WO2024138007A2 - Dérivés de tryptamine - Google Patents

Dérivés de tryptamine Download PDF

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Publication number
WO2024138007A2
WO2024138007A2 PCT/US2023/085462 US2023085462W WO2024138007A2 WO 2024138007 A2 WO2024138007 A2 WO 2024138007A2 US 2023085462 W US2023085462 W US 2023085462W WO 2024138007 A2 WO2024138007 A2 WO 2024138007A2
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WO
WIPO (PCT)
Prior art keywords
crystalline
meo
dimethyl
purified
crystalline form
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PCT/US2023/085462
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English (en)
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Andrew R. Chadeayne
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Caamtech, Inc.
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Publication of WO2024138007A2 publication Critical patent/WO2024138007A2/fr

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  • the disclosure relates to 2-(5-methoxy-lH-indol-3-yl)ethanamine (5-methoxytryptamine or 5-MeO-T), crystalline 5-MeO-T, and specific crystalline forms thereof, including crystalline form 1 of 5-MeO-T; to pharmaceutical compositions containing 5-MeO-T or crystalline 5-MeO-T, including crystalline form 1 of 5-MeO-T; and to methods of treatment/therapeutic uses of 5-MeO-T or crystalline 5-MeO-T, including crystalline form 1 of 5-MeO-T.
  • 5-MeO-T 2-(5-methoxy-lH-indol-3-yl)ethanamine
  • 5-MeO-T 2-(5-methoxytryptamine or 5-MeO-T), crystalline 5-MeO-T, and specific crystalline forms thereof, including crystalline form 1 of 5-MeO-T
  • the disclosure further relates to [2-(5-chloro-lH-indol-3-yl)ethyl]dimethyl(propan-2- yl)azanium iodide (5-chloro-A/,A/-dimethyl-/V-isopropyltryptammonium iodide or 5-CI-DMiPT iodide), crystalline 5-CI-DMiPT iodide, and specific crystalline forms thereof, including crystalline form 1 of 5- CI-DMiPT iodide; to pharmaceutical compositions containing 5-CI-DMiPT iodide or crystalline 5-CI- DMiPT iodide, including crystalline form 1 of 5-CI-DMiPT iodide; and to methods of treatment/therapeutic uses of 5-CI-DMiPT iodide or crystalline 5-CI-DMiPT iodide, including crystalline form 1 of 5-CI-DMiPT iodide.
  • This disclosure further relates to relates to [2-(5-chloro-lH-indol-3- yl)ethyl]dimethyl(propan-2-yl)azanium iodide (5-chloro-A/,A/-dimethyl-/V-isopropyltryptammonium iodide or 5-CI-DMiPT iodide), crystalline 5-CI-DMiPT iodide, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of 5-CI-DMiPT iodide, including crystalline form 1 of 5-CI-DMiPT iodide.
  • the disclosure also provides a composition comprising 5-MeO-T, crystalline 5-MeO-
  • FIG. 8 shows the unit cell of crystalline form 1 of 5-chloro-/V,A/-dimethyl-/V- isopropyltryptammonium iodide along the a-axis.
  • 5-CI-DMiPT iodide has the following chemical formula:
  • 5-MeO-T crystalline 5-MeO-T, 5-MeO-T fumarate dihydrate, crystalline 5-MeO-T fumarate dihydrate, 5-CI-DMiPT iodide, crystalline 5-CI-DMiPT iodide, 5-CI-DiPT, crystalline 5-CI-DiPT, N,N-dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide, crystalline N,N-dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide, or specific crystalline forms thereof, such as crystalline form 1 of 5-MeO-T, crystalline form 1 of 5-MeO-T fumarate dihydrate, crystalline form 1 of 5-CI-DMiPT iodide, crystalline form 1 of 5-CI-DiPT, and crystalline form 1 of N,N-dimethyl-a-oxo-4-(pheny
  • 5-MeO-T crystalline 5-MeO-T, 5-MeO-T fumarate dihydrate, crystalline 5-MeO-T fumarate dihydrate, 5-CI-DMiPT iodide, crystalline 5-CI- DMiPT iodide, 5-CI-DiPT, crystalline 5-CI-DiPT, N,N-dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3- acetamide, crystalline N,N-dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide, or specific crystalline forms thereof, such as crystalline form 1 of 5-MeO-T, crystalline form 1 of 5-MeO-T fumarate dihydrate, crystalline form 1 of 5-CI-DMiPT iodide, crystalline form 1 of 5-CI-DiPT, and crystalline form 1 of N,N-dimethyl-a-oxo-4-(phenylme
  • the disclosure provides a method for preventing and/or treating a psychological disorder by administering to a subject in need thereof a therapeutically effective amount of 5-MeO-T, crystalline 5-MeO-T, 5-MeO-T fumarate dihydrate, crystalline 5-MeO-T fumarate dihydrate, 5-CI-DMiPT iodide, crystalline 5-CI-DMiPT iodide, 5-CI-DiPT, crystalline 5-CI-DiPT, N,N-dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide, crystalline N,N-dimethyl-a-oxo-4- (phenylmethoxy)-lH-indole-3-acetamide, or specific crystalline forms thereof, such as crystalline form 1 of 5-MeO-T, crystalline form 1 of 5-MeO-T fumarate dihydrate, crystalline form 1 of 5-CI- DMiPT iodide, crystalline form 1
  • the disclosure provides a method for preventing and/or treating these disorders by administering to a subject in need thereof a therapeutically effective amount of 5-MeO-T, crystalline 5-MeO-T, 5-MeO-T fumarate dihydrate, crystalline 5-MeO-T fumarate dihydrate, 5-CI-DMiPT iodide, crystalline 5-CI-DMiPT iodide, 5-CI-DiPT, crystalline 5-CI-DiPT, N,N- dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide, crystalline N,N-dimethyl-a-oxo-4- (phenylmethoxy)-lH-indole-3-acetamide, or specific crystalline forms thereof, such as crystalline form 1 of 5-MeO-T, crystalline form 1 of 5-MeO-T fumarate dihydrate, crystalline form 1 of 5-CI- DMiPT iodide, crystalline form 1 of 5-CI
  • compositions comprising an effective amount of 5-
  • MeO-T crystalline 5-MeO-T, 5-MeO-T fumarate dihydrate, crystalline 5-MeO-T fumarate dihydrate, 5-CI-DMiPT iodide, crystalline 5-CI-DMiPT iodide, 5-CI-Di PT, crystalline 5-CI-DiPT, N,N-dimethyl-a- oxo-4-(phenylmethoxy)-lH-indole-3-acetamide, crystalline N,N-dimethyl-a-oxo-4-(phenylmethoxy)- lH-indole-3-acetamide, or specific crystalline forms thereof, such as crystalline form 1 of 5-MeO-T, crystalline form 1 of 5-MeO-T fumarate dihydrate, crystalline form 1 of 5-CI-DMiPT iodide, crystalline form 1 of 5-CI-DiPT, and crystalline form 1 of N,N-dimethyl-a-oxo-4-(phenylmeth
  • this disclosure provides a composition
  • a composition comprising: a first component comprising 5- MeO-T, crystalline 5-MeO-T, 5-MeO-T fumarate dihydrate, crystalline 5-MeO-T fumarate dihydrate, 5-CI-DMiPT iodide, crystalline 5-CI-DMiPT iodide, 5-CI-Di PT, crystalline 5-CI-DiPT, N,N-dimethyl-a- oxo-4-(phenylmethoxy)-lH-indole-3-acetamide, crystalline N,N-dimethyl-a-oxo-4-(phenylmethoxy)- lH-indole-3-acetamide, or specific crystalline forms thereof, such as crystalline form 1 of 5-MeO-T, crystalline form 1 of 5-MeO-T fumarate dihydrate, crystalline form 1 of 5-CI-DMiPT iodide, crystalline form 1 of 5-CI-DiPT, and crystalline form 1
  • the term "purified" refers to a compound or composition that has been chromatographed, for example by gas chromatography, liquid chromatography (e.g., LC, HPLC, etc.), etc.
  • the term “purified” refers to a compound that is between 95-
  • 5-MeO-T crystalline 5-MeO-T, 5-MeO-T fumarate dihydrate, crystalline 5-MeO-T fumarate dihydrate, 5-CI-DMiPT iodide, crystalline 5-CI-DMiPT iodide, 5-CI-DiPT, crystalline 5-CI-DiPT, N,N-dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide, crystalline
  • O.1:100 to about 100:0.1 from about 1:100 to about 100:1, from about 1:50 to about 50:1, from about 1:25 to about 25:1, from about 1:20 to about 20:1, from about 1:10 to about 10:1, from about 1:5 to about 5:1, from about 1:2 to about 2:1 or may be about 1:1.
  • compositions comprising a combination of a purified psilocybin derivative with a second purified psilocybin derivative, with one or two purified cannabinoids or with a purified terpene.
  • the term "dopaminergic drug” refers to a compound that binds, blocks, or otherwise influences (e.g., via an allosteric reaction) activity at a dopamine receptor.
  • a dopaminergic drug binds to a dopamine receptor.
  • a dopaminergic drug indirectly affects a dopamine receptor, e.g., via interactions affecting the reactivity of other molecules at the dopamine receptor.
  • a dopaminergic drug is an agonist, e.g., a compound activating a dopamine receptor.
  • 5-MeO-T crystalline 5-MeO-T, 5-MeO-T fumarate dihydrate, crystalline 5-MeO-T fumarate dihydrate, 5-CI- DMiPT iodide, crystalline 5-CI-DMiPT iodide, 5-CI-DiPT, crystalline 5-CI-DiPT, N,N-dimethyl-a-oxo-4- (phenylmethoxy)-lH-indole-3-acetamide, crystalline N,N-dimethyl-a-oxo-4-(phenylmethoxy)-lH- indole-3-acetamide, or specific crystalline forms thereof, such as crystalline form 1 of 5-MeO-T, crystalline form 1 of 5-MeO-T fumarate dihydrate, crystalline form 1 of 5-CI-DMiPT iodide, crystalline form 1 of 5-CI-DiPT, and crystalline form 1 of N,N-dimethyl-a-oxo-4-(phenylmeth
  • Solid dosage forms for oral administration which includes capsules, tablets, pills, powders, and granules, may be used.
  • the active compound may be mixed with at least one inert, pharmaceutically acceptable excipient (also known as a pharmaceutically acceptable carrier).
  • E6 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5- methoxytryptamine according to any one of E1-E3.
  • E7 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E4 or E5.
  • E15 A composition comprising crystalline 5-methoxytryptammonium fumarate dihydrate according to any one of E11-E13 and an excipient.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5- methoxytryptammonium fumarate dihydrate according to E10.
  • E19 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5- methoxytryptammonium fumarate dihydrate according to any one of E11-E13.
  • E22 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5- methoxytryptammonium fumarate dihydrate according to E10.
  • E31 A composition comprising crystalline 5-chloro-A/,A/-dimethyl-/V- isopropyltryptammonium iodide according to any one of E27-E29 and an excipient.
  • E32 A composition comprising 5-chloro-/V,A/-dimethyl-A/-isopropyltryptammonium iodide according to E26 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.
  • E37 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E31 or E33.
  • E38 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5-chloro-A/,/V- dimethyl-A/-isopropyltryptammonium iodide according to E26.
  • E40 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E30 or E32.
  • E41 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E31 or E33.
  • E46 A composition comprising 5-chloro-/V z /V-diisopropyltryptamine according to E42 and an excipient.
  • E47 A composition comprising crystalline 5-chloro-A/,A/-diisopropyltryptamine according to any one of E43-E45 and an excipient.
  • E48 A composition comprising 5-chloro-A/,A/-diisopropyltryptamine according to E42 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.
  • E50 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5-chloro-/V,/V- diisopropyltryptamine according to E42.
  • E51 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5- chloro-/V,/V-diisopropyltryptamine according to any one of E43-E45.
  • E52 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E46 or E48.
  • E53 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E47 or E49.
  • E54 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5-chloro-A/,/V- diisopropyltryptamine according to E42.
  • E55 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5- chloro-A/,A/-diisopropyltryptamine according to any one of E43- E45.
  • E56 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E46 or E48.
  • E57 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E47 or E49.
  • E59 Crystalline form 1 of /V z /V-dimethyl-2-oxo-2-(4-phenylmethoxy-lH-indol-3- yljacetamide (A/ z A/-dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide).
  • E61 A composition comprising crystalline /V z /V-dimethyl-a-oxo-4-(phenylmethoxy)-lH- indole-3-acetamide according to any one of E58-E60 and an excipient.
  • E62 A composition comprising crystalline A/ z /V-dimethyl-a-oxo-4-(phenylmethoxy)-lH- indole-3-acetamide according to any one of E58-E60 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.
  • E63 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline N,N- dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide according to any one of E58-E60.
  • E64 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E61 or E62.
  • E65 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline N,N- dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide according to any one of E58-E60 [00165]
  • E66 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E61 or E62.
  • SCXRD Single Crystal X-Ray Diffraction
  • FIG. 1 shows the molecular structure of crystalline form 1 of 5-MeO-T, showing the atomic labeling.
  • FIG. 2 shows the molecular structure of crystalline form 1 of 5-MeO-T fumarate dihydrate, showing the atomic labeling.
  • FIG. 3 shows the molecular structure of crystalline form 1 of 5-CI-DMiPT iodide, showing the atomic labeling.
  • FIG. 4 shows the molecular structure of crystalline form 1 of 5-CI-DiPT, showing the atomic labeling.
  • FIG. 5 shows the molecular structure of crystalline form 1 of N,N-dimethyl-a-oxo-4- (phenylmethoxy)-lH-indole-3-acetamide, showing the atomic labeling.
  • FIG. 6 shows the unit cell of crystalline form 1 of 5-MeO-T along the c-axis.
  • FIG. 7 shows the unit cell of crystalline form 1 of 5-MeO-T fumarate dihydrate along the a-axis.
  • FIG. 8 shows the unit cell of crystalline form 1 of 5-CI-DMiPT iodide along the a-axis.
  • FIG. 9 shows the unit cell of crystalline form 1 of 5-CI-DiPT along the a-axis.
  • FIG. 10 shows the unit cell of crystalline form 1 of N,N-dimethyl-a-oxo-4- (phenylmethoxy)-lH-indole-3-acetamide along the a-axis.
  • FIG. 11 shows the 2:1 ratio of crystalline form 1 of 5-MeO-T fumarate dihydrate as a dimer.
  • FIG. 12 shows a simulated X-ray powder diffraction pattern (XRPD) for crystalline form 1 of 5-MeO-T generated from its single crystal data.
  • Table 4 lists the angles, °26 ⁇ O.2°20, and d-spacing of the peaks identified in the experimental XRPD pattern of FIG. 12. The entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 13.7, 17.4, and 20.3 °26 ⁇ O.2°20 or their corresponding d-spacing as well as by an XRPD pattern substantially similar to FIG. 12.
  • FIG. 13 shows a simulated X-ray powder diffraction pattern (XRPD) for crystalline form 1 of 5-MeO-T fumarate dihydrate generated from its single crystal data.
  • Table 5 lists the angles, °26 ⁇ 0.2°2S, and d-spacing of the peaks identified in the experimental XRPD pattern of FIG. 13. The entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 7.3, 10.6, and 12.4 °20 ⁇ O.2°20 or their corresponding d-spacing as well as by an XRPD pattern substantially similar to FIG. 13.
  • FIG. 14 shows a simulated X-ray powder diffraction pattern (XRPD) for crystalline form 1 of 5-CI-DMIPT iodide generated from its single crystal data.
  • Table 6 lists the angles, ”20 ⁇ O.2°20, and d-spacing of the peaks identified in the experimental XRPD pattern of FIG. 14. The entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 13.1, 20.0, and 21.2 °20 ⁇ O.2°20 or their corresponding d-spacing as well as by an XRPD pattern substantially similar to FIG. 14.
  • FIG. 15 shows a simulated X-ray powder diffraction pattern (XRPD) for crystalline form 1 of 5-CI-DIPT generated from its single crystal data.
  • Table 7 lists the angles, °20 ⁇ O.2°20, and d-spacing of the peaks identified in the experimental XRPD pattern of FIG. 15. The entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 9.2, 17.1, and 18.8 °20 ⁇ O.2°20 or their corresponding d-spacing as well as by an XRPD pattern substantially similar to FIG. 15.
  • FIG. 16 shows a simulated X-ray powder diffraction pattern (XRPD) for crystalline form 1 of N,N-dimethyl-a-oxo-4-(phenylmethoxy)-lH-indole-3-acetamide generated from its single crystal data.
  • Table 8 lists the angles, “20 ⁇ O.2°20, and d-spacing of the peaks identified in the experimental XRPD pattern of FIG. 16. The entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 13.6, 16.2, and 18.3 °20 ⁇ O.2°20 or their corresponding d-spacing as well as by an XRPD pattern substantially similar to FIG. 16.

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Abstract

La présente divulgation concerne de la 2-(5-méthoxy-1H-indol-3-yl)éthanamine (5-méthoxytryptamine ou 5-MeO-T), de la 5-MeO-T cristalline, du dihydrate de bis(2-(5-méthoxy-1H-indol-3-yl)éthan-1-aminium) (2E)-but-2-énedioate (dihydrate de fumarate de 5-méthoxytryptammonium ou dihydrate de fumarate de 5-MeO-T), du dihydrate de fumarate de 5-MeO-T cristallin, de l'iodure de [2-(5-chloro-1H-indol-3-yl)éthyl]diméthyl(propan-2-yl)azanium (iodure de 5-chloro-N,N-diméthyl-N-isopropyltryptammonium ou iodure de 5-CI-DMiPT), de l'iodure de 5-CI-DMiPT cristallin, de la [2-(5-chloro-1H-indol-3-yl)éthyl]bis(propan-2-yl)amine (5-chloro-N,N-diisopropyltryptamine ou 5-CI-DiPT), de la 5-CI-DiPT cristalline, du N,N-diméthyl-2-oxo-2-(4-phénylméthoxy-1H-indol-3-yl)acétamide (N, N-diméthyl-α-oxo-4-(phénylméthoxy)-1H-indole-3-acétamide), du N,N-diméthyl-α-oxo-4-(phénylméthoxy)-1H-indole-3-acétamide cristallin, et des formes cristallines spécifiques de ceux-ci, telles que la forme cristalline 1 de 5-MeO-T, la forme cristalline 1 de fumarate dihydrate de 5-MeO-T, la forme cristalline 1 d'iodure de 5-CI-DMiPT, la forme cristalline 1 de 5-CI-DiPT, et la forme cristalline 1 de N,N-diméthyl-α-oxo-4-(phénylméthoxy)-1H-indole-3-acétamide, des compositions les contenant, et un procédé de traitement les utilisant.
PCT/US2023/085462 2022-12-21 2023-12-21 Dérivés de tryptamine WO2024138007A2 (fr)

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US202263476401P 2022-12-21 2022-12-21
US202263476402P 2022-12-21 2022-12-21
US202263476557P 2022-12-21 2022-12-21
US202263476559P 2022-12-21 2022-12-21
US202263476417P 2022-12-21 2022-12-21
US63/476,417 2022-12-21
US63/476,559 2022-12-21
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