【药物名称】Cefpirome, HR-810, Cefrom(sulfate), Broact(sulfate), Keiten(sulfate)
化学结构式(Chemical Structure):
参考文献No.9845
标题:Cephalosporin derivatives
作者:Lattrell, R.; Wieduwilt, M.; Duerckheimer, W.; Blumbach, J.; Seeger, K. (Aventis SA)
来源:EP 0064740; FR 2511682; FR 2515654; GB 2098216; JP 57192394; US 5071979
合成路线图解说明:

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.

合成路线图解说明:

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No.65156
标题:Cefpirome
作者:Casta馿r, J.; Serradell, M.N.
来源:Drugs Fut 1984,9(4),252
合成路线图解说明:

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.

合成路线图解说明:

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No.604475
标题:HR-810, a new parenteral cephalosporin with a broad antibacterial spectrum
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.
来源:Arzneim-Forsch Drug Res 1983,33(8),1084-1086
合成路线图解说明:

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.

合成路线图解说明:

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No.605765
标题:HR-810, a new parenteral cephalosporin. I. Chemistry and physical properties
作者:Klesel, N.; Seibert, G.; Lattrell, R.; Wieduwilt, M.; D黵ckheimer, W.; Kirrstetter, R.
来源:Int Con Chemother 1983,PS 4.2/11-1
合成路线图解说明:

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.

合成路线图解说明:

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

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