Claims
- 1. A compound of the formula whereinR1 and R2 are independently hydrogen or lower alkyl, lower alkenyl or lower alkynyl; R2 is hydrogen nitro, cyano, halogen, lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy; and R2′ is a heteroaryl, heterocycle, ethyl substituted with a heteroaryl, or ethoxy substituted with a heteroaryl or heterocycle; or a pharmaceutically acceptable salt thereof.
- 2. A compound of claim 1, wherein R2′ is a heteroaryl.
- 3. A compound of claim 2, wherein at least one of R1 and R1′ is lower alkyl.
- 4. A compound of claim 3 wherein at least one of R1 and R1′ is methyl.
- 5. A compound of claim 4, wherein R2′ is thiophenyl.
- 6. A compound of claim 5, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-thiophen-2-yl-1H-indol-3-yl)pyrrole-2,5 dione.
- 7. A compound of claim 5, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-thiophen-3-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 8. A compound of claim 5, wherein the compound is 3-(1-methyl-6-nitro-1H-indol-3-yl)-4-(1-methyl-6-thiophen-2-yl-1H-indol-3-yl)-pyrrole-2,5-dione.
- 9. A compound of claim 5, wherein the compound is 3-(1-methyl-6-nitro-1H-indol-3-yl)-4-(1-methyl-6-thiophen-3-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 10. A compound of claim 4, wherein R2′ is furanyl.
- 11. A compound of claim 10, wherein the compound is 3-(6-furan-2-yl-1-methyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)pyrrole-2,5-dione.
- 12. A compound of claim 10, wherein the compound is 3-(6-furan-2-yl-1-methyl-1H-indol-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione.
- 13. A compound of claim 10, wherein the compound is 3-(6-furan-2-yl-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)pyrrole-2,5-dione.
- 14. A compound of claim 4, wherein R2′ is imidazolyl which is unsubstituted or substituted with lower alkyl.
- 15. A compound of claim 14, wherein the compound is 3-[1-methyl-6-(1-methyl-1H -imidazol-2-yl)-1H-indol-3-yl ]-4-(1-methyl-6-nitro-1H-indol-3-yl)pyrrole-2,5-dione.
- 16. A compound of claim 14, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-[1-methyl-6-(1-methyl-1H-imidazol-2-yl)-1H-indol-3-yl]-pyrrole-2,5-dione.
- 17. A compound of claim 14, wherein the compound is 3-[1-methyl-6-(3-methyl-3H-imidazol-4-yl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione.
- 18. A compound of claim 14, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-[1-methyl-6-(3-methyl-3H-imidazol-4-yl)-1H-indol-3-yl]pyrrole-2,5-dione.
- 19. A compound of claim 14, wherein the compound is 3-(6-methoxy-1-methyl-1H-indol-3-yl)-4-[1-methyl-6-(3-methyl-3H-imidazol-4-yl)-1H-indol-3-yl]pyrrole-2,5-dione.
- 20. A compound of claim 14, wherein the compound is 3-[6-(1-ethyl-1H-imidazol-2-yl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)pyrrole-2,5-dione.
- 21. A compound of claim 14, wherein the compound is 3-[6-(1H-imidazol-2-yl)-1-methyl-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)pyrrole-2,5-dione.
- 22. A compound of claim 14, wherein the compound is 3-[6-(3H-imidazol-4-yl)-1-methyl-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)pyrrole-2,5-dione hydrochloride.
- 23. A compound of claim 14, wherein the compound is 3-(6-imidazol-1-yl-1-methyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)pyrrole-2,5-dione.
- 24. A compound of claim 14, wherein the compound is 3-(6-imidazol-1-yl-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione.
- 25. A compound of claim 14, wherein the compound is 3-(6-imidazol-1-yl-1-methyl-1H-indol-3-yl)-4-(6-methoxy-1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione.
- 26. A compound of claim 14, wherein the compound is 3-(6-bromo-1-methyl-1H-indol-3-yl)-4-(6-imidazol-1-yl-1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione.
- 27. A compound of claim 14, wherein the compound is 3-[4-(6-imidazol-1-yl-1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-1-methyl-1H-indole-6-carbonitrile.
- 28. A compound of claim 14, wherein the compound is 3-[1-methyl-6-(2-methyl-imidazol-1-yl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione.
- 29. A compound of claim 14, wherein the compound is 3-[6-(1H-imidazol-2-yl)-1-methyl-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione.
- 30. A compound of claim 4, wherein R2 is thiazolyl.
- 31. A compound of claim 30, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-thiazol-2-yl-1H-indol-3-yl)-pyrrole-2,5-dione.
- 32. A compound of claim 30, wherein the compound is 3-(1-methyl-6-nitro-1H-indol-3-yl)-4-(1-methyl-6-thiazol-2-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 33. A compound of claim 4, wherein R2 is pyrazolyl, which is unsubstituted or substituted with lower alkyl.
- 34. A compound of claim 33, wherein the compound is 3-(1-methyl-6-nitro-1H-indol-3-yl)-4-(1-methyl-6-pyrazol-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 35. A compound of claim 33, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-pyrazol-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 36. A compound of claim 33, wherein the compound is 3-(6-bromo-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-pyrazol-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 37. A compound of claim 33, wherein the compound is 3-[1-methyl-6-(2-methyl-2H-pyrazol-3-yl)-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)pyrrole-2,5dione.
- 38. A compound of claim 33, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-[1-methyl-6-(2-methyl-2H-pyrazol-3-yl)-1H-indol-3-yl]pyrrole-2,5-dione.
- 39. A compound of claim 33, wherein the compound is 3-(6-bromo-1-methyl-1H-indol-3-yl)-4-[1-methyl-6-(2-methyl-2H-pyrazol-3-yl)-1H-indol-3-yl]pyrrole-2,5-dione.
- 40. A compound of claim 4, wherein R2′ is a pyrimidinyl.
- 41. A compound of claim 40, wherein the compound is 3-(1-methyl-6-nitro-1H-indol-3-yl)-4-(1-methyl-6-pynimidin-5-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 42. A compound of claim 40, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-pyrimidin-5-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 43. A compound of claim 4, wherein R2′ is an isothiazolyl.
- 44. A compound of claim 43, wherein the compound is 3-(6-isothiazol-5-yl-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)pyrrole-2,5-dione.
- 45. A compound of claim 43, wherein the compound is 3-(6-isothiazol-5-yl-1-methyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione.
- 46. A compound of claim 1, wherein R2′ is a heterocycle.
- 47. A compound of claim 46, wherein at least one of R1 and R1′ is lower alkyl.
- 48. A compound of claim 47, wherein at least one of R1 and R1′ is methyl.
- 49. A compound of claim 48, wherein R2′ is piperazine which is unsubstituted or substituted with lower alkyl, lower alkoxy or carbonyl.
- 50. A compound of claim 49, wherein R2′ is piperazine which is substituted with lower alkyl.
- 51. A compound of claim 50, wherein R2′ is 4-methyl-piperazinyl.
- 52. A compound of claim 51, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-[1-methyl-6-(4-methyl-piperazin-1-yl)-1H-indol-3-yl]pyrrole-2,5-dione.
- 53. A compound of claim 48, wherein R2′ is pyrrolidinyl.
- 54. A compound of claim 53, wherein the compound is 3-(1-methyl-6-nitro-1H-indol-3-yl)-4-(1-methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 55. A compound of claim 53, wherein the compound is 3-(1-methyl-6-nitro-1H-indol-3-yl)-4-(6-pyrrolidin-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 56. A compound of claim 53, wherein the compound is 3-(6-fluoro-1-methyl-1H-indol-3-yl)-4-(6-pyrrolidin-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 57. A compound of claim 53, wherein the compound is 3-(6-chloro-1-methyl-1H-indol-3-yl)-4-(6-pyrrolidin-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 58. A compound of claim 53, wherein the compound is 3-(1-methoxymethyl-6-pyrrolidin-1-yl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)pyrrole-2,5-dione.
- 59. A compound of claim 53, wherein the compound is 3-(6-bromo-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 60. A compound of claim 53, wherein the compound is 3-(6-methoxy-1-methyl-1 1H-indol-3-yl)-4-(1-methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 61. A compound of claim 53, wherein the compound is 3-(1-methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)-4-(1-methyl-6-trifluoromethyl-1H-indol-3-yl)pyrrole-2,5-dione.
- 62. A compound of claim 53 wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 63. A compound of claim 53, wherein the compound is 1-methyl-3-[4-(1-methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-1H-6-carbonitrile.
- 64. A compound of claim 53, wherein the compound is 3-(1H-indol-3-yl)-4-(1-methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)-pyrrole-2,5-dione.
- 65. A compound of claim 53, wherein the compound is 3-(6-chloro-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-pyrrolidin-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 66. A compound of claim 48, wherein R2′ is piperidinyl.
- 67. A compound of claim 66, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-piperidin-1-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 68. A compound of claim 48, wherein R2′ is morpholinyl.
- 69. A compound of claim 68, wherein the compound is 3-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)pyrrole-2,5-dione.
- 70. A compound of claim 68, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 71. A compound of claim 68, wherein the compound is 1-methyl-3-[4-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-1H-indole-6-carbonitrile.
- 72. A compound of claim 68, wherein the compound is 3-(6-methoxy-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 73. A compound of claim 68, wherein the compound is 3-(6-fluoro-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 74. A compound of claim 68, wherein the compound is 3-(6-chloro-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 75. A compound of claim 68, wherein the compound is 3-(6-bromo-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 76. A compound of claim 68, wherein the compound is 3-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)-4-(1-methyl-6-trifluoromethyl-1H-indol-3-yl)pyrrole-2,5-dione.
- 77. A compound of claim 68, wherein the compound is 3-(1,6-dimethyl-1H-indol-3-yl)-4-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 78. A compound of claim 68, wherein the compound is 3-(1H-indol-3-yl)-4-(1-methyl-6-morpholin-4-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 79. A compound of claim 68, wherein the compound is 3-(6-fluoro-1-methyl-1H-indol-3-yl)-4-(1-methoxymethyl-6-morpholin-4-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 80. A compound of claim 68, wherein the compound is 3-(6-fluoro-1-methyl-1H-indol-3-yl)-4-(6-morpholin-4-yl-1H-indol-3-yl)-pyrrole-2,5-dione.
- 81. A compound of claim 68, wherein the compound is 3-(1-methyl-1H-indol-3-yl)-4-(6-morpholin-4-yl-1H-indol-3-yl)pyrrole-2,5-dione.
- 82. A compound of claim 1, wherein R2′ is an ethoxy substituted by a heteroaryl or heterocycle.
- 83. A compound of claim 82, wherein at least one of R1 and R1′ is lower alkyl.
- 84. A compound of claim 82, wherein at least one of R1 and R1′ is methyl.
- 85. A compound of claim 84, wherein R2′ is ethoxy substituted by a heteroaryl.
- 86. A compound of claim 85, wherein the heteroaryl is imidazolyl.
- 87. A compound of claim 86, wherein the compound is 3-[6-(2-imidazol-1-yl-ethoxy)-1-methyl-1H-indol-3-yl]-4-(1-methyl-6-nitro-1H-indol-3-yl)pyrrole-2,5-dione.
Parent Case Info
This application claims priority under 35 U.S.C. §119(e) of provisional application Ser. No. 60/171,557, filed Dec. 22, 1999.
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