Promoiety strategy to enhance drug activity
AssigneeUniversity of Southern California
InventorCharles E. Mckenna
Life of this patent
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Abstract
Various nucleoside phosphate and phosphonate analogues are provided for treatment of viral infections. Methods of preparing the analogues, pharmaceutical compositions containing the analogues, and methods of using the analogues as antiviral compounds, especially against adenoviruses, coronaviruses, and varicella zoster viruses, are also provided.
Claims17
A nucleoside phosphonate having formula (3) or (4):
- B is a purine or pyrimidine base;
- X is CH2Ph, CH2, CH2CH2, or CHCH3;
- R is C(O)R2;
- R1 is H or alkyl, alkene, ether or thioether;
- and
- R2 is alkyl or alkene.
A nucleoside phosphonate having formula (3) or (4):
- wherein:
- B is a purine or pyrimidine base;
- X is CH2, CH2CH2, or CHCH3;
- R is H or C(O)R2;
- R1 is H or alkyl, alkene, ether or thioether;
- and
- R2 is alkyl or alkene.
A nucleoside phosphonate having formula (1):
- wherein:
- Z is a cyclic or acyclic sugar-derived bivalent group;
- X is CH2, CH2CH2, or CHCH3;
- R is C(O)R2;
- R1 is H or alkyl, alkene, ether or thioether;
- and
- R2 is alkyl or alkene.
A compound selected from the group consisting of:
A method of preparing a nucleoside phosphate (NP), comprising conjugation of phosphorylated amino acid with pyrophosphate, as outlined in the following reaction scheme:
- wherein B is a purine or pyrimidine base;
- R is H or C(O)NHR2, wherein R2 is C8-18 alkyl;
- and R1 is NHR1a, wherein R1a is H, alkyl, alkene, ether or thioether, and Y is O, NH, CH2, CHF, CHCl, CHBr, CF2, CCl2, CBr2, CCH3, C(CH3)2, CHN3, or CCH3N3.
Dependencies are inferred from the claim text.