Non-beta lactam antibiotics

US10662164B2 · kind B2 · utility

Assignee

• University of Notre Dame du Lac · US

Inventors

• Mayland Chang · Granger, US
• Shahriar Mobashery · Notre Dame, US
• Edward F. Spink · Waterloo, CA
• Derong Ding · South Bend, US
• Sebastian Testero · Rosario, AR
• Erika Leemans · Hamme, BE
• Marc Boudreau · Ste. Anne, CA

Key dates

• Filing date: Sep 25, 2015
• Grant date: May 26, 2020
• Expiry date: Sep 18, 2036

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F9/65318
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention provides a newly discovered oxadiazole class of antibiotics. The oxadiazoles impair cell-wall biosynthesis and exhibit activities against the Gram-positive bacteria such as the bacterium Staphylococcus aureus, including methicillin-resistant S. aureus (MRSA) and vancomycin-resistant and linezolid-resistant S. aureus. For example, 5-(1H-indol-5-yl)-3-(4-(4-(trifluoromethyl)phenoxy)phenyl)-1,2,4-oxadiazole (antibiotic 75b) was efficacious in a mouse model of MRSA infection, exhibiting a long half-life, a high volume of distribution, and low clearance. Antibiotic 75b antibiotic is bactericidal and is orally bioavailable. This class of antibiotics can be used as a therapeutic agent against infections by Gram-positive bacteria such as MRSA.