5-Amino-3-(N-methylpyrrolidin-3-yl)-1H-indole | 156499-26-2

• 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: 5-Amino-3-(N-methylpyrrolidin-3-yl)-1H-indole
• 英文别名: 3-(1-methylpyrrolidin-3-yl)-1H-indol-5-amine
• CAS: 156499-26-2
• 化学式: C₁₃H₁₇N₃
• 分子量: 215.298
• InChiKey: NEQAWYTYZBCYHY-UHFFFAOYSA-N

物化性质

• 沸点：
  432.9±40.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-3-硝基吡啶 、 5-Amino-3-(N-methylpyrrolidin-3-yl)-1H-indole 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 以44%的产率得到3-(1-甲基吡咯烷-3-基)-N-(3-硝基吡啶-2-基)-1H-吲哚-5-胺
  参考文献：
  名称：

  Macor; Blank; Fox, Journal of Medicinal Chemistry, 1994, vol. 37, # 16, p. 2509 - 2512

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氨基吲哚 在 palladium dihydroxide lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 为溶剂， 生成 5-Amino-3-(N-methylpyrrolidin-3-yl)-1H-indole
  参考文献：
  名称：

  Macor; Blank; Fox, Journal of Medicinal Chemistry, 1994, vol. 37, # 16, p. 2509 - 2512

  摘要：

  DOI：

文献信息

• [EN] INDOLE COMPOUNDS AND METHODS FOR TREATING VISCERAL PAIN<br/>[FR] COMPOSÉS D'INDOLE ET PROCÉDÉS DE TRAITEMENT DE LA DOULEUR VISCÉRALE
  申请人：NEURAXON INC

  公开号：WO2009062319A1

  公开（公告）日：2009-05-22

  The invention features methods of treating visceral pain or a condition in a mammal caused by the action of nitric oxide synthase (NOS) or by the action of serotonin 5HT1D/1B receptors, by administering to a patient in need thereof a therapeutically effective amount of an indole compound of Formula (I), or a pharmaceutically acceptable salt or prodrug thereof. The methods of the invention may further comprise the administration of additional therapeutic agent. The invention also features new compounds of Formula (I), pharmaceutical compositions thereof, and methods of resolving enantiomeric mixtures.

  该发明涉及治疗哺乳动物体内因一氧化氮合酶（NOS）或5-羟色胺受体5HT1D/1B的作用引起的内脏疼痛或疾病的方法，通过向需要治疗的患者施用式(I)的吲哚化合物的治疗有效量，或其药学上可接受的盐或前药。该发明的方法还可以包括额外治疗剂的施用。该发明还涉及式(I)的新化合物、其药物组合物以及解决对映体混合物的方法。
• Substituted indole compounds having NOS inhibitory activity
  申请人：Maddaford Shawn

  公开号：US20060258721A1

  公开（公告）日：2006-11-16

  The present invention features inhibitors of nitric oxide synthase (NOS), particularly those that selectively inhibit neuronal nitric oxide synthase (nNOS) in preference to other NOS isoforms. The NOS inhibitors of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing conditions such as, for example, stroke, reperfusion injury, neurodegeneration, head trauma, CABG, migraine headache with and without aura, migraine with allodynia, central post-stroke pain (CPSP), neuropathic pain, morphine/opioid induced tolerance and hyperalgesia.

  本发明涉及一种一氧化氮合酶（NOS）的抑制剂，特别是那些选择性地抑制神经型一氧化氮合酶（nNOS）而不是其他NOS同工酶的抑制剂。本发明的NOS抑制剂，单独或与其他药用活性剂结合使用，可用于治疗或预防诸如中风、再灌注损伤、神经退行性疾病、头部创伤、冠状动脉搭桥术（CABG）、伴或不伴有先兆的偏头痛、伴有疼痛性过敏的偏头痛、中枢性中风后疼痛（CPSP）、神经痛、吗啡/阿片类药物引起的耐受性和过度疼痛等疾病。
• 5-arylindole derivatives
  申请人：Pfizer Inc.

  公开号：US05886008A1

  公开（公告）日：1999-03-23

  Compounds of formula (I), wherein R.sub.1 is (a), (b), (c) or (d); n is 0, 1 or 2; A, B, C and D are each independently nitrogen or carbon; R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently hydrogen, C.sub.1 to C.sub.6 alkyl, aryl, C.sub.1 to C.sub.3 alkyl-aryl, halogen (e.g. fluorine, chlorine, bromine or iodine), cyano, nitro, --(CH.sub.2).sub.m NR.sub.14 R.sub.15, --(CH.sub.2).sub.m OR.sub.9, --SR.sub.9, --SO.sub.2 NR.sub.14 R.sub.15, --(CH.sub.2).sub.m NR.sub.14 SO.sub.2 R.sub.15 --(CH.sub.2).sub.m NR.sub.14 CO.sub.2 R.sub.9, --(CH.sub.2).sub.m NR.sub.14 COR.sub.9, --(CH.sub.2).sub.m NR.sub.14 CONHR.sub.9, --CONR.sub.14 R.sub.15, or --CO.sub.2 R.sub.9 ; R.sub.2 and R.sub.3, R.sub.3 and R.sub.4, or R.sub.4 and R.sub.5 may be taken together to form a five- to seven-membered alkyl ring, a six-membered aryl ring, a five- to seven-membered heteroalkyl ring having 1 heteroatom of N, O, or S, or a five- to six-membered heteroaryl ring having H 1 or 2 heteroatoms of N, O, or S and the pharmaceutically acceptable salts thereof. These compounds are useful in treating migraine and other disorders. These compounds are useful psychotherapeutics and are potent serotonin (5-HT.sub.1) agonists and benzodiazepine agonists and antagonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain and chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vosodilators. ##STR1##

  式（I）的化合物，其中R.sub.1为（a）、（b）、（c）或（d）；n为0、1或2；A、B、C和D分别独立为氮或碳；R.sub.2、R.sub.3、R.sub.4和R.sub.5分别独立为氢、C.sub.1至C.sub.6烷基、芳基、C.sub.1至C.sub.3烷基-芳基、卤素（例如氟、氯、溴或碘）、氰基、亚硝基、--（CH.sub.2）.sub.m NR.sub.14 R.sub.15、--（CH.sub.2）.sub.m OR.sub.9、--SR.sub.9、--SO.sub.2 NR.sub.14 R.sub.15、--（CH.sub.2）.sub.m NR.sub.14 SO.sub.2 R.sub.15、--（CH.sub.2）.sub.m NR.sub.14 CO.sub.2 R.sub.9、--（CH.sub.2）.sub.m NR.sub.14 COR.sub.9、--（CH.sub.2）.sub.m NR.sub.14 CONHR.sub.9、--CONR.sub.14 R.sub.15，或--CO.sub.2 R.sub.9；R.sub.2和R.sub.3、R.sub.3和R.sub.4，或R.sub.4和R.sub.5可以结合在一起形成五至七元烷基环、六元芳基环、具有1个N、O或S杂原子的五至七元杂烷基环，或具有1个或2个N、O或S杂原子的五至六元杂芳基环及其药学上可接受的盐。这些化合物在治疗偏头痛和其他疾病方面很有用。这些化合物是有用的精神疗法药物，是有效的5-羟色胺（5-HT.sub.1）激动剂和苯二氮䓬类激动剂和拮抗剂，可用于治疗抑郁症、焦虑症、进食障碍、肥胖症、药物滥用、集群头痛、偏头痛、疼痛和慢性阵发性半边头痛以及与血管疾病相关的头痛等因缺乏5-羟色胺神经递质而引起的其他疾病。这些化合物还可用作中枢作用降压药和血管扩张剂。
• Indole derivatives
  申请人：Pfizer Inc

  公开号：US05639752A1

  公开（公告）日：1997-06-17

  Compounds of the formula ##STR1## wherein Z is ##STR2## R.sub.1 is ##STR3## X is O, NH, or S; A, B, D, E, and F are each independently C, N, O, or S; wherein the remaining variables are defined in the specification, and the pharmaceutically acceptable salts thereof. These compounds are useful psychotherapeutics and are potent serotonin (5-HT.sub.1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vasodilators.

  该公式化合物为##STR1##，其中Z为##STR2##，R.sub.1为##STR3##，X为O、NH或S；A、B、D、E和F分别独立地为C、N、O或S；其余变量在说明书中有定义，以及其药用盐。这些化合物是有用的精神治疗药物，是有效的5-羟色胺（5-HT.sub.1）激动剂，可用于治疗抑郁症、焦虑症、进食障碍、肥胖症、药物滥用、簇状头痛、偏头痛、疼痛、慢性阵发性半头痛和与血管疾病相关的头痛，以及其他由5-羟色胺能神经传导不足引起的疾病。这些化合物还可用作中枢作用的降压药和扩血管药。
• SUBSTITUTED INDOLE COMPOUNDS HAVING NOS INHIBITORY ACTIVITY
  申请人：Maddaford Shawn

  公开号：US20080249302A1

  公开（公告）日：2008-10-09

  The present invention features inhibitors of nitric oxide synthase (NOS), particularly those that selectively inhibit neuronal nitric oxide synthase (nNOS) in preference to other NOS isoforms. The NOS inhibitors of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing conditions such as, for example, stroke, reperfusion injury, neurodegeneration, head trauma, CABG, migraine headache with and without aura, migraine with allodynia, central post-stroke pain (CPSP), neuropathic pain, morphine/opioid induced tolerance and hyperalgesia.

  本发明涉及一种一氧化氮合酶（NOS）抑制剂，特别是那些选择性地抑制神经元一氧化氮合酶（nNOS）而不是其他NOS亚型。本发明的NOS抑制剂，单独或与其他药理活性剂联合使用，可用于治疗或预防诸如中风、再灌注损伤、神经退行性疾病、头部创伤、CABG、偏头痛（有和无先兆）、伴有痛觉过敏的偏头痛、中枢后中风疼痛（CPSP）、神经病性疼痛、吗啡/阿片类药物引起的耐受和高敏感性等疾病。