3-(4-chlorophenyl)-4-phenyl-N-(piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide | 505031-19-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-(4-chlorophenyl)-4-phenyl-N-(piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
• 英文别名: Piperidine-1-sulfonic acid [3-(4-chloro-phenyl)-4-phenyl-4,5-dihydro-pyrazole-1-carbothioyl]-amide；3-(4-chlorophenyl)-4-phenyl-N-((piperidin-1-yl)sulfonyl)-4,5-dihydro-1H-pyrazole-1-thiocarboxamide；5-(4-chlorophenyl)-4-phenyl-N-piperidin-1-ylsulfonyl-3,4-dihydropyrazole-2-carbothioamide
• CAS: 505031-19-6
• 化学式: C₂₁H₂₃ClN₄O₂S₂
• 分子量: 463.024
• InChiKey: CSGUQIPVGKVYIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-4-phenyl-N-(piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 在 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 18.0h， 生成 N-methyl-N-[(piperidin-1-yl)sulfonyl]-3-(4-chloropheny)-4-phenyl-4,5-dihydro-(1H)-pyrazole-1-carboxamidine
  参考文献：
  名称：

  Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity

  摘要：

  Novel 3,4-diarylpyrazolines 1 as potent CB1 receptor antagonists with lipophilicity lower than that of SLV319 are described. The key change is the replacement of the arylsulfonyl group in the original series by a dialkylaminosulfonyl moiety. The absolute configuration (4S) of eutomer 24 was established by X-ray diffraction analysis and 24 showed a close molecular fit with rimonabant in a CB1 receptor-based model. Compound 17 exhibited the highest CB1 receptor affinity (K-i = 24 nM) in this series, as well as very potent CB1 antagonistic activity (pA(2) = 8.8) and a high CB1/CB2 subtype selectivity (similar to 147-fold). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.054
• 作为产物：
  描述：

  1-哌啶磺酰胺 在 氢氧化钾 、 氯甲酸三氯甲酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 3-(4-chlorophenyl)-4-phenyl-N-(piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
  参考文献：
  名称：

  Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity

  摘要：

  Novel 3,4-diarylpyrazolines 1 as potent CB1 receptor antagonists with lipophilicity lower than that of SLV319 are described. The key change is the replacement of the arylsulfonyl group in the original series by a dialkylaminosulfonyl moiety. The absolute configuration (4S) of eutomer 24 was established by X-ray diffraction analysis and 24 showed a close molecular fit with rimonabant in a CB1 receptor-based model. Compound 17 exhibited the highest CB1 receptor affinity (K-i = 24 nM) in this series, as well as very potent CB1 antagonistic activity (pA(2) = 8.8) and a high CB1/CB2 subtype selectivity (similar to 147-fold). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.054

文献信息

• [EN] 4,5-DIHYDRO-1H-PYRAZOLE DERIVATIVES HAVING POTENT CB1-ANTAGONISTIC ACTIVITY<br/>[FR] DERIVES 4,5-DIHYDRO-1H-PYRAZOLE PRESENTANT UNE PUISSANTE ACTIVITE ANTAGONISTE DU RECEPTEUR CB1
  申请人：SOLVAY PHARM BV

  公开号：WO2003026648A1

  公开（公告）日：2003-04-03

  The present invention relates to a group of novel 4,5-dihydro-1H-pyrazole derivatives which are potent cannabinoid (CB1) receptor antagonists with utility for the treatment of diseases connected with disorders of the cannabinoid system. The compounds have the general formula (Ia) or (Ib) wherein the symbols have the meanings given in the specification. The invention also relates to methods for the preparation of these compounds, and to pharmaceutical compositions containing one or more of these compounds as an active component.

  本发明涉及一组新型的4,5-二氢-1H-吡唑衍生物，它们是有效的大麻素受体（CB1）拮抗剂，适用于治疗与大麻素系统紊乱相关的疾病。这些化合物具有通式（Ia）或（Ib），其中符号具有规范中给出的含义。本发明还涉及制备这些化合物的方法，以及包含其中一种或多种化合物作为活性成分的制药组合物。
• 4,5-Dihydro-1h-pyrazole derivatives having potent cb1-antagonistic activity
  申请人：——

  公开号：US20040106800A1

  公开（公告）日：2004-06-03

  The present invention relates to a group of novel 4,5-dihydro-1H-pyrazole derivatives which are potent cannabinoid (CB 1 ) receptor antagonists with utility for the treatment of diseases connected with disorders of the cannabinoid system. The compounds have the general formula (Ia) or (Ib) wherein the symbols have the meanings given in the specification. The invention also relates to methods for the preparation of these compounds, and to pharmaceutical compositions containing one or more of these compounds as an active component. 1

  本发明涉及一类新型的4,5-二氢-1H-吡唑衍生物，它们是有效的大麻素（CB1）受体拮抗剂，可用于治疗与大麻素系统紊乱相关的疾病。这些化合物具有通式（Ia）或（Ib），其中符号的含义如规范中所述。本发明还涉及制备这些化合物的方法，以及包含其中一种或多种这些化合物作为活性成分的制药组合物。
• 4,5-Dihydro-1H-pyrazole derivatives having potent CB1-antagonistic activity
  申请人：Lange H.M. Josephus

  公开号：US20070259884A1

  公开（公告）日：2007-11-08

  The present invention relates to a group of novel 4,5-dihydro-1H-pyrazole derivatives which are potent cannabinoid (CB 1 ) receptor antagonists with utility for the treatment of diseases connected with disorders of the cannabinoid system. The compounds have the general formula (Ia) or (Ib) wherein the symbols have the meanings given in the specification. The invention also relates to methods for the preparation of these compounds, and to pharmaceutical compositions containing one or more of these compounds as an active component.

  本发明涉及一组新型的4,5-二氢-1H-吡唑衍生物，它们是具有治疗与大麻素系统紊乱相关疾病的功效的强效大麻素（CB1）受体拮抗剂。这些化合物具有通式（Ia）或（Ib），其中符号具有规范中所给定的含义。本发明还涉及制备这些化合物的方法，以及含有这些化合物之一或多个作为活性成分的制药组合物。
• 4,5-dihydro-1H-pyrazole derivatives having potent CB1-antagonistic activity
  申请人：Solvay Pharmaceuticals B.V.

  公开号：US07608718B2

  公开（公告）日：2009-10-27

  The present invention relates to a group of novel 4,5-dihydro-1H-pyrazole derivatives which are potent cannabinoid (CB1) receptor antagonists with utility for the treatment of diseases connected with disorders of the cannabinoid system. The compounds have the general formula (Ia) or (Ib) wherein the symbols have the meanings given in the specification. The invention also relates to methods for the preparation of these compounds, and to pharmaceutical compositions containing one or more of these compounds as an active component.

  本发明涉及一组新型的4,5-二氢-1H-吡唑衍生物，它们是有效的大麻素（CB1）受体拮抗剂，可用于治疗与大麻素系统紊乱相关的疾病。该化合物具有通式（Ia）或（Ib），其中符号具有规范中给出的含义。本发明还涉及制备这些化合物的方法，以及包含其中一种或多种该化合物作为活性成分的药物组合物。
• 4,5-DIHYDRO-1H-PYRAZOLE DERIVATIVES HAVING POTENT CB1-ANTAGONISTIC ACTIVITY
  申请人：Solvay Pharmaceuticals B.V.

  公开号：EP1429762A1

  公开（公告）日：2004-06-23