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Neuraminidase inhibitor zanamivir derivative and preparation method thereof

A technology of neuraminidase and zanamivir, which is applied in the field of medicine and biology, can solve the problems of limited range of vaccine use and inability to effectively prevent and treat influenza viruses, and achieve the effect of saving time and simplifying the preparation process

Inactive Publication Date: 2017-10-20
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the vaccine not only has certain limitations in the scope of use, but also the conventional seasonal influenza vaccine is not effective enough to prevent and control the continuously mutating influenza virus

Method used

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  • Neuraminidase inhibitor zanamivir derivative and preparation method thereof
  • Neuraminidase inhibitor zanamivir derivative and preparation method thereof
  • Neuraminidase inhibitor zanamivir derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (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.

[0021] (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 of the reaction.

[0022] (3) After the reaction is over, filter with medium-speed filter paper to remove most of the urea by-products; add dichloromethane and water to the filtrate, extract, remove unreacted 4-fluorophenylacetic acid and active esters, and ...

Embodiment 2

[0025] (1) Accurately weigh 118.2mg (0.767mmol) of 4-fluorophenylacetic acid, 172.9mg (0.902mmol) of EDC, and 121.9mg (0.902mmol) of HoBt into a round bottom flask, then add 3.0mL of anhydrous dimethyl sulfoxide Dissolve and mix, stir evenly, vacuumize, protect with nitrogen, and react at room temperature for 1 hour to obtain the active ester.

[0026] (2) Accurately weigh 150.0 mg (0.451 mmol) of zanamivir, dissolve it with 2 mL of dimethyl sulfoxide, slowly add it dropwise to the active ester reaction solution, and then add dropwise 0.13 mL of triethylamine and 2.75 mg (0.022 mmol) 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 of the reaction.

[0027] (3) After the reaction, add dichloromethane and water to the reaction solution, extract, remove unreacted 4-fluorophenylacetic acid and active ester, obtain the water phase, and remove the dichlorom...

Embodiment 3

[0029] Same as in Example 1, in the first step reaction to generate the active ester reaction solution, under nitrogen protection, react at room temperature for half an hour to obtain the active ester, and the final product yield is 61.5%.

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Abstract

The invention discloses a neuraminidase inhibitor zanamivir derivative and a preparation method thereof. Different from the previous synthetic route of zanamivir derivatives, the present invention uses zanamivir as the starting material for the first time to prepare derivatives; the one-step reaction obtains the product, which greatly simplifies the synthesis steps; the prepared compounds are all New compound molecules with high predicted biological activity.

Description

technical field [0001] The invention belongs to the technical field of medicine and biology, and in particular relates to a neuraminidase inhibitor zanamivir derivative and a preparation method thereof. Background technique [0002] Influenza is an acute viral respiratory infectious disease caused by influenza virus that seriously endangers human health, especially among children, the elderly, and people with chronic cardiovascular and respiratory diseases, which has a high morbidity and mortality rate. There have been many large-scale influenza epidemics in history, which have brought huge disasters to human beings. According to the statistics of the World Health Organization, 100 million people in the northern hemisphere are infected with influenza every year, 5 million visits to the doctor, 300,000 hospitalizations, 10,000 people die from influenza, and the annual economic loss exceeds 10 billion US dollars. [0003] Vaccination is one of the main means of protecting the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/28A61K31/351A61P31/16
CPCC07D309/28
Inventor 程利平王天池黄金文谢达
Owner SHANGHAI INST OF TECH
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