CA2709776A1 - Substituted pyrrolo[2, 3-b] and pyrazolo[3, 4-b] pyridines for use as adenosine receptor ligands - Google Patents
Substituted pyrrolo[2, 3-b] and pyrazolo[3, 4-b] pyridines for use as adenosine receptor ligands Download PDFInfo
- Publication number
- CA2709776A1 CA2709776A1 CA2709776A CA2709776A CA2709776A1 CA 2709776 A1 CA2709776 A1 CA 2709776A1 CA 2709776 A CA2709776 A CA 2709776A CA 2709776 A CA2709776 A CA 2709776A CA 2709776 A1 CA2709776 A1 CA 2709776A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- group
- alkoxy
- hydroxyl
- alkyl
- 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
- 102000009346 Adenosine receptors Human genes 0.000 title 1
- 108050000203 Adenosine receptors Proteins 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title 1
- 238000011282 treatment Methods 0.000 claims abstract 12
- 239000003814 drug Substances 0.000 claims abstract 9
- 230000002265 prevention Effects 0.000 claims abstract 7
- 238000000034 method Methods 0.000 claims abstract 5
- 230000006806 disease prevention Effects 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 23
- -1 pyrrolidino, piperidino, morpholino, piperazino Chemical group 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 12
- 229910052731 fluorine Inorganic materials 0.000 claims 12
- 239000011737 fluorine Substances 0.000 claims 12
- 125000001153 fluoro group Chemical group F* 0.000 claims 12
- 125000004043 oxo group Chemical group O=* 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 239000000460 chlorine Chemical group 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 7
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 4
- 206010002383 Angina Pectoris Diseases 0.000 claims 4
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims 4
- 206010019280 Heart failures Diseases 0.000 claims 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 4
- 208000029078 coronary artery disease Diseases 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 4
- 239000012442 inert solvent Substances 0.000 claims 4
- 208000010125 myocardial infarction Diseases 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 206010020772 Hypertension Diseases 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- PKTJKKARCIJTJR-UHFFFAOYSA-N 2,2-difluoro-1,3-dioxolane Chemical compound FC1(F)OCCO1 PKTJKKARCIJTJR-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- 229940127088 antihypertensive drug Drugs 0.000 claims 1
- 229940127217 antithrombotic drug Drugs 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000000464 thioxo group Chemical group S=* 0.000 claims 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical class C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- NABZXASCLFSKLF-UHFFFAOYSA-N [1,2]oxazolo[4,3-b]pyridine Chemical class C1=CC=NC2=CON=C21 NABZXASCLFSKLF-UHFFFAOYSA-N 0.000 abstract 1
- 150000005255 pyrrolopyridines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007061763A DE102007061763A1 (de) | 2007-12-20 | 2007-12-20 | Substituierte azabicyclische Verbindungen und ihre Verwendung |
| DE102007061763.3 | 2007-12-20 | ||
| PCT/EP2008/010409 WO2009080197A1 (de) | 2007-12-20 | 2008-12-09 | Substituierte pyrrolo[2, 3-b]- und pyrazolo[3, 4-b] pyridine als adenosin rezeptor liganden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2709776A1 true CA2709776A1 (en) | 2009-07-02 |
Family
ID=40436470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2709776A Abandoned CA2709776A1 (en) | 2007-12-20 | 2008-12-09 | Substituted pyrrolo[2, 3-b] and pyrazolo[3, 4-b] pyridines for use as adenosine receptor ligands |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8609686B2 (en:Method) |
| EP (1) | EP2235011B1 (en:Method) |
| JP (1) | JP5479360B2 (en:Method) |
| AT (1) | ATE542819T1 (en:Method) |
| CA (1) | CA2709776A1 (en:Method) |
| DE (1) | DE102007061763A1 (en:Method) |
| ES (1) | ES2379308T3 (en:Method) |
| WO (1) | WO2009080197A1 (en:Method) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007035367A1 (de) * | 2007-07-27 | 2009-01-29 | Bayer Healthcare Ag | Substituierte Aryloxazole und ihre Verwendung |
| DE102007061764A1 (de) * | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Anellierte Cyanopyridine und ihre Verwendung |
| DE102009006602A1 (de) * | 2009-01-29 | 2010-08-05 | Bayer Schering Pharma Aktiengesellschaft | Alkylamino-substituierte Dicyanopyridine und deren Aminosäureester-Prodrugs |
| DE102010030688A1 (de) * | 2010-06-30 | 2012-01-05 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dicyanopyridine und ihre Verwendung |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US11014904B2 (en) | 2017-01-13 | 2021-05-25 | Jiangsu Hengrui Medicine Co., Ltd. | 1,2,4-triazine-3-amine derivative, preparation method therefor, and use thereof in medicine |
| WO2018153899A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit stimulatoren und/oder aktivatoren der löslichen guanylatcyclase (sgc) |
| WO2018153895A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit einem inhibitor der neutralen endopeptidase und/oder einem angiotensin ii rezeptor-antagonisten |
| WO2018153898A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit mineralocorticoid-rezeptor-antagonisten |
| WO2018153900A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit sglt-2-hemmern |
| WO2018153897A1 (de) | 2017-02-22 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit hcn-kanal-hemmern |
| CN108467386B (zh) * | 2017-02-23 | 2020-11-17 | 江苏恒瑞医药股份有限公司 | 稠杂芳基取代的1,2,4-三嗪-3-胺类衍生物、其制备方法及其在医药上的应用 |
| UA125592C2 (uk) | 2017-03-16 | 2022-04-27 | Джянгсу Хенгруй Медісін Ко., Лтд. | ПОХІДНА ГЕТЕРОАРИЛ[4,3-c]ПІРИМІДИН-5-АМІНУ, СПОСІБ ЇЇ ОТРИМАННЯ ТА ЇЇ МЕДИЧНІ ЗАСТОСУВАННЯ |
| US20210032253A1 (en) | 2018-02-06 | 2021-02-04 | Jiangsu Hengrui Medicine Co., Ltd. | Pyrazolo[1,5-a][1,3,5]triazine-2-amine derivative, preparation method therefor and medical use thereof |
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| US4052510A (en) | 1974-12-18 | 1977-10-04 | Sandoz, Inc. | 4-alkyl-2,6-di(secondary or tertiary alkylamino) pyridines, compositions thereof and methods for treating diabetes and obesity |
| TW299333B (en:Method) | 1992-12-29 | 1997-03-01 | Takeda Pharm Industry Co Ltd | |
| PL181895B1 (pl) | 1994-06-16 | 2001-10-31 | Pfizer | Nowe pirazolo-i pirolopirydyny _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ PL PL PL PL |
| DE4430638A1 (de) | 1994-08-29 | 1996-03-07 | Bayer Ag | Verwendung von substituierten 4-Phenyl-6-amino-nicotinsäurederivaten als Arzneimittel |
| JPH09132529A (ja) | 1995-11-09 | 1997-05-20 | Ono Pharmaceut Co Ltd | 一酸化窒素合成酵素阻害剤 |
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| AU709190B2 (en) | 1996-01-29 | 1999-08-26 | United States Of America, Represented By The Secretary, Department Of Health And Human Services, The | Dihydropyridine-, pyridine-, benzopyran- one- and triazoloquinazoline derivative, their preparation and their use as adenosine receptor antagonists |
| JPH10324687A (ja) | 1997-02-19 | 1998-12-08 | Nippon Soda Co Ltd | ピロール化合物、製法および農園芸用殺菌剤 |
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| DE19834047A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
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| DE19943639A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Dicarbonsäurederivate mit neuartigen pharmazeutischen Eigenschaften |
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| DE102006009813A1 (de) | 2006-03-01 | 2007-09-06 | Bayer Healthcare Ag | Verwendung von A2b/A1 Rezeptor Agonisten zur Modulation der Lipidspiegel |
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| DE102006056739A1 (de) | 2006-12-01 | 2008-06-05 | Bayer Healthcare Ag | Substituierte 4-Amino-3,5-dicyano-2-thiopyridine und ihre Verwendung |
| DE102006056740A1 (de) | 2006-12-01 | 2008-06-05 | Bayer Healthcare Ag | Cyclisch substituierte 3,5-Dicyano-2-thiopyridine und ihre Verwendung |
| DE102007035367A1 (de) | 2007-07-27 | 2009-01-29 | Bayer Healthcare Ag | Substituierte Aryloxazole und ihre Verwendung |
| DE102007036076A1 (de) | 2007-08-01 | 2009-02-05 | Bayer Healthcare Aktiengesellschaft | Dipeptoid-Produgs und ihre Verwendung |
| DE102007061764A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Anellierte Cyanopyridine und ihre Verwendung |
| DE102008013587A1 (de) | 2008-03-11 | 2009-09-17 | Bayer Schering Pharma Aktiengesellschaft | Heteroaryl-substituierte Dicyanopyridine und ihre Verwendung |
| US8791146B2 (en) | 2008-05-29 | 2014-07-29 | Bayer Intellectual Property Gmbh | 2-alkoxy-substituted dicyanopyridines and their use |
| DE102008062566A1 (de) | 2008-12-16 | 2010-06-17 | Bayer Schering Pharma Aktiengesellschaft | Aminosäureester-Prodrugs und ihre Verwendung |
-
2007
- 2007-12-20 DE DE102007061763A patent/DE102007061763A1/de not_active Withdrawn
-
2008
- 2008-12-09 AT AT08864918T patent/ATE542819T1/de active
- 2008-12-09 US US12/809,674 patent/US8609686B2/en not_active Expired - Fee Related
- 2008-12-09 ES ES08864918T patent/ES2379308T3/es active Active
- 2008-12-09 JP JP2010538405A patent/JP5479360B2/ja not_active Expired - Fee Related
- 2008-12-09 CA CA2709776A patent/CA2709776A1/en not_active Abandoned
- 2008-12-09 WO PCT/EP2008/010409 patent/WO2009080197A1/de not_active Ceased
- 2008-12-09 EP EP08864918A patent/EP2235011B1/de not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| EP2235011B1 (de) | 2012-01-25 |
| EP2235011A1 (de) | 2010-10-06 |
| ATE542819T1 (de) | 2012-02-15 |
| JP5479360B2 (ja) | 2014-04-23 |
| JP2011506501A (ja) | 2011-03-03 |
| DE102007061763A1 (de) | 2009-06-25 |
| ES2379308T3 (es) | 2012-04-24 |
| WO2009080197A1 (de) | 2009-07-02 |
| US20110003845A1 (en) | 2011-01-06 |
| US8609686B2 (en) | 2013-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20131120 |
|
| FZDE | Discontinued |
Effective date: 20170502 |