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WO2024216042A1 - Compositions pharmaceutiques comprenant de la (r)-1-(5-méthoxy-1h-indol-1-yl)-n,n-diméthylpropan-2-amine ou un sel pharmaceutiquement acceptable de celle-ci - Google Patents

Compositions pharmaceutiques comprenant de la (r)-1-(5-méthoxy-1h-indol-1-yl)-n,n-diméthylpropan-2-amine ou un sel pharmaceutiquement acceptable de celle-ci Download PDF

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Publication number
WO2024216042A1
WO2024216042A1 PCT/US2024/024287 US2024024287W WO2024216042A1 WO 2024216042 A1 WO2024216042 A1 WO 2024216042A1 US 2024024287 W US2024024287 W US 2024024287W WO 2024216042 A1 WO2024216042 A1 WO 2024216042A1
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WO
WIPO (PCT)
Prior art keywords
dimethylpropan
indol
methoxy
amine
pharmaceutical composition
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
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PCT/US2024/024287
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English (en)
Inventor
Samuel CLARK
Gary Goodson
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Terran Biosciences Inc
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Terran Biosciences Inc
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Publication of WO2024216042A1 publication Critical patent/WO2024216042A1/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Definitions

  • the present disclosure relates to pharmaceutical compositions comprising (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or pharmaceutically acceptable salts thereof.
  • pharmaceutical compositions comprising (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or pharmaceutically acceptable salts thereof, and excipients, for the treatment of diseases and disorders.
  • the present disclosure addresses the need.
  • the present disclosure provides a pharmaceutical composition
  • a pharmaceutical composition comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or a pharmaceutically acceptable salt thereof, and an excipient.
  • the present disclosure relates to a pharmaceutical composition
  • a pharmaceutical composition comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate salt (e.g., amorphous (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, a crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, such as (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A, (R)- 1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B, (R)-1-(5- methoxy
  • the present disclosure provides a pharmaceutical composition for use in treating or preventing a disease or disorder disclosed herein.
  • the present disclosure provides a pharmaceutical composition for use in treating a disease or disorder disclosed herein.
  • the present disclosure provides use of a pharmaceutical composition in the manufacture of a medicament for treating or preventing a disease or disorder disclosed herein.
  • the present disclosure provides use of a pharmaceutical composition in the manufacture of a medicament for treating a disease or disorder disclosed herein. [0009] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs.
  • FIG. 1 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A.
  • FIG. 2 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A.
  • FIG. 2 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A.
  • FIG. 3 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form A (wet pellet).
  • FIG. 4 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form A. Cooley Docket No.: STBI-081/001WO [0015] FIG.
  • FIG. 5 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form A prepared as outlined in Example 1.
  • FIG. 6 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form A prepared as outlined in Example 1.
  • FIG. 6 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form A prepared as outlined in Example 1.
  • FIG. 7 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form B (wet pellet).
  • FIG. 8 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form B.
  • FIG. 8 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form B.
  • FIG. 9 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I prepared as outlined in Example 2.
  • FIG. 10 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I (wet pellet).
  • FIG. 10 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I (wet pellet).
  • FIG. 11 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II prepared as outlined in Example 2.
  • FIG. 12 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a (wet pellet).
  • FIG. 12 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a (wet pellet).
  • FIG. 13 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a (wet pellet).
  • FIG. 14 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5, isolated from MIBK overlaid with a XRPD diffractogram for the amorphous fumarate salt.
  • FIG. 14 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5, isolated from MIBK overlaid with a XRPD diffractogram for the amorphous fumarate salt.
  • FIG. 15 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 6 (wet pellet).
  • FIG. 16 illustrates a UV Spectrum of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine.
  • FIG. 17 illustrates (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Injector Linearity.
  • FIG. 16 illustrates a UV Spectrum of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine.
  • FIG. 17 illustrates (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine In
  • FIG. 18 illustrates a 2 ⁇ L (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine Injection, Full Scale.
  • FIG. 19 illustrates a 2 ⁇ L (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine Injection, Expanded Scale.
  • FIG. 20 illustrates an Example T30 day API Chromatogram.
  • the present disclosure relates to pharmaceutical compositions comprising (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine having the following chemical structure: [0032] The present disclosure relates to a pharmaceutical composition comprising (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or a pharmaceutically acceptable salt thereof, and an excipient.
  • the pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine. [0034] In some embodiments, the pharmaceutical composition of the present disclosure comprises a pharmaceutically acceptable salt of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine.
  • the pharmaceutically acceptable salt of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine is (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate salt, also known as (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate, and having the structural formula: .
  • the pharmaceutical composition of the present disclosure comprises a (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine racemate, or a pharmaceutically acceptable salt thereof.
  • the pharmaceutical composition of the present disclosure comprises a pharmaceutically acceptable salt of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine.
  • the pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate salt.
  • the pharmaceutical composition of the present disclosure comprises amorphous (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, a crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, such as (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I, (R)-1-(5-methoxy-1H-indol-1-y
  • the pharmaceutical composition of the present disclosure comprises a crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, such as (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II, (R)-1-(5-methoxy-1H-indol
  • the pharmaceutical composition of the present disclosure comprises pure (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A (i.e., Form A not in mixture with one or more of Form B, Form I, Form II, Pattern 3a, Pattern 5, and Pattern 6).
  • the pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A, wherein the (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine fumarate monoForm A is mixed with Form B, Form I, Form II, Pattern 3a, Pattern 5, and Pattern 6.
  • the amount of one or more of Form B, Form I, Form II, Pattern 3a, Pattern 5, and Pattern 6 as present in the mixture with the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Cooley Docket No.: STBI-081/001WO monofumarate Form A is less than 50%, less than 40%, less than 30%, less than 20%, less than 15%, less than 10%, less than 9%, less than 8%, less than 7%, less than 6%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than 0.2%, or less than 0.1%, wt/wt, individually or in aggregate.
  • the pharmaceutical composition comprises one or more excipients selected from the group consisting of a filler, a binder, a glidant, a lubricant, a disintegrant, and a plasticizer.
  • the filler is selected from the group consisting of lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, silicified microcrystalline cellulose, and maltose, and a combination thereof.
  • the binder is selected from the group consisting of povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, ethyl cellulose, and PEO 1NF, and a combination thereof.
  • the glidant is selected from the group consisting of talc and colloidal silicon dioxide, and a combination thereof.
  • the lubricant is selected from the group consisting of magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, and PEO 1NF, and a combination thereof.
  • the disintegrant is selected from the group consisting of sodium starch glycolate, croscarmellose sodium, polyplasdone, and L-HPC, and a combination thereof.
  • the plasticizer comprises polyethylene glycol.
  • the pharmaceutical composition may further comprise a film coating.
  • the film coating comprises Opadry.
  • the pharmaceutical composition may further comprise a release controlling polymer.
  • the release controlling polymer is selected from the group consisting of hypromellose, ethyl cellulose, and methacrylic acid copolymer, and a combination thereof.
  • the pharmaceutical composition may further comprise a capsule shell. Cooley Docket No.: STBI-081/001WO [0055]
  • the capsule shell is selected from the group consisting of HPMC capsule shell and gelatin capsule shell.
  • the pharmaceutical composition of the present disclosure optionally comprises a capsule shell selected from the group consisting of HPMC capsule shell and gelatin capsule shell and one or more excipients, wherein the excipient is selected from the group consisting of lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, talc, colloidal silicon dioxide, magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, sodium starch glycolate, croscarmellose sodium, polyplasdone, L-HPC, Opadry, ethyl cellulose, silicified microcrystalline cellulose, maltose, polyethylene glycol, PEO 1NF, and methacrylic acid cop
  • the excipient is not Neusilin UFL2, sodium carboxy methyl cellulose, polyplasdone, or Opadry.
  • the pharmaceutical composition of the present disclosure optionally comprises a capsule shell comprising an HPMC capsule shell and one or more excipients, wherein the excipient is selected from the group consisting of lactose monohydrate, maize starch, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, povidone, hydroxypropyl cellulose, hypromellose, dextrates, alginic acid, talc, colloidal silicon dioxide, magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, sodium starch glycolate, croscarmellose sodium, L-HPC, ethyl cellulose, silicified microcrystalline cellulose, maltose, polyethylene glycol, PEO 1NF,
  • the one or more excipients comprise lactose monohydrate. [0060] In some embodiments, the one or more excipients comprise maize starch. [0061] In some embodiments, the one or more excipients comprise microcrystalline cellulose. [0062] In some embodiments, the one or more excipients comprise dicalcium phosphate. [0063] In some embodiments, the one or more excipients comprise mannitol. [0064] In some embodiments, the one or more excipients comprise PROSOLV® EASYtab Nutra CM. [0065] In some embodiments, the one or more excipients comprise isomalt.
  • the one or more excipients comprise povidone. Cooley Docket No.: STBI-081/001WO [0067] In some embodiments, the one or more excipients comprise hydroxypropyl cellulose. [0068] In some embodiments, the one or more excipients comprise hypromellose. [0069] In some embodiments, the one or more excipients comprise dextrates. [0070] In some embodiments, the one or more excipients comprise alginic acid. [0071] In some embodiments, the one or more excipients comprise talc. [0072] In some embodiments, the one or more excipients comprise colloidal silicon dioxide.
  • the one or more excipients comprise magnesium stearate.
  • the one or more excipients comprise sodium stearyl fumarate.
  • the one or more excipients comprise hydrogenated vegetable oil.
  • the one or more excipients comprise stearic acid.
  • the one or more excipients comprise sodium starch glycolate.
  • the one or more excipients comprise croscarmellose sodium.
  • the one or more excipients comprise L-HPC.
  • the one or more excipients comprise ethyl cellulose.
  • the one or more excipients comprise silicified microcrystalline cellulose.
  • the present disclosure relates to a pharmaceutical composition comprising (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or a pharmaceutically acceptable salt thereof, and a one or more excipients, wherein the one or more excipients comprise maltose.
  • the one or more excipients comprise polyethylene glycol.
  • the one or more excipients comprise PEO 1NF.
  • the one or more excipients comprise methacrylic acid copolymer.
  • the pharmaceutical composition is stable (e.g., no or little impurity from (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof) under various storage conditions (e.g., at an elevated temperature and/or elevated humidity).
  • the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 95% pure when measured by high pressure liquid chromatography (HPLC).
  • the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable Cooley Docket No.: STBI-081/001WO salt thereof is at least 96% pure when measured by high pressure liquid chromatography (HPLC).
  • the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 97% pure when measured by high pressure liquid chromatography (HPLC).
  • the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 98% pure when measured by high pressure liquid chromatography (HPLC).
  • the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 99% pure when measured by high pressure liquid chromatography (HPLC).
  • the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 95% pure when measured by high pressure liquid chromatography (HPLC).
  • the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 96% pure when measured by high pressure liquid chromatography (HPLC).
  • the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 97% pure when measured by high pressure liquid chromatography (HPLC).
  • the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 98% pure when measured by high pressure liquid chromatography (HPLC).
  • the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 99% pure when measured by high pressure liquid chromatography (HPLC).
  • compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A.
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- Cooley Docket No.: STBI-081/001WO amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-y
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-di
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- Cooley Docket No.: STBI-081/001WO amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG ⁇ IURP ⁇ WKH ⁇ JURXS ⁇ FRQVLVWLQJ ⁇ RI ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ ⁇ DQG ⁇ or ⁇ 0.0 °2 ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ ⁇ ⁇ DQG ⁇ RU ⁇ ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0114]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW ⁇ Cooley Docket No.: STBI-081/001WO ⁇ ⁇ ⁇ ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, or nineteen XRPD peaks selected from those set forth in Table A, as PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ.
  • Table A A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A as shown in FIG.1, as measured ZLWK ⁇ &X ⁇ . ⁇ UDGLDtion. Net Gross Rel.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A.
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 14.0 ⁇ 15.9 ⁇ and 22.3 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG ⁇ IURP ⁇ WKH ⁇ JURXS ⁇ FRQVLVWLQJ ⁇ RI ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG ⁇ IURP ⁇ WKH ⁇ JURXS ⁇ FRQVLVWLQJ ⁇ RI ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 13.4 ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0123]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG ⁇ IURP ⁇ WKH ⁇ JURXS ⁇ FRQVLVWLQJ ⁇ RI ⁇ Cooley Docket No.: STBI-081/001WO ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0131]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ 1 radiation).
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG ⁇ IURP ⁇ WKH ⁇ JURXS ⁇ FRQVLVWLQJ ⁇ RI ⁇ ⁇ 21.3 ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, or eighteen XRPD peaks selected from those set forth in Table B, as measured ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ.
  • Table B A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A as shown in FIG.2, as measured ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ. Signal 2- ⁇ (°) d Value Net Gross Rel.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A.
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 19.3 ⁇ 19.6 ⁇ and 22.6 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- Cooley Docket No.: STBI-081/001WO amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 18.5 ⁇ 19.3 ⁇ 19.6 ⁇ 21.6 ⁇ and 22.6 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, where
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 18.5 ⁇ 19.3 ⁇ 19.6 ⁇ 21.6 ⁇ 21.7 ⁇ 22.6 ⁇ and 25.2 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 18.5 ⁇ 19.3 ⁇ 19.6 ⁇ 21.6 ⁇ 21.7 ⁇ 22.6 ⁇ and 25.2 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0142]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Cooley Docket No.: STBI-081/001WO polymorph Form A, wherein the (R)-1-(
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 18.5 ⁇ 19.3 ⁇ 19.6 ⁇ 21.6 ⁇ 21.7 ⁇ 22.6 ⁇ 23.6 ⁇ and 25.2 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0143]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ⁇ ⁇ DQG ⁇ ( ⁇ 0.2 ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ SKDUPDFHXWLFDO ⁇ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0151]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ⁇ ⁇ DQG ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0152]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the grouS ⁇ FRQVLVWLQJ ⁇ RI ⁇ ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A.
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ⁇ DQG ⁇ ( ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Cooley Docket No.: STBI-081/001WO polymorph Form A is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0163]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofum
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0165]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG ⁇ IURP ⁇ WKH ⁇ JURXS ⁇ FRQVLVWLQJ ⁇ RI ⁇ ⁇ DQG ⁇ ⁇ or ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ WKH ⁇ FRPSRXQG ⁇ PRQRIXPDUDWH ⁇ VDOW ⁇ LV ⁇ crystalline polymorphic Form A is crystalline and is characterized by XRPD peaks at 15.9 ⁇ ⁇ DQG ⁇
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical Cooley Docket No.: STBI-081/001WO composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0173]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- Cooley Docket No.: STBI-081/001WO amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ ⁇ DQG ⁇ RU ⁇ ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0174]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0175]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Cooley Docket No.: STBI-081/001WO polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, or eighteen XRPD peaks selected from those set forth in Table D, as measured ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Table D: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Cooley Docket
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A.
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 22.5 ⁇ 16.0 ⁇ DQG ⁇ 14.1 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ⁇ 16.0 ⁇ DQG ⁇ 14.1 ⁇ , and 13.5 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ⁇ 16.0 ⁇ 14.1 ⁇ , 13.5 ⁇ , and 19.5 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ Vome embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ⁇ 16.0 ⁇ 14.1 ⁇ , 13.5 ⁇ , 19.5 ⁇ , 21.7 ⁇ , and 21.4 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ⁇ 16.0 ⁇ 14.1 ⁇ , 13.5 ⁇ , 19.5 ⁇ , 21.7 ⁇ , and 21.4 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0184]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ⁇ 16.0 ⁇ 14.1 Cooley Docket No.: STBI-081/001WO ⁇ , 13.5 ⁇ , 19.5 ⁇ , 21.7 ⁇ , 21.4 ⁇ , 21.0 ⁇ , 19.1 ⁇ , 15.7 ⁇ , and 18.5 ⁇ ( ⁇ 0.2 ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ SKDUPDFHXWLFDO ⁇ composition of the present disclosure
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ⁇ 16.0 ⁇ 14.1 ⁇ , 13.5 ⁇ , 19.5 ⁇ , 21.7 ⁇ , 21.4 ⁇ , 21.0 ⁇ , 19.1 ⁇ , 15.7 ⁇ , 18.5 ⁇ , 10.2 ⁇ , 28.2 ⁇ , 29.2 ⁇ , 23.3 ⁇ , 25.2 ⁇ , and 24.5 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0194]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-in
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and is non-hygroscopic.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and is solvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and is unsolvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and is anhydrous.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate.
  • compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form B [0201]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 17.8 ⁇ 19.5 ⁇ and 20.3 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at 17.8 ⁇ 19.5 ⁇ and 20.3 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Cooley Docket No.: STBI-081/001WO polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17.8 ⁇ 19.5 ⁇ 20.3 ⁇ and 23.6 ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Cooley Docket No.: STBI-081/001WO polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 9.5 ⁇ 15.1 ⁇ 16.8 ⁇ 17.8 ⁇ 19.5 ⁇ 20.3 ⁇ and 23.6 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at 9.5 ⁇ 15.1 ⁇ 16.8 ⁇ 17.8 ⁇ 19.5 ⁇ 20.3 ⁇ and 23.6 ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0207]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ⁇ DQG ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at ⁇ DQG ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17 ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG ⁇ IURP ⁇ WKH ⁇ JURXS ⁇ FRQVLVWLQJ ⁇ RI ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Cooley Docket No.: STBI-081/001WO [0215]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofum
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW ⁇ 23.5 ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0217]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG ⁇ IURP ⁇ WKH ⁇ JURXS ⁇ FRQVLVWLQJ ⁇ RI ⁇ ⁇ 28.3 ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ Cooley Docket No.: STBI-081/001WO pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethyl
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG ⁇ IURP ⁇ WKH ⁇ JURXS ⁇ FRQVLVWLQJ ⁇ RI ⁇ ⁇ ⁇ ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5- methoxy-1H
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and is non-hygroscopic. Cooley Docket No.: STBI-081/001WO [0226] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and is solvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and is unsolvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and is anhydrous.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate.
  • compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine Hemi-fumarate Form I [0230]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 15.9 ⁇ 19.4 ⁇ and 21.0 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.9 ⁇ 19.4 ⁇ and 21.0 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.9 ⁇ 19.4 ⁇ 21.0 ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-ind
  • composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.2 ⁇ ⁇ 19.4 ⁇ ⁇ 22.5 ⁇ DQG 27.1 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.2 ⁇ 15.9 ⁇ 18.9 ⁇ 19.4 ⁇ 21.0 ⁇ 22.5 ⁇ and 27.1 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.2 ⁇ 15.9 ⁇ 18.9 ⁇ 19.4 ⁇ 21.0 ⁇ 22.5 ⁇ and 27.1 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0235]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.4 ⁇ 16.0 ⁇ 19.2 ⁇ 19.5 ⁇ 21.2 ⁇ 22.6 ⁇ and 27.2 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.4 ⁇ 16.0 ⁇ 19.2 ⁇ 19.5 ⁇ 21.2 ⁇ 22.6 ⁇ and 27.2 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0248]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 13.7 ⁇ 15.4 ⁇ 16.0 ⁇ 19.2 ⁇ 19.5 ⁇ 21.2 ⁇ 22.6 ⁇ and 27.2 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0249]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-ind
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi- fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized Cooley Docket No.: STBI-081/001WO by XRPD peaks at 13.7 ⁇ 15.4 ⁇ 16.0 ⁇ 19.2 ⁇ 19.5 ⁇ 21.2 ⁇ 22.6 ⁇ 27.2 ⁇ and 30.4 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and is non-hygroscopic.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and is solvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and is unsolvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and is anhydrous.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate.
  • compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate Form II [0263]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at ⁇ DQG ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.8 ⁇ 19.2 ⁇ 20.9 ⁇ and 26.9 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.1 ⁇ 15.8 ⁇ 18.8 ⁇ 19.2 ⁇ 20.9 ⁇ 22.4 ⁇ and 26.9 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 15.1 ⁇ 15.8 ⁇ 18.8 ⁇ 19.2 ⁇ 20.9 ⁇ 22.4 ⁇ and 26.9 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ).
  • composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 13.3 ⁇ 13.5 ⁇ 15.1 ⁇ 15.8 ⁇ 18.8 ⁇ 19.2 ⁇ 20.9 ⁇ 21.4 ⁇ 22.4 ⁇ 23.1 ⁇ 24.7 ⁇ 26.9 ⁇ 28.2 ⁇ and 30.2 ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0276]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks Cooley Docket No.: STBI-081/001WO at 11.5 ⁇ 13.3 ⁇ 13.5 ⁇ 15.1 ⁇ 15.8 ⁇ 18.8 ⁇ 19.2 ⁇ 20.9 ⁇ 21.4 ⁇ 22.4 ⁇ 23.1 ⁇ 24.0 ⁇ 24.7 ⁇ 26.9 ⁇ 28.2 ⁇ and 30.2 ⁇ RU ⁇ ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0278]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H
  • Table I A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form II as shown in FIG. 11, as PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Gross Rel.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and is non-hygroscopic.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and is solvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and is unsolvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and is anhydrous.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate.
  • compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a [0285]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- Cooley Docket No.: STBI-081/001WO amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at ⁇ DQG ⁇ RU ⁇ ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17.9 ⁇ ⁇ ⁇ and 23.9 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5- methoxy-1H-indol-1-
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 16.9 ⁇ 17.9 ⁇ 19.7 ⁇ 20.5 ⁇ 23.9 ⁇ 24.9 ⁇ and 25.2 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 16.9 °2 ⁇ 17.9 ⁇ 19.7 ⁇ 20.5 ⁇ 23.9 ⁇ 24.9 ⁇ and 25.2 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0291]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 13.9 ⁇ 16.9 ⁇ 17.9 ⁇ 19.7 ⁇ 20.5 ⁇ 23.9 ⁇ 24.9 ⁇ and 25.2 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0292]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Cooley Docket No.: STBI-081/001WO polymorph Pattern 3a, wherein the (R)-1-
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 18.1 ⁇ 19.8 ⁇ and 19.9 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 18.1 ⁇ 19.8 ⁇ and 19.9 ⁇ ⁇ RU ⁇ ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- Cooley Docket No.: STBI-081/001WO amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5- methoxy
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- Cooley Docket No.: STBI-081/001WO amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17.6 ⁇ 18.1 ⁇ 19.0 ⁇ 19.8 ⁇ 19.9 ⁇ 23.6 ⁇ and 24.0 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 17.6 ⁇ 18.1 ⁇ 19.0 ⁇ 19.8 ⁇ 19.9 ⁇ 23.6 ⁇ and 24.0 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0304]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 16.8 ⁇ 17.6 ⁇ 18.1 ⁇ 19.0 ⁇ 19.8 ⁇ 19.9 ⁇ 23.6 ⁇ and 24.0 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLon).
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 14.1 ⁇ 16.8 ⁇ 17.6 ⁇ 18.1 ⁇ 19.0 ⁇ 19.8 ⁇ 19.9 ⁇ 23.6 ⁇ and 24.0 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ SKDUPDFHXWLFDO ⁇ FRPSRVLWLRQ ⁇ RI ⁇ WKH ⁇ SUHVHQW ⁇ disclosure comprises (R)-1-(5-methoxy-1H-indol
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeen XRPD peaks selected from those set forth in Table K ⁇ DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ radiation.
  • Table K A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a as shown in FIG. 13, as measured ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Cooley Docket No.: STBI-081/001WO Gross Rel.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and is non-hygroscopic.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and is solvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and is unsolvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and is anhydrous.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate.
  • compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 5 [0320]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 5 is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 7.9 ⁇ 20.2 ⁇ and 21.6 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5 is crystalline and is characterized by XRPD peaks at 7.9 ⁇ 20.2 ⁇ and 21.6 ⁇ ⁇ RU ⁇ ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 5 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylprop
  • Table L A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 5 as shown in FIG. 14, as measured ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Gross Rel.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- Cooley Docket No.: STBI-081/001WO amine fumarate polymorph Pattern 5 is crystalline and is characterized by two or more or three or more XRPD
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and is non-hygroscopic.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and is solvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and is unsolvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and is anhydrous.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate.
  • compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6 [0331]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6.
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting ⁇ DQG ⁇ ( ⁇ 0.2 ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at ⁇ DQG ⁇ RU ⁇ ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Cooley Docket No.: STBI-081/001WO polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ⁇ , and ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ ,Q ⁇ VRPH ⁇ HPERGLPHQWV ⁇ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5- methoxy-1H-indol
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Cooley Docket No.: STBI-081/001WO polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ⁇ 18.4 ⁇ 19.3 ⁇ 20.2 ⁇ 21.7 ⁇ 23.2 ⁇ and 23.8 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ⁇ 19.3 ⁇ 20.2 ⁇ 21.7 ⁇ 23.2 ⁇ and 23.8 ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0337]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6,
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ⁇ 12.3 ⁇ 18.4 ⁇ 19.3 ⁇ , 20.2 ⁇ 21.7 ⁇ 23.2 ⁇ and 23.8 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0338]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N,N
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ⁇ 12.3 ⁇ 13.4 ⁇ 13.9 ⁇ 14.9 ⁇ 16.7 ⁇ 18.4 ⁇ 19.3 ⁇ 20.2 ⁇ 20.9 ⁇ 21.7 ⁇ 22.4 ⁇ 23.2 ⁇ 23.8 ⁇ 24.4 ⁇ 26.1 ⁇ and 29.1 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ⁇ 12.3 ⁇ 13.4 ⁇ 13.9 ⁇ 14.9 ⁇ 16.7 ⁇ 18.4 ⁇ 19.3 ⁇ 20.2 ⁇ 20.9 ⁇ Cooley Docket No.: STBI-081/001WO 21.7 ⁇ 22.4 ⁇ 23.2 ⁇ 23.8 ⁇ 24.4 ⁇ 26.1 ⁇ and 29.1 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0347]
  • pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-
  • composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, or twenty-one XRPD peaks selected from those set forth in Table M ⁇ DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Cooley Docket No.: STBI-081/001WO Table M: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N,N
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and is non-hygroscopic.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and is solvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and is unsolvated.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and is anhydrous.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate.
  • the mammal can be e.g., a human or appropriate non-human mammal, such as primate, mouse, rat, dog, cat, cow, horse, goat, camel, sheep or a pig.
  • the subject can also be a bird or fowl.
  • the subject is a human.
  • the term “subject in need thereof” refers to a subject having a disease or having an increased risk of developing the disease.
  • a subject in need thereof can be one who has been previously diagnosed or identified as having a disease or disorder disclosed herein.
  • a subject in need thereof can also be one who is suffering from a disease or disorder disclosed herein.
  • a subject in need thereof can be one who has an increased risk of developing such disease or disorder relative to the population at large (i.e., a subject who is predisposed to developing such disorder relative to the population at large).
  • a subject in need thereof can have a refractory or resistant a disease or disorder disclosed herein (i.e., a disease or disorder disclosed herein that does not respond or has not yet responded to treatment). The subject may be resistant at start of treatment or may become resistant during treatment.
  • the subject in need thereof received and failed all known Cooley Docket No.: STBI-081/001WO effective therapies for a disease or disorder disclosed herein.
  • the subject in need thereof received at least one prior therapy.
  • the term “treating” or “treat” describes the management and care of a patient for the purpose of combating a disease, condition, or disorder and includes the administration of a compound of the present disclosure, or a pharmaceutically acceptable salt, polymorph or solvate thereof, to alleviate the symptoms or complications of a disease, condition or disorder, or to eliminate the disease, condition or disorder.
  • the term “treat” can also include treatment of a cell in vitro or an animal model. It is to be appreciated that references to “treating” or “treatment” include the alleviation of established symptoms of a condition.
  • Treating” or “treatment” of a state, disorder or condition therefore includes: (1) preventing or delaying the appearance of clinical symptoms of the state, disorder or condition developing in a human that may be afflicted with or predisposed to the state, disorder or condition but does not yet experience or display clinical or subclinical symptoms of the state, disorder or condition, (2) inhibiting the state, disorder or condition, i.e., arresting, reducing or delaying the development of the disease or a relapse thereof (in case of maintenance treatment) or at least one clinical or subclinical symptom thereof, or (3) relieving or attenuating the disease, i.e., causing regression of the state, disorder or condition or at least one of its clinical or subclinical symptoms.
  • a compound of the present disclosure can or may also be used to prevent a relevant disease, condition or disorder, or used to identify suitable candidates for such purposes.
  • the term “preventing,” “prevent,” or “protecting against” describes reducing or eliminating the onset of the symptoms or complications of such disease, condition or disorder.
  • the present disclosure also provides pharmaceutical compositions comprising any compound described herein in combination with at least one pharmaceutically acceptable excipient or carrier.
  • pharmaceutical composition is a formulation containing the compounds of the present disclosure in a form suitable for administration to a subject.
  • the pharmaceutical composition is in bulk or in unit dosage form.
  • the unit dosage form is any of a variety of forms, including, for example, a capsule, an IV bag, a tablet, a single pump on an aerosol inhaler or a vial.
  • the active Cooley Docket No.: STBI-081/001WO compound is mixed under sterile conditions with a pharmaceutically acceptable carrier, and with any preservatives, buffers, or propellants that are required.
  • the term “pharmaceutically acceptable” refers to those compounds, anions, cations, materials, compositions, carriers, and/or dosage forms which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of human beings and animals without excessive toxicity, irritation, allergic response, or other problem or complication, commensurate with a reasonable benefit/risk ratio.
  • pharmaceutically acceptable excipient means an excipient that is useful in preparing a pharmaceutical composition that is generally safe, non-toxic and neither biologically nor otherwise undesirable, and includes excipient that is acceptable for veterinary use as well as human pharmaceutical use.
  • compositions containing active compounds of the present disclosure may be manufactured in a manner that is generally known, e.g., by means of conventional mixing, dissolving, granulating, dragee-making, levigating, emulsifying, encapsulating, entrapping, or lyophilising processes.
  • Pharmaceutical compositions may be formulated in a conventional manner using one or more pharmaceutically acceptable carriers comprising excipients and/or auxiliaries that facilitate processing of the active compounds into preparations that can be used pharmaceutically.
  • the active compounds can be prepared with pharmaceutically acceptable carriers that will protect the compound against rapid elimination from the body, such as a controlled release formulation, including implants and microencapsulated delivery systems.
  • pharmaceutically acceptable carriers that will protect the compound against rapid elimination from the body, such as a controlled release formulation, including implants and microencapsulated delivery systems.
  • pharmaceutically acceptable salts refer to derivatives of the compounds of the present disclosure wherein the parent compound is modified by making acid or base salts thereof.
  • the ratio of the compound to the cation or anion of the salt can be 1:1, or any ratio other than 1:1, e.g., 3:1, 2:1, 1:2, or 1:3.
  • the presentation of a compound herein in a particular configuration intends to encompass, and to refer to, each of the available isomers, tautomers, regioisomers, and VWHUHRLVRPHUV ⁇ RI ⁇ WKH ⁇ FRPSRXQG ⁇ RU ⁇ DQ ⁇ PL[WXUH ⁇ WKHUHRI ⁇ ZKLOH ⁇ WKH ⁇ SUHVHQWDWLRQ ⁇ IXUWKHU ⁇ LQWHQGV ⁇ to refer to the specific configuration of the compound. [0377] It will be understood that while compounds disclosed herein may be presented without specified configuration (e.g., without specified stereochemistry).
  • Such presentation intends to encompass all available isomers, tautomers, regioisomers, and stereoisomers of the compound.
  • the presentation of a compound herein without specified configuration intends to refer to each of the available isomers, tautomers, regioisomers, and stereoisomers of the compound, or any mixture thereof.
  • the term “isomerism” means compounds that have identical molecular formulae but differ in the sequence of bonding of their atoms or in the arrangement of their atoms in space.
  • stereoisomers that differ in the arrangement of their atoms in space are termed “stereoisomers.” Stereoisomers that are not mirror images of one another are termed “diastereoisomers,” and stereoisomers that are non-superimposable mirror images of each other are termed “enantiomers” or sometimes optical isomers. A mixture containing equal amounts of individual enantiomeric forms of opposite chirality is termed a “ mixture.” [0379] As used herein, the term “chiral center” refers to a carbon atom bonded to four nonidentical substituents. [0380] As used herein, the term “chiral isomer” means a compound with at least one chiral center.
  • a stereoisomer may be characterized by the absolute configuration (R or S) of that chiral center.
  • Absolute configuration refers to the arrangement in space of the substituents attached to the chiral center.
  • the substituents attached to the chiral center under Cooley Docket No.: STBI-081/001WO consideration are ranked in accordance with the Sequence Rule of Cahn, Ingold and Prelog. (Cahn et al., Angew. Chem. Inter. Edit.
  • the term “geometric isomer” means the diastereomers that owe their existence to hindered rotation about double bonds or a cycloalkyl linker (e.g., 1,3- cyclobutyl).
  • atropic isomers are a type of stereoisomer in which the atoms of two isomers are arranged differently in space. Atropic isomers owe their existence to a restricted rotation caused by hindrance of rotation of large groups about a central bond. Such atropic isomers typically exist as a mixture, however as a result of recent advances in chromatography techniques, it has been possible to separate mixtures of two atropic isomers in select cases.
  • tautomer is one of two or more structural isomers that exist in equilibrium and is readily converted from one isomeric form to another. This conversion results in the formal migration of a hydrogen atom accompanied by a switch of adjacent conjugated double bonds. Tautomers exist as a mixture of a tautomeric set in solution. In solutions where tautomerisation is possible, a chemical equilibrium of the tautomers will be reached. The exact ratio of the tautomers depends on several factors, including temperature, solvent and pH. The concept of tautomers that are interconvertible by tautomerisations is called tautomerism. Of the various types of tautomerism that are possible, two are commonly observed.
  • keto-enol tautomerism a simultaneous shift of electrons and a hydrogen atom occurs.
  • Ring-chain tautomerism arises as a result of the aldehyde group (- Cooley Docket No.: STBI-081/001WO CHO) in a sugar chain molecule reacting with one of the hydroxy groups (-OH) in the same molecule to give it a cyclic (ring-shaped) form as exhibited by glucose.
  • -OH hydroxy groups
  • stereoisomers that are not mirror images of one another are termed “diastereomers” and those that are non-superimposable mirror images of each other are termed “enantiomers”.
  • enantiomers When a compound has an asymmetric center, for example, it is bonded to four different groups, a pair of enantiomers is possible.
  • An enantiomer can be characterized by the absolute configuration of its asymmetric center and is described by the R- and S-sequencing rules of Cahn and Prelog, or by the manner in which the molecule rotates the plane of polarised light and designated as dextrorotatory or levorotatory (i.e., as (+) or (-)-isomers respectively).
  • a chiral compound can exist as either individual enantiomer or as a mixture thereof.
  • a mixture containing equal proportions of the enantiomers is called a “ mixture”.
  • the compounds of this disclosure may possess one or more asymmetric centerV ⁇ VXFK ⁇ compounds can therefore be produced as individual (R)- or (S)-stereoisomers or as mixtures thereof. Unless indicated otherwise, the description or naming of a particular compound in the specification and claims is intended to include both individual enantiomers and mixtures, or otherwise, thereof.
  • the methods for the determination of stereochemistry and the separation of stereoisomers are well-known in the art (see discussion in Chapter 4 of “Advanced Organic Chemistry”, 4th edition J.
  • the present disclosure also encompasses compounds of the disclosure as defined herein which comprise one or more isotopic substitutions.
  • Cooley Docket No.: STBI-081/001WO Biological Assays Compounds designed, selected and/or optimized by methods described above, once produced, can be characterized using a variety of assays known to those skilled in the art to determine whether the compounds have biological activity.
  • the molecules can be characterized by conventional assays, including but not limited to those assays described below, to determine whether they have a predicted activity, binding activity and/or binding specificity.
  • high-throughput screening can be used to speed up analysis using such assays. As a result, it can be possible to rapidly screen the molecules described herein for activity, using techniques known in the art.
  • Embodiment 1 A pharmaceutical composition comprising (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine, or a pharmaceutically acceptable salt thereof, and an excipient.
  • Embodiment 2. The pharmaceutical composition of embodiment 1, comprising (R)- 1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine free base.
  • Embodiment 3 Embodiment 3.
  • Embodiment 4 The pharmaceutical composition of embodiment 1, comprising a pharmaceutically acceptable salt of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine.
  • Embodiment 4 The pharmaceutical composition of embodiment 1 or 3, wherein the pharmaceutically acceptable salt is a fumarate salt.
  • Embodiment 4a The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt polymorphic Form A, Form B, Form I, Form II, Pattern 3a, Pattern 5, Pattern 6, or mixtures thereof. Cooley Docket No.: STBI-081/001WO [0399] Embodiment 4b.
  • composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a monofumarate salt polymorphic Form A, Form B, or a mixture thereof.
  • Embodiment 4c The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a substantially pure monofumarate salt polymorphic Form A.
  • Embodiment 4d The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a monofumarate salt and comprises a mixture of polymorphic Form A and Form B.
  • Embodiment 4d’ Embodiment 4d’.
  • Embodiment 4d’ The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt comprises a mixture of polymorphic Form A and Form II.
  • Embodiment 4d’’ The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt comprises a mixture of polymorphic Form A and Pattern 3a.
  • the pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt comprises a mixture of polymorphic Form A and Pattern 5.
  • the pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt comprises a mixture of polymorphic Form A and Pattern 6.
  • Embodiment 5a The pharmaceutical composition of any one of embodiments 1-4, wherein the excipient comprises a filler, a binder, a glidant, a lubricant, a disintegrant, and/or a plasticizer.
  • Embodiment 5b The pharmaceutical composition of any one of embodiments 1-4, wherein the excipient comprises a filler, a binder, a glidant, a lubricant, a disintegrant, and a plasticizer.
  • Embodiment 6a Embodiment 6a.
  • composition of embodiment 5 wherein the filler is selected from the group consisting of lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, silicified microcrystalline cellulose, and maltose, and a combination thereof.
  • Embodiment 6b The pharmaceutical composition of embodiment 5, wherein the filler comprises lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, silicified microcrystalline cellulose, or maltose, or combinations thereof.
  • Embodiment 7a The pharmaceutical composition of embodiment 5, wherein the binder is selected from the group consisting of povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, ethyl cellulose, and PEO 1NF, and a combination thereof. Cooley Docket No.: STBI-081/001WO [0427]
  • Embodiment 7b The pharmaceutical composition of embodiment 5, wherein the binder comprises povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, ethyl cellulose, or PEO 1NF, or combinations thereof.
  • Embodiment 8a Embodiment 8a.
  • Embodiment 9a The pharmaceutical composition of embodiment 5, wherein the lubricant is selected from the group consisting of magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, and PEO 1NF, and a combination thereof.
  • Embodiment 10a The pharmaceutical composition of embodiment 5, wherein the disintegrant is selected from the group consisting of sodium starch glycolate, croscarmellose sodium, polyplasdone, and L-HPC, and a combination thereof.
  • Embodiment 10b The pharmaceutical composition of embodiment 5, wherein the disintegrant comprises sodium starch glycolate, croscarmellose sodium, polyplasdone, and L- HPC, or combinations thereof.
  • Embodiment 12 The pharmaceutical composition of any one of embodiments 1-4, wherein the excipient is selected from lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, talc, colloidal silicon dioxide, magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, sodium starch glycolate, croscarmellose sodium, polyplasdone, L-HPC, Opadry, ethyl cellulose, silicified microcrystalline cellulose, maltose, polyethylene glycol, PEO 1NF, and methacrylic acid copolymer, and a combination thereof.
  • the excipient is selected from lactose monohydrate, maize starch, Neusilin U
  • Embodiment 13 The pharmaceutical composition of any one of embodiments 1-12, further comprising a film coating. Cooley Docket No.: STBI-081/001WO [0437] Embodiment 14. The pharmaceutical composition of 13, wherein the film coating comprises Opadry. [0438] Embodiment 15. The pharmaceutical composition of any one of embodiments 1-14, further comprising a release controlling polymer. [0439] Embodiment 16a. The pharmaceutical composition of 15, wherein the release controlling polymer is selected from the group consisting of hypromellose, ethyl cellulose, and methacrylic acid copolymer, and a combination thereof. [0440] Embodiment 16b.
  • Embodiment 17 The pharmaceutical composition of any one of embodiments 1-16, further comprising a capsule shell.
  • Embodiment 18a The pharmaceutical composition of 15, wherein the capsule shell is an HPMC capsule shell.
  • Embodiment 18b The pharmaceutical composition of 15, wherein the capsule shell comprises an HPMC capsule or a gelatin capsule shell.
  • Embodiment 19 A method of treating or preventing a disease or condition, comprising administering to a subject in need thereof an effective amount of the pharmaceutical composition of any one of embodiments 1-18.
  • Embodiment 20 Embodiment 20.
  • Embodiment 21 Use of the pharmaceutical composition of any one of embodiments 1-18 in the manufacture of a medicament for the treatment or prevention of a disease or condition.
  • Embodiment 22 The pharmaceutical composition according to any one of the previous embodiments, wherein the pharmaceutical composition does not comprise a gelatin capsule.
  • Embodiment 23 The pharmaceutical composition according to any one of the previous embodiments, wherein the pharmaceutical composition does not comprise high moisture containing excipients.
  • methyl ethyl ketone also known as 2-butanone ⁇ 0(. ⁇ P/ ⁇ ZLWK ⁇ VRQLFDWLRQ ⁇ DQG ⁇ WR ⁇ WKH ⁇ VWLUULQJ ⁇ VROXWLRQ ⁇ ZDV ⁇ DGGHG ⁇ FU ⁇ VWDOV ⁇ FD ⁇ PJ ⁇ RI ⁇ > ⁇ 5 ⁇ PHWKR[ ⁇ + ⁇ LQGRO ⁇ O ⁇ SURSDQ ⁇ O@GLPHWK ⁇ ODPLQH ⁇ IXPDUDWH ⁇ VDOW ⁇ SRO ⁇ PRUSK ⁇ form A). A fine precipitate was observed after 10 min. The suspension was stirred for 24 hours at rt. The solid was isolated by filtration and the filter cake was washed with MEK (ca.
  • (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate is characterized as having an XRPD with representative peaks at 22.5 ⁇ 16.0 ⁇ and 14.1 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • (R)- 1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate is characterized as having an XRPD with representative peaks at 22.5 ⁇ 16.0 ⁇ 14.1 ⁇ , 13.5 ⁇ , and 19.5 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Cooley Docket No.: STBI-081/001WO Example 2.
  • Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Monofumarate, Form A [0456] In some embodiments, the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate is Form A. [0457] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 1.
  • XRPD X-ray powder diffraction
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising characteristic peaks at ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern further comprising one or more peaks at ⁇ ⁇ 22.3 ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising one or more peaks selected from those set forth in Table A, DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0458]
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 2.
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising characteristic peaks at 14.0 ⁇ 15.9 ⁇ and 22.3 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern further comprising one or more peaks at ⁇ ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ Cooley Docket No.: STBI-081/001WO radiation).
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising one or more peaks selected from those set forth in Table B ⁇ DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0459]
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 3.
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising characteristic peaks at 19.3 ⁇ 19.6 ⁇ and 22.6 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern further comprising one or more peaks at ⁇ ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising one or more peaks selected from those set forth in Table C, as measured ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0460] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has an X-ray powder diffraction (XRPD) pattern substantially
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising characteristic peaks at ⁇ DQG ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern further comprising one or more peaks DW ⁇ ⁇ ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising one or more peaks selected from those set forth in Table D ⁇ DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Monofumarate, Form B Cooley Docket No.: STBI-081/001WO [0461]
  • the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate is Form B.
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form B has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 7.
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern comprising characteristic peaks at 17.8 ⁇ 19.5 ⁇ and 20.3 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern further comprising one or more peaks at 5.9 ⁇ 9.5 ⁇ 15.1 ⁇ 16.8 ⁇ 17.8 ⁇ 19.5 ⁇ 20.3 ⁇ 23.6 ⁇ and 29.8 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ radiation).
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form B has a XRPD pattern comprising one or more peaks selected from those set forth in Table E, DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0463]
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form B has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 8.
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern comprising characteristic peaks at ⁇ DQG ⁇ ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern further comprising one or more peaks at DW ⁇ ⁇ ⁇ DQG ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern comprising one or more peaks selected from those set forth in Table F, as PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Hemi-fumarate, Form I and Form II Production of the Hemi-fumarate Salt
  • the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate is Form I.
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate Form I has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 9.
  • XRPD X-ray powder diffraction
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern comprising characteristic peaks at 15.9 ⁇ 19.4 ⁇ and 21.0 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern further comprising one or more peaks at 11.7 ⁇ 13.4 ⁇ 13.7 ⁇ 15.2 ⁇ 15.9 ⁇ 18.9 ⁇ 19.4 ⁇ 21.0 ⁇ 21.6 ⁇ 22.5 ⁇ 23.2 ⁇ and 27.1 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern comprising one or more peaks selected from those set forth in Table G ⁇ DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0468]
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern comprising characteristic peaks at 16.0 ⁇ 21.2 ⁇ and 27.2 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern further comprising one or more peaks at 11.8 ⁇ 13.7 ⁇ 15.4 ⁇ 16.0 ⁇ 19.2 ⁇ 19.5 ⁇ 21.2 ⁇ 21.7 ⁇ 22.6 ⁇ 23.4 ⁇ 24.3 ⁇ 25.0 ⁇ 27.2 ⁇ 28.5 ⁇ and 30.4 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD Cooley Docket No.: STBI-081/001WO pattern comprising one or more peaks selected from those set forth in Table H, as measured ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate Form II has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 11.
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II has a XRPD pattern comprising characteristic peaks at ⁇ DQG ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II has a XRPD pattern further comprising one or more peaks at 11.5 ⁇ 13.3 ⁇ 13.5 ⁇ 15.1 ⁇ 15.8 ⁇ 18.8 ⁇ 19.2 ⁇ 20.9 ⁇ 21.4 ⁇ 22.4 ⁇ 23.1 ⁇ 24.0 ⁇ 24.7 ⁇ 26.9 ⁇ 28.2 ⁇ and 30.2 ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II has a XRPD pattern comprising one or more peaks selected from those set forth in Table I ⁇ DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Crystalline (R
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Pattern 3a has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 12.
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern comprising characteristic peaks at ⁇ ⁇ DQG ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern further comprising one or more peaks at 9.6 ⁇ 13.9 ⁇ 15.2 ⁇ 16.9 ⁇ 17.9 ⁇ 19.7 ⁇ 20.5 ⁇ 23.9 ⁇ 24.9 ⁇ 25.2 ⁇ 28.5 ⁇ and 29.8 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- Cooley Docket No.: STBI-081/001WO dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern comprising one or more peaks selected from those set forth in Table J ⁇ DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ [0473]
  • crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern comprising characteristic peaks at 18.1 ⁇ 19.8 ⁇ and 19.9 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern further comprising one or more peaks at 9.5 ⁇ 11.9 ⁇ 14.1 ⁇ 15.1 ⁇ 16.8 ⁇ 17.6 ⁇ 18.1 ⁇ 19.0 ⁇ 19.8 ⁇ 19.9 ⁇ 23.6 ⁇ 24.0 ⁇ 25.7 ⁇ 28.3 ⁇ 30.0 ⁇ and 31.7 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern comprising one or more peaks selected from those set forth in Table K, DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Crystalline (R)-1-(5-(5-
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Pattern 5 has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 14.
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5 has a XRPD pattern comprising characteristic peaks at 7.9 ⁇ 20.2 ⁇ , and 21.6 ⁇ ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5 has a XRPD pattern further comprising one or more peaks at 7.9 ⁇ 15.7 ⁇ 20.2 ⁇ 21.6 ⁇ and 23.7 ⁇ ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5 has a XRPD pattern comprising one or more peaks selected from those set forth in Table L, as measured ZLWK ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Fumarate, Pattern 6 Cooley Docket No.: STBI-081/001WO [0476]
  • crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Pattern 6 has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 15.
  • crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 6 has a XRPD pattern comprising characteristic peaks at ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ .
  • crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 6 has a XRPD pattern further comprising one or more peaks at 8.2 ⁇ 12.3 ⁇ 13.4 ⁇ 13.9 ⁇ 14.9 ⁇ 16.7 ⁇ 17.2 ⁇ 18.4 ⁇ 19.3 ⁇ 20.2 ⁇ 20.9 ⁇ 21.7 ⁇ 22.4 ⁇ 23.2 ⁇ 23.8 ⁇ 24.4 ⁇ 25.1 ⁇ 26.1 ⁇ 27.6 ⁇ 29.1 ⁇ DQG ⁇ RU ⁇ &X ⁇ . ⁇ UDGLDWLRQ ⁇ In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Pattern 6 has a XRPD pattern comprising one or more peaks selected from those set forth in Table M ⁇ DV ⁇ PHDVXUHG ⁇ ZLWK ⁇ &X ⁇ . ⁇ UD
  • the dry mixtures were prepared by weighing using a balance, Cooley Docket No.: STBI-081/001WO followed by gentle mixing using a spatula in transparent glass vials.
  • Binary mixture of API with selected excipient were prepared. Compatibility of the binary mixture of 50% excipient and 50% API which is equivalent to 1:1 excipient ratio.
  • Samples were prepared and packed in glass vials with cap. These vials were kept at stress condition of 40°C ⁇ 2 /75% RH ⁇ 5 for period of 15 and 30 days in closed condition.
  • the pure drug substance was also be used as a reference in the compatibility studies at all storage conditions. Also, the pure excipients were stored at all storage conditions and analyzed along with the binary mixture.
  • Table 4 Appearance of Samples ((R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine: Excipients) Sr. E xcipient/substrate Initi 15 days 30 days N o al 40°C/75%RH 40°C/75%RH (R)-1-(5-methoxy-1H-indol- No ch -2- White to off-whi ange No change 1 1-yl)-N,N-dimethylpropan te po from initial from initial amine Fumarate (Form A) wder. timepoint. timepoint. Lactose monohydrate White to off-white No change No change 2 powder.

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Abstract

La présente divulgation concerne des compositions pharmaceutiques comprenant de la (R)-1-(5-méthoxy-1H-indol-1-yl)-N,N-diméthylpropan-2-amine, des sels pharmaceutiquement acceptables de celle-ci et un ou plusieurs excipients.
PCT/US2024/024287 2023-04-14 2024-04-12 Compositions pharmaceutiques comprenant de la (r)-1-(5-méthoxy-1h-indol-1-yl)-n,n-diméthylpropan-2-amine ou un sel pharmaceutiquement acceptable de celle-ci Pending WO2024216042A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12435036B2 (en) 2021-11-16 2025-10-07 Terran Biosciences Inc. Salts and solid forms of (R)-1-(5-methoxy-1H-indol-1-yl)-n,n-dimethylpropan-2-amine

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020176597A1 (fr) * 2019-02-27 2020-09-03 The Regents Of The University Of California Indoles n-substitués et autres hétérocycles destinés au traitement des troubles du cerveau
WO2022081631A1 (fr) * 2020-10-13 2022-04-21 The Regents Of The University Of California Méthode de criblage de gpcr permettant d'identifier des composés non hallucinogènes
WO2023091974A2 (fr) * 2021-11-16 2023-05-25 Terran Biosciences, Inc. Formes salines et solides de (r)-1-(5-méthoxy-1 h-indol-1-yl)-n,n-diméthylpropan-2-amine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020176597A1 (fr) * 2019-02-27 2020-09-03 The Regents Of The University Of California Indoles n-substitués et autres hétérocycles destinés au traitement des troubles du cerveau
WO2022081631A1 (fr) * 2020-10-13 2022-04-21 The Regents Of The University Of California Méthode de criblage de gpcr permettant d'identifier des composés non hallucinogènes
WO2023091974A2 (fr) * 2021-11-16 2023-05-25 Terran Biosciences, Inc. Formes salines et solides de (r)-1-(5-méthoxy-1 h-indol-1-yl)-n,n-diméthylpropan-2-amine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12435036B2 (en) 2021-11-16 2025-10-07 Terran Biosciences Inc. Salts and solid forms of (R)-1-(5-methoxy-1H-indol-1-yl)-n,n-dimethylpropan-2-amine

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