1-(3-methoxypropyl)-1H-indole-3-carbaldehyde | 897949-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(3-methoxypropyl)-1H-indole-3-carbaldehyde
• 英文别名: 1-(3-methoxypropyl)indole-3-carbaldehyde
• CAS: 897949-13-2
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: UQFDWIPHFBIHPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-methoxypropyl)-1H-indole-3-carbaldehyde 在 2,6-二甲基吡啶 、 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 三氟甲磺酸三甲基硅酯 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (3R*,5S*)-3-Amino-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Structure-Based Design of Substituted Piperidines as a New Class of Highly Efficacious Oral Direct Renin Inhibitors

  摘要：

  A cis-configured 3,5-disubstituted piperidine direct renin inhibitor, (syn,rac)-1, was discovered as a high-throughput screening hit from a target-family tailored library. Optimization of both the prime and the nonprime site residues flanking the central piperidine transition-state surrogate resulted in analogues with improved potency and pharmacokinetic (PK) properties, culminating in the identification of the 4-hydroxy-3,5-substituted piperidine 31. This compound showed high in vitro potency toward human renin with excellent off-target selectivity, 60% oral bioavailability in rat, and dose-dependent blood pressure lowering effects in the double-transgenic rat model.

  DOI：

  10.1021/ml500137b
• 作为产物：
  描述：

  3-吲哚甲醛 、 3-methoxypropyl p-toluenesulfonate 在 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-(3-methoxypropyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Substituted Piperdines as Renin Inhibitors

  摘要：

  该发明涉及替代的3,4-或更高替代的哌啶基化合物，其用于制备用于治疗依赖肾素活性的疾病的药物配方；该类化合物在治疗依赖肾素活性的疾病中的应用；这些化合物用于诊断和治疗温血动物，特别是用于治疗依赖肾素活性的疾病的治疗；包括上述化合物的药物配方或产品，以及/或包括上述化合物的给药方法，制备上述化合物的方法，以及用于其合成的新中间体、起始材料和/或部分步骤。这些化合物优选具有公式 I，其中基团 R1、R2、R11 和 W 如规范中所定义。

  公开号：

  US20090137566A1

文献信息

• [EN] 3, 4 - SUBSTITUTED PIPERIDINE DERIVATIVES AS RENIN INHIBITORS<br/>[FR] DÉRIVÉS DE PIPÉRIDINE 3,4-SUBSTITUÉE CONVENANT COMME INHIBITEURS DE LA RÉNINE
  申请人：MERCK FROSST CANADA LTD

  公开号：WO2009140769A1

  公开（公告）日：2009-11-26

  The present invention relates to 3,4-substituted piperidinyl - based renin inhibitor compounds bearing at 4-position lsoqumolone and having the Formula (I) : The invention further relates to pharmaceutical compositions containing said compounds, as well as their use in treating cardiovascular events and renal insufficiency.

  本发明涉及具有4-位lsoqumolone的3,4-取代哌啶基肾素抑制剂化合物，其化学式为（I）：该发明还涉及含有上述化合物的药物组合物，以及它们在治疗心血管事件和肾功能不全中的用途。
• [EN] 3, 4 - SUBSTITUTED PIPERIDINE DERIVATIVES AS RENIN INHIBITORS<br/>[FR] DÉRIVÉS DE PIPÉRIDINE SUBSTITUÉS EN 3,4 UTILISÉS EN TANT QU'INHIBITEURS DE LA RÉNINE
  申请人：MERCK FROSST CANADA LTD

  公开号：WO2009135299A1

  公开（公告）日：2009-11-12

  The present invention relates to 3,4-substituted piperidinyl-based renin inhibitor compounds bearing at 4-position oxopyridine and having the formula (I). The invention further relates to pharmaceutical compositions containing said compounds, as well as their use in treating cardiovascular events and renal insufficiency.

  本发明涉及具有在4位氧吡啶基的3,4-取代哌啶基肾素抑制剂化合物，其化学式为(I)。该发明还涉及含有上述化合物的药物组合物，以及它们在治疗心血管事件和肾功能不全中的用途。
• ORGANIC COMPOUNDS
  申请人：Breitenstein Werner

  公开号：US20090233920A1

  公开（公告）日：2009-09-17

  The invention relates to 3,5-substituted piperidine compounds, these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (=disorder) that depends on activity of renin; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; pharmaceutical formulations comprising a 3,5-substituted piperidine compound, and/or a method of treatment comprising administering a 3,5-substituted piperidine compound, a method for the manufacture of a 3,5-substituted piperidine compound, and novel intermediates and partial steps for its synthesis. The preferred compounds (which can also be present as salts) have the formula I wherein R1, R2, T, R3 and R4 are as defined in the specification.

  该发明涉及3,5-取代哌啶化合物，这些化合物用于诊断和治疗温血动物，特别是用于治疗依赖肾素活性的疾病（=紊乱）；该类化合物用于制备用于治疗依赖肾素活性疾病的药物配方；该类化合物用于治疗依赖肾素活性的疾病；包括3,5-取代哌啶化合物的药物配方，和/或包括给予3,5-取代哌啶化合物的治疗方法，一种用于制造3,5-取代哌啶化合物的方法，以及其合成的新中间体和部分步骤。优选的化合物（也可以存在为盐）具有式I的结构，其中R1、R2、T、R3和R4如规范中定义。
• Organic Compounds
  申请人：Nihonyanagi Atsuko

  公开号：US20080242662A1

  公开（公告）日：2008-10-02

  The invention relates to substituted 3,4- or higher substituted piperazine compounds, the use thereof for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (=disorder) that depends on activity of renin; pharmaceutical formulations or products comprising said compounds, and/or a method of treatment comprising administering said compounds, a method for the manufacture of said compounds as well as novel intermediates, starting materials and/or partial steps for their synthesis. The compounds are especially of the formula I, wherein R1, R2, R11, C, E and D are as defined in the specification.

  本发明涉及取代的3,4-或更高取代的哌嗪化合物，其用于制备治疗依赖于肾素活性的疾病的药物配方；该类化合物在治疗依赖于肾素活性的疾病中的应用；这些化合物用于诊断和治疗温血动物，特别是用于治疗依赖于肾素活性的疾病（=紊乱）；包括上述化合物和/或其制剂的制药制剂或产品，以及包括给予上述化合物的治疗方法，制造上述化合物的方法以及新的中间体，起始材料和/或其合成的部分步骤。这些化合物特别是公式I，其中R1、R2、R11、C、E和D如规范中所定义。
• 3,4,(5)-SUBSTITUTED TETRAHYDROPHYRIDINES
  申请人：Masuya Keiichi

  公开号：US20100029647A1

  公开（公告）日：2010-02-04

  3,4(,5)-substituted tetrahydropyridine compounds, these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease that depends on activity of renin; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; pharmaceutical formulations comprising a 3,4(,5)-substituted tetrahydropyridine compound, and/or a method of treatment comprising administering a 3,4(,5)-substituted tetrahydropyridine compound, a method for the manufacture of a 3,4(,5)-substituted tetrahydropyridine compound, and novel intermediates and partial steps for its synthesis. The 3,4(,5)-substituted tetrahydropyridine compounds have the formula I wherein the substituents and symbols are as described in the specification.

  3,4(,5)-取代四氢吡啶化合物，这些化合物用于温血动物的诊断和治疗，特别是用于治疗依赖于肾素活性的疾病；该类化合物用于制备治疗依赖于肾素活性疾病的制药配方；该类化合物用于治疗依赖于肾素活性的疾病；包含3,4(,5)-取代四氢吡啶化合物的制药配方，和/或包括给予3,4(,5)-取代四氢吡啶化合物的治疗方法，以及制备3,4(,5)-取代四氢吡啶化合物的方法，以及其合成的新中间体和部分步骤。3,4(,5)-取代四氢吡啶化合物的化学式为I，其中取代基和符号如说明书所述。