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Aibomycin analogue, its preparation method, medicinal composition and use

A composition and drug technology, applied in the field of epothilone analogues, can solve problems such as weakening natural products

Inactive Publication Date: 2006-03-29
BETA PHARMA (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no other way in nature such as direct carbon-carbon single bond or double bond linkage for macrocyclization, which weakens the ability of nature to generate more metabolically stable natural products

Method used

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  • Aibomycin analogue, its preparation method, medicinal composition and use
  • Aibomycin analogue, its preparation method, medicinal composition and use
  • Aibomycin analogue, its preparation method, medicinal composition and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0179] 4-Oxo-pentanoyl chloride

[0180]

[0181] Dissolving 4-oxo-pentanoic acid in CH 2 Cl 2 , add 0.01 equivalent of DMF, and then add 1.1 equivalent of oxalyl chloride. The mixture was stirred at room temperature for 6 hours and concentrated to give the crude title compound which was used without further purification.

Embodiment 2

[0183] 1-(4-Benzyl-2-oxo-oxazolidin-3-yl)-pentan-1,4-dione

[0184]

[0185] 4-Benzyl-oxazolidin-2-one was dissolved in THF (tetrahydrofuran) at -78°C, and 1.1 equivalents of n-butyllithium dissolved in hexane was added. The mixture was stirred at -78°C for 10 minutes, followed by the addition of 1 equivalent of the product of Example 1 in THF. The resulting mixture was stirred for another 30 min and washed with NH 4 The reaction was quenched with Cl solution and extracted with EtOAc. use Na 2 SO 4 The EtOAc extracts were dried and concentrated. The residue was purified by silica gel chromatography to give the title compound.

Embodiment 3

[0187] 4-Benzyl-3-[3-(2-methyl[1,3]-dioxol-2-yl)-propionyl]-oxazolidin-2-one

[0188]

[0189] The product of Example 2 was dissolved in -40°C CH 2 Cl 2 1.2 equivalents of 1,2-bis-trimethylsiloxyethane and 0.05 equivalents of TMSOTf (trimethylsilyltrifluoromethanesulfonic acid) were added. Stir the mixture at -40°C for 6 hours, add 0.2 equivalent of Et 3 N(triethylammonium). The solvent was removed under reduced pressure to give the crude title compound which was used without further purification.

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Abstract

An Aibomycine analog, its preparing process, its composite medicines, and its application for treating cancers and hyperplastic diseases and inducing apoptosis are disclosed.

Description

field of invention [0001] The present invention relates to a macrocyclic compound with antitumor activity, a preparation method of the compound, a pharmaceutical composition containing the compound and a use method of the compound. More specifically, the present invention relates to a series of stable metabolized epothilone analogs as antineoplastic agents. Background of the invention [0002] Macrolide compounds useful in the pharmaceutical field of epothilones. For example, epothilones A and B were found to have the structure [0003] [0004] R in epothilone A stands for H, and R in epothilone B stands for Me [0005] Plays a microtubule stabilizing effect similar to paclitaxel, and thus has cytotoxic activity against rapidly proliferating cells (such as tumor cells or other hyperproliferative cell diseases). Hofle, G. et al [Angew.Chem.Int.Ed.Engl., Vol. 35, No.13 / 14, 1567-1569 (1996); WO93 / 10121 published on May 27, 1993 and May ...

Claims

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Application Information

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IPC IPC(8): C07D277/10C07D413/06A61K31/426A61K45/06A61P35/00
Inventor 张晓东谢国建郇正伟查理斯·大卫王印祥陈杭
Owner BETA PHARMA (SHANGHAI) CO LTD
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