CZ20011465A3 - Způsob přípravy 4-arylpiperidin-3-methanolů a příbuzných sloučenin - Google Patents

Způsob přípravy 4-arylpiperidin-3-methanolů a příbuzných sloučenin Download PDF

Info

Publication number: CZ20011465A3
Authority: CZ; Czechia
Prior art keywords: formula; compound; group; hydrogen; trans
Prior art date: 1998-11-02

Application number

CZ20011465A

Other languages

Czech (cs)

English (en)

Inventor

Theodorus Hendricus Antonius Peters

Franciscus Bernardus Gemma Benneker

Hans Jan Hoorn

Frantisek Picha

Original Assignee

Synthon B. V.

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.)

1998-11-02

Filing date

1999-11-01

Publication date

2001-08-15

1999-11-01 Application filed by Synthon B. V. filed Critical Synthon B. V.

2001-08-15 Publication of CZ20011465A3 publication Critical patent/CZ20011465A3/cs

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 137
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125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 42
-1 paroxetine Chemical class 0.000 claims abstract description 29
125000003118 aryl group Chemical group 0.000 claims abstract description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims abstract description 15
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AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims abstract description 14
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238000000034 method Methods 0.000 claims description 66
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MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
239000003245 coal Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000008094 contradictory effect Effects 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000003759 ester based solvent Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
230000008570 general process Effects 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
CEXCHYIGFUAPKW-UHFFFAOYSA-N methanol;piperidine Chemical class OC.C1CCNCC1 CEXCHYIGFUAPKW-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
231100000189 neurotoxic Toxicity 0.000 description 1
230000002887 neurotoxic effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
125000004950 trifluoroalkyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CZ20011465A 1998-11-02 1999-11-01 Způsob přípravy 4-arylpiperidin-3-methanolů a příbuzných sloučenin CZ20011465A3 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US10667398P	1998-11-02	1998-11-02

Publications (1)

Publication Number	Publication Date
CZ20011465A3 true CZ20011465A3 (cs)	2001-08-15

Family

ID=22312658

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ20011465A CZ20011465A3 (cs)	1998-11-02	1999-11-01	Způsob přípravy 4-arylpiperidin-3-methanolů a příbuzných sloučenin

Country Status (5)

Country	Link
EP (1)	EP1124802A1 (fr)
AU (1)	AU6360999A (fr)
CZ (1)	CZ20011465A3 (fr)
NO (1)	NO20012099L (fr)
WO (1)	WO2000026187A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR9809687A (pt)	1997-05-29	2000-07-11	Smithkline Beecham Corp	Processo novo
US20010053862A1 (en) *	1998-12-22	2001-12-20	Bruce Ronsen	Process for preparing arylpiperidine carbinol intermediates and derivatives
WO2000037443A1 (fr) *	1998-12-22	2000-06-29	Pentech Pharmaceuticals, Inc.	Procede de preparation d'intermediaires et de derives de arylpiperidine carbinol
CZ20023694A3 (cs) *	2000-05-12	2003-05-14	Synthon B. V.	Tosylátové soli 4-(p-fluorfenyl)-piperidin-3-methanolů
NZ526874A (en)	2001-01-04	2005-07-29	Ferrer Internacional S	Process for preparing (+/-) trans-4-p-fluorophenyl-3-hydroxymethyl-1-methylpiperidine
NZ532432A (en)	2001-10-22	2005-02-25	Synthon Bv	N-formyl paroxetine compounds and their use in a synthetic route for obtaining paroxetine
WO2007089193A1 (fr) *	2006-02-02	2007-08-09	Astrazeneca Ab	Procédé de synthèse du 2-hydroxy-3-[5-(morpholin-4-ylméthyl)pyridin-2-yl]1h-indole-5-carbonitrile sous forme de base libre ou de ses sels

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI792076A7 (fi) *	1978-07-05	1981-01-01	Ciba Geigy Ag	Menetelmä uusien fenyylipiperidiinijohdannaisten valmistamiseksi.
EP0223334B1 (fr) *	1985-08-10	1991-07-10	Beecham Group Plc	Procédé de préparation d'aryl-pipéridine-carbinols
US5258517A (en) *	1992-08-06	1993-11-02	Sepracor, Inc.	Method of preparing optically pure precursors of paroxetine
GB9526645D0 (en) *	1995-12-28	1996-02-28	Chiroscience Ltd	Stereoselective synthesis
JP3446468B2 (ja) *	1996-04-15	2003-09-16	旭硝子株式会社	ピペリジンカルビノール類の製造方法
BR9809687A (pt) *	1997-05-29	2000-07-11	Smithkline Beecham Corp	Processo novo

1999
- 1999-11-01 EP EP99951035A patent/EP1124802A1/fr not_active Withdrawn
- 1999-11-01 CZ CZ20011465A patent/CZ20011465A3/cs unknown
- 1999-11-01 WO PCT/IB1999/001762 patent/WO2000026187A1/fr not_active Ceased
- 1999-11-01 AU AU63609/99A patent/AU6360999A/en not_active Abandoned
2001
- 2001-04-27 NO NO20012099A patent/NO20012099L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
NO20012099L (no)	2001-07-02
EP1124802A1 (fr)	2001-08-22
AU6360999A (en)	2000-05-22
NO20012099D0 (no)	2001-04-27
WO2000026187A1 (fr)	2000-05-11

Publication	Publication Date	Title
US5948914A (en)	1999-09-07	Piperidine derivative and process for preparing the same
EP0923554B1 (fr)	2002-01-09	Derives de n-benzylpiperidine et de tetrahydropyridine
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FR2674849A1 (fr)	1992-10-09	Nouveaux derives de n-cyclohexyl benzamides ou thiobenzamides, leurs preparations et leurs applications en therapeutique.
US6100401A (en)	2000-08-08	Process for preparing the d-threo isomer of methylphenidate hydrochloride
EP0374674A2 (fr)	1990-06-27	Etherification et désalcoylation de dérivés de pipéridine et intermédiaires
RU2167868C2 (ru)	2001-05-27	Способ получения норбензоморфана
CZ20011465A3 (cs)	2001-08-15	Způsob přípravy 4-arylpiperidin-3-methanolů a příbuzných sloučenin
US6225473B1 (en)	2001-05-01	Method for producing (−)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-piperidine
JP2001504081A (ja)	2001-03-27	パロキセチン合成用中間体としての光学的に濃縮された４―アリール―３―ヒドロメチル置換ピペリジンの製法
WO2004080959A2 (fr)	2004-09-23	Procede de preparation de dexmethylphenidate hydrochlorure
EP0365064B1 (fr)	1992-10-21	Composés aromatiques substitués ayant une action sur le système nerveux
US6444822B1 (en)	2002-09-03	Process for the preparation of 3-substituted 4-phenyl-piperidine derivative
EP1347960B1 (fr)	2004-11-17	Procede de preparation de (+)-trans-4-p-fluorophenyl-3-hydroxymethyl-1-methylpiperidine
US6437136B2 (en)	2002-08-20	Process for the preparation of (−)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidine
US5585500A (en)	1996-12-17	Method of producing optically active pyrrolidines with high enantiomeric purity
FI80261B (fi)	1990-01-31	Foerfarande foer optisk upploesning av en blandning av enantiomerer av trans-3-/(4-metoxifenoxi)-metyl/-1-metyl-4- fenylpiperidin.
CA2012569A1 (fr)	1990-09-22	Benzothiopyranylamines
US6031114A (en)	2000-02-29	Process for pyrrolidinyl hydroxamic acid compounds
US4833169A (en)	1989-05-23	Hydropyridine derivatives
CN1989097A (zh)	2007-06-27	用于制备非对映异构体富集的化合物的方法
US4387230A (en)	1983-06-07	Process for preparing a dihydropyridine derivative
US20010053862A1 (en)	2001-12-20	Process for preparing arylpiperidine carbinol intermediates and derivatives
PL182914B1 (pl)	2002-04-30	Sposób wytwarzania (-)-N-metylo-N-[4-(4-fenylo-4-acetyloaminopiperydyn-1-ylo)-2-(3,4-dichlorofenylo)butylo]benzamidu
EP1140832A1 (fr)	2001-10-10	Procede de preparation d'intermediaires et de derives de arylpiperidine carbinol