CO5261613A1 - INHIBITORS OF PHOSPHODIESTERASA-4 8-SUBSTITUTED ARILQUINOLINES - Google Patents

INHIBITORS OF PHOSPHODIESTERASA-4 8-SUBSTITUTED ARILQUINOLINES

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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
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Colombia
Prior art keywords
alkyl
group
son
aryl
heteroaryl
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CO00096650A
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Spanish (es)
Inventor
Denis Deschenes
Daniel Dube
Michael Gallant
Girard Yves
Patrick Lacombe
Macdonald Dwight
Anthony Mastracchio
Helene Perrier
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Merck Frosst Canada Inc
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Publication of CO5261613A1 publication Critical patent/CO5261613A1/en

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    • 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

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Dermatology (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Oncology (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Communicable Diseases (AREA)
  • Heart & Thoracic Surgery (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, ...A compound represented by Formula (I): <EMI FILE = "00096650_1" ID = "1" MFI = JPEG> or a pharmaceutically acceptable salt thereof, wherein: S1, S2, and S3 are independently H, -OH, halogen, -C1-C6 alkyl, -NO2, -CN, or -C1-C6 alkoxy, wherein the alkyl and alkoxy groups are optionally substituted with 1-5 substituents; wherein each substituent is independently a halogen or an OH; R1 is H, OH, halogen, or a carbonyl group, -C1-C6 alkyl group, C3-C6 alkylcyclo group, C1-C6 alkenyl group, C1-C6 alkoxy group, aryl group, heteroaryl group, -CN, group - C1-C6 heterocyclo-alkyl, -amino group, C1-C6 -alkylamino group, group- (C1-C6 alkyl) (C1-C6 alkyl) amino, C1-C6 alkyl- (oxy) -C1-C6 alkyl group, group -C (O) NH (aryl), group -C (O) NH (heteroaryl), group -SOnNH (aryl), group -SOnNH (heteroaryl), group -SOnNH (C1-C6 alkyl), group -C ( O) N (C0-C6 alkyl) (C0-C6 alkyl), group -NH-SOn- (C1-C6 alkyl), group -SOn- (C1-C6 alkyl), group - (C1-C6 alkyl) -OC (CN) -dialkylamino, or a group - (C1-C6 alkyl) -SOn- (C1-C6 alkyl), groups each of which is optionally substituted with 1-5 substituents; wherein each substituent is independently halogen -OH, -CN, C1-C6 alkyl, C3-C6 cycloalkyl, -C (O) (heterocycle-C3-C6 alkyl), -C (O) -O- (C0-C6 alkyl ), -C (O) -aryloxy, -C1-C6 alkoxy, (C0-C6 alkyl) (C0-C6 alkyl) amino, cycloalkyloxy, acyl, acyloxy, -C3-C6 -cycloalkyl, C3-C6 heterocycloalkyl, aryl, heteroaryl , carbonyl, carbamoyl, or -SOn- (C1-C6 alkyl); A is CH, C-ester, or C-R4; R2 and R3 independently are aryl, heteroaryl, H, halogen, -CN, -C1-C6 alkyl, -C3-C6 heterocycloalkyl, a C1-C6 alkoxy a carbonyl group, carbamoyl, -C (O) OH, - (C1-C6 alkyl) -SOn- (C1-C6 alkyl), -C (O) N (C0-C6 alkyl) (C0-C6 alkyl), or a -alkylamino group C1-C6 groups which are optionally substituted with 1-5 substituents, wherein each substituent is independently halogen, -NO2, -C (O) OH, -CN, N-oxide, -OH, or an aryl, heteroaryl substituent group , carbonyl, -C1-C6 alkyl, -SOn- (C1-C6 alkyl), -SOn- (aryl), aryloxy, -heteroaryloxy, C1-C6 alkoxy, -C (O) -heterocycloalkyl C3-C6, ...

CO00096650A 1999-12-22 2000-12-20 INHIBITORS OF PHOSPHODIESTERASA-4 8-SUBSTITUTED ARILQUINOLINES CO5261613A1 (en)

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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)
HK (1) HK1057560A1 (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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