SALTS AND CRYSTALLINE FORMS OF OMECAMTIV MECARBIL
Patent Information
- Application Number
- MX2023013372
- Authority / Receiving Office
- MX · MX
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2018-08-17
- Filing Date
- 2021-02-12
- Publication Date
- 2026-02-25
- Estimated Expiration
- 2039-08-16
AI Technical Summary
There is a need for various new salts and crystalline forms of omecamtiv mecarbil with different chemical and physical stabilities, as well as formulations and uses thereof, to address the limitations of current cardiac muscle myosin activators that do not increase intracellular calcium concentration, thereby avoiding potentially fatal side effects.
The development of salts and crystalline forms of omecamtiv mecarbil, including free base and crystalline salts, such as hydrochloride, bis-fumarate, and oxalate forms, which are characterized by specific X-ray powder diffraction patterns, differential scanning calorimetry, and thermogravimetric analysis to ensure stability and efficacy.
These forms provide enhanced chemical and physical stability, enabling effective treatment of heart failure by prolonging systolic ejection time and improving cardiac muscle contractility without increasing intracellular calcium concentration, thus reducing side effects.
Abstract
Description
SALTS AND CRYSTALLINE FORMS OF OMECAMTIV MECARBIL TECHNICAL FIELD OF THE INVENTION This disclosure relates to salts and crystalline forms of omecamtiv mecarbil, to pharmaceutical compositions thereof and to methods of use thereof. BACKGROUND The cardiac sarcomere is the basic unit of muscle contraction in the heart. It is a highly organized cytoskeletal structure composed of actin, cardiac muscle myosin, and a set of regulatory proteins. The discovery and development of small-molecule cardiac muscle myosin activators will lead to promising treatments for acute and chronic heart failure, dilated cardiomyopathy (DCM), and conditions associated with left and / or right ventricular systolic dysfunction or systolic reserve. Cardiac muscle myosin is the cytoskeletal motor protein in the cardiac muscle cell. It is directly responsible for converting chemical energy into mechanical force, resulting in cardiac muscle contraction. Current positive inotropic agents, such as beta-adrenergic receptor agonists or phosphodiesterase inhibitors, increase intracellular calcium concentration, thereby increasing cardiac sarcomere contractility. However, increased calcium levels increase the rate of cardiac muscle contraction and shorten systolic ejection time, which has been associated with potentially fatal side effects. In contrast, cardiac muscle myosin activators work by directly stimulating the activity of the cardiac muscle myosin motor protein without increasing intracellular calcium concentration. They accelerate the rate-limiting step of the myosin enzyme cycle, shifting it toward the force-producing state.Instead of increasing the speed of cardiac contraction, this mechanism, on the contrary, prolongs the systolic ejection time, resulting in a possibly more efficient use of oxygen by the heart muscle and cardiac output. Omecamtiv mecarbil is the first of the direct class activators of cardiac myosin, the motor protein that triggers heart contraction. It is being evaluated as a potential treatment for heart failure in both intravenous and oral formulations with the aim of establishing a new spectrum of patient care in both hospital and outpatient settings. Omecamtiv mecarbil has a structure of j co in / cznz / e / YiAi (see, e.g., US Patent n.s7 507 > cu K cr\ G c GG > N 735) and, as an alternative, it has been named methyl 4-(2-fluoro-3-(3-(6-methylpyridine-3-yl)ureido)benzyl)piperazin-1-carboxylate, AMG 423 and CK 1827452. There is a need for various new salts and crystalline forms of omecamtiv mecarbil with different chemical and physical stabilities, and for formulations and uses of these. SUMMARY The present provides salts and crystalline forms of omecamtiv mecarbil, including free-base crystalline forms, crystalline salts, and amorphous salt forms of omecamtiv mecarbil. In some embodiments, the free-base crystalline form III of omecamtiv mecarbil is provided. In some embodiments, the free-base crystalline form IV of omecamtiv mecarbil is provided. In some embodiments, the free-base crystalline form V of omecamtiv mecarbil is provided. In some embodiments, the free-base crystalline form VI of omecamtiv mecarbil is provided. In some embodiments, the free-base crystalline form VII of omecamtiv mecarbil is provided. In some embodiments, the amorphous hydrochloride salt of omecamtiv mecarbil is provided. In some embodiments, the ethanesulfonate crystalline salt of omecamtiv mecarbil is provided.In some embodiments, including the present one, form A of the omecamtiv mecarbil bis-fumarate crystalline salt is provided. In some embodiments, including the present one, form B of the omecamtiv mecarbil bis-fumarate crystalline salt is provided. In some embodiments, including the present one, form C of the omecamtiv mecarbil bis-fumarate crystalline salt is provided. In some embodiments, including the present one, form D of the omecamtiv mecarbil mono-fumarate crystalline salt is provided. In some embodiments, including the present one, the omecamtiv mecarbil bis-maleate crystalline salt is provided. In some embodiments, including the present one, the omecamtiv mecarbil bis-malonate crystalline salt is provided. In some embodiments, including the present one, form A of the omecamtiv mecarbil mesylate crystalline salt is provided. In some embodiments, including the present one, form B of the crystalline salt bis-mesylate of omecamtiv mecarbil is provided.In some embodiments, including the present one, the bis-naphthalate-2-sulfonate crystalline salt of omecamtiv mecarbil is provided. In some embodiments, including the present one, the mono-napadisylate crystalline salt of omecamtiv mecarbil is provided. In some embodiments, including the present one, the nicotinate crystalline salt of omecamtiv mecarbil is provided. In some embodiments, including the present one, form A of the oxalate crystalline salt of omecamtiv mecarbil is provided. In some embodiments, including the present one, form B of the oxalate crystalline salt of omecamtiv mecarbil is provided. In some embodiments, including the present one, the salicylate crystalline salt of omecamtiv mecarbil is provided. In some embodiments, including the present one, the hemisuccinate crystalline salt of omecamtiv mecarbil is provided. In some embodiments, including the present one, form A of the crystalline salt bis-sulfate of omecamtiv mecarbil is provided.In some embodiments, including the present one, form B of the omecamtiv mecarbil bis-sulfate crystalline salt is provided. In some embodiments, including the present one, form C of the omecamtiv mecarbil bis-sulfate crystalline salt is provided. In some embodiments, including the present one, form D of the omecamtiv mecarbil sulfate crystalline salt is provided. In some embodiments, including the present one, the 2-hydroxyethane-sulfonate crystalline salt of omecamtiv mecarbil is provided. In some embodiments, including the present one, form A of the omecamtiv mecarbil bis-tartrate crystalline salt is provided. In some embodiments, including the present one, form B of the omecamtiv mecarbil bis-tartrate crystalline salt is provided. In some embodiments, including the present one, form C of the omecamtiv mecarbil bis-tartrate crystalline salt is provided. In some embodiments, including the present one, the D form of the crystalline salt mono-tartrate of omecamtiv mecarbil is provided. Pharmaceutical compositions comprising a salt or crystalline form of omecamtiv mecarbil as described herein and a pharmaceutically acceptable excipient are also provided. Methods of treating heart failure in a subject in need are further provided, comprising administering to the subject a salt or crystalline form of omecamtiv mecarbil as described herein in an amount effective to treat heart failure. BRIEF DESCRIPTION OF THE FIGURES Figure 1 represents an X-ray powder diffraction (XRPD) pattern of the free-base crystal form III. Figure 2 represents a differential scanning calorimetry (DSC) thermograph of the free-base crystalline form III. Figure 3 represents a trace of thermogravimetric analysis (TGA) of the free-base crystalline form III. Figure 4 represents an XRPD pattern of the freebase crystal form IV. Figure 5 represents a DSC thermography of the free-base crystalline form IV. Figure 6 represents a TGA trace of the freebase crystalline form IV. Figure 7 represents an XRPD pattern of the freebase V crystal form. Figure 8 represents a DSC thermograph of the free-base V crystalline form. Figure 9 represents a TGA trace of the free-base V crystal form. cc in / C7n7 / e / YiAi Figure 10 represents an XRPD pattern of the freebase VI crystal form. Figure 11 represents a DSC thermograph of the free-base crystalline form VI. Figure 12 represents an XRPD pattern of the free-base Vil crystal form. Figure 13 represents an overlay of XRPD patterns of the base-free l-VII crystal forms. Figure 14 represents an XRPD pattern of the amorphous hydrochloride salt. Figure 15 represents a DSC thermograph of the amorphous hydrochloride salt indicating a Tv of -149.16 °C. Figure 16 represents a TGA trace of the amorphous hydrochloride salt indicating a weight loss of -7.9% from -26 °C to 160 °C. Figure 17 represents a moisture sorption profile of the amorphous hydrochloride salt indicating a weight gain of -11% at 50% RH and then a weight loss due to crystallization in Form A up to 95% RH. Figure 18 represents an XRPD pattern of the ethane-sulfonate crystalline salt. Figure 19 represents a thermogravimetric and differential thermal analysis (TG / DTA) thermograph of the ethane-sulfonate crystalline salt. Figure 20 represents an XRPD pattern of the A form of the bisfumarate crystalline salt. Figure 21 represents a TGA trace of form A of the crystalline bis-fumarate salt. Figure 22 represents an XRPD pattern of the B form of the bisfumarate crystalline salt. Figure 23 represents a TGA trace of form B of the crystalline bis-fumarate salt. Figure 24 represents an XRPD pattern of the C form of the bisfumarate crystalline salt. Figure 25 represents a TGA trace of form C of the crystalline bis-fumarate salt. Figure 26 represents an XRPD pattern of the D form of the monofumarate crystalline salt. Figure 27 represents a DSC thermography of the D form of the monofumarate crystalline salt. Figure 28 represents a TGA trace of the d form of the monofumarate crystalline salt. Figure 29 represents an overlap of XRPD patterns of the AD fumarate crystalline salts. z ¡ cc in / C7n7 / e / YiAi Figure 30 represents an XRPD pattern of the bis-maleate crystalline salt. Figure 31 represents a DSC thermography of the bis-maleate crystalline salt. Figure 32 represents a TGA trace of the crystalline bis-maleate salt. Figure 33 represents an XRPD pattern of the bis-malonate crystalline salt. Figure 34 represents a TGA trace of the bis-malonate crystalline salt. Figure 35 represents an XRPD pattern of form A of the mesylate crystalline salt. Figure 36 represents a TGA trace of form A of the mesylate crystalline salt. Figure 37 represents an XRPD of the B form of the bis-mesylate crystalline salt. Figure 38 represents a thermogravimetric and differential thermal (TG / DTA) analysis of form B of the bis-mesylate crystalline salt. Figure 39 represents an overlay of XRPD patterns of forms A and B of the mesylate crystalline salt. Figure 40 represents an XRPD pattern of the bis-naphthalate-2-sulfonate crystalline salt. Figure 41 represents a TG / DTA of the bis-naphthalate-2-sulfonate crystalline salt. Figure 42 represents an XRPD pattern of the mono-napadisylate crystalline salt. Figure 43 represents a DSC thermography of the mono-napadisylate crystalline salt. Figure 44 represents a TGA trace of the mono-napadisylate crystalline salt. Figure 45 represents an XRPD pattern of the nicotinate crystalline salt. Figure 46 represents a TG / DTA of the crystalline salt nicotinate. Figure 47 represents an XRPD pattern of form A of the oxalate crystalline salt. Figure 48 represents a DSC thermography of form A of the crystalline salt oxalate. Figure 49 represents a TGA trace of form A of the crystalline salt oxalate. Figure 50 represents an XRPD pattern of the B form of the oxalate crystalline salt. Figure 51 represents a TGA trace of the B form of the oxalate crystalline salt. Figure 52 represents an XRPD superposition of forms A and B of the oxalate crystalline salt. Figure 53 represents an XRPD pattern of the salicylate crystalline salt. Figure 54 represents a TG / DTA of the crystalline salt salicylate. Figure 55 represents superimposed XRPD patterns of the hemisuccinate crystalline salts. Figure 56 represents a DSC thermograph of the crystalline salt hemisuccinate. Figure 57 represents an XRPD pattern of the A form of the bis-sulfate crystalline salt. Figure 58 represents an XRPD pattern of the B form of the bis-sulfate crystalline salt. Figure 59 represents a TGA trace of the B form of the bis-sulfate crystalline salt. Figure 60 represents an XRPD pattern of the C form of the bis-sulfate crystalline salt. Figure 61 represents a TGA trace of the C form of the bis-sulfate crystalline salt. Figure 62 represents an XRPD pattern of the D form of the bis-sulfate crystalline salt. / co in / cznz / e / YiAi Figure 63 represents a TG / DTA of the D form of the crystalline sulfate salt. Figure 64 represents an overlay of XRPD patterns of the AD forms of the sulfate crystalline salt. Figure 65 represents an XRPD pattern of the crystalline salt 2-hydroxyethane-sulfonate. Figure 66 represents a TG / DTA of the crystalline salt 2-hydroxyethane-sulfonate. Figure 67 represents an XRPD pattern of the A form of the bis-tartrate crystalline salt. Figure 68 represents a TGA trace of the A form of the bis-tartrate crystalline salt. Figure 69 represents an XRPD pattern of the B form of the bis-tartrate crystalline salt. Figure 70 represents a TGA trace of the B form of the bis-tartrate crystalline salt. Figure 71 represents an XRPD pattern of the C form of the bis-tartrate crystalline salt. Figure 72 represents a TGA trace of the C form of the bis-tartrate crystalline salt. Figure 73 represents an XRPD pattern of the D form of the monotartrate crystalline salt. Figure 74 represents a trace of TGA of the D form of the mono-tartrate crystalline salt. Figure 75 represents an overlay of XRPD patterns of the AD forms of the crystalline salt tartrate. DETAILED DESCRIPTION This disclosure provides salts and crystalline forms of omecamtiv mecarbil. The realizations of the free-base crystalline forms, crystalline salts, and amorphous salt of omecamtiv mecarbil can be characterized by one or more of the parameters described in more detail below. Free-base crystalline forms of omecamtiv mecarbil Free-base crystal forms of omecamtiv mecarbil are provided herein. In some embodiments, the free-base crystal forms of omecamtiv mecarbil may be non-ionic forms of omecamtiv mecarbil. In some embodiments, the III-VII free-base crystal forms of omecamtiv mecarbil may be anhydrous. The free-base crystal forms I and II of omecamtiv mecarbil, represented in Figure 13, are prepared and analyzed in detail in Morrison et al., Organic Process Research & Development, 2015, 19, 1842-1848. Free-base crystal form III The free-base crystal form III of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 9.50, 19.06, and 23.01 ± 0.2° 20 using Cu Ka radiation. Optionally, the free-base crystal form III can be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 14.27, 15.25, 16.10, 17.78, and 23.87 ± 0.2° 20 using Cu Ka radiation. The free-base crystal form III z ¡ cc in / C7n7 / e / YiAi can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 7.91, 20.65, 28.11, 31.01, 31.95, and 32.34 ± 0.2° using Cu Ka radiation. The free-base crystal form III can optionally be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 1, which is discussed in the examples.In some embodiments, the free-base crystalline form III has a powder X-ray diffraction pattern substantially as shown in Figure 1, where substantially means that the peaks exhibited can vary by approximately ±0.2°. It is well known in the field of XRPD that, although the relative heights of the peaks in the spectra depend on a number of factors, such as sample preparation and instrument geometry, the positions of the peaks are relatively insensitive to experimental details. Differential scanning calorimetry (DSC) thermographs, as shown in the examples, were obtained for the free-base crystalline form III. The DSC curve indicates an endothermic transition at approximately 186 °C ± 3 °C. Therefore, in some embodiments, the free-base crystalline form III can be characterized by a DSC thermograph exhibiting decomposition endothermy with an onset in the range of approximately 175 °C to approximately 190 °C. For example, in some embodiments, the free-base crystalline form III is characterized by a DSC, as shown in Figure 2. The free-base crystal form III can also be characterized by thermogravimetric analysis (TGA). Thus, the free-base crystal form III can be characterized by a weight loss ranging from approximately 0% to approximately 1% with a starting temperature ranging from approximately 25°C to approximately 100°C. For example, the free-base crystal form III can be characterized by a weight loss of approximately 0% up to approximately 150°C. In some embodiments, the free-base crystal form III has a thermogravimetric analysis substantially like that depicted in Figure 3, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Free-base crystal form IV The free-base crystal form V of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 5.18, 10.35, 14.84, 15.54, 18.10, and 19.92 ± 0.2° 2Θ using Cu Ka radiation. The free-base crystal form IV can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 14.21, 20.62, 20.77, 22.86, 24.05, 24.36, 27.81, and 29.42 ± 0.2° 26 using Cu Ka radiation. The optionally free-base crystalline form IV can be further characterized by a powder X-ray diffraction pattern having additional maxima aj cc in / C7n7 / e / YiAi approximately 7.42, 7.70, 21.70, 22.40, 23.09, 25.20, 25.72, 27.40, 28.18, 28.63, 28.98 and 30.51 ± 0.2° 29 using Cu Ka radiation.The free-base crystal form IV can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 2, which is discussed in the examples. In some embodiments, the free-base crystal form IV has a powder X-ray diffraction pattern substantially as shown in Figure 4, where "substantially" means that the indicated maxima may vary by approximately ±0.2°. Differential scanning calorimetry (DSC) thermographs, as shown in the examples, were obtained for the free-base crystalline form IV. The DSC curve indicates an endothermic transition at approximately 185 °C ± 3 °C. Therefore, in some embodiments, the free-base crystalline form IV can be characterized by a DSC thermograph exhibiting decomposition endothermy with onset in the range of approximately 175 °C to approximately 190 °C. For example, in some embodiments, the free-base crystalline form IV is characterized by a DSC, as shown in Figure 5. The free-base crystalline form IV can also be characterized by thermogravimetric analysis (TGA). Thus, the free-base crystalline form IV can be characterized by a weight loss ranging from approximately 0% to approximately 1% with a starting temperature ranging from approximately 25°C to approximately 100°C. For example, the free-base crystalline form IV can be characterized by a weight loss of approximately 0% up to approximately 150°C. In some embodiments, the free-base crystalline form IV has a thermogravimetric analysis substantially like that depicted in Figure 6, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Free-base V crystal form The free-base V crystal form of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 7.38, 8.56, 9.14, and 18.28 ± 0.2° 29 using Cu Ka radiation. Optionally, the free-base V crystal form can be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 8.93, 10.03, 10.73, 11.71, 13.69, 15.08, 16.85, 17.85, 18.86, 20.05, 20.72, 21.74, 23.56, 24.03, 26.23, and 27.62 ± 0.2° 29 using Cu Ka radiation. The optionally free-base V crystal form can be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 5.40, 16.04, 22.83, 25.45, 26.23, 27.62, 28.58, 29.85, 32.10 and 33.37 ± 0.2° 29 using Cu Ka radiation.The free-ground V crystal form can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 3, which is discussed in the examples. In some embodiments, the free-ground V crystal form has a powder X-ray diffraction pattern substantially as shown in Figure 7, where substantially means that the indicated maxima may vary by approximately ±0.2°. Differential scanning calorimetry (DSC) thermographs, as shown in the examples, were obtained for Form V. The DSC curve indicates an endothermic transition at approximately 185 °C ± 3 °C. Therefore, in some embodiments, the free-base crystalline form V can be characterized by a DSC thermograph that has a decomposition endotherm with an onset in the range of approximately 175 °C to approximately 190 °C. For example, in some embodiments, the free-base crystalline form V is characterized by a DSC, as shown in Figure 8. The free-base V crystal form can also be characterized by thermogravimetric analysis (TGA). Thus, the free-base V crystal form can be characterized by a weight loss ranging from approximately 2% to approximately 6% with a starting temperature ranging from approximately 25°C to approximately 100°C. For example, the free-base V crystal form can be characterized by a weight loss of approximately 4.2% up to approximately 150°C. In some embodiments, the free-base V crystal form has a thermogravimetric analysis substantially like that depicted in Figure 9, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Free-base crystal form VI The free-base VI crystal form of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 9.07, 16.67, 18.18, 19.70, 20.89, and 21.28 ± 0.2° 29 using Cu Ka radiation. The free-base VI crystal form can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 15.88, 17.81, 18.80, 23.72, 24.26, 26.80, 27.59, and 29.82 ± 0.2° 29 using Cu Ka radiation. The free-base VI crystal form can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 14.28, 20.23, 26.19, and 28.90 ± 0.2° using Cu Ka radiation. The free-base VI crystal form can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 4, which is discussed in the examples.In some embodiments, the free-base VI crystal form has a powder X-ray diffraction pattern substantially as shown in Figure 10, where substantially means that the indicated maxima may vary by approximately ± 0.2°. Differential scanning calorimetry (DSC) thermographs were obtained, as shown in the examples, for Form VI. The DSC curve indicates an endothermic transition at approximately 185 °C ± 3 °C. Therefore, in some embodiments, the free-base crystalline form VI can be characterized by a DSC thermograph that has a decomposition endotherm with an onset in the range of approximately 175 °C to approximately 190 °C. For example, in some embodiments, the free-base crystalline form VI is characterized by a DSC, as shown in Figure 11. Free-base vile crystalline form The base-free Vil crystalline form of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 8.40, 8.71, 13.08, 15.66, and 19.61 ± 0.2° 20 using Cu Ka radiation. The base-free Vil crystalline form can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 4.37, 16.83, 18.92, 20.32, 20.49, 22.26, 24.21, and 25.41 ± 0.2° 20 using Cu Ka radiation. The optionally free-base Vil crystalline form can be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 7.84, 10.81, 21.61, 23.22, 23.46, 27.58, 29.53, 30.13 and 31.32 ± 0.2° 20 using Cu Ka radiation.The free-ground Vil crystal form can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 5, which is discussed in the examples. In some embodiments, the free-ground Vil crystal form has a powder X-ray diffraction pattern substantially as shown in Figure 12, where "substantially" means that the indicated maxima may vary by approximately ±0.2°. Crystalline salts of omecamtiv mecarbil The present provides various crystalline salts of omecamtiv mecarbil. Specifically, crystalline salts of omecamtiv mecarbil are provided, wherein the salt is an ethanesulfonate salt, a fumarate salt, a maleate salt, a malonate salt, a mesylate salt, a naphthalate-2-sulfonate salt, a napadisylate salt, a nicotinate salt, an oxalate salt, a salicylate salt, a succinate salt, a sulfate salt, a hydroxyethanesulfonate salt, or a tartrate salt. Crystalline ethanesulfonate salt The ethane-sulfonate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 8.61, 16.14, 16.76, 16.97, 20.73, 20.96, 25.95, and 26.30 ± 0.2° 2Θ using Cu Ka radiation. The ethane-sulfonate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 17.23, 18.35, 19.20, 20.27, 23.73, 25.24, and 27.09 ± 0.2° 2Θ using Cu Ka radiation. The ethane-sulfonate crystalline salt can be characterized by a powder X-ray diffraction pattern ! cc in / C7n7 / e / YiAi that has the maxima shown in Table 7 which is discussed in the examples.In some embodiments, the ethanesulfonate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 18, where substantially means that the indicated maxima may vary by approximately ±0.2°. In some embodiments, the ethanesulfonate crystalline salt has a TG / DTA substantially as shown in Figure 19. Bis-fumarate crystalline salt Form A Form A of the bis-fumarate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 5.64, 15.76, 22.03, and 23.87 ± 0.2° 29 using Cu Ka radiation. Form A of the bis-fumarate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 16.80, 21.55, 21.87, 23.61, 23.87, 26.01, and 27.20 ± 0.2° 29 using Cu Ka radiation. The A form of the bis-fumarate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 10.80, 12.04, 15.76, 16.40, 17.94, 18.32, 19.87, 20.61, 22.88, 27.86, 32.73 and 36.54 ± 0.2° 29 using Cu Ka radiation.Form A of the bis-fumarate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 8, which is discussed in the examples. In some embodiments, form A of the bis-fumarate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 20, where "substantially" means that the indicated maxima may vary by approximately ±0.2°. Bis-fumarate crystalline salt form A can also be characterized by thermogravimetric analysis (TGA). Thus, bis-fumarate crystalline salt form A can be characterized by a weight loss ranging from approximately 6% to approximately 10% with a starting temperature ranging from approximately 25°C to approximately 100°C. For example, bis-fumarate crystalline salt form A can be characterized by a weight loss of approximately 7.9% up to approximately 150°C. In some embodiments, bis-fumarate crystalline salt form A has a thermogravimetric analysis substantially like that depicted in Figure 21, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Bis-fumarate crystalline salt form B The B form of the bis-fumarate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 5.68, 6.11, 13.13, 18.08, and 22.47 ± 0.2° using Cu βα radiation. The B form of the bis-fumarate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 9.69, 11.43, 12.92, 15.95, 20.81, 22.95, 26.04, 27.01, and 28.43 ± 0.2° using Cu βα radiation. The B form of the bis-fumarate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 19.52, 24.53, 31.37, 32.32, 34.89, 35.89 and 37.16 ± 0.2° 29 using Cu Κα radiation.The B form of the bis-fumarate crystalline salt can optionally be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 9, which is discussed in the examples. In some embodiments, the B form of the bis-fumarate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 22, where "substantially" means that the indicated maxima may vary by approximately ±0.2°. The B form of bis-fumarate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Thus, the B form of bis-fumarate crystalline salt can be characterized by a weight loss ranging from approximately 4% to approximately 8% with an onset temperature ranging from approximately 25°C to approximately 100°C. For example, the B form of bis-fumarate crystalline salt can be characterized by a weight loss of approximately 5.6% up to approximately 150°C. In some embodiments, the B form of bis-fumarate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 23, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Bis-fumarate crystalline salt form C The C form of the crystalline salt bis-fumarate of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, having maxima at approximately 5.88, 18.79, 25.41 and 26.86 ± 0.2° 29 using Cu Κα radiation. The C form of the bis-fumarate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 12.74, 13.56, 17.15, 17.63, 20.29, 21.47, 21.77, 22.21, 22.92, 23.58, 24.15, 25.41, 26.78, and 27.83 ± 0.2° using Cu Κα radiation. The C form of the bis-fumarate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 10, which is discussed in the examples.In some embodiments, the C form of the bis-fumarate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 24, where substantially means that the indicated maxima may vary by approximately ± 0.2°. The C form of bis-fumarate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Therefore, the C form of bis-fumarate crystalline salt can be characterized by a weight loss ranging from approximately 6% to approximately 10% with an onset temperature ranging from approximately 25°C to approximately 100°C. For example, the C form of bis-fumarate crystalline salt can be characterized by a weight loss of approximately 8.4% up to approximately 150°C. In some embodiments, the C form of bis-fumarate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 25, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. This weight loss was determined to be water by Karl Fischer (KF) analysis.The KF analysis shows that the water content of the C form of the bis-fumarate crystalline salt can be approximately 8.4%, corresponding to a trihydrate. Form D of the mono-fumarate crystalline salt The D form of the crystalline salt mono-fumarate of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, having maxima at approximately 8.01, 15.20 and 20.02 ± 0.2° 20 using Cu Ka radiation. The D form of the mono-fumarate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 12.11, 12.67, 14.46, 16.01, 16.57, 17.04, 17.63, 20.51, 21.75, 22.86, 24.25, 24.97, 25.84, 26.17, 27.10, 27.97, and 29.21 ± 0.2° using Cu Ka radiation. The D form of the mono-fumarate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 11, which is discussed in the examples.In some embodiments, the D form of the crystalline mono-fumarate salt has a powder X-ray diffraction pattern substantially as shown in Figure 26, where substantially means that the indicated maxima may vary by approximately ± 0.2°. Differential scanning calorimetry (DSC) thermographs, as shown in the examples, were obtained for form D of the mono-fumarate crystalline salt. The DSC curve indicates an endothermic transition at approximately 125 °C ± 3 °C. Therefore, in some embodiments, form D of the mono-fumarate crystalline salt can be characterized by a DSC thermograph exhibiting endothermic decomposition with an onset in the range of approximately 110 °C to approximately 130 °C. For example, in some embodiments, form D of the mono-fumarate crystalline salt is characterized by a DSC, as shown in Figure 27. The D form of the mono-fumarate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Therefore, the D form of the mono-fumarate crystalline salt can be characterized by a weight loss ranging from approximately 5% to approximately 9% with an onset temperature ranging from approximately 25°C to approximately 100°C. For example, the D form of the mono-fumarate crystalline salt can be characterized by a weight loss of approximately 6.7% up to approximately 150°C. In some embodiments, the D form of the mono-fumarate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 28, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. bis-maleate crystalline salt The crystalline salt bis-maleate of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, having maxima at approximately 9.97, 15.31, 16.04 and 26.96 ± 0.2° 2Θ using Cu Ka radiation. The bis-maleate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 10.56, 13.25, 15.53, 16.38, 17.44, 17.70, 18.17, 19.00, 20.13, 21.47, 22.31, 22.44, 24.38, 24.64, 25.66, 26.66 and 27.83 ± 0.2° 20 using Cu Ka radiation. The bis-maleate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 4.99, 14.83, 17.10, 22.02, 28.55, 30.76, 32.01, 34.39 and 34.51 ± 0.2° 20 using Cu Ka radiation.The bis-maleate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 13, which is discussed in the examples. In some embodiments, the bis-maleate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 30, where "substantially" means that the indicated maxima may vary by approximately ±0.2°. Differential scanning calorimetry (DSC) thermographs, as shown in the examples, were obtained for the bis-maleate crystalline salt. The DSC curve indicates an endothermic transition at approximately 190 °C ± 3 °C. Therefore, in some embodiments, the bis-maleate crystalline salt can be characterized by a DSC thermograph exhibiting decomposition endothermy with an onset in the range of approximately 160 °C to approximately 210 °C. For example, in some embodiments, the bis-maleate crystalline salt is characterized by a DSC, as shown in Figure 31. The bis-maleate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Therefore, the bis-maleate crystalline salt can be characterized by a weight loss ranging from approximately 0% to approximately 1% with a starting temperature ranging from approximately 25°C to approximately 150°C. For example, the bis-maleate crystalline salt can be characterized by a weight loss of approximately 0% up to approximately 150°C. In some embodiments, the bis-maleate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 32, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. bis-malonate crystalline salt The bis-malonate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, having maxima at approximately 4.74, 11.37, 14.25, 15.13, 18.29, 20.14, 23.87, 27.78 and 28.01 ± 0.2° 20 using Cu Ka radiation. The bis-malonate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 9.30, 13.73, 16.45, 16.83, 18.08, 18.88, 19.54, 20.77, 21.21, 23.32, 24.67, 26.51, 27.59, and 28.90 ± 0.2° 20 using Cu Ka radiation. The bis-malonate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 15.69, 25.72, 30.18, 33.70, and 34.19 ± 0.2° 20 using Cu Ka radiation.The bis-malonate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 14, which is discussed in the examples. In some embodiments, the bis-malonate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 33, where "substantially" means that the indicated maxima may vary by approximately ±0.2°. Bis-malonate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Thus, bis-malonate crystalline salt can be characterized by a weight loss ranging from approximately 0% to approximately 1% with a starting temperature ranging from approximately 25°C to approximately 140°C. For example, bis-malonate crystalline salt can be characterized by a weight loss of approximately 0% up to approximately 140°C. In some embodiments, bis-malonate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 34, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Form A of the mesylate crystalline salt Form A of the mesylate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 4.02, 4.87, 15.21, 15.86, 20.53, and 24.39 ± 0.2° 20 using Cu Ka radiation. Form A of the mesylate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 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° 20 using Cu Ka radiation. The A form of the mesylate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 15, which is discussed in the examples.In some embodiments, form A of the mesylate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 35, where substantially means that the indicated maxima may vary by approximately ± 0.2°. Form A of the mesylate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Therefore, form A of the mesylate crystalline salt can be characterized by a weight loss ranging from approximately 0% to approximately 2% with a starting temperature ranging from approximately 25°C to approximately 175°C. For example, form A of the mesylate crystalline salt can be characterized by a weight loss of approximately 1.0% up to approximately 200°C. In some embodiments, form A of the mesylate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 36, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Form B of the bis-mesylate crystalline salt The crystalline salt bis-mesylate of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, having maxima at approximately 8.30, 8.94, 9.59, 12.15, 14.37, 19.82, 20.29, 22.04 and 25.02 ± 0.2° 26 using Cu Ka radiation. The B form of the bis-mesylate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 11.66, 16.18, 16.64, 16.81, 17.07, 17.19, 17.41, 17.76, 19.24, 20.66, 21.62, 22.39, 23.95, 24.60, 25.59, 25.89, 27.14, 27.35, 27.41 and 29.45 ± 0.2° 26 using Cu Ka radiation. The B form of the bis-mesylate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 10.78, 11.15, 14.93, 15.36, 15.57, 23.54, 26.14, 26.49, 27.89, 28.86, 29.89, 31.11, 32.47, 33.10, 33.51, 34.56 ± 0.2° 26 using Cu Ka radiation.The B form of the bis-mesylate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 16, which is discussed in the examples. In some embodiments, the B form of the bis-mesylate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 37, where "substantially" means that the indicated maxima may vary by approximately ±0.2°. In some embodiments, the B form of the bis-mesylate crystalline salt has a TG / DTA substantially as shown in Figure 38. Crystalline salt bis-naphthalate-2-sulfonate The bis-naphthalate-2-sulfonate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, having maxima at approximately 4.49, 18.20, 18.62, 21.38, 21.52 and 26.11 ± 0.2° 20 using Cu Ka radiation. The bis-naphthalate-2-sulfonate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 6.25, 6.65, 13.44, 14.39, 14.92, 16.28, 18.90, 19.53, 20.82, 22.02, 22.43, 22.80, 24.40, 25.16, 27.01, 29.67, 31.63, and 33.42 ± 0.2° using Cu Ka radiation. The bis-naphthalate-2-sulfonate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 18, which is discussed in the examples.In some embodiments, the bis-naphthalate-2-sulfonate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 40, where substantially means that the indicated maxima may vary by approximately ±0.2°. In some embodiments, the bis-naphthalate-2-sulfonate crystalline salt has a TG / DTA substantially as shown in Figure 41. Mono-napadisylate crystalline salt The mono-napadisylate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 12.27, 15.75, 16.5, 17.83, 19.94, 21.83, and 22.87 ± 0.2° 20 using Cu Ka radiation. The mono-napadisylate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 13.41, 14.57, 15.14, 18.82, 23.49, 24.34, and 25.26 ± 0.2° 20 using Cu Ka radiation. The crystalline salt mono-napadisylate can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 19, which is discussed in the examples. In some embodiments, the crystalline salt mono-napadisylate has a powder X-ray diffraction pattern substantially as shown in Figure 42, where substantially means that the indicated maxima may vary by approximately ±0.2°. Differential scanning calorimetry (DSC) thermographs were obtained, as shown in the examples, for the mono-napadisylate crystalline salt. The DSC curve indicates an endothermic transition at approximately 100 °C ± 3 °C. Therefore, in some embodiments, the mono-napadisylate crystalline salt can be characterized by a DSC thermograph that exhibits decomposition endothermy with an onset in the range of approximately 80 °C to approximately 115 °C. For example, in some embodiments, the mono-napadisylate crystalline salt is characterized by DSC, as shown in Figure 43. The crystalline salt mono-napadisylate can also be characterized by thermogravimetric analysis (TGA). Therefore, the crystalline salt mono-napadisylate can be characterized by a weight loss in the range of approximately 4% to approximately 8% with a starting temperature in the range of approximately 20 °C to approximately z! cc in / C7n7 / e / YiAi 100 °C. For example, the mono-napadisylate crystalline salt can be characterized by a weight loss of approximately 5.8% up to approximately 100 °C. In some embodiments, the mono-napadisylate crystalline salt has a thermogravimetric analysis substantially like that represented in Figure 44, where substantially means that the presented TGA characteristics may vary by approximately ± 5 °C. Nicotinate crystalline salt The crystalline salt nicotinate of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, which has maxima at approximately 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° 26 using Cu Ka radiation. The crystalline nicotinate salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 7.36, 10.01, 12.43, 14.74, 15.50, 17.62, 18.58, 19.59, 20.34, 21.32, 22.03, 22.91, 23.87, 24.92, 25.40, 26.85, 26.94, 27.32, 28.01, and 28.94 ± 0.2° using Cu Ka radiation. The crystalline nicotinate salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 20, which is discussed in the examples.In some embodiments, the nicotinate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 45, where substantially means that the indicated maxima may vary by approximately ±0.2°. In some embodiments, form D of the nicotinate crystalline salt has a TG / DTA substantially as shown in Figure 46. Form A of the crystalline salt oxalate Form A of the omecamtiv mecarbil oxalate crystalline salt can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 6.48, 13.01, and 23.82 ± 0.2° 26 using Cu Ka radiation. Form A of the oxalate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 10.36, 11.85, 14.79, 15.35, 17.11, 19.23, 19.91, 21.48, 22.07, 22.75, 25.70, 28.55, and 30.71 ± 0.2° 26 using Cu Ka radiation. The A form of the crystalline salt oxalate can be characterized by a powder X-ray diffraction pattern that has the maxima shown in Table 21, which is discussed in the examples.In some embodiments, form A of the crystalline salt oxalate has a powder X-ray diffraction pattern substantially as shown in Figure 47, where substantially means that the indicated maxima may vary by approximately ± 0.2°. Differential scanning calorimetry (DSC) thermographs, as shown in the examples, were obtained for form A of the crystalline salt oxalate. The DSC curve indicates an endothermic transition at approximately 209 °C ± 3 °C. Therefore, in some embodiments, form A of the crystalline salt oxalate can be characterized by a DSC thermograph that has a decomposition endotherm with an onset in the range of approximately 190 °C to approximately 230 °C. For example, in some embodiments, form A of the crystalline salt oxalate is characterized by a DSC, as shown in Figure 48. Form A of the crystalline oxalate salt can also be characterized by thermogravimetric analysis (TGA). Thus, form A of the crystalline oxalate salt can be characterized by a weight loss ranging from approximately 0.5% to approximately 4.5% with a starting temperature ranging from approximately 25°C to approximately 100°C. For example, form A of the crystalline oxalate salt can be characterized by a weight loss of approximately 2.5% up to approximately 150°C. In some embodiments, form A of the crystalline oxalate salt has a thermogravimetric analysis substantially like that depicted in Figure 49, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Form B of the crystalline salt oxalate The B form of the omecamtiv mecarbil oxalate crystalline salt can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 7.38, 13.30, and 16.54 ± 0.2° 29 using Cu Ka radiation. The B form of the oxalate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 17.11, 17.95, 18.45, 21.25, 22.63, 24.82, and 25.77 ± 0.2° 29 using Cu Ka radiation. The B form of the oxalate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 14.76, 24.35, 28.61, 29.58, 30.49, 31.76, 34.46, and 37.35 ± 0.2° using Cu Ka radiation. The B form of the oxalate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 22, which is discussed in the examples.In some embodiments, the B form of the crystalline salt oxalate has a powder X-ray diffraction pattern substantially as shown in Figure 50, where substantially means that the indicated maxima may vary by approximately ± 0.2°. The B form of the crystalline oxalate salt can also be characterized by thermogravimetric analysis (TGA). Therefore, the B form of the crystalline oxalate salt can be characterized by a weight loss ranging from approximately 0% to approximately 1% with a starting temperature ranging from approximately 25°C to approximately 100°C. For example, the B form of the crystalline oxalate salt can be characterized by a weight loss of approximately 0% up to approximately 150°C. In some embodiments, the B form of the crystalline oxalate salt has a thermogravimetric analysis substantially like that depicted in Figure 51, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. crystalline salicylate salt The salicylate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 8.36, 16.75, 17.56, 23.58, and 28.21 ± 0.2° 20 using Cu Ka radiation. The salicylate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 10.08, 11.30, 13.69, 17.77, 17.86, 18.67, 19.11, 20.22, 21.07, 25.23, and 27.40 ± 0.2° 20 using Cu Ka radiation. The salicylate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 9.78, 12.00, 13.80, 15.51, 19.27, 19.62, 20.02, 20.79, 22.19, 22.39, 22.75, 22.92, 24.99, 25.59, 26.79, 29.94 and 34.07 ± 0.2° 20 using Cu Ka radiation.The salicylate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 24, which is discussed in the examples. In some embodiments, the salicylate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 53, where "substantially" means that the indicated maxima may vary by approximately ±0.2°. In some embodiments, the salicylate crystalline salt has a TG / DTA substantially as shown in Figure 54. Crystalline salt hemisuccinate The hemisuccinate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 6.32, 18.87, 19.32, 20.5, 21.24, 21.89, 23.49, 24.23, and 26.71 ± 0.2° 20 using Cu Ka radiation. The hemisuccinate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 12.93, 15.08, 16.97, 25.36, 27.39, and 28.32 ± 0.2° 20 using Cu Ka radiation. The crystalline salt hemisuccinate can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 25, which is discussed in the examples. In some embodiments, the crystalline salt hemisuccinate has a powder X-ray diffraction pattern substantially as shown in Figure 55, where substantially means that the indicated maxima may vary by approximately ±0.2°. Differential scanning calorimetry (DSC) thermographs, as shown in the examples, were obtained for the hemisuccinate crystalline salt. The DSC curve indicates an endothermic transition at approximately 171 °C ± 3 °C. Therefore, in some embodiments, the hemisuccinate crystalline salt can be characterized by a DSC thermograph that has a decomposition endotherm with an onset in the range of approximately 155 °C to approximately 190 °C. For example, in some embodiments, the hemisuccinate crystalline salt is characterized by a DSC, as shown in Figure 56. Form A of the bis-sulfate crystalline salt The A form of the crystalline salt omecamtiv mecarbil bis-sulfate can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, having maxima at approximately 5.39, 7.55, 14.35, 19.26 and 20.22 ± 0.2° 20 using Cu Ka radiation. Form A of the bis-sulfate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 16.17, 16.71, 16.92, 17.07, 18.60, 20.83, 21.38, 22.27, 22.77, 23.14, 23.42, 23.76, 24.32, 25.11, 25.74, 26.46, 27.71, 28.15, and 29.92 ± 0.2° using Cu Ka radiation. Form A of the bis-sulfate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 26, which is discussed in the examples.In some embodiments, form A of the bis-sulfate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 57, where substantially means that the indicated maxima may vary by approximately ± 0.2°. Form B of the bis-sulfate crystalline salt The B form of the bis-sulfate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as described in the examples, having maxima at approximately 11.72 and 20.48 ± 0.2° 20 using Cu Ka radiation. The B form of the bis-sulfate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 12.17, 12.93, 17.79, 18.39, 18.76, 19.84, 23.60, 25.13, 25.63, and 30.12 ± 0.2° 20 using Cu Ka radiation. The B form of the bis-sulfate crystalline salt can be characterized by a powder X-ray diffraction pattern that has the maxima shown in Table 27, which is discussed in the examples.In some embodiments, the B form of the bis-sulfate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 58, where substantially means that the indicated maxima may vary by approximately ± 0.2°. The B form of bis-sulfate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Therefore, the B form of bis-sulfate crystalline salt can be characterized by a weight loss ranging from approximately 10% to approximately 14% with an onset temperature ranging from approximately 25°C to approximately 100°C. For example, the B form of bis-sulfate crystalline salt can be characterized by a weight loss of approximately 12.2% up to approximately 150°C. In some embodiments, the B form of bis-sulfate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 59, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. This weight loss was determined to be water by Karl Fischer (KF) analysis.The KF analysis shows that the water content of form B of the bis-sulfate crystalline salt can be approximately 12%, corresponding to a pentahydrate. Form C of the bis-sulfate crystalline salt The C form of the bis-sulfate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 10.98, 11.49, 18.04, and 19.60 ± 0.2° 20 using Cu Ka radiation. The C form of the bis-sulfate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 10.39, 10.72, 12.52, 12.99, 17.11, 17.43, 20.94, 24.76, 25.25, 25.87, and 26.51 ± 0.2° 20 using Cu Ka radiation. The C form of the bis-sulfate crystalline salt can be characterized by a powder X-ray diffraction pattern that has the maxima shown in Table 28, which is discussed in the examples.In some embodiments, the C form of the bis-sulfate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 60, where substantially means that the indicated maxima may vary by approximately ± 0.2°. The C form of bis-sulfate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Thus, the C form of bis-sulfate crystalline salt can be characterized by a weight loss ranging from approximately 7% to approximately 11% with a starting temperature ranging from approximately 25°C to approximately 60°C. For example, the C form of bis-sulfate crystalline salt can be characterized by a weight loss of approximately 9.0% up to approximately 150°C. In some embodiments, the C form of bis-sulfate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 61, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Form D of the crystalline sulfate salt The D form of the crystalline salt omecamtiv mecarbil sulfate can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, having maxima at approximately 7.32, 8.02 and 20.44 ± 0.2° 20 using Cu Ka radiation. The D form of the crystalline sulfate salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 13.57, 14.54, 16.29, 16.41, 16.91, 17.36, 18.70, 21.02, 21.77, 22.37, 22.90, 23.72, 24.28, 25.14, 25.88, 26.58, 27.25, 28.10, and 29.43 ± 0.2° using Cu Ka radiation. The D form of the crystalline sulfate salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 29, which is discussed in the examples.In some embodiments, the D form of the crystalline sulfate salt has a powder X-ray diffraction pattern substantially as shown in Figure 62, where substantially means that the indicated maxima may vary by approximately ±0.2°. In other embodiments, the D form of the crystalline sulfate salt has a TG / DTA substantially as shown in Figure 63. 2-Hydroxyethane-sulfonate crystalline salt The crystalline salt 2-hydroxyethanesulfonate of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 9.95, 17.85, 19.93, 20.07, 20.46, 25.06, and 26.20 ± 0.2° 29 using Cu Ka radiation. The crystalline salt 2-hydroxyethanesulfonate can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 6.26, 6.69, 14.99, 16.37, 19.61, 20.95, 29.98, 32.16, and 34.39 ± 0.2° 29 using Cu Ka radiation. The crystalline salt 2-hydroxyethane-sulfonate can be characterized by a powder X-ray diffraction pattern that has the maxima shown in Table 31, which is discussed in the examples.In some embodiments, the crystalline salt 2-hydroxyethanesulfonate has a powder X-ray diffraction pattern substantially as shown in Figure 65, where substantially means that the indicated maxima may vary by approximately ±0.2°. In some embodiments, the crystalline salt 2-hydroxyethanesulfonate has a TG / DTA substantially as shown in Figure 66. Form A of the bis-tartrate crystalline salt The A form of the crystalline salt bis-tartrate of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as set out in the examples, having maxima at approximately 4.20, 7.49, 8.22, 11.88, 16.42 and 21.19 ± 0.2° 29 using Cu Ka radiation. Form A of the bis-tartrate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 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° using Cu Ka radiation. Form A of the bis-tartrate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 32, which is discussed in the examples.In some embodiments, form A of the bis-tartrate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 67, where substantially means that the indicated maxima may vary by approximately ± 0.2°. Form A of bis-tartrate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Thus, form A of bis-tartrate crystalline salt can be characterized by a weight loss ranging from approximately 1% to approximately 5% with a starting temperature ranging from approximately 1000°C to approximately 120°C. For example, form A of bis-tartrate crystalline salt can be characterized by a weight loss of approximately 3.2% up to approximately 150°C. In some embodiments, form A of bis-tartrate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 68, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Form B of the bis-tartrate crystalline salt The B form of the bis-tartrate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 3.77, 5.69, and 10.07 ± 0.2° 29 using Cu Ka radiation. The B form of the bis-tartrate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 4.72, 6.95, 9.34, 11.18, 12.63, 15.18, 17.69, 22.35, and 25.46 ± 0.2° 29 using Cu Ka radiation. The B form of the bis-tartrate crystalline salt can be characterized by a powder X-ray diffraction pattern that has the maxima shown in Table 33, which is discussed in the examples.In some embodiments, the B form of the bis-tartrate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 69, where substantially means that the indicated maxima may vary by approximately ± 0.2°. The B form of bis-tartrate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Thus, the B form of bis-tartrate crystalline salt can be characterized by a weight loss ranging from approximately 3% to approximately 7% with a starting temperature ranging from approximately 20°C to approximately 100°C. For example, the B form of bis-tartrate crystalline salt can be characterized by a weight loss of approximately 5.4% up to approximately 150°C. In some embodiments, the B form of bis-tartrate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 70, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Form C of the bis-tartrate crystalline salt The C form of the bis-tartrate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 3.57, 6.23, and 15.84 ± 0.2° using Cu Ka radiation. The C form of the bis-tartrate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 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 [unclear text - likely a typo or ... 28.61 ± 0.2° 2θ using Cu Ka radiation. The C form of the bis-tartrate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 34, which is discussed in the examples. In some embodiments, the C form of the bis-tartrate crystalline salt has a powder X-ray diffraction pattern substantially as shown in Figure 71, where substantially means that the indicated maxima may vary by approximately ± 0.2°. The C form of bis-tartrate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Thus, the C form of bis-tartrate crystalline salt can be characterized by a weight loss ranging from approximately 12% to approximately 17% with an initial temperature ranging from approximately 20°C to approximately 100°C. For example, the C form of bis-tartrate crystalline salt can be characterized by a weight loss of approximately 14.6% up to approximately 150°C. In some embodiments, the C form of bis-tartrate crystalline salt has a thermogravimetric analysis substantially like that depicted in Figure 72, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. Form D of the crystalline salt mono-tartrate The D form of the mono-tartrate crystalline salt of omecamtiv mecarbil can be characterized by a powder X-ray diffraction pattern, obtained as shown in the examples, having maxima at approximately 9.77 and 15.40 ± 0.2° 20 using Cu Ka radiation. The D form of the mono-tartrate crystalline salt can optionally be further characterized by a powder X-ray diffraction pattern having additional maxima at approximately 10.87, 13.79, 17.36, 17.74, 18.58, 18.87, 21.78, 25.43, and 26.24 ± 0.2° 20 using Cu Ka radiation. The D form of the mono-tartrate crystalline salt can be characterized by a powder X-ray diffraction pattern having the maxima shown in Table 35, which is discussed in the examples.In some embodiments, the D form of the crystalline mono-tartrate salt has a powder X-ray diffraction pattern substantially as shown in Figure 73, where substantially means that the indicated maxima may vary by approximately ± 0.2°. The D form of the mono-tartrate crystalline salt can also be characterized by thermogravimetric analysis (TGA). Therefore, the D form of the mono-tartrate crystalline salt can be characterized by a weight loss ranging from approximately 4% to approximately 8% with an initial temperature ranging from approximately 20°C to approximately 75°C. For example, the D form of the mono-tartrate crystalline salt can be characterized by a weight loss of approximately 6.4% up to approximately 150°C. In some embodiments, the D form of the mono-tartrate crystalline salt (cc in / C7n7 / e / YiAi) has a thermogravimetric analysis substantially like that depicted in Figure 74, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. This weight loss was determined to be water by Karl Fischer (KF) analysis.KF analysis shows that the water content of the D form of the crystalline mono-tartrate salt can be approximately 6.9%, corresponding to a dihydrate. Amorphous hydrochloride salt. In the present, an amorphous hydrochloride salt of omecamtiv mecarbil is also provided, and its powder X-ray diffraction pattern as shown in Figure 14 provides confirmation of its amorphous nature. Differential scanning calorimetry (DSC) thermographs, as shown in the examples, were obtained for the amorphous hydrochloride salt. The DSC curve indicates an endothermic transition at approximately 171 °C ± 3 °C. Therefore, in some embodiments, the amorphous hydrochloride salt can be characterized by a DSC thermograph that has a decomposition endotherm with an onset in the range of approximately 155 °C to approximately 190 °C. For example, in some embodiments, the amorphous hydrochloride salt is characterized by a DSC, as shown in Figure 15. Amorphous hydrochloride salt can also be characterized by thermogravimetric analysis (TGA). Thus, amorphous hydrochloride salt can be characterized by a weight loss ranging from approximately 6% to approximately 10% with an initial temperature ranging from approximately 20°C to approximately 60°C. For example, amorphous hydrochloride salt can be characterized by a weight loss of approximately 7.9% up to approximately 150°C. In some embodiments, amorphous hydrochloride salt has a thermogravimetric analysis substantially like that depicted in Figure 16, where "substantially" means that the presented TGA characteristics may vary by approximately ±5°C. In some embodiments, amorphous hydrochloride salt has a moisture sorption profile substantially like that depicted in Figure 17. Pharmaceutical compositions Pharmaceutical compositions comprising a salt or crystalline form of omecamtiv mecarbil described herein are also provided; and a pharmaceutically acceptable excipient. The term "pharmaceutically acceptable" is used herein to refer to those ligands, materials, compositions, and / or pharmaceutical forms that are, to the best of sound medical judgment, suitable for use in contact with human and animal tissues without excessive toxicity, irritation, allergic response, or other problems or complications, and with a correspondingly appropriate benefit-risk ratio. The compositions described herein may be formulated for any route of administration. In several cases, the composition is for oral administration. In several cases, the composition is in tablet form. In some embodiments, pharmaceutical compositions may include a pharmaceutically acceptable vehicle. The term "pharmaceutically acceptable vehicle" as used herein refers to a pharmaceutically acceptable material, composition, or vehicle, such as a filler, diluent, excipient, solvent, or liquid or solid encapsulating material. As used herein, the term "pharmaceutically acceptable vehicle" includes lamps, sterile water for injection, solvents, dispersion media, coatings, antibacterial and antifungal agents, isotonic and absorption-delaying agents, and the like, compatible with pharmaceutical administration. Each vehicle must be acceptable in the sense of being compatible with the other ingredients of the formulation and not harmful to the patient. Examples of materials that may serve as pharmaceutically acceptable vehicles include: (1) sugars, such as lactose,(1) glucose and sucrose; (2) starches, such as maize starch, potato starch, and substituted and unsubstituted β-cyclodextrin; (3) cellulose and its derivatives, such as sodium carboxymethylcellulose, ethylcellulose, and cellulose acetate; (4) tragacanth powder; (5) malt; (6) gelatin; (7) talc; (8) excipients such as cocoa butter and suppository waxes; (9) oils, such as peanut oil, cottonseed oil, safflower oil, sesame oil, olive oil, maize oil, and soybean oil; (10) glycols, such as propylene glycol; (11) polyols, such as glycerin, sorbitol, mannitol, and polyethylene glycol; (12) esters, such as ethyl oleate and ethyl laurate; (13) agar; (14) buffering agents,such as magnesium hydroxide and aluminum hydroxide; (15) alginic acid; (16) pyrogen-free water; (17) isotonic saline solution; (18) Ringer's solution; (19) ethyl alcohol; (20) phosphate buffer solutions; and (21) other compatible non-toxic substances used in pharmaceutical formulations. In certain embodiments, the pharmaceutical compositions provided herein are non-pyrogenic, i.e., they do not induce significant temperature elevations when administered to a patient. They may also be present in the compositions as excipients, wetting agents, emulsifiers and lubricants, such as sodium lauryl sulfate and magnesium stearate, as well as coloring agents, release agents, coating agents, sweetening agents, flavorings and perfumes, preservatives and antioxidants. Examples of pharmaceutically acceptable antioxidants as excipients include: (1) water-soluble antioxidants such as ascorbic acid, cysteine hydrochloride, sodium bisulfate, sodium metabisulfite, sodium sulfite, and the like; (2) oil-soluble antioxidants such as ascorbyl palmitate, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), lecithin, propyl gallate, alpha-tocopherol, and the like; and (3) metal chelating agents such as citric acid, ethylenediaminetetraacetic acid (EDTA), sorbitol, tartaric acid, phosphoric acid, and the like. This pharmaceutical composition may also contain adjuvants such as preservatives, wetting agents, emulsifying agents, and dispersing agents. The prevention of microbial activity can be ensured by the inclusion of various antibacterial and antifungal agents, for example, parabens, chlorobutanol, phenol, sorbic acid, and similar substances. It may also be desirable to include agents that adjust the dosage, such as sugars and similar components, in the composition. Furthermore, prolonged absorption of the injectable dosage form can be achieved by including absorption-delaying agents such as aluminum monostearate and gelatin. In some cases, to prolong the effect of one or more compounds provided herein, it is desirable to slow the absorption of the compound by subcutaneous or intramuscular injection. For example, delayed absorption of a compound administered parenterally can be achieved by dissolving or suspending the compound in an oily vehicle. The composition must be stable under manufacturing and storage conditions and protected from contamination by microorganisms such as bacteria and fungi. Prevention of microbial activity can be achieved through the inclusion of various antibacterial and antifungal agents, such as parabens, chlorobutanol, phenol, sorbic acid, thimerosal, and similar substances. In many cases, it is preferable to include isotonic agents, such as sugars, polyalcohols like mannitol and sorbitol, and sodium chloride, in the composition. Prolonged absorption of injectable compositions can be achieved by including an absorption-delaying agent, such as aluminum monostearate and gelatin. Sterile injectable solutions can be prepared by incorporating the required amount of the active ingredient into an appropriate solvent with one or a combination of the ingredients listed above, as needed, followed by sterilization by filtration. Dispersions are generally prepared by incorporating the active ingredient into a sterile vehicle containing a basic dispersion medium and the other required ingredients mentioned above. For sterile powders used in the preparation of sterile injectable solutions, the preparation method is cryopreservation (lyophilization), which produces a powder of the active ingredient plus any desired additional ingredients from a solution previously filtered under sterile conditions. / co in / C7n7 / e / YiAi Injectable depot formulations can be prepared by forming microencapsulation or nanoencapsulation matrices of a pre-existing compound within biodegradable polymers such as polylactide-polyglycolide. Depending on the drug-to-polymer ratio and the specific polymer used, the drug release rate can be controlled. Examples of other biodegradable polymers include poly(orthoesters) and poly(anhydrides). Injectable depot formulations are also prepared by encapsulating the drug in liposomes, microemulsions, or nanoemulsions, which are compatible with body tissue. In one embodiment, therapeutic crystalline salts are prepared with vehicles that will protect the therapeutic compounds from rapid elimination from the body, such as a controlled-release formulation, including implants and microencapsulated delivery systems. Biodegradable and biocompatible polymers, such as ethylene vinyl acetate, polyanhydrides, polyglycolic acid, collagen, polyorthoesters, and polylactic acid, may be used. Such formulations may be prepared using conventional techniques or may be obtained commercially, for example, from Alza Corporation and Nova Pharmaceuticals, Inc. Liposomal suspensions (including liposomes targeting selected cells with monoclonal antibodies against cellular antigens) may also be used as pharmaceutically acceptable vehicles. These may be prepared according to methods known to those skilled in the art, for example, as described in U.S. Patent No.24 522 811, which is incorporated herein by reference in its entirety. Pharmaceutical compositions may be included in a container, package, or dispenser along with administration instructions. Controlled-release compositions In several cases, the pharmaceutical formulations described herein are capable of uniformly releasing omecamtiv mecarbil at a rate controlled by diffusion of omecamtiv mecarbil through a gel layer formed by the hydration of the controlled-release agents in the tablets. In some embodiments, along with other prior or subsequent embodiments, the present modified-matrix tablets demonstrate minimal pH-dependent release in vitro. In some embodiments, along with other prior or subsequent embodiments, complete release of omecamtiv mecarbil is achieved in dissolution media at pH 2 and 6.8 within 24 hours, potentially resulting in less variability and a reduced dietary effect between and within individuals.The present modified-release matrix tablet formulation is found to be superior to the previous immediate-release formulation in minimizing the peak-to-trough ratio in plasma. As a result, the present modified-release matrix tablets reduce plasma concentration fluctuations, leading to fewer side effects and improved safety and efficacy. It is also expected that the present modified-release matrix tablets will improve patient adherence to treatment by reducing dosing frequency. Furthermore, the present modified-release matrix tablets are physicochemically stable, exhibiting no changes in physical attributes, assays, impurities, or dissolution profiles after storage at 40°C / 75% RH for 6 months. Pharmaceutical formulations comprising the crystalline salt or omecamtiv mecarbil as disclosed herein; a controlled-release agent; a pH-modifying agent; a filler; and a lubricant are provided. As used herein, the term controlled-release agents refers to agents that facilitate the controlled release of the active ingredient of this composition. In some embodiments, in conjunction with other prior or subsequent embodiments, the controlled-release agents form a gel upon hydration. Controlled-release agents include pullulan, dextrin, sodium and calcium acid, polyacrylic acid, polymethacrylic acid, polymethylvinyl ether-co-maleic anhydride, polyvinylpyrrolidone, polyethylene oxide, polyethylene glycol, hydroxypropylcellulose, hydroxypropylmethylcellulose, hydroxyethylcellulose, hydroxymethyl methacrylate, sodium carboxymethylcellulose, calcium carboxymethylcellulose, methylcellulose, maltodextrin, xanthan gum, tragacanth gum, agar, gellan gum, kayara gum, alginic acids, pectins, pregelatinized starch, polyvinyl alcohol, carboxymethyl ethylcellulose, cellulose acetate phthalate,cellulose acetate succinate, methylcellulose phthalate, hydroxymethylethylcellulose phthalate, hydroxypropylmethylcellulose phthalate, hydroxypropylmethylcellulose acetate succinate, polyvinyl alcohol phthalate, polyvinyl butylate phthalate, polyvinyl acetate phthalate, a vinyl acetate / maleic anhydride copolymer, a styrene / maleic acid monoester copolymer, a methyl acrylate / methacrylic acid copolymer, a styrene / acrylic acid copolymer, a methyl acrylate / methacrylic acid / octyl acrylate copolymer, a methacrylic acid / methyl methacrylate copolymer, benzylaminomethylcellulose, diethylaminomethylcellulose, piperidylethylhydroxyethylcellulose, dimethylaminoacetate, cellulose acetate copolymer vinyl / vinyl acetate, vinyl benzylamine / vinyl acetate copolymer, polyvinyl acetaldiethylamino acetate, vinylpiperidylacetoacetal / vinyl acetate copolymer, polydiethylaminomethylstyrene,a copolymer of methyl methacrylate / butyl methacrylate / dimethylaminoethyl methacrylate and polydimethylaminoethyl methacrylate, a copolymer of 2-methyl-5-vinylpyridine / methyl methacrylate / methacrylic acid, a copolymer of 2-methyl-5-vinylpyridine / methyl acrylate / methacrylic acid, a copolymer of 2-vinyl-5-ethylpyridine / methacrylic acid / methyl acrylate, a copolymer of 2-vinylpyridine / methacrylic acid / acrylonitrile, carboxymethylpiperidyl starch, carboxymethylbenzylaminocellulose, a copolymer of vinylglycine / styrene, chitosan, poly(vinyl alcohol), maleic anhydride copolymer, polyvinylpyrrolidone), starch and starch-based polymers, poly(2-ethyl-2-oxazoline), / co in / C7n7 / e / YiAi poly(ethyleneimine), polyurethane hydrogels, Welan gum, Rhamsan gum, polyvinyl acetates, ethylcellulose, Eudragit RL, RS, NE 30D, Kollicoat EMM 30D or combinations thereof. In some embodiments, along with other earlier or later embodiments, the controlled-release agent is a polymer. In some embodiments, along with other prior or subsequent embodiments, the control release agent is selected from pullulan, dextrin, sodium and calcium acid, polyacrylic acid, polymethacrylic acid, polymethylvinyl ether-co-maleic anhydride, polyvinylpyrrolidone, polyethylene oxide, polyethylene glycol, hydroxypropylcellulose, hydroxypropylmethylcellulose, hydroxyethylcellulose, hydroxymethyl methacrylate, sodium carboxymethylcellulose, calcium carboxymethylcellulose, methylcellulose, maltodextrin, xanthan gum, tragacanth gum, agar, gellan gum, kayara gum, alginic acids, pectins, pregelatinized starch, polyvinyl alcohol, carboxymethyl ethylcellulose, cellulose acetate phthalate, cellulose acetate succinate, methylcellulose phthalate, hydroxymethylethylcellulose phthalate, hydroxypropyl methylcellulose phthalate, acetate succinate of hydroxypropyl methylcellulose, polyvinyl alcohol phthalate, polyvinyl butylate phthalate,polyvinyl acetate phthalate, a vinyl acetate / maleic anhydride copolymer, a styrene / maleic acid monoester copolymer, a methyl acrylate / methacrylic acid copolymer, a styrene / acrylic acid copolymer, a methyl acrylate / methacrylic acid / octyl acrylate copolymer, a methacrylic acid / methyl methacrylate copolymer, benzylaminomethylcellulose, diethylaminomethylcellulose, piperidylethylhydroxyethylcellulose, dimethylaminoacetate, a diethylvinyl acetate / vinyl acetate copolymer, a benzylamine vinyl acetate / vinyl acetate copolymer, acetaldiethylaminopolyvinyl acetate, a vinylpiperidylacetalacetal / vinyl acetate copolymer, polydiethylaminomethylstyrene, a methyl methacrylate / methacrylate copolymer butyl / dimethylaminoethyl methacrylate and polydimethylaminoethyl methacrylate, a copolymer of 2-methyl-5-vinylpyridine / methyl methacrylate / methacrylic acid,a copolymer of 2-methyl-5-vinylpyridine / methyl acrylate / methacrylic acid, a copolymer of 2-vinyl-5-ethylpyridine / methacrylic acid / methyl acrylate, a copolymer of 2-vinylpyridine / methacrylic acid / acrylonitrile, carboxymethylpiperidyl starch, carboxymethylbenzylaminocellulose, a copolymer of vinylglycine / styrene, chitosan, poly(vinyl alcohol), maleic anhydride copolymer, poly(vinylpyrrolidone), starch and starch-based polymers, poly(2-ethyl-2-oxazoline), poly(ethyleneimine), polyurethane hydrogels, Welan gum, Rhamsan gum, polyvinyl acetates, ethylcellulose, Eudragit RL, RS, NE 30D and Kollicoat EMM 30D or any combination thereof. / co in / C7n7 / e / YiAi As used herein, the term “pH modifying agent” refers to an agent capable of modulating pH within a desired range. In some embodiments, in conjunction with other prior or subsequent embodiments, the pH modifying agent is an acidifying agent. In some embodiments, in conjunction with other prior or subsequent embodiments, the pH modifying agent is present in a sufficient amount to lower the pH. pH modifying agents include maleic acid, citric acid, tartaric acid, pamoic acid, fumaric acid, salicylic acid, 2,6-diaminohexanoic acid, camphorsulfonic acid, glycerophosphoric acid, 2-hydroxyethanesulfonic acid, isethionic acid, succinic acid, carbonic acid, p-toluenesulfonic acid, aspartic acid, 8-chlorotheophylline, benzenesulfonic acid, melic acid, orotic acid, oxalic acid, benzoic acid, 2-naphthalenesulfonic acid, stearic acid, adipic acid, and other acids. p-aminosalicylic acid,5-Aminosalicylic acid, ascorbic acid, sulfuric acid, cyclamic acid, sodium lauryl sulfate, glucoheptonic acid, glucuronic acid, glycine, sulfuric acid, mandelic acid, 1,5-naphthalenedisulfonic acid, nicotinic acid, oleic acid, 2-oxoglutaric acid, pyridoxal-5-phosphate, undecanoic acid, p-acetamidobenzoic acid, o-acetamidobenzoic acid, m-acetamidobenzoic acid, N-acetyl-L-aspartic acid, camphoric acid, dehydrocholic acid, malonic acid, edetic acid, ethylenediainetetraacetic acid, ethylsulfuric acid, hydroxyphenylbenzoylbenzoic acid, glutamic acid, glycyrrhizic acid, 4-hexylresorcinol, hippuric acid, p-phenolsulfonic acid, 4-hydroxybenzoic acid 3-hydroxybenzoic acid, 3-hydroxy-2-naphthoic acid, 1-hydroxy-2-naphthoic acid, lactobionic acid, 3'-adenylic acid, 5'-adenylic acid, mucic acid, galactaric acid, pantothenic acid, pectic acid, polygalacturonic acid, 5-sulfosalicylic acid, 1,2,3,6-tetrahydro-1,3-dimethyl-2-6-dioxopurine-7-propanesulfonic acid, terephthalic acid, 1-hydroxy-2-naphthoic acid, and combinations thereof. In some embodiments, along with other prior or subsequent embodiments, the pH-modifying agents include, for example, maleic acid, citric acid, malic acid, fumaric acid, sulfuric acid, tartaric acid, lactoic acid, salicylic acid, aspartic acid, aminosalicylic acid, malonic acid, glutamic acid, and combinations thereof. In some embodiments, along with other prior or subsequent embodiments, the pH-modifying agent comprises fumaric acid, tartaric acid, glutamic acid, or a combination thereof. In some embodiments, along with other prior or subsequent embodiments, the pH-modifying agent includes maleic acid, citric acid, tartaric acid, pamoic acid, fumaric acid, salicylic acid, 2,6-diaminohexanoic acid, camphorsulfonic acid, glycerophosphoric acid, 2-hydroxyethanesulfonic acid, isethionic acid, succinic acid, carbonic acid, p-toluenesulfonic acid, aspartic acid, 8-chlorotheophylline, benzenesulfonic acid, melic acid, orotic acid, oxalic acid, benzoic acid, 2-naphthalenesulfonic acid, stearic acid, adipic acid, p-aminosalicylic acid, 5-aminosalicylic acid, ascorbic acid, sulfuric acid, cyclamic acid, sodium lauryl sulfate, glucoheptonic acid, glucuronic acid, glycine, sulfuric acid, mandelic acid, acid 1,5-naphthalenedisulfonic acid, nicotinic acid, oleic acid, 2-oxoglutaric acid, pyridoxal-5-phosphate, undecanoic acid, p-acetamidobenzoic acid, o-acetamidobenzoic acid,m-acetamidobenzoic acid, N-acetyl-L-aspartic acid, camphoric acid, dehydrocholic acid, malonic acid, edetic acid, ethylenediaminetetraacetic acid, ethylsulfuric acid, hydroxyphenylbenzoylbenzoic acid, glutamic acid, glycyrrhizic acid, 4-hexylresorcinol, hippuric acid, p-phenolsulfonic acid, 4-hydroxybenzoic acid, 3-hydroxybenzoic acid, 3-hydroxy-2-naphthoic acid, 1-hydroxy-2-naphthoic acid, lactobionic acid, 3'-adenylic acid, 5'-adenylic acid, mucic acid, galactaric acid, pantothenic acid, pectic acid, polygalacturonic acid, 5-sulfosalicylic acid 1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxopurine-7-propanesulfonic acid, terephthalic acid, 1-hydroxy-2-naphthoic acid and combinations thereof. In some embodiments, along with other prior or subsequent embodiments, the pH modifying agent is selected from maleic acid, citric acid, malic acid, fumaric acid, sulfuric acid, tartaric acid, lactoic acid, salicylic acid, aspartic acid, aminosalicylic acid, malonic acid, glutamic acid, and any combination thereof. In some embodiments, in conjunction with other prior or subsequent embodiments, fumaric acid is used as a pH-modifying agent because it is less hygroscopic and more compatible with omecamtiv mecarbil dihydrochloride hydrate than citric acid. This results in little or no transformation of the active form and no change in the appearance of the tablets when stored at approximately 40°C / 75% RH for approximately 6 months, leading to improved final product quality. Furthermore, fumaric acid is more acidic (approximately twice as acidic) as citric acid. Therefore, it is more effective—i.e., at a weight ratio of approximately 1:1 with respect to the active ingredient rather than approximately 2:1—to use fumaric acid to modulate the microenvironmental pH in order to enhance the release of omecamtiv mecarbil in a neutral environment. Fumaric acid also has a very slow dissolution rate.As a result, fumaric acid will remain in the tablet longer and better maintain the low microenvironmental pH, resulting in a more complete release of omecamtiv mecarbil in approximately 24 hours. As used herein, the term fillers refers to one or more substances that may be added to the components of a pharmaceutical composition to increase the total weight of the material to be formulated, e.g., in tablets, to achieve the desired weight. Fillers include, but are not limited to, starches, lactose, mannitol (such as Pearlitol™ SD 200), cellulose derivatives, calcium phosphate, sugar, and the like. The different grades of lactose include, but are not limited to, lactose monohydrate, lactose DT (direct tablet forming), anhydrous lactose, Flowlac™ (available in Meggle products), Pharmatose™ (available from DMV), and others. The different grades of starch include, but are not limited to, corn starch, potato starch, rice starch, wheat starch, pregelatinized starch (commercially available as PCS PC10 from Signet Chemical Corporation), Colorcon Starch 1500, Colorcon Starch 1500 LM (low moisture) grade, fully pregelatinized starch (commercially available as National 78-1551 from Essex Grain Products), and others. The different cellulose compounds that may be used include crystalline cellulose and powdered cellulose.Examples of crystalline cellulose products include, but are not limited to, CEOLUS™ KG801, Avicel™ PH 101, PH102, PH301, PH302 and PH-F20, microcrystalline cellulose 114 and microcrystalline cellulose 112. Other payloads include, but are not limited to, carmellose, sugar alcohols such as mannitol, sorbitol and xylitol, calcium carbonate, magnesium carbonate, dibasic calcium phosphate and tribasic calcium phosphate. In some embodiments, along with other earlier or later embodiments, the filler is selected from starch, lactose, mannitol (such as Pearlitol™ SD 200), cellulose derivatives, calcium phosphate, and a sugar. In some embodiments, along with other preceding or subsequent embodiments, the load is anhydrous lactose or lactose monohydrate. In some embodiments, along with other preceding or subsequent embodiments, the load is DT lactose, Flowlac™, or Pharmatose™. In some embodiments, along with other earlier or lower embodiments, the filler is corn starch, potato starch, rice starch, wheat starch, pregelatinized starch (such as Starch 1500 or Starch 1500 LM quality (low moisture quality)), or fully pregelatinized starch. In some embodiments, along with other earlier or later embodiments, the filler is microcrystalline cellulose, such as CEOLUS™ KG801, Avicel™ PH 101, PH102, PH301, PH302 and PH-F20, microcrystalline cellulose 114 or microcrystalline cellulose 112. In some embodiments, along with other earlier or later embodiments, the filler is carmellose, mannitol, sorbitol, xylitol, calcium carbonate, magnesium carbonate, dibasic calcium phosphate, or tribasic calcium phosphate. As used herein, the term lubricants refers to one or more substances that may be added to the components of these compositions to reduce the adhesion of a solid formulation to the equipment used for the production of a unit dosage form. Lubricants include stearic acid, hydrogenated vegetable oils, hydrogenated soybean oil, hydrogenated soybean oil and castor wax, stearyl alcohol, leucine, polyethylene glycol, magnesium stearate, glyceryl monostearate, stearic acid, glyceryl behenate, polyethylene glycol, ethylene oxide polymers, sodium lauryl sulfate, magnesium lauryl sulfate, sodium oleate, sodium stearyl fumarate, DL-leucine, colloidal silica, and mixtures thereof. In some embodiments, along with other prior or subsequent embodiments, the lubricant is stearic acid, hydrogenated vegetable oil, hydrogenated soybean oil, hydrogenated soybean oil and castor wax, stearyl alcohol, leucine, polyethylene glycol, magnesium stearate, glyceryl monostearate, stearic acid, glyceryl behenate, polyethylene glycol, ethylene oxide polymers, sodium lauryl sulfate, magnesium lauryl sulfate, sodium oleate, sodium stearyl fumarate, DL-leucine, colloidal silica, or any mixture thereof. Inflatable core formulations Pharmaceutical formulations comprising: a drug layer comprising omecamtiv mecarbil as a salt or crystalline form as disclosed herein; a swelling agent layer; and a semipermeable membrane coating having at least one administration access. Formulations comprising a drug layer comprising: omecamtiv mecarbil as a salt or crystalline form as revealed herein; a drug-coating polymer; and a lubricant; a layer of swelling agent comprising: a swelling layer polymer; an osmotic agent; a diluent; and a lubricant and a semipermeable membrane coating having at least one administration access comprising: an insoluble polymer; and a pore-forming polymer. In some embodiments, together with other prior or subsequent embodiments, the pharmaceutical formulation comprises: a drug layer comprising: 10-20 (% w / w) of salt or crystalline form of omecamtiv mecarbil; 40-60 (% w / w) polyethylene oxide; and 0-2% (% w / w) of lubricant; a swelling agent layer comprising: 12-30 (% w / w) of polyethylene oxide; 2-10 (% w / w) of an osmotic agent; 1-8 (% w / w) of microcrystalline cellulose; and 0.1-2 (% w / w) of lubricant; and a semipermeable membrane having at least one administration access comprising: 5-15 (% w / w) of cellulose acetate; 0.3-5 (% w / w) of polyethylene glycol. In some embodiments, together with other prior or subsequent embodiments, the pharmaceutical formulation comprises: / co in / C7n7 / e / YiAi a drug layer comprising: 14-17 (% w / w) salt or crystalline form of omecamtiv mecarbil; 48-55 (% w / w) polyethylene oxide; and 0.1-0.5% (% w / w) of lubricant; a swelling agent layer comprising: 18-25 (% w / w) of polyethylene oxide; 4-9 (% w / w) of an osmotic agent; 3-6 (% w / w) of microcrystalline cellulose; and 0.1-0.5 (% w / w) of lubricant; and a semipermeable membrane having at least one administration access comprising: 8-10 (% w / w) of cellulose acetate; 0.5-3 (% w / w) of polyethylene glycol. In some embodiments, together with other prior or subsequent embodiments, the pharmaceutical formulation comprises: a drug layer comprising: 10-20 (% w / w) salt or crystalline form of omecamtiv mecarbil; 40-60 (% w / w) polyethylene oxide; and 0-2% (% w / w) magnesium stearate; a swelling agent layer comprising: 12-30 (% w / w) polyethylene oxide; 2-10 (% w / w) sodium chloride; 1-8 (% w / w) microcrystalline cellulose; and 0.1-2 (% w / w) magnesium stearate; and a semipermeable membrane having at least one administration access comprising: 5-15 (% w / w) cellulose acetate; 0.3-5 (% w / w) polyethylene glycol 3350. In some embodiments, together with other prior or subsequent embodiments, the pharmaceutical formulation comprises: a drug layer comprising: 15-16 (% w / w) salt or crystalline form of omecamtiv mecarbil; 50-52 (% w / w) of PoIyOx™ WSR N-80; and 0.1-0.5% (% w / w) magnesium stearate; a swelling agent layer comprising: 20-23 (% w / w) of PoIyOx™ WSR coagulant; 4-9 (% w / w) of sodium chloride; 3-6 (% w / w) of Avicel PH 200; and 0.1-0.5 (% w / w) of lubricant; and a semipermeable membrane having at least one administration access comprising: 8-10 (% w / w) of cellulose acetate; 0.5-3 (% w / w) of polyethylene glycol 3350. In some embodiments, together with other prior or subsequent embodiments, the pharmaceutical formulation comprises: a drug layer comprising: 15-16 (% w / w) salt or crystalline form of omecamtiv mecarbil; 50-52 (% w / w) of PoIyOx™ WSR N-80; and 0.1-0.5% (% w / w) magnesium stearate; a swelling agent layer comprising: 20-23 (% w / w) of PoIyOx™ WSR coagulant; 4-9 (% w / w) of sodium chloride; 3-6 (% w / w) of Avicel PH 200; and 0.1-0.5 (% w / w) of lubricant; and a semipermeable membrane having at least one administration access comprising: 8-9 (% w / w) of cellulose acetate; 2-3 (% w / w) of polyethylene glycol 3350. In some embodiments, together with other prior or subsequent embodiments, the pharmaceutical formulation comprises: a drug layer comprising: 15-16 (% w / w) salt or crystalline form of omecamtiv mecarbil; 50-52 (% w / w) of PoIyOx™ WSR N-80; and 0.1-0.5% (% w / w) magnesium stearate; a swelling agent layer comprising: 20-23 (% w / w) of PoIyOx™ WSR coagulant; 4-9 (% w / w) of sodium chloride; 3-6 (% w / w) of Avicel PH 200; and 0.1-0.5 (% w / w) of lubricant; and a semipermeable membrane having at least one administration access comprising: 9-10 (% w / w) of cellulose acetate; 0.5-2 (% w / w) of polyethylene glycol 3350. Methods of use The salts or crystalline forms of omecamtiv mecarbil disclosed herein, or the pharmaceutical compositions described herein, may be used in the treatment or prevention of heart failure, including, but not limited to: acute (or decompensated) congestive heart failure and chronic congestive heart failure; particularly diseases associated with systolic cardiac dysfunction. Methods for treating or preventing heart failure in a subject in need are also provided herein, comprising administering to the subject one or more of the salts or crystalline forms of omecamtiv mecarbil disclosed herein, or one or more of the pharmaceutical compositions described herein, in an amount effective to treat or prevent heart failure. Methods for using the disclosed salts and crystalline forms of omecamtiv mecarbil, or compositions thereof, for the treatment or prevention of heart failure are further provided, including, but not limited to, acute (or decompensated) congestive heart failure and chronic congestive heart failure; particularly diseases associated with systolic cardiac dysfunction. This disclosure also provides for the use of the salts or crystalline forms of omecamtiv mecarbil disclosed herein, or the pharmaceutical compositions described herein, in the manufacture of a medicament for the treatment or prevention of heart failure. In some embodiments, this disclosure provides for the use of the salts or crystalline forms of omecamtiv mecarbil disclosed herein, or the pharmaceutical compositions described herein, in the manufacture of a medicament for the treatment of acute (or decompensated) congestive heart failure and chronic congestive heart failure; particularly, diseases associated with systolic cardiac dysfunction. j co in / C7n7 / e / YiAi Treatment includes one or more of the following: a) inhibiting a disease or disorder; b) slowing or stopping the development of clinical symptoms of a disease or disorder; and / or c) alleviating a disease or disorder, i.e., causing the regression of clinical symptoms. The term covers both complete and partial reduction of the condition or disorder, and complete or partial reduction of the clinical symptoms of a disease or disorder. Therefore, the salts or crystalline forms of omecamtiv mecarbil described herein, or the pharmaceutical compositions described herein, may prevent the worsening of an existing disease or disorder, assist in the treatment of the disease or disorder, or reduce or eliminate the disease or disorder.Prevention, i.e., preventing the development of clinical symptoms of the disease or disorder, includes the prophylactic administration of a pharmaceutical formulation described herein to a subject (i.e., an animal, preferably a mammal, most preferably a human) believed to require preventive treatment, such as, for example, for chronic heart failure. EXAMPLES Methods X-ray diffraction in powder Procedure A: XRPD analysis was performed on a PANalytical X'pert pro, scanning samples between 3 and 35° 2Θ. The material was gently ground to release any agglomeration and loaded onto a multi-well plate with Kapton or Mylar polymer film to support the sample. The multi-well plate was then placed in the diffractometer and analyzed using Cu K radiation (α1λ = 1.54060 A; α2 = 1.54443 A; β = 1.39225 A; α1:α2 ratio = 0.5) operating in transmission mode (step size 0.0130° 2Θ) using 40 kV / 40 mA generator settings. Procedure B: XRPD analysis was performed on a PANalytical X'pert pro, scanning samples between 3 and 40° 2Θ. The material was loaded into a zero-background sample holder, then placed in the diffractometer on a spin stage at 1 rotation per second and analyzed using Cu K radiation (α1 λ = 1.54060 A; α2 = 1.54443 A; β = 1.39225 A; α1:α2 ratio = 0.5) operating in transmission mode (step size 0.0167° 2Θ) using 45 kV / 40 mA generator settings. Procedure C: Powder X-ray diffraction patterns were collected on a Bruker AXS C2 GADDS diffractometer using Cu Ka radiation (40 kV, 40 mA), an automated XYZ stage, a laser video microscope for automatic sample positioning, and a HiStar two-dimensional area detector. The X-ray optics consisted of a single GObel multilayer mirror coupled with a collimator with 0.3 mm pores. The beam divergence, i.e., the effective size of the X-ray beam on the sample, was approximately 4 mm. A continuous θ-θ scan mode was employed with a sample-detector distance of 20 cm, giving an effective range of 3.2°–29.7°. Typically, the sample was exposed to the X-ray beam for 120 seconds. Environmental conditions. Samples processed under ambient conditions were prepared as flat plate samples using powder as received with and without crushing.Approximately 1-2 mg of the sample was lightly pressed onto a glass slide to obtain a flat surface. Differential scanning calorimetry (DSC) Procedure A: Thermal properties were characterized using a TA Instruments Q1000 or Q100 DSC model, differential scanning calorimetry, and a TA Instruments Q500 thermogravimetric analyzer. Data analysis was performed using TA Instruments Universal Analysis 2000. Heating rates of 1, 10, and 100 °C / min were used at a variety of temperature ranges for differential scanning calorimetry and thermogravimetric analysis. Samples ranging from 1 to 5 mg were prepared in corrugated, airtight, or open aluminum trays for DSC analysis. Procedure B: DSC data were collected on a TA Instruments Q2000 equipped with a 50-position autosampler. The instrument was calibrated for power and temperature using certified indium. Typically, 0.5–3 mg of each sample was heated in a porous aluminum tray at 10 °C / min from 25 °C to 350 °C. A nitrogen purge of 50 mL / min was maintained over the sample. The instrument control software was Thermal Advantage v4.6.6, and the data were analyzed using Universal Analysis v4.3A. Thermogravimetric and differential thermal analysis (TG / DTA) Approximately 5 mg of material were weighed into an open aluminum tray and loaded into a simultaneous differential thermal and thermogravimetric analyzer (TG / DTA) and kept at room temperature. The sample was then heated at a rate of 10 °C / min from 20 °C to 300 °C, during which time the change in sample weight was recorded along with any differential thermal events (DTA). Nitrogen was used as the purge gas at a flow rate of 300 cm³ / min. Thermogravimetric analysis Procedure A: Thermograms were collected using a TA Instruments Q500 thermogravimetric analyzer. Samples were loaded onto a platinum tray, from 1 to 10 mg, and heated at 10 °C / min from room temperature to 300 °C. Procedure B: TGA data were collected on a TA Instruments Q500 TGA equipped with a 16-position autosampler. The instrument was temperature calibrated using certified Alumel. Typically, 5–30 mg of each sample was loaded into a pre-tared platinum crucible and aluminum DSC tray and heated at 10 °C / min from room temperature to 350 °C. A nitrogen purge of 60 mL / min was maintained over the sample. The instrument control software was Thermal Advantage v4.6.6, and the data were analyzed using Universal Analysis v4.3A. Moisture sorption The moisture balance was collected using a dynamic vapor sorption (DVS) analyzer. Relative humidity (RH) was set at 0, 5, 15, 25, 35, 45, 55, 65, 75, 85, and 95% RH for two sorption / desorption cycles at 25 °C. The equilibrium criterion was set at 0.001 wt%. Approximately 10 mg of sample were used. Solubility An excess of solid was added to water, pH 1.0 buffer, or pH 4.5 buffer to produce a suspension, and the suspension was dispersed for at least 24 hours at room temperature. The suspensions were filtered. The filtrate was analyzed by HPLC-UV (High-Performance Liquid Chromatography with UV Detector) and compared to a standard curve to determine the concentration of the crystalline form in solution. Experimental section Freebase crystalline form III: Procedure A: was prepared by adding 429 mg of omecamtiv mecarbil to 20 ml of 2-propanol and 20 ml of water, then heating to 50 °C to dissolve, and then precipitated with 200 ml of water. Procedure B: This was prepared during a solubility sieve from seven different solvents (2-BuOAc suspension, eumene suspension, isopropyl acetate suspension, MTBE suspension, heptane suspension, tBuOAc suspension, or toluene suspension). Ten mg of free base were placed in a vial, and 50 µL aliquots of the solvents were added to the vial, followed by 100 µL additions (up to 1 µL). Between each addition, the dissolution of the mixture was checked, and if no apparent dissolution occurred, the mixture was heated to approximately 50 °C and checked again. This procedure was continued until dissolution was observed or until 100 volumes of solvent had been added. If no dissolution occurred, the solid was filtered out, and an XRPD was collected. If dissolution occurred, the lid was removed to allow evaporation of the solvent and an XRPD sample of the remaining solid was collected.The freebase crystalline form III was then reproduced from a suspension in eumene, isopropyl acetate, MTBE or tBuOAc by adding 60 mg of lyophilized freebase to the solvent and gently heating to approximately 40 °C. The base-free III crystal form of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 1. cc in / C7n7 / e / YiAi Table 1 Pos. [°2Th.] FWHM (Full Width at Half Maximum, width at half height) Interplanar distance [Á] Height [cts] Int. reí. [%] 7.91 0.07 11.17 533.03 2.67 9.50 0.08 9.31 3776.76 18.91 14.27 0.10 6.21 15559.92 77.89 15.25 0.08 5.81 1095.46 5.48 16.10 0.10 5.51 1128.65 5.65 17.78 0.10 4.99 19975.52 100.00 19.06 0.10 4.66 2511.63 12.57 19.64 0.20 4.52 143.81 0.72 20.65 0.13 4.30 421.10 2.11 21.24 0.15 4.18 293.88 1.47 23.01 0.10 3.87 1285.85 6.44 23.87 0.10 3.73 1434.94 7.18 24.83 0.13 3.59 201.27 1.01 25.59 0.10 3.48 226.37 1.13 26.23 0.20 3.40 166.45 0.83 27.23 0.20 3.28 89.66 0.45 28.11 0.15 3.17 805.44 4.03 28.80 0.13 3.10 362.99 1.82 31.01 0.17 2.88 701.54 3.51 31.95 0.12 2.80 844.68 4.23 32.34 0.20 2.77 605.43 3.03 33.67 0.13 2.66 248.53 1.24 34.69 0.13 2.59 293.11 1.47 37.26 0.13 2.41 245.07 1.23 38.73 0.23 2.33 152.34 0.76 Freebase crystalline form IV: was prepared by precipitation of 46 mg of omecamtiv mecarbil from 2 ml of THF with 2 ml of n-butyl ether. The base-free crystalline form IV of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 2. Table 2 Pos. [°2Th.] FWHM [°2Th.] Interplanar Distance [A] Height [cts] Internal Reí. [%] 5.18 0.07 17.04 12067.81 100.00 7.42 0.10 11.91 322.11 2.67 / pp in / pznz / e / viAi 7.70 0.08 11.48 416.99 3.46 10.35 0.07 8.55 814.51 6.75 10.81 0.10 8.19 170.45 1.41 14.21 0.08 6.23 789.68 6.54 14.84 0.07 5.97 1276.45 10.58 15.54 0.08 5.70 2686.48 22.26 17.10 0.10 5.18 122.93 1.02 18.10 0.10 4.90 10344.17 85.72 19.92 0.08 4.46 939.94 7.79 20.62 0.07 4.31 802.71 6.65 20.77 0.07 4.28 931.21 7.72 21.70 0.08 4.10 481.64 3.99 22.40 0.12 3.97 418.41 3.47 22.86 0.10 3.89 673.49 5.58 23.09 0.08 3.85 571.53 4.74 24.05 0.08 3.70 774.58 6.42 24.36 0.12 3.65 752.02 6.23 25.20 0.10 3.53 582.91 4.83 25.72 0.07 3.46 378.21 3.13 26.00 0.10 3.43 138.03 1.14 26.68 0.27 3.34 93.44 0.77 27.40 0.10 3.26 400.49 3.32 27.81 0.12 3.21 724.88 6.01 28.18 0.10 3.17 278.71 2.31 28.63 0.08 3.12 399.78 3.31 28.98 0.08 3.08 480.22 3.98 29.42 0.10 3.04 644.30 5.34 30.51 0.13 2.93 247.42 2.05 32.80 0.13 2.73 137.46 1.14 33.98 0.20 2.64 155.02 1.28 35.34 0.20 2.54 147.52 1.22 36.38 0.20 2.47 110.92 0.92 37.12 0.20 2.42 126.42 1.05 Freebase crystal form V: Procedure A: was prepared by adding 50 mg of omecamtiv mecarbil to 2 ml of THF at 60 °C, filtered and then rapidly cooled by placing the sample in an acetone / dry ice bath. Procedure B: The crystalline form V of the free base was prepared during a solubility sieving from a 1,4-dioxane suspension. Ten mg of the free base were placed in a vial, and 50 µL aliquots of the first 300 µL, followed by 100 µL aliquots (up to 1 µL), of the solvent were added to the vial. Between each addition, the dissolution of the mixture was checked, and if no apparent dissolution was observed, the mixture was heated to approximately 50 °C and checked again. This procedure was continued until dissolution was observed or until 100 volumes of solvent had been added. If no dissolution occurred, the solid was filtered out, and an XRPD was collected. If dissolution occurred, the cap was removed to allow evaporation of the solvent, and an XRPD was collected from the remaining solid. The base-free V crystal form of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 3. Table 3 j co in / C7n7 / e / YiAi Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 5.40 0.10 16.37 213.79 7.88 7.38 0.07 11.98 470.25 17.33 8.56 0.07 10.33 430.26 15.86 8.93 0.08 9.91 563.71 20.78 9.14 0.07 9.67 392.66 14.47 10.03 0.08 8.82 375.08 13.82 10.73 0.13 8.25 332.70 12.26 11.71 0.12 7.56 840.50 30.98 13.69 0.17 6.47 335.68 12.37 15.08 0.18 5.88 653.88 24.10 16.04 0.33 5.52 105.31 3.88 16.85 0.08 5.26 920.36 33.92 17.85 0.13 4.97 2713.30 100.00 18.28 0.10 4.85 347.67 12.81 18.86 0.12 4.71 1897.24 69.92 20.05 0.20 4.43 1456.16 53.67 20.72 0.07 4.29 659.49 24.31 21.74 0.17 4.09 354.74 13.07 22.83 0.27 3.90 189.17 6.97 23.56 0.10 3.78 1152.90 42.49 24.03 0.20 3.70 645.49 23.79 25.45 0.20 3.50 217.43 8.01 26.23 0.10 3.40 366.63 13.51 27.62 0.23 3.23 654.84 24.13 28.58 0.23 3.12 253.96 9.36 29.85 0.27 2.99 254.72 9.39 32.10 0.20 2.79 233.50 8.61 33.37 0.33 2.69 165.44 6.10 35.47 0.27 2.53 105.15 3.88 37.02 0.40 2.43 122.14 4.50 Free-base crystal form VI: was prepared by heating the free-base crystal form V to 150 °C. The base-free VI crystal form of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 4. Table 4 / co in / C7n7 / e / YiAi Pos. [°2Th.] FWHM [°2Th.] Distance , interplanar [Á] Height [cts] Int. reí. [%] 9.07 0.08 9.75 895.54 31.71 14.28 0.13 6.20 147.01 5.20 15.19 0.20 5.83 42.70 1.51 15.88 0.12 5.58 539.11 19.09 16.67 0.08 5.32 796.74 28.21 17.81 0.08 4.98 1094.93 38.77 18.18 0.17 4.88 2824.51 100.00 18.80 0.12 4.72 850.75 30.12 19.70 0.10 4.51 1045.62 37.02 20.23 0.13 4.39 185.58 6.57 20.89 0.10 4.25 1310.32 46.39 21.28 0.12 4.18 925.51 32.77 23.72 0.08 3.75 691.60 24.49 24.26 0.08 3.67 784.97 27.79 26.19 0.20 3.40 146.84 5.20 26.80 0.17 3.33 235.58 8.34 27.59 0.13 3.23 347.69 12.31 28.90 0.33 3.09 163.33 5.78 29.82 0.12 3.00 368.54 13.05 Freebase crystalline form Vil: This was prepared during a solubility sieve from an aqueous suspension. 10 mg of freebase were placed in a vial, and 50 mL aliquots of water were added to the vial, starting with 300 mL and continuing with 100 mL additions (up to 1 mL). Between each addition, the dissolution of the mixture was checked, and if no apparent dissolution occurred, the mixture was heated to approximately 50 °C and checked again. This procedure was continued until dissolution was observed or until 100 volumes of solvent had been added. The solid was filtered out, and an XRP (X-ray precipitate) was collected. The base-free Vil crystalline form of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 5. Table 5 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 4.37 0.08 20.24 4137.34 100.00 7.84 0.13 11.27 89.35 2.16 8.40 0.06 10.52 285.34 6.90 8.71 0.08 10.15 172.30 4.16 10.81 0.15 8.19 74.73 1.81 13.08 0.08 6.77 387.47 9.37 15.66 0.08 5.66 481.77 11.64 16.83 0.10 5.27 1596.66 38.59 18.92 0.10 4.69 1248.28 30.17 19.61 0.09 4.53 1696.18 41.00 20.32 0.05 4.37 584.96 14.14 20.49 0.10 4.33 961.99 23.25 21.61 0.08 4.11 319.30 7.72 22.26 0.10 3.99 1149.06 27.77 23.22 0.08 3.83 265.13 6.41 23.46 0.10 3.79 299.05 7.23 24.21 0.13 3.68 1205.74 29.14 25.41 0.05 3.51 1016.23 24.56 27.58 0.13 3.23 318.93 7.71 29.53 0.15 3.02 279.27 6.75 30.13 0.15 2.97 221.71 5.36 31.32 0.61 2.86 95.23 2.30 / co in / C7n7 / e / YiAi Table 6 shows the unique XRPD maxima for each of the base-free III-VII crystal forms revealed herein. Table 6 Free-base crystal form Unique maximums for each form (KA1°) Form III 9.50 19.06 23.01 Form IV 5.18 10.35 14.84 15.54 18.10 19.92 Form V 7.38 8.56 9.14 18.28 Form VI 9.07 16.67 18.18 19.70 20.89 21.28 Form VII 8.40 8.71 13.08 15.66 19.61 Amorphous hydrochloride salt: An amorphous bis-hydrochloride salt was prepared by dissolving 0.505 g of form A of the monohydrated bis-hydrochloride salt in 20 mL of water, flash-freezing it in liquid nitrogen, and then lyophilizing it. Chloride analysis yielded a result of 14.6% IO, consistent with a bis-hydrochloride. Thermal analysis indicated a weight loss of approximately 7.9% upon heating due to water loss and a melting point (Tv) of around 149 °C. Vapor sorption studies showed that the amorphous form is hygroscopic and converts to the crystalline form A of the monohydrated bis-hydrochloride. Ethane sultanate crystalline salt: It was prepared by sieving primary salt. A 2 mL aliquot of acetone was added to ~40 mg of free base. 1.05 equivalents of ethane sultanate in the form of a 1 M solution in THF were added, and the sample was subjected to temperature cycling for 3–5 days. The ethane-sulfonate crystalline salt of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 7. Table 7 / pp in / pznz / R / viAi Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 8.61 0.10 10.27 1864.81 100.00 13.61 0.15 6.51 141.09 7.57 16.14 0.10 5.49 1152.97 61.83 16.76 0.13 5.29 825.27 44.26 16.97 0.08 5.22 914.05 49.02 17.23 0.13 5.15 1148.35 61.58 18.35 0.15 4.84 579.44 31.07 19.20 0.20 4.62 710.28 38.09 20.27 0.20 4.38 781.89 41.93 20.73 0.08 4.28 1275.35 68.39 20.96 0.10 4.24 1275.82 68.42 23.73 0.20 3.75 494.48 26.52 25.24 0.15 3.53 262.30 14.07 25.95 0.15 3.43 442.47 23.73 26.30 0.10 3.39 512.57 27.49 27.09 0.20 3.29 204.40 10.96 29.01 0.41 3.08 74.97 4.02 Form A of bis-fumarate crystalline salt: was prepared by dissolving 1 equivalent of free base (4.104 g) and 2.1 equivalents of fumaric acid (as 84 ml in a 95% EtOH / water solution) in 20 ml of 90% THF in water, and then domestic vacuum distillation at 50 °C. A further 92 ml of water and mono-fumarate form A seeds were added to induce precipitation. Form A of the crystalline salt bis-fumarate of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 8. Table 8 77OPI n / cznz / e / viAi Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 5.64 0.18 15.67 1058.97 74.12 8.83 0.27 10.01 92.99 6.51 10.80 0.17 8.20 144.21 10.09 12.04 0.20 7.35 271.90 19.03 15.76 0.17 5.62 249.66 17.47 16.40 0.10 5.41 417.23 29.20 16.80 0.13 5.28 1428.74 100.00 17.94 0.20 4.94 167.95 11.76 18.32 0.13 4.84 247.68 17.34 19.38 0.17 4.58 130.62 9.14 19.87 0.13 4.47 159.85 11.19 20.61 0.27 4.31 198.11 13.87 21.55 0.13 4.12 445.40 31.17 21.87 0.13 4.06 589.24 41.24 22.03 0.13 4.04 583.89 40.87 22.88 0.13 3.89 300.01 21.00 23.61 0.10 3.77 1008.70 70.60 23.87 0.13 3.73 1042.62 72.97 25.07 0.27 3.55 109.91 7.69 26.01 0.18 3.43 795.76 55.70 27.20 0.27 3.28 900.61 63.04 27.86 0.23 3.20 317.54 22.23 29.55 0.27 3.02 61.88 4.33 31.04 0.20 2.88 103.03 7.21 32.73 0.27 2.74 145.12 10.16 35.00 0.20 2.56 80.10 5.61 36.01 0.27 2.49 62.22 4.35 36.54 0.23 2.46 138.74 9.71 Form B of the bis-fumarate crystalline salt: was prepared during the DVS cycle of Form A of bis-fumarate. The B form of the crystalline salt omecamtiv mecarbil bis-fumarate was characterized by an XRPD pattern comprising the maxima in Table 9. Table 9 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. laughter. [%] 5.68 0.20 15.57 557.86 53.41 6.11 0.15 14.47 941.86 90.18 9.69 0.07 9.13 213.36 20.43 11.43 0.17 7.74 195.35 18.70 12.92 0.10 6.85 428.18 41.00 13.13 0.08 6.74 739.41 70.80 14.34 0.40 6.18 52.05 4.98 15.95 0.20 5.56 656.27 62.84 16.83 0.23 5.27 142.59 13.65 17.22 0.20 5.15 178.09 17.05 18.08 0.20 4.91 494.57 47.35 19.05 0.20 4.66 135.39 12.96 19.52 0.33 4.55 99.22 9.50 20.81 0.20 4.27 362.18 34.68 22.47 0.15 3.96 547.41 52.41 22.95 0.27 3.87 553.11 52.96 24.53 0.20 3.63 147.89 14.16 26.04 0.20 3.42 434.11 41.57 27.01 _ 0.13 3.30 1044.39 100.00 28.43 0.13 3.14 313.18 29.99 31.37 0.27 2.85 59.28 5.68 32.32 0.23 2.77 49.90 4.78 34.89 0.40 2.57 65.58 6.28 35.89 0.23 2.50 54.73 5.24 37.16 0.20 2.42 68.51 6.56 77OPI n / cznz / e / viAi Form C of the bis-fumarate crystalline salt: was prepared from a suspension of Forms A and B of bis-fumarate in 2 ml of water at room temperature. The solubility in water was determined to be 13.7 mg / ml (pH 3.1). The C form of the crystalline salt omecamtiv mecarbil bis-fumarate was characterized by an XRPD pattern comprising the maxima in Table 10. Table 10 Pos. [°2Th.] FWHM [°2Th.] Interplanar Distance [A] Height [cts] Internal Interval [%] 5.88 0.17 15.03 5167.95 100.00 10.38 0.54 8.53 75.90 1.47 10.70 0.10 8.27 162.04 3.14 11.56 0.12 7.65 325.84 6.30 12.74 0.10 6.95 1330.99 25.75 13.56 0.12 6.53 529.65 10.25 15.33 0.13 5.78 181.25 3.51 16.85 0.10 5.26 336.53 6.51 17.15 0.12 5.17 1259.92 24.38 17.63 0.10 5.03 864.50 16.73 18.79 0.12 4.72 557.14 10.78 19.52 0.12 4.55 229.88 4.45 20.29 0.12 4.38 906.12 17.53 20.60 0.12 4.31 510.74 9.88 20.86 0.10 4.26 460.43 8.91 21.47 0.07 4.14 668.33 12.93 21.77 0.08 4.08 697.87 13.50 22.21 0.13 4.00 865.69 16.75 22.92 0.13 3.88 864.48 16.73 23.58 0.13 3.77 792.02 15.33 24.15 0.07 3.68 600.60 11.62 24.55 0.13 3.63 373.42 7.23 25.41 0.17 3.51 1064.69 20.60 26.37 0.12 3.38 254.11 4.92 26.78 0.12 3.33 1601.63 30.99 26.86 0.06 3.33 1640.39 31.74 27.31 0.12 3.26 450.94 8.73 27.83 0.16 3.20 618.62 11.97 28.97 0.06 3.08 340.41 6.59 29.93 0.24 2.98 283.61 5.49 30.37 0.24 2.94 102.99 1.99 31.97 0.20 2.80 88.93 1.72 32.37 0.29 2.76 67.32 1.30 33.10 0.16 2.70 128.77 2.49 34.02 0.33 2.63 173.14 3.35 35.76 0.29 2.51 160.08 3.10 38.14 0.24 2.36 76.60 1.48 38.88 0.33 2.31 187.08 3.62 39.55 0.20 2.28 104.38 2.02 Form D of the mono-fumarate crystalline salt: It was first prepared during a high-performance sieving by adding 0.3 ml of a 0.05 M free base solution in methanol and 0.3 ml of a 0.05 M fumaric acid solution in methanol to a glass plate, and then the solvent was evaporated, after which 0.4 ml of solvent (water, 0.001 M aqueous HCl, acetone, acetonitrile or hexanes) was added and heated to 50 °C for 4 hours, and then it was evaporated. The D form of the crystalline salt omecamtiv mecarbil mono-fumarate was characterized by an XRPD pattern comprising the maxima in Table 11. Table 11 j co in / C7n7 / e / YiAi Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 8.01 0.09 11.04 102.83 59.94 12.11 0.11 7.31 72.99 42.55 12.67 0.13 6.99 50.43 29.40 14.46 0.13 6.12 83.35 48.59 15.20 0.19 5.83 , 55.38 32.28 16.01 0.19 5.54 50.34 29.34 16.57 0.11 5.35 76.69 44.71 17.04 0.14 5.20 32.05 18.69 17.63 0.16 5.03 37.88 22.08 18.48 0.16 4.80 16.35 9.53 20.02 0.11 4.43 34.71 20.23 20.51 0.22 4.33 31.27 18.23 21.75 0.16 4.09 37.60 21.92 22.86 0.19 3.89 18.19 10.60 24.25 0.13 3.67 171.54 100.00 24.97 0.19 3.57 82.03 47.82 25.84 0.13 3.45 41.01 23.91 26.17 0.16 3.41 74.19 43.25 27.10 0.13 3.29 37.05 21.60 27.97 0.19 3.19 21.24 12.38 28.61 0.19 3.12 11.11 6.48 29.21 0.16 3.06 37.43 21.82 30.69 0.25 2.91 10.74 6.26 34.70 0.50 2.59 7.97 4.64 37.41 0.19 2.40 11.12 6.48 38.48 0.38 2.34 6.46 3.77 Table 12 shows the unique XRPD maxima for each of the AD forms of fumarate crystalline salts disclosed herein. Table 12 Fumarate Form Unique maxima for each form (°2Th.) Form A 5.64 15.76 22.03 23.87 Form B 5.68 6.11 13.13 18.08 22.47 Form C 5.88 18.79 25.41 26.86 Form D 8.01 15.20 20.02 / co in / C7n7 / e / YiAi Form A of the bis-maleate crystalline salt: Procedure A: It was first prepared during high-throughput sieving by adding 0.2 mL of a 0.124 M solution of free base in methanol and 0.2 mL of a 0.25 M solution of maleic acid in methanol to a glass plate, then evaporating the solvent, and then adding 0.2 mL of solvent (water, 0.001 M aq HCl, or acetone) and heating to 50 °C for 4 hours, then evaporating. The salt was scaled up by adding 100 mg of free base to an 8 mL vial and 5 mL of methanol and heating gently to dissolve. Maleic acid (2 mL of a 0.25 M solution in acetone) was added at room temperature. The precipitate was isolated by filtration. Procedure B: Form A of the bis-maleate crystalline salt was prepared by dissolving 3.011 g of free base (1 eq) and 1.828 g of maleic acid (solution in 8 ml of MeOH; 2.1 eq) in 45 ml of methanol at 60 °C and then cooling to precipitate. The solubility in water was determined to be 3.8 mg / ml (pH 3.7). Procedure C: Form A of the bis-maleate crystalline salt was also prepared by sieving the primary salt. A 2 mL aliquot of 2-propanol, THF, acetonitrile, isopropyl acetate, or acetone was added to approximately 40 mg of free base. 1.05 equivalents of maleic acid in the form of a 1 M solution in THF were added, and the sample was subjected to temperature cycling for 3–5 days. Form A of the crystalline salt omecamtiv mecarbil bis-maleate was characterized by an XRPD pattern comprising the maxima in Table 13. Table 13 Pos. [°2Th.] FWHM [°2Th.] Interplanar Distance [A] Height [cts] Internal Interplanarity [%] 3.32 0.82 26.60 267.10 3.31 4.99 0.05 17.71 482.89 5.98 6.60 0.08 13.38 216.56 2.68 6.95 0.41 12.72 56.27 0.70 7.25 0.08 12.19 198.55 2.46 9.17 0.15 9.64 73.48 0.91 9.97 0.08 8.87 7989.17 98.97 10.56 0.08 8,38 1761.58 21.82 12.96 0.09 6.83 311.81 3.86 13.25 0.09 6.68 1227.24 15.20 14.54 0.12 6.09 356.32 4.41 14.83 0.08 5.98 743.84 9.21 15.31 0.10 5.79 8072.29 100.00 15.53 0.09 5.71 2487.57 30.82 16.04 0.10 5.52 6086.12 75.40 16.38 0.10 5.41 2253.00 27.91 17.10 0.08 5.19 675.31 8.37 17.44 0.12 5.08 3071.51 38.05 17.70 0.13 5.01 2667.01 33.04 18.17 0.10 4.88 932.80 11.56 18.45 0.10 4.81 273.07 3.38 19.00 0.13 4.67 2099.18 26.00 19.33 0.08 4.59 392.68 4.86 20.13 0.14 4.41 1667.83 20.66 21.47 0.12 4.14 2989.90 37.04 21.83 0.08 4.07 1329.81 16.47 22.02 0.06 4.04 747.10 9.26 22.31 0.10 3.98 822.83 10.19 22.44 0.09 3.96 1010.70 12.52 23.02 0.10 3.86 347.42 4.30 23.15 0.10 3.84 372.20 4.61 23.58 0.13 3.77 194.06 2.40 24.38 0.06 3.65 1003.21 12.43 24.64 0.09 3.61 876.08 10.85 25.66 0.15 3.47 924.66 11.45 26.66 0.13 3.34 1042.71 12.92 26.96 0.13 3.31 4976.38 61.65 27.83 0.13 3.21 845.81 10.48 28.10 0.10 3.18 293.57 3.64 28.55 0.15 3.13 766.92 9.50 29.31 0.08 3.05 151.67 1.88 30.17 0.20 2.96 186.07 2.31 30.76 0.23 2.91 458.79 5.68 31.67 0.13 2.83 362.78 4.49 32.01 0.13 2.80 453.36 5.62 32.25 0.13 2.78 561.46 6.96 32.67 0.18 2.74 427.72 5.30 33.11 0.20 2.71 342.20 4.24. zjcci n / cznz / e / γι 33.65 0.13 2.66 375.70 4.65 34.17 0.10 2.62 370.55 4.59 34.39 0.10 2.61 643.90 7.98 34.51 0.15 2.60 639.10 7.92 zvcci n / cznz / e / vi Bis-malonate crystalline salt: It was prepared by dissolving 200.7 mg of free base (1 eq) and 525 μL of malonic acid in methanol (2.1 eq) in 5 mL of methanol at 50 °C, then adding 0.5 mL of IPAc for precipitation and subsequently subjecting it to thermal cycling twice at 40 °C / TA. The solubility in water was determined to be greater than 62 mg / mL (pH 3.69). The bis-malonate crystalline salt of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 14. Table 14 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [A] Height [cts] Int. reí. [%] 4.74 0.09 18.64 734.38 65.86 9.30 0.13 9.51 262.93 23.58 11.37 0.13 7.78 1115.14 100.00 13.73 0.13 6.45 154.92 13.89 14.25 0.11 6.22 902.82 80.96 15.13 0.16 5.86 567.42 50.88 15.69 0.11 5.65 94.13 8.44 16.45 0.13 5.39 438.97 39.36 16.83 0.13 5.27 165.27 14.82 18.08 0.13 4.91 552.17 49.52 18.29 0.11 4.85 855.08 76.68 18.88 0.16 4.70 287.13 25.75 19.54 0.13 4.54 232.73 20.87 20.14 0.08 4.41 819.11 73.45 20.77 0.11 4.28 300.42 26.94 21.21 0.25 4.19 192.92 17.30 23.32 0.16 3.81 218.40 19.58 23.87 0.13 3.73 766.34 68.72 24.67 0.13 3.61 193.04 17.31 25.72 0.22 3.46 82.90 7.43 26.51 0.22 3.36 211.46 18.96 27.59 0.13 3.23 520.24 46.65 27.78 0.08 3.21 805.51 72.23 28.01 0.20 3.19 630.55 56.54 28.90 0.28 3.09 273.00 24.48 29.68 0.22 3.01 33.94 3.04 30.18 0.22 2.96 51.90 4.65 33.70 0.22 2.66 96.86 8.69 34.19 0.19 2.62 54.63 4.90 35.52 0.22 2.53 39.53 3.54 36.82 0.19 2.44 42.45 3.81 37.62 0.63 2.39 36.76 3.30 / co in / C7n7 / e / YiAi Form A of the mesylate crystalline salt: It was prepared by dissolving 200.7 mg of free base (1 eq) and 68.1 μL of methanesulfonic acid (2.1 eq) in 5 mL of methanol at 50 °C, and adding 2 mL of IPAc and 5 mL of acetone for precipitation. The solubility in water was determined to be greater than 72 mg / mL (pH 1.39). Form A of the crystalline salt omecamtiv mecarbil mesylate was characterized by an XRPD pattern comprising the maxima in Table 15. Table 15 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 4.02 0.38 21.96 492.38 100.00 4.87 0.25 18.15 472.41 95.94 7.79 0.19 11.35 87.26 17.72 11.61 0.25 7.62 110.78 22.50 15.21 0.25 5.82 120.46 24.46 15.86 0.25 5.59 76.35 15.51 16.51 0.19 5.37 103.12 20.94 17.57 0.28 5.05 160.72 32.64 18.42 0.31 4.82 126.44 25.68 19.26 038 4.61 218.37 44.35 20.53 0.19 4.33 98.62 20.03 21.55 0.13 4.12 184.64 37.50 23.17 0.50 3.84 115.61 23.48 24.39 0.28 3.65 207.28 42.10 25.51 0.16 3.49 126.17 25.63 26.38 0.25 3.38 65.52 13.31 27.63 0.25 3.23 83.43 16.94 30.85 0.38 2.90 29.23 5.94 Bis-mesylate crystalline salt form B: It was prepared by sieving the primary salt. A 2 mL aliquot of 2-propanol was added to approximately 40 mg of free base. 1.05 equivalents of methanesulfonic acid were added as a 1 M solution in THF, the sample was subjected to temperature cycling for 3–5 days, and then tert-butyl methyl ether was added as an antisolvent. The solubility in pH 1 and 4.5 buffers was determined to be greater than mg / mL. The B form of the crystalline salt bis-mesylate of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 16. j co in / C7n7 / e / YiAi Table 16 Pos. [°2Th.] FWHM [°2Th.] Distance = interplanar [Á] Height [cts] Int. reí. [%] 8.30 0.08 10.65 4139.68 77.69 8.94 0.06 9.89 358.87 6.73 9.59 0.08 9.22 222.95 4.18 10.78 0.08 8.21 360.97 6.77 11.15 0.05 7.94 127.57 2.39 11.66 0.09 7.59 724.49 13.60 12.15 0.09 7.28 3000.51 56.31 14.37 0.12 6.17 521.87 9.79 14.93 0.10 5.93 402.24 7.55 15.36 0.08 5.77 258.87 4.86 15.57 0.08 5.69 436.88 8.20 16.18 0.10 5.48 560.02 10.51 16.64 0.08 5.33 1864.30 34.99 16.81 0.08 5.27 744.70 13.98 17.07 0.06 5.19 2428.76 45.58 17.19 0.09 5.16 3783.32 71.00 17.41 0.10 5.09 2291.40 43.00 17.76 0.12 4.99 1630.15 30.59 19.24 0.09 4.61 757.57 14.22 19.82 0.10 4.48 1081.40 20.29 20.29 0.12 4.38 2158.58 40.51 20.66 0.14 4.30 1716.49 32.21 21.62 0.13 4.11 1236.28 23.20 22.04 0.13 4.03 739.53 13.88 22.39 0.15 3.97 5328.66 100.00 23.54 0.18 3.78 176.98 3.32 23.95 0.06 3.72 593.98 11.15 24.60 0.12 3.62 1334.05 25.04 25.02 0.13 3.56 2954.89 55.45 25.59 0.17 3.48 1527.25 28.66 25.89 0.12 3.44 581.20 10.91 26.14 0.18 3.41 329.04 6.17 26.49 0.13 3.36 171.39 3.22 27.14 0.12 3.29 637.23 11.96 27.35 0.08 3.26 1259.20 23.63. 27.41 0.05 3.26 1229.76 23.08 27.89 0.19 3.20 181.37 3.40 28.86 0.09 3.09 126.53 2.37 29.45 0.16 3.03 536.88 10.08 29.89 0.25 2.99 142.78 2.68 31.11 0.31 2.87 220.88 4.15 32.47 0.25 2.76 129.04 2.42 33.10 0.19 2.70 166.58 3.13 33.51 0.25 2.67 417.91 7.84 34.56 0.16 2.59 235.62 4.42 Table 17 shows the unique XRPD maximums for each of the shapes A and B of mesylate crystalline salts revealed herein. Table 17 Mesylate Form Unique Maximums for Each Form (°2Th.) Form A 4.02 4.87 15.21 15.86 20.53 24.39 Form B 8.30 8.94 9.59 12.15 14.37 19.82 20.29 22.04 25.02 Crystalline bis-naphthalate-2-sulfonate salt: was prepared. For primary (small-scale) sieving, a 2 mL aliquot of 2-propanol, THF, acetonityl, isopropyl acetate, acetone, or toluene was added to 40 mg of free base, and 1.05 equivalents of sodium naphthalate-2-sulfonate salt and 1.0 eq of 1 M hydrochloric acid were added, and then subjected to temperature cycling for 3–5 days. The salt was analyzed by XRPD. For secondary sieving (scaled up), 1.05 eq of naphthalene-2-sulfonate and 2 M hydrochloric acid were added to 700 mg of free base in 7 mL of 2-propanol, and the mixture was then subjected to temperature cycling (from room temperature to 40 °C) for 3 days, filtered, and dried in a vacuum oven at room temperature. The salt was analyzed by XRPD, IR, HPLC, 1H NMR, PLM, TG / DTA, DSC, DVS, VH-XRPD, stability studies, thermodynamic solubility studies, disproportionation studies, and hydration studies. Solubility in pH 1 and 4 buffers was determined.5 was greater than 10 mg / ml. The bis-naphthalate-2-sulfonate crystalline salt of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 18. Table 18 Pos. [°2Th.] FWHM [°2Th.] Distance ° Height [cts] Int. reí. [%] 4.49 0.06 19.70 5776.56 100.00 6.25 0.08 14.14 572.59 9.91 6.65 0.20 13.29 561.77 9.73 8.95 0.10 9.88 138.06 2.39 9.72 0.15 9.10 54.78 0.95 13.44 0.08 6.59 367.63 6.36 14.39 0.10 6.16 341.11 5.91 14.92 0.12 5.94 904.43 15.66 15.51 0.20 5.71 276.65 4.79 16.28 0.08 5.44 918.98 15.91 17.02 0.20 5.21 280.34 4.85 18.20 0.10 4.87 1575.43 27.27 18.62 0.13 4.77 3005.63 52.03 18.90 0.12 4.69 792.38 13.72 19.53 0.15 4.54 806.67 13.96 20.82 0.26 4.27 664.39 11.50 21.38 0.06 4.16 1580.84 27.37 21.52 0.13 4.13 1906.58 33.01 22.02 0.18 4.04 410.81 7.11 22.43 0.15 3.96 364.89 6.32 22.80 0.23 3.90 479.37 8.30 24.40 0.10 3.65 608.59 10.54 25.16 0.09 3.54 424.12 7.34 26.11 0.10 3.41 2521.03 43.64 27.01 0.13 3.30 388.79 6.73 27.77 0.15 3.21 210.15 3.64 29.67 0.15 3.01 314.29 5.44 30.21 0.26 2.96 233.20 4.04 30.78 0.20 2.90 266.96 4.62 31.63 0.36 2.83 418.96 7.25 33.42 0.31 2.68 268.71 4.65 34.00 0.20 2.64 207.67 3.60 Mono-napadisylate crystalline salt: It was prepared during high-throughput sieving by adding 0.2 mL of a 0.124 M free base solution in methanol and 0.2 mL of a 0.25 M 1,5-naphthalenedisulfonic acid solution in methanol to a glass plate, then evaporating the solvent. Afterward, 0.2 mL of solvent (acetonitrile or 0.001 M aqueous HCl) was added, and the mixture was heated to 50 °C for 4 hours, followed by evaporation. The salt was scaled up by adding 100 mg of free base to an 8 mL vial containing 3 mL of methanol and gently heating to dissolve. 1,5-Naphthalenedisulfonic acid (2 mL of a 0.25 M solution) was added at room temperature. The solids were collected after evaporation and filtration. The solubility in water was determined to be 0.3 mg / ml (pH 2.35). / co in / C7n7 / e / YiAi The mono-napadisylate crystalline salt of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 19. Table 19 / oo in / cznz / e / YiAi Angle 2-Theta° Interplanar distance value Angstrom Intensity Count (height) Int. rei. [%] 6.671 13.251 82.2 6.4 7.052 12.535 171 13.2 10.837 8.1642 360 27.9 12.266 7.2159 516 39.9 13.409 6.6034 442 34.2 14.572 6.0789 460 35.6 15.144 5.8503 356 27.6 15.75 5.6266 753 58.3 16.466 5.3837 788 61 17.831 4.9745 1292 100 18.824 4.7141 469 36.3 19.938 4.4533 955 73.9 21.828 4.0716 829 64.2 22.868 3.8888 605 46.9 23.487 3.7877 477 36.9 24.339 3.6571 307 23.8 25.263 3.5253 393 30.5 Nicotinate crystalline salt: It was prepared by sieving the primary salt. A 2 ml aliquot of THF was added to ~40 mg of free base. 1.05 equivalents of nicotinic acid were added, and the sample was subjected to temperature cycling for 3-5 days and then evaporated. The crystalline salt nicotinate of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 20. Table 20 Pos, [°2Th.] FWHM [°2Th.] Distance Height [cts] Int. laugh. [%] 3.69 0.05 23.96 4182.86 73.17 7.36 0.06 12.01 1796.70 31.43 8.55 0.08 10.34 3192.46 55.85 9.13 0.08 9.69 3381.54 59.16 10.01 0.08 8.84 1830.40 32.02 11.70 0.10 7.56 135.02 2.36 12.43 0.09 7.12 759.00 13.28 13.83 0.08 6.40 329.03 5.76 14.74 0.10 6.01 648.74 11.35 15.04 0.15 5.89 392.48 6.87 15.50 0.12 5.72 2090.66 36.57 16.70 0.09 5.31 3962.66 69.32 16.84 0.09 5.27 5013.53 87.70 17.62 0.10 5.03 2110.97 36.93 17.87 0.12 4.96 510.00 8.92 18.30 0.12 4.85 3434.06 60.07 18.58 0.13 4.78 1509.52 26.41 18.85 0.10 4.71 353.23 6.18 19.59 0.13 4.53 2097.05 36.69 19.99 0.15 4.44 5716.36 100.00 20.34 0.17 4.37 2282.98 39.94 20.76 0.15 4.28 2868.05 50.17 21.32 0.15 4.17 2273.73 39.78 22.03 0.14 4.03 1235.06 21.61 22.91 0.13 3.88 1620.93 28.36 23.43 0.14 3.80 3577.00 62.57 23.87 0.12 3.73 895.16 15.66 24.83 0.20 3.58 3276.98 57.33 24.92 0.05 3.58 2632.73 46.06 25.40 0.16 3.50 1715.21 30.01 25.95 0.23 3.43 2961.06 51.80 26.85 0.11 3.32 1483.29 25.95 26.94 0.09 3.31 1729.54 30.26 27.32 0.14 3.26 2177.84 38.10 28.01 0.19 3.18 1526.39 26.70 28.94 0.09 3.08 887.28 15.52 29.34 0.22 3.04 154.50 2.70 29.93 0.19 2.98 217.00 3.80 31.00 0.22 2.88 319.34 5.59 31.44 0.12 2.84 286.19 5.01 31.78 0.16 2.81 214.18 3.75 32.10 0.22 2.79 385.58 6.75 32.59 0.19 2.75 320.31 5.60 32.94 0.12 2.72 259.73 4.54 33.23 0.22 2.69 207.23 3.63 34.14 0.28 2.62 300.22 5.25 34.65 0.22 2.59 283.29 4.96. Form A of the crystalline salt oxalate: Procedure A: a high-yield sieving was prepared by adding 0.3 ml of a 0.05 M free base solution in methanol and 7J0PI n / P7n7 / e / Yi 0.3 ml of a 0.05 M oxalic acid solution in methanol to a glass plate, and then the solvent was evaporated, then 0.4 ml of solvent (water, 0.001 M aqueous HCl, acetone, acetonitrile or hexanes) was added and heated to 50 °C for 4 hours, and then evaporated. Procedure B: It was prepared by dissolving 47 mg of free base in ~10 ml of methanol, then 145 µL of a 102 mg / ml oxalic acid solution were added and the sample was placed in an N2 box. The solids were then suspended in water / ethanol at ATA. Form A of the crystalline salt omecamtiv mecarbil oxalate was characterized by an XRPD pattern comprising the maxima in Table 21. Table 21 77OPI n / O7n7 / e / YiAi Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 6.48 0.16 13.64 163.25 62.74 10.36 0.22 8.54 17.19 6.61 11.85 0.14 7.47 24.67 9.48 13.01 0.16 6.81 86.11 33.10 14.79 0.11 5.99 75.91 29.17 15.35 0.13 5.77 45.24 17.39 17.11 0.14 5.18 260.20 100.00 18.24 0.50 4.86 7.90 3.04 19.23 0.13 4.62 28.45 10.94 19.91 0.31 4.46 40.62 15.61 21.48 0.19 4.14 55.28 21.25 22.07 0.19 4.03 25.22 9.69 22.75 0.19 3.91 42.95 16.50 23.82 0.08 3.74 258.28 99.26 24.88 0.38 3.58 9.55 3.67 25.70 0.16 3.47 30.99 11.91 28.55 0.44 3.13 31.95 12.28 29.86 0.19 2.99 16.81 6.46 30.71 0.19 2.91 31.18 11.98 33.32 0.19 2.69 16.02 6.16 Form B of the oxalate crystalline salt: was prepared during the vapor sorption analysis of form A of the oxalate crystalline salt. The B form of the crystalline salt omecamtiv mecarbil oxalate was characterized by an XRPD pattern comprising the maxima in Table 22. Table 22 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 7.38 0.11 11.97 219.37 77.59 13.30 0.14 6.66 127.50 45.10 14.76 0.19 6.00 21.36 7.55 16.54 0.13 5.36 64.20 22.71 17.11 0.13 5.18 245.68 86.90 17.95 0.09 4.94 166.30 58.82 18.45 0.11 4.81 91.52 32.37 21.25 0.09 4.18 106.18 37.56 22.63 0.13 3.93 114.73 40.58 24.35 0.19 3.66 25.92 9.17 24.82 0.19 3.59 73.08 25.85 25.77 0.16 3.46 282.73 100.00 28.61 0.25 3.12 25.78 9.12 29.58 0.13 3.02 25.44 9.00 30.49 0.38 2.93 17.89 6.33 31.76 0.25 2.82 24.02 8.50 34.46 0.50 2.60 17.34 6.13 36.26 0.63 2.48 8.50 3.00 37.35 0.19 2.41 14.20 5.02 / co in / cznz / e / YiAi Table 23 shows the unique XRPD maxima for each of the A and B forms of oxalate crystalline salts disclosed herein. Table 23 Oxalate Form Maximum unique values for each form (°2Th.) Form A 6.48 13.01 23.82 Form B 7.38 13.30 16.54 Crystalline salicylate salt: It was prepared by sieving primary salt. A 2 mL aliquot of 2-propanol or toluene was added to ~40 mg of free base. 1.05 equivalents of salicylic acid in the form of a 1 M solution in THF were added, and the sample was subjected to temperature cycling for 3–5 days, after which the 2-propanol was evaporated. The crystalline salt of omecamtiv mecarbil salicylate was characterized by an XRPD pattern comprising the maxima in Table 24. Table 24 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 8.36 0.06 10.58 5425.26 100.00 9.78 0.06 9.05 634.48 11.69 10.08 0.06 8.78 1112.62 20.51 10.37 0.05 8.53 164.07 3.02 11.30 0.06 7.83 1739.85 32.07 11.82 0.05 7.48 271.53 5.00 12.00 0.05 7.38 412.51 7.60 13.69 0.06 6.47 843.47 15.55 13.80 0.04 6.42 717.86 13.23 14.25 0.15 6.21 74.68 1.38 15.51 0.09 5.71 588.40 10.85 16.75 0.09 5.29 3941.54 72.65 17.56 0.06 5.05 2277.70 41.98 17.77 0.05 4.99 1649.96 30.41 17.86 0.08 4.97 2140.62 39.46 18.67 0.09 4.75 1989.60 36.67 19.11 0.08 4.64 1216.29 22.42 19.27 0.06 4.61 812.90 14.98 19.62 0.08 4.52 795.44 14.66 20.02 0.08 4.43 709.58 13.08 20.22 0.13 4.39 1916.47 35.33 20.79 0.08 4.27 721.20 13.29 21.07 0.13 4.22 1935.15 35.67 21.78 0.09 4.08 313.94 5.79 22.19 0.05 4.01 532.25 9.81 22.39 0.10 3.97 665.30 12.26 22.75 0.08 3.91 677.94 12.50 22.92 0.06 3.88 673.25 12.41 23.58 0.13 3.77 3464.58 63.86 24.10 0.10 3.69 257.32 4.74 24.99 0.10 3.56 457.77 8.44 25.23 0.09 3.53 1162.00 21.42 25.59 0.09 3.48 506.81 9.34 26.79 0.09 3.33 620.95 11.45 27.40 0.17 3.26 1709.43 31.51 27.78 0.15 3.21 231.91 4.27 28.21 0.18 3.16 2479.45 45.70 28.76 0.10 3.10 278.54 5.13. / ce in / C7n7 / e / YiAi 29.32 0.13 3.05 236.55 4.36 29.65 0.15 3.01 309.68 5.71 29.94 0.06 2.98 491.39 9.06 30.50 0.13 2.93 198.15 3.65 31.34 0.31 2.85 86.35 1.59 32.15 0.20 2.78 138.16 2.55 32.74 0.10 2.74 175.34 3.23 — 0.06 2.63 656.95 12.11 7 / cpi n / cznz / R / vi Crystalline hemisuccinate salt: It was prepared during a high-performance sieving by adding 0.3 mL of a 0.05 M free base solution in methanol and 0.3 mL of a 0.05 M succinic acid solution in methanol to a glass plate, then evaporating the solvent, and then adding 0.4 mL of solvent (water, 0.001 M aqueous HCl, acetone, acetonitrile, or hexanes) and heating to 50 °C for 4 hours, and then evaporating. The solubility in water was determined to be 7.4 mg / mL (pH 4.7). The crystalline salt omecamtiv mecarbil hemi-succinate was characterized by an XRPD pattern comprising the maxima in Table 25. Table 25 Angle 2-Theta° Interplanar distance value Angstrom Intensity Count (height) Int. rei. [%] 5.488 16.102 191 11.5 6.319 13.988 504 30.5 7.596 11.638 237 14.3 12.932 6.8459 437 26.4 14.092 6.2847 245 14.8 15.079 5.8756 361 21.8 16.971 5.2244 307 18.6 18.768 4.728 1654 100 19.318 4.5947 1074 64.9 20.495 4.3334 1229 74.3 21.244 4.1822 790 47.8 21.889 4.0604 849 51.4 23.492 3.7869 1651 99.8 24.228 3.6736 531 32.1 25.364 3.5116 488 29.5 26.671 3.3424 749 45.3 27.389 3.2563 636 38.5 28.316 3.1518 635 38.4 Form A of the bis-sulfate crystalline salt: Procedure A: It was prepared during high-throughput sieving by adding 0.2 mL of a 0.124 M solution of free base in methanol and 0.2 mL of a 0.25 M solution of sulfuric acid in methanol to a glass plate, then evaporating the solvent, and then adding 0.2 mL of solvent (0.001 M THF or HCl aq) and heating to 50 °C for 4 hours and then evaporating. The salt was scaled up by adding 100 mg of free base to an 8 mL vial and 4 mL of methanol and heating gently to dissolve. Sulfuric acid (2 mL of a 0.25 M solution) was added at room temperature. The solids were collected after evaporation to dryness. Procedure B: It was prepared by dissolving 200.7 mg of free base (1 eq) and 1.05 ml of 1 M sulfuric acid (2.1 eq) in 5 ml of methanol at 50 °C, and then cooled for precipitation. Procedure C: was formed when Form D was exposed to storage conditions of 40 °C / 75% RH for 3 days. The solubility in water was determined to be 16 mg / ml (pH 1.5). Form A of the crystalline salt omecamtiv mecarbil bis-sulfate was characterized by an XRPD pattern comprising the maxima in Table 26. Table 26 / co in / cznz / e / YiAi Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 5.39 0.05 16.40 803.64 14.66 7.55 0.06 11.71 915.17 16.70 8.33 0.05 10.62 247.72 4.52 10.13 0.08 8.73 62.00 1.13 14.35 0.09 6.17 3211.66 58.60 14.63 0.08 6.05 340.15 6.21 15.12 0.09 5.86 414.53 7.56 15.64 0.09 5.66 517.83 9.45 16.00 0.10 5.54 503.75 9.19 16.17 0.09 5.48 833.42 15.21 16.39 0.08 5.41 379.73 6.93 16.71 0.08 5.31 565.39 10.32 16.92 0.06 5.24 1727.49 31.52 17.07 0.08 5.19 1764.97 32.20 17.68 0.09 5.02 464.46 8.47 18.33 0.09 4.84 344.30 6.28 18.60 0.08 4.77 648.56 11.83 19.26 0.12 4.61 5480.54 100.00 19.75 0.10 4.50 350.13 6.39 20.22 0.08 4.39 1216.75 22.20 20.83 0.10 4.26 1272.51 23.22 21.03 0.08 4.23 507.32 9.26 21.38 0.09 4.16 1278.02 23.32 22.27 0.12 3.99 1717.52 31.34 22.77 0.09 3.90 602.87 11.00 23.14 0.13 3.84 1861.14 33.96 23.42 0.08 3.80 727.12 13.27 23.76 0.12 3.75 1376.36 25.11 24.32 0.12 3.66 1360.34 24.82 25.11 0.13 3.55 1608.13 29.34 25.48 0.41 3.50 169.13 3.09 25.74 0.13 3.46 2483.24 45.31 26.30 0.08 3.39 445.14 8.12 26.46 0.06 3,37 589.33 10.75 27.71 0.06 3.22 1509.03 27.53 28.15 0.08 3.17 1156.37 21.10 28.90 0.08 3.09 415.94 7.59 29.24 0.09 3.05 516.64 9.43 29.92 0.06 2.99 927.24 16.92 30.38 0.13 2.94 210.94 3.85 30.65 0.08 2.92 266.96 4.87 31.57 0.13 2.83 212.99 3.89 32.14 0.09 2.79 339.08 6.19 33.10 0.18 2.71 172.88 3.15 33.78 0.20 2.65 181.24 3.31 34.22 0.15 2.62 131.00 2.39 Form B of the bis-sulfate crystalline salt: was prepared by dissolving 150 mg of free base in 20 mL of acetone and adding 22 mL of 17.6 M sulfuric acid, and then subjecting it to sonication. The isolated solids were suspended in water at room temperature. The solubility in water was determined to be 9 mg / mL (pH 3.5). The B form of the crystalline salt omecamtiv mecarbil bis-sulfate was characterized by an XRPD pattern comprising the maxima in Table 27. 77OPI n / P7n7 / e / Yi Table 27 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 10.67 0.19 8.29 12.89 6.12 11.72 0.19 7.55 160.31 76.09 12.17 0.19 7.27 80.11 38.02 12.93 0.13 6.85 43.21 20.51 14.57 0.22 6.08 17.85 8.47 17.79 0.13 4.99 30.92 14.67 18.39 0.11 4.82 82.79 39.29 18.76 0.09 4.73 32.73 15.54 19.84 0.22 4.47 101.51 48.18 20.48 0.11 4.34 124.27 58.98 21.34 0.25 4.16 11.41 5.41 21.90 0.25 4.06 10.23 4.86 23.60 0.17 3.77 210.68 100.00 24.23 0.13 3.67 35.79 16.99 25.13 0.16 3.54 44.10 20.93 25.63 0.19 3.48 98.90 46.94 29.30 0.31 3.05 29.96 14.22 30.12 0.13 2.97 47.50 22.55 30.98 0.19 2.89 15.83 7.51 31.48 0.19 2.84 18.11 8.60 31.94 0.19 2.80 13.68 6.49 36.02 0.25 2.49 10.23 4.86 36.85 0.50 2.44 7.64 3.63 38.16 0.25 2.36 11.73 5.57 j pp in / P7n7 / e / YiAi Form C of the bis-sulfate crystalline salt: was prepared by heating Form B of bis-sulfate in TGA. The C form of the crystalline salt omecamtiv mecarbil bis-sulfate was characterized by an XRPD pattern comprising the maxima in Table 28. Table 28 Pos. [°2Th.] FWHM [°2Th.] Interplanar Distance [A] Height [cts] Internal Interplanarity [%] 8.20 0.19 10.79 30.31 4.27 10.39 0.13 8.51 179.40 25.28 10.72 0.09 8.25 226.72 31.94 10.98 0.13 8.06 252.05 35.51 11.49 0.22 7.70 136.57 19.24 12.17 0.19 7.27 132.34 18.65 12.52 0.16 7.07 159.11 22.42 12.99 0.22 6.82 238.57 33.61 13.56 0.22 6.53 122.29 17.23 15.98 0.25 5.55 37.67 5.31 16.74 0.19 5.30 135.94 19.15 17.11 0.16 5.18 296.18 41.73 17.43 0.22 5.09 332.88 46.90 18.04 0.31 4.92 107.59 15.16 19.60 0.14 4.53 249.29 35.12 20.94 0.22 4.24 215.86 30.41 21.53 0.22 4.13 109.98 15.50 22.47 0.31 3.96 100.45 14.15 23.09 0.28 3.85 136.51 19.23 23.98 0.31 3.71 58.62 8.26 24.76 0.19 3.60 230.19 32.43 25.25 0.31 3.53 709.74 100.00 25.87 0.16 3.44 263.23 37.09 26.51 0.19 3.36 179.86 25.34 27.63 0.76 3.23 91.65 12.91 29.33 0.50 3.04 30.11 4.24 32.14 0.38 2.79 44.36 6.25 33.91 0.38 2.64 17.82 2.51 35.27 0.38 2.55 15.44 2.18 39.25 0.25 2.30 22.20 3.13 77OPI n / P7n7 / e / Yi Form D of the crystalline sulfate salt: was prepared by sieving the primary salt. To prepare form D, a 2 mL aliquot of acetone was added to approximately 40 mg of free base. 1.05 equivalents of sulfuric acid in the form of a 1 M solution in THF were added, and the sample was subjected to temperature cycling for 3–5 days. The D form of the crystalline salt omecamtiv mecarbil sulfate was characterized by an XRPD pattern comprising the maxima in Table 29. Table 29 Pos. [°2Th.] FWHM [°2Th.] Interplanar Distance [A] Height [cts] Internal Interplanarity [%] 7.32 0.08 12.08 844.93 59.30 8.02 0.05 11.03 224.63 15.77 11.67 0.10 7.58 138.68 9.73 12.20 0.10 7.25 169.56 11.90 12.55 0.10 7.05 121.39 8.52 13.57 0.08 6.52 1067.44 74.92 14.54 0.10 6.09 805.82 56.56 16.29 0.08 5.44 758.59 53.24 16.41 0.08 5.40 705.84 49.54 16.91 0.15 5.24 520.14 36.51 17.36 0.20 5.11 373.69 26.23 18.70 0.06 4.74 783.62 55.00 20.44 0.15 4.34 1424.79 100.00 21.02 0.15 4.23 587.18 41.21 21.77 0.15 4.08 625.52 43.90 22.37 0.15 3.97 403.56 28.32 22.90 0.15 3.88 1136.86 79.79 23.72 0.15 3.75 749.74 52.62 24.28 0.08 3.67 771.24 54.13 25.14 0.13 3.54 490.08 34.40 25.88 0.10 3.44 399.16 28.02 26.58 0.09 3.35 808.90 56.77 27.25 0.15 3.27 783.97 55.02 28.10 0.15 3.18 200.02 14.04 29.43 0.18 3.04 218.32 15.32 30.45 0.41 2.94 99.72 7.00 33.15 0.31 2.70 89.81 6.30 33.88 0.15 2.65 121.18 8.51 zvcci n / cznz / e / Yi Table 30 shows the unique XRPD maxima for each of the AD forms of sulfate crystal salts disclosed herein. Table 30 Sulfate Form Unique Maximums for Each Form (°2Th.) Form A 5.39 7.55 14.35 19.26 20.22 Form B 11.72 20.48 Form C 10.98 11.49 18.04 19.60 Form D 7.32 8.02 20.44 2-Hydroxyethanesulfonate crystalline salt: was prepared by sieving primary salt. A 2 mL aliquot of THF, acetonitrile, or isopropyl acetate was added to ~40 mg of free base. 1.05 equivalents of 2-hydroxyethanesulfonic acid as a solid and 1 equivalent of 1 M hydrochloric acid were added, and the sample was subjected to temperature cycling for 3–5 days. The crystalline salt 2-hydroxyethane-sulfonate of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 31. Table 31 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 6.26 0.08 14.13 219.45 9.02 6.69 0.18 13.21 374.53 15.39 9.95 0.06 8.89 2434.20 100.00 14.43 0.15 6.14 98.15 4.03 14.99 0.23 5.91 360.35 14.80 15.51 0.15 5.71 182.59 7.50 16.37 0.09 5.41 438.44 18.01 17.06 0.26 5.20 148.91 6.12 17.85 0.08 4.97 916.01 37.63 19.61 0.15 4.53 272.20 11.18 19.93 0.05 4.46 695.74 28.58 20.07 0.06 4.42 590.93 24.28 20.46 0.12 4.34 487.31 20.02 20.95 0.18 4.24 261.07 10.73 22.06 0.18 4.03 158.42 6.51 22.89 0.26 3.88 158.38 6.51 23.96 0.15 3.71 128.47 5.28 24.41 0.13 3.65 155.88 6.40 25.06 0.15 3.55 488.47 20.07 26.20 0.18 3.40 632.72 25.99 26.98 0.20 3.30 133.39 5.48 27.92 0.08 3.20 162.41 6.67 28.43 0.15 3.14 116.74 4.80 29.98 0.04 2.98 438.04 18.00 32.16 0.04 2.78 443.24 18.21 33.38 0.41 2.68 86.61 3.56 34.39 0.06 2.61 387.48 15.92 Form A of the bis-tartrate crystalline salt: was prepared by dissolving 200.7 mg (1 eq) of free base and 525 μL (30.02 g in 100 mL of methanol, 2.1 eq) in 20 mL of methanol and thermal cycling at 40 °C / TA twice. The solubility in water was determined to be > 53 mg / mL (pH 3.28). Form A of the crystalline salt bis-tartrate of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 32. Table 32 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 4.20 0.19 21.02 968.44 59.18 4.77 0.19 18.52 1062.98 64.96 7.49 0.16 11.80 715.72 43.74 7.67 0.09 11.52 629.63 38.48 8.22 0.19 10.75 793.41 48.48 8.43 0.09 10.49 699.24 42.73 9.49 0.19 9.32 377.23 23.05 11.18 0.25 7.91 193.33 11.81 11.88 0.31 7.45 208.48 12.74 13.05 0.22 6.79 590.85 36.11 13.26 0.13 6.68 608.71 37.20 14.98 0.11 5.92 1399.17 85.50 15.14 0.22 5.85 1490.06 91.05 16.42 0.35 5.40 437.01 26.70 17.34 0.08 5.11 983.61 60.11 17.47 0.14 5.08 1247.90 76.26 18.02 0.19 4.92 1121.36 68.52 18.23 0.16 4.87 911.65 55.71 18.72 0.13 4.74 441.84 27.00 19.20 0.16 4.62 370.82 22.66 21.19 0.11 4.19 1636.46 100.00 22.50 0.19 3.95 667.89 40.81 23.86 0.16 3.73 212.59 12.99 24.53 0.41 3.63 339.28 20.73 25.67 0.38 3.47 528.93 32.32 26.30 0.31 3.39 451.92 27.62 28.14 0.25 3.17 388.50 23.74 28.44 0.22 3.14 285.60 17.45 29.87 0.38 2.99 258.33 15.79 31.32 0.31 2.86 101.08 6.18 32.48 0.25 2.76 128.85 7.87 33.69 0.25 2.66 103.91 6.35 34.42 0.25 2.61 158.44 9.68 35.36 0.31 2.54 97.83 5.98 35.92 0.19 2.50 84.54 5.17 36.60 0.31 2.46 82.62 5.05 37.41 0.25 2.40 136.23 8.32 37.88 0.25 2.38 96.44 5.89. / ce in / C7n7 / e / YiAi Form B of the bis-tartrate crystalline salt: was prepared by dissolving 1.004 g of omecamtiv mecarbil and 0.788 g of L-tartaric acid (2.1 eq) in 50 ml of MeOH at 50 °C, and then cooled for precipitation. The B form of the crystalline salt bis-tartrate of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 33. Table 33 77ORI n / cznz / R / viAi Pos. [°2Th.] FWHM [°2Th.] Distance = interplanar [Á] Height [cts] Int. reí. [%] 3.77 0.17 23.43 971.26 100.00 4.72 0.27 18.74 635.71 65.45 5.69 0.27 15.52 516.33 53.16 6.95 0.27 12.73 358.34 36.89 9.34 0.27 9.46 200.35 20.63 10.07 0.23 8.78 434.70 44.76 11.18 0.54 7.92 167.11 17.21 12.63 0.20 7.01 158.00 16.27 15.18 0.20 5.84 190.67 19.63 17.69 0.17 5.01 282.08 29.04 22.35 0.20 3.98 177.49 18.27 25.46 0.40 3.50 62.01 6.38 Form C of the bis-tartrate crystalline salt: was prepared by suspending Form B of bis-tartrate in water. The C form of the crystalline salt bis-tartrate of omecamtiv mecarbil was characterized by an XRPD pattern comprising the maxima in Table 34. Table 34 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 3.57 0.13 24.73 920.53 89.99 3.86 0.15 22.88 1022.92 100.00 4.78 0.40 18.49 513.98 50.25 6.23 0.20 14.19 427.74 41.82 7.04 0.13 12.56 270.90 26.48 9.36 0.17 9.45 637.85 62.36 13.08 0.10 6.77 549.91 53.76 13.96 0.17 6.34 239.78 23.44 15.84 0.17 5.59 348.37 34.06 16.88 0.20 5.25 121.74 11.90 17.60 0.27 5.04 146.72 14.34 18.20 0.20 4.87 147.06 14.38 18.73 0.23 4.74 245.18 23.97 20.40 0.20 4.35 268.32 26.23 22.58 0.27 3.94 120.04 11.73 25.44 0.40 3.50 192.03 18.77 26.06 0.47 3.42 213.11 20.83 28.61 0.40 3.12 106.58 10.42 zvcci n / cznz / e / Yi Form D of the crystalline mono-tartrate salt: was prepared by mixing 1.004 g of omecamtiv mecarbil and 0.375 g of L-tartaric acid (1 eq) in 10 ml of H2O at 5% in THF at 50 °C, and then cooled for precipitation. The D form of the crystalline salt omecamtiv mecarbil mono-tartrate was characterized by an XRPD pattern comprising the maxima in Table 35. Table 35 Pos. [°2Th.] FWHM [°2Th.] Interplanar distance [Á] Height [cts] Int. reí. [%] 6.94 0.12 12.74 377.02 15.46 9.77 0.17 9.05 478.47 19.62 10.87 0.17 8.14 2097.98 86.02 12.74 0.13 6.95 204.81 8.40 13.04 0.13 6.79 144.17 5.91 13.79 0.15 6.42 871.83 35.75 14.54 0.20 6.09 418.22 17.15 14.86 0.13 5.96 315.83 12.95 15.40 0.18 5.75 2345.40 96.17 17.36 0.18 5.11 1127.77 46.24 17.74 0.17 5.00 512.38 21.01 18.58 0.12 4.78 598.49 24.54 18.87 0.17 4.70 693.22 28.42 19.25 0.17 4.61 322.02 13.20 20.71 0.13 4.29 293.45 12.03 21.78 0.17 4.08 1734.64 71.13 23.11 0.20 3.85 97.51 4.00 23.58 0.13 3.77 214.55 8.80 24.69 0.12 3.61 423.81 17.38 25.43 0.17 3.50 2438.82 100.00 26.24 0.20 3.40 529.42 21.71 26.50 0.13 3.36 437.75 17.95 26.99 0.27 3.30 259.96 10.66 28.58 0.27 3.12 73.70 3.02 29.43 0.27 3.03 100.12 4.11 30.40 0.13 2.94 161.38 6.62 32.74 0.27 2.74 127.69 5.24 34.76 0.17 2.58 210.18 8.62 35.46 0.17 2.53 118.22 4.85 36.31 0.20 2.47 191.26 7.84 37.01 0.13 2.43 138.71 5.69 37.64 0.27 2.39 131.07 5.37 / co in / C7n7 / e / YiAi Table 36 shows the unique XRPD maxima for each of the AD forms of tartrate crystalline salts disclosed herein. Table 36 Tartrate Form Maximum unique values for each form (°2Th.) Form A 4.20 7.49 8.22 11.88 16.42 21.19 Form B 3.77 5.69 10.07 Form C 3.57 6.23 15.84 Form D 9.77 15.40
Claims
1. A crystalline salt of omecamtiv mecarbil ethane sulfonate, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 8.61, 16.14, 16.76, 16.97, 20.73, 20.96, 25.95 and 26.30 ± 0.2° 20 using Cu Ka radiation.
2. The omecamtiv mecarbil according to claim 1, further characterized by XRPD pattern maxima at 17.23, 18.35, 19.20, 20.27, 23.73, 25.24 and 27.09 ± 0.2° 20 using Cu Ka radiation.
3. The omecamtiv mecarbil according to claim 1 or 2, having an XRPD pattern as shown in Figure 18, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
4. A crystalline salt bis-fumarate of omecamtiv mecarbil, form A, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 5.64, 15.76, 22.03 and 23.87 ± 0.2° 20 using Cu Ka radiation.
5. The omecamtiv mecarbil according to claim 4, further characterized by XRPD pattern maxima at 16.80, 21.55, 21.87, 23.61, 23.87, 26.01 and 27.20 ± 0.2° 20 using Cu Ka radiation.
6. The omecamtiv mecarbil according to claim 5, further characterized by XRPD pattern maxima at 10.80, 12.04, 15.76, 16.40, 17.94, 18.32, 19.87, 20.61, 22.88, 27.86, 32.73 and 36.54 ± 0.2° 20 using Cu Ka radiation.
7. The omecamtiv mecarbil according to any of claims 4 to 6, having an XRPD pattern as shown in Figure 20, wherein said XRPD pattern comprises maxima that may vary by ± 0.2°.
8. The omecamtiv mecarbil in accordance with any of claims 4 to 7, having a thermogravimetric analysis (TGA) as shown in Figure 21.
9. A crystalline salt bis-fumarate of omecamtiv mecarbil, form B, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 5.68, 6.11, 13.13, 18.08 and 22.47 ± 0.2° 20 using Cu Ka radiation.
10. The omecamtiv mecarbil according to claim 9, further characterized by XRPD pattern maxima at 9.69, 11.43, 12.92, 15.95, 20.81, 22.95, 26.04, 27.01 and 28.43 ± 0.2° 20 using Cu Ka radiation.
11. The omecamtiv mecarbil according to claim 10, further characterized by XRPD pattern maxima at 19.52, 24.53, 31.37, 32.32, 34.89, 35.89 and 37.16 ± 0.2° 20 using Cu Ka radiation.
12. The omecamtiv mecarbil according to any of claims 9 to 11, having an XRPD pattern as shown in Figure 22, wherein said XRPD pattern 7 j co in / C7n7 / e / YiAi comprises maxima that may vary by ± 0.2°.
13. The omecamtiv mecarbil in accordance with any of claims 9 to 12, having a thermogravimetric analysis (TGA) as shown in Figure 23.
14. A crystalline salt bis-fumarate of omecamtiv mecarbil, form C, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 5.88, 18.79, 25.41 and 26.86 ± 0.2° 20 using Cu Ka radiation.
15. The omecamtiv mecarbil according to claim 14, further characterized by XRPD pattern maxima at 12.74, 13.56, 17.15, 17.63, 20.29, 21.47, 21.77, 22.21, 22.92, 23.58, 24.15, 25.41, 26.78 and 27.83 ± 0.2° 20 using Cu Ka radiation.
16. The omecamtiv mecarbil according to claim 14 or 15, having an XRPD pattern as shown in Figure 24, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
17. The omecamtiv mecarbil in accordance with any of claims 14 to 16, having a thermogravimetric analysis (TGA) as shown in Figure 25.
18. A crystalline salt mono-fumarate of omecamtiv mecarbil, form D, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 8.01, 15.20 and 20.02 ± 0.2° 20 using Cu Ka radiation.
19. The omecamtiv mecarbil according to claim 18, further characterized by XRPD pattern maxima at 12.11, 12.67, 14.46, 16.01, 16.57, 17.04, 17.63, 20.51, 21.75, 22.86, 24.25, 24.97, 25.84, 26.17, 27.10, 27.97 and 29.21 ± 0.2° 20 using Cu Ka radiation.
20. The omecamtiv mecarbil according to claim 18 or 19, having an XRPD pattern as shown in Figure 26, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
21. The omecamtiv mecarbil according to any of claims 18 to 20, having an endothermic transition of 110 °C to 130 °C, as measured by differential scanning calorimetry.
22. The omecamtiv mecarbil according to claim 21, wherein the endothermic transition is at 125 °C ± 3 °C.
23. The omecamtiv mecarbil in accordance with any of claims 18 to 22, having a thermogravimetric analysis (TGA) as shown in Figure 28.
24. A bis-maleate crystalline salt of omecamtiv mecarbil, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 9.97, 15.31, 16.04 and 26.96 ± 0.2° 20 using Cu Ka radiation.
25. The omecamtiv mecarbil according to claim 24, further characterized by XRPD pattern maxima at 10.56, 13.25, 15.53, 16.38, 17.44, 17.70, 18.17, 19.00, 20.13, 21.47, 22.31, 22.44, 24.38, 24.64, 25.66, 26.66 and 27.83 ± 0.2° 26 using Cu Κα radiation.
26. The omecamtiv mecarbil according to claim 25, further characterized by XRPD pattern maxima at 4.99, 14.83, 17.10, 22.02, 28.55, 30.76, 32.01, 34.39 and 34.51 ± 0.2° 26 using Cu Κα radiation.
27. The omecamtiv mecarbil according to any of claims 24 to 26, having an XRPD pattern as shown in Figure 30, wherein said XRPD pattern comprises maxima that may vary by ± 0.2°.
28. The omecamtiv mecarbil according to any of claims 24 to 27, having an endothermic transition of 160 °C to 210 °C, as measured by differential scanning calorimetry.
29. The omecamtiv mecarbil according to claim 28, wherein the endothermic transition is at 190 °C ± 3 °C.
30. The omecamtiv mecarbil in accordance with any of claims 24 to 29, having a thermogravimetric analysis (TGA) as shown in Figure 32.
31. A bis-malonate crystalline salt of omecamtiv mecarbil, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 4.74, 11.37, 14.25, 15.13, 18.29, 20.14, 23.87, 27.78 and 28.01 ± 0.2° 26 using Cu Κα radiation.
32. The omecamtiv mecarbil according to claim 31, further characterized by XRPD pattern maxima at 9.30, 13.73, 16.45, 16.83, 18.08, 18.88, 19.54, 20.77, 21.21, 23.32, 24.67, 26.51, 27.59 and 28.90 ± 0.2° 26 using Cu Κα radiation.
33. The omecamtiv mecarbil according to claim 32, further characterized by XRPD pattern maxima at 15.69, 25.72, 30.18, 33.70, 34.19 ± 0.2° 26 using Cu KA radiation.
34. The omecamtiv mecarbil according to any of claims 31 to 33, having an XRPD pattern as shown in Figure 33, wherein said XRPD pattern comprises maxima that may vary by ± 0.2°.
35. The omecamtiv mecarbil in accordance with any of claims 31 to 34, having a thermogravimetric analysis (TGA) as shown in Figure 34.
36. A form A of omecamtiv mecarbil mesylate crystalline salt, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 4.02, 4.87, 15.21, 15.86, 20.53 and 24.39 ± 0.2° 26 using Cu Κα radiation.
37. The omecamtiv mecarbil according to claim 36, further characterized by XRPD pattern maxima 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° 26 using Cu Κα radiation.
38. The omecamtiv mecarbil according to claim 36 or 37, having an XRPD pattern as shown in Figure 35, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
39. The omecamtiv mecarbil in accordance with any of claims 36 to 38, having a thermogravimetric analysis (TGA) as shown in Figure 36.
40. A B form of omecamtiv mecarbil bis-mesylate crystalline salt, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 8.30, 8.94, 9.59, 12.15, 14.37, 19.82, 20.29, 22.04 and 25.02 ± 0.2° 20 using Cu Ka radiation.
41. The omecamtiv mecarbil according to claim 40, further characterized by XRPD pattern maxima at 11.66, 16.18, 16.64, 16.81, 17.07, 17.19, 17.41, 17.76, 19.24, 20.66, 21.62, 22.39, 23.95, 24.60, 25.59, 25.89, 27.14, 27.35, 27.41 and 29.45 ± 0.2° 20 using Cu Ka radiation.
42. The omecamtiv mecarbil according to claim 41, further characterized by XRPD pattern maxima at 10.78, 11.15, 14.93, 15.36, 15.57, 23.54, 26.14, 26.49, 27.89, 28.86, 29.89, 31.11, 32.47, 33.10, 33.51, 34.56 ± 0.2° 20 using Cu Ka radiation.
43. The omecamtiv mecarbil according to any of claims 40 to 42, having an XRPD pattern as shown in Figure 37, wherein said XRPD pattern comprises maxima that may vary by ± 0.2°.
44. A bis-naphthalate-2-sulfonate crystalline salt of omecamtiv mecarbil, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 4.49, 18.20, 18.62, 21.38, 21.52 and 26.11 ±0.2° 20 using Cu Ka radiation.
45. The omecamtiv mecarbil according to claim 44, further characterized by XRPD pattern maxima at 6.25, 6.65, 13.44, 14.39, 14.92, 16.28, 18.90, 19.53, 20.82, 22.02, 22.43, 22.80, 24.40, 25.16, 27.01, 29.67, 31.63 and 33.42 ± 0.2° 20 using Cu Ka radiation.
46. The omecamtiv mecarbil according to claim 44 or 45, having an XRPD pattern as shown in Figure 40, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
47. A mono-napadisylate crystalline salt of omecamtiv mecarbil, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 12.27, 15.75, 16.5, 17.83, 19.94, 21.83 and 22.87 ± 0.2° 20 using Cu Ka radiation.
48. The omecamtiv mecarbil according to claim 47, further comprising XRPD pattern maxima at 10.84, 13.41, 14.57, 15.14, 18.82, 23.49, 24.34 and 25.26 ± 0.2° 20 using Cu Ka radiation.
49. The omecamtiv mecarbil according to claim 47 or 48, having an XRPD pattern as shown in Figure 42, wherein said XRPD pattern comprises z / co in / cznz / e / YiAi 78 maxima that may vary by ± 0.2°.
50. The omecamtiv mecarbil according to any of claims 47 to 49, having a differential scanning calorimetry (DSC) as shown in Figure 43.
51. The omecamtiv mecarbil in accordance with any of claims 47 to 50, having a thermogravimetric analysis (TGA) as shown in Figure 44.
52. A crystalline salt of omecamtiv mecarbil nicotinate, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima 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 Ka radiation.
53. The omecamtiv mecarbil according to claim 52, further characterized by XRPD pattern maxima at 7.36, 10.01, 12.43, 14.74, 15.50, 17.62, 18.58, 19.59, 20.34, 21.32, 22.03, 22.91, 23.87, 24.92, 25.40, 26.85, 26.94, 27.32, 28.01 and 28.94 ± 0.2° 20 using Cu Ka radiation.
54. The omecamtiv mecarbil according to claim 52 or 53, having an XRPD pattern as shown in Figure 45, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
55. A crystalline salt omecamtiv mecarbil oxalate, form A, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 6.48, 13.01 and 23.82 ± 0.2° 20 using Cu Ka radiation.
56. The omecamtiv mecarbil according to claim 55, further characterized by XRPD pattern maxima at 10.36, 11.85, 14.79, 15.35, 17.11, 19.23, 19.91, 21.48, 22.07, 22.75, 25.70, 28.55 and 30.71 ± 0.2° 2Θ using Cu Ka radiation.
57. The omecamtiv mecarbil according to claim 55 or 56, having an XRPD pattern as shown in Figure 47, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
58. The omecamtiv mecarbil according to any of claims 55 to 57, having an endothermic transition of 190 °C to 230 °C, as measured by differential scanning calorimetry.
59. The omecamtiv mecarbil according to claim 58, wherein the endothermic transition is at 209 °C ± 3 °C.
60. The omecamtiv mecarbil in accordance with any of claims 55 to 56, having a thermogravimetric analysis (TGA) as shown in Figure 49.
61. A crystalline salt of omecamtiv mecarbil oxalate, form B, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 7.38, 13.30 and 16.54 ± 0.2° 20 using Cu Ka radiation. 7 j co in / C7n7 / e / YiAi 62. The omecamtiv mecarbil according to claim 61, further characterized by XRPD pattern maxima at 17.11, 17.95, 18.45, 21.25, 22.63, 24.82 and 25.77 ± 0.2° 20 using Cu Ka radiation.
63. The omecamtiv mecarbil according to claim 62, further characterized by XRPD pattern maxima at 14.76, 24.35, 28.61, 29.58, 30.49, 31.76, 34.46 and 37.35 ± 0.2° 20 using Cu Ka radiation.
64. The omecamtiv mecarbil according to any of claims 61 to 63, having an XRPD pattern as shown in Figure 50, wherein said XRPD pattern comprises maxima that may vary by ± 0.2°.
65. The omecamtiv mecarbil in accordance with any of claims 61 to 64, having a thermogravimetric analysis (TGA) as shown in Figure 51.
66. A crystalline salt of omecamtiv mecarbil salicylate, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 8.36, 16.75, 17.56, 23.58 and 28.21 ± 0.2° 20 using Cu Ka radiation.
67. The omecamtiv mecarbil according to claim 66, further characterized by XRPD pattern maxima at 10.08, 11.30, 13.69, 17.77, 17.86, 18.67, 19.11, 20.22, 21.07, 25.23 and 27.40 ± 0.2° 20 using Cu Ka radiation.
68. The omecamtiv mecarbil according to claim 67, further characterized by XRPD pattern maxima at 9.78, 12.00, 13.80, 15.51, 19.27, 19.62, 20.02, 20.79, 22.19, 22.39, 22.75, 22.92, 24.99, 25.59, 26.79, 29.94 and 34.07 ± 0.2° 20 using Cu Ka radiation.
69. The omecamtiv mecarbil according to any of claims 66 to 68, having an XRPD pattern as shown in Figure 53, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
70. A crystalline salt of omecamtiv mecarbil hemisuccinate, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 6.32, 18.87, 19.32, 20.5, 21.24, 21.89, 23.49, 24.23 and 26.71 ± 0.2° 20 using Cu Ka radiation.
71. The omecamtiv mecarbil according to claim 70, further comprising XRPD pattern maxima at 12.93, 15.08, 16.97, 25.36, 27.39 and 28.32 ± 0.2° 20 using Cu Ka radiation.
72. The omecamtiv mecarbil according to claim 70 or 71, having an XRPD pattern as shown in Figure 55, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
73. The omecamtiv mecarbil according to any of claims 70 to 72, having an endothermic transition of 155 °C to 190 °C, measured by 7 / co in / cznz / e / YiAi 80 differential scanning calorimetry.
74. The omecamtiv mecarbil according to claim 73, wherein the endothermic transition is at 171 °C ± 3 °C.
75. A crystalline salt bis-sulfate of omecamtiv mecarbil, form A, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 5.39, 7.55, 14.35, 19.26 and 20.22 ± 0.2° 20 using Cu Ka radiation.
76. The omecamtiv mecarbil according to claim 75, further characterized by XRPD pattern maxima at 16.17, 16.71, 16.92, 17.07, 18.60, 20.83, 21.38, 22.27, 22.77, 23.14, 23.42, 23.76, 24.32, 25.11, 25.74, 26.46, 27.71, 28.15 and 29.92 ± 0.2° 20 using Cu Ka radiation.
77. The omecamtiv mecarbil according to claim 75 or 76, having an XRPD pattern as shown in Figure 57, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
78. A crystalline salt bis-sulfate of omecamtiv mecarbil, form B, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 11.72 and 20.48 ± 0.2° 20 using Cu Ka radiation.
79. The omecamtiv mecarbil according to claim 78, further characterized by XRPD pattern maxima at 12.17, 12.93, 17.79, 18.39, 18.76, 19.84, 23.60, 25.13, 25.63 and 30.12 ± 0.2° 20 using Cu Ka radiation.
80. The omecamtiv mecarbil according to claim 78 or 79, having an XRPD pattern as shown in Figure 58, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
81. The omecamtiv mecarbil in accordance with any of claims 78 to 80, having a thermogravimetric analysis (TGA) as shown in Figure 59.
82. A crystalline salt bis-sulfate of omecamtiv mecarbil, form C, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 10.98, 11.49, 18.04 and 19.60 ± 0.2° 26 using Cu Ka radiation.
83. The omecamtiv mecarbil according to claim 82, further characterized by XRPD pattern maxima at 10.39, 10.72, 12.52, 12.99, 17.11, 17.43, 20.94, 24.76, 25.25, 25.87 and 26.51 ± 0.2° 26 using Cu Ka radiation.
84. The omecamtiv mecarbil according to claim 82 or 83, having an XRPD pattern as shown in Figure 60, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
85. The omecamtiv mecarbil according to any of claims 82 to 84, having a thermogravimetric analysis (TGA) as shown in Figure 61. 7 / co in / C7n7 / e / YiAi 86. A crystalline salt omecamtiv mecarbil sulfate, form D, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 7.32, 8.02 and 20.44 ± 0.2° 20 using Cu Ka radiation.
87. The omecamtiv mecarbil according to claim 86, further characterized by XRPD pattern maxima at 13.57, 14.54, 16.29, 16.41, 16.91, 17.36, 18.70, 21.02, 21.77, 22.37, 22.90, 23.72, 24.28, 25.14, 25.88, 26.58, 27.25, 28.10 and 29.43 ± 0.2° 2Θ using Cu Ka radiation.
88. The omecamtiv mecarbil according to claim 86 or 87, having an XRPD pattern as shown in Figure 62, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
89. A crystalline salt 2-hydroxyethane-sulfonate of omecamtiv mecarbil, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 9.95, 17.85, 19.93, 20.07, 20.46, 25.06 and 26.20 ± 0.2° 20 using Cu Ka radiation.
90. The omecamtiv mecarbil according to claim 89, further characterized by XRPD pattern maxima at 6.26, 6.69, 14.99, 16.37, 19.61, 20.95, 29.98, 32.16 and 34.39 ± 0.2° 20 using Cu Ka radiation.
91. The omecamtiv mecarbil according to claim 89 or 90, having an XRPD pattern as shown in Figure 65, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
92. A crystalline salt bis-tartrate of omecamtiv mecarbil, form A, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 4.20, 7.49, 8.22, 11.88, 16.42 and 21.19 ± 0.2° 20 using Cu Ka radiation.
93. The omecamtiv mecarbil according to claim 92, further characterized by XRPD pattern maxima 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° 20 using Cu Ka radiation.
94. The omecamtiv mecarbil according to claim 92 or 93, having an XRPD pattern as shown in Figure 67, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
95. The omecamtiv mecarbil in accordance with any of claims 92 to 94, having a thermogravimetric analysis (TGA) as shown in Figure 68.
96. A crystalline salt bis-tartrate of omecamtiv mecarbil, form B, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 3.77, 5.69 and 10.07 ± 0.2° 20 using Cu Ka radiation.
97. The omecamtiv mecarbil according to claim 96, further characterized by XRPD pattern maxima at 4.72, 6.95, 9.34, 11.18, 12.63, 15.18, 17.69, 22.35 7 / co in / C7n7 / e / YiAi and 25.46 ± 0.2° 20 using Cu Ka radiation.
98. The omecamtiv mecarbil according to claim 96 or 97, having an XRPD pattern as shown in Figure 69, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
99. The omecamtiv mecarbil in accordance with any of claims 96 to 98, having a thermogravimetric analysis (TGA) as shown in Figure 70.
100. A crystalline salt bis-tartrate of omecamtiv mecarbil, form C, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 3.57, 6.23 and 15.84 ± 0.2° 20 using Cu Ka radiation.
101. The omecamtiv mecarbil according to claim 100, further characterized by XRPD pattern maxima 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° 20 using Cu Ka radiation.
102. The omecamtiv mecarbil according to claim 100 or 101, having an XRPD pattern as shown in Figure 71, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
103. The omecamtiv mecarbil according to any of claims 100 to 102, having a thermogravimetric analysis (TGA) as shown in Figure 72, wherein said TGA comprises features that can vary by ± 5 °C.
104. A crystalline salt mono-tartrate of omecamtiv mecarbil, form D, characterized by a powder X-ray diffraction (XRPD) pattern comprising maxima at 9.77 and 15.40 ± 0.2° 28 using Cu Ka radiation.
105. The omecamtiv mecarbil according to claim 104, further characterized by XRPD pattern maxima at 10.87, 13.79, 17.36, 17.74, 18.58, 18.87, 21.78, 25.43 and 26.24 ± 0.2° 28 using Cu Ka radiation.
106. The omecamtiv mecarbil according to claim 104 or 105, having an XRPD pattern as shown in Figure 73, wherein said XRPD pattern comprises maxima that can vary by ± 0.2°.
107. The omecamtiv mecarbil in accordance with any of claims 104 to 106, having a thermogravimetric analysis (TGA) as shown in Figure 74.
108. An amorphous hydrochloride salt of omecamtiv mecarbil.
109. The omecamtiv mecarbil according to claim 108, having a differential scanning calorimetry (DSC) transition as shown in Figure 15.
110. The mecarbil omecamtiv according to claim 108 or 109, having a TGA as shown in Figure 16, wherein said TGA comprises features that can vary by ± 5 °C. 7 / co in / C7n7 / e / YiAi 111. The omecamtiv mecarbil in accordance with any of claims 108 to 110, having a moisture sorption profile as shown in Figure 17.
112. A pharmaceutical composition comprising the omecamtiv mecarbil of any of claims 1 to 111 and a pharmaceutically acceptable excipient.
113. The omecamtiv mecarbil according to any of claims 1 to 111 or the composition according to claim 112, for use in the treatment of heart failure in a subject in need thereof, wherein the omecamtiv mecarbil or said composition is adapted to be administered in an effective amount to said subject.