Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

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
View PDF4 Cites 2 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com