[(R)-1-piperidin-4-yl-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester | 1097880-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(R)-1-piperidin-4-yl-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1R)-1-piperidin-4-yl-2-(2,4,5-trifluorophenyl)ethyl]carbamate
• CAS: 1097880-58-4
• 化学式: C₁₈H₂₅F₃N₂O₂
• 分子量: 358.404
• InChiKey: IOMVZXHLMGLTQW-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(R)-1-piperidin-4-yl-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester 、 2,4-二甲基嘧啶-5-甲酸 在 N-甲基吗啉 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 [(R)-1-[1-(2,4-Dimethyl-pyrimidine-5-carbonyl)-piperidin-4-yl]-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Dpp-IV inhibitors

  摘要：

  本发明涉及式（I）化合物，其中R1、R2、R3和n的含义如描述和权利要求中所述。所述化合物可用作DPP-IV抑制剂。本发明还涉及制备这种化合物以及将其作为药物的生产和使用。

  公开号：

  EP2019099A1
• 作为产物：
  描述：

  在 Adam’s catalyst 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 [(R)-1-piperidin-4-yl-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Piperidinyl-2-phenethylamino inhibitors of DPP-IV for the treatment of Type 2 diabetes

  摘要：

  A highly ligand efficient lead molecule was rapidly developed into a DPP-IV selective candidate series using focused small library synthesis. A significant hurdle for series advancement was genetic safety since some agents in this series impaired chromosome division that was detected using the in vitro micronucleus assay. A recently developed high-throughput imaging-based in vitro micronucleus assay enabled the identification of chemical space with a low probability of micronucleus activity. Advanced profiling of a subset within this space identified a compound with a clean safety pro. le, an acceptable human DPP-IV inhibition pro. le based on the rat PK/PD model and a projected human dose that was suitable for clinical development. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.099

文献信息

• Dpp-IV Inhibitors
  申请人：Edwards John Paul

  公开号：US20070265261A1

  公开（公告）日：2007-11-15

  The invention relates to compounds of formula (1) wherein Z, R 1-3 and A have the meaning as cited in the description and the claims. Said compounds are useful as DPP-IV inhibitors. The invention also relates to the preparation of such compounds as well as the production and use thereof as medicament.

  本发明涉及式（1）的化合物，其中Z，R1-3和A的含义如所述及权利要求中所述。所述化合物可用作DPP-IV抑制剂。本发明还涉及制备这些化合物以及将其作为药物的生产和使用。
• [EN] DPP-IV INHIBITORS<br/>[FR] INHIBITEURS DE DPP-IV
  申请人：SANTHERA PHARMACEUTICALS CH

  公开号：WO2009003681A1

  公开（公告）日：2009-01-08

  The invention relates to compounds of formula (I) wherein R1, R2, R3 and n have the meaning as cited in the description and the claims. Said compounds are useful as DPP-IV inhibitors. The invention also relates to the preparation of such compounds as well as the production and use thereof as medicament.
• Dpp-IV inhibitors
  申请人：Santhera Pharmaceuticals (Schweiz) AG

  公开号：EP2019099A1

  公开（公告）日：2009-01-28

  The invention relates to compounds of formula (I) wherein R1, R2, R3 and n have the meaning as cited in the description and the claims. Said compounds are useful as DPP-IV inhibitors. The invention also relates to the preparation of such compounds as well as the production and use thereof as medicament.

  本发明涉及式（I）化合物，其中R1、R2、R3和n的含义如描述和权利要求中所述。所述化合物可用作DPP-IV抑制剂。本发明还涉及制备这种化合物以及将其作为药物的生产和使用。
• Piperidinyl-2-phenethylamino inhibitors of DPP-IV for the treatment of Type 2 diabetes
  作者：John W. Benbow、Kim A. Andrews、Jiri Aubrecht、David Beebe、David Boyer、Shawn Doran、Michael Homiski、Yu Hui、Kirk McPherson、Janice C. Parker、Judith Treadway、Maria VanVolkenberg、William J. Zembrowski

  DOI：10.1016/j.bmcl.2009.02.099

  日期：2009.4

  A highly ligand efficient lead molecule was rapidly developed into a DPP-IV selective candidate series using focused small library synthesis. A significant hurdle for series advancement was genetic safety since some agents in this series impaired chromosome division that was detected using the in vitro micronucleus assay. A recently developed high-throughput imaging-based in vitro micronucleus assay enabled the identification of chemical space with a low probability of micronucleus activity. Advanced profiling of a subset within this space identified a compound with a clean safety pro. le, an acceptable human DPP-IV inhibition pro. le based on the rat PK/PD model and a projected human dose that was suitable for clinical development. (c) 2009 Elsevier Ltd. All rights reserved.