4-acetyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-1-ylamine | 57756-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 4-acetyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-1-ylamine
• 英文别名: 1-(1-amino-3,5-dihydro-2H-1,4-benzodiazepin-4-yl)ethanone
• CAS: 57756-40-8
• 化学式: C₁₁H₁₅N₃O
• 分子量: 205.26
• InChiKey: KTFXQZFRQRTKBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  411.7±44.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-1-ylamine 在 sodium hydroxide 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 9,9,Dimethyl-1,2,3,4,8,9,10,11-octahydro[1,4]diazepino[6,7,1-jk]carbazole
  参考文献：
  名称：

  Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT2C receptor

  摘要：

  Evaluation of selected compounds from our Corporate Compound Library in a human 5-HT2C receptor binding assay led to the discovery of WAY-629, a cyclohexyl[b][1,4]benzodiazepinoindole (K-i 56nM, E-max 90%), which is selective for the 5-HT2C receptor versus other serotonin receptor subtypes, and dopamine, histamine, adrenergic, and muscarinic receptors. In addition, WAY-629 was active in vivo in a rat model of feeding behavior. An SAR study based on WAY-629 led to compound 11 (K-i 13 nM, E-max 102%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.100
• 作为产物：
  描述：

  3,4-二氢-1H-苯并[e][1,4]二氮杂卓-2,5-二酮 在 盐酸 、 lithium aluminium tetrahydride 、 TEA 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 4-acetyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-1-ylamine
  参考文献：
  名称：

  Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT2C receptor

  摘要：

  Evaluation of selected compounds from our Corporate Compound Library in a human 5-HT2C receptor binding assay led to the discovery of WAY-629, a cyclohexyl[b][1,4]benzodiazepinoindole (K-i 56nM, E-max 90%), which is selective for the 5-HT2C receptor versus other serotonin receptor subtypes, and dopamine, histamine, adrenergic, and muscarinic receptors. In addition, WAY-629 was active in vivo in a rat model of feeding behavior. An SAR study based on WAY-629 led to compound 11 (K-i 13 nM, E-max 102%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.100

文献信息

• [1,4]Diazepino [6,7,1-jk] carbazoles and derivatives
  申请人：American Home Products Corporation

  公开号：US20020086860A1

  公开（公告）日：2002-07-04

  This invention provides [1,4]diazepino[6,7,1-jk]carbazole compounds of the formula: 1 wherein: R 1 and R 2 are H, alkyl, alkoxy, halogen, fluorinated alkyl, —CN, —NH—SO 2 -alkyl, —SO 2 —NH-alkyl, alkyl amide, amino, alkylamino, dialkylamino, fluorinated alkoxy, acyl, phenoyl or thiophenoyl; R 3 , R 4 , R 5 and R 6 are H, alkyl, cycloalkyl, alkoxy or cycloalkoxy; R 7 is H or alkyl; R 8 is H or alkyl; and the dashed line indicates an optional double bond; or a pharmaceutically acceptable salt thereof, as well as methods and pharmaceutical compositions utilizing them for the treatment or prevention of disorders such as obsessive-compulsive disorder, depression, anxiety, schizophrenia, migraine, sleep disorders, eating disorders, obesity, epilepsy, and spinal cord injury.

  这项发明提供了一种公式为1的[1,4]二氮杂二环[6,7,1-jk]吲哚类化合物，其中：R1和R2为H、烷基、烷氧基、卤素、氟代烷基、—CN、—NH—SO2-烷基、—SO2—NH-烷基、烷基酰胺、氨基、烷基氨基、二烷基氨基、氟代烷氧基、酰基、苯甲酰基或硫代苯甲酰基；R3、R4、R5和R6为H、烷基、环烷基、烷氧基或环烷氧基；R7为H或烷基；R8为H或烷基；虚线表示可选的双键；或其药学上可接受的盐，以及利用它们用于治疗或预防强迫症、抑郁症、焦虑症、精神分裂症、偏头痛、睡眠障碍、饮食障碍、肥胖症、癫痫和脊髓损伤等疾病的方法和药物组合物。
• Processes for preparation of cyclopenta [b] [1,4] diazepino [6,7,1-hi] indoles and derivatives
  申请人：American Home Products Corporation

  公开号：US20020062022A1

  公开（公告）日：2002-05-23

  This invention provides processes for synthesizing compounds of formula I: 1 wherein R is H or alkyl; R 1 , R 2 are H, alkyl, alkoxy, halogen, fluorinated alkyl, —CN, alkyl sulfonamide, alkyl amide, amino, alkylamino, dialkylamino, fluorinated alkoxy, acyl, or aroyl; R 3 and R 4 are H, alkyl or cycloalkyl; the dashed line indicates an optional double bond; as well as intermediates and pharmaceutically acceptable salts thereof.

  本发明提供了合成式I的化合物的方法：其中R为H或烷基；R1，R2为H，烷基，烷氧基，卤素，氟化烷基，-CN，烷基磺酰胺，烷基酰胺，氨基，烷基氨基，二烷基氨基，氟化烷氧基，酰基或芳酰基；R3和R4为H，烷基或环烷基；虚线表示可选的双键；以及其中间体和药学上可接受的盐。
• Processes for preparation of cyclopenta[b][1,4]diazepino[6,7,1-hi]indoles and derivatives
  申请人：Wyeth

  公开号：US06784172B2

  公开（公告）日：2004-08-31

  This invention provides processes for synthesizing compounds of formula I: wherein R is H or alkyl; R1, R2 are H, alkyl, alkoxy, halogen, fluorinated alkyl, —CN, alkyl sulfonamide, alkyl amide, amino, alkylamino, dialkylamino, fluorinated alkoxy, acyl, or aroyl; R3 and R4 are H, alkyl or cycloalkyl; the dashed line indicates an optional double bond; as well as intermediates and pharmaceutically acceptable salts thereof.

  本发明提供了合成式I的化合物的过程：其中R为H或烷基；R1，R2为H，烷基，烷氧基，卤素，氟代烷基，-CN，烷基磺酰胺，烷基酰胺，氨基，烷基氨基，二烷基氨基，氟代烷氧基，酰基或芳酰基；R3和R4为H，烷基或环烷基；虚线表示可选的双键；以及其中间体和药学上可接受的盐。
• CYCLOPENTA[b][1,4]DIAZEPINO[6,7,1-hi]INDOLES AND DERIVATIVES
  申请人：Sabb Louise Annmarie

  公开号：US20080009480A1

  公开（公告）日：2008-01-10

  This invention provides compounds of the formulae: wherein: R 1 is hydrogen, —C(O)CH 3 or alkyl of 1-6 carbon atoms; R 2 and R 3 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, cycloalkyl, alkoxy of 1-6 carbon atoms, —CH 2 OH, fluoroalkyl, alkyl sulfonamide of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluoroalkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, aryl, or aroyl; R 4 and R 5 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, halogen, fluoroalkyl, —CN, alkyl sulfonamide of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluoroalkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, or aroyl; R 6 and R 7 are each independently hydrogen, C 1 -C 6 alkyl or cycloalkyl; or a pharmaceutically acceptable salt thereof, as well as pharmaceutical compositions containing these compounds and methods for their use, including treatment of obsessive-compulsive disorder, panic disorder, depression, anxiety, generalized anxiety disorder, schizophrenia, migraine, sleep disorders, eating disorders, obesity, epilepsy, and spinal cord injury.

  这项发明提供了以下式子的化合物：其中：R1为氢、—C（O）CH3或1-6个碳原子的烷基；R2和R3各自独立地为氢、1-6个碳原子的烷基、环烷基、1-6个碳原子的烷氧基、—CH2OH、氟代烷基、1-6个碳原子的烷基磺酰胺、1-6个碳原子的烷基酰胺、氨基、1-6个碳原子的烷基氨基、每个烷基成分的1-6个碳原子的双烷基氨基、1-6个碳原子的氟代烷氧基、2-7个碳原子的酰基、芳基或芳酰基；R4和R5各自独立地为氢、1-6个碳原子的烷基、1-6个碳原子的烷氧基、卤素、氟代烷基、—CN、1-6个碳原子的烷基磺酰胺、1-6个碳原子的烷基酰胺、氨基、1-6个碳原子的烷基氨基、每个烷基成分的1-6个碳原子的双烷基氨基、1-6个碳原子的氟代烷氧基、2-7个碳原子的酰基或芳酰基；R6和R7各自独立地为氢、C1-C6烷基或环烷基；或其药学上可接受的盐，以及包含这些化合物的制药组合物和它们的使用方法，包括治疗强迫症、恐慌症、抑郁症、焦虑症、广泛性焦虑症、精神分裂症、偏头痛、睡眠障碍、进食障碍、肥胖症、癫痫和脊髓损伤。
• CYCLOPENTA[B][1,4] DIAZEPINO[6,7,1-HI]INDOLES AS 5HT2C ANTAGONISTS
  申请人：Wyeth

  公开号：EP1330457A2

  公开（公告）日：2003-07-30