Urethane mediated, GST specific molecular release systems

US5908919A · kind A · utility

Assignee

• Terrapin Technologies, Inc. · US

Inventors

• Lawrence M. Kauvar · San Francisco, US
• Matthew H. Lyttle · Fairfax, US
• Apparao Satyam · Fremont, US

Key dates

• Filing date: Jun 7, 1995
• Grant date: Jun 1, 1999
• Expiry date: Jun 7, 2015

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61K38/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Compounds of the formula ##STR1## or of the formula ##STR2## or the amides, esters or salts thereof, wherein: S.sup.x is S.dbd.O, O.dbd.S.dbd.O, S.dbd.NH, HN.dbd.S.dbd.O, Se.dbd.O, O.dbd.Se.dbd.O, Se.dbd.NH, HN.dbd.Se.dbd.O, S.sup.+ R.sup.3 wherein R.sup.3 is alkyl (1-6C) or O--C.dbd.O or HN--C.dbd.O; PA1 each R of R.sup.1, and R.sup.2 is independently H or a noninterfering substituent; PA1 wherein (conj) represents a conjugated system capable of transmitting electrons; PA1 n is 0 or 1; PA1 YCO is selected from the group consisting of .gamma.-Glu, .gamma.-Glu-Gly, Glu, Glu-Gly, .beta.Asp, .beta.-Asp-Gly, Asp and Asp-Gly; PA1 AA.sub.C is an amino acid linked through a peptide bond to the remainder of said compound of Formula 1; and PA1 N(Z) represents a reduced nitrogen-containing leaving group and L represents an electron-withdrawing leaving group, PA1 are useful as prodrugs and to generate active components released by the activity of glutathione S-transferase.