CO5261613A1 - Inhibidores de la fosfodiesterasa-4 8-arilquinolinas sustituidas - Google Patents

Inhibidores de la fosfodiesterasa-4 8-arilquinolinas sustituidas

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Publication number
CO5261613A1
CO5261613A1 CO00096650A CO00096650A CO5261613A1 CO 5261613 A1 CO5261613 A1 CO 5261613A1 CO 00096650 A CO00096650 A CO 00096650A CO 00096650 A CO00096650 A CO 00096650A CO 5261613 A1 CO5261613 A1 CO 5261613A1
Authority
CO
Colombia
Prior art keywords
alkyl
group
son
aryl
heteroaryl
Prior art date
Application number
CO00096650A
Other languages
English (en)
Inventor
Denis Deschenes
Daniel Dube
Michael Gallant
Girard Yves
Patrick Lacombe
Macdonald Dwight
Anthony Mastracchio
Helene Perrier
Original Assignee
Merck Frosst Canada Inc
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 Inc filed Critical Merck Frosst Canada Inc
Publication of CO5261613A1 publication Critical patent/CO5261613A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/10—Heterocyclic 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/16—Central respiratory analeptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
    • 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
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic 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
    • C07D215/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic 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
    • C07D215/12—Heterocyclic 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
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/14—Heterocyclic 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic 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
    • C07D413/10—Heterocyclic 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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic 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
    • C07D417/02—Heterocyclic 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
    • C07D417/10—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic 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
    • C07D417/02—Heterocyclic 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
    • C07D417/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic 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
    • C07D417/14—Heterocyclic 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Communicable Diseases (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (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

Un compuesto representado por la Fórmula (I): <EMI FILE="00096650_1" ID="1" IMF=JPEG >ó una sal farmacéuticamente aceptable de éste, en donde: S1, S2, y S3 son independientemente H, -OH, halógeno, -alquil C1-C6, -NO2, -CN, ó -alcoxi C1-C6, en donde los grupos alquil y alcoxi van opcionalmente sustituidos con 1-5 sustituyentes; en donde cada sustituyente es independientemente un halógeno ó un OH; R1 es H, OH, halógeno, ó un grupo carbonilo, grupo -alquil C1-C6 grupo -cicloalquil C3-C6, grupo -alquenil C1-C6 grupo -alcoxi C1-C6, grupo aril, grupo heteroaril, -CN, grupo -heterociclo-alquil C1-C6, grupo -amino, grupo -alquilamino C1-C6, grupo -(alquil C1-C6)(alquil C1-C6)amino, grupo -alquil C1-C6-(oxi)-alquil C1-C6, grupo -C(O)NH(aril), grupo -C(O)NH(heteroaril), grupo -SOnNH(aril), grupo -SOnNH(heteroaril), grupo -SOnNH(alquil C1-C6), grupo -C(O)N(alquil C0-C6)(alquil C0-C6), grupo -NH-SOn-(alquil C1-C6), grupo -SOn-(alquil C1-C6), grupo -(alquil C1-C6)-O-C(CN)-dialquilamino, ó un grupo -(alquil C1-C6)-SOn-(alquil C1-C6), grupos cada uno de los cuales va opcionalmente sustituido con 1-5 sustituyentes; en donde cada sustituyente es independiente halógeno -OH, -CN, alquil C1-C6, cicloalquil C3-C6, -C(O)(heterociclo-alquil C3-C6), -C(O)-O-(alquil C0-C6), -C(O)-ariloxi, -alcoxi C1-C6, (alquil C0-C6)(alquil C0-C6)amino, cicloalquiloxi, acil, aciloxi, -cicloalquil C3-C6, heterocicloalquil C3-C6, aril, heteroaril, carbonil, carbamoil, ó -SOn-(alquil C1-C6); A es CH, C-éster, ó C-R4;R2 y R3 independientemente son aril, heteroaril, H, halógeno, -CN, -alquil C1-C6, -heterocicloalquil C3-C6, -alcoxi C1-C6 un grupo carbonilo, carbamoil, -C(O)OH, -(alquil C1-C6)-SOn-(alquil C1-C6), -C(O)N(alquil C0-C6)(alquil C0-C6), ó un grupo -alquilamino C1-C6 grupos los cuales van opcionalmente sustituidos con 1-5 sustituyentes, en donde cada sustituyente es independientemente halógeno, -NO2, -C(O)OH, -CN, N-óxido, -OH, ó un grupo sustituyente aril, heteroaril, carbonil, -alquil C1-C6, -SOn-(alquil C1-C6), -SOn-(aril), ariloxi, -heteroariloxi, alcoxi C1-C6, -C(O)-heterocicloalquil C3-C6, ...
CO00096650A 1999-12-22 2000-12-20 Inhibidores de la fosfodiesterasa-4 8-arilquinolinas sustituidas CO5261613A1 (es)

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US17152299P 1999-12-22 1999-12-22

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CO00096650A CO5261613A1 (es) 1999-12-22 2000-12-20 Inhibidores de la fosfodiesterasa-4 8-arilquinolinas sustituidas

Country Status (32)

Country Link
EP (1) EP1244628A1 (es)
JP (1) JP3782011B2 (es)
KR (1) KR20020082839A (es)
CN (1) CN1221534C (es)
AR (1) AR029214A1 (es)
AU (1) AU778531B2 (es)
BG (1) BG65403B1 (es)
BR (1) BR0016651A (es)
CA (1) CA2393749C (es)
CO (1) CO5261613A1 (es)
CZ (1) CZ20022171A3 (es)
DZ (1) DZ3244A1 (es)
EA (1) EA004747B1 (es)
EE (1) EE200200342A (es)
GE (1) GEP20053626B (es)
HK (1) HK1057560A1 (es)
HR (1) HRP20020545A2 (es)
HU (1) HUP0203896A3 (es)
IL (1) IL150114A0 (es)
IS (1) IS6413A (es)
MX (1) MXPA02006329A (es)
MY (1) MY134008A (es)
NO (1) NO20023013L (es)
NZ (1) NZ520258A (es)
PE (1) PE20010989A1 (es)
PL (1) PL355752A1 (es)
SK (1) SK8972002A3 (es)
TW (1) TWI280240B (es)
UA (1) UA74815C2 (es)
WO (1) WO2001046151A1 (es)
YU (1) YU47102A (es)
ZA (1) ZA200204862B (es)

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NZ526143A (en) * 2000-12-20 2004-05-28 Merck & Co Inc Process for making substituted 8-arylquinolinium benzenesulfonate
AU2002344885C1 (en) * 2001-06-27 2006-11-09 Merck Frosst Canada Ltd Substituted 8-arylquinoline PDE4 Inhibitors
WO2003010137A1 (en) * 2001-07-24 2003-02-06 Merck & Co., Inc. Preparation of sulfonyl quinoline
HUP0500078A3 (en) * 2001-09-19 2010-07-28 Nycomed Gmbh Pharmaceutical composition containing a combination of a pde inhibitor and a leukotriene receptor antagonist
CA2479069A1 (en) * 2002-03-18 2003-09-25 Merck Frosst Canada & Co./Merck Frosst Canada & Cie Hetero-bridge substituted 8-arylquinoline pde4 inhibitors
JP2006519874A (ja) * 2003-03-05 2006-08-31 セルジーン・コーポレーション ジフェニルエチレン化合物およびその使用
EP1732900A4 (en) * 2004-03-25 2007-12-12 Synta Pharmaceuticals Corp ACRYLONITRILE DERIVATIVES FOR THE TREATMENT OR PREVENTION OF INFLAMMATION AND IMMUNE DISORDERS
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JP5280357B2 (ja) * 2006-07-07 2013-09-04 スティーブン・ピー・ガベック Ｐｄｅ４の二環式ヘテロアリール阻害剤
AU2007299726A1 (en) * 2006-09-22 2008-03-27 Braincells, Inc. Combination comprising an HMG-COA reductase inhibitor and a second neurogenic agent for treating a nervous system disorder and increasing neurogenesis
AU2008215948A1 (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
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CN111406051A (zh) * 2017-09-03 2020-07-10 安吉昂生物医药公司 作为rho相关卷曲螺旋激酶(rock)抑制剂的乙烯基杂环

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YU47102A (sh) 2005-06-10
HK1057560A1 (en) 2004-04-08
EA200200702A1 (ru) 2003-02-27
CN1434801A (zh) 2003-08-06
IL150114A0 (en) 2002-12-01
UA74815C2 (en) 2006-02-15
DZ3244A1 (fr) 2001-06-28
AR029214A1 (es) 2003-06-18
BG106840A (en) 2003-01-31
JP2003531112A (ja) 2003-10-21
NO20023013L (no) 2002-08-22
AU778531B2 (en) 2004-12-09
JP3782011B2 (ja) 2006-06-07
EP1244628A1 (en) 2002-10-02
CA2393749C (en) 2008-06-17
HUP0203896A3 (en) 2003-05-28
CZ20022171A3 (cs) 2002-11-13
HRP20020545A2 (en) 2005-10-31
PE20010989A1 (es) 2001-10-01
EE200200342A (et) 2003-06-16
MXPA02006329A (es) 2004-05-14
BR0016651A (pt) 2002-09-10
EA004747B1 (ru) 2004-08-26
MY134008A (en) 2007-11-30
TWI280240B (en) 2007-05-01
CN1221534C (zh) 2005-10-05
IS6413A (is) 2002-06-11
HUP0203896A2 (hu) 2003-04-28
BG65403B1 (bg) 2008-06-30
NZ520258A (en) 2004-05-28
PL355752A1 (en) 2004-05-17
AU2336201A (en) 2001-07-03
NO20023013D0 (no) 2002-06-21
SK8972002A3 (en) 2002-11-06
KR20020082839A (ko) 2002-10-31
WO2001046151A1 (en) 2001-06-28
ZA200204862B (en) 2003-03-17
CA2393749A1 (en) 2001-06-28
GEP20053626B (en) 2005-10-10

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