sulfuric acid mono[2-(N'-[(R)-pyrrolidin-2-ylcarbonyl]hydrazinocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] ester | 1452460-35-3

• 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: sulfuric acid mono[2-(N'-[(R)-pyrrolidin-2-ylcarbonyl]hydrazinocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] ester
• 英文别名: trans-sulfuric acid mono-[2-(N'-[(R)-pyrrolidin-2-carbonyl]hydrazinocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl]ester；(2S,5R)-7-oxo-N'-[(2R)-pyrrolidin-2-ylcarbonyl]-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide；[(2S,5R)-7-oxo-2-[[[(2R)-pyrrolidine-2-carbonyl]amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
• CAS: 1452460-35-3
• 化学式: C₁₂H₁₉N₅O₇S
• 分子量: 377.378
• InChiKey: FFQDXPFDLOHIKI-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  166
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  tetrabutylammonium tert-butyl (2R)-2-[(2-{[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}hydrazinyl)carbonyl]pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以27.4%的产率得到sulfuric acid mono[2-(N'-[(R)-pyrrolidin-2-ylcarbonyl]hydrazinocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] ester
  参考文献：
  名称：

  NOVEL ß-LACTAMASE INHIBITOR AND METHOD FOR PRODUCING SAME

  摘要：

  公开号：

  EP2857401B8

文献信息

• NOVEL BETA-LACTAMASE INHIBITOR AND PROCESS FOR PREPARING THE SAME
  申请人：MEIJI SEIKA PHARMA CO., LTD.

  公开号：US20150141401A1

  公开（公告）日：2015-05-21

  A diazabicyclooctane compound, which is a beta-lactame inhibitor, represented by the following formula (I): wherein A represents Ra(Rb)N— or RcO—; B represents NH or NC 1-6 alkyl; C represents benzyl, H or SO 3 M, wherein M represents H, an inorganic or an organic cation; Ra and Rb represent H, C 1-6 alkyl or acyl; Rc represents C 1-6 alkyl or a heterocyclyl; A is unsubstituted or substituted with 0 to 4 substituents Fn1, wherein Fn1 represents C 1-6 alkyl, O═, or Rg-(CH 2 ) 0-3 —, wherein Rg represents a heterocyclyl, phenyl, heteroaryl, acyl, RdO 2 S—, Re(Rf)N—, Re(Rf)NCO—, ReO—, ReOCO— or a protective group, wherein Rd represents C 1-6 alkyl or MO—; Re and Rf represent H or C 1-6 alkyl, and a heterocycle having at least one nitrogen atom may be formed between Ra and Rb, between Rc and B, or between Re and Rf.

  这是一种二氮杂双环辛烷化合物，是一种β-内酰胺酶抑制剂，化学式为(I)，其中A代表Ra(Rb)N—或RcO—；B代表NH或NC1-6烷基；C代表苄基、氢或SO3M，其中M代表氢、无机或有机阳离子；Ra和Rb代表氢、C1-6烷基或酰基；Rc代表C1-6烷基或杂环基；A未被取代或被0至4个取代基Fn1取代，其中Fn1代表C1-6烷基、O═或Rg-(CH2)0-3—，其中Rg代表杂环基、苯基、杂环芳基、酰基、RdO2S—、Re(Rf)N—、Re(Rf)NCO—、ReO—、ReOCO—或保护基，其中Rd代表C1-6烷基或MO—；Re和Rf代表氢或C1-6烷基，Ra和Rb之间、Rc和B之间或Re和Rf之间可以形成至少一个含有氮原子的杂环。
• BETA-LACTAMASE INHIBITOR AND PROCESS FOR PREPARING THE SAME
  申请人：MEIJI SEIKA PHARMA CO., LTD.

  公开号：US20160024090A1

  公开（公告）日：2016-01-28

  A diazabicyclooctane compound, which is a beta-lactame inhibitor, represented by the following formula (I): wherein A represents Ra(Rb)N— or RcO—; B represents NH or NC 1-6 alkyl; C represents benzyl, H or SO 3 M, wherein M represents H, an inorganic or an organic cation; Ra and Rb represent H, C 1-6 alkyl or acyl; Rc represents C 1-6 alkyl or a heterocyclyl; A is unsubstituted or substituted with 0 to 4 substituents Fn1, wherein Fn1 represents C 1-6 alkyl, O═, or Rg-(CH 2 ) 0-3 —, wherein Rg represents a heterocyclyl, phenyl, heteroaryl, acyl, RdO 2 S—, Re(Rf)N—, Re(Rf)NCO—, ReO—, ReOCO— or a protective group, wherein Rd represents C 1-6 alkyl or MO—; Re and Rf represent H or C 1-6 alkyl, and a heterocycle having at least one nitrogen atom may be formed between Ra and Rb, between Rc and B, or between Re and Rf.

  一种二氮杂双环辛烷化合物，其为β-内酰胺酶抑制剂，由以下式子（I）表示：其中，A代表Ra（Rb）N-或RcO-；B代表NH或NC1-6烷基；C代表苄基、H或SO3M，其中M代表H、无机或有机阳离子；Ra和Rb代表H、C1-6烷基或酰基；Rc代表C1-6烷基或杂环基；A未被取代或被0至4个Fn1取代，其中Fn1代表C1-6烷基、O═或Rg-(CH2)0-3-，其中Rg代表杂环基、苯基、杂环芳基、酰基、RdO2S-、Re(Rf)N-、Re(Rf)NCO-、ReO-、ReOCO-或保护基，其中Rd代表C1-6烷基或MO-；Re和Rf代表H或C1-6烷基，Ra和Rb之间、Rc和B之间或Re和Rf之间可以形成至少一个含有氮原子的杂环。
• NOVEL -LACTAMASE INHIBITOR AND METHOD FOR PRODUCING SAME
  申请人：Meiji Seika Pharma Co., Ltd.

  公开号：EP2857401A1

  公开（公告）日：2015-04-08

  The currently available β-lactamase inhibitors are insufficient to inhibit the incessantly increasing β-lactamase, and novel β-lactamase inhibitors has been required today for the difficult treatment for bacterial infectious diseases caused by resistant bacteria which produce class C β-lactamase, extended-spectrum β-lactamase (ESBL) belonging to class A and D, or class A KPC-2 decomposing even carbapenem as a last resort for β-lactam antibiotic. A compound represented by the the formula (I), preparation process of the same, β-lactamase inhibitors and method for treating bacterial infectious diseases are provided.

  目前现有的β-内酰胺酶抑制剂不足以抑制不断增加的β-内酰胺酶，而新型β-内酰胺酶抑制剂已成为当今治疗由产生C类β-内酰胺酶、属于A类和D类的广谱β-内酰胺酶（ESBL）或A类KPC-2的耐药菌引起的细菌感染性疾病的难题所必需的，甚至可以分解碳青霉烯作为β-内酰胺抗生素的最后手段。 本发明提供了一种由式（I）代表的化合物、其制备工艺、β-内酰胺酶抑制剂以及治疗细菌感染性疾病的方法。
• Beta-lactamase inhibitor and process for preparing the same
  申请人：MEIJI SEIKA PHARMA CO., LTD.

  公开号：US10023573B2

  公开（公告）日：2018-07-17

  A process for preparing a diazabicyclooctane compound represented by the following formula (I): wherein A represents RcO—; B represents NH or NC1-6 alkyl; C represents a benzyl group; Rc represents a C1-6 alkyl group; A is substituted with one substituent Fn1, wherein Fn1 represents an azetidine group; the process including: (a) silylating the compound represented by the following formula (IV-c): wherein in the formula (IV-c), OBn represents benzyloxy, and (b) carrying out an intramolecular urea formation reaction.

  一种制备下式(I)所代表的重氮双环辛烷化合物的工艺： 其中A代表RcO-；B代表NH或NC1-6烷基；C代表苄基；Rc代表C1-6烷基；A被一个取代基Fn1取代，其中Fn1代表氮杂环丁烷基团；该工艺包括：(a)将下式(IV-c)代表的化合物硅烷化： 其中，在式 (IV-c) 中，OBn 代表苄氧基，以及 (b) 进行分子内脲形成反应。
• Processes for preparing a diazabicyclooctane compound
  申请人：MEIJI SEIKA PHARMA CO., LTD.

  公开号：US10556905B2

  公开（公告）日：2020-02-11

  A process for preparing a diazabicyclooctane compound represented by the following formula (I): wherein A represents RcO—; B represents NH or NC1-6 alkyl; C represents a benzyl group; Rc represents a C1-6 alkyl group; A is substituted with one substituent Fn1, wherein Fn1 represents an azetidine group; the process including: (a) silylating the compound represented by the following formula (IV-c): wherein in the formula (IV-c), OBn represents benzyloxy, and (b) carrying out an intramolecular urea formation reaction.

  一种制备下式(I)所代表的重氮双环辛烷化合物的工艺： 其中A代表RcO-；B代表NH或NC1-6烷基；C代表苄基；Rc代表C1-6烷基；A被一个取代基Fn1取代，其中Fn1代表氮杂环丁烷基团；该工艺包括：(a)将下式(IV-c)代表的化合物硅烷化： 其中，在式 (IV-c) 中，OBn 代表苄氧基，以及 (b) 进行分子内脲形成反应。