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Cefpirome, HR-810, Cefrom(sulfate), Broact(sulfate), Keiten(sulfate)

头孢匹罗 硫酸头孢匹罗 Chemical Name: 1-[[(6R,7R)-7-[2-(2-Amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-5H-1-pyrindinium hydroxide,inner salt,7(2)-(Z)-(O-methyloxime); (6R,7R)-7-[2-(2-Aminothiazol-4-yl)-2(Z)-(methoxyimino)acetamido]-3-(6,7-dihydro-5H-pyrindinio-1-ylmethyl)-3-cephem-4-carboxylate
CAS No. 84957-29-9, 98753-19-6 (monosulfate)
项目整合开发状态: Launched-1992
项目研究机构: Aventis Pharma (Originator), Fujisawa (Licensee), Shionogi (Licensee)
合成路线:The protection of 7-aminocephalosporanic acid (I) with di-tert-butyl dicarbonate gives 7-(tert-butoxycarbonylamino)cephalosporanic acid (II),which is condensed with 2,3-cyclopentenopyridine (III) by means of KI and NaHCO3 in hot water affording 7-(tert-butoxycarbonylamino)-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (IV).Deprotection of (IV) with trifluoroacetic acid anisole gives 7-amino-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (V),which is finally condensed with 2-(2-aminothiazol-4-yl)-2-syn-methoxyiminoacetic acid (VI) by means of phosgene in toluene.

合成路线:By condensation of (III) with 7-[2-syn-methoxyimino-2-(2-aminothiazo)-4-yl(acetamido]cephalosporanic acid (VII) with KI and NaHCO3.
📌 参考资料/链接:
参考文献标题:Cephalosporin derivatives
文献作者:Lattrell,R.; Wieduwilt,M.; Duerckheimer,W.; Blumbach,J.; Seeger,K.(Aventis SA)
参考来源:EP 0064740; FR 2511682; FR 2515654; GB 2098216; JP 57192394; US 5071979

📄 详细内容


合成路线:The protection of 7-aminocephalosporanic acid (I) with di-tert-butyl dicarbonate gives 7-(tert-butoxycarbonylamino)cephalosporanic acid (II),which is condensed with 2,3-cyclopentenopyridine (III) by means of KI and NaHCO3 in hot water affording 7-(tert-butoxycarbonylamino)-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (IV).Deprotection of (IV) with trifluoroacetic acid anisole gives 7-amino-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (V),which is finally condensed with 2-(2-aminothiazol-4-yl)-2-syn-methoxyiminoacetic acid (VI) by means of phosgene in toluene.

合成路线:By condensation of (III) with 7-[2-syn-methoxyimino-2-(2-aminothiazo)-4-yl(acetamido]cephalosporanic acid (VII) with KI and NaHCO3.

参考文献标题:Cefpirome
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1984,9(4),252


合成路线:The protection of 7-aminocephalosporanic acid (I) with di-tert-butyl dicarbonate gives 7-(tert-butoxycarbonylamino)cephalosporanic acid (II),which is condensed with 2,3-cyclopentenopyridine (III) by means of KI and NaHCO3 in hot water affording 7-(tert-butoxycarbonylamino)-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (IV).Deprotection of (IV) with trifluoroacetic acid anisole gives 7-amino-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (V),which is finally condensed with 2-(2-aminothiazol-4-yl)-2-syn-methoxyiminoacetic acid (VI) by means of phosgene in toluene.

合成路线:By condensation of (III) with 7-[2-syn-methoxyimino-2-(2-aminothiazo)-4-yl(acetamido]cephalosporanic acid (VII) with KI and NaHCO3.

参考文献标题:HR-810,a new parenteral cephalosporin with a broad antibacterial spectrum
文献作者:Klesel,N.; D黵ckheimer,W.; Blumbach,J.; Lattrell,R.; Scheunemann,K.H.; Wieduwilt,M.; Schwab,W.; Ross,B.C.; Limbert,M.; Winkler,I.; Seibert,G.; Mencke,B.; Kirrstetter,R.; Seeger,K.; Schrinner,E.; Fleischmann,K.
参考来源:Arzneim-Forsch Drug Res 1983,33(8),1084-1086


合成路线:The protection of 7-aminocephalosporanic acid (I) with di-tert-butyl dicarbonate gives 7-(tert-butoxycarbonylamino)cephalosporanic acid (II),which is condensed with 2,3-cyclopentenopyridine (III) by means of KI and NaHCO3 in hot water affording 7-(tert-butoxycarbonylamino)-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (IV).Deprotection of (IV) with trifluoroacetic acid anisole gives 7-amino-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (V),which is finally condensed with 2-(2-aminothiazol-4-yl)-2-syn-methoxyiminoacetic acid (VI) by means of phosgene in toluene.

合成路线:By condensation of (III) with 7-[2-syn-methoxyimino-2-(2-aminothiazo)-4-yl(acetamido]cephalosporanic acid (VII) with KI and NaHCO3.
参考文献标题:HR-810,a new parenteral cephalosporin.I.Chemistry and physical properties
文献作者:Klesel,N.; Seibert,G.; Lattrell,R.; Wieduwilt,M.; D黵ckheimer,W.; Kirrstetter,R.
参考来源:Int Con Chemother 1983,PS 4.2/11-1


产品链接: CAS No. 84957-29-9››

产品链接: CAS No.98753-19-6››