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Containing 2-anilino-4-thiazolyl pyridine derivative and its preparation method, pharmaceutical composition and application

A technology of methylthiazole and pyridine, applied in the field of treating tumor diseases

Active Publication Date: 2019-10-01
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, existing evidence shows that most tumors are not dominated by a single signaling pathway, and inhibition of multiple targets may achieve greater efficacy
Although many inventions have made great contributions to this field, in order to improve the therapeutic effect of drugs, this field is still researching

Method used

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  • Containing 2-anilino-4-thiazolyl pyridine derivative and its preparation method, pharmaceutical composition and application
  • Containing 2-anilino-4-thiazolyl pyridine derivative and its preparation method, pharmaceutical composition and application
  • Containing 2-anilino-4-thiazolyl pyridine derivative and its preparation method, pharmaceutical composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0214] Example 1.2-(m-trifluoromethylanilino)-4-(2-amino-4-methylthiazol-5-yl)pyridine

[0215]

[0216] 2-Bromo-4-(2-amino-4-methylthiazol-5-yl)pyridine (270mg, 1mmol) was added to 10ml of mixed solvent (1N HCl / H 2 O / Dioxane=2 / 4 / 1), heated to 80°C with stirring, added m-trifluoromethylaniline (242mg, 1.5mmol) after dissolution, raised the temperature, and refluxed until the reaction was complete. Cool to room temperature, pour the reaction solution into saturated aqueous sodium bicarbonate solution, filter, collect the solid, and purify by column chromatography to obtain the product 2-(m-trifluoromethylanilino)-4-(2-amino-4-methyl thiazol-5-yl)pyridine. 1 H-NMR(400MHz,DMSO-d6):δ(ppm):9.43(s,1H,-N H -),9.23(s,1H,Ar H ),8.14(d,1H,Ar H ),7.86(d,1H,Ar H ),7.47(t,1H,Ar H ),7.26(s,2H,-N H 2 ),7.18(d,1H,Ar H ),6.81(s,1H,Ar H ),6.77(d,1H,Ar H ),2.32(s,3H,-C H 3 ); m / z351.0[M+H] + .

Embodiment 2

[0217] Example 2.2-(2-chloro-6-methylanilino)-4-(2-amino-4-methylthiazol-5-yl)pyridine

[0218]

[0219] Replace m-trifluoromethylaniline with 2-chloro-6-methylaniline, and refer to the operation process of Example 1 to obtain 2-(2-chloro-6-methylanilino)-4-(2-amino-4 -Methylthiazol-5-yl)pyridine. 1 H-NMR(300MHz,DMSO-d6):δ(ppm):8.30(s,1H,-N H -),7.89(d,1H,Ar H ),7.36-7.34(d,1H,Ar H ),7.26-7.24(d,1H,Ar H ),7.19-7.14(m,3H,Ar H ,-N H 2 ),6.60-6.58(dd,1H,Ar H ),6.37(s,1H,Ar H ),2.23(s,3H,-C H 3 ),2.18(s,3H,-C H 3 ); m / z331.0[M+H] + .

Embodiment 3

[0220] Example 3.2-(2-fluoroanilino)-4-(2-amino-4-methylthiazol-5-yl)pyridine

[0221]

[0222] Replace m-trifluoromethylaniline with 2-fluoroaniline, and refer to the operation process of Example 1 to obtain 2-(2-fluoroanilino)-4-(2-amino-4-methylthiazol-5-yl)pyridine . 1 H-NMR(300MHz,DMSO-d6):δ(ppm):8.71(s,1H,-N H -),8.26-8.20(m,1H,Ar H ),8.05(d,1H,Ar H ),7.22-7.09(m,4H,-N H 2 , Ar H ),6.99-6.93(m,2H,Ar H ),6.73-6.70(m,1H,Ar H ),2.30(s,3H,-C H 3 ); m / z301.0[M+H] + .

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Abstract

The invention relates to 2-phenylamino-4-thiazolyl pyridine derivatives shown as a formula I, pharmaceutical salts thereof, a preparing method of the derivatives and the pharmaceutical salts, compositions containing one or more compounds selected from the derivatives and the pharmaceutical salts, and uses of the derivatives and the pharmaceutical salts in the field of tumor disease treatment.

Description

[0001] field of invention [0002] The present invention relates to 2-anilino-4-thiazolylpyridine derivatives shown in formula I, pharmaceutically acceptable salts thereof, and preparation methods thereof, compositions containing one or more of these compounds, and the use of such compounds in the treatment of tumors Disease use. [0003] Background of the invention [0004] In recent years, due to the improved understanding of enzymes and other disease-related biomolecules, the discovery or development of new drugs for the treatment of diseases has been greatly promoted. Protein kinases are an important class that has been extensively studied. It is a A large family involved in the control of various signal transduction processes in cells. Due to the conservation of their structure and catalytic function they are thought to have evolved from a common ancestral gene. Almost all kinases contain a similar 250-300 amino acid catalytic domain. These protein kinases are divided i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04A61K31/5377A61K31/4439A61K31/496A61P35/00A61P35/02
Inventor 冯志强陈晓光李燕张莉婧
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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