Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin III

A C1-C20, C1-C12 technology, applied in the field of semi-synthetic routes of other taxane compounds, can solve the problems of no side chain, no acyl group and the like

Inactive Publication Date: 2009-09-09
6570763 CANADA
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AI Technical Summary

Problems solved by technology

10-DABIII has the basic diterpene structure of paclitaxel, but has no acyl group at C-10 and no side chain at C-13

Method used

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  • Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin III
  • Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin III
  • Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin III

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[0091] The present invention relates to taxane derivatives of 9,10-diketones, which are useful in the efficient production of paclitaxel and docetaxel analogues from 9-dihydro-13-acetylbaccatin III (9-DHAB). Formed during the chemical transformation of compounds and their intermediates. These transformations can include protection of the 7-OH of 9-DHAB, deacetylation at the C-10 position, and oxidation of the C-9 and C-10 hydroxyl groups to yield the intermediate compound 7-triethylsilyl-9 , 10-diketo-13-acetyl ccatin III ( 6 ). These processes may also include combining paclitaxel and docetaxel side chains with 9,10-diketone moieties (compound 7 ), through which paclitaxel, docetaxel and analogs thereof with different C-13 side chain structures can be synthesized, as well as intermediates thereof.

[0092] The first major aspect of the present invention is to provide a novel process for the preparation of paclitaxel and docetaxel utilizing a novel precursor, 9-dihydro-13-a...

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Abstract

The present invention provides a novel semi-synthetic route in the preparation of docetaxel and paclitaxel. This new process involves the conversion of 9-dihydro-13-acetylbaccatinIII to docetaxel and paclitaxel by the step of converting 9-dihydro-13-acetylbaccatin III into 7-O-triethylsilyl-9,10-diketobaccatin III, and adding docetaxel and paclitaxel side chain precursors, respectively, to form a new class of taxane intermediates, such as 7-O-triethylsilyl-9,10-diketodocetaxel and 7-O-triethylsilyl-9,10-diketopaclitaxeltaxel. These new intermediates then by a series reduction, acetylation of the 10-hydroxyl position for paclitaxel and finally deprotection to yield docetaxel and paclitaxel, the most important anti-cancer drugs.

Description

technical field [0001] The present invention relates to a semi-synthesis for the preparation of the anticancer drugs paclitaxel, docetaxel and the precursor 10-deacetylbaccatin III which can be used in the production of these most prestigious anticancer drugs, as well as other taxane compounds route. More specifically the present invention relates to a new semi-synthetic route for the synthesis of paclitaxel, docetaxel and 10-deacetylbaccatin III from 9-dihydro-13-acetylbaccatin III, wherein 9 -Dihydro-13-acetylbaccatin III is a taxane compound isolated from the Canadian yew (Taxus Canadensis), a long green shrub that grows in eastern Canada and the northeastern United States. Background technique [0002] Taxanes are a class of substances that occur naturally in yew trees such as Taxus brevifolia, European yew (Taxus baccata), and Canadian yew, which are common in eastern Canada and the northeastern United States. 9-Dihydro-13-acetylbaccatin III is one of the chemicals ex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/14C07F7/18
CPCC07F7/186C07D305/14C07F7/1804
Inventor 刘健
Owner 6570763 CANADA
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