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Application of zanamivir analogues for preparing anti-H1N1 influenza virus drug

A technology of zanamivir and influenza virus, which is applied to the application field of zanamivir analogs in the preparation of anti-H1N1 influenza virus drugs, can solve the problems of single route of administration, high price of Tamiflu, and difficulty in popularization, etc. , to achieve excellent anti-H1N1 influenza virus activity, good inhibitory effect, and good druggability.

Inactive Publication Date: 2019-01-01
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, Tamiflu is relatively expensive, it is difficult to popularize in the general population, and it has developed drug resistance to influenza virus in Duzhong, which has many limitations. Because of its low oral utilization and rapid renal elimination, zanamivir is only It can be administered by inhalation or injection, the route of administration is single, and the patient's compliance is poor. Therefore, it is urgent to develop more effective and durable anti-influenza virus drugs

Method used

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  • Application of zanamivir analogues for preparing anti-H1N1 influenza virus drug
  • Application of zanamivir analogues for preparing anti-H1N1 influenza virus drug
  • Application of zanamivir analogues for preparing anti-H1N1 influenza virus drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] A preparation method of zanamivir derivative neuraminidase inhibitor is as follows:

[0013] Synthesis of compounds W-1 and W-2

[0014]

[0015]

[0016] The preparation method of zanamivir derivative neuraminidase inhibitor is as follows:

[0017] (1) Accurately weigh 118.2mg (0.767mmol) of 4-fluorophenylacetic acid and 186.1mg (0.902mmol) of DCC into a round bottom flask, then add 3.0mL of anhydrous dimethyl sulfoxide to dissolve and mix, stir evenly, and vacuumize , under nitrogen protection, and react at room temperature for 1 hour to obtain the active ester.

[0018] (2) Accurately weigh 150.0mg (0.451mmol) of zanamivir, dissolve it with 2ml dimethyl sulfoxide, slowly add it dropwise to the active ester reaction solution, then add dropwise 0.13mL triethylamine and 2.75mg (0.022mmol) DMAP, mixed, stirred evenly, vacuumed, under nitrogen protection, reacted at room temperature for 15 hours, TLC (ethyl hexanoate:methanol:water=4:2:1) monitored the completion ...

Embodiment 2

[0025] The present invention is further described in detail through examples below, and the technical solution of the present invention is not limited to the specific embodiments listed below.

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Abstract

The invention belongs to the technical field of antiviral drugs, and particularly relates to application of zanamivir analogues for preparing an anti-H1N1 influenza virus drug. The two zanamivir analogues have stronger anti-A / WSN / 33H1N1 virus activity, median inhibitory concentration (IC50) values thereof are 0.669 mu M(W-1) and 6.949 mu M(W-2) respectively, wherein the IC50 value of the W-1 is lower than the IC50 value (0.873 mu M) of zanamivir. Therapeutic index SI (SI=CC50 / IC50) values are 149 (W-1) and 14 (W-2) respectively, wherein the SI value of the W-1 is higher than the SI value (115)of the zanamivir. The toxicity is smaller, the druggability is better, and a potential pharmaceutical value is higher.

Description

technical field [0001] The invention relates to the technical field of antiviral drugs, in particular to the application of a zanamivir analogue in the preparation of anti-H1N1 influenza virus drugs. Background technique [0002] The H1N1 influenza virus is a type of influenza A virus, an RNA virus belonging to the Orthomyxoviridae family. At present, H1N1 is one of the influenza viruses that are more likely to cause a pandemic and seriously threaten human health. Neuraminidase, also known as sialidase, is a glycoprotein touched by influenza virus. It was first discovered by the British Wilson Smith in 1933, and its enzymatic code is EC3.3.1.18. It has the activity of hydrolyzing sialic acid, so that it can cut off the connection between the virus and the host cell, and form a new infection. Its role in the physiological cycle of the virus has been systematically studied and widely concerned. Neuraminidase inhibitors are currently one of the most widely used anti-influenza...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/351A61P31/16
CPCA61K31/351A61P31/16
Inventor 程利平于娆王天池肖秀珍
Owner SHANGHAI INST OF TECH