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Intermediate compound of cabazitaxel

A cabazitaxel and compound technology, applied in the field of new taxane compounds, can solve the problems of increasing the synthesis cost and low yield of cabazitaxel

Active Publication Date: 2016-10-05
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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  • Intermediate compound of cabazitaxel
  • Intermediate compound of cabazitaxel
  • Intermediate compound of cabazitaxel

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 the protection, 10-DAB (10.01g, 18.4mMol) was dissolved in 490ml DMF, imidazole (4.99g, 73.3mMol) was added to it, the ice bath was cooled to 0 °C, and Et was added dropwise to the system. 3 SiCl (11.10 g, 73.6 mMol) was dripped, and the temperature was maintained at 0 °C for the reaction, and TLC detected the disappearance of the starting material after 2 hours.

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

[0144]The obtained cr...

example 2

[0164] Example 2 Preparation of Cabazitaxel

[0165] (1) Preparation of compound 6

[0166]

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

[0168] The obtained 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...

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Abstract

The invention relates to an intermediate compound for cabazitaxel and in particular relates to an intermediate compound 6 for preparing cabazitaxel, a preparation method of the intermediate compound and a method for preparing cabazitaxel by using the compound. In each step in the process of preparing cabazitaxel by using the intermediate, the reaction time is greatly shortened and the reaction yield is substantially increased, thus greatly lowering the synthesis cost of cabazitaxel.

Description

technical field [0001] The present invention relates to a new taxane compound, in particular to an intermediate compound for preparing cabazitaxel, a preparation method thereof, and a method for preparing cabazitaxel with the compound. Background technique [0002] Taxane compounds have strong antitumor activity, and such compounds have been marketed at present, such as paclitaxel, docetaxel and cabazitaxel, etc. They have good inhibitory activity on various solid tumor cells. Among them, cabazitaxel (structure shown below) is a taxane antitumor drug developed and marketed by Sanofi, France. The drug has a good effect on patients with advanced prostate cancer. Compared with other antitumor drugs, the drug It can significantly improve the vitality of patients with advanced prostate cancer and prolong the life of patients. [0003] [0004] Cabazitaxel [0005] International application WO9630355 discloses two methods for preparing cabazitaxel, but the yields of these two...

Claims

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Application Information

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