IP Library Granted Patent US 8,846,727
Granted Patent B2
US 8,846,727 · App. 12/777,383 · Granted Sep 30, 2014

Haloalkyl heteroaryl benzamide compounds

Inventors: Jean-Francois Rossignol (St. Petersburg, FL); J. Edward Semple (Tampa, FL)
Assignee: Romark Laboratories, L.C.
C07D277/46C07D261/14C07D275/03C07D285/135C07D403/12C07D249/14C07D277/56C07D233/90C07D231/40C07D233/88C07D417/12C07D271/113C07D413/12C07D263/48C07D231/44C07D285/08C07D409/06C07D403/06C07D417/06C07D405/12C07D271/07
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Quick Facts
Patent No.
US 8,846,727
App. No.
12/777,383
Granted
Sep 30, 2014
Kind
B2
Abstract

A new class of haloalkyl heteroaryl benzamides is described. These compounds show strong activity against hepatitis viruses.

Claims (332)

1. A compound of Formula I:

wherein:

R 1 through R 5 are, independently, hydrogen, CN, F, Cl, Br, hydroxy, alkyl, alkoxy, hydroxyalkyl, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, carbamoyloxy, alkylamino, haloalkyl, perhaloalkyl, perhaloalkoxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, or cycloalkylalkylsulfonyl, any of which may be optionally substituted with halogen, alkoxy, perhalo-C 1 -C 3 -alkyl, or C 1 -C 3 alkyl;

wherein at least one of R 1 , R 2 and R 3 is hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, or carbamoyloxy, any of which may be optionally substituted;

wherein R 6 is selected from the group consisting of perhaloalkyl, S(O) m C(R 7 R 8 ) n CF 3 , and C(R 7 R 8 ) n CF 3 ;

wherein W, X and Y are, independently, S, O, N, NR 9 or CR 10 where at least two of W, X, and Y are S, O, N, or NR 9 ;

R 7 , R 8 , and R 9 are independently selected from the group consisting of hydrogen, fluoro, chloro, alkyl, and perhaloalkyl, any of which may be optionally substituted;

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkoxyalkyl, cycloalkoxy, cycloalkylalkoxy, acyl, alkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, heteroaryloxycarbonyl, heteroarylalkoxycarbonyl, carbamoyl, alkylamino, amido, alkylamido, dialkylamido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, alkylsulfonamido, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino, arylalkylamino, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkoxy, heteroarylamino, heteroarylalkylamino, heteroarylthio, heteroarylalkylthio, heteroarylalkylamino, heterocycloalkyl, heterocycloalkenyl, heterocycloalkoxy, and heterocycloalkenyloxy;

m is an integer between 0 and 2; and

n is an integer between 0 and 5;

or a pharmaceutically acceptable salt or ester thereof.

2. The compound according to claim 1 , wherein:

R 6 is selected from the group consisting of perhaloalkyl and C(R 7 R 8 ) n CF 3 ;

W, X and Y are S, N, or CR 10 wherein one of W, X, and Y is S, one of W, X, and Y is N, and one of W, X, and Y is CR 10 .

3. The compound according to claim 1 having the structural Formula II:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

4. The compound according to claim 3 , wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

5. The compound according to claim 2 , wherein:

R 1 is hydroxy or acetoxy; and R 2 -R 5 and R 10 are hydrogen.

6. The compound according to claim 1 having the structural Formula III:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

7. The compound according to claim 6 , wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

8. The compound according to claim 7 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

9. The compound according to claim 1 having the structural Formula IV

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, alkyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl; and

with the proviso that when R 4 is Br, R 10 may not be unsubstituted phenyl.

10. The compound according to claim 9 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

11. The compound according to claim 8 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

12. The compound according to claim 1 having the structural Formula V:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

13. The compound according to claim 12 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

14. The compound according to claim 13 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

15. The compound according to claim 1 having the structural Formula VI:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

16. The compound according to claim 15 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

17. The compound according to claim 16 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

18. The compound according to claim 1 having the structural Formula VII:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

19. The compound according to claim 18 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

20. The compound according to claim 19 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

21. The compound according to claim 1 having the structural Formula VIII:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

22. The compound according to claim 21 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

23. The compound according to claim 22 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

24. The compound according to claim 1 having the structural Formula IX:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

25. The compound according to claim 24 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

26. The compound according to claim 25 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

27. The compound according to claim 1 having the structural Formula X:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

28. The compound according to claim 27 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted;

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted; and

R 9 is selected from the group consisting of hydrogen, alkyl, and perhaloalkyl, any of which may be optionally substituted.

29. The compound according to claim 28 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy;

R 2 through R 5 and R 10 are hydrogen; and

R 9 is alkyl, which may be optionally substituted.

30. The compound according to claim 1 having the structural Formula XI:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

31. The compound according to claim 30 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted;

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted; and

R 9 is selected from the group consisting of hydrogen, alkyl, and perhaloalkyl, any of which may be optionally substituted.

32. The compound according to claim 31 , wherein:

R I is chosen from the group consisting of hydroxy and acetoxy;

R 2 through R 5 and R 10 are hydrogen; and

R 9 is alkyl, which may be optionally substituted.

33. The compound according to claim 1 having the structural Formula XII:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

34. The compound according to claim 33 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted;

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted; and

R 9 is selected from the group consisting of hydrogen, alkyl, and perhaloalkyl, any of which may be optionally substituted.

35. The compound according to claim 34 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy;

R 2 through R 5 and R 10 are hydrogen; and

R 9 is alkyl, which may be optionally substituted.

36. The compound according to claim 1 having the structural Formula XIII:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

37. The compound according to claim 36 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted;

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted; and

R 9 is selected from the group consisting of hydrogen, alkyl, and perhaloalkyl, any of which may be optionally substituted.

38. The compound according to claim 37 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy;

R 2 through R 5 and R 10 are hydrogen; and

R 9 is alkyl, which may be optionally substituted.

39. The compound according to claim 1 having the structural Formula XIV:

wherein:

R 1 and R 2 are, independently, hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, or carbamoyloxy, any of which may be optionally substituted;

R 3 is selected from the group consisting of acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

40. The compound according to claim 39 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

41. The compound according to claim 39 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy: and

R 2 through R 5 and R 10 are hydrogen.

42. The compound according to claim 1 having the structural Formula XV:

wherein:

R 1 and R 2 are, independently, hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, or carbamoyloxy, any of which may be optionally substituted;

R 3 is selected from the group consisting of acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

43. The compound according to claim 42 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkenoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

44. The compound according to claim 43 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

45. The compound according to claim 1 having the structural Formula XVI:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

46. The compound according to claim 45 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

47. The compound according to claim 46 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

48. The compound according to claim 1 having the structural Formula XVII:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

49. The compound according to claim 48 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

50. The compound according to claim 49 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 and R 10 are hydrogen.

51. The compound according to claim 1 having the structural Formula XVIII:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

52. The compound according to claim 51 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted;

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted; and

R 9 is selected from the group consisting of hydrogen, alkyl, and perhaloalkyl, any of which may be optionally substituted.

53. The compound according to claim 52 , wherein: R 1 is hydroxy or acetoxy;

R 2 through R 5 and R 10 are hydrogen; and

R 9 is methyl.

54. The compound according to claim 1 having the structural Formula XIX:

wherein:

R 10 is selected from the group consisting of hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, dialkylamido, perhaloalkyl, alkylsulfonyl, alkylsulfonylalkyl, cycloalkylsulfonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, and heterocycloalkenyl.

55. The compound according to claim 54 wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted:

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted; and

R 9 is selected from the group consisting of hydrogen, alkyl, and perhaloalkyl, any of which may be optionally substituted.

56. The compound according to claim 55 , wherein:

R 1 is hydroxy or acetoxy; R 2 through R 5 and R 10 are hydrogen; and R 9 is methyl.

57. The compound according to claim 1 having the structural Formula XX

wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl; alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted;

with the following provisos when R 6 is trifluoromethyl:

when R 1 is selected from the group consisting of hydroxy, and acetoxy, R 2 -R 5 cannot be hydrogen;

when R 1 is hydroxy, R 4 cannot be selected from the group consisting of Cl and Br; and

when R 3 is acetoxy, R 1 , R 2 , R 4 and R 5 may not be hydrogen.

58. The compound according to claim 57 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy;

R 2 through R 5 are hydrogen; and R 6 is perfluoroethyl, CF 3 CH 2 —, and CH 3 CF 2 —.

59. The compound according to claim 1 having the structural Formula XXI:

wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, all optionally substituted.

60. The compound according to claim 59 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 are hydrogen.

61. The compound according to claim 1 having the structural Formula XXII:

wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, all optionally substituted.

62. The compound according to claim 61 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 are hydrogen.

63. The compound according to claim 1 having the structural Formula XXIII:

wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, any of which may be optionally substituted.

64. The compound according to claim 63 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 are hydrogen.

65. The compound according to claim 1 having the structural Formula XXIV:

wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, all optionally substituted.

66. The compound according to claim 65 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 are hydrogen.

67. The compound according to claim 1 having the structural Formula XXV:

wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, all optionally substituted.

68. The compound according to claim 67 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy; and

R 2 through R 5 are hydrogen.

69. The compound according to claim 1 having the structural Formula XXVI:

wherein:

R 9 is selected from the group consisting of hydrogen, alkyl, and perhaloalkyl, any of which may be optionally substituted.

70. The compound according to claim 69 , wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, all optionally substituted.

71. The compound according to claim 70 , wherein:

R 1 is hydroxy or acetoxy; R 2 through R 5 are hydrogen; and R 9 is methyl.

72. The compound according to claim 1 having the structural Formula XXVII:

wherein:

R 9 is hydrogen or alkyl, optionally substituted, or perhaloalkyl.

73. The compound of claim 72 , wherein R 9 is perhaloalkyl.

74. The compound according to claim 73 , wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, all optionally substituted.

75. The compound according to claim 74 , wherein:

R 1 is chosen from the group consisting of hydroxy and acetoxy;

R 2 through R 5 are hydrogen; and

R 9 is methyl.

76. The compound according to claim 1 having the structural Formula XXVIII:

wherein:

R 9 is alkyl, optionally substituted, hydrogen, or perhaloalkyl.

77. The compound according to claim 76 , wherein:

R 1 is chosen from the group consisting of hydroxy, acyloxy, aroyloxy, arylalkanoyloxy, arylalkenoyloxy, heteroaroyloxy, heteroarylalkanoyloxy, heteroarylalkenoyloxy, alkoxycarbonyloxy, and carbamoyloxy, any of which may be optionally substituted; and

R 2 through R 5 are, independently, hydrogen, CN, NO 2 , F, Cl, Br, alkyl, cycloalkyl, alkoxy, cycloalkoxy, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, carbamoyl, amido, perhaloalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylsulfonyl, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heteroarylalkylthio, heterocycloalkyl, or heterocycloalkoxy, all optionally substituted.

78. The compound according to claim 77 , wherein:

R 1 is hydroxy or acetoxy; R 2 through R 5 are hydrogen; and R 9 is methyl.

79. The compound according to claim 1 , wherein the salt is selected from the group consisting of acetate, adipate, alginate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, citrate, camphorate, camphorsulfonate, cyclopentanepropionate, digluconate, dodecylsulfate, ethanesulfonate, fumarate, glucoheptanoate, glycerophosphate, hemisulfate, heptanoate, hexanoate, hydrochloride, hydrobromide, hydroiodide, 2-hydroxyethane-sulfonate, lactate, malate, maleate, methanesulfonate, 2-naphthalenesulfonate, nicotinate, oxalate, thiocyanate, tosylate, undecanoate, lithium, sodium, calcium, potassium, aluminum, ammonium, tetraethylammonium, methylammonium, dimethylammonium, N-methylmorpholinium and ethanolammonium.

80. A composition comprising any of the compounds of claim 1 and a carrier.

81. A pharmaceutical composition comprising a compound of Formula I as claimed in claim 1 , and a pharmaceutically acceptable carrier.

82. A compound as shown in Table 1:

1

2

3

4

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

83. A compound according to claim 82 , selected from examples 1 through 4 of Table 1.

84. A compound of Formula I as claimed in claim 1 , comprising one or more radioactive isotopes.

Assignments (8)
SECURITY INTEREST Recorded Nov 16, 2019
From: ROMARK BIOSCIENCES S.À R.L. LLC; ROMARK LABORATORIES, L.C.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 051030/0613 →
SECURITY INTEREST Recorded Jul 2, 2018
From: ROMARK BIOSCIENCES S.À R.L. LLC; ROMARK LABORATORIES, L.C.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 046254/0524 →
SECURITY INTEREST Recorded Dec 22, 2017
From: ROMARK BIOSCIENCES S.À R.L. LLC; ROMARK LABORATORIES, L.C.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 044472/0001 →
RELEASE OF SECURITY INTEREST Recorded Mar 6, 2015
From: U.S. BANK NATIONAL ASSOCIATION
To: ROMARK LABORATORIES, L.C.; ROMARK MANUFACTURING, LLC; LAPICOR, N.V.
Reel/Frame 035108/0474 →
SECURITY AGREEMENT Recorded Sep 4, 2013
From: ROMARK LABORATORIES, L.C.; ROMARK MANUFACTURING, LLC; LAPICOR, N.V.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 031156/0923 →
RELEASE OF SECURITY INTEREST Recorded Sep 3, 2013
From: PAUL CAPITAL FUND MANAGEMENT, L.L.C.
To: ROMARK LABORATORIES, L.C.
Reel/Frame 031159/0636 →
SECURITY AGREEMENT Recorded Jul 29, 2011
From: ROMARK LABORATORIES, L.C.
To: PAUL CAPITAL FUND MANAGEMENT, L.L.C.
Reel/Frame 026676/0635 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 11, 2010
From: ROSSIGNOL, JEAN-FRANCOIS; SEMPLE, J. EDWARD
To: ROMARK LABORATORIES L.C.
Reel/Frame 024364/0392 →
Continuity (2)
Provisional Application 61177626 · May 12, 2009
Related Publication 20100292274A1 · Nov 18, 2010