KR20010108032A - 갑상선 수용체 리간드 - Google Patents
갑상선 수용체 리간드 Download PDFInfo
- Publication number
- KR20010108032A KR20010108032A KR1020017007766A KR20017007766A KR20010108032A KR 20010108032 A KR20010108032 A KR 20010108032A KR 1020017007766 A KR1020017007766 A KR 1020017007766A KR 20017007766 A KR20017007766 A KR 20017007766A KR 20010108032 A KR20010108032 A KR 20010108032A
- Authority
- KR
- South Korea
- Prior art keywords
- hydroxy
- isopropylphenoxy
- dibromo
- benzoyl
- phenylacetyl
- 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.)
- Ceased
Links
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Classifications
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- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
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- C07C235/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C07C307/04—Diamides of sulfuric acids
- C07C307/06—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to acyclic carbon atoms
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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Applications Claiming Priority (3)
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| GB9828442.5 | 1998-12-24 | ||
| GBGB9828442.5A GB9828442D0 (en) | 1998-12-24 | 1998-12-24 | Novel thyroid receptor ligands and method II |
| PCT/IB1999/002084 WO2000039077A2 (en) | 1998-12-24 | 1999-12-23 | Thyroid receptor ligands |
Publications (1)
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| KR20010108032A true KR20010108032A (ko) | 2001-12-07 |
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| KR1020017007766A Ceased KR20010108032A (ko) | 1998-12-24 | 1999-12-23 | 갑상선 수용체 리간드 |
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| TR (1) | TR200101834T2 (enExample) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190042029A (ko) * | 2016-08-12 | 2019-04-23 | 오레곤 헬스 앤드 사이언스 유니버시티 | 아마이드 화합물, 이의 약학 조성물 및 이들을 이용하는 방법 |
Families Citing this family (132)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1127882A1 (en) * | 2000-01-25 | 2001-08-29 | Pfizer Products Inc. | Tetrazole compounds as thyroid receptor ligands |
| US6664291B2 (en) | 2000-03-31 | 2003-12-16 | Pfizer, Inc. | Malonamic acids and derivatives thereof as thyroid receptor ligands |
| FI107018B (fi) * | 2000-04-06 | 2001-05-31 | Ipsat Therapies Oy | Dermatologinen käyttö ja valmiste |
| US6395784B1 (en) * | 2000-06-07 | 2002-05-28 | Bristol-Myers Squibb Company | Benzamide ligands for the thyroid receptor |
| DE10038007A1 (de) * | 2000-08-04 | 2002-02-14 | Bayer Ag | Neue Amino-und Amido-Diphenylether für Arzneimittel |
| US7163918B2 (en) | 2000-08-22 | 2007-01-16 | New River Pharmaceuticals Inc. | Iodothyronine compositions |
| GB0029100D0 (en) * | 2000-11-29 | 2001-01-10 | Karobio Ab | Compounds active at the glucocorticoid receptor |
| CA2433100A1 (en) | 2000-12-27 | 2002-07-04 | Helmut Haning | Indole derivatives as ligands of thyroid receptors |
| US7504435B2 (en) | 2001-01-31 | 2009-03-17 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Method for stimulating weight loss and/or for lowering triglycerides in patients |
| JP2004531479A (ja) * | 2001-02-08 | 2004-10-14 | カロ バイオ アクチェブラーグ | 甲状腺受容体リガンドとしてのフェノキシ置換されたベンゾ縮合ヘテロアリール誘導体 |
| US6777442B2 (en) | 2001-03-12 | 2004-08-17 | Bayer Aktiengesellschaft | Diphenyl derivatives |
| DE10122443A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Ag | Amido-Diphenyl-Derivate |
| GB0120691D0 (en) * | 2001-08-24 | 2001-10-17 | Karobio Ab | Novel Compounds |
| KR20040027927A (ko) | 2001-08-24 | 2004-04-01 | 카로 바이오 아베 | 심장 및 대사 장애의 치료를 위해 주요 환이 치환된갑상선 수용체 길항근 |
| DE60208132T2 (de) | 2001-09-26 | 2006-07-20 | Pfizer Products Inc., Groton | Indolcaroboxylsäure als Thyroidrezeptor-Liganden |
| WO2003064369A1 (en) * | 2002-01-30 | 2003-08-07 | Kissei Pharmaceutical Co., Ltd. | Novel thyroid hormone receptor ligand, medicinal compositions containing the same and use thereof |
| GB0208384D0 (en) * | 2002-04-11 | 2002-05-22 | Karobio Ab | Novel compounds |
| GB0215978D0 (en) * | 2002-07-10 | 2002-08-21 | Karobio Ab | Novel compounds |
| ES2392200T3 (es) * | 2002-09-19 | 2012-12-05 | Eli Lilly & Company | Ésteres de diarilo como antagonistas del receptor opiáceo |
| EP1477475A1 (en) * | 2003-05-16 | 2004-11-17 | Procorde GmbH | Compounds for use as a medicine increasing the contractility of a heart, a heart muscle or cells of a heart muscle |
| ITRM20030363A1 (it) * | 2003-07-24 | 2005-01-25 | Fernando Goglia | Composizioni comprendenti la 3, 5diiodotironina e uso farmaceutico di esse. |
| US7767828B2 (en) * | 2003-11-12 | 2010-08-03 | Phenomix Corporation | Methyl and ethyl substituted pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| AR046778A1 (es) | 2003-11-12 | 2005-12-21 | Phenomix Corp | Compuestos heterociclicos de acido boronico. metodos de obtencion y composiciones farmaceuticas. |
| US7576121B2 (en) * | 2003-11-12 | 2009-08-18 | Phenomix Corporation | Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| US7317109B2 (en) * | 2003-11-12 | 2008-01-08 | Phenomix Corporation | Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| AU2006249350B2 (en) | 2003-11-19 | 2012-02-16 | Metabasis Therapeutics, Inc. | Thyromimetics for the treatment of fatty liver diseases |
| JP2007512359A (ja) | 2003-11-19 | 2007-05-17 | メタバシス・セラピューティクス・インコーポレイテッド | 新規なリン含有甲状腺ホルモン様物質 |
| US7795448B2 (en) | 2004-05-06 | 2010-09-14 | Cytokinetics, Incorporated | Imidazoyl-benzamide anti-cancer agents |
| US7618981B2 (en) | 2004-05-06 | 2009-11-17 | Cytokinetics, Inc. | Imidazopyridinyl-benzamide anti-cancer agents |
| US7504413B2 (en) | 2004-05-06 | 2009-03-17 | Cytokinetics, Inc. | N-(4-(imidazo[1,2A]pyridin-YL)phenethyl)benzamide inhibitors of the mitotic kinesin CENP-E for treating certain cellular proliferation diseases |
| UA87854C2 (en) | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
| US7317024B2 (en) | 2005-01-13 | 2008-01-08 | Bristol-Myers Squibb Co. | Heterocyclic modulators of the glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| WO2006113261A2 (en) | 2005-04-14 | 2006-10-26 | Bristol-Myers Squibb Company | Inhibitors of 11-beta hydroxysteroid dehydrogenase type i |
| US7521557B2 (en) | 2005-05-20 | 2009-04-21 | Bristol-Myers Squibb Company | Pyrrolopyridine-based inhibitors of dipeptidyl peptidase IV and methods |
| US7825139B2 (en) * | 2005-05-25 | 2010-11-02 | Forest Laboratories Holdings Limited (BM) | Compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| US7317012B2 (en) | 2005-06-17 | 2008-01-08 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoind-1 receptor modulators |
| US7632837B2 (en) | 2005-06-17 | 2009-12-15 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid-1 receptor modulators |
| US7629342B2 (en) | 2005-06-17 | 2009-12-08 | Bristol-Myers Squibb Company | Azabicyclic heterocycles as cannabinoid receptor modulators |
| US7572808B2 (en) | 2005-06-17 | 2009-08-11 | Bristol-Myers Squibb Company | Triazolopyridine cannabinoid receptor 1 antagonists |
| US7452892B2 (en) | 2005-06-17 | 2008-11-18 | Bristol-Myers Squibb Company | Triazolopyrimidine cannabinoid receptor 1 antagonists |
| RU2394560C2 (ru) | 2005-07-19 | 2010-07-20 | Дайити Санкио Компани, Лимитед | Замещенное пропанамидное производное и фармацевтическая композиция, содержащая такое производное |
| BRPI0615150A2 (pt) * | 2005-08-10 | 2017-06-20 | Takeda Pharmaceuticals Co | agente para a profilaxia ou tratamento de diabete, sensibilizador de insulina, composto, pró-droga, agente farmacêutico, e, uso do composto ou um sal do mesmo ou uma pró-droga do mesmo |
| US7795436B2 (en) | 2005-08-24 | 2010-09-14 | Bristol-Myers Squibb Company | Substituted tricyclic heterocycles as serotonin receptor agonists and antagonists |
| AR056155A1 (es) | 2005-10-26 | 2007-09-19 | Bristol Myers Squibb Co | Antagonistas del receptor 1 de la hormona de concentracion de melanina no basica |
| US7488725B2 (en) | 2005-10-31 | 2009-02-10 | Bristol-Myers Squibb Co. | Pyrrolidinyl beta-amino amide-based inhibitors of dipeptidyl peptidase IV and methods |
| TW200738621A (en) * | 2005-11-28 | 2007-10-16 | Astrazeneca Ab | Chemical process |
| US7553836B2 (en) | 2006-02-06 | 2009-06-30 | Bristol-Myers Squibb Company | Melanin concentrating hormone receptor-1 antagonists |
| CN101466676B (zh) * | 2006-04-12 | 2012-07-18 | 默沙东公司 | 吡啶基酰胺类t-型钙通道拮抗剂 |
| WO2007120083A1 (en) * | 2006-04-13 | 2007-10-25 | Astrazeneca Ab | The use of carboxamide derivatives in the manufacture of a medicament for the treatment of inflammatory, allergic and dermatological conditions |
| FR2900404B1 (fr) * | 2006-04-27 | 2008-07-18 | Sod Conseils Rech Applic | Nouveaux derives d'imidazoles, leur preparation et leur utilisation en tant que medicament |
| WO2007132475A1 (en) * | 2006-05-15 | 2007-11-22 | Cadila Healthcare Limited | Selective tr-beta 1 agonist |
| WO2007139589A1 (en) | 2006-05-26 | 2007-12-06 | Bristol-Myers Squibb Company | Sustained release glp-1 receptor modulators |
| US7919598B2 (en) | 2006-06-28 | 2011-04-05 | Bristol-Myers Squibb Company | Crystal structures of SGLT2 inhibitors and processes for preparing same |
| US7727978B2 (en) | 2006-08-24 | 2010-06-01 | Bristol-Myers Squibb Company | Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| JP2010508358A (ja) | 2006-11-01 | 2010-03-18 | 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、並びにその使用 |
| EP2089355A2 (en) | 2006-11-01 | 2009-08-19 | Brystol-Myers Squibb Company | Modulators of glucocorticoid receptor, ap-1, and/or nf- kappa b activity and use thereof |
| RU2395489C2 (ru) * | 2006-11-01 | 2010-07-27 | Институт элементоорганических соединений имени А.Н.Несмеянова Российской академии наук (ИНЭОС РАН) | [f-18] меченная l-глютаминовая кислота, [f-18] меченный l-глютамин, их производные и их применение, а также способ их получения |
| JP5362585B2 (ja) | 2007-01-31 | 2013-12-11 | チバ ホールディング インコーポレーテッド | カチオン性染料 |
| US8399518B2 (en) | 2007-02-27 | 2013-03-19 | University Of Arizona Office Of Technology Transfer | Administration of 3,5-diiodothyropropionic acid for stimulating weight loss, and/or lowering triglyceride levels, and/or treatment of metabolic syndrome |
| PE20090185A1 (es) | 2007-03-22 | 2009-02-28 | Bristol Myers Squibb Co | Formulaciones farmaceuticas que contienen un inhibidor sglt2 |
| EP2474549A1 (en) | 2007-04-17 | 2012-07-11 | Bristol-Myers Squibb Company | Fused heterocyclic 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| PE20090696A1 (es) | 2007-04-20 | 2009-06-20 | Bristol Myers Squibb Co | Formas cristalinas de saxagliptina y procesos para preparar las mismas |
| US20090011994A1 (en) | 2007-07-06 | 2009-01-08 | Bristol-Myers Squibb Company | Non-basic melanin concentrating hormone receptor-1 antagonists and methods |
| CN101808995A (zh) | 2007-07-27 | 2010-08-18 | 百时美施贵宝公司 | 新颖的葡糖激酶激活剂及其使用方法 |
| EP2197873B1 (en) * | 2007-09-20 | 2014-07-16 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
| CA2701594C (en) * | 2007-10-24 | 2014-02-18 | Merck Sharp & Dohme Corp. | Heterocycle phenyl amide t-type calcium channel antagonists |
| US8309730B2 (en) | 2007-11-01 | 2012-11-13 | Bristol-Myers Squibb Company | Nonsteroidal compounds useful as modulators of glucocorticoid receptor AP-1 and/or NF-kappab acitivity and use thereof |
| GB0725214D0 (en) * | 2007-12-24 | 2008-02-06 | Karobio Ab | Pharmaceutical compounds |
| PE20091928A1 (es) | 2008-05-29 | 2009-12-31 | Bristol Myers Squibb Co | Tienopirimidinas hidroxisustituidas como antagonistas de receptor-1 de hormona concentradora de melanina no basicos |
| KR20110077018A (ko) * | 2008-10-27 | 2011-07-06 | 카딜라 핼쓰캐어 리미티드 | 갑상선 수용체 리간드 |
| KR101657323B1 (ko) | 2008-11-19 | 2016-09-13 | 포라 가세이 고교 가부시키가이샤 | 주름 개선제 |
| WO2010086878A2 (en) | 2009-01-09 | 2010-08-05 | Cadila Healthcare Limited | Thyroid receptor modulators |
| CA2756786A1 (en) | 2009-03-27 | 2010-09-30 | Bristol-Myers Squibb Company | Methods for preventing major adverse cardiovascular events with dpp-iv inhibitors |
| JP5487202B2 (ja) * | 2009-04-20 | 2014-05-07 | 田辺三菱製薬株式会社 | 新規甲状腺ホルモンβ受容体作動薬 |
| ES2693686T3 (es) | 2009-11-13 | 2018-12-13 | Astrazeneca Ab | Formulaciones de comprimidos de liberación inmediata |
| BR112012011274A2 (pt) | 2009-11-13 | 2016-04-12 | Astrazeneca Uk Ltd | formulação de metformina de massa reduzida e sua combinação |
| WO2011060256A2 (en) | 2009-11-13 | 2011-05-19 | Bristol-Myers Squibb Company | Bilayer tablet formulations |
| WO2011103126A1 (en) * | 2010-02-17 | 2011-08-25 | Ampla Pharmaceuticals Inc. | Treatment of metabolic syndrome with piperidine amides |
| CN102971313A (zh) | 2010-04-14 | 2013-03-13 | 百时美施贵宝公司 | 新颖的葡糖激酶激活剂及其使用方法 |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| EP2590951B1 (en) | 2010-07-09 | 2015-01-07 | Pfizer Limited | Benzenesulfonamides useful as sodium channel inhibitors |
| WO2012007868A2 (en) | 2010-07-12 | 2012-01-19 | Pfizer Limited | Chemical compounds |
| CA2804351A1 (en) | 2010-07-12 | 2012-01-19 | Pfizer Limited | Chemical compounds |
| ES2525581T3 (es) | 2010-07-12 | 2014-12-26 | Pfizer Limited | Derivados de N-sulfonilbenzamida útiles como inhibidores del canal de sodio dependiente de voltaje |
| EP2593427B1 (en) | 2010-07-12 | 2014-12-24 | Pfizer Limited | Sulfonamide derivatives as nav1.7 inhibitors for the treatment of pain |
| US9102621B2 (en) | 2010-07-12 | 2015-08-11 | Pfizer Limited | Acyl sulfonamide compounds |
| US9630929B2 (en) | 2011-10-31 | 2017-04-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| RU2014121983A (ru) | 2011-10-31 | 2015-12-10 | Ксенон Фармасьютикалз Инк. | Биарильные простоэфирные сульфонамиды и их применение в качестве терапевтических средств |
| EP2791108B1 (en) | 2011-12-15 | 2016-07-27 | Pfizer Limited | Sulfonamide derivatives |
| WO2013102826A1 (en) * | 2012-01-04 | 2013-07-11 | Pfizer Limited | N-aminosulfonyl benzamides |
| US8952169B2 (en) | 2012-05-22 | 2015-02-10 | Xenon Pharmaceuticals Inc. | N-substituted benzamides and methods of use thereof |
| CN102718718B (zh) * | 2012-05-31 | 2014-09-24 | 绍兴文理学院 | 一种3,5-二溴-4-(5-苯并咪唑氧基)苯乙酸的制备方法 |
| CN104797555B (zh) * | 2012-07-06 | 2017-12-22 | 基因泰克公司 | N‑取代的苯甲酰胺及其使用方法 |
| EP2892897A1 (en) | 2012-09-05 | 2015-07-15 | Bristol-Myers Squibb Company | Pyrrolone or pyrrolidinone melanin concentrating hormone receptor-1 antagonists |
| WO2014039411A1 (en) | 2012-09-05 | 2014-03-13 | Bristol-Myers Squibb Company | Pyrrolone or pyrrolidinone melanin concentrating hormore receptor-1 antagonists |
| HK1213476A1 (zh) | 2013-03-14 | 2016-07-08 | 基因泰克公司 | 取代的三唑並吡啶及其使用方法 |
| CA2898680A1 (en) | 2013-03-15 | 2014-09-18 | Genentech,Inc. | Substituted benzoxazoles and methods of use thereof |
| US9593113B2 (en) | 2013-08-22 | 2017-03-14 | Bristol-Myers Squibb Company | Imide and acylurea derivatives as modulators of the glucocorticoid receptor |
| CA2931732A1 (en) | 2013-11-27 | 2015-06-04 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| CN103709094B (zh) * | 2014-01-07 | 2016-04-06 | 厦门大学 | 4-苯氧基苯甲酰胺类化合物及其制备方法和应用 |
| WO2016007534A1 (en) | 2014-07-07 | 2016-01-14 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| PE20180575A1 (es) | 2015-05-22 | 2018-04-04 | Genentech Inc | Benzamidas sustituidas y metodos para utilizarlas |
| MA42683A (fr) | 2015-08-27 | 2018-07-04 | Genentech Inc | Composés thérapeutiques et leurs méthodes utilisation |
| BR112018006189A2 (pt) | 2015-09-28 | 2018-10-09 | Genentech Inc | compostos da fórmula, composição farmacêutica, métodos de tratamento de uma doença, de diminuição do fluxo de íons e de tratamento de prurido em um mamífero, método para tratamento de dores em um mamífero e uso de um composto |
| JP2018535234A (ja) | 2015-11-25 | 2018-11-29 | ジェネンテック, インコーポレイテッド | ナトリウムチャネル遮断薬として有用な置換ベンズアミド |
| CN109071426A (zh) | 2016-03-30 | 2018-12-21 | 基因泰克公司 | 取代的苯甲酰胺及其使用方法 |
| ES2940611T3 (es) * | 2016-04-18 | 2023-05-09 | Novartis Ag | Compuestos y composiciones para el tratamiento de afecciones asociadas a la actividad de NLRP |
| WO2018072602A1 (en) | 2016-10-17 | 2018-04-26 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| KR20190104524A (ko) | 2016-11-21 | 2019-09-10 | 바이킹 테라퓨틱스 인코포레이티드 | 당원축적질환의 치료 방법 |
| CN106588690B (zh) * | 2016-12-19 | 2019-06-04 | 广西中医药大学 | 毛鸡骨草甲素Abrusamide的制备方法 |
| JP2020511511A (ja) | 2017-03-24 | 2020-04-16 | ジェネンテック, インコーポレイテッド | ナトリウムチャネル阻害剤としての4−ピペリジン−n−(ピリミジン−4−イル)クロマン−7−スルホンアミド誘導体 |
| EA201992703A1 (ru) | 2017-06-05 | 2020-04-15 | Вайкинг Терапьютикс, Инк. | Композиции для лечения фиброза |
| US12090252B2 (en) | 2017-09-14 | 2024-09-17 | Riken | Method for producing retinal tissues |
| EP3697758B1 (en) * | 2017-10-17 | 2022-07-06 | Novartis AG | Sulphonamides and compositions thereof for treating conditions associated with nlrp activity |
| WO2019119673A1 (zh) | 2017-12-19 | 2019-06-27 | 北京吉源生物科技有限公司 | 一种双基因修饰的干细胞及其用途 |
| EP3759098A1 (en) | 2018-02-26 | 2021-01-06 | Genentech, Inc. | Pyridine-sulfonamide compounds and their use against pain and related conditions |
| KR20200138283A (ko) | 2018-03-22 | 2020-12-09 | 바이킹 테라퓨틱스 인코포레이티드 | 결정질 형태, 및 결정질 형태의 화합물을 제조하는 방법 |
| US10947251B2 (en) | 2018-03-30 | 2021-03-16 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
| PE20210644A1 (es) | 2018-07-19 | 2021-03-23 | Astrazeneca Ab | METODOS DE TRATAMIENTO DE HFpEF EMPLEANDO DAPAGLIFLOZINA Y COMPOSICIONES QUE COMPRENDEN LA MISMA |
| US12102646B2 (en) | 2018-12-05 | 2024-10-01 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis and inflammation |
| US11827596B2 (en) | 2018-12-12 | 2023-11-28 | Autobahn Therapeutics, Inc. | Thyromimetics |
| AU2020232205A1 (en) | 2019-03-01 | 2021-10-21 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
| US20220170098A1 (en) | 2019-03-13 | 2022-06-02 | Sumitomo Dainippon Pharma Co., Ltd. | Method for Evaluating Quality of Transplant Neural Retina, and Transplant Neural Retina Sheet |
| WO2021026179A1 (en) * | 2019-08-06 | 2021-02-11 | Bristol-Myers Squibb Company | AGONISTS OF ROR GAMMAt |
| CA3163089A1 (en) | 2019-11-29 | 2021-06-03 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
| CA3194226A1 (en) | 2020-09-11 | 2022-03-17 | Riken | Complex containing neural retina-containing cell aggregates and matrix, and method for manufacturing same |
| EP4201428A4 (en) | 2020-09-11 | 2024-09-11 | Sumitomo Pharma Co., Ltd. | MEDIUM FOR TISSUE INTENDED FOR TRANSPLANTATION |
| JPWO2023090427A1 (enExample) | 2021-11-19 | 2023-05-25 | ||
| US12377058B1 (en) | 2024-04-29 | 2025-08-05 | Imam Mohammad Ibn Saud Islamic University | Method for inhibiting proliferation of cancer cells |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3231541A1 (de) | 1982-08-25 | 1984-03-01 | Henning Berlin Gmbh Chemie- Und Pharmawerk, 1000 Berlin | Arzneimittel, enthaltend 3,3',5-trijodthyronamin und verfahren zu seiner herstellung |
| US4741897A (en) * | 1986-07-08 | 1988-05-03 | Baxter Travenol | Thyroxine analogs and reagents for thyroid hormone assays |
| DE69314718T2 (de) * | 1992-07-21 | 1998-02-26 | Ciba Geigy Ag | Oxamidsäure-Derivate als hypocholesterämische Mittel |
| DK0831769T3 (da) * | 1995-06-07 | 2004-02-23 | Karobio Ab | Hidtil ukendte anvendelser af thyroideahormoner eller thyroideahormon-lignende forbindelser |
| US6335459B1 (en) | 1998-12-23 | 2002-01-01 | Syntex (U.S.A.) Llc | Aryl carboxylic acid and aryl tetrazole derivatives as IP receptor modulators |
| US6395784B1 (en) * | 2000-06-07 | 2002-05-28 | Bristol-Myers Squibb Company | Benzamide ligands for the thyroid receptor |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190042029A (ko) * | 2016-08-12 | 2019-04-23 | 오레곤 헬스 앤드 사이언스 유니버시티 | 아마이드 화합물, 이의 약학 조성물 및 이들을 이용하는 방법 |
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| BR9916851A (pt) | 2001-10-16 |
| US6989402B1 (en) | 2006-01-24 |
| AU1885500A (en) | 2000-07-31 |
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| ID29013A (id) | 2001-07-26 |
| HUP0104666A3 (en) | 2003-05-28 |
| HUP0104666A2 (hu) | 2002-03-28 |
| NO20012931D0 (no) | 2001-06-13 |
| JP4405088B2 (ja) | 2010-01-27 |
| ZA200104932B (en) | 2003-01-15 |
| GB9828442D0 (en) | 1999-02-17 |
| WO2000039077A2 (en) | 2000-07-06 |
| CN1186332C (zh) | 2005-01-26 |
| JP2002533432A (ja) | 2002-10-08 |
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