Patent ID: 7598230

Claim:
A compound of Formula (I) which may be a D- or L-nucleotide: wherein A is O; R 4′ is -L-R 5 L is CY 2 O, CY 2 S, wherein Y is selected from the group consisting of H, F, Cl, Br, and alkyl; R 5 is a tri-phosphate moiety of Formula (II): X 2 , X 3 , and X 4 are selected independently from the group consisting of O and S; X 5 is O or S; X 6 is selected from the group consisting of NH, and CY 2 ; X 8 , X 9 , and X 10 are selected independently from the group consisting of OH, SH, NH 2 , R, OR, SR, NHR, NR 2 , and R*, wherein R* is a prodrug substituent selected from the group consisting of acylthioethoxy, (SATE) RCOSCH 2 CH 2 O—, RCOSCH 2 CH 2 O—W—O—, RCOSCH 2 CH 2 O—W—S—, RCOSCH 2 CH 2 O—W—NH—, RCOSCH 2 CH 2 O—W—, RCOSCH 2 CH 2 O—W—CY 2 —, acyloxymethoxy, RCOOCH 2 O—, RCOOCH 2 O—W—O—, RCOOCH 2 O—W—S—, RCOOCH 2 O—W—NH—, RCOOCH 2 O—W—, RCOOCH 2 O—W—CY 2 —, alkoxycarbonyloxymethoxy, ROCOOCH 2 O—, ROCOOCH 2 O—W—O—, ROCOOCH 2 O—W—S—ROCOOCH 2 O—W—NH—, ROCOOCH 2 O—W—, ROCOOCH 2 O—W—CY 2 —acylthioethyldithioethoxy (DTE) RCOSCH 2 CH 2 SSCH 2 CH 2 O—, RCOSCH 2 CH 2 SSCH 2 CH 2 O—W—, RCOSCH 2 CH 2 SSCH 2 CH 2 O—W—O—, RCOSCH 2 CH 2 SSCH 2 CH 2 O—W—S—, RCOSCH 2 CH 2 SSCH 2 CH 2 O—W—NH—, RCOSCH 2 CH 2 SSCH 2 CH 2 O—CY 2 —acyloxymethyiphenylmethoxy, (PAOB) RCO 2 -C 6 H 4 —CH 2 —O—RCO 2 —C 6 H 4 —CH 2 —O—W—RCO 2 —C 6 H 4 —CH 2 —O—W—O—, RCO 2 —C 6 H 4 —CH 2 —O—W—S—, RCO 2 —C 6 H 4 —CH 2 —O—W—NH—RCO 2 —C 6 H 4 —CH 2 —O—W—CY 2 —, 1,2-O-diacyl-glyceryloxy, RCOO—CH 2 —CH(OCOR)—CH 2 O—, 1,2-O-dialkyl-glyceryloxy, RO—CH 2 —CH(OR)—CH 2 O—, 1,2-S-dialkyl-glyceryloxy, RS—CH 2 —CH(SR)—CH 2 O—,1-O-alkyl-2-O-acyl-glyceryloxy, RO—CH 2 —CH(OCOR)—CH 2 O—, 1-S-alkyl-2-O-acyl-glyceryloxy, RS—CH 2 —CH(OCOR)—CH 2 O—, 1-O-acyl-2-O-alky-glyceryloxy, RCOO—CH 2 —CH(OR)—CH 2 O—, 1-O-acyl-2-S-alkyl-glyceryloxy, RCOO—CH 2 —CH(SR)—CH 2 O—, where W is alkyl; wherein at least one of X 8 , X 9 and X 10 is R*; X 7 is − BH 3 M + ; R* may be conjugated to one or more X 8 -X 10 positions; R is selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, acyl, and aralkyl, each optionally containing one or more heteroatoms; M + is a cation; n is 1; R 1 , R 2 , R 3 , and R 4 each represent H, F, Cl or R; R 2′ and R 3′ are selected independently from the group consisting of H, F, Cl, Br, OH, SH, NH 2 , NHOH, N 3 , CN, R, OR, SR, NHR, and NR 2 ; D is a nucleoside base of Formula (III): Z 1 is N, CH or C-G 3 ; and G 1 , G 2 , and G 3 are selected independently from the group consisting of H, F, Cl, Br, I, OH, SH, NH 2 , R, OR, SR, NHR, and NR 2 .