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US 2014/0274959 A1Published application
Acyclic nucleoside phosphonate diesters
AssigneeThe Regents of the University of California, a California corporation
InventorsKarl Y. Hostetler, James R. Beadle, Nadejda Valiaeva
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Abstract
The present disclosure relates, inter alia, to compositions and methods for treating viral diseases and cancer. There are disclosed lipophilic antiviral and anticancer acyclic nucleoside phosphonate diesters, preparation thereof, and methods of using the compounds to treat viral diseases and cancer.
Claims7
A compound with structure of Formula (I):
- or stereoisomer, salt, hydrate, solvate, or crystalline form thereof,
- wherein
- BNuc is a naturally occurring purine or pyrimidine base, or analog thereof;
- L is a lipophilic promoiety, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, or O-substituted glyceryl having the formula —CH2CH(OR1)—CH2(OR2) (II), wherein R1 and R2 are independently substituted or unsubstituted alkyl, or substituted or unsubstituted aryl;
- R is substituted or unsubstituted lower alkyl, substituted or unsubstituted lower heteroalkyl, substituted or unsubstituted lower cycloalkyl, substituted or unsubstituted lower heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted lower heteroaryl;
- and
- X is hydrogen, substituted or unsubstituted lower alkyl, or substituted or unsubstituted lower heteroalkyl.
4 more elements
A method for synthesis of a compound with structure of Formula (I) according to Scheme 2:
- wherein
- BNuc is a naturally occurring purine or pyrimidine base, or analog thereof;
- L is a lipophilic promoiety, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, or O-substituted glyceryl having the formula —CH2CH(OR1)—CH2(OR2) (II), wherein R1 and R2 are independently substituted or unsubstituted alkyl, or substituted or unsubstituted aryl;
- R is substituted or unsubstituted lower alkyl, substituted or unsubstituted lower heteroalkyl, substituted or unsubstituted lower cycloalkyl, substituted or unsubstituted lower heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted lower heteroaryl;
- and
- X is hydrogen, substituted or unsubstituted lower alkyl, or substituted or unsubstituted lower heteroalkyl;
- and
- Y is a leaving group;
- said method comprising:
- 1) contacting a protected nucleoside BNuc with structure of Formula (2-1) with an ester with structure of Formula (2-2) in the presence of a strong base under conditions suitable to afford a monoester with structure of Formula (2-3);
- and
- 2) reacting said monoester with structure of Formula (2-3) with L-OH in the presence of a coupling agent,
- thereby synthesizing a compound with structure of Formula (I).
10 more elements
Dependencies are inferred from the claim text.