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US 5,792,756 AGranted
Prodrugs of phosphonates
AssigneesInstitute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.
InventorsJohn E. Starrett, Jr., Muzammil M. Mansuri, John C. Martin, David R. Tortolani, Joanne J. Bronson
Life of this patent
Estimating the term…
Abstract
There are disclosed novel oral prodrugs of phosphonate nucleotide analogs which are hydrolyzable under physiological conditions to yield compounds which are useful as antiviral agents, especially as agents effective against RNA and DNA viruses. They may also find use as antitumor agents.
Claims7
The compound having formula II ##STR25## wherein B is cytosine or Z;
- R.sup.1 and R.sup.2 are independently OH or OR.sup.4 provided that at least one of R.sup.1 or R.sup.2, is OR.sup.4, or one of R.sup.1 or R.sup.2 is linked to X to form a cyclic compound having Formula V ##STR26## * stereochemistry R, S, or RS;
- R.sup.13 is OR.sup.4 ;
- X is CH.sub.2 OR.sup.6 (R, S or RS stereochemistry) or hydroxymethyl with the proviso that when X is CH.sub.2 OR.sup.6, then R.sup.1 and R.sup.2 may additionally be independently chosen from OH;
- R.sup.6 is a hydrolyzable ester;
- R.sup.4 is CH.sub.2 C(O)NR.sup.5.sub.2, CH.sub.2 C(O)OR.sup.5, CH.sub.2 OC(O)R.sup.5, CH(R.sup.5)OC(O)R.sup.5 (R, S, or RS stereochemistry), CH.sub.2 C(R.sup.5.sub.2 CH.sub.2 OH, or CH.sub.2 OR.sup.5 ;
- R.sup.4 may also be R.sup.5' ;
- R.sup.5 is C.sub.1 -C.sub.20 alkyl, aryl or aryl-alkyl which is unsubstituted or is substituted by hydroxy, oxygen, nitrogen or halogen;
- R.sup.5' is C.sub.4 -C.sub.20 alkyl, aryl or aryl-alkyl which is substituted by hydroxy, oxygen, nitrogen or halogen;
- Z is ##STR27## O is independently H, Cl, NHR.sup.5, NR.sup.5.sub.2, NHC(O)R.sup.5, N(C(O)R.sup.5).sub.2, OH or NCHN(R.sup.5).sub.2 provided that when O is NCHN(R.sup.5).sub.2, then R.sup.5 is not CH.sub.3.
6 more elements
Dependencies are inferred from the claim text.