【药物名称】Cefozopran hydrochloride, SCE-2787.HCl, Firstcin
化学结构式(Chemical Structure):
参考文献No.3141
标题:Antibacterial cpds., their production and use
作者:Miyake, A.; Kondo, M.; Fujino, M. (Takeda Chemical Industries, Ltd.)
来源:AU 8541700; AU 8654168; EP 0160252; EP 0203271; ES 8606363; ES 8705892; ES 8706692; ES 8707245; JP 1985231684; JP 1987149682; WO 8504879; WO 8505620; WO 8605183; WO 8605184
合成路线图解说明:

This compound can be prepared by two related ways: 1) The condensation of (6R,7R)-7-amino-3-(3-oxobutyryloxy)-3-cephem-4-carboxylic acid (I) with 2-[5-(tert-butoxycarbonylamino)-1,2,4-thiadiazol-3-yl]-2(Z)-(methoxyimino)acetic acid (II), by means of PCl5 and bis(trimethylsilyl)acetamide (BSA) gives the corresponding amide (III), which is thencondensed with imidazo[1,2-b]pyridazine (IV) by means of KI in hot aqueous acetonitrile. 2) The condensation of 2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]-2(Z)-(methoxyimino)acetic acid (V) with cephem compound (I) by means of PCl5 and triethylamine yields the corresponding amide (VI), which is deprotected with trifluoroacetic acid to afford free amide (III), already obtained.

参考文献No.58266
标题:Process for the production of cephem cpds.
作者:Hamamura, K.; Shinohara, H.; Kodama, M.; Kuroda, H. (Eisai Co., Ltd.)
来源:EP 0832893
合成路线图解说明:

Alternatively, the title compound can be prepared by acylation of the imidazopyridazinium cephem derivative (IX) with acid chloride (II) in the presence of NaOAc.

参考文献No.181894
标题:Cefozopran Hydrochloride
作者:Prous, J.; Casta馿r, J.
来源:Drugs Fut 1992,17(9),771
合成路线图解说明:

This compound can be prepared by two related ways: 1) The condensation of (6R,7R)-7-amino-3-(3-oxobutyryloxy)-3-cephem-4-carboxylic acid (I) with 2-[5-(tert-butoxycarbonylamino)-1,2,4-thiadiazol-3-yl]-2(Z)-(methoxyimino)acetic acid (II), by means of PCl5 and bis(trimethylsilyl)acetamide (BSA) gives the corresponding amide (III), which is thencondensed with imidazo[1,2-b]pyridazine (IV) by means of KI in hot aqueous acetonitrile. 2) The condensation of 2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]-2(Z)-(methoxyimino)acetic acid (V) with cephem compound (I) by means of PCl5 and triethylamine yields the corresponding amide (VI), which is deprotected with trifluoroacetic acid to afford free amide (III), already obtained.

参考文献No.189568
标题:Studies on condensed-heterocyclic azolium cephalosporins. IV. Synthesis and antibacterial activity of 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-alkoxyiminoacetamido]-3-(condensed-heterocyclic azolium)methyl cephalosporins including SCE-2787
作者:Miyake,A.; Yoshimura, Y.; Yamaoka, M.; Nishimura, T.; Hashimoto, N.; Imada, A.
来源:J Antibiot 1992,45(5),709-20
合成路线图解说明:

This compound can be prepared by two related ways: 1) The condensation of (6R,7R)-7-amino-3-(3-oxobutyryloxy)-3-cephem-4-carboxylic acid (I) with 2-[5-(tert-butoxycarbonylamino)-1,2,4-thiadiazol-3-yl]-2(Z)-(methoxyimino)acetic acid (II), by means of PCl5 and bis(trimethylsilyl)acetamide (BSA) gives the corresponding amide (III), which is thencondensed with imidazo[1,2-b]pyridazine (IV) by means of KI in hot aqueous acetonitrile. 2) The condensation of 2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]-2(Z)-(methoxyimino)acetic acid (V) with cephem compound (I) by means of PCl5 and triethylamine yields the corresponding amide (VI), which is deprotected with trifluoroacetic acid to afford free amide (III), already obtained.

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