N-thiolated &bgr;-lactam antibiotics

US6476015B1 · kind B1 · utility

Assignee

• University of South Florida · US

Inventors

• Edward Turos · Tampa, US
• Edward T. Carpenter · Tampa, US
• Timothy E. Long · Blacksburg, US
• Daniel V. Lim · Tampa, US
• Sonja S. Dickey · Tampa, US

Key dates

• Filing date: Jul 24, 2000
• Grant date: Nov 5, 2002
• Expiry date: Jul 24, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D205/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Substituted monocyclic &bgr;-lactam compounds that are N-1-thiolated monolactams, and which exhibit wide-ranging antibacterial activities, having a single 4-membered azetidinone ring in which: the N-1 nitrogen atom of the azetidinone ring is bonded to sulfur but is not sulfonated, of the formula: wherein R1-5 are independently hydrogen, alkyl, heteroalkyl, aryl, heteroaryl, alkenyl, or alkynyl; X is H, C, or O; and n=0-3. Chemical synthesis of these compounds by a [2+2]-imine-acid chloride cycloaddition, and methods for subsequent derivatization, are also disclosed. The compounds and compositions disclosed herein are useful as antibacterial and antibiotic agents.