AU2015343083B2 - Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods - Google Patents

Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods Download PDF

Info

Publication number
AU2015343083B2
AU2015343083B2 AU2015343083A AU2015343083A AU2015343083B2 AU 2015343083 B2 AU2015343083 B2 AU 2015343083B2 AU 2015343083 A AU2015343083 A AU 2015343083A AU 2015343083 A AU2015343083 A AU 2015343083A AU 2015343083 B2 AU2015343083 B2 AU 2015343083B2
Authority
AU
Australia
Prior art keywords
pharmaceutically acceptable
acceptable salt
compound
ketamine
norketamine
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.)
Active
Application number
AU2015343083A
Other languages
English (en)
Other versions
AU2015343083A1 (en
Inventor
Nelson Landrau
Alex Nivorozhkin
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.)
Acadia Pharmaceuticals Inc
Original Assignee
Acadia Pharmaceuticals 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 Acadia Pharmaceuticals Inc filed Critical Acadia Pharmaceuticals Inc
Publication of AU2015343083A1 publication Critical patent/AU2015343083A1/en
Application granted granted Critical
Publication of AU2015343083B2 publication Critical patent/AU2015343083B2/en
Assigned to ACADIA PHARMACEUTICALS INC. reassignment ACADIA PHARMACEUTICALS INC. Request for Assignment Assignors: AMORSA THERAPEUTICS, INC.
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/13Amines
    • A61K31/133Amines having hydroxy groups, e.g. sphingosine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/13Amines
    • A61K31/135Amines having aromatic rings, e.g. ketamine, nortriptyline
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/21Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2009Inorganic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • A61K9/2018Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2022Organic macromolecular compounds
    • A61K9/2027Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2022Organic macromolecular compounds
    • A61K9/2031Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2022Organic macromolecular compounds
    • A61K9/205Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2022Organic macromolecular compounds
    • A61K9/205Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001Acyclic or carbocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/20Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05Isotopically modified compounds, e.g. labelled
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Inorganic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
AU2015343083A 2014-11-04 2015-11-04 Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods Active AU2015343083B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201462074645P 2014-11-04 2014-11-04
US62/074,645 2014-11-04
PCT/US2015/059113 WO2016073653A1 (en) 2014-11-04 2015-11-04 Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods

Publications (2)

Publication Number Publication Date
AU2015343083A1 AU2015343083A1 (en) 2017-06-08
AU2015343083B2 true AU2015343083B2 (en) 2020-07-23

Family

ID=55909773

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2015343083A Active AU2015343083B2 (en) 2014-11-04 2015-11-04 Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods

Country Status (18)

Country Link
US (6) US10252982B2 (https=)
EP (2) EP4393487A3 (https=)
JP (2) JP6882180B2 (https=)
KR (1) KR102604397B1 (https=)
CN (2) CN115521217A (https=)
AU (1) AU2015343083B2 (https=)
CA (1) CA2966737A1 (https=)
DK (1) DK3215147T3 (https=)
ES (1) ES2977383T3 (https=)
FI (1) FI3215147T3 (https=)
HU (1) HUE066468T2 (https=)
LT (1) LT3215147T (https=)
PL (1) PL3215147T3 (https=)
PT (1) PT3215147T (https=)
RS (1) RS65411B1 (https=)
RU (1) RU2771275C2 (https=)
SI (1) SI3215147T1 (https=)
WO (1) WO2016073653A1 (https=)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI3043785T1 (sl) 2013-09-13 2022-02-28 National University Corporation Chiba University Uporaba R-ketamina in njegove soli kot farmacevtska sredstva
WO2015065547A1 (en) 2013-10-31 2015-05-07 Cima Labs Inc. Immediate release abuse-deterrent granulated dosage forms
DK3272338T3 (da) 2014-04-17 2020-11-02 Develco Pharma Schweiz Ag Oral doseringsform for ketamin
AU2015343083B2 (en) * 2014-11-04 2020-07-23 Acadia Pharmaceuticals Inc. Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods
WO2016186968A1 (en) * 2015-05-15 2016-11-24 The Arizona Board Of Regents On Behalf Of The University Of Arizona Compositions and methods for treating motor disorders
US11191734B2 (en) 2015-06-27 2021-12-07 Shenox Pharmaceuticals, Llc Ketamine transdermal delivery system
WO2017180589A1 (en) * 2016-04-11 2017-10-19 Auspex Pharmaceuticals, Inc. Deuterated ketamine derivatives
CN110035997A (zh) * 2016-09-16 2019-07-19 生物制药沃克斯有限公司 羟基去甲氯胺酮前药
US20190240184A1 (en) * 2016-10-27 2019-08-08 National University Corporation Chiba University Pharmaceutical applications for (s)-norketamine and salts thereof
WO2018191482A2 (en) 2017-04-13 2018-10-18 Ovid Therapeutics Inc. Methods of treating developmental encephalopathies
EP3641742B1 (en) * 2017-06-23 2026-03-25 Ketabon GmbH Hydroxynorketamine for the use in the treatment of depression
EP3532457B1 (en) 2017-07-31 2020-03-18 Small Pharma Ltd Crystalline forms of hydroxynorketamine
US10869838B2 (en) 2017-10-10 2020-12-22 Douglas Pharmaceuticals, Ltd. Extended release pharmaceutical formulation
US11471415B2 (en) 2017-10-10 2022-10-18 Douglas Pharmaceuticals, Ltd. Extended release pharmaceutical formulation and methods of treatment
MX2020003546A (es) 2017-10-10 2020-08-03 Douglas Pharmaceuticals Ltd Formulacion farmaceutica de liberacion prolongada y metodos de tratamiento.
US10441544B2 (en) 2017-10-10 2019-10-15 Douglas Pharmaceuticals, Ltd. Extended release pharmaceutical formulation
US12090123B2 (en) 2017-10-10 2024-09-17 Douglas Pharmaceuticals Ltd. Extended release pharmaceutical formulation
EP3501503A1 (en) * 2017-12-22 2019-06-26 Cosmo Technologies Ltd. Solid delivery composition
PL3505157T3 (pl) 2017-12-29 2022-04-11 Celon Pharma S.A. Kompozycja ketaminy w postaci suchego proszku do podawania dopłucnego w leczeniu depresji opornej na leczenie
JP7548669B2 (ja) 2018-02-15 2024-09-10 国立大学法人千葉大学 炎症性疾患若しくは骨疾患の予防又は治療剤及び医薬組成物
AU2019262197B2 (en) 2018-05-04 2024-12-19 Perception Neuroscience, Inc. Methods of treating substance abuse
JP2021529732A (ja) 2018-06-27 2021-11-04 クレキシオ バイオサイエンシーズ エルティーディー. 大うつ病性障害の処置方法
KR20210074275A (ko) 2018-10-05 2021-06-21 클렉시오 바이오사이언시스 리미티드 주요 우울 장애를 치료하기 위한 에스케타민의 복용 요법
US12364672B2 (en) 2018-10-11 2025-07-22 Clexio Biosciences Ltd. Esketamine for use in treating major depressive disorder
KR20220002905A (ko) * 2019-03-25 2022-01-07 더글라스 파머수티클스 리미티드 서방형 약학 제제
US11324707B2 (en) 2019-05-07 2022-05-10 Clexio Biosciences Ltd. Abuse-deterrent dosage forms containing esketamine
US12589083B2 (en) 2019-05-07 2026-03-31 Clexio Biosciences Ltd. Abuse-deterrent dosage forms containing esketamine
CN120817937A (zh) * 2019-08-06 2025-10-21 加利福尼亚大学董事会 聚酮化合物及其制备方法和中间体
CA3155176A1 (en) 2019-10-11 2021-04-15 Pike Therapeutics, Inc., 1219014 B.C. Ltd. Transdermal compositions comprising cannabidiol (cbd) for use in the treatment of seizure disorders
WO2021137148A1 (en) * 2019-12-30 2021-07-08 Clexio Biosciences Ltd. Dosage regime with esketamine for treating neuropsychiatric or neurological conditions
WO2021137147A1 (en) 2019-12-30 2021-07-08 Clexio Biosciences Ltd. Dosage regime with esketamine for treating major depressive disorder
JP2023507926A (ja) 2019-12-30 2023-02-28 クレキシオ バイオサイエンシーズ エルティーディー. 神経精神状態または神経学的状態を治療するためのエスケタミンを用いた投与計画
MX2022014599A (es) * 2020-05-20 2022-12-16 Certego Therapeutics Inc Gaboxadol deuterado en anillo y su uso para el tratamiento de trastornos psiquiatricos.
JP2023543211A (ja) * 2020-09-24 2023-10-13 ダグラス ファーマシューティカルズ エルティーディー. 徐放性医薬製剤
CN114524737B (zh) * 2020-11-23 2024-10-22 江苏恒瑞医药股份有限公司 一种取代的环己酮类化合物
GB202019952D0 (en) * 2020-12-17 2021-02-03 Neurocentrx Pharma Ltd Novel compositions
JP2024515891A (ja) * 2021-04-30 2024-04-10 プログレッシブ セラピューティクス インコーポレーテッド 情緒障害の処置のためのケタミン及びカンナビス
CN116730853A (zh) * 2022-03-04 2023-09-12 上海致根医药科技有限公司 新型氨基酮类化合物及其制备方法和用途

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004045601A1 (en) * 2002-11-18 2004-06-03 Yaupon Therapeutics, Inc. Analgesic uses of norketamine and ketamine/norketamine prodrugs
US20080268071A1 (en) * 2007-04-26 2008-10-30 Auspex Pharmaceuticals, Inc. Substituted cyclohexanones

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5250732A (en) 1991-07-18 1993-10-05 Genentech, Inc. Ketamine analogues for treatment of thrombocytopenia
AUPN605795A0 (en) 1995-10-19 1995-11-09 F.H. Faulding & Co. Limited Analgesic pharmaceutical composition
US20100076087A1 (en) * 2005-10-06 2010-03-25 Auspex Pharmaceuticals, Inc. Methods of reduction of interpatient variability
US8765178B2 (en) * 2006-07-19 2014-07-01 Watson Laboratories, Inc. Controlled release formulations and associated methods
US8710070B2 (en) 2008-03-27 2014-04-29 University Of Kentucky Research Foundation Opioid-ketamine and norketamine codrug combinations for pain management
US9913803B2 (en) 2013-08-26 2018-03-13 Amorsa Therapeutics, Inc. Single-layer oral dose of neuro-attenuating ketamine
AU2015343083B2 (en) 2014-11-04 2020-07-23 Acadia Pharmaceuticals Inc. Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004045601A1 (en) * 2002-11-18 2004-06-03 Yaupon Therapeutics, Inc. Analgesic uses of norketamine and ketamine/norketamine prodrugs
US20080268071A1 (en) * 2007-04-26 2008-10-30 Auspex Pharmaceuticals, Inc. Substituted cyclohexanones

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
DUMONT ET AL, "Prospects in the use of deuterated molecules as therapeutic agents", REVUE, INSTITUT NATIONAL DES RADIOELEMENTS, BELGIUM, (1982-01), vol. 6, no. 4, ISSN 0770-1160, pages 2 - 10 *
EBERT B ET AL, "Norketamine, the main metabolite of ketamine, is a non-competitive NMDA receptor antagonist in the rat cortex and spinal cord", EUROPEAN JOURNAL OF PHARMACOLOGY, (1997-08-20), vol. 333, no. 1, pages 99 - 104 *
FOSTER A B, "Deuterium isotope effects in the metabolism of drugs and xenobiotics: implications for drug design", ADVANCES IN DRUG RESEA, ACADEMIC PRESS, LONDON, GB, (1985-01), vol. 14, ISSN 0065-2490, pages 1 - 40 *
LEUNG ET AL, "Comparative pharmacology in the rat of ketamine and its two principal metabolites, norketamine and (Z)-6-hydroxynorketamine", JOURNAL OF MEDICINAL CHEMISTRY, (1986-01), vol. 29, no. 11, pages 2396 - 2399 *
NORLIDA HARUN ET AL, "Validation of an Enzyme-Linked Immunosorbent Assay Screening Method and a Liquid Chromatography-Tandem Mass Spectrometry Confirmation . . .", JOURNAL OF ANALYTICAL TOXICOLOGY, (2009-07), vol. 33, no. 6, pp 310 - 321 *
REGISTRY, CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US, (2013-06-07), Database accession no. 1435934-57-8 *
ROHIDAS S SULAKE ET AL, "Synthesis of deuterium labeled ketamine metabolite dehydronorketamine-", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 21, no. 19, pages 5719 - 5721, (2011-08-08) *
YARNELL, "Heavy-Hydrogen Drugs Turn Heads, Again", INTERNET CITATION, (2009-06-22), pages 36 - 39, URL: http://pubs.acs.org/cen/science/87/8725sci1.html, (2009-09-16) *
ZHAO XIAOCHEN ET AL, "Simultaneous population pharmacokinetic modelling of ketamine and three major metabolites in patients with treatment - resistant bipolar depression", BRITISH JOURNAL OF CLINICAL PHARMACOL, vol. 74, no. 2, pp 304 - 314 *

Also Published As

Publication number Publication date
US20230192593A1 (en) 2023-06-22
CN115521217A (zh) 2022-12-27
RU2017119222A3 (https=) 2019-06-07
KR102604397B1 (ko) 2023-11-21
PT3215147T (pt) 2024-04-18
US12466783B2 (en) 2025-11-11
LT3215147T (lt) 2024-04-25
RS65411B1 (sr) 2024-05-31
US20260109663A1 (en) 2026-04-23
SI3215147T1 (sl) 2024-05-31
EP4393487A2 (en) 2024-07-03
ES2977383T3 (es) 2024-08-22
HUE066468T2 (hu) 2024-08-28
CA2966737A1 (en) 2016-05-12
JP2018501299A (ja) 2018-01-18
JP6882180B2 (ja) 2021-06-02
WO2016073653A1 (en) 2016-05-12
RU2771275C2 (ru) 2022-04-29
EP4393487A3 (en) 2024-08-21
US20220106258A1 (en) 2022-04-07
PL3215147T3 (pl) 2024-06-24
RU2017119222A (ru) 2018-12-06
US11613515B2 (en) 2023-03-28
KR20170083575A (ko) 2017-07-18
CN107106529A (zh) 2017-08-29
US20220402863A1 (en) 2022-12-22
US20170355663A1 (en) 2017-12-14
US10252982B2 (en) 2019-04-09
AU2015343083A1 (en) 2017-06-08
US11603348B2 (en) 2023-03-14
EP3215147B1 (en) 2024-02-28
EP3215147A4 (en) 2018-05-30
EP3215147A1 (en) 2017-09-13
FI3215147T3 (fi) 2024-04-18
DK3215147T3 (da) 2024-04-02
JP2021120389A (ja) 2021-08-19
US10981859B2 (en) 2021-04-20
US20190263749A1 (en) 2019-08-29

Similar Documents

Publication Publication Date Title
AU2015343083B2 (en) Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods
USRE50805E1 (en) Single-layer oral dose of neuro-attenuating ketamine
JP2019513707A (ja) 重水素化ケタミン誘導体
KR20240088949A (ko) 질병 및 질환의 치료를 위한 lsd 유도체, 합성 및 방법
CN109641849A (zh) 氘代右美沙芬的合成方法
WO2023028091A1 (en) Deuterated empathogens
US20120046302A1 (en) Methods of treating cns disorders
WO2010126527A1 (en) Methods of treating cns disorders
US20250339403A1 (en) Tryptamine Formulations and Uses Thereof
US9763904B2 (en) Position-specific asymmetric deuterium enriched catecholamine derivatives and medicaments comprising said compounds

Legal Events

Date Code Title Description
FGA Letters patent sealed or granted (standard patent)
PC Assignment registered

Owner name: ACADIA PHARMACEUTICALS INC.

Free format text: FORMER OWNER(S): AMORSA THERAPEUTICS, INC.