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N-pyridyl-2-phenoxy fatty amide and medical application thereof

A technology of phenoxy fatty acid amide and pyridyl, which is applied in the field of compounds, can solve the problems of no research and development reports on the inhibitory activity of influenza virus neuraminidase, and achieve the effect of easy industrial production and simple preparation methods

Active Publication Date: 2015-08-05
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] N-pyridyl-2-phenoxy fatty acid amide has no research and development report on the inhibitory activity of influenza virus neuraminidase

Method used

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  • N-pyridyl-2-phenoxy fatty amide and medical application thereof
  • N-pyridyl-2-phenoxy fatty amide and medical application thereof
  • N-pyridyl-2-phenoxy fatty amide and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of (R)-N-(6-chloropyridine-3-methyl)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide

[0022]

[0023] (R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionyl chloride 3.3mmol, dichloromethane 40mL, 5-aminomethyl-2-chloropyridine 3.3mmol and catalyst Amount of 4-dimethylaminopyridine (DMAP), stirred for 10 min under ice bath, dripped into 10 mmol of triethylamine, continued to stir for 2 h at 10°C, poured into 150 mL of ice water, extracted with dichloromethane, dried, precipitated, and reduced Pressure column chromatography obtains (R)-N-(6-chloropyridine-3-methyl)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanamide, yield 77.5%, m.p.130.7~131.3℃; 1 H NMR (300MHz, CDCl 3 )δ: 1.60 (d, J=6.9Hz, 3H, CH 3 ), 4.40~4.58 (m, 2H, CH 2 ), 4.74 (q, J=6.9Hz, 1H, CH), 6.87~7.01 (m, 5H, phenyl-H, NH), 7.04 (d, J=6.6Hz, 1H, pyridine ring-H), 7.27 (d, J=6.6Hz, 1H, pyridine ring-H), 7.37~7.56 (m, 3H, phenyl-H), 8.22 (d, J=1.8Hz, 1H, pyridine ring-H); LC-MS , m / z: 4...

Embodiment 2

[0025] Preparation of N-ethyl-N-(6-cyano-5-nitropyridin-2-yl)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide

[0026]

[0027] 2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionyl chloride (3.3mmol), dichloromethane or 1,2-dichloroethane (40mL), 2-cyano- 6-Amino-3-nitropyridine (3.3mmol) and a catalytic amount of 4-dimethylaminopyridine (DMAP) were stirred for 10min, and triethylamine (1.0g, 10mmol) was added dropwise. Reflux for 8 hours, pour the reaction solution into 150ml of ice water, extract with dichloromethane, dry over anhydrous sodium sulfate, solvent removal, and column chromatography to obtain N-ethyl-N-(6-cyano-5-nitropyridine-2- Base)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionamide, yield 21.2%, m.p.95.7~97.0℃; 1 H NMR (300MHz, CDCl 3 )δ: 1.26(t, J=6.9Hz, 3H, CH 3 ), 1.68 (d, J=6.6Hz, 3H, CH 3 ), 4.06~4.15 (m, 2H, CH 2 ), 5.36 (q, J = 6.6Hz, 1H, CH), 6.74 (d, J = 9.0Hz, 2H, phenyl-H), 6.88 (t, J = 7.8Hz, 1H, phenyl-H), 6.95 (d, J=9.0Hz, 2H, phenyl-H),...

Embodiment 3

[0029] Anti-influenza virus neuraminidase activity of N-pyridyl-2-phenoxy fatty acid amides

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Abstract

The invention discloses N-pyridyl-2-phenoxy fatty amide and medical application thereof. The chemical structural formula of N-pyridyl-2-phenoxy fatty amide is shown as formula I or II in the specification, wherein R1 and R2 are selected from hydrogen and C1-C12 alkyl, X1 is selected from fluorine, chlorine, bromine or iodine, and X2 is selected from fluorine, chlorine, bromine or iodine. The invention also relates to a pharmaceutical composition containing the compound and application of N-pyridyl-2-phenoxy fatty amide in preparation of anti-influenza virus neuraminidase inhibitors.

Description

technical field [0001] The invention relates to a compound, in particular to an N-pyridyl-2-phenoxy fatty acid amide and its medical application. Background technique [0002] 4-Aryloxyphenoxyalkanoic acid derivatives have also been widely reported in the research of anticancer drugs [Investigational New Drugs, 1999, 16:287–296; Investigational New Drugs, 1998, 16:129–139; Acta Pharmaceutica Sinica, 2005, 40(9):814-819], wherein XK469 (2-(4-(7-chloroquinoxalin-2-yloxy)phenoxy)propionic acid) is a phase I clinical study conducted by DuPont Company of the United States A new type of antitumor drug, XK469 has a wide antitumor spectrum, few side effects, and is effective for a variety of solid tumor models, such as colon cancer Colon38 and breast cancer [J Med Chem, 2001, 44 (11): 1758-76 ]. The Chinese invention patents for the application of 2-phenoxyalkanamide are as follows: (1) 2-[4-(Benzoxazol-2-yloxy)phenoxy]alkanamide and its application, CN103086995A, published on May...

Claims

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Application Information

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IPC IPC(8): C07D213/61C07D213/84A61K31/44A61P31/16
CPCC07D213/61C07D213/84
Inventor 刘祈星胡艾希
Owner CHINA THREE GORGES UNIV
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