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Method for producing epothilone derivatives by means of selective catalytic epoxidation

A technology of epothilone and derivatives, applied in the field of new selective epoxidation method, which can solve the problems of unsatisfactory regioselectivity, poor selectivity, and extensive attack of external double bonds

Inactive Publication Date: 2012-10-10
BAYER SCHERING PHARMA OY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0021] The drawback of all these reagents is that, in addition to poor α / β selectivity on epoxides, there is also extensive attack (sometimes > > 5%) on the outer double bond formation, which means that the regioselectivity is also unsatisfactory
[0049] The results show that the methods of the prior art are still unsatisfactory for the synthesis of epothilone derivatives of formula I

Method used

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  • Method for producing epothilone derivatives by means of selective catalytic epoxidation
  • Method for producing epothilone derivatives by means of selective catalytic epoxidation
  • Method for producing epothilone derivatives by means of selective catalytic epoxidation

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Embodiment 1

[0153] 1.000 kg of a diene of formula II (prepared according to WO 00 / 66589), 14.17 g (3 mol%) of rhenium trioxide and 35.5 g (18 mol.%) of 4-cyanopyridine were dissolved in 10 liters of dichloromethane , and then cooled to -50 °C. 579 ml of a 30% aqueous hydrogen peroxide solution (3 eq.) was added, and the mixture was stirred at -50°C for about 70 hours. The reaction was followed to completion by HPLC. As soon as the precursor substance (compound of formula II) falls below 1%, the reaction is stopped by adding 580 ml of a 20% strength aqueous solution of sodium thiosulfate. Then a further 7000 ml of sodium thiosulfate solution are added and then warmed to +10°C. The mixture is stirred at +10° C. for 1 hour, the organic phase is separated off and the aqueous phase is re-extracted with 5000 ml of dichloromethane. The combined organic phases were washed with 5000 ml of saturated aqueous sodium chloride solution. The organic phase was concentrated in vacuo. The residue was ...

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Abstract

The invention relates to a novel method for producing an epothilone derivative using substituted pyridines and methyltrioxorhenium as catalysts.

Description

technical field [0001] The present invention relates to a novel selective epoxidation process for the preparation of epothilone derivatives of formula I. The method of the present invention can obtain the target compound of formula I with high chemical purity and diastereomer purity and good yield, and can be produced on a large scale. Background technique [0002] For example in Angew.Chem.1996, 108, 1671-1673, describe the cytotoxic effects of the natural products epothilone A (R=hydrogen) as well as epothilone B (R=methyl). [0003] [0004] Epothilone A (R=H), Epothilone B (R=CH 3 ) [0005] Epothilones represent a very promising class of antineoplastic agents that have been tested for efficacy against a variety of cancer lines. A review of various syntheses has been described, for example, by J. Mulzer in Monatsh. Chem. 2000, 131, 205-238. These drugs exhibit the same biological mechanism of action as paclitaxel or other taxanes (for paclitaxel see: D.G.I. King...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04
CPCC07D417/04A61P35/00C07D417/02
Inventor J·普拉策克O·彼得罗夫S·普吕斯
Owner BAYER SCHERING PHARMA OY
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