Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Reexamination Certificate
2005-08-09
2005-08-09
McKenzie, Thomas C. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
Reexamination Certificate
active
06927291
ABSTRACT:
An efficient synthetic route to antiviral 2′,3′-dideoxy-2′,3′-didehydro-nucleosides, such as 2′,3′-dideoxy and 2′- or 3′-deoxyribo-nucleoside analogs, from available precursors is disclosed, with the option of introducing functionality as needed. In one embodiment, a method for the preparation of β-D and β-L-2′,3′-dideoxy-2′,3′-didehydro-nucleosides is described that includes: activating a compound of structure (1)wherein B is a pyrimidine or purine base and Y is O, S or CH2with an acyl halide of the formula X—C(═O)R1, X—C(═O)C(R1)2OC(═O)R1or X—C(═O)OR1(wherein X is a halogen, and each R1is independently hydrogen, lower alkyl, alkyl, aryl or phenyl); reducing the resulting compound with a reducing agent to form a 2′,3′-dideoxy-2′,3′-didehydro-nucleoside; and optionally deprotecting the nucleoside. The haloacylation of the first step can form the 2′-acyl-3′-halonucleoside, the 3′-acyl-2′-halonucleoside, or a mixture thereof.
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Confalone Pasquale N.
Jin Fuqiang
King & Spalding LLP
Knowles, Esq. Sherry M.
McKenzie Thomas C.
Pharmasset, Ltd.
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