N-(2-fluoro-4-methoxyphenyl)-4-hydroxy-1H-indole-3-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-fluoro-4-methoxyphenyl)-4-hydroxy-1H-indole-3-carboxamide
• 化学式: C₁₆H₁₃FN₂O₃
• 分子量: 300.289
• InChiKey: NKJRLBQTDOOCLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-Fluoro-4-methoxyphenyl)-4-benzyloxy-1H-indole-3-carboxamide 在 钯 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 N-(2-fluoro-4-methoxyphenyl)-4-hydroxy-1H-indole-3-carboxamide
  参考文献：
  名称：

  Substituted fused pyrroleoximes and fused pyrazoleoximes

  摘要：

  揭示了公式1的化合物及其药学上可接受的盐，其中R、Ar、A、n、R1和R2在此处定义。这些化合物是高度选择性的GABAA脑受体的激动剂、拮抗剂或逆拮抗剂，或者是GABAA脑受体的激动剂、拮抗剂或逆拮抗剂的前药，因此在焦虑、抑郁、唐氏综合症、睡眠和癫痫障碍、苯二氮卓类药物过量和增强记忆的诊断和治疗中非常有用。还披露了包括包装的药物组合物在内的药物组合物。

  公开号：

  US20020128236A1
• 作为试剂：
  描述：

  N-(2-Fluoro-4-methoxyphenyl)-4-benzyloxy-1H-indole-3-carboxamide 、 甲醇 、 氢气 在 钯 N-(2-fluoro-4-methoxyphenyl)-4-hydroxy-1H-indole-3-carboxamide 作用下， 以 乙醇 为溶剂， 反应 23.0h， 以to afford N-(2-fluoro-4-methoxyphenyl)-4-hydroxy-1H-indole-3-carboxamide (Compound 2) as a beige solid的产率得到N-(2-fluoro-4-methoxyphenyl)-4-hydroxy-1H-indole-3-carboxamide
  参考文献：
  名称：

  Substituted Fused Pyrroleoximes and Fused Pyrazoleoximes

  摘要：

  本发明涉及以下式的化合物及其药学上可接受的盐，其中R、Ar、A、n、R1和R2的定义如下。这些化合物是高度选择性的GABAA脑受体的激动剂、拮抗剂或反向激动剂，或者是GABAA脑受体激动剂、拮抗剂或反向激动剂的前药，因此可用于诊断和治疗焦虑症、抑郁症、唐氏综合征、睡眠和癫痫障碍、苯二氮卓类药物过量和增强记忆。还公开了包括包装的药物组合物在内的制药组合物。

  公开号：

  US20080032975A1

文献信息

• Certain pyrrolo pyridine-3-carboxamides; a new class of GABA brain
  申请人：Neurogen Corporation

  公开号：US05750702A1

  公开（公告）日：1998-05-12

  The present invention encompasses structures of the formula: ##STR1## or the pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## wherein: W represents substituted or unsubstituted phenyl; X is hydrogen, hydroxy or lower alkyl; T is hydrogen, halogen, hydroxy, nitro, amino or alkyl; R.sub.3 is hydrogen or an organic group; R.sub.4 is hydrogen or substituted or unsubstituted organic substituent; R.sub.5 and R.sub.6 represent organic, and inorganic substituents; and n is 1, 2, 3, or 4, which compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compounds are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.

  本发明涵盖了以下结构的化合物：##STR1##或其药学上可接受的非毒性盐，其中：##STR2##其中：W代表取代或未取代的苯基；X为氢、羟基或较低的烷基；T为氢、卤素、羟基、硝基、氨基或烷基；R.sub.3为氢或有机基团；R.sub.4为氢或取代或未取代的有机取代基；R.sub.5和R.sub.6代表有机和无机取代基；n为1、2、3或4，这些化合物是GABAa脑受体的高度选择性激动剂、拮抗剂或逆拮抗剂，或者是GABAa脑受体激动剂、拮抗剂或逆拮抗剂的前药。这些化合物在焦虑、睡眠和癫痫障碍的诊断和治疗、苯二氮卓类药物过量和增强记忆方面是有用的。
• Certain fused pyrrolecarboxanilides and their use as GABA brain receptor
  申请人：Neurogen Corporation

  公开号：US05484944A1

  公开（公告）日：1996-01-16

  The present invention encompasses structures of the formula I: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## wherein: W represents substituted or unsubstituted aryl groups; X is hydrogen, hydroxy or lower alkyl; T is hydrogen, halogen, hydroxyl, amino or alkyl; R.sub.3 is hydrogen or an organic group; R.sub.4 is hydrogen or substituted or unsubstituted organic substituent; R.sub.5 and R.sub.6 represent organic, and inorganic substituents; and n is 1, 2, 3, or 4. These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compounds are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.

  本发明涵盖了以下结构的化合物I：其中：W代表取代或未取代的芳基；X为氢、羟基或较低的烷基；T为氢、卤素、羟基、氨基或烷基；R.sub.3为氢或有机基团；R.sub.4为氢或取代或未取代的有机取代基；R.sub.5和R.sub.6代表有机和无机取代基；n为1、2、3或4。这些化合物是GABAa脑受体的高度选择性激动剂、拮抗剂或逆拮抗剂，或者是GABAa脑受体的激动剂、拮抗剂或逆拮抗剂的前药。这些化合物在焦虑、睡眠和癫痫障碍的诊断和治疗、苯二氮䓬类药物过量和增强记忆方面具有用途。
• Certain fused pyrrolecarboxanilides; a new class of GABA brain receptor
  申请人：Neurogen Corporation

  公开号：US05608079A1

  公开（公告）日：1997-03-04

  The present invention encompasses structures of the formula I: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## wherein: W represents substituted or unsubstituted aryl groups; X is hydrogen, hydroxy or lower alkyl; T is hydrogen, halogen, hydroxyl, amino or alkyl; R.sub.3 is hydrogen or an organic group; R.sub.4 is hydrogen or substituted or unsubstituted organic substituent; R.sub.5 and R.sub.6 represent organic, and inorganic substituents; and n is 1, 2, 3, or 4. These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain recpetors. These compounds are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.

  本发明涵盖了I式结构和其药学上可接受的无毒盐，其中：W代表取代或未取代的芳基基团；X为氢、羟基或低碳基；T为氢、卤素、羟基、氨基或烷基；R3为氢或有机基团；R4为氢或取代或未取代的有机取代基；R5和R6代表有机和无机取代基；n为1、2、3或4。这些化合物是高度选择性的GABAa脑受体激动剂、拮抗剂或反向激动剂，或是GABAa脑受体激动剂、拮抗剂或反向激动剂的前药。这些化合物在焦虑、睡眠和癫痫障碍、苯二氮平类药物过量和增强记忆方面的诊断和治疗中有用。
• Certain fused pyrrolecarboxanilides; a new class of gaba brain receptor
  申请人：Neurogen Corporation

  公开号：US05925770A1

  公开（公告）日：1999-07-20

  The present invention encompasses structures of the formula: ##STR1## or the pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## wherein: W represents substituted or unsubstituted phenyl; X is hydrogen, T is hydrogen, and n is 3, which compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compounds are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.

  本发明涵盖以下结构的化合物：## STR1 ## 或其药学上可接受的非毒性盐，其中：## STR2 ## 其中：W代表取代或未取代的苯基；X为氢，T为氢，n为3，这些化合物是高度选择性的GABAa脑受体的激动剂，拮抗剂或反向激动剂或GABAa脑受体激动剂，拮抗剂或反向激动剂的前药。这些化合物在焦虑，睡眠和癫痫障碍，苯二氮平类药物过量和增强记忆方面有用。
• Substituted fused pyrroleimines and pyrazoleimines
  申请人：Neurogen Corporation

  公开号：US06743817B2

  公开（公告）日：2004-06-01

  Disclosed are compounds of the formula and the pharmaceutically acceptable salts thereof wherein R, Ar, A, n, R1 and R2 are defined herein. These compounds are highly selective agonists, antagonists or inverse agonists for GABAA brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAA brain receptors and are therefore useful in the diagnosis and treatment of anxiety, depression, Down Syndrome, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory. Pharmaceutical compositions, including packaged pharmaceutical compositions, are also disclosed.

  本发明揭示了具有以下公式及其药学上可接受的盐的化合物，其中R，Ar，A，n，R1和R2在此定义。这些化合物是高度选择性的GABAA脑受体激动剂，拮抗剂或反向激动剂，或是GABAA脑受体激动剂，拮抗剂或反向激动剂的前药，因此可用于诊断和治疗焦虑、抑郁、唐氏综合症、睡眠和癫痫障碍、苯二氮卓类药物过量以及增强记忆。还揭示了包括包装的制药组合物在内的制药组合物。