4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ol | 1033214-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ol
• 英文别名: 2,1,3-Benzothiadiazole-1(3H)-propanol, 3-(2-fluorophenyl)-alpha-[(methylamino)methyl]-, 2,2-dioxide, (alphaS)-；4-[3-(2-fluorophenyl)-2,2-dioxo-2λ6,1,3-benzothiadiazol-1-yl]-1-(methylamino)butan-2-ol
• CAS: 1033214-86-6
• 化学式: C₁₇H₂₀FN₃O₃S
• 分子量: 365.429
• InChiKey: PHSDSMUCNUCJGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  557.8±60.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ol 以 甲醇 为溶剂， 以99.9%的产率得到
  参考文献：
  名称：

  WO2008/73459

  摘要：

  公开号：
• 作为产物：
  描述：

  3-(2-Fluorophenyl)-1-[2-(oxiran-2-yl)ethyl]-2lambda6,1,3-benzothiadiazole 2,2-dioxide 、 甲胺 以 乙醇 为溶剂， 反应 0.05h， 以300 mg的产率得到4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ol
  参考文献：
  名称：

  Discovery of Novel Selective Norepinephrine Reuptake Inhibitors: 4-[3-Aryl-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ols (WYE-103231)

  摘要：

  Structural modification of a virtual screening hit led to the identification of a new series of 4-[3-aryl-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ols which are potent and selective inhibitors of the norepinephrine transporter over both the serotonin and dopamine transporters. One representative compound S-17b (WYE-103231) had low nanomolar hNET potency (IC(50) = 1.2 nM) and excellent selectivity for hNET over hsERT (> 1600-fold) and hDAT (> 600-fold). S-17b additionally had a good pharmacokinetic profile and demonstrated oral efficacy in rat models of ovariectomized-induced thermoregulatory dysfunction and morphine dependent flush as well as the hot plate and spinal nerve ligation (SNL) models of acute and neuropathic pain.

  DOI：

  10.1021/jm100053t

文献信息

• HYDROXY-SUBSTITUTED ARYL SULFAMIDE DERIVATIVES AND METHODS OF THEIR USE
  申请人：McComas Casey Cameron

  公开号：US20080194654A1

  公开（公告）日：2008-08-14

  The present invention is directed to hydroxy-substituted aryl sulfamide derivatives of formula I: or a pharmaceutically acceptable salt, stereoisomer or tautomer thereof, which are monoamine reuptake inhibitors, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions, including, inter alia, vasomotor symptoms, sexual dysfunction, gastrointestinal disorders and genitourinary disorder, depression disorders, endogenous behavioral disorders, cognitive disorders, diabetic neuropathy, pain, and other diseases or disorders.

  本发明涉及式I的羟基取代芳基磺酰胺衍生物：或其药学上可接受的盐、立体异构体或互变异构体，它们是单胺再摄取抑制剂，包含这些衍生物的组合物，以及它们用于预防和治疗包括血管运动症状、性功能障碍、胃肠障碍和泌尿系障碍、抑郁症、内源性行为障碍、认知障碍、糖尿病神经病变、疼痛和其他疾病或障碍的方法。
• ARYL SULFAMIDE DERIVATIVES AND METHODS OF THEIR USE
  申请人：McComas Casey Cameron

  公开号：US20100029641A1

  公开（公告）日：2010-02-04

  The present invention is directed to aryl sulfamide derivatives of formula I: or a pharmaceutically acceptable salt, stereoisomer or tautomer thereof, which are monoamine reuptake inhibitors, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions, including, inter alia, vasomotor symptoms, sexual dysfunction, gastrointestinal disorders and genitourinary disorder, depression disorders, endogenous behavioral disorders, cognitive disorders, diabetic neuropathy, pain, and other diseases or disorders.

  本发明涉及公式I的芳基磺酰胺衍生物： 或其药学上可接受的盐、立体异构体或互变异构体，它们是单胺再摄取抑制剂，包含这些衍生物的组合物以及它们的使用方法，用于预防和治疗多种疾病或疾病，包括但不限于血管运动症状、性功能障碍、胃肠障碍和泌尿生殖障碍、抑郁症、内源性行为障碍、认知障碍、糖尿病神经病变、疼痛和其他疾病或障碍。
• WO2008/73459
  申请人：——

  公开号：——

  公开（公告）日：——
• US7601722B2
  申请人：——

  公开号：US7601722B2

  公开（公告）日：2009-10-13
• [EN] ARYL SULFAMIDE DERIVATIVES AND METHODS OF THEIR USE<br/>[FR] DÉRIVÉS D'ARYL SULFAMIDE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：WYETH CORP

  公开号：WO2008073459A1

  公开（公告）日：2008-06-19

  [EN] The present invention is directed to aryl sulfamide derivatives of formula (I): or a pharmaceutically acceptable salt, stereoisomer or tautomer thereof, which are monoamine reuptake inhibitors, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions, including, inter alia, vasomotor symptoms, sexual dysfunction, gastrointestinal disorders and genitourinary disorder, depression disorders, endogenous behavioral disorders, cognitive disorders, diabetic neuropathy, pain, and other diseases or disorders.
  [FR] La présente invention concerne des dérivés d'aryl sulfamide de formule (I) ou un sel pharmacocompatible, un stéréoisomère ou un tautomère de ceux-ci, qui sont des inhibiteurs du recaptage de la monoamine, des compositions contenant ces dérivés, et leurs méthodes d'utilisation dans la prévention et le traitement de troubles comprenant, entres autres, des symptômes vasomoteurs, des dysfonctions sexuelles, des troubles gastrointestinaux et des troubles génito-urinaires, des troubles associés à la dépression, des troubles endogènes du comportement, des troubles cognitifs, la neuropathie diabétique, des douleurs et autres maladies ou troubles.