A kind of medicine for treating hepatitis B and its preparation method

A pharmacy and compound technology, applied in the field of medicine, can solve the problems of poor curative effect, easy recurrence of drug withdrawal, drug resistance, etc., and achieve the effects of good inhibitory effect, excellent anti-hepatitis B virus activity, and low toxicity.

Active Publication Date: 2018-08-03
MUDANJIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nucleoside analogues against HBV have the characteristics of significant curative effect, convenient administration, high bioavailability, and good tolerance of patients. The disadvantages are that the curative effect is not long-lasting, the disease is prone to relapse after drug withdrawal, and the virus develops drug-resistant mutations.
[0004] To sum up, there is a very large market demand for anti-hepatitis drugs, but the problem of drug resistance is common in clinically used anti-hepatitis drugs. A new generation of anti-hepatitis B drug with high clinical efficiency and less toxic side effects

Method used

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  • A kind of medicine for treating hepatitis B and its preparation method
  • A kind of medicine for treating hepatitis B and its preparation method
  • A kind of medicine for treating hepatitis B and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: (E)-3-((5-methylpyrimidin-4-yl)methylene)-6-(pyrrolidin-1-ylmethyl)isoindol-1-one (MIDO-1 )Synthesis

[0048]

[0049] Step 1: Mix 3.71 g of 6-(bromomethyl)isoindol-1-one, 1.42 g of tetrahydropyrrole, and 7.31 g of cesium carbonate in 50 mL of THF under a nitrogen atmosphere at -5°C. The reaction solution was warmed to room temperature and stirred overnight. The resulting solution was diluted with 200 mL water and then extracted with 3×100 mL ethyl acetate. The combined organic layer was washed once with 100 mL water and 100 mL brine each and dried over anhydrous calcium chloride. The solvent was removed by rotary evaporation, and the residue was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1:5) to obtain 3.17 g of intermediate 6-(pyrrolidin-1-ylmethyl)isoindol-1-one , The yield is 89.0%.

[0050] ESI-MS: 217.13[M+H] +

[0051] Step 2: Dissolve 1.46g of 5-methylpyrimidine-4-carbaldehyde in 150ml of absolute ethanol, then add 2....

Embodiment 2

[0055] Example 2: (E)-3-((6-hydroxypyrimidin-4-yl)methylene)-6-(piperazin-1-ylmethyl)isoindol-1-one (MIDO-2) Synthesis

[0056]

[0057] Step 1: Mix 3.71 g of 6-(bromomethyl)isoindol-1-one, 1.72 g of piperazine, and 7.31 g of cesium carbonate in 80 mL of THF at -5°C under a nitrogen atmosphere. The reaction solution was warmed to room temperature and stirred overnight. The resulting solution was diluted with 200 mL water and then extracted with 3×100 mL ethyl acetate. The combined organic layer was washed once with 100 mL water and 100 mL brine each and dried over anhydrous calcium chloride. The solvent was removed by rotary evaporation, and the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to obtain 3.33 g of intermediate 6-(piperazin-1-ylmethyl)isoindol-1-one , The yield is 87.3%.

[0058] ESI-MS: 232.14[M+H] +

[0059] Step 2: Dissolve 1.48g of 6-hydroxypyrimidine-4-carbaldehyde in 100ml of absolute ethanol, then add 2.32g of 6-(piperaz...

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PUM

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Abstract

The invention relates to a medicine with a remarkable anti-hepatitis B effect. A structure of the medicine is shown as a formula 1 as shown in the specification. A compound which is low in toxicity has a great inhibition effect on HBsAg and HBeAg secreted by Hep G2.2.15 cells in vitro and has a therapeutic index remarkably higher than lamivudine, thereby being suitable for serving as the medicinefor hepatitis B treatment.

Description

Technical field [0001] The present invention belongs to the technical field of medicines. Specifically, the present invention relates to a medicine for treating hepatitis B, a preparation method thereof, and application of the medicine for treating hepatitis B. Background technique [0002] Hepatitis B is a viral infectious disease that seriously endangers human health. According to the World Health Organization, there are more than 2 billion people in the world who are carriers of the hepatitis B virus, and about 300 million of them have chronic lifelong infections with the disease. These patients with chronic hepatitis tend to become chronic hepatitis, which is the main cause of liver cirrhosis and liver cancer. Hepatitis B virus (HBV) belongs to the DNA hepatitis virus family, which is mainly transmitted through blood products, mother-to-child and sexual contact. Its replication process involves 5 steps: binding, invasion, transcription, translation, and gene replication And...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/06A61K31/506A61K31/5377A61P1/16A61P31/20
CPCC07D403/06
Inventor 乔宏王永波韩莹刘洋毕莉莉张春红
Owner MUDANJIANG MEDICAL UNIV
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