Solid forms comprising an AMPA positive allosteric modulator

Abstract

Solid forms comprising 9-(4-(cyclohexyloxy)phenyl)-7-methyl-3,4-dihydropyrazino[2,1-c][1,2,4]thiadiazine 2,2-dioxide (Compound (I)), compositions comprising the same, and methods of making and using the same, for example, in the prevention or treatment of a central nervous system disease.

Description

Attomey Docket No. 15496.0048-00304SOLID FORMS COMPRISING AN AMPA POSITIVE ALLOSTERIC MODULATOR

[0001] This application claims the benefit of priority of U.S. Provisional Patent Application No. 63 / 737,443, filed December 20, 2024, and of U.S. Provisional Patent Application No. 63 / 938,432, filed December 11, 2025, the contents of each of which are incorporated by reference herein in their entirety.

[0002] Disclosed herein are solid forms of 9-(4-(cyclohexyloxy)phenyl)-7-methyl-3,4- dihydropyrazino[2,l-c][l,2,4]thiadiazine 2,2-dioxide (Compound (I)), including co-crystals and polymorphs comprising Compound (I), processes for preparing the same, and uses of the same, for example, in the treatment or prevention of a disease, such as, e.g., a central nervous system disease, such as, e.g., depression, schizophrenia, Alzheimer’s disease, attention deficit hyperactivity disorder, or the like.

[0003] Glutamate is the most abundant excitatory neurotransmitter in the mammalian central nervous system. Glutamate plays a pivotal role in cognition, mood, and motor function, and its neurotransmission becomes unstable in psychiatric diseases and neurological disorder. Glutamate receptors are divided into ligand gated ion channels and G protein-coupled receptors. The ligand gated ion channels are further divided into a-amino-3 -hydroxy-5 - methyl-4-isoxazolepropionic acid (AMPA) receptors, N-methyl-D-aspartic acid (NMDA) receptors, and kainic acid (KA) receptors. R. Dingledine et aL, Pharmacological Reviews 1999, 51(1), 7-61.

[0004] AMPA receptor is one kind of receptor for excitatory neurotransmitter glutamate and was named for the selective activation of the receptor by AMPA. AMPA receptors are composed of four subunits (GluRl, GluR2, GluR3, GluR4). Each subunit exists in flip and flop alternatively spliced variants. AMPA receptors form homo- or hetero-tetramers composed of these subunits in vivo. The physiological property of AMPA receptor has been reported to change depending on the subunit composition. B. Bettier et al., Neuropharmacology 1995, 34(2), 123-139; R. Malinow et al., Ann. Rev. Neurosci. 2002, 25(1), 103-126.

[0005] The importance of AMPA receptor in cerebrophysiology is well known, and a compound having an AMPA receptor potentiating action is expected to be useful as a prophylactic or therapeutic drug for psychiatric diseases, neurodegenerative diseases, cognitive disorders, sleep disorders and the like. D. Bowie, CNS & Neurological Disorders-Attorney Docket No. 15496.0048-00304Drug Targets 2008, 7(2), 129-143; J. A. Morrow el al., Current Opinion in Drug Discovery and Development 2006, 9(5), 571-579.

[0006] Compound (I) and various solid forms thereof may have an AMPA receptor potentiating action (AMPA receptor potentiator; sometimes to be also referred to as AMPA receptor positive modulator, AMPAkine, AMPA receptor allosteric modulator, AMPA receptor positive allosteric modulator, or positive allosteric activator of AMPA receptor) and be useful in the treatment of diseases mediated by the AMPA receptor, including, for example, a central nervous system disease, such as, e.g., depression, schizophrenia, Alzheimer’s disease, attention deficit hyperactivity disorder, or the like. Compound (I) is disclosed in, for example, Example 169 of PCT International ApplicationNo. PCT / JP2011 / 068497, filed August 9, 2011, published as WO 2012 / 020848 Al, and incorporated by reference herein in its entirety. Compound (I) has the following structure:

[0007] Solid forms (e.g, crystalline forms, such as, e.g, co-crystal forms) of bioactive compounds, such as Compound (I), are of interest in the pharmaceutical industry, where solid forms with specific physical, chemical, or pharmaceutical properties, such as solubility, dissociation, true density, dissolution, melting point, morphology, compaction behavior, particle size, flow properties, or solid-state stability, may be desirable or even required for pharmaceutical development. Crystalline forms occur where the same composition of matter crystallizes in different lattice arrangements, resulting in different thermodynamic properties and stabilities specific to each crystalline form. Each unique crystal form is known as a “polymorph.”

[0008] While polymorphs of a given substance have the same chemical composition, they may differ from each other with respect to at least one physical, chemical, and / or pharmaceutical property, such as solubility, dissociation, true density, dissolution, melting point, crystal habit or morphology, compaction behavior, particle size, flow properties, and / or solid-state stability. The solid-state form of a bioactive compound may determine its ease of preparation, ease of isolation, hygroscopicity, stability, solubility, storage stability, ease of formulation, rate of dissolution in gastrointestinal fluids, and in vivo bioavailability.Attorney Docket No. 15496.0048-00304

[0009] A co-crystal is a crystalline material composed of the compound molecule (in most cases, an active pharmaceutical ingredient or API) and one or more different molecules (called coformers). The compound and coformer molecules exist in a unit cell within the crystal lattice together in a defined stoichiometric ratio and are associated by nonionic bonding. A coformer is typically a solid at room temperature, thus differs from a solvent, and is nonvolatile. Co-crystal preparation routes involve stoichiometric mixtures of Active Pharmaceutical Ingredient (API) and coformers subjected to solution-based or solid-based crystallization techniques.

[0010] It is not possible to predict the possible solid forms (e.g., crystalline forms, such as, e.g., co-crystal forms) of a compound, whether any such forms will be suitable for commercial use in a pharmaceutical composition, or which form or forms will display desirable properties. Because different solid forms (e.g., crystalline forms, such as, e.g, co-crystal forms) may possess different properties, reproducible processes for producing a substantially pure solid form are also desirable for bioactive compounds intended for use as pharmaceuticals.

[0011] Accordingly, there is a need for novel solid forms, including novel crystalline and / or co-crystal forms, which are useful for treating disorders and conditions mediated by the activity of the AMP A receptor, e.g., Compound (I), and reproducible, scalable methods of making the same.

[0012] Disclosed herein are novel solid forms comprising Compound (I), compositions comprising the same, and methods of using and making the same. In some embodiments, the solid forms disclosed herein have properties that are useful for large-scale manufacturing, pharmaceutical formulation, and / or storage. In some embodiments, the solid forms disclosed herein consist of one crystalline form. In some embodiments, the solid forms are substantially pure. In some embodiments, the solid forms are chosen from co-crystals comprising Compound (I). In some embodiments, the solid forms are chosen from solvates of Compound (I). In some embodiments, the solid forms are chosen from crystalline forms of Compound (I).

[0013] Some embodiments of the disclosure relate to a pharmaceutical composition comprising at least one pharmaceutically acceptable excipient and at least one solid form which is chosen from solid forms comprising Compound (I).

[0014] In some embodiments, the at least one solid form is a solvate of Compound (I). In some embodiments, the at least one solid form is a chloroform solvate of Compound (I).Attorney Docket No. 15496.0048-00304

[0015] In some embodiments, the at least one solid form comprises Compound (I) and a coformer. In some embodiments, the coformer is camphorsulfonic acid (CSA). In some embodiments of a solid form comprising Compound (I) and a coformer, Compound (I) and the coformer are present in about a 1 :0.9 stoichiometric ratio. In some embodiments of a solid form comprising Compound (I) and a coformer, Compound (I) and camphorsulfonic acid are present in about a 1 :0.9 stoichiometric ratio.

[0016] In some embodiments, the at least one solid form is a co-crystal comprising Compound (I) and a co-crystal former. In some embodiments, the co-crystal former is camphorsulfonic acid (CSA). In some embodiments of a co-crystal comprising Compound (I) and a co-crystal former, Compound (I) and the co-crystal former are present in about a 1 :0.9 stoichiometric ratio. In some embodiments of a co-crystal comprising Compound (I) and a co-crystal former, Compound (I) and camphorsulfonic acid are present in about a 1 :0.9 stoichiometric ratio.

[0017] In some embodiments, the at least one solid form comprises Compound (I) and a Lewis base. In some embodiments of a solid form comprising Compound (I) and a Lewis base, Compound (I) and the Lewis base are present in an about 1 : 1 stoichiometric ratio. In some embodiments of a solid form comprising Compound (I) and a Lewis base, the solid form is a co-crystal. In some embodiments of a solid form comprising Compound (I) and a Lewis base, the solid form is a salt.

[0018] In some embodiments, the at least one solid form comprises Compound (I) and benzamide. In some embodiments of a solid form comprising Compound (I) and benzamide, Compound (I) and benzamide are present in an about 1 : 1 stoichiometric ratio. In some embodiments of a solid form comprising Compound (I) and benzamide, the solid form is a co-crystal. In some embodiments of a solid form comprising Compound (I) and benzamide, the solid form is a salt.

[0019] In some embodiments, the at least one solid form comprises Compound (I) and a Lewis acid. In some embodiments of a solid form comprising Compound (I) and a Lewis acid, Compound (I) and the Lewis acid are present in an about 1 : 1 stoichiometric ratio. In some embodiments of a solid form comprising Compound (I) and a Lewis acid, the solid form is a co-crystal. In some embodiments of a solid form comprising Compound (I) and a Lewis acid, the solid form is a salt.

[0020] In some embodiments, the at least one solid form comprises Compound (I) and manganese (II) chloride (MnCL). In some embodiments of a solid form comprising Compound (I) and manganese (II) chloride, Compound (I) and manganese (II) chloride areAttorney Docket No. 15496.0048-00304 present in an about 1 : 1 stoichiometric ratio. In some embodiments of a solid form comprising Compound (I) and manganese (II) chloride, the solid form is a co-crystal. In some embodiments of a solid form comprising Compound (I) and manganese (II) chloride, the solid form is a salt.

[0021] Some embodiments of the disclosure relate to methods of potentiating an AMPA receptor in a subject in need thereof, comprising administering a therapeutically effective amount of at least one solid form which is chosen from solid forms comprising Compound (I) to the subject.

[0022] Some embodiments of the disclosure relate to methods of preventing or treating depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder in a subject in need thereof, comprising administering a therapeutically effective amount of at least one solid form which is chosen from solid forms comprising Compound (I) to the subject. In some embodiments, the depression is major depressive disorder. In some embodiments, the depression is treatment-resistant depression.

[0023] Some embodiments of the disclosure relate to methods of treating depressive disorders, treating cognitive impairment, and / or improving cognition in a subject in need thereof, comprising administering a therapeutically effective amount of at least one solid form which is chosen from solid forms comprising Compound (I) to the subject. In some embodiments, the cognitive impairment is cognitive impairment associated with Parkinson’s disease. In some embodiments, the cognitive impairment is cognitive impairment associated with Alzheimer’s disease. In some embodiments, the cognitive impairment is cognitive impairment associated with schizophrenia.

[0024] Some embodiments of the disclosure relate to methods of treating bipolar depression, depression associated with Parkinson’s disease, one or more affective symptoms associated with dementia, one or more symptoms associated with autism, one or more symptoms associated with Rett syndrome, one or more symptoms associated with Fragile X syndrome, obsessive compulsive disorder (OCD), narcolepsy, and / or one or more symptoms associated with hypermobile Ehler-Danlos syndrome (hEDS), chronic pain, respiratory depression, attention deficit hyperactivity disorder (ADHD), post-traumatic stress disorder (PTSD), and / or sundowning in a subject in need thereof, comprising administering a therapeutically effective amount of at least one solid form which is chosen from solid forms comprising Compound (I) to the subject.

[0025] It should be understood that references herein to methods of treatment and / or preventing (e.g., methods of treating and / or preventing a central nervous system disease, suchAttorney Docket No. 15496.0048-00304 as, e.g., depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder) using at least one solid form of the present disclosure should also be interpreted as references to: at least one solid form of the present disclosure for use in methods of treatment and / or prevention (e.g., methods of treating and / or preventing a central nervous system disease, such as, e.g., depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder); and / or the use of at least one solid form of the present disclosure in the manufacture of a medicament for use in methods of treatment and / or prevention (e.g., methods of treating and / or preventing a central nervous system disease, such as, e.g., depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder).

[0026] Also disclosed herein are methods of preparing at least one solid form which is chosen from solid forms comprising Compound (I).BRIEF DESCRIPTION OF THE DRAWINGS

[0027] FIG. 1 shows an exemplary X-ray powder diffractogram for Form I of Compound (I), showing degrees 20 (2 -theta) on the X-axis and relative intensity on the Y-axis.

[0028] FIG. 2 shows an exemplary differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for Form I of Compound (I).

[0029] FIG. 3 shows an exemplary X-ray powder diffractogram for Mono-Chloroform Solvate Form of Compound (I), showing degrees 20 (2 -theta) on the X-axis and relative intensity on the Y-axis.

[0030] FIG. 4 shows an exemplary overlay of X-ray powder diffractograms for Form I of Compound (I) and Mono-Chloroform Solvate Form of Compound (I), showing degrees 20 (2 -theta) on the X-axis and relative intensity on the Y-axis.

[0031] FIG. 5 shows an exemplary differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for Mono-Chloroform Solvate Form of Compound (I).

[0032] FIG. 6 shows an exemplary X-ray powder diffractogram for CSA Solid Form of Compound (I), showing degrees 20 (2 -theta) on the X-axis and relative intensity on the Y- axis.

[0033] FIG. 7 shows an exemplary overlay of X-ray powder diffractograms for Form I of Compound (I), CSA Solid Form of Compound (I), Mono-Chloroform Solvate Form of Compound (I), and (+)-(! S)-camphor-10-sulfonic acid.Attorney Docket No. 15496.0048-00304

[0034] FIG. 8 shows an exemplary differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for CSA Solid Form of Compound (I).

[0035] FIG. 9 shows an exemplaryXH NMR spectrum for CSA Solid Form of Compound(I), showing chemical shift 6 (ppm) on the X-axis and intensity on the Y-axis.

[0036] FIG. 10 shows the results of a homonuclear correlation spectroscopy (COSY) NMR experiment of CSA Solid Form of Compound (I).

[0037] FIG. 11 shows the results of a heteronuclear single quantum coherence (HSQC) NMR experiment of CSA Solid Form of Compound (I).

[0038] FIG. 12 shows the results of a homonuclear correlation spectroscopy (COSY) NMR experiment of Form I of Compound (I).

[0039] FIG. 13 shows an exemplary X-ray powder diffractogram for Benzamide Solid Form of Compound (I), showing degrees 20 (2 -theta) on the X-axis and relative intensity on the Y- axis.

[0040] FIG. 14 shows an exemplary overlay of X-ray powder diffractograms for MonoChloroform Solvate Form of Compound (I), Form I of Compound (I), benzamide, and Benzamide Solid Form of Compound (I).

[0041] FIG. 15 shows an exemplary differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for Benzamide Solid Form of Compound (I).

[0042] FIG. 16 shows an exemplary X-ray powder diffractogram for Manganese (II) Chloride Solid Form of Compound (I), showing degrees 20 (2 -theta) on the X-axis and relative intensity on the Y-axis.

[0043] FIG. 17 shows an exemplary overlay of X-ray powder diffractograms for Manganese(II) Chloride Solid Form of Compound (I), manganese (II) chloride, Mono-Chloroform Solvate Form of Compound (I), and Form I of Compound (I).

[0044] FIG. 18 shows an exemplary differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for Manganese (II) Chloride Solid Form of Compound (I).Definitions:

[0045] As used herein, “a” or “an” entity refers to one or more of that entity, e.g., “a compound” refers to one or more compounds or at least one compound unless statedAttorney Docket No. 15496.0048-00304 otherwise. As such, the terms “a” (or “an”), “one or more”, and “at least one” are used interchangeably herein.

[0046] As used herein, the term “about,” when used to modify a numeric value or numeric range, indicate that deviations of up to 10% above and down to 10% below the value or range remain within the intended meaning of the recited value or range. In some embodiments, “about” refers to ± 10%. In some embodiments, “about” refers to ± 9%. In some embodiments, “about” refers to ± 8%. In some embodiments, “about” refers to ± 7%. In some embodiments, “about” refers to ± 6%. In some embodiments, “about” refers to ± 5%. In some embodiments, “about” refers to ± 4%. In some embodiments, “about” refers to ± 3%. In some embodiments, “about” refers to ± 2%. In some embodiments, “about” refers to ± 1%. It is understood that wherever aspects are described herein with the language “about” a numeric value or range, otherwise analogous aspects referring to the specific numeric value or range (without “about”) are also provided. It is also understood that wherever aspects are described herein referring to a numeric value or range without the language “about,” otherwise analogous aspects referring to “about” the specific numeric value or range are also provided.

[0047] As used herein, the term “active pharmaceutical ingredient” or “therapeutic agent” (“API”) refers to a biologically active compound.

[0048] As used herein, “administration” of an API to a patient refers to any route (e.g., oral delivery) of introducing or delivering the API to the patient. Administration includes self-administration and the administration by another.

[0049] As used herein, the term “solid form” includes any solid form of a compound, such as Compound (I), including a substantially crystalline form, a crystalline form, an amorphous form, a solid dispersion, a solvate, a co-crystal, or a salt of the compound that is in solid form.

[0050] As used herein, the terms “crystalline form,” “crystal form,” and “Form” interchangeably refer to a solid having a particular molecular packing arrangement in the crystal lattice. Crystalline forms can be identified and distinguished from each other by one or more characterization techniques including, for example, X-ray powder diffraction (XRPD), single crystal X-ray diffraction, solid state nuclear magnetic resonance (SS-NMR), differential scanning calorimetry (DSC), dynamic vapor sorption (DVS), and / or thermogravimetric analysis (TGA). Accordingly, as used herein, a reference to a Form of a compound, such as a Form of Compound (I), including, but not limited to, Form I of Compound (I), Mono-Chloroform Solvate Form of Compound (I), CSA Solid Form of Compound (I), Benzamide Solid Form of Compound (I), and Manganese (II) Chloride SolidAttorney Docket No. 15496.0048-00304Form of Compound (I), refers to a unique crystalline form that can be identified and distinguished from other forms using one or more characterization techniques including, for example, X-ray powder diffraction (XRPD), single crystal X-ray diffraction, SS-NMR, differential scanning calorimetry (DSC), dynamic vapor sorption (DVS), and / or thermogravimetric analysis (TGA). In some embodiments, the novel crystalline forms of this disclosure are characterized by an X-ray powder diffractogram having one or more signals at one or more specified two-theta values (° 29).

[0051] As used herein, the term “solvate” refers to a crystal form comprising one or more molecules of a compound of the present disclosure and one or more molecules of a solvent or solvents incorporated into the crystal lattice in stoichiometric or nonstoichiometric amounts. When the solvent incorporated into the crystal lattice is water, the solvate is referred to as a “hydrate.”

[0052] As used herein, the term “co-crystal” refers to a crystalline material composed of two or more different molecules, such as Compound (I) and at least one co-crystal former (or coformer), in the same crystal lattice. In some embodiments, co-crystals components are in a neutral state and interact nonionically.

[0053] As used herein, the term “coformer” refers to a component that interacts nonionically with the API in the crystal lattice, is not a solvent (including water), and is typically nonvolatile.

[0054] As used herein, the terms “X-ray powder diffractogram,” “X-ray powder diffraction pattern,” and “XRPD pattern” interchangeably refer to an experimentally obtained pattern plotting signal positions (on the abscissa) versus signal intensities (on the ordinate). For an amorphous material, an X-ray powder diffractogram may comprise one or more broad signals. For a crystalline material, an X-ray powder diffractogram may comprise one or more signals, each identified by its angular value as measured in degrees 29 (° 29), depicted on the abscissa of an X-ray powder diffractogram, which may be expressed as “a signal at . . . degrees two-theta,” “a signal at [a] two-theta value(s) of . . .,” “a signal at . . . two-theta value(s) chosen from . . .,” “a signal at . . . or more two-theta value(s) chosen from . . .,” and / or “a signal at at least . . . two-theta value(s) chosen from . . . .”

[0055] As used herein, a “signal” or “peak” refers to a point in the XRPD pattern where the intensity as measured in counts is at a local maximum. One of ordinary skill in the art would recognize that one or more signals (or peaks) in an XRPD pattern may overlap and may, for example, not be apparent to the naked eye. Illustratively, one of ordinary skill in the artAttorney Docket No. 15496.9948-99394 would recognize that some art-recognized methods are capable of and suitable for determining whether a signal exists in a pattern, such as, for example, Rietveld refinement.

[0056] As used herein, “a signal at . . . degrees two-theta,” “a signal at [a] two-theta valuef] of . . “a signal at . . . two-theta value(s) chosen from . . . ,” “a signal at . . . or more two- theta value(s) chosen from . . .,” and / or “a signal at at least . . . two-theta value(s) chosen from . . . ” refers to an XRPD pattern that comprises X-ray reflection positions as measured and observed in X-ray powder diffraction experiments (° 29).

[0057] The repeatability of the angular values is in the range of ± 0.2° 29, z.e., the angular value can be at the recited angular value + 0.2 degrees two-theta, the angular value - 0.2 degrees two-theta, or any value between those two end points (angular value +0.2 degrees two-theta and angular value -0.2 degrees two-theta).

[0058] As used herein, the terms “signal intensities” and “peak intensities” interchangeably refer to relative signal intensities within a given X-ray powder diffractogram. Non-limiting examples of factors that can affect the relative signal or peak intensities include sample thickness and preferred orientation (e.g., the crystalline particles are not distributed randomly). It is understood that peak intensities can vary from one diffractogram to another for the same crystalline form based on any number of factors that are known to those skilled in the art, such as, preferred orientation effects, preparation technique, the sample mounting procedure, the instrument employed, etc. Accordingly, the diffraction peak intensities shown herein are illustrative and identical diffraction peak intensities are not necessarily required. One skilled in the art would readily be capable of comparing the diffractogram provided herein with a diffractogram generated for an unknown crystal form and confirm whether the diffractogram is characterizing the same crystal form as provided herein or a different form.

[0059] The term “X-ray powder diffractogram comprising a signal at . . . two-theta values,” as used herein, refers to an XRPD pattern comprising X-ray reflection positions as measured and observed in X-ray powder diffraction experiments (° 29).

[0060] As used herein, the term “amorphous” refers to a solid material having no long-range order in the position of its molecules. Amorphous solids may be supercooled liquids in which the molecules are arranged in a random manner such that there is no well-defined arrangement, e.g., molecular packing, and no long-range order. For example, an amorphous material is a solid material with no sharp characteristic signal(s) in its X-ray power diffractogram (z.e., is not crystalline as determined by XRPD). Instead, one or more broad peaks (e.g., halos) may appear in its diffractogram.Attorney Docket No. 15496.0048-00304

[0061] As used herein, an X-ray powder diffractogram is “substantially similar to [a particular] Figure” when at least 90%, such as, for example, at least 95%, at least 98%, or at least 99% of the signals in the two diffractograms overlap ± 0.2 ° 20. In determining “substantial similarity,” one of ordinary skill in the art will understand that there may be variation in the intensities and / or signal positions in the measurements of X-ray powder diffraction signal values even for the same crystalline form. As such, a person of ordinary skill in the art would appreciate that there may be variability of up to ± 0.2 ° 20 in signal value for the same signal in different samples. Additionally, it is well known to one of ordinary skill in the art that there can be variability in the measurements of relative signal intensities in X-ray powder diffraction experiments. Illustratively, non-limiting factors that can affect the relative signal intensities include sample thickness and preferred orientation (e.g., the crystalline particles are not distributed randomly).

[0062] As used herein, a DSC thermogram is “substantially similar to [a particular] Figure,” wherein by “substantially” is meant that the reported DSC features can vary by about ± 5°C and the reported DSC features can vary by about ± 20 joules per gram.

[0063] As used herein, a DSC thermogram is “substantially similar to [a particular] Figure,” wherein by “substantially” is meant that the reported TGA features can vary by about ± 5°C, and the reported TGA features can vary by about ± 2% weight change (i.e., ± about 2% weight change).

[0064] As used herein, a crystalline form is “substantially pure” when it accounts for an amount by weight equal to or greater than 90% of the sum of all solid form(s) in a sample as determined by a method in accordance with the art, such as quantitative XRPD. In some embodiments, the solid form is “substantially pure” when it accounts for an amount by weight equal to or greater than 95% of the sum of all solid form(s) in a sample. In some embodiments, the solid form is “substantially pure” when it accounts for an amount by weight equal to or greater than 99% of the sum of all solid form(s) in a sample.

[0065] As used herein, the term “DSC” refers to the analytical method of differential scanning calorimetry.

[0066] As used herein, the term “TGA” refers to the analytical method of thermo gravimetric (or thermogravimetric) analysis.

[0067] As used herein, the term “endothermic event” refers to the occurrence of an endothermic event, as measured by differential scanning calorimetry (DSC), in a sample of a solid form of Compound (I) described herein.Attorney Docket No. 15496.0048-00304

[0068] As used herein, the term “exothermic event” refers to the occurrence of an exothermic event, as measured by differential scanning calorimetry (DSC), in a sample of a solid form of Compound (I) described herein.

[0069] As used herein, a “condition,” “disorder,” or “disease” relates to any unhealthy or abnormal state.

[0070] As used herein, an “effective amount” or a “therapeutically effective amount” refers to an amount of a molecule that treats, upon single or multiple dose administration, a patient suffering from a condition. An effective amount can be determined by the attending diagnostician through the use of known techniques and by observing results obtained under analogous circumstances. In determining the effective amount, a number of factors are considered by the attending diagnostician, including, but not limited to: the species of patient; its size, age, and general health; the specific condition, disorder, or disease involved; the degree of or involvement or the severity of the condition, disorder, or disease; the response of the individual patient; the particular compound administered; the mode of administration; the bioavailability characteristics of the preparation administered; the dose regimen selected; the use of concomitant medication; and other relevant circumstances.

[0071] As used herein, the term “increase” refers to altering positively by at least 5%, including, but not limited to, altering positively by 5%, altering positively by 10%, altering positively by 25%, altering positively by 30% altering positively by 50%, altering positively by 75%, or altering positively by 100%.

[0072] As used herein, a “mammal” refers to domesticated animals (e.g., dogs, cats, and horses) and humans. In some embodiments, the mammal is a human.

[0073] As used herein, the term “modulate” refers to altering positively or negatively. Non-limiting example modulations include a 1% change, a 2% change, a 5% change, a 10% change, a 25% change, a 50% change, a 75% change, or a 100% change.

[0074] As used herein, the terms “patient” and “subject” are used interchangeably and refer to a mammal, such as, e.g, a human.

[0075] As used herein, a “pharmaceutically acceptable excipient” refers to a carrier or an excipient that is useful in preparing a pharmaceutical composition. For example, a pharmaceutically acceptable excipient is generally safe and includes carriers and excipients that are generally considered acceptable for mammalian pharmaceutical use. As a nonlimiting example, pharmaceutically acceptable excipients may be solid, semi-solid, or liquid materials which in the aggregate can serve as a vehicle or medium for the active ingredient. Some examples of pharmaceutically acceptable excipients are found in Remington’sAttorney Docket No. 15496.0048-00304Pharmaceutical Sciences and the Handbook of Pharmaceutical Excipients and include diluents, vehicles, carriers, ointment bases, binders, disintegrates, lubricants, glidants, sweetening agents, flavoring agents, gel bases, sustained release matrices, stabilizing agents, preservatives, solvents, suspending agents, buffers, emulsifiers, dyes, propellants, coating agents, and others.

[0076] As used herein, the term “reduce” refers to altering negatively by at least 5% including, but not limited to, altering negatively by 5%, altering negatively by 10%, altering negatively by 25%, altering negatively by 30%, altering negatively by 50%, altering negatively by 75%, or altering negatively by 100%.

[0077] As used herein, the term “treat,” “treating,” or “treatment,” when used in connection with a disorder or condition, includes any effect, e.g., lessening, reducing, modulating, ameliorating, or eliminating, that results in the improvement of the disorder or condition. Improvements in or lessening the severity of any symptom of the disorder or condition can be readily assessed according to standard methods and techniques known in the art.

[0078] Throughout the present disclosure, the following abbreviations are used:ACE acetoneACN acetonitrileCPS counts per secondCHCh chloroformCOSY homonuclear correlation spectroscopyCSA camphorsulfonic acidDCM dichloromethaneDME 1,2-dimethoxy ethaneDMSO dimethyl sulfoxideDSC differential scanning calorimetryEtOAc ethyl acetateEtOH ethanolFWHM full width at half maximumHPLC high-performance liquid chromatographyHSQC heteronuclear single quantum coherenceIP Ac isopropyl acetate pL microliterAttorney Docket No. 15496.0048-00304 mg milligram mL milliliterNMR nuclear magnetic resonanceTGA thermogravimetric analysisTHF tetrahydrofuranXRD x-ray diffractionXRPD x-ray powder diffractionNon-Limiting Example Embodiments:

[0079] Without limitation, some embodiments of the disclosure include:1. A solvate comprising Compound (I):and chloroform.2. The solvate according to embodiment 1, wherein Compound (I) and chloroform are present in an about 1 : 1 stoichiometric ratio.3. Mono-Chloroform Solvate Form of Compound (I):4. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-3, characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 + 0.2.Attorney Docket No. 15496.0048-003045. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-3, characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 + 0.2.6. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-3, characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 + 0.2.7. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-3, characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 4.2 + 0.2, 10.2 + 0.2, 12.6 + 0.2, 20.6 + 0.2, and 25.7 + 0.2.8. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-7, characterized by an X-ray powder diffractogram substantially similar to FIG. 39. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-8, characterized by a DSC thermogram substantially similar to FIG. 5.10. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-9, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 122 °C to about 128 °C.11. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-10, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 124 °C to about 125 °C.12. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-11, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 124.6 °C.Attorney Docket No. 15496.0048-0030413. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-12, characterized by a DSC thermogram comprising an exothermic event at a temperature of from about 193 °C to about 198 °C.14. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-13, characterized by a DSC thermogram comprising an exothermic event at a temperature of from about 195 °C to about 196 °C.15. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-14, characterized by a DSC thermogram comprising an exothermic event at a temperature of about 195.4 °C.16. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-15, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 218 °C to about 223 °C.17. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-16, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 220.4 °C.18. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-17, characterized by a TGA thermogram substantially similar to FIG. 5.19. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-18 characterized by a weight loss of from about 20.0% to about 30.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C.20. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-19, characterized by a weight loss of from about 20.0% to about 25.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C.21. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-20, characterized by a weight loss of from about 23.0% to about 24.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C.Attorney Docket No. 15496.0048-0030422. The solvate comprising Compound (I) and chloroform according to any one of embodiments 1-21, characterized by a weight loss of about 23.3% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C.23. A solid form comprising Compound (I):and camphorsulfonic acid.24. The solid form according to embodiment 23, wherein Compound (I) and camphorsulfonic acid are present in about a 1 :0.9 stoichiometric ratio.25. The solid form according to embodiment 23 or embodiment 24, wherein the camphorsulfonic acid is (+)-(! S)-camphor-10-sulfonic acid.26. CS A Solid Form of Compound (I):27. The solid form according to any one of embodiments 23-26, characterized by an X- ray powder diffractogram comprising a signal at two or more two-theta values chosen from 5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.28. The solid form according to any one of embodiments 23-26, characterized by an X- ray powder diffractogram comprising a signal at three or more two-theta values chosen from 5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.Attorney Docket No. 15496.0048-0030429. The solid form according to any one of embodiments 23-26, characterized by an X- ray powder diffractogram comprising a signal at four or more two-theta values chosen from5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.30. The solid form according to any one of embodiments 23-26, characterized by an X- ray powder diffractogram comprising a signal at five or more two-theta values chosen from5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.31. The solid form according to any one of embodiments 23-26, characterized by an X- ray powder diffractogram comprising a signal at two-theta values of 5.6 ± 0.2, 11.4 ± 0.2,13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.32. The solid form according to any one of embodiments 23-26, characterized by an X- ray powder diffractogram comprising a signal at two or more two-theta values of 5.6 ± 0.2,13.6 ± 0.2, and 18.1 ± 0.2.33. The solid form according to any one of embodiments 23-26, characterized by an X- ray powder diffractogram comprising a signal at two-theta values of 5.6 ± 0.2, 13.6 ± 0.2, and 18.1 ± 0.2.34. The solid form according to any one of embodiments 23-33, characterized by an X- ray powder diffractogram substantially similar to FIG. 6.35. The solid form according to any one of embodiments 23-34, characterized by a DSC thermogram substantially similar to FIG. 8.36. The solid form according to any one of embodiments 23-35, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 183 °C to about 188 °C.37. The solid form according to any one of embodiments 23-36, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 185.9 °C.Attorney Docket No. 15496.0048-0030438. The solid form according to any one of embodiments 23-37, characterized by a TGA thermogram substantially similar to FIG. 8.39. The solid form according to any one of embodiments 23-38, characterized by a weight loss of less than about 1.5 wt. % as determined by thermogravimetric analysis when heated from about 25 °C to about 75 °C.40. The solid form according to any one of embodiments 23-39, characterized by a weight loss of less than about 1.2 wt. % as determined by thermogravimetric analysis when heated from about 25 °C to about 75 °C.41. The solid form according to any one of embodiments 23-40, characterized by a weight loss of about 1.1 wt. % as determined by thermogravimetric analysis when heated from about 25 °C to about 75 °C.42. A solid form comprising Compound (I):and a Lewis base.43. A solid form comprising Compound (I):and benzamide.44. The solid form according to embodiment 43, wherein Compound (I) and benzamide are present in about a 1 : 1 stoichiometric ratio.45. Benzamide Solid Form of Compound (I):Attorney Docket No. 15496.0048-0030446. The solid form according to any one of embodiments 42-45, characterized by an X- ray powder diffractogram comprising a signal at two or more two-theta values chosen from5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.47. The solid form according to any one of embodiments 42-45, characterized by an X- ray powder diffractogram comprising a signal at three or more two-theta values chosen from5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.48. The solid form according to any one of embodiments 42-45, characterized by an X- ray powder diffractogram comprising a signal at four or more two-theta values chosen from5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.49. The solid form according to any one of embodiments 42-45, characterized by an X- ray powder diffractogram comprising a signal at five or more two-theta values chosen from5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.50. The solid form according to any one of embodiments 42-45, characterized by an X- ray powder diffractogram comprising a signal at two-theta values of 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.51. The solid form according to any one of embodiments 42-50, characterized by an X- ray powder diffractogram substantially similar to FIG. 13.52. The solid form according to any one of embodiments 42-51, characterized by a DSC thermogram substantially similar to FIG. 15.Attorney Docket No. 15496.0048-0030453. The solid form according to any one of embodiments 42-52, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 84 °C to about 90 °C.54. The solid form according to any one of embodiments 42-53, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 87 °C to about 88 °C.55. The solid form according to any one of embodiments 42-54, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 87.1 °C.56. The solid form according to any one of embodiments 42-55, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 116 °C to about 120 °C.57. The solid form according to any one of embodiments 42-56, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 117 °C to about 118 °C.58. The solid form according to any one of embodiments 42-57, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 117.8 °C.59. The solid form according to any one of embodiments 42-58, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 160 °C to about 166 °C.60. The solid form according to any one of embodiments 42-59, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 163 °C to about 164 °C.61. The solid form according to any one of embodiments 42-60, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 163.4 °C.62. The solid form according to any one of embodiments 42-61, characterized by a TGA thermogram substantially similar to FIG. 15.Attorney Docket No. 15496.0048-0030463. The solid form according to any one of embodiments 42-62, characterized by a weight loss of from about 10.0% to about 25.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.64. The solid form according to any one of embodiments 42-63, characterized by a weight loss of from about 12.0% to about 18.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.65. The solid form according to any one of embodiments 42-64, characterized by a weight loss of from about 14.0% to about 15.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.66. The solid form according to any one of embodiments 42-65, characterized by a weight loss of about 14.8% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.67. The solid form according to any one of embodiments 42-66, characterized by a weight loss of from about 10.0% to about 25.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C.68. The solid form according to any one of embodiments 42-67, characterized by a weight loss of from about 11.0% to about 17.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C.69. The solid form according to any one of embodiments 42-68, characterized by a weight loss of from about 13.5% to about 14.5% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C.70. The solid form according to any one of embodiments 42-69, characterized by a weight loss of about 13.9% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C.Attorney Docket No. 15496.0048-0030471. A solid form comprising Compound (I):and a Lewis acid.72. A solid form comprising Compound (I):and manganese (II) chloride.73. The solid form according to embodiment 72, wherein Compound (I) and manganese(II) chloride are present in about a 1 : 1 stoichiometric ratio.74. Manganese (II) Chloride Solid Form of Compound (I):75. The solid form according to any one of embodiments 71-74, characterized by an X- ray powder diffractogram comprising a signal at two or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.76. The solid form according to any one of embodiments 71-74, characterized by an X- ray powder diffractogram comprising a signal at three or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.Attorney Docket No. 15496.0048-0030477. The solid form according to any one of embodiments 71-74, characterized by an X- ray powder diffractogram comprising a signal at four or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.78. The solid form according to any one of embodiments 71-74, characterized by an X- ray powder diffractogram comprising a signal at five or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.79. The solid form according to any one of embodiments 71-74, characterized by an X- ray powder diffractogram comprising a signal at two-theta values of 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.80. The solid form according to any one of embodiments 71-79, characterized by an X- ray powder diffractogram substantially similar to FIG. 16.81. The solid form according to any one of embodiments 71-80, characterized by a DSC thermogram substantially similar to FIG. 18.82. The solid form according to any one of embodiments 71-81, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 33 °C to about 38 °C.83. The solid form according to any one of embodiments 71-82, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 35 °C to about 36 °C.84. The solid form according to any one of embodiments 71-83, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 35.7 °C.85. The solid form according to any one of embodiments 71-84, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 56 °C to about 61 °C.Attorney Docket No. 15496.0048-0030486. The solid form according to any one of embodiments 71-85, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 58 °C to about 59 °C.87. The solid form according to any one of embodiments 71-86, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 58.6 °C.88. The solid form according to any one of embodiments 71-87, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 63 °C to about 69 °C.89. The solid form according to any one of embodiments 71-88, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 66 °C to about 67 °C.90. The solid form according to any one of embodiments 71-89, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 66.1 °C.91. The solid form according to any one of embodiments 71-90, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 119 °C to about 124 °C.92. The solid form according to any one of embodiments 71-91, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 121 °C to about 122 °C.93. The solid form according to any one of embodiments 71-92, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 121.7 °C.94. The solid form according to any one of embodiments 71-93, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 164 °C to about 171 °C.Attorney Docket No. 15496.0048-0030495. The solid form according to any one of embodiments 71-94, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 167 °C to about 168 °C.96. The solid form according to any one of embodiments 71-95, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 167.4 °C.97. The solid form according to any one of embodiments 71-96, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 205 °C to about 209 °C.98. The solid form according to any one of embodiments 71-97, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 207 °C to about 208 °C.99. The solid form according to any one of embodiments 71-98, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 207.4 °C.100. The solid form according to any one of embodiments 71-99, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 271 °C to about 276 °C.101. The solid form according to any one of embodiments 71-100, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 273 °C to about 274 °C.102. The solid form according to any one of embodiments 71-101, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 273.8 °C.103. The solid form according to any one of embodiments 71-102, characterized by a TGA thermogram substantially similar to FIG. 18.Attorney Docket No. 15496.0048-00304104. The solid form according to any one of embodiments 71-103, characterized by a weight loss of from about 1.0% to about 8.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.105. The solid form according to any one of embodiments 71-104, characterized by a weight loss of from about 2.0% to about 6.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.106. The solid form according to any one of embodiments 71-105, characterized by a weight loss of from about 3.0% to about 5.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.107. The solid form according to any one of embodiments 71-106, characterized by a weight loss of about 4.6% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.108. The solid form according to any one of embodiments 71-107, characterized by a weight loss of from about 1.0% to about 7.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C.109. The solid form according to any one of embodiments 71-108, characterized by a weight loss of from about 2.0% to about 6.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C.110. The solid form according to any one of embodiments 71-109, characterized by a weight loss of from about 3.0% to about 4.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C.111. The solid form according to any one of embodiments 71-110, characterized by a weight loss of about 3.8% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C.112. A pharmaceutical composition comprising: at least one solid form of Compound (I) according to any one of embodiments 1-111; and at least one pharmaceutically acceptable excipient.Attorney Docket No. 15496.0048-00304113. A method for the prophylaxis or treatment of depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder in a subject in need thereof, comprising administering a therapeutically effective amount of at least one solid form of Compound (I) according to any one of embodiments 1-111 or a pharmaceutical composition according to embodiment 112 to the subject.114. The method of embodiment 113, wherein the depression is major depressive disorder.115. The method of embodiment 113, wherein the depression is treatment-resistant depression.116. The solid form of Compound (I) according to any one of embodiments 1-111 or the pharmaceutical composition according to embodiment 112 for use in prevention or treatment of depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder.117. The solid form for use of embodiment 116, wherein the depression is major depressive disorder.118. The solid form for use of embodiment 116, wherein the depression is treatmentresistant depression.119. Use of a solid form of Compound (I) according to any one of embodiments 1-111 or the pharmaceutical composition according to embodiment 112 for the manufacture of a medicament for preventing or treating depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder.120. The use of embodiment 119, wherein the depression is major depressive disorder.121. The use of embodiment 119, wherein the depression is treatment-resistant depression.122. A process for preparing the solvate according to any one of embodiments 1-22, comprising:Attorney Docket No. 15496.0048-00304(a) combining Compound (I) with chloroform to provide a composition comprising Compound (I); and(b) stirring the composition at room temperature.123. The process according to embodiment 122, further comprising:(c) filtering the composition to isolate the solvate.124. The process according to embodiment 122 or embodiment 123, wherein (b) comprises stirring the composition for two weeks.125. A process for preparing the solid form according to any one of embodiments 23-41, comprising:(a) combining Compound (I) with one or more solvents to provide a first composition comprising Compound (I);(b) adding an aqueous solution of camphorsulfonic acid to the first composition to provide a second composition; and(c) stirring the second composition at room temperature.126. The process according to embodiment 125, further comprising:(d) filtering the second composition to isolate the solid form.127. The process according to embodiment 125 or embodiment 126, wherein (a) comprises combining Compound (I) with chloroform and dichloromethane.128. The process according to embodiment 127, wherein (a) comprises combining Compound (I) with a 1 : 1 ratio of chloroform and dichloromethane.129. The process according to any one of embodiments 125-128, wherein (b) comprises adding an equimolar amount of camphorsulfonic acid to the amount of Compound (I) combined with the one or more solvents in (a).130. The process according to any one of embodiments 125-129, wherein the concentration of the aqueous solution of camphorsulfonic acid in (b) is 2 molar (2 M).Attorney Docket No. 15496.0048-00304131. The process according to any one of embodiments 125-130, wherein (c) comprises stirring the second composition for three days.132. A process for preparing the solid form according to any one of embodiments 42-70, comprising:(a) combining Compound (I) with one or more solvents to provide a composition;(b) adding benzamide to the composition;(c) heating the composition;(d) stirring the composition; and(e) cooling the composition to room temperature.133. The process according to embodiment 132, further comprising:(f) evaporating the solvent from the composition to provide the solid form.134. The process according to embodiment 132 or embodiment 133, wherein (a) comprises combining Compound (I) with a mixture of chloroform and dichloromethane.135. The process according to any one of embodiments 132-134, wherein (b) comprises adding an amount of benzamide that is equimolar to the amount of Compound (I) to the composition.136. The process according to any one of embodiments 132-135, wherein (c) comprises heating the composition to 50 °C.137. The process according to any one of embodiments 132-136, wherein (d) comprises stirring the composition for two days.138. A process for preparing the solid form according to any one of embodiments 42-70, comprising:(a) providing a first composition comprising one or more solvents;(b) adding Compound (I) to a ball mill vial;(c) adding benzamide to the ball mill vial;(d) adding at least a portion of the first composition to the ball mill vial to form a reaction mixture; andAttorney Docket No. 15496.0048-00304(e) ball milling the reaction mixture in the ball mill vial.139. The process according to embodiment 138, further comprising:(f) isolating the solid form from the ball mill vial.140. The process according to embodiment 138 or embodiment 139, wherein (a) comprises providing a first composition comprising chloroform and dichloromethane.141. The process according to any one of embodiments 138-140, wherein (c) comprises adding an amount of benzamide that is equimolar to the amount of Compound (I) to the ball mill vial.142. The process according to any one of embodiments 138-141, wherein (e) comprises ball milling the reaction mixture for 30 minutes.143. A process for preparing the solid form according to any one of embodiments 71-111, comprising:(a) combining Compound (I) with one or more solvents to provide a composition;(b) adding manganese (II) chloride to the composition;(c) heating the composition;(d) stirring the composition; and(e) cooling the composition to room temperature.144. The process according to embodiment 143, further comprising:(f) evaporating the solvent from the composition to provide the solid form.145. The process according to embodiment 143 or embodiment 144, wherein (a) comprises combining Compound (I) with a mixture of dioxane and dichloromethane.146. The process according to any one of embodiments 143-145, wherein (b) comprises adding an amount of manganese (II) chloride that is equimolar to the amount of Compound (I) to the composition.Attorney Docket No. 15496.0048-00304147. The process according to any one of embodiments 143-146, wherein (c) comprises heating the composition to 50 °C.148. The process according to any one of embodiments 143-147, wherein (d) comprises stirring the composition for two days.149. A process for preparing the solid form according to any one of embodiments 71-111, comprising:(a) providing a first composition comprising one or more solvents;(b) adding Compound (I) to a ball mill vial;(c) adding manganese (II) chloride to the ball mill vial;(d) adding at least a portion of the first composition to the ball mill vial to form a reaction mixture; and(e) ball milling the reaction mixture in the ball mill vial.150. The process according to embodiment 149, further comprising:(f) isolating the solid form from the ball mill vial.151. The process according to embodiment 149 or embodiment 150, wherein (a) comprises providing a first composition comprising dioxane and dichloromethane.152. The process according to any one of embodiments 149-151, wherein (c) comprises adding an amount of manganese (II) chloride that is equimolar to the amount of Compound (I) to the ball mill vial.153. The process according to any one of embodiments 149-152, wherein (e) comprises ball milling the reaction mixture for 30 minutes.

[0080] Some embodiments of the present disclosure relate to a solid form of Compound (I):Attorney Docket No. 15496.0048-00304

[0081] In some embodiments, the solid form of Compound (I) is Form I of Compound (I).FIG. 1 shows an X-ray powder diffractogram for Form I of Compound (I). FIG. 2 shows a differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for Form I of Compound (I).

[0082] In some embodiments, the solid form of Compound (I) is a solvate of Compound (I). In some embodiments, the solid form of Compound (I) is a solvate comprising Compound (I) and chloroform. In some embodiments, the solvate of Compound (I) is Mono-ChloroformSolvate Form of Compound (

[0083] FIG. 3 shows an X-ray powder diffractogram for Mono-Chloroform Solvate Form of Compound (I).

[0084] In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 ± 0.2. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X- ray powder diffractogram comprising a signal at three or more two-theta values chosen from 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 ± 0.2. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from 4.2 ± 0.2, 10.2 ± 0.2, 12.6± 0.2, 20.6 ± 0.2, and 25.7 ± 0.2. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 ± 0.2.

[0085] In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram substantially similar to FIG. 3.

[0086] In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at two two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at three two-theta valuesAttorney Docket No. 15496.0048-00304 chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at four two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at five two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at six two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at seven two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at eight two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at nine two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at ten two-theta values chosen from the list of two-theta values in Table 1.

[0087] In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at three or more two- theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at five or more two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X- ray powder diffractogram comprising a signal at six or more two-theta values chosen fromAttorney Docket No. 15496.0048-00304 the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at seven or more two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at eight or more two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at nine or more two-theta values chosen from the list of two-theta values in Table 1. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at ten or more two-theta values chosen from the list of two-theta values in Table 1.

[0088] In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from 4.2 ± 0.2, 8.4 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 15.0 ± 0.2, 15.8 ± 0.2, 16.5 ± 0.2, 17.7 ± 0.2, 18.6 ± 0.2, 19.2 ± 0.2, 19.7 ± 0.2, 20.2 ± 0.2, 20.6 ± 0.2, 20.9 ± 0.2, 21.5± 0.2, 21.9 ± 0.2, 22.5 ± 0.2, 22.7 ± 0.2, 23.3 ± 0.2, 23.8 ± 0.2, 24.2 ± 0.2, 24.7 ± 0.2, 25.0± 0.2, 25.7 ± 0.2, 26.5 ± 0.2, 27.1 ± 0.2, 27.4 ± 0.2, 28.0 ± 0.2, 28.5 ± 0.2, 29.0 ± 0.2, 29.6± 0.2, 30.1 ± 0.2, 30.5 ± 0.2, 31.2 ± 0.2, 31.7 ± 0.2, 32.2 ± 0.2, 32.6 ± 0.2, 33.5 ± 0.2, 34.0± 0.2, 34.3 ± 0.2, 35.3 ± 0.2, 35.7 ± 0.2, 36.5 ± 0.2, 37.3 ± 0.2, 37.5 ± 0.2, 38.3 ± 0.2, 39.0± 0.2, 40.3 ± 0.2, 42.2 ± 0.2, 42.6 ± 0.2, 43.5 ± 0.2, and 43.8 ± 0.2.

[0089] FIG. 4 shows an overlay of X-ray powder diffractograms for Form I of Compound (I) and Mono-Chloroform Solvate Form of Compound (I).

[0090] FIG. 5 shows a differential scanning calorimetry (DSC) thermogram for MonoChloroform Solvate Form of Compound (I). FIG. 5 also shows a thermogravimetric analysis (TGA) thermal curve for Mono-Chloroform Solvate Form of Compound (I).

[0091] In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 122 °C to about 128 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 124 °C to about 125 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 124.6 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized byAttorney Docket No. 15496.0048-00304 a DSC thermogram comprising an exothermic event at a temperature of from about 193 °C to about 198 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a DSC thermogram comprising an exothermic event at a temperature of from about 195 °C to about 196 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a DSC thermogram comprising an exothermic event at a temperature of about 195.4 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 218 °C to about 223 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 220.4 °C.

[0092] In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a weight loss of from about 20.0% to about 30.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a weight loss of from about 20.0% to about 25.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a weight loss of from about 23.0% to about 24.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a weight loss of about 23.3% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C.

[0093] In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a DSC thermogram substantially similar to FIG. 5. In some embodiments, the solvate comprising Compound (I) and chloroform is characterized by a TGA thermal curve substantially similar to FIG. 5.

[0094] In some embodiments, the solid form of Compound (I) is a co-crystal comprising Compound (I) and a co-crystal former. In some embodiments, the co-crystal former is camphorsulfonic acid (CSA). In some embodiments, the co-crystal former is (+)-(lS)- camphor-10-sulfonic acid. In some embodiments, the co-crystal former is (-)-(lR)-camphor- 10-sulfonic acid. In some embodiments of a co-crystal comprising Compound (I) and a cocrystal former, Compound (I) and the co-crystal former are present in a 1 :0.9 stoichiometric ratio.

[0095] Some embodiments of the disclosure relate to a solid form comprising Compound (I) and camphorsulfonic acid. Some embodiments of the disclosure relate to a co-crystalAttorney Docket No. 15496.0048-00304 comprising Compound (I) and camphorsulfonic acid. In some embodiments, the camphorsulfonic acid is (+)-(lS)-camphor-10-sulfonic acid. In some embodiments, the camphorsulfonic acid is (-)-(lR)-camphor-10-sulfonic acid. In some embodiments, the camphorsulfonic acid is a mixture of (+)-(lS)-camphor-10-sulfonic acid and (-)-(lR)- camphor-10-sulfonic acid. In some embodiments, the camphorsulfonic acid may contain at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95%, at least about 99%, or at least about 99.9% enantiomeric excess, or an enantiomeric excess within a range defined by any of the preceding numbers. In some embodiments of a solid form comprising Compound (I) and camphorsulfonic acid, Compound (I) and the camphorsulfonic acid are present in a 1 :0.9 stoichiometric ratio.

[0096] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is CSA Solid Form of Compound

[0097] FIG. 6 shows an X-ray powder diffractogram for CSA Solid Form of Compound (I).

[0098] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at 5.6 ± 0.2 degrees two-theta. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at 11.4 ± 0.2 degrees two-theta. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at 13.6 ± 0.2 degrees two-theta. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at 18.1 ± 0.2 degrees two-theta. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at 22.8 ± 0.2 degrees two-theta. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at 24.3 ± 0.2 degrees two-theta.Attomey Docket No. 15496.0048-00304

[0099] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from 5.6 ± 0.2, 13.6 ± 0.2, and 18.1 ± 0.2. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from 5.6 ± 0.2, 13.6 ± 0.2, and 18.1 ± 0.2. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 5.6 ± 0.2, 13.6 ± 0.2, and 18.1 ± 0.2.

[0100] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from 5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from 5.6 ± 0.2, 11.4 + 0.2, 13.6 + 0.2, 18.1 + 0.2, 22.8 + 0.2, and 24.3 + 0.2. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from 5.6 + 0.2, 11.4 + 0.2, 13.6 + 0.2, 18.1 + 0.2, 22.8 + 0.2, and 24.3 + 0.2. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from 5.6 + 0.2, 11.4 + 0.2, 13.6 + 0.2, 18.1 + 0.2, 22.8 + 0.2, and 24.3 + 0.2. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at five or more two-theta values chosen from 5.6 + 0.2, 11.4 ± 0.2, 13.6 + 0.2, 18.1 + 0.2, 22.8 + 0.2, and 24.3 + 0.2. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 5.6 + 0.2, 11.4 + 0.2, 13.6 + 0.2, 18.1 + 0.2, 22.8 + 0.2, and 24.3 + 0.2.

[0101] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram substantially similar to FIG. 6.

[0102] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-Attorney Docket No. 15496.0048-00304 ray powder diffractogram comprising a signal at two two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at three two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at four two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at five two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at six two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at seven two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at eight two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at nine two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at ten two-theta values chosen from the list of two-theta values in Table 4.

[0103] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X- ray powder diffractogram comprising a signal at two or more two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from the list of two-theta values in Table 4. In someAttorney Docket No. 15496.0048-00304 embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at five or more two- theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at six or more two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at seven or more two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at eight or more two- theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at nine or more two-theta values chosen from the list of two-theta values in Table 4. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at ten or more two-theta values chosen from the list of two-theta values in Table 4.

[0104] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from 3.6 ± 0.2, 5.6 ± 0.2, 11.1 ± 0.2, 11.4 ± 0.2, 12.8 ± 0.2, 13.6± 0.2, 14.3 ± 0.2, 14.8 ± 0.2, 16.5 ± 0.2, 17.1 ± 0.2, 18.0 ± 0.2, 18.8 ± 0.2, 19.2 ± 0.2, 20.1± 0.2, 20.5 ± 0.2, 22.2 ± 0.2, 22.8 ± 0.2, 23.2 ± 0.2, 24.3 ± 0.2, 24.7 ± 0.2, 25.0 ± 0.2, 26.6± 0.2, 29.8 ± 0.2, 31.0 ± 0.2, 33.4 ± 0.2, 37.8 ± 0.2, 39.2 ± 0.2, 41.4 ± 0.2, 42.6 ± 0.2, and43.3 + 0.2.

[0105] FIG. 7 shows an overlay of X-ray powder diffractograms for Form I of Compound (I), CSA Solid Form of Compound (I), Mono-Chloroform Solvate Form of Compound (I), and (+)-(lS)-camphor-10-sulfonic acid.

[0106] FIG. 8 shows a differential scanning calorimetry (DSC) thermogram for CSA Solid Form of Compound (I). FIG. 8 also shows a thermogravimetric analysis (TGA) thermal curve for CSA Solid Form of Compound (I).

[0107] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by a DSC thermogram substantially similar to FIG. 8. In someAttorney Docket No. 15496.0048-00304 embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by a TGA thermal curve substantially similar to FIG. 8.

[0108] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 183 °C to about 188 °C. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 185 °C to about 187 °C. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 185.9 °C.

[0109] In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by a weight loss of less than about 1.5 wt. % as determined by thermogravimetric analysis when heated from about 25 °C to about 75 °C. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by a weight loss of less than about 1.2 wt. % as determined by thermogravimetric analysis when heated from about 25 °C to about 75 °C. In some embodiments, the solid form comprising Compound (I) and camphorsulfonic acid is characterized by a weight loss of about 1.1 wt. % as determined by thermogravimetric analysis when heated from about 25 °C to about 75 °C.

[0110] FIG. 9 shows aNMR spectrum for CSA Solid Form of Compound (I).

[0111] FIG. 10 shows the results of a homonuclear correlation spectroscopy (COSY) experiment of CSA Solid Form of Compound (I).

[0112] FIG. 11 shows the results of a heteronuclear single quantum coherence (HSQC) experiment of CSA Solid Form of Compound (I).

[0113] In some embodiments, the solid form of Compound (I) is a solid form comprising Compound (I) and benzamide. In some embodiments, the solid form comprising Compound (I) and benzamide is crystalline. In some embodiments of a solid form comprising Compound (I) and benzamide, Compound (I) and benzamide are present in about a 1 : 1 stoichiometric ratio.Attorney Docket No. 15496.0048-00304

[0114] In some embodiments, the solid form of Compound (I) is Benzamide Solid Form ofCompound

[0115] FIG. 13 shows an X-ray powder diffractogram for Benzamide Solid Form ofCompound (I).

[0116] In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at five or more two-theta values chosen from 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 5.4 ± 0.2, 10.6 ± 0.2,15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.

[0117] In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram substantially similar to FIG. 13.

[0118] In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at two two-theta values chosen from the list of two-thetaAttorney Docket No. 15496.0048-00304 values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at three two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at four two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at five two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at six two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at seven two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at eight two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at nine two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at ten two-theta values chosen from the list of two-theta values in Table 6.

[0119] In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at five or more two-theta values chosen from the list of two-theta values in Table 6.Attorney Docket No. 15496.0048-00304In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at six or more two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at seven or more two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at eight or more two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at nine or more two-theta values chosen from the list of two-theta values in Table 6. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at ten or more two-theta values chosen from the list of two-theta values in Table 6.

[0120] In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from 3.6 ± 0.2, 4.2 ± 0.2, 5.4 ± 0.2, 7.9 ± 0.2, 8.3 ± 0.2, 10.0 ± 0.2, 10.2 ± 0.2,10.7 ± 0.2, 12.6 ± 0.2, 15.3 ± 0.2, 15.7 ± 0.2, 16.0 ± 0.2, 16.9 ± 0.2, 18.0 ± 0.2, 18.3 ± 0.2,18.7 ± 0.2, 19.2 ± 0.2, 20.1 ± 0.2, 20.3 ± 0.2, 20.6 ± 0.2, 21.1 ± 0.2, 21.6 ± 0.2, 22.4 ± 0.2,23.1 ± 0.2, 23.6 ± 0.2, 24.0 ± 0.2, 25.0 ± 0.2, 26.5 ± 0.2, 26.9 ± 0.2, 27.5 ± 0.2, 28.3 ± 0.2,28.6 ± 0.2, 28.8 ± 0.2, 29.1 ± 0.2, 29.9 ± 0.2, 30.6 ± 0.2, 31.2 ± 0.2, 31.8 ± 0.2, 32.3 ± 0.2,32.9 ± 0.2, 33.4 ± 0.2, 35.0 ± 0.2, 35.5 ± 0.2, 36.0 ± 0.2, 36.3 ± 0.2, 37.4 ± 0.2, 38.3 ± 0.2,39.7 ± 0.2, 40.1 ± 0.2, 40.7 ± 0.2, 41.2 ± 0.2, 42.8 ± 0.2, and 44.2 ± 0.2.

[0121] FIG. 14 shows an overlay of X-ray powder diffractograms for Mono-Chloroform Solvate Form of Compound (I), Form I of Compound (I), benzamide, and Benzamide Solid Form of Compound (I).

[0122] FIG. 15 shows a differential scanning calorimetry (DSC) thermogram for Benzamide Solid Form of Compound (I). FIG. 15 also shows a therm ogravimetric analysis (TGA) thermal curve for Benzamide Solid Form of Compound (I).

[0123] In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram substantially similar to FIG. 15. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a TGA thermal curve substantially similar to FIG. 15.Attorney Docket No. 15496.0048-00304

[0124] In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 84 °C to about 90 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 87 °C to about 88 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 87.1 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 116 °C to about 120 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 117 °C to about 118 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 117.8 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 160 °C to about 166 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 163 °C to about 164 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 163.4 °C.

[0125] In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a weight loss of from about 10.0% to about 25.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a weight loss of from about 12.0% to about 18.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a weight loss of from about 14.0% to about 15.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a weight loss of about 14.8% as determined by thermogravimetric analysis when heated from about 25 °C to about 100°C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a weight loss of from about 10.0% to about 25.0% as determined by thermogravimetricAttorney Docket No. 15496.0048-00304 analysis when heated from about 100 °C to about 180 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a weight loss of from about 11.0% to about 17.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C. In some embodiments, the solid form comprising Compound(I) and benzamide is characterized by a weight loss of from about 13.5% to about 14.5% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C. In some embodiments, the solid form comprising Compound (I) and benzamide is characterized by a weight loss of about 13.9% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C.

[0126] In some embodiments, the solid form of Compound (I) is a solid form comprising Compound (I) and manganese (II) chloride. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is crystalline. In some embodiments of a solid form comprising Compound (I) and manganese (II) chloride, Compound (I) and manganese(II) chloride are present in about a 1 : 1 stoichiometric ratio.

[0127] In some embodiments, the solid form of Compound (I) is Manganese (II) ChlorideSolid Form of Compound

[0128] FIG. 16 shows an X-ray powder diffractogram for Manganese (II) Chloride Solid Form of Compound (I).

[0129] In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from 16.0 + 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-rayAttorney Docket No. 15496.0048-00304 powder diffractogram comprising a signal at four or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X- ray powder diffractogram comprising a signal at five or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.

[0130] In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram substantially similar to FIG. 16.

[0131] In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at two two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at three two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at four two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at five two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at six two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at seven two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at eight two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powderAttorney Docket No. 15496.0048-00304 diffractogram comprising a signal at nine two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at ten two-theta values chosen from the list of two-theta values in Table 7.

[0132] In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at five or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at six or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at seven or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at eight or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at nine or more two-theta values chosen from the list of two-theta values in Table 7. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at ten or more two-theta values chosen from the list of two-theta values in Table 7.Attorney Docket No. 15496.0048-00304

[0133] FIG. 17 shows an overlay of X-ray powder diffractograms for Manganese (II) Chloride Solid Form of Compound (I), manganese (II) chloride, Mono-Chloroform Solvate Form of Compound (I), and Form I of Compound (I).

[0134] In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by an X-ray powder diffractogram comprising a signal at one or more two-theta values chosen from 3.6 ± 0.2, 11.0 + 0.2, 12.8 + 0.2, 14.3 + 0.2, 14.7 + 0.2,15.6 + 0.2, 16.0 + 0.2, 16.5 + 0.2, 17.2 + 0.2, 17.9 + 0.2, 18.5 + 0.2, 19.2 + 0.2, 20.1 + 0.2,21.8 + 0.2, 22.2 + 0.2, 23.2 + 0.2, 24.7 + 0.2, 25.1 + 0.2, 26.0 + 0.2, 26.6 + 0.2, 27.2 + 0.2,27.6 + 0.2, 28.9 + 0.2, 29.2 + 0.2, 29.8 + 0.2, 30.6 + 0.2, 31.0 + 0.2, 31.7 + 0.2, 32.0 + 0.2,32.4 + 0.2, 32.8 + 0.2, 33.0 + 0.2, 33.4 + 0.2, 34.0 + 0.2, 34.5 + 0.2, 36.0 + 0.2, 37.1 + 0.2,37.9 + 0.2, 38.1 + 0.2, 39.3 + 0.2, 40.9 + 0.2, 41.3 + 0.2, 42.2 + 0.2, 42.6 + 0.2, 43.4 + 0.2,44.0 + 0.2, 44.5 + 0.2, and 44.9 + 0.2.

[0135] FIG. 18 shows a differential scanning calorimetry (DSC) thermogram for Manganese (II) Chloride Solid Form of Compound (I). FIG. 18 also shows a thermogravimetric analysis (TGA) thermal curve for Manganese (II) Chloride Solid Form of Compound (I).

[0136] In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram substantially similar to FIG. 18. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a TGA thermal curve substantially similar to FIG. 18.

[0137] In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 33 °C to about 38 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 35 °C to about 36 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 35.7 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 56 °C to about 61 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 58 °C to about 59 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogramAttorney Docket No. 15496.0048-00304 comprising an endothermic event at a temperature of about 58.6 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 63 °C to about 69 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 66 °C to about 67 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 66.1 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 119 °C to about 124 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 121 °C to about 122 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 121.7 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 164 °C to about 171 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 167 °C to about 168 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 167.4 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 205 °C to about 209 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 207 °C to about 208 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 207.4 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 271 °C to about 276 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermicAttorney Docket No. 15496.0048-00304 event at a temperature of from about 273 °C to about 274 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a DSC thermogram comprising an endothermic event at a temperature of about 273.8 °C.

[0138] In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a weight loss of from about 1.0% to about 8.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a weight loss of from about 2.0% to about 6.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a weight loss of from about 3.0% to about 5.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a weight loss of about 4.6% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a weight loss of from about 1.0% to about 7.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a weight loss of from about 2.0% to about 6.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a weight loss of from about 3.0% to about 4.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C. In some embodiments, the solid form comprising Compound (I) and manganese (II) chloride is characterized by a weight loss of about 3.8% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C.

[0139] Some embodiments of the present disclosure provide a process for preparing a solid form of Compound (I):Attorney Docket No. 15496.0048-00304

[0140] In some embodiments, the present disclosure provides a process for preparing a solvate of Compound (I). In some embodiments, the present disclosure provides a process for preparing a solvate comprising Compound (I) and chloroform. In some embodiments, the present disclosure provides a process for preparing Mono-Chloroform Solvate Form of Compound (I).

[0141] In some embodiments, the process comprises: (a) combining Compound (I) with chloroform to provide a composition comprising Compound (I); and (b) stirring the composition at room temperature. In some embodiments, the process further comprises: (c) filtering the composition to isolate the solvate. In some embodiments of said process, (b) comprises stirring the composition for one, two, three, four, or five days. In some embodiments of said process, (b) comprises stirring the composition for one week. In some embodiments of said process, (b) comprises stirring the composition for two weeks.

[0142] Some embodiments of the present disclosure provide a process for preparing a solid form of Compound (I):some embodiments, the present disclosure provides a process for preparing CSA Solid Form of Compound (I).

[0143] In some embodiments, the process comprises: (a) combining Compound (I) with one or more solvents to provide a first composition comprising Compound (I); (b) adding an aqueous solution of camphorsulfonic acid to the first composition to provide a second composition; and (c) stirring the second composition at room temperature. In some embodiments, the process further comprises: (d) filtering the second composition to isolate the solid form. In some embodiments, (a) comprises combining Compound (I) with chloroform and dichloromethane. In some embodiments, (a) comprises combining Compound (I) with a 1 : 1 ratio of chloroform and dichloromethane. In some embodiments, (b) comprises adding camphorsulfonic acid in an amount that is equimolar to the amount of Compound (I) combined with the one or more solvents in (a). In some embodiments, the concentration of the aqueous solution of camphorsulfonic acid in (b) is 2 molar (2 M). In some embodiments, (c) comprises stirring the second composition for one, two, three, four, or five days. In some embodiments, (c) comprises stirring the second composition for one day.Attorney Docket No. 15496.0048-00304In some embodiments, (c) comprises stirring the second composition for two days. In some embodiments, (c) comprises stirring the second composition for three days.

[0144] In some embodiments, the present disclosure provides a process for preparing a solid form comprising Compound (I) and benzamide. In some embodiments, the present disclosure provides a process for preparing a solid form comprising Compound (I) and benzamide, wherein the solid form is crystalline. In some embodiments, the present disclosure provides a process for preparing Benzamide Solid Form of Compound (I).

[0145] In some embodiments, the process comprises: (a) combining Compound (I) with one or more solvents to provide a composition; (b) adding benzamide to the composition; (c) heating the composition; (d) stirring the composition; and (e) cooling the composition to room temperature. In some embodiments, the process further comprises: (f) evaporating the solvent from the composition to provide the solid form. In some embodiments, (a) comprises combining Compound (I) with a mixture of chloroform and dichloromethane. In some embodiments, (a) comprises combining Compound (I) with a mixture of chloroform and dichloromethane, wherein the mixture of chloroform and dichloromethane comprises chloroform and dichloromethane in a 1 : 1 ratio. In some embodiments, (b) comprises adding an amount of benzamide that is equimolar to the amount of Compound (I) to the composition. In some embodiments, (c) comprises heating the composition to 50 °C. In some embodiments, (d) comprises stirring the composition for one, two, three, four, or five days. In some embodiments, (d) comprises stirring the composition for two days.

[0146] In some embodiments, the process comprises: (a) providing a first composition comprising one or more solvents; (b) adding Compound (I) to a ball mill vial; (c) adding benzamide to the ball mill vial; (d) adding at least a portion of the first composition to the ball mill vial to form a reaction mixture; and (e) ball milling the reaction mixture in the ball mill vial. In some embodiments, the process further comprises: (f) isolating the solid form from the ball mill vial. In some embodiments, (a) comprises providing a first composition comprising chloroform and dichloromethane. In some embodiments, (a) comprises providing a first composition comprising chloroform and dichloromethane, wherein the first composition comprises chloroform and dichloromethane in a 1 : 1 ratio. In some embodiments, (c) comprises adding an amount of benzamide that is equimolar to the amount of Compound (I) to the ball mill vial. In some embodiments, (e) comprises ball milling the reaction mixture for 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, or 60 minutes. In some embodiments, (e) comprises ball milling the reaction mixture for 30 minutes.Attorney Docket No. 15496.0048-00304

[0147] In some embodiments, the present disclosure provides a process for preparing a solid form comprising Compound (I) and manganese (II) chloride. In some embodiments, the present disclosure provides a process for preparing a solid form comprising Compound (I) and manganese (II) chloride, wherein the solid form is crystalline. In some embodiments, the present disclosure provides a process for preparing Manganese (II) Chloride Solid Form of Compound (I).

[0148] In some embodiments, the process comprises: (a) combining Compound (I) with one or more solvents to provide a composition; (b) adding manganese (II) chloride to the composition; (c) heating the composition; (d) stirring the composition; and (e) cooling the composition to room temperature. In some embodiments, the process further comprises: (f) evaporating the solvent from the composition to provide the solid form. In some embodiments, (a) comprises combining Compound (I) with a mixture of dioxane and dichloromethane. In some embodiments, (a) comprises combining Compound (I) with a mixture of dioxane and dichloromethane, wherein the mixture of dioxane and dichloromethane comprises dioxane and dichloromethane in a 1 : 1 ratio. In some embodiments, (b) comprises adding an amount of manganese (II) chloride that is equimolar to the amount of Compound (I) to the composition. In some embodiments, (c) comprises heating the composition to 50 °C. In some embodiments, (d) comprises stirring the composition for one, two, three, four, or five days. In some embodiments, (d) comprises stirring the composition for two days.

[0149] In some embodiments, the process comprises: (a) providing a first composition comprising one or more solvents; (b) adding Compound (I) to a ball mill vial; (c) adding manganese (II) chloride to the ball mill vial; (d) adding at least a portion of the first composition to the ball mill vial to form a reaction mixture; and (e) ball milling the reaction mixture in the ball mill vial. In some embodiments, the process further comprises: (f) isolating the solid form from the ball mill vial. In some embodiments, (a) comprises providing a first composition comprising dioxane and dichloromethane. In some embodiments, (a) comprises providing a first composition comprising dioxane and dichloromethane, wherein the first composition comprises dioxane and dichloromethane in a 1 : 1 ratio. In some embodiments, (c) comprises adding an amount of manganese (II) chloride that is equimolar to the amount of Compound (I) to the ball mill vial. In some embodiments, (e) comprises ball milling the reaction mixture for 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, or 60 minutes. In some embodiments, (e) comprises ball milling the reaction mixture for 30 minutes.Attorney Docket No. 15496.0048-00304

[0150] Claims or descriptions that include “or” or “and / or” between at least one members of a group are considered satisfied if one, more than one, or all of the group members are present in, employed in, or otherwise relevant to a given product or process unless indicated to the contrary or otherwise evident from the context. The disclosure includes embodiments in which exactly one member of the group is present in, employed in, or otherwise relevant to a given product or process. The disclosure includes embodiments in which more than one, or all the group members are present in, employed in, or otherwise relevant to a given product or process.

[0151] Furthermore, the disclosure encompasses all variations, combinations, and permutations in which at least one limitation, element, clause, and descriptive term from at least one of the listed claims is introduced into another claim. For example, any claim that is dependent on another claim can be modified to include at least one limitation found in any other claim that is dependent on the same base claim. Where elements are presented as lists, such as, e.g., in Markush group format, each subgroup of the elements is also disclosed, and any element(s) can be removed from the group. It should be understood that, in general, where the disclosure, or aspects of the disclosure, is / are referred to as comprising particular elements and / or features, embodiments of the disclosure or aspects of the disclosure consist, or consist essentially of, such elements and / or features. For purposes of simplicity, those embodiments have not been specifically set forth in haec verba herein. Where ranges are given (such as, e.g., from [X] to [Y]), endpoints (such as, e.g., [X] and [Y] in the phrase “from [X] to [Y]”) are included unless otherwise indicated. Furthermore, unless otherwise indicated or otherwise evident from the context and understanding of one of ordinary skill in the art, values that are expressed as ranges can assume any specific value or sub-range within the stated ranges in different embodiments of the disclosure, to the tenth of the unit of the lower limit of the range, unless the context clearly dictates otherwise.EXAMPLES

[0152] The following examples are intended to be illustrative and are not meant to limit the scope of the disclosure in any way.Example 1: Preparation of Compound (I)

[0153] A) 3-(4-(cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine

[0154] Tetrakis(triphenylphosphine)palladium(0) (0.922 g) was added to a suspension of 3- bromo-5-methylpyrazin-2-amine (5 g), 4-(cyclohexyloxy)phenylboronic acid (7.61 g) and sodium carbonate decahydrate (15.2 g) in DME (200 mL) and water (40 mL), and theAttorney Docket No. 15496.0048-00304 mixture was stirred at 80 °C under nitrogen overnight. The insoluble material was removed by filtration (eluted with EtOAc), silica-gel was added, and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (7.5 g) as a pale orange solid. MS (ESI+), found: 284.1.

[0155] B) 9-[4-(cyclohexyloxy)phenyl]-7-methyl-3, 4-dihydropyrazino[2, 1-c] [1,2,4 [thiadiazine 2, 2 -dioxide

[0156] To a suspension of NaH (60%, 5.29 g) in THF (dry) (100 mL) was added 2- chloroethanesulfonyl chloride (5.57 mL) at 0 °C and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-(cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine (7.5 g) in THF (dry) (75 mL) was added at 0 °C and the mixture was stirred at room temperature under nitrogen for 2 days. The mixture was quenched with water / THF at 0 °C carefully and water was added to form precipitates which were washed with EtOAc and water and dried in vacuo to give crude title compound (4.7 g). The part of this material (ca. 4.3 g) was crystallized from DMSO (200 mL) - EtOH (40 mL) / water (400 mL) to give 9-[4- (cyclohexyloxy)phenyl]-7-methyl-3,4-dihydropyrazino[2,l-c] [l,2,4]thiadiazine 2,2-dioxide as light yellow crystals (3.6 g), which was recrystallized from DMSO (100 mL) - EtOH (15 mL) / water (100 mL) at 80 °C to room temperature to give the title compound (3.09 g) as light-yellow crystals. 'HNMR (300 MHz, DMSO ) 8 1.17-1.59 (6H, m), 1.62-1.82 (2H, m), 1.85-2.03 (2H, m), 2.29 (3H, s), 3.42-3.55 (2H, m), 4.34-4.50 (1H, m), 4.51-4.62 (2H, m), 6.99 (2H, d, J= 8.7 Hz), 7.52 (1H, s), 8.00 (2H, d, J= 8.7 Hz). X-ray powder diffraction pattern with specific peaks at d-value (or d-spacing) = 23.99, 7.98, 5.99, 4.60, 3.99 and 3.42 A.Example 2: X-Ray Powder Diffraction (XRPD) Measurements

[0157] XRPD analysis for samples described in Examples 5, 6, 7, and 8 was performed on a Rigaku Powder X-Ray Diffractometer Miniflex Plus Serial Number BD70000351-01, outfitted with a Cu (copper) X-Ray tube, K-alpha X-ray type, and K-beta filters. For analysis, about 1 to 5 mg of sample was added to a XRPD zero-background sample holder. The powder was pressed down gently with a piece of weigh paper, and the sample holder was placed in the sample changer. Run Parameters: Miniflex Counter Detector, Kb Filter, Scan Axis Theta / 2-Theta, Mode Continuous, Start (deg) 3.0, Stop (deg) 45.0, Step (deg) 0.020, Speed (deg / min) 1.0, Spin-yes, Voltage (kV) 30, Current (mA) 15.Attorney Docket No. 15496.0048-00304Example 3: Differential Scanning Calorimetry (DSC) and Thermal Gravimetric Analysis (TGA):

[0158] DSC and TGA analysis for samples described in Examples 5, 6, 7, and 8 was performed on TA Instruments Discovery 2500 calorimeter with serial number: 2500-00547 (DSC) and Discovery 5500 with serial number: 5500-0126 (TGA). For DSC analysis, the weight of a Tzero pan and a Tzero lid were recorded. About 1 to 3 mg of sample was weighed into the Tzero Pan, and the Tzero lid was pressed on with tweezers. The pan was transferred to the DSC autosampler for analysis. The method for analysis was a ramp at 10 °C / min to about 350 °C or to the point of degradation as determined by TGA analysis. The reference pan was prepared with the same procedures, absent the sample. For TGA analysis, a standard aluminum sample pan was placed into the platinum TGA pan, and the blank was tared with the instrument. About 1 to 5 mg of sample was added to the standard aluminum pan and analyzed at 10 °C / min up to about 400 °C.Example 4: Nuclear Magnetic Resonance (NMR), Solution State

[0159] XH NMR spectra for samples described in Examples 5 and 6 were acquired on a Bruker Ascend 400 MHz spectrometer at an observing frequency of 400.1325 MHz. Samples were prepared in DMSO-t / e, vortexed / sonicated to ensure full dissolution, and then filtered through Spin-X 0.45 pm nylon centrifuge tube filters before transferring to 5 mm x 7” EVA NMR tubes for spectral acquisition.Example 5: Preparation and Characterization of Mono-Chloroform Solvate Form of Compound (I)Preparation

[0160] To a vial of around 500 pL of neat chloroform, Compound (I) was added scoop-wise until a saturated slurry was obtained (around 10 mg; solubility of Compound (I) in chloroform is 13.1 mg / mL). A stir bar was added, and the saturated slurry was stirred at room temperature for two weeks. The solids were filtered via a 0.22 pm Nylon centrifuge filter tube and dried to afford Mono-Chloroform Solvate Form of Compound (I), which was analyzed via X-ray powder diffraction, DSC, and TGA.Characterization

[0161] Table 1 below provides a list of peaks identified in the diffractogram of MonoChloroform Solvate Form of Compound (I).Attorney Docket No. 15496.0048-00304Table 1 : List of XRPD peaks for Mono-Chloroform Solvate Form of Compound (I)

[0162] FIG. 3 shows the X-ray powder diffractogram of the Mono-Chloroform Solvate Form of Compound (I) obtained through the synthesis procedure above. The X-ray powder diffractogram indicates that the sample is crystalline. A direct overlay of the X-ray powder diffractogram of Mono-Chloroform Solvate Form of Compound (I) with that of Form I of Compound (I), which is depicted in FIG. 4, showed the presence of distinct peaks compared to those of Form I of Compound (I), which confirmed the formation of a solid form other than Form I of Compound (I).

[0163] FIG. 5 shows a differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for Mono-Chloroform Solvate Form of Compound (I). The thermogram depicted in FIG. 5 shows a weight loss of 23.274% that occurred when the Mono-Chloroform Solvate Form of Compound (I) was heated from 25 °CAttorney Docket No. 15496.0048-00304 to 133 °C. An endothermic event with onset of about 124.6 °C was associated with the weight loss, followed by an exothermic event that occurred with onset of about 195.4 °C and a second endothermic event that occurred with onset of about 220 °C. These results suggest that the solid form is a mono-chloroform solvate (theoretical 1 : 1 chloroform solvate is 24.2%), which disassociated at about 55 °C (chloroform has a boiling point of 61 °C), along with the loss of solvent, then recrystallized into Form I of Compound (I), which then melted at about 220 °C (the onset melt of Form I of Compound (I) has been measured at 218 °C).Example 6: Preparations and Characterization of CSA Solid Form of Compound (I) Preparations

[0164] In a first experiment, supersaturated stock suspensions or solutions of Compound (I) were prepared in the following solvent systems: 1 :1 ACN / DCM; ACN / 20% DMSO; 1 : 1 THF / DCM; THF / 12% DMSO; 1 : 1 dioxane / DCM; IPAc / 20% DMSO; 1 : 1 chloroform / DCM; ACE / 20% DMSO; 25% CHCh / DCM; H2O; DCM; and 1 : 1 EtOAc / DCM. To prepare the supersaturated stock suspensions or solutions of Compound (I), scintillation vials were charged with Compound (I) and the respective solvent system, targeting about 50 mg / mL of Compound (I) in each solvent system. The samples were sonicated, vortex-mixed, and / or heated as needed to produce homogenous suspensions or solutions. 200 pL aliquots of each stock suspension or solution of Compound (I) were then charged to separate vials, each of which was then charged with 12 pL of a 2 molar (2 M) solution of (+)-(lS)-camphor-10- sulfonic acid in water (H2O) or DMSO, targeting a 1 : 1 molar ratio of Compound (I):(+)-(l S)- camphor-10-sulfonic acid. The vials were placed into a CrystalBreeder reactor with overhead stir hooks, and the reactor was programmed as follows:• equilibrate at 25 °C;• heat to 55 °C, 5 °C / min, with stirring, hold 10 minutes;• cool to -5 °C, 1 °C / min, no stirring, hold 1 hour;• heat to 40 °C, 5 °C / min, with stirring, hold 10 minutes; and• cool to -5 °C, 0.1 °C / min, no stirring, hold until prompted.

[0165] Upon completion of the program, the solvent was evaporated, and the solids were collected for analysis by X-ray powder diffraction. In some instances, additional characterization though DSC and TGA was performed. The results of the experiments are summarized in Table 2 below. Comments regarding the experiments are provided in the “Notes” column.Attorney Docket No. 15496.0048-00304Table 2: Results of Experiments on Solid Forms of Compound (I) Using CSAAttorney Docket No. 15496.0048-00304

[0166] Experiment 4 of Table 2 led to the formation of solids, for which the XRPD indicated formation of a new solid form. In a second set of experiments, the solvent system of Experiment 4 (chloroform / DCM) was employed.

[0167] In the second set of experiments (Exp. Nos. 13-19), the following procedure was employed except where otherwise indicated in Table 3. Samples were individually prepared. Approximately 50 mg of Compound (I) was weighed into an HPLC vial. The solvent system indicated in Table 3 was added to the vial until a supersaturated slurry was obtained, targeting a concentration of about 25 mg / mL. A vial containing the volume of the supersaturated slurry listed in Table 3 (fourth column) was placed on a ReactiTherm (Thermo Scientific; Catalog No. #TS- 18823) unit in an aluminum block and heated to approximately 40-50 °C if needed to dissolve Compound (I) (otherwise, the vial was kept at room temperature). At either room temperature or, if the vial had been heated, at approximately 40-50 °C, a 1 : 1 molar equivalent of a 2 molar (2 M) CSA stock solution in water was added to the vial. If the vial had been heated, the heat was turned off, and the sample was slowly allowed to reach room temperature. If no solids were present at room temperature, the solvent was evaporated using a nitrogen (N2) stream or, in some instances, placed in a freezer to cool further to promote precipitation. Solids were filtered and analyzed through X-ray powder diffraction and, in some instances, through DSC and TGA. The results of the experiments are summarized in Table 3 below. Comments regarding the experiments are provided in the “Notes” column.Table 3: Results of Experiments on Solid Forms of Compound (I) Using CSAAttorney Docket No. 15496.0048-00304Attorney Docket No. 15496.0048-00304'This experiment was performed in a PolarBear programmable temperature and stirring unit (PolarBear Plus, Cottenham, England, UK; Serial No.: A1914-27) instead of a ReactiTherm unit.

[0168] The solids obtained in Exp. 17 were filtered and dried to afford CSA Solid Form of Compound (I), which was analyzed via X-ray powder diffraction, DSC, TGA, and NMR. Characterization

[0169] FIG. 6 shows the X-ray powder diffractogram of CSA Solid Form of Compound (I).The X-ray powder diffractogram indicates that the sample is crystalline.

[0170] Table 4 below provides a list of peaks identified in the diffractogram of CSA SolidForm of Compound (I).Table 4: List of XRPD peaks for CSA Solid Form of Compound (I)Attorney Docket No. 15496.0048-00304

[0171] As shown in FIG. 7, an overlay of the X-ray powder diffractogram for CSA Solid Form of Compound (I) and that of Form I of Compound (I) indicates the presence of residual Form I of Compound (I) that did not form CSA Solid Form of Compound (I) in the sample. Nonetheless, several unique peaks were identified that could not be associated with any one of Form I of Compound (I), Mono-Chloroform Solvate Form, or CSA. These new peaks are unique to CSA Solid Form of Compound (I).

[0172] FIG. 8 shows a differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for CSA Solid Form of Compound (I). The thermogram depicted in FIG. 8 shows that a weight loss of 1.124% occurred when the CSA Solid Form of Compound (I) was heated from 25 °C to 75 °C. As also shown in the thermogram depicted in FIG. 8, CSA Solid Form of Compound (I) underwent an endothermic event with onset of about 185.9 °C, which occurred in parallel with degradation / decomposition.

[0173] TheXH NMR spectrum of CSA Solid Form of Compound (I) was measured on a Bruker Ascend 400 MHz spectrometer using DMSO-t / 6 to prepare the measurement sample. The1H NMR spectrum measured for CSA Solid Form of Compound (I) is depicted in FIG. 9 and indicated the presence of Compound (I) and CSA in a 1 :0.88 Compound (I):CSA ratio ( / .< ., a 1 :0.9 ratio of Compound (I) to CSA when rounded to one decimal place). A slight excess Form I of Compound (I) was present, which explains the sub-stoichiometric ratio of CSA. There are no signals present that suggested chemical degradation of Compound (I).Attorney Docket No. 15496.0048-00304Proton assignments are labeled above the peaks and correspond to the atom numbering of the structure displayed in the figure. All signals of the1H NMR spectrum of CSA Solid Form are further listed in Table 5 below.Table 5: List ofXH NMR peaks for CSA Solid Form of Compound (I)Footnote 1 : TheXH NMR peaks for the two hydrogen atoms corresponding to position 7 (as labeled in FIG. 9), which appeared in theXH NMR spectrum in the shift range of 4.49-4.60 ppm, and / or the!H NMR peaks for the one hydrogen atom corresponding to position 18 (as labeled in FIG. 9), which appeared in theXH NMR spectrum in the shift range of 4.39-4.47, overlapped with protons from water in the sample, resulting in an integration of a greater number of hydrogen atoms than would have been expected ( / .< ., greater than three hydrogen atoms in total for the two hydrogen atoms corresponding to position 7 and the one hydrogen atom corresponding to position 18).

[0174] There are several factors that confirm the formation of CSA Solid Form of Compound(I) including, but not limited to, unique X-ray powder diffraction peaks, unique thermal profile, unique singular melt, NMR confirming presence of Compound (I) and CSA, and no indication of degradation of Compound (I) or CSA.

[0175] A homonuclear correlation spectroscopy (COSY) NMR experiment was performed on CSA Solid Form of Compound (I) using a Bruker Ascend 400 MHz spectrometer. The measurement sample was the same sample used to acquire the1H NMR spectrum as described above. FIG. 10 shows the results of the COSY NMR experiment performed on CSA Solid Form of Compound (I). Additionally, a heteronuclear single quantum coherence (HSQC) NMR experiment was performed on CSA Solid Form of Compound (I) using a Bruker Ascend 400 MHz spectrometer. The measurement sample was the same sample usedAttorney Docket No. 15496.0048-00304 to acquire the1H NMR spectrum and used in the COSY NMR experiment as described above. FIG. 11 shows the results of the HSQC experiment performed on CSA Solid Form of Compound (I). For comparative purposes, a homonuclear correlation spectroscopy (COSY) NMR experiment was also performed on Form (I) of Compound (I) using a Bruker Ascend 400 MHz spectrometer. FIG. 12 shows the results of the COSY NMR experiment performed on Form (I) of Compound (I). The correlation of chemical shifts in the COSY and HSQC experiments further confirm the identity of CSA Solid Form of Compound (I) as described herein. Further support for the remarks in Footnote 1 to Table 5 regarding protons overlapping with protons from water in the sample can be seen in the presence of a water peak in the COSY and HSQC spectra (FIG. 10 and FIG. 11).Example 7: Preparations and Characterization of Benzamide Solid Form of Compound (I)Preparation #1

[0176] A 2 mL solution of 1 : 1 chloroform: di chloromethane (CHCh:DCM) was prepared and stirred for approximately five minutes to ensure complete homogenization. 51 mg of Form I of Compound (I) was added to the solution, and the combination was stirred for about one minute. 16.61 mg of ground benzamide was added, and the mixture was gradually heated to 50 °C and stirred at that temperature for two days. Subsequently, the mixture was slowly cooled to room temperature, yielding a clear yellow solution. This solution was allowed to evaporate in a laboratory fume hood for three days, resulting in the formation of a crystalline, yellow solid, which was characterized and identified as Benzamide Solid Form of Compound (I). The same Benzamide Solid Form of Compound (I) was also obtained using the alternative preparation described below (Preparation #2).Preparation #2

[0177] A 2 mL solution of 1 : 1 chloroform: di chloromethane (CHCh:DCM) was prepared and stirred for approximately five minutes to ensure homogenization. 25.6 mg of Form I of Compound (I) was added to an empty ball mill vial, followed by 8.63 mg of ground benzamide. Then, 34 pL of the 2 mL solution was added to the ball mill vial. The mixture was ball-milled for 30 minutes, resulting in the formation of an off-white precipitate. The product was immediately analyzed and identified as Benzamide Solid Form of Compound (I), a crystalline solid.Characterization

[0178] Benzamide Solid Form of Compound (I) obtained using Preparation #1 was analyzed via X-ray powder diffraction, DSC, and TGA.Attorney Docket No. 15496.0048-00304

[0179] Table 6 below provides a list of peaks identified in the diffractogram of Benzamide Solid Form of Compound (I).Table 6: List of XRPD peaks for Benzamide Solid Form of Compound (I)Attorney Docket No. 15496.0048-00304

[0180] FIG. 13 shows the X-ray powder diffractogram of Benzamide Solid Form of Compound (I). The X-ray powder diffractogram indicates that the sample is crystalline.

[0181] FIG. 14 depicts a direct overlay of the X-ray powder diffractograms for, from top to bottom, Mono-Chloroform Solvate Form of Compound (I), Form I of Compound (I), benzamide, and Benzamide Solid Form of Compound (I). That direct overlay showed the presence, in the X-ray powder diffractogram for Benzamide Solid Form of Compound (I), of distinct peaks compared to those of Form I of Compound (I), Mono-Chloroform SolvateAttorney Docket No. 15496.0048-00304Form of Compound (I), and benzamide, which confirmed the formation of a solid form other than Form I of Compound (I) and Mono-Chloroform Solvate Form of Compound (I). In the X-ray powder diffractogram for Benzamide Solid Form of Compound (I), some peaks believed to be associated with Mono-Chloroform Solvate Form of Compound (I) remained visible. It is believed those peaks may correspond to a minor amount of Mono-Chloroform Solvate Form of Compound (I) in the sample of Benzamide Solid Form of Compound (I).

[0182] FIG. 15 shows a differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for Benzamide Solid Form of Compound (I). The thermogram depicted in FIG. 15 shows that a weight loss of 14.764% occurred when Benzamide Solid Form of Compound (I) was heated from room temperature to 100 °C and that a weight loss of 13.948% occurred when Benzamide Solid Form of Compound (I) was heated from 100 °C to 180 °C. As also shown in FIG. 15, Benzamide Solid Form of Compound (I) underwent an endothermic event with onset of about 87.1 °C, an endothermic event with onset of about 117.8 °C, and an endothermic event with onset of about 163.5 °C. Those thermal events were not observed for Form I of Compound (I) or Mono-Chloroform Solvate Form of Compound (I).Example 8: Preparations and Characterization of Manganese (II) Chloride Solid Form of Compound (I)Preparation #1

[0183] A 2 mL solution of 1 : 1 dioxane:dichloromethane (Diox:DCM) was prepared and stirred for approximately five minutes to ensure homogenization. 50.6 mg of Form I of Compound (I) was added to the solution, and the combination was stirred for about one minute. 18.48 mg of manganese (II) chloride was added, and the mixture was slowly heated to 50 °C and stirred at that temperature for two days, during which time the mixture developed a milky yellow appearance. Subsequently, the mixture was slowly cooled to room temperature, still appearing as a milky yellow solution. An aliquot of the mixture was filtered and analyzed, while the remaining mixture was left to evaporate in a laboratory fume hood over two days, resulting in a yellow precipitate that was subsequently analyzed and identified as Manganese (II) Chloride Solid Form of Compound (I), a crystalline solid. The same Manganese (II) Chloride Solid Form of Compound (I) was also obtained using the alternative preparation described below (Preparation #2).Attorney Docket No. 15496.0048-00304Preparation #2

[0184] A 2 mL solution of 1 : 1 dioxane:dichloromethane (Diox:DCM) was prepared and stirred for approximately five minutes to ensure homogenization. 25.77 mg of Form I of Compound (I) was added to an empty ball mill vial, followed by 9.00 mg manganese (II) chloride. Subsequently, 34 pL of the 2 mL solvent solution was added to the ball mill vial. The mixture was ball-milled for 30 min, during which time a yellow precipitate was observed. The material was immediately analyzed and identified as Manganese (II) Chloride Solid Form of Compound (I), a crystalline solid.Characterization

[0185] Manganese (II) Chloride Solid Form of Compound (I) obtained using Preparation #1 was analyzed via X-ray powder diffraction, DSC, and TGA.

[0186] Table 7 below provides a list of peaks identified in the diffractogram of Manganese (II) Chloride Solid Form of Compound (I).Table 7: List of XRPD peaks for Manganese (II) Chloride Solid Form of Compound (I)Attorney Docket No. 15496.0048-00304Attorney Docket No. 15496.0048-00304

[0187] FIG. 16 shows the X-ray powder diffractogram of Manganese (II) Chloride Solid Form of Compound (I). The X-ray powder diffractogram indicates that the sample is crystalline.

[0188] FIG. 17 depicts a direct overlay of the X-ray powder diffractograms for, from top to bottom, Manganese (II) Chloride Solid Form of Compound (I), manganese (II) chloride, Mono-Chloroform Solvate Form of Compound (I), and Form I of Compound (I). That direct overlay showed the presence, in the X-ray powder diffractogram for Manganese (II) Chloride Solid Form of Compound (I), of distinct peaks compared to those of Form I of Compound (I), Mono-Chloroform Solvate Form of Compound (I), and manganese (II) chloride, which confirmed the formation of a solid form other than Form I of Compound (I) and MonoChloroform Solvate Form of Compound (I). In the X-ray powder diffractogram for Manganese (II) Chloride Solid Form of Compound (I), some peaks believed to be associated with Form I of Compound (I) remained visible. It is believed those peaks may correspond to a minor amount of Form I of Compound (I) in the sample of Manganese (II) Chloride Solid Form of Compound (I).

[0189] FIG. 18 shows a differential scanning calorimetry (DSC) thermogram and a thermogravimetric analysis (TGA) thermal curve for Manganese (II) Chloride Solid Form of Compound (I). The thermogram depicted in FIG. 18 shows that a weight loss of 4.609% occurred when Manganese (II) Chloride Solid Form was heated from room temperature to 100 °C and that a weight loss of 3.802% occurred when Manganese (II) Chloride Solid Form was heated from 100 °C to 170 °C. As also shown in FIG. 18, Manganese (II) Chloride Solid Form underwent an endothermic event with onset of about 35.7 °C, an endothermic event with onset of about 58.6 °C, an endothermic event with onset of about 66.1 °C, an endothermic event with onset of about 121.7 °C, an endothermic event with onset of about 167.4 °C, an endothermic event with onset of about 207.4 °C, and an endothermic event with onset of about 273.8 °C. It is believed that the endothermic event with onset of about 273.8 °C occurred concurrently with degradation / decomposition of Manganese (II) Chloride Solid Form. Those thermal events were not observed for Form I of Compound (I) or MonoChloroform Solvate Form of Compound (I).

[0190] In general, in the following claims, the terms used should not be construed to limit the claims to the specific embodiments disclosed in the specification and the claims but should be construed to include all possible embodiments along with the full scope of equivalents to which such claims are entitled. Accordingly, the claims are not limited by the disclosure.

Claims

Attorney Docket No. 15496.0048-00304What is claimed is:

1. A solvate comprising Compound (I):and chloroform.

2. The solvate according to claim 1, wherein Compound (I) and chloroform are present in an about 1 : 1 stoichiometric ratio.

3. Mono-Chloroform Solvate Form of Compound (I):

4. The solvate comprising Compound (I) and chloroform according to any one of claims 1-3, characterized by an X-ray powder diffractogram comprising a signal at two or more two- theta values chosen from 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 ± 0.2.

5. The solvate comprising Compound (I) and chloroform according to any one of claims 1-3, characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 ± 0.2.

6. The solvate comprising Compound (I) and chloroform according to any one of claims 1-3, characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 ± 0.2.

7. The solvate comprising Compound (I) and chloroform according to any one of claims 1-3, characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 4.2 ± 0.2, 10.2 ± 0.2, 12.6 ± 0.2, 20.6 ± 0.2, and 25.7 ± 0.2.Attorney Docket No. 15496.0048-003048. The solvate comprising Compound (I) and chloroform according to any one of claims 1-7, characterized by an X-ray powder diffractogram substantially similar to FIG. 3.

9. The solvate comprising Compound (I) and chloroform according to any one of claims 1-8, characterized by a DSC thermogram substantially similar to FIG. 5.

10. The solvate comprising Compound (I) and chloroform according to any one of claims 1-9, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 122 °C to about 128 °C.

11. The solvate comprising Compound (I) and chloroform according to any one of claims 1-10, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 124 °C to about 125 °C.

12. The solvate comprising Compound (I) and chloroform according to any one of claims 1-11, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 124.6 °C.

13. The solvate comprising Compound (I) and chloroform according to any one of claims 1-12, characterized by a DSC thermogram comprising an exothermic event at a temperature of from about 193 °C to about 198 °C.

14. The solvate comprising Compound (I) and chloroform according to any one of claims 1-13, characterized by a DSC thermogram comprising an exothermic event at a temperature of from about 195 °C to about 196 °C.

15. The solvate comprising Compound (I) and chloroform according to any one of claims 1-14, characterized by a DSC thermogram comprising an exothermic event at a temperature of about 195.4 °C.

16. The solvate comprising Compound (I) and chloroform according to any one of claims 1-15, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 218 °C to about 223 °C.Attorney Docket No. 15496.0048-0030417. The solvate comprising Compound (I) and chloroform according to any one of claims 1-16, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 220.4 °C.

18. The solvate comprising Compound (I) and chloroform according to any one of claims 1-17, characterized by a TGA thermogram substantially similar to FIG. 5.

19. The solvate comprising Compound (I) and chloroform according to any one of claims 1-18 characterized by a weight loss of from about 20.0% to about 30.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C.

20. The solvate comprising Compound (I) and chloroform according to any one of claims 1-19, characterized by a weight loss of from about 20.0% to about 25.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C.

21. The solvate comprising Compound (I) and chloroform according to any one of claims 1-20, characterized by a weight loss of from about 23.0% to about 24.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C.

22. The solvate comprising Compound (I) and chloroform according to any one of claims 1-21, characterized by a weight loss of about 23.3% as determined by thermogravimetric analysis when heated from about 25 °C to about 133 °C.

23. A solid form comprising Compound (I):and camphorsulfonic acid.

24. The solid form according to claim 23, wherein Compound (I) and camphorsulfonic acid are present in about a 1 :0.9 stoichiometric ratio.

25. The solid form according to claim 23 or claim 24, wherein the camphorsulfonic acid is (+)-(! S)-camphor-10-sulfonic acid.Attorney Docket No. 15496.0048-0030426. CSA Solid Form of Compound (I):

27. The solid form according to any one of claims 23-26, characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from 5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.

28. The solid form according to any one of claims 23-26, characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from 5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.

29. The solid form according to any one of claims 23-26, characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from 5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.

30. The solid form according to any one of claims 23-26, characterized by an X-ray powder diffractogram comprising a signal at five or more two-theta values chosen from 5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.

31. The solid form according to any one of claims 23-26, characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 5.6 ± 0.2, 11.4 ± 0.2, 13.6 ± 0.2, 18.1 ± 0.2, 22.8 ± 0.2, and 24.3 ± 0.2.

32. The solid form according to any one of claims 23-26, characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values of 5.6 ± 0.2, 13.6 ± 0.2, and 18.1 ± 0.2.Attorney Docket No. 15496.0048-0030433. The solid form according to any one of claims 23-26, characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 5.6 + 0.2, 13.6 + 0.2, and 18.1 + 0.2.

34. The solid form according to any one of claims 23-33, characterized by an X-ray powder diffractogram substantially similar to FIG. 6.

35. The solid form according to any one of claims 23-34, characterized by a DSC thermogram substantially similar to FIG. 8.

36. The solid form according to any one of claims 23-35, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 183 °C to about 188 °C.

37. The solid form according to any one of claims 23-36, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 185.9 °C.

38. The solid form according to any one of claims 23-37, characterized by a TGA thermogram substantially similar to FIG. 8.

39. The solid form according to any one of claims 23-38, characterized by a weight loss of less than about 1.5 wt. % as determined by thermogravimetric analysis when heated from about 25 °C to about 75 °C.

40. The solid form according to any one of claims 23-39, characterized by a weight loss of less than about 1.2 wt. % as determined by thermogravimetric analysis when heated from about 25 °C to about 75 °C.

41. The solid form according to any one of claims 23-40, characterized by a weight loss of about 1.1 wt. % as determined by thermogravimetric analysis when heated from about 25 °C to about 75 °C.Attorney Docket No. 15496.0048-0030442. A solid form comprising Compound (I):and a Lewis base.

43. A solid form comprising Compound (I):and benzamide.

44. The solid form according to claim 43, wherein Compound (I) and benzamide are present in about a 1 : 1 stoichiometric ratio.

45. Benzamide Solid Form of Compound (I):

46. The solid form according to any one of claims 42-45, characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.

47. The solid form according to any one of claims 42-45, characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.Attorney Docket No. 15496.0048-0030448. The solid form according to any one of claims 42-45, characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.

49. The solid form according to any one of claims 42-45, characterized by an X-ray powder diffractogram comprising a signal at five or more two-theta values chosen from 5.4 ± 0.2, 10.6 ± 0.2, 15.3 ± 0.2, 18.2 ± 0.2, 21.1 ± 0.2, and 21.6 ± 0.2.

50. The solid form according to any one of claims 42-45, characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 5.4 + 0.2, 10.6 + 0.2, 15.3 + 0.2, 18.2 + 0.2, 21.1 + 0.2, and 21.6 + 0.2.

51. The solid form according to any one of claims 42-50, characterized by an X-ray powder diffractogram substantially similar to FIG. 13.

52. The solid form according to any one of claims 42-51, characterized by a DSC thermogram substantially similar to FIG. 15.

53. The solid form according to any one of claims 42-52, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 84 °C to about 90 °C.

54. The solid form according to any one of claims 42-53, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 87 °C to about 88 °C.

55. The solid form according to any one of claims 42-54, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 87.1 °C.

56. The solid form according to any one of claims 42-55, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 116 °C to about 120 °C.Attorney Docket No. 15496.0048-0030457. The solid form according to any one of claims 42-56, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 117 °C to about 118 °C.

58. The solid form according to any one of claims 42-57, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 117.8 °C.

59. The solid form according to any one of claims 42-58, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 160 °C to about 166 °C.

60. The solid form according to any one of claims 42-59, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 163 °C to about 164 °C.

61. The solid form according to any one of claims 42-60, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 163.4 °C.

62. The solid form according to any one of claims 42-61, characterized by a TGA thermogram substantially similar to FIG. 15.

63. The solid form according to any one of claims 42-62, characterized by a weight loss of from about 10.0% to about 25.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.

64. The solid form according to any one of claims 42-63, characterized by a weight loss of from about 12.0% to about 18.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.

65. The solid form according to any one of claims 42-64, characterized by a weight loss of from about 14.0% to about 15.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.

66. The solid form according to any one of claims 42-65, characterized by a weight loss of about 14.8% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.Attorney Docket No. 15496.0048-0030467. The solid form according to any one of claims 42-66, characterized by a weight loss of from about 10.0% to about 25.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C.

68. The solid form according to any one of claims 42-67, characterized by a weight loss of from about 11.0% to about 17.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C.

69. The solid form according to any one of claims 42-68, characterized by a weight loss of from about 13.5% to about 14.5% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C.

70. The solid form according to any one of claims 42-69, characterized by a weight loss of about 13.9% as determined by thermogravimetric analysis when heated from about 100 °C to about 180 °C.

71. A solid form comprising Compound (I):and a Lewis acid.

72. A solid form comprising Compound (I):and manganese (II) chloride.

73. The solid form according to claim 72, wherein Compound (I) and manganese (II) chloride are present in about a 1 : 1 stoichiometric ratio.Attorney Docket No. 15496.0048-0030474. Manganese (II) Chloride Solid Form of Compound (I):

75. The solid form according to any one of claims 71-74, characterized by an X-ray powder diffractogram comprising a signal at two or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.

76. The solid form according to any one of claims 71-74, characterized by an X-ray powder diffractogram comprising a signal at three or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.

77. The solid form according to any one of claims 71-74, characterized by an X-ray powder diffractogram comprising a signal at four or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.

78. The solid form according to any one of claims 71-74, characterized by an X-ray powder diffractogram comprising a signal at five or more two-theta values chosen from 16.0 ± 0.2, 17.9 ± 0.2, 18.5 ± 0.2, 27.6 ± 0.2, 32.4 ± 0.2, and 34.5 ± 0.2.

79. The solid form according to any one of claims 71-74, characterized by an X-ray powder diffractogram comprising a signal at two-theta values of 16.0 + 0.2, 17.9 + 0.2, 18.5 + 0.2, 27.6 + 0.2, 32.4 + 0.2, and 34.5 + 0.2.

80. The solid form according to any one of claims 71-79, characterized by an X-ray powder diffractogram substantially similar to FIG. 16.

81. The solid form according to any one of claims 71-80, characterized by a DSC thermogram substantially similar to FIG. 18.Attorney Docket No. 15496.0048-0030482. The solid form according to any one of claims 71-81, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 33 °C to about 38 °C.

83. The solid form according to any one of claims 71-82, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 35 °C to about 36 °C.

84. The solid form according to any one of claims 71-83, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 35.7 °C.

85. The solid form according to any one of claims 71-84, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 56 °C to about 61 °C.

86. The solid form according to any one of claims 71-85, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 58 °C to about 59 °C.

87. The solid form according to any one of claims 71-86, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 58.6 °C.

88. The solid form according to any one of claims 71-87, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 63 °C to about 69 °C.

89. The solid form according to any one of claims 71-88, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 66 °C to about 67 °C.

90. The solid form according to any one of claims 71-89, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 66.1 °C.Attorney Docket No. 15496.0048-0030491. The solid form according to any one of claims 71-90, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 119 °C to about 124 °C.

92. The solid form according to any one of claims 71-91, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 121 °C to about 122 °C.

93. The solid form according to any one of claims 71-92, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 121.7 °C.

94. The solid form according to any one of claims 71-93, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 164 °C to about 171 °C.

95. The solid form according to any one of claims 71-94, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 167 °C to about 168 °C.

96. The solid form according to any one of claims 71-95, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 167.4 °C.

97. The solid form according to any one of claims 71-96, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 205 °C to about 209 °C.

98. The solid form according to any one of claims 71-97, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 207 °C to about 208 °C.

99. The solid form according to any one of claims 71-98, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 207.4 °C.Attorney Docket No. 15496.0048-00304100. The solid form according to any one of claims 71-99, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 271 °C to about 276 °C.

101. The solid form according to any one of claims 71-100, characterized by a DSC thermogram comprising an endothermic event at a temperature of from about 273 °C to about 274 °C.

102. The solid form according to any one of claims 71-101, characterized by a DSC thermogram comprising an endothermic event at a temperature of about 273.8 °C.

103. The solid form according to any one of claims 71-102, characterized by a TGA thermogram substantially similar to FIG. 18.

104. The solid form according to any one of claims 71-103, characterized by a weight loss of from about 1.0% to about 8.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.

105. The solid form according to any one of claims 71-104, characterized by a weight loss of from about 2.0% to about 6.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.

106. The solid form according to any one of claims 71-105, characterized by a weight loss of from about 3.0% to about 5.0% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.

107. The solid form according to any one of claims 71-106, characterized by a weight loss of about 4.6% as determined by thermogravimetric analysis when heated from about 25 °C to about 100 °C.

108. The solid form according to any one of claims 71-107, characterized by a weight loss of from about 1.0% to about 7.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C.Attorney Docket No. 15496.0048-00304109. The solid form according to any one of claims 71-108, characterized by a weight loss of from about 2.0% to about 6.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C.

110. The solid form according to any one of claims 71-109, characterized by a weight loss of from about 3.0% to about 4.0% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C.

111. The solid form according to any one of claims 71-110, characterized by a weight loss of about 3.8% as determined by thermogravimetric analysis when heated from about 100 °C to about 170 °C.

112. A pharmaceutical composition comprising: at least one solid form of Compound (I) according to any one of claims 1-111; and at least one pharmaceutically acceptable excipient.

113. A method for the prophylaxis or treatment of depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder in a subject in need thereof, comprising administering a therapeutically effective amount of at least one solid form of Compound (I) according to any one of claims 1-111 or a pharmaceutical composition according to claim112 to the subject.

114. The method of claim 113, wherein the depression is major depressive disorder.

115. The method of claim 113, wherein the depression is treatment-resistant depression.

116. The solid form of Compound (I) according to any one of claims 1-111 or the pharmaceutical composition according to claim 112 for use in prevention or treatment of depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder.

117. The solid form for use of claim 116, wherein the depression is major depressive disorder.Attorney Docket No. 15496.0048-00304118. The solid form for use of claim 116, wherein the depression is treatment-resistant depression.

119. Use of a solid form of Compound (I) according to any one of claims 1-111 or the pharmaceutical composition according to claim 112 for the manufacture of a medicament for preventing or treating depression, schizophrenia, Alzheimer’s disease, or attention deficit hyperactivity disorder.

120. The use of claim 119, wherein the depression is major depressive disorder.

121. The use of claim 119, wherein the depression is treatment-resistant depression.

122. A process for preparing the solvate according to any one of claims 1-22, comprising:(a) combining Compound (I) with chloroform to provide a composition comprising Compound (I); and(b) stirring the composition at room temperature.

123. The process according to claim 122, further comprising:(c) filtering the composition to isolate the solvate.

124. The process according to claim 122 or claim 123, wherein (b) comprises stirring the composition for two weeks.

125. A process for preparing the solid form according to any one of claims 23-41, comprising:(a) combining Compound (I) with one or more solvents to provide a first composition comprising Compound (I);(b) adding an aqueous solution of camphorsulfonic acid to the first composition to provide a second composition; and(c) stirring the second composition at room temperature.

126. The process according to claim 125, further comprising:(d) filtering the second composition to isolate the solid form.Attorney Docket No. 15496.0048-00304127. The process according to claim 125 or claim 126, wherein (a) comprises combining Compound (I) with chloroform and dichloromethane.

128. The process according to claim 127, wherein (a) comprises combining Compound (I) with a 1 : 1 ratio of chloroform and dichloromethane.

129. The process according to any one of claims 125-128, wherein (b) comprises adding an equimolar amount of camphorsulfonic acid to the amount of Compound (I) combined with the one or more solvents in (a).

130. The process according to any one of claims 125-129, wherein the concentration of the aqueous solution of camphorsulfonic acid in (b) is 2 molar (2 M).

131. The process according to any one of claims 125-130, wherein (c) comprises stirring the second composition for three days.

132. A process for preparing the solid form according to any one of claims 42-70, comprising:(a) combining Compound (I) with one or more solvents to provide a composition;(b) adding benzamide to the composition;(c) heating the composition;(d) stirring the composition; and(e) cooling the composition to room temperature.

133. The process according to claim 132, further comprising:(f) evaporating the solvent from the composition to provide the solid form.

134. The process according to claim 132 or claim 133, wherein (a) comprises combining Compound (I) with a mixture of chloroform and dichloromethane.

135. The process according to any one of claims 132-134, wherein (b) comprises adding an amount of benzamide that is equimolar to the amount of Compound (I) to the composition.Attorney Docket No. 15496.0048-00304136. The process according to any one of claims 132-135, wherein (c) comprises heating the composition to 50 °C.

137. The process according to any one of claims 132-136, wherein (d) comprises stirring the composition for two days.

138. A process for preparing the solid form according to any one of claims 42-70, comprising:(a) providing a first composition comprising one or more solvents;(b) adding Compound (I) to a ball mill vial;(c) adding benzamide to the ball mill vial;(d) adding at least a portion of the first composition to the ball mill vial to form a reaction mixture; and(e) ball milling the reaction mixture in the ball mill vial.

139. The process according to claim 138, further comprising:(f) isolating the solid form from the ball mill vial.

140. The process according to claim 138 or claim 139, wherein (a) comprises providing a first composition comprising chloroform and dichloromethane.

141. The process according to any one of claims 138-140, wherein (c) comprises adding an amount of benzamide that is equimolar to the amount of Compound (I) to the ball mill vial.

142. The process according to any one of claims 138-141, wherein (e) comprises ball milling the reaction mixture for 30 minutes.

143. A process for preparing the solid form according to any one of claims 71-111, comprising:(a) combining Compound (I) with one or more solvents to provide a composition;(b) adding manganese (II) chloride to the composition;(c) heating the composition;(d) stirring the composition; and(e) cooling the composition to room temperature.Attorney Docket No. 15496.0048-00304144. The process according to claim 143, further comprising:(f) evaporating the solvent from the composition to provide the solid form.

145. The process according to claim 143 or claim 144, wherein (a) comprises combining Compound (I) with a mixture of dioxane and dichloromethane.

146. The process according to any one of claims 143-145, wherein (b) comprises adding an amount of manganese (II) chloride that is equimolar to the amount of Compound (I) to the composition.

147. The process according to any one of claims 143-146, wherein (c) comprises heating the composition to 50 °C.

148. The process according to any one of claims 143-147, wherein (d) comprises stirring the composition for two days.

149. A process for preparing the solid form according to any one of claims 71-111, comprising:(a) providing a first composition comprising one or more solvents;(b) adding Compound (I) to a ball mill vial;(c) adding manganese (II) chloride to the ball mill vial;(d) adding at least a portion of the first composition to the ball mill vial to form a reaction mixture; and(e) ball milling the reaction mixture in the ball mill vial.

150. The process according to claim 149, further comprising:(f) isolating the solid form from the ball mill vial.

151. The process according to claim 149 or claim 150, wherein (a) comprises providing a first composition comprising dioxane and dichloromethane.Attorney Docket No. 15496.0048-00304152. The process according to any one of claims 149-151, wherein (c) comprises adding an amount of manganese (II) chloride that is equimolar to the amount of Compound (I) to the ball mill vial.

153. The process according to any one of claims 149-152, wherein (e) comprises ball milling the reaction mixture for 30 minutes.

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