JP4974463B2 - インダン酢酸誘導体ならびに製薬学的薬剤としてのそれらの使用、中間体及び製造方法 - Google Patents

インダン酢酸誘導体ならびに製薬学的薬剤としてのそれらの使用、中間体及び製造方法 Download PDF

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JP4974463B2
JP4974463B2 JP2004563903A JP2004563903A JP4974463B2 JP 4974463 B2 JP4974463 B2 JP 4974463B2 JP 2004563903 A JP2004563903 A JP 2004563903A JP 2004563903 A JP2004563903 A JP 2004563903A JP 4974463 B2 JP4974463 B2 JP 4974463B2
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propoxy
acetic acid
indanyl
alkyl
mmol
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JP2006516251A (ja
JP2006516251A5 (enExample
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カンタン,ルイ−デイビツド
チヨイ,ソーンギユ
クラーク,ロジヤー・ビー
ヘンテマン,マーテイン・エフ
マー,シン
ルドルフ,ヨアヒム
リアング,シドニー・エツクス
アクシエ,クリステイアナ
ラボワ,リコ・シー
チエン,リビング
マジヤンダー,デユテイ
ウイケンズ,フイリツプ・エル
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ニツポネツクス・インコーポレーテツド
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Families Citing this family (26)

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Publication number Priority date Publication date Assignee Title
PT1599468E (pt) 2003-01-14 2008-01-14 Arena Pharm Inc Derivados de arilo e heteroarilo 1,2,3.-trissubstituídos comomoduladores do metabolismo, e profilaxia e tratamento dedesordens relacionadas tais como diabetes e hiperglicemia
JP2006523698A (ja) * 2003-04-17 2006-10-19 カリプシス・インコーポレーテッド Ppar変調薬としての(3−{3−(2,4−ビス−トリフルオロメチル−ベンジル)−(5−エチル−ピリミジン−2−イル)−アミノ−プロポキシ}−フェニル)−酢酸および関連化合物、ならびに代謝性障害の処置方法
WO2004106276A1 (ja) * 2003-05-30 2004-12-09 Takeda Pharmaceutical Company Limited 縮合環化合物
JP4805552B2 (ja) * 2003-05-30 2011-11-02 武田薬品工業株式会社 縮合環化合物
EP2287165A3 (en) 2003-07-14 2011-06-22 Arena Pharmaceuticals, Inc. Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
AU2004285530A1 (en) * 2003-10-31 2005-05-12 Janssen Pharmaceutica N.V. Phenoxyacetic acids derivatives useful as peroxisome proliferator-activated receptor (PPAR) dual agonists
EP1687274A1 (en) * 2003-11-20 2006-08-09 Warner-Lambert Company LLC Androgen receptor modulators
US7622491B2 (en) * 2004-08-13 2009-11-24 Metabolex Inc. Modulators of PPAR and methods of their preparation
MY148521A (en) 2005-01-10 2013-04-30 Arena Pharm Inc Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto
US20100130737A1 (en) * 2005-02-18 2010-05-27 Takeda Pharmaceutical Company Limited Regulating Agent of GPR34 Receptor Function
EP1866293A1 (en) * 2005-03-31 2007-12-19 UCB Pharma, S.A. Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses
US7816536B2 (en) 2005-06-10 2010-10-19 The Research Foundation Of State University Of New York 4-substituted and 7-substituted indoles, benzofurans, benzothiophenes, benzimidazoles, benzoxazoles, and benzothiazoles and methods for making same
US8653115B2 (en) 2006-06-13 2014-02-18 Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences Heterocyclic non-nucleoside compounds, their preparation, pharmaceutical composition and their use as antiviral agents
TW200936130A (en) * 2008-02-26 2009-09-01 Lundbeck & Co As H Uses of indane compounds
EP2389368B1 (en) 2009-01-23 2015-06-17 Merck Sharp & Dohme Corp. Bridged and fused antidiabetic compounds
AU2010206786A1 (en) * 2009-01-23 2011-07-28 Merck Sharp & Dohme Corp. Bridged and fused heterocyclic antidiabetic compounds
TW201040186A (en) 2009-02-05 2010-11-16 Schering Corp Phthalazine-containing antidiabetic compounds
WO2010141696A1 (en) * 2009-06-04 2010-12-09 Dara Biosciences, Inc. Methods of treating or preventing psoriasis, and/or alzheimer's disease using indane acetic acid derivatives
JP2012188352A (ja) * 2009-07-13 2012-10-04 Dainippon Sumitomo Pharma Co Ltd 3−(4−置換アルキル−フェニル)−2−フランカルボン酸誘導体およびその薬学的に許容される塩
JP5941916B2 (ja) 2010-09-22 2016-06-29 アリーナ ファーマシューティカルズ, インコーポレイテッド Gpr119レセプターのモジュレーターおよびそれに関連する障害の処置
WO2012074980A2 (en) * 2010-12-01 2012-06-07 Dara Biosciences, Inc. Methods of treating or preventing autoimmune disorders and liver disorders using indane acetic acid derivatives
PL3242666T3 (pl) 2015-01-06 2025-02-17 Arena Pharmaceuticals, Inc. Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1
DK3310760T3 (da) 2015-06-22 2022-10-24 Arena Pharm Inc Krystallinsk L-argininsalt af (R)-2-(7-(4-cyclopentyl-3-(trifluormethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3- yl)eddikesyre til anvendelse ved S1P1-receptor-associerede lidelser
CN110520124A (zh) 2017-02-16 2019-11-29 艾尼纳制药公司 用于治疗原发性胆汁性胆管炎的化合物和方法
BR112020024762A2 (pt) 2018-06-06 2021-03-23 Arena Pharmaceuticals, Inc. métodos de tratamento de condições relacionadas ao receptor s1p1
BR112021013807A2 (pt) * 2019-01-18 2021-11-30 Astrazeneca Ab Inibidores de pcsk9 e seus métodos de uso

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6197241A (ja) * 1984-10-16 1986-05-15 Yamanouchi Pharmaceut Co Ltd 新規カルボン酸誘導体
CA1314224C (en) * 1987-07-07 1993-03-09 Shinichiro Ashida Antidiabetic agent
AR036237A1 (es) * 2001-07-27 2004-08-25 Bayer Corp Derivados del acido indan acetico, intermediarios, y metodo para su preparacion, composicion farmaceutica y el uso de dichos derivados para la manufactura de un medicamento
UA79755C2 (en) 2002-04-16 2007-07-25 Bayer Pharmaceuticals Corp Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation

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