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
Authority
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

    • 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
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
    • A61K9/0007—Effervescent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2063—Proteins, e.g. gelatin
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • 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
    • C07B2200/05—Isotopically 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
PCT/EP2022/056991 WO2022195011A1 (en) 2021-03-18 2022-03-17 Psilocybin analogs, salts, compositions, and methods of use
EPPCT/EP2022/056991 2022-03-17
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 (enExample)
EP (1) EP4426675A1 (enExample)
JP (1) JP2024540282A (enExample)
KR (1) KR20240095294A (enExample)
CN (1) CN117177959A (enExample)
AU (2) AU2022381220B2 (enExample)
CA (1) CA3236624A1 (enExample)
IL (1) IL312175A (enExample)
WO (1) WO2023078604A1 (enExample)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2021009037A (es) 2019-01-30 2021-10-13 Diamond Therapeutics Inc Composiciones y metodos para el manejo de trastornos.
IL297861A (en) 2020-05-08 2023-01-01 Psilera Inc Novel compositions of matter and pharmaceutical compositions
KR20240013170A (ko) 2021-05-25 2024-01-30 아타이 테라퓨틱스, 인크. 신규 n,n-디메틸트립타민 염 및 결정질 염 형태
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
CA3238440A1 (en) 2021-12-30 2023-07-06 Atai Therapeutics, Inc. Dimethyltryptamine analogues as nitric oxide delivery drugs
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
CA3267523A1 (en) * 2022-09-12 2024-03-21 Tryp Therapeutics, Inc CRYSTALLINE FORMS OF PSILOCIN
CN120813349A (zh) 2023-02-27 2025-10-17 赛本爱尔兰有限公司 用裸头草碱类似物治疗抑郁障碍的方法
EP4746873A1 (en) * 2023-07-19 2026-05-27 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 (8)

* 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
US9421266B2 (en) * 2007-05-22 2016-08-23 Pisgah Laboratories, Inc. Safety of pseudoephedrine drug products
KR101837896B1 (ko) * 2016-04-12 2018-03-12 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
JP7273731B2 (ja) * 2017-02-09 2023-05-15 カームテック、エルエルシー シロシビン誘導体を含む組成物及び方法
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.
US11312684B1 (en) 2021-02-10 2022-04-26 Eleusis Therapeutics Us, Inc. Pharmaceutically acceptable salts of psilocin and uses thereof
AU2022239825C1 (en) * 2021-03-18 2026-08-13 Cybin Irl Limited Psilocybin analogs, salts, compositions, and methods of use

Also Published As

Publication number Publication date
US20250213527A1 (en) 2025-07-03
IL312175A (en) 2024-06-01
EP4426675A1 (en) 2024-09-11
WO2023078604A1 (en) 2023-05-11
JP2024540282A (ja) 2024-10-31
KR20240095294A (ko) 2024-06-25
CN117177959A (zh) 2023-12-05
AU2022381220B2 (en) 2026-03-05
AU2026204043A1 (en) 2026-06-11
AU2022381220A1 (en) 2024-05-02

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