CA3229363A1 - 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 Download PDF

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Publication number
CA3229363A1
CA3229363A1 CA3229363A CA3229363A CA3229363A1 CA 3229363 A1 CA3229363 A1 CA 3229363A1 CA 3229363 A CA3229363 A CA 3229363A CA 3229363 A CA3229363 A CA 3229363A CA 3229363 A1 CA3229363 A1 CA 3229363A1
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CA
Canada
Prior art keywords
solvate
mdma
salt
disorder
formula
Prior art date
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
CA3229363A
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English (en)
French (fr)
Inventor
Nicholas KADYSH
Leonard HOWELL
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
Original Assignee
Pharmala Biotech Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Pharmala Biotech Inc filed Critical Pharmala Biotech Inc
Publication of CA3229363A1 publication Critical patent/CA3229363A1/en
Pending legal-status Critical Current

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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]

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  • 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)
CA3229363A 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 Pending CA3229363A1 (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 (1)

Publication Number Publication Date
CA3229363A1 true CA3229363A1 (en) 2023-02-23

Family

ID=85239329

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3229363A Pending CA3229363A1 (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

Also Published As

Publication number Publication date
AU2022330718B2 (en) 2026-02-19
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
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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