4-[2-(5-fluoro-2-methyl-phenoxy)-6-methyl-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester | 1175015-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-[2-(5-fluoro-2-methyl-phenoxy)-6-methyl-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: 4-[2-(5-Fluoro-2-methyl-phenoxy)-6-methyl-1-phenyl-1h-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester；tert-butyl 4-[2-(5-fluoro-2-methylphenoxy)-6-methyl-1-phenylpyrrolo[3,2-b]pyridine-3-carbonyl]piperazine-1-carboxylate
• CAS: 1175015-85-6
• 化学式: C₃₁H₃₃FN₄O₄
• 分子量: 544.626
• InChiKey: NWNLUOGVPJURBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[2-(5-fluoro-2-methyl-phenoxy)-6-methyl-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester 、 盐酸 、 [2-(5-fluoro-2-methyl-phenoxy)-6-methyl-1-phenyl-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone dihydrochloride 反应 16.0h， 以lyophilization overnight yielded 2.4 mg of the title compound in the form of the [2-(5-fluoro-2-methyl-phenoxy)-6-methyl-1-phenyl-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone dihydrochloride的产率得到[2-(5-Fluoro-2-methyl-phenoxy)-6-methyl-1-phenyl-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone
  参考文献：
  名称：

  CYCLIC AZAINDOLE-3-CARBOXAMIDES, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICALS

  摘要：

  本发明涉及公式I的环状氮杂吲哚-3-羧酰胺，其中A、R、R10、R20、R30、R40、Y1、Y2、Y3、Y4、n、p和q具有所述要求中指示的含义，它们是有价值的药物活性化合物。具体来说，它们抑制酶肾素并调节肾素-血管紧张素系统的活性，可用于治疗高血压等疾病。此外，本发明还涉及制备公式I化合物的方法、它们的使用以及包含它们的药物组合物。

  公开号：

  US20110039861A1
• 作为产物：
  描述：

  在 N-甲基吗啉 、 O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate 、 sodium hydride 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[2-(5-fluoro-2-methyl-phenoxy)-6-methyl-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Structure-based optimization of potent 4- and 6-azaindole-3-carboxamides as renin inhibitors

  摘要：

  The control of hypertension and associated cardiovascular risk factors is possible by selective inhibition of the aspartyl protease renin due to its unique position in the renin-angiotensin system. Starting from a previously disclosed series of potent and nonchiral indole-3-carboxamides, we further explored this motif by structure-based drug design guided by X-ray crystallography in combination with efficient parallel synthesis. This resulted in the discovery of 4- or 6-azaindole derivatives with remarkable potency for renin inhibition. The best compound from these series showed an IC(50) value of 1.3 nM. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.06.114

文献信息

• CYCLIC AZAINDOLE-3-CARBOXAMIDES, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICALS
  申请人：STEINHAGEN Henning

  公开号：US20110039861A1

  公开（公告）日：2011-02-17

  The present invention relates to cyclic azaindole-3-carboxamides of the formula I, wherein A, R, R 10 , R 20 , R 30 , R 40 , Y 1 , Y 2 , Y 3 , Y 4 , n, p and q have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. Specifically, they inhibit the enzyme renin and modulate the activity of the renin-angiotensin system, and are useful for the treatment of diseases such as hypertension, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.

  本发明涉及公式I的环状氮杂吲哚-3-羧酰胺，其中A、R、R10、R20、R30、R40、Y1、Y2、Y3、Y4、n、p和q具有所述要求中指示的含义，它们是有价值的药物活性化合物。具体来说，它们抑制酶肾素并调节肾素-血管紧张素系统的活性，可用于治疗高血压等疾病。此外，本发明还涉及制备公式I化合物的方法、它们的使用以及包含它们的药物组合物。
• US8580813B2
  申请人：——

  公开号：US8580813B2

  公开（公告）日：2013-11-12
• [EN] CYCLIC AZAINDOLE-3-CARBOXAMIDES, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICALS<br/>[FR] AZAINDOLE-3-CARBOXAMIDES CYCLIQUES, LEUR PRÉPARATION ET LEUR UTILISATION COMME PRODUITS PHARMACEUTIQUES
  申请人：SANOFI AVENTIS

  公开号：WO2009095162A1

  公开（公告）日：2009-08-06

  The present invention relates to cyclic azaindole-3-carboxamides of the formula (I) wherein A, R, R10, R20, R30, R40, Y1, Y2, Y3, Y4, n, p and q have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. Specifically, they inhibit the enzyme renin and modulate the activity of the renin-angiotensin system, and are useful for the treatment of diseases such as hypertension, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.
• Structure-based optimization of potent 4- and 6-azaindole-3-carboxamides as renin inhibitors
  作者：Bodo Scheiper、Hans Matter、Henning Steinhagen、Zsolt Böcskei、Valérie Fleury、Gary McCort

  DOI：10.1016/j.bmcl.2011.06.114

  日期：2011.9

  The control of hypertension and associated cardiovascular risk factors is possible by selective inhibition of the aspartyl protease renin due to its unique position in the renin-angiotensin system. Starting from a previously disclosed series of potent and nonchiral indole-3-carboxamides, we further explored this motif by structure-based drug design guided by X-ray crystallography in combination with efficient parallel synthesis. This resulted in the discovery of 4- or 6-azaindole derivatives with remarkable potency for renin inhibition. The best compound from these series showed an IC(50) value of 1.3 nM. (C) 2011 Published by Elsevier Ltd.
• Cyclic azaindole-3-carboxamides, their preparation and their use as pharmaceuticals
  申请人：Steinhagen Henning

  公开号：US08580813B2

  公开（公告）日：2013-11-12

  The present invention relates to cyclic azaindole-3-carboxamides of the formula I, wherein A, R, R10, R20, R30, R40, Y1, Y2, Y3, Y4, n, p and q have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. Specifically, they inhibit the enzyme renin and modulate the activity of the renin-angiotensin system, and are useful for the treatment of diseases such as hypertension, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.

  本发明涉及公式I的环状氮杂吲哚-3-羧酰胺，其中A、R、R10、R20、R30、R40、Y1、Y2、Y3、Y4、n、p和q具有所述权利要求中指示的含义，这些化合物是有价值的药物活性化合物。具体而言，它们抑制酶肾素并调节肾素-血管紧张素系统的活性，可用于治疗高血压等疾病。本发明还涉及制备公式I化合物的方法，以及包含它们的药物组合物的使用。