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N'-straight chain alkylacyl o-pyridine hydrazide derivative, its preparation method, medicinal composition and use

A technology of straight-chain alkanoyl-o-pyridine hydrazides, which is applied in drug combinations, active ingredients of heterocyclic compounds, antineoplastic drugs, etc.

Inactive Publication Date: 2014-02-12
INST OF MATERIA MEDICA AN INST OF THE 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'-straight chain alkylacyl o-pyridine hydrazide derivative, its preparation method, medicinal composition and use
  • N'-straight chain alkylacyl o-pyridine hydrazide derivative, its preparation method, medicinal composition and use
  • N'-straight chain alkylacyl o-pyridine hydrazide derivative, its preparation method, medicinal composition and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1.1-(4-chloro-3-trifluoromethylphenyl)-3-(4-(2-(2-(n-butyryl)hydrazinecarbonyl)pyridine-4-oxyl)phenyl)urea

[0056]

[0057] Synthesis of N'-n-butyryl-4-chloropyridine-2-hydrazide

[0058] Dissolve 0.6g (7.0mmol) of butyric acid in 3mL of DMF, add 2.1g (5.8mmol) of raw materials 4-chloropyridine-2-hydrazide, 2.7g (7.0mmol) of HATU, 1.8g (17.4mmol) of triethylamine, Stir at room temperature, TLC monitors that the reaction of raw materials is complete, add 100mL of water, a large amount of off-white solid precipitates, and 1.39g of the product is obtained. 1 H NMR (400MHz, DMSO-d 6 ):10.51(s,1H,-CONH-),9.98(s,1H,-CONH-),8.66(d,1H,Ar-H),8.03(d,1H,Ar-H),7.81(dd, 1H, Hz, Ar-H), 2.16(t, 2H, -COCH 2 -),1.56(m,2H,-CH 2 -Me),0.92(t,3H,-CH 3 ).MS(FAB):(M + +1=242).

[0059] Synthesis of N'-n-butyryl-4-(p-aminophenoxy)pyridine-2-hydrazide

[0060] Dissolve 295 mg (2.7 mmol) of p-aminophenol in 5 mL of DMF, add 416 mg (3.4 mmol) of potassium tert-butoxide under n...

Embodiment 2

[0065] Example 2.1-(4-(2-(2-acetylhydrazidecarbonyl)pyridine-4-oxyl)phenyl)-3-(4-chloro-3-trifluoromethylphenyl)urea

[0066]

[0067] Utilizing acetic acid instead of n-butyric acid, referring to the operation of Example 1, 175 mg of the target compound was obtained as a white solid. 1 HNMR (300MHz, DMSO-d 6 ):δ(ppm):10.38(s,1H,-NHCO-CH 3 ),9.99(s,1H,-NHCO-),9.21(s,1H,-NHCO-),9.00(s,1H,-NHCO-),8.53(d,1H,ArH),8.11(s,1H, ArH),7.67~7.62(m,2H,ArH),7.59(d,2H,ArH),7.36(d,1H,ArH),7.20~7.17(m,3H,ArH),1.88(s,3H,- CH 3 ).MS(FAB)(M + +1=508)

Embodiment 3

[0068] Example 3.1-(4-(2-(2-propionylhydrazidecarbonyl)pyridine-4-oxyl)phenyl)-3-(4-chloro-3-trifluoromethylphenyl)urea

[0069]

[0070] Using n-propionic acid instead of n-butyric acid, refer to the operation of Example 1 to obtain 135 mg of the target compound as a white solid. 1 H NMR (400MHz, DMSO-d 6 ):δ(ppm):10.37(s,1H,-NHCO-CH 2 -),9.94(s,1H,-NHCO-),9.22(s,1H,-NHCO-),9.01(s,1H,-NHCO-),8.55(d,1H,ArH),8.12(s,1H ,ArH),7.68~7.63(m,2H,ArH),7.60(d,2H,ArH),7.37(d,1H,ArH),7.20~7.18(m,3H,ArH),2.16(q,2H, -CH 2 -),1.04(t,3H,-CH 3 ).MS(FAB)(M + +1=522)

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Abstract

The invention relates to an N'-straight chain alkylacyl o-pyridine hydrazide derivative shown as formula I, its pharmaceutically acceptable salts, hydrates and solvates, a preparation method thereof, a composition containing one or more of the compounds, and the use of the compounds in the treatment of protein kinase related diseases like immune disorder and tumor diseases.

Description

field of invention [0001] The present invention relates to N′-straight-chain alkanoyl o-pyridine hydrazide derivatives shown in formula I, their pharmaceutically acceptable salts, their hydrates and solvates, their polycrystals and cocrystals, their precursors or Derivatives, their preparation methods, compositions containing one or more of these compounds, and uses of these compounds in treating diseases related to protein kinases, such as immune disorders and tumor diseases. 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 evolv...

Claims

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Application Information

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IPC IPC(8): C07D213/86A61K31/44A61P37/02A61P35/00A61P25/00
CPCC07D213/86
Inventor 冯志强陈晓光王克李燕秦爱芳唐克
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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