tetra-n-butylammonium salt of penicillanic acid 1,1-dioxide

• 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: tetra-n-butylammonium salt of penicillanic acid 1,1-dioxide
• 英文别名: tetrabutylammonium salt of penicillanic acid 1,1-dioxide；4,4-dioxopenicillanic acid tetrabutylammonium salt；tetrabutylammonium penicillanate 1,1-dioxide；tetrabutylammonium 1,1-dioxopenicillanate；(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;tetrabutylazanium；(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;tetrabutylazanium
• 化学式: C₈H₁₀NO₅S*C₁₆H₃₆N
• 分子量: 474.706
• InChiKey: CNVADCOQWUDNHD-BCBTXJGPSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tetra-n-butylammonium salt of penicillanic acid 1,1-dioxide 生成 氯甲基(2S,5R)-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸酯4,4-二氧化物
  参考文献：
  名称：

  ADAMS, RICHARD C.

  摘要：

  DOI：
• 作为产物：
  描述：

  舒巴坦酸 在 四丁基氢氧化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 tetra-n-butylammonium salt of penicillanic acid 1,1-dioxide
  参考文献：
  名称：

  Process and intermediates for preparation of

  摘要：

  一种制备1,1-二氧代青霉烷酰氧甲基6-β-氨基青霉素酸酯的方法，包括在无水条件下，将1,1-二氧代青霉烷酰氧甲基6-苯乙酰胺青霉素酸酯或相应的苯氧乙酰胺青霉素酸酯与卤化剂在反应惰性溶剂的存在下反应，形成中间体亚胺卤化物，加入含有1至4个碳原子的初级醇将亚胺卤化物转化为亚胺醚，然后进行水解以得到所需的产物。

  公开号：

  US04530792A1

文献信息

• Derivatives of ampicillin and amoxicillin with beta-lactamase inhibitors
  申请人：Pfizer Inc.

  公开号：US04377590A1

  公开（公告）日：1983-03-22

  Certain beta-lactamase inhibitors which have a beta-lactam ring as well as a carboxy group have been linked through their carboxy group to either the amino group of ampicillin, the amino group of amoxicillin or the phenolic hydroxy group of amoxicillin. This affords novel antibacterial agents.

  某些β-内酰胺酶抑制剂具有β-内酰胺环和羧基，通过它们的羧基与氨苄青霉素的氨基、氨基苄青霉素的氨基或氨基苄青霉素的酚羟基相连，从而提供了新型抗菌剂。
• 1,1-Alkanediol dicarboxylate linked antibacterial agents
  申请人：Pfizer, Inc.

  公开号：US04457924A1

  公开（公告）日：1984-07-03

  Useful antibacterial agents in which a penicillin and/or a beta-lactamase inhibitor are linked via 1,1-alkanediol dicarboxylates are of the formula ##STR1## where A is the residue of certain dicarboxyic acids, R.sup.3 is H or (C.sub.1 -C.sub.3), n is zero or 1 such that when n is zero R is P or B and R.sup.1 is the residue of certain esters, H or a salt thereof; and when n is 1, one of R and R.sup.1 is P and the other is B, and P is ##STR2## where R.sup.2 is H or certain acyl groups, and B is the residue of a beta-lactamase inhibiting carboxylic acid; a method for their use, pharmaceutical compositions thereof and intermediates useful in their production.

  有用的抗菌剂，其中通过1,1-烷二醇二羧酸酯连接了青霉素和/或β-内酰胺酶抑制剂，其化学公式为##STR1##，其中A是某些二羧酸的残基，R.sup.3是H或(C.sub.1-C.sub.3)，n是0或1，当n为0时，R是P或B，R.sup.1是某些酯的残基，H或其盐；当n为1时，R和R.sup.1中的一个为P，另一个为B，P为##STR2##，其中R.sup.2是H或某些酰基团，B是β-内酰胺酶抑制羧酸的残基；其使用方法、药物组合物及其生产中有用的中间体。
• Bis-esters of dicarboxylic acids with amoxicillin and certain
  申请人：Pfizer Inc.

  公开号：US04462934A1

  公开（公告）日：1984-07-31

  Antibacterial bis-esters of 1,4-cyclohexanedicarboxylic acids and alkane dicarboxylic acids wherein the ester moieties are derived from different alcohols; one alcohol being hydroxymethylpenicillanate 1,1-dioxide, or the 6-beta-hydroxymethyl or the 6-alpha-aminomethyl derivative thereof; and the other being 6-[D-(2-amino-2-(p-hydroxyphenyl)acetamido)]penicillanic acid (amoxicillin); and pharmaceutically acceptable salts thereof; a method for the use of said esters and their salts, and methods for their preparation.

  1,4-环己二羧酸和烷二羧酸的抗菌双酯，其中酯基来源于不同的醇类；一种醇为羟甲基青霉素酸1,1-二氧化物，或其6-β-羟甲基或6-α-氨基甲基衍生物；另一种为6-[D-(2-氨基-2-(对羟基苯基)乙酰基)]青霉素酸（阿莫西林）；及其药用可接受盐；一种使用所述酯及其盐的方法，以及其制备方法。
• Process for the preparation of penicillanic acid esters
  申请人：Pfizer Inc.

  公开号：US04381263A1

  公开（公告）日：1983-04-26

  A process for the preparation of chloromethyl esters of penicillanic acids, using iodochloromethane or bromochloromethane and a tetraalkylammonium salt of the penicillanic acid, and their use in processes for the synthesis of penicillanic acid esters, using a halomethyl ester and the tetraalkylammonium salt of the penicillanic acid, which readily hydrolyze in vivo to antibacterial penicillins and the beta-lactamase inhibitor penicillanic acid sulfone.

  一种制备青霉素酸氯甲酯的方法，使用碘氯甲烷或溴氯甲烷和青霉素酸四烷基铵盐，以及它们在合成青霉素酸酯的过程中的应用，使用卤代甲酯和青霉素酸四烷基铵盐，这些酯在体内容易水解成抗菌青霉素和β-内酰胺酶抑制剂青霉素酸磺酮。
• Process for 6'-amino-penicillanoyloxymethyl penicillanate 1,1-dioxide
  申请人：Pfizer Inc.

  公开号：US04375434A1

  公开（公告）日：1983-03-01

  6'-Aminopenicillanoyloxymethyl penicillanate 1,1-dioxide is prepared by a two-step procedure. The first step consists of coupling a salt of a 6-(protected amino)penicillanic acid with a halomethyl, an alkylsulfonyloxymethyl or an arylsulfonyloxymethyl ester of penicillanic acid 1,1-dioxide, to give a 6'-(protected amino)penicillanoyloxymethyl penicillanate 1,1-dioxide, wherein the protection at the 6-position has been achieved by coupling the 6-aminopenicillanic acid with a beta-dicarbonyl compound. The second step consists of removal of the protecting group on the 6'-amino group, using aqueous acid. 6'-Aminopenicillanoyloxymethyl penicillanate 1,1-dioxide is a chemical intermediate for preparing antibacterial agents. Also claimed are the 6'-(protected amino)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds used as intermediates in the process of this invention.

  6'-氨基青霉素酰氧甲基青霉素酯1,1-二氧化物是通过两步法制备的。第一步包括将6-(保护氨基)青霉素酸的盐与青霉素酸1,1-二氧化物的卤甲基、烷基磺酰氧甲基或芳基磺酰氧甲基酯偶联，得到6'-(保护氨基)青霉素酰氧甲基青霉素酯1,1-二氧化物，其中6-位置的保护是通过将6-氨基青霉素酸与β-二羰基化合物偶联实现的。第二步包括使用水溶酸去除6'-氨基基团的保护基。6'-氨基青霉素酰氧甲基青霉素酯1,1-二氧化物是制备抗菌药物的化学中间体。还声明了作为本发明过程中间体使用的6'-(保护氨基)青霉素酰氧甲基青霉素酯1,1-二氧化物化合物。