(6R,7R)-7-amino-3-[[(3-carbamoyl-5-methylpyrazolo[1,5-a]-pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid

• 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: (6R,7R)-7-amino-3-[[(3-carbamoyl-5-methylpyrazolo[1,5-a]-pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: (6R,7R)-7-amino-3-[[(3-carbamoyl-5-methylpyrazolo[1,5-a]-pyrimidin-7-yl) thio]methyl]-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid；(6R,7R)-7-amino-3-[(3-carbamoyl-5-methylpyrazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 化学式: C₁₆H₁₆N₆O₄S₂
• 分子量: 420.473
• InChiKey: GQMBLYZBRLINDL-MEBBXXQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  208
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  、 7-氨基头孢烷酸 、 、 三氟化硼 、 sodium hydroxide 以 乙腈 、 水 为溶剂， 反应 0.67h， 以There was obtained (6R,7R)-7-amino-3-[[(3-carbamoyl-5-methylpyrazolo[1,5-a]-pyrimidin-7-yl) thio]methyl]-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid的产率得到(6R,7R)-7-amino-3-[[(3-carbamoyl-5-methylpyrazolo[1,5-a]-pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Intermediates for cephalosporins with sulfur-containing oxyimino side

  摘要：

  化合物的抗菌成分的公式为##STR1##其中R是单核芳香碳环基团，5-成员芳香杂环基团，其中包含杂（非碳）环成员的氧或硫原子或亚胺或低烷基亚胺基团，并且可选地包含一个或两个氮原子，或者是包含1至3个氮原子的6-成员芳香杂环基团；R.sup.1是氢或可用于头孢菌素化学的3-取代基；A是低烷基或C.sub.3-7-环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基；Q是低烷基或C.sub.3-7-环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基，或者是--NR.sup.2--或--NR.sup.2NR.sup.3--基团；R.sup.2和R.sup.3独立地是氢或低烷基；p和m为0或1，n为0、1或2；R.sup.4是氢，低烷酰基或三（低烷基）硅基；两个R.sup.4基团一起代表二苯甲基；R.sup.5是氢，低烷基，羟基，低烷氧基，卤素，硝基，--OCOR.sup.7，--OCOOR.sup.71，--N（R.sup.7）.sub.2，--NHCOR.sup.7，--NHCOOR.sup.71，--COR.sup.7，--SR.sup.7，--SOR.sup.7，--SO.sub.2R.sup.7，--SO.sub.3H，--COOR.sup.7或--CON（R.sup.7）.sub.2；R.sup.6是氢，低烷基或卤素，R.sup.7是氢或低烷基；R.sup.71是低烷基，两个--OR.sup.4基团通过相邻碳原子连接到苯环上，以及这些化合物的容易水解的酯和药学上可接受的盐以及公式I和它们的酯和盐的化合物和水合物。

  公开号：

  US05138066A1

文献信息

• Cephalosporins with sulfur-containing oxyimino side chain
  申请人：Hoffmann-La Roche Inc.

  公开号：US05036064A1

  公开（公告）日：1991-07-30

  Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hetero (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hetero ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl, or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.4 is hydrogen, lower alkanoyl or tri(lower alkyl)silyl; two R.sup.4 groups together represent diphenylmethylene; R.sup.5 is hydrogen, lower alkyl, hydroxy, lower alkoxy, halogen, nitro, --OCOR.sup.7, --OCOOR.sup.71, --N(R.sup.7).sub.2, --NHCOR.sup.7, --NHCOOR.sup.71, --COR.sup.7, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --SO.sub.3 H, --COOR.sup.7 or --CON(R.sup.7).sub.2 ; R.sup.6 is hydrogen, lower alkyl or halogen, R.sup.7 is hydrogen or lower alkyl; R.sup.71 is lower alkyl, and the two --OR.sup.4 groups are attached to the phenyl ring via adjacent carbon atoms, as well as readily hydrolyzable esters and pharmaceutically acceptable salts of these compounds and hydrates of compounds of formula I and of their esters and salts.

  式子为##STR1##的抗菌化合物，其中R是单核芳香碳环基团，5元杂环芳香基团，其中包含作为杂原子（非碳）环成员的氧或硫原子或亚胺或低烷基亚胺基团，以及可选地，一个或两个氮原子，或者是含有一个到三个氮原子作为杂环成员的6元杂环芳香基团；R.sup.1是氢或可用于头孢菌素化学的3-取代基；A是低烷基或C.sub.3-7-环烷基，它可选地被羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基取代；Q是低烷基或C.sub.3-7-环烷基，它可选地被羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基取代，或者是--NR.sup.2 --或--NR.sup.2 NR.sup.3 --基团；R.sup.2和R.sup.3独立地是氢或低烷基；p和m为零或1，n为零，1或2；R.sup.4是氢，低烷酰基或三（低烷基）硅基；两个R.sup.4基团共同代表二苯基甲烯基；R.sup.5是氢，低烷基，羟基，低烷氧基，卤素，硝基，--OCOR.sup.7，--OCOOR.sup.71，--N（R.sup.7）.sub.2，--NHCOR.sup.7，--NHCOOR.sup.71，--COR.sup.7，--SR.sup.7，--SOR.sup.7，--SO.sub.2 R.sup.7，--SO.sub.3 H，--COOR.sup.7或--CON（R.sup.7）.sub.2；R.sup.6是氢，低烷基或卤素，R.sup.7是氢或低烷基；R.sup.71是低烷基，而两个--OR.sup.4基团通过相邻的碳原子连接到苯环上，以及这些化合物的容易水解的酯和药学上可接受的盐以及式I和它们的酯和盐的化合物的水合物。
• Cephalosphorins with sulfur-containing oxyimino side chain
  申请人：Hoffmann-La Roche Inc.

  公开号：US05073550A1

  公开（公告）日：1991-12-17

  Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hetero (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hetero ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di-(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl, or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.4 is hydrogen, lower alkanoyl or tri(lower alkyl)silyl; two R.sup.4 groups together represent diphenylmethylene; R.sup.5 is hydrogen, lower alkyl, hydroxy, lower alkoxy, halogen, nitro, --OCOR.sup.7, --OCOOR.sup.71, --N(R.sup.7).sub.2, --NHCOR.sup.7, --NHCOOR.sup.71, --COR.sup.7, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --SO.sub.3 H, --COOR.sup.7 or --CON(R.sup.7).sub.2 R.sup.6 is hydrogen, lower alkyl or halogen, R.sup.7 is hydrogen or lower alkyl; R.sup.71 is lower alkyl, and the two --OR.sup.4 groups are attached to the phenyl ring via adjacent carbon atoms, as well as readily hydrolyzable esters and pharmaceutically acceptable salts of these compounds and hydrates of compounds of formula I and of their esters and salts.

  化合物的抗菌化合物公式为##STR1##其中R是单核芳香环烃基，5-成员芳香杂环基，其包含氧或硫原子或亚胺或低烷基亚胺基作为杂（非碳）环成员，可选地含有一个或两个氮原子，或者是含有一个到三个氮原子作为杂环成员的6-成员芳香杂环基; R.sup.1是氢或可在头孢菌素化学中使用的3-取代基; A是低烷基或C.sub.3-7环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基; Q是低烷基或C.sub.3-7环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基，或者是--NR.sup.2 --或--NR.sup.2 NR.sup.3 --基团; R.sup.2和R.sup.3独立地是氢或低烷基; p和m为零或1，n为零，1或2; R.sup.4是氢，低烷酰基或三（低烷基）硅基; 两个R.sup.4基团共同代表二苯基甲烯基; R.sup.5是氢，低烷基，羟基，低烷氧基，卤素，硝基，--OCOR.sup.7，--OCOOR.sup.71，--N（R.sup.7）.sub.2，--NHCOR.sup.7，--NHCOOR.sup.71，--COR.sup.7，--SR.sup.7，--SOR.sup.7，--SO.sub.2 R.sup.7，--SO.sub.3 H，--COOR.sup.7或--CON（R.sup.7）.sub.2 R.sup.6是氢，低烷基或卤素，R.sup.7是氢或低烷基; R.sup.71是低烷基，两个--OR.sup.4基团通过相邻的碳原子连接到苯环上，以及这些化合物的易水解酯和药学上可接受的盐以及公式I和其酯和盐的化合物和水合物。
• Intermediates for cephalosporins with sulfur containing oxyimino side
  申请人：Hoffmann-La Roche Inc.

  公开号：US05319140A1

  公开（公告）日：1994-06-07

  Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hereto (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hereto ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.4 is hydrogen, lower alkanoyl or tri(lower alkyl)silyl; two R.sup.4 groups together represent diphenylmethylene; R.sup.5 is hydrogen, lower alkyl, hydroxy, lower alkoxy, halogen, nitro, --OCOR.sup.7, --OCOOR.sup.71, --N(R.sup.7).sub.2, --NHCOR.sup.7, --NHCOOR.sup.71, --COR.sup.7, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --SO.sub.3 H, --COOR.sup.7 or --CON(R.sup.7).sub.2 ; R.sup.6 is hydrogen, lower alkyl or halogen, R.sup.7 is hydrogen or lower alkyl; R.sup.71 is lower alkyl, and the two --OR.sup.4 groups are attached to the phenyl ring via adjacent carbon atoms, as well as readily hydrolyzable esters and pharmaceutically acceptable salts of these compounds and hydrates of compounds of formula I and of their esters and salts.

  公式为 ##STR1## 的抗菌化合物，其中 R 是单核芳香烃基，5-成员芳香杂环基，其中含有氧或硫原子或亚胺或低烷基亚胺基作为其（非碳）环成员，可选地含有一或两个氮原子，或6-成员芳香杂环基，其中含有一到三个氮原子作为其环成员; R.sup.1 是氢或可用于头孢菌素化学中的3-取代基; A 是低烷基或C.sub.3-7-环戊烷基，可选地取代为羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基; Q 是低烷基或C.sub.3-7-环戊烷基，可选地取代为羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基或基团--NR.sup.2--或--NR.sup.2NR.sup.3--; R.sup.2 和 R.sup.3 分别是氢或低烷基; p 和 m 为零或1，n 为零、1或2; R.sup.4 是氢、低烷酰基或三（低烷基）硅基; 两个 R.sup.4 组成二苯甲基; R.sup.5 是氢、低烷基、羟基、低烷氧基、卤素、硝基、--OCOR.sup.7、--OCOOR.sup.71、--N(R.sup.7).sub.2、--NHCOR.sup.7、--NHCOOR.sup.71、--COR.sup.7、--SR.sup.7、--SOR.sup.7、--SO.sub.2R.sup.7、--SO.sub.3H、--COOR.sup.7或--CON(R.sup.7).sub.2; R.sup.6 是氢、低烷基或卤素，R.sup.7 是氢或低烷基; R.sup.71 是低烷基，两个--OR.sup.4基通过相邻碳原子连接到苯环上，以及这些化合物的容易水解的酯和药学上可接受的盐以及公式I和其酯和盐的化合物和水合物。
• Intermediates for cephalosporins with sulfur-containing oxyimino side
  申请人：Hoffmann-La Roche, Inc.

  公开号：US05138066A1

  公开（公告）日：1992-08-11

  Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hetero (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hetero ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl, or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.4 is hydrogen, lower alkanoyl or tri(lower alkyl)silyl; two R.sup.4 groups together represent diphenylmethylene; R.sup.5 is hydrogen, lower alkyl, hydroxy, lower alkoxy, halogen, nitro, --OCOR.sup.7, --OCOOR.sup.71, --N(R.sup.7).sub.2, --NHCOR.sup.7, --NHCOOR.sup.71, --COR.sup.7, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --SO.sub.3 H, --COOR.sup.7 or --CON(R.sup.7).sub.2 ; R.sup.6 is hydrogen, lower alkyl or halogen, R.sup.7 is hydrogen or lower alkyl; R.sup.71 is lower alkyl, and the two --OR.sup.4 groups are attached to the phenyl ring via adjacent carbon atoms, as well as readily hydrolyzable esters and pharmaceutically acceptable salts of these compounds and hydrates of compounds of formula I and of their esters and salts.

  化合物的抗菌成分的公式为##STR1##其中R是单核芳香碳环基团，5-成员芳香杂环基团，其中包含杂（非碳）环成员的氧或硫原子或亚胺或低烷基亚胺基团，并且可选地包含一个或两个氮原子，或者是包含1至3个氮原子的6-成员芳香杂环基团；R.sup.1是氢或可用于头孢菌素化学的3-取代基；A是低烷基或C.sub.3-7-环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基；Q是低烷基或C.sub.3-7-环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基，或者是--NR.sup.2--或--NR.sup.2NR.sup.3--基团；R.sup.2和R.sup.3独立地是氢或低烷基；p和m为0或1，n为0、1或2；R.sup.4是氢，低烷酰基或三（低烷基）硅基；两个R.sup.4基团一起代表二苯甲基；R.sup.5是氢，低烷基，羟基，低烷氧基，卤素，硝基，--OCOR.sup.7，--OCOOR.sup.71，--N（R.sup.7）.sub.2，--NHCOR.sup.7，--NHCOOR.sup.71，--COR.sup.7，--SR.sup.7，--SOR.sup.7，--SO.sub.2R.sup.7，--SO.sub.3H，--COOR.sup.7或--CON（R.sup.7）.sub.2；R.sup.6是氢，低烷基或卤素，R.sup.7是氢或低烷基；R.sup.71是低烷基，两个--OR.sup.4基团通过相邻碳原子连接到苯环上，以及这些化合物的容易水解的酯和药学上可接受的盐以及公式I和它们的酯和盐的化合物和水合物。
• US5036064A
  申请人：——

  公开号：US5036064A

  公开（公告）日：1991-07-30