Solid forms of 1-ethyl-7-(2-methyl-6-(1H-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one, as TOR kinase inhibitors

Patent metadata

Field	Value
Publication number	US-9416134-B2
Application number	US-201514686879-A
Country	US
Kind code	B2
Filing date	Apr 15, 2015
Priority date	Apr 16, 2014
Publication date	Aug 16, 2016
Grant date	Aug 16, 2016

Abstract

Provided herein are formulations, processes, solid forms and methods of use relating to the Compound for formula 1:

having the name 1-ethyl-7-(2-methyl-6-(1H-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4 -dihydropyrazino[2,3-b]pyrazin-2(1H)-one and tautomers thereof.

First claim

What is claimed is:

1. A crystal form comprising the compound of formula (I), or a tautomer thereof:

which has an X-ray powder diffraction pattern comprising peaks at 6.18±0.2°, 21.74 ±0.2° and 26.7±0.2° 2θ.

2. The crystal form of claim 1 which has an X-ray powder diffraction pattern further comprising peaks at 12.34±0.2°, 22.5±0.2° and 23.42±0.2° 2θ.

3. The crystal form of claim 1 which has a thermogravimetric analysis thermogram comprising a total mass loss of 15.5% of the total mass of the crystal form when heated from 25° C. to 300° C.

4. The crystal form of claim 1 which has a single differential thermal analysis thermogram comprising an endotherm between 90° C. and 185° C. with a maximum at 140° C. when heated from 25° C. to 300° C.

5. The crystal form of claim 4 wherein the single differential thermal analysis thermogram further comprises an endotherm between 240° C. and 285° C. with a maximum at 264° C.

6. The crystal form of claim 1 which is at least 90% pure.

7. A crystal form of the compound of formula (I), or a tautomer thereof:

which has an X-ray powder diffraction pattern comprising peaks at 3.5±0.2°, 9.26±0.2° and 18.62±0.2° 2θ.

8. The crystal form of claim 7 which has an X-ray powder diffraction pattern further comprising peaks at 7.06±0.2°, 12.66±0.2° and 15.3±0.2° 2θ.

9. The crystal form of claim 7 which has a thermogravimetric analysis thermogram comprising a total mass loss of 12.8% of the total mass of the crystal form when heated from 25° C. to 300° C.

10. The crystal form of claim 7 which has a single differential thermal analysis thermogram comprising an endotherm between 110° C. and 175° C. with a maximum at 160° C. when heated from 25° C. to 300° C.

11. The crystal form of claim 10 wherein the single differential thermal analysis thermogram further comprises an endotherm between 225° C. and 275° C. with a maximum at 254° C.

12. The crystal form of claim 7 which is at least 90% pure.

13. A crystal form of the compound of formula (I), or a tautomer thereof:

which has an X-ray powder diffraction pattern comprising peaks at 10.66±0.2°, 21.94±0.2° and 26.26±0.2° 2θ.

14. The crystal form of claim 13 which has an X-ray powder diffraction pattern further comprising peaks at 10.14±0.2°, 18.1±0.2° and 22.66±0.2° 2θ.

15. The crystal form of claim 13 which has a thermogravimetric analysis thermogram comprising a total mass loss of 16.4% of the total mass of the crystal form when heated from 25° C. to 300° C.

16. The crystal form of claim 13 which has a single differential thermal analysis thermogram comprising an endotherm between 100° C. and 175° C. with a maximum at 140° C. when heated from 25° C. to 300° C.

17. The crystal form of claim 16 wherein the single differential thermal analysis thermogram further comprises an endotherm between 235° C. and 275° C. with a maximum at 258° C.

18. The crystal form of claim 13 which is at least 90% pure.

19. A crystal form of the compound of formula (I), or a tautomer thereof:

which has an X-ray powder diffraction pattern comprising peaks at 9.26±0.2°, 11.7±0.2° and 26.18±0.2° 2θ.

20. The crystal form of claim 19 which has an X-ray powder diffraction pattern further comprising peaks at 7.46±0.2°, 24.26±0.2° and 24.94±0.2° 2θ.

21. The crystal form of claim 19 which has a thermogravimetric analysis thermogram comprising a total mass loss of 9.4% of the total mass of the crystal form when heated from 25° C. to 300° C.

22. The crystal form of claim 19 which has a single differential thermal analysis thermogram comprising an endotherm between 50° C. and 140° C. with a maximum at 80° C. when heated from 25° C. to 300° C.

23. The crystal form of claim 22 wherein the single differential thermal analysis thermogram further comprises an exotherm between 160° C. and 200° C. with a maximum at 181° C.

24. The crystal form of claim 23 wherein the single differential thermal analysis thermogram further comprises an endotherm between 225° C. and 275° C. with a maximum at 251° C.

25. The crystal form of claim 19 which is at least 90% pure.

Assignees

• Signal Pharm Llc

Inventors

• Eckert Jeffrey

Classifications

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P37/02

  Immunomodulators · CPC title