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YU47102A - Substituted 8-arylquinoline phosphodiesterase-4 inhibitors - Google Patents

Substituted 8-arylquinoline phosphodiesterase-4 inhibitors

Info

Publication number
YU47102A
YU47102A YU47102A YUP47102A YU47102A YU 47102 A YU47102 A YU 47102A YU 47102 A YU47102 A YU 47102A YU P47102 A YUP47102 A YU P47102A YU 47102 A YU47102 A YU 47102A
Authority
YU
Yugoslavia
Prior art keywords
c6alkyl
son
aryl
heteroaryl
halogen
Prior art date
Application number
YU47102A
Other languages
Serbo-Croatian (sh)
Inventor
Denis Deschenes
Daniel Dube
Michel Gallant
Yves Girard
Patrick Lacombe
Dwight Macdonald
Anthony Mastracchio
Helene Perrier
Original Assignee
Merck Frosst Canada & Co.
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 Merck Frosst Canada & Co. filed Critical Merck Frosst Canada & Co.
Publication of YU47102A publication Critical patent/YU47102A/en

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    • 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
    • C07D401/10Heterocyclic 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 carbon chain containing aromatic rings
    • 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
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/16Central respiratory analeptics
    • AHUMAN NECESSITIES
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    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P17/00Drugs for dermatological disorders
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/04Antipruritics
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P25/00Drugs for disorders of the nervous system
    • 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
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/12Antidiuretics, e.g. drugs for diabetes insipidus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07ORGANIC CHEMISTRY
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    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14Radicals substituted by oxygen atoms
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    • 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
    • C07D401/14Heterocyclic 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 three or more hetero rings
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/12Heterocyclic 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
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • 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
    • C07D417/10Heterocyclic 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 carbon chain containing aromatic rings
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    • 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
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    • 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
    • C07D417/14Heterocyclic 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 three or more hetero rings

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  • Organic Chemistry (AREA)
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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pain & Pain Management (AREA)
  • Oncology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Communicable Diseases (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Novel substituted 8-arylquinolines represented by Formula (I), or a pharmaceutically acceptable salt thereof, wherein S1, S2 and S3 are independently H, -OH; halogen, -C1-C6alkyl, -NO2, -CN, or -C1-C6alkoxy, wherein the alkyl and alkoxy groups are optionally substituted with 1-5 substituents; wherein each substituent is independently a halogen or OH; R1 is a H, OH, halogen, carbonyl, or -C1-C6alkyl, -cycloC3-C6alkyl, -C1-C6alkenyl, -C1-C6alkoxy, aryl, heteroaryl, -CN, -heterocycloC3-C6alkyl, -amino, -C1- C6alkylamino, -(C1-C6alkyl)(C1-C6alkyl)amino, -C1-C6alkyl(oxy)C1-C6alkyl, -C(O)NH(aryl), -C(O)NH(heteroaryl), -SOnNH(aryl), -SOnNH(heteroaryl), -SOnNH(C1-C6alkyl), -C(O)N(C0-C6alkyl) (C0-C6alkyl), -NH-SOn-(C1-C6alkyl), -SOn-(C1-C6alkyl), -(C1-C6alkyl)- O-C(CN)-dialkylamino, or -(C1-C6alkyl)-SOn-(C1-C6alkal) group, wherein any of the groups is optionally substituted with 1-5 substituents; wherein each substituent is independently a halogen, -OH, -CN, -C1-C6alkyl, -cycloC3-C6alkyl, -C(O)(heterocycloC3- C6alkyl), -C(O)-O-(C0-C6alkyl), -C(O)- aryloxy, -C1-C6alkoxy, -(C0-C6alkyl)amino, cycloalkyloxy, acyl, acyloxy, -cycloC3- C6alkyl, heterocycloC3-C6alkyl, aryl, heteroaryl, carbonyl, carbamoyl, or -SOn-(C1-C6alkyl); A is CH, C-ester, or C-R4; R2 and R3 independently is an aryl, heteroaryl, H, halogen, -CN, -C1-C6alkyl, heterocycloC3-C6alkyl, -C1-C6alkoxy, carbonyl, carbamoyl, -C(O)OH, -C1-C6alkyl)-SOn-(C1-C6alkyl), -C(O)N(C0-C6alkyl)(C0-C6alkyl), or -C1-C6alkylacylamino group, wherein any of the groups is optionally substituted with 1-5 substituents, wherein each substituent is independently an aryl, heteroaryl, halogen, -NO2, -C(O)OH, carbonyl, -CN, -C1-C6alkyl, -SOn-(C1-C6alkyl), -SOn-(aryl), aryloxy, -heteroaryloxy, C1-C6alkoxy, N-oxide, -C(O)-heterocycloC3-C6alkyl, -NH-cycloC3-C6alkyl, amino, -OH, or.
YU47102A 1999-12-22 2000-12-20 Substituted 8-arylquinoline phosphodiesterase-4 inhibitors YU47102A (en)

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US17152299P 1999-12-22 1999-12-22

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YU47102A true YU47102A (en) 2005-06-10

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EP (1) EP1244628A1 (en)
JP (1) JP3782011B2 (en)
KR (1) KR20020082839A (en)
CN (1) CN1221534C (en)
AR (1) AR029214A1 (en)
AU (1) AU778531B2 (en)
BG (1) BG65403B1 (en)
BR (1) BR0016651A (en)
CA (1) CA2393749C (en)
CO (1) CO5261613A1 (en)
CZ (1) CZ20022171A3 (en)
DZ (1) DZ3244A1 (en)
EA (1) EA004747B1 (en)
EE (1) EE200200342A (en)
GE (1) GEP20053626B (en)
HR (1) HRP20020545A2 (en)
HU (1) HUP0203896A3 (en)
IL (1) IL150114A0 (en)
IS (1) IS6413A (en)
MX (1) MXPA02006329A (en)
MY (1) MY134008A (en)
NO (1) NO20023013L (en)
NZ (1) NZ520258A (en)
PE (1) PE20010989A1 (en)
PL (1) PL355752A1 (en)
SK (1) SK8972002A3 (en)
TW (1) TWI280240B (en)
UA (1) UA74815C2 (en)
WO (1) WO2001046151A1 (en)
YU (1) YU47102A (en)
ZA (1) ZA200204862B (en)

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DE10110772A1 (en) * 2001-03-07 2002-09-12 Boehringer Ingelheim Pharma New drug compositions based on anticholinergics and PDE-IV inhibitors
US7776315B2 (en) 2000-10-31 2010-08-17 Boehringer Ingelheim Pharma Gmbh & Co. Kg Pharmaceutical compositions based on anticholinergics and additional active ingredients
US6740666B2 (en) * 2000-12-20 2004-05-25 Merck & Co., Inc. Substituted 8-arylquinoline phosphodiesterase-4 inhibitors
EA005864B1 (en) * 2000-12-20 2005-06-30 Мерк Энд Ко., Инк. Process for making substituted 8-arylquinolinium benzenesulfonate
ES2242036T3 (en) 2001-06-27 2005-11-01 MERCK FROSST CANADA & CO. 8-REPLACED ARILQUINOLINE PDE4 INHIBITORS.
WO2003010137A1 (en) * 2001-07-24 2003-02-06 Merck & Co., Inc. Preparation of sulfonyl quinoline
US20050014762A1 (en) * 2001-09-19 2005-01-20 Rolf Beume Combination
DE60327750D1 (en) 2002-03-18 2009-07-09 Merck Frosst Canada Ltd PDE4 INHIBITORS HAVING HETEROBRESS-SUBSTITUTED 8-ARYLCHINOLINE
JP2006519874A (en) * 2003-03-05 2006-08-31 セルジーン・コーポレーション Diphenylethylene compounds and uses thereof
AU2005226741A1 (en) * 2004-03-25 2005-10-06 Synta Pharmaceuticals Corp. Acrylonitrile derivatives for inflammation and immune-related uses
WO2006123954A1 (en) * 2005-05-19 2006-11-23 Synergenz Bioscience Limited Methods and compositions for assessment of pulmonary function and disorders
EP2363130B1 (en) 2006-07-05 2014-05-07 Takeda GmbH Combination of HMG-CoA reductase inhibitors atorvastatin or simvastatin with a phosphodiesterase 4 inhibitor, such as roflumilast for the treatment of inflammatory pulmonary diseases
WO2008006051A2 (en) * 2006-07-07 2008-01-10 Govek Steven P Bicyclic heteroaryl inhibitors of pde4
US20080103105A1 (en) * 2006-09-22 2008-05-01 Braincells, Inc. HMG CoA REDUCTASE MEDIATED MODULATION OF NEUROGENESIS
CA2676715A1 (en) 2007-02-12 2008-08-21 Merck & Co., Inc. Piperazine derivatives for treatment of ad and related conditions
US8461389B2 (en) 2008-04-18 2013-06-11 University College Dublin, National University Of Ireland, Dublin Psycho-pharmaceuticals
CN107260736A (en) 2010-02-12 2017-10-20 株式会社AskAt The 5 HT4 receptor stimulating agents for treating dementia
US20140271680A1 (en) 2011-08-12 2014-09-18 Universite Paris-Est Creteil Val De Marne Methods and pharmaceutical compositions for treatment of pulmonary hypertension
US20140328893A1 (en) 2011-10-11 2014-11-06 Institut National De La Sante Et De La Recherche Medicale (Inserm) Nutlin compounds for use in the treatment of pulmonary hypertension
CN111406051A (en) * 2017-09-03 2020-07-10 安吉昂生物医药公司 Vinylheterocycles as RHO-associated coiled coil kinase (ROCK) inhibitors

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GB9226830D0 (en) * 1992-12-23 1993-02-17 Celltech Ltd Chemical compounds
US5455252A (en) * 1993-03-31 1995-10-03 Syntex (U.S.A.) Inc. Optionally substituted 6,8-quinolines
US6245774B1 (en) * 1994-06-21 2001-06-12 Celltech Therapeutics Limited Tri-substituted phenyl or pyridine derivatives
JPH11209350A (en) * 1998-01-26 1999-08-03 Eisai Co Ltd Nitrogen-containing heterocyclic derivative and medicine containing the same

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UA74815C2 (en) 2006-02-15
JP3782011B2 (en) 2006-06-07
NO20023013L (en) 2002-08-22
PE20010989A1 (en) 2001-10-01
ZA200204862B (en) 2003-03-17
CO5261613A1 (en) 2003-03-31
EE200200342A (en) 2003-06-16
EP1244628A1 (en) 2002-10-02
MXPA02006329A (en) 2004-05-14
HUP0203896A2 (en) 2003-04-28
GEP20053626B (en) 2005-10-10
NO20023013D0 (en) 2002-06-21
EA004747B1 (en) 2004-08-26
CN1434801A (en) 2003-08-06
AU2336201A (en) 2001-07-03
KR20020082839A (en) 2002-10-31
AR029214A1 (en) 2003-06-18
BG106840A (en) 2003-01-31
NZ520258A (en) 2004-05-28
IL150114A0 (en) 2002-12-01
HK1057560A1 (en) 2004-04-08
HRP20020545A2 (en) 2005-10-31
CN1221534C (en) 2005-10-05
EA200200702A1 (en) 2003-02-27
WO2001046151A1 (en) 2001-06-28
PL355752A1 (en) 2004-05-17
IS6413A (en) 2002-06-11
HUP0203896A3 (en) 2003-05-28
JP2003531112A (en) 2003-10-21
BG65403B1 (en) 2008-06-30
AU778531B2 (en) 2004-12-09
TWI280240B (en) 2007-05-01
SK8972002A3 (en) 2002-11-06
CA2393749C (en) 2008-06-17
CZ20022171A3 (en) 2002-11-13
BR0016651A (en) 2002-09-10
DZ3244A1 (en) 2001-06-28
MY134008A (en) 2007-11-30
CA2393749A1 (en) 2001-06-28

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