UA75520C2 - Fluorosubstituted cycloalkanoindoles, a composition containing them - Google Patents
Fluorosubstituted cycloalkanoindoles, a composition containing them Download PDFInfo
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- UA75520C2 UA75520C2 UA20040807066A UA20040807066A UA75520C2 UA 75520 C2 UA75520 C2 UA 75520C2 UA 20040807066 A UA20040807066 A UA 20040807066A UA 20040807066 A UA20040807066 A UA 20040807066A UA 75520 C2 UA75520 C2 UA 75520C2
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- C07—ORGANIC CHEMISTRY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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US35138402P | 2002-01-24 | 2002-01-24 | |
PCT/CA2003/000084 WO2003062200A2 (en) | 2002-01-24 | 2003-01-22 | Fluoro substituted cycloalkanoindoles and their use as prostaglandin d2 receptor antagonists |
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UA20040807066A UA75520C2 (en) | 2002-01-24 | 2003-01-22 | Fluorosubstituted cycloalkanoindoles, a composition containing them |
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EP (3) | EP2295409B1 (ru) |
JP (2) | JP4008885B2 (ru) |
KR (2) | KR100859230B1 (ru) |
CN (3) | CN1902176A (ru) |
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AT (1) | ATE414690T1 (ru) |
AU (1) | AU2003202343B2 (ru) |
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DO (1) | DOP2003000566A (ru) |
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EC (1) | ECSP045203A (ru) |
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ES (2) | ES2391747T3 (ru) |
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SI (2) | SI2045241T1 (ru) |
TW (1) | TWI259080B (ru) |
UA (1) | UA75520C2 (ru) |
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Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7217725B2 (en) * | 2000-09-14 | 2007-05-15 | Allergan, Inc. | Prostaglandin D2 antagonist |
US7273883B2 (en) * | 2000-09-14 | 2007-09-25 | Allergan, Inc. | Prostaglandin EP4 antagonist |
AR038136A1 (es) * | 2002-01-24 | 2004-12-29 | Merck Frosst Canada Inc | Cicloalcanindoles con sustitucion con fluor composiciones que contienen estos compuestos y metodos de tratamiento |
AR041089A1 (es) * | 2003-05-15 | 2005-05-04 | Merck & Co Inc | Procedimiento y composiciones farmaceutiicas para tratar aterosclerosis, dislipidemias y afecciones relacionadas |
WO2004104205A2 (en) * | 2003-05-16 | 2004-12-02 | Merck & Co., Inc. | Enzymatic preparation of chiral indole esters |
US20070054951A1 (en) * | 2003-05-20 | 2007-03-08 | Lianhai Li | Fluoro-methanesulfonyl-substituted cycloalkanoindoles and their use as prostaglandin D2 antagonists |
EP1656141B1 (en) * | 2003-08-07 | 2010-04-14 | MERCK SHARP & DOHME LTD. | Treatment for alzheimer s disease and related conditions |
TWI258478B (en) | 2003-10-31 | 2006-07-21 | Arena Pharm Inc | Tetrazole derivatives and methods of treatment of metabolic-related disorders thereof |
US7019022B2 (en) * | 2003-12-15 | 2006-03-28 | Merck Frosst Canada & Co. | Substituted tetrahydrocarbazole and cyclopentanoindole derivatives |
DK1725553T3 (da) | 2004-03-11 | 2008-08-18 | Actelion Pharmaceuticals Ltd | Tetrahydropyridoindolderivater |
AU2005230897B2 (en) * | 2004-04-02 | 2011-03-03 | Merck Sharp & Dohme Corp. | Asymmetric hydrogenation process useful for the preparation of cycloalkanoindole derivatives |
HN2005000795A (es) * | 2004-10-15 | 2010-08-19 | Aventis Pharma Inc | Pirimidinas como antagonistas del receptor de prostaglandina d2 |
WO2006052798A2 (en) * | 2004-11-08 | 2006-05-18 | Merck & Co., Inc. | Method of treating pathological blushing |
PE20060949A1 (es) | 2004-12-23 | 2006-10-11 | Arena Pharm Inc | Derivados fusionados de pirazol como agonistas del receptor de niacina |
JPWO2006068162A1 (ja) * | 2004-12-24 | 2008-06-12 | 塩野義製薬株式会社 | 慢性閉塞性肺疾患の治療剤 |
BRPI0519280A2 (pt) * | 2004-12-27 | 2009-01-06 | Actelion Pharmaceuticals Ltd | composto, composiÇço farmacÊutica e uso de um composto |
CA2598273A1 (en) * | 2005-02-17 | 2006-08-24 | Merck & Co., Inc. | Method of treating atherosclerosis, dyslipidemias and related conditions |
CA2603757A1 (en) * | 2005-04-13 | 2006-10-26 | Merck & Co., Inc. | Niacin receptor agonists, compositions containing such compounds and methods of treatment |
WO2007010965A1 (ja) | 2005-07-22 | 2007-01-25 | Shionogi & Co., Ltd. | Pgd2受容体アンタゴニスト活性を有するアザインドール酸誘導体 |
EP1916245B1 (en) | 2005-07-22 | 2011-10-26 | Shionogi & Co., Ltd. | Indole derivative having pgd2 receptor antagonist activity |
JP5147401B2 (ja) | 2005-09-06 | 2013-02-20 | 塩野義製薬株式会社 | Pgd2受容体アンタゴニスト活性を有するインドールカルボン酸誘導体 |
SI2037967T1 (sl) | 2006-06-16 | 2017-04-26 | The Trustees Of The University Of Pennsylvania | Antagonisti receptorja za prostaglandin d2 za zdravljenje androgene alopecije |
CN101500996B (zh) | 2006-08-07 | 2012-07-04 | 埃科特莱茵药品有限公司 | (3-胺基-1,2,3,4-四氢-9h-咔唑-9-基)-乙酸衍生物 |
WO2008097535A2 (en) * | 2007-02-08 | 2008-08-14 | Merck & Co., Inc. | Method of treating atherosclerosis, dyslipidemias and related conditions |
US20090076117A1 (en) * | 2007-09-17 | 2009-03-19 | Protia, Llc | Deuterium-enriched laropiprant |
WO2010008864A2 (en) | 2008-06-24 | 2010-01-21 | Amira Pharmaceuticals, Inc. | Cycloalkane[b]indole angtagonists of prostaglandin d2 receptors |
US8507473B2 (en) | 2008-09-11 | 2013-08-13 | Arena Pharmaceuticals, Inc. | 3H-imidazo[4,5-b]pyridin-5-ol derivatives useful in the treatment of GPR81 receptor disorders |
JP2012503605A (ja) * | 2008-09-25 | 2012-02-09 | メルク カナダ インコーポレイテッド | Ep4受容体アンタゴニストとしてのベータ−カルボリンスルホニルウレア誘導体 |
GB2463788B (en) * | 2008-09-29 | 2010-12-15 | Amira Pharmaceuticals Inc | Heteroaryl antagonists of prostaglandin D2 receptors |
GB2465062B (en) | 2008-11-06 | 2011-04-13 | Amira Pharmaceuticals Inc | Cycloalkane(B)azaindole antagonists of prostaglandin D2 receptors |
US9180114B2 (en) * | 2008-11-26 | 2015-11-10 | President And Fellows Of Harvard College | Neurodegenerative diseases and methods of modeling |
US8882678B2 (en) | 2009-03-13 | 2014-11-11 | Atrium Medical Corporation | Pleural drainage system and method of use |
SI2558447T1 (sl) | 2010-03-22 | 2015-01-30 | Actelion Pharmaceuticals Ltd. | Derivati 3-(heteroaril-amino)-1,2,3,4-tetrahidro-9h-karbazola in njihova uporaba kot modulatorji prostaglandinskega receptorja d2 |
BR112013026283A8 (pt) | 2011-04-14 | 2018-01-30 | Actelion Pharmaceuticals Ltd | derivados de ácido 7-(heteroaril-amino)-6,7,8,9-tetrahidropirido[1,2-a]indol acético e seu uso como moduladores do receptor d2 de prostaglandina |
JP5841361B2 (ja) * | 2011-06-29 | 2016-01-13 | 壽製薬株式会社 | 三環性化合物及びそれを含有する医薬組成物 |
AR088377A1 (es) | 2011-10-20 | 2014-05-28 | Siena Biotech Spa | Proceso para la preparacion de 6-cloro-2,3,4,9-tetrahidro-1h-carbazol-1-carboxamida y compuestos intermedios de esta |
CN102659664B (zh) * | 2012-03-28 | 2015-01-21 | 中国计量学院 | 合成分离拉洛皮兰及其类似物的方法 |
FR3000395A1 (fr) * | 2012-12-31 | 2014-07-04 | Galderma Res & Dev | Combinaison de laropiprant et d'oxymetazoline pour le traitement de la rosacee |
FR3000399B1 (fr) * | 2012-12-31 | 2015-03-27 | Galderma Res & Dev | Utilisation topique du laropiprant pour le traitement de la rosacee |
AR099767A1 (es) | 2014-03-17 | 2016-08-17 | Actelion Pharmaceuticals Ltd | Derivados del ácido acético azaindol y su uso como moduladores del receptor de prostaglandina d2 |
CN106103437A (zh) | 2014-03-18 | 2016-11-09 | 埃科特莱茵药品有限公司 | 氮杂吲哚乙酸衍生物及其作为前列腺素d2受体调节剂的用途 |
EP4420734A2 (en) | 2015-02-13 | 2024-08-28 | Institut National de la Santé et de la Recherche Médicale | Ptgdr-1 and/or ptgdr-2 antagonists for preventing and/or treating systemic lupus erythematosus |
US10351560B2 (en) | 2015-09-15 | 2019-07-16 | Idorsia Pharmaceuticals Ltd | Crystalline forms |
WO2019181592A1 (ja) | 2018-03-19 | 2019-09-26 | 三井化学株式会社 | 表示素子用封止材およびその硬化物、有機el素子用枠封止材、ならびに有機el素子用面封止材 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3535326A (en) * | 1967-03-06 | 1970-10-20 | Sumitomo Chemical Co | Certain tetrahydro carboline derivatives |
BE787444A (fr) * | 1971-08-13 | 1973-02-12 | Hoffmann La Roche | Composes polycycliques |
US4009181A (en) * | 1973-01-22 | 1977-02-22 | Hoffmann-La Roche Inc. | Cyclopenta[b]indole-2-carboxylic acids and derivatives thereof |
US4057559A (en) * | 1973-10-01 | 1977-11-08 | American Home Products Corporation | Carbazole acetic acid derivatives |
US4166452A (en) | 1976-05-03 | 1979-09-04 | Generales Constantine D J Jr | Apparatus for testing human responses to stimuli |
US4256108A (en) | 1977-04-07 | 1981-03-17 | Alza Corporation | Microporous-semipermeable laminated osmotic system |
US4265874A (en) | 1980-04-25 | 1981-05-05 | Alza Corporation | Method of delivering drug with aid of effervescent activity generated in environment of use |
US5021447A (en) * | 1986-01-23 | 1991-06-04 | Merck Frosst Canada, Inc. | Tetrahydrocarbazole 1-alkanoic acids and pharmaecutical compositions |
US4808608A (en) * | 1986-01-23 | 1989-02-28 | Merck & Co., Inc. | Tetrahydrocarbazole 1-alkanoic acids, pharmaceutical compositions and use |
ES2038653T3 (es) * | 1986-01-23 | 1993-08-01 | Merck Frosst Canada Inc. | Acidos 1-alcanoicos tetrahidrocarbazol. |
US4940719A (en) * | 1986-03-27 | 1990-07-10 | Merck Frosst Canada, Inc. | Tetrahydrocarbazole esters, pharmaceutical compositions and use |
US4775680A (en) * | 1987-07-21 | 1988-10-04 | Merck & Co., Inc. | Cyclohept[b]indolealkanoic acids, pharmaceutical compositions and use |
US5221678A (en) | 1990-07-26 | 1993-06-22 | Merck Frosst Canada, Inc. | (quinolin-2-ylmethoxy)tetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes |
GB9101375D0 (en) | 1991-01-22 | 1991-03-06 | Erba Carlo Spa | N-imidazolyl derivatives of substituted tetrahydrocarbazole and cyclohepht(b)indole |
AU693143B2 (en) | 1993-12-06 | 1998-06-25 | Cytel Corporation | CS-1 peptidomimetics, compositions and methods of using the same |
US5510332A (en) | 1994-07-07 | 1996-04-23 | Texas Biotechnology Corporation | Process to inhibit binding of the integrin α4 62 1 to VCAM-1 or fibronectin and linear peptides therefor |
ATE237342T1 (de) | 1994-07-11 | 2003-05-15 | Athena Neurosciences Inc | Inhibitoren der leukozytenadhäsion |
US5811391A (en) | 1994-08-25 | 1998-09-22 | Cytel Corporation | Cyclic CS-1 peptidomimetics, compositions and methods of using same |
GB9524630D0 (en) | 1994-12-24 | 1996-01-31 | Zeneca Ltd | Chemical compounds |
US6306840B1 (en) | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
WO1996031206A2 (en) | 1995-04-07 | 1996-10-10 | Warner-Lambert Company | Flavones and coumarins as agents for the treatment of atherosclerosis |
WO1996040781A1 (en) | 1995-06-07 | 1996-12-19 | Tanabe Seiyaku Co., Ltd. | CYCLIC PEPTIDE INHIBITORS OF β1 AND β2 INTEGRIN-MEDIATED ADHESION |
CA2225250C (en) | 1995-06-21 | 2005-03-22 | Shionogi & Co., Ltd. | Bicyclic amino derivatives and pgd2 antagonist containing the same |
EP0842195A1 (en) | 1995-07-06 | 1998-05-20 | Zeneca Limited | Peptide inhibitors of fibronectine |
US6248713B1 (en) | 1995-07-11 | 2001-06-19 | Biogen, Inc. | Cell adhesion inhibitors |
CZ297324B6 (cs) | 1996-12-13 | 2006-11-15 | Shionogi & Co., Ltd. | Benzothiofenkarboxamidové deriváty a antagonisty PGD2, které je obsahují |
JP3857525B2 (ja) | 1998-06-03 | 2006-12-13 | 塩野義製薬株式会社 | Pgd2拮抗剤を含有する痒みの治療剤 |
US20010047027A1 (en) | 2000-04-12 | 2001-11-29 | Marc Labelle | Prostaglandin D2 receptor antagonists |
US6410583B1 (en) * | 2000-07-25 | 2002-06-25 | Merck Frosst Canada & Co. | Cyclopentanoindoles, compositions containing such compounds and methods of treatment |
AR038136A1 (es) * | 2002-01-24 | 2004-12-29 | Merck Frosst Canada Inc | Cicloalcanindoles con sustitucion con fluor composiciones que contienen estos compuestos y metodos de tratamiento |
US7019022B2 (en) * | 2003-12-15 | 2006-03-28 | Merck Frosst Canada & Co. | Substituted tetrahydrocarbazole and cyclopentanoindole derivatives |
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