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US 2019/0315792 A1Published application
Modified fluorinated nucleoside analogues
AssigneeGilead Pharmasset LLC
InventorJeremy Clark
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Abstract
The disclosed invention provides compositions and methods of treating a Flaviviridae infection, including hepatitis C virus, West Nile Virus, yellow fever virus, and a rhinovirus infection in a host, including animals, and especially humans, using a (2′R)-2′-deoxy-2′-fluoro-2′-C-methyl nucleosides, or a pharmaceutically acceptable salt or prodrug thereof.
Claims5
1-129. (canceled)
130:
- A method of synthesizing a compound of formula 1-3:
- comprising reacting a compound of formula 1-2:
- with (diethylamino)sulfur trifluoride, wherein:
- R is lower alkyl, acyl, benzoyl, or mesyl;
- and
- Pg is selected from among C(O)-alkyl, C(O)Ph, C(O)aryl, CH3, CH2-alkyl, CH2-alkenyl, CH2Ph, CH2-aryl, CH2O-alkyl, CH2O-aryl, SO2-alkyl, SO2-aryl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, or both Pg's may come together to form a 1,3-(1,1,3,3-tetraisopropyl-disiloxanylidene).
3 more elements
131:
- The method of claim 130, wherein:
- R is methyl;
- and
- Pg is CH2Ph.
1 more element
132:
- A method of synthesizing a compound of formula 2-5:
- comprising reacting a compound of formula 2-4:
- with (diethylamino)sulfur trifluoride, wherein:
- R4 is NH2, NH-acyl, OH, O-acyl, or O-sulfonyl;
- and
- PG is selected from among C(O)-alkyl, C(O)Ph, C(O)aryl, CH3, CH2-alkyl, CH2-alkenyl, CH2Ph, CH2-aryl, CH2O-alkyl, CH2O-aryl, SO2-alkyl, SO2-aryl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, or both Pg's may come together to form a 1,3-(1,1,3,3-tetraisopropyl-disiloxanylidene).
3 more elements
133:
- The method of claim 132 wherein:
- R4 is NHBz;
- and
- Pg is C(O)Ph.
1 more element