CA2671127A1 - Substituted 4-amino-3,5-dicyano-2-thiopyridines and use thereof - Google Patents
Substituted 4-amino-3,5-dicyano-2-thiopyridines and use thereof Download PDFInfo
- Publication number
- CA2671127A1 CA2671127A1 CA002671127A CA2671127A CA2671127A1 CA 2671127 A1 CA2671127 A1 CA 2671127A1 CA 002671127 A CA002671127 A CA 002671127A CA 2671127 A CA2671127 A CA 2671127A CA 2671127 A1 CA2671127 A1 CA 2671127A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- mono
- formula
- alkylamino
- hydroxyl
- 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
- 238000011282 treatment Methods 0.000 claims abstract 10
- 239000003814 drug Substances 0.000 claims abstract 9
- 238000011321 prophylaxis Methods 0.000 claims abstract 9
- 201000010099 disease Diseases 0.000 claims abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- -1 pyrrolidino, piperidino, morpholino, piperazino Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 3
- 206010002383 Angina Pectoris Diseases 0.000 claims 3
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 3
- 208000029078 coronary artery disease Diseases 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 208000010125 myocardial infarction Diseases 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000000464 thioxo group Chemical group S=* 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 206010020852 Hypertonia Diseases 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- 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
- A61P9/10—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006056739.0 | 2006-12-01 | ||
| DE102006056739A DE102006056739A1 (de) | 2006-12-01 | 2006-12-01 | Substituierte 4-Amino-3,5-dicyano-2-thiopyridine und ihre Verwendung |
| PCT/EP2007/009963 WO2008064789A1 (de) | 2006-12-01 | 2007-11-17 | Substituierte 4-amino-3,5-dicyano-2-thiopyridine und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2671127A1 true CA2671127A1 (en) | 2008-06-05 |
Family
ID=39101374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002671127A Abandoned CA2671127A1 (en) | 2006-12-01 | 2007-11-17 | Substituted 4-amino-3,5-dicyano-2-thiopyridines and use thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8703934B2 (enExample) |
| EP (1) | EP2099781B1 (enExample) |
| JP (1) | JP5317980B2 (enExample) |
| CA (1) | CA2671127A1 (enExample) |
| DE (1) | DE102006056739A1 (enExample) |
| ES (1) | ES2397947T3 (enExample) |
| WO (1) | WO2008064789A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004042607A1 (de) | 2004-09-03 | 2006-03-09 | Bayer Healthcare Ag | Substituierte Phenylaminothiazole und ihre Verwendung |
| DE102006042143A1 (de) | 2006-09-08 | 2008-03-27 | Bayer Healthcare Aktiengesellschaft | Neue substituierte Bipyridin-Derivate 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 |
| DE102007061763A1 (de) * | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte azabicyclische Verbindungen und ihre Verwendung |
| DE102008013587A1 (de) * | 2008-03-11 | 2009-09-17 | Bayer Schering Pharma Aktiengesellschaft | Heteroaryl-substituierte Dicyanopyridine und ihre Verwendung |
| EP2297104B1 (de) * | 2008-05-29 | 2013-08-07 | Bayer Intellectual Property GmbH | 2-alkoxy-substituierte dicyanopyridine und ihre verwendung |
| DE102008062567A1 (de) | 2008-12-16 | 2010-06-17 | Bayer Schering Pharma Aktiengesellschaft | Dipeptoid-Prodrugs und ihre Verwendung |
| DE102009006602A1 (de) * | 2009-01-29 | 2010-08-05 | Bayer Schering Pharma Aktiengesellschaft | Alkylamino-substituierte Dicyanopyridine und deren Aminosäureester-Prodrugs |
| EP2575821B1 (en) | 2010-05-26 | 2015-08-12 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| DE102010030688A1 (de) | 2010-06-30 | 2012-01-05 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dicyanopyridine und ihre Verwendung |
| US20120058983A1 (en) | 2010-09-02 | 2012-03-08 | Bayer Pharma Aktiengesellschaft | Adenosine A1 agonists for the treatment of glaucoma and ocular hypertension |
| 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 |
| PL2771003T3 (pl) | 2011-10-28 | 2017-10-31 | Lumena Pharmaceuticals Llc | Inhibitory ponownego wykorzystania kwasów żółciowych do leczenia pediatrycznych cholestatycznych chorób wątroby |
| KR20210131431A (ko) | 2011-10-28 | 2021-11-02 | 샤이어 휴먼 지네틱 테라피즈 인크. | 고담혈증 및 담즙 정체성 간 질환 치료용 담즙산 재순환 억제제 |
| RU2015139732A (ru) | 2013-03-15 | 2017-04-24 | ЛУМЕНА ФАРМАСЬЮТИКАЛС ЭлЭлСи | Ингибиторы рециркуляции желчных кислот для лечения пищевода барретта и гастроэзофагеальной рефлюксной болезни |
| BR112015023646A2 (pt) | 2013-03-15 | 2017-07-18 | Lumena Pharmaceuticals Inc | inibidores de ácidos biliares de reciclagem para tratamento de colangite esclerosante primária e doença inflamatória do intestino |
| 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 |
| 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 |
| 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) |
| CN109651358B (zh) * | 2017-10-11 | 2023-04-07 | 上海迪诺医药科技有限公司 | 4-氨基吡啶衍生物、其药物组合物、制备方法及应用 |
| CN109957584A (zh) * | 2017-12-25 | 2019-07-02 | 尚科生物医药（上海）有限公司 | 一种用于制备（r）-(4-氯苯基)-2-吡啶甲醇的生物催化方法 |
| EP3746081A4 (en) * | 2018-01-31 | 2021-10-27 | Intra-Cellular Therapies, Inc. | Novel uses |
| JP7592606B2 (ja) | 2019-02-12 | 2024-12-02 | ミルム ファーマシューティカルズ インコーポレイテッド | 胆汁酸塩排出ポンプ欠損症の患者における遺伝子型およびａｓｂｔｉに対する用量依存的反応 |
| CN116745289A (zh) * | 2020-10-20 | 2023-09-12 | 奥洛治疗有限公司 | 游离脂肪酸受体1的激动剂及其在与所述受体相关的疾病中的用途 |
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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 |
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| 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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| JP4431638B2 (ja) | 1996-01-29 | 2010-03-17 | アメリカ合衆国 | ジヒドロピリジン―、ピリジン―、ベンゾピラン―オン―およびトリアゾロキナゾリン誘導体、それらの製造およびそれらのアデノシン受容体アンタゴニストとしての用途 |
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| US6632823B1 (en) | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| 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 |
| DE19943636A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| 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 |
| KR100521735B1 (ko) | 2000-02-25 | 2005-10-17 | 에프. 호프만-라 로슈 아게 | 아데노신 수용체 조절인자 |
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| DE102008062567A1 (de) | 2008-12-16 | 2010-06-17 | Bayer Schering Pharma Aktiengesellschaft | Dipeptoid-Prodrugs und ihre Verwendung |
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-
2006
- 2006-12-01 DE DE102006056739A patent/DE102006056739A1/de not_active Withdrawn
-
2007
- 2007-11-17 JP JP2009538617A patent/JP5317980B2/ja not_active Expired - Fee Related
- 2007-11-17 EP EP07846652A patent/EP2099781B1/de not_active Not-in-force
- 2007-11-17 US US12/516,939 patent/US8703934B2/en not_active Expired - Fee Related
- 2007-11-17 ES ES07846652T patent/ES2397947T3/es active Active
- 2007-11-17 CA CA002671127A patent/CA2671127A1/en not_active Abandoned
- 2007-11-17 WO PCT/EP2007/009963 patent/WO2008064789A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP5317980B2 (ja) | 2013-10-16 |
| US20100069363A1 (en) | 2010-03-18 |
| EP2099781A1 (de) | 2009-09-16 |
| US8703934B2 (en) | 2014-04-22 |
| JP2010510999A (ja) | 2010-04-08 |
| DE102006056739A1 (de) | 2008-06-05 |
| ES2397947T3 (es) | 2013-03-12 |
| WO2008064789A1 (de) | 2008-06-05 |
| EP2099781B1 (de) | 2012-10-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20151223 |