IL127026A - Process for the resolution of racemic ketamine - Google Patents
Process for the resolution of racemic ketamineInfo
- Publication number
- IL127026A IL127026A IL12702697A IL12702697A IL127026A IL 127026 A IL127026 A IL 127026A IL 12702697 A IL12702697 A IL 12702697A IL 12702697 A IL12702697 A IL 12702697A IL 127026 A IL127026 A IL 127026A
- Authority
- IL
- Israel
- Prior art keywords
- methylaminocyclohexanone
- water
- chlorophenyl
- tartaric acid
- process according
- Prior art date
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 31
- 238000000034 method Methods 0.000 title claims abstract description 20
- 229960003299 ketamine Drugs 0.000 title description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 150000003892 tartrate salts Chemical class 0.000 claims abstract description 14
- 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 abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003513 alkali Substances 0.000 claims abstract description 6
- 239000011975 tartaric acid Substances 0.000 claims abstract description 6
- 235000002906 tartaric acid Nutrition 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 238000002955 isolation Methods 0.000 claims abstract description 4
- 150000002576 ketones Chemical class 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 52
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 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
- 239000007864 aqueous solution Substances 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 22
- 238000003756 stirring Methods 0.000 description 16
- 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 14
- 229940095064 tartrate Drugs 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000007605 air drying Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 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
- 239000000047 product Substances 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
- 238000001035 drying Methods 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 238000010992 reflux Methods 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- VCMGMSHEPQENPE-ZOWNYOTGSA-N esketamine hydrochloride Chemical compound [Cl-].C=1C=CC=C(Cl)C=1[C@@]1([NH2+]C)CCCCC1=O VCMGMSHEPQENPE-ZOWNYOTGSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- ITBBBZIIFJJMDU-UHFFFAOYSA-N n-ethylnorketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NCC)CCCCC1=O ITBBBZIIFJJMDU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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)
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 (2)
Publication Number | Publication Date |
---|---|
IL127026A0 IL127026A0 (en) | 1999-09-22 |
IL127026A true IL127026A (en) | 2004-02-19 |
Family
ID=7794445
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL12702697A IL127026A (en) | 1996-05-15 | 1997-05-07 | Process for the resolution of racemic ketamine |
Country Status (20)
Country | Link |
---|---|
US (1) | US6040479A (et) |
EP (1) | EP0918744B1 (et) |
JP (1) | JP4151988B2 (et) |
AT (1) | ATE272606T1 (et) |
AU (1) | AU727528B2 (et) |
CA (1) | CA2253575C (et) |
CZ (1) | CZ293546B6 (et) |
DE (2) | DE19619665C2 (et) |
DK (1) | DK0918744T3 (et) |
EE (1) | EE03436B1 (et) |
ES (1) | ES2224247T3 (et) |
HU (1) | HU225773B1 (et) |
IL (1) | IL127026A (et) |
NO (1) | NO311565B1 (et) |
PL (1) | PL187625B1 (et) |
PT (1) | PT918744E (et) |
SK (1) | SK282699B6 (et) |
TR (1) | TR199802317T2 (et) |
WO (1) | WO1997043244A1 (et) |
ZA (1) | ZA974216B (et) |
Families Citing this family (17)
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 |
US20140275278A1 (en) | 2013-03-15 | 2014-09-18 | Janssen Pharmaceutica Nv | Pharmaceutical composition of s-ketamine hydrochloride |
WO2015037248A1 (en) | 2013-09-13 | 2015-03-19 | 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. |
MA40620A (fr) | 2014-09-15 | 2016-03-24 | Janssen Pharmaceutica Nv | Régimes posologiques spécifiques au génotype val66met (snp rs6265) et méthodes pour le traitement de la dépression |
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 |
US20190240184A1 (en) | 2016-10-27 | 2019-08-08 | National University Corporation Chiba University | Pharmaceutical applications for (s)-norketamine and salts thereof |
US20200009081A1 (en) | 2017-09-13 | 2020-01-09 | Janssen Pharmaceutica N.V. | Delivery Of Esketamine For The Treatment Of Depression |
WO2019065900A1 (ja) | 2017-09-27 | 2019-04-04 | 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 |
KR20240011237A (ko) | 2017-12-22 | 2024-01-25 | 얀센 파마슈티카 엔브이 | 우울증 치료를 위한 에스케타민 |
US11980595B2 (en) | 2018-02-15 | 2024-05-14 | National University Corporation Chiba University | Preventive or therapeutic agent and pharmaceutical composition for inflammatory diseases or bone diseases |
AU2019262197A1 (en) | 2018-05-04 | 2020-11-26 | 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 |
CN114126595A (zh) | 2019-03-05 | 2022-03-01 | 杨森制药公司 | 用于治疗抑郁症的艾司氯胺酮 |
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)-氯胺酮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 | 一种氯胺酮、其衍生物或其盐的消旋化方法 |
Family Cites Families (1)
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 TR TR1998/02317T patent/TR199802317T2/xx unknown
- 1997-05-07 SK SK1529-98A patent/SK282699B6/sk not_active IP Right Cessation
- 1997-05-07 HU HU9903085A patent/HU225773B1/hu unknown
- 1997-05-07 AU AU28943/97A patent/AU727528B2/en not_active Expired
- 1997-05-07 CA CA002253575A patent/CA2253575C/en not_active Expired - Lifetime
- 1997-05-07 PT PT97923022T patent/PT918744E/pt unknown
- 1997-05-07 AT AT97923022T patent/ATE272606T1/de active
- 1997-05-07 JP JP54048797A patent/JP4151988B2/ja not_active Expired - Lifetime
- 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 US US09/180,530 patent/US6040479A/en not_active Expired - Lifetime
- 1997-05-07 EE EE9800394A patent/EE03436B1/et unknown
- 1997-05-07 IL IL12702697A patent/IL127026A/en not_active IP Right Cessation
- 1997-05-07 ES ES97923022T patent/ES2224247T3/es not_active Expired - Lifetime
- 1997-05-07 CZ CZ19983558A patent/CZ293546B6/cs not_active IP Right Cessation
- 1997-05-07 DE DE59711834T patent/DE59711834D1/de not_active Expired - Lifetime
- 1997-05-07 DK DK97923022T patent/DK0918744T3/da active
- 1997-05-07 PL PL97329743A patent/PL187625B1/pl 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 |
---|---|
EE03436B1 (et) | 2001-06-15 |
AU727528B2 (en) | 2000-12-14 |
HU225773B1 (en) | 2007-08-28 |
DE59711834D1 (de) | 2004-09-09 |
PT918744E (pt) | 2004-10-29 |
TR199802317T2 (xx) | 1999-02-22 |
WO1997043244A1 (de) | 1997-11-20 |
PL187625B1 (pl) | 2004-08-31 |
NO985300D0 (no) | 1998-11-13 |
EP0918744B1 (de) | 2004-08-04 |
EP0918744A1 (de) | 1999-06-02 |
DE19619665C2 (de) | 2001-03-08 |
ES2224247T3 (es) | 2005-03-01 |
SK282699B6 (sk) | 2002-11-06 |
JP4151988B2 (ja) | 2008-09-17 |
CZ355898A3 (cs) | 1999-04-14 |
ATE272606T1 (de) | 2004-08-15 |
DK0918744T3 (da) | 2004-12-06 |
IL127026A0 (en) | 1999-09-22 |
CA2253575A1 (en) | 1997-11-20 |
ZA974216B (en) | 1997-12-10 |
HUP9903085A3 (en) | 2000-05-29 |
PL329743A1 (en) | 1999-04-12 |
DE19619665A1 (de) | 1997-11-20 |
HUP9903085A1 (hu) | 2000-04-28 |
US6040479A (en) | 2000-03-21 |
CA2253575C (en) | 2005-11-29 |
CZ293546B6 (cs) | 2004-06-16 |
NO311565B1 (no) | 2001-12-10 |
JP2000510135A (ja) | 2000-08-08 |
NO985300L (no) | 1998-11-13 |
EE9800394A (et) | 1999-06-15 |
AU2894397A (en) | 1997-12-05 |
SK152998A3 (en) | 1999-07-12 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ERR | Corrigendum |
Free format text: JOURNAL 12/2003 P. 3619, PATENT APPLICATION NO. 127026 CORRECT INTERNATIONAL PUBLICATION NUMBER TO- WO 97/43244 |
|
FF | Patent granted | ||
EXP | Patent expired |