AU2011297961B2 - Pyrazolopyridinone derivatives as LPA receptor antagonists - Google Patents
Pyrazolopyridinone derivatives as LPA receptor antagonists Download PDFInfo
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- AU2011297961B2 AU2011297961B2 AU2011297961A AU2011297961A AU2011297961B2 AU 2011297961 B2 AU2011297961 B2 AU 2011297961B2 AU 2011297961 A AU2011297961 A AU 2011297961A AU 2011297961 A AU2011297961 A AU 2011297961A AU 2011297961 B2 AU2011297961 B2 AU 2011297961B2
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- pyrazolo
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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| PCT/EP2011/003949 WO2012028243A1 (en) | 2010-09-02 | 2011-08-05 | Pyrazolopyridinone derivatives as lpa receptor antagonists |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG2014011555A (en) | 2011-08-15 | 2014-08-28 | Intermune Inc | Lysophosphatidic acid receptor antagonists |
| EP2850062B1 (en) | 2012-05-18 | 2017-07-19 | Sanofi | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
| RU2645344C2 (ru) * | 2012-05-18 | 2018-02-21 | Санофи | Производные пиразола и их применение в качестве lpar5 антагонистов |
| TWI633087B (zh) | 2012-06-13 | 2018-08-21 | 赫孚孟拉羅股份公司 | 新穎二氮雜螺環烷及氮雜螺環烷 |
| CN104781257A (zh) | 2012-06-14 | 2015-07-15 | 第一三共株式会社 | 哌啶基吡唑并吡啶衍生物 |
| HRP20191937T1 (hr) | 2012-09-25 | 2020-01-10 | F. Hoffmann - La Roche Ag | Derivati heksahidropirolo [3,4-c]pirola i srodni spojevi kao inhibitori autotaksina (atx) i kao inhibitori proizvodnje lizofosfatidne kiseline (lpa) za liječenje npr. bubrežnih bolesti |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
| WO2015050148A1 (ja) * | 2013-10-04 | 2015-04-09 | 第一三共株式会社 | ３－アリールピラゾロピリジン誘導体 |
| WO2015076353A1 (ja) * | 2013-11-25 | 2015-05-28 | 第一三共株式会社 | ３－アルキルピラゾロピリジン誘導体 |
| LT3074400T (lt) | 2013-11-26 | 2018-02-12 | F. Hoffmann-La Roche Ag | Oktahidro-ciklobuta [1,2-c;3,4-c`]dipirolo dariniai kaip autotaksino inhibitoriai |
| WO2015087995A1 (ja) * | 2013-12-13 | 2015-06-18 | 第一三共株式会社 | シクロアルキル又はヘテロシクリルピラゾロピリジン誘導体 |
| KR20160096612A (ko) * | 2013-12-13 | 2016-08-16 | 다이이찌 산쿄 가부시키가이샤 | 5-하이드록시-4-(트리플루오로메틸)피라졸로피리딘 유도체 |
| WO2015087996A1 (ja) * | 2013-12-13 | 2015-06-18 | 第一三共株式会社 | イミダゾピリジン誘導体 |
| US9567288B2 (en) | 2013-12-30 | 2017-02-14 | Rxbio, Inc. | Crystalline salts of (Z)-O-octadec-9-en-1-yl O,O-dihydrogen phosphorothioate |
| WO2015111545A1 (ja) * | 2014-01-21 | 2015-07-30 | 第一三共株式会社 | 縮合ピラゾール誘導体 |
| PE20161223A1 (es) | 2014-03-26 | 2016-11-12 | Hoffmann La Roche | Compuestos condensados de [1,4]diazepina como inhibidores de la produccion de autotaxina (atx) y acido lisofosfatidico (lpa) |
| EA037928B1 (ru) | 2014-03-26 | 2021-06-08 | Ф. Хоффманн-Ля Рош Аг | Бициклические соединения в качестве ингибиторов продукции аутотаксина (atx) и лизофосфатидиловой кислоты (lpa) |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| WO2016197009A1 (en) | 2015-06-05 | 2016-12-08 | Vertex Pharmaceuticals Incorporated | Triazoles for the treatment of demyelinating diseases |
| TWI713534B (zh) * | 2015-06-11 | 2020-12-21 | 日商第一三共股份有限公司 | 5-羥基-4-(三氟甲基)吡唑并吡啶衍生物之結晶及其用途 |
| MX377277B (es) | 2015-09-04 | 2025-03-07 | Hoffmann La Roche | Derivados de fenoximetilo. |
| EP3353178B1 (en) | 2015-09-24 | 2021-07-14 | F. Hoffmann-La Roche AG | Bicyclic compounds as dual atx/ca inhibitors |
| AU2016328535A1 (en) | 2015-09-24 | 2017-11-09 | F. Hoffmann-La Roche Ag | Bicyclic compounds as ATX inhibitors |
| AU2016328365B2 (en) | 2015-09-24 | 2020-04-23 | F. Hoffmann-La Roche Ag | New bicyclic compounds as dual ATX/CA inhibitors |
| CA2991615A1 (en) | 2015-09-24 | 2017-03-30 | F. Hoffmann-La Roche Ag | Bicyclic compounds as atx inhibitors |
| JP7039483B2 (ja) * | 2016-04-14 | 2022-03-22 | マース インコーポレーテッド | Ｇｐｒ９２の調節因子の同定方法 |
| JOP20190024A1 (ar) | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| WO2018106641A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Pyrazoles for the treatment of demyelinating diseases |
| WO2018106646A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Aminotriazoles for the treatment of demyelinating diseases |
| WO2018106643A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Heterocyclic azoles for the treatment of demyelinating diseases |
| BR112019019017A2 (pt) | 2017-03-16 | 2020-04-14 | Hoffmann La Roche | compostos heterocíclicos de utilidade como inibidores duplos de atx/ca |
| JP7090099B2 (ja) | 2017-03-16 | 2022-06-23 | エフ．ホフマン－ラ ロシュ アーゲー | Ａｔｘインヒビターとしての新規二環式化合物 |
| CA3091142C (en) | 2018-02-26 | 2023-04-11 | Gilead Sciences, Inc. | Substituted pyrrolizine compounds and uses thereof |
| US20210024520A1 (en) * | 2018-03-30 | 2021-01-28 | Daiichi Sankyo Company, Limited | Therapeutic agent for lcat deficiency |
| CN108558876B (zh) * | 2018-05-28 | 2020-08-04 | 中南大学 | 吡唑[3,4-b]并吡啶类衍生物及其制备方法和应用 |
| CN108379275B (zh) * | 2018-05-29 | 2020-05-22 | 中国医学科学院阜外医院 | 溶血磷脂酸、溶血磷脂酸受体3以及溶血磷脂酸受体3激动剂的应用 |
| WO2020051551A1 (en) | 2018-09-07 | 2020-03-12 | Mars, Incorporated | Compounds that modulate gpr92 receptor activity and pet food products containing the same |
| US12479816B2 (en) | 2019-02-08 | 2025-11-25 | University of Pittsburgh—of the Commonwealth System of Higher Education | 20-HETE formation inhibitors |
| CA3144075A1 (en) * | 2019-06-20 | 2020-12-24 | University Of Kentucky Research Foundation | Pharmaceutically active pyrazolo-pyridone modulators of dcn1/2-mediated cullin neddylation |
| WO2021116257A1 (en) | 2019-12-12 | 2021-06-17 | Chiesi Farmaceutici S.P.A. | Thienopyrimidine derivatives as lpa receptor 2 inhibitors |
| US12404270B2 (en) | 2019-12-12 | 2025-09-02 | Chiesi Farmaceutici S.P.A. | Quinazoline derivatives as LPA receptor 2 inhibitors |
| WO2021116259A1 (en) | 2019-12-12 | 2021-06-17 | Chiesi Farmaceutici S.P.A. | Aromatic amido derivatives as lpa receptor 2 inhibitors |
| ES2991765T3 (es) | 2020-07-16 | 2024-12-04 | Chiesi Farm Spa | Derivados del ácido amido ciclohexano como inhibidores del receptor de LPA |
| WO2022174882A1 (en) | 2021-02-16 | 2022-08-25 | Chiesi Farmaceutici S.P.A. | 5-membered heterocyclyl carbamate derivatives as dual lpa receptor 1 and lpa receptor 2 inhibitors |
| WO2022174883A1 (en) | 2021-02-16 | 2022-08-25 | Chiesi Farmaceutici S.P.A. | 5-membered heterocyclyl derivatives as dual lpa receptor 1 and lpa receptor 2 inhibitors |
| EP4313956A1 (en) | 2021-03-24 | 2024-02-07 | Chiesi Farmaceutici S.p.A. | 8-cyclo-substituted quinazoline derivatives as lpa receptor 2 inhibitors |
| EP4452965A1 (en) | 2021-12-23 | 2024-10-30 | Chiesi Farmaceutici S.p.A. | Cyclohexane acid derivatives as lpa receptor inhibitors |
| US20250188068A1 (en) | 2022-03-08 | 2025-06-12 | Chiesi Farmaceutici S.P.A. | Amido cyclopropyl derivatives as lpa receptor inhibitors |
| WO2025247961A1 (en) | 2024-05-31 | 2025-12-04 | Centre Hospitalier Universitaire Vaudois (C.H.U.V.) | Lpa-lpar signaling as a therapeutic target or diagnostic tool for brain diseases |
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| GB9904387D0 (en) | 1999-02-25 | 1999-04-21 | Pharmacia & Upjohn Spa | Antitumour synergistic composition |
| AU4972900A (en) | 1999-04-08 | 2000-11-14 | Arch Development Corporation | Use of anti-vegf antibody to enhance radiation in cancer therapy |
| KR100732206B1 (ko) | 2000-09-11 | 2007-06-27 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 티로신 키나제 억제제로서의 퀴놀리논 유도체 |
| ATE447970T1 (de) | 2001-02-08 | 2009-11-15 | Ono Pharmaceutical Co | Mittel zur behandlung von harnwegserkrankungen, umfassend mittel zur kontrolle des lpa-rezeptors |
| EP1513522A2 (en) | 2002-01-18 | 2005-03-16 | Sri International | Methods of treating conditions associated with an edg receptor |
| US20040038856A1 (en) | 2002-05-17 | 2004-02-26 | Sarvajit Chakravarty | Treatment of fibroproliferative disorders using TGF-beta inhibitors |
| PA8580301A1 (es) | 2002-08-28 | 2005-05-24 | Pfizer Prod Inc | Nuevos derivados de benzoimidazol utiles como agentes antiproliferativos |
| US20040167192A1 (en) * | 2003-01-16 | 2004-08-26 | David Solow-Cordero | Methods of treating conditions associated with an Edg-7 receptor |
| EP1641455B1 (en) * | 2003-06-27 | 2008-08-06 | Pfizer Products Inc. | Pyrazolo[3,4-b]pyridin-6-ones as gsk-3 inhibitors |
| DK1678096T3 (da) | 2003-10-09 | 2012-04-23 | Univ Tennessee Res Foundation | LPA-receptoragonister og -antagonister og anvendelsesfremgangsmåder |
| US7820703B2 (en) | 2004-05-06 | 2010-10-26 | University Of Virginia Patent Foundation | Lysophosphatidic acid receptor selective antagonists |
| US20090029949A1 (en) | 2006-05-25 | 2009-01-29 | Parrill-Baker Abby L | GPCR Ligands Identified by Computational Modeling |
| ES2637805T3 (es) | 2008-05-05 | 2017-10-17 | Sanofi | Derivados de ácido ciclopentanocarboxílico fusionados sustituidos por acilamino y su uso como productos farmacéuticos |
| GB2466121B (en) | 2008-12-15 | 2010-12-08 | Amira Pharmaceuticals Inc | Antagonists of lysophosphatidic acid receptors |
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- 2011-08-05 EP EP11741410.2A patent/EP2611808B1/en not_active Not-in-force
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- 2011-08-05 WO PCT/EP2011/003949 patent/WO2012028243A1/en not_active Ceased
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2014
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Non-Patent Citations (1)
| Title |
|---|
| Balicki, R., Polish Journal of Chemistry, 1983, vol. 57, pages 789-797 * |
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| CN103189378A (zh) | 2013-07-03 |
| US20140350046A1 (en) | 2014-11-27 |
| US9067938B2 (en) | 2015-06-30 |
| JP6039559B2 (ja) | 2016-12-07 |
| CA2809892A1 (en) | 2012-03-08 |
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| CA2809892C (en) | 2019-05-28 |
| US20130165478A1 (en) | 2013-06-27 |
| CN103189378B (zh) | 2016-03-02 |
| EP2611808B1 (en) | 2014-11-12 |
| EP2611808A1 (en) | 2013-07-10 |
| ES2530345T3 (es) | 2015-03-02 |
| US8859775B2 (en) | 2014-10-14 |
| IL225015A (en) | 2016-06-30 |
| AU2011297961A1 (en) | 2013-04-18 |
| WO2012028243A1 (en) | 2012-03-08 |
| AR082880A1 (es) | 2013-01-16 |
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