IP Library Granted Patent US 8,148,392
Granted Patent B2
US 8,148,392 · App. 11/915,257 · Granted Apr 3, 2012

2-indolyl imidazo [4,5-d] phenanthroline derivatives and their use in the treatment of cancer

Assignee: Lorus Therapeutics Inc.
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Quick Facts
Patent No.
US 8,148,392
App. No.
11/915,257
Granted
Apr 3, 2012
Kind
B2
Abstract

2-indolyl imidazo[4,5-d]phenanthroline compounds of Formula (I) and methods of using same in the treatment of cancer, in particular, solid cancers and leukemia are provided. Pharmaceutical compositions comprising the compounds are also provided.

Claims (50)

1. A compound of Formula (I):

or a salt thereof, wherein:

R1, R3, R4, R5, and R7 are hydrogen;

R2 is halogen; and

R6 is C1-C4 alkyl.

2. The compound according to claim 1 , wherein:

R6 is CH 3 , isopropyl, or t-butyl.

3. The compound according to claim 1 , wherein:

R6 is CH 3 .

4. The compound according to claim 1 , wherein:

R2 is F or Br.

5. The compound according to claim 1 , wherein:

R2 is F.

6. The compound according to claim 1 , wherein said compound is selected from the group consisting of:

or a salt thereof.

7. The compound according to claim 1 , wherein said compound is:

or a salt thereof.

8. A pharmaceutical composition comprising the compound according to claim 1 , or a salt thereof, and a pharmaceutically acceptable carrier.

9. The pharmaceutical composition according to claim 8 , wherein in the compound of Formula I: R6 is CH 3 , isopropyl, or t-butyl.

10. The pharmaceutical composition according to claim 8 , wherein in the compound of Formula I: R6 is CH 3 .

11. The pharmaceutical composition according to claim 8 , wherein in the compound of Formula I: R2 is F or Br.

12. The pharmaceutical composition according to claim 8 , wherein in the compound of Formula I: R2 is F.

13. The pharmaceutical composition according to claim 8 , wherein the compound is selected from the group consisting of:

or a salt thereof.

14. The pharmaceutical composition according to claim 8 , wherein the compound is:

or a salt thereof.

15. A method of treating cancer in a mammal, comprising administering to said mammal an effective amount of a compound according to claim 1 , or a salt thereof, wherein said cancer is non-small cell lung cancer, colon cancer, breast cancer, ovarian cancer, leukemia, renal cancer, melanoma, prostate cancer or CNS cancer.

16. The method according to claim 15 , wherein in the compound of Formula I: R6 is CH 3 , isopropyl, or t-butyl.

17. The method according to claim 15 , wherein in the compound of Formula I: R6 is CH 3 .

18. The method according to claim 15 , wherein in the compound of Formula I: R2 is F or Br.

19. The method according to claim 15 , wherein in the compound of Formula I: R2 is F.

20. The method according to claim 15 , wherein the compound is selected from the group consisting of:

or a salt thereof.

21. The method according to claim 15 , wherein the compound is:

or a salt thereof.

22. The method according to claim 15 , wherein said cancer is a solid tumour.

23. The method according to claim 22 , wherein said solid tumour is selected from the group of: non-small cell lung tumour, colon tumour, prostate tumour, breast tumour, and melanoma tumour.

24. The method according to claim 15 , wherein said cancer is a leukaemia.

25. The compound according to claim 1 , wherein said salt is an HCl salt.

26. The pharmaceutical composition according to claim 8 , wherein said composition is a liposomal or lipid micelle formulation.

27. The pharmaceutical composition according to claim 8 , wherein said salt is an HCl salt.

28. The pharmaceutical composition according to claim 8 , wherein said composition is formulated for intravenous administration.

29. The method according to claim 15 , wherein said compound is administered as a liposomal or lipid micelle formulation.

30. The method according to claim 15 , wherein said salt is an HCl salt.

31. The method according to claim 15 , wherein said compound is administered to said mammal intravenously.

32. The method according to claim 15 , wherein said CNS cancer is a glioma.

33. The method according to claim 15 , wherein said cancer is non-small cell lung cancer.

34. The method according to claim 15 , wherein said cancer is colon cancer.

35. The method according to claim 21 , wherein said cancer is non-small cell lung cancer.

36. The method according to claim 21 , wherein said cancer is colon cancer.

Assignments (5)
CHANGE OF NAME Recorded Sep 22, 2014
From: LORUS THERAPEUTICS INC.
To: APTOSE BIOSCIENCES INC.
Reel/Frame 033793/0620 →
CHANGE OF NAME Recorded Jun 8, 2009
From: LORUS THERAPEUTICS INC.
To: 4325231 CANADA INC.
Reel/Frame 022794/0140 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2009
From: 4325231 CANADA INC.
To: GENESENSE TECHNOLOGIES INC.
Reel/Frame 022794/0416 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2009
From: GENESENSE TECHNOLOGIES INC.
To: LORUS THERAPEUTICS INC.
Reel/Frame 022794/0635 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2008
From: HUESCA, MARIO; YOUNG, AIPING H.; LEE, YOON; KHINE, AYE AYE; WRIGHT, JIM A.; LOCK, LISA; AL-QAWASMEH, RAED
To: LORUS THERAPEUTICS INC.
Reel/Frame 021851/0490 →
Continuity (4)
Provisional Application 60684162 · May 25, 2005
Provisional Application 60710551 · Aug 22, 2005
Provisional Application 60787526 · Mar 31, 2006
Related Publication 20100168417A1 · Jul 1, 2010