(2S,5R)-7-oxo-N-(piperidin-4-ylmethyl)-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide | 1174019-36-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5R)-7-oxo-N-(piperidin-4-ylmethyl)-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
• 英文别名: [(2S,5R)-7-oxo-2-(piperidin-4-ylmethylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
• CAS: 1174019-36-3
• 化学式: C₁₃H₂₂N₄O₆S
• 分子量: 362.407
• InChiKey: DSIOHNDCLFKUPP-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2S,5R)-6-(苄氧基)-7-氧代-1,6-二氮杂双环[3.2.1]辛烷-2-羧酸 在 吡啶 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 三氧化硫吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2S,5R)-7-oxo-N-(piperidin-4-ylmethyl)-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
  参考文献：
  名称：

  Discovery of MK-7655, a β-lactamase inhibitor for combination with Primaxin®

  摘要：

  beta-Lactamase inhibitors with a bicyclic urea core and a variety of heterocyclic side chains were prepared and evaluated as potential partners for combination with imipenem to overcome class A and C beta-lactamase mediated antibiotic resistance. The piperidine analog 3 (MK-7655) inhibited both class A and C beta-lactamases in vitro. It effectively restored imipenem's activity against imipenem-resistant Pseudomonas and Klebsiella strains at clinically achievable concentrations. A combination of MK-7655 and Primaxin (R) is currently in phase II clinical trials for the treatment of Gram-negative bacterial infections. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.101

文献信息

• BETA-LACTAMASE INHIBITORS
  申请人：Blizzard Timothy A.

  公开号：US20110294777A1

  公开（公告）日：2011-12-01

  Substituted bicyclic beta-lactams of Formula I: (I), are β-lactamase inhibitors, wherein a, X, R 1 and R 2 are defined herein. The compounds and pharmaceutically acceptable salts thereof are useful in the treatment of bacterial infections in combination with β-lactam antibiotics. In particular, the compounds can be employed with a β-lactam antibiotics (e.g., imipenem, piperacillin, or ceftazidime) against microorganisms resistant to β-lactam antibiotics due to the presence of the β-lactamases.

  化合物I的替代双环β-内酰胺(I)是β-内酰胺酶抑制剂，其中a、X、R1和R2如此定义。该化合物及其药学上可接受的盐在与β-内酰胺类抗生素联合治疗细菌感染方面是有用的。特别地，该化合物可与β-内酰胺类抗生素（例如亚胺培南、哌拉西林或头孢他啶）一起用于对抗由β-内酰胺酶存在而对β-内酰胺类抗生素产生耐药性的微生物。
• BICYCLIC COMPOUNDS AND THEIR USE AS ANTIBACTERIAL AGENTS AND BETALACTAMASE INHIBITORS
  申请人：NAEJA PHARMACEUTICAL INC.

  公开号：US20140221341A1

  公开（公告）日：2014-08-07

  A compound of formula (I): wherein: M is hydrogen or a pharmaceutically acceptable salt-forming cation; Y is OR 1 or NR 2 R 3 , and R 1 , R 2 , R 3 and M are as defined herein. Also, methods of treating bacterial infection, pharmaceutical compositions, molecular complexes and processes for preparing compounds.

  化合物的式子(I)：其中：M是氢或药用可接受的盐形成阳离子；Y是OR1或NR2R3，而R1、R2、R3和M的定义如本文所述。此外，还提供了治疗细菌感染的方法、制药组合物、分子复合物和制备化合物的过程。
• Beta-lactamase Inhibitors
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2666774A1

  公开（公告）日：2013-11-27

  Substituted bicyclic beta-lactams of Formula I: are β-lactamase inhibitors, wherein a, X, R1 and R2 are defined herein. The compounds and pharmaceutically acceptable salts thereof are useful in the treatment of bacterial infections in combination with β-lactam antibiotics. In particular, the compounds can be employed with a β-lactam antibiotics (e.g., imipenem, piperacillin, or ceftazidime) against microorganisms resistant to β-lactam antibiotics due to the presence of the β-lactamases.

  式 I 的取代双环β-内酰胺： 是 β-内酰胺酶抑制剂，其中 a、X、R1 和 R2 在本文中定义。这些化合物及其药学上可接受的盐类可与β-内酰胺类抗生素联合用于治疗细菌感染。特别是，本发明化合物可与β-内酰胺类抗生素（如亚胺培南、哌拉西林或头孢他啶）一起使用，以对抗因存在β-内酰胺酶而对β-内酰胺类抗生素产生耐药性的微生物。
• BICYCLIC COMPOUNDS AND THEIR USE AS ANTIBACTERIAL AGENTS AND BETA-LACTAMASE INHIBITORS
  申请人：FEDORA PHARMACEUTICALS INC.

  公开号：US20160297817A1

  公开（公告）日：2016-10-13

  A compound of formula (I): wherein: M is hydrogen or a pharmaceutically acceptable salt-forming cation; Y is OR 1 or NR 2 R 3 , and R 1 , R 2 , R 3 and M are as defined herein. Also, methods of treating bacterial infection, pharmaceutical compositions, molecular complexes and processes for preparing compounds.
• US8487093B2
  申请人：——

  公开号：US8487093B2

  公开（公告）日：2013-07-16