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Benzimidazole compounds and their applications

A technology of benzimidazoles and compounds, applied in the field of biopharmaceuticals, can solve problems such as high toxicity and side effects, high treatment costs, and poor efficacy

Inactive Publication Date: 2015-08-05
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is currently no cure for autoimmune diseases, and most of the existing therapeutic drugs are in the form of injections, with poor curative effect, high toxicity and side effects, and very expensive treatment costs. There is an urgent need to develop new oral therapeutic drugs that meet pharmacoeconomics

Method used

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  • Benzimidazole compounds and their applications
  • Benzimidazole compounds and their applications
  • Benzimidazole compounds and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of compound 1

[0034]

[0035] N, the preparation of 4-dimethyl-2-nitroaniline (A)

[0036] Add 4-methyl-2-nitroaniline (3g, 0.02mol), NaH (60%, 1.2g, 0.03mol), THF (50ml) in the 100ml round bottom flask, after stirring for 0.5h, add MeI (4.26g , 0.03mol), react overnight. Post-reaction treatment: After cooling the reaction system, add saturated brine and ethyl acetate, separate the layers, and wash the organic layer once with saturated brine. Purification by dry concentration and column chromatography (developing solvent: PE:EA=8:1) gave N,4-dimethyl-2-nitroaniline (A) with a yield of 91%.

[0037] N1, the preparation of 4-dimethyl-o-phenylenediamine (B)

[0038] Add N,4-dimethyl-2-nitroaniline (A) (1 g, 6 mmol), Pd / C (0.1 g), MeOH (30 ml) into a 100 ml round-bottomed flask and react overnight with hydrogen. Post-reaction treatment: Pd / C was removed by filtration, and the filtrate was dried and concentrated to obtain Compound B with a yield of 95%. ...

Embodiment 2

[0142] 1. Pharmacological tests of benzimidazole compounds

[0143] 1) Proliferation test of mouse T cells activated by anti-CD3 / anti-CD28

[0144] Four lymph nodes in the groin and armpit of the mice were taken to prepare a single cell suspension. Make 3×10 with complete medium RPMI-1640 6 / ml of cell suspension, seeded in 96-well plate, 3×10 5 Cells per well were stimulated with a final concentration of 10 μg / ml anti-CD3 and 1 μg / ml anti-CD28 (purchased from BD PharMingen) for 72 hours, incubated with compounds, and the proliferation of lymphocytes was detected by isotope tritium labeling.

[0145] 2) Anti-CD3 / anti-CD28 activated mouse T cells secreted cytokine IFN-γ test

[0146] Four lymph nodes in the groin and armpit of the mice were taken to prepare a single cell suspension. Make 3×10 with complete medium RPMI-1640 6 / ml of cell suspension, seeded in 96-well plate, 3×10 5 Cells per well were stimulated with a final concentration of 10 μg / ml anti-CD3 and 1 μg / ml an...

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Abstract

The invention belongs to the technical field of bio-pharmaceuticals, and provides application of a benzimidazole compound serving as an immunosuppressor in preparation of medicines for treating autoimmune diseases in the presence of T cells, such as inflammatory bowel disease, rheumatoid arthritis, multiple sclerosis, systemic lupus erythematosus and autoimmunenephritis. A series of novel compounds synthesized by the benzimidazole compound have the advantages of being remarkable in efficacy, novel in mechanism, effective in oral taking, and less in toxic and side effects; and compared with a conventional medicine, the benzimidazole compound is remarkably advantaged in simple synthesis route and environment-friendly.

Description

technical field [0001] The invention particularly belongs to benzimidazole compounds and applications thereof, and belongs to the technical field of biopharmaceuticals. Background technique [0002] Autoimmune diseases are a kind of refractory diseases, and their pathogenesis is mostly related to the overactivation of T lymphocytes. At present, immunosuppressants are often used for treatment. Common autoimmune diseases include inflammatory bowel disease, rheumatoid arthritis, multiple sclerosis, systemic lupus erythematosus, autoimmune nephritis, etc. There is currently no cure for autoimmune diseases. Most of the existing therapeutic drugs are in the form of injections, which have poor curative effect, high toxicity and side effects, and very expensive treatment costs. There is an urgent need to develop new oral therapeutic drugs that meet pharmacoeconomics. Contents of the invention [0003] The object of the present invention is to provide a class of benzimidazole comp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/18A61P37/02A61P29/00A61P1/00A61P19/02A61P25/00A61P19/04A61P13/12
Inventor 徐强孙洋刘雯吴静郭文洁
Owner NANJING UNIV
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