N-[4-(methoxymethyl)phenyl]-4-oxo-4,5,6,7-tetrahydro-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-[4-(methoxymethyl)phenyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide
• 英文别名: N-[4-(methoxymethyl)phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: JOFPKRNBIGBSOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

文献信息

• Fused pyrrolecarboxamides: GABA brain receptor ligands
  申请人：Albaugh Pamela

  公开号：US20050014939A1

  公开（公告）日：2005-01-20

  Substituted pyrrolecarboxamide compounds are disclosed. These compounds are highly selective agonists, antagonists or inverse agonists for GABA A brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABA A brain receptors and are therefore useful in the diagnosis and treatment of anxiety, depression, Alzheimer's dementia, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory. Pharmaceutical compositions, including packaged pharmaceutical compositions, are further provided. Compounds of the invention are also useful as probes for the localization of GABA A receptors in tissue samples.

  揭示了取代吡咯甲酰胺化合物。这些化合物是高度选择性的GABAA脑受体的激动剂、拮抗剂或逆向激动剂，或者是GABAA脑受体的激动剂、拮抗剂或逆向激动剂的前药，因此在焦虑、抑郁、阿尔茨海默病痴呆、睡眠和癫痫障碍、苯二氮卓类药物过量以及增强记忆的诊断和治疗中非常有用。此外，还提供了包括包装的药物组合物在内的制药组合物。该发明的化合物还可用作定位组织样本中GABAA受体的探针。
• Fused pyrrolecarboxamides; a new class of GABA brain receptor ligands
  申请人：Neurogen

  公开号：US20010029299A1

  公开（公告）日：2001-10-11

  Disclosed are compounds of the formula: 1 or the pharmaceutically acceptable non-toxic salts thereof wherein: G, X, T, n, and R 3 -R 6 are as defined herein, 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.

  本发明涉及以下公式的化合物：1或其药学上可接受的非毒性盐，其中：G、X、T、n和R3-R6的定义如本文所述，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，或是GABAa脑受体的激动剂、拮抗剂或反向激动剂的前药。这些化合物在焦虑、睡眠和癫痫障碍的诊断和治疗、苯二氮卓类药物过量和增强记忆方面有用。
• Certain fused pyrrolecarboxanilides; a new class of gaba brain receptor ligands
  申请人：NEUROGEN CORPORATION

  公开号：EP0825193A1

  公开（公告）日：1998-02-25

  The present invention encompasses structures of the formula (I) and the pharmaceutically acceptable non-toxic salts thereof wherein T is halogen, hydrogen, hydroxyl, amino or straight or branched chain lower alkoxy having 1-6 carbon atoms; X is hydrogen, hydroxyl or straight or branched chain lower alkyl having 1-6 carbon atoms; W is phenyl substituted with a 3,4-methylenedioxy, 3,4-ethylenedioxy, or 3,4-isopropylidenedioxy group, or a 2-naphthyridinyl group which may be substituted with halogen; and represents wherein Y represents nitrogen or C-R4; Z represents N-R7 or a carbon atom substituted with R8 and R9, i.e., C(R8)(R9); n is 1, 2, 3, or 4; R3 is hydrogen, phenyl, 2, 3 or 4-pyridyl, straight or branched chain lower alkyl having 1-6 carbon atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl where each alkyl is straight or branched chain lower alkyl having 1-6 carbon atoms; R4 is halogen or trifluoromethyl; or -OR10, - COR10, -CO2R10, -OCOR10, or -R10, where R10 is hydrogen, phenyl, 2, 3 or 4-pyridyl, straight or branched chain lower alkyl having 1-6 carbon atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl where each alkyl is straight or branched chain lower alkyl having 1-6 carbon atoms; or -CONR11R12 or -(CH2)mNR11R12, where m is 0, 1, or 2; R11 represents hydrogen, straight or branched chain lower alkyl having 1-6 carbon atoms; and R12 is hydrogen, phenyl, 2, 3 or 4-pyridyl, straight or branched chain lower alkyl having 1-6 carbon atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl where each alkyl is straight or branched chain lower alkyl having 1-6 carbon atoms; or NR11R12 forms a heterocyclic group which is morpholyl, piperidyl, pyrrolidyl, or N-alkyl piperazyl; R5 and R6 are the same or different and represent hydrogen, halogen, straight or branched chain lower alkyl having 1-6 carbon atoms, or straight or branched chain lower alkoxy having 1-6 carbon atoms; R7 is hydrogen, phenyl, 2, 3 or 4-pyridyl, straight or branched chain lower alkyl having 1-6 carbon atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl where each alkyl is straight or branched chain lower alkyl having 1-6 carbon atoms; R8 is hydrogen or straight or branched chain lower alkyl having 1-6 carbon atoms; and R9 is -COR13, -CO2R13 or -R13, where R13 is hydrogen, phenyl, 2, 3 or 4-pyridyl, straight or branched chain lower alkyl having 1-6 carbon atoms, or phenylalkyl or 2, 3, or 4-pyridylalkyl where each alkyl is straight or branched chain lower alkyl having 1-6 carbon atoms; or - CONR14R15 or - (CH2)kNR14R15, where k is 0, 1, or 2; R14 represents hydrogen, straight or branched chain lower alkyl having 1-6 carbon atoms; and R15 is hydrogen, phenyl, 2, 3, or 4-pyridyl, straight or branched chain lower alkyl having 1-6 carbon atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl where each alkyl is straight or branched chain lower alkyl having 1-6 carbon atoms; or NR14R15 forms a heterocyclic group which is morpholyl, piperidyl, pyrrolidyl, or N-alkyl piperazyl; or (b) T and X are as defined above; W is phenyl, 2 or 3-thienyl, 2, 3, or 4-pyridyl or 6-quinolinyl, each of which may be mono or disubstituted with halogen, cyano, hydroxy, straight or branched chain lower alkyl having 1-6 carbon atoms, amino, mono or dialkylamino where each alkyl is independently straight or branched chain lower alkyl having 1-6 carbon atoms, straight or branched chain lower alkoxy having 1-6 carbon atoms, or NR1COR2, COR2, CONR1R2 where R1 and R2 are the same or different and represent hydrogen or straight or branched chain lower alkyl having 1-6 carbon atoms; and represents or a compound of the formula:

  本发明包括式 (I) 结构及其可接受的无毒盐 及其药学上可接受的无毒盐 其中 T 是卤素、氢、羟基、氨基或具有 1-6 个碳原子的直链或支链低级烷氧基；X 是氢、羟基或具有 1-6 个碳原子的直链或支链低级烷基；W 是被 3,4-亚甲二氧基、3,4-亚乙二氧基或 3,4-异亚丙基二氧基取代的苯基，或可被卤素取代的 2-萘啶基团；以及 代表 其中 Y 代表氮或 C-R4； Z 代表 N-R7 或被 R8 和 R9 取代的碳原子，即C(R8)(R9)；n 是 1、2、3 或 4；R3 是氢、苯基、2、3 或 4-吡啶基、具有 1-6 个碳原子的直链或支链低级烷基、或苯基烷基或 2、3 或 4-吡啶基烷基，其中每个烷基是具有 1-6 个碳原子的直链或支链低级烷基；R4 是卤素或三氟甲基；或-OR10、-COR10、-CO2R10、-OCOR10 或-R10，其中 R10 是氢、苯基、2、3 或 4-吡啶基、具有 1-6 个碳原子的直链或支链低级烷基或苯基烷基或 2、3 或 4-吡啶基烷基，其中每个烷基是具有 1-6 个碳原子的直链或支链低级烷基；或 -CONR11R12 或 -(CH2)mNR11R12，其中 m 为 0、1 或 2；R11 代表氢、具有 1-6 个碳原子的直链或支链低级烷基；而 R12 是氢、苯基、2、3 或 4-吡啶基、具有 1-6 个碳原子的直链或支链低级烷基、或苯基烷基或 2、3 或 4-吡啶基烷基，其中每个烷基是具有 1-6 个碳原子的直链或支链低级烷基；或 NR11R12 形成一个杂环基团，该杂环基团是吗啉基、哌啶基、吡咯烷基或 N-烷基哌嗪基；R5 和 R6 相同或不同，代表氢、卤素、具有 1-6 个碳原子的直链或支链低级烷基，或具有 1-6 个碳原子的直链或支链低级烷氧基；R7 是氢、苯基、2、3 或 4-吡啶基、具有 1-6 个碳原子的直链或支链低级烷基，或苯基烷基或 2、3 或 4-吡啶基烷基，其中每个烷基都是具有 1-6 个碳原子的直链或支链低级烷基；R8 是氢或具有 1-6 个碳原子的直链或支链低级烷基；以及 R9 是-COR13、-CO2R13 或-R13，其中 R13 是氢、苯基、2、3 或 4-吡啶基、具有 1-6 个碳原子的直链或支链低级烷基或苯基烷基或 2、3 或 4-吡啶基烷基，其中每个烷基是具有 1-6 个碳原子的直链或支链低级烷基；或-CONR14R15 或-(CH2)kNR14R15，其中 k 为 0、1 或 2；R14 代表氢、具有 1-6 个碳原子的直链或支链低级烷基；R15 代表氢、苯基、2、3 或 4-吡啶基、具有 1-6 个碳原子的直链或支链低级烷基或苯基烷基或 2、3 或 4-吡啶基烷基，其中每个烷基都是具有 1-6 个碳原子的直链或支链低级烷基；或 NR14R15 形成一个杂环基团，该杂环基团为吗啉基、哌啶基、吡咯烷基或 N-烷基哌嗪基；或 (b) T 和 X 如上文所定义；W 是苯基、2 或 3-噻吩基、2、3 或 4-吡啶基或 6-喹啉基，其中每个基团可被卤素、氰基、羟基、具有 1-6 个碳原子的直链或支链低级烷基、氨基、单烷基氨基或二烷基氨基单取代或二取代，其中每个烷基独立地为具有 1-6 个碳原子的直链或支链低级烷基、具有 1-6 个碳原子的直链或支链低级烷氧基，或 NR1COR2、COR2、CONR1R2，其中 R1 和 R2 相同或不同，代表氢或具有 1-6 个碳原子的直链或支链低级烷基；和 代表 或以下式子的化合物
• CERTAIN FUSED PYRROLECARBOXANILIDES; A NEW CLASS OF GABA BRAIN RECEPTOR LIGANDS
  申请人：NEUROGEN CORPORATION

  公开号：EP0725775B1

  公开（公告）日：1998-07-22
• NOVEL FUSED PYRROLECARBOXAMIDES; A NEW CLASS OF GABA BRAIN RECEPTOR LIGANDS
  申请人：NEUROGEN CORPORATION

  公开号：EP1019372A1

  公开（公告）日：2000-07-19