NO320028B1 - Substituerte 1-Okso- og 1,3-dioksoisoindoliner og deres anvendelse i farmasoytiske preparater for a redusere inflammatoriske cykotin nivaer - Google Patents
Substituerte 1-Okso- og 1,3-dioksoisoindoliner og deres anvendelse i farmasoytiske preparater for a redusere inflammatoriske cykotin nivaer Download PDFInfo
- Publication number
- NO320028B1 NO320028B1 NO20013982A NO20013982A NO320028B1 NO 320028 B1 NO320028 B1 NO 320028B1 NO 20013982 A NO20013982 A NO 20013982A NO 20013982 A NO20013982 A NO 20013982A NO 320028 B1 NO320028 B1 NO 320028B1
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- Norway
- Prior art keywords
- acid
- dioxoisoindolin
- oxoisoindolin
- carbamoylbutanoic
- nitro
- Prior art date
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Classifications
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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
- A61P35/00—Antineoplastic agents
-
- 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
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US12494299P | 1999-03-18 | 1999-03-18 | |
PCT/US2000/007029 WO2000055134A1 (fr) | 1999-03-18 | 2000-03-17 | 1-oxo- et 1,3-dioxoisoindolines substituees et leur utilisation dans des compositions pharmaceutiques afin de reduire les taux de cytokines inflammatoires |
Publications (3)
Publication Number | Publication Date |
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NO20013982D0 NO20013982D0 (no) | 2001-08-16 |
NO20013982L NO20013982L (no) | 2001-11-16 |
NO320028B1 true NO320028B1 (no) | 2005-10-10 |
Family
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NO20013982A NO320028B1 (no) | 1999-03-18 | 2001-08-16 | Substituerte 1-Okso- og 1,3-dioksoisoindoliner og deres anvendelse i farmasoytiske preparater for a redusere inflammatoriske cykotin nivaer |
NO20054581A NO20054581L (no) | 1999-03-18 | 2005-10-05 | Substituerte 1-oksoisoindoliner og deres anvendelse i farmasoytiske preparater for a redusere inflammatoriske cykotinnivaer |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
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NO20054581A NO20054581L (no) | 1999-03-18 | 2005-10-05 | Substituerte 1-oksoisoindoliner og deres anvendelse i farmasoytiske preparater for a redusere inflammatoriske cykotinnivaer |
Country Status (22)
Country | Link |
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US (1) | US6380239B1 (fr) |
EP (1) | EP1163219B1 (fr) |
JP (1) | JP4728487B2 (fr) |
KR (1) | KR100672892B1 (fr) |
CN (1) | CN1342146A (fr) |
AT (1) | ATE306469T1 (fr) |
AU (1) | AU771015B2 (fr) |
BR (1) | BR0010042A (fr) |
CA (1) | CA2361806C (fr) |
CZ (1) | CZ20013338A3 (fr) |
DE (1) | DE60023123T2 (fr) |
DK (1) | DK1163219T3 (fr) |
ES (1) | ES2250121T3 (fr) |
FI (1) | FI119881B (fr) |
HK (1) | HK1042494A1 (fr) |
HU (1) | HUP0200499A3 (fr) |
NO (2) | NO320028B1 (fr) |
NZ (1) | NZ513953A (fr) |
RU (1) | RU2001121987A (fr) |
TR (1) | TR200102688T2 (fr) |
TW (1) | TWI229074B (fr) |
WO (1) | WO2000055134A1 (fr) |
Families Citing this family (109)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6228879B1 (en) * | 1997-10-16 | 2001-05-08 | The Children's Medical Center | Methods and compositions for inhibition of angiogenesis |
US5629327A (en) | 1993-03-01 | 1997-05-13 | Childrens Hospital Medical Center Corp. | Methods and compositions for inhibition of angiogenesis |
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DK1353672T3 (da) * | 2000-11-30 | 2008-01-21 | Childrens Medical Center | Syntese af 4-amino-thalidomidenantiomerer |
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US20100129363A1 (en) * | 2002-05-17 | 2010-05-27 | Zeldis Jerome B | Methods and compositions using pde4 inhibitors for the treatment and management of cancers |
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US20040087558A1 (en) * | 2002-10-24 | 2004-05-06 | Zeldis Jerome B. | Methods of using and compositions comprising selective cytokine inhibitory drugs for treatment, modification and management of pain |
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CH696542A5 (de) * | 2003-07-09 | 2007-07-31 | Siegfried Ltd | Verfahren zur Herstellung von substituierten 2,6-Dioxopiperidin-3-yl-Verbindungen. |
GB0319069D0 (en) * | 2003-08-14 | 2003-09-17 | Glaxo Group Ltd | Therapeutically useful compounds |
UA83504C2 (en) * | 2003-09-04 | 2008-07-25 | Селджин Корпорейшн | Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione |
US20080027113A1 (en) * | 2003-09-23 | 2008-01-31 | Zeldis Jerome B | Methods of Using and Compositions Comprising Immunomodulatory Compounds for Treatment and Management of Macular Degeneration |
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US20060270707A1 (en) * | 2005-05-24 | 2006-11-30 | Zeldis Jerome B | Methods and compositions using 4-[(cyclopropanecarbonylamino)methyl]-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione for the treatment or prevention of cutaneous lupus |
AU2011221383B2 (en) * | 2005-06-30 | 2013-08-01 | Celgene Corporation | Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds |
JP2008544818A (ja) * | 2005-06-30 | 2008-12-11 | アントフロゲネシス コーポレーション | 胎盤由来コラーゲンバイオ線維を用いた鼓膜の修復 |
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WO2007009061A2 (fr) * | 2005-07-13 | 2007-01-18 | Anthrogenesis Corporation | Obturateur oculaire forme a partir dun tissu biologique a base de collagene derive du placenta |
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CL2007002218A1 (es) * | 2006-08-03 | 2008-03-14 | Celgene Corp Soc Organizada Ba | Uso de 3-(4-amino-1-oxo-1,3-dihidro-isoindol-2-il)-piperidina 2,6-diona para la preparacion de un medicamento util para el tratamiento de linfoma de celula de capa. |
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WO2008060377A2 (fr) | 2006-10-04 | 2008-05-22 | Anthrogenesis Corporation | Compositions de tissu du cordon ombilical ou placentaire |
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CA2677679A1 (fr) * | 2007-02-12 | 2008-08-21 | Anthrogenesis Corporation | Hepatocytes et chondrocytes provenant de cellules souches placentaires adherentes ; et populations de cellules enrichies avec des cellules souches placentaires cd34+, cd45- |
MX349225B (es) * | 2007-02-12 | 2017-07-19 | Anthrogenesis Corp | Uso de celulas madre placentarias para preparar medicamentos utiles en el tratamiento de padecimientos inflamatorios. |
WO2009020590A1 (fr) * | 2007-08-07 | 2009-02-12 | Celgene Corporation | Procédés de traitement de lymphomes chez certaines populations de patients et criblage de patients pour ladite thérapie |
US20090082368A1 (en) * | 2007-09-24 | 2009-03-26 | Painceptor Pharma Corporation | Methods of modulating neurotrophin-mediated activity |
KR20210022148A (ko) | 2007-09-28 | 2021-03-02 | 안트로제네시스 코포레이션 | 인간 태반 관류액 및 인간 태반-유래 중간체 천연 킬러 세포를 사용한 종양 억제 방법 |
JP2011505336A (ja) * | 2007-11-01 | 2011-02-24 | セルジーン コーポレイション | 骨髄異形成症候群治療のためのシチジンアナログ |
WO2009085234A2 (fr) * | 2007-12-20 | 2009-07-09 | Signal Pharmaceuticals, Inc. | Utilisation d'un micro-arn à titre de marqueur biologique d'une activité médicamenteuse immunomodulatoire |
WO2009105256A2 (fr) * | 2008-02-20 | 2009-08-27 | Celgene Corporation | Procédé de traitement du cancer par administration d'un composé immunomodulateur en association avec un anticorps cd40 ou un ligand cd40 |
RU2742171C2 (ru) | 2009-03-25 | 2021-02-02 | Антродженезис Корпорейшн | Супрессия опухолей с использованием полученных из плаценты человека промежуточных естественных киллерных клеток и иммуномодулирующих соединений |
JP5645816B2 (ja) | 2009-05-25 | 2014-12-24 | 国立大学法人東京工業大学 | 中枢神経細胞の増殖及び分化に係る中核因子を含む医薬組成物 |
CN101580501B (zh) | 2009-06-01 | 2011-03-09 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚酮-2-基)-2,6-哌啶二酮的合成方法及其中间体 |
CA2786266A1 (fr) | 2010-01-05 | 2011-07-14 | Celgene Corporation | Association d'un compose immunomodulateur et d'une artemisinine ou de son derive pour le traitement du cancer |
MX341050B (es) | 2010-04-07 | 2016-08-05 | Celgene Corp * | Metodos para tratar infeccion viral respiratoria. |
JP2014517915A (ja) | 2011-04-18 | 2014-07-24 | セルジーン コーポレイション | 多発性骨髄腫治療のためのバイオマーカー |
MX353482B (es) | 2011-04-29 | 2018-01-16 | Celgene Corp | Metodos para el tratamiento del cancer y enfermedades inflamatorias utilizando cereblon como predictor. |
EP3967323A3 (fr) | 2012-06-06 | 2022-05-04 | Bionor Immuno AS | Vaccin contre le vih |
CA3136093A1 (fr) | 2012-06-29 | 2014-01-03 | Celgene Corporation | Procedes pour determiner l'efficacite d'un medicament en utilisant des proteines associees au cereblon |
US9587281B2 (en) | 2012-08-14 | 2017-03-07 | Celgene Corporation | Cereblon isoforms and their use as biomarkers for therapeutic treatment |
CN105142651A (zh) | 2013-02-05 | 2015-12-09 | 人类起源公司 | 来自胎盘的自然杀伤细胞 |
US20140314752A1 (en) | 2013-04-17 | 2014-10-23 | Signal Pharmaceuticals, Llc | Methods for treating cancer using tor kinase inhibitor combination therapy |
CN103232380A (zh) * | 2013-05-08 | 2013-08-07 | 中国药科大学 | 一种泊马度胺关键中间体的制备方法 |
WO2015007337A1 (fr) | 2013-07-19 | 2015-01-22 | Bionor Immuno As | Procédé de vaccination contre le vih |
JP6640126B2 (ja) | 2014-06-27 | 2020-02-05 | セルジーン コーポレイション | セレブロン及び他のe3ユビキチンリガーゼの立体構造の変化を誘導するための組成物及び方法 |
SI3182996T1 (sl) | 2014-08-22 | 2023-04-28 | Celgene Corporation | Postopki zdravljenja multiplega mieloma z imunomodulatornimi spojinami v kombinaciji s protitelesi |
CN105440013B (zh) * | 2014-08-29 | 2018-10-09 | 杭州和泽医药科技有限公司 | 一种泊马度胺的制备方法 |
HUE065109T2 (hu) | 2015-06-26 | 2024-05-28 | Celgene Corp | Eljárások Kaposi-szarkóma vagy KSHV-indukált limfóma kezelésére immunomodulátor vegyületek alkalmazásával, valamint biomarkerek alkalmazása |
WO2017117118A1 (fr) | 2015-12-28 | 2017-07-06 | Celgene Corporation | Compositions et méthodes pour induire des modifications conformationnelles dans céréblon et d'autres ubiquitine ligases e3 |
CN107365295B (zh) * | 2016-05-11 | 2020-07-07 | 常州制药厂有限公司 | 一种泊马度胺合成工艺的改进方法 |
CN106432045B (zh) * | 2016-06-29 | 2018-12-18 | 深圳海王医药科技研究院有限公司 | 一种泊马度胺杂质的合成方法 |
CN110248678A (zh) | 2016-12-03 | 2019-09-17 | 朱诺治疗学股份有限公司 | 调节car-t细胞的方法 |
PT3618842T (pt) | 2017-05-01 | 2024-01-12 | Juno Therapeutics Inc | Combinação de uma terapia celular e de um composto imunomodulador |
EP3630132A1 (fr) | 2017-06-02 | 2020-04-08 | Juno Therapeutics, Inc. | Articles de fabrication et procédés de traitement utilisant une thérapie cellulaire adoptive |
WO2019006427A1 (fr) | 2017-06-29 | 2019-01-03 | Juno Therapeutics, Inc. | Modèle murin pour évaluer des toxicités associées à des immunothérapies |
US20200246393A1 (en) | 2017-09-28 | 2020-08-06 | Celularity, Inc. | Tumor suppression using human placenta-derived intermediate natural killer (pink) cells in combination with an antibody |
US12031975B2 (en) | 2017-11-01 | 2024-07-09 | Juno Therapeutics, Inc. | Methods of assessing or monitoring a response to a cell therapy |
WO2019089969A2 (fr) | 2017-11-01 | 2019-05-09 | Juno Therapeutics, Inc. | Anticorps et récepteurs antigéniques chimériques spécifiques de l'antigene de maturation des lymphocytes b |
EP3724225A1 (fr) | 2017-12-15 | 2020-10-21 | Juno Therapeutics, Inc. | Molécules de liaison à l'anti-cct5 et procédés d'utilisation associés |
EP3755718A1 (fr) | 2018-02-21 | 2020-12-30 | Celgene Corporation | Anticorps de liaison à bcma et leurs utilisations |
AU2019377854A1 (en) | 2018-11-08 | 2021-05-27 | Juno Therapeutics, Inc. | Methods and combinations for treatment and T cell modulation |
WO2020102770A1 (fr) | 2018-11-16 | 2020-05-22 | Juno Therapeutics, Inc. | Méthodes de posologie pour cellules t modifiées pour le traitement de cancers à cellules b |
SG11202105502RA (en) | 2018-11-30 | 2021-06-29 | Juno Therapeutics Inc | Methods for treatment using adoptive cell therapy |
JP2022518925A (ja) | 2019-01-29 | 2022-03-17 | ジュノー セラピューティクス インコーポレイテッド | 受容体チロシンキナーゼ様オーファン受容体1(ror1)に特異的な抗体およびキメラ抗原受容体 |
WO2023250400A1 (fr) | 2022-06-22 | 2023-12-28 | Juno Therapeutics, Inc. | Méthodes de traitement pour thérapie de deuxième ligne par cellules car-t ciblées par cd19 |
WO2024097905A1 (fr) | 2022-11-02 | 2024-05-10 | Celgene Corporation | Méthodes de traitement au moyen d'une thérapie par lymphocytes t et d'une thérapie d'entretien par agent immunomodulateur |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5855459A (ja) * | 1981-09-26 | 1983-04-01 | Dai Ichi Pure Chem Co Ltd | 光学活性トリプトフアン誘導体の製造法 |
EP0088488B1 (fr) * | 1982-01-22 | 1986-10-01 | Beecham Group Plc | Agents antibactériens, leur préparation et leur utilisation |
DE3631229A1 (de) * | 1986-09-13 | 1988-03-24 | Basf Ag | Monoklonale antikoerper gegen humanen tumornekrosefaktor (tnf) und deren verwendung |
GB9109645D0 (en) * | 1991-05-03 | 1991-06-26 | Celltech Ltd | Recombinant antibodies |
GB9028123D0 (en) * | 1990-12-28 | 1991-02-13 | Erba Carlo Spa | Monoclonal antibodies against human tumor necrosis factor alpha |
NL9300354A (nl) * | 1993-02-25 | 1994-09-16 | Futura Nova Bv | Universeel toepasbare celverzamelinrichting. |
US5629327A (en) | 1993-03-01 | 1997-05-13 | Childrens Hospital Medical Center Corp. | Methods and compositions for inhibition of angiogenesis |
US5798368A (en) | 1996-08-22 | 1998-08-25 | Celgene Corporation | Tetrasubstituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines and method of reducing TNFα levels |
HU228769B1 (en) | 1996-07-24 | 2013-05-28 | Celgene Corp | Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and their use for production of pharmaceutical compositions for mammals to reduce the level of tnf-alpha |
CZ304569B6 (cs) | 1996-07-24 | 2014-07-09 | Celgene Corporation | 1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindolin pro použití pro snížení nežádoucí hladiny TNFα u savce |
US5635517B1 (en) | 1996-07-24 | 1999-06-29 | Celgene Corp | Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines |
JP2002513391A (ja) | 1996-11-05 | 2002-05-08 | ザ チルドレンズ メディカル センター コーポレイション | 血管形成の抑制のための方法と組成物 |
AU7449198A (en) * | 1997-05-21 | 1998-12-11 | Japan Tobacco Inc. | Phthalimide derivatives and pharmaceutical containing said derivatives |
-
2000
- 2000-03-17 DE DE60023123T patent/DE60023123T2/de not_active Expired - Lifetime
- 2000-03-17 US US09/528,785 patent/US6380239B1/en not_active Expired - Lifetime
- 2000-03-17 DK DK00916444T patent/DK1163219T3/da active
- 2000-03-17 EP EP00916444A patent/EP1163219B1/fr not_active Expired - Lifetime
- 2000-03-17 HU HU0200499A patent/HUP0200499A3/hu unknown
- 2000-03-17 TR TR2001/02688T patent/TR200102688T2/xx unknown
- 2000-03-17 AT AT00916444T patent/ATE306469T1/de active
- 2000-03-17 JP JP2000605565A patent/JP4728487B2/ja not_active Expired - Fee Related
- 2000-03-17 CZ CZ20013338A patent/CZ20013338A3/cs unknown
- 2000-03-17 AU AU37550/00A patent/AU771015B2/en not_active Ceased
- 2000-03-17 KR KR1020017011582A patent/KR100672892B1/ko not_active IP Right Cessation
- 2000-03-17 NZ NZ513953A patent/NZ513953A/en not_active IP Right Cessation
- 2000-03-17 RU RU2001121987/04A patent/RU2001121987A/ru unknown
- 2000-03-17 BR BR0010042-0A patent/BR0010042A/pt active Search and Examination
- 2000-03-17 ES ES00916444T patent/ES2250121T3/es not_active Expired - Lifetime
- 2000-03-17 CA CA2361806A patent/CA2361806C/fr not_active Expired - Fee Related
- 2000-03-17 CN CN00804440A patent/CN1342146A/zh active Pending
- 2000-03-17 WO PCT/US2000/007029 patent/WO2000055134A1/fr active IP Right Grant
- 2000-05-29 TW TW089104963A patent/TWI229074B/zh not_active IP Right Cessation
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2001
- 2001-08-16 NO NO20013982A patent/NO320028B1/no not_active IP Right Cessation
- 2001-09-18 FI FI20011839A patent/FI119881B/fi not_active IP Right Cessation
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2002
- 2002-06-07 HK HK02104317.6A patent/HK1042494A1/zh unknown
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JP2002539197A (ja) | 2002-11-19 |
HUP0200499A2 (en) | 2002-06-29 |
AU771015B2 (en) | 2004-03-11 |
FI119881B (fi) | 2009-04-30 |
NO20013982L (no) | 2001-11-16 |
DE60023123D1 (de) | 2006-02-23 |
CZ20013338A3 (cs) | 2002-03-13 |
KR100672892B1 (ko) | 2007-01-23 |
DE60023123T2 (de) | 2006-06-22 |
NO20054581L (no) | 2001-11-16 |
CA2361806A1 (fr) | 2000-09-21 |
EP1163219B1 (fr) | 2005-10-12 |
DK1163219T3 (da) | 2006-02-27 |
RU2001121987A (ru) | 2004-02-27 |
BR0010042A (pt) | 2002-01-15 |
EP1163219A1 (fr) | 2001-12-19 |
CA2361806C (fr) | 2012-03-13 |
HUP0200499A3 (en) | 2002-12-28 |
JP4728487B2 (ja) | 2011-07-20 |
ES2250121T3 (es) | 2006-04-16 |
NO20013982D0 (no) | 2001-08-16 |
TR200102688T2 (tr) | 2002-01-21 |
FI20011839A (fi) | 2001-09-18 |
US6380239B1 (en) | 2002-04-30 |
CN1342146A (zh) | 2002-03-27 |
TWI229074B (en) | 2005-03-11 |
WO2000055134A1 (fr) | 2000-09-21 |
NZ513953A (en) | 2001-09-28 |
ATE306469T1 (de) | 2005-10-15 |
AU3755000A (en) | 2000-10-04 |
HK1042494A1 (zh) | 2002-08-16 |
KR20010109310A (ko) | 2001-12-08 |
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