CA3078765A1 - Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use - Google Patents

Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use Download PDF

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Publication number
CA3078765A1
CA3078765A1 CA3078765A CA3078765A CA3078765A1 CA 3078765 A1 CA3078765 A1 CA 3078765A1 CA 3078765 A CA3078765 A CA 3078765A CA 3078765 A CA3078765 A CA 3078765A CA 3078765 A1 CA3078765 A1 CA 3078765A1
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CA
Canada
Prior art keywords
polymorph
psilocybin
crystalline
stage
crystalline psilocybin
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
CA3078765A
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English (en)
French (fr)
Inventor
Derek John Londesbrough
Christopher Brown
Julian Scott Northen
Gillian Moore
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.)
Compass Pathfinder Ltd
Original Assignee
Compass Pathways PLC
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
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=60326674&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA3078765(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Compass Pathways PLC filed Critical Compass Pathways PLC
Publication of CA3078765A1 publication Critical patent/CA3078765A1/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
    • 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
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4866—Organic macromolecular compounds
    • 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
    • A61P25/24—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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • 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
    • 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
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • 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
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
CA3078765A 2017-10-09 2018-10-09 Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use Pending CA3078765A1 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
GB1716505.1 2017-10-09
GB1716505.1A GB2571696B (en) 2017-10-09 2017-10-09 Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced
GB1810588.2A GB2572023C2 (en) 2017-10-09 2018-06-28 Crystaline psilocybin polymorph A, a formulation and uses thereof together with a method of preparation
GB1810588.2 2018-06-28
GB1816438.4 2018-10-09
PCT/IB2018/057811 WO2019073379A1 (en) 2017-10-09 2018-10-09 PREPARATION OF PSILOCYBIN, DIFFERENT POLYMORPHIC FORMS, INTERMEDIAIRES, FORMULATIONS AND THEIR USE
GB1816438.4A GB2576059B (en) 2017-10-09 2018-10-09 A pharmaceutical formulation comprising psilocybin

Publications (1)

Publication Number Publication Date
CA3078765A1 true CA3078765A1 (en) 2019-04-18

Family

ID=60326674

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3078765A Pending CA3078765A1 (en) 2017-10-09 2018-10-09 Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use

Country Status (19)

Country Link
US (15) US10519175B2 (https=)
EP (1) EP3694835A1 (https=)
JP (4) JP2020536960A (https=)
KR (2) KR20250041070A (https=)
CN (1) CN111491919A (https=)
AU (3) AU2018349279B2 (https=)
BR (1) BR112020006947A2 (https=)
CA (1) CA3078765A1 (https=)
CO (1) CO2020005643A2 (https=)
DE (1) DE202018006384U1 (https=)
EA (1) EA202090917A1 (https=)
GB (4) GB2571696B (https=)
IL (3) IL322447A (https=)
MX (3) MX2020003910A (https=)
MY (1) MY205385A (https=)
PH (1) PH12020550246A1 (https=)
SG (1) SG11202003198RA (https=)
WO (1) WO2019073379A1 (https=)
ZA (1) ZA202407520B (https=)

Cited By (10)

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WO2021155470A1 (en) * 2020-02-04 2021-08-12 Mindset Pharma Inc. Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders
WO2021253123A1 (en) * 2020-06-17 2021-12-23 Psilo Scientific Ltd Extraction of psychoactive compounds from psychedelic fungus
WO2022016289A1 (en) * 2020-07-24 2022-01-27 Mindset Pharma Inc. Scalable synthetic route for psilocin and psilocybin
US11298388B2 (en) 2020-06-17 2022-04-12 Psilo Scientific Ltd. Psychoactive alkaloid extraction and composition with controlled dephosphorylation
US11382942B2 (en) 2020-06-17 2022-07-12 Psilo Scientific Ltd. Extraction of psychoactive compounds from psilocybin fungus
US11491138B2 (en) 2020-12-28 2022-11-08 Psilo Scientific Ltd. Injectable psychoactive alkaloid composition and preparation thereof
US11510952B2 (en) 2020-06-17 2022-11-29 Psilo Scientific Ltd. Ethanol extraction of psychoactive compounds from psilocybin fungus
WO2024003610A1 (en) * 2022-06-30 2024-01-04 Zylorion Health Inc. Compositions and uses of psilocybin and psilocin
US12233355B2 (en) 2020-06-17 2025-02-25 Psilo Scientific Ltd. Methanol-based extraction of psychoactive alkaloids from fungus
US12280068B1 (en) 2023-11-09 2025-04-22 Zylorion Health Inc. Uses of a co-crystal of psilocybin and psilocin

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US11974984B2 (en) 2017-02-09 2024-05-07 Caamtech, Inc. Compositions and methods comprising a combination of serotonergic drugs
US12414936B2 (en) 2017-02-09 2025-09-16 Caamtech, Inc. Compositions comprising a serotonergic tryptamine compound
GB2571696B (en) 2017-10-09 2020-05-27 Compass Pathways Ltd Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced
US12459965B2 (en) 2017-10-09 2025-11-04 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
MA54877A (fr) * 2019-01-30 2021-12-08 Diamond Therapeutics Inc Compositions et méthodes comprenant un agoniste de récepteur 5ht destinées au traitement de troubles psychologiques, cognitifs, comportementaux et/ou d'humeur
US12377112B2 (en) * 2019-04-17 2025-08-05 Compass Pathfinder Limited Methods of treating neurocognitive disorders, chronic pain and reducing inflammation
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CA3152752A1 (en) 2019-10-01 2021-04-08 Thomas Henley Genetic engineering of fungi to modulate tryptamine expression
KR20220082092A (ko) 2019-11-07 2022-06-16 스몰 파마 엘티디 화합물
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US11332441B2 (en) * 2020-03-23 2022-05-17 Caamtech, Inc. Crystalline N-methyl tryptamine derivatives
US12240813B2 (en) 2020-05-19 2025-03-04 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
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WO2022204323A1 (en) * 2021-03-24 2022-09-29 The Trustees Of Columbia University In The City Of New York Non-hallucinogenic ariadne analogs for treatment of neurological and psychiatric disorders
TW202304466A (zh) * 2021-03-30 2023-02-01 英商康派斯開拓者公司 賽洛西賓（ｐｓｉｌｏｃｙｂｉｎ）組成物，其製備方法及使用方法
EP4334284A1 (en) * 2021-05-07 2024-03-13 Canna-Chemistries LLC New crystalline polymorphic form of psilocin
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