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Benzimidazole compounds, its prepn. and uses

A technology of benzimidazoles and compounds, applied in the field of benzimidazoles compounds, can solve the problems of inability to be universally vaccinated due to immune effects, treatment of hepatitis B patients, serious side effects, etc.

Inactive Publication Date: 2006-09-20
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] To sum up, the current treatment of hepatitis B is an arduous and urgent task for our country and even the world. Although the hepatitis B vaccine has been successfully developed, it cannot be used due to many problems in its promotion, use and immune effect. For the tens of millions of chronic hepatitis B patients in my country, drug treatment is still the main way
Although several drugs including α-interferon, lamivudine, and Adefovir have been used clinically, they cannot achieve better treatment for hepatitis B patients due to their relatively serious side effects. The advent of new anti-HBV drugs is still urgently needed, especially the advent of drugs with new mechanisms of action

Method used

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  • Benzimidazole compounds, its prepn. and uses
  • Benzimidazole compounds, its prepn. and uses
  • Benzimidazole compounds, its prepn. and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0591] Example 1 Synthesis of 2-[2-(1H-benzimidazol-2-yl)-ethyl]-isoindole-1,3-dione (BMHPY)

[0592] Mix 11g (0.05mole) 3-phthalimidopropionic acid and 5.4g (0.05mole) o-phenylenediamine evenly, add 50g polyphosphoric acid (PPA), react at 175-180°C for 6 hours, cool Then pour into cold water, filter, and the filtrate is neutralized to alkaline (pH>12) with concentrated ammonia water, and the product is filtered out, which can be directly used in the next step without purification. A total of 12.4 g was obtained after drying, and the yield was 85.1%. 1 H-NMR (400Hz, DMSO-d 6 )δ12.2-12.4 (br s, 1H), 7.82-7.87 (m, 4H), 7.42-7.46 (m, 2H), 7.10-7.13 (m, 2H), 4.01-4.05 (t, 2H, J= 7.2Hz), 3.14-3.18(t, 2H, J=7.2Hz); MS (M + )291.

Embodiment 2

[0593] Example 2 Synthesis of 2-[2-(5,6-dichloro-1H-benzimidazol-2-yl)-ethyl]-isoindole-1,3-dione (BMCPY)

[0594] 3-phthalimidopropionic acid and equivalent 4,5-dichloro-o-phenylenediamine were prepared according to the method of BMHPY to obtain 14.8 g of the product with a yield of 82.2%.

[0595] 1 H-NMR (400Hz, DMSO-d 6 )δ12.5-12.7 (br s, 1H), 7.81-7.86 (br s, 4H), 7.71 (s, 2H), 4.00-4.03 (t, 2H, J=7.2Hz), 3.15-3.18 (t, 2H, J=7.0Hz);

[0596] MS (M + )359.

Embodiment 3

[0597] Example 3 Synthesis of 2-[2-(5,6-difluoro-1H-benzimidazol-2-yl)-ethyl]-isoindole-1,3-dione (BMFPY)

[0598] 3-phthalimidopropionic acid and equivalent 4,5-difluoro-o-phenylenediamine were prepared according to the method of BMHPY to obtain 13.6 g of the product with a yield of 82.9%.

[0599] 1 H-NMR (400Hz, DMSO-d 6 )δ12.4-12.6 (br s, 1H), 7.82-7.86 (br s, 4H), 7.46-7.50 (m, 2H), 3.98-4.02 (t, 2H, J=7.6Hz), 3.13-3.17 ( t, 2H, J=7.6Hz);

[0600] MS (M + )327.

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Abstract

This invention provides substituted benzimidazole compounds shown in common formula (I) and their pharmacologically permitted salts. The definitions of R1, R2, R3, R4 and n in common formula (I) are mentioned in the instruction. Pharmacological experiments show that, this kind of compounds and their pharmacologically permitted salts or their solvates or hydrates perform excellent anti-hepatitis B virus (anti-HBV) activities and are especially inhibitory to DNA replication of HBV. They are thus promising as anti-HBV drugs. This invention also provides a method to prepare this kind of compounds.

Description

technical field [0001] The invention relates to a class of benzimidazole compounds with anti-hepatitis B virus activity and a preparation method of the compounds. And the application of this type of compound in anti-hepatitis B virus treatment. Background technique [0002] Hepatitis B virus (HBV) belongs to the hepadanaviridae family and is one of the main pathogens causing viral hepatitis. Among the currently known pathogens causing viral hepatitis (mainly including hepatitis A, B, C, D, E, and G viruses, Epstein-Barr virus, cytomegalovirus, rubella virus, etc.), hepatitis B caused by HBV It is an infectious disease that has been popular for a long time, spread widely and is seriously harmful. At present, there are about 2 billion people infected with HBV in the world, and it is estimated that there are more than 350 million people with chronic hepatitis B infection (such as hepatitis B virus carriers). As a high-endemic area of ​​hepatitis B, China accounts for nearly ...

Claims

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Application Information

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IPC IPC(8): C07D235/06C07D403/04C07D403/06C07D471/04A61P31/14A61P1/16
Inventor 吕伟左建平李云飞王桂凤
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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