5-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazole-2-carbonitrile | 916889-35-5

• 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: 5-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazole-2-carbonitrile
• 英文别名: 5-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,3,4-thiadiazole-2-carbonitrile
• CAS: 916889-35-5
• 化学式: C₁₅H₁₃F₃N₄OS
• 分子量: 354.356
• InChiKey: HIJVMZVRXFXSIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazole-2-carbonitrile 在 吡啶 、 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 1-[5-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3,4-thiadiazol-2-yl]-4-[2-(trifluoromethyl)phenoxy]piperidine
  参考文献：
  名称：

  WO2006/130986

  摘要：

  公开号：
• 作为产物：
  描述：

  4-(2-(三氟甲基)苯氧基)哌啶盐酸盐 在 亚硝酸特丁酯 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 5-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazole-2-carbonitrile
  参考文献：
  名称：

  WO2006/130986

  摘要：

  公开号：

文献信息

• Azacycloalkane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase
  申请人：Lachance Nicolas

  公开号：US20080132542A1

  公开（公告）日：2008-06-05

  Azacycloalkane derivatives of structural formula I are selective inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD1) relative to other known stearoyl-coenzyme A desaturases. The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, such as atherosclerosis; obesity; diabetes; neurological disease; metabolic syndrome; insulin resistance; and liver steatosis.

  结构式I的氮代环烷衍生物是选择性抑制剂，相对于其他已知的硬脂酰辅酶A delta-9去饱和酶（SCD1）。本发明的化合物可用于预防和治疗与异常脂质合成和代谢相关的疾病，包括心血管疾病，如动脉粥样硬化；肥胖；糖尿病；神经系统疾病；代谢综合征；胰岛素抵抗；和肝脂肪变性。
• Azacyclohexane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase
  申请人：Li Chun Sing

  公开号：US20090099200A1

  公开（公告）日：2009-04-16

  Azacyclohexane derivatives of structural formula I are selective inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD1) relative to other known stearoyl-coenzyme A desaturases. The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, atherosclerosis; obesity; diabetes; neurological disease; metabolic syndrome; insulin resistance; and liver steatosis.

  结构式I的脂环己基衍生物是选择性抑制硬脂酰辅酶A delta-9去饱和酶（SCD1）相对于其他已知的硬脂酰辅酶A去饱和酶的化合物。本发明的化合物可用于预防和治疗与异常脂质合成和代谢有关的疾病，包括心血管疾病、动脉粥样硬化、肥胖症、糖尿病、神经系统疾病、代谢综合征、胰岛素抵抗和肝脂肪变性。
• Development of a Liver-Targeted Stearoyl-CoA Desaturase (SCD) Inhibitor (MK-8245) to Establish a Therapeutic Window for the Treatment of Diabetes and Dyslipidemia
  作者：Renata M. Oballa、Liette Belair、W. Cameron Black、Kelly Bleasby、Chi Chung Chan、Carole Desroches、Xiaobing Du、Robert Gordon、Jocelyne Guay、Sebastien Guiral、Michael J. Hafey、Emelie Hamelin、Zheng Huang、Brian Kennedy、Nicolas Lachance、France Landry、Chun Sing Li、Joseph Mancini、Denis Normandin、Alessandro Pocai、David A. Powell、Yeeman K. Ramtohul、Kathryn Skorey、Dan Sørensen、Wayne Sturkenboom、Angela Styhler、Deena M. Waddleton、Hao Wang、Simon Wong、Lijing Xu、Lei Zhang

  DOI：10.1021/jm200319u

  日期：2011.7.28

  The potential use of SCD inhibitors for the chronic treatment of diabetes and dyslipidemia has been limited by preclinical adverse events associated with inhibition of SCD in skin and eye tissues. To establish a therapeutic window, we embarked on designing liver-targeted SCD inhibitors by utilizing molecular recognition by liver-specific organic anion transporting polypeptides (OATPs). In doing so, we set out to target the SCD inhibitor to the organ believed to be responsible for the therapeutic efficacy (liver) while minimizing its exposure in the tissues associated with mechanism-based SCD depletion of essential lubricating lipids (skin and eye). These efforts led to the discovery of MK-8245 (7), a potent, liver-targeted SCD inhibitor with preclinical antidiabetic and antidyslipidemic efficacy with a significantly improved therapeutic window.
• AZACYCLOHEXANE DERIVATIVES AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE
  申请人：Merck Frosst Canada Ltd.

  公开号：EP1902051A1

  公开（公告）日：2008-03-26
• AZACYCLOALKANE DERIVATIVES AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE
  申请人：Merck Canada Inc.

  公开号：EP2099793B1

  公开（公告）日：2012-02-01