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Details for Patent: 8,629,263

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Details for Patent: 8,629,263

Title:Nucleoside phosphoramidates
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.
Inventor(s): Ross; Bruce (El Granada, CA), Sofia; Michael Joseph (Doylestown, PA), Pamulapati; Ganapati Reddy (San Ramon, CA), Rachakonda; Suguna (Twinsburg, OH), Zhang; Hai-Ren (San Jose, CA), Chun; Byoung-Kwon (Robbinsville, NJ), Wang; Peiyuan (Totowa, NJ)
Assignee: Gilead Pharmasset LLC (Foster City, CA)
Filing Date:Jan 25, 2013
Application Number:13/750,474
Claims:1. A compound represented by the structure: ##STR00041## wherein LG' is tosylate, camphorsulfonate, an aryloxide, or an aryloxide substituted with at least one electron withdrawing group.

2. The compound according to claim 1, wherein LG' is p-nitrophenoxide, p-chlorophenoxide, o-chlorophenoxide, 2,4-dinitrophenoxide, or pentafluorophenoxide.

3. The compound according to claim 1, wherein LG' is p-nitrophenoxide.

4. The compound according to claim 1, wherein LG' is p-chlorophenoxide.

5. The compound according to claim 1, wherein LG' is o-chlorophenoxide.

6. The compound according to claim 1, wherein LG' is pentafluorophenoxide.

7. A process for preparing the compound according to claim 1, which comprises: reacting (LG')P(O)(LG).sub.2, wherein LG and LG' are independently leaving groups, with isopropyl-alanate and a first base to obtain (LG')P(O)(LG)(NHAla-.sup.iPr), followed by reacting (LG')P(O)(LG)(NHAla-.sup.iPr) with phenol and a second base.

8. A process for preparing the compound according to claim 1, which comprises: reacting (LG')P(O)(LG).sub.2, wherein LG and LG' are independently leaving groups, with phenol and a first base to obtain (LG')P(O)(LG)(OPh), followed by reacting (LG')P(O)(LG)(OPh) with isopropyl-alanate and a second base.

9. A process for preparing the compound according to claim 1, which comprises: reacting (LG')P(O)(LG).sub.2, wherein LG and LG' are independently leaving groups, with a combination of isopropyl-alanate, phenol, and at least one base.

10. A process for preparing the compound according to claim 1, which comprises: reacting (PhO)P(O)(LG).sub.2, wherein LG and LG' are independently leaving groups, with isopropyl-alanate and a first base to obtain (PhO)P(O)(LG)(NHAla-.sup.iPr), followed by reacting (PhO)P(O)(LG)(NHAla-.sup.iPr) with a leaving group precursor and a second base.

11. A compound represented by the structure: ##STR00042## wherein LG' is a leaving group.

12. The compound according to claim 11, wherein LG' is tosylate, camphorsulfonate, an aryloxide, or an aryloxide substituted with at least one electron withdrawing group.

13. The compound according to claim 11, wherein LG' is p-nitrophenoxide, p-chlorophenoxide, o-chlorophenoxide, 2,4-dinitrophenoxide, or pentafluorophenoxide.

14. The compound according to claim 11, wherein the compound is represented by the structure: ##STR00043##

15. The compound according to claim 14, wherein LG' is p-nitrophenoxide, 2,4-dinitrophenoxide, or pentafluorophenoxide.

16. The compound according to claim 11, wherein the compound is represented by the structure: ##STR00044##

17. The compound according to claim 16, wherein LG' is p-nitrophenoxide, 2,4-dinitrophenoxide, or pentafluorophenoxide.

18. A process for preparing the compound according to claim 11, which comprises: reacting (LG')P(O)(LG).sub.2, wherein LG and LG' are independently leaving groups, with isopropyl-alanate and a first base to obtain (LG')P(O)(LG)(NHAla-.sup.iPr), followed by reacting (LG')P(O)(LG)(NHAla-.sup.iPr) with phenol and a second base.

19. A process for preparing the compound according to claim 11, which comprises: reacting (LG')P(O)(LG).sub.2, wherein LG and LG' are independently leaving groups, with phenol and a first base to obtain (LG')P(O)(LG)(OPh), followed by reacting (LG')P(O)(LG)(OPh) with isopropyl-alanate and a second base.

20. A process for preparing the compound according to claim 11, which comprises: reacting (LG')P(O)(LG).sub.2, wherein LG and LG' are independently leaving groups, with a combination of isopropyl-alanate, phenol, and at least one base.

21. A process for preparing the compound according to claim 11, which comprises: reacting (PhO)P(O)(LG).sub.2, wherein LG and LG' are independently leaving groups, with isopropyl-alanate and a first base to obtain (PhO)P(O)(LG)(NHAla-.sup.iPr), followed by reacting (PhO)P(O)(LG)(NHAla-.sup.iPr) with a leaving group precursor and a second base.

22. A compound represented by the following structure: ##STR00045##

23. A compound represented by the following structure: ##STR00046##

24. The compound according to claim 22 in crystalline form.

25. The compound according to claim 23 in crystalline form.
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