Granted Patent B2

US 12,275,704 · App. 18/531,424 · Granted Apr 15, 2025

Inventors: Mingda Bi (Simi Valley, CA); Robert Kuehl (San Francisco, CA)

Assignee: CYTOKINETICS, INC.

C07D213/75A61K9/2013A61K9/2018A61K9/2054A61K31/496A61K47/38

Abstract

Claims (22)

1. A pharmaceutical formulation comprising:

omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof;

a control release agent comprising hydroxypropylmethylcellulose;

a pH modifying agent comprising fumaric acid;

a filler; and

a lubricant.

2. The pharmaceutical formulation of claim 1 , wherein the omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof is crystalline.

3. The pharmaceutical formulation of claim 2 , wherein the omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof has an x-ray powder diffraction pattern (XRPD) comprising peaks at 6.6±0.2, 14.9±0.2, 20.1±0.2, 21.4±0.2, and 26.8±0.2° 2θ using Cu Kα radiation.

4. The pharmaceutical formulation of claim 3 , wherein the XRPD pattern further comprises peaks at 8.4±0.2, 24.2±0.2, 26.0±0.2, and 33.3±0.2° 2θ using Cu Kα radiation.

5. The pharmaceutical formulation of claim 2 , wherein the omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof has an x-ray powder diffraction pattern (XRPD) comprising peaks at 6.6±0.2, 8.4±0.2, 14.9±0.2, 15.4±0.2, and 26.8±0.2° 2θ using Cu Kα radiation.

6. The pharmaceutical formulation of claim 5 , wherein the XRPD pattern further comprises peaks at 16.3±0.2, 19.5±0.2, 21.8±0.2, 22.8±0.2, 27.7±0.2, and 28.4±0.2° 2θ using Cu Kα radiation.

7. The pharmaceutical formulation of claim 2 , wherein the omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof has an x-ray powder diffraction pattern (XRPD) comprising peaks at 6.6±0.2, 14.9±0.2, 16.3±0.2, 19.5±0.2, and 26.8±0.2° 2θ using Cu Kα radiation.

8. The pharmaceutical formulation of claim 7 , wherein the XRPD pattern further comprises peaks at 21.8±0.2, 22.8±0.2, 27.7±0.2, and 28.4±0.2° 2θ using Cu Kα radiation.

9. The pharmaceutical formulation of claim 1 , comprising 3-30% w/w omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof.

10. The pharmaceutical formulation of claim 9 , comprising 12-25% w/w omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof.

11. The pharmaceutical formulation of claim 9 , comprising 3-10% w/w omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof.

12. The pharmaceutical formulation of claim 11 , comprising 5-7% w/w omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof.

13. The pharmaceutical formulation of claim 1 , comprising 15-35% w/w control release agent.

14. The pharmaceutical formulation of claim 1 , comprising 4-11% w/w fumaric acid.

15. The pharmaceutical formulation of claim 1 , comprising 12-25% w/w fumaric acid.

16. The pharmaceutical formulation of claim 1 , comprising a weight ratio of fumaric acid to omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate thereof of less than 2:1 to 1:1.

17. The pharmaceutical formulation of claim 16 , wherein the weight ratio of fumaric acid to omecamtiv mecarbil dihydrochloride salt or a pharmaceutically acceptable hydrate is about 1:1.

Assignments (3)

Continuity (6)

References Cited (173)

Cited By (2)

US 12,583,821 US 12,612,366