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Method for purifying cabazitaxel

A technology of cabazitaxel and purity, which is applied in organic chemistry and other fields, can solve problems such as the complex chemical structure of cabazitaxel, and achieve the effects of reducing production costs, improving production efficiency, and being convenient to use

Inactive Publication Date: 2013-01-23
JIANGSU HONGDOUSHAN BIOLOGICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The chemical structure of cabazitaxel is complex, and process impurities with similar structures will be produced during the synthesis process. How to remove these impurities produced during the synthesis process is the technical bottleneck in the R&D stage of the cabazitaxel process
At present, there are no relevant patents and literatures to report on the removal of process impurities

Method used

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  • Method for purifying cabazitaxel
  • Method for purifying cabazitaxel
  • Method for purifying cabazitaxel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]Dissolve 0.2 g of cabazitaxel with a purity of 99.5% in a mixed solvent of 100 ml of ethyl acetate and ethanol; stir and dissolve at a stirring speed of 150 rpm; the ratio of ethyl acetate and ethanol is 10:1; Add cyclohexane to the taxel solution and stir until turbidity occurs. The temperature in this process is maintained at 50°C. After turbidity is generated, the temperature is slowly lowered to 20°C. The cooling time is 3 hours, and the holding time is 3 hours for crystallization; filter, The crystallized sample was washed with purified water, and the washed sample was dried at 50° C. under reduced pressure for 2 hours. The dried sample was dissolved in 200 ml of methanol, 2.0 g of silica gel was added to the methanol solution of cabazitaxel, the stirring speed was 150 rpm, the adsorption time was 1 hour, filtered, and the sample after evaporating to dryness was placed under reduced pressure at 50°C Drying for 3 hours under high pressure liquid chromatography can ob...

Embodiment 2

[0052] Dissolve 0.25 g of cabazitaxel with a purity of 99.5% in a mixed solvent of 100 ml of dichloromethane and acetone; stir and dissolve at a stirring speed of 100 rpm; the ratio of dichloromethane and acetone is 15:1, and then add cabazitaxel Petroleum ether was added to the solution and stirred until turbidity occurred. The temperature during this process was maintained at 55°C. After turbidity occurred, the temperature was slowly lowered to 25°C within 3 hours, and the temperature was kept for 3 hours to carry out crystallization. The crystallized sample was filtered and washed, and the washed sample was dried at 40° C. under reduced pressure for 2 hours. Dissolve the dried sample in 200 ml of ethanol, add 1.0 g of silica gel to the ethanol solution of cabazitaxel, stir at 100 rpm, and absorb for 2 hours, filter, and evaporate the sample to dryness at 50 °C under reduced pressure After drying for 3 hours, 0.142 g of cabazitaxel with a single impurity content of less than...

Embodiment 3

[0054] Dissolve 0.3 g of cabazitaxel with a purity of 99.5% in 90 ml of a mixed solvent of chloroform and n-butanol; stir to dissolve at a stirring speed of 300 rpm; the ratio of chloroform and n-butanol is 8:1, and then add Add n-heptane to the taxel solution and stir until turbidity occurs. The temperature during this process is maintained at 45°C and stirred. After turbidity occurs, slowly cool down to 15°C within 3 hours and keep warm for 4 hours for crystallization. The crystallized sample was filtered and washed, and the washed sample was dried at 45° C. under reduced pressure for 2 hours. The dried sample was dissolved in 200 ml of acetone, 4.0 g of diatomaceous earth was added to the methanol solution of cabazitaxel, the stirring speed was 300 rpm, the adsorption time was 2 hours, filtered, and the sample after evaporating to dryness was desorbed at 55°C. Drying under high pressure conditions for 3 hours, the cabazitaxel 0.124g with a single impurity content of less th...

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Abstract

The invention discloses a method for purifying cabazitaxel. The method comprises the following steps of: obtaining a crystallized sample by taking cabazitaxel with purity over 98% as a start raw material and cyclohexane, ethyl acetate and ethanol as crystallization solvents; filtering, washing and drying the crystallized sample, and dissolving with methanol; adding a proper amount of adsorbent into the methanol solution of cabazitaxel; sufficiently adsorbing the sample by the adsorbent; filtering the sample again, and evaporating the solvent to dryness; and drying, wherein the impurity content of the dried sample in single technology is reduced to below 0.1% according to the high performance liquid chromatography detection. According to the invention, the impurity content of single cabazitaxel synthesis technology is effectively reduced by a separation and purification method combining crystallization and adsorption, and the requirement that the impurity content of single technology of cabazitaxel is lower than 0.1% is met.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for purifying cabazitaxel. Background technique [0002] Cabazitaxel, trade name Jevtana, chemical name 4-acetoxy-2-α-benzoyloxy-2α-5β, 20-epoxy-1-hydroxy-7β, 10β-di Methoxy-9-oxotaxane-11-en-13α-yl(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate. Molecular formula is C 45 h 57 NO 14 , the structural formula is shown in formula (I). Cabazitaxel is a second-line drug for the treatment of prostate cancer developed by Sanofi-Aventis. It is a semi-synthetic taxane-like small molecule compound, and its anticancer mechanism is similar to that of docetaxel. On June 17, 2010, the US Food and Drug Administration (FDA) approved the combination of cabazitaxel and prednisolone acetate for the treatment of advanced prostate cancer. [0003] [0004] Cabazitaxel structural formula. [0005] The chemical structure of cabazitaxel is complex, and pro...

Claims

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Application Information

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IPC IPC(8): C07D305/14
Inventor 王永毅陈磊汤志伟赵洪涛罗金龙黄春王琼
Owner JIANGSU HONGDOUSHAN BIOLOGICAL TECH
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