(S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl]-oxazolidin-2-one | 475481-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl]-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-[7-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-1-benzothiophen-4-yl]propanoyl]-1,3-oxazolidin-2-one
• CAS: 475481-53-9
• 化学式: C₃₄H₃₂N₂O₇S
• 分子量: 612.703
• InChiKey: ZDHYLZABGTZBCA-NSQMQTOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl]-oxazolidin-2-one 在 三乙基硅烷 作用下， 以 三氟乙酸 为溶剂， 生成 (S)-4-benzyl-3-(2(S)-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl)-oxazolidin-2-one
  参考文献：
  名称：

  Oxazole derivatives

  摘要：

  本发明涉及新型噁唑化合物，其作为PPAR&agr;和PPAR&ggr;激动剂，并因此可用于治疗由PPAR&agr;和PPAR&ggr;调节的疾病，如糖尿病。

  公开号：

  US20030055265A1
• 作为产物：
  描述：

  7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-4-carbaldehyde 、 (S)-4-苄基-3-(2-甲氧基乙酰基)噁唑烷-2-酮 在 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl]-oxazolidin-2-one
  参考文献：
  名称：

  Aleglitazar, a new, potent, and balanced dual PPARα/γ agonist for the treatment of type II diabetes

  摘要：

  Design, synthesis, and SAR of novel alpha-alkoxy-beta-arylpropionic acids as potent and balanced PPARalphagamma coagonists are described. One representative thereof, Aleglitazar ((S)-2Aa), was chosen for clinical development. Its X-ray structure in complex with both receptors as well as its high efficacy in animal models of T2D and dyslipidemia are also presented.

  DOI：

  10.1016/j.bmcl.2009.03.036

文献信息

• [EN] CARBOXYLIC ACID SUBSTITUTED OXAZOLE DERIVATIVES FOR USE AS PPAR-ALPHA AND -GAMMA ACTIVATORS IN THE TREATMENT OF DIABETES<br/>[FR] DERIVES D'OXAZOLE SUBSTITUES PAR DE L'ACIDE CARBOXYLIQUE UTILES EN TANT QU'ACTIVATEURS PPAR-ALPHA ET GAMMA DANS LE TRAITEMENT DU DIABETE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002092084A1

  公开（公告）日：2002-11-21

  The present invention relates to compounds of formula (I) wherein R1 to R7 are as defined in the description and claims, and pharmaceutically acceptable salts and esters thereof. The compounds are useful for the treatment of diseases such as diabetes.

  本发明涉及式(I)的化合物，其中R1至R7如描述和权利要求中所定义，并且其药学上可接受的盐和酯。该化合物可用于治疗糖尿病等疾病。
• CARBOXYLIC ACID SUBSTITUTED OXAZOLE DERIVATIVES FOR USE AS PPAR-ALPHA AND -GAMMA ACTIVATORS IN THE TREATMENT OF DIABETES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1392295B1

  公开（公告）日：2006-05-31
• US6642389B2
  申请人：——

  公开号：US6642389B2

  公开（公告）日：2003-11-04
• Oxazole derivatives
  申请人：——

  公开号：US20030055265A1

  公开（公告）日：2003-03-20

  The present invention relates to novel oxazole compounds which act as PPAR&agr; and PPAR&ggr; agonists and are accordingly useful for the treatment of diseases modulated by PPAR&agr; and PPAR&ggr; such as diabetes.

  本发明涉及新型噁唑化合物，其作为PPAR&agr;和PPAR&ggr;激动剂，并因此可用于治疗由PPAR&agr;和PPAR&ggr;调节的疾病，如糖尿病。
• Aleglitazar, a new, potent, and balanced dual PPARα/γ agonist for the treatment of type II diabetes
  作者：Agnes Bénardeau、Jörg Benz、Alfred Binggeli、Denise Blum、Markus Boehringer、Uwe Grether、Hans Hilpert、Bernd Kuhn、Hans Peter Märki、Markus Meyer、Kurt Püntener、Susanne Raab、Armin Ruf、Daniel Schlatter、Peter Mohr

  DOI：10.1016/j.bmcl.2009.03.036

  日期：2009.5

  Design, synthesis, and SAR of novel alpha-alkoxy-beta-arylpropionic acids as potent and balanced PPARalphagamma coagonists are described. One representative thereof, Aleglitazar ((S)-2Aa), was chosen for clinical development. Its X-ray structure in complex with both receptors as well as its high efficacy in animal models of T2D and dyslipidemia are also presented.