Method for rapidly preparing remdesivir intermediate

A technology for remdesivir and intermediates, which is applied in the field of rapid preparation of remdesivir pharmaceutical intermediates, can solve the problems of unfavorable large-scale production, triazineamine intermediates, multi-step column chromatographic separation steps, etc., and achieve operational The effect of simplicity and convenience, high yield and short synthesis steps

Pending Publication Date: 2020-06-05
UNIV OF SCI & TECH OF CHINA
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Problems solved by technology

Robert S.Klein et al. in the article Syntheses ofPyrrolo[7,1-f][1,2,4]triazine Congeners of Nucleic Acid Purines via the N-Amination of 2-Substituted Pyrroles Using Orthogonal Suzuki-Miyaura Cross-Coupling Reactions(J .Heterocyclic.Chem., 31,781,1994), the triazineamine intermediate of the remdesivir drug used in the post-synthesis treatment requires many multi-step column chromatography separation steps, and is not conducive to large-scale production

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  • Method for rapidly preparing remdesivir intermediate
  • Method for rapidly preparing remdesivir intermediate
  • Method for rapidly preparing remdesivir intermediate

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Embodiment Construction

[0031] The present invention provides a method for preparing the Remdesivir pharmaceutical intermediate of formula (I),

[0032]

[0033] where X is a halogen atom. In the present invention, the halogen atom means a Cl, Br or I atom.

[0034] The method of the present invention comprises the following four consecutive steps:

[0035] (1) Combining the aldehyde compound of formula (II) with sulfamic acid (NH 2 OSO 3 H) reacting in an aqueous solvent to obtain a cyanide compound of formula (III);

[0036] (2) The cyanamide compound of formula (IV) is obtained from the cyanide compound of formula (III) by adding a base to the reaction aqueous solution obtained in step (1) to make it basic;

[0037] (3) in the presence of a base and an organic solvent, the cyanamide compound of formula (IV) obtained in step (2) is reacted with formamidine acetate (C3H8N2O2), thereby obtaining a triazineamine compound of formula (V); and

[0038] (4) reacting the triazineamine compound of f...

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Abstract

The present invention relates to a method for rapidly preparing a remdesivir intermediate represented by a following formula (I) without complex purification and separation, wherein X represents a halogen element. The method is simple, high in yield and single in product, and can be obtained through simple filtration and separation; complicated separation operation such as column chromatography isnot needed; the remdesivir intermediate represented by the formula (I) can be rapidly, efficiently, and massively prepared; and sufficient intermediates are provided for large-scale preparation of remdesivir drugs that may be used to treat new corona viruses.

Description

technical field [0001] The invention relates to a method for rapidly preparing a Remdecivir pharmaceutical intermediate. Background technique [0002] Since the outbreak of the novel coronavirus pneumonia (COVID-19), how to prevent and treat COVID-19 has become an urgent problem. China's National Health Commission pointed out in the "Diagnosis and Treatment Plan for Novel Coronavirus Infected Pneumonia (Trial Version 5)" announced on February 5, 2020 that there is no confirmed effective antiviral treatment method, so the screening of antiviral drugs And large-scale preparation has become the key work of epidemic prevention and control. Remdesivir, an antiviral nucleoside analog, has previously demonstrated activity against the severe acute respiratory syndrome (SARS) and Middle East respiratory syndrome (MERS) viral pathogens in in vitro and in vivo animal models. Both coronaviruses are structurally similar to the new coronavirus COVID-19: both are coronaviruses, encoding ...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 杜平武葛治伸汪峰韩志勇刘世勇
Owner UNIV OF SCI & TECH OF CHINA
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