ES2171299T3 - Procedimiento quimico para la reduccion de 3-hidroximetil-4-(4-fluorofenil)tetrahidropiridinas substituidas en 1. - Google Patents
Procedimiento quimico para la reduccion de 3-hidroximetil-4-(4-fluorofenil)tetrahidropiridinas substituidas en 1.Info
- Publication number
- ES2171299T3 ES2171299T3 ES98929307T ES98929307T ES2171299T3 ES 2171299 T3 ES2171299 T3 ES 2171299T3 ES 98929307 T ES98929307 T ES 98929307T ES 98929307 T ES98929307 T ES 98929307T ES 2171299 T3 ES2171299 T3 ES 2171299T3
- Authority
- ES
- Spain
- Prior art keywords
- tetrahydropiridins
- hydroximethyl
- fluorophenyl
- substituted
- reduction
- Prior art date
- 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
Links
- -1 4-FLUOROPHENYL Chemical class 0.000 title abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 125000006242 amine protecting group Chemical group 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 229910052746 lanthanum Inorganic materials 0.000 abstract 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 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 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- C07D211/34—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D211/70—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1. Un procedimiento para la preparación de un compuesto de fórmula I en la que R1 representa un grupo protector de amina, en el que un compuesto de fórmula II en la que R1 es como se define previamente se reduce mediante un hidruro metálico en presencia de una sal inorgánica en presencia de un diluyente, en donde la sal inorgánica es una sal de haluro de litio, sodio, magnesio, calcio, zinc, lantano o hierro.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9710004.4A GB9710004D0 (en) | 1997-05-17 | 1997-05-17 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2171299T3 true ES2171299T3 (es) | 2002-09-01 |
Family
ID=10812456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98929307T Expired - Lifetime ES2171299T3 (es) | 1997-05-17 | 1998-05-13 | Procedimiento quimico para la reduccion de 3-hidroximetil-4-(4-fluorofenil)tetrahidropiridinas substituidas en 1. |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6326496B1 (es) |
| EP (1) | EP0983237B1 (es) |
| JP (1) | JP4463883B2 (es) |
| KR (1) | KR100515852B1 (es) |
| CN (1) | CN1121386C (es) |
| AR (1) | AR012688A1 (es) |
| AT (1) | ATE212013T1 (es) |
| AU (1) | AU748902B2 (es) |
| BG (1) | BG63847B1 (es) |
| BR (1) | BR9809809B1 (es) |
| CA (1) | CA2289013C (es) |
| CZ (1) | CZ292282B6 (es) |
| DE (1) | DE69803178T2 (es) |
| DK (1) | DK0983237T3 (es) |
| ES (1) | ES2171299T3 (es) |
| GB (1) | GB9710004D0 (es) |
| HU (1) | HUP0002709A3 (es) |
| ID (1) | ID24181A (es) |
| IL (1) | IL132360A (es) |
| NO (1) | NO313326B1 (es) |
| NZ (1) | NZ501692A (es) |
| PL (1) | PL189464B1 (es) |
| PT (1) | PT983237E (es) |
| RU (1) | RU2205178C2 (es) |
| SK (1) | SK149599A3 (es) |
| TR (1) | TR199902823T2 (es) |
| UA (1) | UA61952C2 (es) |
| WO (1) | WO1998052920A1 (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1280775A1 (en) * | 2000-05-12 | 2003-02-05 | Synthon B.V. | TOSYLATE SALTS OF 4-(p-FLUOROPHENYL)-PIPERIDINE-3-CARBINOLS |
| GB0021147D0 (en) | 2000-08-30 | 2000-10-11 | Knoll Ag | Chemical process |
| US6777554B2 (en) | 2001-02-05 | 2004-08-17 | Teva Pharmaceutical Industries Ltd. | Preparation of N-methylparoxetine and related intermediate compounds |
| AU2002318185A1 (en) * | 2001-06-13 | 2002-12-23 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of paroxetine substantially free of alkoxy impurities |
| US20050266082A1 (en) * | 2004-05-26 | 2005-12-01 | Patel Satishkumar A | Preparation of stable paroxetine HC1 ER tablets using a melt granulation process |
| CA2629514A1 (en) * | 2005-11-14 | 2007-05-24 | Auspex Pharmaceuticals, Inc. | Substituted phenylpiperidines with serotoninergic activity and enhanced therapeutic properties |
| US20080033050A1 (en) | 2006-08-04 | 2008-02-07 | Richards Patricia Allison Tewe | Method of treating thermoregulatory disfunction with paroxetine |
| US9138430B2 (en) * | 2007-12-27 | 2015-09-22 | Mylan Specialty L.P. | Formulation and method for the release of paroxetine in the large intestine |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3849542A (en) * | 1966-05-09 | 1974-11-19 | Dow Chemical Co | Lithium magnesium aluminum hydride |
| GB1422263A (en) | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| EP0223334B1 (en) * | 1985-08-10 | 1991-07-10 | Beecham Group Plc | Process for the preparation of aryl-piperidine carbinols |
| EP0299549A3 (en) * | 1987-07-09 | 1989-02-08 | Duphar International Research B.V | Tertiary 2,5-dialkyl-3-phenyl-piperidine derivatives having opiate-antagonistic activity |
| GB9100505D0 (en) * | 1991-01-10 | 1991-02-20 | Shell Int Research | Piperidine derivatives |
| US5258517A (en) * | 1992-08-06 | 1993-11-02 | Sepracor, Inc. | Method of preparing optically pure precursors of paroxetine |
| GB9305175D0 (en) * | 1993-03-13 | 1993-04-28 | Smithkline Beecham Plc | Novel process |
| NZ307479A (en) | 1995-05-17 | 1999-08-30 | Novo Nordisk As | A process for preparing 4-(4-halo substituted phenyl)-3-(3,4-methylenedioxy phenoxy methyl)piperidine derivatives |
| EP1384720A1 (en) * | 1996-06-13 | 2004-01-28 | SUMIKA FINE CHEMICALS Co., Ltd. | Process for drying paroxetine hydrochloride |
| HU221921B1 (hu) | 1996-07-08 | 2003-02-28 | Richter Gedeon Vegyészeti Gyár Rt. | N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására |
| GB9623359D0 (en) * | 1996-11-09 | 1997-01-08 | Smithkline Beecham Plc | Novel process |
-
1997
- 1997-05-17 GB GBGB9710004.4A patent/GB9710004D0/en active Pending
-
1998
- 1998-05-12 AR ARP980102206A patent/AR012688A1/es unknown
- 1998-05-13 US US09/423,749 patent/US6326496B1/en not_active Expired - Fee Related
- 1998-05-13 KR KR10-1999-7010581A patent/KR100515852B1/ko not_active Expired - Fee Related
- 1998-05-13 NZ NZ501692A patent/NZ501692A/en unknown
- 1998-05-13 RU RU99127285/04A patent/RU2205178C2/ru not_active IP Right Cessation
- 1998-05-13 HU HU0002709A patent/HUP0002709A3/hu unknown
- 1998-05-13 PT PT98929307T patent/PT983237E/pt unknown
- 1998-05-13 ID IDW991271A patent/ID24181A/id unknown
- 1998-05-13 CN CN98805113A patent/CN1121386C/zh not_active Expired - Fee Related
- 1998-05-13 SK SK1495-99A patent/SK149599A3/sk unknown
- 1998-05-13 ES ES98929307T patent/ES2171299T3/es not_active Expired - Lifetime
- 1998-05-13 EP EP98929307A patent/EP0983237B1/en not_active Expired - Lifetime
- 1998-05-13 WO PCT/EP1998/002826 patent/WO1998052920A1/en not_active Ceased
- 1998-05-13 BR BRPI9809809-8A patent/BR9809809B1/pt not_active IP Right Cessation
- 1998-05-13 PL PL98336796A patent/PL189464B1/pl not_active IP Right Cessation
- 1998-05-13 CZ CZ19994081A patent/CZ292282B6/cs not_active IP Right Cessation
- 1998-05-13 UA UA99126877A patent/UA61952C2/uk unknown
- 1998-05-13 DE DE69803178T patent/DE69803178T2/de not_active Expired - Lifetime
- 1998-05-13 DK DK98929307T patent/DK0983237T3/da active
- 1998-05-13 AT AT98929307T patent/ATE212013T1/de not_active IP Right Cessation
- 1998-05-13 AU AU79121/98A patent/AU748902B2/en not_active Ceased
- 1998-05-13 JP JP54990898A patent/JP4463883B2/ja not_active Expired - Fee Related
- 1998-05-13 TR TR1999/02823T patent/TR199902823T2/xx unknown
- 1998-05-13 CA CA002289013A patent/CA2289013C/en not_active Expired - Fee Related
- 1998-05-13 IL IL13236098A patent/IL132360A/xx not_active IP Right Cessation
-
1999
- 1999-10-26 BG BG103834A patent/BG63847B1/bg unknown
- 1999-11-16 NO NO19995619A patent/NO313326B1/no unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
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