(R)-5-bromo-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one | 1189569-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: (R)-5-bromo-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one
• 英文别名: (2R)-5-bromo-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one；(2R)-5-bromospiro[1,3-dihydroindene-2,3'-1H-pyrrolo[2,3-b]pyridine]-2'-one
• CAS: 1189569-86-5
• 化学式: C₁₅H₁₁BrN₂O
• 分子量: 315.169
• InChiKey: XBFJVCVAXFLHTN-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-5-bromo-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 、 在 N-甲基二环己基胺 、 bis(tributylphosphine)palladium 0 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,2-dimethyl-N-[3-[(2R)-2'-oxospiro[1,3-dihydroindene-2,3'-1H-pyrrolo[2,3-b]pyridine]-5-yl]prop-2-ynyl]-N-[(1R)-1-phenylethyl]propanamide
  参考文献：
  名称：

  (E)-Alkenes as replacements of amide bonds: Development of novel and potent acyclic CGRP receptor antagonists

  摘要：

  A new class of CGRP receptor antagonists was identified by replacing the central amide of a previously identified anilide lead structure with ethylene, ethane, or ethyne linkers. (E)-Alkenes as well as alkynes were found to preserve the proper bioactive conformation of the amides, necessary for efficient receptor binding. Further exploration resulted in several potent compounds against CGRP-R with low susceptibility to P-gp mediated efflux. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.027
• 作为产物：
  描述：

  7-氮杂吲哚 在 palladium 10% on activated carbon 、 copper(I) bromide 盐酸 、 水 、 氢溴酸 、 氢气 、 pyridinium hydrobromide perbromide 、 sodium hydride 、 氯化铵 、 caesium carbonate 、 乙二胺 、 sodium hydroxide 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 60.5h， 生成 (R)-5-bromo-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one
  参考文献：
  名称：

  [EN] MONOCYCLIC CGRP RECEPTOR ANTAGONISTS
  [FR] ANTAGONISTES DES RÉCEPTEURS CGRP MONOCYCLIQUES

  摘要：

  公开号：

  WO2009120652A3

文献信息

• [EN] IMIDAZOLINONE DERIVATIVES AS CGRP RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS D'IMIDAZOLINONE EN TANT QU'ANTAGONISTES DE RÉCEPTEURS CGRP
  申请人：MERCK SHARP & DOHME

  公开号：WO2010077752A1

  公开（公告）日：2010-07-08

  The present invention is directed to imidazolinone derivatives which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

  本发明涉及嘧啶啉酮衍生物，其为CGRP受体拮抗剂，可用于治疗或预防涉及CGRP的疾病，如偏头痛。该发明还涉及包含这些化合物的药物组合物，以及在预防或治疗涉及CGRP的这类疾病中使用这些化合物和组合物。
• [EN] NON-AMIDIC LINKERS WITH BRANCHED TERMINI AS CGRP RECEPTOR ANTAGONISTS<br/>[FR] LIEURS NON AMIDIQUES AVEC TERMINAISON RAMIFIÉE CONSTITUANT DES ANTAGONISTES DE RÉCEPTEURS DE PEPTIDES ASSOCIÉS AU GÈNE DE LA CALCITONINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2010021864A1

  公开（公告）日：2010-02-25

  The present invention is directed to novel non-amidic linkers with branched termini derivatives which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

  本发明涉及具有分支末端衍生物的新型非酰胺连接剂，这些衍生物是CGRP受体拮抗剂，可用于治疗或预防涉及CGRP的疾病，如偏头痛。该发明还涉及包含这些化合物的药物组合物以及在涉及CGRP的这类疾病的预防或治疗中使用这些化合物和组合物。
• NON-AMIDIC LINKERS WITH BRANCHED TERMINI AS CGRP RECEPTOR ANTAGONISTS
  申请人：Wood Michael R.

  公开号：US20110190329A1

  公开（公告）日：2011-08-04

  The present invention is directed to novel non-amidic linkers with branched termini derivatives which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

  本发明涉及一种新型的非酰胺连接剂，其具有分支末端衍生物，可作为CGRP受体拮抗剂，用于治疗或预防CGRP参与的疾病，如偏头痛。本发明还涉及包含这些化合物的制药组合物，以及在预防或治疗CGRP参与的这些疾病中使用这些化合物和组合物的方法。
• IMIDAZOLINONE DERIVATIVES AS CGRP RECEPTOR ANTAGONISTS
  申请人：Selnick Harold G.

  公开号：US20110306626A1

  公开（公告）日：2011-12-15

  The present invention is directed to imidazolinone derivatives which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

  本发明涉及咪唑啉酮衍生物，其是CGRP受体拮抗剂，可用于治疗或预防涉及CGRP的疾病，如偏头痛。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗涉及CGRP的这些疾病中使用这些化合物和组合物的用途。
• RADIOLABELED CGRP ANTAGONISTS
  申请人：Bell Ian M.

  公开号：US20120121508A1

  公开（公告）日：2012-05-17

  The present invention is directed to radiolabeled CGRP receptor antagonists which are useful for the quantitative imaging of CGRP receptors in mammals.

  本发明涉及用于哺乳动物中CGRP受体定量成像的放射性标记的CGRP受体拮抗剂。