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Neuraminidase inhibitor and preparation method thereof

A technology for neuraminidase and inhibitors, which is applied in the field of neuraminidase inhibitors and their preparation, can solve the problems of low yield of neuraminidase inhibitors, achieve economic benefits, enhance electrophilicity, and avoid Effect of overprotonation of amines

Inactive Publication Date: 2016-11-16
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Aiming at the problem of low yield of synthetic neuraminidase inhibitors in the prior art, the object of the present invention is a kind of neuraminidase inhibitors and preparation method thereof

Method used

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  • Neuraminidase inhibitor and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0022] (1) First, mix 0.5582g of raw material oseltamivir phosphate and 0.3203g of biphenylaldehyde into 25ml of ethanol solution, add 0.012g of anhydrous acetic acid as a catalyst and react at 25°C for 15 hours; then slowly add 0.1229g Sodium cyanoborohydride was solid, reacted at 25°C for 15 hours, the reaction was complete as monitored by TLC, and the intermediate was obtained by post-experimental treatment.

[0023] (2) Accurately weigh 0.4643g of the intermediate compound and add it to a mixed solvent of methanol and deionized water (v / v, 3:1), add 0.1179g of solid sodium hydroxide, and react at 50°C for 6 hours. After the reaction was completed, the pH of the solution was adjusted to weak acidity with anhydrous acetic acid, the plate was monitored by TLC, and the final product was obtained by column chromatography separation with a final yield of 58.7%.

[0024] For the target compound C 28 h 36 N 2 o 4 Carry out high-resolution mass spectrometry and nuclear magnetic...

Embodiment 2

[0026] Same as Example 1, in the first step reaction solution of the synthetic intermediate, slowly add 0.012g of anhydrous acetic acid as a catalyst, and increase the reaction time of the synthetic intermediate to 20 hours, and increase the reaction time of the synthetic final product to 8 hours hours, the product yield was 31.7%.

Embodiment 3

[0028] Same as in Example 1, slowly add 0.012 g of anhydrous acetic acid as a catalyst to the first step reaction liquid for synthesizing the intermediate, raise the reaction temperature of the synthetic intermediate compound to 30°C, and raise the reaction temperature of the synthetic final product to 55°C °C, the yield of the final product was 36.3%.

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Abstract

The invention discloses a neuraminidase inhibitor and a preparation method thereof. The preparation method comprises the following steps: with oseltamivir phosphate and biphenyl aldehyde substances as raw materials, carrying out a reaction with a reducing agent under the action of a catalyst so as to obtain the neuraminidase inhibitor, wherein the catalyst is acetic acid. The invention has the following beneficial effects: by adopting a one-pot method, a final product with high purity and high yield can be obtained; meanwhile, practicability and effectiveness in economy and environmental friendliness are realized.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and specifically relates to a neuraminidase inhibitor and a preparation method thereof. Background technique [0002] Neuraminidase (NA, also known as sialidase) is a glycoprotein on the envelope of influenza virus. It has antigenicity, can catalyze the hydrolysis of sialic acid, assist mature influenza virus to escape from host cells and infect new cells, and plays an important role in the life cycle of influenza virus, so it has become one of the four major targets on the surface of influenza virus. Viral neuraminidase inhibitors are a new class of influenza prevention and treatment drugs following amantadine and influenza vaccines, which can selectively inhibit the activity of neuraminidase on the surface of respiratory viruses and prevent progeny virus particles from Replication and release, effectively relieve symptoms. Currently the most widely used neuraminidase inhibit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/52C07C231/12A61P31/16
CPCC07C233/52C07C231/12
Inventor 程利平王震张兴华李亮
Owner SHANGHAI INST OF TECH
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