(1S,3R)-3-amino-N-[(2R)-1-[(4S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl]-3-methyl-1-oxobutan-2-yl]cyclopentane-1-carboxamide | 946588-46-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (1S,3R)-3-amino-N-[(2R)-1-[(4S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl]-3-methyl-1-oxobutan-2-yl]cyclopentane-1-carboxamide
• CAS: 946588-46-1
• 化学式: C₂₄H₃₆ClN₃O₃
• 分子量: 450.021
• InChiKey: QXDGTGQXDUXRFU-CDNOPDGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  95.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(4-chloro-phenyl)-3,3-dimethyl-piperidin-4-ol 在 盐酸 、 L-酒石酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 (1S,3R)-3-amino-N-[(2R)-1-[(4S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl]-3-methyl-1-oxobutan-2-yl]cyclopentane-1-carboxamide
  参考文献：
  名称：

  The discovery of BMS-457, a potent and selective CCR1 antagonist

  摘要：

  A series of compounds which exhibited good human CCR1 binding and functional potency was modified resulting in the discovery of a novel series of high affinity, functionally potent antagonists of the CCR1 receptor. Issues of PXR activity, ion-channel potency, and poor metabolic stability were addressed by the addition of a hydroxyl group to an otherwise lipophilic area in the molecule resulting in the discovery of preclinical candidate BMS-457 for the treatment of rheumatoid arthritis. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.079

文献信息

• PIPERIDINYL DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Carter Percy H.

  公开号：US20070208056A1

  公开（公告）日：2007-09-06

  The present application describes substituted piperidinyl modulators of MIP-1α or CCR-1 or stereoisomers or pharmaceutically acceptable salts thereof. In addition, methods of treating and preventing inflammatory diseases such as asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and transplant rejection using said modulators are disclosed.

  本申请描述了MIP-1α或CCR-1的取代哌啶调节剂或其立体异构体或药学上可接受的盐。此外，还公开了使用上述调节剂治疗和预防炎症性疾病，如哮喘和过敏性疾病，以及自身免疫病理学，如类风湿性关节炎和移植排斥等方法。
• Piperidinyl derivatives as modulators of chemokine receptor activity
  申请人：Bristol-Myers Squibb Company

  公开号：EP2471773B1

  公开（公告）日：2016-03-23
• US7601844B2
  申请人：——

  公开号：US7601844B2

  公开（公告）日：2009-10-13
• US7985861B2
  申请人：——

  公开号：US7985861B2

  公开（公告）日：2011-07-26
• The discovery of BMS-457, a potent and selective CCR1 antagonist
  作者：Daniel S. Gardner、Joseph B. Santella、John V. Duncia、Percy H. Carter、T.G.Murali Dhar、Hong Wu、Weiwei Guo、Cullen Cavallaro、Katy Van Kirk、Melissa Yarde、Stephanie W. Briceno、R. Robert Grafstrom、Richard Liu、Sima R. Patel、Andrew J. Tebben、Dan Camac、Javed Khan、Andrew Watson、Guchen Yang、Anne Rose、William R. Foster、Mary Ellen Cvijic、Paul Davies、John Hynes

  DOI：10.1016/j.bmcl.2013.04.079

  日期：2013.7

  A series of compounds which exhibited good human CCR1 binding and functional potency was modified resulting in the discovery of a novel series of high affinity, functionally potent antagonists of the CCR1 receptor. Issues of PXR activity, ion-channel potency, and poor metabolic stability were addressed by the addition of a hydroxyl group to an otherwise lipophilic area in the molecule resulting in the discovery of preclinical candidate BMS-457 for the treatment of rheumatoid arthritis. (c) 2013 Elsevier Ltd. All rights reserved.