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

Info

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
Authority
AU
Australia
Prior art keywords
hydroxynorketamine
compound
formula
hydrochloride
hnk
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
AU2017238859A
Other languages
English (en)
Other versions
AU2017238859A1 (en
Inventor
Todd GOULD
Ruin Moaddel
Patrick Morris
Craig Thomas
Panos ZANOS
Carlos Zarate
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
US Department of Health and Human Services
Original Assignee
University of Maryland Baltimore
University of Maryland College Park
Government of the United States of America
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 University of Maryland Baltimore, University of Maryland College Park, Government of the United States of America filed Critical University of Maryland Baltimore
Publication of AU2017238859A1 publication Critical patent/AU2017238859A1/en
Application granted granted Critical
Publication of AU2017238859B2 publication Critical patent/AU2017238859B2/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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

Landscapes

  • 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

Family

ID=58503714

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2017238859A Active AU2017238859B2 (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 (https=)
EP (1) EP3433230A1 (https=)
JP (3) JP7603368B2 (https=)
CN (2) CN109311801B (https=)
AU (1) AU2017238859B2 (https=)
CA (2) CA3018959C (https=)
WO (1) WO2017165878A1 (https=)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11191734B2 (en) 2015-06-27 2021-12-07 Shenox Pharmaceuticals, Llc Ketamine transdermal delivery system
JP7603368B2 (ja) 2016-03-25 2024-12-20 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 （２ｒ，６ｒ）－ヒドロキシノルケタミン塩酸塩の結晶形態
WO2017180589A1 (en) * 2016-04-11 2017-10-19 Auspex Pharmaceuticals, Inc. 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
CN112424157B (zh) * 2018-06-04 2024-02-20 美国政府健康及人类服务部 用于合成和纯化(2r,6r)-羟基去甲氯胺酮的方法
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
JP2023503271A (ja) 2019-11-18 2023-01-27 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 （２ｒ，６ｒ）－ヒドロキシノルケタミンの塩、それらの結晶形、およびその製造方法
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
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
WO2022041174A1 (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衍生物及其制备方法
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
US12466785B2 (en) 2020-08-31 2025-11-11 Shenzhen Ruijian Biotechnology Co., Ltd Long-acting low-addiction HNK derivative and preparation method therefor
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

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

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE435499B (sv) * 1974-12-13 1984-10-01 Merck & Co Inc Diastereomert salt av s-1-t-butylamino-2,3-dihydroxipropan
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
EA201590697A1 (ru) 2012-10-08 2015-09-30 Окленд Юнисервисиз Лимитед Производные кетамина
US9096537B1 (en) * 2014-12-31 2015-08-04 Mahesh Kandula Compositions and methods for the treatment of mucositis
CA3019012A1 (en) * 2016-03-25 2017-09-28 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services 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
JP7603368B2 (ja) 2016-03-25 2024-12-20 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 （２ｒ，６ｒ）－ヒドロキシノルケタミン塩酸塩の結晶形態
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
CA3228060A1 (en) 2017-09-28
CA3018959C (en) 2024-03-12
JP7379567B2 (ja) 2023-11-14
US20230192594A1 (en) 2023-06-22
WO2017165878A1 (en) 2017-09-28
CN109311801B (zh) 2022-07-26
JP2024015334A (ja) 2024-02-01
JP2019510768A (ja) 2019-04-18
US10919842B2 (en) 2021-02-16
JP7603368B2 (ja) 2024-12-20
AU2017238859A1 (en) 2018-10-18
US20190135732A1 (en) 2019-05-09
US12473251B2 (en) 2025-11-18
JP2022069595A (ja) 2022-05-11
US11613514B2 (en) 2023-03-28
EP3433230A1 (en) 2019-01-30
US20210139411A1 (en) 2021-05-13
CA3018959A1 (en) 2017-09-28
CN109311801A (zh) 2019-02-05
CN115108927A (zh) 2022-09-27

Similar Documents

Publication Publication Date Title
AU2017238859B2 (en) Crystal forms and methods of synthesis of (2R, 6R)-hydroxynorketamine and (2S, 6S)-hydroxynorketamine
ES2333488T3 (es) Procedimiento para la preparacion de asenapina y productos intermedios usados en dicho proceso.
Overman et al. Use of aza-Cope rearrangement-Mannich cyclization reactions to achieve a general entry to Melodinus and Aspidosperma alkaloids. Stereocontrolled total syntheses of (.+-.)-deoxoapodine,(.+-.)-meloscine, and (.+-.)-epimeloscine and a formal synthesis of (.+-.)-1-acetylaspidoalbidine
JP2018523633A (ja) ブリバラセタムを製造する方法
ES2553387T3 (es) Compuestos heterocíclicos para el tratamiento o la prevención de trastornos causados por neurotransmisión reducida de serotonina, norepinefrina o dopamina
Williams et al. An alkaloid-like 3-azabicyclo [3.3. 1] non-3-ene library obtained from the bridged Ritter reaction
CN120166992A (zh) 一种((2R,7aS)-2-氟六氢-1H-吡咯嗪-7a-基)甲醇的制备方法
JP4742239B2 (ja) ビシクロ［３．１．０］ヘキサン誘導体およびその中間体の製造方法
WO2016090461A1 (en) Salts of prostaglandin analog intermediates
CN119841759B (zh) 一种沙库必曲中间体的制备方法
EP3381900A1 (en) New synthetic path to pharmaceutically acceptable vismodegib
CA2786646A1 (en) Method for producing 3,4-disubstituted pyrrolidine derivative and production intermediate thereof
AU2013286077B2 (en) Process for preparing enantiomerically enriched oxamides
US20030004208A1 (en) Process for producing stereoisomer of pyrrolidine derivative
CN121913944A (zh) 用于合成二氮杂二环[6.2.0]癸烷相关化合物的方法
Samame Assignment of Configuration Using Kinetic Resolution Reagents and Total Synthesis of (+)-Fastigiatine
Ribelin π-and n-cation through-space interactions in asymmetric nitrogen ring expansion reactions of hydroxyalkyl azides
MXPA06005039A (en) Processes for preparing bicyclo [3.1.0]hexane derivatives, and intermediates thereto
KR20020010931A (ko) 의약품 중간체 화합물의 제조 방법
WO2007052642A1 (ja) カルバペネム化合物
HK1185878B (en) Heterocyclic compounds for treating or preventing disorders caused by reduced neurotransmission of serotonin, norephnephrine or dopamine

Legal Events

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