N-{(2R)-3-[4-(3,4-Dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl}-6-fluoroimidazo[1,2-a]pyridine-2-carboxamide | 583881-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: N-{(2R)-3-[4-(3,4-Dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl}-6-fluoroimidazo[1,2-a]pyridine-2-carboxamide
• 英文别名: N-[(2R)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-6-fluoroimidazo[1,2-a]pyridine-2-carboxamide
• CAS: 583881-21-4
• 化学式: C₂₂H₂₃Cl₂FN₄O₃
• 分子量: 481.354
• InChiKey: PCRWWFINVOSHRN-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4(3,4-二氯苯氧基)哌啶 在 sodium azide 、 三乙胺 、 三苯基膦 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-{(2R)-3-[4-(3,4-Dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl}-6-fluoroimidazo[1,2-a]pyridine-2-carboxamide
  参考文献：
  名称：

  Discovery and evolution of phenoxypiperidine hydroxyamide dual CCR3/H1 antagonists. Part I

  摘要：

  The discovery of potent small molecule dual antagonists of the human CCR3 and H-1 receptors is described for the treatment of allergic diseases, for example, asthma and allergic rhinitis. Optimizing in vitro potency and metabolic stability, starting from a CCR1 lead compound, led to compound 20 with potent dual CCR3/H-1 activity and in vitro metabolic stability. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.113

文献信息

• Chemical compounds
  申请人：AstraZeneca AB

  公开号：US07709500B2

  公开（公告）日：2010-05-04

  The invention provides compounds of formula (I): wherein: X is CH2, O, S(O)2 or NR10; Y is a bond, CH2, NR35, CH2NH, CH2NHC(O), CH(OH), CH(NHCOR33), CH(NHSO2R34), CH2O or CH2S; Z is C(O), or when Y is a bond Z can also be S(O)2; R1 is optionally substituted aryl, optionally substituted heterocyclyl or C4-6 cycloalkyl fused to a benzene ring; and R2, R3, R4, R5, R6, R7 and R8, R9, R10, R32, R33, R34 and R35 are as defined herein; are modulators of chemokine (especially CCR3) activity (for use in, for example, treating asthma). The invention also provides a process for making 4-(3,4-dichlorophenoxy)piperidine, which is useful as an intermediate for making certain compounds of the invention.

  该发明提供了式（I）的化合物：其中：X是CH2，O，S（O）2或NR10; Y是键，CH2，NR35，CH2NH，CH2NHC（O），CH（OH），CH（NHCOR33），CH（NHSO2R34），CH2O或CH2S; Z是C（O），或者当Y是键时，Z也可以是S（O）2; R1是可选取代芳基，可选取代杂环基或与苯环融合的C4-6环烷基; R2，R3，R4，R5，R6，R7和R8，R9，R10，R32，R33，R34和R35如本文所定义; 是趋化因子（特别是CCR3）活性调节剂（例如用于治疗哮喘）。该发明还提供了制备4-（3,4-二氯苯氧基）哌啶的方法，该方法对于制备本发明的某些化合物是有用的。
• Inhibition of chemokine CCL7 or receptor CCR3 of same for the treatment and diagnosis of prostate cancer
  申请人：Universite Paul Sabatier (Toulouse III)

  公开号：US10401365B2

  公开（公告）日：2019-09-03

  The invention concerns an inhibitor of the expression of chemokine CCL7 or an inhibitor of the expression of the receptor CCR3 or an inhibitor of CCL7/CCR3 interaction for the use of same to prevent or treat the extension of prostate cancer outside the prostatic capsule in a subject. The invention also concerns a method for determining the degree of aggressiveness of a prostate cancer tumor in a subject suffering from prostate cancer, comprising a step of determining the concentration or level of expression of the receptor CCR3 in a sample of prostate tumor cells obtained from said subject.

  本发明涉及一种趋化因子CCL7表达抑制剂或受体CCR3表达抑制剂或CCL7/CCR3相互作用抑制剂，用于预防或治疗受试者的前列腺癌向前列腺囊外延伸。本发明还涉及一种确定前列腺癌患者前列腺癌肿瘤侵袭程度的方法，该方法包括一个步骤，即确定从所述患者处获得的前列腺肿瘤细胞样本中受体CCR3的浓度或表达水平。
• CHEMICAL COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1478624B1

  公开（公告）日：2010-09-08
• Inhibition of Chemokine CCL7 or Receptor CCR3 of Same for the Treatment and Diagnosis of Prostate Cancer
  申请人：Universite Paul Sabatier (Toulouse III)

  公开号：US20170131282A1

  公开（公告）日：2017-05-11

  The invention concerns an inhibitor of the expression of chemokine CCL7 or an inhibitor of the expression of the receptor CCR3 or an inhibitor of CCL7/CCR3 interaction for the use of same to prevent or treat the extension of prostate cancer outside the prostatic capsule in a subject. The invention also concerns a method for determining the degree of aggressiveness of a prostate cancer tumour in a subject suffering from prostate cancer, comprising a step of determining the concentration or level of expression of the receptor CCR3 in a sample of prostate tumour cells obtained from said subject.
• US7709500B2
  申请人：——

  公开号：US7709500B2

  公开（公告）日：2010-05-04