Method for preparing key intermediate of anti-influenza drug peramivir

An anti-influenza drug and intermediate technology, applied in the field of drug synthesis, can solve the problems of increasing the pressure of waste water discharge, scarcity and large amount of nickel ore, etc., and achieve the effects of reducing the pressure of the three wastes, high reaction conversion rate, and cheap use.

Active Publication Date: 2017-05-10
ZENJI RES LAB
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has the following disadvantages: 1. It needs to use a large amount of nickel chloride hexahydrate, which increases the pressure of wastewater discharge; 2. The product contains a small amount of toxic nickel, which needs to be strictly controlled; 3. Use nickel chloride hexahydrate Cooperate with sodium borohydride reduction, the conversion rate is only 80%, and the isomer content is about 10% (the inventor repeats the data, the predecessors have no public data); 4, my country's nickel ore is scarce, mainly by importing from countries such as the Philippines
Peramivir is a drug that can treat severe influenza that endangers public health safety. If the raw materials produced cannot be made domestically, it will increase uncertainty in solving public health problems in the future

Method used

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  • Method for preparing key intermediate of anti-influenza drug peramivir
  • Method for preparing key intermediate of anti-influenza drug peramivir
  • Method for preparing key intermediate of anti-influenza drug peramivir

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Add compound A (1 mmol) and copper acetate monohydrate (0.5 mmol) into a 250 ml three-necked flask, dissolve with methanol, and cool to 0-5°C. Take another beaker, add sodium hydroxide (0.02mmol) and sodium borohydride (1.5mmol), dissolve in methanol and slowly drop into the three-necked flask, after the drop is complete, stir and react at room temperature for 12 hours. Samples were taken and the results analyzed by HPLC. In the post-treatment, ammonia water was added to quench the reaction, the solvent was spin-dried, and compound B was obtained by column chromatography.

Embodiment 2

[0034]

[0035] Add compound A (1 mmol) into a 250 ml three-necked flask, add nickel chloride hexahydrate (0.5 mmol), dissolve with methanol, and cool to 0-5°C. Take another beaker, add sodium hydroxide (0.02mmol) and sodium borohydride (1.5mmol), dissolve in methanol and slowly drop into the three-necked flask, after the drop is complete, stir and react at room temperature for 12 hours. Samples were taken and the results analyzed by HPLC. In the post-treatment, ammonia water was added to quench the reaction, the solvent was spin-dried, and compound B was obtained by column chromatography.

Embodiment 3

[0037]

[0038] Add compound A (1 mmol) into a 250 ml three-necked flask, add cobalt chloride hexahydrate (0.5 mmol), dissolve with methanol, and cool to 0-5°C. Take another beaker, add sodium hydroxide (0.02mmol) and sodium borohydride (1.5mmol), dissolve in methanol and slowly drop into the three-necked flask, after the drop is complete, stir and react at room temperature for 12 hours. Samples were taken and the results analyzed by HPLC. In the post-treatment, ammonia water was added to quench the reaction, the solvent was spin-dried, and compound B was obtained by column chromatography.

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PUM

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Abstract

The invention discloses a method for preparing a key intermediate of an anti-influenza drug peramivir and belongs to the technical field of drug synthesis. The method includes taking a combination of cobalt and iron in a specific ratio as an additive and sodium borohydride as a reducing agent and reacting in an alcohol solvent. The method has the advantages of mild reaction conditions, simplicity and convenience in operation, low cost, high yield and high chiral purity.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, in particular, the invention relates to a preparation method of a key intermediate of peramivir, an anti-influenza drug. Background technique [0002] Peramivir (Peramivir) was developed by American Biocrystal Pharmaceutical Co., Ltd. It is another new type of neuraminidase (NA) inhibitor after the successful development of Zanamivir and Oseltamivir and its launch in 1999 Anti-influenza-like drugs for the treatment and prevention of influenza A and B in adults and children. [0003] The chemical name of peramivir is (1S, 2S, 3R, 4R, 1'S)-(-)-3-[(1'-acetylamino-2'-ethyl)butyl]-4-[[(aminosub Amino)methyl]amino]-2-hydroxycyclopentane-1-carboxylic acid trihydrate, the chemical structural formula is as follows: [0004] [0005] At present, the patents related to the synthetic method of peramivir are CN1282316, CN1358170, CN1367776 and J.Med.Chem.2001, 44, 4379-4392, etc., using Wens l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/06C07C271/24
CPCC07B2200/07C07C269/06C07C271/24
Inventor 葛敏刘惠敏
Owner ZENJI RES LAB
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