Taxane-based prodrugs

US5824701A · kind A · utility

Assignee

• Enzon, Inc. · US

Inventors

• Richard B. Greenwald · Cambridge, US
• Annapurna Pendri · South Glastonbury, US

Key dates

• Filing date: Feb 3, 1997
• Grant date: Oct 20, 1998
• Expiry date: Feb 3, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D305/14
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Taxane-based compositions of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of aryls, substituted aryls, aralkyls, substituted aralkyls, alkyls and substituted alkyls; PA0 R.sub.2 is an aryl or substituted aryl, preferably phenyl; PA0 R.sub.3 is H, a C.sub.1-10 alkoxy, SiEt.sub.3 or ##STR2## Y is O or S; (n) is zero or a positive integer; PA0 X is oxygen, S, SO.sub.2 or NL, where L is selected from the group consisting of H, C.sub.1-8 alkyls, aryls and aralkyls; PA0 R.sub.4 is H or an aroyl of the formula: ##STR3## wherein Ar is an aromatic, substituted aromatic or heteroaromatic group; R.sub.5 is H, CH.sub.3 CO or a substituted acetic acid derivative; PA0 Z is H or OR.sub.6 where R.sub.6 is selected from the group consisting of H, C.sub.1-8 alkyls, C.sub.1-8 substituted alkyls, C.sub.1-8 aralkyls, substituted aryls, aralkyls, substituted aralkyls, C.sub.1-10 alkoxy, SiEt.sub.3, ##STR4## P is O or OH; R.sub.8 is one of H, S(CH.sub.3).sub.3, Si(C.sub.2 H.sub.5).sub.3, CH.sub.3 CO, or substituted acetic acid derivatives of the formula; ##STR5## where R.sub.10 is an alkyl, aryl, halogen, or hydrogen alkoxy or ##STR6## R.sub.9 is selected from the group cons…