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Phenyl benzylamine compound and application thereof

A technology of phenylbenzylamine and compounds, applied in the field of biopharmaceuticals, can solve the problems of high toxicity and side effects, high treatment costs, and poor curative effect

Inactive Publication Date: 2012-08-08
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 therapeutic drugs that meet pharmacoeconomics

Method used

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  • Phenyl benzylamine compound and application thereof
  • Phenyl benzylamine compound and application thereof
  • Phenyl benzylamine compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081]

[0082] Preparation of N-benzyl-4-methyl-o-nitroaniline (II)

[0083] Add 4-methyl-o-nitroaniline (200g, 1.32mol) to the four-necked bottle, K 2 CO 3 (20g, 0.5mol) and benzyl bromide (200ml), DMF (1.2ml) were slowly added dropwise to the reaction solution. Raise the temperature to 190°C to 200°C. The degree of reaction was detected by TLC (developing solvent: PE:EA=1:9). The reaction product was poured into distilled water, and a solid precipitated out. Suction filtration, filtrate with CH 2 Cl 2 Extract 3 (200ml*3) times, combine CH 2 Cl 2 layer and suction filtered the resulting solid. It was washed once more with water, dried and concentrated. Finally, the pure product was obtained by recrystallization from ethyl acetate with a yield of 58%.

[0084] Preparation of N1-benzyl-4-methyl-o-phenylenediamine (III)

[0085] Add N-benzyl-4-methyl-o-nitroaniline (10g, 0.04mol) in a 500ml eggplant-shaped bottle, SnCl 2 .2H 2 O (95g, 0.44mol), ethanol (80ml), s...

Embodiment 2

[0182] 1. Pharmacological tests of phenylbenzylamine compounds

[0183] 1) Proliferation test of mouse T cells activated by anti-CD3 / anti-CD28

[0184] 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.

[0185] 2) MOG 35-55 T-lymphocyte proliferation and cytokine release test in EAE-induced model mice

[0186] Take MOG 35-55 (purchased from Shanghai Qiangyao Biotechnology Co., Ltd.) and complete Freund's adjuvant (purchased from sigma company) emulsion sensitized for 10 days, four lymph nodes in the inguinal and axilla of mice were prepared into a single cell suspension. Make 3...

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Abstract

The invention belongs to the technical field of biological pharmacy and provides application of phenyl benzylamine compounds as immunosuppressant in preparation of medicament for treating T cell participated autoimmune diseases, such as multiple sclerosis, systemic lupus erythematosus, rheumatoid arthritis, autoimmune nephritis and inflammatory bowel disease. A series of novel compounds synthesized from phenyl benzylamine compounds have significant efficacy, novel mechanism, little toxic or side effects; and as the synthetic route is simple and environment-friendly, the novel compounds have obvious advantages compared with existing ones.

Description

technical field [0001] The invention particularly belongs to phenylbenzylamine 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 multiple sclerosis, systemic lupus erythematosus, rheumatoid arthritis, autoimmune nephritis, inflammatory bowel disease, etc. There is currently no cure for autoimmune diseases. 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 therapeutic drugs that meet pharmacoeconomics. 3. Contents of the invention [0003] The object of the present invention is to provide a class of phenylbenzylamine comp...

Claims

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Application Information

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IPC IPC(8): C07C237/04C07C237/40C07C237/20C07C231/12C07C323/60C07C319/20C07D209/20A61K31/167A61K31/405A61P37/02A61P19/02A61P29/00A61P13/12A61P1/00
Inventor 谭仁祥徐强孙洋吴汉夔戈惠明龚方苑罗琼郭文洁
Owner NANJING UNIV
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