[go: up one dir, main page]

UY24735A1 - Procedimiento para la preparacion de antagonistas del receptor de vitronectina.- - Google Patents

Procedimiento para la preparacion de antagonistas del receptor de vitronectina.-

Info

Publication number
UY24735A1
UY24735A1 UY24735A UY24735A UY24735A1 UY 24735 A1 UY24735 A1 UY 24735A1 UY 24735 A UY24735 A UY 24735A UY 24735 A UY24735 A UY 24735A UY 24735 A1 UY24735 A1 UY 24735A1
Authority
UY
Uruguay
Prior art keywords
alkyl
formula
compound
represented
acid
Prior art date
Application number
UY24735A
Other languages
English (en)
Inventor
Francis Callahan James
Donovan Cousins Russell
Mccullock Keenan Richard
Chet Kwon
William Miller
Nijole Uzinkas Irene
Original Assignee
Smithkline Beecham Corp
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 Smithkline Beecham Corp filed Critical Smithkline Beecham Corp
Publication of UY24735A1 publication Critical patent/UY24735A1/es

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D223/00Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16Benzazepines; Hydrogenated benzazepines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00Medicinal preparations containing inorganic active ingredients
    • A61K33/24Heavy metals; Compounds thereof
    • A61K33/243Platinum; Compounds thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D223/00Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/08Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/04Antineoplastic agents specific for metastasis
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/582Recycling of unreacted starting or intermediate materials

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Inorganic Chemistry (AREA)
  • Oncology (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Procedimiento para preparar un compuestos de fórmula (I) representada en la figura 1,o una de sus sales farmacéuticamente aceptables, caracterizados porque: R1 es R7, o A-alquilo, A-alquenilo, A-alquinilo, A-oxoalquenilo, A-oxoalquinilo, A-aminoalquilo, A-aminoalquenilo, A-aminoalquilino, opcionalmente sustituidos por cualquier combinación accesible de uno o más de R10 o R7; donde A es H, cicloalquilo, het o ar; R2 es uno de los grupos representados en la figura 2, donde W es -(CHRg)a-U-(CHRg)b-, con Rg H, alquilo, het-alquilo, cicloalquil-alquilo, o ar-alquilo. El procedimiento comprende en hacer reaccionar un compuesto de fórmula (IV), con un compuesto de fórmula (VI) ambos representados en la figura 3, estando protegidos cualesquiera grupos funcionales reactivos; por intermedio del complejo formado entre diazodicarboxilato y la trifenilfosfina en un solvente adecuado como THF, CH2Cl2 y DMF, seguido de condiciones para la transferencia protónica, usando cilcohexano, 1,4ciclohexadieno, ácido fórmico o sales del mismo en presencia de un catalizador de paladio en metanol, etanol o 2-propanol y después de ello eliminar cualesquiera grupos protectores, y opcionalmente formar una sal farmacéuticamente aceptable. Ejemplos de compuestos de fórmula (I): Ácido (+)-8-[3-(2-piridilamino)-1-propiloxi]-3-oxo-2,3,4,5-tetrahidro-1H-2-benzepina-4-acético; Ácido (R)-8-[3-(4-aminopiridin)-2-ilamino]-1-propil-oxi]-3-oxo-2,3,4,5-tetrahidro-1H-2-benzepina-4-acético; entre otros. Estos compuestos son antagonistas del receptor de vitronectina y son útiles en el tratamiento de la osteoporosis.
UY24735A 1996-10-02 1997-10-01 Procedimiento para la preparacion de antagonistas del receptor de vitronectina.- UY24735A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2732096P 1996-10-02 1996-10-02
US4377697P 1997-04-11 1997-04-11

Publications (1)

Publication Number Publication Date
UY24735A1 true UY24735A1 (es) 1998-03-30

Family

ID=26702318

Family Applications (2)

Application Number Title Priority Date Filing Date
UY24735A UY24735A1 (es) 1996-10-02 1997-10-01 Procedimiento para la preparacion de antagonistas del receptor de vitronectina.-
UY24935A UY24935A1 (es) 1996-10-02 1998-03-25 Antagonistas del receptor de vitronectina

Family Applications After (1)

Application Number Title Priority Date Filing Date
UY24935A UY24935A1 (es) 1996-10-02 1998-03-25 Antagonistas del receptor de vitronectina

Country Status (36)

Country Link
EP (1) EP0957917B1 (es)
JP (2) JP4491072B2 (es)
KR (1) KR100589578B1 (es)
CN (1) CN1114403C (es)
AP (1) AP1463A (es)
AR (1) AR008878A1 (es)
AT (1) ATE312089T1 (es)
AU (1) AU733417B2 (es)
BG (1) BG64581B1 (es)
BR (1) BR9712248B1 (es)
CA (1) CA2267224C (es)
CO (1) CO4900046A1 (es)
CY (1) CY2576B1 (es)
CZ (1) CZ299076B6 (es)
DE (1) DE69734833T2 (es)
DK (1) DK0957917T3 (es)
DZ (1) DZ2320A1 (es)
EA (1) EA002419B1 (es)
ES (1) ES2252775T3 (es)
HU (1) HU229221B1 (es)
ID (1) ID19623A (es)
IL (1) IL129243A (es)
MA (1) MA24361A1 (es)
MY (1) MY137606A (es)
NO (1) NO320194B1 (es)
NZ (1) NZ334953A (es)
PE (1) PE10499A1 (es)
PL (1) PL190859B1 (es)
RO (1) RO119881B1 (es)
SA (1) SA98180936B1 (es)
SK (1) SK285029B6 (es)
TR (1) TR199900737T2 (es)
TW (1) TW487702B (es)
UA (1) UA60311C2 (es)
UY (2) UY24735A1 (es)
WO (1) WO1998014192A1 (es)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA60311C2 (uk) * 1996-10-02 2003-10-15 Смітклайн Бічам Корпорейшн Антагоністи рецептора вітронектину, спосіб одержання цих сполук та фармацевтична композиція
TW527355B (en) 1997-07-02 2003-04-11 Bristol Myers Squibb Co Inhibitors of farnesyl protein transferase
TR200000786T2 (tr) * 1997-09-24 2000-08-21 Smithkline Beecham Corporation Vitronektin reseptör antagonisti
CN1273529A (zh) * 1997-09-24 2000-11-15 史密丝克莱恩比彻姆公司 玻连蛋白受体拮抗剂
US6372719B1 (en) 1998-03-04 2002-04-16 Jay Cunningham ανβ3 integrin antagonists in combination with chemotherapeutic agents
DE19842415A1 (de) * 1998-09-16 2000-03-23 Merck Patent Gmbh Pharmazeutische Zubereitung
IL143901A0 (en) * 1998-12-23 2002-04-21 Searle & Co Use of cyclooxygenase-2- inhibitor, a matrix metallaproteinase inhibitor, an antineoplastic agent and optionally radiation as a combination treatment of neoplasia
EP1150965A4 (en) * 1999-02-03 2002-05-15 Merck & Co Inc BENZAZEPINE DERIVATIVES AS ALPHA-V INTGRIN RECEPTOR ANTAGONISTS
MXPA01011052A (es) * 1999-04-30 2002-11-22 Univ Michigan Aplicaciones terapeuticas de benzodiazepinas pro-apoctoticas.
JP2003506452A (ja) * 1999-08-06 2003-02-18 スミスクライン・ビーチャム・コーポレイション 発作の治療に有用なビトロネクチン受容体アンタゴニスト
US6514964B1 (en) 1999-09-27 2003-02-04 Amgen Inc. Fused cycloheptane and fused azacycloheptane compounds and their methods of use
DE10028575A1 (de) 2000-06-14 2002-03-14 Basf Ag Integrinliganden
DE10027514A1 (de) * 2000-06-06 2002-01-03 Basf Ag Liganden von Integrinrezeptoren
FR2806082B1 (fr) * 2000-03-07 2002-05-17 Adir Nouveaux composes bicycliques antagonistes des recepteurs de la vitronectine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
WO2002060438A1 (en) 2001-01-29 2002-08-08 3-Dimensional Pharmaceuticals, Inc. Substituted indoles and their use as integrin antagonists
ES2319877T3 (es) * 2001-04-10 2009-05-14 Smithkline Beecham Corporation Metodo para inhibir la formacion de adherencias.
SE0101386D0 (sv) 2001-04-20 2001-04-20 Astrazeneca Ab New compounds
CA2445679A1 (en) 2001-05-03 2002-11-14 Paul J. Coleman Benzazepinone alpha v integrin receptor antagonists
CA2464472C (en) 2001-10-22 2014-01-07 The Scripps Research Institute Antibody targeting compounds
GB0215867D0 (en) * 2002-07-09 2002-08-14 Glaxosmithkline Spa Novel method and compounds
WO2004089890A2 (en) * 2003-04-04 2004-10-21 Smithkline Beecham Corporation Process and intermediates for preparing benzazepines
EP1734996B1 (en) * 2004-04-02 2013-05-22 The Regents of The University of California Methods and compositions for treating and preventing disease associated with alpha v beta 5 integrin
AU2012216372B2 (en) * 2004-04-02 2015-01-22 The Regents Of The University Of California Methods and compositions for treating and preventing disease associated with alphaVbeta5 integrin
UA87854C2 (en) 2004-06-07 2009-08-25 Мерк Энд Ко., Инк. N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators
WO2006069079A2 (en) * 2004-12-21 2006-06-29 Smithkline Beecham Corporation Methods and formulations
PL1968594T3 (pl) * 2005-11-29 2011-03-31 Glaxosmithkline Llc Leczenie zaburzeń neowaskularyzacyjnych oka, takich jak zwyrodnienie plamki żółtej, rozszerzenie naczyń siatkówki w zespole Hippla i Lindaua, zapalenie błony naczyniowej oka i obrzęk plamki
JP5637855B2 (ja) 2007-11-08 2014-12-10 ザ ジェネラル ホスピタル コーポレイション 蛋白尿症の治療のための方法及び組成物
AU2008321770B2 (en) * 2007-11-16 2012-09-06 Ube Industries, Ltd. Benzazepinone compound
US8076475B2 (en) * 2008-03-06 2011-12-13 Glaxosmithkline Llc Process
WO2010093706A2 (en) 2009-02-10 2010-08-19 The Scripps Research Institute Chemically programmed vaccination
AU2010231631A1 (en) 2009-03-30 2011-11-10 Ube Industries, Ltd. Pharmaceutical composition for treatment or prevention of ophthalmic diseases
JP5572996B2 (ja) * 2009-05-15 2014-08-20 宇部興産株式会社 ベンズアゼピノン化合物を有効成分として含有する医薬
CN102481347A (zh) 2009-07-24 2012-05-30 加州大学董事会 治疗和预防整合素αvβ5相关疾病的方法及组合物
WO2011062765A2 (en) 2009-11-17 2011-05-26 The Regents Of The University Of Michigan 1,4-benzodiazepine-2,5-diones and related compounds with therapeutic properties
EP2325194A1 (en) * 2009-11-24 2011-05-25 Glycotope GmbH Process for the purification of glycoproteins
WO2015181676A1 (en) 2014-05-30 2015-12-03 Pfizer Inc. Carbonitrile derivatives as selective androgen receptor modulators
CA3172692C (en) * 2020-04-26 2024-05-14 Jiangsu Nhwa Pharmaceutical Co., Ltd 1,5-dihydro-2,4-benzodiazepine-3-one derivative and application thereof
WO2023275715A1 (en) 2021-06-30 2023-01-05 Pfizer Inc. Metabolites of selective androgen receptor modulators

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2152631A1 (en) * 1992-12-21 1994-07-07 William Edward Bondinell Bicyclic fibrinogen antagonists
AU702661B2 (en) * 1994-06-29 1999-02-25 Smithkline Beecham Corporation Vitronectin receptor antagonists
WO1996000574A1 (en) * 1994-06-29 1996-01-11 Smithkline Beecham Corporation Vitronectin receptor antagonists
US6008214A (en) * 1994-08-22 1999-12-28 Smithkline Beecham Corporation Bicyclic compounds
WO1996026190A1 (en) * 1995-02-22 1996-08-29 Smithkline Beecham Corporation Integrin receptor antagonists
UA60311C2 (uk) * 1996-10-02 2003-10-15 Смітклайн Бічам Корпорейшн Антагоністи рецептора вітронектину, спосіб одержання цих сполук та фармацевтична композиція

Also Published As

Publication number Publication date
NO991590D0 (no) 1999-03-31
BG103299A (en) 2000-01-31
TW487702B (en) 2002-05-21
NO320194B1 (no) 2005-11-14
CA2267224C (en) 2007-03-13
CZ113299A3 (cs) 2000-03-15
DE69734833D1 (de) 2006-01-12
ID19623A (id) 1998-07-23
EP0957917A1 (en) 1999-11-24
JP2001501936A (ja) 2001-02-13
HUP9903769A3 (en) 2000-07-28
PE10499A1 (es) 1999-03-27
WO1998014192A1 (en) 1998-04-09
TR199900737T2 (xx) 1999-07-21
EP0957917B1 (en) 2005-12-07
MY137606A (en) 2009-02-27
CY2576B1 (en) 2008-07-02
UA60311C2 (uk) 2003-10-15
HUP9903769A2 (hu) 2000-03-28
BR9712248B1 (pt) 2010-06-29
DZ2320A1 (fr) 2002-12-28
SK285029B6 (sk) 2006-04-06
UY24935A1 (es) 2001-07-31
IL129243A (en) 2004-07-25
AU733417B2 (en) 2001-05-17
AP1463A (en) 2005-09-10
KR100589578B1 (ko) 2006-06-15
CN1238689A (zh) 1999-12-15
JP4491072B2 (ja) 2010-06-30
CZ299076B6 (cs) 2008-04-16
DE69734833T2 (de) 2006-07-13
EA199900356A1 (ru) 2000-02-28
SK42599A3 (en) 1999-12-10
CO4900046A1 (es) 2000-03-27
ATE312089T1 (de) 2005-12-15
CA2267224A1 (en) 1998-04-09
HK1023730A1 (en) 2000-09-22
CN1114403C (zh) 2003-07-16
EA002419B1 (ru) 2002-04-25
IL129243A0 (en) 2000-02-17
ES2252775T3 (es) 2006-05-16
NZ334953A (en) 2000-01-28
PL190859B1 (pl) 2006-02-28
HU229221B1 (en) 2013-09-30
JP2010006838A (ja) 2010-01-14
AU4746297A (en) 1998-04-24
SA98180936B1 (ar) 2006-05-30
PL332674A1 (en) 1999-09-27
DK0957917T3 (da) 2006-04-18
AP9901493A0 (en) 1999-03-31
MA24361A1 (fr) 1998-07-01
KR20000048816A (ko) 2000-07-25
NO991590L (no) 1999-05-31
AR008878A1 (es) 2000-02-23
BG64581B1 (bg) 2005-08-31
BR9712248A (pt) 1999-08-24
RO119881B1 (ro) 2005-05-30
EP0957917A4 (en) 2002-05-15

Similar Documents

Publication Publication Date Title
UY24735A1 (es) Procedimiento para la preparacion de antagonistas del receptor de vitronectina.-
Chen et al. Synthesis of the 5-HT1D receptor agonist MK-0462 via a Pd-catalyzed coupling reaction
WO2021179091A1 (en) 3-(2-(aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-ht2 receptor modulators
US5525624A (en) Non-peptide tachykinin receptor antagonists to treat psycological disorder
CN118108700A (zh) 补体因子b抑制剂及其药物组合物、制备方法和用途
US6995176B2 (en) 1-heterocyclylalkyl-3-sulfonyl-indole or -indazole derivatives as 5-hydroxytryptamine-6 ligands
NO171078B (no) Pumpe
JP3152440B2 (ja) ニューロキニンアンタゴニストとして有用な置換オキシム誘導体
AU2003235259B2 (en) Benzimidazole derivatives
EP0737189B1 (en) Heterocyclic compounds for the treatment of cns and cardiovascular disorders
SE504184C2 (sv) Användning av vissa 3-HT3-antagonister för framställning av läkemedel
JP2004517072A (ja) Cns障害の治療において有用な化合物
Tapia et al. 2, 3-Dihydro-2-oxo-1 H-benzimidazole-1-carboxamides with Selective Affinity for the 5-HT4 Receptor: Synthesis and Structure− Affinity and Structure− Activity Relationships of a New Series of Partial Agonist and Antagonist Derivatives
MX9605838A (es) Cierre de anillo de triazoliltriptamina catalizado con paladio.
OA10189A (en) Use of indole derivatives as 5htl agonists
KR20100046064A (ko) 인다졸 아크릴산 아미드 화합물
NO964551L (no) Imidazolderivater og fremgangsmåte for fremstilling av slike
EP2736906B1 (en) N-(IMIDAZOLIDIN-2-YLIDENE)-HETEROCYCLOPENTA[b]PYRIDINE DERIVATIVES AS MODULATORS OF ALPHA 2 ADRENERGIC RECEPTORS
KR970001347A (ko) 벤즈이소티아졸릴 치환 아미노메틸크로만
Heinzelman et al. Recent studies in the field of indole compounds
JP2902484B2 (ja) 5ht1−様作動薬としてのインドール誘導体
EP0699665A1 (en) Imidazoline derivatives, their preparation and their use as tachykinin receptor antagonists
JP2001526674A (ja) 5ht2c受容体アンタゴニストとしてのインドリン誘導体
TWI311557B (en) Pharmaceutically active diazepanes
HU211701A9 (en) Hydroxy-1,2,3,4-tetrahydroaminoacridines, a process for their preparation and their use as medicaments

Legal Events

Date Code Title Description
VENC Patent expired

Effective date: 20171001