DK2444399T3 - Oxadiazole derivatives and their use as enhancers of metabotropic glutamate receptors - 842 - Google Patents
Oxadiazole derivatives and their use as enhancers of metabotropic glutamate receptors - 842 Download PDFInfo
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- DK2444399T3 DK2444399T3 DK11195016T DK11195016T DK2444399T3 DK 2444399 T3 DK2444399 T3 DK 2444399T3 DK 11195016 T DK11195016 T DK 11195016T DK 11195016 T DK11195016 T DK 11195016T DK 2444399 T3 DK2444399 T3 DK 2444399T3
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| US94255307P | 2007-06-07 | 2007-06-07 | |
| EP08779348.5A EP2167502B3 (en) | 2007-06-07 | 2008-06-05 | Oxadiazole derivatives and their use as metabotropic glutamate receptor potentiators - 842 |
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| TW200804281A (en) * | 2006-02-16 | 2008-01-16 | Astrazeneca Ab | New metabotropic glutamate receptor-potentiating isoindolones |
| AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TWI417100B (zh) * | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-８４２之用途 |
| TW200911255A (en) | 2007-06-07 | 2009-03-16 | Astrazeneca Ab | Metabotropic glutamate receptor oxadiazole ligands and their use as potentiators-841 |
| US8722894B2 (en) | 2007-09-14 | 2014-05-13 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
| CA2697399C (en) | 2007-09-14 | 2016-01-19 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
| MX2010002536A (es) | 2007-09-14 | 2010-08-10 | Ortho Mcneil Janssen Pharm | 4-fenil-3,4,5,6-tetrahidro-2h, 1'h-[1,4]bipiridinil-2'-onas 1',3'-disubstituidas. |
| MX2010005110A (es) * | 2007-11-14 | 2010-09-09 | Ortho Mcneil Janssen Pharm | Derivados de imidazo[1,2-a]piridina y su uso como moduladores alostericos positivos de los receptores de glutamato metabotropico 2. |
| SA109300358B1 (ar) * | 2008-06-06 | 2012-11-03 | استرازينيكا ايه بي | مقويات مستقبل جلوتامات ذي انتحاء أيضي من أيزو إندولون |
| TWI488854B (zh) | 2008-06-20 | 2015-06-21 | Astrazeneca Ab | 二苯并噻氮呯衍生物及其用途 |
| BRPI0918055A2 (pt) | 2008-09-02 | 2015-12-01 | Addex Pharmaceuticals Sa | derivados de 3-azabiciclo[3,1,0]hexila como moduladores de receptores metabotrópicos de glutamato. |
| JP5656848B2 (ja) | 2008-10-16 | 2015-01-21 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | 代謝型グルタミン酸受容体モジュレーターとしてのインドールおよびベンゾモルホリンの誘導体 |
| CA2744138C (en) | 2008-11-28 | 2015-08-11 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| SG176021A1 (en) | 2009-05-12 | 2011-12-29 | Janssen Pharmaceuticals Inc | 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
| ES2409006T3 (es) | 2009-05-12 | 2013-06-24 | Janssen Pharmaceuticals Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de los receptores mGluR2 |
| KR20120112749A (ko) | 2010-01-07 | 2012-10-11 | 아스트라제네카 아베 | 대사성 글루타메이트 수용체 양성 알로스테릭한 모듈레이터 - 874 제조 방법 |
| AU2011245737A1 (en) * | 2010-04-30 | 2012-12-20 | Astrazeneca Ab | Polymorphs of a metabotropic glutamate receptor positive allosteric modulator |
| PL2649069T3 (pl) | 2010-11-08 | 2016-01-29 | Janssen Pharmaceuticals Inc | Pochodne 1,2,4-triazolo[4,3-a]pirydyny i ich zastosowanie jako dodatnich allosterycznych modulatorów receptorów mGluR2 |
| WO2012062759A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| US9012448B2 (en) | 2010-11-08 | 2015-04-21 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| CN102180872B (zh) * | 2011-04-01 | 2014-04-02 | 华中科技大学 | [1,3,4]噁二唑类衍生物及其应用 |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| PT3096790T (pt) | 2014-01-21 | 2019-10-15 | Janssen Pharmaceutica Nv | Combinações compreendendo moduladores alostéricos positivos ou agonistas ortostéricos do recetor glutamatérgico metabotrópico do subtipo 2 e seu uso |
| EA202192105A3 (ru) | 2014-02-04 | 2022-02-28 | Янссен Фармацевтика Нв | Комбинации, содержащие положительные аллостерические модуляторы или ортостерические агонисты метаботропного глутаматергического рецептора 2 подтипа, и их применение |
| US10357484B2 (en) * | 2015-07-17 | 2019-07-23 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| BR112018000906A2 (pt) | 2015-07-17 | 2018-09-11 | Takeda Pharmaceuticals Co | ?composto, medicamento, métodos de inibição da histona desacetilase em um mamífero, e para a profilaxia ou o tratamento de doenças, e, uso de um composto? |
| JPWO2017033946A1 (ja) | 2015-08-25 | 2018-06-07 | 武田薬品工業株式会社 | 複素環化合物 |
| US11396502B2 (en) | 2018-11-13 | 2022-07-26 | Incyte Corporation | Substituted heterocyclic derivatives as PI3K inhibitors |
| US11161838B2 (en) | 2018-11-13 | 2021-11-02 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
| US11078204B2 (en) | 2018-11-13 | 2021-08-03 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
| IL289891B2 (en) * | 2019-07-18 | 2025-06-01 | Abaxys Therapeutics | Solid formulation of a 1,2,4-oxadiazole derivative |
| GB2621323A (en) * | 2022-08-03 | 2024-02-14 | Sirgartan Holdings Ltd | Treatments for obsessive compulsive disorder |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2008803A (en) * | 1932-04-18 | 1935-07-23 | Stephan Engineering Corp | Fuel atomizing and igniting means |
| US3993617A (en) | 1975-10-30 | 1976-11-23 | Morton-Norwich Products, Inc. | Antifungal 2-substituted phthalimidines |
| US5175157A (en) | 1985-11-27 | 1992-12-29 | Boehringer Ingelheim Gmbh | Cyclic amine derivatives, pharmaceutical compositions containing these compounds and methods for preparing them |
| WO1992017448A1 (fr) | 1991-04-01 | 1992-10-15 | Kyowa Hakko Kogyo Co., Ltd. | Derive de 3-methylenisoindolin-1-one |
| TW219935B (enExample) | 1991-12-25 | 1994-02-01 | Mitsubishi Chemicals Co Ltd | |
| EP0602814A1 (en) | 1992-12-18 | 1994-06-22 | Takeda Chemical Industries, Ltd. | Crystal forms of optically active isoindolines and their use |
| RU2124511C1 (ru) * | 1993-05-14 | 1999-01-10 | Фармасьютикал Ко., Лтд | Производные пиперазина |
| US5681954A (en) | 1993-05-14 | 1997-10-28 | Daiichi Pharmaceutical Co., Ltd. | Piperazine derivatives |
| WO1997029079A1 (en) | 1996-02-06 | 1997-08-14 | Japan Tobacco Inc. | Novel compounds and pharmaceutical use thereof |
| EP0999208A4 (en) | 1997-05-30 | 2001-08-08 | Meiji Seika Kaisha | NITROGEN-BASED HETEROCYCLIC COMPOUNDS AND MEDICINES FOR TREATING HYPERLIPEMIA THAT CONTAIN THEM |
| CA2311131A1 (en) | 1997-11-21 | 1999-06-03 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists for treating central nervous system diseases |
| ATE366249T1 (de) | 2000-02-29 | 2007-07-15 | Mitsubishi Pharma Corp | Zyklische amid-derivate |
| CN1444573A (zh) | 2000-07-31 | 2003-09-24 | 史密丝克莱恩比彻姆有限公司 | 甲酰胺化合物及其作为人11cby受体拮抗剂的用途 |
| DE60231608D1 (de) * | 2001-04-19 | 2009-04-30 | Eisai R&D Man Co Ltd | Cyclische amidinderivate |
| PL368129A1 (en) | 2001-08-09 | 2005-03-21 | Ono Pharmaceutical Co, Ltd. | Carboxylic acid derivative compounds and drugs comprising these compounds as the active ingredient |
| WO2003087044A2 (en) | 2002-04-09 | 2003-10-23 | 7Tm Pharma A/S | Novel carboxamide compounds for use in mch receptor related disorders |
| FR2840302B1 (fr) | 2002-06-03 | 2004-07-16 | Aventis Pharma Sa | Derives d'isoindolones, procede de preparation et intermediaire de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
| DE10238865A1 (de) | 2002-08-24 | 2004-03-11 | Boehringer Ingelheim International Gmbh | Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| GB0223232D0 (en) | 2002-10-07 | 2002-11-13 | Pfizer Ltd | Chemical compounds |
| WO2004048332A1 (ja) * | 2002-11-26 | 2004-06-10 | Maruishi Pharmaceutical Co., Ltd. | イソインドリン誘導体 |
| JP2006521358A (ja) | 2003-03-26 | 2006-09-21 | メルク エンド カムパニー インコーポレーテッド | 代謝調節型グルタミン酸受容体のベンズアミドモジュレータ |
| GB0308025D0 (en) | 2003-04-07 | 2003-05-14 | Glaxo Group Ltd | Compounds |
| US7129260B2 (en) | 2003-06-02 | 2006-10-31 | Abbott Laboratories | Isoindolinone kinase inhibitors |
| CA2542220A1 (en) | 2003-10-22 | 2005-05-06 | Eli Lilly And Company | Novel mch receptor antagonists |
| EP1713775A4 (en) | 2004-01-30 | 2009-08-12 | Smithkline Beecham Corp | CHEMICAL COMPOUNDS |
| MY152888A (en) * | 2004-02-18 | 2014-11-28 | Astrazeneca Ab | Fused heterocyclic compounds and their use as metabotropic glutamate receptor antagonists. |
| CN102558082B (zh) | 2004-03-05 | 2015-09-30 | 日产化学工业株式会社 | 异噁唑啉取代苯甲酰胺化合物的制备中间体 |
| CN1934094A (zh) | 2004-03-05 | 2007-03-21 | 万有制药株式会社 | 二芳基取代杂环5元环衍生物 |
| SE0400970D0 (sv) | 2004-04-14 | 2004-04-14 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| TW200613272A (en) * | 2004-08-13 | 2006-05-01 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
| CN101048157A (zh) | 2004-10-25 | 2007-10-03 | 默克公司 | 代谢型谷氨酸受体的杂环二氢茚酮增强剂 |
| WO2006091496A2 (en) | 2005-02-24 | 2006-08-31 | Merck & Co., Inc. | Benzazole potentiators of metabotropic glutamate receptors |
| JP2008540635A (ja) * | 2005-05-18 | 2008-11-20 | アデックス ファーマ ソシエテ アノニム | 代謝型グルタミン酸受容体の正のアロステリック調節因子としての置換されたオキシジアゾール誘導体 |
| GB0510142D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| TW200728277A (en) | 2005-06-29 | 2007-08-01 | Palau Pharma Sa | Bicyclic derivatives as P38 inhibitors |
| US7807706B2 (en) | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
| JP5031745B2 (ja) * | 2005-08-12 | 2012-09-26 | アストラゼネカ アクチボラグ | 代謝型グルタミン酸受容体増強性イソインドロン |
| US7868008B2 (en) | 2005-08-12 | 2011-01-11 | Astrazeneca Ab | Substituted isoindolones and their use as metabotropic glutamate receptor potentiators |
| ES2340321T3 (es) * | 2005-09-27 | 2010-06-01 | F.Hoffmann-La Roche Ag | Oxadiazolilpirazolo-pirimidinas, como antagonistas de mglur2. |
| TW200804281A (en) | 2006-02-16 | 2008-01-16 | Astrazeneca Ab | New metabotropic glutamate receptor-potentiating isoindolones |
| TWI417100B (zh) * | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-８４２之用途 |
| TW200911255A (en) | 2007-06-07 | 2009-03-16 | Astrazeneca Ab | Metabotropic glutamate receptor oxadiazole ligands and their use as potentiators-841 |
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