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WO2024118767A3 - Tryptamine derivatives - Google Patents

Tryptamine derivatives Download PDF

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Publication number
WO2024118767A3
WO2024118767A3 PCT/US2023/081591 US2023081591W WO2024118767A3 WO 2024118767 A3 WO2024118767 A3 WO 2024118767A3 US 2023081591 W US2023081591 W US 2023081591W WO 2024118767 A3 WO2024118767 A3 WO 2024118767A3
Authority
WO
WIPO (PCT)
Prior art keywords
indol
crystalline
ethan
aminium
meo
Prior art date
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.)
Ceased
Application number
PCT/US2023/081591
Other languages
French (fr)
Other versions
WO2024118767A2 (en
Inventor
Andrew R. Chadeayne
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Caamtech Inc
Original Assignee
Caamtech Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Caamtech Inc filed Critical Caamtech Inc
Publication of WO2024118767A2 publication Critical patent/WO2024118767A2/en
Publication of WO2024118767A3 publication Critical patent/WO2024118767A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16—Tryptamines
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/15—Fumaric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

This disclosure relates to bis(2-(5-methoxy-1H-indol-3-yl)ethan-1-aminium) (2E)-but-2 enedioate (5-MeO-T fumarate), crystalline 5-MeO-T fumarate, 2-(1H-indol-3-yl)ethan-1-aminium 3- carboxy-2-hydroxypropanoate (tryptammonium hydromalate), crystalline tryptammonium hydromalate, 2-(1H-indol-3-yl)ethan-1-aminium 2-carboxybenzoate (tryptammonium hydrophthalate), crystalline tryptammonium hydrophthalate, bis([2-(4-methoxy-1H-indol-3- yl)ethyl](methyl)(propan-2-yl)azanium) (2E)-but-2-enedioate (4-MeO-MiPT fumarate), crystalline 4- MeO-MiPT fumarate, [2-(4-hydroxy-1H-indol-3-yl)ethyl](propan-2-yl)propylazanium (2E)-3 carboxyprop-2-enoate (4-HO-PiPT hydrofumarate), crystalline 4-HO-PiPT hydrofumarate, 2-(5- chloro-1H-indol-3-yl)ethan-1-aminium 2-{[2-(5-chloro-1H-indol-3-yl)ethyl]azaniumyl}butanedioate (5-CI-T-N-Suc-5-CI-T), crystalline 5-CI-T- N-Suc-5-CI-T, 2-(5-chloro-1H-indol-3-yl)ethan-1-aminium 3- carboxy-2-hydroxypropanoate (5-CI-T hydromaleate), crystalline 5-CI-T hydromaleate, 2-(5-chloro- 1H-indol-3-yl)ethan-1-aminium 2-carboxybenzoate (5-CI-T hydrophthalate), crystalline 5-CI-T hydrophthalate, bis(2-(5-chloro-1H-indol-3-yl)ethan-1-aminium) 2-hydroxybutanedioate (5-CI-T malate), crystalline 5-CI-T malate, 2-(5-methoxy-1H-indol-3-yl)ethan-1-aminium 2-{[2-(5-methoxy- 1H-indol-3-yl)ethyl]azaniumyl}butanedioate (5-MeO-T-N-Suc-5-MeO-T), crystalline 5-MeO-T- N-Suc-5-MeO-T, 2-(5-methyl-lH-indol-3-yl)ethan-l-amine (5-Me-T), crystalline 5-Me-T, bis(N-[2-(4-hydroxy- 1H-indol-3-yl)ethyl]-N-methylcyclopropanaminium) (2E)-but-2-enedioate (4-HO-MCPT fumarate), crystalline 4-HO-MCPT fumarate, [2-(4-hydroxy-1H-indol-3-yl)ethyl]bis(propan-2-yl)azanium (2 E)-3- carboxyprop-2-enoate (4-HO-DiPT hydrofumarate), crystalline 4-HO-DiPT hydrofumarate, and specific crystalline forms thereof, including crystalline form 1 of each of the previously recited compounds, to compositions containing the same, and to methods of treatment using them.
PCT/US2023/081591 2022-11-29 2023-11-29 Tryptamine derivatives Ceased WO2024118767A2 (en)

Applications Claiming Priority (26)

Application Number Priority Date Filing Date Title
US202263385261P 2022-11-29 2022-11-29
US202263385287P 2022-11-29 2022-11-29
US63/385,261 2022-11-29
US63/385,287 2022-11-29
US202263385448P 2022-11-30 2022-11-30
US63/385,448 2022-11-30
US202263385667P 2022-12-01 2022-12-01
US202263385664P 2022-12-01 2022-12-01
US202263385666P 2022-12-01 2022-12-01
US202263385662P 2022-12-01 2022-12-01
US202263385665P 2022-12-01 2022-12-01
US63/385,665 2022-12-01
US63/385,666 2022-12-01
US63/385,662 2022-12-01
US63/385,667 2022-12-01
US63/385,664 2022-12-01
US202263386501P 2022-12-08 2022-12-08
US202263386523P 2022-12-08 2022-12-08
US202263386534P 2022-12-08 2022-12-08
US202263386502P 2022-12-08 2022-12-08
US202263386503P 2022-12-08 2022-12-08
US63/386,523 2022-12-08
US63/386,534 2022-12-08
US63/386,502 2022-12-08
US63/386,501 2022-12-08
US63/386,503 2022-12-08

Publications (2)

Publication Number Publication Date
WO2024118767A2 WO2024118767A2 (en) 2024-06-06
WO2024118767A3 true WO2024118767A3 (en) 2024-07-18

Family

ID=91324905

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2023/081591 Ceased WO2024118767A2 (en) 2022-11-29 2023-11-29 Tryptamine derivatives

Country Status (1)

Country Link
WO (1) WO2024118767A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA3182156A1 (en) 2020-05-08 2021-11-11 Psilera Inc. Novel compositions of matter and pharmaceutical compositions
EP4347562A4 (en) 2021-05-25 2025-04-30 ATAI Therapeutics, Inc. New n,n-dimethyltryptamine salts and crystalline salt forms
WO2024227149A2 (en) * 2023-04-27 2024-10-31 Atai Therapeutics, Inc. Alkoxy and carbamoyl quaternary amine salts as prodrugs of trpytamines
WO2025042937A1 (en) * 2023-08-22 2025-02-27 Caamtech, Inc. 5-methoxytryptammonium hydrophthalate
WO2025043053A1 (en) * 2023-08-23 2025-02-27 Caamtech, Inc. 4-methoxy-n,n-dicyclopropyltryptammonium chloride

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210145851A1 (en) * 2019-11-19 2021-05-20 Paul Edward Stamets Tryptamine compositions for enhancing neurite outgrowth
US20220143051A1 (en) * 2019-03-07 2022-05-12 Arbormentis LLC Compositions and methods of use comprising substances with neural plasticity actions administered at non-psychedelic/psychotomimetic dosages and formulations

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220143051A1 (en) * 2019-03-07 2022-05-12 Arbormentis LLC Compositions and methods of use comprising substances with neural plasticity actions administered at non-psychedelic/psychotomimetic dosages and formulations
US20210145851A1 (en) * 2019-11-19 2021-05-20 Paul Edward Stamets Tryptamine compositions for enhancing neurite outgrowth

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE PubChem 1 August 2011 (2011-08-01), ANONYMOUS: "124441911", XP093196886, Database accession no. SID 124441911 *
DATABASE PubChem 12 December 2011 (2011-12-12), ANONYMOUS: "2-(5-methoxy-1H-indol-3- yl)ethylammonium", XP093196888, Database accession no. SID 131323082 *
DATABASE PubChem 13 January 2022 (2022-01-13), ANONYMOUS: "61-54-1", XP093196878, Database accession no. SID 459199938 *
DATABASE PubChem 14 September 2022 (2022-09-14), ANONYMOUS: "Tryptaminium", XP093196882, Database accession no. SID 471270160 *
PHAM DUYEN N. K., SAMMETA VAMSHIKRISHNA REDDY, CHADEAYNE ANDREW R., GOLEN JAMES A., MANKE DAVID R.: "`Foxtrot' fumarate: a water-soluble salt of N , N -diallyl-5-methoxytryptamine (5-MeO-DALT)", ACTA CRYSTALLOGRAPHICA SECTION E CRYSTALLOGRAPHIC COMMUNICATIONS, vol. 77, no. 4, 1 April 2021 (2021-04-01), pages 416 - 419, XP055864001, DOI: 10.1107/S2056989021002838 *

Also Published As

Publication number Publication date
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