6-bromo-10-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-8-carbonitrile | 1558046-20-0

• 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: 6-bromo-10-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-8-carbonitrile
• 英文别名: 6-Bromo-10-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile；6-bromo-10-methyl-1-oxo-3,4-dihydro-2H-pyrazino[1,2-a]indole-8-carbonitrile
• CAS: 1558046-20-0
• 化学式: C₁₃H₁₀BrN₃O
• 分子量: 304.146
• InChiKey: UTSWVDWUMYKXLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  、 6-bromo-10-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-8-carbonitrile 、 2,4-二氯苯硼酸 生成 6-(2,4-dichlorophenyl)-10-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-8-carbonitrile
  参考文献：
  名称：

  Piperazino[1,2-a]indol-1-ones and [1,4]diazepino[1,2-a]indol-1-one

  摘要：

  本发明涉及一般式I的化合物或其药学上可接受的盐，其中R1、R2、R3、X、R和n的定义如本文所述。这些化合物可用于治疗精神分裂症、强迫症人格障碍、重度抑郁症、双相障碍、焦虑症、正常衰老、癫痫、视网膜退化、创伤性脑损伤、脊髓损伤、创伤后应激障碍、惊恐障碍、帕金森病、痴呆症、阿尔茨海默病、轻度认知障碍、化疗引起的认知功能障碍、唐氏综合症、自闭症谱系障碍、听力损失、耳鸣、脊髓小脑性共济失调、肌萎缩侧索硬化症、多发性硬化症、亨廷顿病、中风、放射治疗、慢性压力、对神经活性药物的滥用，如酒精、鸦片类、甲基苯丙胺、苯环利定和可卡因等。

  公开号：

  US09284321B2

文献信息

• [EN] PIPERAZINO[1,2-A]INDOL-1-ONES AND [1,4]DIAZEPINO[1,2-A]INDOL-1-ONE<br/>[FR] PIPÉRAZINO[1,2-A]INDOL-1-ONES ET [1,4]DIAZÉPINO[1,2-A]INDOL-1-ONE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014161801A1

  公开（公告）日：2014-10-09

  The present invention relates to compounds of general formula I wherein R1 is halogen, lower alkyl, lower alkoxy, lower alkyl substituted by halogen, lower alkoxy substituted by halogen or cyano; R2 is hydrogen, CF3 or lower alkyl; R3 is hydrogen, lower alkyl, lower alkenyl, lower alkinyl, heterocycloalkyl, lower alkyl substitueted by cyano, cyano, benzyl substituted by halogen, 2-oxa-6-aza-spiro[3.3]hept-6-yl or is lower alkoxy substituted by halogen; X is -CH2- or -CH2-CH2-; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomers thereof. The compounds may be used for the treatment of schizophrenia, obsessive-compulsive personality disorder, major depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, mild cognitive impairment, chemotherapy-induced cognitive dysfunction, Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of neuro-active drugs, such as alcohol, opiates, methamphetamine, phencyclidine and cocaine.

  本发明涉及一般式I的化合物，其中R1是卤素、较低的烷基、较低的烷氧基、由卤素取代的较低的烷基、由卤素取代的较低的烷氧基或氰基；R2是氢、三氟甲基或较低的烷基；R3是氢、较低的烷基、较低的烯基、较低的炔基、杂环烷基、由氰基取代的较低的烷基、氰基、由卤素取代的苄基、2-氧-6-氮杂螺[3.3]庚-6-基或由卤素取代的较低的烷氧基；X是-CH2-或-CH2-CH2-；或是其对应的对映体和/或光学异构体的药用可接受的酸盐，或是一个外消旋混合物。这些化合物可用于治疗精神分裂症、强迫性人格障碍、重性抑郁症、躁郁症、焦虑障碍、正常衰老、癫痫、视网膜退化、创伤性脑损伤、脊髓损伤、创伤后应激障碍、恐慌障碍、帕金森病、痴呆症、阿尔茨海默病、轻度认知障碍、化疗引起的认知功能障碍、唐氏综合征、自闭症谱系障碍、听力丧失、耳鸣、脊髓小脑共济失调、肌萎缩侧索硬化、多发性硬化、亨廷顿病、中风、放射治疗、慢性压力、对神经活性药物的滥用，如酒精、阿片类药物、甲基苯丙胺、芬太尼和可卡因。
• PIPERAZINO[1,2-A]INDOL-1-ONES AND [1,4]DIAZEPINO[1,2-A]INDOL-1-ONE
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150246922A1

  公开（公告）日：2015-09-03

  The present invention relates to compounds of general formula I or pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , X, R and n are as defined herein. The compounds may be used for the treatment of schizophrenia, obsessive-compulsive personality disorder, major depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, mild cognitive impairment, chemotherapy-induced cognitive dysfunction, Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of neuro-active drugs, such as alcohol, opiates, methamphetamine, phencyclidine and cocaine.

  本发明涉及公式I或其药学上可接受的盐的化合物，其中R1、R2、R3、X、R和n的定义如本文所述。这些化合物可用于治疗精神分裂症、强迫症人格障碍、重度抑郁症、双相障碍、焦虑症、正常衰老、癫痫、视网膜退化、创伤性脑损伤、脊髓损伤、创伤后应激障碍、恐慌障碍、帕金森病、痴呆症、阿尔茨海默病、轻度认知障碍、化疗引起的认知功能障碍、唐氏综合症、自闭症谱系障碍、听力损失、耳鸣、脊髓小脑性共济失调、肌萎缩性侧索硬化症、多发性硬化症、亨廷顿病、中风、放射治疗、慢性压力、神经活性药物滥用，如酒精、鸦片类、甲基苯丙胺、苯环利定和可卡因。
• Piperazino[1,2-a]indol-1-ones and [1,4]diazepino[1,2-a]indol-one
  申请人：Hoffmann-La Roche Inc.

  公开号：US20160016963A1

  公开（公告）日：2016-01-21

  The present invention relates to compounds of general formula I wherein R 1 is halogen, lower alkyl, lower alkoxy, lower alkyl substituted by halogen, lower alkoxy substituted by halogen or cyano; R 2 is hydrogen, CF 3 or lower alkyl; R 3 is hydrogen, lower alkyl, lower alkenyl, lower alkinyl, heterocycloalkyl, lower alkyl substituted by cyano, cyano, benzyl substituted by halogen, 2-oxa-6-aza-spiro[3.3]hept-6-yl or is lower alkoxy substituted by halogen; X is —CH 2 — or —CH 2 —CH 2 —; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomers thereof. The compounds may be used for the treatment of schizophrenia, obsessive-compulsive personality disorder, major depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, mild cognitive impairment, chemotherapy-induced cognitive dysfunction, Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of neuro-active drugs, such as alcohol, opiates, methamphetamine, phencyclidine and cocaine.

  本发明涉及一般式I的化合物，其中R1为卤素，低碳基，低烷氧基，低碳基取代的卤素，低烷氧基取代的卤素或氰基; R2为氢，CF3或低碳基; R3为氢，低碳基，低烯基，低炔基，杂环烷基，低碳基取代的氰基，氰基，卤素取代的苄基，2-氧杂-6-氮-螺[3.3]庚-6-基或低烷氧基取代的卤素; X为-CH2-或-CH2-CH2-; 或其对应的对映体和/或光学异构体的药学上可接受的酸加合物或外消旋混合物。这些化合物可用于治疗精神分裂症、强迫性人格障碍、重度抑郁症、双相障碍、焦虑症、正常衰老、癫痫、视网膜退行性疾病、创伤性脑损伤、脊髓损伤、创伤后应激障碍、惊恐障碍、帕金森病、痴呆、阿尔茨海默病、轻度认知障碍、化疗引起的认知功能障碍、唐氏综合症、自闭症谱系障碍、听力损失、耳鸣、脊髓小脑性共济失调、肌萎缩性侧索硬化症、多发性硬化症、亨廷顿病、中风、放射治疗、慢性压力、神经活性药物滥用，如酒精、鸦片类、甲基苯丙胺、苯环利定和可卡因。
• US9284321B2
  申请人：——

  公开号：US9284321B2

  公开（公告）日：2016-03-15
• US9586966B2
  申请人：——

  公开号：US9586966B2

  公开（公告）日：2017-03-07