ES2191587T3 - Procedimiento para la preparacion de derivados de 4-fenil-piperidina 3-sustituida. - Google Patents

Procedimiento para la preparacion de derivados de 4-fenil-piperidina 3-sustituida.

Info

Publication number
ES2191587T3
ES2191587T3 ES00116505T ES00116505T ES2191587T3 ES 2191587 T3 ES2191587 T3 ES 2191587T3 ES 00116505 T ES00116505 T ES 00116505T ES 00116505 T ES00116505 T ES 00116505T ES 2191587 T3 ES2191587 T3 ES 2191587T3
Authority
ES
Spain
Prior art keywords
formula
phenyl
piperidine
preparation
derivatives
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
Application number
ES00116505T
Other languages
English (en)
Inventor
Ferra Lorenzo De
Pietro Massardo
Oreste Piccolo
Giorgio Cignarella
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.)
Chemi SpA
Original Assignee
Chemi SpA
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.)
Filing date
Publication date
Application filed by Chemi SpA filed Critical Chemi SpA
Application granted granted Critical
Publication of ES2191587T3 publication Critical patent/ES2191587T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • 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
    • C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Un procedimiento para la preparación de derivados de 4 - fenil - piperidina 3 - sustituida de fórmula **(Fórmula)** en la que X se selecciona entre H y F, y R se selecciona del grupo que consiste en H, alquilo C1 - C6, alquenilo C3 - C6, y bencilo, comprendiendo las siguientes etapas: a) Adición de Michael entre el aldehído cinámico de fórmula (II) y la amida de fórmula (III) en la que R1 se selecciona del grupo que consiste en alquilo C1 - C6, alquenilo C3 - C6, y bencilo, para obtener 2 - ceto - 3 - carboxialquil - 4 - fenil - 6 - hidroxi - piperidina de fórmula (IV), enriquecida opcionalmente en el isómero (3S, 4R) al usar los catalizadores quirales adecuados: **(Fórmula)** b) reducción de 2 - ceto - 3 - carboxialquil - 4 - fenil - 6 - hidroxi - piperidina de fórmula (IV) proveniente de la etapa a) para obtener 3 - hidroximetil - 4 - fenil - piperidina de fórmula (V): **(Fórmula)** c) reacción de 3 - hidroximetil - 4 - fenilpiperidina de fórmula (V) proveniente de la etapa b) con sesamol(VI) para obtener 3 - [(1, 3 - benzodioxol - 5 - iloxi)metil] - 4 - fenil - piperidina de fórmula (I): **(Fórmula)**
ES00116505T 1999-08-02 2000-07-31 Procedimiento para la preparacion de derivados de 4-fenil-piperidina 3-sustituida. Expired - Lifetime ES2191587T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT1999MI001731A IT1313702B1 (it) 1999-08-02 1999-08-02 Processo per la preparazione di derivati 3-sostituiti di 4-fenil-piperidine.

Publications (1)

Publication Number Publication Date
ES2191587T3 true ES2191587T3 (es) 2003-09-16

Family

ID=11383481

Family Applications (1)

Application Number Title Priority Date Filing Date
ES00116505T Expired - Lifetime ES2191587T3 (es) 1999-08-02 2000-07-31 Procedimiento para la preparacion de derivados de 4-fenil-piperidina 3-sustituida.

Country Status (8)

Country Link
US (1) US6444822B1 (es)
EP (1) EP1074550B1 (es)
JP (1) JP2001081089A (es)
AT (1) ATE231858T1 (es)
CA (1) CA2314750A1 (es)
DE (1) DE60001296T2 (es)
ES (1) ES2191587T3 (es)
IT (1) IT1313702B1 (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1384711A1 (en) * 1996-06-13 2004-01-28 SUMIKA FINE CHEMICALS Co., Ltd. Optical resolution of a piperidine derivative
GB9930577D0 (en) * 1999-12-23 2000-02-16 Smithkline Beecham Plc Novel process
IL161521A0 (en) 2001-10-22 2004-09-27 Synthon Bv N-formyl derivatives of paroxetine
CN102008978B (zh) * 2010-11-24 2012-10-03 郑州大学 手性催化剂及其制备方法和应用
WO2017037662A1 (en) * 2015-09-03 2017-03-09 Piramal Enterprises Limited An improved process for the preparation of paroxetine and its intermediate
WO2023102477A1 (en) * 2021-12-02 2023-06-08 The Johns Hopkins University Peripherally and luminally-restricted inhibitors of the serotonin transporter as treatments for disorders of gastrointestinal motility

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1422263A (en) 1973-01-30 1976-01-21 Ferrosan As 4-phenyl-piperidine compounds
EP0190496A3 (en) 1984-12-13 1987-05-27 Beecham Group Plc Piperidine derivatives having a gastro-intestinal activity
EP0223334B1 (en) 1985-08-10 1991-07-10 Beecham Group Plc Process for the preparation of aryl-piperidine carbinols
DK716088D0 (da) * 1988-12-22 1988-12-22 Ferrosan As Reduktion af piperidin-dion-derivater samt intermediat
DK715988D0 (da) * 1988-12-22 1988-12-22 Ferrosan As Etherifikation og dealkylering af piperidin-derivater samt intermediater
US5258517A (en) * 1992-08-06 1993-11-02 Sepracor, Inc. Method of preparing optically pure precursors of paroxetine
WO1996036636A1 (en) 1995-05-17 1996-11-21 Novo Nordisk A/S Process for preparing 4-aryl-piperidine derivatives
NZ315677A (en) * 1995-09-07 2000-02-28 F 4-(oxyalkoxyphenyl)-3-oxy-piperidines for treating heart and kidney insufficiency
HU221921B1 (hu) * 1996-07-08 2003-02-28 Richter Gedeon Vegyészeti Gyár Rt. N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására
AP9901698A0 (en) * 1997-05-29 1999-12-31 Smithkline Beecham Corp Novel process.

Also Published As

Publication number Publication date
JP2001081089A (ja) 2001-03-27
EP1074550B1 (en) 2003-01-29
US6444822B1 (en) 2002-09-03
ITMI991731A1 (it) 2001-02-02
ATE231858T1 (de) 2003-02-15
ITMI991731A0 (it) 1999-08-02
DE60001296T2 (de) 2003-12-11
CA2314750A1 (en) 2001-02-02
IT1313702B1 (it) 2002-09-09
EP1074550A1 (en) 2001-02-07
DE60001296D1 (de) 2003-03-06

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