US 8,940,313 B2 · Tyrosine-based prodrugs of antiviral agents

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.

Claims17

Dependent claims

A compound of the formula

or a salt thereof, wherein:
B is a purine or pyrimidine base;
R is H, an amino acid residue or a derivative thereof, or a C1-C4 alkyl, substituted alkyl, cycloalkyl, or substituted cycloalkyl group;
and
R1 is H or a C1-C4 alkyl, substituted alkyl, cycloalkyl, or substituted cycloalkyl group.

2 more elements

Dependencies are inferred from the claim text.

Facts

Application

13/092,939Filed 23 Apr 2011 · us provisional application

Priority

23 Apr 2010

Published

US 2011/0263535 A127 Oct 2011

Granted

27 Jan 2015

Term ends

Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07F 9/65616
Containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system,…:…
A61K 31/675
Phosphorus compounds: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
A61P 31/12
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antivirals
A61P 31/20
Antivirals: for DNA viruses

Tyrosine-based prodrugs of antiviral agents

Life of this patent

Tyrosine-based prodrugs of antiviral agents

Life of this patent

Abstract

Claims17