4-{[3-(methylthio)phenyl]thio}benzaldehyde | 1159113-26-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-{[3-(methylthio)phenyl]thio}benzaldehyde
• 英文别名: 4-(3-methylsulfanylphenyl)sulfanylbenzaldehyde
• CAS: 1159113-26-4
• 化学式: C₁₄H₁₂OS₂
• 分子量: 260.381
• InChiKey: JXXWDNSASPWNBL-UHFFFAOYSA-N

物化性质

• 沸点：
  441.8±30.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-{[3-(methylthio)phenyl]thio}benzaldehyde 、 6-alpha,9-alpha-二氟-11-beta,16-alpha,17-alpha,21-四羟基孕甾-1,4-二烯-3,20-二酮 在 三氟甲磺酸 、 magnesium sulfate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以18%的产率得到(4aS,4bR,5S,6aS,6bS,8R,9aR,10aS,10bS,12S)-4b,12-difluoro-6b-glycoloyl-5-hydroxy-4a,6a-dimethyl-8-(4-{[3-(methylthio)phenyl]thio}phenyl)-4a,4b,5,6,6a,6-b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho-[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
  参考文献：
  名称：

  [EN] NOVEL GLUCOCORTICOID RECEPTOR AGONISTS
  [FR] NOUVEAUX AGONISTES DES RÉCEPTEURS DES GLUCOCORTICOÏDES

  摘要：

  公开号：

  WO2009069032A3
• 作为产物：
  描述：

  苯硫醇 在 potassium carbonate 、 sodium hydroxide 作用下， 以 2-甲基四氢呋喃 、 水 、 乙腈 为溶剂， 反应 0.42h， 生成 4-{[3-(methylthio)phenyl]thio}benzaldehyde
  参考文献：
  名称：

  Kilogram-Scale Synthesis of an Inhaled Corticosteroid

  摘要：

  The development and implementation of a safe and scalable process for the manufacture of corticosteroid PF-4714224 (1) is described. Initial routes used to synthesise analogues from this series directly from fluocinolone acetonide (2) were unsuitable for large-scale use. Key aspects of the route are the efficient and simple method for the preparation of the steroid tetraol (6), acetal formation by reaction of the tetraol with a bisulphite adduct (12), and isolation of the product by sequential recrystallisations.

  DOI：

  10.1021/op200257g

文献信息

• Novel Glucocorticoid Receptor Agonists
  申请人：Glossop Paul Alan

  公开号：US20090227548A1

  公开（公告）日：2009-09-10

  This Invention Relates To Novel Glucocorticoid Receptor Agonists of Formula (I): and to processes and intermediates for their preparation. The present invention also relates to pharmaceutical compositions containing these compounds, to their combination with one or more other therapeutic agents, as well as to their use for the treatment of a number of inflammatory and allergic diseases, disorders and conditions.

  本发明涉及一种新型的糖皮质激素受体激动剂，其化学式为(I)，以及用于其制备的工艺和中间体。本发明还涉及含有这些化合物的制药组合物，以及它们与一个或多个其他治疗剂的联合使用，以治疗多种炎症和过敏性疾病、紊乱和病况。
• Glucocorticoid receptor agonists
  申请人：Glossop Paul Alan

  公开号：US08822439B2

  公开（公告）日：2014-09-02

  This invention relates to novel glucocorticoid receptor agonists of formula (I): and to processes and intermediates for their preparation. The present invention also relates to pharmaceutical compositions containing these compounds, to their combination with one or more other therapeutic agents, as well as to their use for the treatment of a number of inflammatory and allergic diseases, disorders and conditions.

  本发明涉及一种新型糖皮质激素受体激动剂，其化学式为(I)，以及其制备过程和中间体。本发明还涉及含有这些化合物的制药组合物，以及它们与一个或多个其他治疗剂的联合使用，以及它们用于治疗多种炎症和过敏性疾病、疾病和病况。
• NOVEL GLUCOCORTICOLD RECEPTOR AGONISTS
  申请人：Pfizer Inc.

  公开号：US20140336160A1

  公开（公告）日：2014-11-13

  This invention relates to novel glucocorticoid receptor agonists of formula (I): and to processes and intermediates for their preparation. The present invention also relates to pharmaceutical compositions containing these compounds, to their combination with one or more other therapeutic agents, as well as to their use for the treatment of a number of inflammatory and allergic diseases, disorders and conditions.

  本发明涉及一种新型糖皮质激素受体激动剂，其化学式为（I），以及其制备过程和中间体。本发明还涉及含有这些化合物的制药组合物，以及它们与一种或多种其他治疗剂的组合，以及它们用于治疗多种炎症和过敏性疾病、障碍和病况。
• Design and synthesis of long acting inhaled corticosteroids for the treatment of asthma
  作者：David S. Millan、Stephen A. Ballard、Sara Chunn、Joseph A. Dybowski、Craig K. Fulton、Paul A. Glossop、Edouard Guillabert、Christopher A. Hewson、Rhys M. Jones、David J. Lamb、Carolyn M. Napier、Toby A. Payne-Cook、Emmanuelle R. Renery、Matthew D. Selby、Michelle F. Tutt、Michael Yeadon

  DOI：10.1016/j.bmcl.2011.07.106

  日期：2011.10

  In this Letter we present data for a novel series of ICS for the treatment of asthma. 'Inhalation by design' principles have been applied to a series of highly potent steroidal GR agonists, with a focus on optimising the potential therapeutic index in human. Pharmacokinetic properties were tuned with high intrinsic clearance and low oral bioavailability in mind, to minimise systemic exposure and reduce systemically driven adverse events. High CYP mediated clearance as well as glucuronidation were targeted to achieve high intrinsic clearance coupled with multiple routes of clearance to minimise drug-drug interactions. Furthermore, pharmaceutical properties such as stability, crystallinity and solubility were considered to ensure compatibility with a dry powder inhaler. This work culminated in the identification of the clinical candidate 15, which demonstrates preclinically the desired efficacy and safety profiles confirming its potential as an inhaled agent for the treatment of asthma. (C) 2011 Elsevier Ltd. All rights reserved.
• NOVEL GLUCOCORTICOID RECEPTOR AGONISTS
  申请人：Pfizer Limited

  公开号：EP2225256A2

  公开（公告）日：2010-09-08