Ether lipid-nucleoside covalent conjugates
AssigneesWake Forest University, The University of North Carolina at Chapel Hill
InventorsClaude Piantadosi, Canio J. Marasco, Jr., Louis S. Kucera
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Abstract
Ether lipid nucleoli covalent conjugates and derivatives thereof are disclosed, along with pharmaceutical compositions containing the same and methods of using the same to combat HIV-1 infections. Illustrative are 3'-Azido-3'-deoxythmidine-5'-monophosphate-D,L-3-octadecanamido-2-ethoxypr opane and 3'-Azido-3'-deoxythymidine-5'-butyrate-.gamma.-N,N,N-trimethyl -ammonium-.beta.-(1-phospho-2-ethoxy-3-hexadecyloxypropane).
Claims21
A lipid-nucleoside conjugate or a salt thereof having the formula:
- ##STR8## wherein:
- R.sub.1 is C15-C20 saturated or unsaturated alkyl containing not more than three double bonds;
- R.sub.2 is H or C1-C3 saturated alkyl;
- W.sub.1 is NHC(.dbd.O) or NH;
- W.sub.2 is S, O, NHC(.dbd.O), NH or a covalent bond;
- n is zero or one;
- X.sub.1 and X.sub.2 are each independently oxygen or a covalent bond, subject to the proviso that when n is zero, then at least either X.sub.1 or X.sub.2 is oxygen;
- B is selected from the group consisting of adenine, thymine, cytosine, guanine, hypoxanthine, and uracil;
- and
- Y is H, F, or N.sub.3 ;
- Z is H or F;
- or Y and Z together are a covalent bond.
A lipid-nucleoside conjugate or a salt thereof having the formula:
- ##STR9## wherein:
- R.sub.1 is C10-C20 saturated or unsaturated alkyl containing not more than three double bonds;
- R.sub.2 is H or C1-C3 alkyl;
- W.sub.1 is S, O, NH or NHC(.dbd.O);
- W.sub.2 is S, O, NHC(.dbd.O), NH or a covalent bond;
- n is zero or one;
- X.sub.1 and X.sub.2 are each independently oxygen or a covalent bond, subject to the proviso that when n is zero, then at least either X.sub.1 or X.sub.2 is oxygen;
- m is 1 to 3;
- B is selected from the group consisting of adenine, thymine, cytosine, guanine, hypoxanthine, and uracil;
- Y is H, F, or N.sub.3 ;
- Z is H or F;
- or Y and Z together are a covalent bond;
- and R.sub.13, R.sub.14, and R.sub.15 are each independently either hydrogen or methyl.
A lipid-nucleoside conjugate or a salt thereof having the formula:
- ##STR10## wherein:
- R.sub.1 is C10-C20 saturated or unsaturated alkyl containing not more than three double bonds;
- R.sub.2 is H or C1-C20 saturated alkyl;
- W.sub.1 is NHC(.dbd.O);
- W.sub.2 is O;
- n is zero or one;
- X.sub.1 and X.sub.2 are each independently oxygen or a covalent bond, subject to the proviso that when n is zero, then at least either X.sub.1 or X.sub.2 is oxygen;
- B is selected from the group consisting of adeninc, thymine, cytosine, guanine, hypoxanthine, and uracil;
- and
- Y is H, F, or N.sub.3 ;
- Z is H or F;
- or Y and Z together are a covalent bond.
Dependencies are inferred from the claim text.