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N'-aryl acetyl o-pyridine hydrazide derivatives, and preparation methods, pharmaceutical composition and application thereof

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

Active Publication Date: 2014-10-22
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'-aryl acetyl o-pyridine hydrazide derivatives, and preparation methods, pharmaceutical composition and application thereof
  • N'-aryl acetyl o-pyridine hydrazide derivatives, and preparation methods, pharmaceutical composition and application thereof
  • N'-aryl acetyl o-pyridine hydrazide derivatives, and preparation methods, pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Example 1.1-(4-(2-(2-(3-fluorophenylacetyl)hydrazinecarbonyl)pyridine-4-oxyl)phenyl)-3-(4-chloro-3-trifluoromethylphenyl) Urea

[0076]

[0077] Synthesis of 4-(p-aminophenoxy)pyridine-2-hydrazide

[0078] Add 1.6g of methyl 4-(p-aminophenoxy)pyridine-2-carboxylate into 10mL of methanol, add 0.5mL of hydrazine hydrate dropwise at 0°C, after the addition is complete, move to room temperature and react for 18 hours. TLC monitors that the reaction is complete , most of the solvent was distilled off under reduced pressure, filtered, and the filter cake was washed 3 times with methanol to obtain 1.4 g of off-white solid. 1 HNMR (300MHz, DMSO-d 6 ):9.84(s,1H,-CONH-),8.43(d,1H,Ar-H),7.30(s,1H,Ar-H),7.04(m,1H,Ar-H),6.88(s, 1H,Ar-H),6.85(s,1H,Ar-H),6.66(s,1H,Ar-H),6.63(s,1H,Ar-H),5.18(s,2H,Ar-NH 2 ),4.52(br,2H,CONH-NH 2 ).MS(FAB):(M + +1=245).

[0079] Synthesis of N'-m-fluorophenylacetyl-4-(p-aminophenoxy)pyridine-2-hydrazide

[0080] Dissolve 105mg (0.43mmol) of com...

Embodiment 2

[0086] Example 2.1-(4-(2-(2-(3-fluorophenylacetyl)hydrazinecarbonyl)pyridine-4-oxyl)o-fluorophenyl)-3-(4-chloro-3-trifluoromethylbenzene base) urea

[0087]

[0088] Utilize 4-(p-amino-m-fluorophenoxy)pyridine-2-methyl carboxylate to replace 4-(p-aminophenoxy)pyridine-2-methyl carboxylate, carry out with reference to the operation of Example 1, and obtain the target compound as white Solid 135mg. 1 H NMR (300MHz, DMSO-d 6 ):10.56(br,1H,-CONH-),10.30(br,1H,-CONH-),9.57(s,1H,-CONH-),8.77(s,1H,-CONH-),8.56(d, 1H,Ar-H),8.16(m,2H,Ar-H),7.63(s,2H,Ar-H),7.37(m,3H,Ar-H),7.17(m,5H,Ar-H) ,3.56(s,2H,-CH 2 -Ar).MS(FAB)(M + +1=620)

Embodiment 3

[0089] Example 3.1-(4-(2-(2-(3,5-dichlorophenylacetyl)hydrazine carbonyl)pyridine-4-oxyl)phenyl)-3-(4-chloro-3-trifluoromethyl Phenyl)urea

[0090]

[0091] Using 3,5-dichlorophenylacetic acid instead of m-fluorophenylacetic acid, the operation was carried out with reference to Example 1, and 135 mg of the target compound was obtained as a white solid. 1 H NMR (400MHz, DMSO-d 6 ): 10.53(s,1H,-CONH-),10.34(br,1H,-CONH-),9.37(s,1H,-CONH-),9.14(s,1H,-CONH-),8.54(s, 1H,Ar-H),8.12(s,1H,Ar-H),7.60(m,4H,Ar-H),7.38(s,1H,Ar-H),7.06(m,6H,Ar-H) ,3.57(s,2H,-CH 2 -).MS(FAB)(M + +1=653)

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Abstract

The invention discloses N'-aryl acetyl 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 acetyl-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 kin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/86C07D409/12C07D401/12C07D417/12A61K31/44A61K31/444A61K31/4439A61K31/4436A61K31/5415A61P35/00A61P37/02A61P25/00
CPCC07D213/86C07D401/12C07D409/12C07D417/12
Inventor 冯志强陈晓光张莉婧李燕王克唐克
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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