Nitrobenzyl mustard quaternary salts and their use as hypoxia-selective cytotoxic agents

US5872129A · kind A · utility

Assignee

• AUCKLAND UNISERVICES LIMITED · NZ

Inventors

• William Alexander Denny · Beachlands, NZ
• William Robert Wilson · Waiuku, NZ
• Moana Tercel · Auckland, NZ

Key dates

• Filing date: Jul 31, 1997
• Grant date: Feb 16, 1999
• Expiry date: Jul 31, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D233/95
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

##STR1## Nitrobenzyl mustard quaternary salts of formula (I), and the pharmaceutically acceptable salts thereof, process for their manufacture and their chemotherapeutic use as hypoxia selective cytotoxic agents. Wherein, X represents a linker chain --CR.sub.1 R.sub.3 -- or CR.sub.1 .dbd.CR.sub.2 -- (where R.sub.1 and R.sub.2 are separately H, lower alkyl, phenyl or nitrophenyl; Y is halogen or OSO.sub.2 R; Q is lower alkyl (optionally substituted with alkyl and/or ether groups and containing up to 6 carbons) or nitrophenyl; Ar represents a mono- or bicyclic aromatic unit, R is lower alkyl optionally substituted with alkyl and/or ether groups, and may contain up to eight carbon atoms. Z represents one or more of the groups NO.sub.2, SO.sub.2 R, CONHR, R, OR, SR, CF.sub.3 and aza (ring --CH-- replared by --N.dbd.); with the proviso that when Y=Cl or Br, Q=Me, and X=--CH.sub.2 -- then Ar.noteq.2-nitrophanyl or 4-nitrophenyl.