CA2393749C - Substituted 8-arylquinoline phosphodiesterase-4 inhibitors - Google Patents

Substituted 8-arylquinoline phosphodiesterase-4 inhibitors Download PDF

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Publication number
CA2393749C
CA2393749C CA002393749A CA2393749A CA2393749C CA 2393749 C CA2393749 C CA 2393749C CA 002393749 A CA002393749 A CA 002393749A CA 2393749 A CA2393749 A CA 2393749A CA 2393749 C CA2393749 C CA 2393749C
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CA
Canada
Prior art keywords
c6alkyl
phenyl
methylsulfonyl
aryl
alkyl
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
CA002393749A
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English (en)
French (fr)
Other versions
CA2393749A1 (en
Inventor
Denis Deschenes
Daniel Dube
Michel Gallant
Yves Girard
Patrick Lacombe
Dwight Macdonald
Anthony Mastracchio
Helene Perrier
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.)
Merck Canada Inc
Original Assignee
Merck Frosst Canada Ltd
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Publication date
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Publication of CA2393749A1 publication Critical patent/CA2393749A1/en
Application granted granted Critical
Publication of CA2393749C publication Critical patent/CA2393749C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • 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
    • C07D401/10Heterocyclic 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
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/16Central respiratory analeptics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/04Antipruritics
    • AHUMAN NECESSITIES
    • 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
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • 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
    • 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
    • C07D215/14Radicals substituted by oxygen atoms
    • 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
    • C07D401/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • 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
    • CCHEMISTRY; METALLURGY
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • 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
    • C07D413/02Heterocyclic 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
    • C07D413/10Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • 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
    • 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
    • C07D417/10Heterocyclic 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
    • 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
    • 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
    • C07D417/14Heterocyclic 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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  • 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)
CA002393749A 1999-12-22 2000-12-20 Substituted 8-arylquinoline phosphodiesterase-4 inhibitors Expired - Fee Related CA2393749C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US17152299P 1999-12-22 1999-12-22
US60/171,522 1999-12-22
PCT/CA2000/001559 WO2001046151A1 (en) 1999-12-22 2000-12-20 Substituted 8-arylquinoline phosphodiesterase-4 inhibitors

Publications (2)

Publication Number Publication Date
CA2393749A1 CA2393749A1 (en) 2001-06-28
CA2393749C true CA2393749C (en) 2008-06-17

Family

ID=22624050

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002393749A Expired - Fee Related CA2393749C (en) 1999-12-22 2000-12-20 Substituted 8-arylquinoline phosphodiesterase-4 inhibitors

Country Status (32)

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

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7776315B2 (en) 2000-10-31 2010-08-17 Boehringer Ingelheim Pharma Gmbh & Co. Kg Pharmaceutical compositions based on anticholinergics and additional active ingredients
DE10110772A1 (de) * 2001-03-07 2002-09-12 Boehringer Ingelheim Pharma Neue Arzneimittelkompositionen auf der Basis von Anticholinergika und PDE-IV-Inhibitoren
US6740666B2 (en) * 2000-12-20 2004-05-25 Merck & Co., Inc. Substituted 8-arylquinoline phosphodiesterase-4 inhibitors
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
CA2608158A1 (en) * 2005-05-19 2006-11-23 Synergenz Bioscience Limited Methods and compositions for assessment of pulmonary function and disorders
ATE535244T1 (de) 2006-07-05 2011-12-15 Nycomed Gmbh Kombination aus atorvastatin mit einem phosphodiesterase-4-hemmer zur behandlung von entzündlichen lungenerkrankungen
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
WO2011099305A1 (en) 2010-02-12 2011-08-18 Raqualia Pharma Inc. 5-ht4 receptor agonists for the treatment of dementia
EP2741777B1 (en) 2011-08-12 2017-01-18 INSERM - Institut National de la Santé et de la Recherche Médicale Methods and pharmaceutical compositions for treatment of pulmonary hypertension
WO2013054153A1 (en) 2011-10-11 2013-04-18 INSERM (Institut National de la Santé et de la Recherche Médicale) Nutlin compounds for use in he treatment of pulmonary hypertension
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

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (ja) * 1998-01-26 1999-08-03 Eisai Co Ltd 含窒素複素環誘導体およびその医薬

Also Published As

Publication number Publication date
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
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
CO5261613A1 (es) 2003-03-31
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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