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US 8,642,756 B2Granted
Nucleoside phosphoramidates
AssigneeGilead Pharmasset LLC
InventorsBruce Ross, Michael Joseph Sofia, Ganapati Reddy Pamulapati, Suguna Rachakonda, Hai-Ren Zhang, Byoung-Kwon Chun, Peiyuan Wang
Life of this patent
Estimating the term…
Abstract
Disclosed herein are nucleoside phosphoramidates and their use as agents for treating viral diseases. These compounds are inhibitors of RNA-dependent 5 RNA viral replication and are useful as inhibitors of HCV NS5B polymerase, as inhibitors of HCV replication and for treatment of hepatitis C infection in mammals.
Claims23
A process for preparing a compound represented by formula (4), or a phosphorous-based diastereomer thereof:
- wherein P* represents a chiral phosphorus atom, and wherein said phosphorous-based diastereomer is represented by formula (Rp-4) or (Sp-4):
- which comprises:
- a) reacting a mixture comprising an isopropyl-alanate (A), a di-X′-phenylphosphate (B), 2′-deoxy-2′-fluoro-2′-C-methyluridine (3), and a base to obtain a first mixture comprising (4), or the phosphorous-based diastereomer thereof:
- wherein X is a conjugate base of an acid, n is 0 or 1, and X′ is a halogen;
- b) reacting the first mixture with a protecting compound to obtain a second mixture comprising protected (4), or the phosphorous-based diastereomer thereof;
- and
- c) optionally subjecting the second mixture to crystallization, chromatography, or extraction in order to obtain (4), or the phosphorous-based diastereomer thereof.
4 more elements
A process for preparing a crystalline compound (Rp-4) or (Sp-4):
- which comprises:
- a) reacting a mixture comprising an isopropyl-alanate (A), a di-X′-phenylphosphate (B), 2′-deoxy-2′-fluoro-2′-C-methyluridine (3), and a base to obtain a first mixture comprising (Rp-4) or (Sp-4):
- wherein X is a conjugate base of an acid, n is 0 or 1, and X′ is a halogen;
- b) reacting the first mixture with a protecting compound to obtain a second mixture;
- and
- c) optionally subjecting the second mixture to crystallization, chromatography, or extraction in order to obtain a third mixture.
3 more elements
Dependencies are inferred from the claim text.