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
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  • 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

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  • 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

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Experimental program
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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...

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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

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Application Information

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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
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