CA3208152A1 - Multi-substituent psilocybin derivatives and methods of using - Google Patents

Multi-substituent psilocybin derivatives and methods of using Download PDF

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Publication number
CA3208152A1
CA3208152A1 CA3208152A CA3208152A CA3208152A1 CA 3208152 A1 CA3208152 A1 CA 3208152A1 CA 3208152 A CA3208152 A CA 3208152A CA 3208152 A CA3208152 A CA 3208152A CA 3208152 A1 CA3208152 A1 CA 3208152A1
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CA
Canada
Prior art keywords
group
nucleic acid
acid sequence
seq
formula
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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
CA3208152A
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English (en)
French (fr)
Inventor
Jillian M. HAGEL
Peter J. Facchini
Chang-Chun LING
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.)
Enveric Biosciences Canada Inc
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Enveric Biosciences Canada Inc
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Filing date
Publication date
Application filed by Enveric Biosciences Canada Inc filed Critical Enveric Biosciences Canada Inc
Publication of CA3208152A1 publication Critical patent/CA3208152A1/en
Pending legal-status Critical Current

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    • 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
    • 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
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1025—Acyltransferases (2.3)
    • C12N9/1029—Acyltransferases (2.3) transferring groups other than amino-acyl groups (2.3.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1085—Transferases (2.) transferring alkyl or aryl groups other than methyl groups (2.5)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/88—Lyases (4.)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y205/00—Transferases transferring alkyl or aryl groups, other than methyl groups (2.5)
    • C12Y205/01—Transferases transferring alkyl or aryl groups, other than methyl groups (2.5) transferring alkyl or aryl groups, other than methyl groups (2.5.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y401/00—Carbon-carbon lyases (4.1)
    • C12Y401/01—Carboxy-lyases (4.1.1)
    • C12Y401/0102—Diaminopimelate decarboxylase (4.1.1.20)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y401/00—Carbon-carbon lyases (4.1)
    • C12Y401/01—Carboxy-lyases (4.1.1)
    • C12Y401/01028—Aromatic-L-amino-acid decarboxylase (4.1.1.28), i.e. tryptophane-decarboxylase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y402/00—Carbon-oxygen lyases (4.2)
    • C12Y402/01—Hydro-lyases (4.2.1)
    • C12Y402/0102—Tryptophan synthase (4.2.1.20)

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychiatry (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
CA3208152A 2021-02-12 2022-02-11 Multi-substituent psilocybin derivatives and methods of using Pending CA3208152A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US202163149001P 2021-02-12 2021-02-12
US63/149,001 2021-02-12
US202163247881P 2021-09-24 2021-09-24
US63/247,881 2021-09-24
PCT/CA2022/050206 WO2022170438A1 (en) 2021-02-12 2022-02-11 Multi-substituent psilocybin derivatives and methods of using

Publications (1)

Publication Number Publication Date
CA3208152A1 true CA3208152A1 (en) 2022-08-18

Family

ID=82838865

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3208152A Pending CA3208152A1 (en) 2021-02-12 2022-02-11 Multi-substituent psilocybin derivatives and methods of using

Country Status (9)

Country Link
US (4) US11918594B2 (enExample)
EP (1) EP4291549A4 (enExample)
JP (1) JP2024506667A (enExample)
KR (1) KR20230157342A (enExample)
AU (1) AU2022218921A1 (enExample)
CA (1) CA3208152A1 (enExample)
IL (1) IL305125A (enExample)
MX (1) MX2023009491A (enExample)
WO (1) WO2022170438A1 (enExample)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11312684B1 (en) 2021-02-10 2022-04-26 Eleusis Therapeutics Us, Inc. Pharmaceutically acceptable salts of psilocin and uses thereof
CA3219577A1 (en) * 2021-05-27 2022-12-01 Nicholas Stuart William MILNE Methods for producing tryptamine derivatives.
WO2023168023A1 (en) 2022-03-04 2023-09-07 Reset Pharmaceuticals, Inc. Co-crystals or salts comprising psilocin
GB202315025D0 (en) * 2023-09-29 2023-11-15 Psylink Uab Production and medical use of psilocybin and related compounds
WO2025099444A1 (en) * 2023-11-09 2025-05-15 Beckley Psytech Limited N-Acetylserotonin (NAS) Analogues

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3182071A (en) * 1961-06-27 1965-05-04 Warner Lambert Pharmaceutical Acylated indole derivatives
US4803218A (en) * 1982-09-29 1989-02-07 Mcneilab, Inc. 3-aminoalkyl-1H-indole-5-urea and amide derivatives
DK1859798T3 (en) * 2001-03-29 2016-03-21 Lilly Co Eli N- (2-arylethyl) -BENZYLAMINER as antagonists of 5-HT6 receptor
ATE553190T1 (de) * 2006-02-22 2012-04-15 Brain Biotechnology Res & Information Network Ag Neue halogenase
US10138205B2 (en) * 2015-02-19 2018-11-27 University Of Florida Research Foundation, Incorporated Artificial self-sufficient cytochrome P450s
KR101934048B1 (ko) * 2017-03-09 2019-03-26 고려대학교 산학협력단 플라빈-의존형 할로게나아제 및 이를 이용한 할로겐화 인돌 화합물의 제조방법
US11591627B2 (en) * 2018-03-21 2023-02-28 University Of Florida Research Foundation, Incorporated Modified bacteria for production of nitroaromatics
CA3132731A1 (en) * 2019-03-07 2020-09-10 University Of Padova Compositions and methods of use comprising substances with neural plasticity actions administered at non-psychedelic/psychotomimetic dosages and formulations
WO2021226416A1 (en) * 2020-05-08 2021-11-11 Psilera Inc. Novel compositions of matter and pharmaceutical compositions
WO2022047583A1 (en) * 2020-09-02 2022-03-10 Magicmed Industries Inc. Nitrated psilocybin derivatives and use thereof for modulating 5-ht2a receptor and for treating a psychiatric disorder
WO2022115944A1 (en) * 2020-12-01 2022-06-09 Magicmed Industries Inc. Carboxylated psilocybin derivatives and methods of using

Also Published As

Publication number Publication date
JP2024506667A (ja) 2024-02-14
KR20230157342A (ko) 2023-11-16
AU2022218921A9 (en) 2024-01-11
WO2022170438A1 (en) 2022-08-18
US12133856B2 (en) 2024-11-05
US20250025483A1 (en) 2025-01-23
IL305125A (en) 2023-10-01
MX2023009491A (es) 2023-10-13
US11918594B2 (en) 2024-03-05
US20230270768A1 (en) 2023-08-31
US20240122950A1 (en) 2024-04-18
US20240173340A1 (en) 2024-05-30
EP4291549A1 (en) 2023-12-20
US12128058B2 (en) 2024-10-29
AU2022218921A1 (en) 2023-09-21
EP4291549A4 (en) 2025-01-22

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