AU2022330718B2 - Compositions comprising non-racemic mixtures of (r)- and (s)-3,4-methylenedioxymethamphetamine or (r) and (s) n-methyl-1,3-benzodioxolylbutanamine and uses thereof - Google Patents

Compositions comprising non-racemic mixtures of (r)- and (s)-3,4-methylenedioxymethamphetamine or (r) and (s) n-methyl-1,3-benzodioxolylbutanamine and uses thereof

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Publication number
AU2022330718B2
AU2022330718B2 AU2022330718A AU2022330718A AU2022330718B2 AU 2022330718 B2 AU2022330718 B2 AU 2022330718B2 AU 2022330718 A AU2022330718 A AU 2022330718A AU 2022330718 A AU2022330718 A AU 2022330718A AU 2022330718 B2 AU2022330718 B2 AU 2022330718B2
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AU
Australia
Prior art keywords
mdma
solvate
btbr
lights
mice
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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.)
Active
Application number
AU2022330718A
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English (en)
Other versions
AU2022330718A1 (en
Inventor
Leonard HOWELL
Nicholas KADYSH
Harpreet Kaur
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.)
Pharmala Biotech Inc
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Pharmala Biotech Inc
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Application filed by Pharmala Biotech Inc filed Critical Pharmala Biotech Inc
Publication of AU2022330718A1 publication Critical patent/AU2022330718A1/en
Application granted granted Critical
Publication of AU2022330718B2 publication Critical patent/AU2022330718B2/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • 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
    • A61P25/18—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
    • A61P25/30—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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34—Tobacco-abuse
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
AU2022330718A 2021-08-20 2022-08-22 Compositions comprising non-racemic mixtures of (r)- and (s)-3,4-methylenedioxymethamphetamine or (r) and (s) n-methyl-1,3-benzodioxolylbutanamine and uses thereof Active AU2022330718B2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US202163235460P 2021-08-20 2021-08-20
US63/235,460 2021-08-20
US202263298820P 2022-01-12 2022-01-12
US63/298,820 2022-01-12
PCT/CA2022/051269 WO2023019369A1 (en) 2021-08-20 2022-08-22 Compositions comprising non-racemic mixtures of (r)- and (s)-3,4-methylenedioxymethamphetamine or (r) and (s) n-methyl-1,3-benzodioxolylbutanamine and uses thereof

Publications (2)

Publication Number Publication Date
AU2022330718A1 AU2022330718A1 (en) 2024-03-28
AU2022330718B2 true AU2022330718B2 (en) 2026-02-19

Family

ID=85239329

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2022330718A Active AU2022330718B2 (en) 2021-08-20 2022-08-22 Compositions comprising non-racemic mixtures of (r)- and (s)-3,4-methylenedioxymethamphetamine or (r) and (s) n-methyl-1,3-benzodioxolylbutanamine and uses thereof

Country Status (8)

Country Link
US (3) US12053452B2 (https=)
EP (1) EP4387612A4 (https=)
JP (1) JP2024531437A (https=)
KR (1) KR20240061644A (https=)
AU (1) AU2022330718B2 (https=)
CA (1) CA3229363A1 (https=)
IL (1) IL310937A (https=)
WO (1) WO2023019369A1 (https=)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2022283967A1 (en) * 2021-06-03 2024-01-18 Arcadia Medicine, Inc. Enantiomeric entactogen compositions and methods of their use
US12492178B2 (en) 2021-09-01 2025-12-09 Empathbio, Inc. Stable polymorph of R-MDMA HCl
US11912680B2 (en) 2021-12-28 2024-02-27 Empathbio, Inc. Nitric oxide releasing prodrugs of MDA and MDMA
KR20240165982A (ko) * 2022-03-31 2024-11-25 트랜센드 테라퓨틱스 인코퍼레이티드 향정신성 의약품과 정신 및 신경계 병태 및 장애를 치료하기 위한 이의 용도

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022150525A1 (en) * 2021-01-06 2022-07-14 Awakn Life Sciences Mdma in the treatment of alcohol use disorder
WO2022235500A1 (en) 2021-05-03 2022-11-10 Mind Medicine, Inc. Psychedelics for treatment of pain
JP2024517194A (ja) 2021-05-03 2024-04-19 マインド メディシン， インコーポレイテッド サイケデリック薬の用量を漸増する方法
US12611399B2 (en) 2021-05-04 2026-04-28 Definium Therapeutics US, Inc. Movement disorders
WO2022235514A1 (en) 2021-05-04 2022-11-10 Mind Medicine, Inc. Liposome delivery of psychedelics
US20220354822A1 (en) * 2021-05-05 2022-11-10 Mind Medicine, Inc. Mdma enantiomers
WO2022232948A1 (en) * 2021-05-06 2022-11-10 Pharmala Biotech Inc. Processes for the preparation of the enantiomers of 3,4-methylenedioxymethamphetamine (mdma) and n-methyl-1,3-benzodioxolylbutanamine (mbdb)
WO2022232949A1 (en) * 2021-05-06 2022-11-10 Pharmala Biotech Inc. Processes for the preparation of the enantiomers of 3,4-methylenedioxymethamphetamine (mdma) and n-methyl-1,3-benzodioxolylbutanamine (mbdb)
AU2022283967A1 (en) 2021-06-03 2024-01-18 Arcadia Medicine, Inc. Enantiomeric entactogen compositions and methods of their use
WO2023056472A1 (en) 2021-09-30 2023-04-06 ATAI Life Sciences AG Enantiomeric ratios of 3,4-methylenedioxymethamphetamine and related metabolites and uses thereof
CA3242786A1 (en) 2022-01-07 2023-07-13 Universitatsspital Basel R-mdma and s-mdma to assist psychotherapy

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CURRY ET AL., NEUROPHARMACOLOGY, 2018, vol. 128, pages 196 - 206. DOI: 10.1016/j.neuropharm.2017.10.003 *
LYKOS THERAPEUTICS: clinicaltrials.gov, NCT02008396 version 19, 11 Jun 2021. URL: https://clinicaltrials.gov/study/NCT02008396?tab=history&a=19 [retrieved online 05 Sep 2025]. *
PITTS ELIZABETH G et al., "(±)-MDMA and its enantiomers: potential therapeutic advantages ofR(−)-MDMA", PSYCHOPHARMACOLOGY, 2017, vol. 235, no. 2, pages 377 - 392. DOI: 10.1007/s00213-017-4812-5 *

Also Published As

Publication number Publication date
US12053452B2 (en) 2024-08-06
EP4387612A1 (en) 2024-06-26
WO2023019369A1 (en) 2023-02-23
IL310937A (en) 2024-04-01
AU2022330718A1 (en) 2024-03-28
CA3229363A1 (en) 2023-02-23
JP2024531437A (ja) 2024-08-29
US20250170095A1 (en) 2025-05-29
EP4387612A4 (en) 2025-07-23
KR20240061644A (ko) 2024-05-08
US20230201159A1 (en) 2023-06-29
US20240335419A1 (en) 2024-10-10

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