NO311565B1 - Fremgangsmåte for spalting av racemisk ketamin - Google Patents

Fremgangsmåte for spalting av racemisk ketamin Download PDF

Info

Publication number: NO311565B1
Authority: NO; Norway
Prior art keywords: water; chlorophenyl; methylaminocyclohexanone; tartaric acid; acetone
Prior art date: 1996-05-15

Application number

NO19985300A

Other languages

English (en)

Norwegian (no)

Other versions

NO985300L (no

NO985300D0 (no

Inventor

Klaus Steiner

Stefan Gangkofner

Jean-Marie Grunenwald

Original Assignee

Uetikon Chemie Gmbh

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.)

1996-05-15

Filing date

1998-11-13

Publication date

2001-12-10

1998-11-13 Application filed by Uetikon Chemie Gmbh filed Critical Uetikon Chemie Gmbh

1998-11-13 Publication of NO985300L publication Critical patent/NO985300L/no

1998-11-13 Publication of NO985300D0 publication Critical patent/NO985300D0/no

2001-12-10 Publication of NO311565B1 publication Critical patent/NO311565B1/no

Links

YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 title claims abstract description 29
238000000034 method Methods 0.000 title claims abstract description 19
238000003776 cleavage reaction Methods 0.000 title claims description 6
230000007017 scission Effects 0.000 title claims description 6
229960003299 ketamine Drugs 0.000 title abstract description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 52
229910001868 water Inorganic materials 0.000 claims description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 18
150000003892 tartrate salts Chemical class 0.000 claims description 12
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 6
239000003513 alkali Substances 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
235000002906 tartaric acid Nutrition 0.000 claims description 4
239000011975 tartaric acid Substances 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 19
238000003756 stirring Methods 0.000 description 17
238000001035 drying Methods 0.000 description 12
YQEZLKZALYSWHR-ZDUSSCGKSA-N (S)-ketamine Chemical class C=1C=CC=C(Cl)C=1[C@@]1(NC)CCCCC1=O YQEZLKZALYSWHR-ZDUSSCGKSA-N 0.000 description 10
229940095064 tartrate Drugs 0.000 description 10
239000013078 crystal Substances 0.000 description 8
239000002585 base Substances 0.000 description 7
239000001358 L(+)-tartaric acid Substances 0.000 description 6
235000011002 L(+)-tartaric acid Nutrition 0.000 description 6
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1

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
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Indole Compounds (AREA)
Pyrrole Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

NO19985300A 1996-05-15 1998-11-13 Fremgangsmåte for spalting av racemisk ketamin NO311565B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19619665A DE19619665C2 (de)	1996-05-15	1996-05-15	Racemattrennung von Ketamin
PCT/EP1997/002360 WO1997043244A1 (de)	1996-05-15	1997-05-07	Racemattrennung von ketamin

Publications (3)

Publication Number	Publication Date
NO985300L NO985300L (no)	1998-11-13
NO985300D0 NO985300D0 (no)	1998-11-13
NO311565B1 true NO311565B1 (no)	2001-12-10

Family

ID=7794445

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19985300A NO311565B1 (no)	1996-05-15	1998-11-13	Fremgangsmåte for spalting av racemisk ketamin

Country Status (20)

Country	Link
US (1)	US6040479A (hu)
EP (1)	EP0918744B1 (hu)
JP (1)	JP4151988B2 (hu)
AT (1)	ATE272606T1 (hu)
AU (1)	AU727528B2 (hu)
CA (1)	CA2253575C (hu)
CZ (1)	CZ293546B6 (hu)
DE (2)	DE19619665C2 (hu)
DK (1)	DK0918744T3 (hu)
EE (1)	EE03436B1 (hu)
ES (1)	ES2224247T3 (hu)
HU (1)	HU225773B1 (hu)
IL (1)	IL127026A (hu)
NO (1)	NO311565B1 (hu)
PL (1)	PL187625B1 (hu)
PT (1)	PT918744E (hu)
SK (1)	SK282699B6 (hu)
TR (1)	TR199802317T2 (hu)
WO (1)	WO1997043244A1 (hu)
ZA (1)	ZA974216B (hu)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BRPI0002693B8 (pt) *	2000-06-19	2021-05-25	Cristalia Produtos Quim Farmaceuticos Ltda	processo de obtenção dos enantiômeros da cetamina e seus sais farmaceuticamente aceitáveis
BR112015022972B1 (pt)	2013-03-15	2023-02-14	Janssen Pharmaceutica Nv	Composição farmacêutica de cloridrato de s-cetamina e formas de dosagem da mesma
EP3964203A1 (en)	2013-09-13	2022-03-09	National University Corporation Chiba University	Application of r-ketamine and salt thereof as pharmaceuticals
MX2017001908A (es)	2014-08-13	2017-08-08	Janssen Pharmaceutica Nv	Metodo para el tratamiento de la depresion.
WO2016044150A1 (en)	2014-09-15	2016-03-24	Janssen Pharmaceutica Nv	VAL66MET (SNP rs6265) GENOTYPE SPECIFIC DOSING REGIMENS AND METHODS FOR THE TREATMENT OF DEPRESSION
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
CN110167541A (zh)	2016-10-27	2019-08-23	国立大学法人千叶大学	(s)-去甲***及其盐作为药物的应用
US20200009081A1 (en)	2017-09-13	2020-01-09	Janssen Pharmaceutica N.V.	Delivery Of Esketamine For The Treatment Of Depression
JP7265990B2 (ja)	2017-09-27	2023-04-27	国立大学法人千葉大学	神経変性疾患あるいは認知機能障害の予防または治療剤としてのｒ－ケタミンおよびその誘導体
KR20200113197A (ko)	2017-12-22	2020-10-06	얀센 파마슈티칼즈, 인코포레이티드	우울증 치료를 위한 에스케타민
BR112020016500A2 (pt)	2018-02-15	2020-12-15	National University Corporation Chiba University	Agente preventivo ou terapêutico e composição farmacêutica para doença inflamatória ou doença óssea
CA3099293A1 (en)	2018-05-04	2019-11-07	Perception Neuroscience, Inc.	Methods of treating substance abuse
JP7483630B2 (ja)	2018-12-27	2024-05-15	国立大学法人千葉大学	神経発達障害の予防または治療剤としてのｒ－ケタミンおよびその誘導体
CA3131929A1 (en)	2019-03-05	2020-09-10	Janssen Pharmaceuticals, Inc.	Esketamine for the treatment of depression
EP3956300A1 (en) *	2019-04-16	2022-02-23	Janssen Pharmaceutica NV	Synthetic methods of preparing esketamine
CN112409195A (zh) *	2020-03-17	2021-02-26	国药集团工业有限公司	一种(s)-***盐酸盐的制备方法及其中间体、其晶型
CN112125816A (zh) *	2020-03-17	2020-12-25	国药集团工业有限公司	一种***、其衍生物或其盐的消旋化方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH535201A (de) *	1969-12-19	1973-03-31	Bristol Myers Co	Verfahren zur Spaltung von racemischen 2-(o-Chlorphenyl)-2-methylaminocyclohexanon in die optisch-aktiven Isomeren

1996
- 1996-05-15 DE DE19619665A patent/DE19619665C2/de not_active Expired - Lifetime
1997
- 1997-05-07 JP JP54048797A patent/JP4151988B2/ja not_active Expired - Lifetime
- 1997-05-07 CA CA002253575A patent/CA2253575C/en not_active Expired - Lifetime
- 1997-05-07 PL PL97329743A patent/PL187625B1/pl unknown
- 1997-05-07 IL IL12702697A patent/IL127026A/en not_active IP Right Cessation
- 1997-05-07 DK DK97923022T patent/DK0918744T3/da active
- 1997-05-07 TR TR1998/02317T patent/TR199802317T2/xx unknown
- 1997-05-07 HU HU9903085A patent/HU225773B1/hu unknown
- 1997-05-07 WO PCT/EP1997/002360 patent/WO1997043244A1/de active IP Right Grant
- 1997-05-07 EP EP97923022A patent/EP0918744B1/de not_active Expired - Lifetime
- 1997-05-07 AU AU28943/97A patent/AU727528B2/en not_active Expired
- 1997-05-07 ES ES97923022T patent/ES2224247T3/es not_active Expired - Lifetime
- 1997-05-07 SK SK1529-98A patent/SK282699B6/sk not_active IP Right Cessation
- 1997-05-07 CZ CZ19983558A patent/CZ293546B6/cs not_active IP Right Cessation
- 1997-05-07 AT AT97923022T patent/ATE272606T1/de active
- 1997-05-07 DE DE59711834T patent/DE59711834D1/de not_active Expired - Lifetime
- 1997-05-07 PT PT97923022T patent/PT918744E/pt unknown
- 1997-05-07 US US09/180,530 patent/US6040479A/en not_active Expired - Lifetime
- 1997-05-07 EE EE9800394A patent/EE03436B1/xx unknown
- 1997-05-15 ZA ZA9704216A patent/ZA974216B/xx unknown
1998
- 1998-11-13 NO NO19985300A patent/NO311565B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
CZ293546B6 (cs)	2004-06-16
JP4151988B2 (ja)	2008-09-17
JP2000510135A (ja)	2000-08-08
NO985300L (no)	1998-11-13
SK282699B6 (sk)	2002-11-06
IL127026A0 (en)	1999-09-22
CA2253575A1 (en)	1997-11-20
PT918744E (pt)	2004-10-29
TR199802317T2 (xx)	1999-02-22
SK152998A3 (en)	1999-07-12
ATE272606T1 (de)	2004-08-15
IL127026A (en)	2004-02-19
AU2894397A (en)	1997-12-05
DK0918744T3 (da)	2004-12-06
AU727528B2 (en)	2000-12-14
HU225773B1 (en)	2007-08-28
CZ355898A3 (cs)	1999-04-14
EP0918744B1 (de)	2004-08-04
PL187625B1 (pl)	2004-08-31
HUP9903085A3 (en)	2000-05-29
DE19619665A1 (de)	1997-11-20
US6040479A (en)	2000-03-21
WO1997043244A1 (de)	1997-11-20
NO985300D0 (no)	1998-11-13
EP0918744A1 (de)	1999-06-02
EE03436B1 (et)	2001-06-15
EE9800394A (et)	1999-06-15
ZA974216B (en)	1997-12-10
CA2253575C (en)	2005-11-29
ES2224247T3 (es)	2005-03-01
PL329743A1 (en)	1999-04-12
DE19619665C2 (de)	2001-03-08
HUP9903085A1 (hu)	2000-04-28
DE59711834D1 (de)	2004-09-09

Legal Events

Date	Code	Title	Description
2017-05-15	MK1K	Patent expired

Publication	Publication Date	Title
NO311565B1 (no)	2001-12-10	Fremgangsmåte for spalting av racemisk ketamin
RU2544856C2 (ru)	2015-03-20	НОВЫЕ ПРОИЗВОДНЫЕ 2,3,4,5-ТЕТРАГИДРО-1-ПИРИДО[4,3-b]ИНДОЛА И СПОСОБЫ ИХ ПРИМЕНЕНИЯ
BG61323B2 (bg)	1997-05-30	Производни на пиперидина,тяхното получаване и използването им като лекарства
US20090192210A1 (en)	2009-07-30	Polymorphs of n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino]methyl]phenyl]-2e-2-propenamide
US5354760A (en)	1994-10-11	Crystalline Tiagabine monohydrate, its preparation and use
US4968837A (en)	1990-11-06	Resolution of racemic mixtures
US4777291A (en)	1988-10-11	Racemization process
NZ548041A (en)	2010-04-30	Crystal form of quinoline compound and process for its production
EP1490333B1 (en)	2010-01-20	New atorvastatin salts and pharmaceutical compositions containing them
FR2493315A1 (fr)	1982-05-07	Derive de piperazine, procede pour sa preparation et composition analgesique en contenant
AU632844B2 (en)	1993-01-14	Halogenoalkylphenyl-alcohols, -keytones and hydrates thereof
EP3286168A1 (en)	2018-02-28	A solid form of apremilast and a process for preparing the same
HU221793B1 (hu)	2003-01-28	Eljárás ropivakain-hidroklorid-monohidrát előállítására
EP2358369A1 (en)	2011-08-24	Process for the preparation of substantially optically pure repaglinide and precursors thereof
US7696372B2 (en)	2010-04-13	Process for preparing R-gossypol L-phenylalaninol dienamine
US5808088A (en)	1998-09-15	Preparation of mibefradil via an acetamide anion
KR100275978B1 (ko)	2000-12-15	(-)-n-메틸-n-(4-(4-페닐-4-아세틸아미노피페리딘-1-일)-2-(3,4-디클로로페닐)부틸)벤즈아미드 및 약학적으로 허용가능한 그의 염의 제조방법
GB2341386A (en)	2000-03-15	Synthesis of 1,4-oxazin-2-ones
SK278528B6 (en)	1997-08-06	5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indole derivatives, preparation method thereof and pharmaceutical compositions containing them
EP0916657B9 (en)	2006-05-17	1-phenylpyrrolidone derivatives having optical activity
NO162461B (no)	1989-09-25	Fremgangsm te for fremstilling av aminderivater.
FR2510560A1 (fr)	1983-02-04	Procede de preparation d'amino-4 butyramide
EP2177221A1 (en)	2010-04-21	Process for the preparation of substantially optically pure Repaglinide and precursors thereof
BE565941A (hu)
JPH09268178A (ja)	1997-10-14	光学活性な４，５−ジフェニル−２−イミダゾリジノン誘導体