N-thiolated β-lactam antibiotics

Authors

Edward Turos
Edward T. Carpenter
Timothy Long
Daniel V. Lim
Sonja S. Dickey

Document Type

Patent

Publication Date

November 2002

Patent Number

6476015

Abstract

Substituted monocyclic β-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 R_1-5 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.

Application Number

09/621,646

Recommended Citation

Turos, Edward; Carpenter, Edward T.; Long, Timothy; Lim, Daniel V.; and Dickey, Sonja S., "N-thiolated β-lactam antibiotics" (2002). USF Patents. 783.
https://digitalcommons.usf.edu/usf_patents/783

Assignees

University of South Florida

Filing Date

07/24/2000

Primary/U.S. Class

514/210