A method for obtaining impurities by photodegradation of paclitaxel

A paclitaxel and photodegradation technology, applied in the direction of organic chemistry, etc., can solve the problems of difficult control of photodegradation conditions, inability to obtain impurities, and low yield.

Active Publication Date: 2020-12-08
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

At present, the method of photodegradation is generally used to obtain this impurity, but the conditions of photodegradation are not easy to control. If the conditions of photodegradation are severe, it will be over-degraded into other molecular structures; if the conditions of photodegradation are too mild, it will not be possible to obtain enough Impurities, very low yield

Method used

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  • A method for obtaining impurities by photodegradation of paclitaxel
  • A method for obtaining impurities by photodegradation of paclitaxel
  • A method for obtaining impurities by photodegradation of paclitaxel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Put the paclitaxel raw material in a light-shielding container; place it in a microwave generator, and when using microwaves at a frequency of 2450MHz, stop for 5 minutes after every 3 seconds of microwave treatment, turn over the paclitaxel raw material, and then microwave for 3 seconds and then stop for 5 minutes , so processed 5 times.

[0031] The mixed gas of oxygen and nitrogen is supplemented throughout the microwave treatment process; the volume content of oxygen in the mixed gas is 25%, and the volume of the mixed gas supplemented per second is 1 / 20 of the volume of the light-shielding container.

[0032] (2) Dissolve the paclitaxel raw material (4.2g, 4.9mmol) after microwave treatment in carbon tetrachloride (100ml), add azobisisobutylcyanide (1.6g, 9.8mmol), put the reaction bottle into a 254nm In the light box, react at room temperature (20-30° C.) for 10 days.

[0033] After the reaction solution was concentrated, it was passed through the column, and...

Embodiment 2

[0035] (1) Put the paclitaxel raw material into a light-shielding container; place it in a microwave generator, and when using microwaves with a frequency of 2450MHz, stop for 10 minutes after every 5 seconds of microwave treatment, turn over the paclitaxel raw material, and then microwave for 5 seconds and then stop for 10 minutes , so processed 3 times.

[0036] A mixed gas of oxygen and nitrogen is supplemented throughout the microwave treatment process; the volume content of oxygen in the mixed gas is 30%, and the volume of the mixed gas supplemented per second is 1 / 30 of the volume of the light-shielding container.

[0037] (2) Dissolve the microwave-treated paclitaxel raw material (4.2g, 4.9mmol) in toluene (150ml), add azobisisobutylcyanide (3.2g, 19.6mmol), and put the reaction bottle into a 254nm light box , react at room temperature (20-30°C) for 3 days.

[0038] The reaction solution was concentrated and passed through the column, and eluted with the mobile phase n...

Embodiment 3

[0040] (1) Put the paclitaxel raw material into a light-shielding container; place it in a microwave generator, and when using microwaves with a frequency of 915MHz, stop for 10 minutes after every 12 seconds of microwave treatment, turn over the paclitaxel raw material, and then microwave for 12 seconds and then stop for 10 minutes , so processed 3 times.

[0041] A mixed gas of oxygen and nitrogen is supplemented throughout the microwave treatment process; the volume content of oxygen in the mixed gas is 30%, and the volume of the mixed gas supplemented per second is 1 / 30 of the volume of the light-shielding container.

[0042] (2) Dissolve the microwave-treated paclitaxel raw material (4.2g, 4.9mmol) in benzene (210ml), add azobisisobutylcyanide (4.0g, 24.5mmol), and put the reaction bottle into a 254nm light box In the reaction at 50°C for 12h.

[0043] The reaction solution was concentrated and passed through the column, and eluted with the mobile phase n-hexane: ethyl a...

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Abstract

The invention provides a method performing photo-degradation on taxol to obtain impurities. The method includes the steps of firstly, placing a taxol raw material into a lightproof container, placing in a microwave generator, performing microwave treatment under the frequency of 2450MHz or 915MHz, and supplementing the mixed gas of oxygen and nitrogen in the whole microwave treatment process; secondly, placing the taxol raw material after the microwave treatment into a solvent, adding a radical initiator, performing degradation under an illumination effect, and performing column chromatography separation and purification after the degradation to obtain the impurities. The method is simple to operate, low in cost, high in yield and good in product purity and plays an important role in taxol quality researches.

Description

technical field [0001] The invention relates to the technical field of medicine preparation, in particular to a method for photodegrading paclitaxel to obtain required impurities. Background technique [0002] Paclitaxel is the best natural anticancer drug discovered so far, and it has been widely used clinically in the treatment of breast cancer, ovarian cancer, some head and neck cancers and lung cancer. As a diterpene alkaloid compound with anticancer activity, paclitaxel has attracted botanists and chemists due to its novel and complex chemical structure, extensive and significant biological activities, new and unique mechanism of action, and scarce natural resources. The great favor of scientists, pharmacologists, and molecular biologists made it a world-renowned anti-cancer star and research focus in the second half of the 20th century. Its structure is shown in formula (A): [0003] [0004] There is an impurity in paclitaxel, as shown in the following formula (1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D305/14
CPCC07D305/14
Inventor 黄春葛月兰汤伟彬
Owner 无锡紫杉药业股份有限公司
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