CA3236624A1 - Formulations of psilocybin analogs and methods of use - Google Patents

Formulations of psilocybin analogs and methods of use Download PDF

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Publication number
CA3236624A1
CA3236624A1 CA3236624A CA3236624A CA3236624A1 CA 3236624 A1 CA3236624 A1 CA 3236624A1 CA 3236624 A CA3236624 A CA 3236624A CA 3236624 A CA3236624 A CA 3236624A CA 3236624 A1 CA3236624 A1 CA 3236624A1
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CA
Canada
Prior art keywords
salt
pharmaceutical composition
compound
formula
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
CA3236624A
Other languages
English (en)
French (fr)
Inventor
Alex Nivorozhkin
Michael Palfreyman
Pradip M. Pathare
Kenneth L. Avery
Mohammed I. SHUKOOR
James He HUANG
Michael E. Morgan
Joan M. Krakowsky
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.)
Cybin IRL Ltd
Original Assignee
Cybin IRL Ltd
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
Priority claimed from PCT/EP2022/056991 external-priority patent/WO2022195011A1/en
Application filed by Cybin IRL Ltd filed Critical Cybin IRL Ltd
Publication of CA3236624A1 publication Critical patent/CA3236624A1/en
Pending legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40Heterocyclic 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
    • A61K31/403Heterocyclic 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
    • A61K31/404Indoles, e.g. pindolol
    • A61K31/4045Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0002Galenical forms characterised by the drug release technique; Application systems commanded by energy
    • A61K9/0007Effervescent
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0087Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2022Organic macromolecular compounds
    • A61K9/2063Proteins, e.g. gelatin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002Heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05Isotopically modified compounds, e.g. labelled

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychiatry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
CA3236624A 2021-11-05 2022-09-20 Formulations of psilocybin analogs and methods of use Pending CA3236624A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US202163276117P 2021-11-05 2021-11-05
US63/276,117 2021-11-05
EPPCT/EP2022/056991 2022-03-17
PCT/EP2022/056991 WO2022195011A1 (en) 2021-03-18 2022-03-17 Psilocybin analogs, salts, compositions, and methods of use
PCT/EP2022/076073 WO2023078604A1 (en) 2021-11-05 2022-09-20 Formulations of psilocybin analogs and methods of use

Publications (1)

Publication Number Publication Date
CA3236624A1 true CA3236624A1 (en) 2023-05-11

Family

ID=83558221

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3236624A Pending CA3236624A1 (en) 2021-11-05 2022-09-20 Formulations of psilocybin analogs and methods of use

Country Status (9)

Country Link
US (1) US20250213527A1 (https=)
EP (1) EP4426675A1 (https=)
JP (1) JP2024540282A (https=)
KR (1) KR20240095294A (https=)
CN (1) CN117177959A (https=)
AU (1) AU2022381220B2 (https=)
CA (1) CA3236624A1 (https=)
IL (1) IL312175A (https=)
WO (1) WO2023078604A1 (https=)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2021268204A1 (en) 2020-05-08 2022-12-08 Psilera Inc. Novel compositions of matter and pharmaceutical compositions
IL308816A (en) 2021-05-25 2024-01-01 Atai Therapeutics Inc New n,n-dimethyltryptamine salts and crystalline salt forms
WO2023018864A1 (en) 2021-08-12 2023-02-16 Psilosterics, Llc Hallucinogenic and non-hallucinogenic serotonin receptor agonists and methods of making and using the same
JP2024545787A (ja) 2021-12-30 2024-12-11 アタイ セラピューティクス, インコーポレイテッド 一酸化窒素送達剤としてのジメチルトリプタミン類似体
CA3247344A1 (en) * 2022-06-09 2023-12-14 Diamond Therapeutics Inc. AMORPHIC PSILOCYBIN (A-POLYMORPHIC)
US12049447B2 (en) 2022-06-30 2024-07-30 Zylorion Health Inc. Crystalline forms of compositions comprising psilocin and psilocybin
AU2023343417B2 (en) * 2022-09-12 2026-02-19 Tryp Therapeutics, Inc Psilocin crystalline forms
WO2024180030A1 (en) 2023-02-27 2024-09-06 Cybin Irl Limited Methods of treating depressive disorders with a psilocybin analog
WO2025019800A1 (en) * 2023-07-19 2025-01-23 Atai Therapeutics, Inc. Novel prodrugs and conjugates of dimethyltryptamine and methods of using the same
US12280068B1 (en) 2023-11-09 2025-04-22 Zylorion Health Inc. Uses of a co-crystal of psilocybin and psilocin
US20250302075A1 (en) * 2024-04-01 2025-10-02 Tsi Group Co., Ltd. Compositions and methods of preparation of a clear, effervescent delivery form for nutritional ingredients
US20260021070A1 (en) * 2024-07-19 2026-01-22 Compass Pathfinder Limited Subcutaneous formulations comprising psilocybin derivatives
CN119610304A (zh) * 2024-12-10 2025-03-14 澳创新耐火材料(中山)有限公司 一种低值植物纤维材料重组防火门芯及其制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5612059A (en) 1988-08-30 1997-03-18 Pfizer Inc. Use of asymmetric membranes in delivery devices
US5798119A (en) 1995-06-13 1998-08-25 S. C. Johnson & Son, Inc. Osmotic-delivery devices having vapor-permeable coatings
PH12022551981A1 (en) * 2020-02-04 2023-10-16 Mindset Pharma Inc Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders
US11312684B1 (en) 2021-02-10 2022-04-26 Eleusis Therapeutics Us, Inc. Pharmaceutically acceptable salts of psilocin and uses thereof
WO2022195011A1 (en) * 2021-03-18 2022-09-22 Cybin Irl Limited Psilocybin analogs, salts, compositions, and methods of use

Also Published As

Publication number Publication date
IL312175A (en) 2024-06-01
AU2022381220B2 (en) 2026-03-05
AU2022381220A1 (en) 2024-05-02
EP4426675A1 (en) 2024-09-11
CN117177959A (zh) 2023-12-05
US20250213527A1 (en) 2025-07-03
WO2023078604A1 (en) 2023-05-11
KR20240095294A (ko) 2024-06-25
JP2024540282A (ja) 2024-10-31

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