CA2341991C - Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists - Google Patents

Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists Download PDF

Info

Publication number
CA2341991C
CA2341991C CA002341991A CA2341991A CA2341991C CA 2341991 C CA2341991 C CA 2341991C CA 002341991 A CA002341991 A CA 002341991A CA 2341991 A CA2341991 A CA 2341991A CA 2341991 C CA2341991 C CA 2341991C
Authority
CA
Canada
Prior art keywords
dihydro
pyrrolo
carboxaldehyde
disorders
indol
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 - Fee Related
Application number
CA002341991A
Other languages
English (en)
French (fr)
Other versions
CA2341991A1 (en
Inventor
David Reginald Adams
Jonathan Mark Bentley
Jonathan Richard Anthony Roffey
Richard John Hamlyn
Suneel Gaur
Matthew Alexander James Duncton
James Edward Paul Davidson
Michael John Bickerdike
Ian Anthony Cliffe
Howard Langham Mansell
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.)
Ligand UK Research Ltd
Original Assignee
Vernalis Research Ltd
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 Vernalis Research Ltd filed Critical Vernalis Research Ltd
Publication of CA2341991A1 publication Critical patent/CA2341991A1/en
Application granted granted Critical
Publication of CA2341991C publication Critical patent/CA2341991C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10Drugs for genital or sexual disorders; Contraceptives for impotence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/06Antimigraine agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/20Hypnotics; Sedatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32Alcohol-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (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)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Diabetes (AREA)
  • Addiction (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Reproductive Health (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Anesthesiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Cardiology (AREA)
  • Psychology (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA002341991A 1998-09-01 1999-09-01 Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists Expired - Fee Related CA2341991C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9819035.8A GB9819035D0 (en) 1998-09-01 1998-09-01 Chemical compounds VII
GB9819035.8 1998-09-01
PCT/GB1999/002884 WO2000012510A1 (en) 1998-09-01 1999-09-01 Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists

Publications (2)

Publication Number Publication Date
CA2341991A1 CA2341991A1 (en) 2000-03-09
CA2341991C true CA2341991C (en) 2009-04-07

Family

ID=10838167

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002341991A Expired - Fee Related CA2341991C (en) 1998-09-01 1999-09-01 Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists

Country Status (29)

Country Link
US (1) US6433175B1 (enExample)
EP (1) EP1109813B1 (enExample)
JP (1) JP2002523508A (enExample)
KR (2) KR100768595B1 (enExample)
CN (1) CN1165537C (enExample)
AT (1) ATE273308T1 (enExample)
AU (1) AU758084B2 (enExample)
BR (1) BR9913477A (enExample)
CA (1) CA2341991C (enExample)
CZ (1) CZ296275B6 (enExample)
DE (1) DE69919364T2 (enExample)
DK (1) DK1109813T3 (enExample)
ES (1) ES2226430T3 (enExample)
GB (1) GB9819035D0 (enExample)
HR (1) HRP20010126B1 (enExample)
HU (1) HUP0103333A3 (enExample)
ID (1) ID28842A (enExample)
IL (2) IL141659A0 (enExample)
MX (1) MXPA01002101A (enExample)
NO (1) NO321527B1 (enExample)
NZ (1) NZ510097A (enExample)
PL (1) PL346427A1 (enExample)
PT (1) PT1109813E (enExample)
RU (1) RU2232162C2 (enExample)
SI (1) SI1109813T1 (enExample)
TR (2) TR200100659T2 (enExample)
WO (1) WO2000012510A1 (enExample)
YU (1) YU16001A (enExample)
ZA (1) ZA200101457B (enExample)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6960579B1 (en) 1998-05-19 2005-11-01 Alcon Manufacturing, Ltd. Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders
GB9902047D0 (en) * 1999-01-29 1999-03-17 Cerebrus Ltd Chemical compounds XI
US6465467B1 (en) 1999-05-21 2002-10-15 Biovitrum Ab Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases
GB9918965D0 (en) 1999-08-11 1999-10-13 Cerebrus Ltd Chemical compounds xxi
US6818639B2 (en) 2000-07-21 2004-11-16 Biovitrum Ab Pharmaceutical combination formulation and method of treatment with the combination
SE0002754D0 (sv) * 2000-07-21 2000-07-21 Pharmacia & Upjohn Ab New pharmaceutical combination formulation and method of treatment with the combination
WO2002040457A1 (en) 2000-11-20 2002-05-23 Biovitrum Ab Piperazinylpyrazines compounds as antagonists of serotonin 5-ht2 receptor
SE0004245D0 (sv) 2000-11-20 2000-11-20 Pharmacia Ab Novel compounds and their use
JP2005506280A (ja) 2000-12-20 2005-03-03 ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー アリールおよびアミノアリール置換セロトニン受容体アゴニストおよびアンタゴニストリガンド
ATE369368T1 (de) 2000-12-27 2007-08-15 Hoffmann La Roche Indolderivate und deren verwendung als 5-ht2b- und 5-ht2c-rezeptorliganden
JP2004535418A (ja) 2001-06-01 2004-11-25 アルコン,インコーポレイテッド ピラノインダゾールおよび緑内障治療への使用
EP1392658A4 (en) 2001-06-01 2004-10-13 Alcon Inc NOVEL FUSED INDAZOLES AND INDOLES AND THEIR USE IN THE TREATMENT OF GLAUCOMES
AU2002259312B2 (en) 2001-06-01 2007-01-04 Alcon, Inc. Novel arylaminopropane analogues and their use for the treatment of glaucoma
TW593302B (en) 2001-12-20 2004-06-21 Alcon Inc Novel benzodifuranimidazoline and benzofuranimidazoline derivatives and their use for the treatment of glaucoma
NZ536664A (en) 2002-06-19 2007-07-27 Biovitrum Ab Piperazinylpyrazine derivative compounds, their use and preparation
WO2004019874A2 (en) * 2002-08-30 2004-03-11 Alcon, Inc. Substituted 5-chroman-5-yl-ethylamine compounds and their use for the treatment of glaucoma
EP1581209A4 (en) 2002-12-13 2009-03-11 Alcon Inc NEW BENZOPYRAN ANALOGUE AND ITS USE FOR THE TREATMENT OF GLAUKOM
CL2004000826A1 (es) 2003-04-25 2005-03-04 Pfizer Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129
GB0314967D0 (en) * 2003-06-26 2003-07-30 Hoffmann La Roche Piperazine derivatives
US7435837B2 (en) * 2003-10-24 2008-10-14 Wyeth Dihydrobenzofuranyl alkanamine derivatives and methods for using same
WO2005053688A1 (en) 2003-11-26 2005-06-16 Alcon, Inc. Substituted furo[2,3-g] indazoles for the treatment of glaucoma
US7338972B1 (en) 2003-12-15 2008-03-04 Alcon, Inc. Substituted 1-alkylamino-1H-indazoles for the treatment of glaucoma
WO2005058911A2 (en) 2003-12-15 2005-06-30 Alcon, Inc. Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma
US7129257B1 (en) 2003-12-15 2006-10-31 Alcon, Inc. Pyrazolo[3,4- e]benzoxazoles for the treatment of glaucoma
EP1792629A4 (en) 2004-08-25 2010-08-25 Takeda Pharmaceutical MEANS FOR THE PREVENTION / TREATMENT OF STRESS-RELATED HARNINE INCONTINENCE AND PRECAUTIONARY METHOD FOR THIS
US7608626B2 (en) 2004-11-01 2009-10-27 Wyeth Substituted indolizines and derivatives as CNS agents
US7425572B2 (en) 2004-12-08 2008-09-16 Alcon, Inc. Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma
JP4318744B2 (ja) 2005-03-31 2009-08-26 ファイザー・プロダクツ・インク シクロペンタピリジンおよびテトラヒドロキノリン誘導体
FR2884252B1 (fr) * 2005-04-08 2007-05-18 Aventis Pharma Sa Nouveaux derives d'isoindoles, compositions les contenant, leur preparation et leurs utilisations pharmaceutiques notamment en tant qu'inhibiteurs d'activites de la proteine chaperone hsp90
AU2006239897A1 (en) * 2005-04-22 2006-11-02 Wyeth Crystal forms of {[(2R)-7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine hydrochloride
EP1888585B1 (en) * 2005-05-03 2011-06-29 F. Hoffmann-La Roche AG Tetracyclic azapyrazinoindolines as 5-ht2 ligands
EP2727585A1 (en) 2006-05-16 2014-05-07 Takeda Pharmaceutical Company Limited In-vivo screening method
CN101506172A (zh) * 2006-07-14 2009-08-12 辉瑞产品公司 (7S)-7-[(5-氟-2-甲基-苄基)氧基]-2-[(2R)-2-甲基哌嗪-1-基]-6,7-二氢-5H-环戊烷并[b]吡啶的酒石酸盐
US20100266504A1 (en) 2007-11-15 2010-10-21 Takahiro Matsumoto Condensed pyridine derivative and use thereof
KR101062376B1 (ko) 2008-04-10 2011-09-06 한국화학연구원 신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물
US20120253036A1 (en) 2009-12-11 2012-10-04 Yukinori Nagakura Agent for treating fibromyalgia
US20130267500A1 (en) 2010-09-01 2013-10-10 Arena Pharmaceuticals, Inc. 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level
CN102964352B (zh) * 2012-11-23 2015-04-08 华中师范大学 具有生物活性的手性2,3-二氢吡咯[1,2-a]吲哚衍生物及其不对称合成方法
WO2015066344A1 (en) 2013-11-01 2015-05-07 Arena Pharmaceuticals, Inc. 5-ht2c receptor agonists and compositions and methods of use
US20210052600A1 (en) 2017-12-27 2021-02-25 Takeda Pharmaceutical Company Limited Therapeutic agents for stress urinary incontinence and incotinence of feces
US11485734B2 (en) 2018-10-02 2022-11-01 Northwestern University Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2C (5-HT2C)

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3250783A (en) * 1964-09-21 1966-05-10 American Cyanamid Co Novel pyrrolo (1, 2-alpha) indoles
US4134894A (en) * 1978-05-04 1979-01-16 Warner-Lambert Company Pyrrolo[1,2-a]indole compounds
GB8416724D0 (en) * 1984-06-30 1984-08-01 Sorbio Sa Lab Active compounds
US4778812A (en) * 1987-06-12 1988-10-18 American Home Products Corporation 2,3-dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-amines and derivatives thereof
GB8802127D0 (en) * 1988-02-01 1988-03-02 Glaxo Group Ltd Chemical compounds
MC2096A1 (fr) * 1989-02-23 1991-02-15 Hoffmann La Roche Pyrroles substitues
DE69325167T2 (de) * 1992-03-12 2000-01-20 Smithkline Beecham P.L.C., Brentford Kondensierte indol-derivate als 5-ht4-rezeptor-antagonisten
EP0572863A1 (de) * 1992-06-05 1993-12-08 F. Hoffmann-La Roche Ag ZNS Pyrazinoindole
TW251284B (enExample) * 1992-11-02 1995-07-11 Pfizer
AU683447B2 (en) * 1993-03-08 1997-11-13 Fujisawa Pharmaceutical Co., Ltd. Medicament for treating or preventing cerebrovascular diseases
US5629427A (en) * 1993-08-26 1997-05-13 Peterson; Dwight M. 2,7-diaminomitosene analogues

Also Published As

Publication number Publication date
MXPA01002101A (es) 2002-08-20
CA2341991A1 (en) 2000-03-09
DK1109813T3 (da) 2004-12-20
KR20070062609A (ko) 2007-06-15
HRP20010126B1 (en) 2005-06-30
DE69919364D1 (de) 2004-09-16
TR200100659T2 (tr) 2001-10-22
ATE273308T1 (de) 2004-08-15
JP2002523508A (ja) 2002-07-30
IL141659A0 (en) 2002-03-10
YU16001A (sh) 2003-10-31
CN1325399A (zh) 2001-12-05
NO20010991L (no) 2001-04-23
RU2232162C2 (ru) 2004-07-10
AU758084B2 (en) 2003-03-13
EP1109813A1 (en) 2001-06-27
PL346427A1 (en) 2002-02-11
CN1165537C (zh) 2004-09-08
CZ296275B6 (cs) 2006-02-15
KR100768595B1 (ko) 2007-10-18
AU5637599A (en) 2000-03-21
HK1034967A1 (en) 2001-11-09
DE69919364T2 (de) 2005-08-04
ES2226430T3 (es) 2005-03-16
BR9913477A (pt) 2001-10-09
NO20010991D0 (no) 2001-02-27
GB9819035D0 (en) 1998-10-28
IL141659A (en) 2007-10-31
US6433175B1 (en) 2002-08-13
TR200501110T2 (tr) 2005-07-21
KR20010079715A (ko) 2001-08-22
NZ510097A (en) 2003-06-30
HUP0103333A2 (hu) 2002-01-28
HRP20010126A2 (en) 2002-02-28
SI1109813T1 (en) 2005-02-28
PT1109813E (pt) 2004-11-30
WO2000012510A1 (en) 2000-03-09
EP1109813B1 (en) 2004-08-11
ZA200101457B (en) 2002-02-21
NO321527B1 (no) 2006-05-15
ID28842A (id) 2001-07-05
HUP0103333A3 (en) 2002-07-29
CZ2001772A3 (cs) 2001-07-11

Similar Documents

Publication Publication Date Title
CA2341991C (en) Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists
US6583134B2 (en) Aza- indolyl derivatives for treating obesity
US7145009B2 (en) Pirazino(aza)indole derivatives
EP1109809B1 (en) Pyrroloquinolines for treatment of obesity
US6962939B1 (en) Condensed indoline derivatives and their use as 5HT, in particular 5HT2C, receptor ligands
HK1034967B (en) Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed