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ES2128266A1 - Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes. - Google Patents

Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes.

Info

Publication number
ES2128266A1
ES2128266A1 ES09701517A ES9701517A ES2128266A1 ES 2128266 A1 ES2128266 A1 ES 2128266A1 ES 09701517 A ES09701517 A ES 09701517A ES 9701517 A ES9701517 A ES 9701517A ES 2128266 A1 ES2128266 A1 ES 2128266A1
Authority
ES
Spain
Prior art keywords
alkyl
halogen
thophene
utilisation
benzothiophene
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.)
Granted
Application number
ES09701517A
Other languages
English (en)
Other versions
ES2128266B1 (es
Inventor
Vega Antonio Monge
Rio Zambrana Joaquin Del
Aldaz Berta Lasheras
Cubillo Juan Antonio Palop
Rovira Ana Bosch
Castillo Nieto Juan Carlos Del
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.)
Vita Invest SA
Original Assignee
Vita Invest SA
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 to ES009701517A priority Critical patent/ES2128266B1/es
Application filed by Vita Invest SA filed Critical Vita Invest SA
Priority to DE69822478T priority patent/DE69822478D1/de
Priority to TR2000/00058T priority patent/TR200000058T2/xx
Priority to PCT/ES1998/000191 priority patent/WO1999002516A1/es
Priority to CN98807490A priority patent/CN1125821C/zh
Priority to PL98337930A priority patent/PL337930A1/xx
Priority to AU81113/98A priority patent/AU735637B2/en
Priority to SK27-2000A priority patent/SK272000A3/sk
Priority to AT98930807T priority patent/ATE261956T1/de
Priority to BR9810557-4A priority patent/BR9810557A/pt
Priority to EA200000101A priority patent/EA002687B1/ru
Priority to KR1020007000190A priority patent/KR20010021632A/ko
Priority to CA002295715A priority patent/CA2295715A1/en
Priority to JP50819399A priority patent/JP2002511883A/ja
Priority to IL13356698A priority patent/IL133566A/xx
Priority to HU0002861A priority patent/HUP0002861A3/hu
Priority to NZ502128A priority patent/NZ502128A/en
Priority to EP98930807A priority patent/EP1008594B1/en
Publication of ES2128266A1 publication Critical patent/ES2128266A1/es
Priority to IS5328A priority patent/IS5328A/is
Priority to OA1200000002A priority patent/OA11274A/en
Priority to US09/480,120 priority patent/US6262056B1/en
Application granted granted Critical
Publication of ES2128266B1 publication Critical patent/ES2128266B1/es
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/24—Antidepressants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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 with nitro or nitroso radicals directly attached to ring carbon atoms
    • C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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 with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/64—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Saccharide Compounds (AREA)
  • Cosmetics (AREA)

Abstract

Compuestos derivados de tiofeno y benzotiofeno y utilización y composición correspondientes; los compuestos son de fórmula (I) donde Z es -CO-, -CH(OR6)-, -C(NOR7)-, R1 es: H, alquilo C1-C6, halógeno, o -O-R12, R2 y R3 son H, alquilo, halógeno, nitro o -O-R12 o bien R2 y R3 juntos son: -CR8=CR9-CR10=CR11-; R4 y R5 son H, alquilo, halógeno, haloalquilo, -OR12, nitro, -NR13R14; -COR12, -CO2 R12; -SO2NR13R14; -SO2R12; -SR12, ciano; -CONR13R14 o bien R4 y R5 forman un anillo de benceno; R6 es: H, alquilo, -CO2R12, -C(O)NR13R14 naftilo ó fenilo; R7 es: H o alquilo; R8, R9, R10 y R11 son H, alquilo, halógeno, -OR12, nitro, ciano, -NR13R14, -COR12, -CO2R12, -SO2NR13R14, -SO2 R12, -SR12, -CONR13R14; R12 es H, alquilo C1-C6, o fenilo; y R13 y R14 son H, alquilo o fenilo o bien R13 y R14 un anillo de 5 ó 6. Estos compuestos son eficaces para el tratamiento de la ansiedad o de la depresión.
ES009701517A 1997-07-08 1997-07-08 Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes. Expired - Fee Related ES2128266B1 (es)

Priority Applications (21)

Application Number Priority Date Filing Date Title
ES009701517A ES2128266B1 (es) 1997-07-08 1997-07-08 Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes.
JP50819399A JP2002511883A (ja) 1997-07-08 1998-07-01 ベンゾチオフェン誘導体ならびに対応する使用および組成物
PCT/ES1998/000191 WO1999002516A1 (es) 1997-07-08 1998-07-01 Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes
CN98807490A CN1125821C (zh) 1997-07-08 1998-07-01 苯并噻吩衍生物及其相应的用途和组合物
PL98337930A PL337930A1 (en) 1997-07-08 1998-07-01 Derivatives of benzothiophene as well as their application and compositions
AU81113/98A AU735637B2 (en) 1997-07-08 1998-07-01 Benzothiophene derivative and corresponding use and composition
SK27-2000A SK272000A3 (en) 1997-07-08 1998-07-01 Compounds derived from thiophene and benzothiophene, and related utilisation and composition
AT98930807T ATE261956T1 (de) 1997-07-08 1998-07-01 Thiophen- und benzothiophenderivate, deren verwendung und sie enthaltende zubereitung
BR9810557-4A BR9810557A (pt) 1997-07-08 1998-07-01 Compostos derivados de tiofeno e benzotiofeno e utilização e composição correspondentes
TR2000/00058T TR200000058T2 (tr) 1997-07-08 1998-07-01 Benzotiyofen türevleri-kullanım ve terkipleri.
DE69822478T DE69822478D1 (de) 1997-07-08 1998-07-01 Thiophen- und benzothiophenderivate, deren verwendung und sie enthaltende zubereitung
CA002295715A CA2295715A1 (en) 1997-07-08 1998-07-01 Compounds derived from thophene and benzothiophene, and related utilisation and composition
HU0002861A HUP0002861A3 (en) 1997-07-08 1998-07-01 Benzothiophene derivatives, and compositions containing the same
KR1020007000190A KR20010021632A (ko) 1997-07-08 1998-07-01 티오펜 및 벤조티오펜으로부터 유도된 화합물, 그 관련용도 및 조성물
IL13356698A IL133566A (en) 1997-07-08 1998-07-01 Compounds derived from benzothiophene, and related utilisation and composition
NZ502128A NZ502128A (en) 1997-07-08 1998-07-01 Benzothiophene compounds and their use in treating neurological disorders
EP98930807A EP1008594B1 (en) 1997-07-08 1998-07-01 Compounds derived from thophene and benzothiophene, and related utilisation and composition
EA200000101A EA002687B1 (ru) 1997-07-08 1998-07-01 Производные бензотиофена, их применение и композиции
IS5328A IS5328A (is) 1997-07-08 1999-12-29 Bensóþíófenafleiður og samsvarandi notkun þeirra og sametning
OA1200000002A OA11274A (en) 1997-07-08 2000-01-06 Benzothiophene derivatives and corresponding use and composition.
US09/480,120 US6262056B1 (en) 1997-07-08 2000-01-10 Benzothiophene derivatives and corresponding use and composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES009701517A ES2128266B1 (es) 1997-07-08 1997-07-08 Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes.

Publications (2)

Publication Number Publication Date
ES2128266A1 true ES2128266A1 (es) 1999-05-01
ES2128266B1 ES2128266B1 (es) 2000-01-16

Family

ID=8299986

Family Applications (1)

Application Number Title Priority Date Filing Date
ES009701517A Expired - Fee Related ES2128266B1 (es) 1997-07-08 1997-07-08 Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes.

Country Status (21)

Country Link
US (1) US6262056B1 (es)
EP (1) EP1008594B1 (es)
JP (1) JP2002511883A (es)
KR (1) KR20010021632A (es)
CN (1) CN1125821C (es)
AT (1) ATE261956T1 (es)
AU (1) AU735637B2 (es)
BR (1) BR9810557A (es)
CA (1) CA2295715A1 (es)
DE (1) DE69822478D1 (es)
EA (1) EA002687B1 (es)
ES (1) ES2128266B1 (es)
HU (1) HUP0002861A3 (es)
IL (1) IL133566A (es)
IS (1) IS5328A (es)
NZ (1) NZ502128A (es)
OA (1) OA11274A (es)
PL (1) PL337930A1 (es)
SK (1) SK272000A3 (es)
TR (1) TR200000058T2 (es)
WO (1) WO1999002516A1 (es)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU6050500A (en) * 1999-07-21 2001-02-13 Eli Lilly And Company Benzothiophene derivatives
TR200201683T2 (tr) 1999-12-30 2002-12-23 H. Lundbeck A/S İkameli fenil-piperazin türevleri, bunların hazırlanması ve kullanımları
DE10043659A1 (de) * 2000-09-05 2002-03-14 Merck Patent Gmbh Arylpiperazinderivate
ES2188344B1 (es) * 2000-11-29 2004-09-16 Laboratorios Vita, S.A. Compuestos derivados de benzotiofeno, su procedimiento de obtencion y utilizacion de los mismos.
NZ541009A (en) 2003-01-13 2007-09-28 Dynogen Pharmaceuticals Inc Method of treating nausea, vomiting, retching or any combination thereof
WO2004082686A2 (en) * 2003-03-13 2004-09-30 Dynogen Pharmaceuticals, Inc. Use of compounds with combined 5-ht1a and ssri activities to treat sexual dysfunction
TWI320783B (en) 2005-04-14 2010-02-21 Otsuka Pharma Co Ltd Heterocyclic compound
US8541409B2 (en) 2007-05-14 2013-09-24 Sk Biopharmaceuticals Co., Ltd. Carbamoyloxy arylalkanoyl arylpiperazine analgesics
CN101613347B (zh) * 2008-06-23 2012-07-04 中国人民解放军军事医学科学院毒物药物研究所 胺类化合物及其医药用途
CN101619056B (zh) * 2008-07-02 2013-07-17 石药集团中奇制药技术（石家庄）有限公司 苯并噻吩烷醇哌嗪衍生物及其作为抗抑郁症药物的应用
US9273027B2 (en) * 2010-02-24 2016-03-01 Research Triangle Institute Arylpiperazine opioid receptor antagonists
WO2015090235A1 (en) 2013-12-20 2015-06-25 Sunshine Lake Pharma Co., Ltd. Substituted piperazine compounds and methods of use thereof
WO2021152113A1 (en) 2020-01-31 2021-08-05 Bayer Aktiengesellschaft Substituted 2,3-benzodiazepines derivatives

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2979507A (en) * 1959-03-26 1961-04-11 Paul Adriaan J Janssen 1-(2-thenoyl) alkyl-4-arylpiperazines
US3002976A (en) * 1959-10-12 1961-10-03 Paul A J Janssen 1-(2-thienyl)-omega-(4-arylpiperazine)alkanols
GB1096341A (en) * 1965-03-09 1967-12-29 Mauvernay Roland Yves Novel derivatives of the phenyl-piperazine series and process for their preparation
US4515793A (en) * 1983-07-27 1985-05-07 Edna Mcconnell Clark Foundation Phenylpiperazines which are useful in the treatment of schistosomiasis
EP0574313A1 (fr) * 1992-06-12 1993-12-15 Adir Et Compagnie Pipérazines 1,4-disubstituées pour le traitement des maladies du système nerveux central et des maladies neuro endocriniennes
EP0596120A1 (en) * 1991-08-09 1994-05-11 Yoshitomi Pharmaceutical Industries, Ltd. Thiophene compound

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5632898A (en) * 1996-08-13 1997-05-27 Isis Pharmaceuticals, Inc. Method for removing unreacted electrophiles from a reaction mixture

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2979507A (en) * 1959-03-26 1961-04-11 Paul Adriaan J Janssen 1-(2-thenoyl) alkyl-4-arylpiperazines
US3002976A (en) * 1959-10-12 1961-10-03 Paul A J Janssen 1-(2-thienyl)-omega-(4-arylpiperazine)alkanols
GB1096341A (en) * 1965-03-09 1967-12-29 Mauvernay Roland Yves Novel derivatives of the phenyl-piperazine series and process for their preparation
US4515793A (en) * 1983-07-27 1985-05-07 Edna Mcconnell Clark Foundation Phenylpiperazines which are useful in the treatment of schistosomiasis
EP0596120A1 (en) * 1991-08-09 1994-05-11 Yoshitomi Pharmaceutical Industries, Ltd. Thiophene compound
EP0574313A1 (fr) * 1992-06-12 1993-12-15 Adir Et Compagnie Pipérazines 1,4-disubstituées pour le traitement des maladies du système nerveux central et des maladies neuro endocriniennes

Also Published As

Publication number Publication date
CN1125821C (zh) 2003-10-29
TR200000058T2 (tr) 2000-09-21
JP2002511883A (ja) 2002-04-16
NZ502128A (en) 2001-09-28
BR9810557A (pt) 2000-08-08
HUP0002861A3 (en) 2001-09-28
DE69822478D1 (de) 2004-04-22
IL133566A (en) 2003-10-31
HUP0002861A2 (hu) 2001-08-28
PL337930A1 (en) 2000-09-11
SK272000A3 (en) 2000-07-11
IL133566A0 (en) 2001-04-30
AU735637B2 (en) 2001-07-12
IS5328A (is) 1999-12-29
CA2295715A1 (en) 1999-01-21
EA002687B1 (ru) 2002-08-29
OA11274A (en) 2003-07-29
EP1008594B1 (en) 2004-03-17
CN1265106A (zh) 2000-08-30
ATE261956T1 (de) 2004-04-15
KR20010021632A (ko) 2001-03-15
EA200000101A1 (ru) 2000-08-28
US6262056B1 (en) 2001-07-17
AU8111398A (en) 1999-02-08
WO1999002516A1 (es) 1999-01-21
ES2128266B1 (es) 2000-01-16
EP1008594A1 (en) 2000-06-14

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