IP Library › Granted Patent US 12,398,133
Granted Patent B2
US 12,398,133 · App. 18/382,927 · Granted Aug 26, 2025

Solid state forms

Inventors: Mary Chaves (Arlington, MA); Patricia Lopez (Woodland Hills, CA); Prashant Agarwal (Chelsea, MA); Albert Amegadzie (Westlake Village, CA); Stephanie Azali (Woodland Hills, CA); Roman Shimanovich (Brighton, MA); Ron C. Kelly (Westlake Village, CA); Darren Leonard Reid (Belmont, MA)
Assignee: Amgen Inc.
C07D471/04C07B2200/13
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Quick Facts
Patent No.
US 12,398,133
App. No.
18/382,927
Granted
Aug 26, 2025
Kind
B2
Abstract

The present disclosure provides crystalline and amorphous forms of 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-(2-propanyl)-3-pyridinyl)-4-((2S)-2-methyl-4-(2-propenoyl)-1-piperazinyl)pyrido[2,3-d]pyrimidin-2(1H)-one, including several anhydrous, hydrate and solvate forms, and solid state forms thereof, pharmaceutical compositions, and methods of treating a disease mediated by KRAS G12C inhibition.

Claims (42)

1. A compound, wherein the compound is a crystalline form of the M atropisomer of 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-(2-propanyl)-3-pyridinyl)-4-((2S)-2-methyl-4-(2-propenoyl)-1-piperazinyl)pyrido[2,3-d]pyrimidin-2(1H)-one (Compound 1) and wherein the compound is characterized by 19 F solid state NMR comprising peaks at approximately −109 and −120 ppm.

2. The compound of claim 1 , wherein the compound is characterized by 19 F solid state NMR comprising peaks at approximately −49, −60, −79, −90, −109, −120, −138, −150, −168, and −179 ppm.

3. The compound of claim 2 , wherein the 19 F solid state NMR is measured at a spinning frequency of 14 kHz.

4. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient.

5. The pharmaceutical composition of claim 4 , wherein the pharmaceutical composition is a tablet.

6. The pharmaceutical composition of claim 5 , wherein the tablet comprises 120 mg of the compound.

7. A pharmaceutical composition comprising the compound of claim 2 and a pharmaceutically acceptable excipient.

8. The pharmaceutical composition of claim 7 , wherein the pharmaceutical composition is a tablet.

9. The pharmaceutical composition of claim 8 , wherein the tablet comprises 120 mg of the compound.

10. A pharmaceutical composition comprising the compound of claim 3 and a pharmaceutically acceptable excipient.

11. The pharmaceutical composition of claim 10 , wherein the pharmaceutical composition is a tablet.

12. The pharmaceutical composition of claim 11 , wherein the tablet comprises 120 mg of the compound.

13. A method of treating cancer having a KRAS G12C mutation in a patient in need thereof, the method comprising administering to the patient a therapeutically effective amount of the compound of claim 1 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer, small intestine cancer, appendix cancer, colorectal cancer, endometrial cancer, pancreatic cancer, liver cancer, small cell lung cancer, cervical cancer, germ cell tumor, ovarian cancer, pancreatic neuroendocrine tumor, bladder cancer, myelodysplastic/myeloproliferative neoplasms, head and neck cancer, esophageal cancer, soft tissue sarcoma, malignant mesothelioma, thyroid cancer, skin cancer, gastric cancer, or bile duct cancer.

14. The method of claim 13 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer, small intestine cancer, appendix cancer, colorectal cancer, endometrial cancer, pancreatic cancer, skin cancer, gastric cancer, or bile duct cancer.

15. The method of claim 14 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer.

16. The method of claim 14 , wherein the cancer having a KRAS G12C mutation is colorectal cancer.

17. The method of claim 14 , wherein the cancer having a KRAS G12C mutation is pancreatic cancer.

18. The method of claim 14 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer, colorectal cancer, or pancreatic cancer.

19. The method of claim 15 , wherein the compound is administered to an adult.

20. The method of claim 16 , wherein the compound is administered to an adult.

21. The method of claim 17 , wherein the compound is administered to an adult.

22. The method of claim 18 , wherein the compound is administered to an adult.

23. A method of treating cancer having a KRAS G12C mutation in a patient in need thereof, the method comprising administering to the patient a therapeutically effective amount of the compound of claim 2 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer, small intestine cancer, appendix cancer, colorectal cancer, endometrial cancer, pancreatic cancer, liver cancer, small cell lung cancer, cervical cancer, germ cell tumor, ovarian cancer, pancreatic neuroendocrine tumor, bladder cancer, myelodysplastic/myeloproliferative neoplasms, head and neck cancer, esophageal cancer, soft tissue sarcoma, malignant mesothelioma, thyroid cancer, skin cancer, gastric cancer, or bile duct cancer.

24. The method of claim 23 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer, small intestine cancer, appendix cancer, colorectal cancer, endometrial cancer, pancreatic cancer, skin cancer, gastric cancer, or bile duct cancer.

25. The method of claim 24 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer.

26. The method of claim 24 , wherein the cancer having a KRAS G12C mutation is colorectal cancer.

27. The method of claim 24 , wherein the cancer having a KRAS G12C mutation is pancreatic cancer.

28. The method of claim 24 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer, colorectal cancer, or pancreatic cancer.

29. The method of claim 25 , wherein the compound is administered to an adult.

30. The method of claim 26 , wherein the compound is administered to an adult.

31. The method of claim 27 , wherein the compound is administered to an adult.

32. The method of claim 28 , wherein the compound is administered to an adult.

33. A method of treating cancer having a KRAS G12C mutation in a patient in need thereof, the method comprising administering to the patient a therapeutically effective amount of the compound of claim 3 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer, small intestine cancer, appendix cancer, colorectal cancer, endometrial cancer, pancreatic cancer, liver cancer, small cell lung cancer, cervical cancer, germ cell tumor, ovarian cancer, pancreatic neuroendocrine tumor, bladder cancer, myelodysplastic/myeloproliferative neoplasms, head and neck cancer, esophageal cancer, soft tissue sarcoma, malignant mesothelioma, thyroid cancer, skin cancer, gastric cancer, or bile duct cancer.

34. The method of claim 33 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer, small intestine cancer, appendix cancer, colorectal cancer, endometrial cancer, pancreatic cancer, skin cancer, gastric cancer, or bile duct cancer.

35. The method of claim 34 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer.

36. The method of claim 34 , wherein the cancer having a KRAS G12C mutation is colorectal cancer.

37. The method of claim 34 , wherein the cancer having a KRAS G12C mutation is pancreatic cancer.

38. The method of claim 34 , wherein the cancer having a KRAS G12C mutation is non-small cell lung cancer, colorectal cancer, or pancreatic cancer.

39. The method of claim 35 , wherein the compound is administered to an adult.

40. The method of claim 36 , wherein the compound is administered to an adult.

41. The method of claim 37 , wherein the compound is administered to an adult.

42. The method of claim 38 , wherein the compound is administered to an adult.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 15, 2023
From: CHAVEZ, MARY; LOPEZ, PATRICIA; AGARWAL, PRASHANT; AMEGADZIE, ALBERT; AZALI, STEPHANIE; SHIMANOVICH, ROMAN; KELLY, RON C.; REID, DARREN LEONARD
To: AMGEN INC.
Reel/Frame 065563/0394 →
Continuity (4)
Continuation 17553598 · Dec 16, 2021
Continuation 16878824 · May 20, 2020
Provisional Application 62851044 · May 21, 2019
Related Publication 20240067647A1 · Feb 29, 2024
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