Bicyclol-based derivative, preparation and applications thereof

A derivative, bicyclic alcohol technology, applied in the field of medicinal chemistry, to achieve the effect of improving the pathological damage of liver tissue, improving the survival rate of liver cells, and prolonging the survival time

Active Publication Date: 2017-12-19
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, less specifically bicyclols

Method used

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  • Bicyclol-based derivative, preparation and applications thereof
  • Bicyclol-based derivative, preparation and applications thereof
  • Bicyclol-based derivative, preparation and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis of embodiment 1 compound WLP-S-17

[0036]

[0037] a. SOCl 2 / DMF; b.TEA / CH 2 Cl 2 or CH 3 COCH 3 ; c.CH 3 SO 3 H / CH 3 Oh

[0038] 5.1g (13.1mmol) of compound 1 (i.e., bicyclic alcohol) was placed in a 100ml three-neck flask with magnetic stirring and a thermometer, and 50ml of dry DMF was added to dissolve the solid completely. After cooling to 0°C in an ice bath, slowly add 4.5ml ( 61.8mmol) of SOCl 2 , control the system temperature not to exceed 5°C. After the dropwise addition, the mixture was reacted in an ice bath for 30 min until TLC showed that the reaction of the raw materials was complete. Pour the reaction system into about 100 g of crushed ice, stir well, a large amount of white solid precipitates out, filter it, wash the filter cake with a small amount of distilled water and diethyl ether successively, and drain it. Air-dried and weighed to obtain a total of 4.9 g of white solid (compound 2), yield: 91.7%. MS-FAB: [M+2H]+=410....

experiment example 1

[0042] Experimental example 1 utilizes CCl 4 Induced mouse acute liver injury model detects embodiment compounds

[0043] 1 CCl 4 Establishment of induced acute liver injury model in mice and administration method

[0044] SPF grade male ICR mice (20-22g), were randomly divided into 14 groups after adapting to the environment, blank control group, CCl 4 Model group, WLP-S-17 tail vein 0.5mg / kg group, WLP-S-17 tail vein 1.6mg / kg group, WLP-S-17 tail vein 5mg / kg group, WLP-S-17 tail vein 16mg / kg group kg group, WLP-S-17 tail vein 50mg / kg group, WLP-S-17 oral 1mg / kg group, WLP-S-17 oral 3.2mg / kg group, WLP-S-17 oral 10mg / kg group, WLP - S-17 oral administration 32mg / kg group, WLP-S-17 oral administration 100mg / kg group, bicyclol 200mg / kg group and Ganlixin 100mg / kg group, 8-10 rats in each group. Each tail vein administration group of WLP-S-17 and Ganlixin injection group started tail vein administration 3 days before modeling, and administered once a day for a total of 3 day...

experiment example 2

[0077] Experimental Example 2 Using the ConA-induced acute immune liver injury model in mice to detect the compounds of the examples

[0078] 1. Establishment of ConA-induced acute immune liver injury model in mice and administration method

[0079] SPF male ICR mice (20-22g) were randomly divided into 9 groups after adapting to the environment, blank control group, model group, WLP-S-17 100mg / kg orally administered group, WLP-S-17 50mg / kg orally administered Group, WLP-S-17 tail vein 50mg / kg group, WLP-S-17 tail vein 25mg / kg group, WLP-S-17 tail vein 12.5mg / kg group, positive control drug bicyclol 200mg / kg group, positive Control drug Ganlixin 100mg / kg group. There are 9-10 animals in each group. Each tail vein administration group of WLP-S-17 and Ganlixin injection group started tail vein administration 3 days before modeling, and administered once a day for a total of 3 days. Bicyclol group and WLP-S-17 The intragastric administration group was intragastrically administe...

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PUM

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Abstract

The present invention belongs to the field of medicinal chemistry, and particularly relates to a bicyclol-based derivative and a pharmaceutically acceptable salt thereof, a preparation method of the bicyclol-based derivative, and applications of the bicyclol-based derivative in preparation of drugs for prevention and/or treatment of liver diseases and the like. The formula I is defined in the specification.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a therapeutic bicyclic alcohol derivative and its preparation and application, especially the application in the treatment and / or prevention of liver diseases and related diseases. Background technique [0002] Liver disease is a worldwide disease, and my country is a big country with liver disease. At present, there are a large number of patients with liver injury and liver inflammation caused by various reasons in my country, mainly viral hepatitis. According to statistics, the direct economic loss due to chronic hepatitis (including liver cirrhosis and liver cancer caused in the later stage) in my country reaches 900 billion yuan every year. In recent years, the incidence of drug-induced liver disease, alcoholic and non-alcoholic fatty liver disease, and autoimmune liver disease has also been increasing year by year. Finding safe and effective drugs for the prev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/68A61K31/5377A61P1/16A61P31/14A61P31/20A61P37/02
CPCC07D317/68Y02A50/30
Inventor 吴松孙华张文轩王少媛武丽萍童元峰刘宁张丹
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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