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US 2017/0253584 A1Published application
Preparation of 2'-fluoro-2'-alkyl-substituted or other optionally substituted ribofuranosyl pyrimidines and purines and their derivatives
AssigneeGilead Pharmasset LLC
InventorsByoung Kwon Chun, Jinfa Du, Suguna Rachakonda, Peiyuan Wang
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Abstract
The present invention provides (i) processes for preparing a 2′-deoxy-2′-fluoro-2′-methyl-D-ribonolactone derivatives, (ii) conversion of intermediate lactones to nucleosides with potent anti-HCV activity, and their analogues, and (iii) methods to prepare the anti-HCV nucleosides containing the 2′-deoxy-2′-fluoro-2′-C-methyl-β-D-ribofuranosyl nucleosides from a preformed, preferably naturally-occurring, nucleoside.
Claims12
A compound of formula
- wherein
- R′ and R″ are independently H, lower alkyl (C1-C6), aryl (C6-C20), optionally substituted benzyl, trialkylsilyl, t-butyl-dialkylsilyl, t-butyldiphenylsilyl, TIPDS, THP, MOM, MEM, acetyl, benzoyl, or optionally substituted acyl;
- or R′ and R″ form a cyclopentyl or cyclohexanyl group;
- R1 and R2 are independently H, lower alkyl (C1-C6), aryl (C6-C20), hydroxymethyl, methoxymethyl, halomethyl, optionally substituted ethenyl, halovinyl, optionally substituted ethynyl, or optionally substituted allyl;
- and
- R3 is H, aryl, arylalkyl, or lower alkyl (C1-C6).
3 more elements
A compound of formula
- wherein
- each R1 is independently lower alkyl (C1-C6), optionally substituted phenyl, or optionally substituted benzyl;
- or R1 forms a cyclopentyl or cyclohexanyl group;
- R2 and R3 are independently hydrogen, lower alkyl (C1-C6), hydroxymethyl, methoxymethyl, halomethyl, optionally substituted ethenyl, halovinyl, optionally substituted ethynyl, or optionally substituted allyl;
- and
- R4 is independently arylalkyl, or lower alkyl (C1-C10).
3 more elements
A compound of formula
- wherein
- R2 and R3 are independently H, alkyl (C1-C10), hydroxymethyl, methoxymethyl, halomethyl, optionally substituted ethenyl, halovinyl, optionally substituted ethynyl, or optionally substituted allyl;
- R5 and R6 are methoxymethyl, methoxyethyl, benzyloxymethyl, ethoxymethyl, trityl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, acetyl, pivaloyl, benzoyl, toluoyl, 4-phenyl benzoyl, 2-nitrobenzoyl, 3-nitrobenzoyl, 4-nitrobenzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, or substituted benzoyl;
- Nu is F, Cl, Br, N3, CN, NO3, SCN, OR or NR2 wherein R is acyl or lower alkyl (C1-C10);
- and
- L is a leaving group.
3 more elements
A compound of formula
A compound of formula IIIa, IIIb or IIIc
- wherein
- each R1 is independently lower alkyl (C1-C6), optionally substituted phenyl, or optionally substituted benzyl;
- R2 and R3 are independently hydrogen, lower alkyl (C1-C6), hydroxymethyl, methoxymethyl, halomethyl, optionally substituted ethenyl, optionally substituted ethynyl, or optionally substituted allyl;
- and
- R4 is independently hydrogen, aryl, arylalkyl, or lower alkyl (C1-C10).
2 more elements
Dependencies are inferred from the claim text.