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BR9911175A - Derivados de ftalazina, composições farmacêuticas contendo os mesmos e uso como inibidores de fosfodiesterase 4 - Google Patents

Derivados de ftalazina, composições farmacêuticas contendo os mesmos e uso como inibidores de fosfodiesterase 4

Info

Publication number
BR9911175A
BR9911175A BR9911175-6A BR9911175A BR9911175A BR 9911175 A BR9911175 A BR 9911175A BR 9911175 A BR9911175 A BR 9911175A BR 9911175 A BR9911175 A BR 9911175A
Authority
BR
Brazil
Prior art keywords
alkyl
aryl
heterocycle
optionally substituted
alkoxy
Prior art date
Application number
BR9911175-6A
Other languages
English (en)
Inventor
Mauro Napoletano
Franco Pellacini
Gian Marco Leali
Gabriele Norcini
Giancarlo Grancini
Gabriele Morazzoni
Original Assignee
Zambon Spa
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 Zambon Spa filed Critical Zambon Spa
Publication of BR9911175A publication Critical patent/BR9911175A/pt

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Classifications

    • 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
    • C07D401/06—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 only aliphatic carbon atoms
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C07D237/34—Phthalazines with nitrogen atoms directly attached to carbon atoms of the nitrogen-containing ring, e.g. hydrazine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pulmonology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

<B>DERIVADOS DE FTALAZINA, COMPOSIçõES FARMACêUTICAS CONTENDO OS MESMOS E USO COMO INIBIDORES DE FOSFODIESTERASE 4 Compostos da fórmula (I), onde - - - - é uma ligação simples ou dupla; Z é NH, metileno, uma cadeia de alquileno (C~ 2~-C~ 6~) opcionalmente ramificada e/ou insaturada e/ou interrompida por um resíduo cicloalquila (C~ 5~-C~ 7~); A é fenila ou heterociclo opcionalmente substituído por um ou mais substitutos selecionados entre oxo, nitro, grupos carbóxi e átomos de halogênio ou um grupo COR~ 4~ onde R~ 4~ é hidróxi, alcóxi (C~ 1~-C~ 6~), amino opcionalmente substituído por um ou dois grupos alquila (C~ 1~-C~ 6~) ou por hidróxi; R é alquila (C~ 1~-C~ 6~) ou grupo poliflúor alquila (C~ 1~-C~ 6~); R~ 1~ está ausente quando - - - - é uma ligação dupla ou, quando - - - - é uma ligação simples, é a) hidrogênio; b) alquila (C~ 1~-C~ 6~) opcionalmente substituída por arila, por heterociclo ou por um grupo COR~ 5~, onde R~ 5~ é hidróxi, alcóxi (C~ 1~-C~ 4~) ou hidroxiamino; c) -COR~ 6~ onde R~ 6~ é hidrogênio, arila, aril-alquila (C~ 1~-C~ 6~), amino opcionalmente alquilado ou monohidroxilado, hidróxi, alcóxi (C~ 1~-C~ 4~), carbóxi, alcoxicarbonila (C~ 1~-C~ 4~), fórmula (1) ou ou alquila (C~ 1~-C~ 4~) opcionalmente substituída por heterociclo; d) alquilssulfonila (C~ 1~-C~ 4~); R~ 2~ representa dois átomos de hidrogênio ou um grupo =O quando - - - - é uma ligação simples, ou, quando - - - - é uma ligação dupla, R~ 2~ é hidrogênio, ciano, alcoxicarbonila (C~ 1~-C~ 4~), amido, arila opcionalmente substituída ou heterociclo, alquila (C~ 1~-C~ 8~), alquenila (C~ 2~-C~ 8~) ou alquinila (C~ 2~-C~ 8~) opcionalmente ramificada e/ou substituída por arila ou heterociclo; arilóxi, heterociclilóxi, aril-alcóxi (C~ 1~-C~ 4~), heterociclil-alcóxi (C~ 1~-C~ 4~), amino substituído por um ou dois grupos alquila (C~ 1~-C~ 4~), arilamino, heterociclilamino, aril-alquilamino (C~ 1~-C~ 4~), heterociclil-alquilamino (C~ 1~-C~ 4~); R~ 3~ é hidrogênio ou uma alquila (C~ 1~-C~ 8~), alquenila (C~ 2~-C~ 8~) ou grupo alquinila (C~ 2~-C~ 8~) opcionalmente substituído por hidróxi, oxo, aril ou heterociclo e, opcionalmente interrompido por um ou mais heteroátomos ou heterogrupos; os derivados N<sym>O dos compostos da fórmula (1) e os sais farmaceuticamente aceitáveis dos mesmos são inibidores de PDE4.
BR9911175-6A 1998-07-21 1999-07-13 Derivados de ftalazina, composições farmacêuticas contendo os mesmos e uso como inibidores de fosfodiesterase 4 BR9911175A (pt)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT98MI001670A ITMI981670A1 (it) 1998-07-21 1998-07-21 Derivati ftalazinici inibitori della fosfodiesterasi 4
PCT/EP1999/004904 WO2000005218A1 (en) 1998-07-21 1999-07-13 Phthalazine derivatives phosphodiesterase 4 inhibitors

Publications (1)

Publication Number Publication Date
BR9911175A true BR9911175A (pt) 2001-03-20

Family

ID=11380474

Family Applications (1)

Application Number Title Priority Date Filing Date
BR9911175-6A BR9911175A (pt) 1998-07-21 1999-07-13 Derivados de ftalazina, composições farmacêuticas contendo os mesmos e uso como inibidores de fosfodiesterase 4

Country Status (35)

Country Link
US (2) US6329370B1 (pt)
EP (2) EP1097142B1 (pt)
JP (1) JP2002521370A (pt)
KR (1) KR20010087161A (pt)
CN (1) CN1127486C (pt)
AP (1) AP2000001993A0 (pt)
AR (1) AR019409A1 (pt)
AT (1) ATE279397T1 (pt)
AU (1) AU765457B2 (pt)
BG (1) BG105063A (pt)
BR (1) BR9911175A (pt)
CA (1) CA2338044A1 (pt)
CO (1) CO5090842A1 (pt)
DE (1) DE69921139T2 (pt)
EA (1) EA200100062A1 (pt)
EE (1) EE200100039A (pt)
HK (1) HK1039124B (pt)
HR (1) HRP20010057A2 (pt)
HU (1) HUP0102646A3 (pt)
ID (1) ID28874A (pt)
IL (1) IL139490A0 (pt)
IS (1) IS5772A (pt)
IT (1) ITMI981670A1 (pt)
MX (1) MXPA01000670A (pt)
NO (1) NO318988B1 (pt)
NZ (1) NZ507926A (pt)
OA (1) OA11582A (pt)
PA (1) PA8478301A1 (pt)
PE (1) PE20000755A1 (pt)
PL (1) PL345187A1 (pt)
SK (1) SK1002001A3 (pt)
TW (1) TW509682B (pt)
UA (1) UA68383C2 (pt)
WO (1) WO2000005218A1 (pt)
YU (1) YU77500A (pt)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CO4950519A1 (es) * 1997-02-13 2000-09-01 Novartis Ag Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion
IT1296984B1 (it) * 1997-12-19 1999-08-03 Zambon Spa Derivati ftalazinici inibitori della fosfodiesterasi 4
ITMI981671A1 (it) 1998-07-21 2000-01-21 Zambon Spa Derivati ftalazinici inibitori della fosfodisterasi 4
DE19921567A1 (de) 1999-05-11 2000-11-16 Basf Ag Verwendung von Phthalazine-Derivaten
DE19963607B4 (de) * 1999-12-23 2005-12-15 Schering Ag Verfahren zur Herstellung von 4-(Heteroaryl-methyl) halogen-1(2H)-phthalazinonen
ITMI20000261A1 (it) 2000-02-16 2001-08-16 Zambon Group Processo per la preparazione di piridiniliden-ftalidi
US6703390B2 (en) * 2000-04-13 2004-03-09 Transgenomic, Inc. Sulfur containing dihydrophthalazine antagonists of excitatory amino acid receptors
US6525049B2 (en) * 2000-07-05 2003-02-25 Pharmacia & Upjohn Company Pyrroloquinolones as antiviral agents
WO2002044157A2 (en) * 2000-12-01 2002-06-06 Iconix Pharmaceuticals, Inc. Parb inhibitors
ITMI20022739A1 (it) * 2002-12-23 2004-06-24 Zambon Spa Derivati ftalazinici inibitori della fosfodiesterasi 4.
ITMI20022738A1 (it) * 2002-12-23 2004-06-24 Zambon Spa Derivati ftalazinici inibitori della fosfodiesterasi 4.
US7652036B2 (en) 2003-02-25 2010-01-26 Topotarget Uk Limited Carbamic acid compounds comprising a bicyclic heteroaryl group as HDAC inhibitors
ITMI20031451A1 (it) * 2003-07-16 2005-01-17 Zambon Spa Derivati diidro-ftalazinici inibitori della fosfodiesterasi 4
CN1984904A (zh) * 2004-05-08 2007-06-20 神经能质公司 3－芳基－5,6－二取代哒嗪
CA2593005A1 (en) * 2005-01-03 2006-07-13 Myriad Genetics Inc. Pharmaceutical compounds as activators of caspases and inducers of apoptosis and the use thereof
BRPI0617674A2 (pt) 2005-10-19 2011-08-02 Ranbaxy Lab Ltd composições farmacêuticas e seus usos
WO2008061108A2 (en) 2006-11-15 2008-05-22 Forest Laboratories Holdings Limited Phthalazine derivatives
CA2733128C (en) * 2008-08-13 2016-05-24 Boehringer Ingelheim International Gmbh Phthalazinone compounds as chymase inhibitors
CN102108078B (zh) * 2009-12-24 2013-10-30 沈阳药科大学 1,4-取代酞嗪类化合物及其制备方法和用途
KR20140090665A (ko) * 2011-11-09 2014-07-17 아비에 도이치란트 게엠베하 운트 콤파니 카게 포스포디에스테라제 타입 １０ａ의 억제제로서 유용한 헤테로사이클릭 카복스아미드

Family Cites Families (6)

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GB2063249A (en) * 1979-10-09 1981-06-03 Mitsubishi Yuka Pharma 4-Phenylphthalazine derivatives
JPH03106873A (ja) * 1989-09-20 1991-05-07 Morishita Pharmaceut Co Ltd １―ピリジルフタラジン誘導体及びそれらを含有する血小板凝集抑制剤
ES2068413T3 (es) * 1990-03-30 1995-04-16 Mitsubishi Chem Ind Derivados de 4-fenilftalazina.
EP0634404A1 (en) * 1993-07-13 1995-01-18 Rhone Poulenc Agriculture Ltd. Phtalazin derivatives and their use as pesticides
DE69533057T2 (de) * 1994-08-09 2005-06-16 Eisai Co., Ltd. Kondensierte pyridazinverbindungen
IT1296984B1 (it) * 1997-12-19 1999-08-03 Zambon Spa Derivati ftalazinici inibitori della fosfodiesterasi 4

Also Published As

Publication number Publication date
IL139490A0 (en) 2001-11-25
PL345187A1 (en) 2001-12-03
NO20010331L (no) 2001-03-20
HK1039124B (zh) 2005-04-01
EA200100062A1 (ru) 2001-08-27
AR019409A1 (es) 2002-02-20
JP2002521370A (ja) 2002-07-16
TW509682B (en) 2002-11-11
HUP0102646A3 (en) 2003-01-28
BG105063A (en) 2001-07-31
AP2000001993A0 (en) 2000-12-31
HK1039124A1 (en) 2002-04-12
CA2338044A1 (en) 2000-02-03
DE69921139T2 (de) 2005-10-13
US6492360B1 (en) 2002-12-10
NZ507926A (en) 2002-10-25
OA11582A (en) 2004-07-26
MXPA01000670A (es) 2002-05-14
ID28874A (id) 2001-07-12
ITMI981670A1 (it) 2000-01-21
CN1127486C (zh) 2003-11-12
DE69921139D1 (de) 2004-11-18
HUP0102646A2 (hu) 2001-12-28
ITMI981670A0 (it) 1998-07-21
AU765457B2 (en) 2003-09-18
US6329370B1 (en) 2001-12-11
PA8478301A1 (es) 2000-09-29
AU5281099A (en) 2000-02-14
CO5090842A1 (es) 2001-10-30
WO2000005218A1 (en) 2000-02-03
EP1097142A1 (en) 2001-05-09
PE20000755A1 (es) 2000-09-01
EP1097142B1 (en) 2004-10-13
EP1371648A1 (en) 2003-12-17
ATE279397T1 (de) 2004-10-15
YU77500A (sh) 2002-11-15
NO318988B1 (no) 2005-05-30
SK1002001A3 (en) 2001-12-03
IS5772A (is) 2000-12-15
KR20010087161A (ko) 2001-09-15
UA68383C2 (en) 2004-08-16
NO20010331D0 (no) 2001-01-19
HRP20010057A2 (en) 2002-04-30
CN1305467A (zh) 2001-07-25
EE200100039A (et) 2002-06-17

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