N-[endo-(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-3-(n-butyl)-5,5-dimethyl-4-phenyl-4,5-dihydro-(1H)-pyrazole-1-carboxamide | 1092694-73-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-[endo-(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-3-(n-butyl)-5,5-dimethyl-4-phenyl-4,5-dihydro-(1H)-pyrazole-1-carboxamide
• 英文别名: 3-butyl-5,5-dimethyl-4-phenyl-N-((1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-4,5-dihydro-1H-pyrazole-1-carboxamide；3-butyl-5,5-dimethyl-4-phenyl-N-[(1R,2S,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-4H-pyrazole-1-carboxamide
• CAS: 1092694-73-9
• 化学式: C₂₆H₃₉N₃O
• 分子量: 409.615
• InChiKey: BTHUUYVJKCBODB-CUFOWWEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(n-butyl)-5,5-dimethyl-4-phenyl-4,5-dihydropyrazole 、 bornyl isocyanate 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 N-[endo-(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-3-(n-butyl)-5,5-dimethyl-4-phenyl-4,5-dihydro-(1H)-pyrazole-1-carboxamide
  参考文献：
  名称：

  新型吡唑啉甲酰胺两类不同的有效大麻素CB 1受体激动剂

  摘要：

  的3-烷基-4-芳基-4,5-二氢吡唑-1-羧酰胺的合成和SAR 1 - 23和1-烷基-5-芳基-4,5-二氢吡唑-3-甲酰胺24 - 27作为两个新的大麻素描述了CB 1受体激动剂类别。目标化合物引起对CB 1和CB 2受体的高亲和力，并被发现可作为CB 1受体激动剂。关键化合物19在体外引起强效的CB 1激动剂和CB 2反向激动剂特性，并且在啮齿动物模型中口服给药后在多发性硬化中表现出体内活性。

  DOI：

  10.1016/j.bmcl.2010.07.056

文献信息

• 4,5 Dihydro-(1H)-Pyrazole Derivatives as Cannabinoid CB1 Receptor Modulators
  申请人：Lange Josephus H.M.

  公开号：US20080312276A1

  公开（公告）日：2008-12-18

  The invention is directed to 4,5-dihydro-(1H)-pyrazole (pyrazoline) derivatives as cannabinoid CB 1 receptor modulators, to pharmaceutical compositions comprising these compounds, to methods for their syntheses, to methods for preparing novel intermediates useful for their syntheses, and to methods for preparing compositions. The invention also relates to the uses of compounds and compositions administered to patients to achieve a therapeutic effect in multiple sclerosis, traumatic brain injury, pain including chronic pain, neuropathic pain, acute pain and inflammatory pain, osteoporosis, appetite disorders, epilepsy, Alzheimer's disease, Tourette's syndrome, cerebral ischaemia, emesis, nausea, and gastrointestinal disorders. Compounds of the present disclosure are directed to formula (I): wherein the substituents have the definitions given in the specification.

  这项发明涉及作为大麻素CB1受体调节剂的4,5-二氢-(1H)-吡唑烯（吡唑啉）衍生物，包括这些化合物的制药组合物，用于它们的合成的方法，用于制备有用于它们的合成的新颖中间体的方法，以及用于制备组合物的方法。该发明还涉及将化合物和组合物用于治疗多发性硬化症、创伤性脑损伤、疼痛（包括慢性疼痛、神经痛、急性疼痛和炎症性疼痛）、骨质疏松症、食欲障碍、癫痫、阿尔茨海默病、抽动症、脑缺血、呕吐、恶心和胃肠道疾病以实现治疗效果。本公开的化合物的结构如下式（I）：其中取代基的定义如规范中所述。
• US8410135B2
  申请人：——

  公开号：US8410135B2

  公开（公告）日：2013-04-02
• [EN] 4,5-DIHYDRO-(1H)-PYRAZOLE DERIVATIVES AS CANNABINOID CB1 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE 4,5-DIHYDRO-(1H)-PYRAZOLE EN TANT QUE MODULATEURS DES RÉCEPTEURS CB1 CANNABINOÏDES
  申请人：SOLVAY PHARM BV

  公开号：WO2008152086A2

  公开（公告）日：2008-12-18

  [EN] This invention relates to 4,5-dihydro-(1 H)-pyrazole (pyrazoline) derivatives as cannabinoid CB1 receptor modulators, to pharmaceutical compositions containing these compounds, to methods for their syntheses, methods for preparing novel intermediates useful for their syntheses, and methods for preparing compositions. The invention also relates to the uses of such compounds and compositions, particularly their use in administering them to patients to achieve a therapeutic effect in disorders in which CB1 receptors are involved, or that can be treated via manipulation of those receptors. The compounds have formula (I) wherein the symbols have the meanings given in the specification.
  [FR] Cette invention porte sur des dérivés de 4,5-dihydro-(1 H)-pyrazole (pyrazoline) en tant que modulateurs des récepteurs CB1 cannabinoïdes, sur des compositions pharmaceutiques contenant ces composés, sur des procédés pour leurs synthèses, sur des procédés pour préparer de nouveaux intermédiaires utiles pour leurs synthèses et sur des procédés pour préparer les compositions. L'invention porte également sur les utilisations de tels composés et de telles compositions, en particulier sur leur utilisation dans leur administration à des patients pour obtenir un effet thérapeutique dans les cas de troubles impliquant des récepteurs CB1 ou de troubles qui peuvent être traités par manipulation de ces récepteurs. Les composés ont une formule (I) dans laquelle les symboles ont les significations données dans la description.
• Two distinct classes of novel pyrazolinecarboxamides as potent cannabinoid CB1 receptor agonists
  作者：Jos H.M. Lange、Amos Attali、Martina A.W. van der Neut、Henri C. Wals、Arie Mulder、Hicham Zilaout、Ate Duursma、Hans H.M. van Aken、Bernard J. van Vliet

  DOI：10.1016/j.bmcl.2010.07.056

  日期：2010.9

  The synthesis and SAR of 3-alkyl-4-aryl-4,5-dihydropyrazole-1-carboxamides 1–23 and 1-alkyl-5-aryl-4,5-dihydropyrazole-3-carboxamides 24–27 as two novel cannabinoid CB1 receptor agonist classes were described. The target compounds elicited high affinities to the CB1 as well as the CB2 receptor and were found to act as CB1 receptor agonists. The key compound 19 elicited potent CB1 agonistic and CB2 inverse

  的3-烷基-4-芳基-4,5-二氢吡唑-1-羧酰胺的合成和SAR 1 - 23和1-烷基-5-芳基-4,5-二氢吡唑-3-甲酰胺24 - 27作为两个新的大麻素描述了CB 1受体激动剂类别。目标化合物引起对CB 1和CB 2受体的高亲和力，并被发现可作为CB 1受体激动剂。关键化合物19在体外引起强效的CB 1激动剂和CB 2反向激动剂特性，并且在啮齿动物模型中口服给药后在多发性硬化中表现出体内活性。