6-bromo-8-fluoro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one | 1558046-10-8

• 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-8-fluoro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one
• CAS: 1558046-10-8
• 化学式: C₁₂H₁₀BrFN₂O
• 分子量: 297.127
• InChiKey: UMFQTJZWIQXGEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.03
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-bromo-8-fluoro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 为溶剂， 反应 20.0h， 生成 8-fluoro-10-methyl-6-(thiazol-2-yl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one
  参考文献：
  名称：

  [EN] PIPERAZINO[1,2-A]INDOL-1-ONES AND [1,4]DIAZEPINO[1,2-A]INDOL-1-ONE
  [FR] PIPÉRAZINO[1,2-A]INDOL-1-ONES ET [1,4]DIAZÉPINO[1,2-A]INDOL-1-ONE

  摘要：

  本发明涉及一般式（I）的化合物，其中R1是氢、卤素、较低烷基、较低烷氧基、被卤素或氰基取代的较低烷氧基；R2是氢、较低烷基或被卤素取代的较低烷基；R3是苯基、苯并[1,3]二噁英基、2,3-二氢-苯并呋喃-5-基或5-和6-成员杂芳基，其中苯基和5-和6-成员杂芳基可能被氰基、硝基、氨基和较低二烷基氨基、较低烷基磺酰基、较低烷氧基、被卤素取代的较低烷氧基、卤素、较低烷基、被卤素取代的较低烷基或被羟基取代的较低烷基等一个或多个取代基取代；X是-CH（较低烷基）-、-CH2-、-CH2CH2-或-CH（较低烷基）CH2-；R是氢或较低烷基；n是1或2；或是药学上可接受的酸盐，或是外消旋混合物，或是其对映体和/或光学异构体。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、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、惊恐障碍、帕金森病、痴呆症、阿尔茨海默病、轻度认知障碍、化疗诱导的认知功能障碍、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、肌萎缩性侧索硬化、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、芬西克林和可卡因。

  公开号：

  WO2014023674A1

文献信息

• 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-1-one
  申请人：Hoffmann-La Roche Inc.

  公开号：US09284321B2

  公开（公告）日：2016-03-15

  The present invention relates to compounds of general formula I or pharmaceutically acceptable salts thereof, wherein R1, R2, R3, 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。
• 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