Method to improve antiviral activity of nucleotide analogue drugs
US9550803B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | May 7, 2012 |
| Grant date | Jan 24, 2017 |
| Priority date | — |
| Expiry date | Aug 14, 2032 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H19/20
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
An amino acid conjugate of a cyclic or acyclic nucleoside phosphonate is provided. In some cases, the amino acid conjugate is a tyrosine alkyl amide phosphonate ester conjugate of a cyclic or acyclic nucleoside phosphonate, and is useful as an antiviral compound. In certain cases, the tyrosine conjugate includes a long chain alkyl group on the carboxamide group of the tyrosine residue. In a method of preparing an acyclic tyrosine conjugate, a tert-butyloxycarbonyl (Boc) protected tyrosine residue containing a long chain alkyl group is reacted with an acyclic nucleoside phosphonate mono-ethyl ester in the presence of benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate to produce a Boc-protected nucleoside phosphonate di-ester, and the di-ester is deethylated and deprotected to produce the tyrosine conjugate. Methods of inhibiting viral replication and methods of treating a viral infection using the amino acid conjugate are also provided.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.