Granted Patent B2

US 12,612,366 · App. 18/416,741 · Granted Apr 28, 2026

Inventors: Henry Morrison (Thousand Oaks, CA); Sheng Cui (Thousand Oaks, CA); Kyle Quasdorf (Thousand Oaks, CA); Evelyn Yanez (Thousand Oaks, CA); Bin Peter Quan (Thousand Oaks, CA); Ron C. Kelly (Thousand Oaks, CA); Sebastien Caille (Thousand Oaks, CA); Lingyun Xiao (Thousand Oaks, CA)

Assignee: AMGEN INC.

C07D213/75C07B2200/13

Abstract

Claims (21)

1 . An omecamtiv mecarbil tartrate crystalline salt form which is any one of the following forms:

i) an omecamtiv mecarbil bis-tartrate crystalline salt form A, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 4.20, 7.49, 8.22, 11.88, 16.42, and 21.19±0.2° 2θ using Cu Kα radiation;

ii) an omecamtiv mecarbil bis-tartrate crystalline salt form B, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 3.77, 5.69, and 10.07±0.2° 2θ using Cu Kα radiation;

iii) an omecamtiv mecarbil bis-tartrate crystalline salt form C, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 3.57, 6.23, and 15.84±0.2° 2θ using Cu Kα radiation; or

iv) an omecamtiv mecarbil mono-tartrate crystalline salt form D, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 9.77 and 15.40±0.2° 2θ using Cu Kα radiation.

2 . The omecamtiv mecarbil tartrate crystalline salt form of claim 1 , wherein the crystalline salt form is omecamtiv mecarbil bis-tartrate crystalline salt form A, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 4.20, 7.49, 8.22, 11.88, 16.42, and 21.19±0.2° 2θ using Cu Kα radiation.

3 . The omecamtiv mecarbil bis-tartrate crystalline salt form A of claim 2 , further characterized by XRPD pattern peaks at 4.77, 7.67, 8.43, 9.49, 13.05, 13.26, 14.98, 15.14, 17.34, 17.47, 18.02, 18.23, 18.72, 19.20, 22.50, 24.53, 25.67, 26.30, and 28.14±0.2° 2θ using Cu Kα radiation.

4 . The omecamtiv mecarbil bis-tartrate crystalline salt form A of claim 2 , having an XRPD pattern substantially as shown in FIG. 67 .

5 . The omecamtiv mecarbil bis-tartrate crystalline salt form A of claim 2 , having a thermogravimetric analysis (TGA) as shown in FIG. 68 .

6 . The omecamtiv mecarbil tartrate crystalline salt form of claim 1 , wherein the crystalline salt form is omecamtiv mecarbil bis-tartrate crystalline salt form B, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 3.77, 5.69, and 10.07±0.2° 2θ using Cu Kα radiation.

7 . The omecamtiv mecarbil bis-tartrate crystalline salt form B of claim 6 , further characterized by XRPD pattern peaks at 4.72, 6.95, 9.34, 11.18, 12.63, 15.18, 17.69, 22.35, and 25.46±0.2° 2θ using Cu Kα radiation.

8 . The omecamtiv mecarbil bis-tartrate crystalline salt form B of claim 6 , having an XRPD pattern substantially as shown in FIG. 69 .

9 . The omecamtiv mecarbil bis-tartrate crystalline salt form B of claim 6 , having a thermogravimetric analysis (TGA) as shown in FIG. 70 .

10 . The omecamtiv mecarbil tartrate crystalline salt form of claim 1 , wherein the crystalline salt form is omecamtiv mecarbil bis-tartrate crystalline salt form C, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 3.57, 6.23, and 15.84±0.2° 2θ using Cu Kα radiation.

11 . The omecamtiv mecarbil bis-tartrate crystalline salt form C of claim 10 , further characterized by XRPD pattern peaks at 3.86, 4.78, 7.04, 9.36, 13.08, 13.96, 16.88, 17.60, 18.20, 18.73, 20.40, 22.58, 25.44, 26.06, and 28.61±0.2° 2θ using Cu Kα radiation.

12 . The omecamtiv mecarbil bis-tartrate crystalline salt form C of claim 10 , having an XRPD pattern substantially as shown in FIG. 71 .

13 . The omecamtiv mecarbil bis-tartrate crystalline salt form C of claim 10 , having a thermogravimetric analysis (TGA) as substantially shown in FIG. 72 .

14 . The omecamtiv mecarbil tartrate crystalline salt form of claim 1 , wherein the crystalline salt form is omecamtiv mecarbil mono-tartrate crystalline salt form D, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 9.77 and 15.40±0.2° 2θ using Cu Kα radiation.

15 . The omecamtiv mecarbil mono-tartrate crystalline salt form D of claim 14 , further characterized by XRPD pattern peaks at 10.87, 13.79, 17.36, 17.74, 18.58, 18.87, 21.78, 25.43, and 26.24±0.2° 2θ using Cu Kα radiation.

16 . The omecamtiv mecarbil mono-tartrate crystalline salt form D of claim 14 , having an XRPD pattern substantially as shown in FIG. 73 .

17 . The omecamtiv mecarbil mono-tartrate crystalline salt form D of claim 14 , having a thermogravimetric analysis (TGA) as shown in FIG. 74 .

Assignments (1)

Continuity (4)

References Cited (118)