C-10 carbon-substituted artemisinin-like trioxane compounds having antimalarial, antiproliferative and antitumor activities

US6156790A · kind A · utility

Assignees

• Hauser, Inc. · US
• THE JOHNS HOPKINS UNIVERSITY · US

Inventors

• Gary H. Posner · Baltimore, US
• Soon Hyung Woo · Baltimore, US
• Poonsakdi Ploypradith · Baltimore, US
• Michael H. Parker · Doylestown, US
• Theresa A. Shapiro · Towson, US
• Qun Zheng · Surrey, CA
• Christopher K. Murray · Lexington, US
• Randall J. Daughenbaugh · Longmont, US

Key dates

• Filing date: Dec 30, 1997
• Grant date: Dec 5, 2000
• Expiry date: Dec 30, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D519/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides a two-step procedure for the replacement of the pyranose anomeric 10-OH group in dihydroartemisinin by a variety of carbon nucleophiles, resulting in the novel C-10 carbon-substituted trioxanes of structure: ##STR1## wherein, when n is 1, R is selected from a group of unsubstituted or substituted aryls, heteroaryls, polyethylene glycol, acetylenics, or benzoylmethylenes, or alkanoylmethylenes; or when n is 2, R is selected from a group of unsubstituted or substituted aryls, heteroaryls, polyethylene glycol, alkenyls, alkyls, diketones or bis-acetylenes.