Synthesis method of anti-influenza and avian influenza virus resistant medicine peramivir

A technology of avian influenza virus and synthesis method, which is applied in the field of organic drug synthesis and can solve the problems of environmental pollution, unapproved marketing, and long route.

Inactive Publication Date: 2012-03-14
JINAN UNIVERSITY
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0011] The synthetic route is to use (1R, 4S)-2-azabicyclo[2.2.1]hept-5-en-3-one as raw material, through nine-step reaction to synthesize peramivir, the route is longer and the yield low rate
In the cycloaddition process, highly toxic benzene and phenyl isocyanate are used; and in the hydrogenation reduction process, the relatively expensive platinum dio

Method used

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  • Synthesis method of anti-influenza and avian influenza virus resistant medicine peramivir
  • Synthesis method of anti-influenza and avian influenza virus resistant medicine peramivir
  • Synthesis method of anti-influenza and avian influenza virus resistant medicine peramivir

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Embodiment Construction

[0064] The present invention will be further described in detail below in conjunction with the embodiments and the accompanying drawings, but the embodiments of the present invention are not limited thereto.

[0065] Below is the preparation embodiment of Peramivir, including following 9 parts:

[0066] 1. Preparation of (1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid methyl ester hydrochloride

[0067] Dissolve 10g of (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one in 120ml of dry anhydrous methanol, stir and pass in dry hydrogen chloride gas at room temperature for 3h, Hydrogen chloride gas was no longer introduced; the reaction was carried out at 50° C. for 2 h, monitored by TLC. After the reaction was completed, the reaction solution was concentrated to dryness to obtain a black viscous liquid. Add 120ml of ice-free anhydrous ether to the viscous substance, and stir overnight at room temperature. A white solid precipitated, and was filtered with suction, and the filter cake ...

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Abstract

The invention belongs to the synthesis technical field of organic medicine, and discloses a synthesis method of anti-influenza and avian influenza virus resistant medicine peramivir, which is characterized by adopting (1R, 4S)-2-azabicyclo[2.2.1]hept-5-en-3-one as a raw material and by comprising the following steps: step I: catalyzing, loop-opening and amino protection; step II: 1,3-dipolarcycloaddition; step II: sodium borohydride and nickel chloride hexahydrate reduction and acetylization; and step IV: amino protection removal, and chloroformamidine hydrochloride is adopted as reaction agent to generate guanidyl and hydrolysis methyl ester to prepare peramivir. The sodium borhydride and the nickelous chloride reduction system is used for substituting the expensive platinum dioxide to be used as reducing agent during the hydrogenation reduction process, and the self-produced chloroformamidine hydrochloride is used during the process for feeding the guanidyl reagent, so the cost is reduced, and the operation procedures are simplified. The synthesis method has short reaction routine and moderate reaction condition, is simple and convenient to operate, has low cost, and is suitable for the industrialized production.

Description

technical field [0001] The invention belongs to the technical field of organic medicine synthesis. Specifically, the invention relates to a synthesis method of an anti-influenza and avian influenza virus drug and an influenza virus neuraminidase inhibitor peramivir. Background technique [0002] Influenza, referred to as influenza for short, is an acute respiratory disease caused by influenza virus, which has the characteristics of strong infectivity, fast transmission speed, high morbidity and mortality. [0003] The structure of influenza virus is actually not complicated. It is a fat globule with eight RNA strands inside. There are many important proteins on the surface of the globule. They are "nailed" on the surface like "nails". figure 1 . These "nails" are divided into two categories, one is hemagglutinin (HA), which is used for virus infection of host cells, and the other is neuraminidase (NA), which is responsible for cutting off host cells and determines the effic...

Claims

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Application Information

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IPC IPC(8): C07C279/16C07C277/08
Inventor 陈卫民贾飞陈建新孙平华
Owner JINAN UNIVERSITY
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