NO995065L - Indole derivatives with combined 5HT1A, 5HT1B and 5HT1D receptor antagonist activity - Google Patents

Indole derivatives with combined 5HT1A, 5HT1B and 5HT1D receptor antagonist activity

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Publication number
NO995065L
NO995065L NO995065A NO995065A NO995065L NO 995065 L NO995065 L NO 995065L NO 995065 A NO995065 A NO 995065A NO 995065 A NO995065 A NO 995065A NO 995065 L NO995065 L NO 995065L
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NO
Norway
Prior art keywords
alkyl
nitrogen
oxygen
sulfur
hydrogen
Prior art date
Application number
NO995065A
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Norwegian (no)
Other versions
NO995065D0 (en
Inventor
Laramie Mary Gaster
Harshad Kantilal Rami
Paul Adrian Wyman
Original Assignee
Smithkline Beecham Plc
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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 NO995065D0 publication Critical patent/NO995065D0/en
Publication of NO995065L publication Critical patent/NO995065L/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)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

Forbindelser med formel(l), fremgangsmåter for deres fremstilling og anvendelse av dem som CNS-midler er beskrevet: hvor Ra er en gruppe med formel (i) hvor P1 er fenyl, bicyklisk aryl, en 5- til 7-leddet heterocyklisk ring inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen og svovel eller en bicyklisk, heterocyklisk ring inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen og svovel; R1 er hydrogen, halogen, C-j^alkyl. Cs.øcykloalkyl, COCi^alkyl, C-i.galkoksy, hydroksy, hydroksyCi.ealkyl, hydroksyC-i-ealkoksy, Ci_6alkoksyCi_6alkoksy, C-|_6alkanoyl, nitro, trifluormetyl, cyano, SR9, SOR9, SO2R9. SO2NR10R11, CO2R10, CONR1°R11, C02NR10R11, (CH2)cNR10R11. (CH2)CCONR1°R11, 6alkyl, CO2(CH2)COR10, NR10R11, NR1°CO2R11, NR10CONR10R11, CR1°=NOR11, NR10COOR11, CNR1°=NOR11. hvor R10 og R11 uavhengig er hydrogen eller C-j.salkyl og c er 1 til 4 R2 er hydrogen, halogen, C^alkyl, Cs.ecykloalkyl, Cs.gcykloalkenyl, C-i.galkoksy, acyl, aryl, acyloksy, hydroksy, nitro, trinuormetyl, cyano, CO2R10PCONR1 OR! 1, NR1°R11 hvor R10 og R11 er som definert for R1; aerl, 2 eller 3; eller Ra er en gruppe med formel (ii) (ii) hvor P2 og P3 uavhengig er fenyl, bicyklisk aryl, en 5- til 7- leddet heterocyklisk ring inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen og svovel eller en bicyklisk heterocyklisk gruppe inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen eller svovel; A er en binding eller oksygen, S (O)m hvor m er O til 2, karbonyl, CH2 eller NR4 hvor R4 er hydrogen eller C-i-øalkyl; R1 er som definert ovenfor for formel (l) eller R"! er en eventuelt substituert 5- til 7-leddet heterocyklisk ring inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen eller svovel; R2 og R3 er uavhengig hydrogen, halogen, C-i-salkyl, Cs.øcykloalkyl, C3_6cykloalkenyl, C^alkoksy, acyl, aryl, acyloksy, hydroksy, nitro, trifluormetyl, cyano, CO2R10, CONR10R11, NR10R11 hvor R10 og R11 er som definert for R1; og a og b er uavhengig 1, 2 eller 3; Y er - NH -, NR$ hvor R5 er C-|_6alkyl eller Y er - CH2 - eller - O -; V er oksygen eller svovel; D er nitrogen, karbon eller en CH gruppe; Wer (CR16R17)t hvor t er 2, 3 eller 4 og R16 og R17 er uavhengig hydrogen eller Ci^alkyl eller Wer (CR16R17)U-J hvor u er O, 1, 2 eller 3 og J er oksygen, svovel, CR16=CR17, CR16=N, =CR16Q, =CR16S eller =CR16-NR17; X er nitrogen eller karbon; Rb er hydrogen, halogen, hydroksy, Ci-galkyl, trifluormetyl, C-^alkoksy, C2- salkenyl, Cs.ycykloalkyl eventuelt substituert med C^alkyl eller aryl; Rc er hydrogen eller Ci_salkyl; og ¿ er en enkeltbinding når X er nitrogen eller en enkelt- eller dobbeltbinding når X er karbon.Compounds of formula (I), processes for their preparation and use of them as CNS agents are described: wherein Ra is a group of formula (i) wherein P1 is phenyl, bicyclic aryl, a 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur or a bicyclic heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur; R 1 is hydrogen, halogen, C 1-6 alkyl. C 1-6 cycloalkyl, CO C 1-6 alkyl, C 1-6 alkoxy, hydroxy, hydroxyC 1-6 alkyl, hydroxyC 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkoxy, C 1-6 alkanoyl, nitro, trifluoromethyl, cyano, SR9, SOR9, SO2R9. SO2NR10R11, CO2R10, CONR1 ° R11, CO2NR10R11, (CH2) cNR10R11. (CH2) CCONR1 ° R11, 6alkyl, CO2 (CH2) COR10, NR10R11, NR1 ° CO2R11, NR10CONR10R11, CR1 ° = NOR11, NR10COOR11, CNR1 ° = NOR11. wherein R 10 and R 11 are independently hydrogen or C 1-6 alkyl and c is 1 to 4 R2 is hydrogen, halogen, C 1-6 alkyl, C 6 -cycloalkyl, C 6 , cyano, CO2R10PCONR1 OR! 1, NR1 ° R11 wherein R10 and R11 are as defined for R1; aerl, 2 or 3; or Ra is a group of formula (ii) (ii) wherein P2 and P3 are independently phenyl, bicyclic aryl, a 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur or a bicyclic heterocyclic group containing 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 heteroatoms selected from oxygen, nitrogen or sulfur; R 2 and R 3 are independently hydrogen, halogen, C alkyl, C 6 cycloalkyl, C 3-6 cycloalkenyl, C 1-4 alkoxy, acyl, aryl, acyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO2R10, CONR10R11, NR10R11 where R10 and R11 are as defined for R1 and a and b are independently 1 or 3; Y is - NH -, NR $ 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; Wer (CR16R17) t where t is 2, 3 or 4 and R16 and R17 are independently hydrogen or C1-4 alkyl or Wer (CR16R17) UJ where u is O, 1, 2 or 3 and J is oxygen, sulfur, CR16 = CR17, CR16 = N, = CR16Q, = CR16S or = CR16-NR17; X is nitrogen or carbon; Rb is hydrogen, halogen, hydroxy, C1-6 alkyl, trifluoromethyl, C1-6 alkoxy, C2-salkenyl, C1- cycloalkyl optionally substituted with C1-6 alkyl or aryl; Rc is hydrogen or C1-6 alkyl; and ¿is a single bond when X is nitrogen or a single or double bond when X is carbon.

NO995065A 1997-04-18 1999-10-15 Indole derivatives with combined 5HT1A, 5HT1B and 5HT1D receptor antagonist activity NO995065L (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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NO995065L true NO995065L (en) 1999-10-15

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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) NO995065L (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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GB9725931D0 (en) * 1997-12-05 1998-02-04 Smithkline Beecham Plc Novel compounds
AU753360B2 (en) * 1998-07-31 2002-10-17 Nippon Soda Co., Ltd. Phenylazole compounds, process for producing the same and drugs for hyperlipemia
GB9827882D0 (en) * 1998-12-17 1999-02-10 Smithkline Beecham Plc Novel compounds
UA62015C2 (en) * 1998-12-28 2003-12-15 Pfizer Prod Inc Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants)
GB9912413D0 (en) * 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912417D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
JP2003505369A (en) * 1999-07-15 2003-02-12 エヌピーエス アレリックス コーポレーション Heterocyclic compounds for treating migraine
KR20020030126A (en) * 1999-09-25 2002-04-22 피터 기딩스 Piperazine Derivatives as 5-HT1B Antagonists
GB9926303D0 (en) * 1999-11-05 2000-01-12 Smithkline Beecham Plc Novel compounds
DE60017446T2 (en) * 1999-11-05 2006-03-02 Smithkline Beecham P.L.C., Brentford Isoquinoline and quinazoline derivatives with combined 5-HT1A, 5-HT1B and 5-HT1D receptor affinity
DE10051981A1 (en) 2000-10-20 2002-05-02 Bayer Ag Substituted phenyluracile
GB0106419D0 (en) * 2001-03-15 2001-05-02 Smithkline Beecham Plc Novel compounds
GB0106586D0 (en) * 2001-03-16 2001-05-09 Smithkline Beecham Plc Novel compounds
CZ20033529A3 (en) * 2001-06-07 2004-04-14 F. Hoffman-La Roche Ag Novel indole derivatives exhibiting affinity for 5-HT6 receptor
TW200403223A (en) * 2002-02-15 2004-03-01 Glaxo Group Ltd Novel compounds
WO2003095434A1 (en) 2002-05-13 2003-11-20 F. Hoffmann-La Roche Ag Benzoxazine derivatives as 5-ht6 modulators and uses thereof
JP4527730B2 (en) 2003-12-09 2010-08-18 エフ．ホフマン−ラ ロシュ アーゲー Benzoxazine derivatives and uses thereof
CA2707492A1 (en) * 2007-12-13 2009-06-18 Amgen Inc. Gamma secretase modulators
BR112012024380A2 (en) 2010-03-25 2015-09-15 Glaxosmithkline Llc chemical compounds
GB201106817D0 (en) 2011-04-21 2011-06-01 Astex Therapeutics Ltd New compound
CN102924330A (en) * 2012-09-03 2013-02-13 华东理工大学 Method for large-scale preparation of 5-amino-1-naphthyl nitrile
GB201218850D0 (en) 2012-10-19 2012-12-05 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy
GB201218864D0 (en) 2012-10-19 2012-12-05 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy
GB201218862D0 (en) 2012-10-19 2012-12-05 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy
US9980973B2 (en) 2012-10-19 2018-05-29 Astex Therapeutics Limited Bicyclic heterocycle compounds and their uses in therapy
CN103467374A (en) * 2013-08-30 2013-12-25 江苏弘和药物研发有限公司 Synthesis method of 8-bromine-4-carboxyl quinoline
MX2016008131A (en) 2013-12-20 2016-09-16 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy.
CN115197099A (en) * 2022-05-30 2022-10-18 安徽昊帆生物有限公司 Preparation method of N-Boc-1,4-phenylenediamine

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GB9119920D0 (en) * 1991-09-18 1991-10-30 Glaxo Group Ltd Chemical compounds
DE69232003T2 (en) * 1991-09-18 2002-04-25 Glaxo Group Ltd Benzanilide derivatives as 5-HT1D antagonists
GB9119932D0 (en) * 1991-09-18 1991-10-30 Glaxo Group Ltd Chemical compounds
EP0712397B1 (en) * 1993-08-06 1999-04-21 Smithkline Beecham Plc Amide derivatives as 5ht1d receptor antagonists
JPH09504004A (en) * 1993-08-20 1997-04-22 スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー Amide and urea derivatives for 5HT1D receptor antagonists
EP0716650B1 (en) * 1993-09-03 1999-03-24 Smithkline Beecham Plc Indole and indoline derivatives as 5ht1d receptor antagonists

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JP2001524116A (en) 2001-11-27
WO1998050358A1 (en) 1998-11-12
AU7431098A (en) 1998-11-27
PL336317A1 (en) 2000-06-19
AU732863B2 (en) 2001-05-03
TR199902590T2 (en) 2000-06-21
TW509687B (en) 2002-11-11
EP0975593A1 (en) 2000-02-02
NZ500252A (en) 2001-07-27
BR9809092A (en) 2002-01-22
CA2288662A1 (en) 1998-11-12
NO995065D0 (en) 1999-10-15
CO4950608A1 (en) 2000-09-01
HUP0001123A3 (en) 2002-04-29
AR013076A1 (en) 2000-12-13
CN1260781A (en) 2000-07-19
KR20010006487A (en) 2001-01-26
HUP0001123A2 (en) 2001-04-28
IL132409A0 (en) 2001-03-19

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