GB2613993B - Novel psilocin derivatives having prodrug properties - Google Patents

Novel psilocin derivatives having prodrug properties Download PDF

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Publication number
GB2613993B
GB2613993B GB2304067.8A GB202304067A GB2613993B GB 2613993 B GB2613993 B GB 2613993B GB 202304067 A GB202304067 A GB 202304067A GB 2613993 B GB2613993 B GB 2613993B
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psilocin
derivatives
novel
prodrug properties
prodrug
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GB2613993A (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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Priority to GB2412449.7A priority Critical patent/GB2632056B/en
Publication of GB2613993A publication Critical patent/GB2613993A/en
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    • 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
    • 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
    • A61K31/41—Heterocyclic 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
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • 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
    • A61P25/18—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
    • A61P25/22—Anxiolytics
    • 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
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • 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
    • 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
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals 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
    • 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
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design 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)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychology (AREA)
  • Addiction (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Otolaryngology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
GB2304067.8A 2020-08-21 2021-08-23 Novel psilocin derivatives having prodrug properties Active GB2613993B (en)

Priority Applications (1)

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

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
PCT/EP2021/073303 WO2022038299A1 (en) 2020-08-21 2021-08-23 Novel psilocin derivatives having prodrug properties

Publications (2)

Publication Number Publication Date
GB2613993A GB2613993A (en) 2023-06-21
GB2613993B true GB2613993B (en) 2024-10-09

Family

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Family Applications (2)

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

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2412449.7A Active GB2632056B (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) GB2613993B (https=)
IL (1) IL300455A (https=)
MX (1) MX2023002133A (https=)
WO (1) WO2022038299A1 (https=)
ZA (1) ZA202301693B (https=)

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US12414936B2 (en) 2017-02-09 2025-09-16 Caamtech, Inc. Compositions comprising a serotonergic tryptamine compound
CA3152752A1 (en) 2019-10-01 2021-04-08 Thomas Henley Genetic engineering of fungi to modulate tryptamine expression
KR20220137081A (ko) 2020-02-04 2022-10-11 마인드셋 파마 인크. Cns 장애의 치료를 위한 세로토닌성 사이키델릭 작용제로서의 실로신 유도체
EP4255422A4 (en) 2020-12-03 2024-12-18 Mydecine Innovations Group Inc. NEW PSILOCIN ANALOGUE COMPOSITIONS AND METHODS OF THEIR SYNTHESIS
KR20230109765A (ko) * 2020-12-09 2023-07-20 캄테크, 인크. 다이알킬 트립타민 및 이의 치료적 용도
EP4155306A1 (en) 2021-01-15 2023-03-29 Beckley Psytech Limited Neuroactive ergoline analogue
US12534441B2 (en) 2021-01-15 2026-01-27 Beckley Psytech Limited Tryptamine analogues
US11312684B1 (en) 2021-02-10 2022-04-26 Eleusis Therapeutics Us, Inc. Pharmaceutically acceptable salts of psilocin and uses thereof
JP2024534801A (ja) * 2021-08-20 2024-09-26 テラン バイオサイエンシズ インコーポレイテッド サイロシンのプロドラッグ及び誘導体ならびにその使用
EP4452939A4 (en) * 2021-12-24 2025-12-10 Kuleon Llc SEROTONINERGIC COMPOUNDS, POLYPODS, AND PROMEDICINAL PRODIGITS OF SEROTONIN RECEPTOR AGONISTS AND ANTAGONISTS
CN118984868A (zh) 2021-12-31 2024-11-19 恩派瑞安神经科学公司 用于产生精神药物生物碱的遗传修饰的生物体
WO2023168023A1 (en) 2022-03-04 2023-09-07 Reset Pharmaceuticals, Inc. Co-crystals or salts comprising psilocin
AU2023234202A1 (en) * 2022-03-18 2024-11-07 Enveric Biosciences Canada Inc. Salts of c4-carboxylic acid- and c4-carbonothioate-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
WO2023173196A1 (en) * 2022-03-18 2023-09-21 Enveric Biosciences Canada Inc. C4-carboxylic acid-substituted tryptamine derivatives and methods of using
CA3248442A1 (en) * 2022-04-13 2023-10-19 Caamtech, Inc. TRYPTAMINE DERIVATIVES
WO2023219789A1 (en) * 2022-05-10 2023-11-16 Mydecine Innovations Group Inc. Novel psilocin prodrug compounds and methods of synthesizing the same
AU2023269880A1 (en) * 2022-05-10 2024-01-18 Mydecine Innovations Group Inc. Novel psilocin prodrug compounds and methods of synthesizing the same
US11981637B2 (en) * 2022-06-09 2024-05-14 Caamtech, Inc. 4-pivaloyloxy-n-methyltryptammonium chloride
AU2023319280A1 (en) * 2022-08-05 2025-03-20 Mindset Pharma Inc. 3-ethylamino-indole dimers as serotonergic agents useful for the treatment of disorders related thereto
CN120091999A (zh) * 2022-08-05 2025-06-03 思维模式制药公司 作为血清素能剂用于治疗相关病症的3-吡咯烷-吲哚二聚体
US12264131B2 (en) 2022-08-19 2025-04-01 Beckley Psytech Limited Pharmaceutically acceptable salts and compositions thereof
US20260085040A1 (en) * 2022-09-12 2026-03-26 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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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
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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
WO2021155470A1 (en) * 2020-02-04 2021-08-12 Mindset Pharma Inc. Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders
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Publication number Publication date
CO2023003282A2 (es) 2023-04-17
IL300455A (en) 2023-04-01
WO2022038299A1 (en) 2022-02-24
JP2023538402A (ja) 2023-09-07
EP4200279A1 (en) 2023-06-28
CA3188636A1 (en) 2022-02-24
KR20230054397A (ko) 2023-04-24
MX2023002133A (es) 2023-05-12
CN120904096A (zh) 2025-11-07
BR112023003153A2 (pt) 2023-04-04
CN116075499B (zh) 2025-07-25
GB2632056A (en) 2025-01-22
GB2613993A (en) 2023-06-21
GB202412449D0 (en) 2024-10-09
AU2021328726A1 (en) 2023-03-02
ZA202301693B (en) 2026-01-28
CN116075499A (zh) 2023-05-05
GB2632056B (en) 2025-04-16
US20230295086A1 (en) 2023-09-21

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