DE102004043153B4 - Erfindung betreffend GLP-1 und Exendin - Google Patents
Erfindung betreffend GLP-1 und Exendin Download PDFInfo
- Publication number
- DE102004043153B4 DE102004043153B4 DE102004043153A DE102004043153A DE102004043153B4 DE 102004043153 B4 DE102004043153 B4 DE 102004043153B4 DE 102004043153 A DE102004043153 A DE 102004043153A DE 102004043153 A DE102004043153 A DE 102004043153A DE 102004043153 B4 DE102004043153 B4 DE 102004043153B4
- Authority
- DE
- Germany
- Prior art keywords
- exendin
- glp
- amino acid
- peptide derivatives
- chimeric peptides
- 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.)
- Expired - Fee Related
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- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](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](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 title claims abstract description 127
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Classifications
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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
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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
- C07K14/605—Glucagons
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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
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- 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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- A—HUMAN NECESSITIES
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- 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)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Food Science & Technology (AREA)
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Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004043153A DE102004043153B4 (de) | 2004-09-03 | 2004-09-03 | Erfindung betreffend GLP-1 und Exendin |
| CN2011101471272A CN102304179A (zh) | 2004-09-03 | 2005-08-26 | 与GLP-1和肠促胰岛素类似物(exendin)有关的发明 |
| EP10012756.2A EP2301962B1 (de) | 2004-09-03 | 2005-08-26 | Erfindung betreffend GLP-1 und Exendin |
| RU2010148447/10A RU2489443C2 (ru) | 2004-09-03 | 2005-08-26 | Изобретение, относящееся к glp-1 и эксендинам |
| AT05778889T ATE486090T1 (de) | 2004-09-03 | 2005-08-26 | Erfindung betreffend glp-1 und exendin |
| PCT/DE2005/001503 WO2006024275A2 (de) | 2004-09-03 | 2005-08-26 | Erfindung betreffend glp-1 und exendin |
| MX2007002455A MX2007002455A (es) | 2004-09-03 | 2005-08-26 | Invencion relacionada con glp-1 y exendida. |
| CA002578252A CA2578252A1 (en) | 2004-09-03 | 2005-08-26 | Glp-1 and exendin related invention |
| BRPI0515624-6A BRPI0515624A (pt) | 2004-09-03 | 2005-08-26 | invenção referente ao glp-1 e à exendina |
| CN2005800297604A CN101010340B (zh) | 2004-09-03 | 2005-08-26 | 与GLP-1和肠促胰岛素类似物（exendin)有关的发明 |
| EP05778889A EP1784422B1 (de) | 2004-09-03 | 2005-08-26 | Erfindung betreffend glp-1 und exendin |
| CN201110114845.XA CN102358752B (zh) | 2004-09-03 | 2005-08-26 | 与GLP-1和肠促胰岛素类似物(exendin)有关的发明 |
| HR20110061T HRP20110061T1 (hr) | 2004-09-03 | 2005-08-26 | Izum koji se odnosi na glp-1 i eksendin |
| DE502005010449T DE502005010449D1 (de) | 2004-09-03 | 2005-08-26 | Erfindung betreffend glp-1 und exendin |
| CA2797666A CA2797666A1 (en) | 2004-09-03 | 2005-08-26 | Peptide derivatives of exendin-3 |
| KR1020077007577A KR101237152B1 (ko) | 2004-09-03 | 2005-08-26 | Ｇｌｐ-１ 및 엑센딘 관련 발명 |
| PL08020703T PL2070946T3 (pl) | 2004-09-03 | 2005-08-26 | Wynalazek dotyczący GLP-1 i eksendyny |
| PL10012756T PL2301962T3 (pl) | 2004-09-03 | 2005-08-26 | Wynalazek dotyczący glp-1 i eksendyny |
| AU2005279537A AU2005279537C1 (en) | 2004-09-03 | 2005-08-26 | GLP-1 and exendin related invention |
| EP08020703.8A EP2070946B1 (de) | 2004-09-03 | 2005-08-26 | Erfindung betreffend GLP-1 und Exendin |
| JP2007528593A JP5047795B2 (ja) | 2004-09-03 | 2005-08-26 | Ｇｌｐ−１およびエキセンディンに関する発明 |
| RU2007112115/10A RU2420536C2 (ru) | 2004-09-03 | 2005-08-26 | Пептидные производные эксендина-4 |
| US11/712,978 US8268781B2 (en) | 2004-09-03 | 2007-03-02 | Peptide derivatives of exendin-4 |
| NO20071592A NO20071592L (no) | 2004-09-03 | 2007-03-27 | GLP-1 og exendinrelatert oppfinnelse |
| RU2010148446/10A RU2486197C2 (ru) | 2004-09-03 | 2010-11-26 | Изобретение, относящееся к glp-1 и эксендинам |
| US13/593,866 US20130095037A1 (en) | 2004-09-03 | 2012-08-24 | Peptide derivatives of exendin-4 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004043153A DE102004043153B4 (de) | 2004-09-03 | 2004-09-03 | Erfindung betreffend GLP-1 und Exendin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE102004043153A1 DE102004043153A1 (de) | 2006-03-23 |
| DE102004043153B4 true DE102004043153B4 (de) | 2013-11-21 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004043153A Expired - Fee Related DE102004043153B4 (de) | 2004-09-03 | 2004-09-03 | Erfindung betreffend GLP-1 und Exendin |
| DE502005010449T Expired - Lifetime DE502005010449D1 (de) | 2004-09-03 | 2005-08-26 | Erfindung betreffend glp-1 und exendin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| DE502005010449T Expired - Lifetime DE502005010449D1 (de) | 2004-09-03 | 2005-08-26 | Erfindung betreffend glp-1 und exendin |
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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 |
| SI3456340T1 (sl) | 2007-01-08 | 2022-08-31 | The Trustees Of The University Of Pennsylvania | Antagonisti receptorja za GLP-1 za uporabo pri zdravljenju prirojenega hiperinsulinizma |
| WO2010032509A1 (ja) * | 2008-09-20 | 2010-03-25 | 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前駆体及びその使用 |
| CN102256618A (zh) | 2008-10-17 | 2011-11-23 | 赛诺菲-安万特德国有限公司 | 胰岛素和glp-1激动剂的组合 |
| 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 |
| EP2418216B1 (en) * | 2009-08-10 | 2015-10-28 | Kyoto University | Molecular probe for imaging of pancreatic islet and precursor thereof, and use of the molecular probe or the precursor |
| 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 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5424286A (en) * | 1993-05-24 | 1995-06-13 | Eng; John | Exendin-3 and exendin-4 polypeptides, and pharmaceutical compositions comprising same |
| WO1997046584A1 (de) * | 1996-06-05 | 1997-12-11 | Boehringer Mannheim Gmbh | Exendin-analoga, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| 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 |
| WO2000069900A2 (en) * | 1999-05-17 | 2000-11-23 | Conjuchem, Inc. | Protection of endogenous therapeutic peptides from peptidase activity through conjugation to blood components |
| WO2001004156A1 (en) * | 1999-07-12 | 2001-01-18 | Zealand Pharmaceuticals A/S | Peptides that lower blood glucose levels |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2070329T3 (es) | 1989-07-20 | 1995-06-01 | Sandoz Ltd | Derivados de polipeptidos. |
| 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 |
| US7259136B2 (en) * | 1999-04-30 | 2007-08-21 | Amylin Pharmaceuticals, Inc. | Compositions and methods for treating peripheral vascular disease |
| DE69922043T2 (de) * | 1998-12-07 | 2005-11-24 | Société de Conseils de Recherches et d'Applications Scientifiques S.A.S. | Glp-1 analoge |
| JP2002544127A (ja) * | 1999-04-30 | 2002-12-24 | アミリン・ファーマシューティカルズ，インコーポレイテッド | 修飾されたエキセンジンおよびエキセンジン・アゴニスト |
| CA2363712C (en) * | 1999-05-17 | 2011-05-10 | Conjuchem Inc. | Long lasting insulinotropic peptides |
| US6528486B1 (en) * | 1999-07-12 | 2003-03-04 | Zealand Pharma A/S | Peptide agonists of GLP-1 activity |
| CA2396157A1 (en) * | 2000-01-10 | 2001-07-19 | Amylin Pharmaceuticals, Inc. | Use of exendins and agonists thereof for modulation of triglyceride levels and treatment of dyslipidemia |
| 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 |
| AU2003268621B2 (en) * | 2002-10-02 | 2009-01-15 | Zealand Pharma A/S | Stabilized exendin-4 compounds |
| CA2502118A1 (en) * | 2002-10-11 | 2004-05-06 | Sanwa Kagaku Kenkyusho Co., Ltd. | Glp-1 derivatives and transmicosal absorption preparations thereof |
-
2004
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-
2005
- 2005-08-26 EP EP08020703.8A patent/EP2070946B1/de not_active Expired - Lifetime
- 2005-08-26 HR HR20110061T patent/HRP20110061T1/hr unknown
- 2005-08-26 EP EP10012756.2A patent/EP2301962B1/de not_active Expired - Lifetime
- 2005-08-26 RU RU2007112115/10A patent/RU2420536C2/ru not_active IP Right Cessation
- 2005-08-26 CN CN2005800297604A patent/CN101010340B/zh not_active Expired - Fee Related
- 2005-08-26 WO PCT/DE2005/001503 patent/WO2006024275A2/de not_active Ceased
- 2005-08-26 DE DE502005010449T patent/DE502005010449D1/de not_active Expired - Lifetime
- 2005-08-26 CA CA002578252A patent/CA2578252A1/en not_active Abandoned
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- 2005-08-26 MX MX2007002455A patent/MX2007002455A/es active IP Right Grant
- 2005-08-26 EP EP05778889A patent/EP1784422B1/de not_active Expired - Lifetime
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- 2005-08-26 PL PL08020703T patent/PL2070946T3/pl unknown
- 2005-08-26 AU AU2005279537A patent/AU2005279537C1/en not_active Ceased
- 2005-08-26 AT AT05778889T patent/ATE486090T1/de active
- 2005-08-26 KR KR1020077007577A patent/KR101237152B1/ko not_active Expired - Fee Related
- 2005-08-26 PL PL10012756T patent/PL2301962T3/pl unknown
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- 2005-08-26 JP JP2007528593A patent/JP5047795B2/ja not_active Expired - Fee Related
-
2007
- 2007-03-02 US US11/712,978 patent/US8268781B2/en not_active Expired - Fee Related
- 2007-03-27 NO NO20071592A patent/NO20071592L/no not_active Application Discontinuation
-
2010
- 2010-11-26 RU RU2010148446/10A patent/RU2486197C2/ru not_active IP Right Cessation
-
2012
- 2012-08-24 US US13/593,866 patent/US20130095037A1/en not_active Abandoned
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5424286A (en) * | 1993-05-24 | 1995-06-13 | Eng; John | Exendin-3 and exendin-4 polypeptides, and pharmaceutical compositions comprising same |
| WO1997046584A1 (de) * | 1996-06-05 | 1997-12-11 | Boehringer Mannheim Gmbh | Exendin-analoga, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| 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 |
| WO2000069900A2 (en) * | 1999-05-17 | 2000-11-23 | Conjuchem, Inc. | Protection of endogenous therapeutic peptides from peptidase activity through conjugation to blood components |
| WO2001004156A1 (en) * | 1999-07-12 | 2001-01-18 | Zealand Pharmaceuticals A/S | Peptides that lower blood glucose levels |
Non-Patent Citations (2)
| Title |
|---|
| Datenbank PubMed, Zusammenfassung zu: KNUDSEN, L.B. [u.a.]: Potent derivatives of glucagon-like peptide-1 with pharmacokinetic properties suitable for once daily administration. J. Med. Chem. (2000) 43 (9) 1664-9 * |
| Datenbank PubMed, Zusammenfassung zu: XIAO, Q. [u.a.]: Biological activities of glucagon-like peptide-1 analogues in vitro and in vivo. Biochemistry (06.03.2001) 40 (9) 2860-9 * |
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