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Bicyclo-amino pyrazol compound and application of bicycle-amino pyrazol compound in resisting coxsackie virus

A technology of bicyclic aminopyrazoles and cyclic aminopyrazoles, applied in the field of bicyclic aminopyrazoles and their application in anti-Coxsackie virus

Inactive Publication Date: 2012-11-28
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The bicyclic aminopyrazole compound of the present invention and its application in anti-Coxsackie virus have not yet seen relevant reports both at home and abroad

Method used

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  • Bicyclo-amino pyrazol compound and application of bicycle-amino pyrazol compound in resisting coxsackie virus
  • Bicyclo-amino pyrazol compound and application of bicycle-amino pyrazol compound in resisting coxsackie virus
  • Bicyclo-amino pyrazol compound and application of bicycle-amino pyrazol compound in resisting coxsackie virus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Intermediate N-tert-butoxycarbonyl-3-cyano-4-pyrrolidone

[0059] Glycine ethyl ester hydrochloride (139.5g, 1.0mol), NaOH (40.0g, 1.0mol) and methanol (600mL) were stirred at room temperature for 0.5h, and acrylonitrile (58.3g, 1.10mol) was added dropwise to the reaction system for 40min. complete. The reaction mixture was heated to 65° C. and continued to stir for 3 h, and the product obtained after the reaction was complete could be carried out to the next reaction without purification. To the above reaction mixture at room temperature was added (Boc) 2 O (218.0g, 1.0mol), after the addition was complete, react at 55-60°C for 1h and then filter with suction. The filtrate was concentrated to dryness under reduced pressure, and ethyl acetate (400 mL) was added. The organic phase was washed with water and saturated brine respectively, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain a col...

Embodiment 2

[0061] Intermediate 2-(2-hydroxy)-ethyl-3-amino-4,6-dihydro-1H-pyrrole[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester

[0062] N-tert-butoxycarbonyl-3-cyano-4-pyrrolidone (8.0g, 85.7mmol) was suspended in 250mL of absolute ethanol, stirred at room temperature for a while, insoluble clear, and 53.74g of 2-hydroxyethylhydrazine was added under vigorous stirring ( 0.685mol), the addition was completed, the reaction solution was gradually dissolved, and after stirring at room temperature for 24 hours, TLC followed the completion of the reaction. The reaction solution was light yellow and clear, concentrated to dryness under reduced pressure, added 300mL ethyl acetate, washed with water and dried, and the filtrate was concentrated under reduced pressure (15.8 g, 69%) as a pink solid.

[0063] 1 H NMR (400MHz, DMSO-d 6 ) δppm: 1.42 (9H, s), 2.96-3.01 (2H, m), 3.61-3.66 (2H, m), 4.12-4.31 (4H, m), 5.03 (2H, br.).

[0064] MS (ESI, m / z): 268 (M + +1)

Embodiment 3

[0065] Intermediate 2-(2-hydroxy)-ethyl-3-amino-4,6-dihydro-1H-pyrrole[3,4-c]pyrazole hydrochloride

[0066] 2-(2-Hydroxy)-ethyl 3-amino-4,6-dihydro-1H-pyrrole[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (21.45 g, 80.0 mmol) dissolved In anhydrous dichloromethane (300mL), pass anhydrous HCl gas under room temperature magnetic stirring, a large amount of powdery white solid precipitates, filter with suction, wash the filter cake with a little absolute ethanol, and dry under reduced pressure to obtain 15.74g off-white solid .

[0067] 1 H NMR (400MHz, DMSO-d 6 ) δppm: 2.96-3.01 (2H, m), 3.65-3.68 (2H, m), 4.01-4.15 (4H, m), 5.13 (2H, br.).

[0068] MS (ESI, m / z): 169 (M + +1)

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Abstract

The invention provides a bicyclo-amino pyrazol derivative with good coxsackie virus-resisting activity and a pharmaceutical composition containing the compound. An experiment indicates that the derivative has the strong coxsackie virus-resisting activity and is helpful to be developed into clinically effective antiviral medicaments.

Description

Technical field: [0001] The present invention relates to the synthesis of aminopyrazole compounds and their application in anti-Coxsackie virus. Background technique: [0002] Coxsackievirus (coxackievirus) belongs to the genus Enterovirus of the Picornaviridae family. Coxsackievirus infection can cause a wide range of diseases, ranging from mild respiratory infections to severe myocarditis, pericarditis and neurological diseases. A large number of studies have shown that Coxsackie virus B3 (CoxB3) is the main pathogenic factor of viral myocarditis. Searching for CoxB3 drugs from natural medicines has become a new trend in the world. Many studies have been carried out especially in China. Many single Chinese medicines or compound prescriptions have been found to have anti-CoxB3 effects in vivo and / or in vitro. Green leaves, rhubarb, Bupleurum, knotweed, skullcap, flavescens and bitter melon, etc. Compound prescriptions include Qihong Capsules, Xinxinkang Granules, Qishao S...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C07D471/04A61K31/4162A61K31/437A61P31/14
Inventor 王玉成王菊仙陶佩珍董彪章天刘洪涛许乐幸
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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