5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride | 205055-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride
• CAS: 205055-20-5
• 化学式: C₇H₃Cl₂NO₂S₂
• 分子量: 268.144
• InChiKey: DDOAASFFFGZAFG-UHFFFAOYSA-N

物化性质

• 沸点：
  410.8±40.0 °C(Predicted)
• 密度：
  1.731±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3-amino-1-[(1S)-1-methyl-2-(morpholin-4-yl)-2-oxoethyl]pyrrolidin-2-one 、 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride 生成 5-chloro-N-[(3S)-1-[(2S)-1-(morpholin-4-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]thieno[3,2-b]pyridine-2-sulfonamide
  参考文献：
  名称：

  Factor Xa Inhibitors:  S1 Binding Interactions of a Series of N-{(3S)-1-[(1S)-1-Methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides

  摘要：

  Factor Xa inhibitory activities for a series of N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides with different P1 groups are described. These data provide insight into binding interactions within the S1 primary specificity pocket; rationales are presented for the derived SAR on the basis of electronic interactions through crystal structures of fXa-ligand complexes and molecular modeling studies. A good correlation between in vitro anticoagulant activities with lipophilicity and the extent of human serum albumin binding is observed within this series of potent fXa inhibitors. Pharmacokinetic profiles in rat and dog, together with selectivity over other trypsin-like serine proteases, identified 1f as a candidate for further evaluation.

  DOI：

  10.1021/jm060870c
• 作为试剂：
  描述：

  3-(3-(S)-amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochloride 以 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride 为溶剂， 生成 5-chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide
  参考文献：
  名称：

  Substituted sulfonic acid

  摘要：

  公式I的化合物表现出有用的药理活性，因此被纳入药物组合物中，并用于治疗患有某些医学疾病的患者。更具体地说，它们是凝血因子Xa活性的抑制剂。本发明涉及公式I的化合物、含有公式I化合物的组合物，以及它们的用途，用于治疗患有或受到可通过给予凝血因子Xa活性抑制剂而得到改善的生理状况的患者。

  公开号：

  US06034093A1

文献信息

• Synthesis, SAR and in vivo activity of novel thienopyridine sulfonamide pyrrolidinones as factor Xa inhibitors
  作者：Michael R. Becker、William R. Ewing、Roderick S. Davis、Henry W. Pauls、Cuong Ly、Aiwen Li、Helen J. Mason、Yong Mi Choi-Sledeski、Alfred P. Spada、Valeria Chu、Karen D. Brown、Dennis J. Colussi、Robert J. Leadley、Ross Bentley、Jeff Bostwick、Charles Kasiewski、Suzanne Morgan

  DOI：10.1016/s0960-894x(99)00466-7

  日期：1999.9

  Thienopyridine sulfonamide pyrrolidinones were found to be potent and selective inhibitors of the coagulation cascade enzyme factor Xa. SAR studies led to several compounds that were selected for further in vivo investigation. These novel aryl binding pocket moieties represent a structural modification to a series of fXa inhibitors. Several compounds proved to be efficacious i.v. antithrombotic agents

  发现噻吩并吡啶磺酰胺吡咯烷酮是凝血级联酶因子Xa的有效和选择性抑制剂。SAR研究导致选择了几种化合物进行进一步的体内研究。这些新颖的芳基结合口袋部分代表了一系列fXa抑制剂的结构修饰。几种化合物被证明是有效的静脉抗血栓药。
• Pyrrolidine derivatives as factor xa inhibitors
  申请人：Chan Chuen

  公开号：US20050107379A1

  公开（公告）日：2005-05-19

  The invention relates to compounds of formula (I) processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  本发明涉及公式（I）的化合物、其制备方法、包含它们的药物组合物以及它们在医学中的使用，特别是在改善需要使用Xa因子抑制剂的临床病情方面的使用。
• Chemical compounds
  申请人：Chan Chuen

  公开号：US20060160886A1

  公开（公告）日：2006-07-20

  The invention relates to compounds of formula (Ic) processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  本发明涉及式(Ic)化合物，其制备方法，含有它们的药物组合物以及它们在医学上的应用，特别是在改善适应于Xa因子抑制剂的临床状况方面的应用。
• Pyrrolidin-2-one derivatives as inhibitors of factor xa
  申请人：——

  公开号：US20040152697A1

  公开（公告）日：2004-08-05

  The invention relates to compounds of formula (Ic) processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated. 1

  本发明涉及公式（Ic）化合物，它们的制备过程，含有它们的药物组合物，以及它们在医学上的应用，特别是在改善适合使用因子Xa抑制剂的临床症状方面的应用。
• Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors
  申请人：Smallheer M. Joanne

  公开号：US20060247243A1

  公开（公告）日：2006-11-02

  The present application describes sulfonylaminovalerolactams and derivatives thereof of Formula I: or pharmaceutically acceptable salt forms thereof, wherein ring G is a mono- or bicyclic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了公式I的磺酰氨基戊内酰内酰胺及其衍生物，或其药学上可接受的盐形式，其中环G是单环或双环的碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是因子Xa的抑制剂。