CA2306692C - Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers - Google Patents

Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers Download PDF

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Publication number
CA2306692C
CA2306692C CA2306692A CA2306692A CA2306692C CA 2306692 C CA2306692 C CA 2306692C CA 2306692 A CA2306692 A CA 2306692A CA 2306692 A CA2306692 A CA 2306692A CA 2306692 C CA2306692 C CA 2306692C
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asp
ch2f
compound
cbz
pharmaceutically acceptable
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Expired - Fee Related
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CA2306692A
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CA2306692A1 (fr
Inventor
John F. W. Keana
Sui Xiong Cai
John Guastella
Wu Yang
John A. Drewe
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Cytovia Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • A61P7/06—Antianaemics
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • 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
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D277/16—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2810/00—Vectors comprising a targeting moiety
    • C12N2810/40—Vectors comprising a peptide as targeting moiety, e.g. a synthetic peptide, from undefined source

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Immunology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Rheumatology (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Endocrinology (AREA)
  • Transplantation (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Emergency Medicine (AREA)
  • Vascular Medicine (AREA)
  • Biophysics (AREA)
  • Obesity (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Orthopedic Medicine & Surgery (AREA)

Abstract

La présente invention concerne de nouveaux dipeptides représentés par la formule générale (I), dans laquelle R1-R3 et AA sont définis. Les composés correspondant à la formule (I) sont de puissants inhibiteurs de la mort cellulaire programmée. Par conséquent, les inhibiteurs décrits dans la présente invention peuvent retarder ou bloquer la mort cellulaire dans diverses conditions cliniques pouvant donner lieu à la perte de cellules, de tissus ou de la totalité des organes.
CA2306692A 1997-10-10 1998-10-09 Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers Expired - Fee Related CA2306692C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US6167697P 1997-10-10 1997-10-10
US60/061,676 1997-10-10
PCT/US1998/021232 WO1999018781A1 (fr) 1997-10-10 1998-10-09 Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers

Publications (2)

Publication Number Publication Date
CA2306692A1 CA2306692A1 (fr) 1999-04-22
CA2306692C true CA2306692C (fr) 2010-09-21

Family

ID=22037372

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2306692A Expired - Fee Related CA2306692C (fr) 1997-10-10 1998-10-09 Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers

Country Status (10)

Country Link
EP (1) EP1033910A4 (fr)
JP (1) JP4439111B2 (fr)
KR (1) KR100580333B1 (fr)
CN (1) CN1138472C (fr)
AU (1) AU741203B2 (fr)
BR (1) BR9814817A (fr)
CA (1) CA2306692C (fr)
EA (1) EA200000409A1 (fr)
NO (1) NO20001323L (fr)
WO (1) WO1999018781A1 (fr)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6184210B1 (en) 1997-10-10 2001-02-06 Cytovia, Inc. Dipeptide apoptosis inhibitors and the use thereof
KR20010041905A (ko) * 1998-03-16 2001-05-25 시토비아 인크. 디펩티드 카스파제 억제제 및 이의 용도
DE69932434D1 (de) 1998-05-29 2006-08-31 Mochida Pharm Co Ltd Prophylaxe und Behandlung von autoimmunen Entmyelinisierungserkrankungen durch Fas-antagonisten
US7488590B2 (en) 1998-10-23 2009-02-10 Amgen Inc. Modified peptides as therapeutic agents
US6660843B1 (en) 1998-10-23 2003-12-09 Amgen Inc. Modified peptides as therapeutic agents
MEP42108A (en) 1998-10-23 2011-02-10 Kiren Amgen Inc Dimeric thrombopoietin peptide mimetics binding to mp1 receptor and having thrombopoietic activity
WO2000044216A2 (fr) 1999-02-01 2000-08-03 Cytovia Inc Acide de gomme-gute,. analogues et derives en tant qu'activateurs de caspases et inducteurs d'apoptose
AU3876600A (en) 1999-03-16 2000-10-04 Cytovia, Inc. Substituted 2-aminobenzamide caspase inhibitors and the use thereof
US6355618B1 (en) * 1999-04-09 2002-03-12 Cytovia, Inc. Caspase inhibitors and the use thereof
US6495522B1 (en) 1999-08-27 2002-12-17 Cytovia, Inc. Substituted alpha-hydroxy acid caspase inhibitors and the use thereof
US6566338B1 (en) 1999-10-12 2003-05-20 Cytovia, Inc. Caspase inhibitors for the treatment and prevention of chemotherapy and radiation therapy induced cell death
US6303374B1 (en) 2000-01-18 2001-10-16 Isis Pharmaceuticals Inc. Antisense modulation of caspase 3 expression
DE10006889A1 (de) * 2000-02-16 2001-09-06 Procorde Gmbh Verwendung von Inhibitoren von Caspase-3 oder der Caspase-aktivierten Desoxyribonuclease (CAD) zur Behandlung von Herzerkrankungen
EP1923386A3 (fr) 2000-03-29 2008-05-28 Vertex Pharmceuticals Incorporated Dérivés de carbamates en tant qu'inhibiteurs de caspase et leurs utilisations
AU2001249619B2 (en) * 2000-03-29 2006-08-17 Vertex Pharmaceuticals Incorporated Carbamate caspase inhibitors and uses thereof
KR20020025959A (ko) 2000-05-23 2002-04-04 버텍스 파마슈티칼스 인코포레이티드 카스파제 억제제 및 이의 용도
US20020052323A1 (en) * 2000-08-30 2002-05-02 Jinhai Wang Quinoline-(C=O)-(multiple amino acids)-leaving group compounds for pharmaceutical compositions and reagents
CA2418720A1 (fr) 2000-09-13 2002-03-21 Vertex Pharmaceuticals Incorporated Inhibiteurs de caspase et leurs utilisations
WO2002022605A1 (fr) 2000-09-15 2002-03-21 Vertex Pharmaceuticals Incorporated Composes de pyrazole utiles comme inhibiteurs de proteine kinase
US7473691B2 (en) 2000-09-15 2009-01-06 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
US6660731B2 (en) 2000-09-15 2003-12-09 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
US6989385B2 (en) 2000-12-21 2006-01-24 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
US20030096737A1 (en) 2001-04-19 2003-05-22 Anita Diu-Hercend Caspase inhibitors and uses thereof
MY141867A (en) 2002-06-20 2010-07-16 Vertex Pharma Substituted pyrimidines useful as protein kinase inhibitors
CN1319968C (zh) 2002-08-02 2007-06-06 沃泰克斯药物股份有限公司 用作gsk－3的抑制剂的吡唑组合物
EP1549224A1 (fr) * 2002-10-10 2005-07-06 Becton Dickinson and Company Systeme collecteur d'echantillons avec inhibiteur de caspase
WO2006036834A2 (fr) 2004-09-24 2006-04-06 Amgen Inc. Molecules fc modifiees
US8008453B2 (en) 2005-08-12 2011-08-30 Amgen Inc. Modified Fc molecules
MX2008005814A (es) 2005-11-03 2008-10-15 Vertex Pharma Aminopirimidinas utiles como inhibidores de cinasa.
JP5389785B2 (ja) 2007-05-02 2014-01-15 バーテックス ファーマシューティカルズ インコーポレイテッド キナーゼ阻害剤として有用なチアゾールおよびピラゾール
NZ582879A (en) 2007-07-31 2012-03-30 Vertex Pharma Process for preparing 5-fluoro-1h-pyrazolo [3, 4-b] pyridin-3-amine and derivatives thereof
FR2923160B1 (fr) * 2007-11-02 2013-07-26 Pasteur Institut Composes destines a prevenir ou traiter une infection virale.
MX2011002312A (es) 2008-09-03 2011-04-26 Vertex Pharma Co-cristales y formulaciones farmaceuticas que comprenden los mismos.
CN106317161B (zh) * 2015-06-29 2020-05-15 深圳翰宇药业股份有限公司 一种氟甲基酮肽系列化合物的制备方法
CN117045634B (zh) * 2022-05-06 2025-10-10 北京康蒂尼药业股份有限公司 一种二肽衍生物组合物及其制备方法和用途

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WO1991015577A1 (fr) * 1990-04-04 1991-10-17 Black, Roy, A. INTERLEUKIN 1'beta' PROTEASE
DE69226820T2 (de) * 1991-06-21 1999-05-12 Merck & Co., Inc., Rahway, N.J. Peptidylderivate als Inhibitoren von Interleukin-1B-konvertierenden Enzymen
AU657701B2 (en) * 1991-08-30 1995-03-23 Vertex Pharmaceuticals Incorporated Interleukin 1beta protease and interleukin 1beta protease inhibitors
US5462939A (en) * 1993-05-07 1995-10-31 Sterling Winthrop Inc. Peptidic ketones as interleukin-1β-converting enzyme inhibitors
JPH0789951A (ja) * 1993-06-03 1995-04-04 Sterling Winthrop Inc インターロイキン−１β転換酵素阻害剤
US5565430A (en) * 1994-08-02 1996-10-15 Sterling Winthrop Inc. Azaaspartic acid analogs as interleukin-1β converting enzyme inhibitors
AU738048B2 (en) * 1996-09-12 2001-09-06 Idun Pharmaceuticals, Inc. Inhibition of apoptosis using interleukin-1beta-converting enzyme (ICE)/CED-3 family inhibitors

Also Published As

Publication number Publication date
KR20010031053A (ko) 2001-04-16
CA2306692A1 (fr) 1999-04-22
KR100580333B1 (ko) 2006-05-16
NO20001323L (no) 2000-06-13
AU741203B2 (en) 2001-11-22
EP1033910A4 (fr) 2004-11-24
NO20001323D0 (no) 2000-03-14
BR9814817A (pt) 2002-01-08
CN1138472C (zh) 2004-02-18
WO1999018781A1 (fr) 1999-04-22
JP2001519358A (ja) 2001-10-23
CN1301131A (zh) 2001-06-27
AU9793098A (en) 1999-05-03
JP4439111B2 (ja) 2010-03-24
EP1033910A1 (fr) 2000-09-13
EA200000409A1 (ru) 2000-10-30

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