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N'-Aroyl o-pyridine hydrazide derivatives and its preparation method, pharmaceutical composition and application

A kind of technology of pyridine hydrazide and derivatives, applied in the field of medicine

Active Publication Date: 2018-09-25
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

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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  • N'-Aroyl o-pyridine hydrazide derivatives and its preparation method, pharmaceutical composition and application
  • N'-Aroyl o-pyridine hydrazide derivatives and its preparation method, pharmaceutical composition and application
  • N'-Aroyl o-pyridine hydrazide derivatives and its preparation method, pharmaceutical composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Example 1.1-(4-(2-(2-(3-p-chlorophenylacryloyl)hydrazinecarbonyl)pyridine-4-oxyl)phenyl)-3-(4-chloro-3-trifluoromethyl Phenyl)urea

[0074]

[0075] Synthesis of N'-(3-p-chlorophenylacryloyl)-4-(p-aminophenoxy)pyridine-2-hydrazide

[0076] Dissolve 105mg (0.43mmol) of compound 4-(p-aminophenoxy)pyridine-2-hydrazide in 7ml THF, add 0.09mL (0.64mmol) TEA, dropwise add 2ml dissolved in 0.52mmol 3-p-chlorophenylacryloyl chloride After refluxing for 4 hours, a white solid was formed, the reaction was stopped, filtered, washed with a small amount of tetrahydrofuran, washed with water, and dried to obtain N'-(3-p-chlorophenylacryloyl)-4-(p-aminophenoxy Base) pyridine-2-hydrazide, white solid 60mg. 1 H NMR (400MHz, DMSO-d 6 ):10.59(br,1H,-CONH 2 -),10.48(s,1H,-CONH-),8.52(d,1H,Ar-H),7.56(m,3H,Ar-H),7.49(m,4H,Ar-H),6.88(d ,2H,Ar-H),6.73(d,1H,-CH=CH-Ar),6.65(d,1H,Ar-H),5.19(s,2H,Ar-NH 2 ).MS(FAB):(M + +1=409).

[0077] 1-(4-(2-(2-(3-p-chlorophenylacryloyl)hydrazinecarb...

Embodiment 2

[0082] Example 2.1-(4-(2-(2-(3-trifluoromethylphenylacryloyl)hydrazine carbonyl)pyridine-4-oxyl)phenyl)-3-(4-chloro-3-tri Fluoromethylphenyl) urea

[0083]

[0084] Using 3-m-trifluoromethylphenylacrylic acid instead of 3-p-chlorophenylacrylic acid, the procedure of Example 1 was followed to obtain 175 mg of the target compound as a white solid. 1 H NMR (400MHz, DMSO-d 6 ):10.65(m,2H,-CONH-),9.39(s,1H,-CONH-),9.16(s,1H,-CONH-),8.57(d,1H,Ar-H),8.03(m, 3H,Ar-H),7.61(m,7H,Ar-H,=CH-Ph),7.40(s,1H,Ar-H),7.20(m,3H,Ar-H),6.86(d,1H ,-COCH=).MS(FAB)(M + +1=664)

Embodiment 3

[0085] Example 3.1-(4-(2-(2-(3-o-p-dichlorophenylacryloyl)hydrazinecarbonyl)pyridine-4-oxyl)phenyl)-3-(4-chloro-3-trifluoro Methylphenyl) urea

[0086]

[0087] Using 3-o-p-dichlorophenylacrylic acid instead of 3-p-chlorophenylacrylic acid, and referring to the operation of Example 1, 135 mg of the target compound was obtained as a white solid. 1 H NMR (400MHz, DMSO-d 6 ):10.64(br,2H,-CONH-),9.46(s,1H,-CONH-),9.23(s,1H,-CONH-),8.56(d,1H,Ar-H),8.12(s, 1H,Ar-H),7.87(m,1H,Ar-H),7.72(m,3H,Ar-H,=CHPh),7.40(m,3H,Ar-H),7.40(m,3H,Ar -H),6.78(d,1H,-COCH=);MS(FAB)(M + +1=664)

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Abstract

The invention discloses N'-aryl acryloyl o-pyridine hydrazide derivatives represented by the formula I and pharmaceutically acceptable salts and preparation methods thereof, a composition containing one or more of the compounds, and an application of the compounds in treatment of protein kinase related diseases, such as immune disorder and tumor disease.

Description

field of invention [0001] The present invention relates to N′-aryl acryloyl o-pyridine hydrazide 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 The protein kinase-related diseases, such as immune disorders and tumor diseases, belong to the field of medical technology. Background of the invention [0002] 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 k...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/86C07D405/12C07D409/12A61K31/44A61K31/443A61K31/4436A61K31/4406A61P35/00A61P35/02
CPCC07D213/86C07D405/12C07D409/12
Inventor 冯志强陈晓光王克李燕张莉婧唐克
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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