6-(α-carboxy-α-phenylacetamido)penicillanic acid

• 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: 6-(α-carboxy-α-phenylacetamido)penicillanic acid
• 英文别名: 6-(2-carboxy-2-phenylacetamido)penicillanic acid；(2S,5R)-6-[(2-carboxy-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 化学式: C₁₇H₁₈N₂O₆S
• 分子量: 378.406
• InChiKey: FPPNZSSZRUTDAP-YXLKDIQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  8-苯基-6,10-二氧杂螺[4.5]癸烷-7,9-二酮 、 6-aminopenicillanic acid 生成 6-(α-carboxy-α-phenylacetamido)penicillanic acid
  参考文献：
  名称：

  Intermediates for preparing

  摘要：

  一种制备α-羧基-α-苯基（或3-噻吩基）青霉素和头孢菌素衍生物的新工艺被披露。该工艺包括将1,3-二氧六环四酮衍生物与所需的青霉素酸或头孢菌素酸衍生物反应。

  公开号：

  US04066664A1

文献信息

• 6-(2-Aryl-2-(1,1-dioxopenicillanoyloxy-methoxycarbonyl)acetamido) Penicillanic acids
  申请人：PFIZER INC.

  公开号：EP0055933A2

  公开（公告）日：1982-07-14

  6-[2-(1,1-Dioxopenicillanoyloxymethoxycarbonyl)-2-phenylacetamido]penicillanic acid, 6-[2-(1,1-dioxopenicil- lanoyloxymethoxycarbonyl)-2-(3-thienyl)acetamido]-penicillanic acid and salts thereof with pharmaceutically acceptabie bases; their use as antibacterial agents; processes and intermediates for their preparation,

  6-[2-(1,1-二氧代苯甲酰氧基甲氧基羰基)-2-苯乙酰胺基]青霉烷酸、6-[2-(1,1-二氧代苯甲酰氧基甲氧基羰基)-2-(3-噻吩基)乙酰胺基]-青霉烷酸及其与药学上可接受的碱的盐类；它们作为抗菌剂的用途；制备它们的工艺和中间体、
• 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。
• 6-Substituted penicillanic acid 1,1-dioxide compounds
  申请人：PFIZER INC.

  公开号：EP0181702A1

  公开（公告）日：1986-05-21

  @ A series of novel derivatives of penicillanic acid 1,1-dioxide, having a disubstituted methyl group of the formula X-CH-Y at the 6-position, and the pharmaceutically-acceptable salts thereof and the pharmaceutically-acceptable esters thereof readily hydrolyzable in vivo, wherein X is hydroxy, acylated hydroxy or amino and Y is carboxy or esterified carboxy. The compounds of the invention are inhibitors of bacterial beta-lactamases, and they will protect certain beta-lactamase-susceptible beta-lactam antibiotics, e.g. ampicillin, against inactivation by beta-lactamases. Co-administration of a compound of the invention with a beta-lactam antibiotic such as ampicillin to a mammalian subject increases the effectiveness of the beta-lactam antibiotic against infections caused by beta-lactamase-producing bacteria.

  一系列青霉烷酸 1,1-二氧化物的新型衍生物，其 6 位上有一个式 X-CH-Y 的二取代甲基，其药学上可接受的盐及其药学上可接受的酯在体内易于水解，其中 X 是羟基、酰化羟基或氨基，Y 是羧基或酯化羧基。本发明的化合物是细菌β-内酰胺酶的抑制剂，它们能保护某些易受β-内酰胺酶影响的β-内酰胺类抗生素（如氨苄西林）不被β-内酰胺酶灭活。哺乳动物在服用本发明化合物和β-内酰胺类抗生素（如氨苄西林）时，可提高β-内酰胺类抗生素对产β-内酰胺酶细菌引起的感染的疗效。