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A kind of preparation method of paclitaxel

A paclitaxel and compound technology, applied in the field of drug synthesis, can solve the problems of many by-products, long reaction time, and side reactions, and achieve the effect of less reaction by-products, fast reaction time, and less by-products

Active Publication Date: 2016-10-05
无锡紫杉药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The defect of this reaction is that when the protection re-esterification reaction of the 7-hydroxyl group on 10-DAB is carried out using a methylated group, the conversion yield is only 85%, and side reactions are prone to occur.
And the reaction time is long, the reaction requires to be carried out under the protection of an inert gas, and the reaction conditions are strict, which is not conducive to industrial production
[0007] But ring-opening deprotection all is to use solvents such as ethyl acetate, methyl alcohol or ethanol in the method for above-mentioned semi-synthetic paclitaxel, and reaction time is long, and by-product is many

Method used

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  • A kind of preparation method of paclitaxel
  • A kind of preparation method of paclitaxel
  • A kind of preparation method of paclitaxel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] a, the preparation of baccatin III (i.e. formula II compound)

[0056] At room temperature, add 300g 10-DAB and 30g CeCl3 7H2O into 6L tetrahydrofuran, add 700mL acetic anhydride dropwise under stirring, monitor by TLC, the reaction is complete after 1.5 hours, pour the reaction solution into ice water and let it stand until no white particles precipitate out 305.1 g of the compound of formula II was obtained by suction filtration and drying, and the yield was 94.4% in terms of molar yield; molar yield=(actual production amount of baccatin III / theoretical production amount of baccatin III)×100 %.

[0057] Structural identification of the resulting compound:

[0058] LC-MS(ESI):587.3[M+H] + , Elemental analysis: C 63.46%, H 6.52%, O 30.02%

[0059] b, the preparation of 7-TES-baccatin III (i.e. formula III compound)

[0060] At room temperature, dissolve 305.1g of baccatin III in 1200mL of N,N-dimethylformamide, stir and dissolve, add 152.6g of imidazole and 275mL of...

Embodiment 2

[0072] a, the preparation of baccatin III (i.e. formula II compound)

[0073] At room temperature, add 500g 10-DAB and 25g CeCl3 7H2O into 6L tetrahydrofuran, add 1000mL acetic anhydride dropwise under stirring, monitor by TLC, the reaction is complete after 2 hours, pour the reaction solution into ice water and let it stand until no white particles are precipitated 495.5 g of baccatin III was obtained by suction filtration and drying, and the yield was 92.0% in terms of molar yield; molar yield=(actual production amount of baccatin III / theoretical production amount of baccatin III)× 100%.

[0074] b, the preparation of 7-TES-baccatin III (i.e. formula III compound)

[0075] At room temperature, dissolve 495.5g of baccatin III in 1486mL of N,N-dimethylformamide, stir and dissolve, add 148.7g of imidazole and 297.3mL of triethylchlorosilane, monitor by TLC, and the reaction is complete after 3 hours. Add ice water to stop the reaction, extract with dichloromethane, wash the o...

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Abstract

The invention discloses a preparation method of paclitaxel. The side chain that undergoes condensation reaction with the 13-hydroxyl group of 7-TES-Bacca III is bis(3R,4S)-1-benzoyl-3-hydroxyl-4-phenyl protected by diisopropylalkylsilane Azepine-2-butanone. The preparation method of the invention adopts a new side chain for condensation reaction, develops a new preparation method, has few reaction by-products and high yield.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of paclitaxel. Background technique [0002] Paclitaxel (trade name: Taxol) is a taxane diterpenoid isolated from the genus Taxus. Its novel structure, unique anti-cancer mechanism, remarkable anti-cancer effect and broad anti-cancer spectrum are considered to be one of the best anti-cancer drugs discovered so far. After the United States, paclitaxel as a first-line anticancer drug has been approved for marketing in more than 40 countries. However, the lack of paclitaxel supply greatly limits its clinical application. At present, the main source of medicinal paclitaxel is to extract and isolate from the bark of the natural Taxus genus. However, due to the small number of plants in this genus, slow growth, low content, and rather difficult extraction, it is impossible to meet the growing clinical needs in the long run. [0003] In recent years, the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D305/14C07F7/18
CPCY02P20/55
Inventor 龚喜高杰梁翩
Owner 无锡紫杉药业股份有限公司
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