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Semi-synthetic method of antineoplastic drug paclitaxel

A paclitaxel and semi-synthetic technology, applied in the five-step reaction of condensation, deprotection, preparation of paclitaxel, protection, selective acetylation, and ring opening, can solve problems such as research without experiments, and achieve fast reaction speed, mild reaction conditions, The effect of high product purity

Active Publication Date: 2015-09-02
重庆赛诺生物药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although patent CN200610047687 has reports on selective acylation of taxane compounds, there is no follow-up experimental research

Method used

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  • Semi-synthetic method of antineoplastic drug paclitaxel
  • Semi-synthetic method of antineoplastic drug paclitaxel
  • Semi-synthetic method of antineoplastic drug paclitaxel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0043] Paclitaxel semi-synthetic route of the present invention is as follows:

[0044]

[0045] Synthesis of compound 2

[0046] Dissolve 10g (18.4mmol) of 10-deacetylbaccatin III in 1.5L tetrahydrofuran, blow nitrogen gas, stir to dissolve, add 0.684g (1.84mmol) cerium chloride heptahydrate, and cool the reaction solution to 0-5°C. Add 2.81g (27.5mmol) of acetic anhydride dropwise, keep the reaction for 5 hours after dropping, add 1000ml each of ethyl acetate and saturated sodium bicarbonate solution, leave to separate after stirring, and wash the organic layer with saturated brine (1000ml×3) . It was dried over anhydrous sodium sulfate, filtered, and the filtrate was precipitated to obtain 10.9 g of compound 2 (ie, baccatin III), with a yield of 100%.

[0047] Synthesis of Compound 3

[0048] Dissolve 210g (17mmol) of the compound in 100ml of dichloromethane, blow nitrogen, stir to dissolve, add 20ml of anhydrous pyridine, drop the temperature to 0-5°C, and add 5.4g...

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Abstract

The invention relates to a semi-synthesis method of antitumor drug taxol, and more particularly relates to a method for preparing taxol by the processes of taking 10-deacetylbaccatin III (10-DAB) as an initial material, selective acetylation, protection, condensation, open loop, and deprotection.

Description

technical field [0001] The present invention relates to a semi-synthetic method of paclitaxel, more specifically, to a semi-synthetic method using 10-deacetylbaccatin III (10-DAB) as a starting material, which undergoes selective acetylation, protection, condensation, and development. A method for preparing paclitaxel through a five-step reaction of cyclization and deprotection. Background technique [0002] Paclitaxel is a natural molecule with broad-spectrum anti-tumor activity, which has the following structural formula: [0003] [0004] The compound is initially obtained from the bark of Taxus brevifolia and other natural resources. Its chemical structure is novel and complex, its mechanism of action is unique, and its activity is strong. As a new broad-spectrum anti-cancer drug, paclitaxel has been approved for clinical use in more than 40 countries and is considered to be one of the most effective anti-cancer drugs discovered so far. However, the content of pacli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D305/14
CPCY02P20/55
Inventor 冯虓周志成崔英杰
Owner 重庆赛诺生物药业股份有限公司
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