Claims
- 1. A phenyl ring containing the compound of the formula:
- 2. The compound of claim 1 wherein R1 is hydrogen and R3 and R4 are substituted on adjacent carbon atoms and form a lower alkylene dioxy bridge and R2 is selected from lower alkyl and hydrogen.
- 3. The compound of claim 2 wherein said compound is 6-benzo[1,3]dioxol-5-yl-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 4. The compound of claim 2 wherein R1 is hydrogen and R3 and R4 are substituted on adjacent carbon atoms and taken together with their attached carbon atoms form a fused aromatic ring and R2 is selected from hydrogen and lower alkyl.
- 5. The compound of claim 4 wherein said compound is 7-methyl-6-naphthalen-1-yl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 6. The compound of claim 4 wherein said compound is 7-methyl-6-naphthalen-2-yl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 7. The compound of claim 4 wherein said compound is 6-naphthalen-1-yl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 8. The compound of claim 4 wherein said compound is 6-naphthalen-2-yl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 9. The compound of claim 8 wherein said compound is 7-methyl-6-naphthalen-1-yl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 10. The compound of claim 1 wherein
R3 and R4 are substituted on adjacent carbon atoms on the phenyl ring and taken together form a fused heteroaromatic ring; and R1 and R2 are independently selected from hydrogen and lower alkyl.
- 11. The compound of claim 10 wherein said compound is 6-(3,5-6-Benzo[b]thiophen-7-yl-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 12. The compound of claim 1 wherein R3 and R4 are attached on adjacent carbon atoms on the phenyl ring and form a two membered ring system, one of said rings being a heteroaromatic ring and the other being an aromatic ring.
- 13. The compound of claim 12 wherein said compound is 7-methyl-6-phenoxathiin-4-yl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 14. The compound of claim 1 wherein R1 and R2 are independently selected from hydrogen and lower alkyl, and R3 and R4 are independently selected from the group consisting of hydrogen, lower alkyl and lower alkenyl.
- 15. The compound of claim 14 wherein R4 is lower alkenyl and R3 is hydrogen.
- 16. The compound of claim 15 wherein said compound is 7-methyl-6-(4-vinyl-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 17. The compound of claim 14 wherein R4 is selected from lower alkyl and hydrogen, and R3 is lower alkenyl.
- 18. The compound of claim 17 wherein said compound 7-methyl-6-o-tolyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 19. The compound of claim 17 wherein said compound 6-(2,5-dimethyl-phenyl)-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 20. The compound of claim 17 wherein said compound is 7-methyl-6-m-tolyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 21. The compound of claim 17 wherein said compound 6-(4-ethyl-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 22. The compound of claim 17 wherein said compound 6-(4-tert-butyl-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 23. The compound of claim 1 wherein
R1 and R2 are independently selected from hydrogen and lower alkyl, R3 and R4 are independently selected from hydrogen, halogen, trifluoroloweralkyl; and one of R3 and R4 is other than hydrogen.
- 24. The compound of claim 23 wherein said compound is 6-(3,5-bis-trifluoromethyl-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine.
- 25. The compound of claim 23 wherein said compound is 6-(4-fluoro-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 26. The compound of claim 23 wherein said compound is 6-(3-fluoro-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 27. The compound of claim 23 wherein said compound is 6-(2,4-dichloro-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 28. The compound of claim 23 wherein said compound is 6-(2-chloro-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 29. The compound of claim 23 wherein said compound is 6-(2-trifluoromethyl-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine.
- 30. The compound of claim 23 wherein said compound is 6-(3-fluoro-phenyl)-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 31. The compound of claim 23 wherein said compound is 6-(2,4-dichloro-phenyl)-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 32. The compound of claim 23 wherein said compound is 7-methyl-6-(4-trifluoromethoxy-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 33. The compound of claim 23 wherein said compound is 6-(3,4-dichloro-phenyl)-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 34. The compound of claim 1 wherein
R1 and R2 are independently selected from hydrogen and lower alkyl; R3 is selected from hydrogen and halogen; and R4 is selected from the group consisting of halogen, nitro, lower alkoxy, phenoxy, hydroxy, hydroxyalkyl, 141v is an integer selected from 0 to 4; and R12 is selected from hydrogen and lower alkyl.
- 35. The compound of claim 34 wherein R3 is selected from hydrogen and halogen, and R4 is selected from the group consisting of nitro, halogen, phenoxy, lower alkoxy, hydroxy and hydroxyalkyl.
- 36. The compound of claim 35 wherein said compound is 6-(3-ethoxy-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 37. The compound of claim 35 wherein said compound is 6-(3-nitro-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine.
- 38. The compound of claim 35 wherein said compound is 6-(5-chloro-2-methoxy-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 39. The compound of claim 35 wherein said compound is [3-(1,3-diamino-7-methyl-7H-pyrrolo[3,2-f]quinazolin-6-yl)-phenyl]-methanol trifluoro-acetic acid salt.
- 40. The compound of claim 35 wherein said compound is 6-(5-fluoro-2-methoxy-phenyl)-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 41. The compound of claim 35 wherein said compound is 6-(2,6-difluoro-phenyl)-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 42. The compound of claim 35 wherein said compound is 7-methyl-6-(2-phenoxy-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 43. The compound of claim 34 wherein
R3 is hydrogen, R4 is 142and R12 is selected from hydrogen and lower alkyl.
- 44. The compound of claim 43 wherein said compound is 3-(1,3-diamino-7H-pyrrolo[3,2-f]quinazolin-6-yl)-benzaldehyde.
- 45. The compound of claim 43 wherein said compound is 1-[3-(1,3-diamino-7-methyl-7H-pyrrolo[3,2-f]quinazolin-6-yl)-phenyl]-ethanone trifluoro-acetic acid salt.
- 46. The compound of claim 34 wherein
R3 and R4 are independently selected from hydrogen and 143v is as above; R1 and R2 are selected from hydrogen and lower alkyl; and one of R3 and R4is other than hydrogen.
- 47. The compound of claim 46 wherein said compound is 3-[2-(1,3-diamino-7H-pyrrolo[3,2-f]quinazolin-6-yl)-phenyl]-propionic acid.
- 48. The compound of claim 46 wherein said compound is [3-(1,3-diamino-7H-pyrrolo[3,2-f]quinazolin-6-yl)-phenyl]-acetic acid.
- 49. The compound of claim 46 wherein said compound is [4-(1,3-diamino-7H-pyrrolo[3,2-f]quinazolin-6-yl)-phenyl]-acetic acid.
- 50. The compound of claim 46 wherein said compound is 3-[3-(1,3-diamino-7H-pyrrolo[3,2-f]quinazolin-6-yl)-phenyl]-propionic acid.
- 51. The compound of claim 1 wherein
R1 and R2 are independently selected from hydrogen and lower alkyl; R3 and R4 are selected from the group consisting of hydrogen, R5 R6 N—, 144and R7S—; R5 and R6 are independently selected from hydrogen and lower alkyl; R7 is lower alkyl; and one of R3 and R4is other than hydrogen.
- 52. The compound of claim 51 wherein said compound is 6-(3-amino-phenyl)-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 53. The compound of claim 51 wherein said compound is 6-(4-ethylsulfanyl-phenyl)-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 54. The compound of claim 1 wherein
R2 is selected from —(CH2)n—CH2—OR13 or 145R13 is selected from the group consisting of hydrogen, phenyl, benzyl and lower alkyl; and n is an integer from 0 to 4.
- 55. The compound of claim 54 wherein said compound is 2-[1,3-diamino-6-(2-trifluoromethyl-phenyl)-pyrrolo[3,2-f]quinazolin-7-yl]-ethanol trifluoro-acetic acid salt.
- 56. The compound of claim 55 wherein said compound is 7-(2-benzyloxy-ethyl)-6-(2-trifluoromethyl-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 57. The compound of claim 55 wherein said compound is [1,3-diamino-6-(2-trifluoromethyl-phenyl)-pyrrolo[3,2-f]quinazolin-7-yl]-acetic acid trifluoro-acetic acid salt.
- 58. The compound of claim 1 wherein
R2 is 146R10 and R11, are independently selected from hydrogen and lower alkyl.
- 59. The compound of claim 58 wherein said compound is 2-[1,3-diamino-6-(3-methoxy-phenyl)-pyrrolo[3,2-f]quinazolin-7-yl]—N,N-diethyl-acetamide.
- 60. A compound of the formula:
- 61. The compound of claim 60 wherein {circle over (P)} is a heteroaromatic ring containing sulfur as the only hetero atom.
- 62. The compound of claim 61 wherein R3 and R4 are independently selected from hydrogen, halogen and lower alkyl.
- 63. The compound of claim 62 wherein said compound is 7-methanesulfonyl-6-thiophen-2-yl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 64. The compound of claim 62 wherein said compound is 7-methyl-6-thiophen-2-yl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine.
- 65. The compound of claim 62 wherein said compound is 6-(5-chloro-thiophen-2-yl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 66. The compound of claim 61 wherein
R3 and R4 is selected from hydrogen and 150R12 is selected from hydrogen and lower alkyl; and R3 and R4 are other than hydrogen.
- 67. The compound of claim 66 wherein said compound is 1-[5-(1,3-diamino-7H-pyrrolo[3,2-f]quinazolin-6-yl)-thiophen-2-yl]-ethanone trifluoro-acetic acid salt.
- 68. The compound of claim 66 wherein said compound is 1-[5-(1,3-diamino-7-methyl-7H-pyrrolo[3,2-f]quinazolin-6-yl)-thiophen-2-yl]-ethanone trifluoro-acetic acid salt.
- 69. The compound of claim 60 wherein R3 and R4 are attached to the hetero atom ring on adjacent carbon atoms and taken together with their attached carbon atoms a fused phenyl ring.
- 70. The compound of claim 69 wherein said compound is 6-benzo[b]thiophen-2-yl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 71. The compound of claim 69 wherein said compound is 6-benzo[b]thiophen-2-yl-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 72. The compound of claim 66 wherein said compound is 6-benzofuran-2-yl-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine.
- 73. The compound of claim 60 wherein {circle over (P)} is a heteroaromatic ring containing an oxygen atom as the only hetero atom.
- 74. The compound of claim 73 wherein said compound is 6-furan-2-yl-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 75. The compound of claim 73 wherein said compound is 6-benzofuran-2-yl-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine
- 76. The compound of claim 60 wherein {circle over (P)} is a heteroaromatic ring containing a nitrogen hetero atom.
- 77. The compound of claim 76 wherein said compound is 6-(3,5-dimethyl-isoxazol-4-yl)-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine trifluoro-acetic acid salt.
- 78. A pharmaceutical composition comprising one or more of the compounds of the formula:
- 79. A pharmaceutical composition comprising one or more of the formula:
- 80. A method of treating a disease based on high blood glucose concentration comprising administering to a patient in need of such treatment a therapeutically effective amount of at least one compound of the formula:
- 81. A method of treating a disease based on high blood glucose concentration comprising administering to a patient in need of such treatment a therapeutically effective amount of at least one compound of the formula:
PRIORITY TO PROVISIONAL APPLICATION(S) UNDER 35 U.S.C. §119(e)
[0001] This application claims priority under 35 U.S.C. §119(e) of provisional application(s) Ser. No. 60/470,803, filed May 15, 2003 and Ser. No. 60/563,584, filed Apr. 19, 2004.
Provisional Applications (2)
|
Number |
Date |
Country |
|
60470803 |
May 2003 |
US |
|
60563584 |
Apr 2004 |
US |