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Cefodizime, THR-221, HR-221, Timecef, Modivid, Diezime

头孢地嗪酸Chemical Name: [6R-[6alpha,7beta(Z)[[-7-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[[[5-(carboxymethyl)-4-methyl-2-thiazolyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[2-(2-Amino-4-thiazolyl)glyoxylamido]-3-[[[5-(carboxymethyl)-4-methyl-2-thiazolyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 7(2)-(Z)-(O-methyloxime)
CAS No. 69739-16-8
项目整合开发状态: Launched-1990
项目研究机构: Aventis Pharma (Originator), Lyphomed (Licensee), Taiho (Licensee)
合成路线:The condensation of 2-(methoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (I) with 7-aminocephalosporanic acid (II) by means of dicyclohexylcarbodiimide in CH2Cl2 gives 7-[2-(methoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]cephalosporanic acid (III),which is deprotected by means of formic acid in water yielding 7-[2-(methoxyimino)-2-(2-aminothiazol-4-yl)acetamido]cephalosporanic acid (IV).Finally,this compound is condensed with 5-(carboxymethyl)-2-mercapto-4-methyl-1,3-thiazole (V) by means of NaHCO3 or NaOH in hot water.
📌 参考资料/链接:
参考文献标题:Cephem derivative
文献作者:Duerckeimer,W.; et al.(Aventis Pharma AG)
参考来源:BE 0865632; FR 2385722; GB 1604971; JP 5706887; US 4278793

📄 详细内容


合成路线:Using a different protection strategy,aminoacid (IV) was protected as the N-phenylacetyl derivative (VII) by treatment with acid chloride (VI).Subsequent DCC-mediated coupling with the cephem derivative (III) furnished (VIII).The N-phenylacetyl group was then selectively removed by enzymatic hydrolysis with penicillin G amidase.

参考文献标题:A method for the acylation of the 7-amino group of the cephalosporanic ring
文献作者:Zenoni,M.; Fuganti,C.
参考来源:EP 0582102


合成路线:In a further procedure,2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetic acid (IV) was activated as the mixed anhydride (V) by treatment with tosyl chloride and triethylamine.After protection of the cephem thioether (III) by silylation with either chlorotrimethylsilane or with bis(trimethylsilyl)acetamide,coupling with the mixed anhydride (V) gave rise to the title compound.

参考文献标题:Process for the preparation of cefodizime
文献作者:Wagner,H.; Jaenicke,O.; Worm,M.(Aventis Pharma AG)
参考来源:EP 0226093


合成路线:The condensation of 2-(methoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (I) with 7-aminocephalosporanic acid (II) by means of dicyclohexylcarbodiimide in CH2Cl2 gives 7-[2-(methoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]cephalosporanic acid (III),which is deprotected by means of formic acid in water yielding 7-[2-(methoxyimino)-2-(2-aminothiazol-4-yl)acetamido]cephalosporanic acid (IV).Finally,this compound is condensed with 5-(carboxymethyl)-2-mercapto-4-methyl-1,3-thiazole (V) by means of NaHCO3 or NaOH in hot water.

参考文献标题:Cefodizime
文献作者:Serradell,M.N.; Castar,J.
参考来源:Drugs Fut 1984,9(3),177


合成路线:The condensation of 2-(methoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (I) with 7-aminocephalosporanic acid (II) by means of dicyclohexylcarbodiimide in CH2Cl2 gives 7-[2-(methoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]cephalosporanic acid (III),which is deprotected by means of formic acid in water yielding 7-[2-(methoxyimino)-2-(2-aminothiazol-4-yl)acetamido]cephalosporanic acid (IV).Finally,this compound is condensed with 5-(carboxymethyl)-2-mercapto-4-methyl-1,3-thiazole (V) by means of NaHCO3 or NaOH in hot water.

合成路线:Displacement of the acetate group of 7-aminocephalosporanic acid (I) with the mercapto thiazole (II) yielded thioether (III).This was then acylated with 2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetic acid (IV) in the presence of DCC and HOBt to furnish the corresponding amide.
参考文献标题:Results of a multicenter phase III trial of magnetic resonance angiography (MRA) with MS-325 for the detection of peripheral vascular disease in the aortolliac region
文献作者:Wolff,S.; et al.
参考来源:Circulation 2002,106(19,Suppl.2),Abst 3408


产品链接: CAS No. 69739-16-8››