Pharmaceutical formulations, processes, solid forms and methods of use relating to 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

• US 9,827,243 B2
• Filed: 05/10/2016
• Issued: 11/28/2017
• Est. Priority Date: 04/17/2013
• Status: Active Grant

• Current Assignee: Signal Pharmaceuticals, LLC (Bristol-Myers Squibb Company)
• Original Assignee: Signal Pharmaceuticals, LLC (Bristol-Myers Squibb Company)
• Inventors: Kreilein, Matthew Michael, Lee, Thomas, Li, Ying, Xu, Jean, Leong, William Wei-Hwa, Cohen, Benjamin
• Primary Examiner(s): COUGHLIN, MATTHEW P
• Application Number:
  US15/150,577
• Publication Number:
  US 20160250210A1
• Time in Patent Office: 567 Days
• CPC Class Codes: A61K 31/4985 Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
• CPC Class Codes: A61K 9/2018 Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
• CPC Class Codes: A61K 9/2054 Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
• CPC Class Codes: A61K 9/4858 Organic compounds
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems

Abstract

Provided herein are formulations, processes, solid forms and methods of use relating to 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.

Claims

1. A method for treating a cancer, comprising administering to a patient having a cancer a crystal form of Compound 1

2. The method of claim 1, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.8, 12.0 and 17.9±

0.2°

2θ

.

3. The method of claim 1, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 7.5, 10.4 and 11.7±

0.2°

2θ

.

4. The method of claim 1, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.3, 11.7 and 19.9±

0.2°

2θ

.

5. The method of claim 1, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 11.0, 20.2 and 21.9±

0.2°

2θ

.

6. The method of claim 1, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.3, 15.3 and 18.6±

0.2°

2θ

.

7. The method of claim 1, wherein the cancer is glioblastoma multiforme.

8. The method of claim 7, wherein the glioblastoma multiforme is characterized by O6-methylguanine-DNA methyltransferase (MGMT) methylation.

9. The method of claim 1, wherein the cancer is head and neck squamous cell carcinoma.

10. The method of claim 9, wherein the head and neck squamous cell carcinoma is characterized by deletion of chromosome 11q22 or loss of ataxia telangiectasia mutated (ATM) expression.

11. The method of claim 1, wherein the cancer is castration-resistant prostate cancer.

12. The method of claim 11, wherein the castration-resistant prostate cancer is E-twenty six (ETS) overexpressing castration-resistant prostate cancer.

13. The method of claim 1, wherein the cancer is Ewing'"'"'s sarcoma.

14. The method of claim 13, wherein the Ewing'"'"'s sarcoma is E-twenty six (ETS) overexpressing Ewings sarcoma.

15. The method of claim 1, wherein the cancer is chronic lymphocytic leukemia.

16. The method of claim 15, wherein the chronic lymphocytic leukemia is characterized by deletion of chromosome 11q22, loss of ataxia telangiectasia mutated (ATM) expression, mutation of IgVH, wild type IgVH, wild type p53/ATM, mutation of p53 or dysfunctional p53.

17. The method of claim 1, wherein the cancer is small lymphocytic lymphoma.