Granted Patent B2

US 12,338,249 · App. 17/716,963 · Granted Jun 24, 2025

Inventors: Michael Thomas Brandl (Redwood City, CA); Patricia Andres (Bend, OR); Petinka I. Vlahova (West Lafayette, IN); Tsuyoshi Sasaki (Osaka, JP)

Assignees: Sumitomo Pharma Switzerland GmbH; Takeda Pharmaceutical Company Limited

C07D495/04C07B2200/13

Abstract

Claims (20)

1. A crystalline form of an isopropyl alcohol solvate of N-(4-(1-(2,6-difluorobenzyl)-5-((dimethylamino)methyl)-3-(6-methoxy-3-pyridazinyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-N′-methoxyurea.

2. The crystalline form of claim 1 , characterized by an X-ray powder diffraction pattern comprising at least three 2-theta (2θ+0.2° 2θ) peaks selected from 8.4°, 10.6°, 13.6°, 15.4° and 18.8°.

3. The crystalline form of claim 1 , characterized by an X-ray powder diffraction pattern comprising 2-theta (2θ+0.2° 2θ) peaks at 8.4°, 10.6°, 13.6°, 15.4° and 18.8°.

4. The crystalline form of claim 1 , characterized by an X-ray powder diffraction pattern substantially the same as the pattern shown in FIG. 13 .

5. The crystalline form of claim 1 , characterized by a thermogravimetric (TG) thermogram substantially the same as the pattern shown in FIG. 14 .

6. The crystalline form of claim 1 , characterized by a differential scanning calorimetry (DSC) thermogram comprising an endothermic peak at about 147° C.

7. The crystalline form of claim 1 , characterized by a DSC thermogram substantially the same as the pattern shown in FIG. 15 .

8. A crystalline form of a dimethylformamide solvate of N-(4-(1-(2,6-difluorobenzyl)-5-((dimethylamino)methyl)-3-(6-methoxy-3-pyridazinyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-N′-methoxyurea that exhibits an X-ray powder diffraction pattern comprising at least three 2-theta (2θ+0.2° 2θ) peaks selected from 7.0°, 10.3°, 10.5°, 13.0°, 18.4° and 20.8°.

9. The crystalline form of claim 8 , wherein the X-ray powder diffraction pattern comprises at least five 2-theta (2θ+0.2° 2θ) peaks selected from 7.0°, 10.3°, 10.5°, 13.0°, 18.4° and 20.8°.

10. The crystalline form of claim 8 , characterized by an X-ray powder diffraction pattern substantially the same as the pattern shown in FIG. 30 .

11. The crystalline form of claim 8 , characterized by a TG thermogram substantially the same as the pattern shown in FIG. 31 , top panel.

12. The crystalline form of claim 8 , characterized by a DSC thermogram comprising an endothermic peak at about 178° C.

13. The crystalline form of claim 8 , characterized by a DSC thermogram substantially the same as the pattern shown in FIG. 31 , bottom panel.

14. A crystalline form of an acetone solvate of N-(4-(1-(2,6-difluorobenzyl)-5-((dimethylamino)methyl)-3-(6-methoxy-3-pyridazinyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-N′-methoxyurea.

15. The crystalline form of claim 14 , characterized by an X-ray powder diffraction pattern comprising at least three 2-theta (2θ+0.2° 2θ) peaks selected from 10.3°, 10.6°, 11.1°, 13.0°, 15.7°, 18.4°, 19.1°, 20.3° and 20.7°.

16. The crystalline form of claim 14 , characterized by an X-ray powder diffraction pattern comprising at least five 2-theta (2θ+0.2° 2θ) peaks selected from 10.3°, 10.6°, 11.1°, 13.0°, 15.7°, 18.4°, 19.1°, 20.3° and 20.7°.

17. The crystalline form of claim 14 , characterized by an X-ray powder diffraction pattern substantially the same as the pattern shown in FIG. 32 .

18. The crystalline form of claim 14 , characterized by a TG thermogram substantially the same as the pattern shown in FIG. 33 , top panel.

19. The crystalline form of claim 14 , characterized by a DSC thermogram comprising an endothermic peak at about 189° C.

20. The crystalline form of claim 14 , characterized by a DSC thermogram substantially the same as the pattern shown in FIG. 33 , bottom panel.

Assignments (9)

Continuity (3)

References Cited (156)

Cited By (3)

US 12,551,447 US 12,655,154 US 12,735,430