CA1265522A - (+)-mandelate de (+)-trans-3- ¬(4-methoxyphenoxy)-methyl|-1-methyl-4- phenylpiperidine - Google Patents

(+)-mandelate de (+)-trans-3- ¬(4-methoxyphenoxy)-methyl|-1-methyl-4- phenylpiperidine

Info

Publication number: CA1265522A
Authority: CA; Canada
Prior art keywords: methyl; trans; methoxyphenoxy; phenylpiperidine; mixture
Prior art date: 1983-03-07
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.): Expired - Lifetime

Application number

CA000576252A

Other languages

English (en)

Inventor

Jorgen Anders Christensen

Peer Everland

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novo Nordisk AS

Original Assignee

Ferrosan ApS

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.)

1983-03-07

Filing date

1988-08-31

Publication date

1990-02-06

1983-03-07 Priority claimed from DK111583A external-priority patent/DK149624C/da

1988-08-31 Application filed by Ferrosan ApS filed Critical Ferrosan ApS

1988-08-31 Priority to CA000576252A priority Critical patent/CA1265522A/fr

1990-02-06 Application granted granted Critical

1990-02-06 Publication of CA1265522A publication Critical patent/CA1265522A/fr

2007-02-06 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 title abstract description 15
-1 4-methoxyphenoxy Chemical group 0.000 title description 18
VXNWSKOKAILJKO-ZHXLSBKVSA-N 2-hydroxy-2-phenylacetic acid (3S,4R)-3-[(4-methoxyphenoxy)methyl]-1-methyl-4-phenylpiperidine Chemical compound OC(=O)C(O)C1=CC=CC=C1.C1=CC(OC)=CC=C1OC[C@H]1[C@H](C=2C=CC=CC=2)CCN(C)C1 VXNWSKOKAILJKO-ZHXLSBKVSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 23
230000003287 optical effect Effects 0.000 abstract description 15
238000000034 method Methods 0.000 abstract description 14
OJSFTALXCYKKFQ-PXNSSMCTSA-N (3s,4r)-3-[(4-methoxyphenoxy)methyl]-1-methyl-4-phenylpiperidine Chemical compound C1=CC(OC)=CC=C1OC[C@H]1[C@H](C=2C=CC=CC=2)CCN(C)C1 OJSFTALXCYKKFQ-PXNSSMCTSA-N 0.000 abstract description 10
150000001875 compounds Chemical class 0.000 abstract description 10
229960002510 mandelic acid Drugs 0.000 abstract description 9
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 7
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 abstract description 6
230000001376 precipitating effect Effects 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
OJSFTALXCYKKFQ-YLJYHZDGSA-N femoxetine Chemical compound C1=CC(OC)=CC=C1OC[C@@H]1[C@@H](C=2C=CC=CC=2)CCN(C)C1 OJSFTALXCYKKFQ-YLJYHZDGSA-N 0.000 description 6
229950003930 femoxetine Drugs 0.000 description 6
229960004592 isopropanol Drugs 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 3
ZETXHVRPKUXQIT-UHFFFAOYSA-N 1-methyl-4-phenylpiperidine Chemical compound C1CN(C)CCC1C1=CC=CC=C1 ZETXHVRPKUXQIT-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
238000000926 separation method Methods 0.000 description 2
RZQRGNSTDYUDJE-KBPBESRZSA-N (3s,4r)-3-(methoxymethyl)-1-methyl-4-phenylpiperidine Chemical compound COC[C@@H]1CN(C)CC[C@H]1C1=CC=CC=C1 RZQRGNSTDYUDJE-KBPBESRZSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical compound C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 1
OCQAXYHNMWVLRH-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 OCQAXYHNMWVLRH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
125000000393 L-methionino group Chemical group [H]OC(=O)[C@@]([H])(N([H])[*])C([H])([H])C(SC([H])([H])[H])([H])[H] 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Landscapes

Hydrogenated Pyridines (AREA)

CA000576252A 1983-03-07 1988-08-31 (+)-mandelate de (+)-trans-3- ¬(4-methoxyphenoxy)-methyl|-1-methyl-4- phenylpiperidine Expired - Lifetime CA1265522A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000576252A CA1265522A (fr)	1983-03-07	1988-08-31	(+)-mandelate de (+)-trans-3- ¬(4-methoxyphenoxy)-methyl\|-1-methyl-4- phenylpiperidine

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DK1115		1983-03-07
DK111583A DK149624C (da)	1983-03-07	1983-03-07	Fremgangsmaade til fremstilling af (+)-trans-3-((4-methoxyphenoxy)-methyl)-1-methyl-4-phenylpiperidin eller et farmaceutisk acceptabelt salt heraf ud fra en blanding af enantiomererne
CA000448829A CA1257599A (fr)	1983-03-07	1984-03-05	Trans-3-[(4-methoxyphenoxy)-methyl]-1-methyl- 4-phenylpiperidine
CA000576252A CA1265522A (fr)	1983-03-07	1988-08-31	(+)-mandelate de (+)-trans-3- ¬(4-methoxyphenoxy)-methyl\|-1-methyl-4- phenylpiperidine

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000448829A Division CA1257599A (fr)	1983-03-07	1984-03-05	Trans-3-[(4-methoxyphenoxy)-methyl]-1-methyl- 4-phenylpiperidine

Publications (1)

Publication Number	Publication Date
CA1265522A true CA1265522A (fr)	1990-02-06

Family

ID=25670316

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000576252A Expired - Lifetime CA1265522A (fr)	1983-03-07	1988-08-31	(+)-mandelate de (+)-trans-3- ¬(4-methoxyphenoxy)-methyl\|-1-methyl-4- phenylpiperidine

Country Status (1)

Country	Link
CA (1)	CA1265522A (fr)

1988
- 1988-08-31 CA CA000576252A patent/CA1265522A/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1998-02-06	MKLA	Lapsed

Publication	Publication Date	Title
EP0812827B1 (fr)	2009-09-02	Dérivés de pipéridine comme intermédiaire pour la production de paroxétine et procédé pour leur préparation
CA2295800A1 (fr)	1999-01-21	Resolution d'amines
US4968837A (en)	1990-11-06	Resolution of racemic mixtures
US3832388A (en)	1974-08-27	Resolution of 2-(p-hydroxy)phenylglycine
KR960001436B1 (ko)	1996-01-27	광학적 활성인 아테놀롤의 제조방법
US6559338B1 (en)	2003-05-06	Method for racemate splitting of 2-hydroxypropionic acids
US4571424A (en)	1986-02-18	Optical resolution of racemic femoxetine
US6090971A (en)	2000-07-18	Resolution process for cyclohexylphenyl glycolic acid
CA1265522A (fr)	1990-02-06	(+)-mandelate de (+)-trans-3- ¬(4-methoxyphenoxy)-methyl\|-1-methyl-4- phenylpiperidine
JP2546624B2 (ja)	1996-10-23	光学的に純粋なアミノアルコールの製造方法
HU204247B (en)	1991-12-30	Process for optical resolving raceme compositions of alpha-naphtyl-propionic acid derivatives
US6140529A (en)	2000-10-31	Synthesis of optically active cyclohexylphenylglycolate esters
US5087698A (en)	1992-02-11	Process for the optical resolution of dropopizine
JPH05506008A (ja)	1993-09-02	ホモキラルなアミンの製造方法、該アミンを製造するための中間体の製造方法及び該方法に従って製造された中間体
HU194857B (en)	1988-03-28	Process for production of 4-amin-6-fluor-cromane-4-carbonic acid and its 2/r/ methilesther
WO2002068391A1 (fr)	2002-09-06	Procede de dissolution de melanges racemiques de derives de piperidine
US5183922A (en)	1993-02-02	Process for the optical resolution of threo-2-hydroxy-3-(2'-aminophenylthio)-3-(4"-methoxyphenyl)-propionic acid
US5223646A (en)	1993-06-29	Process for producing optically active atenolol and intermediate thereof
EP0427904A1 (fr)	1991-05-22	Procédé de préparation de R(+)-terodiline et de ses sels
WO1990008126A1 (fr)	1990-07-26	Procede de resolution
EP0916657B9 (fr)	2006-05-17	Dérivés optiquement actifs de 1-phényle-pyrrolidone
US20040039206A1 (en)	2004-02-26	Process for resolving racemic mixtures of piperidine derivatives
US6093823A (en)	2000-07-25	Process for the continuous production of basic cyclic optically active α- amino acids
EP0780358B1 (fr)	2000-07-19	Procédé pour la résolution de l'acide 6-méthoxy-alpha-méthyl-2-naphtalémique racémique en ses énantiomères
KR950014521B1 (ko)	1995-12-05	광학적 활성인 글리시딜 에테르의 제조방법