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Last Updated: April 26, 2024

Claims for Patent: 9,738,625


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Summary for Patent: 9,738,625
Title:Therapeutically active compounds and their methods of use
Abstract: Provided are isocitrate dehydrogenase 2 (IDH2) inhibitor compounds useful for treating cancer and methods of treating cancer, comprising administering to a subject in need thereof a compound described herein. Also provided are polymorphic forms of the IDH2 inhibitor compounds characterized by X Ray powder diffraction patterns, having improved physicochemical properties that influence in vivo dissolution rate for formulation purposes.
Inventor(s): Agresta; Samuel V. (Lexington, MA), Gu; Chong-Hui (Waban, MA), Schenkein; David (Boston, MA), Yang; Hua (Acton, MA), Guo; Liting (Suzhou, CN), Tang; Zhen (Suzhou, CN), Wang; Jianming (Suzhou, CN), Zhang; Yanfeng (Suzhou, CN), Zhou; Yan (Suzhou, CN)
Assignee: Agios Pharmaceuticals, Inc. (Cambridge, MA)
Application Number:14/909,451
Patent Claims: 1. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the isolated crystalline form is Form 16, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 6.8, 10.6, 13.6, 14.2, and 19.2.degree..+-.0.2.degree..

2. The isolated crystalline form of claim 1, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 34.

3. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the isolated crystalline form is Form 1, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 8.9, 13.0, 18.9, 23.8, and 28.1.degree..+-.0.2.degree..

4. The isolated crystalline form of claim 3, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 1.

5. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the isolated crystalline form is Form 2, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 12.7, 17.1, 19.2, 23.0, and 24.2.degree..+-.0.2.degree..

6. The isolated crystalline form of claim 5, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 2.

7. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol methanesulfonate, wherein the isolated crystalline form is Form 3, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 7.5, 9.3, 14.5, 18.8, 21.3, and 24.8.degree..+-.0.2.degree..

8. The isolated crystalline form of claim 7, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 5.

9. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol methanesulfonate, wherein the isolated crystalline form is Form 7, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 14.1, 19.1, 21.8, 23.5, and 25.7.degree..+-.0.2.degree..

10. The isolated crystalline form of claim 9, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 15.

11. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol methanesulfonate, wherein the isolated crystalline form is Form 8, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 9.0, 9.2, 21.9, 22.1, 24.2, and 24.6.degree..+-.0.2.degree..

12. The isolated crystalline form of claim 11, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 17.

13. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol methanesulfonate, wherein the isolated crystalline form is Form 9, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 6.5, 19.6, 20.1, and 21.6.degree..+-.0.2.degree..

14. The isolated crystalline form of claim 13, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 19.

15. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the isolated crystalline form is Form 17, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 7.2, 13.6, 18.5, 19.3, 21.9, and 23.5.degree..+-.0.2.degree..

16. The isolated crystalline form of claim 15, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 37.

17. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the isolated crystalline form is Form 18, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 6.4, 8.4, 9.8, 17.8, and 19.7.degree..+-.0.2.degree..

18. The isolated crystalline form of claim 17, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 38.

19. An isolated crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)p- yridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the isolated crystalline form is Form 19, characterized by an X-ray powder diffraction pattern having peaks at 2.theta. angles of 8.1, 14.1, 16.4, 17.3, 20.5, and 24.1.degree..+-.0.2.degree..

20. The isolated crystalline form of claim 19, characterized by an X-ray powder diffraction pattern substantially similar to FIG. 39.

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