4-dimethylamino-4-phenylcyclohexanone, ethylene ketal hydrochloride | 65619-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-dimethylamino-4-phenylcyclohexanone, ethylene ketal hydrochloride
• 英文别名: dimethyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine hydrochloride；dimethyl(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine hydrochloride；N,N-Dimethyl-8-phenyl-1,4-dioxaspiro[4.5]decan-8-amine hydrochloride；N,N-dimethyl-8-phenyl-1,4-dioxaspiro[4.5]decan-8-amine;hydrochloride
• CAS: 65619-19-4
• 化学式: C₁₆H₂₃NO₂*ClH
• 分子量: 297.825
• InChiKey: PVFOAWFRYLEVPD-UHFFFAOYSA-N

物化性质

• 熔点：
  226-229 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-dimethylamino-4-phenylcyclohexanone, ethylene ketal hydrochloride 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 6-fluoro-N,N-dimethyl-1'-phenylspiro[4,9-dihydro-3H-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine
  参考文献：
  名称：

  Discovery of a Potent Analgesic NOP and Opioid Receptor Agonist: Cebranopadol

  摘要：

  In a previous communication, our efforts leading from 1 to the identification of spiro[cyclohexane-dihydropyrano[3,4-b]indole]-amine 2a as analgesic NOP and opioid receptor agonist were disclosed and their favorable in vitro and in vivo pharmacological properties revealed. We herein report our efforts to further optimize lead 2a, toward trans-6'-fluoro-4',9'-dihydro-N,N-dimethyl-4-phenyl-spiro[cyclohexane-1,1'(3'H)-pyrano[3,4-b]indol]-4-amine (cebranopadol, 3a), which is currently in clinical development for the treatment of severe chronic nociceptive and neuropathic pain.

  DOI：

  10.1021/ml500117c
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 4-dimethylamino-4-phenylcyclohexanone, ethylene ketal hydrochloride
  参考文献：
  名称：

  Discovery of a Potent Analgesic NOP and Opioid Receptor Agonist: Cebranopadol

  摘要：

  In a previous communication, our efforts leading from 1 to the identification of spiro[cyclohexane-dihydropyrano[3,4-b]indole]-amine 2a as analgesic NOP and opioid receptor agonist were disclosed and their favorable in vitro and in vivo pharmacological properties revealed. We herein report our efforts to further optimize lead 2a, toward trans-6'-fluoro-4',9'-dihydro-N,N-dimethyl-4-phenyl-spiro[cyclohexane-1,1'(3'H)-pyrano[3,4-b]indol]-4-amine (cebranopadol, 3a), which is currently in clinical development for the treatment of severe chronic nociceptive and neuropathic pain.

  DOI：

  10.1021/ml500117c

文献信息

• SUBSTITUTED HETEROARYL DERIVATIVES
  申请人：Zemolka Saskia

  公开号：US20100009986A1

  公开（公告）日：2010-01-14

  The invention relates to substituted heteroaryl derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted heteroaryl derivatives for producing medicaments.

  这项发明涉及替代杂环芳基衍生物，涉及其生产方法，含有该化合物的药物以及利用替代杂环芳基衍生物生产药物的用途。
• Spirocyclic Azaindole Derivatives
  申请人：Zemolka Saskia

  公开号：US20090156593A1

  公开（公告）日：2009-06-18

  The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.

  该发明涉及取代的氮杂吲哚衍生物，其制备方法，含有该化合物的药物以及使用取代的氮杂吲哚衍生物来生产药物。
• Cis-tetrahydro-spiro(cyclohexane-1,1'-pyrido[3,4-b]indole)-4-amine Compounds
  申请人：Linz Klaus

  公开号：US20120029006A1

  公开（公告）日：2012-02-02

  Cis-tetrahydro-spiro(cyclohexane-1,1′-pyrido[3,4-b]indole)-4-amine compounds which act on the nociceptin/ORL-1 receptor system as well as on the μ-opioid receptor system and which are distinguished in particular by selective effectiveness in the treatment of chronic pain, such as inflammatory pain, visceral pain, tumour pain, and neuropathic pain, without at the same time developing pronounced effectiveness against acute, nociceptive pain.

  Cis-四氢噻吡啶并[环己烷-1,1′-吡啶并[3,4-b]吲哚]-4-胺化合物作用于痛觉素/ORL-1受体系统以及μ-阿片受体系统，特别以其在治疗慢性疼痛（如炎症性疼痛、内脏疼痛、肿瘤疼痛和神经病理性疼痛）方面的选择性有效性而著称，同时不会对急性、痛觉性疼痛表现出显著的有效性。
• Substituted heteroaryl derivatives
  申请人：Gruenenthal GmbH

  公开号：US08138187B2

  公开（公告）日：2012-03-20

  The invention relates to substituted heteroaryl derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted heteroaryl derivatives for producing medicaments.

  本发明涉及取代杂环芳基衍生物，其生产方法，含有该化合物的药物以及利用取代杂环芳基衍生物生产药物的用途。
• Spirocyclic azaindole derivatives
  申请人：Zemolka Saskia

  公开号：US08399503B2

  公开（公告）日：2013-03-19

  The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.

  本发明涉及取代的氮杂吲哚衍生物，其制备方法，含有该化合物的药物以及使用取代的氮杂吲哚衍生物制备药物的用途。