IP Library › Granted Patent US 12,427,154
Granted Patent B2
US 12,427,154 · App. 17/820,779 · Granted Sep 30, 2025

Salts of 2-fluoro-n-methyl-4-[7-(quinolin-6-yl-methyl)-imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide and processes related to preparing the same

Inventors: Lingkai Weng (Malvern, PA); Lei Qiao (Downingtown, PA); Jiacheng Zhou (Newark, DE); Pingli Liu (Newark, DE); Yongchun Pan (Newark, DE)
Assignees: Incyte Holdings Corporation; Incyte Corporation
A61K31/53C07D253/07C07D401/10C07D487/04
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Quick Facts
Patent No.
US 12,427,154
App. No.
17/820,779
Granted
Sep 30, 2025
Kind
B2
Abstract

The present invention is directed to dihydrochloric acid and dibenzenesulfonic acid salts of the c-Met kinase inhibitor 2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)-imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide, and pharmaceutical compositions thereof, useful in the treatment of cancer and other diseases related to the dysregulation of kinase pathways. The present invention further relates to processes and intermediates for preparing 2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide, and salts thereof.

Claims (20)

1. A salt which is 2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide dibenzenesulfonic acid salt, or a hydrate or solvate thereof.

2. The salt of claim 1 , wherein said salt is anhydrous.

3. The salt of claim 1 , which is characterized by a melting point of about 268 to about 272° C.

4. The salt of claim 1 , which is characterized by a melting point of about 270° C.

5. The salt of claim 1 , which is crystalline.

6. The salt of claim 1 , having a DSC thermogram which is characterized by an endothermic peak at about 270° C.

7. The salt of claim 1 , having an X-ray powder diffraction pattern comprising a characteristic peak expressed in degrees 2θ at about 20.2.

8. The salt of claim 1 , having an X-ray powder diffraction pattern comprising a characteristic peak expressed in degrees 2θ at about 15.0.

9. The salt of claim 1 , having an X-ray powder diffraction pattern comprising a characteristic peak expressed in degrees 2θ at about 16.3.

10. The salt of claim 1 , having an X-ray powder diffraction pattern comprising a characteristic peak expressed in degrees 2θ at about 18.3.

11. The salt of claim 1 , having an X-ray powder diffraction pattern comprising a characteristic peak expressed in degrees 2θ at about 23.8.

12. The salt of claim 1 , having an X-ray powder diffraction pattern comprising a characteristic peak expressed in degrees 2θ at about 4.9.

13. The salt of claim 1 , having an X-ray powder diffraction pattern comprising characteristic peaks expressed in degrees 2θ at about 15.0, 16.3, 18.3, 20.2, 23.8, and 4.9.

14. A composition comprising the salt, or a hydrate or solvate thereof, of claim 1 and at least one pharmaceutically acceptable carrier.

15. A method of inhibiting activity of a receptor or non-receptor tyrosine kinase comprising contacting said kinase with the salt of claim 1 , or a hydrate or solvate thereof; wherein said kinase is c-Met.

16. A method of inhibiting the HGF/c-Met kinase signaling pathway in a cell comprising contacting said cell with the salt of claim 1 , or a hydrate or solvate thereof.

17. A method of inhibiting the proliferative activity of a cell comprising contacting said cell with the salt of claim 1 , or a hydrate or solvate thereof.

18. A method of treating a disease in a patient, wherein said disease is associated with dysregulation of the HGF/c-MET signaling pathway, comprising administering to said patient a therapeutically effective amount of the salt of claim 1 , or a hydrate or solvate thereof; wherein said disease is kidney cancer, liver cancer, lung cancer, gastric cancer, breast cancer, or glioblastoma.

19. A method of treating a cancer in a patient comprising administering to said patient a therapeutically effective amount of the salt of claim 1 , or a hydrate or solvate thereof; wherein the cancer is kidney cancer, liver cancer, lung cancer, gastric cancer, breast cancer, or glioblastoma.

20. The method of claim 19 , wherein said cancer is lung cancer.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 17, 2022
From: WENG, LINGKAI; QIAO, LEI; ZHUO, JIACHENG; LIU, PINGLI; PAN, YONGCHUN
To: INCYTE CORPORATION
Reel/Frame 061442/0369 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 17, 2022
From: INCYTE CORPORATION
To: INCYTE CORPORATION; INCYTE HOLDINGS CORPORATION
Reel/Frame 061442/0626 →
Continuity (8)
Continuation 17014414 · Sep 8, 2020
Continuation 16269871 · Feb 7, 2019
Continuation 15355630 · Nov 18, 2016
Continuation 14525381 · Oct 28, 2014
Continuation 13793864 · Mar 11, 2013
Division 12469360 · May 20, 2009
Provisional Application 61054995 · May 21, 2008
Related Publication 20230098850A1 · Mar 30, 2023
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