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Taxane compound and preparation method thereof

A compound and silane-based technology, applied in the preparation of intermediate compounds of cabazitaxel, in the field of preparation of cabazitaxel, can solve problems such as low yield and increased synthesis cost of cabazitaxel

Active Publication Date: 2013-06-26
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] International application WO9630355 discloses two methods for preparing cabazitaxel, but the yields of these two methods are very low, which greatly increases the synthesis cost of cabazitaxel, and it is necessary to find a better method to improve the yield of cabazitaxel. yield, reducing its cost

Method used

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  • Taxane compound and preparation method thereof
  • Taxane compound and preparation method thereof
  • Taxane compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0139] Example 1: Preparation of Compound 1

[0140] (1) Preparation of Compound 3

[0141]

[0142] N 2 Under protection, 10-DAB (10.01g, 18.4mMol) was dissolved in 490ml DMF, and imidazole (4.99g, 73.3mMol) was added thereto, cooled to 0°C in an ice bath, and Et 3 SiCl (11.10g, 73.6mMol), after dropping, the temperature was maintained at 0°C for reaction, and TLC detected that the raw material disappeared after 2 hours.

[0143]Add 100ml of methyl tert-butyl ether and 200ml of water to the system successively, keep the temperature at about 0°C, stir for 15 minutes, separate the organic phase, continue to extract the water phase with methyl tert-butyl ether twice, combine the organic phases, The organic phase was washed twice with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a light yellow solid.

[0144] The resulting crude product was dissolved in 60 ml of dichloromethane, cooled and crystallized,...

example 2

[0164] The preparation of example 2 cabazitaxel

[0165] (1) Preparation of compound 6

[0166]

[0167] N 2 Under protection, compound 1 (5.00g, 4.75mMol) was dissolved in 50ml DCM, and Et was added dropwise thereto at 0°C 3 N.3HF (55.00ml, 341.91mMol), after dropping, the temperature gradually rose to 20°C. After stirring for 2.5 hours, TLC detected that the raw material disappeared, and the reaction solution was added dropwise to 1L saturated NaHCO 3 solution, after stirring for 30min, the organic phase was separated, the aqueous phase was extracted twice with 100ml DCM, and the organic phase was combined; the organic phase was washed twice with water and saturated brine successively, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 4.65g white solid.

[0168] The resulting crude product was recrystallized from dichloromethane / n-hexane (1 / 4, V / V) to obtain 4.26 g of compound 6 as a white solid, with a yield of 95.55%. ...

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Abstract

The invention relates to a taxane compound and a preparation method thereof and in particular relates to an intermediate compound for preparing cabazitaxel, a preparation method of the intermediate compound and a method for preparing cabazitaxel with the compound. The intermediate compound is shown in the formula V in the specification. In each step in the process of preparing cabazitaxel with the intermediate, the reaction time is greatly shortened and the reaction yield is substantially increased, thus greatly lowering the synthesis cost of cabazitaxel. The formula V is shown in the specification.

Description

technical field [0001] The invention relates to a novel taxane compound, in particular to an intermediate compound for preparing cabazitaxel, a preparation method thereof, and a method for preparing cabazitaxel using the compound. Background technique [0002] Taxane compounds have strong anti-tumor activity, and such compounds are currently on the market, such as paclitaxel, docetaxel and cabazitaxel, etc., which have good inhibitory activity on various solid tumor cells. Among them, Cabazitaxel (structure shown below) is a taxane antineoplastic drug developed and marketed by Sanofi, France. This drug has a better effect on patients with advanced prostate cancer. Compared with other antineoplastic drugs, this drug has It can significantly improve the vitality of patients with advanced prostate cancer and prolong the life of patients. [0003] [0004] Cabazitaxel [0005] Two methods for preparing cabazitaxel are disclosed in the international application WO9630355, bu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C07D305/14C07D413/12
CPCY02P20/55
Inventor 胡雪峰袁哲东杨玉雷
Owner SHANGHAI INST OF PHARMA IND CO LTD
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