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Claims for Patent: 7,498,440

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Claims for Patent: 7,498,440

Title:Muscarinic acetylcholine receptor antagonists
Abstract: Muscarinic Acetylcholine Receptor Antagonists and methods of using them are provided.
Inventor(s): Laine; Damane I. (King of Prussia, PA), Palovich; Michael R. (King of Prussia, PA), McCleland; Brent W. (King of Prussia, PA), Neipp; Christopher E. (King of Prussia, PA), Thomas; Sonia M. (King of Prussia, PA)
Assignee: Glaxo Group Limited (Greenford, Middlesex, GB)
Application Number:11/568,330
Patent Claims: 1. A compound of formula (I) ##STR00047## wherein: R1 is ##STR00048## R2 and R3 are independently selected from the group consisting of ##STR00049## F, G, H, K and L are independently selected from the group consisting of hydrogen, halogen, C.sub.1-4 alkyl, halosubstituted C.sub.1-4 alkyl, hydroxy substituted alkyl, and C.sub.1-4alkoxy; R.sub.4 and R.sub.5 are independently selected from the group consisting of hydrogen, halogen, C1-4 alkyl, aryl, C1-4 alkyl aryl, cyano, nitro, (CR7R7)pORb and (CR7R7)pNRbRb; R6 is selected from the group consisting of hydrogen, C1-4 alkyl; m is an integer having a value of 1 to 15; t is 0 or an integer having a value of 1 to 5; p is 0 or an integer having a value of 1 to 4; Rb is selected from the group consisting of hydrogen, C1-4 alkyl, aryl and C1-4 alkyl aryl; R7 is selected from the group consisting of hydrogen, C1-4 alkyl, halosubstituted C1-4 alkyl, and hydroxy substituted C1-4 alkyl; and X.sup.-- is a pharmaceutically acceptable anion.

2. A compound according to claim 1 wherein m is an integer having a value of 1 to 5; t is 0, 1 or 2; p is 0, 1 or 2; R6 is selected from the group consisting of hydrogen and C1-4 alkyl; Rb is selected from the group consisting of hydrogen, C1-4 alkyl and aryl C1-4 alkyl; R7 is selected from the group consisting of hydrogen and C1-4 alkyl; and X.sup.-- is a pharmaceutically acceptable anion selected from the group consisting of chloride, bromide, iodide, hydroxide, sulfate, nitrate, phosphate, acetate, trifluoroacetate, fumarate, citrate, tartrate, oxalate, succinate, mandelate, methanesulfonate and p-tlouenesulfonate.

3. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier thereof.

4. The compound according to claim 1 wherein X.sup.-- is selected from the group consisting of chloride, bromide, iodide, hydroxide, sulfate, nitrate, phosphate, acetate, trifluoroacetate, fumarate, citrate, tartrate, oxalate, succinate, mandelate, methanesulfonate and p-toluenesulfonate.

5. The compound according to claim 1 wherein R2 and R3 are both independently selected from ##STR00050##

6. The compound according to claim 5 wherein F, G, H, K and L are hydrogen.

7. The compound according to claim 1 wherein R2 and R3 are both independently selected from ##STR00051##

8. The compound according to claim 7 wherein F, G and H are hydrogen.

9. The compound according to claim 2 wherein R2 and R3 are both independently selected from ##STR00052##

10. The compound according to claim 9 wherein F, G, H, K and L are hydrogen.

11. The compound according to claim 2 wherein R2 and R3 are both independently selected from ##STR00053##

12. The compound according to claim 11 wherein F, G and H are hydrogen.

13. The compound according to claim 2 wherein F, G, H, K and L are hydrogen.

14. The compound according to claim 1 wherein R4 and R5 are both hydrogen.

15. The compound according to claim 2 wherein R4 and R5 are both hydrogen.

16. The compound according to claim 10 wherein R4 and R5 are both hydrogen.

17. The compound according to claim 1 wherein m is 2, 3 or 4.

18. The compound according to claim 2 wherein m is 2, 3 or 4.

19. The compound according to claim 10 wherein m is 2, 3 or 4.

20. The compound according to claim 1 wherein t is 0 or 1.

21. The compound according to claim 2 wherein t is 0 or 1.

22. The compound according to claim 10 wherein t is 0 or 1.

23. The compound according to claim 19 wherein t is 0 or 1.

24. The compound according to claim 1 wherein m is 2 and t is 1.

25. The compound according to claim 2 wherein m is 2 and t is 1.

26. The compound according to claim 10 wherein m is 2 and t is 1.

27. The compound according to claim 1 wherein R2 and R3 are both phenyl, R4 and R5 are both hydrogen, m is 2 and t is 1.

28. The compound according to claim 1 wherein R6 is hydrogen.

29. The compound according to claim 2 wherein R6 is hydrogen.

30. The compound according to claim 10 wherein R6 is hydrogen.

31. The compound according to claim 1 wherein F, G, H, K and L are independently selected from the group consisting of hydrogen, halogen, methyl and or methoxy.

32. The compound according to claim 2 wherein F, G, H, K and L are independently selected from the group consisting of hydrogen, halogen, methyl and or methoxy.

33. The compound according to claim 1 wherein p is 0.

34. The compound according to claim 2 wherein p is 0.

35. The compound according to claim 1 wherein R7 is hydrogen.

36. The compound according to claim 2 wherein R7 is hydrogen.

37. The pharmaceutically acceptable anion according to claim 1 which is bromide.

38. The pharmaceutically acceptable anion according to claim 1 which is iodide.

39. The pharmaceutically acceptable anion according to claim 2 which is bromide.

40. The pharmaceutically acceptable anion according to claim 2 which is iodide.

41. The compound according to claim 1 which is: 4-[hydroxy(diphenyl)methyl]-1-[2-(phenyloxy)ethyl]-1-azoniabicyclo [2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-[3-(phenyloxy)propyl]-1-azoniabicyclo[2.2.2- ]octane bromide; 4-[hydroxy(di-2-thienyl)methyl]-1-[2-(phenyloxy)ethyl]-1-azoniabicyclo[2.- 2.2]octane bromide; 4-[hydroxy(di-2-thienyl)methyl]-1-[3-(phenyloxy)propyl]-1-azoniabicyclo[2- .2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-[4-(phenyloxy)butyl]-1-azoniabicyclo[2.2.2]- octane bromide; 4-[hydroxy(diphenyl)methyl]-1-{4-[(phenylmethyl)oxy]butyl}-1-azoniabicycl- o[2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-{3-[(phenylmethyl)oxy]propyl}-1-azoniabicyc- lo[2.2.2]octane bromide; 1-{2-[(2,4-dibromophenyl)oxy]ethyl}-4-[hydroxy(diphenyl)methyl]-1-azoniab- icyclo[2.2.2]octane bromide; 4-[hydroxy(di-3-thienyl)methyl]-1-[2-(phenyloxy)ethyl]-1-azoniabicyclo[2.- 2.2]octane bromide; 4-[hydroxy(di-3-thienyl)methyl]-1-[3-(phenyloxy)propyl]-1-azoniabicyclo[2- .2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-(3-{[2-(methyloxy)phenyl]oxy}propyl)-1-azon- iabicyclo[2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-{3-[2-hydroxyphenyl)oxy]propyl}-1-azoniabic- yclo[2.2.2]octane bromide; 1-{3-[(3-chlorophenyl)oxy]propyl}-4-[hydroxy(diphenyl)methyl]-1-azoniabic- yclo[2.2.2]octane bromide; 1-{3-[(4-bromophenyl)oxy]propyl}-4-[hydroxy(diphenyl)methyl]-1-azoniabicy- clo[2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-{3-[(4-nitrophenyl)oxy]propyl}-1-azoniabicy- clo[2.2.2]octane bromide; 1-{3-[(2-bromophenyl)oxy]propyl}-4-[hydroxy(diphenyl)methyl]-1-azoniabicy- clo[2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-(3-{[4-(methyloxy)phenyl]oxy}propyl)-1-azon- iabicyclo[2.2.2]octane bromide; 4-[hydroxy(di-2-naphthalenyl)methyl]-1-[3-(phenyloxy)propyl]-1-azoniabicy- clo[2.2.2]octane bromide; 4-[hydroxy(di-2-naphthalcnyl)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-azo- niabicyclo[2.2.2]octane bromide; 1-{3-[(2-fluorophenyl)oxy]propyl}-4-[hydroxy(diphenyl)methyl]-1-azoniabic- yclo[2.2.2]octane bromide; 1-{3-[(3-fluorophenyl)oxy]propyl}-4-[hydroxy(diphenyl)methyl]-1-azoniabic- yclo[2.2.2]octane bromide; 1-{3-[(4-fluorophenyl)oxy]propyl}-4-[hydroxy(diphenyl)methyl]-1-azoniabic- yclo[2.2.2]octane bromide; 1-[3-(3-biphenylyloxy)propyl]-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo- [2.2.2]octane bromide; 1-[3-(4-biphenylyloxy)propyl]-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo- [2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-{3-[(3-nitrophenyl)oxy]propyl}-1-azoniabicy- clo[2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-{3-[(2-methylphenyl)oxy]propyl}-1-azoniabic- yclo[2.2.2]octane bromide; 1-(3-{[3-(diethylamino)phenyl]oxy}propyl)-4-[hydroxy(diphenyl)methyl]-1-a- zoniabicyclo[2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-[2-({[3 -(methyloxy)phenyl]methyl}oxy)ethyl]-1-azoniabicyclo[2.2.2]octane bromide; 1-[2-( {[4-(1,1-dimethylethyl)phenyl]methyl}oxy)ethyl]-4-[hydroxy(diphenyl)methy- l]-1-azoniabicyclo[2.2.2]octane bromide; 1-(2-{[(4-fluorophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1-az- oniabicyclo[2.2.2]octane bromide; 1-(2-{[(4-chlorophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1-az- oniabicyclo[2.2.2]octane bromide; 1-(2-{[(4-bromophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1-azo- niabicyclo[2.2.2]octane bromide; 1-(2-{[(4-cyanophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1-azo- niabicyclo[2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-{2-[(2-naphthalenylmethyl)oxy]ethyl}-1-azon- iabicyclo[2.2.2]octane bromide; 1-{3-[(4-cyanophenyl)oxy]propyl}-4-[hydroxy(diphenyl)methyl]-1-azoniabicy- clo[2.2.2]octane bromide; 4-[hydroxy(diphenyl)methyl]-1-{2-[(1 -methyl-1-phenylethyl)oxy]ethyl}-1-azoniabicyclo [2.2.2]octane bromide; or 1-(2-{[(3-fluorophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1- -azoniabicyclo[2.2.2]octane bromide.

42. The compound according to claim 1 which is; 4-[bis(4-fluorophenyl)(hydroxy)methyl]-1-[3-(phenyloxy)propyl]-1-azoniabi- cyclo[2.2.2]octane bromide; 4-[bis(4-fluorophenyl)(hydroxy)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-a- zoniabicyclo[2.2.2]octane bromide; 4-(hydroxy {bis[3-(methyloxy)phenyl]}methyl)-1-[3-(phenyloxy)propyl]-1-azoniabicyclo- [2.2.2]octane bromide; 4-(hydroxy {bis[3-(methyloxy)phenyl]}methyl)-1-{2-[(phenylmethyl)oxy]ethyl}-1-azonia- bicyclo[2.2.2]octane bromide; 4-(hydroxy {bis[4-(methyloxy)phenyl]}methyl)-1-[3-(phenyloxy)propyl]-1-azoniabicyclo- [2.2.2]octane bromide; 4-(hydroxy {bis[4-(methyloxy)phenyl]}methyl)-1-{2-[(phenylmethyl)oxy]ethyl}-1-azonia- bicyclo[2.2.2]octane bromide; 4-[bis(3-fluorophenyl)(hydroxy)methyl]-1-[3-(phenyloxy)propyl]-1-azoniabi- cyclo[2.2.2]octane bromide; 4-[bis(3-fluorophenyl)(hydroxy)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-a- zoniabicyclo[2.2.2]octane bromide; 4-{hydroxy[bis(3-methylphenyl)]methyl}-1-[3-(phenyloxy)propyl]-1-azoniabi- cyclo[2.2.2]octane bromide; 4-{hydroxy[bis(3-methylphenyl)]methyl}-1-{2-[(phenylmethyl)oxy]ethyl}-1-a- zoniabicyclo[2.2.2]octane bromide; 4-{hydroxy[bis(4-methylphenyl)]methyl}-1-[3-(phenyloxy)propyl]-1-azoniabi- cyclo[2.2.2]octane bromide; or 4-{hydroxy[bis(4-methylphenyl)]methyl}-1-{2-[(phenylmethyl)oxy]ethyl}-1-a- zoniabicyclo[2.2.2]octane bromide.

43. A pharmaceutical composition comprising a compound according to claim 41 and a pharmaceutically acceptable carrier thereof.

44. A pharmaceutical composition comprising a compound according to claim 42 and a pharmaceutically acceptable carrier thereof.

45. A pharmaceutical composition comprising a compound according to claim 42 and a pharmaceutically acceptable carrier thereof.

46. A pharmaceutical composition according to claim 3 in a form suitable for administration by oral or nasal inhalation.

47. A pharmaceutical composition according to claim 46 wherein the form is suitable for administration by inhalation via a medicament dispenser selected from a reservoir dry powder inhaler, a multi-dose dry powder inhaler, or a metered dose inhaler.

48. A pharmaceutical composition according to claim 3 which is a dry powder composition.

49. A pharmaceutical composition according to claim 3 wherein the pharmaceutically acceptable carrier is lactose.
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