CA2797666A1 - Peptide derivatives of exendin-3 - Google Patents
Peptide derivatives of exendin-3 Download PDFInfo
- Publication number
- CA2797666A1 CA2797666A1 CA2797666A CA2797666A CA2797666A1 CA 2797666 A1 CA2797666 A1 CA 2797666A1 CA 2797666 A CA2797666 A CA 2797666A CA 2797666 A CA2797666 A CA 2797666A CA 2797666 A1 CA2797666 A1 CA 2797666A1
- Authority
- CA
- Canada
- Prior art keywords
- exendin
- glp
- peptide derivative
- agent
- therapy
- 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.)
- Abandoned
Links
- LMHMJYMCGJNXRS-IOPUOMRJSA-N exendin-3 Chemical class C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@H](C)O)[C@H](C)O)C(C)C)C1=CC=CC=C1 LMHMJYMCGJNXRS-IOPUOMRJSA-N 0.000 title claims abstract description 109
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- VGIRNWJSIRVFRT-UHFFFAOYSA-N 2',7'-difluorofluorescein Chemical compound OC(=O)C1=CC=CC=C1C1=C2C=C(F)C(=O)C=C2OC2=CC(O)=C(F)C=C21 VGIRNWJSIRVFRT-UHFFFAOYSA-N 0.000 claims description 4
- ACNUVXZPCIABEX-UHFFFAOYSA-N 3',6'-diaminospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N)C=C1OC1=CC(N)=CC=C21 ACNUVXZPCIABEX-UHFFFAOYSA-N 0.000 claims description 4
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/605—Glucagons
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/57563—Vasoactive intestinal peptide [VIP]; Related peptides
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/74—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving hormones or other non-cytokine intercellular protein regulatory factors such as growth factors, including receptors to hormones and growth factors
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004043153A DE102004043153B4 (de) | 2004-09-03 | 2004-09-03 | Erfindung betreffend GLP-1 und Exendin |
| DE102004043153.1 | 2004-09-03 | ||
| CA002578252A CA2578252A1 (en) | 2004-09-03 | 2005-08-26 | Glp-1 and exendin related invention |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002578252A Division CA2578252A1 (en) | 2004-09-03 | 2005-08-26 | Glp-1 and exendin related invention |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2797666A1 true CA2797666A1 (en) | 2006-03-09 |
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ID=35970651
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2797666A Abandoned CA2797666A1 (en) | 2004-09-03 | 2005-08-26 | Peptide derivatives of exendin-3 |
| CA002578252A Abandoned CA2578252A1 (en) | 2004-09-03 | 2005-08-26 | Glp-1 and exendin related invention |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002578252A Abandoned CA2578252A1 (en) | 2004-09-03 | 2005-08-26 | Glp-1 and exendin related invention |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8268781B2 (OSRAM) |
| EP (3) | EP2301962B1 (OSRAM) |
| JP (1) | JP5047795B2 (OSRAM) |
| KR (1) | KR101237152B1 (OSRAM) |
| CN (3) | CN102358752B (OSRAM) |
| AT (1) | ATE486090T1 (OSRAM) |
| AU (1) | AU2005279537C1 (OSRAM) |
| BR (1) | BRPI0515624A (OSRAM) |
| CA (2) | CA2797666A1 (OSRAM) |
| DE (2) | DE102004043153B4 (OSRAM) |
| HR (1) | HRP20110061T1 (OSRAM) |
| MX (1) | MX2007002455A (OSRAM) |
| NO (1) | NO20071592L (OSRAM) |
| PL (2) | PL2301962T3 (OSRAM) |
| RU (3) | RU2489443C2 (OSRAM) |
| WO (1) | WO2006024275A2 (OSRAM) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0612471A2 (pt) * | 2005-05-05 | 2016-09-06 | Cadila Healthcare Ltd | novos compostos como agonistas glp-1 |
| LT3456340T (lt) | 2007-01-08 | 2022-05-10 | The Trustees Of The University Of Pennsylvania | Glp-1 receptoriaus antagonistas, skirtas įgimto hiperinsulinizmo gydymui |
| KR20110043766A (ko) * | 2008-09-20 | 2011-04-27 | 고쿠리츠 다이가쿠 호진 교토 다이가쿠 | 췌도 이미징용 분자 프로브 전구체 및 그의 사용 |
| PT3228320T (pt) | 2008-10-17 | 2020-03-26 | Sanofi Aventis Deutschland | Combinação de uma insulina e de um agonista do glp-1 |
| WO2010118034A2 (en) * | 2009-04-06 | 2010-10-14 | Board Of Regents, The University Of Texas System | Cyclic peptide analogues for non-invasive imaging of pancreatic beta-cells |
| JP5685401B2 (ja) * | 2009-08-10 | 2015-03-18 | 国立大学法人京都大学 | 膵島イメージング用分子プローブ及びその前駆体、並びに、それらの使用 |
| WO2011027584A1 (ja) * | 2009-09-04 | 2011-03-10 | 国立大学法人京都大学 | 膵島イメージング用分子プローブ及びその使用 |
| WO2011040460A1 (ja) * | 2009-09-30 | 2011-04-07 | 国立大学法人京都大学 | 膵島イメージング用分子プローブ及びその使用 |
| DK2498802T3 (en) | 2009-11-13 | 2015-04-13 | Sanofi Aventis Deutschland | Pharmaceutical composition comprising a GLP-1 agonist, insulin and a methionine |
| KR101337322B1 (ko) | 2009-11-13 | 2013-12-06 | 사노피-아벤티스 도이칠란트 게엠베하 | Ｇｌｐ-1 효능제 및 메티오닌을 포함하는 약제학적 조성물 |
| JP5700835B2 (ja) | 2009-12-10 | 2015-04-15 | 国立大学法人京都大学 | 膵島イメージング用分子プローブ及びその使用 |
| CN101875700B (zh) * | 2010-04-09 | 2012-09-26 | 无锡和邦生物科技有限公司 | 一种增加促胰岛素分泌肽融合蛋白生物活性的方法 |
| ES2606554T3 (es) | 2010-08-30 | 2017-03-24 | Sanofi-Aventis Deutschland Gmbh | Uso de AVE0010 para la fabricación de un medicamento para el tratamiento de la diabetes mellitus de tipo 2 |
| US9278146B2 (en) | 2010-10-08 | 2016-03-08 | Kyoto University | Peptide derivative and use of the same |
| WO2012121746A2 (en) * | 2011-03-09 | 2012-09-13 | The General Hospital Corporation | Imaging beta cell mass |
| US9821032B2 (en) | 2011-05-13 | 2017-11-21 | Sanofi-Aventis Deutschland Gmbh | Pharmaceutical combination for improving glycemic control as add-on therapy to basal insulin |
| EP2729493B1 (en) | 2011-07-04 | 2020-06-10 | IP2IPO Innovations Limited | Novel compounds and their effects on feeding behaviour |
| PL2750699T3 (pl) | 2011-08-29 | 2015-12-31 | Sanofi Aventis Deutschland | Kombinacja farmaceutyczna do stosowania w kontroli glikemii u pacjentów z cukrzycą typu 2 |
| AR087744A1 (es) | 2011-09-01 | 2014-04-16 | Sanofi Aventis Deutschland | Composicion farmaceutica para uso en el tratamiento de una enfermedad neurodegenerativa |
| US8901484B2 (en) * | 2012-04-27 | 2014-12-02 | Sanofi-Aventis Deutschland Gmbh | Quantification of impurities for release testing of peptide products |
| WO2013182217A1 (en) * | 2012-04-27 | 2013-12-12 | Sanofi-Aventis Deutschland Gmbh | Quantification of impurities for release testing of peptide products |
| UA116217C2 (uk) * | 2012-10-09 | 2018-02-26 | Санофі | Пептидна сполука як подвійний агоніст рецепторів glp1-1 та глюкагону |
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| EP3080150B1 (en) | 2013-12-13 | 2018-08-01 | Sanofi | Exendin-4 peptide analogues as dual glp-1/gip receptor agonists |
| WO2015086733A1 (en) | 2013-12-13 | 2015-06-18 | Sanofi | Dual glp-1/glucagon receptor agonists |
| TW201609796A (zh) | 2013-12-13 | 2016-03-16 | 賽諾菲公司 | 非醯化之艾塞那肽－４（ｅｘｅｎｄｉｎ－４）胜肽類似物 |
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| TW201625668A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 作為胜肽性雙重ｇｌｐ－１／昇糖素受體激動劑之艾塞那肽－４衍生物 |
| TW201625670A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自ｅｘｅｎｄｉｎ－４之雙重ｇｌｐ－１／升糖素受體促效劑 |
| US11311519B2 (en) | 2014-05-01 | 2022-04-26 | Eiger Biopharmaceuticals, Inc. | Treatment of hepatitis delta virus infection |
| US9932381B2 (en) | 2014-06-18 | 2018-04-03 | Sanofi | Exendin-4 derivatives as selective glucagon receptor agonists |
| DE102014112747A1 (de) | 2014-09-04 | 2016-03-10 | Eberhard Karls Universität Tübingen Medizinische Fakultät | Verwendung eines Quinoxalinderivats in einem bildgebenden Verfahren |
| AU2015359376B2 (en) | 2014-12-12 | 2021-09-09 | Sanofi-Aventis Deutschland Gmbh | Insulin glargine/lixisenatide fixed ratio formulation |
| TWI748945B (zh) | 2015-03-13 | 2021-12-11 | 德商賽諾菲阿凡提斯德意志有限公司 | 第２型糖尿病病患治療 |
| TW201705975A (zh) | 2015-03-18 | 2017-02-16 | 賽諾菲阿凡提斯德意志有限公司 | 第２型糖尿病病患之治療 |
| SMT202100668T1 (it) | 2015-05-22 | 2022-01-10 | Univ Leland Stanford Junior | Trattamento dell'ipoglicemia post-bariatrica con antagonisti del glp-1 |
| AR105319A1 (es) | 2015-06-05 | 2017-09-27 | Sanofi Sa | Profármacos que comprenden un conjugado agonista dual de glp-1 / glucagón conector ácido hialurónico |
| TW201706291A (zh) | 2015-07-10 | 2017-02-16 | 賽諾菲公司 | 作為選擇性肽雙重ｇｌｐ－１／升糖素受體促效劑之新毒蜥外泌肽（ｅｘｅｎｄｉｎ－４）衍生物 |
| AU2016372245B2 (en) | 2015-12-14 | 2020-07-16 | Antaros Medical Ab | Selective glucagon receptor agonists comprising a chelating moiety for imaging purposes |
| US10653753B2 (en) | 2016-03-04 | 2020-05-19 | Eiger Biopharmaceuticals, Inc. | Treatment of hyperinsulinemic hypoglycemia with exendin-4 derivatives |
| JP7584894B2 (ja) | 2016-11-21 | 2024-11-18 | アイガー・バイオファーマシューティカルズ・インコーポレイテッド | エキセンディン（９－３９）の緩衝製剤 |
| JP7736315B2 (ja) | 2020-03-31 | 2025-09-09 | アンタロス メディカル アクティエボラーグ | イメージング及び治療目的のキレート部分を含む選択的ｇｉｐ受容体アゴニスト |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69018226T2 (de) * | 1989-07-20 | 1995-09-21 | Sandoz-Patent-Gmbh, 79539 Loerrach | Markierte polypeptidderivate. |
| US5424286A (en) * | 1993-05-24 | 1995-06-13 | Eng; John | Exendin-3 and exendin-4 polypeptides, and pharmaceutical compositions comprising same |
| US5705483A (en) * | 1993-12-09 | 1998-01-06 | Eli Lilly And Company | Glucagon-like insulinotropic peptides, compositions and methods |
| US5574008A (en) * | 1994-08-30 | 1996-11-12 | Eli Lilly And Company | Biologically active fragments of glucagon-like insulinotropic peptide |
| AU723694B2 (en) * | 1996-06-05 | 2000-08-31 | Roche Diagnostics Gmbh | Exendin analogues, processes for their preparation and medicaments containing them |
| WO1999043705A1 (en) * | 1998-02-27 | 1999-09-02 | Novo Nordisk A/S | N-terminally truncated glp-1 derivatives |
| WO1999043708A1 (en) * | 1998-02-27 | 1999-09-02 | Novo Nordisk A/S | Glp-1 derivatives of glp-1 and exendin with protracted profile of action |
| US7259136B2 (en) * | 1999-04-30 | 2007-08-21 | Amylin Pharmaceuticals, Inc. | Compositions and methods for treating peripheral vascular disease |
| WO2000034331A2 (en) * | 1998-12-07 | 2000-06-15 | Societe De Conseils De Recherches Et D'applications Scientifiques Sas | Analogues of glp-1 |
| EP1175443A1 (en) * | 1999-04-30 | 2002-01-30 | Amylin Pharmaceuticals, Inc. | Modified exendins and exendin agonists |
| EP1623994A3 (en) * | 1999-05-17 | 2008-07-16 | ConjuChem Biotechnologies Inc. | Protection of endogenous therapeutic peptides from peptidase activity through conjugation to blood components |
| SI1180121T1 (en) * | 1999-05-17 | 2004-04-30 | Conjuchem, Inc. | Long lasting insulinotropic peptides |
| EP1076066A1 (en) * | 1999-07-12 | 2001-02-14 | Zealand Pharmaceuticals A/S | Peptides for lowering blood glucose levels |
| US6528486B1 (en) * | 1999-07-12 | 2003-03-04 | Zealand Pharma A/S | Peptide agonists of GLP-1 activity |
| EP1246638B2 (en) * | 2000-01-10 | 2014-07-30 | Amylin Pharmaceuticals, Inc. | Use of exendins and agonists thereof for the treatment of hypertriglyceridemia |
| US7514078B2 (en) * | 2001-06-01 | 2009-04-07 | Cornell Research Foundation, Inc. | Methods of treating prostate cancer with anti-prostate specific membrane antigen antibodies |
| US20030232761A1 (en) * | 2002-03-28 | 2003-12-18 | Hinke Simon A. | Novel analogues of glucose-dependent insulinotropic polypeptide |
| BR0314996A (pt) * | 2002-10-02 | 2005-08-09 | Zealand Pharma As | Composição, composição farmaceuticamente aceitável, método para produzir a composição, métodos para estabilizar a exendina-4 (1-39) ou uma sua variante, derivado ou análogo contra a degradação, antes, durante ou após o uso pretendido, para tratar doenças, para tratar de estados de doenças associados com nìveis elevados de glicose do sangue, para a regulação dos nìveis de glicose do sangue, para a regulação do esvaziamento gástrico, para estimular a liberação de insulina em um mamìfero para reduzir o nìvel de glicose do sangue em um mamìfero, para reduzir o nìvel de lipìdeos plasmáticos em um mamìfero, para reduzir a mortalidade e a morbidez após o infarto miocárdico em um mamìfero, para estimular a liberação de insulina em um mamìfero, e para produzir uma exendina (1-39) estabilizada, e, exendina (1-39) estabilizada |
| KR20050049525A (ko) * | 2002-10-11 | 2005-05-25 | 가부시키가이샤산와카가쿠켄큐쇼 | Ｇｌｐ-1 유도체 및 그의 경점막 흡수형 제제 |
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2004
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- 2005-08-26 EP EP10012756.2A patent/EP2301962B1/de not_active Expired - Lifetime
- 2005-08-26 AT AT05778889T patent/ATE486090T1/de active
- 2005-08-26 HR HR20110061T patent/HRP20110061T1/hr unknown
- 2005-08-26 PL PL10012756T patent/PL2301962T3/pl unknown
- 2005-08-26 RU RU2010148447/10A patent/RU2489443C2/ru not_active IP Right Cessation
- 2005-08-26 JP JP2007528593A patent/JP5047795B2/ja not_active Expired - Fee Related
- 2005-08-26 EP EP08020703.8A patent/EP2070946B1/de not_active Expired - Lifetime
- 2005-08-26 DE DE502005010449T patent/DE502005010449D1/de not_active Expired - Lifetime
- 2005-08-26 CA CA2797666A patent/CA2797666A1/en not_active Abandoned
- 2005-08-26 CN CN2011101471272A patent/CN102304179A/zh active Pending
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- 2005-08-26 WO PCT/DE2005/001503 patent/WO2006024275A2/de not_active Ceased
- 2005-08-26 EP EP05778889A patent/EP1784422B1/de not_active Expired - Lifetime
- 2005-08-26 PL PL08020703T patent/PL2070946T3/pl unknown
- 2005-08-26 BR BRPI0515624-6A patent/BRPI0515624A/pt not_active IP Right Cessation
- 2005-08-26 RU RU2007112115/10A patent/RU2420536C2/ru not_active IP Right Cessation
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