JP2015535847A5 - - Google Patents
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- Publication number
- JP2015535847A5 JP2015535847A5 JP2015535162A JP2015535162A JP2015535847A5 JP 2015535847 A5 JP2015535847 A5 JP 2015535847A5 JP 2015535162 A JP2015535162 A JP 2015535162A JP 2015535162 A JP2015535162 A JP 2015535162A JP 2015535847 A5 JP2015535847 A5 JP 2015535847A5
- Authority
- JP
- Japan
- Prior art keywords
- oxocyclohexyl
- chlorophenyl
- amino
- alkyl
- compound
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000001931 aliphatic group Chemical group 0.000 claims description 24
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 8
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- QFFBIIVCZDWTKZ-UHFFFAOYSA-N methyl 5-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]pentanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCCC(=O)OC)CCCCC1=O QFFBIIVCZDWTKZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- OSYLIDUZSLQOIW-UHFFFAOYSA-N ethyl 3-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]propanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCC(=O)OCC)CCCCC1=O OSYLIDUZSLQOIW-UHFFFAOYSA-N 0.000 claims description 5
- FZIHUEMGZWQMJF-UHFFFAOYSA-N ethyl 4-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]butanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCC(=O)OCC)CCCCC1=O FZIHUEMGZWQMJF-UHFFFAOYSA-N 0.000 claims description 5
- KFZMXHQTFSGYLL-UHFFFAOYSA-N ethyl 5-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]pentanoate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCCC(=O)OCC)CCCCC1=O KFZMXHQTFSGYLL-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- BEMFAESGNZMDAI-UHFFFAOYSA-N 3-[[1-(2-chlorophenyl)-2-oxocyclohexyl]amino]propyl acetate Chemical compound C=1C=CC=C(Cl)C=1C1(NCCCOC(=O)C)CCCCC1=O BEMFAESGNZMDAI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000001624 sedative effect Effects 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- GODHIFXMNKQHEI-UHFFFAOYSA-N pentanoic acid;hydrochloride Chemical compound Cl.CCCCC(O)=O GODHIFXMNKQHEI-UHFFFAOYSA-N 0.000 description 2
- AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 1
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- -1 rac-Methyl Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ602885 | 2012-10-08 | ||
| NZ60288512 | 2012-10-08 | ||
| NZ61120213 | 2013-05-28 | ||
| NZ611202 | 2013-05-28 | ||
| PCT/IB2013/059191 WO2014057414A1 (en) | 2012-10-08 | 2013-10-08 | Ketamine derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018046540A Division JP2018127466A (ja) | 2012-10-08 | 2018-03-14 | ケタミン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015535847A JP2015535847A (ja) | 2015-12-17 |
| JP2015535847A5 true JP2015535847A5 (OSRAM) | 2018-02-15 |
| JP6309957B2 JP6309957B2 (ja) | 2018-04-11 |
Family
ID=50476991
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015535162A Expired - Fee Related JP6309957B2 (ja) | 2012-10-08 | 2013-10-08 | ケタミン誘導体 |
| JP2018046540A Pending JP2018127466A (ja) | 2012-10-08 | 2018-03-14 | ケタミン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018046540A Pending JP2018127466A (ja) | 2012-10-08 | 2018-03-14 | ケタミン誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US20150259277A1 (OSRAM) |
| EP (1) | EP2903963A4 (OSRAM) |
| JP (2) | JP6309957B2 (OSRAM) |
| KR (1) | KR20150065873A (OSRAM) |
| CN (1) | CN104837810B (OSRAM) |
| AU (1) | AU2013328280B2 (OSRAM) |
| BR (1) | BR112015007647A2 (OSRAM) |
| CA (1) | CA2922340A1 (OSRAM) |
| EA (1) | EA201590697A1 (OSRAM) |
| HK (1) | HK1212673A1 (OSRAM) |
| IN (1) | IN2015DN03854A (OSRAM) |
| MX (1) | MX2015004362A (OSRAM) |
| WO (1) | WO2014057414A1 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2015004362A (es) * | 2012-10-08 | 2015-12-08 | Auckland Uniservices Ltd | Derivados de ketamina. |
| US20160332962A1 (en) * | 2015-05-13 | 2016-11-17 | Janssen Pharmaceutica Nv | (s)-csa salt of s-ketamine, (r)-csa salt of s-ketamine and processes for the preparation of s-ketamine |
| AU2016288188B2 (en) | 2015-06-27 | 2021-08-05 | Shenox Pharmaceuticals, Llc | Ketamine transdermal delivery system |
| US11827606B2 (en) | 2015-11-18 | 2023-11-28 | Spirify Pharma Inc. | Phenyl cyclohexanone derivatives and methods of making and using them |
| US11111210B2 (en) | 2015-11-18 | 2021-09-07 | Spirify Pharma Inc. | Phenyl cyclohexanone derivatives and methods of making and using them |
| US10919842B2 (en) | 2016-03-25 | 2021-02-16 | 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 |
| RU2756512C1 (ru) * | 2018-01-10 | 2021-10-01 | ЭксДабл-ЮФАРМА ЛТД. | Пролекарства кетамина, его композиции и применения |
| WO2019186357A1 (en) * | 2018-03-26 | 2019-10-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| AU2019282560B2 (en) * | 2018-06-04 | 2023-09-28 | 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 |
| CN112125816A (zh) * | 2020-03-17 | 2020-12-25 | 国药集团工业有限公司 | 一种氯胺酮、其衍生物或其盐的消旋化方法 |
| DE102021105268A1 (de) * | 2021-03-04 | 2022-09-08 | Lts Lohmann Therapie-Systeme Ag. | Oraler Dünnfilm |
| US11690811B2 (en) | 2021-08-13 | 2023-07-04 | XWPharma Ltd. | Pharmaceutical compositions and oral dosage forms of ketamine derivatives |
| CN115677444A (zh) * | 2022-10-26 | 2023-02-03 | 公安部第三研究所 | 同位素毒品代谢物标记化合物及其制备方法、用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254124A (en) * | 1962-06-29 | 1966-05-31 | Parke Davis & Co | Aminoketones and methods for their production |
| GB1134146A (en) * | 1967-09-15 | 1968-11-20 | Parke Davis & Co | New organic amines and methods for their production |
| US5019583A (en) | 1989-02-15 | 1991-05-28 | Glaxo Inc. | N-phenyl-N-(4-piperidinyl)amides useful as analgesics |
| US5466700A (en) | 1993-08-30 | 1995-11-14 | Glaxo Wellcome Inc. | Anesthetic use of N-phenyl-N-(4-piperidinyl)amides |
| US5866591A (en) | 1996-09-11 | 1999-02-02 | Glaxo Wellcome Inc. | Stable formulations of remifentanil |
| JP2004501067A (ja) * | 2000-01-28 | 2004-01-15 | ローム アンド ハース カンパニー | 高められた特性をもつ医薬 |
| US20040248963A1 (en) | 2001-11-23 | 2004-12-09 | Bueno Melendo Ana Belen | Prodrugs of excitatory amino acids |
| DE60335428D1 (de) | 2002-01-31 | 2011-02-03 | Randox Lab Ltd | Immunogene, Antikörper und Konjugate für Ketamin und dessen Metaboliten |
| WO2004045601A1 (en) * | 2002-11-18 | 2004-06-03 | Yaupon Therapeutics, Inc. | Analgesic uses of norketamine and ketamine/norketamine prodrugs |
| KR101271263B1 (ko) * | 2005-09-28 | 2013-06-07 | 아우리스 메디칼 아게 | 내이 장애 치료용 약학 조성물 |
| CA2685344A1 (en) | 2007-04-26 | 2008-11-06 | Auspex Pharmaceuticals, Inc. | Deuterium labelled ketamine |
| 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 |
| MX2015004362A (es) * | 2012-10-08 | 2015-12-08 | Auckland Uniservices Ltd | Derivados de ketamina. |
-
2013
- 2013-10-08 MX MX2015004362A patent/MX2015004362A/es unknown
- 2013-10-08 CA CA2922340A patent/CA2922340A1/en not_active Abandoned
- 2013-10-08 US US14/433,957 patent/US20150259277A1/en not_active Abandoned
- 2013-10-08 WO PCT/IB2013/059191 patent/WO2014057414A1/en not_active Ceased
- 2013-10-08 IN IN3854DEN2015 patent/IN2015DN03854A/en unknown
- 2013-10-08 AU AU2013328280A patent/AU2013328280B2/en not_active Ceased
- 2013-10-08 HK HK16100661.0A patent/HK1212673A1/zh unknown
- 2013-10-08 CN CN201380061537.2A patent/CN104837810B/zh not_active Expired - Fee Related
- 2013-10-08 BR BR112015007647A patent/BR112015007647A2/pt not_active Application Discontinuation
- 2013-10-08 KR KR1020157012009A patent/KR20150065873A/ko not_active Ceased
- 2013-10-08 EA EA201590697A patent/EA201590697A1/ru unknown
- 2013-10-08 EP EP13846133.0A patent/EP2903963A4/en not_active Withdrawn
- 2013-10-08 JP JP2015535162A patent/JP6309957B2/ja not_active Expired - Fee Related
-
2017
- 2017-03-20 US US15/463,532 patent/US10239825B2/en not_active Expired - Fee Related
-
2018
- 2018-03-14 JP JP2018046540A patent/JP2018127466A/ja active Pending
-
2019
- 2019-02-06 US US16/269,015 patent/US20190169113A1/en not_active Abandoned