pivaloyloxymethyl 6-(2-phenylacetamido)penicillanate | 25031-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: pivaloyloxymethyl 6-(2-phenylacetamido)penicillanate
• 英文别名: 2,2-dimethylpropanoyloxymethyl (2S,5R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 25031-07-6；54344-23-9
• 化学式: C₂₂H₂₈N₂O₆S
• 分子量: 448.54
• InChiKey: TVPADWYGPIXEDT-BSRYDQRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

制备方法与用途

化学性质：结晶（乙醇），熔点为113-115℃。

用途：作为匹呋氨苄青霉素的中间体。

生产方法：可通过青霉素G钾盐与特戊酸氯甲酯在碘化钠参与下进行酯化反应制得。

文献信息

• Beta-lactamase inhibiting 2-beta-substituted-2-alpha-methyl-(5R) penam-3-alpha-carboxylic acid 1,1-dioxides and intermediates therefor
  申请人：PFIZER INC.

  公开号：EP0074783A1

  公开（公告）日：1983-03-23

  Beta-lactamase inhibiting 2-beta-substituted-2-alphamethyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxides and esters thereof, wherein the 2-beta-substituent is cyano, acetyl, alkoxycarbonyl, omegahydroxyalkoxycarbonyl, car- balkoxymethoxycarbonyl or dialkylaminocarbonyl; intermediates therefor wherein the 2-beta-substituent is carboxy, chlorocarbonyl or aminocarbonyl; methods for their preparation and use as beta-lactamase inhibitors.

  抑制β-内酰胺酶的2-beta-取代基-2-樟脑甲基-(5R)戊-3-α-羧酸1,1-二氧化物及其酯类，其中2-beta-取代基为氰基、乙酰基、烷氧基羰基、ω-羟基烷氧基羰基、car- balkoxymoxycarbonyl或二烷基氨基羰基；其中2-beta-取代基为羧基、氯羰基或氨基羰基的中间体；其制备方法和作为β-内酰胺酶抑制剂的用途。
• 6-Alpha-hydroxymethylpenicillanic acid sulfone as a beta-lactamase inhibitor
  申请人：PFIZER INC.

  公开号：EP0083977A1

  公开（公告）日：1983-07-20

  6-alpha-hydroxymethylpenicillanic acid sulfone as a useful enhancer of the effectiveness of several beta-lactam antibiotics against many beta-lactamase producing bacteria, and 6-alpha-hydroxymethylpenicillanic acid sulfone benzyl ester as a useful intermediate leading to said agent which enhance the effectiveness of beta-lactam antibiotics.

  6-α-羟甲基青霉烷酸砜作为一种有用的增强剂，可增强几种β-内酰胺类抗生素对许多产β-内酰胺酶细菌的效力；6-α-羟甲基青霉烷酸砜苄酯作为一种有用的中间体，可产生上述增强β-内酰胺类抗生素效力的制剂。
• Penicillanic acid dioxide prodrug
  申请人：PFIZER INC.

  公开号：EP0095341A1

  公开（公告）日：1983-11-30

  A compound of the formula is a prodrug of 4,4-dioxopenicillanic acid, wherein R is hydrogen or methyl; R R2 and R3 (a) when taken individually are each alkyl containing one to four carbon atoms, or (b) when taken together with the nitrogen to which they are attached form a five- or six-membered saturated monocyclic moiety, an eight-membered saturated bicyclic moiety or a five- or six-membered aromatic cyclic moiety annulated with zero, one or two fused benzene rings, with the proviso that any Ri, R2 or R3 not part of a cyclic moiety is alkyl containing one to four carbon atoms; and X- is a pharmaceutically-acceptable anion. The prodrug can be included with a beta-lactam antibiotic in a pharmaceutical composition which can be employed in the treatment of infection in mammals. The above-described compounds hydrolyze in vivo to 4.4-dioxopenicillanic acid.

  式中的化合物 是 4,4-二氧代青霉烷酸的原药，其中 R 是氢或甲基；R R2 和 R3 (a) 单个时均为含 1 至 4 个碳原子的烷基，或 (b) 与所连接的氮一起形成五元或六元饱和单环分子、八元饱和双环分子或环有 0、1 或 2 个融合苯环的五元或六元芳香环分子，但任何不属于环分子的 Ri、R2 或 R3 均为含 1 至 4 个碳原子的烷基；X- 是药学上可接受的阴离子。该原药可与β-内酰胺类抗生素一起加入药物组合物中，用于治疗哺乳动物的感染。上述化合物在体内水解为 4.4-二氧代青霉烷酸。
• Penam-3-carboxylic acid 1,1-dioxides, process for their preparation and pharmaceutical compositions
  申请人：PFIZER INC.

  公开号：EP0008917B1

  公开（公告）日：1982-11-24
• US4241050A
  申请人：——

  公开号：US4241050A

  公开（公告）日：1980-12-23