(2S)-(+)-5,5-二甲基-2-吗啉乙酸 | 733717-87-8

• 物质功能分类: 生物化工 - 抑制剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: (2S)-(+)-5,5-二甲基-2-吗啉乙酸
• 英文名称: 2-[(2S)-5,5-dimethylmorpholin-2-yl]acetic acid
• 英文别名: (+)-(S)-5,5-dimethylmorpholinyl-2-acetic acid；(2S)-(+)-5,5-dimethyl-2-morpholineacetic acid；SCH 50911；SCH 50,911；SCH-50911；Sch 50911；2-[(2S)-5,5-dimethylmorpholin-4-ium-2-yl]acetate
• CAS: 733717-87-8
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: SEYCKMQSPUVYEF-LURJTMIESA-N

物化性质

• 溶解度：
  <17.32mg/ml，在水中； <17.32mg/ml，PBS 中

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

生物活性

SCH 50911 是一种具有口服活性的选择性 γ-氨基丁酸 B（GABA(B)）受体拮抗剂，能够与 GABA(B) 受体结合，其 IC50 值为 1.1 μM。此外，SCH 50911 还可以拮抗 GABA(B) 自身受体，增加电刺激下的 3H 溢出，IC50 值为 3 μM。

靶点

GABA(B)
1.1 μM (IC50)

反应信息

• 作为反应物：
  描述：

  4-氯氯苄 、 (2S)-(+)-5,5-二甲基-2-吗啉乙酸 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Substituted morpholine-2S-acetic acid derivatives: Sch 50911 and related compounds as novel GABAB antagonists

  摘要：

  The synthesis and GABA(B) antagonist activity of a series of substituted morpholine-2-acetic acid derivatives is described. Resolution of the lead compound from the series produces one active and one inactive enantiomer. X-ray analysis of a halogenated derivative (25) of the active enantiomer Sch 50911 (23) shows that it possesses the 2S configuration. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00267-3
• 作为产物：
  描述：

  tert-butyl 2-(2-ethoxy-2-oxoethyl)-5,5-dimethylmorpholine-4-carboxylate 在 盐酸 、 Daicel Chiralcel OD 作用下， 以 正己烷 、 水 、 异丙醇 为溶剂， 反应 60.0h， 生成 (2S)-(+)-5,5-二甲基-2-吗啉乙酸
  参考文献：
  名称：

  Substituted morpholine-2S-acetic acid derivatives: Sch 50911 and related compounds as novel GABAB antagonists

  摘要：

  The synthesis and GABA(B) antagonist activity of a series of substituted morpholine-2-acetic acid derivatives is described. Resolution of the lead compound from the series produces one active and one inactive enantiomer. X-ray analysis of a halogenated derivative (25) of the active enantiomer Sch 50911 (23) shows that it possesses the 2S configuration. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00267-3

文献信息

• [EN] 2,3,5 TRISUBSTITUTED ARYL AND HETEROARYL AMINO DERIVATIVES, COMPOSITIONS, AND METHODS OF USE<br/>[FR] DÉRIVÉS AMINÉS D'HÉTÉROARYLE ET D'ARYLE 2,3,5 TRISUBSTITUÉS, COMPOSITIONS ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：NEUROTHERAPEUTICS PHARMA INC

  公开号：WO2013059648A1

  公开（公告）日：2013-04-25

  Compounds are disclosed that have a formula represented by the following:(I) wherein Cy, L1 R1, R2a, R2b, R3, R4, n, and L2 are as described herein. These compounds may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example addictive disorders, Alzheimer's Disease, anxiety disorders, ascites, autism, bipolar disorder, cancer, depression, endothelial corneal dystrophy, edema, epilepsy, glaucoma, Huntington's Disease, inflammatory pain, insomnia, ischemia, migraine, migraine with aura, migraine without aura, neuropathic pain, nociceptive neuralgia, nociceptive pain, ocular diseases, pain, itch, excessive itch, Pruritis, neuropathic pruritis, Parkinson's disease, personality disorders, postherpetic neuralgia, psychosis, schizophrenia, seizure disorders, tinnitus, and withdrawal syndromes.

  已披露具有以下表示的化合物的公式：(I)，其中Cy、L1、R1、R2a、R2b、R3、R4、n和L2如本文所述。这些化合物可以制备为药物组合物，并可用于预防和治疗包括人类在内的哺乳动物的各种疾病，例如成瘾障碍、阿尔茨海默病、焦虑障碍、腹水、自闭症、躁郁症、癌症、抑郁症、内皮角膜营养不良、水肿、癫痫、青光眼、亨廷顿病、炎症性疼痛、失眠、缺血、偏头痛、伴有先兆的偏头痛、无先兆的偏头痛、神经病性疼痛、伤害性神经痛、伤害性疼痛、眼部疾病、疼痛、瘙痒、过度瘙痒、瘙痒、神经性瘙痒、帕金森病、人格障碍、带状疱疹后神经痛、精神病、精神分裂症、癫痫障碍、耳鸣和戒断综合症等。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• Combination of a sedative and a neurotransmitter modulator, and methods for improving sleep quality and treating depression
  申请人：Sepracor Inc.

  公开号：EP2343073A2

  公开（公告）日：2011-07-13

  One aspect of the present invention relates to pharmaceutical compositions containing two or more active agents that when taken together can be used to treat, e.g., insomnia and/or depression. The first component of the pharmaceutical composition is a GABA receptor modulating compound. The second component of the pharmaceutical composition is a serotonin reuptake inhibitor, a norepinephrine reuptake inhibitor, a 5-HT2A modulator, or dopamine reuptake inhibitor. In certain embodiments, the pharmaceutical composition comprises eszopiclone. In a preferred embodiment, the pharmaceutical composition comprises eszopiclone and fluoxetine. The present invention also relates to a method of treating a sleep abnormality, treating insomnia, treating depression, augmenting antidepressant therapy, eliciting a dose-sparing effect, reducing depression relapse, improving the efficacy of antidepressant therapy or improving the tolerability of antidepressant therapy, comprising co-administering to a patient in need thereof a GABA-receptor-modulating compound; and a SRI, NRI, 5-HT2A modulator or DRI.

  本发明的一个方面涉及含有两种或两种以上活性剂的药物组合物，这些活性剂一起服用时可用于治疗失眠和/或抑郁症等。药物组合物的第一种成分是 GABA 受体调节化合物。药物组合物的第二种成分是血清素再摄取抑制剂、去甲肾上腺素再摄取抑制剂、5-HT2A调节剂或多巴胺再摄取抑制剂。在某些实施方案中，药物组合物包含艾佐匹克隆。在一个优选的实施方案中，药物组合物包括艾司佐匹克隆和氟西汀。本发明还涉及一种治疗睡眠异常、治疗失眠、治疗抑郁症、增强抗抑郁治疗、引起剂量节省效应、减少抑郁症复发、改善抗抑郁治疗的疗效或改善抗抑郁治疗的耐受性的方法，包括向有需要的患者联合施用GABA受体调节化合物；和SRI、NRI、5-HT2A调节剂或DRI。
• Methods and treatments for the learning and memory deficits associated with Noonan syndrome
  申请人：The Regents of the University of California

  公开号：US10835513B2

  公开（公告）日：2020-11-17

  Disclosed herein are methods and compositions for treating learning and memory deficits associated with Noonan Syndrome.

  本文公开了治疗与努南综合征相关的学习和记忆缺陷的方法和组合物。
• Melatonin combination therapy for improving sleep quality
  申请人：Barberich J. Timothy

  公开号：US20050164987A1

  公开（公告）日：2005-07-28

  One aspect of the present invention relates to pharmaceutical compositions comprising a sedative agent; and melatonin or a melatonin analog, collectively referred to as “melatonin agents.” In a preferred embodiment, the sedative agent is eszopiclone. The pharmaceutical compositions of the invention are useful in the treatment of various sleep disorders. In addition, the present invention also relates to a method of treating a patient suffering from a sleep abnormality or insomnia comprising administering a therapeutically effective amount of a pharmaceutical composition of the invention.

  本发明的一个方面涉及包含镇静剂、褪黑素或褪黑素类似物的药物组合物，统称为 "褪黑素制剂"。在一个优选的实施方案中，镇静剂是艾佐匹克隆。本发明的药物组合物可用于治疗各种睡眠障碍。此外，本发明还涉及一种治疗睡眠异常或失眠症患者的方法，包括施用治疗有效量的本发明药物组合物。