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 |
|---|---|---|---|
| DE102007061763.3 | 2007-12-20 | ||
| DE102007061763A DE102007061763A1 (de) | 2007-12-20 | 2007-12-20 | Substituierte azabicyclische Verbindungen und ihre Verwendung |
| 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 (OSRAM) |
| EP (1) | EP2235011B1 (OSRAM) |
| JP (1) | JP5479360B2 (OSRAM) |
| AT (1) | ATE542819T1 (OSRAM) |
| CA (1) | CA2709776A1 (OSRAM) |
| DE (1) | DE102007061763A1 (OSRAM) |
| ES (1) | ES2379308T3 (OSRAM) |
| WO (1) | WO2009080197A1 (OSRAM) |
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 |
| CN108884061B (zh) | 2017-01-13 | 2021-11-16 | 江苏恒瑞医药股份有限公司 | 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 |
| 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) |
| 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 |
| 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 |
| 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 |
| CN109963854B (zh) | 2017-03-16 | 2022-04-12 | 江苏恒瑞医药股份有限公司 | 杂芳基并[4,3-c]嘧啶-5-胺类衍生物、其制备方法及其在医药上的应用 |
| CA3089159A1 (en) | 2018-02-06 | 2019-08-15 | 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 (OSRAM) | 1992-12-29 | 1997-03-01 | Takeda Pharm Industry Co Ltd | |
| EP0765327B1 (en) | 1994-06-16 | 1999-07-21 | Pfizer Inc. | Pyrazolo and pyrrolopyridines |
| 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 |
| IL125071A0 (en) | 1996-01-17 | 1999-01-26 | Novo Nordisk As | Fused 1,2,4-thiadiazine and fused 1,4-thiazine derivatives their preparation and use |
| ATE548351T1 (de) | 1996-01-29 | 2012-03-15 | Us Of America Represented By The Secretary Dept Of Health And Human Services | Dihydropyridin-pyridin-, benzopyranon- und triazolochinazolin-derivate, deren herstellung und verwendung als adenosinrezeptor-antagonisten |
| 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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| CA2294830A1 (en) | 1997-07-16 | 1999-01-28 | John Bondo Hansen | Fused 1,2,4-thiadiazine derivatives, their preparation and use |
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| DE19834044A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
| DE19834047A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
| DE19943635A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943639A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Dicarbonsäurederivate mit neuartigen pharmazeutischen Eigenschaften |
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| DE19943634A1 (de) | 1999-09-13 | 2001-04-12 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19947154A1 (de) | 1999-10-01 | 2001-10-04 | Bayer Ag | Substituierte 2-Thio-3,5-dicyano-4-aryl-6-aminopyridine und ihre Verwendung |
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| CN1856307A (zh) | 2003-09-23 | 2006-11-01 | 默克公司 | 喹啉钾通道抑制剂 |
| WO2005046603A2 (en) | 2003-11-10 | 2005-05-26 | Synta Pharmaceuticals, Corp. | Pyridine compounds |
| US20050182105A1 (en) | 2004-02-04 | 2005-08-18 | Nirschl Alexandra A. | Method of using 3-cyano-4-arylpyridine derivatives as modulators of androgen receptor function |
| BRPI0512514A (pt) | 2004-06-25 | 2008-03-11 | Taisho Pharmaceutical Co Ltd | composto, antagonista para receptores de crf, e, uso de um composto |
| JP2007161585A (ja) | 2004-06-25 | 2007-06-28 | Taisho Pharmaceut Co Ltd | 環状アミノ基で置換されているピロロピリミジン及びピロロピリジン誘導体 |
| DE102004032651A1 (de) | 2004-07-06 | 2006-02-16 | Bayer Healthcare Ag | Verwendung von substituierten 2-Thio-3,5-dicyano-4-phenyl-6-aminopyriden bei der Behandlung von Übelkeit und Erbrechen |
| DE102004042607A1 (de) | 2004-09-03 | 2006-03-09 | Bayer Healthcare Ag | Substituierte Phenylaminothiazole und ihre Verwendung |
| CN101090724A (zh) | 2004-09-20 | 2007-12-19 | 泽农医药公司 | 用于抑制人硬脂酰CoA去饱和酶的吡啶衍生物 |
| US20090221649A1 (en) | 2005-03-24 | 2009-09-03 | Bayer Healthcare Ag | Use of substituted 2-thio-3,5-dicyano-4-phenyl-6-aminopyridines for the treatment of reperfusion injury and reperfusion damage |
| US7750015B2 (en) | 2005-05-17 | 2010-07-06 | Schering Corporation | Nitrogen-containing heterocyclic compounds and methods of use thereof |
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| WO2007073855A1 (en) | 2005-12-23 | 2007-07-05 | Bayer Healthcare Ag | Use of adenosine a1 receptor agonists for the protection of renal cells against toxic effects caused by aminoglycosides during treatment of infectious diseases |
| DE102006009813A1 (de) | 2006-03-01 | 2007-09-06 | Bayer Healthcare Ag | Verwendung von A2b/A1 Rezeptor Agonisten zur Modulation der Lipidspiegel |
| CA2647338A1 (en) | 2006-04-28 | 2007-11-08 | Avexa Limited | Integrase inhibitors-3 |
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| DE102006042143A1 (de) | 2006-09-08 | 2008-03-27 | Bayer Healthcare Aktiengesellschaft | Neue substituierte Bipyridin-Derivate und ihre Verwendung |
| 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 JP JP2010538405A patent/JP5479360B2/ja not_active Expired - Fee Related
- 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
- 2008-12-09 CA CA2709776A patent/CA2709776A1/en not_active Abandoned
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| ATE542819T1 (de) | 2012-02-15 |
| WO2009080197A1 (de) | 2009-07-02 |
| US8609686B2 (en) | 2013-12-17 |
| JP5479360B2 (ja) | 2014-04-23 |
| EP2235011B1 (de) | 2012-01-25 |
| ES2379308T3 (es) | 2012-04-24 |
| JP2011506501A (ja) | 2011-03-03 |
| DE102007061763A1 (de) | 2009-06-25 |
| US20110003845A1 (en) | 2011-01-06 |
| EP2235011A1 (de) | 2010-10-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20131120 |
|
| FZDE | Discontinued |
Effective date: 20170502 |