1-[2-(1-pyrrolidinyl)ethylamino]-4-(3-cyanophenyl)-4-hydroxycyclohexane | 540787-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-[2-(1-pyrrolidinyl)ethylamino]-4-(3-cyanophenyl)-4-hydroxycyclohexane
• CAS: 540787-50-6
• 化学式: C₁₉H₂₇N₃O
• 分子量: 313.443
• InChiKey: IWZXVYSHAYQXGO-KDURUIRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  59.29
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[2-(1-pyrrolidinyl)ethylamino]-4-(3-cyanophenyl)-4-hydroxycyclohexane 在 三乙基硅烷 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-[4-(3-Cyano-phenyl)-cyclohex-3-enyl]-3-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-urea
  参考文献：
  名称：

  Bicyclic[4.1.0]heptanes as phenyl replacements for melanin concentrating hormone receptor antagonists

  摘要：

  Melanin concentrating hormone (MCH) receptor antagonists have been proposed as potential treatments of obesity. MCH receptor antagonists with a biphenylamine subunit have been reported previously at Schering-Plough. Herein, we report the discovery of bicyclo[4.1.0]heptanes as replacements for the middle phenyl ring of the biphenylamine moiety, in order to eliminate its potential mutagenic liability. Structure-activity relationships in this series were found to be very similar to those of the original biphenylamine series, suggesting that the two series have similar binding modes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.046
• 作为产物：
  描述：

  4-(3-cyanophenyl)-4-hydroxycyclohexan-1-one ethylene ketal 在 sodium cyanoborohydride 、 对甲苯磺酸 、 丙酮 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-[2-(1-pyrrolidinyl)ethylamino]-4-(3-cyanophenyl)-4-hydroxycyclohexane
  参考文献：
  名称：

  Bicyclic[4.1.0]heptanes as phenyl replacements for melanin concentrating hormone receptor antagonists

  摘要：

  Melanin concentrating hormone (MCH) receptor antagonists have been proposed as potential treatments of obesity. MCH receptor antagonists with a biphenylamine subunit have been reported previously at Schering-Plough. Herein, we report the discovery of bicyclo[4.1.0]heptanes as replacements for the middle phenyl ring of the biphenylamine moiety, in order to eliminate its potential mutagenic liability. Structure-activity relationships in this series were found to be very similar to those of the original biphenylamine series, suggesting that the two series have similar binding modes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.046

文献信息

• [EN] N-ARYL-N'-ARYLCYCLOALKYL-UREA DERIVATIVES AS MCH ANTAGONISTS FOR THE TREATMENT OF OBESITY<br/>[FR] DERIVES DU N-ARYL-N'-ARYLCYCLOALKYL-UREE, ANTAGONISTES DE L'HORMONE MCH, TRAITANT L'OBESITE
  申请人：SCHERING CORP

  公开号：WO2003047568A1

  公开（公告）日：2003-06-12

  The present invention discloses compounds of the formula I which, are novel antagonists for melanin-concentrating hormone (MCH), as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such MCH antagonists as well as methods of using them to treat obesity, metabolic disorders, eating disorders such as hyperphagia, and diabetes.

  本发明揭示了式I的化合物，它们是黑色素浓聚激素（MCH）的新型拮抗剂，以及制备这些化合物的方法。在另一实施例中，本发明揭示了包含这些MCH拮抗剂的药物组合物，以及使用它们治疗肥胖症、代谢紊乱、食欲紊乱（如暴食症）和糖尿病的方法。
• MCH antagonists for the treatment of obesity
  申请人：Schering Corporation

  公开号：US20040122017A1

  公开（公告）日：2004-06-24

  The present invention discloses compounds which, are novel antagonists for melanin-concentrating hormone (MCH), as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such MCH antagonists as well as methods of using them to treat obesity, metabolic disorders, eating disorders such as hyperphagia, and diabetes.

  本发明揭示了一些化合物，这些化合物是黑色素浓聚激素（MCH）的新型拮抗剂，并揭示了制备这些化合物的方法。在另一种实施方式中，本发明揭示了包含这些MCH拮抗剂的药物组合物，以及使用它们治疗肥胖、代谢紊乱、进食障碍如过度进食和糖尿病的方法。
• 肥満の処置のためのＭＣＨアンタゴニストとしてのＮ−アリール−Ｎ’−アリールシクロアルキル−尿素−誘導体
  申请人：シェーリング コーポレイション

  公开号：JP2009235076A

  公开（公告）日：2009-10-15

  【課題】メラニン−濃縮ホルモン（ＭＣＨ）のための新規なアンタゴニストを提供する。【解決手段】例えばｔｒａｎｓまたはｃｉｓ−１−［２−（１−ピロリジニル）エチルアミノ］−４−（３−シアノフェニル）−４−ヒドロキシシクロヘキサンである、Ｎ−アリールウレア誘導体式Ｉ。メラニン−濃縮ホルモン（ＭＣＨ）のアンタゴニスト活性を有し、肥満、代謝障害、摂食障害（例えば、過食症、および糖尿病）に適用される。また、大うつ病、躁鬱病、不安症、精神分裂病および睡眠障害に適用される。【選択図】なし

  提供黑色素浓缩激素（MCH）的新型拮抗剂。解决方法】例如，反式或顺式-1-[2-(1-吡咯烷基)乙基氨基]-4-(3-吡咯烷基)例如，反式或顺式-1-[2-(1-吡咯烷基)乙基氨基]-4-(3-氰基苯基)-4-羟基环己烷。适用于肥胖症、代谢紊乱和饮食失调（如贪食症和糖尿病）。还可用于重度抑郁症、躁狂抑郁症、焦虑症、精神分裂症和睡眠障碍。无。
• N- ARYL-N'-ARYLCYCLOALKYL-UREA DERIVATIVES AS MCH ANTAGONISTS FOR THE TREATMENT OF OBESITY
  申请人：SCHERING CORPORATION

  公开号：EP1453501A1

  公开（公告）日：2004-09-08
• US7348328B2
  申请人：——

  公开号：US7348328B2

  公开（公告）日：2008-03-25