Abstract: In an embodiment, the invention is directed to prodrug compounds of L-BHDU according to the chemical structure I: Where R1 is a —(CH2)n—O—R1a group or a —(CH2)j—O—C(O)Ok—R2a group; R2 is H, a —(CH2)n—O—R1a group or a —(CH2)j—O—C(O)Ok— R2a group; R1a is independently a C6-C30alkyl group, often a C12-C22 alkyl group, often a C14-C20 alkyl group or a C16-C18 alkyl group, often a C16 or C18 alkyl group; R2a is independently a C1-C12 alkyl group, often a C2-C6 alkyl group, a C3-C4 alkyl group, an isopropyl, t-butyl or sec-butyl group, or an isopropyl or t-butyl group; Each j is independently 1-6, 1-3, often 1 or 2; Each k is 0 or 1; Each n is independently 1-6, 1-4, 2-4 or 2 or 3; or A pharmaceutically acceptable salt, solute or polymorph thereof. Additional embodiments are directed to pharmaceutical compositions based upon the disclosed chemical compounds and methods of treating or reducing the likelihood of VZV, HSV-1 or HSV-2 infections.

Abstract: In an embodiment, the invention is directed to prodrug compounds of L-BHDU according to the chemical structure I: Where R1 is a —(CH2)n—O—R1a group or a —(CH2)j—O—C(O)Ok—R2a group; R2 is H, a —(CH2)n—O—R1a group or a —(CH2)j—O—C(O)Ok—R2a group; R1a is independently a C6-C30 alkyl group, often a C12-C22 alkyl group, often a C14-C20 alkyl group or a C16-C18 alkyl group, often a C16 or C18 alkyl group; R2a is independently a C1-C12 alkyl group, often a C2-C6 alkyl group, a C3-C4 alkyl group, an isopropyl, t-butyl or sec-butyl group, or an isopropyl or t-butyl group; Each j is independently 1-6, 1-3, often 1 or 2; Each k is 0 or 1; Each n is independently 1-6, 1-4, 2-4 or 2 or 3; or A pharmaceutically acceptable salt, solute or polymorph thereof. Additional embodiments are directed to pharmaceutical compositions based upon the disclosed chemical compounds and methods of treating or reducing the likelihood of VZV, HSV-1 or HSV-2 infections.

Abstract: In an embodiment, the invention is directed to prodrug compounds of L-BHDU according to the chemical structure I: Where R1 is a —(CH2)n—O—R1a group or a —(CH2)j—O—C(O)Ok—R2a group; R2 is H, a —(CH2)n—O—R1a group or a —(CH2)j—O—C(O)Ok—R2a group; R1a is independently a C6-C30 alkyl group, often a C12-C22 alkyl group, often a C14-C20 alkyl group or a C16-C18 alkyl group, often a C16 or C18 alkyl group; R2a is independently a C1-C12 alkyl group, often a C2-C6 alkyl group, a C3-C4 alkyl group, an isopropyl, t-butyl or sec-butyl group, or an isopropyl or t-butyl group; Each j is independently 1-6, 1-3, often 1 or 2; Each k is 0 or 1; Each n is independently 1-6, 1-4, 2-4 or 2 or 3; or A pharmaceutically acceptable salt, solute or polymorph thereof. Additional embodiments are directed to pharmaceutical compositions based upon the disclosed chemical compounds and methods of treating or reducing the likelihood of VZV, HSV-1 or HSV-2 infections.

Abstract: The invention provides a new convergent approach for the synthesis of 2?-fluoro-6?-methylene-carbocyclic adenosine (FMCA) and 2?-fluoro-6?-methylene-carbocyclic guanosine (FMCG) from a readily available starting material in eight steps. An efficient and practical methodology for stereospecific preparation of a versatile carbocyclic key intermediate, (1S,3R, 4R)-3-tert-butoxy-4-(tert-butoxymethyl)-2-fluoro-5-methylenecyclopentanol (compound 8 of scheme 1A or a) in only six (6) steps is also provided. Prodrugs of these compounds are also prepared.

Abstract: The invention provides a new convergent approach for the synthesis of 2?-fluoro-6?-methylene-carbocyclic adenosine (FMCA) and 2?-fluoro-6?-methylene-carbocyclic guanosine (FMCG) from a readily available starting material in eight steps. An efficient and practical methodology for stereospecific preparation of a versatile carbocyclic key intermediate, (1S,3R, 4R)-3-tert-butoxy -4-(tert-butoxymethyl)-2-fluoro-5-methylenecyclopentanol (compound 8 of scheme 1A or a) in only six (6) steps is also provided. Prodrugs of these compounds are also prepared.

Abstract: The invention provides a new convergent approach for the synthesis of 2?-fluoro-6?-methylene-carbocyclic adenosine (FMCA) and 2?-fluoro-6?-methylene-carbocyclic guanosine (FMCG) from a readily available starting material in eight steps. An efficient and practical methodology for stereospecific preparation of a versatile carbocyclic key intermediate, (1S,3R,4R)-3-tert-butoxy-4-(tert-butoxymethyl)-2-fluoro-5-methylenecyclopentanol (compound 8 of scheme 1A or a) in only six (6) steps is also provided. Prodrugs of these compounds are also prepared.

Abstract: The invention provides a new convergent approach for the synthesis of 2?-fluoro-6?- methylene-carbocyclic adenosine (FMCA) and 2?-fluoro-6?-methylene-carbocyclic guanosine (FMCG) from a readily available starting material in eight steps. An efficient and practical methodology for stereospecific preparation of a versatile carbocyclic key intermediate, (1S,3R,4R)-3-tert-butoxy-4-(tert-butoxymethyl)-2-fluoro-5-methylenecyclopentanol (compound 8 of scheme 1A or a) in only six (6) steps is also provided. Prodrugs of these compounds are also prepared.