CN116782896A - 硝化裸盖菇素衍生物及其用于调节5-ht2a受体和治疗精神障碍的用途 - Google Patents

硝化裸盖菇素衍生物及其用于调节5-ht2a受体和治疗精神障碍的用途 Download PDF

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Publication number
CN116782896A
CN116782896A CN202180068083.6A CN202180068083A CN116782896A CN 116782896 A CN116782896 A CN 116782896A CN 202180068083 A CN202180068083 A CN 202180068083A CN 116782896 A CN116782896 A CN 116782896A
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alkyl
group
hydrogen atom
compound
nitro
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Chinese (zh)
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吉利恩·M·哈格尔
彼得·J·法基尼
林长春
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Nvirick Biosciences Canada Co
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Nvirick Biosciences Canada Co
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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
    • 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
    • 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
    • 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
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09Recombinant DNA-technology
    • C12N15/11DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/52Genes encoding for enzymes or proenzymes
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10Transferases (2.)
    • C12N9/1025Acyltransferases (2.3)
    • C12N9/1029Acyltransferases (2.3) transferring groups other than amino-acyl groups (2.3.1)
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N9/00Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/88Lyases (4.)
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10Nitrogen as only ring hetero atom
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12YENZYMES
    • C12Y203/00Acyltransferases (2.3)
    • C12Y203/01Acyltransferases (2.3) transferring groups other than amino-acyl groups (2.3.1)
    • C12Y203/01005Arylamine N-acetyltransferase (2.3.1.5)
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12YENZYMES
    • C12Y401/00Carbon-carbon lyases (4.1)
    • C12Y401/01Carboxy-lyases (4.1.1)
    • C12Y401/01028Aromatic-L-amino-acid decarboxylase (4.1.1.28), i.e. tryptophane-decarboxylase
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12YENZYMES
    • C12Y402/00Carbon-oxygen lyases (4.2)
    • C12Y402/01Hydro-lyases (4.2.1)
    • C12Y402/0102Tryptophan synthase (4.2.1.20)

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  • Chemical & Material Sciences (AREA)
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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Genetics & Genomics (AREA)
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  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Plant Pathology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
CN202180068083.6A 2020-09-02 2021-09-02 硝化裸盖菇素衍生物及其用于调节5-ht2a受体和治疗精神障碍的用途 Pending CN116782896A (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US202063073534P 2020-09-02 2020-09-02
US63/073,534 2020-09-02
PCT/CA2021/051214 WO2022047583A1 (en) 2020-09-02 2021-09-02 Nitrated psilocybin derivatives and use thereof for modulating 5-ht2a receptor and for treating a psychiatric disorder

Publications (1)

Publication Number Publication Date
CN116782896A true CN116782896A (zh) 2023-09-19

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CN202180068083.6A Pending CN116782896A (zh) 2020-09-02 2021-09-02 硝化裸盖菇素衍生物及其用于调节5-ht2a受体和治疗精神障碍的用途

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US (1) US20230040398A1 (https=)
EP (1) EP4208446A4 (https=)
JP (1) JP2023539390A (https=)
KR (1) KR20230061473A (https=)
CN (1) CN116782896A (https=)
AU (1) AU2021336667A1 (https=)
CA (1) CA3191095A1 (https=)
IL (1) IL301028A (https=)
MX (1) MX2023002619A (https=)
WO (1) WO2022047583A1 (https=)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP4291549A4 (en) 2021-02-12 2025-01-22 Enveric Biosciences Canada Inc. MULTISUBSTITUENT PSILOCYLYBINDER DERIVATIVES AND METHODS OF USE
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
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
KR20250097973A (ko) * 2022-11-18 2025-06-30 인베릭 바이오사이언시스 캐나다 인크. 치환된 n-프로필아민 융합 헤테로사이클릭 메스칼린 유도체

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999064044A1 (en) * 1998-06-08 1999-12-16 Advanced Medicine, Inc. Novel therapeutic agents that modulate 5-ht receptors
CN1450896A (zh) * 2000-07-28 2003-10-22 印斯拜尔药品股份有限公司 用吲哚衍生物降低眼内压的方法
CN1610547A (zh) * 2001-03-29 2005-04-27 伊莱利利公司 用作5-ht6受体拮抗剂的n-(2-芳乙基)苄胺
WO2018081456A1 (en) * 2016-10-26 2018-05-03 University Of Florida Research Foundation, Incorporated Highly active self-sufficient nitration biocatalysts

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2172415B2 (es) * 2000-07-28 2003-11-16 Univ Madrid Complutense Tratamiento del glaucoma y la hipertension ocular por medio de un analogo de la melatonina.
EP1747779A1 (en) * 2005-07-28 2007-01-31 Laboratorios Del Dr. Esteve, S.A. Tetrahydro-b-carbolin-sulfonamide derivatives as 5-HT6 ligands
CN103601662B (zh) * 2013-11-21 2016-04-06 深圳市药品检验所 一种褪黑素半抗原、褪黑素完全抗原及其制备方法和应用
WO2015140799A1 (en) * 2014-03-18 2015-09-24 Carmel-Haifa University Economic Corp. Ltd Methods for improving cognitive function via modulation of quinone reductase 2
WO2018106907A1 (en) * 2016-12-08 2018-06-14 Novatarg, Inc. Fused bicyclic alkylene linked imidodicarbonimidic diamides, methods for synthesis, and uses in therary
US20200147038A1 (en) * 2017-04-20 2020-05-14 Eleusis Benefit Corporation, Pbc Assessing and treating psychedelic-responsive subjects
US10640508B2 (en) * 2017-10-13 2020-05-05 Massachusetts Institute Of Technology Diazene directed modular synthesis of compounds with quaternary carbon centers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999064044A1 (en) * 1998-06-08 1999-12-16 Advanced Medicine, Inc. Novel therapeutic agents that modulate 5-ht receptors
CN1450896A (zh) * 2000-07-28 2003-10-22 印斯拜尔药品股份有限公司 用吲哚衍生物降低眼内压的方法
CN1610547A (zh) * 2001-03-29 2005-04-27 伊莱利利公司 用作5-ht6受体拮抗剂的n-(2-芳乙基)苄胺
WO2018081456A1 (en) * 2016-10-26 2018-05-03 University Of Florida Research Foundation, Incorporated Highly active self-sufficient nitration biocatalysts

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
AURORA FINE CHEMICALS 等提供的产品目录: "STN检索报告", 《数据库REGISTRY(在线)》, 8 July 2020 (2020-07-08), pages 1 - 8 *
BRUCE E. BLOUGH ET AL.: "Alpha-ethyltryptamines as dual dopamine–serotonin releasers", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》, vol. 24, no. 19, 29 July 2014 (2014-07-29), pages 4754 - 4758, XP029064422, DOI: 10.1016/j.bmcl.2014.07.062 *
FABIENNE PEYROT ET AL.: "Nitrosation of N-Terminally Blocked Tryptophan and Tryptophan- Containing Peptides by Peroxynitrite", 《CHEMBIOCHEM》, vol. 8, 20 December 2006 (2006-12-20), pages 217 - 223, XP055911501, DOI: 10.1002/cbic.200600385 *
J. B. MCKAY ET AL.: "ANALOGUES OF PSILOCIN AND LYSERGIC ACID DIETHYLAMIDE I. CHLORO, NITRO, AND AMINO DERIVATIVES OF 3-SUBSTITUTED INDOLES", 《CANADIAN JOURNAL OF CHEMISTRY》, vol. 41, 31 December 1963 (1963-12-31), pages 2585 - 2590, XP055911511, DOI: 10.1139/v63-378 *
JORG HOLENZ ET AL.: "Medicinal Chemistry Driven Approaches Toward Novel and Selective Serotonin 5-HT6 Receptor Ligands", 《J. MED. CHEM.》, vol. 48, no. 6, 31 December 2005 (2005-12-31), pages 1781 - 1795, XP002993846, DOI: 10.1021/jm049615n *
L. KH. VINOGRAD ET AL.: "INDOLE DERIVATIVES.126. SUBSTITUTED NITROTRYPTAMINES", 《CHEM. HETEROCYCL. CMOPD.》, vol. 20, 30 September 1984 (1984-09-30), pages 984 - 988 *
RINAT F. SALIKOV ET AL.: "Synthesis and cytotoxic properties of tryptamine derivatives", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》, 27 June 2015 (2015-06-27), pages 3597, XP029249455, DOI: 10.1016/j.bmcl.2015.06.070 *
VERONIQUE LECLERC ET AL.: "Synthesis of Nitroindole Derivatives with High Affinity and Selectivity for Melatoninergic Binding Sites MT3", 《J. MED. CHEM.》, vol. 45, no. 9, 31 December 2002 (2002-12-31), pages 1853 - 1859, XP002350181, DOI: 10.1021/jm011053+ *

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AU2021336667A1 (en) 2023-03-30
EP4208446A4 (en) 2024-10-30
US20230040398A1 (en) 2023-02-09
CA3191095A1 (en) 2022-03-10
IL301028A (en) 2023-05-01
AU2021336667A8 (en) 2023-04-13
JP2023539390A (ja) 2023-09-13
KR20230061473A (ko) 2023-05-08
EP4208446A1 (en) 2023-07-12
WO2022047583A1 (en) 2022-03-10
MX2023002619A (es) 2023-04-10

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Application publication date: 20230919