Method of preparing taxol by separating 10-deacetyl taxol acylate

A technology for deacetylpaclitaxel and acylated products, which is applied in the direction of organic chemistry and the like, and achieves the effects of high preparation efficiency, low solvent consumption, high reproducibility and high degree of automation

Inactive Publication Date: 2010-11-10
ZHUHAI DAORONG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the separation of taxane semi-synthetic analogues using countercurrent chromatography has not been reported

Method used

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  • Method of preparing taxol by separating 10-deacetyl taxol acylate
  • Method of preparing taxol by separating 10-deacetyl taxol acylate
  • Method of preparing taxol by separating 10-deacetyl taxol acylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A high-efficiency countercurrent chromatography system with a column volume of 25 mL was used to configure n-hexane-ethyl acetate-methanol-water in proportion, and the corresponding volume ratios were: 0.9:1:0.9:1 and n-hexane-ethyl acetate-methanol-water, The corresponding volume ratio is: 0.9: 1: 0.9: 0.8, shake well and let stand to separate layers. Separate the upper and lower layers for later use.

[0027] Weigh 20 mg of 10-deacetylpaclitaxel acylation product containing 92% paclitaxel, and dissolve it in 2 mL of solvent for use. Before sample injection, fill the entire column with the upper layer of solvent system I, adjust the speed of the main engine to 1600rpm, pump the lower layer of solvent system I into the column, and inject the sample after dynamic equilibrium; detect the product at 230nm, receive the target component and The solvent system was switched (I to II) when paclitaxel reached its peak (14-16 minutes). After the target fraction was evaporated t...

Embodiment 2

[0029] A high-efficiency countercurrent chromatography system with a column volume of 134 mL was used to configure n-hexane-ethyl acetate-methanol-water in proportion, and the corresponding volume ratios were: 0.9:1:0.9:1 and n-hexane-ethyl acetate-methanol-water, The corresponding volume ratio is: 0.9: 1: 0.9: 0.8, shake well and let stand to separate layers. Separate the upper and lower layers for later use.

[0030] Weigh 100 mg of 10-deacetylpaclitaxel chemical acylation product containing 70% paclitaxel, and dissolve it in 10 mL of solvent for use. Before sample injection, fill the entire column with the upper layer of solvent system I, adjust the speed of the main engine to 1600rpm, pump the lower layer of solvent system I into the column, and inject the sample after dynamic equilibrium; detect the product at 230nm, receive the target component and When the paclitaxel peaked (14-16 minutes), the solvent system was switched (I to II). The white solid of paclitaxel was o...

Embodiment 3

[0032] A high-efficiency countercurrent chromatographic system with a column volume of 2.5L is used to configure n-hexane-ethyl acetate-methanol-water in proportion, and the corresponding volume ratios are: 0.9:1:0.9:1 and n-hexane-ethyl acetate-methanol-water , the corresponding volume ratio is: 0.9:1:0.9:0.8, shake well and let stand to separate layers. Separate the upper and lower layers for later use.

[0033] Weigh 2 grams of 10-deacetylpaclitaxel chemical acylation product containing 85% paclitaxel, and dissolve it in 200 mL solvent for use. Before sample injection, fill the entire column with the upper layer of solvent system I, adjust the speed of the main engine to 1600rpm, pump the lower layer of solvent system I into the column, and inject the sample after dynamic equilibrium; detect the product at 230nm, receive the target component and When the paclitaxel peaked (14-16 minutes), the solvent system was switched (I to II). The white solid of paclitaxel was obtained ...

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Abstract

The invention relates to a method of preparing taxol by separating 10-deacetyl taxol acylate, which adopts an efficient countercurrent chromatography for separation and is characterized in that the 10-deacetyl taxol (10-DAT) is used as a semi-synthetic precursor, and the acylate thereof is used as the raw material. The whole separation process adopts a stepwise elution mode, and both of the two sets of solvent systems are respectively hexane-ethyl acetate-methanol-water with the corresponding volume ratio of 0.9:1:0.9:1 and hexane-ethyl acetate-methanol-water with the corresponding volume ratio of 0.9:1:0.9:0.8. The invention has simple and controllable operation method, and efficient, cheap and clean process, and is suitable for preparing the chemical derivatives such as taxol or 10-deacetyl-10-propionyl taxol or 2'-acetyl taxol and the like of 10-deacetyl taxol.

Description

technical field [0001] The present invention relates to a kind of separation 10-deacetyl paclitaxel (structural formula sees attached figure 1 Structure in 1) Method for preparing paclitaxel from acylated product. Background technique [0002] Paclitaxel (see structural formula 2) is considered to be one of the most effective anti-solid cancer drugs at present, and is widely used in the treatment of solid tumors such as breast cancer, ovarian cancer and non-small cell lung cancer [Lancet, 2000, 355:1176]. However, the content of paclitaxel in yew is extremely limited, and yew plants generally grow slowly. Paclitaxel's unique anti-cancer mechanism and definite clinical efficacy have made it in short supply since its launch, and the growing demand has led to the logging of a large number of wild yews, which has caused serious ecological problems. In order to solve the source crisis of paclitaxel, the international community advocates artificial planting of yew to alleviate t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/14
Inventor 徐丹
Owner ZHUHAI DAORONG BIOTECH
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