CA3229591A1 - Prodrugs and derivatives of psilocin and uses thereof - Google Patents

Prodrugs and derivatives of psilocin and uses thereof Download PDF

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Publication number
CA3229591A1
CA3229591A1 CA3229591A CA3229591A CA3229591A1 CA 3229591 A1 CA3229591 A1 CA 3229591A1 CA 3229591 A CA3229591 A CA 3229591A CA 3229591 A CA3229591 A CA 3229591A CA 3229591 A1 CA3229591 A1 CA 3229591A1
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CA
Canada
Prior art keywords
compound
alkyl
solvate
isotopolog
pharmaceutically acceptable
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.)
Pending
Application number
CA3229591A
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English (en)
French (fr)
Inventor
Sam CLARK
Matthew Alexander James Duncton
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.)
Terran Biosciences Inc
Original Assignee
Terran Biosciences 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 Terran Biosciences Inc filed Critical Terran Biosciences Inc
Publication of CA3229591A1 publication Critical patent/CA3229591A1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA3229591A 2021-08-20 2022-08-19 Prodrugs and derivatives of psilocin and uses thereof Pending CA3229591A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US202163235543P 2021-08-20 2021-08-20
US63/235,543 2021-08-20
US202163289025P 2021-12-13 2021-12-13
US63/289,025 2021-12-13
PCT/US2022/040922 WO2023023347A1 (en) 2021-08-20 2022-08-19 Prodrugs and derivatives of psilocin and uses thereof

Publications (1)

Publication Number Publication Date
CA3229591A1 true CA3229591A1 (en) 2023-02-23

Family

ID=85241100

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3229591A Pending CA3229591A1 (en) 2021-08-20 2022-08-19 Prodrugs and derivatives of psilocin and uses thereof

Country Status (8)

Country Link
US (1) US20250011344A1 (enExample)
EP (1) EP4387608A4 (enExample)
JP (1) JP2024534801A (enExample)
KR (1) KR20240065084A (enExample)
AU (1) AU2022328556A1 (enExample)
CA (1) CA3229591A1 (enExample)
TW (1) TW202315863A (enExample)
WO (1) WO2023023347A1 (enExample)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2021328726A1 (en) * 2020-08-21 2023-03-02 Compass Pathfinder Limited Novel psilocin derivatives having prodrug properties
WO2022120181A1 (en) * 2020-12-03 2022-06-09 Mydecine Innovations Group Inc. Novel psilocin analog compositions and methods of synthesizing the same
AU2022309017A1 (en) 2021-07-07 2024-01-25 Terran Biosciences Inc. N,n-dimethyltryptamine and related psychedlics and uses thereof
WO2023086962A1 (en) 2021-11-12 2023-05-19 Terran Biosciences Inc. Psilocybin and o-acetylpsilocin, salts and solid state forms thereof
JP2025502615A (ja) 2021-12-15 2025-01-28 デリックス セラピューティクス，インク． フェノキシおよびベンジルオキシ置換サイコプラストゲンならびにその使用
WO2023168023A1 (en) 2022-03-04 2023-09-07 Reset Pharmaceuticals, Inc. Co-crystals or salts comprising psilocin
EP4493541A4 (en) * 2022-03-18 2026-02-25 Enveric Biosciences Canada Inc TRYPTAMINE DERIVATIVES SUBSTITUTED BY C4-CARBOXYLIC ACID AND METHODS OF USE
US12065404B2 (en) 2022-03-18 2024-08-20 Enveric Biosciences Canada Inc. C4-carboxylic acid-substituted tryptamine derivatives and methods of using
AU2023235712A1 (en) * 2022-03-18 2024-11-07 Enveric Biosciences Canada Inc. C4-substituted tryptamine derivatives and methods of using
CA3267605A1 (en) * 2022-09-12 2024-03-21 Bionxt Solutions Inc. PSILOCIN DERIVATIVES BASED ON AMINO ACIDS AND CARBOHYDRATES
WO2024108195A1 (en) 2022-11-17 2024-05-23 Remedi, Inc. Combinations of monoamine oxidase inhibitors and serotonin receptor agonists and their therapeutic use
US20240269113A1 (en) * 2023-01-24 2024-08-15 Compass Pathfinder Limited 3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-4-yl DERIVATIVES
TW202525777A (zh) * 2023-08-25 2025-07-01 英商康派斯開拓者公司 ３－（２－（二甲基胺基）乙基）－１ｈ－吲哚－４－基衍生物
EP4592276A1 (en) 2024-01-29 2025-07-30 Universität Heidelberg Novel acyloxymethyl prodrugs of psilocin and related 4-hydroxytryptamines obtained by an efficient synthetic approach
CN120329323B (zh) * 2025-04-16 2026-01-13 黄冈鲁班药业股份有限公司 一种头孢吡普酯侧链的制备方法及应用

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3075992A (en) * 1958-09-12 1963-01-29 Sandoz Ltd Esters of indoles
US20180021326A1 (en) * 2016-07-23 2018-01-25 Paul Edward Stamets Compositions and methods for enhancing neuroregeneration and cognition by combining mushroom extracts containing active ingredients psilocin or psilocybin with erinacines or hericenones enhanced with niacin
US20190142851A1 (en) * 2017-11-16 2019-05-16 CaaMTech, LLC Compositions comprising a psilocybin derivative and a cannabinoid
KR102316445B1 (ko) * 2019-11-29 2021-10-26 씨제이제일제당 주식회사 신규 세린 프로테아제 변이체
MX2022009527A (es) * 2020-02-04 2022-11-16 Mindset Pharma Inc Derivados de la psilocina como agentes psicodelicos serotoninergicos para el tratamiento de trastornos del snc.
IL297861A (en) * 2020-05-08 2023-01-01 Psilera Inc Novel compositions of matter and pharmaceutical compositions
DK4172145T3 (da) * 2020-06-30 2026-07-20 Reunion Neuroscience Inc Tryptamin-prodrugs som serotonin-receptor-aktivatorer til behandling af f.eks. depression
AU2021328726A1 (en) * 2020-08-21 2023-03-02 Compass Pathfinder Limited Novel psilocin derivatives having prodrug properties
WO2022120181A1 (en) * 2020-12-03 2022-06-09 Mydecine Innovations Group Inc. Novel psilocin analog compositions and methods of synthesizing the same
IL309210A (en) * 2021-06-09 2024-02-01 Atai Therapeutics Inc Parent drugs and conjugates of dimethyltryptamine

Also Published As

Publication number Publication date
EP4387608A4 (en) 2026-01-07
KR20240065084A (ko) 2024-05-14
AU2022328556A1 (en) 2024-03-07
US20250011344A1 (en) 2025-01-09
TW202315863A (zh) 2023-04-16
JP2024534801A (ja) 2024-09-26
WO2023023347A1 (en) 2023-02-23
EP4387608A1 (en) 2024-06-26

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