1,1,1-trifluoro-4-(2-methanesulfonylphenyl)-2-(5-methanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-4-methylpentan-2-ol | 1198786-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1,1,1-trifluoro-4-(2-methanesulfonylphenyl)-2-(5-methanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-4-methylpentan-2-ol
• 英文别名: 1,1,1-trifluoro-4-methyl-4-(2-methylsulfonylphenyl)-2-[(5-methylsulfonyl-1H-pyrrolo[2,3-c]pyridin-2-yl)methyl]pentan-2-ol
• CAS: 1198786-17-2
• 化学式: C₂₂H₂₅F₃N₂O₅S₂
• 分子量: 518.578
• InChiKey: ZHDQJPLHDTXEKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-溴茴香硫醚 在 ruthenium trichloride 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium periodate 、 copper(l) iodide 、 magnesium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 氢化铝 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 39.5h， 生成 1,1,1-trifluoro-4-(2-methanesulfonylphenyl)-2-(5-methanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-4-methylpentan-2-ol
  参考文献：
  名称：

  Optimization of Drug-Like Properties of Nonsteroidal Glucocorticoid Mimetics and Identification of a Clinical Candidate

  摘要：

  A series of nonsteroidal dissociated glucocorticoid receptor agonists was optimized for drug-like properties such as cytochrome P450 inhibition, metabolic stability, aqueous solubility, and hERG ion channel inhibition. This effort culminated in the identification of the clinical candidate compound (R)-39.

  DOI：

  10.1021/ml500387y

文献信息

• Glucocorticoid Mimetics, Methods of Making Them, Pharmaceutical Compositions and Uses Thereof
  申请人：Harcken Christian

  公开号：US20090325988A1

  公开（公告）日：2009-12-31

  Compounds of Formula (I) wherein R 1 , R 2 , X, and Y are as defined herein, or a tautomer, optical isomer, prodrug, co-crystal, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.

  化合物的公式（I），其中R1，R2，X和Y的定义如本文所述，或其互变异构体，光学异构体，前药，共晶体或盐；含有这些化合物的药物组合物，以及使用这些化合物调节糖皮质激素受体功能的方法，治疗由糖皮质激素受体功能介导或以炎症，过敏或增殖过程为特征的疾病状态或病情的方法。
• GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2300472B1

  公开（公告）日：2012-01-18
• US8268859B2
  申请人：——

  公开号：US8268859B2

  公开（公告）日：2012-09-18
• [EN] GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF<br/>[FR] MIMÉTIQUES DE GLUCOCORTICOÏDES, LEURS PROCÉDÉS DE FABRICATION, DES COMPOSITIONS PHARMACEUTIQUES ET LEURS UTILISATIONS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009149139A1

  公开（公告）日：2009-12-10

  Compounds of Formula I wherein R1, R2, X, and Y are as defined herein, or a tautomer, optical isomer, prodrug, co-crystal, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.
• Optimization of Drug-Like Properties of Nonsteroidal Glucocorticoid Mimetics and Identification of a Clinical Candidate
  作者：Christian Harcken、Doris Riether、Pingrong Liu、Hossein Razavi、Usha Patel、Thomas Lee、Todd Bosanac、Yancey Ward、Mark Ralph、Zhidong Chen、Donald Souza、Richard M. Nelson、Alison Kukulka、Tazmeen N. Fadra-Khan、Ljiljana Zuvela-Jelaska、Mita Patel、David S. Thomson、Gerald H. Nabozny

  DOI：10.1021/ml500387y

  日期：2014.12.11

  A series of nonsteroidal dissociated glucocorticoid receptor agonists was optimized for drug-like properties such as cytochrome P450 inhibition, metabolic stability, aqueous solubility, and hERG ion channel inhibition. This effort culminated in the identification of the clinical candidate compound (R)-39.