JP2005514432A5 - - Google Patents
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- Publication number
- JP2005514432A5 JP2005514432A5 JP2003559423A JP2003559423A JP2005514432A5 JP 2005514432 A5 JP2005514432 A5 JP 2005514432A5 JP 2003559423 A JP2003559423 A JP 2003559423A JP 2003559423 A JP2003559423 A JP 2003559423A JP 2005514432 A5 JP2005514432 A5 JP 2005514432A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- phenyl
- fluoro
- yloxy
- nitro
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 claims 37
- 125000001072 heteroaryl group Chemical group 0.000 claims 35
- 150000001875 compounds Chemical class 0.000 claims 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 18
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 14
- -1 cyano, ethoxycarbonyl Chemical group 0.000 claims 13
- 125000003107 substituted aryl group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 10
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 238000009472 formulation Methods 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 claims 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 5
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 4
- AEMOBTAPCIDTGO-UHFFFAOYSA-N 4-fluoro-n-(3-pyrazin-2-yl-5-pyridin-3-yloxyphenyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC(OC=2C=NC=CC=2)=CC(C=2N=CC=NC=2)=C1 AEMOBTAPCIDTGO-UHFFFAOYSA-N 0.000 claims 4
- JIWOQJSUFBYTQZ-UHFFFAOYSA-N 4-fluoro-n-(3-pyridin-2-yl-5-pyridin-3-yloxyphenyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC(OC=2C=NC=CC=2)=CC(C=2N=CC=CC=2)=C1 JIWOQJSUFBYTQZ-UHFFFAOYSA-N 0.000 claims 4
- ISELKUFHSCAZAC-UHFFFAOYSA-N 4-fluoro-n-(3-pyridin-3-yloxyphenyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC=CC(OC=2C=NC=CC=2)=C1 ISELKUFHSCAZAC-UHFFFAOYSA-N 0.000 claims 4
- GYOAZJHFJYVZKX-UHFFFAOYSA-N 5-methyl-n-(3-nitro-5-pyridin-3-yloxyphenyl)thiophene-2-carboxamide Chemical compound S1C(C)=CC=C1C(=O)NC1=CC(OC=2C=NC=CC=2)=CC([N+]([O-])=O)=C1 GYOAZJHFJYVZKX-UHFFFAOYSA-N 0.000 claims 4
- 150000003857 carboxamides Chemical class 0.000 claims 4
- XROWCUJOXCTJHT-UHFFFAOYSA-N ethyl 3-[(4-fluorobenzoyl)amino]-5-pyridin-3-yloxybenzoate Chemical compound C=1C(OC=2C=NC=CC=2)=CC(C(=O)OCC)=CC=1NC(=O)C1=CC=C(F)C=C1 XROWCUJOXCTJHT-UHFFFAOYSA-N 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- FFMJZGQEJFSZQJ-UHFFFAOYSA-N n-(3-fluoro-5-pyridin-3-yloxyphenyl)-3-hydroxybenzamide Chemical compound OC1=CC=CC(C(=O)NC=2C=C(OC=3C=NC=CC=3)C=C(F)C=2)=C1 FFMJZGQEJFSZQJ-UHFFFAOYSA-N 0.000 claims 4
- ZUHYXIFIFNZDOT-UHFFFAOYSA-N n-(3-fluoro-5-pyridin-3-yloxyphenyl)-4-hydroxybenzamide Chemical compound C1=CC(O)=CC=C1C(=O)NC1=CC(F)=CC(OC=2C=NC=CC=2)=C1 ZUHYXIFIFNZDOT-UHFFFAOYSA-N 0.000 claims 4
- APXPHJKKKDJVLH-UHFFFAOYSA-N n-(3-fluoro-5-pyridin-3-yloxyphenyl)pyridine-3-carboxamide Chemical compound C=1C(OC=2C=NC=CC=2)=CC(F)=CC=1NC(=O)C1=CC=CN=C1 APXPHJKKKDJVLH-UHFFFAOYSA-N 0.000 claims 4
- UCTCJVQJGDTWRP-UHFFFAOYSA-N n-ethynylacetamide Chemical group CC(=O)NC#C UCTCJVQJGDTWRP-UHFFFAOYSA-N 0.000 claims 4
- 150000002825 nitriles Chemical class 0.000 claims 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 4
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 3
- KQTKQVOTCPHKGP-UHFFFAOYSA-N 4-fluoro-n-(3-nitro-5-pyridin-2-yloxyphenyl)benzamide Chemical compound C=1C(OC=2N=CC=CC=2)=CC([N+](=O)[O-])=CC=1NC(=O)C1=CC=C(F)C=C1 KQTKQVOTCPHKGP-UHFFFAOYSA-N 0.000 claims 3
- UUNHPTMHLNKHQZ-UHFFFAOYSA-N 4-fluoro-n-[3-pyridin-3-yloxy-5-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC(OC=2C=NC=CC=2)=CC(C(F)(F)F)=C1 UUNHPTMHLNKHQZ-UHFFFAOYSA-N 0.000 claims 3
- NTJQVABAGCEGCL-UHFFFAOYSA-N C1=C(NC(=O)C=2C=CC(F)=CC=2)C([N+](=O)[O-])=CC=C1OC1=CC=CN=C1 Chemical compound C1=C(NC(=O)C=2C=CC(F)=CC=2)C([N+](=O)[O-])=CC=C1OC1=CC=CN=C1 NTJQVABAGCEGCL-UHFFFAOYSA-N 0.000 claims 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- YFFUPDRWGSWXNN-UHFFFAOYSA-N n-(3-cyano-5-pyridin-3-yloxyphenyl)-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC(OC=2C=NC=CC=2)=CC(C#N)=C1 YFFUPDRWGSWXNN-UHFFFAOYSA-N 0.000 claims 3
- BTJHUUVOMQUGSX-UHFFFAOYSA-N n-(3-fluoro-5-pyridin-3-yloxyphenyl)-1,2-oxazole-5-carboxamide Chemical compound C=1C(OC=2C=NC=CC=2)=CC(F)=CC=1NC(=O)C1=CC=NO1 BTJHUUVOMQUGSX-UHFFFAOYSA-N 0.000 claims 3
- PSEXQRDMKFURRU-UHFFFAOYSA-N n-[3-(4-fluorophenoxy)-5-nitrophenyl]pyridine-4-carboxamide Chemical compound C=1C(OC=2C=CC(F)=CC=2)=CC([N+](=O)[O-])=CC=1NC(=O)C1=CC=NC=C1 PSEXQRDMKFURRU-UHFFFAOYSA-N 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010071436 Systolic dysfunction Diseases 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 208000019622 heart disease Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- AJQAVCUZDKXXMC-UHFFFAOYSA-N 4-fluoro-N-[3-(fluoromethyl)-5-pyridin-3-yloxyphenyl]benzamide Chemical compound FC1=CC=C(C(=O)NC2=CC(=CC(=C2)CF)OC=2C=NC=CC2)C=C1 AJQAVCUZDKXXMC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002828 nitro derivatives Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34308801P | 2001-12-21 | 2001-12-21 | |
| PCT/US2002/040996 WO2003059258A2 (en) | 2001-12-21 | 2002-12-20 | Compositions and methods for treating heart failure |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004324438A Division JP2005068160A (ja) | 2001-12-21 | 2004-11-08 | 心不全を処置するための組成物および方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005514432A JP2005514432A (ja) | 2005-05-19 |
| JP2005514432A5 true JP2005514432A5 (en:Method) | 2005-12-22 |
| JP4361800B2 JP4361800B2 (ja) | 2009-11-11 |
Family
ID=23344654
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003559423A Expired - Lifetime JP4361800B2 (ja) | 2001-12-21 | 2002-12-20 | 心不全を処置するための組成物および方法 |
| JP2004324438A Withdrawn JP2005068160A (ja) | 2001-12-21 | 2004-11-08 | 心不全を処置するための組成物および方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004324438A Withdrawn JP2005068160A (ja) | 2001-12-21 | 2004-11-08 | 心不全を処置するための組成物および方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US6908923B2 (en:Method) |
| EP (1) | EP1503986B1 (en:Method) |
| JP (2) | JP4361800B2 (en:Method) |
| AU (1) | AU2002367023A1 (en:Method) |
| CA (1) | CA2470427C (en:Method) |
| WO (1) | WO2003059258A2 (en:Method) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6495337B1 (en) * | 2000-03-29 | 2002-12-17 | Cytokinetics, Inc. | High throughput sarcomeric assay |
| WO2003059258A2 (en) * | 2001-12-21 | 2003-07-24 | Cytokinetics, Inc. | Compositions and methods for treating heart failure |
| JP4613157B2 (ja) * | 2003-01-14 | 2011-01-12 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
| PL216049B1 (pl) | 2004-06-17 | 2014-02-28 | Cytokinetics Inc | Pochodne mocznika, kompozycje zawierajace pochodne mocznika oraz zastosowanie pochodnych mocznika do wytwarzania leku do leczenia niewydolnosci serca |
| KR20210090744A (ko) | 2004-09-02 | 2021-07-20 | 제넨테크, 인크. | 헤지호그 신호전달에 대한 피리딜 억제제 |
| US8003657B2 (en) * | 2004-10-13 | 2011-08-23 | Merck Patent Gmbh | Heterocyclic substituted bisarylurea derivatives |
| US7538223B2 (en) | 2005-08-04 | 2009-05-26 | Cytokinetics, Inc. | Compounds, compositions and methods |
| WO2007075377A2 (en) * | 2005-12-15 | 2007-07-05 | Cytokinetics, Inc. | Certain chemical entities, compositions and methods |
| US20070161617A1 (en) | 2005-12-15 | 2007-07-12 | Morgan Bradley P | Certain chemical entities, compositions and methods |
| WO2007078815A2 (en) | 2005-12-16 | 2007-07-12 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| WO2011035209A1 (en) | 2009-09-17 | 2011-03-24 | Vanderbilt Universtiy | Substituted benzamide analogs as mglur5 negative allosteric modulators and methods of making and using the same |
| AU2014353150A1 (en) | 2013-11-19 | 2016-07-07 | Vanderbilt University | Substituted imidazopyridine and triazolopyridine compounds as negative allosteric modulators of mGluR5 |
| US9533982B2 (en) | 2014-03-20 | 2017-01-03 | Vanderbilt University | Substituted bicyclic heteroaryl carboxamide analogs as mGluR5 negative allosteric modulators |
| US9550778B2 (en) | 2014-10-03 | 2017-01-24 | Vanderbilt University | Substituted 6-aryl-imidazopyridine and 6-aryl-triazolopyridine carboxamide analogs as negative allosteric modulators of mGluR5 |
| AR112804A1 (es) | 2017-09-13 | 2019-12-11 | Amgen Inc | Compuestos de bisamida que activan el sarcómero y sus usos |
| BR112020014428A2 (pt) | 2018-01-19 | 2020-12-01 | Cytokinetics, Inc. | composto, composição farmacêutica, e, métodos para o tratamento de uma doença cardíaca em um indivíduo, para o tratamento de uma doença ou condição que está associada com cavidade ventricular esquerda pequena e obliteração da cavidade, contração hiperdinâmica do ventrículo esquerdo, isquemia do miocárdio ou fibrose cardíaca, para o tratamento de uma doença ou condição selecionada dentre distrofias musculares e doenças de armazenamento do glicogênio e para inibição do sarcômero cardíaco |
| LT3781561T (lt) | 2018-04-18 | 2024-07-10 | Constellation Pharmaceuticals, Inc. | Metilą modifikuojančių fermentų moduliatoriai, kompozicijos ir jų naudojimas |
| WO2019226491A1 (en) | 2018-05-21 | 2019-11-28 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| PE20220562A1 (es) | 2019-07-24 | 2022-04-13 | Constellation Pharmaceuticals Inc | Formas cristalinas de 7-cloro-2-(4-(3-metoxiazetidin-1-il)ciclohexil)-2,4-dimetil-n-((6-metil-4-(metiltio)-2-oxo-1,2-dihidropiridin-3-il)metil)benzo[d][1,3]dioxol-5-carboxamida |
| TWI822140B (zh) * | 2021-06-24 | 2023-11-11 | 南韓商Ｌｇ化學股份有限公司 | 作為ｒｏｎ抑制劑之新穎吡啶衍生物化合物 |
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| US3447922A (en) * | 1964-12-28 | 1969-06-03 | Xerox Corp | Electrically photosensitive particles useful in photoelectrophoretic and xerographic imaging processes |
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| US3674850A (en) * | 1969-12-07 | 1972-07-04 | Lever Brothers Ltd | Substituted salicylanilides |
| DE2248662A1 (de) * | 1972-10-04 | 1974-04-18 | Bayer Ag | Loesliche aromatische copolyamide und daraus hergestellte faeden mit hohem elastizitaetsmodul und hoher reissfestigkeit |
| DE3139457A1 (de) | 1981-10-03 | 1983-04-21 | Bayer Ag, 5090 Leverkusen | Neue substituierte benzanilidether, verfahren zu ihrer herstellung, ihre verwendung als fungizide und zwischenprodukte hierfuer |
| FR2601015B1 (fr) | 1986-07-04 | 1988-08-05 | Rhone Poulenc Sante | Nouveaux derives du 1h,3h-pyrrolo (1,2-c) thiazole, leur preparation et les compositions pharmaceutiques qui les contiennent |
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| JP2795519B2 (ja) | 1990-04-11 | 1998-09-10 | 三井化学株式会社 | 芳香族ポリアミド |
| JP2821564B2 (ja) | 1991-05-29 | 1998-11-05 | 住化ファインケム株式会社 | キナゾリノン誘導体の製造方法 |
| FR2687574B1 (fr) | 1992-02-25 | 1995-05-05 | Rhone Poulenc Rorer Sa | Nouvelle application therapeutique de derives du pyridylpyrrolothiazole carboxamide. |
| WO1994022830A1 (en) * | 1993-03-31 | 1994-10-13 | Smithkline Beecham Corporation | Chemical compounds |
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| WO2001005769A2 (en) | 1999-07-20 | 2001-01-25 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
| US6355660B1 (en) | 1999-07-20 | 2002-03-12 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
| BR0013469B1 (pt) | 1999-08-20 | 2011-01-25 | amidas aromáticas heterocìclicas fungicidas, composição fungicida compreendendo as mesmas, bem como método para o controle ou a prevenção de infestação fúngica. | |
| DE10010002A1 (de) | 2000-03-02 | 2001-09-06 | Celanese Ventures Gmbh | Verfahren zur Nitrierung und Aminierung von Arylpolymer |
| US6495337B1 (en) * | 2000-03-29 | 2002-12-17 | Cytokinetics, Inc. | High throughput sarcomeric assay |
| CA2407587A1 (en) * | 2000-04-28 | 2001-11-08 | Sankyo Company, Limited | Ppar.gamma. modulators |
| DE10110002B4 (de) | 2001-03-01 | 2006-03-09 | Georg Oswald Lange | Toilettensitz |
| JP4933730B2 (ja) | 2001-05-04 | 2012-05-16 | パラテック ファーマシューティカルズ インコーポレイテッド | 転写因子調節化合物およびその使用法 |
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| WO2003059258A2 (en) | 2001-12-21 | 2003-07-24 | Cytokinetics, Inc. | Compositions and methods for treating heart failure |
| JPWO2003103654A1 (ja) * | 2002-06-10 | 2005-10-06 | 株式会社医薬分子設計研究所 | ＮＦ−κＢ活性化阻害剤 |
| EA010835B1 (ru) | 2002-06-10 | 2008-12-30 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | Лекарственное средство для лечения рака |
| TWI280127B (en) | 2002-06-11 | 2007-05-01 | Inst Med Molecular Design Inc | Remedies for neurodegenerative diseases |
-
2002
- 2002-12-20 WO PCT/US2002/040996 patent/WO2003059258A2/en not_active Ceased
- 2002-12-20 JP JP2003559423A patent/JP4361800B2/ja not_active Expired - Lifetime
- 2002-12-20 AU AU2002367023A patent/AU2002367023A1/en not_active Abandoned
- 2002-12-20 US US10/327,219 patent/US6908923B2/en not_active Expired - Lifetime
- 2002-12-20 CA CA2470427A patent/CA2470427C/en not_active Expired - Lifetime
- 2002-12-20 EP EP02806491.3A patent/EP1503986B1/en not_active Expired - Lifetime
-
2004
- 2004-11-08 JP JP2004324438A patent/JP2005068160A/ja not_active Withdrawn
-
2005
- 2005-01-20 US US11/040,478 patent/US7053094B2/en not_active Expired - Lifetime
-
2006
- 2006-02-14 US US11/353,252 patent/US7605164B2/en not_active Expired - Lifetime
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