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BR9809092A - Indole derivatives having combined 5ht1a, 5ht1b and 5ht1d receptor antagonist activity - Google Patents

Indole derivatives having combined 5ht1a, 5ht1b and 5ht1d receptor antagonist activity

Info

Publication number
BR9809092A
BR9809092A BR9809092-5A BR9809092A BR9809092A BR 9809092 A BR9809092 A BR 9809092A BR 9809092 A BR9809092 A BR 9809092A BR 9809092 A BR9809092 A BR 9809092A
Authority
BR
Brazil
Prior art keywords
alkyl
nitrogen
oxygen
sulfur
alkoxy
Prior art date
Application number
BR9809092-5A
Other languages
Portuguese (pt)
Inventor
Laramie Mary Gaster
Harshad Kantilal Rami
Paul Adrian Wyman
Original Assignee
Smithkline Beecham Plc
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
Priority claimed from GBGB9707829.9A external-priority patent/GB9707829D0/en
Priority claimed from GBGB9801882.3A external-priority patent/GB9801882D0/en
Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc
Publication of BR9809092A publication Critical patent/BR9809092A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D409/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D413/12—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 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
    • C07D417/02—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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

"DERIVADOS DE INDOL TENDO ATIVIDADE COMBINADA DE ANTAGONISTA DE RECEPTOR DE 5HT1A, 5HT1B E 5HT1D". A presente invenção refere-se a compostos de fórmula (I), processos para sua preparação e seu uso como agentes de CNS, em que R^ a^ é um grupo de fórmula (i), em que P^ 1^ é uma fenila, arila bicílica, um anel heterocíclico contendo de 5 a 7 membros contendo de 1 a 3 heteroátomos selecionados de oxigênio, nitrogênio e enxofre, ou um anel heterocíclico bicílico contendo de 1 a 3 heteroátomos selecionados de oxigênio, nitrogênio e enxofre; R^ 1^ é hidrogênio, halogênio, alquila C~ 1-6~, cicloalquila C~ 3-6~, COalquila C~ 1-6~, alcóxi C~ 1-6~, hidróxi, hidróxi alquila C~ 1-6~, hidróxi alcóxi C~ 1-6~, alcóxi C~ 1-6, alcóxi C~ 1-6~, alcanoila C~ 1-6~, nitro, trifluor metila, ciano, SR^ 9^, SOR^ 9~, SO~ 2~R^ 9^, SO~ 2~NR^ 10^R^ 11^, CO~ 2~R^ 10^, CONR^ 10^R^ 11^, CO~ 2~NR^ 10^R^ 11^ CONR^ 10^(CH~ 2~)~ c~CO~ 2~R^ 11^, (CH~ 2~)~ c~NR^ 10^R^ 11^, (CH~ 2~)~ c~CONR^ 10^R^ 11^, (CH~ 2~)~ c~NR^ 10^R^ 11^, (CH~ 2~)~ c~CO~ 2~alquila C~ 1-6~, CO~ 2~(CH~ 2~)~ c~ OR^ 10^, NR^ 10^OR^ 11^, NR^ 10^CO~ 2~R^ 11^, NR^ 10^CONR^ 10^R^ 11^, CR^ 11^=NOR^ 11^, NR^ 10^COOR^ 11^, CNR~ 10^=NOR^ 11^, onde R^ 10^ e R^ 11^ são independentemente hidrogênio ou alquila C~ 1-6~ e c é 1 a 4; R^ 2^ é hidrogênio, halogênio, alquila C^ 1-6^, cicloalquila C~ 3-6~, cilcoalquenila C~ 3-6~, alcóxi C~ 1-6~, acila, arila, acilóxi, hidróxi, nitro, trifluormetila, ciano, CO~ 2~R^ 10^, CONR^ 10^R^ 11^, NR^ 10^R^ 11^, onde R^ 10^ e R^ 11^ são como definidos para R^ 1^; a é 1, 2 ou 3; ou R^ a^ é um grupo de fórmula (ii), em que p^ 2^ e P^ 3^ são independentemente fenila, arila bicíclica, um anel heterocíclico de 5 a 7 membros contendo de 1 a 3 heteroátomos selecionados de oxigênio, nitrogênio e enxofre, ou um grupo heterocíclico bicíclico contendo de 1 a 3 heteroátomos selecionados de oxigênio, nitrogênio ou enxofre; A é uma ligação ou oxigênio, S (O)~ m~ onde m é 0 a 2, carbonila, CH~ 2~ ou NR^ 4^~ onde R^ 4^ é hidrogênio ou alquila C~ 1-6~; R^ 1^ é como definido acima para a fórmula (I) ou R^ 1^ é um anel heterocíclico opcionalmente substituído de 5 a 7 membros contendo de 1 a 3 heteroátomos selecionados de oxigênio, nitrogênio ou enxofre; R^ 2^ e R^ 3^ são independentemente hidrogênio, halogênio, alquila C~ 1-6~, cicloalquila C~ 3-6~, cicloalquenila C~ 3-6~, alcóxi C~ 1-6~, acila, arila, acilóxi, hidróxi, nitro, trifluormetila, ciano, CO~ 2~R^ 10^, CONR^ 10^R^ 11^, NR^ 10^R^ 11^, onde R^ 10^ e R^ 11^ são como definidos para R^ 1^; e a e b são, independentemente, 1, 2 ou 3; Y é -NH-, NR^ 5^, onde R^ 5^ é alquila C~ 1-6~, ou Y é -CH~ 2~ ou -O-; V é oxigênio ou enxofre; D é nitrogênio, carbono ou um grupo CH; W é (CR^ 16^R^ 17^)~ t~, onde t é 2, 3 ou 4 e R^ 16^ e R^ 17^ são, independentemente, hidrogênio ou alquila C~ 1-6~ ou W é (CR^ 16~R~ 17~)~ u~- J, onde u é 0, 1, 2 ou 3 e J é oxigênio, enxofre, CR^ 16^=CR^ 17^, CR^ 16^=N, =CR^ 16^O, =CR^ 16^S ou =CR^ 16^ -NR^ 17^; X é nitrogênio ou carbono; R^ b^ é hidrogênio, halogênio, hidróxi, alquila C~ 1-6~, trifluormetila, alkóxi C~ 1-6~, alquenila C~ 2-6~, cicloalquila C~ 3-7~ opcionalmente substituído por alquila C~ 1-4~ ou arila; R^ c^ é hidrogênio ou alquila C~ 1-6~; e <sym> é uma ligação simples quando X é nitrogênio ou uma ligação simples ou dupla quando X é carbono."INDOL DERIVATIVES HAVING COMBINED ACTIVITY OF 5HT1A, 5HT1B AND 5HT1D RECEPTOR ANTAGONIST". The present invention relates to compounds of formula (I), processes for their preparation and use as CNS agents, where R ^ a ^ is a group of formula (i), where P ^ 1 ^ is a phenyl , bicyclic aryl, a heterocyclic ring containing from 5 to 7 members containing from 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur, or a bicyclic heterocyclic ring containing from 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur; R ^ 1 ^ is hydrogen, halogen, C ~ 1-6 ~ alkyl, C ~ 3-6 ~ cycloalkyl, C ~ 1-6 ~ alkyl, C ~ 1-6 ~ alkoxy, hydroxy, C ~ 1-6 alkyl hydroxy ~, C ~ 1-6 ~ alkoxy hydroxide, C ~ 1-6 alkoxy, C ~ 1-6 ~ alkoxy, C ~ 1-6 ~ alkanoyl, nitro, methyl trifluor, cyano, SR ^ 9 ^, SOR ^ 9 ~ , SO ~ 2 ~ R ^ 9 ^, SO ~ 2 ~ NR ^ 10 ^ R ^ 11 ^, CO ~ 2 ~ R ^ 10 ^, CONR ^ 10 ^ R ^ 11 ^, CO ~ 2 ~ NR ^ 10 ^ R ^ 11 ^ CONR ^ 10 ^ (CH ~ 2 ~) ~ c ~ CO ~ 2 ~ R ^ 11 ^, (CH ~ 2 ~) ~ c ~ NR ^ 10 ^ R ^ 11 ^, (CH ~ 2 ~) ~ c ~ CONR ^ 10 ^ R ^ 11 ^, (CH ~ 2 ~) ~ c ~ NR ^ 10 ^ R ^ 11 ^, (CH ~ 2 ~) ~ c ~ CO ~ 2 ~ C ~ 1-6 ~ alkyl, CO ~ 2 ~ (CH ~ 2 ~) ~ c ~ OR ^ 10 ^, NR ^ 10 ^ OR ^ 11 ^, NR ^ 10 ^ CO ~ 2 ~ R ^ 11 ^, NR ^ 10 ^ CONR ^ 10 ^ R ^ 11 ^, CR ^ 11 ^ = NOR ^ 11 ^, NR ^ 10 ^ COOR ^ 11 ^, CNR ~ 10 ^ = NOR ^ 11 ^, where R ^ 10 ^ and R ^ 11 ^ are independently hydrogen or C ~ 1 alkyl -6 ~ ec is 1 to 4; R ^ 2 ^ is hydrogen, halogen, C ^ 1-6 ^ alkyl, C ~ 3-6 ~ cycloalkyl, C ~ 3-6 ~ cycloalkyl, C ~ 1-6 ~ alkoxy, acyl, aryl, acyloxy, hydroxy, nitro , trifluoromethyl, cyano, CO ~ 2 ~ R ^ 10 ^, CONR ^ 10 ^ R ^ 11 ^, NR ^ 10 ^ R ^ 11 ^, where R ^ 10 ^ and R ^ 11 ^ are as defined for R ^ 1 ^ ; a is 1, 2 or 3; or R ^ a ^ is a group of formula (ii), in which p ^ 2 ^ and P ^ 3 ^ are independently phenyl, bicyclic aryl, a 5- to 7-membered heterocyclic ring containing from 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur, or a bicyclic heterocyclic group containing from 1 to 3 heteroatoms selected from oxygen, nitrogen or sulfur; A is a bond or oxygen, S (O) ~ m ~ where m is 0 to 2, carbonyl, CH ~ 2 ~ or NR ^ 4 ^ ~ where R ^ 4 ^ is hydrogen or C ~ 1-6 ~ alkyl; R ^ 1 ^ is as defined above for formula (I) or R ^ 1 ^ is an optionally substituted 5- to 7-membered heterocyclic ring containing 1 to 3 selected heteroatoms of oxygen, nitrogen or sulfur; R ^ 2 ^ and R ^ 3 ^ are independently hydrogen, halogen, C ~ 1-6 ~ alkyl, C ~ 3-6 ~ cycloalkyl, C ~ 3-6 ~ cycloalkenyl, C ~ 1-6 ~ alkoxy, acyl, aryl , acyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO ~ 2 ~ R ^ 10 ^, CONR ^ 10 ^ R ^ 11 ^, NR ^ 10 ^ R ^ 11 ^, where R ^ 10 ^ and R ^ 11 ^ are like defined for R ^ 1 ^; and a and b are, independently, 1, 2 or 3; Y is -NH-, NR ^ 5 ^, where R ^ 5 ^ is C ~ 1-6 ~ alkyl, or Y is -CH ~ 2 ~ or -O-; V is oxygen or sulfur; D is nitrogen, carbon or a CH group; W is (CR ^ 16 ^ R ^ 17 ^) ~ t ~, where t is 2, 3 or 4 and R ^ 16 ^ and R ^ 17 ^ are independently hydrogen or C ~ 1-6 ~ alkyl or W is (CR ^ 16 ~ R ~ 17 ~) ~ u ~ - J, where u is 0, 1, 2 or 3 and J is oxygen, sulfur, CR ^ 16 ^ = CR ^ 17 ^, CR ^ 16 ^ = N, = CR ^ 16 ^ O, = CR ^ 16 ^ S or = CR ^ 16 ^ -NR ^ 17 ^; X is nitrogen or carbon; R ^ b ^ is hydrogen, halogen, hydroxy, C ~ 1-6 ~ alkyl, trifluoromethyl, C ~ 1-6 ~ alkoxy, C ~ 2-6 ~ alkenyl, C ~ 3-7 ~ cycloalkyl optionally substituted by C ~ alkyl 1-4 ~ or aryl; R ^ c ^ is hydrogen or C ~ 1-6 ~ alkyl; and <sym> is a single bond when X is nitrogen or a single or double bond when X is carbon.

BR9809092-5A 1997-04-18 1998-04-14 Indole derivatives having combined 5ht1a, 5ht1b and 5ht1d receptor antagonist activity BR9809092A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9707829.9A GB9707829D0 (en) 1997-04-18 1997-04-18 Novel compounds
GBGB9801882.3A GB9801882D0 (en) 1998-01-29 1998-01-29 Novel compounds
PCT/EP1998/002262 WO1998050358A1 (en) 1997-04-18 1998-04-14 Indole derivatives having combined 5ht1a, 5ht1b and 5ht1d receptor antagonist activity

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BR9809092A true BR9809092A (en) 2002-01-22

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EP (1) EP0975593A1 (en)
JP (1) JP2001524116A (en)
KR (1) KR20010006487A (en)
CN (1) CN1260781A (en)
AR (1) AR013076A1 (en)
AU (1) AU732863B2 (en)
BR (1) BR9809092A (en)
CA (1) CA2288662A1 (en)
CO (1) CO4950608A1 (en)
HU (1) HUP0001123A3 (en)
IL (1) IL132409A0 (en)
NO (1) NO995065D0 (en)
NZ (1) NZ500252A (en)
PL (1) PL336317A1 (en)
TR (1) TR199902590T2 (en)
TW (1) TW509687B (en)
WO (1) WO1998050358A1 (en)

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AU732863B2 (en) 2001-05-03
CA2288662A1 (en) 1998-11-12
PL336317A1 (en) 2000-06-19
NZ500252A (en) 2001-07-27
EP0975593A1 (en) 2000-02-02
HUP0001123A2 (en) 2001-04-28
CN1260781A (en) 2000-07-19
NO995065L (en) 1999-10-15
TR199902590T2 (en) 2000-06-21
IL132409A0 (en) 2001-03-19
CO4950608A1 (en) 2000-09-01
HUP0001123A3 (en) 2002-04-29
AR013076A1 (en) 2000-12-13
JP2001524116A (en) 2001-11-27
WO1998050358A1 (en) 1998-11-12
NO995065D0 (en) 1999-10-15
KR20010006487A (en) 2001-01-26
AU7431098A (en) 1998-11-27
TW509687B (en) 2002-11-11

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