AU2015343083B2 - Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods - Google Patents
Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods Download PDFInfo
- 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
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- 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.)
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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
- A61K31/13—Amines
- A61K31/133—Amines having hydroxy groups, e.g. sphingosine
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2009—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/28—Drugs 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds 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
- C07C225/20—Compounds 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (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)
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 (5) | US10252982B2 (enExample) |
| EP (2) | EP3215147B1 (enExample) |
| JP (2) | JP6882180B2 (enExample) |
| KR (1) | KR102604397B1 (enExample) |
| CN (2) | CN107106529A (enExample) |
| AU (1) | AU2015343083B2 (enExample) |
| CA (1) | CA2966737A1 (enExample) |
| DK (1) | DK3215147T3 (enExample) |
| ES (1) | ES2977383T3 (enExample) |
| FI (1) | FI3215147T3 (enExample) |
| HU (1) | HUE066468T2 (enExample) |
| LT (1) | LT3215147T (enExample) |
| PL (1) | PL3215147T3 (enExample) |
| PT (1) | PT3215147T (enExample) |
| RS (1) | RS65411B1 (enExample) |
| RU (1) | RU2771275C2 (enExample) |
| SI (1) | SI3215147T1 (enExample) |
| WO (1) | WO2016073653A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015065547A1 (en) | 2013-10-31 | 2015-05-07 | Cima Labs Inc. | Immediate release abuse-deterrent granulated dosage forms |
| EP3131533B1 (en) | 2014-04-17 | 2019-06-05 | Develco Pharma Schweiz AG | Oral dosage form of ketamine |
| EP3215147B1 (en) | 2014-11-04 | 2024-02-28 | ACADIA Pharmaceuticals Inc. | Neuro-attenuating norketamine compounds 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 |
| AU2016288188B2 (en) | 2015-06-27 | 2021-08-05 | Shenox Pharmaceuticals, Llc | Ketamine transdermal delivery system |
| CN108884019A (zh) * | 2016-04-11 | 2018-11-23 | 克雷西奥生物科技有限公司 | 氘代氯胺酮衍生物 |
| 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 |
| IL315066A (en) * | 2016-10-27 | 2024-10-01 | Univ Chiba Nat Univ Corp | Application of (s)-norketamine and salt therof as pharmaceutical |
| WO2018191482A2 (en) | 2017-04-13 | 2018-10-18 | Ovid Therapeutics Inc. | Methods of treating developmental encephalopathies |
| WO2018234568A2 (en) * | 2017-06-23 | 2018-12-27 | Develco Pharma Schweiz Ag | Hydroxynorketamine for the use in the treatment of depression |
| US11377416B2 (en) | 2017-07-31 | 2022-07-05 | Small Pharma Ltd. | Crystalline forms of hydroxynorketamine |
| US11471415B2 (en) | 2017-10-10 | 2022-10-18 | Douglas Pharmaceuticals, Ltd. | Extended release pharmaceutical formulation and methods of treatment |
| US10441544B2 (en) | 2017-10-10 | 2019-10-15 | Douglas Pharmaceuticals, Ltd. | Extended release pharmaceutical formulation |
| CN111630026A (zh) * | 2017-10-10 | 2020-09-04 | 道格拉斯制药有限公司 | 缓释药物制剂和治疗方法 |
| US10869838B2 (en) | 2017-10-10 | 2020-12-22 | 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 |
| EP3505157B1 (en) | 2017-12-29 | 2021-12-08 | Celon Pharma S.A. | Dry powder ketamine composition for pulmonary administration in treatment-resistant depression |
| EP3753557B1 (en) | 2018-02-15 | 2025-11-05 | National University Corporation Chiba University | Preventive or therapeutic agent and pharmaceutical composition for inflammatory diseases or bone diseases |
| EP3813808A4 (en) | 2018-05-04 | 2022-01-26 | Perception Neuroscience, Inc. | Methods of treating substance abuse |
| EP3813807A1 (en) | 2018-06-27 | 2021-05-05 | Clexio Biosciences Ltd. | Method of treating major depressive disorder |
| CN112702995A (zh) | 2018-10-05 | 2021-04-23 | 克雷西奥生物科技有限公司 | 治疗重度抑郁症的艾氯胺酮的治疗方案 |
| US12364672B2 (en) | 2018-10-11 | 2025-07-22 | Clexio Biosciences Ltd. | Esketamine for use in treating major depressive disorder |
| JP7381597B2 (ja) * | 2019-03-25 | 2023-11-15 | ダグラス ファーマシューティカルズ エルティーディー. | 持続放出性の医薬製剤 |
| US11324707B2 (en) | 2019-05-07 | 2022-05-10 | Clexio Biosciences Ltd. | Abuse-deterrent dosage forms containing esketamine |
| US20220062200A1 (en) | 2019-05-07 | 2022-03-03 | Clexio Biosciences Ltd. | Abuse-deterrent dosage forms containing esketamine |
| AU2020325035A1 (en) * | 2019-08-06 | 2022-02-24 | The Regents Of The University Of California | Scaleable preparation of polyketides |
| WO2021070120A1 (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 |
| 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 |
| WO2021137148A1 (en) * | 2019-12-30 | 2021-07-08 | Clexio Biosciences Ltd. | Dosage regime with esketamine for treating neuropsychiatric or neurological conditions |
| IL293506A (en) | 2019-12-30 | 2022-08-01 | Clexio Biosciences Ltd | Dosage regime with esketamine for treating major depressive disorder |
| IL298334A (en) | 2020-05-20 | 2023-01-01 | Certego Therapeutics Inc | Ring deuterated gaboxadol and its use for the treatment of psychiatric disorders |
| 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 |
| AU2022267377A1 (en) * | 2021-04-30 | 2023-12-14 | Progressive Therapeutics, Inc. | Ketamine and cannabis for the treatment of emotional disorders |
| 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)
| 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 |
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| 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 |
| WO2009131794A1 (en) * | 2008-03-27 | 2009-10-29 | University Of Kentucky Research Foundation | Opioid-ketamine and norketamine codrug combinations for pain management |
| EP3960162A1 (en) | 2013-08-26 | 2022-03-02 | Amorsa Therapeutics, Inc. | Single-layer oral dose of neuro-attenuating ketamine |
| EP3215147B1 (en) | 2014-11-04 | 2024-02-28 | ACADIA Pharmaceuticals Inc. | Neuro-attenuating norketamine compounds and methods |
-
2015
- 2015-11-04 EP EP15856205.8A patent/EP3215147B1/en active Active
- 2015-11-04 JP JP2017543308A patent/JP6882180B2/ja active Active
- 2015-11-04 SI SI201532004T patent/SI3215147T1/sl unknown
- 2015-11-04 US US15/524,224 patent/US10252982B2/en active Active
- 2015-11-04 CN CN201580072316.4A patent/CN107106529A/zh active Pending
- 2015-11-04 PL PL15856205.8T patent/PL3215147T3/pl unknown
- 2015-11-04 RU RU2017119222A patent/RU2771275C2/ru active
- 2015-11-04 FI FIEP15856205.8T patent/FI3215147T3/fi active
- 2015-11-04 PT PT158562058T patent/PT3215147T/pt unknown
- 2015-11-04 RS RS20240383A patent/RS65411B1/sr unknown
- 2015-11-04 WO PCT/US2015/059113 patent/WO2016073653A1/en not_active Ceased
- 2015-11-04 CN CN202211196697.5A patent/CN115521217A/zh active Pending
- 2015-11-04 DK DK15856205.8T patent/DK3215147T3/da active
- 2015-11-04 ES ES15856205T patent/ES2977383T3/es active Active
- 2015-11-04 HU HUE15856205A patent/HUE066468T2/hu unknown
- 2015-11-04 CA CA2966737A patent/CA2966737A1/en active Pending
- 2015-11-04 EP EP24159685.7A patent/EP4393487A3/en active Pending
- 2015-11-04 KR KR1020177015310A patent/KR102604397B1/ko active Active
- 2015-11-04 LT LTEPPCT/US2015/059113T patent/LT3215147T/lt unknown
- 2015-11-04 AU AU2015343083A patent/AU2015343083B2/en active Active
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2019
- 2019-02-08 US US16/271,767 patent/US10981859B2/en active Active
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2021
- 2021-03-09 US US17/196,986 patent/US11603348B2/en active Active
- 2021-05-06 JP JP2021078368A patent/JP2021120389A/ja active Pending
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2022
- 2022-08-05 US US17/882,046 patent/US11613515B2/en active Active
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2023
- 2023-02-14 US US18/168,950 patent/US12466783B2/en active Active
Patent Citations (2)
| 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 |
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| 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 * |
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