Tyrosine-based prodrugs of antiviral agents

US8940313B2 · kind B2 · utility

Assignee

• University of Southern California · US

Inventors

• Charles E. McKenna · Santa Monica, US
• Boris A. Kashemirov · Los Angeles, US
• Ivan S. Krylov · Los Angeles, US
• Michaela Serpi · Cardiff, GB
• Valeria M. Zakharova · Mannheim, DE
• Larryn W. Peterson · Mountain View, US
• John Hilfinger · Ann Arbor, US

Key dates

• Filing date: Apr 23, 2011
• Grant date: Jan 27, 2015
• Expiry date: May 27, 2031

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F9/657181
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A tyrosine-based (phosphonylmethoxyalkyl)purine or -pyrimidine conjugate is provided. In some embodiments, the conjugate includes tyrosine based amino acid or dipeptide moieties of (S)-9-(3-hydroxy-2-phosphonyl-methoxypropyl)adenine or its cytosine analog. A method of synthesizing such conjugates based on Boc-protected amino acid or dipeptides is also provided. In addition, a method of isomerizing an (S,S)-diastereoisomer to an (S,R)-diastereoisomer of an amino acid-based or dipeptide-based conjugate by a process including transesterification is provided. A method of inhibiting viral infection and a method of treating viral infection based on (phosphonylmethoxyalkyl)purine or -pyrimidine conjugates is also provided.