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Stereoselective synthesis of beta-nucleosides

A technology of nucleoside compounds and compounds, applied in drug combination, organic chemistry, antineoplastic drugs, etc.

Active Publication Date: 2013-05-08
PHARMAESSENTIA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, none of these research and development results are satisfactory.

Method used

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  • Stereoselective synthesis of beta-nucleosides
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Embodiment Construction

[0044] The present invention relates to an efficient method for the stereoselective synthesis of 2'-deoxynucleosides, more specifically gemcitabine, and novel intermediates produced in this method.

[0045] Conventional chemical transformations can be used to practice the invention. Those skilled in the art can determine the appropriate chemicals, solvents, protecting groups and reaction conditions for this transformation. Relevant information is described, for example, in R. Larock, Comprehensive Organic Transformations, VCH Publishers (1989); T.W. Greene and P.G.M. Wuts, Protective Groups in Organic Synthesis, 3rd edition, John Wiley and Sons (1999); L. Fieser and M. . Fieser, Fieser and Fieser's Reagents for Organic Synthesis, John Wiley and Sons (1994); with L. Paquette ed. Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons (1995) and other editions of these. Embodiments of the methods of the invention are described herein for purposes of illustration.

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Abstract

A method of stereoselectively synthesizing a [beta]-nucleoside, e.g., 2'-deoxy-2,2'-difluorocytidine, is described. The method includes reacting a tetrahydrofuran compound of the following formula, wherein R1, R2, R3, R4 and L are defined as in the specification, with a nucleobase derivative in the presence of an oxidizing agent.

Description

technical field [0001] The present invention relates to the synthesis technique of β-nucleoside. Background technique [0002] 2'-Deoxynucleosides and their analogs are important therapeutic agents. For example, gemcitabine, ie, 2'-deoxy-2,2'-difluorocytidine, can be used to treat viral infections and cancer. See, eg, US Patent Nos. 4,526,988 and 4,808,614 applications. [0003] Typically, each 2'-deoxynucleoside has more than one chiral center, and multiple stereoisomers can be formed. Not all stereoisomers are therapeutically active. Several stereoselective synthetic routes to 2-deoxy-β-nucleosides have been developed. But none of these research and development results are satisfactory. [0004] Therefore, there is a need to develop a more efficient route for the stereoselective synthesis of 2'-deoxynucleosides. Contents of the invention [0005] One aspect of the present invention relates to a method for synthesizing a β-nucleoside compound of formula (I): [000...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/12C07H19/06
CPCC07H15/18C07H19/06A61P35/00
Inventor 简崇训简斌书黄正谷
Owner PHARMAESSENTIA CORP
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