Methyl 2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methylideneamino]acetate | 951403-91-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl 2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methylideneamino]acetate
• CAS: 951403-91-1
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: BTXQWXBNJZFBSF-UHFFFAOYSA-N

物化性质

• 沸点：
  548.2±60.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methylideneamino]acetate 在 lithium hydroxide 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 莫格列地
  参考文献：
  名称：

  Design and Synthesis of N-[(4-Methoxyphenoxy)carbonyl]-N-[[4-[2-(5- methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]glycine [Muraglitazar/BMS-298585], a Novel Peroxisome Proliferator-Activated Receptor α/γ Dual Agonist with Efficacious Glucose and Lipid-Lowering Activities

  摘要：

  Muraglitazar/BMS-298585 (2) has been identified as a non-thiazolidinedione PPAR alpha/gamma dual agonist that shows potent activity in vitro at human PPAR alpha (EC50 = 320 nM) and PPAR gamma (EC50 = 110 nM). Compound 2 shows excellent efficacy for lowering glucose, insulin, triglycerides, and free fatty acids in genetically obese, severely diabetic db/db mice and has a favorable ADME profile. Compound 2 is currently in clinical development for the treatment of type 2 diabetes and dyslipidemia.

  DOI：

  10.1021/jm0496436
• 作为产物：
  描述：

  2-(5-甲基-2-苯基-1,3-恶唑-4-基)乙基甲烷磺酸酯 在 4 A molecular sieve 、 magnesium sulfate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 36.0h， 生成 Methyl 2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methylideneamino]acetate
  参考文献：
  名称：

  Design and Synthesis of N-[(4-Methoxyphenoxy)carbonyl]-N-[[4-[2-(5- methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]glycine [Muraglitazar/BMS-298585], a Novel Peroxisome Proliferator-Activated Receptor α/γ Dual Agonist with Efficacious Glucose and Lipid-Lowering Activities

  摘要：

  Muraglitazar/BMS-298585 (2) has been identified as a non-thiazolidinedione PPAR alpha/gamma dual agonist that shows potent activity in vitro at human PPAR alpha (EC50 = 320 nM) and PPAR gamma (EC50 = 110 nM). Compound 2 shows excellent efficacy for lowering glucose, insulin, triglycerides, and free fatty acids in genetically obese, severely diabetic db/db mice and has a favorable ADME profile. Compound 2 is currently in clinical development for the treatment of type 2 diabetes and dyslipidemia.

  DOI：

  10.1021/jm0496436

文献信息

• [EN] PROCESS OF PREPARING SUBSTITUTED CARBAMATES AND INTERMEDIATES THEREOF<br/>[FR] PROCEDE DE PREPARATION DE CARBAMATES SUBSTITUES ET INTERMEDIAIRES DE CEUX-CI
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2005113521A1

  公开（公告）日：2005-12-01

  An improved process of preparing substituted carbamate derivatives, and crystalline forms thereof, useful for the treatment of dyslipidemia and diabetes, and intermediates thereof are provided.

  提供了一种改进的制备替代氨基甲酸酯衍生物及其结晶形式的过程，用于治疗血脂异常和糖尿病，以及其中间体。
• Design and Synthesis of <i>N</i>-[(4-Methoxyphenoxy)carbonyl]-<i>N</i>-[[4-[2-(5- methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]glycine [Muraglitazar/BMS-298585], a Novel Peroxisome Proliferator-Activated Receptor α/γ Dual Agonist with Efficacious Glucose and Lipid-Lowering Activities
  作者：Pratik V. Devasthale、Sean Chen、Yoon Jeon、Fucheng Qu、Chunning Shao、Wei Wang、Hao Zhang、Michael Cap、Dennis Farrelly、Rajasree Golla、Gary Grover、Thomas Harrity、Zhengping Ma、Lisa Moore、Jimmy Ren、Ramakrishna Seethala、Lin Cheng、Paul Sleph、Wei Sun、Aaron Tieman、John R. Wetterau、Arthur Doweyko、Gamini Chandrasena、Shu Y. Chang、W. Griffith Humphreys、Vito G. Sasseville、Scott A. Biller、Denis E. Ryono、Fred Selan、Narayanan Hariharan、Peter T. W. Cheng

  DOI：10.1021/jm0496436

  日期：2005.3.1

  Muraglitazar/BMS-298585 (2) has been identified as a non-thiazolidinedione PPAR alpha/gamma dual agonist that shows potent activity in vitro at human PPAR alpha (EC50 = 320 nM) and PPAR gamma (EC50 = 110 nM). Compound 2 shows excellent efficacy for lowering glucose, insulin, triglycerides, and free fatty acids in genetically obese, severely diabetic db/db mice and has a favorable ADME profile. Compound 2 is currently in clinical development for the treatment of type 2 diabetes and dyslipidemia.