5-(2-chloroethyl)-N-ethyloxindole | 118307-09-8

• 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: 5-(2-chloroethyl)-N-ethyloxindole
• 英文别名: 5-(2-chloroethyl)-1-ethyloxindole；5-(2-chloroethyl)-1-ethyl-3H-indol-2-one
• CAS: 118307-09-8
• 化学式: C₁₂H₁₄ClNO
• 分子量: 223.702
• InChiKey: WKEZOIZTNJYCOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  438.8±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-萘基)对二氮已环 、 5-(2-chloroethyl)-N-ethyloxindole 在 sodium carbonate 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 120.0h， 生成 1-ethyl-5-{2-[4-(1-naphthyl)piperazinyl]ethyl}-2,3-dihydroindol-2-one
  参考文献：
  名称：

  1-Naphthylpiperazine derivatives as potential atypical antipsychotic agents

  摘要：

  The design and synthesis of a series of potential atypical antipsychotic agents based on the structure of 1-naphthylpiperazine are described. The incorporation of dopamine antagonist activity into the parent structure was achieved with heterocyclic surrogates for the catechol moiety of dopamine. Compound 4b from this series showed a biochemical profile that translated to behavioral activity in the rat predictive of an antipsychotic agent with a low propensity to cause extrapyramidal side effects in man.

  DOI：

  10.1021/jm00110a016
• 作为产物：
  描述：

  1-乙基-3H-吲哚-2-酮 在 三乙基硅烷 、 三氯化铝 、 三氟乙酸 作用下， 以 二硫化碳 为溶剂， 反应 43.33h， 生成 5-(2-chloroethyl)-N-ethyloxindole
  参考文献：
  名称：

  1-Naphthylpiperazine derivatives as potential atypical antipsychotic agents

  摘要：

  The design and synthesis of a series of potential atypical antipsychotic agents based on the structure of 1-naphthylpiperazine are described. The incorporation of dopamine antagonist activity into the parent structure was achieved with heterocyclic surrogates for the catechol moiety of dopamine. Compound 4b from this series showed a biochemical profile that translated to behavioral activity in the rat predictive of an antipsychotic agent with a low propensity to cause extrapyramidal side effects in man.

  DOI：

  10.1021/jm00110a016

文献信息

• METHOD OF TREATING GLAUCOMA AND ISCHEMIC RETINOPATHY
  申请人：——

  公开号：US20020004504A1

  公开（公告）日：2002-01-10

  A method for treating glaucoma and ischemic retinopathy in a mammal, comprising administering to said mammal a therapeutically effective amount of a compound of the formula 1 or a pharmaceutically acceptable acid addition salt thereof, wherein n, X, Y and Ar are as defined in the specification.

  在哺乳动物中治疗青光眼和缺血性视网膜病的方法，包括向所述哺乳动物施用公式1的化合物或其药学上可接受的酸盐的治疗有效量，其中n、X、Y和Ar如规范中定义。
• Anxiety treatments with ziprasidone
  申请人：Romano Joseph Steven

  公开号：US20050004138A1

  公开（公告）日：2005-01-06

  The present invention, in one aspect, relates to a method of using piperazinyl-heterocyclic compounds of the formula I, as defined below, for treating, in a mammal, including a human, situational anxiety, for example, anxiety experienced prior to medical procedures (e.g., surgery), public speaking, anxiety associated with swimming or water, anxiety associated with travel (e.g., air travel), or anxiety associated with specific phobias (snakes, spider, rats, sight of blood), comprising administering a pharmaceutically effective amount of a compound of formula I to the mammal. In another aspect, the present invention is directed to a method of using piperazinyl-heterocyclic compounds of the formula I, as defined below, for treating, in a mammal, including a human, treatment-resistant anxiety, which method comprises administering a pharmaceutically effective amount of a compound of formula I to the mammal. The compounds of formula I are defined as follows: or a pharmaceutically acceptable acid addition salt thereof, wherein Ar, n, X, and Y are as defined.

  本发明在某些方面涉及使用以下式子定义的哌嗪基-杂环化合物的方法，用于治疗哺乳动物，包括人类的情境焦虑，例如在医疗程序（例如手术）、公共演讲、与游泳或水有关的焦虑、与旅行（例如空中旅行）有关的焦虑或与特定恐惧症（蛇、蜘蛛、老鼠、血液视觉）有关的焦虑，包括向哺乳动物投与化学有效量的式子I的化合物。在另一个方面，本发明涉及使用以下式子定义的哌嗪基-杂环化合物的方法，用于治疗哺乳动物，包括人类的难治性焦虑，其中该方法包括向哺乳动物投与化学有效量的式子I的化合物。式子I的化合物定义如下：或其药学上可接受的酸盐，其中Ar、n、X和Y如上定义。
• Treatment of bipolar disorders and associated symptoms
  申请人：Romano Joseph Steven

  公开号：US20050038036A1

  公开（公告）日：2005-02-17

  The present invention relates to a method for treatments relating to bipolar disorder in a mammal, including a human, the treatments including treatment of rapid-cycling bipolar disorder, treatment of symptoms of bipolar disorder selected from the group consisting of acute mania and depression, treatment for effecting mood stabilization; treatment for preventing relapse into bipolar episodes, and for the treatment of suicidal thoughts and tendencies associated with bipolar disorder, comprising administering to said mammal an effective amount of a compound of the formula I: or a pharmaceutically acceptable acid addition salt thereof, wherein Ar, n, X, and Y are as defined.

  本发明涉及一种治疗哺乳动物（包括人类）的双相障碍的方法，包括治疗快速循环型双相障碍，治疗选自急性躁狂和抑郁症状的双相障碍症状，治疗以影响情绪稳定为目的的治疗，预防双相障碍复发的治疗，以及治疗与双相障碍相关的自杀思想和倾向。该方法包括向该哺乳动物施用以下化合物的有效量：式I的化合物或其药学上可接受的酸盐加合物，其中Ar、n、X和Y如定义。
• Method for enhancing cognition using ziprasidone
  申请人：Romano Joseph Steven

  公开号：US20050014764A1

  公开（公告）日：2005-01-20

  The present invention, in one aspect, relates to a method of using piperazinyl-heterocyclic compounds of the formula I, as defined below, for enhancing cognition in a mammal, including a human, for example a mammal afflicted with psychosis, autism, dementia, or mental retardation, comprising administering an effective amount of a compound of formula I (for example, ziprasidone) to the mammal. In another aspect, the present invention is directed to a method for reducing or ameliorating in a mammal, including a human, afflicted with a disorder or condition selected from autism, mental retardation, obsessive-compulsive disorder, and dementia, positive symptoms (e.g. excessive aggression, disinhibited sexual behavior, inappropriate sexual behavior, agitation, compulsive behavior such as head banging, lip bighting, self mutilation, or stereotypic behavior) associated with the aforementioned disorders or conditions, which method comprises administering an effective amount of a compound of formula I (for example, ziprasidone) to the mammal. In another aspect, the present invention is directed to a method for treating pediatric bipolar disorder in a mammal, including a human, which method comprises administering an effective amount of a compound of formula I (for example, ziprasidone) to the mammal. The compounds of compound of the formula I are defined as follows: or a pharmaceutically acceptable acid addition salt thereof, wherein Ar, n, X, and Y are as defined.

  本发明在某个方面涉及使用式I的哌嗪基-杂环化合物的方法，如下所定义，用于增强哺乳动物，包括人类，例如患有精神病、自闭症、痴呆或智力障碍的哺乳动物的认知能力，包括向哺乳动物投与式I的化合物的有效量（例如ziprasidone）。在另一个方面，本发明涉及一种用于减轻或改善患有自闭症、智力障碍、强迫症和痴呆等疾病或症状的哺乳动物，包括人类的阳性症状（例如过度攻击、失控的性行为、不当的性行为、激动、强迫性行为，如头撞击、咬唇、自我伤害或刻板行为），该方法包括向哺乳动物投与式I的化合物的有效量（例如ziprasidone）。在另一个方面，本发明涉及一种用于治疗哺乳动物，包括人类的小儿双相情感障碍的方法，该方法包括向哺乳动物投与式I的化合物的有效量（例如ziprasidone）。化合物I的定义如下：或其药学上可接受的酸加成盐，其中Ar、n、X和Y如上所定义。
• METHOD FOR TREATING PEDIATRIC BIPOLAR DISORDER
  申请人：Romano Steven Joseph

  公开号：US20080269246A1

  公开（公告）日：2008-10-30

  The present invention, in one aspect, relates to a method of using piperazinyl-heterocyclic compounds of the formula I, as defined below, for enhancing cognition in a mammal, including a human, for example a mammal afflicted with psychosis, autism, dementia, or mental retardation, comprising administering an effective amount of a compound of formula I (for example, ziprasidone) to the mammal. In another aspect, the present invention is directed to a method for reducing or ameliorating in a mammal, including a human, afflicted with a disorder or condition selected from autism, mental retardation, obsessive-compulsive disorder, and dementia, positive symptoms (e.g. excessive aggression, disinhibited sexual behavior, inappropriate sexual behavior, agitation, compulsive behavior such as head banging, lip biting, self mutilation, or stereotypic behavior) associated with the aforementioned disorders or conditions, which method comprises administering an effective amount of a compound of formula I (for example, ziprasidone) to the mammal. In another aspect, the present invention is directed to a method for treating pediatric bipolar disorder in a mammal, including a human, which method comprises administering an effective amount of a compound of formula I (for example, ziprasidone) to the mammal. The compounds of the formula I are defined as follows: or a pharmaceutically acceptable acid addition salt thereof, wherein Ar, n, X, and Y are as defined.

  本发明在某些方面涉及使用公式I所定义的哌嗪基-杂环化合物的方法，以增强哺乳动物（包括人类）的认知能力，例如患有精神病、自闭症、痴呆或智力低下的哺乳动物，包括给哺乳动物（例如齐拉西酮）的公式I化合物的有效剂量。在另一个方面，本发明涉及一种方法，用于减轻或改善患有自闭症、智力低下、强迫症和痴呆症等疾病或症状的哺乳动物（包括人类）的阳性症状（例如过度攻击、解禁性行为、不当性行为、焦虑、强迫行为，如头撞击、咬唇、自残或刻板行为），该方法包括向哺乳动物（例如齐拉西酮）的有效剂量的公式I化合物的管理。在另一个方面，本发明涉及一种用于治疗哺乳动物（包括人类）的儿童双相情感障碍的方法，该方法包括向哺乳动物（例如齐拉西酮）的有效剂量的公式I化合物的管理。公式I化合物定义如下：或其药学上可接受的酸盐，其中Ar，n，X和Y如定义。