DE69230926D1 - Benzimidazolonderivate als 5-HT1A und 5-HT2-Antagonisten - Google Patents

Benzimidazolonderivate als 5-HT1A und 5-HT2-Antagonisten

Info

Publication number
DE69230926D1
DE69230926D1 DE69230926T DE69230926T DE69230926D1 DE 69230926 D1 DE69230926 D1 DE 69230926D1 DE 69230926 T DE69230926 T DE 69230926T DE 69230926 T DE69230926 T DE 69230926T DE 69230926 D1 DE69230926 D1 DE 69230926D1
Authority
DE
Germany
Prior art keywords
alkyl
substituted
mono
optionally
alkoxy
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
DE69230926T
Other languages
English (en)
Other versions
DE69230926T2 (de
Inventor
Marco Turconi
Giuseppe Bietti
Ettore Giraldo
Franco Borsini
Maura Bignotti
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.)
Boehringer Ingelheim Italia SpA
Original Assignee
Boehringer Ingelheim Italia 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 Boehringer Ingelheim Italia SpA filed Critical Boehringer Ingelheim Italia SpA
Publication of DE69230926D1 publication Critical patent/DE69230926D1/de
Application granted granted Critical
Publication of DE69230926T2 publication Critical patent/DE69230926T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
DE69230926T 1991-07-30 1992-07-30 Benzimidazolonderivate als 5-HT1A und 5-HT2-Antagonisten Expired - Lifetime DE69230926T2 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ITMI912118A IT1251144B (it) 1991-07-30 1991-07-30 Derivati del benzimidazolone

Publications (2)

Publication Number Publication Date
DE69230926D1 true DE69230926D1 (de) 2000-05-25
DE69230926T2 DE69230926T2 (de) 2000-10-05

Family

ID=11360463

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69230926T Expired - Lifetime DE69230926T2 (de) 1991-07-30 1992-07-30 Benzimidazolonderivate als 5-HT1A und 5-HT2-Antagonisten

Country Status (32)

Country Link
US (1) US5576318A (de)
EP (1) EP0526434B1 (de)
JP (1) JP2989667B2 (de)
KR (1) KR100263495B1 (de)
AT (1) ATE191910T1 (de)
AU (1) AU665366B2 (de)
CA (1) CA2114542C (de)
CZ (1) CZ281511B6 (de)
DE (1) DE69230926T2 (de)
DK (1) DK0526434T3 (de)
EE (1) EE03070B1 (de)
ES (1) ES2144412T3 (de)
FI (1) FI111460B (de)
GR (1) GR3033947T3 (de)
HK (1) HK1010725A1 (de)
HU (2) HUT70195A (de)
IE (1) IE922464A1 (de)
IL (1) IL102665A (de)
IT (1) IT1251144B (de)
MX (1) MX9204139A (de)
NO (1) NO304070B1 (de)
NZ (1) NZ243777A (de)
PH (1) PH30998A (de)
PL (1) PL171329B1 (de)
PT (1) PT526434E (de)
RU (1) RU2096411C1 (de)
SG (1) SG52407A1 (de)
SK (1) SK279292B6 (de)
TW (1) TW209862B (de)
UA (1) UA42684C2 (de)
WO (1) WO1993003016A1 (de)
ZA (1) ZA925682B (de)

Families Citing this family (80)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1251144B (it) * 1991-07-30 1995-05-04 Boehringer Ingelheim Italia Derivati del benzimidazolone
US5266571A (en) * 1992-01-09 1993-11-30 Amer Moh Samir Treatment of hemorrhoids with 5-HT2 antagonists
SE9201138D0 (sv) * 1992-04-09 1992-04-09 Astra Ab Novel phthalimidoalkylpiperazines
DK148392D0 (da) * 1992-12-09 1992-12-09 Lundbeck & Co As H Heterocykliske forbindelser
AU6391894A (en) * 1993-03-16 1994-10-11 Pfizer Inc. Naphthalene derivatives
JP3719612B2 (ja) * 1993-06-14 2005-11-24 塩野義製薬株式会社 ヘテロ環を含有する尿素誘導体
IL114027A (en) * 1994-06-08 1999-11-30 Lundbeck & Co As H 4-Phenyl piperazine (piperidine or tetrahydropyridine) derivatives serotinin 5-HT1A and dopamin D2 receptor ligand pharmaceutical compositions containing them
CA2192975C (en) * 1994-06-14 1999-09-21 Anton F. Fliri Benzimidazolone derivatives
CA2196769C (en) * 1994-08-05 2002-10-08 William S. Faraci Benzimidazole derivatives having dopaminergic activity
US5883094A (en) * 1995-04-24 1999-03-16 Pfizer Inc. Benzimidazolone derivatives with central dopaminergic activity
US5889010A (en) * 1995-05-18 1999-03-30 Pfizer Inc. Benzimidazole derivatives having dopaminergic activity
WO1997016187A1 (en) * 1995-10-31 1997-05-09 Merck & Co., Inc. Muscarine antagonists
EP1087954A1 (de) * 1998-06-15 2001-04-04 American Home Products Corporation Cycloalkyl-substituiertte aryl-piperazine, piperidine und tetrahydropyridine als serotonergische agente
US6376494B1 (en) 1998-06-15 2002-04-23 American Home Products Corporation Cycloalkyl-substituted aryl-piperazines, piperidines and tetrahydropyridines as serotonergic agents
AR022303A1 (es) * 1999-01-22 2002-09-04 Lundbeck & Co As H Derivados de piperidina, tetrahidropiridina y piperazina, su preparacion y utilizacion
IT1313625B1 (it) * 1999-09-22 2002-09-09 Boehringer Ingelheim Italia Derivati benzimidazolonici aventi affinita' mista per i recettori diserotonina e dopamina.
ATE341538T1 (de) * 2000-09-19 2006-10-15 Boehringer Ingelheim Pharma Benzimidazolonderivate mit affinität zu serotonin-und dopaminrezeptoren
CA2417081C (en) * 2000-09-19 2008-08-05 Enzo Cereda New n, n'-disubstituted benzimidazolone derivatives with affinity at the serotonin and dopamine receptors
US6586435B2 (en) 2000-09-19 2003-07-01 Boehringer Ingelheim Pharma Kg Benzimidazolone derivatives displaying affinity at the serotonin and dopamine receptors
US6521623B1 (en) 2000-09-19 2003-02-18 Boehringer Ingelheim Pharma Kg N,N'-disubstituted benzimidazolone derivatives with affinity at the serotonin and dopamine receptors
CA2453837C (en) * 2001-07-20 2011-10-04 Psychogenics, Inc. Treatment for attention-deficit hyperactivity disorder using eltoprazine and related compounds
US7183410B2 (en) * 2001-08-02 2007-02-27 Bidachem S.P.A. Stable polymorph of flibanserin
ATE288911T1 (de) * 2001-08-02 2005-02-15 Bidachem Spa Stabiles polymorph von flibanserin, industrielles verfahren zu dessen herstellung und dessen verwendung zur herstellung von medikamenten
US20030060475A1 (en) * 2001-08-10 2003-03-27 Boehringer Ingelheim Pharma Kg Method of using flibanserin for neuroprotection
DE10138273A1 (de) * 2001-08-10 2003-02-27 Boehringer Ingelheim Pharma Arzneimittel mit neuroprotektiver Wirkung
US10675280B2 (en) 2001-10-20 2020-06-09 Sprout Pharmaceuticals, Inc. Treating sexual desire disorders with flibanserin
UA78974C2 (en) 2001-10-20 2007-05-10 Boehringer Ingelheim Pharma Use of flibanserin for treating disorders of sexual desire
US20040048877A1 (en) * 2002-05-22 2004-03-11 Boehringer Ingelheim Pharma Gmbh & Co. Kg Pharmaceutical compositions containing flibanserin
SI1511489T1 (sl) * 2002-05-22 2011-06-30 Boehringer Ingelheim Pharma Novi farmacevtski sestavki, ki vsebujejo polimorf A flibanserina
OA12923A (en) * 2002-09-17 2006-10-13 Warner Lambert Co Heterocyclic substituted piperazines for the treatment of schizophrenia.
PT1664036E (pt) * 2003-09-03 2012-02-16 Pfizer Compostos de benzimidazolona que possuem actividade agonística do receptor 5-ht4
MXPA06012059A (es) * 2004-04-22 2007-01-25 Boehringer Ingelheim Int Nuevas composiciones farmaceuticas para el tratamiento de los trastornos sexuales ii.
US20050239798A1 (en) * 2004-04-22 2005-10-27 Boehringer Ingelheim Pharmaceuticals, Inc. Method for the treatment of premenstrual and other female sexual disorders
US7737163B2 (en) * 2004-06-15 2010-06-15 Pfizer Inc. Benzimidazolone carboxylic acid derivatives
EP1758891A2 (de) * 2004-06-15 2007-03-07 Pfizer Japan Inc. Benzimidazoloncarbonsäurederivate
US20060014757A1 (en) * 2004-07-14 2006-01-19 Boehringer Ingelheim Pharmaceuticals Method for the treatment of anorexia nervosa
US20060025420A1 (en) * 2004-07-30 2006-02-02 Boehringer Ingelheimn International GmbH Pharmaceutical compositions for the treatment of female sexual disorders
EP1789048A1 (de) * 2004-09-03 2007-05-30 Boehringer Ingelheim International GmbH Verfahren zur behandlung von aufmerksamkeitsdefizitstörung mit hyperaktivität
JP4130220B1 (ja) * 2005-02-22 2008-08-06 ファイザー株式会社 ５ｈｔ４受容体アゴニストとしてのオキシインドール誘導体
WO2006096439A2 (en) * 2005-03-04 2006-09-14 Boehringer Ingelheim International Gmbh Pharmaceutical compositions for the treatment and/or prevention of schizophrenia and related diseases
JP2008538741A (ja) * 2005-03-04 2008-11-06 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 鬱病の治療用及び／又は予防用の医薬組成物
WO2006096434A2 (en) * 2005-03-04 2006-09-14 Boehringer Ingelheim International Gmbh Pharmaceutical compositions for the treatment and/or prevention of anxiety disorders
CA2608249A1 (en) * 2005-05-06 2006-11-16 Boehringer Ingelheim International Gmbh Method for the treatment of drug abuse with flibanserin
CA2608713A1 (en) * 2005-05-19 2006-11-23 Boehringer Ingelheim International Gmbh Method for the treatment of sexual dysfunctions due to medical conditions
US20060264511A1 (en) * 2005-05-19 2006-11-23 Boehringer Ingelheim International Gmbh Method for the treatment of drug-induced sexual dysfunction
US8227476B2 (en) 2005-08-03 2012-07-24 Sprout Pharmaceuticals, Inc. Use of flibanserin in the treatment of obesity
US7790726B2 (en) * 2005-08-16 2010-09-07 Chemocentryx, Inc. Monocyclic and bicyclic compounds and methods of use
EP1945214A1 (de) * 2005-10-29 2008-07-23 Boehringer Ingelheim International GmbH Benzimidazolon-derivate zur behandlung von prämenstruellen und anderen sexuellen störungen der frau
US20070123540A1 (en) * 2005-10-29 2007-05-31 Angelo Ceci Sexual desire enhancing medicaments comprising benzimidazolone derivatives
US20070105869A1 (en) * 2005-11-08 2007-05-10 Stephane Pollentier Use of flibanserin for the treatment of pre-menopausal sexual desire disorders
JP2009527525A (ja) * 2006-02-20 2009-07-30 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 尿失禁治療用のベンゾイミダゾロン誘導体
EP1988077A4 (de) * 2006-02-23 2009-09-02 Shionogi & Co Nitrogene heterocyclische derivate, die mit cyclischen gruppen substituiert sind
CA2642368A1 (en) * 2006-02-28 2007-09-07 Boehringer Ingelheim International Gmbh Treatment of prevention of valvular heart disease with flibanserin
CA2649938A1 (en) * 2006-05-09 2007-11-15 Boehringer Ingelheim International Gmbh Use of flibanserin for the treatment of post-menopausal sexual desire disorders
ATE456369T1 (de) 2006-06-30 2010-02-15 Boehringer Ingelheim Int Flibanserin zur behandlung von harninkontinenz und assoziierten erkrankungen
CA2657043A1 (en) * 2006-07-14 2008-01-17 Boehringer Ingelheim International Gmbh Use of flibanserin for the treatment of sexual disorders in females
CL2007002214A1 (es) 2006-08-14 2008-03-07 Boehringer Ingelheim Int Composicion farmaceutica en la forma de comprimido, donde al menos la longitud del comprimido en el estado anterior de la aplicacion es al menos 7/12 del diametro pilorico del paciente y despues de ingerirlo en estado alimentado, la longitud del comp
WO2008019996A2 (en) 2006-08-14 2008-02-21 Boehringer Ingelheim International Gmbh Formulations of flibanserin and method for manufacturing the same
MX2009002031A (es) 2006-08-25 2009-03-06 Boehringer Ingelheim Int Sistema de liberacion controlada y metodo para fabricarlo.
CA2672957C (en) 2006-12-20 2015-04-14 Boehringer Ingelheim International Gmbh Sulfated benzimidazolone derivatives having mixed serotonine receptor affinity
WO2008090742A1 (ja) * 2007-01-23 2008-07-31 National University Corporation Hokkaido University 眼疾患モデル用非ヒト動物
JP5514716B2 (ja) * 2007-05-11 2014-06-04 コリア・リサーチ・インスティテュート・オブ・ケミカル・テクノロジー アリールピペリジン置換基を有するイミダゾール誘導体、その製造方法及びこれを含む医薬組成物
CL2008002693A1 (es) 2007-09-12 2009-10-16 Boehringer Ingelheim Int Uso de flibanserina para el tratamiento de sintomas vasomotores seleccionados de sofocos, sudores nocturnos, cambios de estado de animo e irritabilidad
US20110028490A1 (en) * 2008-01-24 2011-02-03 Neurosearch A/S 4-phenyl-piperazin-1-yl-alkyl-benzoimidazol-2-one derivatives and their use as monoamine neurotransmitter re-uptake in-hibitors
EP2090297A1 (de) 2008-02-13 2009-08-19 Boehringer Ingelheim International GmbH Formulierungen aus Flibanserin
CA2686480A1 (en) * 2008-12-15 2010-06-15 Boehringer Ingelheim International Gmbh New salts
WO2010146595A2 (en) * 2009-06-16 2010-12-23 Symed Labs Limited Novel polymorphs of flibanserin hydrochloride
BRPI1003506B1 (pt) 2010-09-24 2019-12-03 Ache Int Bvi Ltd composto alquil-piperazino-fenil-4(3h)quinazolinonas e uso do composto alquil-piperazino-fenil-4(3h)quinazolinonas associado aos receptores serotoninérgicos 5-ht1a e 5-ht2a
EA029054B1 (ru) * 2012-10-11 2018-02-28 Саузерн Рисерч Инститьют Мочевинные и амидные производные аминоалкилпиперазинов и их применение
CN104926734B (zh) * 2015-07-07 2017-04-05 苏州立新制药有限公司 氟班色林的制备方法
WO2017076213A1 (zh) * 2015-11-02 2017-05-11 苏州旺山旺水生物医药有限公司 苯并咪唑类化合物、其制备方法及用途
WO2017076356A1 (zh) * 2015-11-05 2017-05-11 苏州晶云药物科技有限公司 氟班色林的新晶型及其制备方法
CN106749038A (zh) * 2015-11-25 2017-05-31 山东诚创医药技术开发有限公司 一种氟班色林的制备方法
CN106866546A (zh) * 2015-12-10 2017-06-20 常州爱诺新睿医药技术有限公司 氟班色林或其药学上可接受的盐与药用辅料的固体分散体及其制备方法
CN113683570A (zh) 2016-01-31 2021-11-23 孟晓明 氟班色林的新晶型及其制备方法及其用途
WO2017133337A1 (zh) * 2016-02-02 2017-08-10 深圳市塔吉瑞生物医药有限公司 一种取代的苯并咪唑酮化合物及包含该化合物的组合物
CN107235913B (zh) * 2016-03-29 2020-07-10 苏州科伦药物研究有限公司 工业规模高效制造优质氟班色林的方法
CN106866582A (zh) * 2017-01-10 2017-06-20 广州隽沐生物科技有限公司 一种氟班色林中间体的制备方法
HU231283B1 (hu) 2018-08-01 2022-09-28 Richter Gedeon Nyrt Eljárás a flibanserin többlépéses folyamatos áramú előállítására
EP4308119A1 (de) * 2021-03-19 2024-01-24 Centre National de la Recherche Scientifique <sup2/>? <sub2/>?7?anwendungen von vorbelasteten serotonin 5-ht-rezeptor liganden zur behandlung von schmerzen, multipler sklerose und kontrolle der thermoregulation

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3406178A (en) * 1964-02-04 1968-10-15 Monsanto Chem Australia Ltd Preparation of 2-substituted benzimidazoles
US3362956A (en) * 1965-08-19 1968-01-09 Sterling Drug Inc 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines
YU39992B (en) * 1976-04-02 1985-06-30 Janssen Pharmaceutica Nv Process for obtaining new piperazine and piperidine derivatives
IL57569A0 (en) * 1978-06-20 1979-10-31 Synthelabo Phenylpiperazine derivative,their preparation and pharmaceutical compositions containing them
IT1176613B (it) * 1984-08-14 1987-08-18 Ravizza Spa Derivati piperazinici farmacologicamente attivi e processo per la loro preparazione
IE58370B1 (en) * 1985-04-10 1993-09-08 Lundbeck & Co As H Indole derivatives
GB8607294D0 (en) * 1985-04-17 1986-04-30 Ici America Inc Heterocyclic amide derivatives
HUT43600A (en) * 1985-06-22 1987-11-30 Sandoz Ag Process for production of new thiazole derivatives and medical compound containing those
GB8601160D0 (en) * 1986-01-17 1986-02-19 Fujisawa Pharmaceutical Co Heterocyclic compounds
US5036088A (en) * 1986-06-09 1991-07-30 Pfizer Inc. Antiallergy and antiinflammatory agents, compositions and use
JPH0784462B2 (ja) * 1986-07-25 1995-09-13 日清製粉株式会社 ベンゾイミダゾ−ル誘導体
US4954503A (en) * 1989-09-11 1990-09-04 Hoechst-Roussel Pharmaceuticals, Inc. 3-(1-substituted-4-piperazinyl)-1H-indazoles
IT1251144B (it) * 1991-07-30 1995-05-04 Boehringer Ingelheim Italia Derivati del benzimidazolone

Also Published As

Publication number Publication date
CA2114542A1 (en) 1993-02-18
EP0526434B1 (de) 2000-04-19
JP2989667B2 (ja) 1999-12-13
EP0526434A1 (de) 1993-02-03
WO1993003016A1 (en) 1993-02-18
CZ281511B6 (cs) 1996-10-16
DK0526434T3 (da) 2000-07-17
IE922464A1 (en) 1993-02-10
NO940306L (no) 1994-03-14
EE03070B1 (et) 1998-02-16
KR100263495B1 (ko) 2000-11-01
PH30998A (en) 1997-12-23
JPH06509575A (ja) 1994-10-27
HK1010725A1 (en) 1999-06-25
PL171329B1 (pl) 1997-04-30
CZ17094A3 (en) 1994-05-18
ITMI912118A1 (it) 1993-01-31
NO940306D0 (no) 1994-01-28
FI111460B (fi) 2003-07-31
SG52407A1 (en) 1998-09-28
HU211256A9 (en) 1995-11-28
NO304070B1 (no) 1998-10-19
TW209862B (de) 1993-07-21
FI940420A (fi) 1994-01-28
PL302163A1 (en) 1994-07-11
CA2114542C (en) 2004-02-24
DE69230926T2 (de) 2000-10-05
ZA925682B (en) 1994-01-31
IT1251144B (it) 1995-05-04
PT526434E (pt) 2000-08-31
NZ243777A (en) 1995-04-27
SK279292B6 (sk) 1998-09-09
MX9204139A (es) 1993-01-01
AU2427592A (en) 1993-03-02
GR3033947T3 (en) 2000-11-30
AU665366B2 (en) 1996-01-04
SK10194A3 (en) 1994-12-07
IL102665A (en) 1996-10-31
ATE191910T1 (de) 2000-05-15
ES2144412T3 (es) 2000-06-16
RU2096411C1 (ru) 1997-11-20
HU9400255D0 (en) 1994-05-30
HUT70195A (en) 1995-09-28
ITMI912118A0 (it) 1991-07-30
UA42684C2 (uk) 2001-11-15
US5576318A (en) 1996-11-19
FI940420A0 (fi) 1994-01-28

Similar Documents

Publication Publication Date Title
DE69230926D1 (de) Benzimidazolonderivate als 5-HT1A und 5-HT2-Antagonisten
IT1231413B (it) Derivati dell&#39;acido benzimidazolin-2-osso-1-carbossilico utili come antagonisti dei recettori 5-ht
ATE402151T1 (de) 2-(arylphenyl)amino-imidazolin-derivate

Legal Events

Date Code Title Description
8364 No opposition during term of opposition
R071 Expiry of right

Ref document number: 526434

Country of ref document: EP