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Last Updated: November 26, 2020

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Claims for Patent: 9,493,470

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Summary for Patent: 9,493,470
Title:Crystalline forms of 3-(imidazo[1,2-B] pyridazin-3-ylethynyl)-4-methyl-N-{4-[(4-methylpiperazin-1-yl) methyl]-3-(trifluoromethyl)phenyl}benzamide and its mono hydrochloride salt
Abstract: Novel crystalline forms of 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyi-N-{4-[(4-methylpiperazin- -1-yl)methyl]-3-(trifluoromethyl)phenyljbenzamide free base and 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyi-N-{4-[(4-methyl piperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}benzamide mono hydrochloride, pharmaceutical compositions thereof and methods of their preparation and use are disclosed herein. The instant application is directed to novel crystalline forms of 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyi-N-{4-[(4-methylpiperazin- -1-yl)methyl]-3-(trifluoromethyl}phenyl}benzamide and 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyi-N-{4-[(4-methylpiperazin- -1-yl)methyl]-3-(trifluoromethyl)phenyl}benzamide mono hydrochloride, compositions comprising such crystalline forms, and to methods of their preparation and use.
Inventor(s): Murray; Christopher K. (Lexington, MA), Rozamus; Leonard W. (Andover, MA), Chaber; John J. (Westford, MA), Sharma; Pradeep (Westford, MA)
Assignee: ARIAD PHARMACEUTICALS, INC. (Cambridge, MA)
Application Number:14/651,577
Patent Claims: 1. Crystalline Form A of ponatinib hydrochloride characterized by an x-ray powder diffraction pattern comprising at least five 2.theta. values (.+-.0.3) chosen from 5.9, 7.1, 10.0, 12.5, 16.4, 19.3, 21.8, 23.8, and 26.1.

2. Crystalline ponatinib hydrochloride of which more than 90% is the crystalline Form A of ponatinib hydrochloride of claim 1.

3. The crystalline Form A of ponatinib hydrochloride of claim 1 characterized by an x-ray powder diffraction pattern substantially as shown in FIG. 4.

4. Crystalline Form A ponatinib hydrochloride characterized by an x-ray powder diffraction pattern comprising at least five 2.theta. values (.+-.0.3) chosen from 5.9, 7.1, 10.0, 12.5, 13.6, 14.1, 15.0, 16.4, 17.7, 18.6, 19.3, 20.4, 21.8, 22.3, 23.8, 24.9, 26.1, 27.0, 28.4, 30.3, 31.7, and 35.1.

5. A pharmaceutical composition comprising crystalline Form A ponatinib hydrochloride according to claim 1 and at least one pharmaceutically acceptable carrier, vehicle or excipient.

6. A pharmaceutical composition comprising crystalline Form A ponatinib hydrochloride according to claim 2 and at least one pharmaceutically acceptable carrier, vehicle or excipient.

7. A pharmaceutical composition consisting essentially of the crystalline Form A of ponatinib hydrochloride of claim 1.

8. A method for treating chronic myeloid leukemia or Philadelphia chromosome-positive acute lymphoblastic leukemia in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a pharmaceutical composition of claim 5.

9. A method for treating chronic myeloid leukemia or Philadelphia chromosome-positive acute lymphoblastic leukemia in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a pharmaceutical composition of claim 6.

10. A pharmaceutical composition comprising crystalline Form A ponatinib hydrochloride according to claim 3 and at least one pharmaceutically acceptable carrier, vehicle or excipient.

11. A method for treating chronic myeloid leukemia or Philadelphia chromosome-positive acute lymphoblastic leukemia in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a pharmaceutical composition of claim 10.

12. Crystalline ponatinib hydrochloride of which more than 90% is the crystalline Form A of ponatinib hydrochloride of claim 4.

13. A pharmaceutical composition comprising crystalline Form A ponatinib hydrochloride according to claim 4 and at least one pharmaceutically acceptable carrier, vehicle or excipient.

14. A pharmaceutical composition comprising crystalline Form A ponatinib hydrochloride according to claim 12 and at least one pharmaceutically acceptable carrier, vehicle or excipient.

15. A pharmaceutical composition consisting essentially of the crystalline Form A of ponatinib hydrochloride of claim 4.

16. A method for treating chronic myeloid leukemia or Philadelphia chromosome-positive acute lymphoblastic leukemia in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a pharmaceutical composition of claim 13.

17. A method for treating chronic myeloid leukemia or Philadelphia chromosome-positive acute lymphoblastic leukemia in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a pharmaceutical composition of claim 14.

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