Claims
- 1. A method of treating sexual dysfunction in a mammal comprising administering to said mammal in need of such treatment a therapeutically effective amount of a compound of formula (I)
- 2. The method according to claim 1 wherein
- 3. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 4. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 5. The method according to claim 4 wherein the compound of formula (I) is selected from the group consisting of
1-(1-benzothien-2-ylmethyl)-4-(2-pyridinyl)piperazine; and 2-{1-[4-(2-pyridinyl)-1-piperazinyl]ethyl}-1H-indole.
- 6. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 7. The method according to claim 2 wherein
- 8. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 9. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; Ry is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 10. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 11. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 12. The method according to claim 2 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 13. The method according to claim 2 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 14. The method according to claim 13 wherein the compound of formula (I) is selected from the group consisting of
2-{[4-(3-methyl-2-pyridinyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine; 2-[4-(furo[3,2-b]pyridin-2-ylmethyl)-1-piperazinyl]nicotinonitrile; and 2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine.
- 15. The method according to claim 2 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 16. The method according to claim 2 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 17. The method according to claim 2 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 18. The method according to claim 2 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 19. The method according to claim 2 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is CH; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 20. The method according to claim 2 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is C; — is a bond; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 21. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 22. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 23. The method according to claim 14 wherein the compound of formula (I) is selected from the group consisting of
5-methoxy-2-{[4-(6-methyl-2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 5-methoxy-2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-{[4-(6-methyl-2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-[4-([1,3]thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]nicotinonitrile; and 2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine.
- 24. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is CH; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 25. The method according to claim 14 wherein the compound of formula (I) is 2-{[4-(2-pyridinyl)-1-piperidinyl]methyl}[1,3]thiazolo[5,4-b]pyridine.
- 26. The method according to claim 2 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is C; — is a bond; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 27. The method according to claim 1 wherein
- 28. The method according to claim 27 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 29. The method according to claim 27 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 30. The method according to claim 29 wherein the compound of formula (I) is 5-fluoro-2-{[4-(2-pyridinyl)-1,4-diazepan-1-yl]methyl}-1H-indole.
- 31. The method according to claim 27 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 32. The method according to claim 27 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 33. The method according to claim 27 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 34. The method according to claim 27 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 35. The method according to claim 27 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 36. The method according to claim 27 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 37. The method according to claim 27 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 38. The method according to claim 27 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 39. The method according to claim 1 wherein
- 40. The method according to claim 39 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 41. The method according to claim 39 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 42. The method according to claim 41 wherein the compound of formula (I) is
5-fluoro-2-{[(1S,4S)-5-(2-pyridinyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]methyl}-1H-indole.
- 43. The method according to claim 39 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 44. The method according to claim 39 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 45. The method according to claim 39 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 46. The method according to claim 39 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 47. The method according to claim 39 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 48. The method according to claim 39 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 49. The method according to claim 39 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 50. The method according to claim 39 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 51. The method according to claim 1 wherein
- 52. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 53. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and Rx are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; ——is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 54. The method according to claim 53 wherein the compound of formula (I) is selected from the group consisting of
2-[4-(1-benzothien-2-ylmethyl)-1-piperazinyl]benzonitrile; 1-(1-benzothien-2-ylmethyl)-4-(2-fluorophenyl)piperazine; 2-{1-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl}-1H-indole; and 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}-1-methyl-1H-indole.
- 55. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; ——is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 56. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 57. The method according to claim 51 wherein
- 58. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; ——is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 59. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; ——is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 60. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 61. The method according to claim 51 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 62. The method according to claim 51 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 63. The method according to claim 62 wherein the compound of formula (I) is selected from the group consisting of
4-(4-{[6-(trifluoromethyl)thieno[3,2-b]pyridin-2-yl]methyl}-1-piperazinyl)phenol; 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}-6-(trifluoromethyl)thieno [3,2-b]pyridine; 2-(4-{[6-(trifluoromethyl)thieno[3,2-b]pyridin-2-yl]methyl}-1-piperazinyl)benzonitrile; 4-[4-(furo[3,2-b]pyridin-2-ylmethyl)-1-piperazinyl]phenol; 2-[(4-phenyl-1-piperazinyl)methyl]furo[3,2-b]pyridine; 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine; 2-[4-(furo[3,2-b]pyridin-2-ylmethyl)-1-piperazinyl]benzonitrile; and 2-{[4-(2-fluorophenyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine.
- 64. The method according to claim 51 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 65. The method according to claim 51 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 66. The method according to claim 51 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 67. The method according to claim 51 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 68. The method according to claim 67 wherein the compound of formula (I) is selected from the group consisting of
2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}[1,3]oxazolo[4,5-b]pyridine; and 2-[4-([1,3]oxazolo[4,5-b]pyridin-2-ylmethyl)-1-piperazinyl]benzonitrile.
- 69. The method according to claim 51 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 70. The method according to claim 51 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 71. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 72. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 73. The method according to claim 72 wherein the compound of formula (I) is selected from the group consisting of
4-{4-[(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)methyl]-1-piperazinyl}phenol; 2-{[4-(2-fluorophenyl)-1-piperazinyl]methyl}-5-methoxy[1,3]thiazolo[5,4-b]pyridine; 5-methoxy-2-({4-[2-(methylthio)phenyl]-1-piperazinyl}methyl)[1,3]thiazolo[5,4-b]pyridine; 5-methoxy-2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-{[4-(2-chlorophenyl)-1-piperazinyl]methyl}-5-methoxy[1,3]thiazolo[5,4-b]pyridine; 2-{4-[(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)methyl]-1-piperazinyl}benzonitrile; 2-{[4-(2-chlorophenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-{[4-(5-chloro-2-methoxyphenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 4-[4-([1,3]thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]phenol; 2-({4-[2-(methylthio)phenyl]-1-piperazinyl}methyl)[1,3]thiazolo[5,4-b]pyridine; 2-{[4-(2-fluorophenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-[4-([1,3]thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]benzonitrile; 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; and 2-[(4-phenyl-1-piperazinyl)methyl][1,3]thiazolo[5,4-b]pyridine.
- 74. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is CH; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 75. The method according to claim 51 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is C; — is a bond; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 76. The method according to claim 1 wherein
- 77. The method according to claim 76 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 78. The method according to claim 76 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 79. The method according to claim 78 wherein the compound of formula (I) is
2-{4-[(5-fluoro-1H-indol-2-yl)methyl]-1,4-diazepan-1-yl}benzonitrile.
- 80. The method according to claim 76 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 81. The method according to claim 76 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 82. The method according to claim 76 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 83. The method according to claim 76 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 84. The method according to claim 76 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 85. The method according to claim 76 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 86. The method according to claim 76 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 87. The method according to claim 76 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 88. The method according to claim 1 wherein
- 89. The method according to claim 88 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 90. The method according to claim 88 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 91. The method according to claim 88 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 92. The method according to claim 88 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 93. The method according to claim 88 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 94. The method according to claim 88 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 95. The method according to claim 88 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 96. The method according to claim 88 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 97. The method according to claim 88 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 98. The method according to claim 88 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 99. The method according to claim 98 wherein the compound of formula (I) is selected from the group consisting of
5-methoxy-2-{[4-(2-pyrimidinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; and 2-{[4-(2-pyrimidinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine.
- 100. The method according to claim 1 wherein
- 101. The method according to claim 100 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 102. The method according to claim 100 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; X is CRX; RP, RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; X1 is S; Y1 is N; Z is N; — is absent; and R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 103. The method according to claim 100 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 104. The method according to claim 100 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is CRX; RP, RQ, RS, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; X1 is S; Y1 is N; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R2 and R3 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 105. The method according to claim 100 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; and Y is selected from the group consisting of NRY, O, and S.
- 106. The method according to claim 100 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is CRX; RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; X1 is S; Y1 is N; Z is N; — is absent; and R2 and R3 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 107. The method according to claim 100 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 108. The method according to claim 100 wherein
P is N; Q is CRQ; S is CRS; T is CRT; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; X1 is S; Y1 is N; Z is N; — is absent; and R2 and R3 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 109. The method according to claim 100 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; and Y is selected from the group consisting of NRY, O, and S.
- 110. The method according to claim 100 wherein
P is CRP; Q is CRQ; S is CRS; T is N; X is N; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; X1 is S; Y1 is N; Z is N; — is absent; and R2 and R3 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 111. The method according to claim 110 wherein the compound of formula (I) is
2-{[4-(1,3-thiazol-2-yl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine.
- 112 The method according to claim 1 wherein
- 113. The method according to claim 112 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; and Y is selected from the group consisting of NRY, O, and S.
- 114. The method according to claim 112 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; RP, RQ, RS, RT, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 115. The method according to claim 114 wherein the compound of formula (I) is selected from the group consisting of
1-[(5-chloro-1-benzothien-3-yl)methyl]-4-(6-methyl-2-pyridinyl)piperazine; 1-[(5-chloro-1-benzothien-3-yl)methyl]-4-(2-pyridinyl)piperazine; and 1-(1-benzothien-3-ylmethyl)-4-(2-pyridinyl)piperazine.
- 116. The method according to claim 112 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; RP, RQ, RS, RT, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 117. The method according to claim 116 wherein the compound of formula (I) is
2-{1-[(5-chloro-1-benzothien-3-yl)methyl]-4-piperidinyl}pyridine.
- 118. The method according to claim 112 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; RP, RQ, RS, RT, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 119. The method according to claim 112 wherein
P is CRP; Q is CRQ; S is CRS; T is N; V is CRV; and Y is selected from the group consisting of NRY, O, and S.
- 120. The method according to claim 112 wherein
P is CRP; Q is CRQ; S is CRS; T is N; V is CRV; RP, RQ, RS, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 121. The method according to claim 120 wherein the compound of formula (I) is
2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}-1H-pyrrolo[2,3-b]pyridine.
- 122. The method according to claim 112 wherein
P is CRP; Q is CRQ; S is CRS; T is N; V is CRV; RP, RQ, RS, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 123. The method according to claim 112 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; V is CRV; RP, RQ, RS, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 124. The method according to claim 112 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; and Y is selected from the group consisting of NRY, O, and S;
- 125. The method according to claim 112 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; RQ, RS, RT and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 126. The method according to claim 112 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; RQ, RS, RT and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 127. The method according to claim 112 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; RQ, RS, RT and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 128. The method according to claim 1 wherein
- 129. The method according to claim 128 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; and Y is selected from the group consisting of NRY, O, and S.
- 130. The method according to claim 128 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; RP, RQ, RS, RT, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 131. The method according to claim 130 wherein the compound of formula (I) is selected from the group consisting of
2-{4-[(5-chloro-1-benzothien-3-yl)methyl]-1-piperazinyl}benzonitrile; and 1-[(5-chloro-1-benzothien-3-yl)methyl]-4-(2-fluorophenyl)piperazine.
- 132. The method according to claim 128 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; RP, RQ, RS, RT, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 133. The method according to claim 128 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; RP, RQ, RS, RT, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 134. The method according to claim 128 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; V is CRV; and Y is selected from the group consisting of NRY, O, and S.
- 135. The method according to claim 128 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; V is CRV; RP, RQ, RS, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 136. The method according to claim 120 wherein the compound of formula (I) is selected from the group consisting of
2-[4-(1H-pyrrolo[2,3-b]pyridin-2-ylmethyl)-1-piperazinyl]benzonitrile; 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}-1H-pyrrolo[2,3-b]pyridine; 2-[(4-phenyl-1-piperazinyl)methyl]-1H-pyrrolo[2,3-b]pyridine; 2-{[4-(2-fluorophenyl)-1-piperazinyl]methyl}-1H-pyrrolo[2,3-b]pyridine; and 2-[4-(1H-pyrrolo[2,3-b]pyridin-2-ylmethyl)-1-piperazinyl]nicotinonitrile.
- 137. The method according to claim 128 wherein
P is CRP; Q is CRQ; S is CRS; T is N; V is CRV; RP, RQ, RS, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 138. The method according to claim 128 wherein
P is CRP; Q is CRQ; S is CRS; T is N; V is CRV; RP, RQ, RS, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 139. The method according to claim 128 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; and Y is selected from the group consisting of NRY, O, and S.
- 140. The method according to claim 128 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; RQ, RS, RT and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 141. The method according to claim 128 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; RQ, RS, RT and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is CH; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 142. The method according to claim 128 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; RQ, RS, RT and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is C; — is a bond; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 143. The method according to claim 1 wherein
- 144. The method according to claim 143 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; and Y is selected from the group consisting of NRY, O, and S.
- 145. The method according to claim 143 wherein
P is CRP; Q is CRQ; S is CRS; T is CRT; V is CRV; RP, RQ, RS, RT, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 146. The method according to claim 145 wherein the compound of formula (I) is
2-{4-[(5-chloro-1-benzothien-3-yl)methyl]-1-piperazinyl}pyrimidine.
- 147. The method according to claim 143 wherein
P is CRP; Q is CRQ; S is CRS; Tis N; V is CRV; and Y is selected from the group consisting of NRY, O, and S.
- 148. The method according to claim 143 wherein
P is CRP; Q is CRQ; S is CRS; T is N; V is CRV; RP, RQ, RS, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 149. The method according to claim 148 wherein the compound of formula (I) is.
2-{[4-(2-pyrimidinyl)-1-piperazinyl]methyl}-1H-pyrrolo [2,3-b]pyridine.
- 150. The method according to claim 143 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; and Y is selected from the group consisting of NRY, O, and S.
- 151. The method according to claim 143 wherein
P is N; Q is CRQ; S is CRS; T is CRT; V is CRV; RQ, RS, RT, and RV are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Y is selected from the group consisting of NRY, O, and S; RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 152. The method according to claim 1 wherein
- 153. The method according to claim 152 wherein
RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 154. The method according to claim 153 wherein the compound of formula (I) is selected from the group consisting of
2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}-1H-thieno[3,4-d]imidazole; and 2-[4-(1H-thieno[3,4-d]imidazol-2-ylmethyl)-1-piperazinyl]nicotinonitrile.
- 155. The method according to claim 1 wherein
- 156. The method according to claim 155 wherein
RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 157. The method according to claim 156 wherein the compound of formula (I) is selected from the group consisting of
2-{[4-(2-fluorophenyl)-1-piperazinyl]methyl}-1H-thieno[3,4-d]imidazole; 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}-1H-thieno[3,4-d]imidazole; 4-[4-(1H-thieno[3,4-d]imidazol-2-ylmethyl)-1-piperazinyl]phenol; and 2-({4-[2-(methylthio)phenyl]-1-piperazinyl}methyl)-1H-thieno[3,4-d]imidazole.
- 158. The method according to claim 1 wherein
- 159. The method according to claim 158 wherein
RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 160. The method according to claim 159 wherein the compound of formula (I) is
2-{[4-(2-pyrimidinyl)-1-piperazinyl]methyl}-1H-thieno[3,4-d]imidazole.
- 161. A method of treating sexual dysfunction in a mammal comprising administering to the mammal a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt, ester, amide, N-oxide, or prodrug thereof in combination with a pharmaceutically acceptable carrier.
- 162. A method of treating sexual dysfunction in a mammal comprising administering to the mammal a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt, ester, amide, N-oxide, or prodrug thereof in combination with a phosphodiesterase 5 inhibitor.
- 163. A method of treating sexual dysfunction in a mammal comprising administering to the mammal a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt, ester, amide, N-oxide, or prodrug thereof in combination with an adrenergic receptor antagonist.
- 164. A method of treating sexual dysfunction in a mammal comprising administering to the mammal a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt, ester, amide, N-oxide, or prodrug thereof in combination with a dopamine agonist.
- 165. A method of treating male erectile dysfunction in a mammal comprising administering to the mammal in need of such treatment a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt, ester, amide, N-oxide, or prodrug thereof.
- 166. A method of treating female sexual dysfunction in a mammal comprising administering to the mammal in need of such treatment a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt, ester, amide, N-oxide, or prodrug thereof.
- 167. A method of treating a disorder selected from the group consisting of cardiovascular disorders, inflammatory disorders, attention deficit hyperactivity disorder, Alzheimer's disease, drug abuse, Parkinson's disease, schizophrenia, anxiety, mood disorders and depression in a mammal comprising administering to the mammal in need of such treatment a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt, ester, amide, N-oxide, or prodrug thereof.
- 168. A compound of formula (II)
- 169. The compound according to claim 168 wherein
- 170. The compound according to claim 168 wherein
- 171. The compound according to claim 170 wherein
RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 172. The compound according to claim 171 selected from the group consisting of
2-{[4-(3-methyl-2-pyridinyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine; 2-[4-(furo[3,2-b]pyridin-2-ylmethyl)-1-piperazinyl]nicotinonitrile; and 2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine.
- 173. The compound according to claim 168 wherein
- 174. The compound according to claim 173 wherein
RQ, RS, RT, and RX are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 175. The compound according to claim 174 selected from the group consisting of
4-(4-{[6-(trifluoromethyl)thieno[3,2-b]pyridin-2-yl]methyl}-1-piperazinyl)phenol; 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}-6-(trifluoromethyl)thieno[3,2-b]pyridine; 2-(4-{[6-(trifluoromethyl)thieno [3,2-b]pyridin-2-yl]methyl}-1-piperazinyl)benzonitrile; 4-[4-(furo[3,2-b]pyridin-2-ylmethyl)-1-piperazinyl]phenol; 2-[(4-phenyl-1-piperazinyl)methyl]furo[3,2-b]pyridine; 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine; 2-[4-(furo[3,2-b]pyridin-2-ylmethyl)-1-piperazinyl]benzonitrile; and 2-{[4-(2-fluorophenyl)-1-piperazinyl]methyl}furo[3,2-b]pyridine.
- 176. The compound according to claim 168 wherein
- 177. The compound according to claim 176 wherein
RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 178. The compound according to claim 168 wherein
- 179. The compound according to claim 178 wherein
RQ, RS, and RT are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 180. The compound according to claim 179 selected from the group consisting of
2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}[1,3]oxazolo[4,5-b]pyridine; and 2-[4-([1,3]oxazolo[4,5-b]pyridin-2-ylmethyl)-1-piperazinyl]benzonitrile.
- 181. The compound according to claim 168 wherein
- 182. The compound according to claim 181 wherein
RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 183. The compound according to claim 182 selected from the group consisting of
5-methoxy-2-{[4-(6-methyl-2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 5-methoxy-2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-{[4-(6-methyl-2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-[4-([1,3]thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]nicotinonitrile; and 2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine.
- 184. The compound according to claim 181 wherein RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen;
Z is CH; — is absent; and R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, and halogen.
- 185. The compound according to claim 184 that is 2-{[4-(2-pyridinyl)-1-piperidinyl]methyl}[1,3]thiazolo[5,4-b]pyridine.
- 186. The compound according to claim 168 wherein
- 187. The compound according to claim 186 wherein
RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 188. The compound according to claim 187 selected from the group consisting of
4-{4-[(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)methyl]-1-piperazinyl}phenol; 2-{[4-(2-fluorophenyl)-1-piperazinyl]methyl}-5-methoxy[1,3]thiazolo[5,4-b]pyridine; 5-methoxy-2-({4-[2-(methylthio)phenyl]-1-piperazinyl}methyl)[1,3]thiazolo[5,4-b]pyridine; 5-methoxy-2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-{[4-(2-chlorophenyl)-1-piperazinyl]methyl}-5-methoxy[1,3]thiazolo[5,4-b]pyridine; 2-{4-[(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)methyl]-1-piperazinyl}benzonitrile; 2-{[4-(2-chlorophenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-{[4-(5-chloro-2-methoxyphenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 4-[4-([1,3]thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]phenol; 2-({4-[2-(methylthio)phenyl]-1-piperazinyl}methyl)[1,3]thiazolo[5,4-b]pyridine; 2-{[4-(2-fluorophenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; 2-[4-([1,3]thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]benzonitrile; 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; and 2-[(4-phenyl-1-piperazinyl)methyl][1,3]thiazolo[5,4-b]pyridine.
- 189. The compound according to claim 168 wherein
- 190. The compound according to claim 189 wherein
RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 191. The compound according to claim 190 selected from the group consisting of
5-methoxy-2-{[4-(2-pyrimidinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine; and 2-{[4-(2-pyrimidinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine.
- 192 The compound according to claim 168 wherein
- 193. The compound according to claim 192 wherein
RP, RQ, and RS are independently selected from the group consisting of hydrogen, alkoxy, alkyl, haloalkyl, and halogen; X1 is S; Y1 is N; Z is N; — is absent; and R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 194. The compound according to claim 193 that is 2-{[4-(1,3-thiazol-2-yl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine.
- 195. The compound according to claim 168 wherein
- 196. The compound according to claim 168 wherein
- 197. The compound according to claim 196 selected from the group consisting of
2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}-1H-thieno[3,4-d]imidazole; and 2-[4-(1H-thieno[3,4-d]imidazol-2-ylmethyl)-1-piperazinyl]nicotinonitrile.
- 198. The compound according to claim 168 wherein
- 199. The compound according to claim 198 wherein
RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, alkoxy, alkyl, alkylthio, cyano, halogen, and hydroxy.
- 200. The compound according to claim 199 selected from the group consisting of
2-{[4-(2-fluorophenyl)-1-piperazinyl]methyl}-1H-thieno[3,4-d]imidazole; 2-{[4-(2-methoxyphenyl)-1-piperazinyl]methyl}-1H-thieno[3,4-d]imidazole; 4-[4-(1H-thieno[3,4-d]imidazol-2-ylmethyl)-1-piperazinyl]phenol; and 2-({4-[2-(methylthio)phenyl]-1H-piperazinyl}methyl)-1H-thieno [3,4-d]imidazole.
- 201. The compound according to claim 168 wherein
- 202. The compound according to claim 201 wherein
RY is selected from the group consisting of hydrogen and alkyl; Z is N; — is absent; and R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, and halogen.
- 203. The compound according to claim 202 that is 2-{[4-(2-pyrimidinyl)-1-piperazinyl]methyl}-1H-thieno[3,4-d]imidazole.
Parent Case Info
[0001] This application claims benefit to U.S. Provisional Application Serial No. 60/384,291, filed May 29, 2002, incorporated herein by reference.
Provisional Applications (1)
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Number |
Date |
Country |
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60384291 |
May 2002 |
US |