GB2632056B - Novel psilocin derivatives having prodrug properties - Google Patents

Novel psilocin derivatives having prodrug properties Download PDF

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Publication number
GB2632056B
GB2632056B GB2412449.7A GB202412449A GB2632056B GB 2632056 B GB2632056 B GB 2632056B GB 202412449 A GB202412449 A GB 202412449A GB 2632056 B GB2632056 B GB 2632056B
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Prior art keywords
psilocin
derivatives
novel
prodrug properties
prodrug
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GB2632056A (en
GB202412449D0 (en
Inventor
Grill Matthias
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Compass Pathfinder Ltd
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Compass Pathfinder Ltd
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Priority claimed from DE102020121965.2A external-priority patent/DE102020121965A1/de
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Publication of GB2632056A publication Critical patent/GB2632056A/en
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    • 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
    • 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
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42Oxazoles
    • A61K31/422Oxazoles not condensed and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • A61P25/06Antimigraine agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • 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
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • 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
    • C07D209/16Tryptamines
    • 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
    • C07D209/18Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/12Heterocyclic 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
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychology (AREA)
  • Addiction (AREA)
  • Otolaryngology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
GB2412449.7A 2020-08-21 2021-08-23 Novel psilocin derivatives having prodrug properties Active GB2632056B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102020121965.2A DE102020121965A1 (de) 2020-08-21 2020-08-21 Neuartige Derivate des Psilocins mit Prodrug-Eigenschaften
US202063118842P 2020-11-27 2020-11-27
GB2304067.8A GB2613993B (en) 2020-08-21 2021-08-23 Novel psilocin derivatives having prodrug properties

Publications (3)

Publication Number Publication Date
GB202412449D0 GB202412449D0 (en) 2024-10-09
GB2632056A GB2632056A (en) 2025-01-22
GB2632056B true GB2632056B (en) 2025-04-16

Family

ID=77739049

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2412449.7A Active GB2632056B (en) 2020-08-21 2021-08-23 Novel psilocin derivatives having prodrug properties
GB2304067.8A Active GB2613993B (en) 2020-08-21 2021-08-23 Novel psilocin derivatives having prodrug properties

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2304067.8A Active GB2613993B (en) 2020-08-21 2021-08-23 Novel psilocin derivatives having prodrug properties

Country Status (14)

Country Link
US (1) US20230295086A1 (https=)
EP (1) EP4200279A1 (https=)
JP (1) JP2023538402A (https=)
KR (1) KR20230054397A (https=)
CN (2) CN116075499B (https=)
AU (1) AU2021328726A1 (https=)
BR (1) BR112023003153A2 (https=)
CA (1) CA3188636A1 (https=)
CO (1) CO2023003282A2 (https=)
GB (2) GB2632056B (https=)
IL (1) IL300455A (https=)
MX (1) MX2023002133A (https=)
WO (1) WO2022038299A1 (https=)
ZA (1) ZA202301693B (https=)

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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
CN114787363A (zh) 2019-10-01 2022-07-22 恩派瑞安神经科学公司 对真菌进行遗传工程化以调节色胺表达
PH12022551981A1 (en) 2020-02-04 2023-10-16 Mindset Pharma Inc Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders
WO2022120181A1 (en) * 2020-12-03 2022-06-09 Mydecine Innovations Group Inc. Novel psilocin analog compositions and methods of synthesizing the same
US12343328B2 (en) 2020-12-09 2025-07-01 Caamtech, Inc. Dialkyl tryptamines and their therapeutic uses
US12534441B2 (en) 2021-01-15 2026-01-27 Beckley Psytech Limited Tryptamine analogues
EP4126857A1 (en) 2021-01-15 2023-02-08 Beckley Psytech Limited Ergoline analogues
US11312684B1 (en) 2021-02-10 2022-04-26 Eleusis Therapeutics Us, Inc. Pharmaceutically acceptable salts of psilocin and uses thereof
WO2023023347A1 (en) * 2021-08-20 2023-02-23 Terran Biosciences Inc. Prodrugs and derivatives of psilocin and uses thereof
EP4452939A4 (en) * 2021-12-24 2025-12-10 Kuleon Llc SEROTONINERGIC COMPOUNDS, POLYPODS, AND PROMEDICINAL PRODIGITS OF SEROTONIN RECEPTOR AGONISTS AND ANTAGONISTS
EP4457336A4 (en) 2021-12-31 2026-01-14 Empyrean Neuroscience Inc ORGANISMS GENETICALLY MODIFIED TO PRODUCE PSYCHOTROPIC ALKALOIDS
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
US11707447B1 (en) 2022-03-18 2023-07-25 Enveric Biosciences Canada Inc. C4-carbonothioate-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
WO2023201293A2 (en) * 2022-04-13 2023-10-19 Caamtech, Inc. Tryptamine derivatives
EP4522167A1 (en) * 2022-05-10 2025-03-19 Mydecine Innovations Group Inc. Novel psilocin prodrug compounds and methods of synthesizing the same
WO2023219789A1 (en) * 2022-05-10 2023-11-16 Mydecine Innovations Group Inc. Novel psilocin prodrug compounds and methods of synthesizing the same
JP2025527296A (ja) * 2022-08-05 2025-08-20 マインドセット ファーマ インコーポレイテッド セロトニンに関する障害の治療に有用であるセロトニン作動薬としての3-エチルアミノ-インドール二量体
CA3261814A1 (en) * 2022-08-05 2024-02-08 Mindset Pharma Inc. 3-PYRROLIDINE-INDOLE DIMERS USED AS SEROTONINERGY AGENTS USEFUL FOR THE TREATMENT OF DISORDERS ASSOCIATED WITH THESE
US12264131B2 (en) 2022-08-19 2025-04-01 Beckley Psytech Limited Pharmaceutically acceptable salts and compositions thereof
WO2024055106A1 (en) * 2022-09-12 2024-03-21 Bionxt Solutions Inc. Amino acid and carbohydrate psilocin derivatives
US20240269113A1 (en) * 2023-01-24 2024-08-15 Compass Pathfinder Limited 3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-4-yl DERIVATIVES
US12246005B2 (en) 2023-06-13 2025-03-11 Beckley Psytech Limited 5-methoxy-n,n-dimethyltryptamine (5-MeO-DMT) formulations
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

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Publication number Priority date Publication date Assignee Title
WO2021155470A1 (en) * 2020-02-04 2021-08-12 Mindset Pharma Inc. Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders
WO2023023347A1 (en) * 2021-08-20 2023-02-23 Terran Biosciences Inc. Prodrugs and derivatives of psilocin and uses thereof

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US3075992A (en) 1958-09-12 1963-01-29 Sandoz Ltd Esters of indoles
CH386442A (de) 1959-03-18 1965-01-15 Ciba Geigy Verfahren zur Herstellung neuer 7-Aza-benzimidazole
AU2005300045A1 (en) * 2004-09-27 2006-05-04 Organix, Inc. Indole compounds useful as serotonin selective agents
JP2010507585A (ja) * 2006-10-19 2010-03-11 オースペックス・ファーマシューティカルズ・インコーポレイテッド 置換インドール
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
CA3052974A1 (en) * 2017-02-09 2018-08-16 CaaMTech, LLC Compositions and methods comprising a psilocybin derivative
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

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
WO2021155470A1 (en) * 2020-02-04 2021-08-12 Mindset Pharma Inc. Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders
WO2023023347A1 (en) * 2021-08-20 2023-02-23 Terran Biosciences Inc. Prodrugs and derivatives of psilocin and uses thereof

Also Published As

Publication number Publication date
GB2632056A (en) 2025-01-22
WO2022038299A1 (en) 2022-02-24
EP4200279A1 (en) 2023-06-28
GB202412449D0 (en) 2024-10-09
JP2023538402A (ja) 2023-09-07
GB2613993A (en) 2023-06-21
ZA202301693B (en) 2026-01-28
IL300455A (en) 2023-04-01
GB2613993B (en) 2024-10-09
MX2023002133A (es) 2023-05-12
AU2021328726A1 (en) 2023-03-02
CN120904096A (zh) 2025-11-07
KR20230054397A (ko) 2023-04-24
BR112023003153A2 (pt) 2023-04-04
US20230295086A1 (en) 2023-09-21
CN116075499B (zh) 2025-07-25
CA3188636A1 (en) 2022-02-24
CO2023003282A2 (es) 2023-04-17
CN116075499A (zh) 2023-05-05

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