CA2505752A1 - Imidazo[1,5a]pyridine derivatives and methods for treating aldosterone mediated diseases - Google Patents
Imidazo[1,5a]pyridine derivatives and methods for treating aldosterone mediated diseases Download PDFInfo
- Publication number
- CA2505752A1 CA2505752A1 CA002505752A CA2505752A CA2505752A1 CA 2505752 A1 CA2505752 A1 CA 2505752A1 CA 002505752 A CA002505752 A CA 002505752A CA 2505752 A CA2505752 A CA 2505752A CA 2505752 A1 CA2505752 A1 CA 2505752A1
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- Prior art keywords
- hydrogen
- optionally substituted
- compound
- trifluoromethyl
- alkoxy
- 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
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- 238000000034 method Methods 0.000 title claims description 38
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 title abstract description 6
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 title abstract description 6
- 229960002478 aldosterone Drugs 0.000 title abstract description 6
- 230000001404 mediated effect Effects 0.000 title abstract description 5
- 201000010099 disease Diseases 0.000 title description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 3
- MLXWMEFKFOSOCP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical class C1=CC=CC2=C=N[CH]N21 MLXWMEFKFOSOCP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 108010009911 Cytochrome P-450 CYP11B2 Proteins 0.000 claims abstract description 23
- 102100024329 Cytochrome P450 11B2, mitochondrial Human genes 0.000 claims abstract description 23
- 206010020772 Hypertension Diseases 0.000 claims abstract description 22
- 230000000694 effects Effects 0.000 claims abstract description 18
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- 102000008186 Collagen Human genes 0.000 claims abstract description 11
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- 206010016654 Fibrosis Diseases 0.000 claims abstract description 11
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- 208000008589 Obesity Diseases 0.000 claims abstract description 11
- 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 11
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- 208000024896 potassium deficiency disease Diseases 0.000 claims abstract description 11
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- 208000011580 syndromic disease Diseases 0.000 claims abstract description 11
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- 208000022831 chronic renal failure syndrome Diseases 0.000 claims abstract description 9
- 230000002265 prevention Effects 0.000 claims abstract description 7
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- 150000003839 salts Chemical class 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
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- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
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- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
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- 241000124008 Mammalia Species 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
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- HMNQDXFMYVAXKB-UHFFFAOYSA-N 5-naphthalen-1-ylimidazo[1,5-a]pyridine Chemical compound C1=CC=C2C(C=3N4C=NC=C4C=CC=3)=CC=CC2=C1 HMNQDXFMYVAXKB-UHFFFAOYSA-N 0.000 claims description 3
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- WSPXYMILZMWVRT-UHFFFAOYSA-N 5-(1-benzofuran-3-yl)imidazo[1,5-a]pyridine Chemical compound C1=CC2=CN=CN2C(C=2C3=CC=CC=C3OC=2)=C1 WSPXYMILZMWVRT-UHFFFAOYSA-N 0.000 claims description 2
- PLSQRYHAFQEEBB-UHFFFAOYSA-N 5-(2-phenylphenyl)imidazo[1,5-a]pyridine Chemical compound C=1C=CC2=CN=CN2C=1C1=CC=CC=C1C1=CC=CC=C1 PLSQRYHAFQEEBB-UHFFFAOYSA-N 0.000 claims description 2
- NWFCFXALXRKBCD-UHFFFAOYSA-N 5-(4-phenylphenyl)imidazo[1,5-a]pyridine Chemical compound C=1C=CC2=CN=CN2C=1C(C=C1)=CC=C1C1=CC=CC=C1 NWFCFXALXRKBCD-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims description 2
- ZHDGCLHRFAZRQR-UHFFFAOYSA-N benzyl 4-imidazo[1,5-a]pyridin-5-yl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1CC(C=2N3C=NC=C3C=CC=2)=CCN1C(=O)OCC1=CC=CC=C1 ZHDGCLHRFAZRQR-UHFFFAOYSA-N 0.000 claims description 2
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- 229910020008 S(O) Inorganic materials 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
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- 239000000243 solution Substances 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- KCWZGJVSDFYRIX-YFKPBYRVSA-N N(gamma)-nitro-L-arginine methyl ester Chemical compound COC(=O)[C@@H](N)CCCN=C(N)N[N+]([O-])=O KCWZGJVSDFYRIX-YFKPBYRVSA-N 0.000 description 8
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- 241001465754 Metazoa Species 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
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- 125000002252 acyl group Chemical group 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 125000002883 imidazolyl group Chemical group 0.000 description 6
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- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 5
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- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
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- Organic Chemistry (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42732502P | 2002-11-18 | 2002-11-18 | |
| US60/427,325 | 2002-11-18 | ||
| PCT/EP2003/012851 WO2004046145A1 (en) | 2002-11-18 | 2003-11-17 | Imidazo[1, 5a]pyridine derivatives and methods for treating aldosterone mediated diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2505752A1 true CA2505752A1 (en) | 2004-06-03 |
Family
ID=32326521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002505752A Abandoned CA2505752A1 (en) | 2002-11-18 | 2003-11-17 | Imidazo[1,5a]pyridine derivatives and methods for treating aldosterone mediated diseases |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7223866B2 (enExample) |
| EP (1) | EP1565463B1 (enExample) |
| JP (1) | JP2006508970A (enExample) |
| CN (1) | CN100447142C (enExample) |
| AT (1) | ATE398124T1 (enExample) |
| AU (1) | AU2003292039A1 (enExample) |
| BR (1) | BR0316306A (enExample) |
| CA (1) | CA2505752A1 (enExample) |
| DE (1) | DE60321593D1 (enExample) |
| ES (1) | ES2305520T3 (enExample) |
| PT (1) | PT1565463E (enExample) |
| WO (1) | WO2004046145A1 (enExample) |
Families Citing this family (35)
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| CA2508618C (en) * | 2002-12-06 | 2012-02-21 | Bayer Healthcare Ag | Tetrahydro-naphthalene derivatives |
| AU2003288200A1 (en) * | 2002-12-09 | 2004-06-30 | Bayer Healthcare Ag | Tetrahydro-naphthalene derivatives as vanilloid receptor antagonists |
| EP1853261B1 (de) * | 2005-03-03 | 2017-01-11 | Universität des Saarlandes | Selektive hemmstoffe humaner corticoidsynthasen |
| TW200716105A (en) * | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Imidazole compounds |
| TW200716634A (en) * | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
| TW200716636A (en) * | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
| GT200600381A (es) * | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
| EP1842543A1 (en) | 2006-04-05 | 2007-10-10 | Speedel Pharma AG | Pharmaceutical composition coprising an aldosterone synthase inhibitor and a mineralcorticoid receptor antagonist |
| WO2008110523A1 (en) * | 2007-03-09 | 2008-09-18 | Probiodrug Ag | Imidazo [1,5-a] pyridine derivatives as inhibitors of glutaminyl cyclase |
| JP2011503081A (ja) | 2007-11-01 | 2011-01-27 | ブリストル−マイヤーズ スクイブ カンパニー | グルココルチコイド受容体、ＡＰ−１および／またはＮＦ−κＢ活性の調節剤として有用な非ステロイド性化合物、並びにその使用 |
| EP2095819A1 (en) | 2008-02-28 | 2009-09-02 | Maastricht University | N-benzyl imidazole derivatives and their use as aldosterone synthase inhibitors |
| PL2435409T3 (pl) | 2009-05-28 | 2015-01-30 | Novartis Ag | Podstawione pochodne aminopropionowe jako inhibitory neprylizyny |
| CA2763565A1 (en) | 2009-05-28 | 2010-12-02 | Novartis Ag | Substituted aminobutyric derivatives as neprilysin inhibitors |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| EP2507234B1 (en) * | 2009-11-30 | 2014-03-12 | Novartis AG | Imidazole derivatives as aldosterone synthase inhibitors |
| US8673974B2 (en) | 2010-11-16 | 2014-03-18 | Novartis Ag | Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors |
| CN103648495A (zh) | 2011-07-08 | 2014-03-19 | 诺华股份有限公司 | 在高甘油三酯对象中治疗动脉粥样硬化的方法 |
| EP2757883B1 (en) | 2011-09-22 | 2021-01-13 | Merck Sharp & Dohme Corp. | Triazolopyridyl compounds as aldosterone synthase inhibitors |
| US9351973B2 (en) | 2011-09-22 | 2016-05-31 | Merck Sharp & Dohme Corp. | Pyrazolopyridyl compounds as aldosterone synthase inhibitors |
| WO2013043518A1 (en) * | 2011-09-22 | 2013-03-28 | Merck Sharp & Dohme Corp. | Imidazopyridyl compounds as aldosterone synthase inhibitors |
| AU2013209952B2 (en) | 2012-01-17 | 2016-09-01 | Recordati Ag | New forms and salts of a dihydropyrrolo(1,2-c)imidazolyl aldosterone synthase or aromatase inhibitor |
| UY35144A (es) | 2012-11-20 | 2014-06-30 | Novartis Ag | Miméticos lineales sintéticos de apelina para el tratamiento de insuficiencia cardiaca |
| SG11201506018PA (en) | 2013-02-14 | 2015-08-28 | Novartis Ag | Substituted bisphenyl butanoic phosphonic acid derivatives as nep (neutral endopeptidase) inhibitors |
| EP3024845A1 (en) | 2013-07-25 | 2016-06-01 | Novartis AG | Cyclic polypeptides for the treatment of heart failure |
| WO2015013169A2 (en) | 2013-07-25 | 2015-01-29 | Novartis Ag | Bioconjugates of synthetic apelin polypeptides |
| SG11201704758XA (en) | 2015-01-23 | 2017-08-30 | Novartis Ag | Synthetic apelin fatty acid conjugates with improved half-life |
| GB201511790D0 (en) * | 2015-07-06 | 2015-08-19 | Iomet Pharma Ltd | Pharmaceutical compound |
| JOP20190086A1 (ar) | 2016-10-21 | 2019-04-18 | Novartis Ag | مشتقات نافثيريدينون جديدة واستخدامها في معالجة عدم انتظام ضربات القلب |
| UY38072A (es) | 2018-02-07 | 2019-10-01 | Novartis Ag | Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos |
| UY38485A (es) | 2018-11-27 | 2020-06-30 | Novartis Ag | Compuestos tetrámeros cíclicos como inhibidores de proproteína convertasa subtilisina/kexina tipo 9 (pcsk9), método de tratamiento, uso y su preparación |
| WO2020110008A1 (en) | 2018-11-27 | 2020-06-04 | Novartis Ag | Cyclic pentamer compounds as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorder |
| JP7657151B2 (ja) | 2018-11-27 | 2025-04-04 | ノバルティス アーゲー | 代謝性障害の処置のためのプロタンパク質コンバターゼスブチリシン／ケキシン９型（ｐｃｓｋ９）阻害剤としての環状ペプチド |
| WO2023084449A1 (en) | 2021-11-12 | 2023-05-19 | Novartis Ag | Diaminocyclopentylpyridine derivatives for the treatment of a disease or disorder |
| AR127698A1 (es) | 2021-11-23 | 2024-02-21 | Novartis Ag | Derivados de naftiridinona para el tratamiento de una enfermedad o un trastorno |
| IL324432A (en) | 2023-05-24 | 2026-01-01 | Novartis Ag | Naphthyridinone derivatives for the treatment of a disease or disorder |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1250844A (en) * | 1981-06-22 | 1989-03-07 | Neville Ford | Substituted imidazo¬1,5-a|pyridines, process for their manufacture, pharmaceutical preparations containing these compounds and their therapeutic application |
| US4470986A (en) * | 1982-12-21 | 1984-09-11 | Ciba-Geigy Corporation | Certain imidazo (1,5-A) pyridine aliphatic carboxylic acid derivatives and their use as selective thromboxane inhibitors |
| US4588732A (en) | 1982-12-21 | 1986-05-13 | Ciba-Geigy Corporation | Certain imidazo(1,5-a)pyridine derivatives and their use as thromboxane synthetase inhibitors |
| US4617307A (en) * | 1984-06-20 | 1986-10-14 | Ciba-Geigy Corporation | Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors |
| US4889861A (en) | 1982-12-21 | 1989-12-26 | Ciba-Geigy Corp. | Substituted imidazo[1,5-a]pyridine derivatives and other substituted bicyclic derivatives and their use as aromatase inhibitors |
| US5428160A (en) * | 1982-12-21 | 1995-06-27 | Ciba-Geigy Corporation | Substituted imidazo[5-a]pyridine derviatives and other substituted bicyclic derivatives |
| JPS615076A (ja) * | 1984-06-19 | 1986-01-10 | Toyama Chem Co Ltd | 新規な１，４−ジヒドロピリジン誘導体およびその塩 |
| GB8510541D0 (en) * | 1985-04-25 | 1985-05-30 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| US5798364A (en) * | 1992-03-26 | 1998-08-25 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Imidazopyridines |
| US5529992A (en) | 1992-04-21 | 1996-06-25 | Curators Of The University Of Missouri | Method for inhibiting myocardial fibrosis by administering an aldosterone antagonist which suppresses aldoster one receptors |
| US6150347A (en) | 1992-04-21 | 2000-11-21 | The Curators Of The University Of Missouri | Use of aldosterone antagonists to inhibit myocardial fibrosis |
| JPH0971586A (ja) * | 1995-09-07 | 1997-03-18 | Yamanouchi Pharmaceut Co Ltd | 新規な二環性縮合イミダゾール誘導体 |
| DE19701257A1 (de) * | 1997-01-17 | 1998-07-23 | Hannecke Wolf D Kunststoff | Säulenpräsentationssystem in Modulbauweise zur Schaustellung von Waren oder Prospektmaterial und insbesondere von dünnen Gegenständen |
| US6887870B1 (en) | 1999-10-12 | 2005-05-03 | Bristol-Myers Squibb Company | Heterocyclic sodium/proton exchange inhibitors and method |
-
2003
- 2003-11-17 ES ES03767563T patent/ES2305520T3/es not_active Expired - Lifetime
- 2003-11-17 BR BR0316306-7A patent/BR0316306A/pt not_active IP Right Cessation
- 2003-11-17 US US10/534,631 patent/US7223866B2/en not_active Expired - Fee Related
- 2003-11-17 EP EP03767563A patent/EP1565463B1/en not_active Expired - Lifetime
- 2003-11-17 JP JP2004552632A patent/JP2006508970A/ja active Pending
- 2003-11-17 AU AU2003292039A patent/AU2003292039A1/en not_active Abandoned
- 2003-11-17 AT AT03767563T patent/ATE398124T1/de not_active IP Right Cessation
- 2003-11-17 CN CNB2003801035050A patent/CN100447142C/zh not_active Expired - Fee Related
- 2003-11-17 WO PCT/EP2003/012851 patent/WO2004046145A1/en not_active Ceased
- 2003-11-17 PT PT03767563T patent/PT1565463E/pt unknown
- 2003-11-17 CA CA002505752A patent/CA2505752A1/en not_active Abandoned
- 2003-11-17 DE DE60321593T patent/DE60321593D1/de not_active Expired - Lifetime
-
2007
- 2007-04-24 US US11/739,290 patent/US7713991B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR0316306A (pt) | 2005-09-27 |
| EP1565463A1 (en) | 2005-08-24 |
| ATE398124T1 (de) | 2008-07-15 |
| EP1565463B1 (en) | 2008-06-11 |
| CN100447142C (zh) | 2008-12-31 |
| JP2006508970A (ja) | 2006-03-16 |
| HK1081540A1 (en) | 2006-05-19 |
| US20070197582A1 (en) | 2007-08-23 |
| US7223866B2 (en) | 2007-05-29 |
| US20060058342A1 (en) | 2006-03-16 |
| PT1565463E (pt) | 2008-09-10 |
| ES2305520T3 (es) | 2008-11-01 |
| WO2004046145A1 (en) | 2004-06-03 |
| CN1711262A (zh) | 2005-12-21 |
| DE60321593D1 (de) | 2008-07-24 |
| US7713991B2 (en) | 2010-05-11 |
| AU2003292039A1 (en) | 2004-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |