(3R)-1-(3-fluoro-4-methylphenyl)pyrrolidin-3-amine | 474774-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R)-1-(3-fluoro-4-methylphenyl)pyrrolidin-3-amine
• CAS: 474774-47-5
• 化学式: C₁₁H₁₅FN₂
• 分子量: 194.252
• InChiKey: KVILQWLLZUHSQQ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-1-(3-fluoro-4-methylphenyl)pyrrolidin-3-amine 、 异氰酸2-溴苯酯 以 二氯甲烷 为溶剂， 生成 1-(2-bromophenyl)-3-[(3R)-1-(3-fluoro-4-methylphenyl)pyrrolidin-3-yl]urea
  参考文献：
  名称：

  Discovery of SB-705498: A potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development

  摘要：

  Small molecule antagonists of the vanilloid receptor TRPV1 (also known as VR1) are disclosed. Pyrrolidinyl ureas such as 8 and 15 (SB-705498) emerged as lead compounds following optimisation of the previously described urea SB-452533. Pharmacological studies using electrophysiological and FLIPR-Ca2+-based assays showed that compounds such as 8 and 15 were potent antagonists versus the multiple chemical and physical modes of TRPV1 activation (namely capsaicin, acid and noxious heat). Furthermore, 15 possessed suitable developability properties to enable progression of this compound into in vivo studies and subsequently clinical development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.030
• 作为产物：
  描述：

  4-溴-2-氟甲苯 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (3R)-1-(3-fluoro-4-methylphenyl)pyrrolidin-3-amine
  参考文献：
  名称：

  Discovery of SB-705498: A potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development

  摘要：

  Small molecule antagonists of the vanilloid receptor TRPV1 (also known as VR1) are disclosed. Pyrrolidinyl ureas such as 8 and 15 (SB-705498) emerged as lead compounds following optimisation of the previously described urea SB-452533. Pharmacological studies using electrophysiological and FLIPR-Ca2+-based assays showed that compounds such as 8 and 15 were potent antagonists versus the multiple chemical and physical modes of TRPV1 activation (namely capsaicin, acid and noxious heat). Furthermore, 15 possessed suitable developability properties to enable progression of this compound into in vivo studies and subsequently clinical development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.030

文献信息

• [EN] UREA COMPOUNDS ACTIVE AS VANILLOID RECEPTOR ANTAGONISTS FOR THE TREATMENT OF PAIN<br/>[FR] COMPOSES A BASE D'UREE, ACTIFS EN TANT QU'ANTAGONISTES DU RECEPTEUR DE LA VANILLOIDE ET UTILISES POUR TRAITER LES DOULEURS
  申请人：GLAXO GROUP LTD

  公开号：WO2004024710A1

  公开（公告）日：2004-03-25

  Certain compounds of formula (I): or a pharmaceutically acceptable salt or solvate thereof, wherein R1, R2, P, P', n, p, q, r and s are as defined in the specification, a process for preparing such compounds, a pharmaceutical composition comprising such compounds and the use of such compounds in medicine.

  公式（I）的某些化合物：或其药用可接受的盐或溶剂，其中R1、R2、P、P'、n、p、q、r和s如规范中所定义，一种制备这种化合物的方法，包括这种化合物的药物组合物以及这种化合物在医学上的用途。
• Heterocyclic ureas, their preparation and their use as vanilloid receptor antagonists
  申请人：——

  公开号：US20040171639A1

  公开（公告）日：2004-09-02

  The invention relates to compounds of formula (I) having Vanilloid Receptor (VR1) antagonist activity, processes for their preparation, to compositions containing them and to their use in the treatment of various disorders.

  本发明涉及具有Vanilloid Receptor (VR1)拮抗活性的公式(I)化合物，其制备方法，含有它们的组合物以及它们在治疗各种疾病中的应用。
• Urea-compounds active as vanilloid receptor antagonists for the treatment of pain
  申请人：Rami Harshad Kantilal

  公开号：US20090163506A1

  公开（公告）日：2009-06-25

  Certain compounds of formula (I), or a pharmaceutically acceptable salt thereof, or a solvate thereof, wherein R 1 , R 2 , P, P′, n, p, q, r and s are as defined in the specification, a process for preparing such compounds, a pharmaceutical composition comprising such compounds and the use of such compounds and composition in medicine.

  某些式(I)的化合物，或其药学上可接受的盐，或其溶剂化物，其中R1、R2、P、P′、n、p、q、r和s的定义如规范所述，制备这种化合物的过程，包括这种化合物的药物组成物，以及这种化合物和组成物在医学上的使用。
• US6939891B2
  申请人：——

  公开号：US6939891B2

  公开（公告）日：2005-09-06
• US8063078B2
  申请人：——

  公开号：US8063078B2

  公开（公告）日：2011-11-22