pivaloyloxymethyl (1R,5S,6S)-2-{(3S,5S)-[5-N,N-dimethylaminocarbonyl-1-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl]pyrrolidin-3-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate

• 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 (1R,5S,6S)-2-{(3S,5S)-[5-N,N-dimethylaminocarbonyl-1-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl]pyrrolidin-3-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
• 英文别名: 2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)-1-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• 化学式: C₂₈H₃₉N₃O₁₀S
• 分子量: 609.698
• InChiKey: APFSLCASLLXQMG-VMCOHINHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  sodium (1R,5S,6S)-2-{(3S,5S)-[5-N,N-dimethylaminocarbonyl-1-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl]pyrrolidin-3-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate 、 特戊酸碘甲酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以370 mg的产率得到pivaloyloxymethyl (1R,5S,6S)-2-{(3S,5S)-[5-N,N-dimethylaminocarbonyl-1-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl]pyrrolidin-3-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
  参考文献：
  名称：

  Carbapenem compounds, use thereof, and intermediate compounds of the same

  摘要：

  一种具有如下式(I)的碳青霉烯化合物，其中R1是在体内可水解的基团，R2选自芳基（可选择性地取代1-3个含有1-4个碳原子的烷基基团）、1-烷酰氧基烷基、1-烷氧羰基氧基烷基、邻苯二甲酰基和5-甲基-2-氧代-1,3-二氧杂环戊烷-4-基甲基的基团，R3和R4是较低的烷基基团，可以相同也可以不同，或者与相邻的氮原子形成由azetidinyl、pyrrolidinyl和piperidinyl组成的4-至6-成员环氨基，或者其药用可接受盐。本发明的碳青霉烯化合物(I)及其药用可接受盐经口给药后显示出优越的消化道吸收性能，并对多种细菌种类具有足够的抗菌活性。因此，它们极其有用作为预防和治疗传染病的药物，特别是细菌性传染病。用于预防和治疗传染病的这些药物可以用作温血动物（例如人类、狗、猫、牛、马、大鼠、小鼠等）患由细菌引起的疾病（例如化脓性疾病、呼吸道感染性疾病、胆道炎症性疾病、尿路感染等）的预防和治疗药物。

  公开号：

  US06342494B1

文献信息

• Carbapenem compounds, use thereof, and intermediate compounds of the same
  申请人：Kyoto Pharmaceutical Industries, Ltd.

  公开号：US06342494B1

  公开（公告）日：2002-01-29

  A carbapenem compound of the formula (I) wherein R1 is a group hydrolyzable in the body, R2 is selected from the group consisting of aryl groups optionally substituted by 1-3 alkyl groups having 1-4 carbon atoms, 1-alkanoyloxyalkyl, 1-alkoxycarbonyloxyalkyl, phthalidyl and 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl, R3 and R4 are lower alkyl groups which may be the same or different or instead form a 4- to 6-membered cyclic amino with the adjacent nitrogen selected from the group consisting of azetidinyl, pyrrolidinyl and piperidinyl or a pharmaceutically acceptable salt thereof The carbapenem compound (I) and a pharmaceutically acceptable salt thereof of the present invention show superior absorption from digestive tract by oral administration, and sufficient antibacterial activity against a wide variety of bacterial species. Thus, they are extremely useful as agents for the prophylaxis and treatment of infectious diseases, particularly bacterial infectious diseases. Said agents for the prophylaxis and treatment of infectious diseases can be used as agents for the prophylaxis and treatment of the diseases caused by bacteria (e.g., suppurative diseases, respiratory infectious diseases, inflammatory diseases of biliary tract, urinary tract infection and the like) in warm-blooded animals inclusive of human (e.g., dog, cat, cow, horse, rat, mouse and the like).

  一种具有如下式(I)的碳青霉烯化合物，其中R1是在体内可水解的基团，R2选自芳基（可选择性地取代1-3个含有1-4个碳原子的烷基基团）、1-烷酰氧基烷基、1-烷氧羰基氧基烷基、邻苯二甲酰基和5-甲基-2-氧代-1,3-二氧杂环戊烷-4-基甲基的基团，R3和R4是较低的烷基基团，可以相同也可以不同，或者与相邻的氮原子形成由azetidinyl、pyrrolidinyl和piperidinyl组成的4-至6-成员环氨基，或者其药用可接受盐。本发明的碳青霉烯化合物(I)及其药用可接受盐经口给药后显示出优越的消化道吸收性能，并对多种细菌种类具有足够的抗菌活性。因此，它们极其有用作为预防和治疗传染病的药物，特别是细菌性传染病。用于预防和治疗传染病的这些药物可以用作温血动物（例如人类、狗、猫、牛、马、大鼠、小鼠等）患由细菌引起的疾病（例如化脓性疾病、呼吸道感染性疾病、胆道炎症性疾病、尿路感染等）的预防和治疗药物。