Synthesis of tetracyclines and analogues thereof

US8598148B2 · kind B2 · utility

Assignee

• President and Fellows of Harvard College · US

Inventors

• Andrew G. Myers · Boston, US
• Mark G. Charest · Montgomery, US
• Christian Lerner · Binningen, CH
• Jason D. Brubaker · Cambridge, US
• Dionicio R. Siegel · New York, US

Key dates

• Filing date: May 12, 2010
• Grant date: Dec 3, 2013
• Expiry date: Feb 6, 2031

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D307/77
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The modular synthesis of tetracyclines and tetracycline analogs described provides an efficient and enantioselective route to a variety of tetracycline analogs and polycyclines previously inaccessible via earlier tetracycline syntheses and semi-synthetic methods. These analogs may be used as anti-microbial agents or anti-proliferative agents in the treatment of diseases of humans or other animals.