(S)-(+)-3-Phenyl-3-(4-piperidinyl)-2,6-piperidinedione | 115216-87-0

• 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: (S)-(+)-3-Phenyl-3-(4-piperidinyl)-2,6-piperidinedione
• 英文别名: (S)-3-phenyl-[3,4'-bipiperidine]-2,6-dione；(3S)-3-phenyl-3-piperidin-4-ylpiperidine-2,6-dione
• CAS: 115216-87-0
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: WCKABEIXAFZEIO-MRXNPFEDSA-N

物化性质

• 熔点：
  186-189 °C
• 沸点：
  476.5±45.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-碘苄基溴 、 (S)-(+)-3-Phenyl-3-(4-piperidinyl)-2,6-piperidinedione 在 盐酸 、 potassium carbonate 作用下， 以89%的产率得到(S)-3-Phenyl-3-<1-<(4-iodophenyl)methyl>-4-piperidinyl>-2,6-piperidinedione hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of iodine-125- and iodine-123-4-iododexetimide, a potent muscarinic cholinergic receptor antagonist

  摘要：

  A series of halogenated racemic analogues of dexetimide (1) was synthesized and their affinity for the muscarinic cholinergic receptor measured. One analogue, 4-iododexetimide (21), was efficiently labeled with 125I and 123I at high specific activity. In vitro binding studies and in vivo biodistribution studies suggest that 123I-labeled 21 may be useful for imaging muscarinic cholinergic receptors in the living human brain with single photon emission computed tomography.

  DOI：

  10.1021/jm00125a021
• 作为产物：
  描述：

  右苄替米特 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以93%的产率得到(S)-(+)-3-Phenyl-3-(4-piperidinyl)-2,6-piperidinedione
  参考文献：
  名称：

  Synthesis and biological evaluation of iodine-125- and iodine-123-4-iododexetimide, a potent muscarinic cholinergic receptor antagonist

  摘要：

  A series of halogenated racemic analogues of dexetimide (1) was synthesized and their affinity for the muscarinic cholinergic receptor measured. One analogue, 4-iododexetimide (21), was efficiently labeled with 125I and 123I at high specific activity. In vitro binding studies and in vivo biodistribution studies suggest that 123I-labeled 21 may be useful for imaging muscarinic cholinergic receptors in the living human brain with single photon emission computed tomography.

  DOI：

  10.1021/jm00125a021

文献信息

• WO2007/90826
  申请人：——

  公开号：——

  公开（公告）日：——
• WILSON, ALAN A.;DANNALS, ROBERT F.;RAVERT, HAYDEN T.;FROST, J. JAMES;WAGN+, J. MED. CHEM., 32,(1989) N, C. 1057-1062
  作者：WILSON, ALAN A.、DANNALS, ROBERT F.、RAVERT, HAYDEN T.、FROST, J. JAMES、WAGN+

  DOI：——

  日期：——
• DANNALS, ROBERT F.;LANGSTROM, BENGT;RAVERT, HAYDEN T.;WILSON, ALAN A.;WAG+, APPL. RADIAT. AND ISOTOP., 39,(1988) N 4, 291-295
  作者：DANNALS, ROBERT F.、LANGSTROM, BENGT、RAVERT, HAYDEN T.、WILSON, ALAN A.、WAG+

  DOI：——

  日期：——
• PIPERIDINE DERIVATIVES AS CXCR3 RECEPTOR ANTAGONISTS
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP1984349A1

  公开（公告）日：2008-10-29
• Piperidine Derivatives as Cxcr3 Receptor Antagonists
  申请人：Coesemans Erwin

  公开号：US20090030039A1

  公开（公告）日：2009-01-29

  The present invention relates to a compound of formula (I) a N-oxide thereof, a pharmaceutically acceptable salt thereof, a stereochemically isomeric form thereof or a solvate thereof, wherein X represents N or CH; Y and Z each independently represent C(═O) or CH 2 provided that at least one of Y and Z represents C(═O); R 1 represents CH(R 4 )-aryl or CH(R 4 )-heteroaryl; R 2 represents aryl 2 or heteroaryl; R 3 represents hydrogen; C 1-4 alkylcarbonyl; C 1-6 alkyl optionally substituted with C 1-6 alkyloxy, C 1-6 alkylthio, C 1-6 alkyloxycarbonyl or aryl 1 ; provided that when Y and Z each represent C(═O), X represents CH, R 3 represents hydrogen, R 4 represents hydrogen, and R 2 represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C 1-4 alkyloxy or with one or two C 1-4 alkyl, then aryl in the definition of R 1 is other than phenyl substituted with one halo or with one or two C 1-4 alkyl; and provided that when Y and Z each represent C(═O), X represents CH, R 3 represents hydrogen, and R 2 represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C 1-4 alkyloxy or with one or two C 1-4 alkyl, then heteroaryl in the definition of R 1 is other than unsubstituted thienyl or unsubstituted pyridyl. The present invention also relates to the use of a compound of formula (I) for the manufacture of a medicament for preventing or treating a disease mediated through activation of the CXCR3 receptor; to processes for preparing the compounds of formula (I) and pharmaceutical compositions comprising them.