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硫酸头孢匹罗的合成 被引量：3

Synthesis of Cefpirome Sulfate
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摘要 7-氨基头孢霉烷酸(7-ACA)和2,3-环戊烯并吡啶在三甲基碘硅烷催化下进行3-位取代反应,得到1-[[(6R,7R)-7-氨基-2-羧基-8-氧代-5-硫杂-1-氮杂二环[4.2.0]辛-2-烯-3-基]甲基]-6,7-二氢-5H-环戊烷并[b]吡啶内鎓盐(7-ACP)二氢碘酸盐,转化为盐酸盐后与苯并噻唑硫醇活性酯(MAEM)在三乙胺催化下缩合得到头孢匹罗,最后用硫酸成盐得到硫酸头孢匹罗,总收率约57%。 Cefpirome sulfate was synthesized by 3-substitution from 7-ACA and 2,3-cyclopentenopyridine using TMSI as catalyst to give 1- [ [ （6R,7R）-7-amino-2-carboxy-8-oxo-5-thia- 1-azabicyclo [4.2.0] oct-2-en-3-yl] methyl] - 6,7-dihydro-5H-cyclopenta[b]pyrindinium inner salt dihydroiodide, which underwent salt exchange with hydrochloric acid followed by condensation with S-benzothiazol-2-yl 2-（2-aminothiazol-4-yl）（methoxyimino）thioacetate（MAEM） in presence of Et3N and then formation of sulfate with an overall yield of about 57 %.
作者 杨阳 陈国华 罗小川 王先登
机构地区 中国药科大学药物化学教研室
出处 《中国医药工业杂志》 CAS CSCD 北大核心 2008年第7期483-484,496,共3页 Chinese Journal of Pharmaceuticals
关键词 硫酸头孢匹罗 头孢菌素 抗生素 合成 cefpirome sulfate cephalosporin antibiotic synthesis
分类号 R978.11 [医药卫生—药品]
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参考文献8

  • 1Strenkoski LC, Nix DE. Cefpirome clinical pharmacokinetics[J]. Clin Pharmacokinet, 1993, 25: 263-273.
  • 2王飞,林善良.硫酸头孢匹罗的合成[J].中国医药工业杂志,2005,36(8):455-456. 被引量：12
  • 3程冬萍,于文博,夏成才,颜继忠.头孢匹罗的合成[J].应用化工,2006,35(3):183-184. 被引量：7
  • 4Lattrell R, Blumbach J, Duerckheimer W, et al. Synthesis and structure-activity relationships in the cefpirome series. Ⅱ. Analogues of cefpirome with different 7-heteroarylacetamido and 3'-ammonium substituents [J]. J Antibiot (Tokyo), 1988, 41(10): 1374-1394.
  • 5Schwab W, Duerckheimer W, Kirrstetter R, et al. Process for the preparation of cephem compounds: US, 4667028[P]. 1987-05-19.(CA 1985, 102: 113174)
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二级参考文献11

  • 1Schwab W, Duerckheimer W, Rirrstetter R, et al. Process for the preparation of cephem compounds [P]. US: 4667028,1987-05-19; DE: 3316798, 1984-11-08. (CA 1985, 102:113174)
  • 2Lattrell R, Blumbach J, Duerckheimer W, et al. Synthesis and structure-activity relationships in the cefpirome series. Ⅰ. 7-[2- (2-Aminothiazol-4-yl) -2- (Z) -oxyiminoacetamido]-3-[ (substituted-1-pyridino) methyl]-ceph-3-em-4-carboxylates[J]. JAntibiot, 1988, 41 (10): 1374-1394.
  • 3Kirrstetter R, Duerckheimer W, Lattrell R, et al. Process for the manufacture of 3-pyridinium-methyl-cephalosporins [P].US: 4692516, 1987-09-08; DE: 3316797, 1984-11-08. (CA 1985, 102: 113173)
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  • 7Kirrstetter R,Duerkhelmer W.Process for the preparation of cephem compounds[P].DE:3316798,1983-11-08.
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  • 10Giorgio A,Antonio A,Gabriele B.Sequential amination/annulation/aromatization reaction of carbonyl compounds and propargylamine:A new one-pot approach to functionalized pyridines[J].J Org Chem,2003,68:6959-6966.

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中国医药工业杂志
2008年 第7期

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