Dibenzo[c]chromen-6-one derivatives as anti-cancer agents
AssigneeNanoDesign, Inc.
InventorsJonathan Martin Schmidt, Peter Redden, Julie Mercure, Shuguang Zhu, John Whelan, Natalie Lazarowych
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Abstract
Molecules demonstrating anti-proliferative effects against epithelial cancer cell lines and endothelial cells and methods of synthesis are disclosed. The molecules are intended for use in therapeutic preparations for the treatment of cancer through either anti-angiogenesis or other anti-cancer mechanisms. The compounds specified are 6H-dibenzo[b,d]pyran-6-one derivatives and have been shown to be antiproliferative against human endothelial cells.
Claims14
A compound of Formula I, or a pharmaceutically acceptable salt or ester thereof,
- wherein:
- i) R1 represents a substituent selected from the group consisting of:
- H, OH and OR3;
- ii) R2 represents a substituent selected from the group consisting of:
- iii) R3 is a C1-8 lower alkyl chain;
- and
- iv) R4 is selected from the group consisting of:
- hydrogen, hydroxy, methoxy, ethoxy and trifluoroethoxy.
A process for the preparation of a compound of Formula 1.5
- comprising:
- a) reacting a molecule of Formula 1.4
- wherein
- i) R1 represents a substituent selected from the group consisting of:
- H, OH and OR3;
- ii) R2 represents a substituent selected from the group consisting of:
- iii) R3 is a C1-8 lower alkyl chain;
- and
- iv) R4 is selected from the group consisting of:
- hydrogen, hydroxy, methoxy, ethoxy and trifluoroethoxy
- with a reagent mixture comprising SOCl2 and AlCl3, thereby generating a reaction mixture, and
- b) recovering said compound of Formula 1.5 from said reaction mixture.
A process for the preparation of a compound of Formula III,
- comprising:
- a) reacting a molecule of Formula 1.8:
- wherein R4 is a methoxy group
- with a reagent mixture comprising SOCl2 and AlCl3, thereby generating a reaction mixture, and
- b) recovering said compound of Formula III from said reaction mixture.
A process for the preparation of a compound of Formula II,
- comprising:
- a) reacting a molecule of Formula 1.9:
- wherein R4 it is a methoxy group
- with a reagent mixture comprising HOCH2CH2OH and p-TsOH, thereby generating a reaction mixture, and
- b) recovering said compound of Formula II from said reaction mixture.
A pharmaceutical composition comprising the compound of Formula I or a pharmaceutically acceptable salt or ester thereof and at least one pharmaceutically acceptable carrier.
A method of treating cancer comprising administering a therapeutically effective amount of the compound of Formula I to a patient in need thereof.
Dependencies are inferred from the claim text.