Analogues of N-acetylardeemin, method of preparation and uses thereof

US6147076A · kind A · utility

Assignees

• Sloan Kettering Institute for Cancer Research · US
• The Trustees of Columbia University in the City of New York · US

Inventors

• Samuel J. Danishefsky · New Haven, US
• Kristopher M. Depew · Acton, US
• Stephen Philip Marsden · Leeds, GB
• William Bornmann · Missouri City, US
• Ting-Chao Chou · Paramus, US
• Andrej Zatorski · New York, US

Key dates

• Filing date: Nov 15, 1996
• Grant date: Nov 14, 2000
• Expiry date: Nov 15, 2016

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P35/02
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides a compound having the structure: ##STR1## wherein R.sub.1 R.sub.6 and R.sub.7 are independently hydrogen, OH, NH.sub.2, SH, halogen, C.sub.1 -C.sub.9 linear or branched chain alkyl, alkylmercapto, alkylamino, dialkylamino, alkoxy, phenyl, etc.; wherein R.sub.0 and R.sub.2 are independently hydrogen, OH, linear or branched chain alkyl, --CR.sub.3 R.sub.3 --CH(O)CH.sub.2, --CR.sub.3 R.sub.3 --CH.sub.2 CH.sub.3, --CR.sub.3 R.sub.3 --CH.sub.2 CH.sub.2 OH, --CR.sub.3 R.sub.3 --CH(OH)R.sub.4 or --CR.sub.3 R.sub.3 --CH.dbd.CHR.sub.4 ; wherein R.sub.3 and R.sub.4 are independently hydrogen, halogen, C.sub.1 -C.sub.9 linear or branched chain alkyl, phenyl, etc.; wherein R.sub.5 is hydrogen, C.sub.1 -C.sub.9 linear or branched chain alkyl, phenyl, etc.; and wherein R.sub.8 is hydrogen, C.sub.1 -C.sub.9 linear or branched chain acyl, benzoyl, etc.; with the proviso that (a) when R.sub.2 is --CR.sub.3 R.sub.3 --CH(O)CH.sub.2, --CR.sub.3 R.sub.3 --CH.sub.2 CH.sub.3, --CR.sub.3 R.sub.3 --CH.sub.2 CH.sub.2 OH, --CR.sub.3 R.sub.3 --CH(OH)R.sub.4 or --CR.sub.3 R.sub.3 --CH.dbd.CHR.sub.4, then R.sub.2 is hydrogen; (b) when R.sub.0 is --CR.sub.3 R.sub.3 --CH(O)CH.sub.2,…