tert-butyl 4-(2-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yl]oxy}ethyl)piperidine-1-carboxylate | 1315465-08-7

• 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: tert-butyl 4-(2-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yl]oxy}ethyl)piperidine-1-carboxylate
• 英文别名: Tert-butyl 4-(2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)piperidine-1-carboxylate；tert-butyl 4-[2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yl]oxyethyl]piperidine-1-carboxylate
• CAS: 1315465-08-7
• 化学式: C₂₄H₃₆BF₃N₂O₅
• 分子量: 500.366
• InChiKey: DLMNANIHZWURCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yl]oxy}ethyl)piperidine-1-carboxylate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三环己基膦 盐酸 、 potassium phosphate 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 84.17h， 生成 6-(6-(2-(1-(2-dimethylamino-2-oxo-ethyl)piperidin-4-yl)ethoxy)-5-(trifluoromethyl)pyridin-3-yl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile hydrochloride
  参考文献：
  名称：

  [EN] 1H-[1,2,3]TRIAZOLO[4,5-c]PYRIDINE-4-CARBONITRILE DERIVATIVES
  [FR] DERIVES DE 1H-[1,2,3]TRIAZOLO[4,5-C]PYRIDINE-4-CARBONITRILE

  摘要：

  该发明涉及到1H-[1,2,3]三唑并[4,5-c]吡啶-4-碳腈衍生的Cathepsin S抑制剂的化合物(I)的公式，其中R1为H或(C1-3)烷基；R2为卤素或(C1-4)烷基，可选地取代一个或多个卤素；n为1-3；X为O或CH2；U、V和W为CH；或者U、V和W中的一个为N；Y为能够与Cathepsin S活性位点的Sn....S2取代基相互作用的基团；或其药学上可接受的盐，以及包含它们的药物组合物，以及这些衍生物用于制备用于治疗与Cathepsin S相关疾病的药物，如动脉粥样硬化、肥胖、炎症和免疫紊乱，如类风湿关节炎、牛皮癣、癌症和慢性疼痛，如神经病性疼痛。

  公开号：

  WO2011086125A1
• 作为产物：
  描述：

  N-Boc-4-哌啶乙醇 在 bis-triphenylphosphine-palladium(II) chloride 、 三丁基膦 、 potassium acetate 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 2.0h， 生成 tert-butyl 4-(2-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yl]oxy}ethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  NITROGENATED BICYCLIC AROMATIC HETEROCYCLIC COMPOUND

  摘要：

  公开号：

  EP2840083B1

文献信息

• 1H-[1,2,3]TRIAZOLO[4,5-c]PYRIDINE-4-CARBONITRILE DERIVATIVES
  申请人：Cai Jiaqiang

  公开号：US20120283239A1

  公开（公告）日：2012-11-08

  The invention relates to 1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile derived Cathepsin S inhibitors of Formula (I), wherein R 1 is H or (C 1-3 )alkyl; R 2 is halogen or (C 1-4 )alkyl, optionally substituted with one or more halogens; n is 1-3; X is O or CH 2 ; U, V and W are CH; or one of U, V and W is N; Y is a group capable of interacting with the S n . . . S 2 substites of the active site of Cathepsin S; or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising the same as well as to the use of these derivatives for the preparation of a medicament for the treatment of cathepsin S related diseases such as atherosclerosis, obesity, inflammation and immune disorders, such as rheumatoid arthritis, psoriasis, cancer, and chronic pain, such as neuropathic pain.

  本发明涉及公式（I）中的1H-[1,2,3]三唑并[4,5-c]吡啶-4-羧腈衍生的Cathepsin S抑制剂，其中R1为H或（C1-3）烷基；R2为卤素或（C1-4）烷基，可选地取代一个或多个卤素；n为1-3；X为O或CH2；U、V和W为CH；或其中之一为N；Y为能够与Cathepsin S活性位点的Sn...S2取代基相互作用的基团；或其药学上可接受的盐，以及包含它们的制药组合物，以及这些衍生物用于制备治疗Cathepsin S相关疾病的药物，例如动脉粥样硬化、肥胖症、炎症和免疫性疾病，如类风湿性关节炎、银屑病、癌症和慢性疼痛，如神经病理性疼痛。
• NITROGEN-CONTAINING BICYCLIC AROMATIC HETEROCYCLIC COMPOUND
  申请人：ASTELLAS PHARMA INC.

  公开号：US20150126488A1

  公开（公告）日：2015-05-07

  [Problem] On the basis of a cathepsin S inhibitory effect, an excellent agent for treating or preventing autoimmune disease, allergic disease, graft rejection of an organ, bone marrow or tissue, systemic lupus erythematosus, or the like is provided. [Means for Solution] It was found that a nitrogen-containing bicyclic heterocyclic compound has the excellent cathepsin S inhibitory effect, thereby completing the invention. The compound of the present invention has the cathepsin S inhibitory effect, and can be used as an agent for preventing and/or treating autoimmune disease, allergic disease, graft rejection of an organ, bone marrow or tissue, systemic lupus erythematosus, or the like.

  [问题] 基于对cathepsin S的抑制作用，提供了一种用于治疗或预防自身免疫性疾病、过敏性疾病、器官、骨髓或组织的移植排斥、全身性红斑狼疮等的优秀药剂。 [解决方法] 发现一种含氮的双环杂环化合物具有优异的cathepsin S抑制作用，从而完成了本发明。本发明的化合物具有cathepsin S抑制作用，可用作预防和/或治疗自身免疫性疾病、过敏性疾病、器官、骨髓或组织的移植排斥、全身性红斑狼疮等的药剂。
• 1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile derivatives
  申请人：Cai Jiaqiang

  公开号：US09115126B2

  公开（公告）日：2015-08-25

  The invention relates to 1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile derived Cathepsin S inhibitors of Formula (I), wherein R1 is H or (C1-3)alkyl; R2 is halogen or (C1-4)alkyl, optionally substituted with one or more halogens; n is 1-3; X is O or CH2; U, V and W are CH; or one of U, V and W is N; Y is a group capable of interacting with the Sn . . . S2 substites of the active site of Cathepsin S; or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising the same as well as to the use of these derivatives for the preparation of a medicament for the treatment of cathepsin S related diseases such as atherosclerosis, obesity, inflammation and immune disorders, such as rheumatoid arthritis, psoriasis, cancer, and chronic pain, such as neuropathic pain.

  本发明涉及一种1H-[1,2,3]三唑并[4,5-c]吡啶-4-羧腈衍生的Cathepsin S抑制剂，其化学式为（I），其中R1为H或（C1-3）烷基; R2为卤素或（C1-4）烷基，可选地取代一个或多个卤素; n为1-3; X为O或CH2; U，V和W为CH; 或者U，V和W中的一个为N; Y是一种能够与Cathepsin S活性位点的Sn…S2取代基相互作用的基团; 或其药学上可接受的盐，以及包含它们的制药组合物，以及这些衍生物用于制备治疗与Cathepsin S相关的疾病，如动脉粥样硬化，肥胖，炎症和免疫障碍，如类风湿性关节炎，银屑病，癌症和慢性疼痛，如神经病性疼痛的药物的用途。
• Nitrogen-containing bicyclic aromatic heterocyclic compound
  申请人：ASTELLAS PHARMA INC.

  公开号：US09328118B2

  公开（公告）日：2016-05-03

  [Problem] On the basis of a cathepsin S inhibitory effect, an excellent agent for treating or preventing autoimmune disease, allergic disease, graft rejection of an organ, bone marrow or tissue, systemic lupus erythematosus, or the like is provided. [Means for Solution] It was found that a nitrogen-containing bicyclic heterocyclic compound has the excellent cathepsin S inhibitory effect, thereby completing the invention. The compound of the present invention has the cathepsin S inhibitory effect, and can be used as an agent for preventing and/or treating autoimmune disease, allergic disease, graft rejection of an organ, bone marrow or tissue, systemic lupus erythematosus, or the like.

  【问题】基于对cathepsin S的抑制作用，提供了一种治疗或预防自身免疫疾病、过敏性疾病、器官、骨髓或组织的移植排斥、全身性红斑狼疮等的优秀药剂。 【解决方案】发现一种含氮的双环杂环化合物具有优异的cathepsin S抑制作用，从而完成了该发明。本发明的化合物具有cathepsin S抑制作用，可用作预防和/或治疗自身免疫疾病、过敏性疾病、器官、骨髓或组织的移植排斥、全身性红斑狼疮等的药剂。
• NITROGENATED BICYCLIC AROMATIC HETEROCYCLIC COMPOUND
  申请人：Astellas Pharma Inc.

  公开号：EP2840083B1

  公开（公告）日：2017-09-13