CN109311801B - (2r,6r)-羟基去甲氯胺酮和(2s,6s)-羟基去甲氯胺酮的晶型和合成方法 - Google Patents
(2r,6r)-羟基去甲氯胺酮和(2s,6s)-羟基去甲氯胺酮的晶型和合成方法 Download PDFInfo
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- CN109311801B CN109311801B CN201780027680.8A CN201780027680A CN109311801B CN 109311801 B CN109311801 B CN 109311801B CN 201780027680 A CN201780027680 A CN 201780027680A CN 109311801 B CN109311801 B CN 109311801B
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- Prior art keywords
- hydroxynorketamine
- compound
- hydrochloride
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- hnk
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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
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- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210826464.2A CN115108927A (zh) | 2016-03-25 | 2017-03-27 | (2r,6r)-羟基去甲氯胺酮和(2s,6s)-羟基去甲氯胺酮的晶型和合成方法 |
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 |
|---|---|---|---|
| CN202210826464.2A Division CN115108927A (zh) | 2016-03-25 | 2017-03-27 | (2r,6r)-羟基去甲氯胺酮和(2s,6s)-羟基去甲氯胺酮的晶型和合成方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109311801A CN109311801A (zh) | 2019-02-05 |
| CN109311801B true CN109311801B (zh) | 2022-07-26 |
Family
ID=58503714
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201780027680.8A Active CN109311801B (zh) | 2016-03-25 | 2017-03-27 | (2r,6r)-羟基去甲氯胺酮和(2s,6s)-羟基去甲氯胺酮的晶型和合成方法 |
| CN202210826464.2A Pending CN115108927A (zh) | 2016-03-25 | 2017-03-27 | (2r,6r)-羟基去甲氯胺酮和(2s,6s)-羟基去甲氯胺酮的晶型和合成方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210826464.2A Pending CN115108927A (zh) | 2016-03-25 | 2017-03-27 | (2r,6r)-羟基去甲氯胺酮和(2s,6s)-羟基去甲氯胺酮的晶型和合成方法 |
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)
| 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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009131794A1 (en) * | 2008-03-27 | 2009-10-29 | University Of Kentucky Research Foundation | Opioid-ketamine and norketamine codrug combinations for pain management |
| CN104395283A (zh) * | 2011-10-14 | 2015-03-04 | 美国政府健康及人类服务部 | (2r,6r)-羟基去甲氯胺酮、(s)-脱氢去甲氯胺酮以及(r,s)-氯胺酮的其他立体异构脱氢和羟基化代谢物在治疗忧郁症和神经性疼痛中的应用 |
Family Cites Families (8)
| 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 |
| 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 |
-
2017
- 2017-03-27 JP JP2018550320A patent/JP7603368B2/ja active Active
- 2017-03-27 CN CN201780027680.8A patent/CN109311801B/zh active Active
- 2017-03-27 US US16/088,371 patent/US10919842B2/en active Active
- 2017-03-27 CN CN202210826464.2A patent/CN115108927A/zh active Pending
- 2017-03-27 AU AU2017238859A patent/AU2017238859B2/en active Active
- 2017-03-27 CA CA3018959A patent/CA3018959C/en active Active
- 2017-03-27 WO PCT/US2017/024241 patent/WO2017165878A1/en not_active Ceased
- 2017-03-27 EP EP17716350.8A patent/EP3433230A1/en active Pending
- 2017-03-27 CA CA3228060A patent/CA3228060A1/en active Pending
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2021
- 2021-01-22 US US17/155,162 patent/US11613514B2/en active Active
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2022
- 2022-03-16 JP JP2022041167A patent/JP7379567B2/ja active Active
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2023
- 2023-02-16 US US18/170,048 patent/US12473251B2/en active Active
- 2023-12-11 JP JP2023208374A patent/JP2024015334A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009131794A1 (en) * | 2008-03-27 | 2009-10-29 | University Of Kentucky Research Foundation | Opioid-ketamine and norketamine codrug combinations for pain management |
| CN104395283A (zh) * | 2011-10-14 | 2015-03-04 | 美国政府健康及人类服务部 | (2r,6r)-羟基去甲氯胺酮、(s)-脱氢去甲氯胺酮以及(r,s)-氯胺酮的其他立体异构脱氢和羟基化代谢物在治疗忧郁症和神经性疼痛中的应用 |
Non-Patent Citations (2)
| Title |
|---|
| Relevance of Solid-state Properties;Rolf Hilfiker et al;《Relevance of Solid-state Properties》;20061231;全文 * |
| Stereochemical studies of demethylated ketamine enantiomers;SUK CHANG HONG etal;《Journal of Pharmaceutical Sciences》;19821231;全文 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2017238859B2 (en) | 2021-02-18 |
| 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 |
| 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 |
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