t-butyl (1S,5R)-7-oxo-6-sulfo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate | 145828-06-4

• 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: t-butyl (1S,5R)-7-oxo-6-sulfo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate
• 英文别名: (1S,5R)-2-[(2-methylpropan-2-yl)oxycarbonyl]-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid
• CAS: 145828-06-4
• 化学式: C₁₀H₁₆N₂O₆S
• 分子量: 292.313
• InChiKey: FBCNAOZPYXZOOX-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  t-butyl (1S,5R)-7-oxo-6-sulfo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1S,5R)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-6-sulfonic acid
  参考文献：
  名称：

  [EN] PROCESS FOR THE MANUFACTURE OF BRIDGED MONOBACTAM INTERMEDIATES
  [FR] PROCÉDÉ DE FABRICATION D'INTERMÉDIAIRES DE MONOBACTAM PONTÉ

  摘要：

  一种制造具有顺式构象的化合物的方法，其中R1代表1-苯基-C1-C4烷基或1-萘基-C1-C4烷基基团，其中R1的苯基或萘基部分未取代或取代为一个或多个C1-C4烷氧基团，且R1的烷基部分中的第2、3和/或第4位的碳原子，独立于R1的苯基或萘基部分以及彼此独立地，未取代或取代为C1-C4烷氧基和/或硅氧烷基，或者更好地，未取代或取代为每个碳原子一个C1-C4烷氧基和/或硅氧烷基的R2代表C1-C6烷基或未取代或取代的苄基基团，在该方法中，将具有式（II）的化合物在液态非质子溶剂中以0°C或更低的温度用碱处理足够的时间，以获得式（I）的化合物。

  公开号：

  WO2009037229A1
• 作为产物：
  描述：

  tert-butyl (1S,5R)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate 在 pyridine-SO3 complex 作用下， 以 吡啶 为溶剂， 反应 1.5h， 生成 t-butyl (1S,5R)-7-oxo-6-sulfo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  [EN] PROCESS FOR THE MANUFACTURE OF BRIDGED MONOBACTAM INTERMEDIATES
  [FR] PROCÉDÉ DE FABRICATION D'INTERMÉDIAIRES DE MONOBACTAM PONTÉ

  摘要：

  一种制造具有顺式构象的化合物的方法，其中R1代表1-苯基-C1-C4烷基或1-萘基-C1-C4烷基基团，其中R1的苯基或萘基部分未取代或取代为一个或多个C1-C4烷氧基团，且R1的烷基部分中的第2、3和/或第4位的碳原子，独立于R1的苯基或萘基部分以及彼此独立地，未取代或取代为C1-C4烷氧基和/或硅氧烷基，或者更好地，未取代或取代为每个碳原子一个C1-C4烷氧基和/或硅氧烷基的R2代表C1-C6烷基或未取代或取代的苄基基团，在该方法中，将具有式（II）的化合物在液态非质子溶剂中以0°C或更低的温度用碱处理足够的时间，以获得式（I）的化合物。

  公开号：

  WO2009037229A1

文献信息

• Useful Combinations of Monobactam Antibiotics With Beta-Lactamase Inhibitors
  申请人：Desarbre Eric

  公开号：US20100056478A1

  公开（公告）日：2010-03-04

  A pharmaceutically composition, comprising a combination of an antibiotically active compound of the formula (I): with a β-lactamase inhibitor of one of the formulae (II) to (XIII) are active against Gram-negative bacteria, in particular such bacteria which have become resistant against antibiotics such as aztreonam, carumonam and tigemonam. Optionally the compositions may comprise another β-lactamase inhibitor of one of the formulae (II) to (XIII), particularly of formula (V) or formula (VI).

  一种药物组合物，包括公式（I）的抗生素活性化合物与公式（II）至（XIII）中的β-内酰胺酶抑制剂的组合，对革兰氏阴性菌具有活性，特别是对已经对阿奇霉素、卡鲁莫南和替吉奴等抗生素产生耐药性的细菌具有活性。该组合物还可以包含公式（II）至（XIII）中的另一种β-内酰胺酶抑制剂，特别是公式（V）或公式（VI）的β-内酰胺酶抑制剂。
• USEFUL COMBINATIONS OF MONOBACTAM ANTIBIOTICS WITH BETA-LACTAMASE INHIBITORS
  申请人：Basilea Pharmaceutica AG

  公开号：US20150031662A1

  公开（公告）日：2015-01-29

  A pharmaceutical composition, comprising a combination of an antibiotically active compound of the formula (I): with a β-lactamase inhibitor of one of the formulae (II) to (XIII) are active against Gram-negative bacteria, in particular such bacteria which have become resistant against antibiotics such as aztreonam, carumonam and tigemonam. Optionally the compositions may comprise another β-lactamase inhibitor of one of the formulae (II) to (XIII), particularly of formula (V) or formula (VI).

  一种药物组合物，包括式(I)的抗生素活性化合物与式(II)至式(XIII)中的一种β-内酰胺酶抑制剂的组合，对革兰氏阴性菌有活性，特别是对已经对阿奇霉素、卡鲁莫纳和替莫纳等抗生素产生耐药性的细菌有活性。该组合物可以包括另一种式(II)至式(XIII)中的β-内酰胺酶抑制剂，特别是式(V)或式(VI)的β-内酰胺酶抑制剂。
• Process for the preparation of 2-(primary/secondary amino)hydrocarbyl)-carbamoyl-7-oxo-2,6-diaza-bicyclo [3.2.0.]heptane-6-sulfonic acid derivatives
  申请人：Desarbe Eric

  公开号：US20100305315A1

  公开（公告）日：2010-12-02

  A process for the production of a compound of formula (I) wherein A LINKER B represents a linker moiety of formula (V): A [G1-G2*-G3] B ; wherein A and B indicate the orientation of the group of formula (V) in formula (I); G1, G2 and G3 have specific meanings described herein and may be present or absent, with the proviso that at least one of G1 or G3 is present; which linker group may furthermore optionally contain one or more groups of formula (VI); and/or other substituents; and R1 represents hydrogen or a C 1 -C 4 -alkyl group; R2 represents hydrogen or a C 1 -C 4 -alkyl group; R3 independently at each occurrence, represents hydrogen or a C 1 -C 4 -alkyl group; x is 0 or 1; y is 0 or 1; z independently at each occurrence, is 0 or 1; and (—) represents a single bond between a primary, secondary or tertiary carbon atom of the moiety A LINKER B and the adjacent nitrogen atom; in which process (A) a compound of formula (II) is reacted with a compound of formula (III) wherein Pr represents an amino protecting group selected from t-butyloxy carbonyl (t-Boc), 1-methyl-1-(4-biphenylyl)ethyloxy carbonyl (Bpoc), 1-(1-adamantyl)-1-methylethyloxy carbonyl (Adpoc), 1-(3,5-di-t-butylphenyl)-1-methylethyloxy carbonyl (t-Bumeoc), 1-adamantyloxy carbonyl (Adoc), p-methoxybenzyloxy carbonyl (Moz), o,p-dimethoxybenzyloxy carbonyl, A LINKER B has the same meaning as in formula (I) with the exception that one or more of the optional groups of formula (VII) may be replaced by a group of formula (VII) and R1; R2; R3; x; y; z and (—), at each occurrence, have the same meaning as in formula (I) and Pr is as defined above; in a dipolar aprotic solvent in the presence of a base to obtain a compound of formula (IV) wherein Pr; A LINKER B ; R1; R2; R3; x; y; z; and (—), at each occurrence, have the same meaning as in formula (III); which compound is then (B) deprotected by reaction with formic acid or a mixture of formic acid or acetic acid with hydrochloric acid or hydrobromic acid, to give the compound of formula (I) as well as the compounds of the aforementioned formula (IV).
• US8901293B2
  申请人：——

  公开号：US8901293B2

  公开（公告）日：2014-12-02
• US9346799B2
  申请人：——

  公开号：US9346799B2

  公开（公告）日：2016-05-24