IP Library Granted Patent US 7,985,769
Granted Patent B2
US 7,985,769 · App. 11/042,442 · Granted Jul 26, 2011

Compounds and methods for the treatment or prevention of

Assignee: Vertex Pharmaceuticals Incorporated
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Quick Facts
Patent No.
US 7,985,769
App. No.
11/042,442
Granted
Jul 26, 2011
Kind
B2
Abstract

The present invention provides novel compounds represented by formula I: or pharmaceutically acceptable salts thereof useful for treating flaviviridae viral infection.

Claims (112)

1. A compound having the formula (I):

or a pharmaceutically acceptable salt thereof;

wherein,

X is

M is

J is

Y 1 is a bond;

Y is COOH;

R 1 is C 2-12 alkyl, C 2-12 alkenyl, C 2  alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl or C 6-18 aralkyl;

R 2 is C 2-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl, or C 6-18 aralkyl;

R 3 is H, C 1-12 alkyl, C 2-12 alkenyl, C 2  alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl or C 6-18 aralkyl; and

Z is H, halogen, or C 1-6 alkyl;

with the proviso that: when X is Benzamide and R 1 is phenyl, then R 3 is other than hydrogen;

wherein

alkyl in R 1 , R 2 , R 3 , and Z is in each case optionally substituted by one or more of: halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido;

alkenyl in R 1 , R 2 , and R 3 is in each case optionally substituted by one or more of: halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido;

alkynyl in R 1 , R 2 , and R 3 is in each case optionally substituted by one or more of:: halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido;

aryl in R 1 , R 2 , and R 3 is in each case optionally substituted by one or more of: halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido;

aralkyl in R 1 , R 2 , and R 3 is in each case an aryl group attached to the adjacent atom by a C 1-6 alkyl, C 2-6 alkenyl, or C 2-6 alkynyl, and the aryl group is in each case optionally substituted by one or more of: halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido;

heterocycle in R 1 , R 2 , and R 3 is in each case optionally substituted by one or more of: halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido;

heteroaralkyl in R 1 , R 2 , and R 3 in each case an heterocycle group attached to the adjacent atom by a C 1-6 alkyl, C 2-6 alkenyl, or C 2-6 alkynyl, and the heterocycle group is in each case optionally substituted by one or more of: halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido; and

R 12 , R c , R d , R 13 and R 14 , are each independently H, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl, or C 6-18 aralkyl, or R c and R d are taken together with the oxygens to form a 5 to 10 membered heterocycle, or R 13 and R 14 are taken together with the nitrogen to form a 3 to 10 membered heterocycle,

in each case above alkyl groups include alkyls in which one or more hydrogen atoms are each replaced by a halogen, and

sulfur atoms are in the form of S, SO, or SO 2 .

2. A compound according to claim 1 , wherein said compound is of formula Ia:

or a pharmaceutically acceptable salt thereof.

3. A compound according to claim 1 , wherein X is

4. A compound according to claim 1 , wherein Z is H.

5. A compound according to claim 1 , wherein R 1 is C 2-12 alkyl, C 6-14 aryl, or C 3-12 heterocycle, which in each case is substituted or unsubstituted.

6. A compound according to claim 1 , wherein R 3 is H, C 1-12 alkyl, C 6-18 aralkyl, C 3-12 heterocycle, or C 3-18 heteroaralkyl, which in each case is substituted or unsubstituted.

7. A compound according to claim 6 , wherein R 3 is C 1-12 alkyl which is substituted or unsubstituted.

8. A compound according to claim 1 , wherein

R 3 is H, or R 3 is methyl, ethyl, isopropyl, cyclopropyl, cyclohexyl, allyl, piperidinyl, piperazinyl, pyrrolidinyl, azetidinyl, aziridinyl, pyridinyl, piperidinylmethyl, dioxanyl, azepanyl or benzyl, which in each case is unsubstituted or substituted by one or more substituents chosen from halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido; and

R 12 , R c , R d , R 13 and R 14 are each independently H, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl, or C 6-18 aralkyl,

or R c and R d , taken together with the oxygens, form a 5 to 10 membered heterocycle,

or R 13 and R 14 , taken together with the nitrogen, form a 3 to 10 membered heterocycle.

9. A compound according to claim 1 , wherein R 3 is H, or R 3 is methyl, isopropyl, piperidinyl, piperidinylmethyl, dioxolanyl or cyclohexyl, which in each case is substituted or unsubstituted by one or more substituents chosen from halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido; and

R 12 , R c , R d , R 13 and R 14 are each independently H, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl, or C 6-18 aralkyl,

or R c and R d , taken together with the oxygens, form a 5 to 10 membered heterocycle,

or R 13 and R 14 , taken together with the nitrogen, form a 3 to 10 membered heterocycle.

10. A compound according to claim 9 , wherein R 3 is isopropyl which is substituted or unsubstituted.

11. A compound according to claim 9 , wherein R 3 is cyclohexyl which is substituted or unsubstituted.

12. A compound according to claim 1 , wherein R 2 is C 2-12 alkyl, C 6-14 aryl, or C 3-12 heterocycle, which in each case is substituted or unsubstituted.

13. A compound according to claim 2 , wherein R 2 is C 2-12 alkyl which is substituted or unsubstituted.

14. A compound according to claim 1 , wherein

R 2 is cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl cyclohexyl, cycloheptyl, 2-(cyclopentyl)-ethyl, ethyl, vinyl, propyl, propenyl, isopropyl, butyl, butenyl isobutyl, pentyl, neopentyl or t-butyl, which in each case is unsubstituted or substituted by one or more substituents chosen from halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido; and

R 12 , R c , R d , R 13 and R 14 are each independently H, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl, or C 6-18 aralkyl,

or R c and R d , taken together with the oxygens, form a 5 to 10 membered heterocycle,

or R 13 and R 14 , taken together with the nitrogen, form a 3 to 10 membered heterocycle.

15. A compound according to claim 2 , wherein X is

16. A compound according to claim 2 , wherein Z is H.

17. A compound according to claim 2 , wherein R 1 is C 2-12 alkyl, C 6-14 aryl, or C 3-12 heterocycle, which in each case is substituted or unsubstituted.

18. A compound according to claim 2 , wherein R 3 is H, or R 3 is C 1-12 alkyl, C 6-18 aralkyl, C 3-12 heterocycle, or C 3-18 heteroaralkyl, which in each case is substituted or unsubstituted.

19. A compound according to claim 18 , wherein R 3 is C 1-12 alkyl which is substituted or unsubstituted.

20. A compound according to claim 2 , wherein

R 3 is H, or R 3 is methyl, ethyl, isopropyl, cyclopropyl, cyclohexyl, allyl, piperidinyl, piperazinyl, pyffolidinyl, azetidinyl, aziridinyl, pyridinyl, piperidinylmethyl, dioxanyl, azepanyl or benzyl, which in each case is unsubstituted or substituted by one or more substituents chosen from halogen, nitro, nitroso, S 03 R 12 , PO 3 RRd, C 0 NR 13 R 14 , C 16 alkyl, C 26 alkenyl, C 26 alkynyl, C 6 i 2 aralkyl, C 612 aryl, Ci 6 alkyloxy, C 26 alkenyloxy, C 26 alkynyloxy, C 62 aryloxy, C(O)C 16 alkyl, C(O)C 26 alkenyl, C(O)C 26 alkynyl, C(O)C 612 aryl, C(O)C 612 aralkyl, C 3 ioheterocycle, hydroxyl, NR 13 R 14 , C(O) 0 R 12 , cyano, azido, amidino, and guanido; and R 12 , R, Rd, R 13 and R 14 are each independently H, C 112 alkyl, C 212 alkenyl, C 212 alkynyl, C 614 aryl, C 3 i 2 heterocycle, C 3 i 8 heteroaralkyl, or C 6 i 8 aralkyl, or R and Rd, taken together with the oxygens, form a 5 to 10 membered heterocycle, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido; and

R 12 , R c , R d , R 13 and R 14 are each independently H, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl, or C 6-18 aralkyl,

or R c and R d , taken together with the oxygens, form a 5 to 10 membered heterocycle,

or R 13 and R 14 , taken together with the nitrogen, form a 3 to 10 membered heterocycle.

21. A compound according to claim 2 , wherein R 3 is H or R 3 is methyl, isopropyl, piperidinyl, piperidinylmethyl, dioxolanyl or cyclohexyl, which in each case is substituted or unsubstituted.

22. A compound according to claim 21 , wherein R 3 is isopropyl which is substituted or unsubstituted.

23. A compound according to claim 21 , wherein R 3 is cyclohexyl which is substituted or unsubstituted.

24. A compound according to claim 2 , wherein R 2 is C 2-12 alkyl, C 6-14 aryl, or C 3-12 heterocycle, which in each case is substituted or unsubstituted.

25. A compound according to claim 24 , wherein R 2 is C 2-12 alkyl which is substituted or unsubstituted.

26. A compound according to claim 2 , wherein

R 2 is cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl cyclohexyl, cycloheptyl, 2-(cyclopentyl)-ethyl, ethyl, vinyl, propyl, propenyl, isopropyl, butyl, butenyl isobutyl, pentyl, neopentyl or t-butyl, which in each case is unsubstituted or substituted by one or more substituents chosen from halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido; and

R 12 , R c , R d , R 13 and R 14 are each independently H, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl, or C 6-18 aralkyl,

or R c and R d , taken together with the oxygens, form a 5 to 10 membered heterocycle,

or R 13 and R 14 , taken together with the nitrogen, form a 3 to 10 membered heterocycle.

27. A compound according to claim 2 , wherein Z is H and X is

28. A compound according to claim 27 , wherein

R 1 is C 2-12 alkyl, C 6-14 aryl, or C 3-12 heterocycle, which in each case is substituted or unsubstituted;

R 3 is H, or R 3 is C 1-12 alkyl, C 6-18 aralkyl, C 3-12 heterocycle, or C 3-18 heteroaralkyl, which in each case is substituted or unsubstituted; and

R 2 is C 2-12 alkyl, C 6-14 aryl, or C 3-12 heterocycle, which in each case is substituted or unsubstituted.

29. A compound according to claim 27 , wherein R 3 is C 1-12 alkyl and R 2 is C 2-12 alkyl, which in each case is substituted or unsubstituted.

30. A compound according to claim 28 , wherein R 3 is C 1-12 alkyl and R 2 is C 2-12 alkyl, which in each is substituted or unsubstituted.

31. A compound according to claim 27 , wherein

R 3 is H, or R 3 is methyl, ethyl, isopropyl, cyclopropyl, cyclohexyl, allyl, piperidinyl, piperazinyl, pyffolidinyl, azetidinyl, aziridinyl, pyridinyl, piperidinylmethyl, dioxanyl, azepanyl or benzyl, which in each case is unsubstituted or substituted by one or more substituents chosen from halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido;

R 2 is cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl cyclohexyl, cycloheptyl, 2-(cyclopentyl)-ethyl, ethyl, vinyl, propyl, propenyl, isopropyl, butyl, butenyl isobutyl, pentyl, neopentyl or t-butyl, which in each case is unsubstituted or substituted by one or more substituents chosen from halogen, nitro, nitroso, SO 3 R 12 , PO 3 R c R d , CONR 13 R 14 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-12 aralkyl, C 6-12 aryl, C 1-6 alkyloxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 6-12 aryloxy, C(O)C 1-6 alkyl, C(O)C 2-6 alkenyl, C(O)C 2-6 alkynyl, C(O)C 6-12 aryl, C(O)C 6-12 aralkyl, C 3-10 heterocycle, hydroxyl, NR 13 R 14 , C(O)OR 12 , cyano, azido, amidino or guanido; and

R 12 , R c , R d , R 13 and R 14 are each independently H, C 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl, C 6-14 aryl, C 3-12 heterocycle, C 3-18 heteroaralkyl, or C 6-18 aralkyl,

or R c and R d , taken together with the oxygens, form a 5 to 10 membered heterocycle,

or R 13 and R 14 , taken together with the nitrogen, form a 3 to 10 membered heterocycle.

32. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 1 .

33. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 2 .

34. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 3 .

35. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 4 .

36. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 5 .

37. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 6 .

38. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 7 .

39. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 8 .

40. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 9 .

41. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 10 .

42. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 11 .

43. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 12 .

44. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 13 .

45. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 14 .

46. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 15 .

47. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 16 .

48. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 17 .

49. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 18 .

50. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 19 .

51. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 20 .

52. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 21 .

53. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 22 .

54. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 23 .

55. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 24 .

56. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 25 .

57. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 26 .

58. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 27 .

59. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 28 .

60. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 30 .

61. A method for treating a Hepatitis C virus (HCV) infection in a host comprising administering to the host a therapeutically effective amount of at least one compound according to claim 31 .

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 17, 2013
From: VERTEX PHARMACEUTICALS INCORPORATED
To: VERTEX PHARMACEUTICALS (CANADA) INCORPORATED
Reel/Frame 031424/0361 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 13, 2013
From: VERTEX PHARMACEUTICALS (CANADA) INCORPORATED
To: VERTEX PHARMACEUTICALS INCORPORATED
Reel/Frame 030997/0434 →
CHANGE OF NAME Recorded Aug 13, 2013
From: PEREIRA, OSWY Z.
To: VERTEX PHARMACEUTICALS (CANADA) INCORPORATED
Reel/Frame 030994/0793 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2010
From: CHAN CHUN KONG, LAVAL; BEDARD, JEAN; DAS, SANJOY KUMAR; NGUYEN BA, NGHE; PEREIRA, OZWY Z.; REDDY, THUMKUNTA JAGADEESWAR; SIDDIQUI, MOHAMMAD ARSHAD; WANG, WUYI; YANNOPOULOS, CONSTANTIN
To: SHIRE BIOCHEM INC.
Reel/Frame 025566/0476 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2010
From: SHIRE BIOCHEM INC.
To: VIROCHEM PHARMA INC.
Reel/Frame 025566/0330 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE CITY OF CORPORATION PREVIOUSLY RECORDED ON REEL 024333 FRAME 0387. ASSIGNOR(S) HEREBY CONFIRMS THE MERGER. Recorded Oct 11, 2010
From: VIROCHEM PHARMA INC.
To: VERTEX PHARMACEUTICALS (CANADA) INCORPORATED
Reel/Frame 025119/0863 →
MERGER Recorded May 4, 2010
From: VIROCHEM PHARMA INC.
To: VERTEX PHARMACEUTICALS (CANADA) INCORPORATED
Reel/Frame 024333/0387 →
Continuity (2)
Continuation 10166031 · Jun 11, 2002
Related Publication 20060142347A1 · Jun 29, 2006