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Pyrazine compounds and their compositions and uses

A kind of compound, the technology of composition, be used in pyrazine compound and its field as medicine

Active Publication Date: 2016-08-24
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to literature reports, other anti-influenza virus drugs have good inhibitory effects on viruses and antiviral application prospects, but further demonstration is often needed

Method used

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  • Pyrazine compounds and their compositions and uses
  • Pyrazine compounds and their compositions and uses
  • Pyrazine compounds and their compositions and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0160] Example 1: 6-fluoro-3-((2-(2-hydroxybenzylamino)ethyl)amino)pyrazine-2-carboxamide

[0161]

[0162] Step 1: Synthesis of ethyl 2-hydroxybenzoate

[0163] 2-Hydroxybenzoic acid (10g, 72mmol, 1eq.) was dissolved in EtOH (31.5mL), concentrated sulfuric acid (0.5mL, 9.39mmol) was added dropwise at 0°C, and the reaction solution was heated to 85°C for 16h. After the reaction, the reaction solution was concentrated, the residue was diluted with 20 mL of water, extracted with dichloromethane (20 mL x 2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (5.77 g, 48%) as a colorless oil .

[0164] MS:(ESI,pos.ion)m / z:167.1[M+1] + .

[0165] Step 2: Synthesis of N-(2-aminoethyl)-2-hydroxybenzamide

[0166] A mixture of ethyl 2-hydroxybenzoate (3g, 18.05mmol, 1eq.) and ethylenediamine (1.21mL, 18.1mmol, 1eq.) was reacted and stirred at 110°C for 15h. After the reaction, the reaction solution was concentrated under re...

Embodiment 2

[0177] Example 2: 6-fluoro-3-((4-hydroxybenzyl)amino)pyrazine-2-carboxamide

[0178]

[0179]Step 1: Synthesis of 6-fluoro-3-((4-hydroxybenzyl)amino)pyrazine-2-carbonitrile

[0180] Dissolve 4-(aminomethyl)phenol (87mg, 0.71mmol, 1eq.) in anhydrous THF (8mL), then add 3,6-difluoropyrazine-2-carbonitrile (100mg, 0.71mmol, 1eq .), the reaction mixture was stirred at room temperature for 3 h, then concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: PE / EtOAc (V / V)=3 / 1) to obtain the title compound (66mg, 38 %).

[0181] MS:(ESI,pos.ion)m / z:245.3[M+1] + .

[0182] Step 2: Synthesis of 6-fluoro-3-((4-hydroxybenzyl)amino)pyrazine-2-carboxamide

[0183] 6-Fluoro-3-((4-hydroxybenzyl)amino)pyrazine-2-carbonitrile (60mg, 0.25mmol, 1eq.) was dissolved in DMSO (2mL), and K 2 CO 3 (7mg, 0.05mmol, 0.2eq.) and H 2 o 2 (111mg, 0.98mmol, 4eq.), the reaction solution was stirred at room temperature for 2.5h. After the reactio...

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PUM

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Abstract

The invention relates to a pyrazine compound and application thereof as a medicine, in particular to application thereof to preparation of medicines for preventing and treating various influenza viruses. Particularly, the invention relates to a compound shown in the general formula I and a stereoisomer, a geometrical isomer, a tautomer, a nitrogen oxide, a hydrate, a solvate, a metabolite, pharmaceutically acceptable salt or a prodrug thereof, and all variables are defined in the description. The invention also relates to a compound shown in the general formula I and application of a stereoisomer, a geometrical isomer, a tautomer, a nitrogen oxide, a hydrate, a solvate, a metabolite, pharmaceutically acceptable salt or a prodrug as medicines, particular to application thereof as medicines for preventing and treating influenza viruses.

Description

technical field [0001] The invention relates to a pyrazine compound and its use as medicine, and the compound of the invention is suitable for the use of preparing antiviral medicine. The present invention also relates to pharmaceutical compositions containing these compounds, and to the use of said compounds, alone or in combination with other agents, for the prevention and treatment of various viruses, especially for the prevention and treatment of influenza viruses. Background technique [0002] Influenza (influenza, referred to as influenza) is an acute respiratory infection caused by influenza virus, and it is also a highly contagious and fast-spreading disease. It is mainly spread through droplets in the air, person-to-person contact or contact with contaminated items. Typical clinical symptoms are: sudden onset of high fever, general pain, significant fatigue and mild respiratory symptoms. Generally, autumn and winter are the high-incidence period, and the complicat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/28A61K31/4965A61P31/16
CPCC07D241/28
Inventor 张健存任青云刘辛昌罗慧超张英俊
Owner SUNSHINE LAKE PHARM CO LTD