Salt crystals

Abstract

Disclosed herein are acid addition salts and salt crystals of (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one, compositions containing same, and methods of making and using the salts and crystals.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application is an international application claiming priority to and the benefit of U.S. Provisional Application No. 63 / 267,347, filed January 31, 2022, the contents of which are incorporated herein by reference in their entirety.

[0002] Field of Disclosure

[0003] The present invention relates to acid addition salts and salt crystals of (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one, compositions containing same, and methods of making and using such salts and salt crystals. [Background technology]

[0004] Background of the disclosure The compound (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one is disclosed in WO 2009 / 075784 (U.S. Patent Application Publication No. 2010 / 0273754). The compounds have been found to be potent and selective phosphodiesterase 1 (PDE1) inhibitors useful for treating or preventing disorders characterized by low levels of cAMP and / or cGMP in cells expressing PDE1, and / or reduced dopamine D1 receptor signaling activity (e.g., Parkinson's disease, Tourette's syndrome, autism, fragile X syndrome, ADHD, restless legs syndrome, depression, cognitive impairment in schizophrenia, narcolepsy), and / or any disease or condition that can be ameliorated by enhancing progesterone signaling. This list of disorders is illustrative and is not intended to be exhaustive.

[0005] WO 2009 / 075784 discloses (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one in free base form and in generally pharma- ceutically acceptable salt forms, but no particular salt has been shown to have any particular stability or desirable properties. Since many pharmaceutical compounds can exist in different physical forms (e.g., liquid or solid in different crystalline, amorphous, polymorphic, hydrated or solvated forms) that may alter the stability, solubility, bioavailability or pharmacokinetics (absorption, distribution, metabolism, excretion, etc.) and / or bioequivalence of the drug, identifying the optimal physical form (e.g., free base or salt in a solid, liquid, crystalline, hydrated, solvated, amorphous or polymorphic form) of the pharmaceutical compound is of critical importance in drug development. Summary of the Invention

[0006] Disclosure Summary In a first aspect, the present disclosure is directed to salt forms, such as crystalline salt forms, of (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (Compound A) acid addition salt. These salts and salt crystals are particularly advantageous in the preparation of a wide variety of galenical formulations. In various embodiments, the crystalline salts of the present disclosure are selected from the group consisting of hydrochloride, malate, fumarate, sulfate, esylate, galactarate, adipate, lactate, oxalate, palmitate, 2-oxo-glutarate, xinafoate, tosylate, tartrate, succinate, mesylate, napadisylate, edisylate, propionate, caprylate, besylate, benzoate, nicotinate, isonicotinate, orotate, camsylate, salicylate, aminosalicylate, mandelate, acetamidobenzoate, trifluoroacetate, dichloroacetate, caproate, or laurate. The various crystalline salts of the present disclosure may be in anhydrous or solvate form.

[0007] In a second aspect, the disclosure also provides a method for preparing a stable acid addition salt, e.g., a crystalline acid addition salt, of (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one ("Compound A") with a particular acid, comprising reacting a free base form of Compound A with an acid in a solvent and isolating the resulting salt. In various embodiments, the method further comprises forming a slurry of Compound A and an acid in a solvent at a temperature between about 30° C. and 70° C., e.g., for at least 1 hour. In various embodiments, the method further comprises cooling the solution to a temperature of about −10° C. to about 20° C. In various embodiments, the method further comprises evaporating the solution to dryness, hi various embodiments, the resulting salt is crystalline and is dissolved in a second solvent and subjected to one or more cooling cycles.

[0008] In a third aspect, the disclosure relates to a method for treating a patient, e.g., a patient suffering from a disorder selected from one or more of: a neurodegenerative disease; a psychiatric disorder; a circulatory and cardiovascular disorder; a respiratory and inflammatory disorder; a disease that can be alleviated by enhancing progesterone signaling; a disease or disorder such as psychiatric disease, glaucoma or elevated intraocular pressure; a traumatic brain injury; a cancer or tumor; a renal disorder; a disease or condition characterized by low levels of cAMP and / or cGMP; and a disease or condition characterized by reduced dopamine D1 receptor signaling activity. Methods are provided for the prevention or treatment of humans, comprising administering to a patient in need of said prevention or treatment a therapeutically effective amount of the compound (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (Compound A) in acid addition salt form, for example by any of the salt crystals disclosed herein. [Brief description of the drawings]

[0009] [Figure 1A] FIG. 1A shows the powder X-ray diffraction pattern of the hydrochloride salt 1.

[0010] [Figure 1B] FIG. 1B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of the hydrochloride salt 1.

[0011] [Figure 2A] FIG. 2A shows the powder X-ray diffraction pattern of the hydrochloride salt 2.

[0012] [Figure 2B] FIG. 2B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of the hydrochloride salt 2.

[0013] [Figure 3A] FIG. 3A shows the powder X-ray diffraction pattern of the hydrochloride salt 3.

[0014] [Figure 3B] FIG. 3B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of the hydrochloride salt 3.

[0015] [Figure 4A] FIG. 4A shows the powder X-ray diffraction pattern of the hydrochloride salt 4.

[0016] [Figure 4B] FIG. 4B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of the hydrochloride salt 4.

[0017] [Figure 5A] FIG. 5A shows the powder X-ray diffraction pattern of the hydrochloride salt 5.

[0018] [Figure 5B] FIG. 5B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of the hydrochloride salt 5.

[0019] [Figure 6A] FIG. 6A shows the powder X-ray diffraction pattern of the hydrochloride salt 6.

[0020] [Figure 6B] FIG. 6B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of the hydrochloride salt 6.

[0021] [Figure 7A] FIG. 7A shows the powder X-ray diffraction pattern of the hydrochloride salt 7.

[0022] [Figure 7B] FIG. 7B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of the hydrochloride salt 7.

[0023] [Figure 8A] FIG. 8A shows the powder X-ray diffraction pattern of the hydrochloride salt 8.

[0024] [Figure 8B] FIG. 8B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of the hydrochloride salt 8.

[0025] [Figure 9A] FIG. 9A shows the powder X-ray diffraction pattern of Malate 1.

[0026] [Figure 9B] FIG. 9B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of malate 1.

[0027] [Figure 10A] FIG. 10A shows the powder X-ray diffraction pattern of the tartrate salt 1.

[0028] [Figure 10B] FIG. 10B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of tartrate salt 1.

[0029] [Figure 11A] FIG. 11A shows the powder X-ray diffraction pattern of the tartrate salt 2.

[0030] [Figure 11B] FIG. 11B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of tartrate salt 2.

[0031] [Figure 12A] FIG. 12A shows the powder X-ray diffraction pattern of oxalate 1.

[0032] [Figure 12B] FIG. 12B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of oxalate salt 1.

[0033] [Figure 13A] FIG. 13A shows the powder X-ray diffraction pattern of oxalate salt 2.

[0034] [Figure 13B] FIG. 13B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of oxalate salt 2.

[0035] [Figure 14A] FIG. 14A shows the powder X-ray diffraction pattern of oxalate salt 3.

[0036] [Figure 14B] FIG. 14B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of oxalate salt 3.

[0037] [Figure 15A] FIG. 15A shows the powder X-ray diffraction pattern of oxalate salt 4.

[0038] [Figure 15B]FIG. 15B shows a combined differential scanning calorimetry (DSC) / thermogravimetric analysis (TGA) thermogram of oxalate salt 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0039] Detailed Description As used herein, the term "crystal" or "crystals" or "crystalline" or "crystallinic" refers to a solid that has short-range or long-range order of molecules, atoms or ions in a fixed lattice arrangement. The salt crystal of the present disclosure may be in a single crystal form. Thus, the salt crystal of the present disclosure may be in a triclinic form, a monoclinic form, an orthorhombic form, a tetragonal form, a rhombohedral form, a hexagonal form or a cubic form or a mixture thereof. In particular, the salt crystal of the present disclosure is a dry crystal form. In certain embodiments, the salt crystal of the present disclosure is substantially free of other forms, for example free of amorphous form or other crystalline forms.

[0040] The term "substantially free" of other crystalline forms refers to less than about 10% by weight of other forms or other crystalline forms, such as amorphous or other crystalline forms, preferably less than about 5% by weight, more preferably less than about 2% by weight, even more preferably less than about 1% by weight, even more preferably less than about 0.1% by weight, and more preferably less than about 0.01% by weight.

[0041] The terms "predominantly" or "substantially entirely in a single form" refer to less than about 10% by weight of other solid forms, such as amorphous or other crystalline forms, preferably less than about 5% by weight, more preferably less than about 2% by weight, even more preferably less than about 1% by weight, even more preferably less than about 0.1% by weight, and most preferably less than about 0.01% by weight.

[0042] In certain embodiments, the salt crystals of the present disclosure may contain trace amounts of solvent, for example in the form of a solvate, or may contain trace amounts of water, for example in the form of a hydrate.Preferably, the salt crystals of the present disclosure are in a non-solvated form.More preferably, the crystals of the present disclosure are in a non-solvated form or a non-hydrated form.

[0043] The salt crystals of the present disclosure may have a free base to acid ratio of 1:1, 1:0.5, or 1:>1, such as 1:1.3, or 1:2.

[0044] The term "solvate" refers to a crystalline solid adduct that contains a stoichiometric or non-stoichiometric amount of a solvent within the crystal structure. Thus, the term "non-solvate" form, as used herein, refers to salt crystals that are free or substantially free of solvent molecules within the crystal structure of the present disclosure.

[0045] The term "amorphous" morphology refers to a solid with a disordered arrangement of molecules and does not possess a discernible crystal lattice.

[0046] Unless further modified, the term "compound A" has the following structure: [ka] refers to the free base form of (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one having the formula:

[0047] The crystallinity or morphology of the crystals of the present disclosure can be determined by a number of methods, including, but not limited to, single crystal X-ray diffraction, powder X-ray diffraction, polarized optical microscopy, thermal microscopy, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), infrared adsorption spectroscopy and Raman spectroscopy. Characterization of solvates or hydrates or lack thereof can also be determined by DSC and / or TGA.

[0048] It should be understood that the powder X-ray diffraction pattern or differential scanning calorimetry pattern of a given sample may vary slightly (standard deviation) depending on the equipment used, the time and temperature of the sample when measured, and standard experimental error. Therefore, the temperature, or the 2θ values, d-spacing values, heights and relative intensities of peaks described in tables or figures herein have an acceptable level of deviation. For example, these values ​​may have an acceptable deviation of, for example, about 20%, 15%, 10%, 5%, 3%, 2% or 1%. In certain embodiments, the 2θ values ​​or d-spacing values ​​of the XRPD pattern of the crystal of the present disclosure may have an acceptable deviation of ±0.2° and / or ±0.2Å. Furthermore, the XRPD pattern of the crystal of the present disclosure may be identified by characteristic peaks, as recognized by those skilled in the art. For example, a crystal of the present disclosure may be identified by, e.g., at least five characteristic peaks, e.g., at least three or at least five peaks, e.g., at least three or at least five 2θ values ​​and / or at least three or at least five d-spacing values, as set forth in an XRPD pattern described herein. Thus, the term "corresponding to or substantially corresponding to" set forth in any of the tables or any of the figures refers to a crystal having an XRPD with the major or characteristic peaks set forth in the table / figure.

[0049] The term "about" preceding a numerical value refers to the numerical value itself, ±20%, ±15%, ±10%, preferably ±5%, preferably ±3%, preferably ±2%, preferably ±1% of that value. When referring to temperature, the term about refers to the temperature value itself, ±10°C, preferably ±5°C, preferably ±3°C of the referenced temperature. In another example, when referring to a 2θ angle value, the term "about" refers to the 2θ angle value itself, ±0.2° of the referenced 2θ angle value. In yet another example, when referring to a d-spacing value, the term "about" refers to the 2θ angle value itself, ±0.2 Å of the referenced d-spacing value.

[0050] The crystal of the present disclosure is a selective PDE1 inhibitor.Therefore, the crystal of the present disclosure is useful for treating PDE1-related disorders, such as those described in International Publication No. WO 2014 / 151409, International Publication No. WO 2018 / 049417, International Publication No. WO 2019 / 227004, International Publication No. WO 2019 / 152697, International Publication No. WO 2009 / 075784, International Publication No. WO 2010 / 132127, International Publication No. WO 2006 / 133261 and International Publication No. WO 2011 / 153129 (each of which is incorporated herein by reference in its entirety).

[0051] The term "patient" includes humans and non-humans. In one embodiment, the patient is a human. In another embodiment, the patient is a non-human.

[0052] Salts and salt crystals of the present disclosure In a first aspect, the disclosure is directed to the salts of the compound (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (Compound A) in the form of an acid addition salt [Salt 1]. These salts may be in the form of crystalline salts and are particularly advantageous for the preparation of various types of galenical preparations. Thus, in said first aspect, the present invention provides:

[0053] 1.1 For example, hydrochloride, malate, fumarate, sulfate, esylate, galactarate, adipate, lactate, oxalate, palmitate, 2-oxo-glutarate, xinafoate, tosylate, tartrate, succinate, mesylate, napadisylate, edisylate, propionate, caprylate, besylate, benzoate, nicotinate, isonicotinate, orotate, camsylate, salicylate, aminosalicylate, mandelate, acetamidate, 2. The compound (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (Compound A) in the form of an acid addition salt selected from the group consisting of dibenzoate, trifluoroacetate, dichloroacetate, caproate, or laurate.

[0054] 1.2 Salt 1 or 1.1, wherein the salt is crystalline.

[0055] 1.3 Salt 1 or 1.1, wherein the salt is in anhydrous crystalline form.

[0056] 1.4 Any of salts 1-1.2, wherein the salt is in a solvate crystalline form.

[0057] 1.5 Any of the preceding salts wherein the salt is a hydrochloride salt.

[0058] 1.6 Any of salts 1.1 to 1.4, wherein the salt is a malate.

[0059] 1.7 Any of salts 1.1 to 1.4, wherein the salt is a fumarate salt.

[0060] 1.8 Any of salts 1.1 to 1.4, wherein the salt is a sulfate.

[0061] 1.9 Any of salts 1.1 to 1.4, wherein the salt is an esylate salt.

[0062] 1.10 Any of salts 1.1 to 1.4, wherein the salt is a silate salt.

[0063] 1.11 Any of salts 1.1 to 1.4, wherein the salt is a tartrate.

[0064] 1.12 Any of salts 1.1 to 1.4, wherein the salt is a succinate salt.

[0065] 1.13 Any of salts 1.1 to 1.4, wherein the salt is a mesylate salt.

[0066] 1.14 Any of salts 1.1 to 1.4, wherein the salt is napadisilate.

[0067] 1.15 Any of salts 1.1 to 1.4, wherein the salt is an edisylate salt.

[0068] 1.16 Any of salts 1.1 to 1.4, wherein the salt is a propionate salt.

[0069] 1.17 Any of salts 1.1 to 1.4, wherein the salt is the caprylate salt.

[0070] 1.18 Any of salts 1.1 to 1.4, wherein the salt is a besylate salt.

[0071] 1.19 Any of salts 1.1 to 1.4, wherein the salt is a benzoate salt.

[0072] 1.20 Any of salts 1.1 to 1.4, wherein the salt is a nicotinate salt.

[0073] 1.21 Any of salts 1.1 to 1.4, wherein the salt is an isonicotinate salt.

[0074] 1.22 Any of salts 1.1 to 1.4, wherein the salt is an orotate salt.

[0075] 1.23 Any of salts 1.1 to 1.4, wherein the salt is the camsylate salt.

[0076] 1.24 Any of salts 1.1 to 1.4, wherein the salt is a salicylate.

[0077] 1.25 Any of salts 1.1 to 1.4, wherein the salt is an aminosalicylate.

[0078] 1.26 Any of salts 1.1 to 1.4, wherein the salt is a mandelate salt.

[0079] 1.27 Any of salts 1.1 to 1.4, wherein the salt is an acetamidobenzoate.

[0080] 1.28 Any of salts 1.1 to 1.4, wherein the salt is a trifluoroacetate salt.

[0081] 1.29 Any of salts 1.1 to 1.4, wherein the salt is a dichloroacetate salt.

[0082] 1.30 Any of salts 1.1 to 1.4, wherein the salt is a caproate salt.

[0083] 1.31 Any of salts 1.1 to 1.4, wherein the salt is a laurate salt.

[0084] 1.32 Any of the preceding salts, wherein the salt is crystalline and in the form of a solvate selected from an acetonitrile solvate, an ethyl acetate solvate, an acetone solvate, a 2-butanone solvate, a 2-ethyl-1-butanol solvate, an ethyl salicylate solvate, an ethyl butyl ketone solvate, an acetone solvate, a 3-heptanone solvate, a toluene solvate, a methanol solvate, an ethanol solvate, a propanol (e.g., isopropanol, 2-propanol) solvate, a butanol (e.g., 2-ethyl-1-butanol) solvate, a dimethylsulfoxide (DMSO) solvate, anisole solvate, or an ethyl butyl ketone solvate.

[0085] 1.33 Any of the preceding salts, wherein the salt is crystalline and in the form of a solvate selected from an acetonitrile solvate, an ethyl acetate solvate, a 2-butanone solvate, an acetone solvate, a 3-heptanone solvate, or a 2-butanone solvate.

[0086] 1.34 Any of the preceding salts, wherein the salt is crystalline and the Compound A free base and hydrochloride counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1, e.g., about 1:0.3, about 1:0.4, about 1:0.4, about 1:0.5, about 1:0.6, about 1:0.7, about 1:0.8, about 1:0.9.

[0087] Surprisingly, it has been found that certain salts of the invention are in crystalline form and are therefore preferred for galenical and / or therapeutic use.Accordingly, in a further embodiment, the invention provides the hydrochloride salt of compound A [hydrochloride salt 1].

[0088] 1.1 Crystalline form, hydrochloride salt 1.

[0089] 1.2 The hydrochloride salt 1 or 1.1 in solvate form.

[0090] 1.3 Any of the hydrochloride salts 1-1.2, wherein the salt crystals are in the form of a solvate with one or more of acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, or combinations thereof.

[0091] 1.4 Any of the hydrochlorides 1 to 1.3, wherein the salt crystal is an ethyl acetate solvate.

[0092] 1.5 Any of the hydrochlorides 1 to 1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 7.3°, 9.5°, 9.7°, 12.3°, 14.4°, 14.6°, 19.0°, 19.6° and 21.4°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0093] 1.6 Any of the hydrochlorides 1 to 1.5, wherein the salt crystals show a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 7.3°, 12.3°, 19.0° and 19.6°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0094] 1.7 Any of the hydrochloride salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 17.9 Å, 12.1 Å, 9.3 Å, 9.1 Å, 7.2 Å, 6.2 Å, 6.0 Å, 4.7 Å, 4.5 Å and 4.2 Å.

[0095] 1.8 Any of the hydrochloride salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 17.9 Å, 12.1 Å, 7.2 Å, 4.7 Å and 4.5 Å.

[0096] 1.9 Any of the hydrochloride salts 1-1.8, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 1 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0097] 1.10 Any of the hydrochlorides 1 to 1.9, wherein the salt crystals show a differential scanning calorimetry (DSC) pattern including an endothermic peak at about 169°C to 172°C, for example, about 170°C.

[0098] 1.11 Any of the hydrochloride salts 1-1.10, wherein the Compound A free base and hydrochloride counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, for example about 1:0.9.

[0099] In a further embodiment, the disclosure provides a second hydrochloride salt of Compound A [Hydrogen Salt 2].

[0100] 2.1 Crystalline form, hydrochloride salt2.

[0101] 2.2 The hydrochloride salt 2 or 2.1 in solvate form.

[0102] 2.3 Any of the hydrochloride salts 2-2.2, wherein the salt crystals are in the form of a solvate with one or more of acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, or combinations thereof.

[0103] 2.4 Any of the hydrochlorides 2 to 2.3, wherein the salt crystal is an ethyl butyl ketone solvate.

[0104] 2.5 Any of the hydrochlorides 2 to 2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 7.3°, 12.1°, 13.6°, 15.6°, 16.4°, 18.5°, 20.0°, 21.3°, 21.4° and 21.5°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0105] 2.6 Any of the hydrochlorides 2 to 2.5, wherein the salt crystals show a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 7.3°, 12.1°, 13.6°, 15.6° and 18.5°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0106] 2.7 Any of the hydrochloride salts 2-2.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 12.2 Å, 11.8 Å, 7.3 Å, 6.5 Å, 5.7 Å, 5.4 Å, 4.8 Å, 4.4 Å, 4.2 Å, and 4.1 Å.

[0107] 2.8 Any of the hydrochloride salts 2-2.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 12.2 Å, 7.3 Å, 6.5 Å, 5.7 Å, and 4.8 Å.

[0108] 2.9 Any of the hydrochloride salts 2-2.8, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 2 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0109] 2.10 Any of the hydrochloride salts 2-2.9, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak at about 140°C to 142°C, e.g., about 141°C, and / or between about 190°C to 192°C, e.g., about 191°C.

[0110] 2.11 Any of the hydrochloride salts 2-2.10, wherein the Compound A free base and hydrochloride counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, for example about 1:0.9.

[0111] In a further embodiment, the disclosure provides a third hydrochloride salt of Compound A [Hydrogen Salt 3].

[0112] 3.1 Crystalline form, hydrochloride salt 3.

[0113] 3.2 The hydrochloride salt 3 or 3.1, in solvate form.

[0114] 3.3 Any of the hydrochloride salts 3-3.2, wherein the salt crystals are in the form of a solvate with one or more of acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, or combinations thereof.

[0115] 3.4 Any of the hydrochlorides 3 to 3.3, wherein the salt crystal is an acetonitrile solvate.

[0116] 3.5 Any of the hydrochlorides 3 to 3.4, wherein the salt crystals show a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 6.9°, 7.3°, 7.4°, 12.2°, 12.7°, 14.6°, 20.6°, 27.6° and 32.7°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0117] 3.6 Any of the hydrochlorides 3 to 3.5, wherein the salt crystals show a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 7.3°, 7.4°, 12.2° and 27.6°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0118] 3.7 Any of the hydrochloride salts 3-3.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 18.0 Å, 14.4 Å, 12.8 Å, 12.0 Å, 7.3 Å, 6.9 Å, 6.1 Å, 4.3 Å, 3.2 Å and 2.7 Å.

[0119] 3.8 Any of the hydrochloride salts 3-3.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 18.0 Å, 12.0, 7.3 Å, 6.9 Å and 3.2 Å.

[0120] 3.9 Any of the hydrochloride salts 3-3.8, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 3 as defined herein, the XRPD pattern being measured using a copper anode diffractometer at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0121] 3.10 Any of the hydrochloride salts 3-3.9, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 155°C and 157°C, e.g., about 156°C, and / or between about 275°C and 277°C, e.g., about 276°C.

[0122] 3.11 Any of the hydrochloride salts 3-3.10, wherein said Compound A free base and hydrochloride counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, for example about 1:0.9.

[0123] In a further embodiment, the disclosure provides a fourth hydrochloride salt of Compound A [Hydrogen Salt 4].

[0124] 4.1 Crystalline form, hydrochloride salt 4.

[0125] 4.2 The hydrochloride salt 4 or 4.1 in solvate form.

[0126] 4.3 Any of the hydrochloride salts 4-4.2, wherein the salt crystals are in the form of a solvate with one or more of acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, or combinations thereof.

[0127] 4.4 Any of the hydrochlorides 4 to 4.3, wherein the salt crystal is a 2-butanone solvate.

[0128] 4.5 Any of the hydrochlorides 4 to 4.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 7.6°, 12.0°, 12.7°, 15.0°, 15.1°, 17.9°, 18.8°, 19.3°, 23.1° and 24.0°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0129] 4.6 Any of the hydrochlorides 4 to 4.5, wherein the salt crystals show a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 7.6°, 12.0°, 12.7°, 18.8° and 23.1°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0130] 4.7 Any of the hydrochloride salts 4-4.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 11.7 Å, 7.4 Å, 7.0 Å, 5.9 Å, 5.8 Å, 4.9 Å, 4.7 Å, 4.6 Å, 3.8 Å and 3.7 Å.

[0131] 4.8 Any of the hydrochloride salts 4-4.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 11.7 Å, 7.4 Å, 7.0 Å, 4.7 Å and 3.8 Å.

[0132] 4.9 Any of the hydrochloride salts 4-4.8, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 4 as defined herein, the XRPD pattern being measured using a copper anode diffractometer at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0133] 4.10 Any of the hydrochloride salts 4-4.9, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 194°C and 196°C, e.g., about 195°C, and / or between about 209°C and 211°C, e.g., about 210°C.

[0134] 4.11 Any of the hydrochloride salts 4-4.10, wherein the Compound A free base and hydrochloride counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, for example about 1:0.9.

[0135] In a further embodiment, the present disclosure provides a fifth hydrochloride salt of Compound A [Hydrogen Salt 5].

[0136] 5.1 Crystalline form, hydrochloride salt 5.

[0137] 5.2 The hydrochloride salt 5 or 5.1 in solvate form.

[0138] 5.3 Any of the hydrochloride salts 5-5.2, wherein the salt crystals are in the form of a solvate with one or more of acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, or combinations thereof.

[0139] 5.4 Any of the hydrochlorides 5 to 5.3, wherein the salt crystal is a 2-ethyl-1-butanol solvate.

[0140] 5.5 Any of the hydrochlorides 5 to 5.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.7°, 7.7°, 8.8°, 9.1°, 11.4°, 16.4°, 17.0°, 18.4°, 21.9° and 24.1°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0141] 5.6 Any of the hydrochlorides 5 to 5.5, wherein the salt crystals show a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.7°, 7.7°, 8.8°, 9.1° and 16.4°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0142] 5.7 Any of the hydrochloride salts 5-5.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 13.2 Å, 11.5 Å, 10.0 Å, 9.8 Å, 7.8 Å, 5.4 Å, 5.2 Å, 4.8 Å, 4.1 Å and 3.7 Å.

[0143] 5.8 Any of the hydrochloride salts 5-5.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 13.2 Å, 11.5 Å, 10.0 Å, 9.8 Å and 5.4 Å.

[0144] 5.9 Any of the hydrochloride salts 5-5.8, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 52 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0145] 5.10 Any of the hydrochloride salts 5 to 5.9, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 158°C and 161°C, e.g., about 159°C.

[0146] 5.11 Any of the hydrochloride salts 5-5.10, wherein the Compound A free base and hydrochloride counterion are present in a molar ratio of about 2:1 to about 1:2, for example, about 1:1.

[0147] In a further embodiment, the present disclosure provides a sixth hydrochloride salt of Compound A [hydrochloride salt 6].

[0148] 6.1 Crystalline form, hydrochloride salt 6.

[0149] 6.2 The hydrochloride salt 6 or 6.1 in solvate form.

[0150] 6.3 Any of the hydrochloride salts 6-6.2, wherein the salt crystals are in the form of a solvate with one or more of acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, or combinations thereof.

[0151] 6.4 Any of the hydrochlorides 6 to 6.3, wherein the salt crystal is an ethyl butyl ketone solvate.

[0152] 6.5 Any of the hydrochlorides 6 to 6.4, wherein the salt crystals show a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.0°, 7.1°, 7.5°, 7.8°, 8.5°, 12.4°, 13.0°, 18.7°, 18.8° and 20.8°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0153] 6.6 Any of the hydrochlorides 6 to 6.5, wherein the salt crystals show a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.0°, 7.1°, 7.8°, 12.4° and 18.7°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0154] 6.7 Any of the hydrochloride salts 6-6.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 17.8 Å, 12.5 Å, 11.7 Å, 11.3 Å, 10.4 Å, 7.1 Å, 6.8 Å, 6.0 Å, 4.7 Å and 4.3 Å.

[0155] 6.8 Any of the hydrochloride salts 6-6.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 17.8 Å, 12.5 Å, 11.3 Å, 7.1 Å and 4.7 Å.

[0156] 6.9 Any of the hydrochloride salts 6-6.8, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 53 as defined herein, the XRPD pattern being measured using a copper anode diffractometer at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0157] 6.10 Any of the hydrochloride salts 6-6.9, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 129°C and 133°C, e.g., about 131°C.

[0158] 6.11 Any of the hydrochloride salts 6-6.10, wherein the Compound A free base and hydrochloride counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0159] In a further embodiment, the present disclosure provides a seventh hydrochloride salt of Compound A [HCl 7].

[0160] 7.1 Crystalline form, hydrochloride salt 7.

[0161] 7.2 The hydrochloride salt 7 or 7.1 in solvate form.

[0162] 7.3 Any of the hydrochloride salts 7-7.2, wherein the salt crystals are in the form of a solvate with one or more of acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, or combinations thereof.

[0163] 7.4 Any of the hydrochlorides 7 to 7.3, wherein the salt crystal is an anisole solvate.

[0164] 7.5 Any of the hydrochlorides 7 to 7.4, wherein the salt crystals show a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.6°, 8.7°, 6.1°, 9.2°, 9.8°, 10.7°, 10.9°, 18.9°, 21.8° and 22.0°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0165] 7.6 Any of the hydrochloride salts 7 to 7.5, wherein the salt crystals show a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.6°, 8.7°, 9.8°, 18.9° and 22.0°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0166] 7.7 Any of the hydrochloride salts 7-7.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 15.7 Å, 14.4 Å, 14.6 Å, 10.2 Å, 9.6 Å, 9.0 Å, 8.1 Å, 4.7 Å, 4.0 Å and 4.1 Å.

[0167] 7.8 Any of the hydrochloride salts 7-7.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 15.7 Å, 10.2 Å, 9.0 Å, 4.7 Å and 4.0 Å.

[0168] 7.9 Any of the hydrochloride salts 7-7.8, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 54 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0169] 7.10 Any of the hydrochloride salts 7-7.9, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 144°C and 147°C, e.g., about 145°C.

[0170] 7.11 Any of the hydrochloride salts 7-7.10, wherein the Compound A free base and hydrochloride counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0171] In a further embodiment, the present disclosure provides an eighth hydrochloride salt of Compound A [Hydrogen Salt 8].

[0172] 8.1 Crystalline form, hydrochloride salt 8.

[0173] 8.2 The hydrochloride salt 8 or 8.1 in solvate form.

[0174] 8.3 Any of the hydrochloride salts 8-8.2, wherein the salt crystals are in the form of a solvate with one or more of acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, or combinations thereof.

[0175] 8.4 Any of the hydrochlorides 8 to 8.3, wherein the salt crystal is an ethyl salicylate solvate.

[0176] 8.5 Any of the hydrochloride salts 8 to 8.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.7°, 11.4°, 11.6°, 12.5°, 18.9°, 19.2°, 20.2°, 20.4°, 20.6° and 22.1°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0177] 8.6 Any of the hydrochloride salts 8 to 8.5, wherein the salt crystals show a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.7°, 11.4°, 11.6°, 20.6° and 22.1°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0178] 8.7 Any of the hydrochloride salts 8-8.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 15.4 Å, 7.8 Å, 7.6 Å, 7.1 Å, 5.2 Å, 4.7 Å, 4.6 Å, 4.4 Å, 4.3 Å and 4.0 Å.

[0179] 8.8 Any of the hydrochloride salts 8-8.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 15.4 Å, 7.8 Å, 7.6 Å, 4.3 Å and 4.0 Å.

[0180] 8.9 Any of the hydrochloride salts 8 to 8.8, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 55 as defined herein, the XRPD pattern being measured using a copper anode diffractometer at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0181] 8.10 Any of the hydrochloride salts 8 to 8.9, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 196°C and 200°C, e.g., about 198°C.

[0182] 8.11 Any of the hydrochloride salts 8-8.10, wherein the Compound A free base and hydrochloride counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0183] In a further embodiment, the present disclosure provides a malate salt of Compound A [Malate 1].

[0184] 1.1 Malate salt, a crystalline form.

[0185] 1.2 Malate 1 or 1.1 in solvate form.

[0186] 1.3 Any of the malates 1 to 1.2, wherein the salt crystal is an ethyl acetate solvate.

[0187] 1.4 Any of Malate Salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.9°, 7.2°, 12.0°, 16.0°, 17.7°, 17.8°, 20.9°, 21.2°, 21.7° and 21.8°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0188] 1.5 Any of Malate Salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.9°, 16.0°, 17.8°, 21.7° and 21.8°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0189] 1.6 Any of Malate Salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 15.0 Å, 12.3 Å, 7.4 Å, 5.5 Å, 5.0 Å, 4.5 Å, 4.3 Å, 4.2 Å, 4.1 Å and 3.1 Å.

[0190] 1.7 Any of the malate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 15.0 Å, 5.5 Å, 5.0 Å, 4.2 Å and 4.1 Å.

[0191] 1.8 Any of Malate Salts 1-1.7, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 5 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0192] 1.9 Any of Malate Salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 94°C and 96°C, for example at about 95°C.

[0193] 1.10 Any of the malate salts 1-1.9, wherein Compound A free base and malate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:0.7.

[0194] In a further embodiment, the present disclosure provides a fumarate salt of Compound A [Fumarate Salt 1].

[0195] 1.1 The fumarate salt, a crystalline form.

[0196] 1.2 Fumarate 1 or 1.1 in solvate form.

[0197] 1.3 Any of the fumarates 1 to 1.2, wherein the salt crystal is an ethyl acetate solvate.

[0198] 1.4 Any of Fumarates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.9°, 7.4°, 11.8°, 12.6°, 13.8°, 17.2°, 18.9°, 20.6°, 21.7° and 21.5°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0199] 1.5 Any of Fumarates 1-1.4, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.9°, 7.4°, 13.8°, 17.2° and 21.7°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0200] 1.6 Any of Fumarates 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 14.9 Å, 12.0 Å, 7.5 Å, 7.0 Å, 6.4 Å, 5.6 Å, 4.7 Å, 4.3 Å and 4.1 Å.

[0201] 1.7 Any of the Fumarates 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 14.9 Å, 12.0 Å, 6.4 Å, 5.6 Å and 4.1 Å.

[0202] 1.8 Any of Fumarates 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 6 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0203] 1.9 Any of Fumarates 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 110°C and 112°C, e.g., about 111°C, and / or between about 141°C and 143°C, e.g., about 142°C.

[0204] 1.10 Any of the fumarates 1-1.9, wherein Compound A free base and the fumarate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:0.5.

[0205] In a further embodiment, the disclosure provides a first sulfate salt of Compound A [Sulfate Salt 1].

[0206] 1.1 Sulfate salt, crystalline form.

[0207] 1.2 Sulfate 1 or 1.1 in solvate form.

[0208] 1.3 Any of the sulfates 1 to 1.2, wherein the salt crystal is an ethyl acetate solvate.

[0209] 1.4 Any of Sulfates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 5.9°, 6.5°, 8.0°, 8.5°, 12.3°, 12.5°, 18.0°, 20.8° and 22.7°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0210] 1.5 Any of Sulfates 1 to 1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 5.9°, 6.5°, 8.0° and 22.7°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0211] 1.6 Any of sulfate salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 18.1 Å, 15.1 Å, 13.6 Å, 11.1 Å, 10.5 Å, 7.2 Å, 7.1 Å, 4.9 Å, 4.3 Å and 3.9 Å.

[0212] 1.7 Any of the sulfate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 18.1 Å, 15.1 Å, 13.6 Å, 11.1 Å, and 3.9 Å.

[0213] 1.8 Any of Sulfate Salts 1-1.7, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 7 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0214] 1.9 Any of Sulfates 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 132°C and 134°C, e.g., about 133°C, and / or between about 227°C and 229°C, e.g., about 228°C.

[0215] 1.10 Any of the sulfate salts 1-1.9, wherein Compound A free base and sulfate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, for example about 1:0.4.

[0216] In a further embodiment, the disclosure provides a second sulfate salt of Compound A [Sulfate Salt 2].

[0217] 2.1 Sulfate, in crystalline form.2.

[0218] 2.2 The sulfate 2 or 2.1 in solvate form.

[0219] 2.3 Any of the sulfates 2 to 2.2, wherein the salt crystal is an ethyl acetate solvate.

[0220] 2.4 Any of sulfates 2 to 2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 5.9°, 8.4°, 9.6°, 10.7°, 14.8°, 17.9°, 19.6°, 20.8° and 22.8°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0221] 2.5 Any of sulfates 2 to 2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 5.9°, 8.4°, 10.7° and 17.9°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0222] 2.6 Any of sulfate salts 2-2.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern including at least five peaks having d-spacing values ​​selected from the group consisting of 18.1 Å, 15.0 Å, 10.6 Å, 9.2 Å, 8.3 Å, 6.0 Å, 5.0 Å, 4.5 Å, 4.3 Å and 3.9 Å.

[0223] 2.7 Any of sulfate salts 2-2.6, wherein the salt crystal exhibits an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 18.1 Å, 15.0 Å, 10.6 Å, 8.3 Å, and 5.0 Å.

[0224] 2.8 Any of Sulfate Salts 2-2.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 8 as defined herein, the XRPD pattern being measured using a copper anode diffractometer at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0225] 2.9 Any of sulfates 2-2.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 69°C and 71°C, e.g., about 70°C, and / or between about 114°C and 116°C, e.g., about 115°C.

[0226] 2.10 Any of the sulfate salts 2-2.9, wherein Compound A free base and sulfate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:0.5.

[0227] In a further embodiment, the present disclosure provides an esylate salt of Compound A [esylate salt 1].

[0228] 1.1 Crystalline form, esylate salt 1.

[0229] 1.2 Esylate salt 1 or 1.1 in solvate form.

[0230] 1.3 Any of the esylate salts 1 to 1.2, wherein the salt crystal is an acetone solvate.

[0231] 1.4 Any of the esylate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.2°, 11.7°, 17.0°, 18.7°, 19.1°, 19.3°, 20.3°, 20.5°, 22.8° and 23.4°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0232] 1.5 Any of the esylate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.2°, 19.3°, 20.3°, 20.5° and 22.8°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0233] 1.6 Any of the esylate salts 1-1.5, wherein the salt crystals exhibit a powder X-ray diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 14.3 Å, 7.6 Å, 5.2 Å, 4.7 Å, 4.6 Å, 4.4 Å, 4.3 Å, 3.9 Å, 3.8 Å and 3.7 Å.

[0234] 1.7 Any of the esylate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 14.3 Å, 4.6 Å, 4.4 Å, 4.3 Å and 3.9 Å.

[0235] 1.8 Any of the esylate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 9 as defined herein, the XRPD pattern being measured using a diffractometer with a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0236] 1.9 Any of esylate salts 1 to 1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 304°C and 306°C, for example, at about 305°C.

[0237] 1.10 Any of the esylate salts 1-1.9, wherein Compound A free base and the ethanesulfonic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0238] In a further embodiment, the present disclosure provides a galactarate salt of Compound A [Galactarate Salt 1].

[0239] 1.1 The crystalline form, galactarate salt 1.

[0240] 1.2 Galactarate salt 1 or 1.1 in solvate form.

[0241] 1.3 Any of the galactaric acid salts 1 to 1.2, wherein the salt crystal is a methanol solvate.

[0242] 1.4 Any of the galactaric acid salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 18.2°, 19.7°, 21.5°, 26.8°, 30.7°, 34.5°, 36.7°, 36.8°, 37.6° and 37.7°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0243] 1.5 Any of the galactaric acid salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 19.7°, 30.7°, 34.5°, 36.7° and 37.6°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0244] 1.6 Any of the galactarate salts 1-1.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 6.8 Å, 4.9 Å, 4.5 Å, 4.1 Å, 3.4 Å, 3.3 Å, 2.9 Å, 2.6 Å, 2.4 Å and 2.2 Å.

[0245] 1.7 Any of the galactarate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 4.5 Å, 2.9 Å, 2.6 Å, 2.4 Å and 3.3 Å.

[0246] 1.8 Any of the galactaric acid salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 10 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0247] 1.9 Any of the galactaric acid salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 204°C and 206°C, e.g., about 205°C.

[0248] 1.10 Any of the galactarate salts 1-1.9, wherein Compound A free base and the galactarate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:0.9.

[0249] In a further embodiment, the disclosure provides a first adipate salt of Compound A [Adipate Salt 1].

[0250] 1.1 Crystalline form, adipate salt 1.

[0251] 1.2 Adipate 1 or 1.1 in anhydrous form.

[0252] 1.3 Any of the adipates 1 to 1.1, wherein the salt crystal is an ethyl acetate solvate.

[0253] 1.4 Any of the adipates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.0°, 7.2°, 10.0°, 15.4°, 16.3°, 16.6°, 17.8°, 20.5°, 22.6° and 23.9°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0254] 1.5 Any of the adipates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 7.2°, 10.0°, 16.3°, 17.8° and 23.9°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0255] 1.6 Any of the adipate salts 1-1.5, wherein the salt crystals exhibit a powder X-ray diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 17.8 Å, 12.2 Å, 8.8 Å, 5.7 Å, 5.4 Å, 5.3 Å, 5.0 Å, 4.3 Å, 3.9 Å and 3.7 Å.

[0256] 1.7 Any of the adipates 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 12.2 Å, 8.8 Å, 5.4 Å, 5.0 Å and 3.7 Å.

[0257] 1.8 Any of the adipates 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 11 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0258] 1.9 Any of the adipates 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 119°C and 121°C, e.g., about 120°C, and / or between about 159°C and 161°C, e.g., about 160°C.

[0259] 1.10 Any of the adipates 1-1.9, wherein Compound A free base and adipic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0260] In a further embodiment, the disclosure provides a second adipate salt of Compound A [Adipate Salt 2].

[0261] 2.1 A crystalline form, the adipate salt 2.

[0262] 2.2 Adipate 2 or 2.1, in anhydrous form.

[0263] 2.3 Any of the adipates 2 to 2.1, wherein the salt crystal is an acetonitrile solvate.

[0264] 2.4 Any of the adipates 2-2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 6.7°, 8.9°, 10.7°, 15.7°, 16.9°, 17.8°, 18.0°, 21.3° and 22.3°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0265] 2.5 Any of the adipates 2-2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 6.7°, 8.9°, 10.7° and 18.0°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0266] 2.6 Any of the adipate salts 2-2.5, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having d-spacing values ​​selected from the group consisting of 18.1 Å, 13.2 Å, 9.9 Å, 8.3 Å, 5.6 Å, 5.3 Å, 5.0 Å, 4.9 Å, 4.2 Å and 4.0 Å.

[0267] 2.7 Any of the adipates 2-2.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 18.1 Å, 13.2 Å, 9.9 Å, 8.3 Å and 4.9 Å.

[0268] 2.8 Any of the adipate salts 2-2.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 12 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0269] 2.9 Any of the adipates 2 to 2.8, wherein the salt crystals show a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 159°C and 161°C, for example, about 160°C.

[0270] 2.10 Any of the adipates 2-2.9, wherein Compound A free base and adipic acid counterion are present in a molar ratio of about 4:1 to about 1:2, such as about 2:1, such as about 1:1.

[0271] In a further embodiment, the disclosure provides a third adipate salt of Compound A [Adipate Salt 3].

[0272] 3.1 Crystalline form, adipate salt 3.

[0273] 3.2 Adipate 3 or 3.1 in anhydrous form.

[0274] 3.3 Any of the adipates 3 to 3.1, wherein the salt crystal is an acetone solvate.

[0275] 3.4 Any of the adipates 3-3.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 8.1°, 10.5°, 11.1°, 12.2°, 12.9°, 18.2°, 21.5°, 23.9° and 24.4°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0276] 3.5 Any of the adipates 3-3.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 10.5°, 12.2°, 18.2° and 24.4°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0277] 3.6 Any of the adipate salts 3-3.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern including at least five peaks having d-spacing values ​​selected from the group consisting of 13.6 Å, 10.9 Å, 8.4 Å, 8.0 Å, 7.2 Å, 6.8 Å, 4.9 Å, 4.1 Å, 3.7 Å and 3.6 Å.

[0278] 3.7 Any of the adipate salts 3-3.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 13.6 Å, 8.4 Å, 7.2 Å, 4.9 Å and 3.6 Å.

[0279] 3.8 Any of the adipate salts 3-3.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 12A as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0280] 3.9 Any of adipates 3 to 3.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 109°C and 112°C, for example at about 109°C.

[0281] 3.10 Any of the adipates 3-3.9, wherein Compound A free base and adipic acid counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0282] In a further embodiment, the present disclosure provides a lactate salt of Compound A [Lactate Salt 1].

[0283] 1.1 The crystalline form is the lactate salt.

[0284] 1.2 Lactate salt 1 or 1.1, in anhydrous form.

[0285] 1.3 Any of the lactates 1 to 1.1, wherein the salt crystal is an ethyl acetate solvate or a toluene solvate.

[0286] 1.4 Any of Lactate Salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.4°, 6.5°, 9.0°, 11.9°, 12.3°, 17.1°, 19.4°, 20.5°, 23.3° and 23.2°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0287] 1.5 Any of Lactate Salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.4°, 6.5°, 11.9°, 12.3° and 20.5°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0288] 1.6 Any of Lactate Salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 14.0 Å, 13.8 Å, 13.7 Å, 9.8 Å, 7.5 Å, 7.2 Å, 5.2 Å, 4.6 Å, 4.3 Å and 3.8 Å.

[0289] 1.7 Any of Lactate Salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 13.8 Å, 13.7 Å, 7.5 Å, 7.2 Å and 4.3 Å.

[0290] 1.8 Any of Lactate Salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 13 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0291] 1.9 Any of Lactate Salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 187°C and 190°C, e.g., about 187°C or 188°C.

[0292] 1.10 Any of the lactate salts 1-1.9, wherein Compound A free base and lactate counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0293] In a further embodiment, the disclosure provides a first oxalate salt of Compound A [Oxalate 1].

[0294] 1.1 Crystalline form, oxalate salt1.

[0295] 1.2 Oxalate 1 or 1.1, in anhydrous form.

[0296] 1.3 Any of the oxalates 1 to 1.1, wherein the salt crystal is a 3-heptanone solvate.

[0297] 1.4 Any of the oxalates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 7.1°, 8.5°, 12.2°, 12.3°, 16.3°, 19.2°, 20.7°, 22.9°, 24.1° and 25.4°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0298] 1.5 Any of the oxalates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 8.5°, 12.2°, 12.3°, 16.3° and 20.7°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0299] 1.6 Any of the oxalate salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 12.4 Å, 10.4 Å, 7.2 Å, 5.4 Å, 4.8 Å, 4.6 Å, 4.3 Å, 3.9 Å, 3.7 Å and 3.5 Å.

[0300] 1.7 Any of the oxalate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 10.4 Å, 7.2 Å, 5.4 Å, 4.6 Å and 4.3 Å.

[0301] 1.8 Any of the oxalate salts 1-1.7, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 14 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0302] 1.9 Any of the oxalates 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 218°C and 220°C, for example at about 219°C.

[0303] 1.10 Any of the oxalate salts 1-1.9, wherein Compound A free base and oxalate counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0304] In a further embodiment, the disclosure provides a second oxalate salt of Compound A [Oxalate 2].

[0305] 2.1 Crystalline form, oxalate salt2.

[0306] 2.2 Oxalate 2 or 2.1, in anhydrous form.

[0307] 2.3 Any of the oxalates 2 to 2.1, wherein the salt crystal is an acetonitrile solvate.

[0308] 2.4 Any of the oxalates 2-2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 6.7°, 7.2°, 16.3°, 16.7°, 17.0°, 19.5°, 20.0°, 20.6° and 20.8°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0309] 2.5 Any of the oxalates 2-2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.7°, 7.2°, 16.7°, 17.0° and 20.0°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0310] 2.6 Any of the oxalate salts 2-2.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 13.7 Å, 13.2 Å, 12.2 Å, 5.4 Å, 5.3 Å, 5.2 Å, 5.1 Å, 4.6 Å, 4.4 Å and 4.3 Å.

[0311] 2.7 Any of the oxalate salts 2-2.6, wherein the salt crystal exhibits an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 13.2 Å, 12.2 Å, 5.3 Å, 5.2 Å and 4.4 Å.

[0312] 2.8 Any of the oxalate salts 2-2.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 15 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0313] 2.9 Any of the oxalates 2-2.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including endothermic peaks at about 165°C to 167°C, e.g., about 166°C, about 205°C to 207°C, e.g., about 207°C, and / or about 214°C to 216°C, e.g., about 215°C.

[0314] 2.10 Any of the oxalate salts 2-2.9, wherein Compound A free base and oxalate counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0315] In a further embodiment, the disclosure provides a third oxalate salt of Compound A [Oxalate 3].

[0316] 3.1 Crystalline form, oxalate salt3.

[0317] 3.2 The oxalate salt 3 or 3.1 in solvate form.

[0318] 3.3 Any of the oxalates 3 to 3.1, wherein the salt crystal is a 3-heptanone solvate, a 2-butanone solvate, or an ethyl acetate solvate.

[0319] 3.4 Any of the oxalates 3-3.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.3°, 6.0°, 11.9°, 16.6°, 17.7°, 18.3°, 19.6°, 20.5°, 20.7° and 21.2°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0320] 3.5 Any of the oxalates 3-3.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.3°, 6.0°, 11.9°, 20.7° and 21.2°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0321] 3.6 Any of the oxalate salts 3-3.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 16.6 Å, 14.7 Å, 7.4 Å, 5.3 Å, 5.0 Å, 4.8 Å, 4.5 Å, 4.3 Å, 4.2 Å and 3.7 Å.

[0322] 3.7 Any of the oxalate salts 3-3.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 16.6 Å, 14.7 Å, 7.4 Å, 4.3 Å and 4.2 Å.

[0323] 3.8 Any of the oxalate salts 3-3.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 16 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0324] 3.9 Any of the oxalates 3-3.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern that includes an endothermic peak between about 214°C and 220°C, e.g., about 214°C, 218°C, or 219°C.

[0325] 3.10 Any of the oxalate salts 3-3.9, wherein Compound A free base and oxalate counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0326] In a further embodiment, the present disclosure provides a fourth oxalate salt of Compound A [Oxalate 4].

[0327] 4.1 Crystalline form, oxalate salt 4.

[0328] 4.2 The oxalate salt 4 or 4.1 in solvate form.

[0329] 4.3 Any of the oxalates 4 to 4.1, wherein the salt crystal is an ethyl salicylate solvate.

[0330] 4.4 Any of the oxalates 4-4.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.8°, 11.6°, 12.1°, 18.1°, 18.5°, 20.4°, 21.4°, 21.9°, 27.1° and 23.2°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0331] 4.5 Any of the oxalates 4-4.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.8°, 11.6°, 18.1°, 20.4° and 21.9°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0332] 4.6 Any of the oxalate salts 4-4.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 15.3 Å, 7.6 Å, 7.3 Å, 4.9 Å, 4.8 Å, 4.3 Å, 4.1 Å, 3.8 Å, 3.3 Å and 3.1 Å.

[0333] 4.7 Any of the oxalate salts 4-4.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 15.3 Å, 7.6 Å, 4.9 Å, 4.3 Å and 4.1 Å.

[0334] 4.8 Any of the oxalate salts 4-4.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 57 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0335] 4.9 Any of the oxalates 4-4.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 125°C and 128°C, e.g., about 126°C, and / or between about 138°C and 148°C, e.g., about 139°C.

[0336] 4.10 Any of the oxalate salts 4-4.9, wherein Compound A free base and oxalate counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0337] In a further embodiment, the present disclosure provides a palmitate salt of Compound A [Palmitate Salt 1].

[0338] 1.1 Palmitate salt, a crystalline form.

[0339] 1.2 Palmitate 1 or 1.1, in anhydrous form.

[0340] 1.3 Any of palmitate salts 1 to 1.1, wherein the salt crystal is an ethyl acetate, 2-butanone, acetonitrile or 3-heptanone solvate.

[0341] 1.4 Any of palmitate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 4.3°, 5.5°, 6.5°, 7.3°, 8.5°, 9.5°, 10.9°, 19.2°, 21.6° and 22.8°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0342] 1.5 Any of palmitate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 4.3°, 5.5°, 8.5°, 9.5° and 22.8°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0343] 1.6 Any of palmitate salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 20.5 Å, 16.1 Å, 13.5 Å, 12.0 Å, 10.4 Å, 9.3 Å, 8.1 Å, 4.6 Å, 4.1 Å and 3.9 Å.

[0344] 1.7 Any of palmitate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 20.5 Å, 16.1 Å, 10.4 Å, 9.3 Å and 3.9 Å.

[0345] 1.8 Any of Palmitate Salts 1-1.7, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 17 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0346] 1.9 Any of palmitate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 59°C and 66°C, e.g., about 59°C, 62°C, or 63°C.

[0347] 1.10 Any of the palmitate salts 1-1.9, wherein Compound A free base and palmitate counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0348] In a further embodiment, the present disclosure provides a 2-oxo-glutarate salt of Compound A [2-oxo-glutarate salt 1].

[0349] 1.1 Crystalline form of 2-oxo-glutarate salt 1.

[0350] 1.2 2-oxo-glutarate 1 or 1.1 in solvate form.

[0351] 1.3 Any of 2-oxo-glutarate salts 1 to 1.1, wherein the salt crystal is an ethyl acetate solvate.

[0352] 1.4 Any of 2-oxo-glutarate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.1°, 8.5°, 10.1°, 11.0°, 11.8°, 14.5°, 15.7°, 17.5°, 19.8° and 20.2°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0353] 1.5 Any of 2-oxo-glutarate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.1°, 8.5°, 11.0°, 17.5° and 20.2°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0354] 1.6 Any of 2-oxo-glutarate salts 1-1.5, wherein the salt crystals exhibit a powder X-ray diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 17.4 Å, 10.4 Å, 8.7 Å, 8.0 Å, 7.5 Å, 6.1 Å, 5.6 Å, 5.1 Å, 4.5 Å and 4.4 Å.

[0355] 1.7 Any of 2-oxo-glutarate salts 1-1.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 17.4 Å, 10.4 Å, 8.0, 5.1 Å and 4.4 Å.

[0356] 1.8 Any of 2-oxo-glutarate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 18 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0357] 1.9 Any of 2-oxo-glutarate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak at about 124°C to 126°C, e.g., about 125°C, and / or at about 157°C to 159°C, e.g., about 158°C.

[0358] 1.10 Any of the 2-oxo-glutarate salts 1-1.9, wherein Compound A free base and the 2-oxo-glutarate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as 1:1.1.

[0359] In a further embodiment, the disclosure provides a first xinafoate salt of compound A [Xinafoate Salt 1].

[0360] 1.1 Crystalline form of the xinafoate salt 1.

[0361] 1.2 The xinafoate salt 1 or 1.1 in solvated form.

[0362] 1.3 Any of xinafoate salts 1 to 1.1, wherein the salt crystal is an acetonitrile solvate.

[0363] 1.4 Any of xinafoate salts 1-1.3, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.4°, 6.5°, 6.7°, 12.2°, 13.6°, 14.4°, 14.8°, 18.2°, 18.8° and 22.9°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0364] 1.5 Any of xinafoate salts 1-1.4, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.4°, 6.5°, 6.7°, 12.2° and 14.8°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0365] 1.6 Any of the xinafoate salts 1-1.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 16.3 Å, 13.5 Å, 13.1 Å, 7.3 Å, 6.5 Å, 6.1 Å, 6.0 Å, 4.9 Å, 4.7 Å and 3.9 Å.

[0366] 1.7 Any of the xinafoate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 16.3 Å, 13.5 Å, 13.1 Å, 7.3 Å and 6.0 Å.

[0367] 1.8 Any of xinafoate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 19 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0368] 1.9 Any of the xinafoate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including endothermic peaks at about 130°C to 132°C, e.g., about 131°C, and between about 143°C to 146°C, e.g., about 145°C, and / or between about 171°C to 174°C, e.g., about 172°C.

[0369] 1.10 Any of the xinafoate salts 1-1.9, wherein Compound A free base and the 1-hydroxy-2-naphthoic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0370] In a further embodiment, the disclosure provides a second xinafoate salt of compound A [xinafoate salt 2].

[0371] 2.1 Crystalline form, xinafoate salt 2.

[0372] 2.2 The xinafoate salt 2 or 2.1 in solvate form.

[0373] 2.3 Any of xinafoate salts 2 to 2.1, wherein the salt crystal is a toluene solvate.

[0374] 2.4 Any of xinafoate salts 2-2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 4.2°, 5.3°, 5.4°, 6.1°, 6.5° and 12.4°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0375] 2.5 Any of the xinafoate salts 2-2.4, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 20.9 Å, 16.8 Å, 16.5 Å, 14.6 Å, 14.5 Å, 13.6 Å and 7.1 Å.

[0376] 2.6 Any of the xinafoate salts 2-2.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 20 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0377] 2.7 Any of the xinafoate salts 2-2.6, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including endothermic peaks at about 117°C to 119°C, e.g., about 118°C, about 163°C to 166°C, e.g., about 164°C, and / or about 174°C to 177°C, e.g., about 175°C.

[0378] 2.8 Any of the xinafoate salts 2-2.7, wherein Compound A free base and the 1-hydroxy-2-naphthoic acid counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1.

[0379] In a further embodiment, the disclosure provides a third xinafoate salt of compound A [Xinafoate Salt 3].

[0380] 3.1 Crystalline form of the xinafoate salt 3.

[0381] 3.2 The xinafoate salt 3 or 3.1 in solvate form.

[0382] 3.3 Any of xinafoate salts 3 to 3.1, wherein the salt crystal is an ethyl acetate solvate.

[0383] 3.4 Any of the xinafoates 3-3.3, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.4°, 5.9°, 6.7°, 10.7°, 10.8°, 13.7°, 13.9°, 17.0°, 21.1° and 21.3°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0384] 3.5 Any of the xinafoate salts 3-3.4, wherein the salt crystals show a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.7°, 10.8°, 13.7°, 13.9° and 21.1°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0385] 3.6 Any of the xinafoate salts 3-3.5, wherein the salt crystals exhibit a powder X-ray diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 16.3 Å, 15.0 Å, 13.2 Å, 8.2 Å, 6.5 Å, 6.4 Å, 5.2 Å, 4.3 Å, 4.2 Å and 4.0 Å.

[0386] 3.7 Any of the xinafoate salts 3-3.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 13.2 Å, 8.2 Å, 6.5 Å, 6.4 Å and 4.2 Å.

[0387] 3.8 Any of the xinafoate salts 3-3.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 21 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0388] 3.9 Any of the xinafoate salts 3-3.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 131°C and 133°C, e.g., about 132°C, and / or between about 170°C and 173°C, e.g., about 172°C.

[0389] 3.10 Any of the xinafoate salts 3-3.9, wherein Compound A free base and the 1-hydroxy-2-naphthoic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example, about 1:1.

[0390] In a further embodiment, the disclosure provides a first tosylate salt of Compound A [Tosylate Salt 1].

[0391] 1.1 Crystalline form, tosylate salt 1.

[0392] 1.2 Tosylate salt 1 or 1.1, in anhydrous form.

[0393] 1.3 Any of the tosylates 1 to 1.1, wherein the salt crystal is a 3-heptanone solvate.

[0394] 1.4 Any of the tosylates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.1°, 5.6°, 8.5°, 10.5°, 15.5°, 17.1°, 20.1°, 20.4°, 23.2° and 23.3°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0395] 1.5 Any of the tosylates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.6°, 8.5°, 10.5°, 15.5° and 20.4°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0396] 1.6 Any of the tosylates 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 17.2 Å, 15.7 Å, 10.3 Å, 8.4 Å, 5.7 Å, 5.2 Å, 4.4 Å, 4.3 Å, 4.0 Å and 3.8 Å.

[0397] 1.7 Any of the tosylates 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 15.7 Å, 10.3 Å, 8.4 Å, 5.7 Å and 4.3 Å.

[0398] 1.8 Any of the tosylates 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 22 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0399] 1.9 Any of the tosylates 1 to 1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 216°C and 218°C, for example, at about 217°C.

[0400] 1.10 Any of the tosylate salts 1-1.9, wherein Compound A free base and the p-toluenesulfonic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0401] In a further embodiment, the disclosure provides a first tartrate salt of Compound A [Tartrate Salt 1].

[0402] 1.1 Tartrate salt, a crystalline form.1.

[0403] 1.2 Tartrate 1 or 1.1, in anhydrous form.

[0404] 1.3 Any of the tartrate salts 1-1.1, wherein the salt crystals are in the form of a solvate, for example, the salt crystals are an acetone solvate.

[0405] 1.4 Any of the tartrate salts 1-1.3, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 3.7°, 6.0°, 6.9°, 10.4°, 11.6°, 15.0°, 17.5°, 20.3°, 20.8° and 21.7°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0406] 1.5 Any of the tartrate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.0°, 6.9°, 11.6°, 20.3° and 21.7°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0407] 1.6 Any of the tartrate salts 1-1.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 23.9 Å, 14.8 Å, 12.8 Å, 8.5 Å, 7.6 Å, 5.9 Å, 5.1 Å, 4.4 Å, 4.3 Å and 4.1 Å.

[0408] 1.7 Any of the tartrate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 14.8 Å, 12.8 Å, 7.6 Å, 4.4 Å and 4.1 Å.

[0409] 1.8 Any of the tartrate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 24 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0410] 1.9 Any of the tartrate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 134°C and 136°C, e.g., about 135°C.

[0411] 1.10 Any of the tartrate salts 1-1.9, wherein Compound A free base and the tartrate counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0412] In a further embodiment, the disclosure provides a first tartrate salt of Compound A [Tartrate Salt 2].

[0413] 2.1 Crystalline form, tartrate salt2.

[0414] 2.2 Tartrate salt 2 or 2.1 in solvate form.

[0415] 2.3 Any of the tartrate salts 2 to 2.1, wherein the salt crystal is an ethyl tert-butyl ether solvate.

[0416] 2.4 Any of the tartrate salts 2-2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.9°, 6.3°, 8.0°, 10.2°, 11.1°, 12.2°, 12.6°, 17.0°, 17.4° and 21.5°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0417] 2.5 Any of the tartrate salts 2-2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.9°, 6.3°, 12.2°, 12.6°, and 17.0°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0418] 2.6 Any of the tartrate salts 2-2.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 14.9 Å, 14.1 Å, 11.0 Å, 8.6 Å, 7.9 Å, 7.2 Å, 7.0 Å, 5.2 Å, 5.1 Å and 4.1 Å.

[0419] 2.7 Any of the tartrate salts 2-2.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 14.1 Å, 14.9 Å, 7.2 Å, 7.0 Å and 5.2 Å.

[0420] 2.8 Any of the tartrate salts 2-2.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 56 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0421] 2.9 Any of the tartrate salts 2-2.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including endothermic peaks at about 103°C to 106°C, e.g., about 104°C, about 120°C to 123°C, e.g., about 121°C, and / or about 134°C to 137°C, e.g., about 136°C.

[0422] 2.10 Any of the tartrate salts 2-2.9, wherein Compound A free base and the tartrate counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0423] In a further embodiment, the disclosure provides a first succinate salt of Compound A [Succinate 1].

[0424] 1.1 Crystalline form, succinate salt 1.

[0425] 1.2 Succinate salt 1 or 1.1 in solvate form.

[0426] 1.3 Any of the succinate salts 1 to 1.1, wherein the salt crystal is an acetone solvate.

[0427] 1.4 Any of succinate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.9°, 7.1°, 9.4°, 9.8°, 16.0°, 16.4°, 17.1°, 19.3°, 22.8° and 25.8°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0428] 1.5 Any of succinate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.9°, 7.1°, 9.8°, 16.4° and 19.3°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0429] 1.6 Any of the succinate salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 12.8 Å, 12.5 Å, 9.4 Å, 9.0 Å, 5.5 Å, 5.4 Å, 5.2 Å, 4.6 Å, 3.9 Å and 3.5 Å.

[0430] 1.7 Any of the succinate salts 1-1.6, wherein the salt crystal exhibits an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 12.8 Å, 12.5 Å, 9.0 Å, 5.4 Å and 4.6 Å.

[0431] 1.8 Any of the succinate salts 1-1.7, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 25 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0432] 1.9 Any of succinate salts 1 to 1.8, wherein the salt crystal exhibits a differential scanning calorimetry (DSC) pattern including endothermic peaks at about 153°C to 155°C, e.g., about 154°C, about 172°C to 175°C, e.g., about 173°C, and / or about 178°C to 181°C, e.g., about 180°C.

[0433] 1.10 Any of the succinate salts 1-1.9, wherein Compound A free base and succinate counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:0.6.

[0434] In a further embodiment, the disclosure provides a second succinate salt of Compound A [Succinate Salt 2].

[0435] 2.1 Crystalline form, succinate salt 2.

[0436] 2.2 Succinate 2 or 2.1, in anhydrous form.

[0437] 2.3 Any of the succinate salts 2 to 2.1, wherein the salt crystal is an ethyl acetate solvate.

[0438] 2.4 Any of succinate salts 2 to 2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.9°, 9.4°, 22.4°, 16.3°, 19.3°, 4.6°, 25.7°, 21.4°, 13.6° and 23.9°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0439] 2.5 Any of succinate salts 2 to 2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.9°, 9.4°, 22.4°, 16.3° and 19.3°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0440] 2.6 Any of succinate salts 2-2.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 19.3 Å, 12.8 Å, 9.4 Å, 6.5 Å, 5.4 Å, 4.6 Å, 4.1 Å, 4.0 Å, 3.7 Å and 3.5 Å.

[0441] 2.7 Any of the succinate salts 2-2.6, wherein the salt crystal exhibits an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 12.8 Å, 9.4 Å, 5.4 Å, 4.6 Å and 4.0 Å.

[0442] 2.8 Any of succinate salts 2-2.7, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 26 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0443] 2.9 Any of succinate salts 2 to 2.8, wherein the salt crystal exhibits a differential scanning calorimetry (DSC) pattern including an endothermic peak at about 150°C to 152°C, e.g., about 151°C, about 163°C to 165°C, e.g., about 164°C, about 172°C to 175°C, e.g., about 174°C, and / or about 178°C to 181°C, e.g., about 179°C.

[0444] 2.10 Any of the succinate salts 2-2.9, wherein Compound A free base and succinate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:0.8.

[0445] In a further embodiment, the disclosure provides a first mesylate salt of Compound A [Mesylate Salt 1].

[0446] 1.1 Crystalline form, mesylate salt 1.

[0447] 1.2 Mesylate 1 or 1.1, anhydrous form.

[0448] 1.3 Any of the mesylates 1 to 1.1, wherein the salt crystal is an acetone solvate.

[0449] 1.4 Any of the mesylates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.2°, 6.4°, 11.7°, 12.3°, 17.1°, 18.8°, 20.2°, 21.2°, 29.7° and 29.8°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0450] 1.5 Any of the mesylates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.4°, 18.8°, 20.2°, 21.2° and 29.7°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0451] 1.6 Any of the mesylates 1-1.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 14.2 Å, 13.8 Å, 7.6 Å, 7.2 Å, 5.2 Å, 4.9 Å, 4.7 Å, 4.4 Å, 4.2 Å and 3.0 Å.

[0452] 1.7 Any of the mesylates 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 13.8 Å, 4.7 Å, 4.4 Å, 4.2 Å and 3.0 Å.

[0453] 1.8 Any of the mesylates 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 27 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0454] 1.9 Any of the mesylates 1 to 1.8, wherein the salt crystals show a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 310°C and 312°C, for example, at about 311°C.

[0455] 1.10 Any of the mesylate salts 1-1.9, wherein Compound A free base and the methanesulfonate counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0456] In a further embodiment, the present disclosure provides a napadisylate salt of Compound A [napadisylate salt 1].

[0457] 1.1 Crystalline form of napadisilate salt 1.

[0458] 1.2 Napadisylate 1 or 1.1 in solvate form.

[0459] 1.3 Any of napadisilate salts 1 to 1.1, wherein the salt crystal is an acetonitrile solvate.

[0460] 1.4 Any of napadisilate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 3.1°, 12.6°, 15.8°, 16.1°, 16.7°, 18.6°, 25.3° and 30.5°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0461] 1.5 Any of napadisilate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 3.1°, 12.6°, 15.8°, 16.7° and 25.3°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0462] 1.6 Any of napadisilate salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 28.3 Å, 7.0 Å, 5.6 Å, 5.5 Å, 5.3 Å, 4.8 Å, 3.5 Å and 2.9 Å.

[0463] 1.7 Any of napadisylate salts 1-1.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 28.3 Å, 7.0 Å, 5.6 Å, 5.3 Å and 3.5 Å.

[0464] 1.8 Any of napadisylate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 28 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0465] 1.9 Any of napadisylate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 103°C and 107°C, for example, at about 105°C.

[0466] 1.10 Any of napadisilate salts 1-1.9, wherein Compound A free base and naphthalenedisulfonic acid counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:1.2.

[0467] In a further embodiment, the present disclosure provides an edisylate salt of Compound A [edisylate salt 1].

[0468] 1.1 Crystalline form, edisylate salt 1.

[0469] 1.2 Edisylate 1 or 1.1, in anhydrous form.

[0470] 1.3 Any of the edisylate salts 1 to 1.1, wherein the salt crystal is a 2-butanone solvate.

[0471] 1.4 Any of the edisylate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 4.5°, 4.7°, 11.7°, 12.2°, 12.8°, 17.3°, 18.4°, 18.7°, 21.3° and 25.6°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0472] 1.5 Any of the edisylate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 4.7°, 12.8°, 18.7°, 21.3° and 25.6°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0473] 1.6 Any of the edisylate salts 1-1.5, wherein the salt crystals exhibit a powder X-ray diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 19.7 Å, 18.7 Å, 7.6 Å, 7.2 Å, 6.9 Å, 5.1 Å, 4.8 Å, 4.7 Å, 4.2 Å and 3.5 Å.

[0474] 1.7 Any of the edisylate salts 1-1.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 18.7 Å, 6.9 Å, 4.7 Å, 4.2 Å and 3.5 Å.

[0475] 1.8 Any of the edisylate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 29 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0476] 1.9 Any of the edisylate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 295°C and 298°C, for example, at about 296°C.

[0477] 1.10 Any of the edisylate salts 1-1.9, wherein Compound A free base and the ethanedisulfonic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0478] In a further embodiment, the present disclosure provides a propionate salt of Compound A [Propionate Salt 1].

[0479] 1.1 The crystalline form, the propionate salt.1.

[0480] 1.2 The propionate salt 1 or 1.1, in solvate form.

[0481] 1.3 Any of Propionate Salts 1 to 1.1, wherein the salt crystal is a methanol solvate.

[0482] 1.4 Any of the propionate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.7°, 8.8°, 9.5°, 16.1°, 17.0°, 17.5°, 18.3°, 19.0°, 22.7° and 32.6°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0483] 1.5 Any of the propionate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 16.1°, 17.0°, 18.3°, 22.7° and 32.6°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0484] 1.6 Any of Propionate Salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 15.4 Å, 10.1 Å, 9.3 Å, 5.5 Å, 5.2 Å, 5.1 Å, 4.8 Å, 4.7 Å, 3.9 Å and 2.7 Å.

[0485] 1.7 Any of the propionate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 5.5 Å, 5.2 Å, 4.8 Å, 3.9 Å and 2.7 Å.

[0486] 1.8 Any of Propionate Salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 30 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0487] 1.9 Any of Propionate Salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 109°C and 112°C, e.g., about 111°C, and / or between about 135°C and 137°C, e.g., about 136°C.

[0488] 1.10 Any of the propionate salts 1-1.9, wherein Compound A free base and the propionate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, for example about 1:0.7.

[0489] In a further embodiment, the present disclosure provides a caprylic acid salt of Compound A [Caprylic Acid Salt 1].

[0490] 1.1 The caprylate salt, a crystalline form.

[0491] 1.2 Caprylate 1 or 1.1, in anhydrous form.

[0492] 1.3 Any of the caprylate salts 1 to 1.1, wherein the salt crystal is a methanol solvate.

[0493] 1.4 Any of the caprylate salts 1-1.3, wherein the salt crystals show a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 2.9°, 3.0°, 4.5°, 4.6°, 4.7°, 4.8°, 4.9°, 6.0°, 22.0° and 22.8°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0494] 1.5 Any of the caprylate salts 1-1.4, wherein the salt crystals show a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 4.6°, 4.7°, 4.8°, 4.9° and 22.8°, the XRPD pattern being measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0495] 1.6 Any of the caprylate salts 1-1.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 30.1 Å, 29.2 Å, 19.7 Å, 19.3 Å, 18.7 Å, 18.2 Å, 18.0 Å, 14.8 Å, 4.0 Å and 3.9 Å.

[0496] 1.7 Any of the caprylate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 19.3 Å, 18.7 Å, 18.2 Å, 18.0 Å and 3.9 Å.

[0497] 1.8 Any of Caprylate Salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 31 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0498] 1.9 Any of the caprylate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 102°C and 105°C, e.g., about 104°C.

[0499] 1.10 Any of the caprylate salts 1-1.9, wherein Compound A free base and the caprylate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:1.4.

[0500] In a further embodiment, the present disclosure provides a besylate salt of Compound A [Besylate Salt 1].

[0501] 1.1 Crystalline form, besylate salt 1.

[0502] 1.2 Anhydrous form, besylate 1 or 1.1.

[0503] 1.3 Any of the besylates 1 to 1.1, wherein the salt crystal is a 3-heptanone solvate.

[0504] 1.4 Any of the besylates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 7.7°, 7.8°, 11.7°, 13.9°, 15.9°, 21.4°, 21.9°, 22.1°, 23.4° and 26.5°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0505] 1.5 Any of the besylates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 7.7°, 7.8°, 11.7°, 21.9° and 23.4°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0506] 1.6 Any of the besylates 1-1.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 11.5 Å, 11.4 Å, 7.6 Å, 6.4 Å, 6.3 Å, 5.6 Å, 4.2 Å, 4.1 Å, 3.8 Å and 3.4 Å.

[0507] 1.7 Any of the besylates 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 11.5 Å, 11.4 Å, 7.6 Å, 4.1 Å and 3.8 Å.

[0508] 1.8 Any of the besylates 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 32 as defined herein, the XRPD pattern being measured using a copper anode diffractometer at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0509] 1.9 Any of the besylates 1 to 1.8, wherein the salt crystals show a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 237°C and 240°C, for example, at about 238°C.

[0510] 1.10 Any of the besylates 1-1.9, wherein Compound A free base and the benzenesulfonic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0511] In a further embodiment, the present disclosure provides a benzoate salt of Compound A [Benzoate Salt 1].

[0512] 1.1 The benzoate salt 1, in crystalline form.

[0513] 1.2 Benzoate 1 or 1.1 in anhydrous form.

[0514] 1.3 Any of benzoates 1 to 1.1, wherein the salt crystal is a 3-heptanone solvate.

[0515] 1.4 Any of benzoates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.3°, 5.5°, 5.8°, 6.3°, 6.4°, 11.6°, 12.3°, 13.1°, 19.0° and 19.1°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0516] 1.5 Any of benzoates 1 to 1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.8°, 6.3°, 6.4°, 11.6° and 13.1°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0517] 1.6 Any of Benzoate Salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 16.5 Å, 16.2 Å, 15.2 Å, 14.0 Å, 13.9 Å, 7.7 Å, 7.2 Å, 6.8 Å, 4.6 Å and 4.7 Å.

[0518] 1.7 Any of benzoate salts 1-1.6, wherein the salt crystal exhibits an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 15.2 Å, 14.0 Å, 13.9 Å, 7.7 Å and 6.8 Å.

[0519] 1.8 Any of Benzoate Salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 33 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0520] 1.9 Any of the benzoates 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including endothermic peaks at about 59°C to 62°C, e.g., about 60°C, about 81°C to 84°C, e.g., about 83°C, and / or about 115°C to 118°C, e.g., about 116°C.

[0521] 1.10 Any of the benzoates 1-1.9, wherein Compound A free base and the benzoate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:1.1.

[0522] In a further embodiment, the present disclosure provides a nicotinic acid salt of Compound A [Nicotinic Acid Salt 1].

[0523] 1.1 Nicotinic acid salts in crystalline form.

[0524] 1.2 Nicotinic acid salt 1 or 1.1, in anhydrous form.

[0525] 1.3 Any of nicotinic acid salts 1 to 1.1, wherein the salt crystal is an acetonitrile solvate.

[0526] 1.4 Any of nicotinic acid salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.2°, 8.7°, 10.8°, 12.0°, 12.7°, 17.9°, 20.0°, 20.5°, 20.8° and 21.6°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0527] 1.5 Any of nicotinic acid salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.2°, 10.8°, 12.7°, 20.0° and 20.8°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0528] 1.6 Any of nicotinic acid salts 1-1.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 17.0 Å, 10.1 Å, 8.2 Å, 7.4 Å, 6.9 Å, 5.0 Å, 4.4 Å, 4.3 Å, 4.1 Å and 3.8 Å.

[0529] 1.7 Any of nicotinic acid salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 17.0 Å, 8.2 Å, 6.9 Å, 4.4 Å and 4.3 Å.

[0530] 1.8 Any of nicotinic acid salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 34 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0531] 1.9 Any of nicotinic acid salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 135°C and 138°C, for example at about 137°C.

[0532] 1.10 Any of the nicotinic acid salts 1-1.9, wherein Compound A free base and nicotinic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0533] In a further embodiment, the present disclosure provides an isonicotinic acid salt of Compound A [Isonicotinic Acid Salt 1].

[0534] 1.1 Isonicotinate salt 1, in crystalline form.

[0535] 1.2 Isonicotinate 1 or 1.1 in solvate form.

[0536] 1.3 Any of isonicotinic acid salts 1 to 1.1, wherein the salt crystal is a toluene solvate.

[0537] 1.4 Any of isonicotinic acid salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.5°, 7.3°, 11.7°, 12.8°, 16.7°, 17.1°, 17.3°, 17.9°, 20.4° and 28.0°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0538] 1.5 Any of isonicotinic acid salts 1 to 1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.5°, 7.3°, 16.7°, 17.1° and 17.3°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0539] 1.6 Any of isonicotinic acid salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 16.1 Å, 15.9 Å, 12.1 Å, 7.5 Å, 6.9 Å, 5.3 Å, 5.2 Å, 5.1 Å, 5.0 Å and 3.2 Å.

[0540] 1.7 Any of isonicotinic acid salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 16.1 Å, 15.9 Å, 5.3 Å, 5.2 Å and 5.1 Å.

[0541] 1.8 Any of isonicotinic acid salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 35 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0542] 1.9 Any of isonicotinic acid salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak at between about 111°C and 114°C, e.g., about 113°C, and / or between about 128°C and 130°C, e.g., about 129°C.

[0543] 1.10 Any of the isonicotinate salts 1-1.9, wherein Compound A free base and isonicotinic acid counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:0.7.

[0544] In a further embodiment, the present disclosure provides an orotate salt of Compound A [Orotate Salt 1].

[0545] 1.1 The orotate salt, a crystalline form.

[0546] 1.2 The orotate salt 1 or 1.1 in solvated form.

[0547] 1.3 Any of the orotate salts 1 to 1.1, wherein the salt crystal is a 2-butanone solvate.

[0548] 1.4 Any of orotate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.8°, 7.2°, 10.4°, 11.8°, 12.6°, 13.5°, 16.9°, 21.9°, 22.5° and 28.9°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0549] 1.5 Any of orotate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.8°, 7.2°, 16.9°, 21.9° and 28.9°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0550] 1.6 Any of orotate salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 15.3 Å, 12.3 Å, 8.5 Å, 7.5 Å, 7.0 Å, 6.6 Å, 5.2 Å, 4.1 Å, 4.0 Å and 3.1 Å.

[0551] 1.7 Any of the orotate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 15.3 Å, 12.3 Å, 5.2 Å, 4.1 Å and 3.1 Å.

[0552] 1.8 Any of the orotate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 36 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0553] 1.9 Any of orotate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 137°C and 140°C, for example, at about 138°C.

[0554] 1.10 Any of the orotate salts 1-1.9, wherein Compound A free base and orotic acid counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:2.

[0555] In a further embodiment, the disclosure provides a first camsylate salt of Compound A [Camsylate Salt 1].

[0556] 1.1 The crystalline form, camsylate salt 1.

[0557] 1.2 The anhydrous form, camsylate salt 1 or 1.1.

[0558] 1.3 Any of camsylate salts 1 to 1.1, wherein the salt crystal is a 3-heptanone solvate.

[0559] 1.4 Any of camsylate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.3°, 8.3°, 10.0°, 12.6°, 15.2°, 17.8°, 18.0°, 19.3°, 19.4° and 24.5°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0560] 1.5 Any of camsylate salts 1 to 1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.3°, 10.0°, 15.2°, 18.0° and 19.4°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0561] 1.6 Any of camsylate salts 1-1.5, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 16.6 Å, 10.7 Å, 8.9 Å, 7.0 Å, 5.8 Å, 5.6 Å, 5.0 Å, 4.9 Å, 4.6 Å and 3.6 Å.

[0562] 1.7 Any of camsylate salts 1-1.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 16.6 Å, 8.9 Å, 5.8 Å, 4.9 Å and 4.6 Å.

[0563] 1.8 Any of the camsylate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 37 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0564] 1.9 Any of camsylate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak at about 227°C to 230°C, e.g., about 228°C, and / or about 253°C to 256°C, e.g., about 254°C.

[0565] 1.10 Any of the camsylate salts 1-1.9, wherein Compound A free base and camphorsulfonic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0566] In a further embodiment, the disclosure provides a second camsylate salt of Compound A [camsylate salt 2].

[0567] 2.1 The crystalline form, camsylate salt 2.

[0568] 2.2 The camsylate salt 2 or 2.1 in solvate form.

[0569] 2.3 Any of the camsylate salts 2 to 2.1, wherein the salt crystal is a toluene solvate.

[0570] 2.4 Any of camsylate salts 2 to 2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.7°, 5.4°, 9.1°, 9.4°, 12.6°, 16.0°, 16.5°, 17.6°, 18.3° and 20.2°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0571] 2.5 Any of camsylate salts 2 to 2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.7°, 5.4°, 9.1°, 17.6° and 18.3°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0572] 2.6 Any of camsylate salts 2-2.5, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 18.7 Å, 16.5 Å, 9.8 Å, 9.4 Å, 7.0 Å, 5.5 Å, 5.4 Å, 5.0 Å, 4.8 Å and 4.4 Å.

[0573] 2.7 Any of camsylate salts 2-2.6, wherein the salt crystal exhibits a powder X-ray diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 18.7 Å, 16.5 Å, 9.8 Å, 5.0 Å and 4.8 Å.

[0574] 2.8 Any of camsylate salts 2-2.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 38 as defined herein, the XRPD pattern being measured using a diffractometer with a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0575] 2.9 Any of the camsylate salts 2-2.8, wherein Compound A free base and camphorsulfonic acid counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0576] In a further embodiment, the disclosure provides a first salicylate salt of Compound A [Salicylate Salt 1].

[0577] 1.1 Salicylate salt 1, in crystalline form.

[0578] 1.2 Salicylate 1 or 1.1, in anhydrous form.

[0579] 1.3 Any of the salicylates 1 to 1.1, wherein the salt crystal is an acetonitrile solvate.

[0580] 1.4 Any of the salicylates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 7.0°, 11.0°, 11.5°, 13.3°, 13.8°, 17.2°, 18.9°, 19.8°, 20.3° and 21.0°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0581] 1.5 Any of the salicylates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 7.0°, 11.0°, 13.3°, 13.8° and 17.2°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0582] 1.6 Any of the salicylates 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 12.7 Å, 8.1 Å, 7.7 Å, 6.7 Å, 6.4 Å, 5.1 Å, 4.7 Å, 4.5 Å, 4.4 Å and 4.2 Å.

[0583] 1.7 Any of the salicylates 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 12.7 Å, 8.1 Å, 6.7 Å, 6.4 Å and 5.1 Å.

[0584] 1.8 Any of Salicylates 1-1.7, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 39 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0585] 1.9 Any of the salicylates 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including endothermic peaks at about 146°C to 150°C, e.g., about 147°C, about 153°C to 156°C, e.g., about 155°C, about 196°C to 199°C, e.g., about 197°C, and / or about 244°C to 247°C, e.g., about 245°C.

[0586] 1.10 Any of the salicylates 1-1.9, wherein Compound A free base and salicylic acid counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0587] In a further embodiment, the disclosure provides a second salicylate salt of Compound A [Salicylate Salicylate 2].

[0588] 2.1 The salicylate salt 2, in crystalline form.

[0589] 2.2 Salicylate 2 or 2.1 in solvate form.

[0590] 2.3 Any of the salicylates 2 to 2.1, wherein the salt crystal is a toluene solvate.

[0591] 2.4 Any of the salicylates 2-2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.9°, 11.3°, 12.4°, 14.3°, 16.7°, 19.7°, 21.3°, 22.0°, 24.5° and 25.0°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0592] 2.5 Any of the salicylates 2-2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.9°, 12.4°, 14.3°, 16.7° and 19.7°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0593] 2.6 Any of salicylates 2-2.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 14.1 Å, 12.7 Å, 7.8 Å, 7.1 Å, 6.2 Å, 5.3 Å, 4.5 Å, 4.2 Å, 4.0 Å and 3.6 Å.

[0594] 2.7 Any of salicylates 2-2.6, wherein the salt crystal exhibits an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 12.7 Å, 7.1 Å, 6.2 Å, 5.3 Å and 4.5 Å.

[0595] 2.8 Any of Salicylates 2-2.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 40 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0596] 2.9 Any of the salicylates 2 to 2.8, wherein the salt crystals show a differential scanning calorimetry (DSC) pattern including endothermic peaks at about 127°C to 130°C, e.g., about 128°C, about 143°C to 146°C, e.g., about 144°C, about 180°C to 183°C, e.g., about 181°C, about 196°C to 199°C, e.g., about 197°C, and about 244°C to 247°C, e.g., about 247°C.

[0597] 2.10 Any of the salicylates 2-2.9, wherein Compound A free base and salicylic acid counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0598] In a further embodiment, the disclosure provides an aminosalicylate salt of Compound A [Aminosalicylate Salt 1].

[0599] 1.1, Aminosalicylate 1, in crystalline form.

[0600] 1.2 Aminosalicylate 1 or 1.1, in anhydrous form.

[0601] 1.3 Any of the aminosalicylates 1 to 1.1, wherein the salt crystal is an acetonitrile solvate.

[0602] 1.4 Any of the aminosalicylates 1-1.3, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.8°, 10.7°, 13.5°, 13.9°, 17.0°, 20.4°, 20.7°, 20.8°, 21.3° and 21.5°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0603] 1.5 Any of the aminosalicylates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.8°, 10.7°, 13.9°, 17.0° and 20.7°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0604] 1.6 Any of the aminosalicylates 1-1.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 13.0 Å, 8.3 Å, 7.0 Å, 6.5 Å, 6.4 Å, 5.3 Å, 5.2 Å, 4.3 Å, 4.2 Å and 4.1 Å.

[0605] 1.7 Any of the aminosalicylates 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 13.0 Å, 8.3 Å, 6.4 Å, 5.2 Å and 4.3 Å.

[0606] 1.8 Any of the aminosalicylates 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 42 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0607] 1.9 Any of the aminosalicylates 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak at between about 130°C and 133°C, e.g., about 132°C, and / or between about 161°C and 164°C, e.g., about 162°C.

[0608] 1.10 Any of the aminosalicylates 1-1.9, wherein Compound A free base and the aminosalicylic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0609] In a further embodiment, the disclosure provides a first mandelate salt of Compound A [Mandelate Salt 1].

[0610] 1.1 The mandelate salt 1, in crystalline form.

[0611] 1.2 Mandelate salt 1 or 1.1 in solvate form.

[0612] 1.3 Any of the mandelate salts 1 to 1.1, wherein the salt crystal is a toluene solvate.

[0613] 1.4 Any of the mandelates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 7.7°, 8.5°, 10.0°, 11.4°, 11.9°, 19.8°, 20.0°, 20.1° and 20.8°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0614] 1.5 Any of the mandelates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 8.5°, 11.4°, 20.0° and 20.1°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0615] 1.6 Any of the mandelate salts 1-1.5, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 13.6 Å, 11.5 Å, 10.3 Å, 8.9 Å, 7.8 Å, 7.4 Å, 4.5 Å, 4.4 Å, 4.3 Å and 4.0 Å.

[0616] 1.7 Any of the mandelate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 13.6 Å, 10.3 Å, 8.9 Å, 7.8 Å and 4.4 Å.

[0617] 1.8 Any of the mandelate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 43 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0618] 1.9 Any of the mandelate salts 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 119°C and 128°C, e.g., about 120°C or 126°C.

[0619] 1.10 Any of the mandelate salts 1-1.9, wherein Compound A free base and mandelic acid counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0620] In a further embodiment, the disclosure provides a first mandelate salt of compound A [Mandelate Salt 2].

[0621] 2.1 The mandelate salt 2, in crystalline form.

[0622] 2.2 Mandelate salt 2 or 2.1 in solvate form.

[0623] 2.3 Any of the mandelate salts 2 to 2.1, wherein the salt crystal is a 3-heptanone solvate.

[0624] 2.4 Any of the mandelates 2-2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 6.0°, 8.1°, 8.5°, 8.6°, 8.7°, 12.6°, 17.3°, 20.7°, 22.2° and 22.1°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0625] 2.5 Any of the mandelates 2-2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 8.1°, 8.6°, 8.7°, 12.6° and 22.2°, and the XRPD pattern is measured using a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0626] 2.6 Any of the mandelate salts 2-2.5, wherein the salt crystals exhibit a powder X-ray diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 14.6 Å, 11.0 Å, 10.4 Å, 10.3 Å, 10.2 Å, 7.0 Å, 5.1 Å, 4.3 Å, 4.0 Å and 3.5 Å.

[0627] 2.7 Any of the mandelate salts 2-2.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 11.0 Å, 10.3 Å, 10.2 Å, 7.0 Å and 4.0 Å.

[0628] 2.8 Any of the mandelate salts 2-2.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 44 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0629] 2.9 Any of the mandelates 2-2.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 102°C and 105°C, for example at about 103°C.

[0630] 2.10 Any of the mandelate salts 2-2.9, wherein Compound A free base and mandelic acid counterion are present in a molar ratio of about 2:1 to about 1:2, e.g., about 1:1.

[0631] In a further embodiment, the disclosure provides a first acetamidobenzoate salt of compound A [acetamidobenzoate salt 1].

[0632] 1.1 Acetamidobenzoate 1, in crystalline form.

[0633] 1.2 Acetamidobenzoate 1 or 1.1 in anhydrous form.

[0634] 1.3 Any of acetamide benzoates 1 to 1.1, wherein the salt crystal is an ethyl acetate solvate.

[0635] 1.4 Any of acetamidobenzoates 1 to 1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.0°, 8.3°, 11.8°, 12.9°, 14.2°, 15.2°, 18.7°, 19.6°, 21.4° and 23.4°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0636] 1.5 Any of acetamidobenzoates 1 to 1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.0°, 8.3°, 14.2°, 15.2° and 18.7°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0637] 1.6 Any of acetamidobenzoates 1-1.5, wherein the salt crystals exhibit a powder X-ray diffraction pattern including at least five peaks having d-spacing values ​​selected from the group consisting of 14.7 Å, 10.6 Å, 7.5 Å, 6.8 Å, 6.2 Å, 5.8 Å, 4.7 Å, 4.5 Å, 4.2 Å and 3.8 Å.

[0638] 1.7 Any of acetamidobenzoates 1-1.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 14.7 Å, 10.6 Å, 6.2 Å, 5.8 Å and 4.7 Å.

[0639] 1.8 Any of acetamidobenzoates 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 45 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0640] 1.9 Any of acetamidobenzoates 1 to 1.8, wherein the salt crystals show a differential scanning calorimetry (DSC) pattern including an endothermic peak at about 168°C to 171°C, for example, about 170°C.

[0641] 1.10 Any of the acetamidobenzoates 1-1.9, wherein Compound A free base and 4-acetamido-benzoic acid counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:1.3.

[0642] In a further embodiment, the disclosure provides a first acetamidobenzoate salt of compound A [acetamidobenzoate salt 2].

[0643] 1.1 Acetamidobenzoate, in crystalline form.2.

[0644] 1.2 Acetamidobenzoate 2 or 2.1 in solvate form.

[0645] 1.3 Any of acetamidobenzoates 2 to 2.1, wherein the salt crystal is a 3-heptanone solvate.

[0646] 1.4 Any of acetamidobenzoates 2 to 2.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 6.8°, 10.7°, 11.6°, 13.8°, 14.3°, 15.8°, 16.4°, 19.2° and 21.5°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example, at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0647] 1.5 Any of acetamidobenzoates 2 to 2.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 6.8°, 14.3°, 15.8° and 21.5°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0648] 1.6 Any of acetamidobenzoates 2 to 2.5, wherein the salt crystals exhibit a powder X-ray diffraction pattern including at least five peaks having d-spacing values ​​selected from the group consisting of 18.1 Å, 13.1 Å, 8.3 Å, 7.7 Å, 6.4 Å, 6.2 Å, 5.6 Å, 5.4 Å, 4.6 Å and 4.1 Å.

[0649] 1.7 Any of acetamidobenzoates 2-2.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 18.1 Å, 13.1 Å, 6.2 Å, 5.6 Å and 4.1 Å.

[0650] 1.8 Any of acetamidobenzoates 2-2.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 46 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0651] 1.9 Any of acetamidobenzoates 2 to 2.8, wherein the salt crystals show a differential scanning calorimetry (DSC) pattern including an endothermic peak at about 127°C to 130°C, e.g., about 129°C, and / or about 170°C to 173°C, e.g., about 172°C.

[0652] 1.10 Any of the acetamidobenzoates 2-2.9, wherein Compound A free base and 4-acetamido-benzoic acid counterion are present in a molar ratio of about 2:1 to about 1:2, for example about 1:1.

[0653] In a further embodiment, the disclosure provides a trifluoroacetate salt of Compound A [Trifluoroacetate Salt 1].

[0654] 1.1 Crystalline form of trifluoroacetate salt 1.

[0655] 1.2 Trifluoroacetate salt 1 or 1.1 in anhydrous form.

[0656] 1.3 Any of the trifluoroacetates 1 to 1.1, wherein the salt crystal is an acetonitrile solvate.

[0657] 1.4 Any of trifluoroacetates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 6.6°, 8.7°, 8.9°, 17.0°, 18.8°, 19.5°, 20.4°, 23.4° and 24.6°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0658] 1.5 Any of trifluoroacetates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 6.6°, 8.9°, 17.0° and 23.4°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0659] 1.6 Any of trifluoroacetate salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern including at least five peaks having d-spacing values ​​selected from the group consisting of 13.6 Å, 13.3 Å, 10.2 Å, 10.0 Å, 5.2 Å, 4.7 Å, 4.6 Å, 4.3 Å, 3.8 Å and 3.6 Å.

[0660] 1.7 Any of trifluoroacetate salts 1-1.6, wherein the salt crystal exhibits an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 13.6 Å, 13.3 Å, 10.0 Å, 5.2 Å, and 3.8 Å.

[0661] 1.8 Any of the trifluoroacetates 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 47 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0662] 1.9 Any of trifluoroacetates 1 to 1.8, wherein the salt crystals show a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 253°C and 257°C, for example, about 255°C.

[0663] 1.10 Any of the trifluoroacetates 1-1.9, wherein Compound A free base and trifluoroacetate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, for example about 1:0.9.

[0664] In a further embodiment, the disclosure provides a dichloroacetate salt of Compound A [Dichloroacetate Salt 1].

[0665] 1.1 Dichloroacetate salt, crystalline form.

[0666] 1.2 Dichloroacetate salt 1 or 1.1 in anhydrous form.

[0667] 1.3 Any of dichloroacetates 1 to 1.1, wherein the salt crystal is an acetonitrile solvate.

[0668] 1.4 Any of dichloroacetates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 8.8°, 11.9°, 12.3°, 17.2°, 17.7°, 18.9°, 19.3°, 23.6° and 28.2°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0669] 1.5 Any of dichloroacetates 1 to 1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 11.9°, 17.2°, 17.7° and 18.9°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0670] 1.6 Any of dichloroacetate salts 1-1.5, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having d-spacing values ​​selected from the group consisting of 13.7 Å, 10.1 Å, 7.4 Å, 7.2 Å, 5.2 Å, 5.0 Å, 4.7 Å, 4.6 Å, 3.8 Å and 3.2 Å.

[0671] 1.7 Any of dichloroacetate salts 1-1.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 13.7 Å, 7.4 Å, 5.2 Å, 5.0 Å and 4.7 Å.

[0672] 1.8 Any of dichloroacetate salts 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 48 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0673] 1.9 Any of dichloroacetates 1 to 1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak at about 225°C to 228°C, e.g., about 227°C, and / or about 229°C to 232°C, e.g., about 230°C.

[0674] 1.10 Any of the dichloroacetate salts 1-1.9, wherein Compound A free base and the dichloroacetate counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, for example, about 1:0.8.

[0675] In a further embodiment, the present disclosure provides a caproate salt of Compound A [Caproate Salt 1].

[0676] 1.1 The crystalline form, caproate salt 1.

[0677] 1.2 Caproate 1 or 1.1, in anhydrous form.

[0678] 1.3 Any of caproate salts 1 to 1.1, wherein the salt crystal is a 2-butanone solvate.

[0679] 1.4 Any of caproates 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.2°, 7.5°, 7.8°, 10.2°, 11.3°, 12.2°, 12.6°, 19.6°, 23.0° and 23.4°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0680] 1.5 Any of caproates 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 5.2°, 7.8°, 10.2°, 11.3° and 23.0°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0681] 1.6 Any of caproates 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 17.1 Å, 11.8 Å, 11.3 Å, 8.6 Å, 7.8 Å, 7.2 Å, 7.0 Å, 4.5 Å, 3.9 Å and 3.8 Å.

[0682] 1.7 Any of caproates 1-1.6, wherein the salt crystals exhibit a powder X-ray diffraction pattern comprising peaks having d-spacing values ​​selected from the group consisting of 17.1 Å, 11.3 Å, 8.6 Å, 7.8 Å and 3.9 Å.

[0683] 1.8 Any of Caproates 1-1.7, wherein the salt crystals exhibit an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 49 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0684] 1.9 Any of Caproates 1-1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 89°C and 92°C, e.g., about 90°C, and / or between about 104°C and 107°C, e.g., about 105°C.

[0685] 1.10 Any of the caproates 1-1.9, wherein Compound A free base and caproic acid counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:0.9.

[0686] In a further embodiment, the present disclosure provides a laurate salt of Compound A [Laurate Salt 1].

[0687] 1.1 Laurate salt 1, in crystalline form.

[0688] 1.2 Laurate 1 or 1.1 in anhydrous form.

[0689] 1.3 Any of laurates 1 to 1.1, wherein the salt crystal is a 2-propanol solvate.

[0690] 1.4 Any of the laurate salts 1-1.3, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.3°, 4.6°, 5.5°, 5.9°, 9.2°, 10.9°, 11.0°, 22.1°, 22.0° and 22.7°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0691] 1.5 Any of the laurate salts 1-1.4, wherein the salt crystal exhibits a powder X-ray diffraction pattern including at least five peaks having 2θ angle values ​​selected from the group consisting of 4.3°, 4.6°, 5.5°, 5.9° and 22.7°, and the XRPD pattern is measured with a diffractometer using a copper anode, for example at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

[0692] 1.6 Any of the laurate salts 1-1.5, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having d-spacing values ​​selected from the group consisting of 20.4 Å, 19.1 Å, 16.1 Å, 14.9 Å, 10.4 Å, 9.6 Å, 8.1 Å, 8.0 Å, 4.0 Å and 3.9 Å.

[0693] 1.7 Any of the laurate salts 1-1.6, wherein the salt crystals exhibit an X-ray powder diffraction pattern including peaks having d-spacing values ​​selected from the group consisting of 20.4 Å, 19.1 Å, 16.1 Å, 14.9 Å and 3.9 Å.

[0694] 1.8 Any of the laurate salts 1-1.7, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 50 as defined herein, the XRPD pattern being measured on a diffractometer using a copper anode at wavelengths α1 of 1.5406 Å and α2 of 1.5444 Å.

[0695] 1.9 Any of laurate salts 1 to 1.8, wherein the salt crystals exhibit a differential scanning calorimetry (DSC) pattern including an endothermic peak between about 81°C and 84°C, for example, about 83°C.

[0696] 1.10 Any of the laurate salts 1-1.9, wherein Compound A free base and lauric acid counterion are present in a molar ratio of about 2:1 to about 1:2, such as about 1:1, such as about 1:1.4.

[0697] The above salt crystals (i.e., hydrochloride 1-8 and subsequent ones; malate 1 and subsequent ones; fumarate 1 and subsequent ones; sulfate 1 and subsequent ones; esylate 1 and subsequent ones; galactarate 1 and subsequent ones; adipate 1-3 and subsequent ones; lactate 1 and subsequent ones; oxalate 1-4 and subsequent ones; palmitate 1 and subsequent ones; 2-oxo-glutarate 1 and subsequent ones; xinafoate 1-3 and subsequent ones; tosylate 1-2 and subsequent ones; tartrate 1-2 and subsequent ones; succinate 1-2 and subsequent ones; mesylate 1 and subsequent ones; napadisylate 1 and subsequent ones; edisylate 1 and subsequent ones) and subsequent thereto; propionate 1 and subsequent thereto; caprylate 1 and subsequent thereto; besylate 1 and subsequent thereto; benzoate 1 and subsequent thereto; nicotinate 1 and subsequent thereto; isonicotinate 1 and subsequent thereto; orotate 1 and subsequent thereto; camsylate 1-2 and subsequent thereto; salicylate 1-2 and subsequent thereto; aminosalicylate 1 and subsequent thereto; mandelate 1-2 and subsequent thereto; acetamidobenzoate 1-2 and subsequent thereto; trifluoroacetate 1 and subsequent thereto; dichloroacetate 1 and subsequent thereto; caproate 1 and subsequent thereto; and laurate 1 and subsequent thereto) are collectively referred to as the salt crystals of the present disclosure.

[0698] In some embodiments, the salt crystals of the present disclosure are in a single crystalline form and are free or substantially free of other forms, e.g., have less than 10% by weight, preferably less than about 5% by weight, more preferably less than about 2% by weight, even more preferably less than about 1% by weight, even more preferably less than about 0.1% by weight, and most preferably less than about 0.01% by weight of amorphous form.

[0699] In some embodiments, the salt crystals of the present disclosure are in a single crystalline form and are free or substantially free of other forms, e.g., have less than 10% by weight, preferably less than about 5% by weight, more preferably less than about 2% by weight, even more preferably less than about 1% by weight, even more preferably less than about 0.1% by weight, and most preferably less than about 0.01% by weight of other crystalline forms.

[0700] In some embodiments, the salt crystals of the present disclosure are in a single crystalline form and are free or substantially free of other forms, e.g., have less than 10% by weight, preferably less than about 5% by weight, more preferably less than about 2% by weight, even more preferably less than about 1% by weight, even more preferably less than about 0.1% by weight, and most preferably less than about 0.01% by weight of amorphous and other crystalline forms.

[0701] Methods for producing and using the salt crystals of the present invention The present disclosure further provides a method for preparing a stable acid addition salt, e.g., a crystalline acid addition salt, of (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopent[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one ("Compound A") with a particular acid, the method comprising reacting the free base form of Compound A with an acid in a solvent and isolating the resulting salt [Method 1]. In certain embodiments, the present disclosure provides:

[0702] 1.1 Method 1 further comprising forming a slurry of compound A and an acid in a solvent at a temperature between about 30° C. and 70° C.

[0703] 1.2 Method 1.1, wherein a slurry is formed at a temperature between 30° C. and 70° C. for at least 1 hour (eg, 1 to 5 hours).

[0704] 1.3 Method 1.1 or 1.2, wherein the slurry is formed at a temperature between 30° C. and 70° C. for at least 1 to 3 hours.

[0705] 1.4 Any of methods 1.1-1.3, wherein the slurry is formed at a temperature of about 40°C to 60°C, such as about 45°C to 65°C, for example about 50°C.

[0706] 1.5 Any of Methods 1.1-1.4, wherein the slurry is formed at a temperature of about 50° C.

[0707] 1.6 Any of the preceding processes wherein the acid is hydrochloric acid, malic acid, fumaric acid, sulfuric acid, ethanesulfonic acid, galactaric acid, adipic acid, lactic acid, oxalic acid, palmitic acid, 2-oxo-glutaric acid, xinafoic acid, toluenesulfonic acid, tartaric acid, succinic acid, methanesulfonic acid, naphthalenedisulfonic acid, ethanedisulfonic acid, propionic naphthalenedisulfonic acid, caprylic naphthalenedisulfonic acid, benzenesulfonic acid, benzoic acid, nicotinic acid, isonicotinic acid, orotic acid, camsylic acid, salicylic acid, aminosalicylic acid, mandelic acid, acetamido-benzoic acid, trifluoroacetic acid, dichloroacetic acid, caproic acid, or lauric acid.

[0708] 1.7 Any of the preceding processes wherein the acid is hydrochloric acid, malic acid, tartaric acid or oxalic acid.

[0709] 1.8 Any of the preceding processes wherein the acid is hydrochloric acid.

[0710] 1.9 Any of the preceding processes wherein the acid is malic acid.

[0711] 1.10 Any of the preceding processes wherein the acid is tartaric acid.

[0712] 1.11 Any of the preceding processes wherein the acid is oxalic acid.

[0713] 1.12 Any of the preceding processes wherein the acid and free base forms of compound A are combined in a 1:1 molar ratio.

[0714] 1.13 Any of the preceding processes, wherein the solvent is water, acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, 3-heptanone, toluene, methanol, ethanol, propanol (e.g., isopropanol, 2-propanol), butanol (e.g., 2-ethyl-1-butanol), dimethyl sulfoxide (DMSO), anisole, ethyl butyl ketone, or a combination thereof.

[0715] 1.14 Any of the preceding processes, wherein the solvent is acetonitrile, ethyl acetate, 2-butanone, acetone, 3-heptanone, 2-butanone, or a combination thereof.

[0716] 1.15 Any of the preceding methods, further comprising the step of cooling the solution to a temperature of about -10°C to about 20°C.

[0717] 1.16 Method 1.15, wherein the solution is cooled to a temperature of about 0° C. to about 10° C.

[0718] 1.17 Method 1.15 or 1.16, wherein the solution is cooled to a temperature of about 5° C.

[0719] 1.18 Any of Methods 1.15-1.17, wherein the solution is cooled for at least about 5 hours.

[0720] 1.19 Any of Methods 1.15-1.18, wherein the solution is cooled for about 5 hours to about 24 hours.

[0721] 1.20 Any of Methods 1.15-1.18, wherein the solution is cooled for about 8 hours.

[0722] 1.21 Any of the preceding processes comprising the step of drying the solution by evaporation.

[0723] 1.22 The solution is placed under vacuum to evaporate the solvent, Method 1.21.

[0724] 1.23 Any of the preceding processes wherein the salt is crystalline.

[0725] 1.24 Any of the preceding processes wherein the resulting salt is crystalline, dissolved in a second solvent and subjected to one or more cooling cycles.

[0726] 1.25 Method 1.24, wherein the second solvent is water, acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, 3-heptanone, toluene, methanol, ethanol, propanol (e.g., isopropanol, 2-propanol), butanol (e.g., 2-ethyl-1-butanol), dimethyl sulfoxide (DMSO), anisole, ethyl butyl ketone, or a combination thereof.

[0727] 1.26 Method 1.24 or 1.25, wherein the cooling cycle comprises at least two cycles (eg, at least three cycles, at least four cycles, at least five cycles) of heating the solution followed by cooling.

[0728] 1.27 Any of methods 1.24-1.26, wherein the cooling cycle includes at least four cycles of heating the solution followed by cooling.

[0729] 1.28 The cooling cycle is a. Heating the solution to about 50°C; b. cooling the solution to about 0° C.; c. heating the solution to about 40° C.; d. cooling the solution to about 0° C.; e. heating the solution to about 30°C; f. cooling the solution to about 0° C.; g. heating the solution to about 20° C.; and h. Cool the solution to approximately 0°C. Any of methods 1.24 to 1.27, including

[0730] 1.29 Any of the preceding processes wherein the salt is crystalline.

[0731] The present disclosure further provides salt crystals of the present disclosure that are obtained or obtainable by any of Methods 1 and those that follow, or any of Examples 1-4.

[0732] The following disorders: A. Neurodegenerative diseases, including Parkinson's disease, restless legs, tremors, dyskinesia, Huntington's disease, Alzheimer's disease, and drug-induced movement disorders; B. Psychiatric disorders, including depression, attention deficit disorder, attention deficit hyperactivity disorder, bipolar disorder, anxiety, sleep disorders, e.g. narcolepsy, cognitive disorders, e.g. cognitive impairment in schizophrenia, dementia, Tourette's syndrome, autism, fragile X syndrome, psychostimulant withdrawal, and drug addiction; C. Circulatory and cardiovascular disorders, including cardiovascular diseases and related disorders described in International Application No. PCT / US2014 / 16741, the disclosure of which is incorporated herein by reference, including cerebrovascular disease, stroke, congestive heart disease, hypertension, pulmonary hypertension, e.g., pulmonary arterial hypertension, and sexual dysfunction; D. Respiratory and inflammatory diseases, including asthma, chronic obstructive pulmonary disease, and allergic rhinitis, as well as autoimmune and inflammatory diseases; E. Diseases that may be alleviated by enhancing progesterone signaling, such as female sexual dysfunction; F. Disease or disorder such as psychiatric illness, glaucoma, or elevated intraocular pressure; G. Traumatic brain injury; H. Cancer or tumor, e.g., brain tumor, glioma (e.g., ependymoma, astrocytoma, oligodendroglioma, brain stem glioma, optic nerve glioma, or mixed glioma, e.g., oligoastrocytoma), astrocytoma (e.g., glioblastoma multiforme), osteosarcoma, melanoma, leukemia, neuroblastoma, or leukemia; I. Renal disorders, such as renal fibrosis, chronic kidney disease, renal failure, glomerulosclerosis, and nephritis; J. A disease or condition characterized by low levels of cAMP and / or cGMP (or inhibition of the cAMP and / or cGMP signaling pathways) in cells expressing PDE1; and / or K. Diseases or conditions characterized by decreased dopamine D1 receptor signaling activity A method for preventing or treating a patient, e.g., a human, suffering from a disorder selected from the group consisting of the above, comprising administering to a patient in need of said prevention or treatment (a) a therapeutically effective amount of the compound (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (Compound A) in the form of an acid addition salt with any of the salt crystals disclosed herein [Method 2].

[0733] 2.1 A pharmaceutical composition comprising any of the disclosed crystalline salts for use as a medicament, e.g., for use in the manufacture of a medicament for the treatment or prevention of a disease as described in Method 2.

[0734] 2.2 Use of any of the salt crystals disclosed herein in the treatment or prevention of a disease as described in Method 2.

[0735] 2.3 Method 2, wherein the cocrystal is administered to the patient in an amount equivalent to 1-300 mg of compound 1 per day.

[0736] 2.4 Any of the preceding methods, wherein the co-crystal is administered to the patient in an amount equivalent to 15-180 mg of Compound 1 per day, such as an amount equivalent to 30-90 mg, such as an amount equivalent to 30-60 mg. EXAMPLES

[0737] The structure: [ka] A study is carried out to identify the crystalline form of a salt of compound 1, which is (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one having the formula:

[0738] Counterions are dissolved in methanol or water to obtain a 2M solution. Undissolved counterions are added as solids. 20 mg of compound 1 free base is dispensed into the wells of a master plate, and then counterions are dispensed so that the mixture has a molar ratio of 1:1. The wells are then added with the solvent (800 μl) identified below. The master plate is then stored in a thermoshaker and shaken at 50° C. for 2 hours.

[0739] The clear liquid in the master plate wells is divided and placed onto a cooling plate, an evaporation plate, or an HPLC plate. The cooling plate is cooled to 5° C. and the samples are stored at this temperature for approximately 16 hours. The evaporation plate is stored in a vacuum oven to allow complete evaporation of the solvent. The remaining liquid is absorbed with filter paper and the solids are dried under vacuum. All samples from each of the master plate, cooling plate, and evaporation plate are analyzed using high-throughput (HT)-XRPD.

[0740] XRPD data analysis shows various novel crystalline patterns. Some counterions show multiple patterns that may indicate polymorphism or solvate formation depending on the solvent. After all XRPD patterns are defined, the crystalline patterns are analyzed by thermogravimetry and differential scanning calorimetry.

[0741] XRPD is measured using a Bruker AXS D2 PHASER in Bragg-Brentano configuration with a scan range of 5-45°2θ. TGA measurements are performed using a Mettler Toledo TGA / DSC-3+ instrument. DSC measurements are performed using a Mettler Toledo DSC-3+ instrument. Samples are heated in aluminum (perforated) cups from 20°C to 350°C, applying a heating rate of 10°C / min.

[0742] Hydrochloride Aqueous hydrochloric acid is combined with compound 1 (25 mg) in ethyl acetate, followed by slurrying at 50° C. for 2 hours. The resulting salt is a solvate and is obtained as a white to off-white powder. The XRPD pattern of the hydrochloride salt 1 has the peaks listed in Table 1 below.

[0743] [Table 1]

[0744] The crystals show a thermal melting phenomenon between about 169° C. and 172° C., for example at about 170° C., as determined by differential scanning calorimetry. The hydrochloride salt 1 is in the form of a solvate, and the free base and counter ion are present in the crystals in a ratio of 1:0.9.

[0745] Hydrochloric acid in cyclopentyl methyl ether is combined with compound 1 (25 mg) in acetonitrile and cooled to 5° C. for 8 hours to give the second hydrochloride salt. The resulting salt is a solvate and is obtained as an off-white powder after evaporation. The XRPD pattern of hydrochloride salt 2 has the peaks listed in Table 2 below.

[0746] [Table 2]

[0747] The crystals show thermal events by differential scanning calorimetry at between about 140° C.-142° C., e.g., about 141° C., and between about 190° C.-192° C., e.g., about 191° C. The hydrochloride salt 2 is in a solvate form, with the free base and counterion being present in the crystals in a ratio of 1:0.9.

[0748] Aqueous hydrochloric acid is combined with compound 1 (25 mg) in acetonitrile followed by cooling to 5° C. over 8 hours to give the third hydrochloride salt. The resulting salt is a solvate and is obtained as an off-white powder after evaporation. The XRPD pattern of hydrochloride salt 3 has the peaks listed in Table 3 below.

[0749] [Table 3]

[0750] The crystals show thermal events by differential scanning calorimetry at between about 155° C. and 157° C., e.g., about 156° C., and between about 275° C. and 277° C., e.g., about 276° C. The hydrochloride salt 3 is in a solvate form, with the free base and counterion being present in the crystals in a ratio of 1:0.9.

[0751] Hydrochloric acid in isopropyl alcohol is combined with compound 1 (25 mg) in 2-butanone and cooled to 5° C. for 8 hours to give the fourth hydrochloride salt. The resulting salt is a solvate and is obtained as a crystalline slurry. The XRPD pattern of hydrochloride salt 4 has the peaks listed in Table 4 below.

[0752] [Table 4-1] [Table 4-2] [Table 4-3]

[0753] The crystals show thermal events by differential scanning calorimetry at between about 194° C. and 196° C., e.g., about 195° C., and between about 209° C. and 211° C., e.g., about 210° C. The hydrochloride salt 4 is in a solvate form, with the free base and counterion being present in the crystals in a ratio of 1:0.9.

[0754] Malate L-Malic acid is combined with compound 1 (25 mg) in ethyl acetate, followed by slurrying at 50° C. for 2 hours to give the L-malate salt. The resulting salt is a solvate and is obtained as an off-white powder. The XRPD pattern of L-malate salt 1 has the peaks listed in Table 5 below.

[0755] [Table 5-1] [Table 5-2]

[0756] The above crystals exhibit a thermal melting phenomenon between about 94° C. and 96° C., for example at about 95° C., as determined by differential scanning calorimetry. L-Malate 1 is in a solvate form, and the free base and counter ion are present in the crystals in a ratio of 1:0.7.

[0757] Fumarate Fumaric acid is combined with compound 1 (25 mg) in ethyl acetate, followed by slurrying at 50° C. for 2 hours to obtain the fumarate salt. The resulting salt is a solvate and is obtained as a white powder. The XRPD pattern of fumarate salt 1 has the peaks listed in Table 6 below.

[0758] [Table 6-1] [Table 6-2]

[0759] The crystals exhibit thermal events by differential scanning calorimetry at between about 110° C.-112° C., e.g., about 111° C., and between about 141° C.-143° C., e.g., about 142° C., and between about 164° C.-166° C., e.g., about 165° C. Fumarate 1 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of 1:0.5.

[0760] Sulfate Sulfuric acid is combined with compound 1 (25 mg) in ethyl acetate, followed by cooling to 5° C. over 8 hours to give the sulfate salt. The resulting salt is a solvate and is obtained as an off-white powder after evaporation. The XRPD pattern of sulfate salt 1 has the peaks listed in Table 7 below.

[0761] [Table 7]

[0762] The crystals exhibit thermal events by differential scanning calorimetry at between about 132° C.-134° C., e.g., about 133° C., and between about 227° C.-229° C., e.g., about 228° C. Fumarate 1 is in a solvate form, with the free base and counterion present in the crystals in a ratio of 1:0.4.

[0763] Combining sulfuric acid with compound 1 (25 mg) in ethyl acetate followed by slurrying at 50° C. for 2 hours gives the second sulfate salt. The resulting salt is a solvate and is obtained as an off-white powder after evaporation. The XRPD pattern of sulfate salt 2 has the peaks listed in Table 8 below.

[0764] [Table 8-1] [Table 8-2]

[0765] The crystals exhibit thermal events by differential scanning calorimetry at between about 69° C. and 71° C., e.g., about 70° C., and between about 114° C. and 116° C., e.g., about 115° C. The sulfate salt 2 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of 1:0.5.

[0766] Esylates Ethanesulfonic acid is combined with compound 1 (25 mg) in acetone, followed by slurrying at 50° C. for 2 hours to give the esylate salt. The resulting salt is obtained as a white powder. The XRPD pattern of esylate salt 1 has the peaks listed in Table 9 below.

[0767] [Table 9-1] [Table 9-2]

[0768] The crystals show a thermal event by differential scanning calorimetry between about 304° C. and 306° C., e.g., at about 305° C. The esylate salt 1 is in a solvate form, with the free base and counterion being present in a 1:1 ratio in the crystals.

[0769] Galactarate Galactaric acid is combined with compound 1 (25 mg) in methanol and water (9:1), followed by slurrying at 50° C. for 2 hours to obtain the galactarate salt. The resulting salt is obtained as an off-white powder. The XRPD pattern of galactarate salt 1 has the peaks listed in Table 10 below.

[0770] [Table 10]

[0771] The crystals show a thermal event by differential scanning calorimetry between about 204° C. and 206° C., e.g., at about 205° C. The galactarate salt 1 is in a solvate form, with the free base and counterion being present in the crystals in a ratio of 1:0.9.

[0772] Adipate Adipic acid is combined with compound 1 (25 mg) in ethyl acetate, followed by slurrying at 50° C. for 2 hours to obtain the adipate salt. The resulting salt is obtained as a white powder after evaporation. The XRPD pattern of adipate salt 1 has the peaks listed in Table 11 below.

[0773] [Table 11-1] [Table 11-2]

[0774] The crystals exhibit thermal events by differential scanning calorimetry at between about 119° C. and 121° C., e.g., about 120° C., and between about 159° C. and 161° C., e.g., about 160° C. The adipate salt 1 is in anhydrous form, and the free base and counterion are present in a 1:1 ratio in the crystals.

[0775] Adipic acid is combined with compound 1 (25 mg) in acetonitrile, followed by slurrying at 50° C. for 2 hours to give the second adipate salt. The resulting salt is obtained as an off-white powder. The XRPD pattern of adipate salt 2 has the peaks listed in Table 12 below.

[0776] [Table 12]

[0777] The crystals exhibit a thermal event by differential scanning calorimetry between about 159° C. and 161° C., e.g., at about 160° C. The adipate salt 2 is in anhydrous form, and the free base and counterion are present in the crystals in a 2:1 ratio.

[0778] Adipic acid is combined with compound 1 (25 mg) in acetone, followed by slurrying at 50° C. for 2 hours to give the third adipate salt. The resulting salt is obtained as an off-white powder. The XRPD pattern of adipate salt 2 has the peaks listed in Table 12A below.

[0779] [Table 13-1] [Table 13-2] [Table 13-3]

[0780] The crystals exhibit a thermal event by differential scanning calorimetry between about 109° C. and 112° C., e.g., at about 109° C. The adipate salt 3 is in anhydrous form, and the free base and counterion are present in a 1:1 ratio in the crystals.

[0781] Lactate Lactic acid is combined with compound 1 (25 mg) in ethyl acetate or toluene, followed by slurrying at 50° C. for 2 hours to obtain the lactate salt. The resulting salt is obtained as a white powder. The XRPD pattern of lactate salt 1 has the peaks listed in Table 13 below.

[0782] [Table 14-1] [Table 14-2]

[0783] The crystals exhibit a thermal event by differential scanning calorimetry between about 187° C. and 190° C., for example at about 187° C. or 188° C. The lactate salt 1 is in anhydrous form, and the free base and counterion are present in a 1:1 ratio in the crystals.

[0784] Oxalates Oxalic acid is combined with compound 1 (25 mg) in 3-heptanone, followed by cooling to 5° C. for 8 hours to give the oxalate salt. The resulting salt is obtained as an off-white powder. The XRPD pattern of oxalate salt 1 has the peaks listed in Table 14 below.

[0785] [Table 15-1] [Table 15-2]

[0786] The crystals exhibit a thermal event by differential scanning calorimetry between about 218° C. and 220° C., for example at about 219° C. The oxalate salt 1 is in anhydrous form.

[0787] The second oxalate salt is obtained by combining oxalic acid with compound 1 (25 mg) in acetonitrile, followed by cooling to 5° C. for 8 hours. The resulting salt is obtained as white needles. The XRPD pattern of oxalate salt 2 has the peaks listed in Table 15 below.

[0788] [Table 16]

[0789] The crystals exhibit thermal events by differential scanning calorimetry at between about 165° C.-167° C., e.g., about 166° C., and between about 205° C.-207° C., e.g., about 207° C., and between about 214° C.-216° C., e.g., about 215° C. The oxalate salt 2 is in anhydrous form.

[0790] Oxalic acid is combined with compound 1 (25 mg) in 3-heptanone, 2-butanone or ethyl acetate to obtain the third oxalate salt. The mixture is then slurried at 50° C. for 2 hours and cooled to 5° C. for 8 hours or evaporated under vacuum. The resulting salt is obtained as a white needle shape. The XRPD pattern of oxalate salt 3 has the peaks listed in Table 16 below.

[0791] [Table 17-1] [Table 17-2]

[0792] The crystals above exhibit a thermal event by differential scanning calorimetry between about 214° C. and 220° C., for example at about 214° C., 218° C. or 219° C. Oxalate 3 is in a solvate form.

[0793] Palmitate Palmitic acid is combined with compound 1 (25 mg) in ethyl acetate, 2-butanone, acetonitrile, or 3-heptanone to give the palmitate salt. The mixture is then slurried at 50° C. for 2 hours and cooled to 5° C. for 8 hours or evaporated under vacuum. The resulting salt is obtained as a white to off-white powder. The XRPD pattern of palmitate salt 1 has the peaks listed in Table 17 below.

[0794] [Table 18-1] [Table 18-2]

[0795] The crystals exhibit a thermal event by differential scanning calorimetry between about 59° C. and 66° C., e.g., about 59° C., 62° C., or 63° C. Palmitate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0796] 2-Oxo-glutarate Palmitic acid is combined with compound 1 (25 mg) in ethyl acetate to obtain palmitate. The mixture is then evaporated under vacuum. The resulting salt is obtained as an off-white powder. The XRPD pattern of 2-oxo-glutarate has the peaks listed in Table 18 below.

[0797] [Table 19]

[0798] The crystals exhibit thermal events by differential scanning calorimetry at between about 124° C. and 126° C., e.g., about 125° C., and between about 157° C. and 159° C., e.g., about 158° C. The 2-oxo-glutarate salt is in a solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:1.1.

[0799] Xinafoate 1-Hydroxy-2-naphthoic acid is combined with compound 1 (25 mg) in acetonitrile, followed by slurrying at 50° C. for 2 hours to give the xinafoate salt. The resulting salt is obtained as a brown powder. The XRPD pattern of xinafoate salt 1 has the peaks listed in Table 19 below.

[0800] [Table 20]

[0801] The crystals exhibit thermal events by differential scanning calorimetry at about 130° C.-132° C., e.g., about 131° C., and about 143° C.-146° C., e.g., about 145° C., and about 171° C.-174° C., e.g., about 172° C. Xinafoate salt 1 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0802] 1-Hydroxy-2-naphthoic acid is combined with compound 1 (25 mg) in toluene followed by slurrying at 50° C. for 2 hours to give the second xinafoate salt. The resulting salt is obtained as a white powder. The XRPD pattern of xinafoate salt 2 has the peaks listed in Table 20 below.

[0803] [Table 21]

[0804] The crystals exhibit thermal events by differential scanning calorimetry at about 117° C.-119° C., e.g., about 118° C., about 163° C.-166° C., e.g., about 164° C., and about 174° C.-177° C., e.g., about 175° C. The xinafoate salt 2 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0805] 1-Hydroxy-2-naphthoic acid is combined with compound 1 (25 mg) in ethyl acetate followed by cooling to 5° C. for 8 hours to give the third xinafoate salt. The resulting salt is obtained as a brown powder. The XRPD pattern of xinafoate salt 3 has the peaks listed in Table 21 below.

[0806] [Table 22-1] [Table 22-2]

[0807] The crystals exhibit thermal events by differential scanning calorimetry at between about 131° C. and 133° C., e.g., about 132° C., and between about 170° C. and 173° C., e.g., about 172° C. Xinafoate salt 3 is in a solvate form, with the free base and counterion being present in the crystals in a ratio of about 1:1.

[0808] Tosylate p-Toluenesulfonic acid is combined with compound 1 (25 mg) in 3-heptanone, followed by slurrying at 50° C. for 2 hours to give the tosylate salt. The resulting salt is obtained as a white powder. The XRPD pattern of tosylate salt 1 has the peaks listed in Table 22 below.

[0809] [Table 23-1] [Table 23-2]

[0810] The crystals exhibit a thermal event by differential scanning calorimetry between about 216° C. and 218° C., e.g., at about 217° C. Tosylate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0811] The second tosylate salt is obtained by combining p-toluenesulfonic acid with compound 1 (25 mg) in ethyl acetate followed by slurrying at 50° C. for 2 hours. The resulting salt is obtained as a white powder. The XRPD pattern of tosylate salt 2 has the peaks listed in Table 23 below.

[0812] [Table 24]

[0813] The crystals exhibit thermal events by differential scanning calorimetry at about 87° C.-90° C., e.g., about 89° C., about 109° C.-112° C., e.g., about 111° C., and about 217° C.-220° C., e.g., about 219° C. The tosylate salt 2 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0814] Tartrate Tartaric acid is combined with compound 1 (25 mg) in acetone, followed by slurrying at 50° C. for 2 hours to obtain the tartrate salt. The resulting salt is obtained as a white powder. The XRPD pattern of the tartrate salt 1 has the peaks listed in Table 24 below.

[0815] [Table 25]

[0816] The crystals show a thermal event between about 134° C. and 136° C., e.g., about 135° C., as measured by differential scanning calorimetry. The free base and counterions of tartrate 1 are present in the crystals in a ratio of about 1:1.

[0817] Succinate Succinic acid is combined with compound 1 (25 mg) in acetone, followed by slurrying at 50° C. for 2 hours to obtain the succinate salt. The resulting salt is obtained as a white powder. The XRPD pattern of succinate salt 1 has the peaks listed in Table 25 below.

[0818] [Table 26-1] [Table 26-2]

[0819] The crystals exhibit thermal events by differential scanning calorimetry at about 153° C.-155° C., e.g., about 154° C., about 172° C.-175° C., e.g., about 173° C., and about 178° C.-181° C., e.g., about 180° C. The succinate salt 1 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:0.7.

[0820] The second succinate salt is obtained by combining succinic acid with compound 1 (25 mg) in ethyl acetate, followed by slurrying at 50° C. for 2 hours. The resulting salt is obtained as a white powder. The XRPD pattern of succinate salt 2 has the peaks listed in Table 26 below.

[0821] [Table 27]

[0822] The crystals exhibit thermal events by differential scanning calorimetry at about 150° C.-152° C., e.g., about 151° C., about 163° C.-165° C., e.g., about 164° C., about 172° C.-175° C., e.g., about 174° C., and about 178° C.-181° C., e.g., about 179° C. The succinate salt 2 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:0.8.

[0823] Mesylate Methanesulfonic acid is combined with compound 1 (25 mg) in acetone, followed by slurrying at 50° C. for 2 hours to give the mesylate salt. The resulting salt is obtained as a white powder. The XRPD pattern of mesylate salt 1 has the peaks listed in Table 27 below.

[0824] [Table 28-1] [Table 28-2]

[0825] The crystals exhibit a thermal event by differential scanning calorimetry between about 310° C. and 312° C., e.g., at about 311° C. The mesylate salt 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0826] Napadisilate Naphthalenedisulfonic acid is combined with compound 1 (25 mg) in acetonitrile, followed by slurrying at 50° C. for 2 hours to give the mesylate salt. The resulting salt is obtained as a brown sticky solid. The XRPD pattern of napadisilate salt 1 has the peaks listed in Table 28 below.

[0827] [Table 29]

[0828] The crystals exhibit a thermal event by differential scanning calorimetry between about 103° C. and 107° C., for example at about 105° C. Napadisylate 1 is in a solvate form, with the free base and counterion being present in the crystals in a ratio of about 1:1.2.

[0829] Edisylate Ethanedisulfonic acid is combined with compound 1 (25 mg) in 2-butanone, followed by slurrying at 50° C. for 2 hours to give the edisylate salt. The resulting salt is obtained as an off-white powder. The XRPD pattern of edisylate salt 1 has the peaks listed in Table 29 below.

[0830] [Table 30-1] [Table 30-2]

[0831] The crystals exhibit a thermal event by differential scanning calorimetry between about 295° C. and 298° C., e.g., about 296° C. or 297° C. The edisylate salt 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0832] Propionate Propionic acid is combined with compound 1 (25 mg) in methanol and water (9:1), followed by slurrying at 50° C. for 2 hours to give the propionate salt. The resulting salt is obtained as a brown powder after evaporation. The XRPD pattern of propionate salt 1 has the peaks listed in Table 30 below.

[0833] [Table 31-1] [Table 31-2]

[0834] The crystals exhibit thermal events by differential scanning calorimetry at between about 109° C. and 112° C., e.g., about 111° C., and between about 135° C. and 137° C., e.g., about 136° C. The propionate salt 1 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:0.7.

[0835] Caprylate Caprylic acid is combined with compound 1 (25 mg) in methanol and water (9:1), followed by slurrying at 50° C. for 2 hours to give the caprylic acid salt. The resulting salt is initially obtained as a clear liquid and exists as a hard solid after evaporation. The XRPD pattern of caprylic acid salt 1 has the peaks listed in Table 31 below.

[0836] [Table 32-1] [Table 32-2]

[0837] The crystals exhibit a thermal event by differential scanning calorimetry between about 102° C. and 105° C., e.g., at about 104° C. Caprylate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.4.

[0838] Besylate Benzenesulfonic acid is combined with compound 1 (25 mg) in 3-heptanone, followed by slurrying at 50° C. for 2 hours to give the besylate salt. The resulting salt is obtained as a brown powder. The XRPD pattern of besylate salt 1 has the peaks listed in Table 32 below.

[0839] [Table 33-1] [Table 33-2] [Table 33-3]

[0840] The crystals exhibit a thermal event by differential scanning calorimetry between about 237° C. and 240° C., e.g., at about 238° C. The besylate salt 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0841] Benzoates Benzoic acid is combined with compound 1 (25 mg) in 3-heptanone, followed by evaporation under vacuum to give the benzoate salt. The resulting salt is obtained as a brown / red powder. The XRPD pattern of benzoate salt 1 has the peaks listed in Table 33 below.

[0842] [Table 34]

[0843] The crystals exhibit thermal events by differential scanning calorimetry at about 59° C.-62° C., e.g., about 60° C., about 81° C.-84° C., e.g., about 83° C., and about 115° C.-118° C., e.g., about 116° C. Benzoate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.1.

[0844] Nicotinate Nicotinic acid is combined with compound 1 (25 mg) in acetonitrile, followed by cooling to 5° C. for 8 hours to obtain nicotinic acid salt. The resulting salt is obtained as a white powder. The XRPD pattern of nicotinic acid salt 1 has the peaks listed in Table 34 below.

[0845] [Table 35-1] [Table 35-2]

[0846] The crystals exhibit a thermal event by differential scanning calorimetry between about 135° C. and 138° C., e.g., at about 137° C. Nicotinate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0847] Isonicotinate Isonicotinic acid is combined with compound 1 (25 mg) in toluene, followed by slurrying at 50° C. for 2 hours to give the isonicotinic acid salt. The resulting salt is obtained as a light brown powder. The XRPD pattern of isonicotinic acid salt 1 has the peaks listed in Table 35 below.

[0848] [Table 36-1] [Table 36-2]

[0849] The crystals exhibit thermal events by differential scanning calorimetry at between about 111° C. and 114° C., e.g., about 113° C., and between about 128° C. and 130° C., e.g., about 129° C. Isonicotinate 1 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:0.7.

[0850] Orotate Orotic acid is combined with compound 1 (25 mg) in 2-butanone, followed by slurrying at 50° C. for 2 hours to give the orotate salt. The resulting salt is obtained as a white powder. The XRPD pattern of orotate salt 1 has the peaks listed in Table 36 below.

[0851] [Table 37]

[0852] The crystals show a thermal event by differential scanning calorimetry between about 137° C. and 140° C., for example at about 138° C. The orotate salt 1 is in a solvate form, with the free base and counterion being present in the crystals in a ratio of about 1:2.

[0853] Camsylate Camphor-10-sulfonic acid is combined with compound 1 (25 mg) in 3-heptanone, followed by slurrying at 50° C. for 2 hours to give the camsylate salt. The resulting salt is obtained as a white powder. The XRPD pattern of the camsylate salt 1 has the peaks listed in Table 37 below.

[0854] [Table 38-1] [Table 38-2]

[0855] The crystals exhibit thermal events by differential scanning calorimetry at between about 227° C. and 230° C., e.g., about 228° C., and between about 253° C. and 256° C., e.g., about 254° C. The camsylate salt 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0856] The second camsylate salt is obtained by combining camphor-10-sulfonic acid with compound 1 (25 mg) in toluene, followed by slurrying at 50° C. for 2 hours. The resulting salt is obtained as a white powder. The XRPD pattern of camsylate salt 2 has the peaks listed in Table 38 below.

[0857] [Table 39]

[0858] Camsylate 2 is in a solvate form, with the free base and counterion present in the crystal in approximately a 1:1 ratio.

[0859] Salicylates Salicylic acid is combined with compound 1 (25 mg) in acetonitrile, followed by slurrying at 50° C. for 2 hours to give the salicylate salt. The resulting salt is obtained as a white powder. The XRPD pattern of salicylate salt 1 has the peaks listed in Table 39 below.

[0860] [Table 40]

[0861] The crystals exhibit thermal events by differential scanning calorimetry at about 146° C.-150° C., e.g., about 147° C., about 153° C.-156° C., e.g., about 155° C., about 196° C.-199° C., e.g., about 197° C., and about 244° C.-247° C., e.g., about 245° C. The salicylate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0862] The second salicylate salt is obtained by combining salicylic acid with compound 1 (25 mg) in toluene, followed by cooling to 5° C. for 8 hours. The resulting salt is obtained as a white powder. The XRPD pattern of salicylate salt 2 has the peaks listed in Table 40 below.

[0863] [Table 41-1] [Table 41-2]

[0864] The above crystals exhibit thermal events by differential scanning calorimetry at about 127° C.-130° C., e.g., about 128° C., about 143° C.-146° C., e.g., about 144° C., about 180° C.-183° C., e.g., about 181° C., about 196° C.-199° C., e.g., about 197° C., and about 244° C.-247° C., e.g., about 247° C. The salicylate 2 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0865] Aminosalicylates Aminosalicylic acid is combined with compound 1 (25 mg) in acetonitrile, followed by slurrying at 50° C. for 2 hours to give the aminosalicylate salt. The resulting salt is obtained as an off-white powder. The XRPD pattern of aminosalicylate salt 1 has the peaks listed in Table 42 below.

[0866] [Table 42]

[0867] The crystals exhibit thermal events by differential scanning calorimetry at between about 130° C.-133° C., e.g., about 132° C., and between about 161° C.-164° C., e.g., about 162° C. The aminosalicylate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0868] Mandelates Mandelic acid is combined with compound 1 (25 mg) in toluene, followed by cooling to 5° C. over 8 hours to obtain the mandelate salt. An off-white powder is obtained. Alternatively, the salt is obtained by evaporating the mixture under vacuum. Under this method, the material does not dissolve before evaporation. After centrifugation, the supernatant is removed using a pipette and placed under vacuum until a dry solid is obtained. The XRPD pattern of mandelate salt 1 has the peaks listed in Table 43 below.

[0869] [Table 43-1] [Table 43-2]

[0870] The crystals exhibit a thermal event by differential scanning calorimetry between about 119° C. and 128° C., e.g., about 120° C. or 126° C. The mandelate salt 1 is in a solvate form, with the free base and counterion being present in the crystals in a ratio of about 1:1.

[0871] Combining mandelic acid with compound 1 (25 mg) in 3-heptanone followed by evaporation under vacuum gives the second mandelic acid salt. The resulting salt is obtained as an orange / brown powder. The XRPD pattern of mandelic acid salt 2 has the peaks listed in Table 44 below.

[0872] [Table 44-1] [Table 44-2]

[0873] The crystals show a thermal event by differential scanning calorimetry between about 102° C. and 105° C., e.g., at about 103° C. The mandelate salt 2 is in a solvate form, with the free base and counterion being present in the crystals in a ratio of about 1:1.

[0874] 4-Acetamido-benzoate 4-Acetamido-benzoic acid is combined with compound 1 (25 mg) in ethyl acetate, followed by slurrying at 50° C. for 2 hours to give 4-acetamido-benzoate. The resulting salt is obtained as a white powder. The XRPD pattern of 4-acetamido-benzoate 1 has the peaks listed in Table 45 below.

[0875] [Table 45-1] [Table 45-2]

[0876] The crystals show a thermal event by differential scanning calorimetry between about 168° C. and 171° C., e.g., at about 170° C. 4-acetamido-benzoate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.3.

[0877] 4-Acetamido-benzoic acid is combined with compound 1 (25 mg) in 3-heptanone, followed by slurrying at 50° C. for 2 hours to give a second 4-acetamido-benzoate salt. The resulting salt is obtained as a white powder. The XRPD pattern of 4-acetamido-benzoate salt 2 has the peaks listed in Table 46 below.

[0878] [Table 46-1] [Table 46-2]

[0879] [000209] The crystals exhibit thermal events by differential scanning calorimetry at about 127° C.-130° C., e.g., about 129° C., and at about 170° C.-173° C., e.g., about 172° C. 4-acetamido-benzoate 2 is in a solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:1.

[0880] Trifluoroacetate Trifluoroacetic acid is combined with compound 1 (25 mg) in acetonitrile, followed by slurrying at 50° C. for 2 hours to give the trifluoroacetate salt. The resulting salt is initially obtained as a clear liquid, and after evaporation, as a white powder. The XRPD pattern of trifluoroacetate salt 1 has the peaks listed in Table 47 below.

[0881] [Table 47-1] [Table 47-2]

[0882] The crystals exhibit a thermal event by differential scanning calorimetry between about 253° C. and 257° C., e.g., at about 255° C. Trifluoroacetate salt 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:0.9.

[0883] Dichloroacetate Trifluoroacetic acid is combined with compound 1 (25 mg) in acetonitrile, followed by slurrying at 50° C. for 2 hours to give the dichloroacetate salt. The resulting salt is obtained as a white powder. The XRPD pattern of dichloroacetate salt 1 has the peaks listed in Table 48 below.

[0884] [Table 48-1] [Table 48-2]

[0885] [000213] The crystals exhibit thermal events by differential scanning calorimetry at between about 225° C. and 228° C., e.g., about 227° C., and between about 229° C. and 232° C., e.g., about 230° C. Dichloroacetate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:0.8.

[0886] Caproate Caproic acid is combined with compound 1 (25 mg) in 2-butanone, followed by slurrying at 50° C. for 2 hours to give the caproic acid salt. The resulting salt is initially obtained as a clear liquid, and after evaporation, as an off-white powder. The XRPD pattern of caproic acid salt 1 has the peaks listed in Table 49 below.

[0887] [Table 49-1] [Table 49-2]

[0888] The crystals exhibit thermal events by differential scanning calorimetry at between about 89° C. and 92° C., e.g., about 90° C., and between about 104° C. and 107° C., e.g., about 105° C. Caproate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:0.9.

[0889] Laurate Lauric acid is combined with compound 1 (25 mg) in 2-propanol, followed by vacuum evaporation to obtain the laurate salt. The resulting salt is obtained as a white powder. The XRPD pattern of laurate salt 1 has the peaks listed in Table 50 below.

[0890] [Table 50]

[0891] The crystals exhibit a thermal event by differential scanning calorimetry between about 81° C. and 84° C., e.g., at about 83° C. Laurate 1 is in anhydrous form, and the free base and counterion are present in the crystals in a ratio of about 1:1.4.

[0892] Example 2 - Solubility study of the obtained salt crystals The water solubility of the salt crystals produced in Example 1 is determined by shaking the salt crystals in water for 24 hours. The sample is filtered and diluted for LC analysis (with acetonitrile / water (1 / 1) mixture). The solubility is calculated using a calibration curve. Furthermore, the pH value of the filtered solution is determined using pH indicator paper. The solubility of the salt is compared with that of the free base form of compound 1 and the phosphate comparator of compound 1 disclosed in WO2013192556A2.

[0893] [Table 51-1] [Table 51-2]

[0894] [000219] For the malate, tartrate, oxalate, hydrochloride, and resulting phosphate salts, the aqueous solubilities are equal to or greater than the phosphate comparator, with the hydrochloride salt in particular having good aqueous solubility (i.e., 112 mg / ml or greater).

[0895] Example 3 – Scale-up of the hydrochloride salt Further hydrochloride salts are prepared according to the method generally described above in Example 1. Hydrochloride salt 1 (100 mg) is dissolved in 2-ethyl-1-butanol and temperature cycled using a Technobis Crystal 16 instrument. The salt is cycled successively from 50°C to 0°C, 40°C to 0°C, 30°C to 0°C, and 20°C to 0°C with a heating rate of 10°C / min and a cooling rate of 0.5°C / min. The resulting material was analyzed using XRPD and TGA-DSC. The resulting salt is obtained as an off-white powder. The XRPD pattern of hydrochloride salt 5 has the peaks listed in Table 52 below.

[0896] [Table 52]

[0897] The crystals show a thermal event between about 158° C. and 161° C., e.g., about 159° C., by differential scanning calorimetry. The hydrochloride salt 5 is in a solvate form. This form is reproducible with the amorphous hydrochloride salt of compound 1 as well.

[0898] The sixth hydrochloride salt is prepared according to the method generally described above in Example 1. Hydrochloride salt 1 (100 mg) is dissolved in ethyl butyl ketone and subjected to the temperature cycle described above. The resulting material is analyzed using XRPD and TGA-DSC. The resulting salt is obtained as an off-white powder. The XRPD pattern of hydrochloride salt 6 has the peaks listed in Table 53 below.

[0899] [Table 53]

[0900] The crystals show a thermal event between about 129° C. and 133° C., for example at about 131° C., by differential scanning calorimetry. The hydrochloride salt 6 is a solvate form. This form is similarly reproducible with the amorphous hydrochloride salt of compound 1.

[0901] The seventh hydrochloride salt is prepared according to the method generally described above in Example 1. Hydrochloride salt 1 (100 mg) is dissolved in anisole and subjected to the temperature cycle described above. The resulting material is analyzed using XRPD and TGA-DSC. The resulting salt is obtained as an off-white powder. The XRPD pattern of hydrochloride salt 7 has the peaks listed in Table 54 below.

[0902] [Table 54-1] [Table 54-2]

[0903] The crystals show a thermal event between about 144° C. and 147° C., e.g., at about 145° C., by differential scanning calorimetry. The hydrochloride salt 7 is a solvate form. This form is similarly reproducible with the amorphous hydrochloride salt of compound 1.

[0904] The hydrochloride salt No. 8 is prepared according to the method generally described above in Example 1. Hydrochloride salt 1 (100 mg) is dissolved in ethyl salicylate and subjected to the temperature cycle described above. The resulting material was analyzed using XRPD and TGA-DSC. The resulting salt is obtained as an off-white powder. The XRPD pattern of hydrochloride salt 8 has the peaks listed in Table 55 below.

[0905] [Table 55]

[0906] The crystals show a thermal event between about 196° C. and 200° C., e.g., about 198° C., by differential scanning calorimetry. The hydrochloride salt 8 is in a solvate form. This form is reproducible with the amorphous hydrochloride salt of compound 1 as well.

[0907] Example 4 – Tartrate scale-up Further tartrate salts are prepared according to the method generally described above in Example 1. Tartrate salt 1 (100 mg) is dissolved in methyl tert-butyl ether and temperature cycled using a Technobis Crystal 16 instrument. The salt is cycled continuously from 50°C to 0°C, 40°C to 0°C, 30°C to 0°C, and 20°C to 0°C with a heating rate of 10°C / min and a cooling rate of 0.5°C / min. The resulting material was analyzed using XRPD and TGA-DSC. The resulting salt is obtained as an off-white solid. The XRPD pattern of tartrate salt 2 has the peaks listed in Table 56 below.

[0908] [Table 56]

[0909] The crystals show thermal events between about 103°C and 106°C, e.g., about 104°C, by differential scanning calorimetry. Tartrate 2 is in solvate form, and the free base and counterion are present in the crystals in a ratio of about 1:0.6. Tartrate 2 is reproducible at the 1 g scale of Tartrate 1, but shows thermal events between about 120°C and 123°C, e.g., about 121°C, and between about 134°C and 137°C, e.g., about 136°C.

[0910] Example 5 – Scale-up of oxalate Further tartrate salts are prepared according to the method generally described above in Example 1. Oxalate salt 3 (100 mg) is dissolved in ethyl salicylate and subjected to temperature cycling using a Technobis Crystal 16 instrument. The salt is subjected to successive cycles from 50°C to 0°C, 40°C to 0°C, 30°C to 0°C, and 20°C to 0°C with a heating rate of 10°C / min and a cooling rate of 0.5°C / min. The resulting material is analyzed using XRPD and TGA-DSC. The resulting salt is obtained as an off-white solid. The XRPD pattern of oxalate salt 4 has the peaks listed in Table 57 below.

[0911] [Table 57]

[0912] The crystals exhibit thermal events by differential scanning calorimetry at between about 125° C. and 128° C., such as about 126° C., and between about 138° C. and 148° C., such as about 139° C. Oxalate 4 is in the form of a solvate.

Claims

1. Hydrochloride form, malate form, fumarate form, sulfate form, esylate form, galactarate form, adipate form, lactate form, oxalate form, palmitate form, 2-oxo-glutarate form, xinafoate form, tosylate form, tartrate form, succinate form, mesylate form, napadisylate form, edisylate form, propionate form, caprylate form, besylate form, benzoate form, nicotinate form, isonicotinate form, orotate form, camsylate form, salicylate form a salt comprising (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (Compound A) in the form of an acid addition salt selected from the group consisting of a benzoate salt, an aminosalicylate salt, a mandelate salt, an acetamidobenzoate salt, a trifluoroacetate salt, a dichloroacetate salt, a caproate salt, and a laurate salt.

2. The salt of claim 1 , wherein the salt is crystalline.

3. 3. The salt of claim 2, wherein the salt is a hydrochloride salt.

4. The salt crystals are a. at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 7.3°, 9.5°, 9.7°, 12.3°, 14.4°, 14.6°, 19.0°, 19.6°, and 21.4° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); b. at least five peaks having 2θ angle values ​​selected from the group consisting of 7.3°, 12.1°, 13.6°, 15.6°, 16.4°, 18.5°, 20.0°, 21.3°, 21.4°, and 21.5° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); c. at least five peaks having 2θ angle values ​​selected from the group consisting of 4.9°, 6.9°, 7.3°, 7.4°, 12.2°, 12.7°, 14.6°, 20.6°, 27.6°, and 32.7° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); d. at least five peaks having 2θ angle values ​​selected from the group consisting of 7.6°, 12.0°, 12.7°, 15.0°, 15.1°, 17.9°, 18.8°, 19.3°, 23.1°, and 24.0° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); e. at least five peaks having 2θ angle values ​​selected from the group consisting of 6.7°, 7.7°, 8.8°, 9.1°, 11.4°, 16.4°, 17.0°, 18.4°, 21.9°, and 24.1° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); f. at least five peaks having 2θ angle values ​​selected from the group consisting of 5.0°, 7.1°, 7.5°, 7.8°, 8.5°, 12.4°, 13.0°, 18.7°, 18.8°, and 20.8° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); g. at least five peaks having 2θ angle values ​​selected from the group consisting of 5.6°, 8.7°, 6.1°, 9.2°, 9.8°, 10.7°, 10.9°, 18.9°, 21.8°, and 22.0° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); or h. at least five peaks having 2θ angle values ​​selected from the group consisting of 5.7°, 11.4°, 11.6°, 12.5°, 18.9°, 19.2°, 20.2°, 20.4°, 20.6°, and 22.1° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); 4. The salt of claim 3, which exhibits a powder X-ray diffraction pattern comprising:

5. The salt crystals are a. at least five peaks having d-spacing values ​​selected from the group consisting of 17.9 Å, 12.1 Å, 9.3 Å, 9.1 Å, 7.2 Å, 6.2 Å, 6.0 Å, 4.7 Å, 4.5 Å, and 4.2 Å; b. at least five peaks having d-spacing values ​​selected from the group consisting of 12.2 Å, 11.8 Å, 7.3 Å, 6.5 Å, 5.7 Å, 5.4 Å, 4.8 Å, 4.4 Å, 4.2 Å, and 4.1 Å; c. at least five peaks having d-spacing values ​​selected from the group consisting of 18.0 Å, 14.4 Å, 12.8 Å, 12.0 Å, 7.3 Å, 6.9 Å, 6.1 Å, 4.3 Å, 3.2 Å, and 2.7 Å; d. at least five peaks having d-spacing values ​​selected from the group consisting of 11.7 Å, 7.4 Å, 7.0 Å, 5.9 Å, 5.8 Å, 4.9 Å, 4.7 Å, 4.6 Å, 3.8 Å, and 3.7 Å; e. at least five peaks having d-spacing values ​​selected from the group consisting of 13.2 Å, 11.5 Å, 10.0 Å, 9.8 Å, 7.8 Å, 5.4 Å, 5.2 Å, 4.8 Å, 4.1 Å, and 3.7 Å; f. at least five peaks having d-spacing values ​​selected from the group consisting of 17.8 Å, 12.5 Å, 11.7 Å, 11.3 Å, 10.4 Å, 7.1 Å, 6.8 Å, 6.0 Å, 4.7 Å, and 4.3 Å; g. at least five peaks having d-spacing values ​​selected from the group consisting of 15.7 Å, 14.4 Å, 14.6 Å, 10.2 Å, 9.6 Å, 9.0 Å, 8.1 Å, 4.7 Å, 4.0 Å, and 4.1 Å; or h. at least five peaks having d-spacing values ​​selected from the group consisting of 15.4 Å, 7.8 Å, 7.6 Å, 7.1 Å, 5.2 Å, 4.7 Å, 4.6 Å, 4.4 Å, 4.3 Å, and 4.0 Å; 5. The salt of claim 3 or 4, which exhibits a powder X-ray diffraction pattern comprising:

6. The salt crystals are a. at least five peaks having 2-theta angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 1, as defined herein, wherein the XRPD pattern is measured on a diffractometer using a copper anode at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å; b. at least five peaks having 2θ angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 2, as defined herein, wherein the XRPD pattern is measured on a diffractometer using a copper anode at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å; c. at least five peaks having 2-theta angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 3, as defined herein, wherein the XRPD pattern is measured on a diffractometer using a copper anode at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å; d. at least five peaks having 2-theta angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 4, as defined herein, wherein the XRPD pattern is measured on a diffractometer using a copper anode at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å; e. at least five peaks having 2-theta angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 52, as defined herein, wherein the XRPD pattern is measured on a diffractometer using a copper anode at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å; f. at least five peaks having 2-theta angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 53, as defined herein, wherein the XRPD pattern is measured on a diffractometer using a copper anode at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å; g. at least five peaks having 2-theta angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 54, as defined herein, wherein the XRPD pattern is measured on a diffractometer using a copper anode at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å; or h. at least five peaks having 2-theta angle values ​​or at least five peaks having d-spacing values ​​selected from those set forth in Table 55, as defined herein, wherein the XRPD pattern is measured on a diffractometer using a copper anode at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å.

5. The salt of claim 3 or 4, which exhibits a powder X-ray diffraction pattern comprising:

7. The salt crystals are a. an endothermic peak at about 169°C to 172°C, e.g., about 170°C; b. an endothermic peak at about 140°C to 142°C, e.g., about 141°C, and / or about 190°C to 192°C, e.g., about 191°C; c. an endothermic peak between about 155°C and 157°C, e.g., about 156°C, and / or between about 275°C and 277°C, e.g., about 276°C; d. an endothermic peak between about 194°C and 196°C, e.g., about 195°C, and / or between about 209°C and 211°C, e.g., about 210°C; e. an endothermic peak between about 158°C and 161°C, e.g., about 159°C; f. an endothermic peak between about 129°C and 133°C, e.g., about 131°C; g. an endothermic peak between about 144°C and 147°C, e.g., about 145°C; or h. An endothermic peak between about 196°C and 200°C, e.g., about 198°C 5. The salt of claim 3 or 4, which exhibits a differential scanning calorimetry (DSC) pattern comprising:

8. 5. The salt of claim 3 or 4, wherein the salt is in the form of a solvate with acetonitrile, ethyl acetate, acetone, 2-butanone, 2-ethyl-1-butanol, ethyl salicylate, ethyl butyl ketone, acetone, or a combination thereof.

9. 3. The salt of claim 2, wherein the salt is a malate salt.

10. 10. The salt according to claim 9, wherein the salt crystal exhibits an X-ray powder diffraction pattern comprising at least five peaks having 2θ angle values ​​selected from the group consisting of 5.9°, 7.2°, 12.0°, 16.0°, 17.7°, 17.8°, 20.9°, 21.2°, 21.7°, and 21.8° (the XRPD pattern is measured with a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å).

11. The salt of claim 2, wherein the salt is an oxalate salt.

12. The salt crystals are a. at least five peaks having 2θ angle values ​​selected from the group consisting of 7.1°, 8.5°, 12.2°, 12.3°, 16.3°, 19.2°, 20.7°, 22.9°, 24.1°, and 25.4° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); b. at least five peaks having 2θ angle values ​​selected from the group consisting of 6.5°, 6.7°, 7.2°, 16.3°, 16.7°, 17.0°, 19.5°, 20.0°, 20.6°, and 20.8° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); c. at least five peaks having 2θ angle values ​​selected from the group consisting of 5.3°, 6.0°, 11.9°, 16.6°, 17.7°, 18.3°, 19.6°, 20.5°, 20.7°, and 21.2° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); or d. at least five peaks having 2θ angle values ​​selected from the group consisting of 5.8°, 11.6°, 12.1°, 18.1°, 18.5°, 20.4°, 21.4°, 21.9°, 27.1°, and 23.2° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); 12. The salt of claim 11, which exhibits a powder X-ray diffraction pattern comprising:

13. 3. The salt of claim 2, wherein the salt is a tartrate salt.

14. The salt crystals are a. at least five peaks having 2θ angle values ​​selected from the group consisting of 3.7°, 6.0°, 6.9°, 10.4°, 11.6°, 15.0°, 17.5°, 20.3°, 20.8°, and 21.7° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å); or b. at least five peaks having 2θ angle values ​​selected from the group consisting of 5.9°, 6.3°, 8.0°, 10.2°, 11.1°, 12.2°, 12.6°, 17.0°, 17.4°, and 21.5° (the XRPD pattern is measured on a diffractometer using a copper anode, e.g., at a wavelength α1 of 1.5406 Å and a wavelength α2 of 1.5444 Å).

14. The salt of claim 13, which exhibits a powder X-ray diffraction pattern comprising:

15. (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((4-(6-fluoropyridin-2-yl)phenyl)methyl)-cyclopento[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one ("Compound A") in the presence of any of the following acids: hydrochloric acid, malic acid, fumaric acid, sulfuric acid, ethanesulfonic acid, galactaric acid, adipic acid, lactic acid, oxalic acid, palmitic acid, 2-oxo-glutaric acid, xinafoic acid, toluenesulfonic acid, tartaric acid, succinic acid, methanesulfonic acid, naphtha 1. A method for preparing a stable acid addition salt, e.g., a crystalline acid addition salt, with an acid selected from disulfonic acid, ethanedisulfonic acid, propionic acid naphthalenedisulfonic acid, caprylic acid naphthalenedisulfonic acid, benzenesulfonic acid, benzoic acid, nicotinic acid, isonicotinic acid, orotic acid, camsylic acid, salicylic acid, aminosalicylic acid, mandelic acid, acetamidobenzoic acid, trifluoroacetic acid, dichloroacetic acid, caproic acid, or lauric acid, the method comprising the steps of reacting Compound A in free base form with the acid in a solvent and isolating the resulting salt.

Images