ES2358097T3 - Derivados retinoides con actividades antiangiogénicas, antitumorales y proapoptóticas. - Google Patents

Derivados retinoides con actividades antiangiogénicas, antitumorales y proapoptóticas. Download PDF

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Publication number
ES2358097T3
ES2358097T3 ES02760553T ES02760553T ES2358097T3 ES 2358097 T3 ES2358097 T3 ES 2358097T3 ES 02760553 T ES02760553 T ES 02760553T ES 02760553 T ES02760553 T ES 02760553T ES 2358097 T3 ES2358097 T3 ES 2358097T3
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Spain
Prior art keywords
use according
tumor
compounds
alkyl
adamantyl
Prior art date
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Expired - Lifetime
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ES02760553T
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English (en)
Spanish (es)
Inventor
L. Uni. degli Studi di Milano MERLINI
S. Uni. degli Studi di Milano DALLAVALLE
Sergio Penco
G. Sigma-Tau Ind. Farma. Riunite S.p.a. GIANNINI
C. Sigma-Tau Ind. Farma. Riunite S.p.a. PISANO
L. Sigma-Tau Ind. Farma. Riunite S.p.a. VESCI
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Sigma Tau Industrie Farmaceutiche Riunite SpA
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Sigma Tau Industrie Farmaceutiche Riunite SpA
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Application filed by Sigma Tau Industrie Farmaceutiche Riunite SpA filed Critical Sigma Tau Industrie Farmaceutiche Riunite SpA
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    • 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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • 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
    • 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
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/32—Unsaturated compounds containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Oncology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
  • Cardiology (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Hematology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Indole Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
ES02760553T 2001-07-31 2002-07-18 Derivados retinoides con actividades antiangiogénicas, antitumorales y proapoptóticas. Expired - Lifetime ES2358097T3 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITRM01A0464 2001-07-31
IT2001RM000464A ITRM20010464A1 (it) 2001-07-31 2001-07-31 Derivati retinoidi ad attivita' antiangiogenica, antitumorale e pro-apoptotica.

Publications (1)

Publication Number Publication Date
ES2358097T3 true ES2358097T3 (es) 2011-05-05

Family

ID=11455702

Family Applications (1)

Application Number Title Priority Date Filing Date
ES02760553T Expired - Lifetime ES2358097T3 (es) 2001-07-31 2002-07-18 Derivados retinoides con actividades antiangiogénicas, antitumorales y proapoptóticas.

Country Status (19)

Country Link
US (2) US8101793B2 (enExample)
EP (1) EP1412317B1 (enExample)
JP (1) JP4463550B2 (enExample)
KR (1) KR100888466B1 (enExample)
CN (1) CN1279014C (enExample)
AT (1) ATE492526T1 (enExample)
AU (1) AU2002326144B2 (enExample)
BR (1) BR0211521A (enExample)
CA (1) CA2454532C (enExample)
CY (1) CY1114535T1 (enExample)
DE (1) DE60238683D1 (enExample)
DK (1) DK1412317T3 (enExample)
ES (1) ES2358097T3 (enExample)
HU (1) HU229308B1 (enExample)
IT (1) ITRM20010464A1 (enExample)
MX (1) MXPA04000877A (enExample)
PL (1) PL207530B1 (enExample)
PT (1) PT1412317E (enExample)
WO (1) WO2003011808A1 (enExample)

Families Citing this family (39)

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US20030228309A1 (en) * 2000-11-08 2003-12-11 Theodora Salcedo Antibodies that immunospecifically bind to TRAIL receptors
US20060062786A1 (en) * 2000-11-08 2006-03-23 Human Genome Sciences, Inc. Antibodies that immunospecifically bind to TRAIL receptors
US20090226429A1 (en) * 2001-05-25 2009-09-10 Human Genome Sciences, Inc. Antibodies That Immunospecifically Bind to TRAIL Receptors
US7348003B2 (en) 2001-05-25 2008-03-25 Human Genome Sciences, Inc. Methods of treating cancer using antibodies that immunospecifically bind to TRAIL receptors
US20050214209A1 (en) * 2001-05-25 2005-09-29 Human Genome Sciences, Inc. Antibodies that immunospecifically bind to TRAIL receptors
US7361341B2 (en) * 2001-05-25 2008-04-22 Human Genome Sciences, Inc. Methods of treating cancer using antibodies that immunospecifically bind to trail receptors
US20050129616A1 (en) * 2001-05-25 2005-06-16 Human Genome Sciences, Inc. Antibodies that immunospecifically bind to TRAIL receptors
ITRM20010464A1 (it) * 2001-07-31 2003-01-31 Sigma Tau Ind Farmaceuti Derivati retinoidi ad attivita' antiangiogenica, antitumorale e pro-apoptotica.
EP1456165A1 (en) * 2001-11-30 2004-09-15 The Burnham Institute Induction of apoptosis in cancer cells
CN1610696A (zh) * 2001-12-20 2005-04-27 人体基因组科学有限公司 免疫特异性结合trail受体的抗体
EP1856063B1 (en) 2005-02-22 2012-01-25 Ranbaxy Laboratories Limited 5-phenyl-pentanoic acid derivatives as matrix metalloproteinase inhibitors for the treatment of asthma and other diseases
AU2006233810B2 (en) 2005-04-08 2011-02-17 Galderma Research & Development New method for the preparation of 6-(3-(1-adamantyl)-4-methoxphenyl)-2-naphthoic acid
FR2884248B1 (fr) * 2005-04-08 2007-05-18 Galderma Res & Dev Nouveau procede de preparation de l'acide 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoique
ITRM20050248A1 (it) * 2005-05-20 2006-11-21 Sigma Tau Ind Farmaceuti Uso acido adamantil metossidifenil propenoico per il trattamento di patologie cutanee.
ES2356129T3 (es) * 2005-06-28 2011-04-05 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Derivados de ácido bifenil y naftil-fenil hidroxámico.
WO2007037188A1 (ja) * 2005-09-27 2007-04-05 Sapporo Medical University 血管透過性亢進に起因する眼疾患の予防及び治療のための医薬
WO2007071605A1 (en) * 2005-12-19 2007-06-28 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. The use of st1898 for the treatment of restenosis
JP5054006B2 (ja) * 2006-06-23 2012-10-24 ロート製薬株式会社 ヒアルロン酸産生促進能を有する組成物
WO2008077772A2 (en) * 2006-12-22 2008-07-03 Sigma-Tau Industrie Farmaceutiche Riunite Spa Combination of a retinoid and a platinum anticancer agent
WO2010000784A1 (en) * 2008-07-03 2010-01-07 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Treatment of restenosis
TW201031402A (en) * 2008-12-24 2010-09-01 Sigma Tau Ind Farmaceuti New retinoid derivatives endowed with cytotoxic and/or antiangiogenic properties
US9056085B2 (en) 2009-02-03 2015-06-16 Children's Medical Center Corporation Methods for enhancing hematopoietic stem/progenitor cell engraftment
WO2010091052A2 (en) 2009-02-03 2010-08-12 Children's Medical Center Corporation Methods for enhancing hematopoietic stem/progenitor cell engraftment
WO2010106135A1 (en) 2009-03-20 2010-09-23 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Combined use for the treatment of ovarian carcinoma
US9096544B2 (en) 2009-12-23 2015-08-04 Wayne State University Therapeutic compounds
PT2758371T (pt) * 2011-09-19 2016-07-13 Sigma Tau Ind Farmaceuti Novos tio derivados que contêm lactamas como potentes inibidores de hdac e suas utilizações enquanto medicamentos
JP5757602B2 (ja) * 2012-05-11 2015-07-29 国立大学法人金沢大学 不斉選択性の切り替えが可能なクロマトグラフィー用充填剤
CN104496839B (zh) * 2014-12-03 2016-04-20 广东东阳光药业有限公司 取代环丁烷类神经氨酸酶抑制剂及其使用方法和用途
US11707442B2 (en) 2015-09-25 2023-07-25 The General Hospital Corporation Antibacterial and antifungal compounds
CA3011538A1 (en) 2016-01-18 2017-07-27 Arisan Therapeutics Adamantane derivatives for the treatment of filovirus infection
EP3301085A1 (en) 2016-09-29 2018-04-04 Biogem S.Ca.R.L. Retinoid derivatives with antitumor activity
CN110799182B (zh) * 2017-04-27 2024-02-20 范德比尔特大学 用γ-酮醛清除剂治疗动脉粥样硬化的方法
WO2018213609A1 (en) 2017-05-17 2018-11-22 Ausubel Frederick M Antibiotic compounds
US11548893B2 (en) 2017-07-15 2023-01-10 Arisan Therapeutics Inc. Enantiomerically pure adamantane carboxamides for the treatment of filovirus infection
IT201900003343A1 (it) * 2019-03-07 2020-09-07 Special Product’S Line S P A Derivati fenolici per uso come antimicrobici, antibatterici, battericidi
CN111956806B (zh) * 2020-09-03 2023-04-07 四川大学 一种药物载体、胶束、药剂及其制备方法和应用
IT202000029882A1 (it) * 2020-12-04 2022-06-04 Special Product’S Line S P A Derivati fenolici per uso come antimicrobici, antibatterici, battericidi
IT202000029906A1 (it) * 2020-12-04 2022-06-04 Special Product’S Line S P A Derivati fenolici per uso come antimicrobici, antibatterici, battericidi.
WO2022229017A1 (en) 2021-04-27 2022-11-03 Biogem S.C.A R.L. Adamantyl retinoid derivative with anticancer activity

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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FR2676052B1 (fr) * 1991-05-02 1994-04-29 Cird Galderma Nouveaux composes polycycliques aromatiques et leur utilisation en medecine humaine ou veterinaire et en cosmetique.
CZ3499A3 (cs) * 1996-07-08 1999-11-17 Galderma Research & Development, S. N. C. Adamantylová sloučenina, její použití a farmaceutický prostředek ji obsahující
ITRM20010464A1 (it) * 2001-07-31 2003-01-31 Sigma Tau Ind Farmaceuti Derivati retinoidi ad attivita' antiangiogenica, antitumorale e pro-apoptotica.
EP1456165A1 (en) * 2001-11-30 2004-09-15 The Burnham Institute Induction of apoptosis in cancer cells

Also Published As

Publication number Publication date
BR0211521A (pt) 2004-09-14
HK1068868A1 (en) 2005-05-06
CA2454532A1 (en) 2003-02-13
CN1279014C (zh) 2006-10-11
PT1412317E (pt) 2011-03-21
AU2002326144B2 (en) 2008-04-10
US20080021088A1 (en) 2008-01-24
ITRM20010464A1 (it) 2003-01-31
ITRM20010464A0 (it) 2001-07-31
KR20040028968A (ko) 2004-04-03
DE60238683D1 (de) 2011-02-03
EP1412317A1 (en) 2004-04-28
MXPA04000877A (es) 2004-06-03
PL207530B1 (pl) 2010-12-31
KR100888466B1 (ko) 2009-03-12
US20040235757A1 (en) 2004-11-25
US8101793B2 (en) 2012-01-24
DK1412317T3 (da) 2011-03-28
HUP0401604A2 (hu) 2004-12-28
CY1114535T1 (el) 2016-10-05
CN1537094A (zh) 2004-10-13
ATE492526T1 (de) 2011-01-15
CA2454532C (en) 2011-01-25
HUP0401604A3 (en) 2006-01-30
WO2003011808A1 (en) 2003-02-13
PL368412A1 (en) 2005-03-21
HU229308B1 (en) 2013-10-28
EP1412317B1 (en) 2010-12-22
JP2004536879A (ja) 2004-12-09
JP4463550B2 (ja) 2010-05-19
US7449495B2 (en) 2008-11-11

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