AU2017238859B2 - Crystal forms and methods of synthesis of (2R, 6R)-hydroxynorketamine and (2S, 6S)-hydroxynorketamine - Google Patents

Crystal forms and methods of synthesis of (2R, 6R)-hydroxynorketamine and (2S, 6S)-hydroxynorketamine Download PDF

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Publication number
AU2017238859B2
AU2017238859B2 AU2017238859A AU2017238859A AU2017238859B2 AU 2017238859 B2 AU2017238859 B2 AU 2017238859B2 AU 2017238859 A AU2017238859 A AU 2017238859A AU 2017238859 A AU2017238859 A AU 2017238859A AU 2017238859 B2 AU2017238859 B2 AU 2017238859B2
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Prior art keywords
hydroxynorketamine
compound
formula
hydrochloride
hnk
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AU2017238859A
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AU2017238859A1 (en
Inventor
Todd GOULD
Ruin Moaddel
Patrick Morris
Craig Thomas
Panos ZANOS
Carlos Zarate
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University of Maryland Baltimore
US Department of Health and Human Services
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University of Maryland Baltimore
University of Maryland College Park
Government of the United States of America
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    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • 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
    • C07B2200/07—Optical isomers
    • 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
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • 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
    • 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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Analysing Materials By The Use Of Radiation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
AU2017238859A 2016-03-25 2017-03-27 Crystal forms and methods of synthesis of (2R, 6R)-hydroxynorketamine and (2S, 6S)-hydroxynorketamine Active AU2017238859B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201662313309P 2016-03-25 2016-03-25
US62/313,309 2016-03-25
PCT/US2017/024241 WO2017165878A1 (en) 2016-03-25 2017-03-27 Crystal forms and methods of synthesis of (2r, 6r)-hydroxynorketamine and (2s, 6s)-hydroxynorketamine

Publications (2)

Publication Number Publication Date
AU2017238859A1 AU2017238859A1 (en) 2018-10-18
AU2017238859B2 true AU2017238859B2 (en) 2021-02-18

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AU2017238859A Active AU2017238859B2 (en) 2016-03-25 2017-03-27 Crystal forms and methods of synthesis of (2R, 6R)-hydroxynorketamine and (2S, 6S)-hydroxynorketamine

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US (3) US10919842B2 (enExample)
EP (1) EP3433230A1 (enExample)
JP (3) JP7603368B2 (enExample)
CN (2) CN115108927A (enExample)
AU (1) AU2017238859B2 (enExample)
CA (2) CA3228060A1 (enExample)
WO (1) WO2017165878A1 (enExample)

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Publication number Priority date Publication date Assignee Title
AU2016288188B2 (en) 2015-06-27 2021-08-05 Shenox Pharmaceuticals, Llc Ketamine transdermal delivery system
AU2017238859B2 (en) 2016-03-25 2021-02-18 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Crystal forms and methods of synthesis of (2R, 6R)-hydroxynorketamine and (2S, 6S)-hydroxynorketamine
AU2017250086A1 (en) * 2016-04-11 2018-09-20 Clexio Biosciences Ltd. Deuterated ketamine derivatives
CN110343050B (zh) * 2018-04-04 2021-09-24 上海键合医药科技有限公司 芳香类化合物及其制备方法和用途
ES2960813T3 (es) 2018-06-04 2024-03-06 Us Health Proceso para la síntesis y purificación de (2r,6r)-hidroxinorketamina
CN112299972B (zh) * 2019-08-02 2023-03-14 扬子江药业集团有限公司 一种高纯度盐酸艾司氯胺酮酮体的制备方法
EP4061794A1 (en) 2019-11-18 2022-09-28 The United States of America, as represented by the Secretary, Department of Health and Human Services Salts of (2r, 6r)-hydroxynorketamine, their crystal forms, and methods of making the same
JP7579595B2 (ja) * 2020-08-31 2024-11-08 深▲せん▼瑞健生物科技有限公司 長時間作用性の低嗜癖性ｈｎｋ誘導体及びその製造方法
WO2022041175A1 (zh) * 2020-08-31 2022-03-03 深圳瑞健生物科技有限公司 一种长效低成瘾性hnk衍生物在制备药物中的应用
WO2022041171A1 (zh) * 2020-08-31 2022-03-03 深圳瑞健生物科技有限公司 一种长效低成瘾性化合物及其制备方法
CN112521357B (zh) * 2020-08-31 2021-10-08 深圳瑞健生物科技有限公司 一种长效低成瘾性hnk衍生物及其制备方法
CN112521358B (zh) * 2020-08-31 2021-10-08 深圳瑞健生物科技有限公司 一种长效低成瘾性hnk衍生物在制备药物中的应用
CN112521295B (zh) * 2020-08-31 2021-10-08 深圳瑞健生物科技有限公司 一种长效低成瘾性化合物及其制备方法
CN112516130B (zh) * 2020-08-31 2022-01-04 深圳瑞健生物科技有限公司 一种长效低成瘾性化合物在制备药物中的应用
WO2022041172A1 (zh) * 2020-08-31 2022-03-03 深圳瑞健生物科技有限公司 一种长效低成瘾性化合物在制备药物中的应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013056229A1 (en) * 2011-10-14 2013-04-18 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services The use of (2r, 6r)-hydroxynorketamine, (s)-dehydronorketamine and other stereoisomeric dehydro and hydroxylated metabolites of (r,s)- ketamine in the treatment of depression and neuropathic pain

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DK532575A (da) * 1974-12-13 1976-06-14 Merck & Co Inc Fremgangsmade til racematspaltning af organiske forbindelser
US20070185346A1 (en) 2006-02-03 2007-08-09 Vaidya Niteen A Kit for automated resolving agent selection and method thereof
US8710070B2 (en) * 2008-03-27 2014-04-29 University Of Kentucky Research Foundation Opioid-ketamine and norketamine codrug combinations for pain management
WO2014020155A1 (en) * 2012-08-02 2014-02-06 Clinpharm Reform Gmbh Oral transmucosal adminstration forms of s-ketamine
EP2903963A4 (en) 2012-10-08 2016-05-25 Auckland Uniservices Ltd KETAMINE DERIVATIVES
US9096537B1 (en) * 2014-12-31 2015-08-04 Mahesh Kandula Compositions and methods for the treatment of mucositis
CN109475514A (zh) * 2016-03-25 2019-03-15 美国政府健康及人类服务部 使用(2r,6r)-羟基去甲氯胺酮和(2s,6s)-羟基去甲氯胺酮治疗抑郁、焦虑、快感缺乏、疲劳、自杀意念和创伤后应激障碍的方法
AU2017238859B2 (en) 2016-03-25 2021-02-18 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Crystal forms and methods of synthesis of (2R, 6R)-hydroxynorketamine and (2S, 6S)-hydroxynorketamine
EP3505509A1 (en) 2017-12-29 2019-07-03 Université de Liège Methods for the preparation of arylcycloalkylamine derivatives

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013056229A1 (en) * 2011-10-14 2013-04-18 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services The use of (2r, 6r)-hydroxynorketamine, (s)-dehydronorketamine and other stereoisomeric dehydro and hydroxylated metabolites of (r,s)- ketamine in the treatment of depression and neuropathic pain

Also Published As

Publication number Publication date
JP2019510768A (ja) 2019-04-18
US20230192594A1 (en) 2023-06-22
CA3018959C (en) 2024-03-12
US12473251B2 (en) 2025-11-18
EP3433230A1 (en) 2019-01-30
CA3228060A1 (en) 2017-09-28
WO2017165878A1 (en) 2017-09-28
US20190135732A1 (en) 2019-05-09
JP7603368B2 (ja) 2024-12-20
JP2024015334A (ja) 2024-02-01
CN109311801A (zh) 2019-02-05
US10919842B2 (en) 2021-02-16
US11613514B2 (en) 2023-03-28
AU2017238859A1 (en) 2018-10-18
JP2022069595A (ja) 2022-05-11
CN109311801B (zh) 2022-07-26
US20210139411A1 (en) 2021-05-13
CN115108927A (zh) 2022-09-27
JP7379567B2 (ja) 2023-11-14
CA3018959A1 (en) 2017-09-28

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