Synthesis and antiviral activity of a series of pyrophosphate analogs
AssigneeUniversity of Southern California
InventorsCharles E. McKenna, Zeng-Min Li, Xue-Wei Liu
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Abstract
Preparations of pyrophosphate analogues, including phosphonoformic acid, bisphosphonic acid, and phosphonoacetic acid derivatives, exhibiting antiviral activity. Such compounds, are used directly, or as prodrugs, in compositions and methods for treating viral infections, including but not limited to HIV, herpesviruses including HSV, EBV, VZV, CMV, HHV-6 and HHV-8 (Kaposi's sarcoma); HPV; rhinoviruses; and hepatitis-linked viruses. Compounds of the present invention for use as antiviral agents or their intermediates include sulfur-containing, polyhydroxy, and lipophilic derivatives of phosphonoformic acid.
Claims6
A compound having formula I
- wherein R1 is a cation, C1-C16 alkyl or polyalcohol derivative having the general formula CH2(R4)CH(R5)CH2—, wherein R4 and R5 are each independently C1-C16 alkoxy or O-acyl C1-C16 alkyl;
- R2 and R3 are each independently cation or C1 to C16 alkyl;
- X2 is oxygen;
- and X1, X3, X4, and X5 are each independently sulfur or oxygen, provided at least one of (a), (b), (c) or (d) applies:
- (a) R3 is C7-C16 alkyl;
- or
- (b) X1 is sulfur;
- or
- (c) X3 and X4 are sulfur;
- or
- (d) R1 is C7-C16 alkyl and X3 is sulfur.
An antivirally active compound or intermediate thereof having formula I
- wherein R1 is sodium, dicyclohexylammonium (DCHA), or methyl, R2 is sodium, DCHA, or methyl;
- R3 is sodium, methyl, or C14H29;
- X2 is oxygen, and X1, X3, X4, and X5 are each independently sulfur or oxygen provided at least one of X1, X3, X4, and X5 is oxygen, and at least one of (a), (b), or (c) applies;
- (a) R3 is C14H29;
- or
- (b) X1 is sulfur;
- or
- (c) X3 and X4 are sulfur.
A phosphonoformic acid derivative, selected from the group consisting of:
Dependencies are inferred from the claim text.