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

A kind of arylformyl ortho, pyridine hydrazide technology, applied in the field of medicine

Active Publication Date: 2014-10-22
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although many inventions have made great contributions to this field, in o...

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1.1-(4-chloro-3-trifluoromethylphenyl)-3-(4-(2-(2-(p-methoxybenzoyl)hydrazinecarbonyl)pyridine-4-oxyl)phenyl ) urea

[0075]

[0076] Synthesis of N'-p-methoxybenzoyl-4-chloropyridine-2-hydrazide

[0077] Dissolve 1.1g (7.0mmol) of p-methoxybenzoic acid in 3mL DMF, add raw materials 1g (5.8mmol) of 4-chloropyridine-2-hydrazide, 2.7g (7.0mmol) of HATU, 1.8g of triethylamine ( 17.4mmol), stirred at room temperature, TLC monitored the complete reaction of raw materials, added 100mL of water, a large amount of off-white solid precipitated, and 1.67g of the product was obtained. 1 H NMR (400MHz, DMSO-d 6 ):10.68(s,1H,-CONH-),10.44(s,1H,-CONH-),8.70(d,1H,Ar-H),8.07(s,1H,Ar-H),7.90(d, 2H,Ar-H),7.84(d,1H,Ar-H),7.05(d,2H,Ar-H),3.84(s,3H,-O-CH 3 ).MS(FAB):(M + +1=306).

[0078] Synthesis of N'-p-methoxybenzoyl-4-(p-aminophenoxy)pyridine-2-hydrazide

[0079] Dissolve 469mg (4.3mmol) of p-aminophenol in 10mL of DMF, add 648mg (5.3mmol) of potassium tert-butoxide u...

Embodiment 2

[0081] Example 2.1-(4-(2-(2-(6-Hydroxynicotinoyl)hydrazinecarbonyl)pyridine-4-oxyl)phenyl)-3-(4-chloro-3-trifluoromethylphenyl) Urea

[0082]

[0083] Using 6-hydroxynicotinic acid instead of p-methoxybenzoic acid, referring to the operation of Example 1, 175 mg of the target compound was obtained as a white solid. 1 H NMR (300MHz, DMSO-d 6 ):10.86(m,2H,-CONH-),9.33(s,1H,-CONH-),9.11(s,1H,-CONH-),8.53(dd,1H,Ar-H),8.12(m, 2H,Ar-H),7.86(d,1H,Ar-H),7.63(m,4H,Ar-H),7.36(m,1H,Ar-H),7.19(m,3H,Ar-H) ,6.38(d,1H,Ar-H).MS(FAB)(M + +1=587)

Embodiment 3

[0084] Example 3.1-(4-(2-(2-(pyridine-2-formyl)hydrazinecarbonyl)pyridine-4-oxyl)phenyl)-3-(4-chloro-3-trifluoromethylphenyl ) urea

[0085]

[0086] Pyridine-2-carboxylic acid was used instead of p-methoxybenzoic acid, and the procedure of Example 1 was followed to obtain 135 mg of the target compound as a white solid. 1 H NMR (300MHz, DMSO-d 6 ):10.59(br,2H,-CONH-),9.39(s,1H,-CONH-),9.17(s,1H,-CONH-),8.69(s,1H,Ar-H),8.58(s, 1H,Ar-H),8.13(s,1H,Ar-H),8.04(s,2H,Ar-H),7.63(m,5H,Ar-H),7.41(s,1H,Ar-H) ,7.21(m,3H,Ar-H).MS(FAB)(M + +1=571)

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Abstract

The invention discloses N'-aryl formyl 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′-arylformyl o-pyridine hydrazide derivatives shown in formula I, their pharmaceutically acceptable salts, 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 kinase...

Claims

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Application Information

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IPC IPC(8): C07D213/86C07D213/87C07D401/12C07D417/12A61K31/44A61K31/444A61K31/4402A61K31/4409A61K31/497A61K31/4439A61K31/4406A61P35/00A61P35/02A61P37/02A61P25/00
CPCC07D213/86C07D213/87C07D401/12C07D417/12
Inventor 冯志强陈晓光李燕张莉婧王克唐克
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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