(3R,5R)-7-[4-benzylcarbamoyl-2-(4-fluoro-phenyl)-5-isopropyl-imidazol-1-yl]-3,5-dihydroxy-heptanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3R,5R)-7-[4-benzylcarbamoyl-2-(4-fluoro-phenyl)-5-isopropyl-imidazol-1-yl]-3,5-dihydroxy-heptanoic acid
• 英文别名: (3r,5r)-7-[4-(Benzylcarbamoyl)-2-(4-Fluorophenyl)-5-(1-Methylethyl)-1h-Imidazol-1-Yl]-3,5-Dihydroxyheptanoic Acid；(3R,5R)-7-[4-(benzylcarbamoyl)-2-(4-fluorophenyl)-5-propan-2-ylimidazol-1-yl]-3,5-dihydroxyheptanoic acid
• 化学式: C₂₇H₃₂FN₃O₅
• 分子量: 497.567
• InChiKey: ATGOOVTXNDYCBK-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,5R)-7-[4-benzylcarbamoyl-2-(4-fluoro-phenyl)-5-isopropyl-imidazol-1-yl]-3,5-dihydroxy-heptanoic acid 在 盐酸 作用下， 以 水 、 甲苯 为溶剂， 反应 2.5h， 生成 2-(4-fluoro-phenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-5-isopropyl-1H-imidazole-4-carboxylic acid benzylamide
  参考文献：
  名称：

  WO2007/49121

  摘要：

  公开号：
• 作为产物：
  描述：

  2-(4-fluorobenzoylamino)-4-methyl-3-oxopentanoic acid benzyl ester 在 盐酸 、 苯甲酸 、 苄胺 作用下， 以 甲醇 、 正庚烷 、 水 为溶剂， 反应 29.5h， 生成 (3R,5R)-7-[4-benzylcarbamoyl-2-(4-fluoro-phenyl)-5-isopropyl-imidazol-1-yl]-3,5-dihydroxy-heptanoic acid
  参考文献：
  名称：

  Preparation of a HMG-CoA Reductase Inhibitor via an Optimized Imidazole-Forming Condensation Reaction

  摘要：

  Development work toward an enabling synthesis of preparative scale batches of an imidazole-based HMG-CoA reductase inhibitor is described. The desired target was synthesized in 16% yield over 7 steps, highlighted by an imidazole-forming condensation reaction in which the yield was improved from 20% to >70% via modification of the solvent, acid, and amine equivalents. The step 2 acylation was improved, and a problematic benzyl ester in step 4 was converted into the corresponding benzyl amide to decrease trans-amidation during the step 5 imidazole formation. A highly effective salt formation and crystallization protocol was also developed.

  DOI：

  10.1021/op800092e

文献信息

• Dibenzyl Amine Compounds and Derivatives
  申请人：Chang George

  公开号：US20070213371A1

  公开（公告）日：2007-09-13

  Dibenzyl amine compounds and derivatives, pharmaceutical compositions containing such compounds and the use of such compounds to elevate certain plasma lipid levels, including high density lipoprotein-cholesterol and to lower certain other plasma lipid levels, such as LDL-cholesterol and triglycerides and accordingly to treat diseases which are exacerbated by low levels of HDL cholesterol and/or high levels of LDL-cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases in some mammals, including humans.

  二苯基胺化合物及其衍生物，含有这种化合物的药物组合物以及使用这种化合物提高某些血浆脂质水平，包括高密度脂蛋白胆固醇，并降低其他一些血浆脂质水平，如低密度脂蛋白胆固醇和甘油三酯，并据此治疗由高密度脂蛋白胆固醇水平低和/或低密度脂蛋白胆固醇和甘油三酯水平高加重的疾病，如动脉粥样硬化和心血管疾病在某些哺乳动物，包括人类。
• Novel imidazoles
  申请人：Bolton Louis Gary

  公开号：US20050239857A1

  公开（公告）日：2005-10-27

  Novel imidazoles are provided. The compounds are useful as HMGCo-A Reductase Inhibitor. Also provided are pharmaceutical compositions of the compounds. Methods of making and methods of using the compounds are also provided.

  提供了新型咪唑类化合物。这些化合物可用作HMGCo-A还原酶抑制剂。还提供了这些化合物的药物组合物。还提供了制备这些化合物的方法和使用这些化合物的方法。
• Novel pyrroles and imidazoles
  申请人：Bolton Louis Gary

  公开号：US20060287378A1

  公开（公告）日：2006-12-21

  Novel imidazoles and novel pyrroles are provided. Also provided are pharmaceutical compositions, methods of making and methods of using the compounds.

  本发明提供了新型咪唑和新型吡咯。同时，还提供了制药组合物、制备方法和使用该化合物的方法。
• NOVEL PYRROLE-BASED HMG-COA REDUCTASE INHIBITORS
  申请人：Warner-Lambert Company LLC

  公开号：EP1656132A2

  公开（公告）日：2006-05-17
• NOVEL IMIDAZOLES
  申请人：Warner-Lambert Company LLC

  公开号：EP1740549A2

  公开（公告）日：2007-01-10