Chromatographic separation method of paclitaxel and cephalomannin

A technology of cephalomannine and paclitaxel, which is applied in the fields of pharmaceutical formulations, organic active ingredients, and medical preparations containing active ingredients, and can solve problems such as difficult synthesis methods

Inactive Publication Date: 2005-02-02
INDENA SPA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have the disadvantage of using toxic reagents such as osmium tetroxide and in any case leading to the destruction and conversion of cephalomannine to its derivatives, which can only be obtained by difficult synthetic methods. Regeneration to cephalomanine

Method used

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  • Chromatographic separation method of paclitaxel and cephalomannin
  • Chromatographic separation method of paclitaxel and cephalomannin
  • Chromatographic separation method of paclitaxel and cephalomannin

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Example 1: Isolation of paclitaxel from the extract of Taxus japonica containing cephalomannine

[0036] By HPLC analysis, it was found that 290 g of extract prepared from 620 kg of Taxus densely grown (whole plant) according to the method described by V. Senilh et al. (J. Nat. Prod. 47, 131, 1984) contained 183 g of paclitaxel and 81 g of cephalomannine . This extract was dissolved in 3.5 liters of tert-butyl acetate and loaded onto a column containing 60 kg of silica gel. A total of 1200 liters of tert-butyl were eluted. After elution with 350 liters of solvent, 400 liters of a fraction containing paclitaxel and less than 3% cephalomannine and 200 liters of another fraction containing cephalomannine and less than 3% paclitaxel were obtained. The two fractions are separately concentrated to dryness in vacuo and the residue is crystallized from hexane-acetone. Then, obtained 154g paclitaxel and 70g cephalomannine, their HPLC purity is greater than 99%, and their physic...

Embodiment 2

[0037] Example 2: Separation of paclitaxel and cephalomanine from their mixture

[0038] A mixture containing 70 g of paclitaxel and 30 g of cephalomannine was dissolved in 1.5 liters of tert-butyl formate and loaded onto silica gel containing 10 kg suspended in the same solvent. The column was eluted with tert-butyl formate and the fractions were combined after HPLC / TLC analysis. Fractions containing paclitaxel and cephalomannine were concentrated to dryness, respectively, and these residues were crystallized with appropriate proportions of acetone and heptane to obtain paclitaxel and cephalomannine with HPLC purity over 99%.

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PUM

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Abstract

A method for separating paclitaxel cephalomannin and other related compounds by obtaining a staring material that contains paclitaxel and cephalomannin; dissolving the staring material in any one a number of particularly defined solvents such as butly formate and butly acetate to form a mixture; subjecting the mixture to column chromatography to obtain an eluted fraction of pactitaxel and cephalomannin and a residue ; and separately drying the paclitaxel and cephalomannin fractions to obtain separate crystalline forms of paclitaxel and cephalomannin, respectively.

Description

field of invention [0001] The present invention relates to the isolation of paclitaxel and the paclitaxel analogue cephalomannin starting from plant extracts of the genus Taxus or cell cultures thereof. Specifically, cephalomanine was separated from paclitaxel by chromatography on a normal phase silica gel column. Background technique [0002] Paclitaxel, formerly known as Taxol, is a particularly promising anticancer agent. In 1971, Wani et al. isolated it from the bark of Taxus brevifolia (J.Am.Chem.Soc.93, 2325, 1971), and determined it by chemical methods and X-ray crystallographic analysis. Structure. [0003] [0004] Paclitaxel has been approved by the FDA for the treatment of breast and ovarian cancer, and its treatment for lung and rectal cancer is currently in clinical trials (see, for example, W.P. McGuire and E.K. Rowinsky, Paclitaxel in Cancer Therapy, M. Dekker, New York 1995 , pp. 1 to 337). [0005] The main natural source of paclitaxel is the bark of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/337A61P35/00C07D305/14
CPCC07D305/14A61P35/00C12N5/04B01D15/08
Inventor B·加贝塔G·齐尼
Owner INDENA SPA
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