Cefotetan disodium, ICI-156834(free acid), YM-09330, Cefotan, Apatef, Yamatetan, -Drug Synthesis Database

【结构式】

【药物名称】Cefotetan disodium, ICI-156834(free acid), YM-09330, Cefotan, Apatef, Yamatetan

【化学名称】7beta-[4-(Carbamoylcarboxylatomethylene)-1,3-dithietan-2-yl]carboxamido-7alpha-methoxy-3-(1-methyltetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid disodium salt
　　　　　　(6R,7S)-7-[4-(Carbamoylcarboxymethylene)-1,3-dithietane-2-carboxamido]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid disodium salt
　　　　　　[6R-(6alpha,7alpha)]-7-[[[4-(2-Amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid disodium salt

【CA登记号】69712-56-7 (free acid)

【分子式】C₁₇H₁₅N₇Na₂O₈S₄

【分子量】619.5868

【开发单位】AstraZeneca (Originator), Yamanouchi (Originator)

【药理作用】Cephalosporins

合成路线1

The condensation of 4-carboxy-3-hydroxy-5-mercaptoisothiazol (I) with 7beta-bromoacetamido-7alpha-methoxycephalosporanic acid (II) gives 7beta-(4-carboxy-3-hydroxyisothiazol-5-yl)thioacetamido-7alpha-methoxycephalosporanic acid (III), which by treatment with NaHCO3 in hot water is converted into 7beta-[4-(carbamoyl)(carboxy)methylene-1,3-dithietan-2-yl]carboxamido-7alpha-methoxycephalosporanic acid (IV). Finally, this compound is condensed with 5-mercapto-1-methyltetrazol (V) by means of Na2CO3 in water.

参考文献中间体

【1】 Iwanami, M.; Maeda, T.; Nagano, Y.; Fujimoto, M.; Nagano, N.; Yamazaki, A.; 7alpha-Methoxy-7beta-(1,3-dithietane-2-carboxamido)cephalosporanic acid derivatives. BE 0867994; DE 2824559; FR 2405952; NL 7806208; US 4263432; US 4404373 .
【2】 Blancafort, P.; Castaner, J.; Sweetman, A.J.; Serradell, M.N.; Cefotetan. Drugs Fut 1981, 6, 10, 609.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	32288	3-hydroxy-5-sulfanyl-4-isothiazolecarboxylic acid		C₄H₃NO₃S₂	详情	详情
(II)	31959	(6R,7S)-3-[(acetoxy)methyl]-7-[(2-bromoacetyl)amino]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-beta-bromoacetamido-7-alphamethoxycephalosporanic acid		C₁₃H₁₅BrN₂O₇S	详情	详情
(III)	32289	(6R,7S)-3-[(acetoxy)methyl]-7-([2-[(4-carboxy-3-hydroxy-5-isothiazolyl)sulfanyl]acetyl]amino)-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₇H₁₇N₃O₁₀S₃	详情	详情
(IV)	32290	(6R,7S)-3-[(acetoxy)methyl]-7-([[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino)-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₇H₁₇N₃O₁₀S₃	详情	详情
(V)	28420	5-Mercapto-1-methyl-1H-tetrazole; 1-Methyl-1H-1,2,3,4-tetraazol-5-ylhydrosulfide	13183-79-4	C₂H₄N₄S	详情	详情

Extended Information