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

Prodrugs and derivatives of psilocin and uses thereof Download PDF

Info

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
Authority
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
Other languages
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

Links

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 (https=)
EP (1) EP4387608A4 (https=)
JP (1) JP2024534801A (https=)
KR (1) KR20240065084A (https=)
AU (1) AU2022328556A1 (https=)
CA (1) CA3229591A1 (https=)
TW (1) TW202315863A (https=)
WO (1) WO2023023347A1 (https=)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2632056B (en) * 2020-08-21 2025-04-16 Compass Pathfinder Ltd 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
CA3225133A1 (en) 2021-07-07 2023-01-12 Matthew Alexander James Duncton N,n-dimethyltryptamine and related psychedlics and uses thereof
EP4429672A4 (en) 2021-11-12 2025-04-30 Terran Biosciences Inc. PSILOCYBIN AND O-ACETYLPSILOCIN, SALTS AND SOLID FORMS THEREOF
TW202333668A (zh) 2021-12-15 2023-09-01 美商德利克斯醫療公司 經苯氧基及苄氧基取代之精神成形素(psychoplastogen)及其用途
WO2023168023A1 (en) 2022-03-04 2023-09-07 Reset Pharmaceuticals, Inc. Co-crystals or salts comprising psilocin
US12065404B2 (en) 2022-03-18 2024-08-20 Enveric Biosciences Canada Inc. C4-carboxylic acid-substituted tryptamine derivatives and methods of using
EP4493544A4 (en) * 2022-03-18 2026-03-04 Enveric Biosciences Canada Inc TRYPTAMINE DERIVATIVE SALTS SUBSTITUTED WITH C4-CARBOXYLIC ACID AND C4-CARBONOTHIOATE AND METHODS OF USE
AU2022446955A1 (en) * 2022-03-18 2024-11-07 Enveric Biosciences Canada Inc. C4-carboxylic acid-substituted tryptamine derivatives and methods of using
WO2024055106A1 (en) * 2022-09-12 2024-03-21 Bionxt Solutions Inc. Amino acid and carbohydrate psilocin derivatives
EP4618981A1 (en) 2022-11-17 2025-09-24 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
US20250066394A1 (en) * 2023-08-25 2025-02-27 Compass Pathfinder Limited 3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-4-yl DERIVATIVES
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 (9)

* 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
WO2019099745A1 (en) * 2017-11-16 2019-05-23 CaaMTech, LLC Compositions comprising a psilocybin derivative and a cannabinoid
PH12022551981A1 (en) * 2020-02-04 2023-10-16 Mindset Pharma Inc Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders
AU2021268204A1 (en) * 2020-05-08 2022-12-08 Psilera Inc. Novel compositions of matter and pharmaceutical compositions
CN115867533B (zh) * 2020-06-30 2024-07-23 加拿大瑞安神经科学公司 色胺前药
GB2632056B (en) * 2020-08-21 2025-04-16 Compass Pathfinder Ltd 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
MX2023014620A (es) * 2021-06-09 2024-01-30 Atai Therapeutics Inc Nuevos profarmacos y conjugados de dimetiltriptamina.

Also Published As

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

Similar Documents

Publication Publication Date Title
CA3229591A1 (en) Prodrugs and derivatives of psilocin and uses thereof
CN113631557B (zh) Jak激酶抑制剂及其制备方法和在医药领域的应用
AU2020222881B2 (en) Thioeno(3,2-b) pyridin-7-amine compounds for treating familial dysautonomia
TWI765908B (zh) 苯並咪唑類化合物激酶抑制劑及其製備方法和應用
CA3207392A1 (en) Cdk inhibitor
AU2022325376A1 (en) Naphthyridine derivative as atr inhibitor and method for preparing same
EP3248980A1 (en) Jak inhibitor
CA3225135A1 (en) 3,4-methylenedioxymethamphetamine and related psychedlics and uses thereof
US20240116870A1 (en) N,n-dimethyltryptamine and related psychedelics and uses thereof
KR20250112279A (ko) 헤테로고리 화합물, 이의 제조 방법 및 용도
CA3221997A1 (en) Compound as cdk kinase inhibitor and use thereof
WO2024026479A2 (en) Cdk2 inhibitors and methods of using the same
WO2023115002A1 (en) Analogs of 4-bromo-2,5-dimethoxyphenethylamine
TWI723480B (zh) 用作fgfr4抑制劑的稠環衍生物
CA3231988A1 (en) Azaindazole macrocycle compound and use thereof
AU2020404326A1 (en) Heterocyclic compound, and pharmaceutical composition thereof, preparation method therefor, intermediate thereof and application thereof
JP6454413B2 (ja) アミノスルホニル系化合物、その製造方法、および使用
CN107382967B (zh) 咔唑磺酰胺衍生物或其可药用盐及其制备方法和应用
RU2772274C2 (ru) Селективные ингибиторы hdac6, способ их получения и их применение
CN118119389A (zh) 脱磷酸裸盖菇素的前药和衍生物及其用途
CN119866332A (zh) 铁死亡抑制剂-吩噁嗪乙酰胺
EP2784065B1 (en) Glycine reuptake inhibitor and use thereof
BR112019008656B1 (pt) Composto de aminopirazolopirimidina, composição farmacêutica que compreende o mesmo e uso do dito composto para a profilaxia ou o tratamento de uma doença mediada por receptor de tirosina quinase de fator neurotrófico

Legal Events

Date Code Title Description
MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 2ND ANNIV.) - STANDARD

Year of fee payment: 2

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-1-1-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20240722

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-1-1-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20240722

Free format text: ST27 STATUS EVENT CODE: A-1-1-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20240722

P22 Classification modified

Free format text: ST27 STATUS EVENT CODE: A-1-1-P10-P22-P110 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CLASSIFICATION MODIFIED

Effective date: 20240918

MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 3RD ANNIV.) - STANDARD

Year of fee payment: 3

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-1-1-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250702

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-1-1-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250702