Cefozopran hydrochloride, SCE-2787.HCl, Firstcin
盐酸头孢唑兰 头孢唑兰Chemical Name: [6R-[6alpha,7beta(Z)]]-1-[[7-[[(5-Amino-1,2,4-thiadiazol-3-yl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1H-imidazo[1,2-b]pyridazinium chloride; (6R,7R)-7-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2(Z)-(methoxyimino)acetamido]-3-(imidazo[1,2-b]pyridazinio-1-ylmethyl)-3-cephem-4-carboxylate hydrochloride
CAS No. 125905-00-2, 113981-44-5 (former CAS), 113359-04-9 (free base)
项目整合开发状态: Launched-1995
项目研究机构: Takeda (Originator)
合成路线: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.
📌 参考资料/链接：
参考文献标题:Antibacterial cpds.,their production and use
文献作者:Miyake,A.; Kondo,M.; Fujino,M.(Takeda Chemical Industries,Ltd.)
参考来源: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
📄 详细内容
合成路线:Alternatively,the title compound can be prepared by acylation of the imidazopyridazinium cephem derivative (IX) with acid chloride (II) in the presence of NaOAc.
参考文献标题:Process for the production of cephem cpds.
文献作者:Hamamura,K.; Shinohara,H.; Kodama,M.; Kuroda,H.(Eisai Co.,Ltd.)
参考来源:EP 0832893
合成路线: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.
参考文献标题:Cefozopran Hydrochloride
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1992,17(9),771
合成路线: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
文献作者:Miyake,A.; Yoshimura,Y.; Yamaoka,M.; Nishimura,T.; Hashimoto,N.; Imada,A.
参考来源:J Antibiot 1992,45(5),709-20
产品链接: CAS No.113981-44-5›› 产品链接: CAS No.113359-04-9››