is prepared by the methyl ether reaction of scutellarin functioning as an initial raw material and then the separation by a silica gel column. The compound and the pharmaceutical composition thereof can be used for treating cardiovascular and cerebrovascular disease, phlegmasia and tumor and has the advantages of good dissolvability, high bioavailability and remarkable curative effect.

Description

technical field [0001] The present invention relates to scutellarin derivatives, in particular to a novel scutellarin derivative, a preparation method thereof, a pharmaceutical composition containing the compound, and their application in heart and cerebrovascular diseases and the like. Background technique [0002] Erigeron breviscapus, also known as Erigeron breviscapus, belongs to the genus Fabaceae. Breviscapine is isolated and extracted from the whole plant of Breviscapus breviscapus, mainly containing scutellarin (>90%), and also contains a small amount of scutellarin (effective part). Breviscapine is also called wild scutellaria Glycosides. Breviscapine has the effects of promoting blood circulation and removing blood stasis, dispelling cold and relieving the surface, relaxing tendons and activating collaterals, expelling wind and dampness, and is often used clinically to treat cardiovascular and cerebrovascular diseases. Currently, the active ingredients of scut...

Claims

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Application Information

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IPC IPC(8): C07H17/07A61K31/7048A61P9/00A61P29/00A61P35/00
CPCA61K9/0019C07H17/07A61K9/2054A61K9/19A61K31/7048A61K9/2018A61K47/26A61K9/0043C07H7/033A61K47/10A61K9/0056A61K9/2059A61P9/00A61P29/00A61P35/00
Inventor 朱华结金毅徐树光杨兆祥普俊学
Owner KPC PHARM INC
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