HU230354B1 - Javított szilárd fázisú peptidszintézis és a szintézisben alkalmazható anyagok - Google Patents
Javított szilárd fázisú peptidszintézis és a szintézisben alkalmazható anyagok Download PDFInfo
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- HU230354B1 HU230354B1 HU0102900A HUP0102900A HU230354B1 HU 230354 B1 HU230354 B1 HU 230354B1 HU 0102900 A HU0102900 A HU 0102900A HU P0102900 A HUP0102900 A HU P0102900A HU 230354 B1 HU230354 B1 HU 230354B1
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- peptide
- acid
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- synthesis
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- 238000000465 moulding Methods 0.000 description 1
- UVPHEASGGSCXIY-UHFFFAOYSA-N nitric acid hydrate Chemical group [N+](=O)(O)[O-].[N+](=O)(O)[O-].O.[N+](=O)(O)[O-].[N+](=O)(O)[O-] UVPHEASGGSCXIY-UHFFFAOYSA-N 0.000 description 1
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- WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical class CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
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- 108010091748 peptide A Proteins 0.000 description 1
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Prostheses (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK97196 | 1996-09-09 | ||
| DK0971/96 | 1996-09-09 | ||
| PCT/DK1997/000375 WO1998011125A1 (en) | 1996-09-09 | 1997-09-09 | Improved solid-phase peptide synthesis and agent for use in such synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP0102900A2 HUP0102900A2 (hu) | 2002-01-28 |
| HUP0102900A3 HUP0102900A3 (en) | 2002-02-28 |
| HU230354B1 true HU230354B1 (hu) | 2016-02-29 |
Family
ID=8099561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0102900A HU230354B1 (hu) | 1996-09-09 | 1997-09-09 | Javított szilárd fázisú peptidszintézis és a szintézisben alkalmazható anyagok |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7348404B2 (enExample) |
| EP (1) | EP0929567B1 (enExample) |
| JP (1) | JP4405594B2 (enExample) |
| AT (1) | ATE290014T1 (enExample) |
| AU (1) | AU723268B2 (enExample) |
| CA (1) | CA2265900C (enExample) |
| CZ (1) | CZ295838B6 (enExample) |
| DE (1) | DE69732640T2 (enExample) |
| DK (1) | DK0929567T3 (enExample) |
| ES (1) | ES2239364T3 (enExample) |
| HU (1) | HU230354B1 (enExample) |
| IL (1) | IL128829A (enExample) |
| PT (1) | PT929567E (enExample) |
| WO (1) | WO1998011125A1 (enExample) |
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|---|---|---|---|---|
| IL138214A0 (en) * | 1998-03-09 | 2001-10-31 | Zealand Pharmaceuticals As | Pharmacolgically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
| US6528486B1 (en) | 1999-07-12 | 2003-03-04 | Zealand Pharma A/S | Peptide agonists of GLP-1 activity |
| US7550425B2 (en) | 2000-06-16 | 2009-06-23 | Zealand Pharma A/S | Diuretic peptide conjugates |
| WO2006045503A1 (en) | 2004-10-19 | 2006-05-04 | Lonza Ag | Method for solid phase peptide synthesis |
| AU2006242998B2 (en) | 2005-05-04 | 2012-03-22 | Zealand Pharma A/S | Glucagon-like-peptide-2 (GLP-2) analogues |
| GB0514071D0 (en) | 2005-07-07 | 2005-08-17 | Zealand Pharma As | N- or C- terminally modified small peptides |
| JPWO2007060860A1 (ja) * | 2005-11-22 | 2009-05-07 | 学校法人日本大学 | ピロールイミダゾールポリアミドの固相自動合成 |
| CN101336229B (zh) | 2005-12-23 | 2012-06-13 | 西兰岛药物有限公司 | 改性的拟赖氨酸化合物 |
| EP1991560B1 (en) * | 2006-02-20 | 2018-04-04 | Ewha University-Industry Collaboration Foundation | Peptide having cell membrane penetrating activity |
| CA2647867C (en) * | 2006-03-29 | 2015-11-03 | Otsuka Chemical Co., Ltd. | Method for production of peptide thioester compound |
| EP2051995B1 (en) | 2006-11-08 | 2017-02-08 | Zealand Pharma A/S | Selective glucagon-like-peptide-2 (glp-2) analogues |
| EP2158214B1 (en) | 2007-06-15 | 2011-08-17 | Zealand Pharma A/S | Glucagon analogues |
| JP5635530B2 (ja) | 2008-12-15 | 2014-12-03 | ジーランド ファーマ アクティーゼルスカブ | グルカゴン類似体 |
| DK2370461T3 (da) | 2008-12-15 | 2013-12-16 | Zealand Pharma As | Glucagonanaloger |
| BRPI0823377A2 (pt) | 2008-12-15 | 2016-09-27 | Zealand Pharma As | análogos de glucagon |
| MA32970B1 (fr) | 2008-12-15 | 2012-01-02 | Zealand Pharma As | Analogues du glucagon |
| JP6054742B2 (ja) | 2009-07-13 | 2016-12-27 | ジーランド ファーマ アクティーゼルスカブ | アシル化グルカゴン類似体 |
| JP5969461B2 (ja) | 2010-04-27 | 2016-08-17 | ジーランド ファーマ アクティーゼルスカブ | Glp−1受容体作動薬とガストリンとのペプチド複合体及びその使用 |
| UY33462A (es) | 2010-06-23 | 2012-01-31 | Zealand Pharma As | Analogos de glucagon |
| US9169310B2 (en) | 2010-06-24 | 2015-10-27 | Zealand Pharma A/S | Glucagon analogues |
| PH12013501495A1 (en) | 2011-01-20 | 2013-09-16 | Zealand Pharma As | Combination of acylated glucagon analogues with insulin analogues |
| CN104144704B (zh) | 2011-11-03 | 2018-03-23 | 西兰制药公司 | Glp‑1受体激动剂肽胃泌素缀合物 |
| SG11201403377QA (en) | 2011-12-23 | 2014-07-30 | Zealand Pharma As | Glucagon analogues |
| WO2013098408A1 (en) | 2011-12-30 | 2013-07-04 | Zealand Pharma A/S | Glucagon and cck receptor agonist peptide conjugates |
| TW201336864A (zh) | 2012-02-03 | 2013-09-16 | Zealand Pharma As | 胃飢餓素(ghrelin)類似物 |
| EP2844670B1 (en) | 2012-05-03 | 2017-12-06 | Zealand Pharma A/S | Glucagon-like-peptide-2 (glp-2) analogues |
| JP6228187B2 (ja) | 2012-05-03 | 2017-11-08 | ジーランド ファーマ アクティーゼルスカブ | Gip−glp−1デュアルアゴニスト化合物及び方法 |
| MX356957B (es) | 2012-07-23 | 2018-06-20 | Zealand Pharma As | Analogos del glucagon. |
| TWI608013B (zh) | 2012-09-17 | 2017-12-11 | 西蘭製藥公司 | 升糖素類似物 |
| CN105051067B (zh) | 2013-03-12 | 2020-04-17 | 分子模板公司 | 用于引起细胞内化的cd20结合免疫毒素及其使用方法 |
| US9169287B2 (en) | 2013-03-15 | 2015-10-27 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
| US9695214B2 (en) | 2013-03-15 | 2017-07-04 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
| DK2976325T3 (en) | 2013-03-21 | 2017-06-06 | Sanofi Aventis Deutschland | SYNTHESIS OF PEPTIDE PRODUCTS CONTAINING CYCLIC IMID |
| AU2014234400B2 (en) | 2013-03-21 | 2017-11-16 | Sanofi-Aventis Deutschland Gmbh | Synthesis of hydantoin containing peptide products |
| CA2926314C (en) | 2013-10-17 | 2023-08-29 | Zealand Pharma A/S | Acylated glucagon analogues |
| US9988429B2 (en) | 2013-10-17 | 2018-06-05 | Zealand Pharma A/S | Glucagon analogues |
| CN105829339B (zh) | 2013-11-06 | 2021-03-12 | 西兰制药公司 | 胰高血糖素-glp-1-gip三重激动剂化合物 |
| AU2014345569B2 (en) | 2013-11-06 | 2020-08-13 | Zealand Pharma A/S | GIP-GLP-1 dual agonist compounds and methods |
| US10435474B2 (en) | 2013-12-24 | 2019-10-08 | Ossianix, Inc. | Baff selective binding compounds and related methods |
| KR102500408B1 (ko) | 2014-01-27 | 2023-02-16 | 몰레큘러 템플레이츠, 인코퍼레이션. | 포유류에 적용하기 위한 탈면역된 시가 독소 a 서브유닛 작동체 폴리펩티드 |
| PL3604333T3 (pl) | 2014-03-11 | 2021-11-08 | Molecular Templates, Inc. | Białka zawierające regiony efektorowe podjednostki a toksyny shiga proksymalnie do końca aminowego oraz celujące w komórki regiony wiążące typu immunoglobuliny zdolne do swoistego wiązania cd38 |
| US20170002046A1 (en) | 2014-03-11 | 2017-01-05 | Molecular Templates, Inc. | Proteins comprising binding regions, shiga toxin a subunit effector regions, and carboxy-terminal, endoplasmic reticulum localization signal motifs |
| CN113831416A (zh) | 2014-06-11 | 2021-12-24 | 分子模板公司 | 耐受蛋白酶切割的志贺毒素a亚基效应子多肽和包含其的细胞靶向分子 |
| WO2015200883A2 (en) | 2014-06-26 | 2015-12-30 | Ossianix, Inc. | Semi-synthetic nurse shark vnar libraries for making and using selective binding compounds |
| EP3212218B1 (en) | 2014-10-29 | 2021-06-30 | Zealand Pharma A/S | Gip agonist compounds and methods |
| WO2016077840A2 (en) | 2014-11-14 | 2016-05-19 | Ossianix, Inc. | TfR SELECTIVE BINDING COMPOUNDS AND RELATED METHODS |
| ES2856457T3 (es) | 2015-02-05 | 2021-09-27 | Molecular Templates Inc | Moléculas de unión a CD20 multivalentes que comprenden regiones efectoras de una subunidad de toxina shiga y composiciones enriquecidas de estas |
| JP6769984B2 (ja) | 2015-03-18 | 2020-10-14 | ジーランド ファーマ アクティーゼルスカブ | アミリン類似体 |
| GB201506380D0 (en) | 2015-04-15 | 2015-05-27 | Serodus Asa | Materials and methods for treatment of pulmonary hypertension |
| CA2980978A1 (en) | 2015-04-16 | 2016-10-20 | Zealand Pharma A/S | Acylated glucagon analogue |
| CN107849096B (zh) | 2015-05-30 | 2022-05-24 | 分子模板公司 | 去免疫化的志贺毒素a亚基支架和包含它们的细胞靶向分子 |
| AU2016297920A1 (en) | 2015-07-26 | 2018-01-18 | Molecular Templates, Inc. | Cell-targeting molecules comprising shiga toxin A subunit effectors and CD8+ T-cell epitopes |
| CN108290923A (zh) | 2015-09-17 | 2018-07-17 | 麻省理工学院 | 用于固相肽合成的方法和系统 |
| US11097010B2 (en) | 2016-08-06 | 2021-08-24 | Ossianix, Inc. | In vivo methods for selecting peptides that cross the blood brain barrier, related compositions and methods of use |
| US10071140B2 (en) | 2016-09-09 | 2018-09-11 | Zealand Pharma A/S | Amylin analogues |
| WO2018103868A1 (en) | 2016-12-09 | 2018-06-14 | Zealand Pharma A/S | Acylated glp-1/glp-2 dual agonists |
| BR112019011859A2 (pt) | 2016-12-09 | 2019-10-29 | Zealand Pharma As | agonista duplo de glp-1/glp-2, composição, método para aumentar massa intestinal, método de profilaxia ou tratamento de má-absorção intestinal e uso de um agonista duplo |
| WO2018104559A1 (en) | 2016-12-09 | 2018-06-14 | Zealand Pharma A/S | Glp-1/glp-2 dual agonists |
| WO2018104558A1 (en) | 2016-12-09 | 2018-06-14 | Zealand Pharma A/S | Acylated glp-1/glp-2 dual agonists |
| RU2753193C2 (ru) | 2016-12-09 | 2021-08-12 | Зилэнд Фарма А/С | Ацилированные двойные агонисты glp-1/glp-2 |
| MX2019008840A (es) | 2017-01-25 | 2019-09-09 | Molecular Templates Inc | Moleculas con direccion hacia las celulas que comprenden efectores de la sub-unidad a de la toxina shiga desinmunizados y epitopos de las celulas t cd8+. |
| ES2894629T3 (es) | 2017-06-16 | 2022-02-15 | Zealand Pharma As | Pautas posológicas para la administración de análogos del péptido 2 similar al glucagón (GLP-2) |
| CA3080351A1 (en) | 2017-11-02 | 2019-05-09 | Ossianix, Inc. | Improved tfr-selective binding peptides capable of crossing the blood brain barrier |
| JP7690287B2 (ja) | 2018-02-27 | 2025-06-10 | セトペー エスペーベー 3 コマンディト セルスカブ | コンプスタチン類似体及びその医療用途 |
| AU2019257343A1 (en) | 2018-04-17 | 2020-09-10 | Molecular Templates, Inc. | HER2-targeting molecules comprising de-immunized, Shiga toxin A Subunit scaffolds |
| US12258414B2 (en) | 2018-06-22 | 2025-03-25 | Ossianix, Inc. | Anti-CD98hc VNARs for crossing the blood brain barrier and type IV VNAR libraries |
| CA3100035A1 (en) | 2018-08-27 | 2020-03-05 | Regeneron Pharmaceuticals, Inc. | Use of raman spectroscopy in downstream purification |
| US12351642B2 (en) | 2018-09-14 | 2025-07-08 | Ossianix, Inc. | TFR-specific binding moieties and transcytosis method to select VNARs that cross cellular barriers |
| WO2020081493A1 (en) | 2018-10-16 | 2020-04-23 | Molecular Templates, Inc. | Pd-l1 binding proteins |
| EP3914358A1 (en) | 2019-01-23 | 2021-12-01 | Millennium Pharmaceuticals, Inc. | Anti-cd38 antibodies |
| CA3127660A1 (en) | 2019-01-23 | 2020-07-30 | Millennium Pharmaceuticals, Inc. | Cd38-binding proteins comprising de-immunized shiga toxin a subunit effectors |
| EP3982920A1 (en) | 2019-06-14 | 2022-04-20 | Zealand Pharma A/S | Pharmaceutical parenteral composition of dual glp1/2 agonist |
| CN114630836A (zh) | 2019-08-27 | 2022-06-14 | 西兰制药第三特殊目的公司 | 补体抑制素类似物及其医学用途 |
| US11918649B2 (en) | 2019-09-18 | 2024-03-05 | Molecular Templates, Inc. | PD-L1-binding molecules comprising Shiga toxin a subunit scaffolds |
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| WO2022129311A1 (en) | 2020-12-16 | 2022-06-23 | Zealand Pharma A/S | Pharmaceutical composition of glp-1/glp-2 dual agonists |
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| US20240316155A1 (en) | 2021-02-18 | 2024-09-26 | Zealand Pharma A/S | Composition for treating short bowel syndrome |
| WO2022197945A1 (en) | 2021-03-17 | 2022-09-22 | Molecular Templates, Inc. | Pd-l1 binding proteins comprising shiga toxin a subunit scaffolds and cd8+ t cell antigens |
| AU2022245193A1 (en) | 2021-03-23 | 2023-09-07 | Zealand Pharma A/S | Kv1.3 blockers |
| WO2022260877A1 (en) | 2021-06-07 | 2022-12-15 | Ossianix, Inc. | Shark vnars for treating covid-19 |
| US20240279298A1 (en) | 2021-06-18 | 2024-08-22 | Beijing Tuo Jie Biopharmaceutical Co. Ltd. | Glucagon analog and medical use thereof |
| US20250122298A1 (en) | 2021-08-17 | 2025-04-17 | Ossianix, Inc. | Deimmunized vnar domains and scaffolds |
| JP2024533153A (ja) | 2021-09-03 | 2024-09-12 | ジーランド ファーマ エー/エス | 投薬レジーム |
| EP4440592A1 (en) | 2021-12-01 | 2024-10-09 | Zealand Pharma A/S | Peptide inhibitors of interleukin-23 receptor |
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| WO2025259842A2 (en) | 2024-06-12 | 2025-12-18 | Invaio Sciences, Inc. | Novel alpha-factor based peptides with antifungal activity |
Family Cites Families (6)
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|---|---|---|---|---|
| JPS5116666A (enExample) * | 1974-07-30 | 1976-02-10 | Shionogi Seiyaku Kk | |
| US5021550A (en) * | 1986-10-07 | 1991-06-04 | Thomas Jefferson University | Method for preventing deletion sequences in solid phase synthesis |
| JP2807287B2 (ja) * | 1989-10-13 | 1998-10-08 | 株式会社医学生物学研究所 | ペプチドおよびその用途 |
| EP0719334A1 (en) * | 1993-09-14 | 1996-07-03 | Genentech, Inc. | Pharmaceutical compositions containing ecotin and homologs thereof |
| US7176282B1 (en) * | 1996-09-09 | 2007-02-13 | Zealand Pharma A/S | Solid-phase peptide synthesis and agent for use in such synthesis |
| IL138214A0 (en) * | 1998-03-09 | 2001-10-31 | Zealand Pharmaceuticals As | Pharmacolgically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
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1997
- 1997-09-09 IL IL12882997A patent/IL128829A/xx not_active IP Right Cessation
- 1997-09-09 DK DK97939974T patent/DK0929567T3/da active
- 1997-09-09 EP EP97939974A patent/EP0929567B1/en not_active Expired - Lifetime
- 1997-09-09 DE DE69732640T patent/DE69732640T2/de not_active Expired - Lifetime
- 1997-09-09 PT PT97939974T patent/PT929567E/pt unknown
- 1997-09-09 AT AT97939974T patent/ATE290014T1/de active
- 1997-09-09 JP JP51316698A patent/JP4405594B2/ja not_active Expired - Fee Related
- 1997-09-09 CA CA002265900A patent/CA2265900C/en not_active Expired - Lifetime
- 1997-09-09 HU HU0102900A patent/HU230354B1/hu not_active IP Right Cessation
- 1997-09-09 CZ CZ1999803A patent/CZ295838B6/cs not_active IP Right Cessation
- 1997-09-09 ES ES97939974T patent/ES2239364T3/es not_active Expired - Lifetime
- 1997-09-09 AU AU41993/97A patent/AU723268B2/en not_active Ceased
- 1997-09-09 WO PCT/DK1997/000375 patent/WO1998011125A1/en not_active Ceased
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2006
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Also Published As
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| EP0929567A1 (en) | 1999-07-21 |
| CA2265900A1 (en) | 1998-03-19 |
| IL128829A (en) | 2005-08-31 |
| CZ295838B6 (cs) | 2005-11-16 |
| HUP0102900A3 (en) | 2002-02-28 |
| CZ80399A3 (cs) | 1999-08-11 |
| ES2239364T3 (es) | 2005-09-16 |
| JP4405594B2 (ja) | 2010-01-27 |
| WO1998011125A1 (en) | 1998-03-19 |
| JP2001500134A (ja) | 2001-01-09 |
| AU723268B2 (en) | 2000-08-24 |
| US20070004905A1 (en) | 2007-01-04 |
| DK0929567T3 (da) | 2005-06-27 |
| US7348404B2 (en) | 2008-03-25 |
| HUP0102900A2 (hu) | 2002-01-28 |
| PT929567E (pt) | 2005-07-29 |
| CA2265900C (en) | 2007-07-31 |
| AU4199397A (en) | 1998-04-02 |
| IL128829A0 (en) | 2000-01-31 |
| DE69732640T2 (de) | 2006-01-12 |
| DE69732640D1 (de) | 2005-04-07 |
| EP0929567B1 (en) | 2005-03-02 |
| ATE290014T1 (de) | 2005-03-15 |
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