CA2462110C - Phenyl-piperazine derivatives as serotonin reuptake inhibitors - Google Patents

Phenyl-piperazine derivatives as serotonin reuptake inhibitors Download PDF

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Publication number
CA2462110C
CA2462110C CA2462110A CA2462110A CA2462110C CA 2462110 C CA2462110 C CA 2462110C CA 2462110 A CA2462110 A CA 2462110A CA 2462110 A CA2462110 A CA 2462110A CA 2462110 C CA2462110 C CA 2462110C
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CA
Canada
Prior art keywords
phenyl
piperazine
compound
alkyl
compound according
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
CA2462110A
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English (en)
French (fr)
Other versions
CA2462110E (en
CA2462110A1 (en
Inventor
Thomas Ruhland
Garrick Paul Smith
Benny Bang-Andersen
Ask Pueschl
Ejner Knud Moltzen
Kim Andersen
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H Lundbeck AS
Original Assignee
H Lundbeck AS
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Application filed by H Lundbeck AS filed Critical H Lundbeck AS
Publication of CA2462110E publication Critical patent/CA2462110E/en
Publication of CA2462110A1 publication Critical patent/CA2462110A1/en
Application granted granted Critical
Publication of CA2462110C publication Critical patent/CA2462110C/en
Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • 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
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (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)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
CA2462110A 2001-10-04 2002-10-02 Phenyl-piperazine derivatives as serotonin reuptake inhibitors Expired - Lifetime CA2462110C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DKPA200101466 2001-10-04
DKPA200101466 2001-10-04
PCT/DK2002/000659 WO2003029232A1 (en) 2001-10-04 2002-10-02 Phenyl-piperazine derivatives as serotonin reuptake inhibitors

Publications (3)

Publication Number Publication Date
CA2462110E CA2462110E (en) 2003-04-10
CA2462110A1 CA2462110A1 (en) 2003-04-10
CA2462110C true CA2462110C (en) 2010-05-11

Family

ID=8160750

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2462110A Expired - Lifetime CA2462110C (en) 2001-10-04 2002-10-02 Phenyl-piperazine derivatives as serotonin reuptake inhibitors

Country Status (38)

Country Link
US (10) US7144884B2 (h)
EP (2) EP1749818B1 (h)
JP (3) JP3896116B2 (h)
KR (3) KR100842702B1 (h)
CN (1) CN1319958C (h)
AR (2) AR036659A1 (h)
AT (2) ATE386730T1 (h)
AU (2) AU2002333220C1 (h)
BE (1) BE2014C036I2 (h)
BR (3) BR122012009534C8 (h)
CA (1) CA2462110C (h)
CO (1) CO5580746A2 (h)
CY (3) CY1107924T1 (h)
DE (2) DE60233608D1 (h)
DK (2) DK1749818T3 (h)
EA (2) EA007537B3 (h)
EG (1) EG25095A (h)
ES (2) ES2328725T3 (h)
FR (1) FR14C0033I2 (h)
HR (1) HRP20040220A2 (h)
HU (3) HU228956B1 (h)
IL (1) IL160655A0 (h)
IS (2) IS2578B (h)
LT (1) LTC1436271I2 (h)
LU (1) LU92397I2 (h)
ME (1) ME00039B (h)
MX (1) MXPA04002959A (h)
MY (1) MY140950A (h)
NL (1) NL300652I1 (h)
NO (3) NO326443B1 (h)
NZ (1) NZ531556A (h)
PL (2) PL210551B1 (h)
PT (2) PT1749818E (h)
RS (2) RS52865B (h)
SI (1) SI1436271T1 (h)
UA (2) UA81749C2 (h)
WO (1) WO2003029232A1 (h)
ZA (1) ZA200401583B (h)

Families Citing this family (105)

* Cited by examiner, † Cited by third party
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UA81749C2 (uk) 2001-10-04 2008-02-11 Х. Луннбек А/С Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну
GB0305575D0 (en) * 2003-03-11 2003-04-16 Glaxo Group Ltd Novel compounds
PL1626720T3 (pl) 2003-04-04 2009-02-27 H Lundbeck As Pochodne 4-(2-fenylosulfanylo-fenylo)-piperydyny jako inhibitory wychwytu zwrotnego serotoniny
MXPA05010627A (es) * 2003-04-04 2005-12-12 Lundbeck & Co As H Derivados de 4-(2-feniloxifenil)-piperidina o 1,2,3,6-tetrahidropiridina como inhibidores de la recaptacion de serotonina.
EA009417B1 (ru) * 2003-04-04 2007-12-28 Х. Лундбекк А/С Производные 4-(2-фенилоксифенил)пиперидина или -1,2,3,6-тетрагидропиридина в качестве ингибиторов обратного захвата серотонина
EA010869B1 (ru) * 2003-04-04 2008-12-30 Х. Лундбекк А/С Производные 4-(2-фенилсульфанилфенил)пиперидина в качестве ингибиторов повторного поглощения серотонина
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PT1701940E (pt) 2003-12-23 2008-07-30 Lundbeck & Co As H Derivados de 2-(1h-indolilsulfanil)-benzil-amina como ssri
AR052308A1 (es) * 2004-07-16 2007-03-14 Lundbeck & Co As H Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto
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US7629473B2 (en) 2005-06-17 2009-12-08 H. Lundbeck A/S 2-(1H-indolylsulfanyl)-aryl amine derivatives
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ZA200809917B (en) * 2006-06-16 2010-08-25 Lundbeck & Co As H Crystalline forms of 4- [2-(4-Methylphenylsulfanyl) - Phenyl] piperidine with combined serotonin and norepinephrine reuptake inhibition for the treatment of neuropathic pain
PL2044020T3 (pl) 2006-06-16 2011-09-30 H Lundbeck As Krystaliczne postaci 4-[2-(4-metylofenylosulfanylo)-fenylo]piperydyny z równoczesnym hamowaniem wychwytu zwrotnego serotoniny i norepinefryny do leczenia bólu neuropatycznego
SI2044020T1 (sl) * 2006-06-16 2011-06-30 Lundbeck & Co As H Kristaliniäśne oblike 4-(2-(4-metilfenilsulfanil)-fenil)piperidina s kombiniranim zaviranjem ponovnega privzema serotonina in norepinefrina za zdravljenje nevropatske boleäśine
TWI405588B (zh) * 2007-03-20 2013-08-21 Lundbeck & Co As H ４-〔２-（４-甲苯基硫基）-苯基〕哌啶之鹽類的液體調配物
TWI432194B (zh) * 2007-03-20 2014-04-01 Lundbeck & Co As H ４-〔２-（４-甲基苯硫基）苯基〕哌啶之新穎治療用途
TW200848411A (en) * 2007-03-20 2008-12-16 Lundbeck & Co As H Novel therapeutic uses of 1-[2-(2, 4-dimethylphenylsulfanyl)phenyl]-piperazine
HRP20140044T1 (hr) * 2007-06-15 2014-02-14 H. Lundbeck A/S 4-[2-(4-metilfenilsulfanil)fenil]piperidin za lijeäśenje iritabilnog sindroma crijeva (ibs)
TW200932233A (en) 2007-11-13 2009-08-01 Lundbeck & Co As H Therapeutic uses of compounds having combined SERT, 5-HT3 and 5-HT1a activity
AU2014200364B2 (en) * 2007-11-13 2015-09-17 H. Lundbeck A/S Therapeutic uses of compounds having combined SERT, 5-HT3 and 5-HT1A activity
TW200938194A (en) * 2007-12-14 2009-09-16 Lundbeck & Co As H Therapeutic uses of compounds having affinity to the serotonin transporter, serotonin receptors and noradrenalin transporter
TW200932225A (en) * 2007-12-14 2009-08-01 Lundbeck & Co As H 4-[2,3-difluoro-6-(2-fluoro-4-methyl-phenylsulfanyl)-phenyl]-piperidine
WO2009081259A1 (en) * 2007-12-21 2009-07-02 Pfizer Inc. Phenoxy-pyridyl derivatives
UA98698C2 (en) * 2008-03-03 2012-06-11 Х. Луннбек А/С Phenylsulfanylphenyl-piperidines and process for the preparation thereof
TWI443087B (zh) 2008-11-14 2014-07-01 Theravance Inc ４－〔２－（２－氟苯氧基甲基）苯基〕哌啶化合物
TW201033181A (en) 2009-02-17 2010-09-16 Lundbeck & Co As H Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine
KR101779214B1 (ko) * 2009-04-24 2017-09-18 하. 룬드벡 아크티에셀스카브 １―［２―（２，４―디메틸페닐술파닐）페닐］피페라진 염의 액체 제형
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RS55304B1 (sr) 2011-06-20 2017-03-31 H Lundbeck As Deuterizovani 1-piperazino-3-fenil indani za tretiranje šizofrenije
RU2622082C2 (ru) 2011-11-14 2017-06-09 Нестек С.А. Анализы и способы выбора режима лечения пациента с депрессией
DK2800746T3 (da) * 2012-01-03 2019-05-20 H Lundbeck As Fremgangsmåde til fremstilling af 1-[2-(2,4-dimethyl-phenylsulfanyl)-phenyl]-piperazin
EP2897943B1 (en) 2012-09-19 2019-04-24 Sandoz AG Crystalline form of vortioxetine hydrobromide
KR102171152B1 (ko) 2012-12-13 2020-10-29 하. 룬드벡 아크티에셀스카브 보르티옥세틴 및 도네페질을 포함하는 조성물
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CN104059030B (zh) * 2014-05-30 2016-05-04 镇江圣安医药有限公司 [(苯硫烷基)-苯基]哌嗪的衍生物及其药物组合物和用途
FR3023320B1 (fr) * 2014-07-03 2017-03-10 Ifp Energies Now Systeme et procede de stockage et de recuperation d'energie par gaz comprime avec stockage de la chaleur au moyen d'un echangeur radial
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