Variolin derivatives as anti-cancer agents

US7320981B2 · kind B2 · utility

Assignee

• PHARMA MAR, S.A. · ES

Inventors

• Jonathan Morris · Forbes, AU
• Regan James Anderson · Lower Hutt, NZ
• Modesto Remuinan · Madrid, ES
• Ignacio Manzanares · Madrid, ES

Key dates

• Filing date: Jul 11, 2001
• Grant date: Jan 22, 2008
• Expiry date: Jul 12, 2022

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02A50/30
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention provides variolin derivatives of formula (I), wherein: R1 and R2 are each independently selected from the group consisting of H, OH, OR, SH, SR, SOR, SO2R, NO2, NH2, NHR, N(R)2, NHCOR, N(COR)2, NHSO2R, CN, halogen, C(═O)H, C(═O)R, CO2H, CO2R, C1-C12 alkyl, C1-C12 haloalkyl, C2-C12 alkenyl, C2-C12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl and substituted or unsubstituted heteroaromatic; and R3 is selected from the group consisting of H, OH and OMe; wherein the or each group R is independently selected from the group consisting of OH, C1-C12 alkyl, C1-C12 haloalkyl, C2-C12 alkenyl, C2-C12 alkynyl, substituted or unsubstituted aryl, substituted unsubstituted aralkyl, substituted or unsubstituted arylalkenyl and substituted or unsubstituted heteroaromatic, and wherein the group R1, R2 or R3 is a group of formula N(R)2 or N(COR)2, each of the R groups may be the same or different, or the two R groups, together with the nitrogen atom to which they are attached, may form a 5-14 membered heterocyclic ring. These compounds display activity against a range of mammalian cancer cell lines. New synthetic routes to new and known variolin compo…