CA3018959C - 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
CA3018959C
CA3018959C CA3018959A CA3018959A CA3018959C CA 3018959 C CA3018959 C CA 3018959C CA 3018959 A CA3018959 A CA 3018959A CA 3018959 A CA3018959 A CA 3018959A CA 3018959 C CA3018959 C CA 3018959C
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CA
Canada
Prior art keywords
hydroxynorketamine
formula
compound
hydrochloride
acid
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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CA3018959A
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English (en)
French (fr)
Other versions
CA3018959A1 (en
Inventor
Craig Thomas
Patrick Morris
Carlos Zarate
Ruin Moaddel
Todd GOULD
Panos ZANOS
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.)
University of Maryland, Baltimore
United States Department of Health and Human Services
Original Assignee
University of Maryland, Baltimore
United States Department of Health and Human Services
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Publication date
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Priority to CA3228060A priority Critical patent/CA3228060A1/en
Publication of CA3018959A1 publication Critical patent/CA3018959A1/en
Application granted granted Critical
Publication of CA3018959C publication Critical patent/CA3018959C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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)
CA3018959A 2016-03-25 2017-03-27 Crystal forms and methods of synthesis of (2r, 6r)-hydroxynorketamine and (2s, 6s)-hydroxynorketamine Active CA3018959C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3228060A CA3228060A1 (en) 2016-03-25 2017-03-27 Crystal forms and methods of synthesis of (2r, 6r)-hydroxynorketamine and (2s, 6s)-hydroxynorketamine

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

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3228060A Division CA3228060A1 (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
CA3018959A1 CA3018959A1 (en) 2017-09-28
CA3018959C true CA3018959C (en) 2024-03-12

Family

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Family Applications (2)

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CA3018959A Active CA3018959C (en) 2016-03-25 2017-03-27 Crystal forms and methods of synthesis of (2r, 6r)-hydroxynorketamine and (2s, 6s)-hydroxynorketamine
CA3228060A Pending CA3228060A1 (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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CA3228060A Pending CA3228060A1 (en) 2016-03-25 2017-03-27 Crystal forms and methods of synthesis of (2r, 6r)-hydroxynorketamine and (2s, 6s)-hydroxynorketamine

Country Status (7)

Country Link
US (3) US10919842B2 (enExample)
EP (1) EP3433230A1 (enExample)
JP (4) JP7603368B2 (enExample)
CN (2) CN109311801B (enExample)
AU (1) AU2017238859B2 (enExample)
CA (2) CA3018959C (enExample)
WO (1) WO2017165878A1 (enExample)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107847469A (zh) 2015-06-27 2018-03-27 美国神农制药责任有限公司 氯胺酮透皮递送系统
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
US11186539B2 (en) 2018-06-04 2021-11-30 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Process for synthesis and purification of (2R,6R)-hydroxynorketamine
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
AU2020387937B2 (en) * 2019-11-18 2026-06-18 The United States Government As Represented By The Department Of Veterans Affairs Salts of (2R, 6R)-hydroxynorketamine, their crystal forms, and methods of making the same
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
US12466785B2 (en) 2020-08-31 2025-11-11 Shenzhen Ruijian Biotechnology Co., Ltd Long-acting low-addiction HNK derivative and preparation method therefor
KR102906446B1 (ko) * 2020-08-31 2026-01-02 선전 루이지엔 바이오테크놀로지 컴퍼니 리미티드 장기 작용성 및 저중독성 hnk 유도체 및 그의 제조 방법
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
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
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
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

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2009131794A1 (en) * 2008-03-27 2009-10-29 University Of Kentucky Research Foundation Opioid-ketamine and norketamine codrug combinations for pain management
JP6296985B2 (ja) * 2011-10-14 2018-03-20 ザ ユナイテッド ステイツ オブ アメリカ， アズ リプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ うつ病及び神経障害性疼痛の治療における（２ｒ，６ｒ）−ヒドロキシノルケタミン、（ｓ）−デヒドロノルケタミン及び他の（ｒ，ｓ）−ケタミンの立体異性デヒドロ及びヒドロキシル化代謝生成物の使用
US20140079740A1 (en) * 2012-08-02 2014-03-20 ClinPharm Support GmbH Oral transmucosal adminstration forms of s-ketamine
AU2013328280B2 (en) 2012-10-08 2017-12-21 Auckland Uniservices Limited Ketamine derivatives
US9096537B1 (en) * 2014-12-31 2015-08-04 Mahesh Kandula Compositions and methods for the treatment of mucositis
US20190083420A1 (en) * 2016-03-25 2019-03-21 The Uinited States of America, as represented by the Secretary, Department of Health and Human Serv Methods of using (2r, 6r)-hydroxynorketamine and (2s, 6s)-hydroxynorketamine in the treatment of depression, anxiety, anhedonia, fatigue, suicidal ideation, and post traumatic stress disorders
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

Also Published As

Publication number Publication date
CA3228060A1 (en) 2017-09-28
US12473251B2 (en) 2025-11-18
WO2017165878A1 (en) 2017-09-28
EP3433230A1 (en) 2019-01-30
JP2026094402A (ja) 2026-06-09
JP2019510768A (ja) 2019-04-18
JP2022069595A (ja) 2022-05-11
US10919842B2 (en) 2021-02-16
US11613514B2 (en) 2023-03-28
US20190135732A1 (en) 2019-05-09
JP2024015334A (ja) 2024-02-01
AU2017238859A1 (en) 2018-10-18
US20230192594A1 (en) 2023-06-22
CN109311801A (zh) 2019-02-05
CA3018959A1 (en) 2017-09-28
US20210139411A1 (en) 2021-05-13
CN109311801B (zh) 2022-07-26
CN115108927A (zh) 2022-09-27
JP7379567B2 (ja) 2023-11-14
AU2017238859B2 (en) 2021-02-18
JP7603368B2 (ja) 2024-12-20

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