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AssigneesAmgen Inc., Cytokinetics, Inc.
InventorsHenry MORRISON, Sheng CUI, Kyle QUASDORF, Evelyn YANEZ, Bin Peter QUAN, Ron C. KELLY, Sebastien CAILLE, Lingyun XIAO, David PEARSON, Jaclyn RAEBURN, Alisa GOLIGHTLY, Bradley MORGAN, Matthew PETERSON, Alex EBERLIN, Alexander OBLEZOV
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Provided herein are free base crystalline forms, crystalline salts, and an amorphous salts of omecamtiv mecarbil.
An omecamtiv mecarbil free base crystalline form Ill, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 9.50, 19.06, and 23.01±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil free base crystalline form IV, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 5.18, 10.35, 14.84, 15.54, 18.10, and 19.92±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil free base crystalline form V, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 7.38, 8.56, 9.14, and 18.28±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil free base crystalline form VI, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 9.07, 16.67, 18.18, 19.70, 20.89, and 21.28±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil free base crystalline form VII, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 8.40, 8.71, 13.08, 15.66, and 19.61±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil ethane sulfonate crystalline salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 8.61, 16.14, 16.76, 16.97, 20.73, 20.96, 25.95, and 26.30±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil bis-fumarate crystalline salt, form A, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 5.64, 15.76, 22.03, and 23.87±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil bis-fumarate crystalline salt, form B, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 5.68, 6.11, 13.13, 18.08, and 22.47±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil bis-fumarate crystalline salt, form C, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 5.88, 18.79, 25.41, and 26.86±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil mono-fumarate crystalline salt, form D, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 8.01, 15.20, and 20.02±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil bis-maleate crystalline salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 9.97, 15.31, 16.04, and 26.96±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil bis-malonate crystalline salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 4.74, 11.37, 14.25, 15.13, 18.29, 20.14, 23.87, 27.78, and 28.01±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil mesylate crystalline salt form A, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 4.02, 4.87, 15.21, 15.86, 20.53, and 24.39±0.2° 2θ using Cu Kα radiation.
The omecamtiv mecarbil of claim 68, further characterized by XRPD pattern peaks at 7.79, 11.61, 16.51, 17.57, 18.42, 19.26, 21.55, 23.17, 25.51, 26.38, and 27.63±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil bis-mesylate crystalline salt form B, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 8.30, 8.94, 9.59, 12.15, 14.37, 19.82, 20.29, 22.04, and 25.02±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil bis-naphthalate-2-sulfonate crystalline salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 4.49, 18.20, 18.62, 21.38, 21.52, and 26.11±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil mono-napadisylate crystalline salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 12.27, 15.75, 16.5, 17.83, 19.94, 21.83, and 22.87±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil nicotinate crystalline salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 3.69, 8.55, 9.13, 16.70, 16.84, 18.30, 19.99, 20.76, 23.43, 24.83, and 25.95±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil oxalate crystalline salt, form A, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 6.48, 13.01, and 23.82±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil oxalate crystalline salt, form B, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 7.38, 13.30, and 16.54±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil salicylate crystalline salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 8.36, 16.75, 17.56, 23.58, and 28.21±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil hemi-succinate crystalline salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 6.32, 18.87, 19.32, 20.5, 21.24, 21.89, 23.49, 24.23, and 26.71±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil bis-sulfate crystalline salt, form A, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 5.39, 7.55, 14.35, 19.26, and 20.22±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil bis-sulfate crystalline salt, form B, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 11.72 and 20.48±0.2° 2θ using Cu Kα radiation.
The omecamtiv mecarbil of claim 109 or 111, having an XRPD pattern substantially as shown in FIG. 58.
An omecamtiv mecarbil bis-sulfate crystalline salt, form C, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 10.98, 11.49, 18.04, and 19.60±0.2° 2θ using Cu Kα radiation.
An omecamtiv mecarbil sulfate crystalline salt, form D, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 7.32, 8.02, and 20.44±0.2° 2θ using Cu Kα radiation.
The omecamtiv mecarbil of claim 117 or 119, having an XRPD pattern substantially as shown in FIG. 62.
An omecamtiv mecarbil 2-hydroxyethane sulfonate crystalline salt, characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 9.95, 17.85, 19.93, 20.07, 20.46, 25.06, and 26.20±0.2° 2θ using Cu Kα radiation.
The omecamtiv mecarbil of claim 120 or 122, having an XRPD pattern substantially as shown in FIG. 65.
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.
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.
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.
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.
An omecamtiv mecarbil amorphous hydrochloride salt.
Dependencies are inferred from the claim text.