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Ortho-pyridine hydrazide derivatives and their production methods, pharmaceutical compositions and uses

A technology of hydrazide derivatives and urea derivatives, applied in the fields of o-pyridine hydrazide derivatives and their preparation methods, pharmaceutical compositions and uses

Active Publication Date: 2016-09-14
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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  • Ortho-pyridine hydrazide derivatives and their production methods, pharmaceutical compositions and uses
  • Ortho-pyridine hydrazide derivatives and their production methods, pharmaceutical compositions and uses
  • Ortho-pyridine hydrazide derivatives and their production methods, pharmaceutical compositions and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0054] Embodiment 1.4-Chloro-N-propylidene picoline hydrazide

[0055]

[0056] Add 1.0 g of 4-chloropicoline hydrazide to the flask, add 20 ml of acetone to dissolve it, add 1 drop of glacial acetic acid, stir and react at room temperature for 48 hours, TLC monitors the end of the reaction, concentrate the reaction solution, and add 30 ml of acetic acid Ethyl ester was dissolved, washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 0.9 g of white solid. 1 H NMR (300MHz) (CDCl 3 ), 10.56 (S, 1H, CONH), 8.45 (d, 1H, ArH), 8.31 (S, 1H, ArH), 7.46 (d, 1H, ArH), 2.17 (S, 1H, CH 3 ), 2.04 (S, 1H, CH 3 ).MS(FAB):(M + +1=212).

Embodiment 24

[0057] Example 2.4-p-aminophenoxy-N-propylidene picoline hydrazide

[0058]

[0059] Dissolve 2.46 g of p-aminophenol in 20 ml of DMF at room temperature, add 2.6 g of potassium tert-butoxide, stir for 2 hours, add 3.0 compound and 0.09 g of K2C03 and heat at 80 ° C for 16 h under nitrogen protection. After the reaction, cool to room temperature, evaporate DMF to dryness, add 10ml ethyl acetate and 10ml distilled water for extraction, extract the aqueous layer three times with 10ml ethyl acetate, combine the organic layers, wash three times with 50ml saturated brine, and dry over anhydrous Na2SO4. A purple solid was separated by column chromatography, 1 H NMR (300MHz)(DMSO-d6), 10.69(S, 1H, CONH), 8.47(d, 1H, ArH), 7.37(S, 1H, ArH), 7.11(d, 1H, ArH), 6.87(d , 2H, ArH), 6.65 (d, 2H, ArH), 5.18 (S, 2H, NH 2 ), 2.00 (S, 1H, CH 3 ), 1.93 (S, 1H, CH 3 )., MS(FAB)(M + +1=244)

Embodiment 3

[0060] Example 3.1-p-Chlorotrifluoromethylphenyl-3-(4-(2-propylidene hydrazinoylpyridine-4-oxy)phenyl)urea

[0061]

[0062] 6.076 g of CDI was dissolved in 20 mL of dichloromethane, and a catalytic amount of DMAP was added. Then add dropwise 6.642 g of p-chlorotrifluoromethylaniline in 60 ml of dichloromethane solution at room temperature. After the addition, stir at room temperature for 5 hours. After TLC monitors the disappearance of the raw material, add dropwise 4-p-aminophenoxy-N-propane After the addition of the dichloromethane solution of forked picoline hydrazide, the temperature was raised to 50° C. and the reaction was heated for 7 hours to stop the reaction. The solvent was removed under reduced pressure, and 4.0 g of the product was obtained by column chromatography.

[0063] 1 H NMR (300MHz) (DMSO-d6), 10.72 (S, 1H, NH), 9.23 (S, 1H, NH), 9.02 (S, 1H, NH), 8.54 (d, 1H, ArH), 8.11 (S , 1H, ArH), 7.50-7.75 (m, 4H, ArH), 7.40 (S, 1H, ArH), 7.13-7.28 (m, 3H, ArH...

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Abstract

The invention relates to 1-(4-chloro-3-trifluoromethylphenyl)-3-(4-(2-(2-isopropenylhydrazine carbonyl)pyridine-4-oxo)phenyl)carbamide with the structure represented by formula I and 1-(4-chloro-3-trifluoromethylphenyl)-3-(4-(2-(2-isopropylhydrazine carbonyl)pyridine-4-oxo)phenyl)carbamide with the structure represented by formula II, medicinal salts thereof, preparation methods thereof, a composition containing one or more of above compounds, and uses of the compounds in the treatment of protein kinase associated diseases, such as immune disorder and tumor diseases.

Description

field of invention [0001] The present invention relates to 1-(4-chloro-3-trifluoromethylphenyl)-3-(4-(2-(2-isopropylhydrazine carbonyl)pyridine-4-oxyl) shown in formulas I and II )phenyl)urea and 1-(4-chloro-3-trifluoromethylphenyl)-3-(4-(2-(2-isopropylhydrazinecarbonyl)pyridine-4-oxyl)phenyl) Urea, its pharmaceutically acceptable salt, and its preparation method, the composition containing one or more of these compounds, and the use of these compounds in the treatment of 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 conserv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/86A61K31/44A61P35/00A61P37/02A61P25/00
Inventor 冯志强陈晓光田康李燕唐克
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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