3-(4-chlorophenyl)-N-methyl-4-phenyl-N''-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide | 1204250-59-8

• 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)-N-methyl-4-phenyl-N''-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide
• 英文别名: 5-(4-chlorophenyl)-N'-methyl-4-phenyl-N-[4-(trifluoromethyl)piperidin-1-yl]sulfonyl-3,4-dihydropyrazole-2-carboximidamide
• CAS: 1204250-59-8
• 化学式: C₂₃H₂₅ClF₃N₅O₂S
• 分子量: 527.998
• InChiKey: ABYRMVVDOJFFOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-N-methyl-4-phenyl-N''-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide 生成 (S)-3-(4-chlorophenyl)-N-methyl-4-phenyl-N''-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide 、 (R)-3-(4-chlorophenyl)-N-methyl-4-phenyl-N''-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide
  参考文献：
  名称：

  Synthesis, SAR and intramolecular hydrogen bonding pattern of 1,3,5-trisubstituted 4,5-dihydropyrazoles as potent cannabinoid CB1 receptor antagonists

  摘要：

  The synthesis, structure-activity relationship (SAR) studies and intramolecular hydrogen bonding pattern of 1,3,5-trisubstituted 4,5-dihydropyrazoles are described. The target compounds 6-18 represent a novel class of potent and selective CB1 receptor antagonists. Based on X-ray diffraction data, the orally active 17 is shown to elicit a different intramolecular H-bonding mode as compared to ibipinabant (3) and SLV330 (4). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.049
• 作为产物：
  描述：

  3-(4-chlorophenyl)-4-phenyl-N-((4-(trifluoromethyl)piperidin-1-yl)sulfonyl)-4,5-dihydro-1H-pyrazole-1-carbimidoyl chloride 、 盐酸甲胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-(4-chlorophenyl)-N-methyl-4-phenyl-N''-(4-(trifluoromethyl)piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide
  参考文献：
  名称：

  Synthesis, SAR and intramolecular hydrogen bonding pattern of 1,3,5-trisubstituted 4,5-dihydropyrazoles as potent cannabinoid CB1 receptor antagonists

  摘要：

  The synthesis, structure-activity relationship (SAR) studies and intramolecular hydrogen bonding pattern of 1,3,5-trisubstituted 4,5-dihydropyrazoles are described. The target compounds 6-18 represent a novel class of potent and selective CB1 receptor antagonists. Based on X-ray diffraction data, the orally active 17 is shown to elicit a different intramolecular H-bonding mode as compared to ibipinabant (3) and SLV330 (4). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.049

文献信息

• FLUORO-SUBSTITUTED 3,4-DIARYL-4,5-DIHYDRO-1H-PYRAZOLE-1-CARBOXAMIDINE DERIVATIVES HAVING CB1-ANTAGONISTIC ACTIVITY
  申请人：Lange Josephus H.M.

  公开号：US20110172274A1

  公开（公告）日：2011-07-14

  This invention concerns fluorinated 3,4-diaryl-4,5-dihydro-1H-pyrazole-1-carboxamidine derivatives as cannabinoid-CB 1 receptor antagonists, methods for preparing these compounds, novel intermediates useful for the synthesis of said compounds, methods for the preparation of these intermediates, pharmaceutical compositions containing one or more of these dihydropyrazole derivatives as active ingredient, as well as the use of these pharmaceutical compositions for the treatment of obesity and obesity-related cardiovascular disorders, drug addiction, cognition deficits, liver fibrosis and inflammatory disorders. The compounds have the general formula (I) wherein the symbols have the meanings given in the specification.

  本发明涉及氟化的3,4-二芳基-4,5-二氢-1H-吡唑-1-羧酰胺衍生物，作为大麻素CB1受体拮抗剂，制备这些化合物的方法，用于合成上述化合物的新型中间体，制备这些中间体的方法，含有一种或多种这些二氢吡唑衍生物作为活性成分的制药组合物，以及利用这些制药组合物治疗肥胖和肥胖相关心血管疾病、药物成瘾、认知缺陷、肝纤维化和炎症性疾病的用途。这些化合物的一般式为(I)，其中符号的含义在说明书中给出。
• JP2011524351A
  申请人：——

  公开号：JP2011524351A

  公开（公告）日：2011-09-01
• [EN] FLUORO-SUBSTITUTED 3,4-DIARYL-4,5-DIHYDRO-1H-PYRAZOLE-1-CARBOXAMIDINE DERIVATIVES HAVING CB1-ANTAGONISTIC ACTIVITY<br/>[FR] DÉRIVÉS DE 3,4-DIARYL-4,5-DIHYDRO-1H-PYRAZOLE-1-CARBOXAMIDINE SUBSTITUÉS PAR DU FLUOR AYANT UNE ACTIVITÉ ANTAGONISTE DE CB1
  申请人：SOLVAY PHARM BV

  公开号：WO2010003760A2

  公开（公告）日：2010-01-14

  This invention concerns fluorinated 3,4-diaryl-4,5-dihydro-1H-pyrazole-1-carboxamidine derivatives as cannabinoid-CB1 receptor antagonists, methods for preparing these compounds, novel intermediates useful for the synthesis of said compounds, methods for the preparation of these intermediates, pharmaceutical compositions containing one or more of these dihydropyrazole derivatives as active ingredient, as well as the use of these pharmaceutical compositions for the treatment of obesity and obesity-related cardiovascular disorders, drug addiction, cognition deficits, liver fibrosis and inflammatory disorders. The compounds have the general formula (I) wherein the symbols have the meanings given in the specification.
• Synthesis, SAR and intramolecular hydrogen bonding pattern of 1,3,5-trisubstituted 4,5-dihydropyrazoles as potent cannabinoid CB1 receptor antagonists
  作者：Jos H.M. Lange、Martina A.W. van der Neut、Arnold P. den Hartog、Henri C. Wals、Jan Hoogendoorn、Herman H. van Stuivenberg、Bernard J. van Vliet、Chris G. Kruse

  DOI：10.1016/j.bmcl.2010.01.049

  日期：2010.3

  The synthesis, structure-activity relationship (SAR) studies and intramolecular hydrogen bonding pattern of 1,3,5-trisubstituted 4,5-dihydropyrazoles are described. The target compounds 6-18 represent a novel class of potent and selective CB1 receptor antagonists. Based on X-ray diffraction data, the orally active 17 is shown to elicit a different intramolecular H-bonding mode as compared to ibipinabant (3) and SLV330 (4). (C) 2010 Elsevier Ltd. All rights reserved.