Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

13, 13a- dihydro berberine derivant, pharmaceutical composition and uses of the same

A technology of dihydroberberine and its derivatives, applied in 13 fields, can solve problems such as poor solubility of compounds, difficulty in reaching the body through oral absorption, and restrictions on further application

Inactive Publication Date: 2008-04-02
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
View PDF4 Cites 56 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0024] To sum up, berberine has obvious effects in the treatment of diabetes, but the compound has poor solubility and is difficult to reach the body after oral absorption.
This limits its further application in the treatment of diabetes, so it is necessary to study the relationship between the structure and activity of this compound in depth, and to find berberine derivatives with stronger activity and better absorption in vivo

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 13, 13a- dihydro berberine derivant, pharmaceutical composition and uses of the same
  • 13, 13a- dihydro berberine derivant, pharmaceutical composition and uses of the same
  • 13, 13a- dihydro berberine derivant, pharmaceutical composition and uses of the same

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0062] Preparation of compound 2

[0063] 8-Acetonyl dihydroberberine (3 g) and methyl iodide were dissolved in 100 mL of dichloromethane, heated to 100° C. under pressure and reacted for 3 hours. After the reaction, the solid by-product was filtered off, and the filtrate was evaporated to dryness under reduced pressure. The residue was recrystallized in methanol to obtain compound 2 (1.53 g, 48%).

[0064] Compound 2, C 21 h 20 INO 4 , MW: 477; yellow crystals, easily soluble in mixed solvents of chloroform and methanol.

[0065] 1 H NMR (300MHz, DMSO-d 6 ): δ9.89(1H, s, H-8), 8.20(1H, d, J=9.0Hz, H-12), 8.19(1H, d, J=9.0Hz, H-11), 7.48(1H , s, H-1), 7.15 (1H, s, H-4), 6.18 (2H, s, -OCH 2 O-), 4.80 (2H, m, H-6), 4.10 (3H, s, -OCH 3 ), 4.09 (3H, s, -OCH 3 ), 3.15 (2H, m, H-5), 2.92 (3H, s, -CH 3 ).

[0066] Preparation of compound 3

[0067]8-Acetonyl dihydroberberine (1.5g) and ethyl bromide were dissolved in 100mL of dichloromethane, heated to 100°C under pressu...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention provides a 13,13a-dihydro berberine derivative with a structure shown in the right formula or physiologically acceptable salt, the application and the drug composition containing the derivative. The 13,13a-dihydro berberine derivative has the function of promoting muscle cells to absorb glucose. The overall animal experiment shows that the category of compounds has the functions of improving glucose tolerance and insulin resistance, reducing obesity, easing fatty liver and so on. The category of compounds can be used for treating diabetes, obesity, fatty liver and the complication caused by insulin resistance.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to 13,13a-dihydroberberine derivatives which can be used as insulin sensitizers, pharmaceutical compositions and medical applications thereof. Background technique [0002] Diabetes mellitus (diabetes mellitus) is a group of clinical metabolic diseases caused by the interaction of genetic and environmental factors. Due to the absolute or relative insufficiency of insulin secretion and the decreased sensitivity of target tissue cells to insulin, sugar, protein, fat, water and electrolyte and other metabolic disorders. Clinically, hyperglycemia is the main common sign. Prolonged illness can cause damage to multiple systems. Acute metabolic disorders such as ketoacidosis can occur when the condition is severe and stressful. Severe complications such as cardiovascular disease, kidney damage, blindness, and gangrene of the extremities were significantly highe...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/03A61K31/4375A61P3/10A61P3/04A61P1/16
CPCC07D455/03A61P1/16A61P3/04A61P3/06A61P3/10
Inventor 胡立宏李佳戴维·E·詹姆斯爱德华·W·克如艾根李静雅章涵堃程哲叶冀明
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com