(4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylic acid | 913623-68-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylic acid
• 英文别名: trans-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylic acid；(4R,5S)-5-tert-Butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-cyclohex-1-enecarboxylic acid；(4R,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(2,4,5-trifluorophenyl)cyclohexene-1-carboxylic acid
• CAS: 913623-68-4
• 化学式: C₁₈H₂₀F₃NO₄
• 分子量: 371.356
• InChiKey: MYDINWRSSCPQDT-BMIGLBTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 ((4R,5S)-5-amino-4-(2,4,5-trifluorophenyl)cyclohex-1-enyl)(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone
  参考文献：
  名称：

  Discovery of ((4R,5S)-5-Amino-4-(2,4,5- trifluorophenyl)cyclohex-1-enyl)-(3- (trifluoromethyl)-5,6-dihydro- [1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone (ABT-341), a Highly Potent, Selective, Orally Efficacious, and Safe Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes

  摘要：

  Dipeptidyl peptidase IV (DPP4) deactivates glucose-regulating hormones such as GLP-1 and GIP, thus, DPP4 inhibition has become a useful therapy for type 2 diabetes. Optimization of the high-throughput screening lead 6 led to the discovery of 25 (ABT-341), a highly potent, selective, and orally bioavailable DPP4 inhibitor. When dosed orally, 25 dose-dependently reduced glucose excursion in ZDF rats. Amide 25 is safe in a battery of in vitro and in vivo tests and may represent a new therapeutic agent for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm060955d
• 作为产物：
  描述：

  methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylate 在 甲醇 、 sodium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylic acid
  参考文献：
  名称：

  Pharmaceutical compositions as inhibitors of dipeptidyl peptidase-IV (DPP-IV)

  摘要：

  本发明涉及一种抑制二肽基肽酶IV（DPP-IV）的化合物，可用于预防或治疗糖尿病，特别是II型糖尿病，以及高血糖、代谢综合征、高胰岛素血症、肥胖、动脉粥样硬化、各种免疫调节性疾病和其他疾病。

  公开号：

  US20070049596A1

文献信息

• Pharmaceutical compositions as inhibitors of dipeptidyl peptidase-IV (DPP-IV)
  申请人：Pei Zhonghua

  公开号：US20070049596A1

  公开（公告）日：2007-03-01

  The present invention relates to compounds, which inhibit dipeptidyl peptidase IV (DPP-IV) and are useful for the prevention or treatment of diabetes, especially type II, as well as hyperglycemia, metabolic syndrome, hyperinsulinemia, obesity, atherosclerosis, various immunomodulatory diseases, and other diseases.

  本发明涉及一种抑制二肽基肽酶IV（DPP-IV）的化合物，可用于预防或治疗糖尿病，特别是II型糖尿病，以及高血糖、代谢综合征、高胰岛素血症、肥胖、动脉粥样硬化、各种免疫调节性疾病和其他疾病。
• PHARMACEUTICAL COMPOSITIONS AS INHIBITORS OF DIPEPTIDYL PEPTIDASE-IV (DPP-IV)
  申请人：AbbVie Inc.

  公开号：EP1919854B1

  公开（公告）日：2013-09-18
• US7834012B2
  申请人：——

  公开号：US7834012B2

  公开（公告）日：2010-11-16
• Discovery of ((4<i>R</i>,5<i>S</i>)-5-Amino-4-(2,4,5- trifluorophenyl)cyclohex-1-enyl)-(3- (trifluoromethyl)-5,6-dihydro- [1,2,4]triazolo[4,3-a]pyrazin-7(8<i>H</i>)-yl)methanone (ABT-341), a Highly Potent, Selective, Orally Efficacious, and Safe Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes
  作者：Zhonghua Pei、Xiaofeng Li、Thomas W. von Geldern、David J. Madar、Kenton Longenecker、Hong Yong、Thomas H. Lubben、Kent D. Stewart、Bradley A. Zinker、Bradley J. Backes、Andrew S. Judd、Mathew Mulhern、Stephen J. Ballaron、Michael A. Stashko、Amanda K. Mika、David W. A. Beno、Glenn A. Reinhart、Ryan M. Fryer、Lee C. Preusser、Anita J. Kempf-Grote、Hing L. Sham、James M. Trevillyan

  DOI：10.1021/jm060955d

  日期：2006.11.1

  Dipeptidyl peptidase IV (DPP4) deactivates glucose-regulating hormones such as GLP-1 and GIP, thus, DPP4 inhibition has become a useful therapy for type 2 diabetes. Optimization of the high-throughput screening lead 6 led to the discovery of 25 (ABT-341), a highly potent, selective, and orally bioavailable DPP4 inhibitor. When dosed orally, 25 dose-dependently reduced glucose excursion in ZDF rats. Amide 25 is safe in a battery of in vitro and in vivo tests and may represent a new therapeutic agent for the treatment of type 2 diabetes.