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Aminopyridine derivatives and uses thereof

A compound and pharmacological technology, applied in the field of inhibitors of activated lymphocyte proliferation, can solve the problems of inhibition and decrease of arthritis score

Inactive Publication Date: 2016-09-28
MITSUBISHI TANABE PHARMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, it was reported that in the type II collagen-induced arthritis model, compared with wild-type mice, the incidence of arthritis in IL-17-deficient mice was significantly suppressed (Non-Patent Document 2). Prophylactic or therapeutic administration of anti-mouse IL-17 neutralizing antibody in a protein-induced mouse arthritis model significantly reduces the arthritis score (Non-Patent Document 3), etc.

Method used

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  • Aminopyridine derivatives and uses thereof
  • Aminopyridine derivatives and uses thereof
  • Aminopyridine derivatives and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0345] Reference Example 1: 5-Methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carbonyl chloride

[0346] (1) Add 2-chloro-5-(trifluoromethyl)pyridine (25g) and hydrazine hydrate (100%) (100ml) to ethanol (60ml), stir at 100°C for 3 hours, and remove The reaction solution was concentrated, chloroform and water were added to the residue, the organic layer was separated, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and a 4N hydrochloric acid-ethanol solution was added to the residue to obtain 5-(three Fluoromethyl)pyridin-2-ylhydrazine hydrochloride (15.4 g). MS(ESI)m / z: 178(M+H) + .

[0347] (2) Next, ethyl 2-ethoxymethylene acetoacetate (6.1 g) synthesized according to the method described in J. Chem. Soc. Perkin trans. I), page 1875 (1988) and the above The 5-(trifluoromethyl)pyridin-2-ylhydrazine hydrochloride (7.0g) was added to a mixed solvent of water (40ml) and ethanol (40ml), stirred at reflux temperature for 3 hours, a...

reference example 2

[0349] Reference example 2: 1-(5-chloropyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid

[0350] In Reference Example 1, 2,5-dichloropyridine was used instead of 2-chloro-5-(trifluoromethyl)pyridine, and the title compound was obtained by the same reaction and treatment as (1) and (2). MS(ESI)m / z: 238(M+H) + .

reference example 3

[0351] Reference Example 3: 1-(3,5-Dichloropyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid

[0352] (1) Add 2,3,5-trichloropyridine (25g) and hydrazine monohydrate (109.8g) to ethanol (20ml), stir at 100°C, and then cool to room temperature. The resulting solid was collected by filtration to obtain 3,5-dichloropyridin-2-ylhydrazine (24.07 g).

[0353] (2) Next, 1N was added to ethyl 2-ethoxymethylene acetoacetate (25.1g) synthesized according to the method described in J.Chem.Soc.Perkin trans.I, page 1875 (1988) The aqueous solution of hydrochloric acid (135 ml) and the above-mentioned 3,5-dichloropyridin-2-ylhydrazine (24.02 g) in ethanol (135 ml) were stirred at reflux temperature for 3 hours and then cooled to room temperature. Water was added to the reaction solution, the resulting solid was filtered out, and purified with a mixed solvent of ethyl acetate / n-hexane to obtain 1-(3,5-dichloropyridin-2-yl)-5-methyl-1H -Ethyl pyrazole-4-carboxylate.

[0354] (3) Add 4N sodium ...

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Abstract

The present invention relates to a novel amidopyridine derivative. More specifically, there is provided a drug useful as a prophylactic / therapeutic drug for diseases based on cytokine production by T cells, comprising an amidopyridine derivative or a pharmacologically acceptable salt thereof as an active ingredient. An amidopyridine derivative or a pharmacologically acceptable salt thereof represented by the following general formula (I) [wherein, each symbol has the same meaning as described in the specification] is provided.

Description

Technical field [0001] The present invention relates to a novel amide pyridine derivative. In more detail, it relates to an activated lymphocyte proliferation inhibitor using a novel amide pyridine derivative or a pharmacologically acceptable salt or a solvate thereof as an active ingredient. [0002] The present invention relates to the prevention and / or treatment of autoimmune diseases and inflammatory / allergic diseases by inhibiting the production of cytokines, particularly interleukin 17 (hereinafter, sometimes referred to as "IL-17") by T cells. Useful amide pyridine compounds and their medical uses. Background technique [0003] Autoimmune diseases are diseases induced by incomplete removal of autoreactive lymphocytes in the thymus. Among them, rheumatoid arthritis (hereinafter, sometimes referred to as "RA") is a progressive inflammatory disease that causes joint pain, swelling, and inflammation due to unknown causes and spreads throughout the body. If these symptoms conti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14A61K31/444A61K31/4545A61P19/02A61P29/00A61P37/02A61P43/00C07D409/14C07D417/14C07D491/113
CPCC07D401/14C07D409/14C07D417/14C07D491/113A61P19/02A61P29/00A61P37/00A61P37/02A61P43/00
Inventor 渡边雅之古川博之滨田真以子藤江直人牛尾博之高岛彻
Owner MITSUBISHI TANABE PHARMA CORP