(R)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid | 69126-94-9

• 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: (R)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• 英文别名: (5R)-7-Oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• CAS: 69126-94-9
• 化学式: C₆H₅NO₃S
• 分子量: 171.177
• InChiKey: DUNKKIRUWZSMPT-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

文献信息

• BETA-LACTAMASE INHIBITORS
  申请人：SUTTON Larry

  公开号：US20100261700A1

  公开（公告）日：2010-10-14

  Broad spectrum beta-lactamase inhibitors. Certain inhibitors also exhibit potent antibiotic activity in addition to beta-lactamase inhibition. Compounds of the invention are designed such that on cleavage of the beta-lactam ring reactive moieties are generated which can inactivate beta-lactamase. Also provided are methods of making beta-lactamase inhibitors and beta-lactam antibiotics exhibiting such inhibition. Additionally provided are pharmaceutical compositions for treatment or prevention of bacterial infections and methods of treatment of such infections.

  广谱β-内酰胺酶抑制剂。某些抑制剂除了抑制β-内酰胺酶外，还表现出强效的抗生素活性。本发明的化合物设计成在β-内酰胺环裂解时生成可以灭活β-内酰胺酶的反应性基团。还提供了制备β-内酰胺酶抑制剂和表现出这种抑制作用的β-内酰胺类抗生素的方法。此外还提供了用于治疗或预防细菌感染的药物组合物和治疗此类感染的方法。
• Carbapenem derivatives having antibiotic activity, their preparation and their use
  申请人：Sankyo Company Limited

  公开号：EP0443883A1

  公开（公告）日：1991-08-28

  Carbapenem compounds of formula (I) : [in which : A is a fully saturated heterocyclic group, of which at least one ring atom is nitrogen ; R1 is hydrogen or methyl ; R2 is hydrogen or alkyl ; R3 is hydrogen or a negative ion; Q is: (i) -B-N+R8R9R10, where R8, R9 and R10 are alkenyl, alkynyl or optionally substituted alkyl, and B is alkylene or alkylidene ; (ii) a heterocyclic group of which one ring atom is a >N+R11R12, where R11 and R12 are alkenyl, alkynyl or optionally substituted alkyl ; (iii) alkyl substituted by a heterocyclic group as defined in (ii) above ; or (iv) alkyl substituted by an aromatic heterocyclic group, of which one ring atom is or R2 and Q, and the nitrogen to which they are attached, form a group of formula (II) : where m and n are 1, 2 or 3 ; R6 is optionally substituted alkyl ; and R7 is alkenyl, alkynyl or optionally substituted alkyl] and pharmaceutically acceptable salts and esters thereof have valuable antibacterial activity with enhanced resistance to dehydropeptidase I and β-lactamase. Methods of preparing and using the compounds are also provided.

  式(I)的碳青霉烯化合物：[其中：A是完全饱和的杂环基团，其中至少一个环原子是氮；R1是氢或甲基；R2是氢或烷基；R3是氢或负离子；Q是：(i)-B-N+R8R9R10，其中R8、R9和R10是烯基、炔基或可选取代的烷基，B是烷基或烷基亚甲基；(ii)杂环基团，其中一个环原子是>N+R11R12，其中R11和R12是烯基、炔基或可选取代的烷基；(iii)由(ii)中定义的杂环基团取代的烷基；或(iv)由一个芳香杂环基团取代的烷基，其中一个环原子是R2或Q，它们附着的氮形成式(II)的基团：其中m和n为1、2或3；R6是可选取代的烷基；R7是烯基、炔基或可选取代的烷基。其药学上可接受的盐和酯具有有价值的抗菌活性，并具有对脱氢肽酶I和β-内酰胺酶的增强抗性。还提供了制备和使用这些化合物的方法。
• Penem derivatives and antimicrobial agent containing the same
  申请人：Ishiguro Masaji

  公开号：US20050004092A1

  公开（公告）日：2005-01-06

  A penem derivative represented by the following formula (I): wherein R 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic thio group, a substituted or unsubstituted acylthio group, a mercapto group or a hydrogen atom, and R 2 represents a hydrogen atom or a carboxyl-protecting group; or a pharmacologically acceptable salt thereof. The compound (I) exhibits strong antibacterial activities, and especially, shows strong activities against MRSA. It is therefore useful not only as a general antibacterial agent but also as an antibacterial agent for MRSA against which no general antibacterial agents are recognized to be-effective.

  以下是公式（I）所代表的一种青霉烷衍生物： 其中，R1代表取代或未取代的烷基、取代或未取代的烯基、取代或未取代的芳基烷基、取代或未取代的芳基、取代或未取代的烷基硫基、取代或未取代的烯基硫基、取代或未取代的芳基烷基硫基、取代或未取代的芳基硫基、取代或未取代的杂环基、取代或未取代的杂环硫基、取代或未取代的酰基硫基、巯基或氢原子，R2代表氢原子或羧酸保护基；或其药学上可接受的盐。该化合物（I）表现出强大的抗菌活性，特别是对MRSA表现出强大的活性。因此，它不仅有用作一般抗菌剂，还有用作抗MRSA的抗菌剂，对于这种细菌，一般的抗菌剂被认为无效。
• 6- and 6,6- disubstituted-2-substituted-pen-2-em-3-carboxylic acids; processes for their preparation and pharmaceutical compositions containing such compounds
  申请人：Merck & Co., Inc.

  公开号：EP0002210A1

  公开（公告）日：1979-06-13

  Disclosed are 6- and 6.6-disubstituted-2-substituted-pen-2-em-3-carboxylic acids of the following structure: wherein: R1 and R2 are independently selected from hydrogen, -NHR1' (R1' is H or acyl), alkyl, alkoxyl. aralkyl, aryl. heterocyclyl and heterocycfyl-alkyl: R3 is selected from hydrogen, -R, -OR, -SR. -NR2; R is substituted and unsubstituted alkyl, aryl, aralkyl, hetero-heterocyclyl, or heterocyclylalkyl; n is 0 or 1: when n=1, R3 is not -SR. Such compounds and their pharmaceutically acceptable salt, and ester derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  本发明公开了具有以下结构的 6-和 6.6-二取代-2-取代-戊-2-烯-3-羧酸： 其中R1和R2独立地选自氢、-NHR1'（R1'为H或酰基）、烷基、烷氧基、芳基、杂环基和杂环烷基：R3 选自氢、-R、-OR、-SR.-NR2；R 是取代和未取代的烷基、芳基、烷基、杂杂环基或杂环烷基；n 是 0 或 1：当 n=1 时，R3 不是 -SR。此类化合物及其药学上可接受的盐和酯衍生物可用作抗生素。此外，还公开了制备此类化合物的工艺、包含此类化合物的药物组合物以及治疗方法，包括在需要抗生素效果时施用此类化合物和组合物。
• Process for the preparation of 2-penem compounds
  申请人：SCHERING CORPORATION

  公开号：EP0058317A1

  公开（公告）日：1982-08-25

  in which R1 is hydrogen, lower alkyl, acylamino, wherein R4 is hydrogen, lower alkyl, aryl or heteroaryl, R5 is hydrogen or an hydroxy protecting group, and R8 is halogen, , -SR9 (wherein R9 is lower alkyl, hydrogen or an -S protecting group), or the group in which one of R10 and R11 is an -N protecting group and the other is chosen from hydrogen, lower alkyl, aryl, aralkyl and acyl, or R10 and R11 are independently chosen from hydrogen, lower alkyl, aralkyl, aryl and acyl with the proviso that when one is hydrogen the other is acyl, R2 is lower alkyl, aryl, aralkyl, aminoalkyl, N-protected amino alkyl, hydroxyalkyl, O-protected hydroxyalkyl, thioalkyl, thioaryl, thioheteroaryl, an optionally esterfied a-amino acid residue, an optionally esterfied a-(N protected) amino acid residue or an optionally esterfied alkylcarboxy group; R3 is nitrile, tetrazolyl, or -COOR6 wherein R6 is hydrogen, the radical C(Hal)3 -Alk in which Hal is halogen and Alk represents an alkylene radical, lower alkyl, aryl, an allylic group, a metabolisable ester group, or a carboxy protecting group; X and Z are independently sulfur, oxygen, the radical =NR7 in which R7 is hydrogen, acyl, lower alkyl; aryl, or an N-protecting group, or -(CH2)n- in which n is 1 or 2; subject to the following provisos: (i) Z and X cannot simultaneously be(̵CH2)̵n in which n is 1 or 2; (ii) when X is S, Z is O or =NR7; (iii) when X is O, Z is O, S or =NR7; (iv) when X is -CH2-, Z is =NR7; except that when R7 is H or lower alkyl and R2 is lower alkyl then R1 cannot be acylamino; (v) when X is (̵CH2)̵2, Z is =NR7; and the pharmaceutically acceptable salts. Compounds of formula 1 are antibacterial agents which can be incorporated into pharmaceutical compositions or used as intermediates in the preparation of such agents.

  其中 R1 是氢、低级烷基、酰氨基、 其中 R4 是氢、低级烷基、芳基或杂芳基，R5 是氢或羟基保护基团，R8 是卤素、-SR9（其中 R9 是低级烷基、氢或-S 保护基团），或基团 其中 R10 和 R11 中的一个是-N 保护基团，另一个选自氢、低级烷基、芳基、烷基和酰基，或 R10 和 R11 独立选自氢、低级烷基、烷基、芳基和酰基，但其中一个为氢时，另一个为酰基、 R2 是低级烷基、芳基、芳烷基、氨基烷基、N 保护氨基烷基、羟基烷基、O 保护羟基烷基、硫代烷基、硫代芳基、硫代杂芳基、任选酯化的 a-氨基酸残基、任选酯化的 a-（N 保护）氨基酸残基或任选酯化的烷基羧基； R3 是腈、四唑基或-COOR6，其中 R6 是氢、自由基 C(Hal)3 -Alk （其中 Hal 是卤素，Alk 代表亚烷基、低级烷基、芳基、烯丙基、可代谢酯基或羧基保护基）； X 和 Z 独立地是硫、氧、自由基 =NR7（其中 R7 是氢、酰基、低级烷基、芳基或 N 保护基团）或-(CH2)n-（其中 n 是 1 或 2）；但书如下： (i) Z 和 X 不能同时为(̵CH2)̵n，其中 n 为 1 或 2； (ii) 当 X 为 S 时，Z 为 O 或 =NR7 (iii) 当 X 为 O 时，Z 为 O、S 或 =NR7 (iv) 当 X 为-CH2-时，Z 为 =NR7；但当 R7 为 H 或低级烷基且 R2 为低级烷基时，R1 不能为酰氨基； (v) 当 X 为 (̵CH2)̵2 时，Z 为 =NR7； 以及药学上可接受的盐类。式 1 的化合物是抗菌剂，可掺入药物组合物中或用作制备此类药物的中间体。