N-tert-butyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide

• 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: N-tert-butyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide
• 英文别名: 3-[4-chloro-α-(2-chloropyridin-3-yl)benzyloxy]-N-(tert-butyl)azetidine-1-carboxamide；N-tert-butyl-3-[(4-chlorophenyl)-(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide
• 化学式: C₂₀H₂₃Cl₂N₃O₂
• 分子量: 408.328
• InChiKey: YXUMIJMWSKIONG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯苯基溴化镁 在 sodium tetrahydroborate 、 1-氯乙基氯甲酸酯 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 63.45h， 生成 N-tert-butyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide
  参考文献：
  名称：

  Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity

  摘要：

  We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.032

文献信息

• [EN] AZETIDINECARBOXAMIDE DERIVATIVES AND THEIR USE IN THE TREATMENT OF CB1 RECEPTOR MEDIATED DISORDRS<br/>[FR] DERIVES AZETIDINECARBOXAMIDE ET LEUR UTILISATION POUR LE TRAITEMENT DE TROUBLES A MEDIATION DU RECEPTEUR DU CB1
  申请人：VERNALIS RES LTD

  公开号：WO2004096794A1

  公开（公告）日：2004-11-11

  Compounds of formula (I) and their use in therapy, particularly for the treatment of a disorder mediated by CB1 receptors, such as obesity, wherein: R1 is aryl or heteroaryl; R2 is alkyl, aryl or heteroaryl; R3 is alkyl, aryl, heteroaryl, NR9R10, OR 15, or NR 16C(O)R17; Y is C=O, C=S, SO2, or (CR7R8)p; m = 1 or 2; n = 1 or 2; and p=1,2,3 or 4, R7 to R17 being as defined in the specification; wherein if -Y-R3 is -C(O)NH(alkyl) then: R1 and/or R2 is selected from heteroary1; and/or m and/or n is 2; and/or R11 and/or R12 is lower alkyl, or a pharmaceutically acceptable salt or prodrug thereof.

  化合物的化学式（I）及其在治疗中的应用，特别是用于治疗由CB1受体介导的疾病，如肥胖，其中：R1为芳基或杂环芳基；R2为烷基，芳基或杂环芳基；R3为烷基，芳基，杂环芳基，NR9R10，OR 15，或NR 16C(O)R17；Y为C=O，C=S，SO2，或（CR7R8）p；m = 1或2；n = 1或2；p=1,2,3或4，R7到R17如规范中定义；其中如果-Y-R3为-C(O)NH(烷基)则：R1和/或R2从杂芳基中选择；和/或m和/或n为2；和/或R11和/或R12为较低烷基，或其药用盐或前药。
• Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disordrs
  申请人：Davidson Edward Paul James

  公开号：US20070173486A1

  公开（公告）日：2007-07-26

  Compounds of formula (I) and their use in therapy, particularly for the treatment of a disorder mediated by CB 1 receptors, such as obesity, wherein: R 1 is aryl or heteroaryl; R 2 is alkyl, aryl or heteroaryl; R 3 is alkyl, aryl, heteroaryl, NR 9 R 10 , OR 15 , or NR 16 C(O)R 17 ; Y is C═O, C═S, SO 2 , or (CR 7 R 8 ); m=1 or 2; n=1 or 2; and p=1, 2, 3 or 4, R 7 to R 17 being as defined in the specification; wherein if —Y—R 3 is —C(O)NH(alkyl) then: R 1 and/or R 2 is selected from heteroaryl; and/or m and/or n is 2; and/or R 11 and/or R 12 is lower alkyl, or a pharmaceutically acceptable salt or prodrug thereof.

  式(I)的化合物及其在治疗中的用途，特别是用于治疗由CB1受体介导的疾病，例如肥胖症，其中：R1为芳基或杂环芳基；R2为烷基，芳基或杂环芳基；R3为烷基，芳基，杂环芳基，NR9R10，OR15或NR16C（O）R17；Y为C═O，C═S，SO2或（CR7R8）；m=1或2；n=1或2；p=1、2、3或4，R7到R17如规范所定义；如果—Y—R3为—C（O）NH（烷基），则：R1和/或R2选自杂环芳基；和/或m和/或n为2；和/或R11和/或R12为较低的烷基，或其药学上可接受的盐或前药。
• Azetidinecarboxamide Derivatives And Their Use In The Treatment Of CB1 Receptor Mediated Disorders
  申请人：Davidson James Edward Paul

  公开号：US20090181939A1

  公开（公告）日：2009-07-16

  Compounds of formula (I) and their use in therapy, particularly for the treatment of a disorder mediated by CB 1 receptors, such as obesity, wherein: R 1 is aryl or heteroaryl; R 2 is alkyl, aryl or heteroaryl; R 3 is alkyl, aryl, heteroaryl, NR 9 R 10 , OR 15 , or NR 16 C(O)R 17 ; Y is C═O, C═S, SO 2 , or (CR 7 R 8 ) p ; m=1 or 2; n=1 or 2; and p=1, 2, 3 or 4, R 7 to R 17 being as defined in the specification; wherein if —Y—R 3 is C(O)NH(alkyl) then: R 1 and/or R 2 is selected from heteroaryl; and/or m and/or n is 2; and/or R 11 and/or R 12 is lower alkyl, or a pharmaceutically acceptable salt or prodrug thereof.

  公式（I）的化合物及其在治疗中的应用，特别是用于治疗由CB1受体介导的疾病，如肥胖症，其中：R1为芳基或杂环芳基；R2为烷基，芳基或杂环芳基；R3为烷基，芳基，杂环芳基，NR9R10，OR15或NR16C（O）R17；Y为C═O，C═S，SO2或（CR7R8）p；m=1或2；n=1或2；p=1、2、3或4，R7至R17如规范中所定义；其中，如果—Y—R3为C（O）NH（烷基），则：R1和/或R2选择自杂环芳基；和/或m和/或n为2；和/或R11和/或R12为低碳烷基，或其药学上可接受的盐或前药。
• EP1618105A1
  申请人：——

  公开号：EP1618105A1

  公开（公告）日：2006-01-25
• Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity
  作者：Stephen D. Roughley、Helen Browne、Alba T. Macias、Karen Benwell、Teresa Brooks、Jalanie D’Alessandro、Zoe Daniels、Sarah Dugdale、Geraint Francis、Ben Gibbons、Terance Hart、Timothy Haymes、Guy Kennett、Sean Lightowler、Natalia Matassova、Howard Mansell、Angela Merrett、Anil Misra、Anthony Padfield、Rachel Parsons、Robert Pratt、Alan Robertson、Heather Simmonite、Kiri Tan、Steven B. Walls、Melanie Wong

  DOI：10.1016/j.bmcl.2011.12.032

  日期：2012.1

  We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats. (C) 2011 Elsevier Ltd. All rights reserved.