IL127026A - Process for the resolution of racemic ketamine - Google Patents

Process for the resolution of racemic ketamine

Info

Publication number: IL127026A
Authority: IL; Israel
Prior art keywords: methylaminocyclohexanone; water; chlorophenyl; tartaric acid; process according
Prior art date: 1996-05-15

Application number

IL12702697A

Other languages

English (en)

Other versions

IL127026A0 (en

Original Assignee

Goedecke Ag

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

1997-05-07

Publication date

2004-02-19

1997-05-07 Application filed by Goedecke Ag, Uetikon Chemie Gmbh filed Critical Goedecke Ag

1999-09-22 Publication of IL127026A0 publication Critical patent/IL127026A0/xx

2004-02-19 Publication of IL127026A publication Critical patent/IL127026A/en

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)

IL12702697A 1996-05-15 1997-05-07 Process for the resolution of racemic ketamine IL127026A (en)

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 (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
NO311565B1 (no)	2001-12-10
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
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
2004-05-12	ERR	Corrigendum	Free format text: JOURNAL 12/2003 P. 3619, PATENT APPLICATION NO. 127026 CORRECT INTERNATIONAL PUBLICATION NUMBER TO- WO 97/43244
2004-07-25	FF	Patent granted
2017-12-31	EXP	Patent expired

Publication	Publication Date	Title
US6040479A (en)	2000-03-21	Racemic separation of ketamine
EP1481964B1 (de)	2006-08-23	Stabile Salze neuartiger derivative von 3,3-Diphenylpropylaminen
PT92364B (pt)	1995-07-18	Processo para a preparacao de acido 2-{2-{(4-cloridrato)- fenilmetil}-1- -piperazinil}etoxi}-acetico e do seu cloridrato
US4777291A (en)	1988-10-11	Racemization process
US4968837A (en)	1990-11-06	Resolution of racemic mixtures
EP0413667A1 (de)	1991-02-20	Halogenalkylphenyl-Alkohole, -Ketone und deren Hydrate
Southwick et al.	1958	A New Synthesis of dl-Vasicine and a Methoxy Analog1
AU2019347545B2 (en)	2024-06-13	Novel method for preparing (-)-Cibenzoline succinate
WO2008126075A1 (en)	2008-10-23	Process for preparing montelukast and salts thereof using optically impure 2-(2-(3(s)-(3-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)phenyl-2-propanol
JPH02306947A (ja)	1990-12-20	キラルβ―アミノ酸の製造方法
CA1254208A (en)	1989-05-16	3,7-diazabicyclo¬3.3.1\|nonanes and preparation thereof
WO2008087628A1 (en)	2008-07-24	Process for preparing montelukast sodium containing controlled levels of impurities
JPH06340595A (ja)	1994-12-13	光学的に純粋なアミノアルコールの製造方法
EP2345655A1 (en)	2011-07-20	A process for racemisation of 6-(5-chloropyridin-2-yl)-7-(4-methyl-1-piperazinyl)carbonyloxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine
US4438133A (en)	1984-03-20	Therapeutically effective derivatives of cystine
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
JPS6148839B2 (hu)	1986-10-25
CA1110639A (en)	1981-10-13	Process for producing optically active bases
US20020026069A1 (en)	2002-02-28	Process for manufacture of L-DOPA ethyl ester
JP4532801B2 (ja)	2010-08-25	（−）−（１ｓ，４ｒ）ｎ保護４−アミノ−２−シクロペンテン−１−カルボン酸エステルの調製法
US4078085A (en)	1978-03-07	3-Aminomethyl-4-homoisotwistane and its salt and process for producing same
JPS59155315A (ja)	1984-09-04	イミダゾ−ル誘導体
US5011985A (en)	1991-04-30	Levo-ciprofibrate
US5011986A (en)	1991-04-30	Dextro-ciprofibrate
Erhardt et al.	1987	Facile formation of quaternary azetidinium compounds during triflation of dialkylaminopropanols