ES2305520T3 - Derivados de imidazo(1,5a)piridina y metodos para tratar enfermedades mediadas por aldosterona. - Google Patents
Derivados de imidazo(1,5a)piridina y metodos para tratar enfermedades mediadas por aldosterona. Download PDFInfo
- Publication number
- ES2305520T3 ES2305520T3 ES03767563T ES03767563T ES2305520T3 ES 2305520 T3 ES2305520 T3 ES 2305520T3 ES 03767563 T ES03767563 T ES 03767563T ES 03767563 T ES03767563 T ES 03767563T ES 2305520 T3 ES2305520 T3 ES 2305520T3
- Authority
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- Prior art keywords
- quad
- hydrogen
- trifluoromethyl
- alkoxy
- optionally substituted
- 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 - Lifetime
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- 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 claims description 11
- 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 claims description 11
- 229960002478 aldosterone Drugs 0.000 title claims description 11
- 238000000034 method Methods 0.000 title description 17
- 230000001404 mediated effect Effects 0.000 title description 4
- 201000010099 disease Diseases 0.000 title description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 7
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 3
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
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- 125000004429 atom Chemical group 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
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- 210000004351 coronary vessel Anatomy 0.000 claims description 4
- 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
- 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
- 206010061216 Infarction Diseases 0.000 claims description 2
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- 210000004165 myocardium Anatomy 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 1
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- -1 4,4-dimethylpentyl Chemical group 0.000 description 38
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 125000003396 thiol group Chemical class [H]S* 0.000 description 9
- 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
- 125000005843 halogen group Chemical group 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 125000002883 imidazolyl group Chemical group 0.000 description 6
- 229940002612 prodrug Drugs 0.000 description 6
- 239000000651 prodrug Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
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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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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
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- 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
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- 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)
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- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (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 (2)
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|---|---|---|---|
| US42732502P | 2002-11-18 | 2002-11-18 | |
| US427325P | 2002-11-18 |
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| ES2305520T3 true ES2305520T3 (es) | 2008-11-01 |
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| 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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| JP4422034B2 (ja) * | 2002-12-06 | 2010-02-24 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | テトラヒドロ−ナフタレン誘導体 |
| EP1572632B1 (en) * | 2002-12-09 | 2008-08-13 | Xention Limited | 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 |
| US7803810B2 (en) * | 2007-03-09 | 2010-09-28 | Probiodrug Ag | Inhibitors |
| ES2448839T3 (es) | 2007-11-01 | 2014-03-17 | Bristol-Myers Squibb Company | Compuestos no esteroideos útiles como moderadores de la actividad del receptor de glucocorticoides AP-1 y/o NF-kappa b y uso de los mismos |
| EP2095819A1 (en) | 2008-02-28 | 2009-09-02 | Maastricht University | N-benzyl imidazole derivatives and their use as aldosterone synthase inhibitors |
| JP5420761B2 (ja) | 2009-05-28 | 2014-02-19 | ノバルティス アーゲー | ネプリリシン阻害剤としての置換アミノプロピオン酸誘導体 |
| KR20120041702A (ko) | 2009-05-28 | 2012-05-02 | 노파르티스 아게 | 네프릴리신 억제제로서의 치환된 아미노부티르산 유도체 |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| WO2011064376A1 (en) * | 2009-11-30 | 2011-06-03 | 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 |
| TWI627167B (zh) | 2011-07-08 | 2018-06-21 | 諾華公司 | 用於高三酸甘油酯個體治療動脈粥狀硬化之方法 |
| EP2757882B1 (en) * | 2011-09-22 | 2020-11-04 | Merck Sharp & Dohme Corp. | Imidazopyridyl compounds as aldosterone synthase inhibitors |
| WO2013043521A1 (en) | 2011-09-22 | 2013-03-28 | Merck Sharp & Dohme Corp. | Pyrazolopyridyl compounds as aldosterone synthase inhibitors |
| EP2757883B1 (en) | 2011-09-22 | 2021-01-13 | Merck Sharp & Dohme Corp. | Triazolopyridyl compounds as aldosterone synthase inhibitors |
| JO3137B1 (ar) | 2012-01-17 | 2017-09-20 | Novartis Ag | أملاح وأشكال جديدة لمثبط إنزيم سينثاز أو أروماتاز ثنائي هيدروبيرولو [2،1-c] إيميدازوليل ألدوستيرون |
| UY35144A (es) | 2012-11-20 | 2014-06-30 | Novartis Ag | Miméticos lineales sintéticos de apelina para el tratamiento de insuficiencia cardiaca |
| WO2014126979A1 (en) | 2013-02-14 | 2014-08-21 | Novartis Ag | Substituted bisphenyl butanoic phosphonic acid derivatives as nep (neutral endopeptidase) inhibitors |
| CA2918074A1 (en) | 2013-07-25 | 2015-01-29 | Novartis Ag | Cyclic polypeptides for the treatment of heart failure |
| CA2918077A1 (en) | 2013-07-25 | 2015-01-29 | Novartis Ag | Bioconjugates of synthetic apelin polypeptides |
| AU2016209968B2 (en) | 2015-01-23 | 2018-11-29 | 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 |
| US20230089867A1 (en) | 2018-11-27 | 2023-03-23 | Novartis Ag | Cyclic pentamer compounds as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorder |
| WO2020110011A1 (en) | 2018-11-27 | 2020-06-04 | Novartis Ag | Cyclic peptides as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorders |
| 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 |
| WO2024241229A1 (en) | 2023-05-24 | 2024-11-28 | Novartis Ag | Naphthyridinone derivatives for the treatment of a disease or disorder |
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| 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 |
| 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 |
| US5428160A (en) * | 1982-12-21 | 1995-06-27 | Ciba-Geigy Corporation | Substituted imidazo[5-a]pyridine derviatives and other substituted bicyclic derivatives |
| 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 |
| 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 |
| 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 AU AU2003292039A patent/AU2003292039A1/en not_active Abandoned
- 2003-11-17 AT AT03767563T patent/ATE398124T1/de not_active IP Right Cessation
- 2003-11-17 ES ES03767563T patent/ES2305520T3/es not_active Expired - Lifetime
- 2003-11-17 WO PCT/EP2003/012851 patent/WO2004046145A1/en not_active Ceased
- 2003-11-17 JP JP2004552632A patent/JP2006508970A/ja active Pending
- 2003-11-17 CN CNB2003801035050A patent/CN100447142C/zh not_active Expired - Fee Related
- 2003-11-17 BR BR0316306-7A patent/BR0316306A/pt not_active IP Right Cessation
- 2003-11-17 PT PT03767563T patent/PT1565463E/pt unknown
- 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 DE DE60321593T patent/DE60321593D1/de not_active Expired - Lifetime
- 2003-11-17 CA CA002505752A patent/CA2505752A1/en not_active Abandoned
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2007
- 2007-04-24 US US11/739,290 patent/US7713991B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PT1565463E (pt) | 2008-09-10 |
| WO2004046145A1 (en) | 2004-06-03 |
| US7223866B2 (en) | 2007-05-29 |
| HK1081540A1 (en) | 2006-05-19 |
| US7713991B2 (en) | 2010-05-11 |
| CN1711262A (zh) | 2005-12-21 |
| AU2003292039A1 (en) | 2004-06-15 |
| JP2006508970A (ja) | 2006-03-16 |
| DE60321593D1 (de) | 2008-07-24 |
| BR0316306A (pt) | 2005-09-27 |
| CN100447142C (zh) | 2008-12-31 |
| EP1565463A1 (en) | 2005-08-24 |
| EP1565463B1 (en) | 2008-06-11 |
| US20070197582A1 (en) | 2007-08-23 |
| US20060058342A1 (en) | 2006-03-16 |
| CA2505752A1 (en) | 2004-06-03 |
| ATE398124T1 (de) | 2008-07-15 |
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