• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】CM-40874

【化学名称】7-[2-(2-Amino-4-thiazolyl)-2-[(2-carboxy-2-propoxy)imino]acetamido]-3-[[(1-allylpyridinium-2-yl)thio]methyl]-3-cephem-4-carboxylic acid 1-oxide bromide

【CA登记号】87286-08-6

【 分 子 式 】C25H27BrN6O8S3

【 分 子 量 】715.62534

【开发单位】Sanofi-synthélabo (Originator)

【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Cephalosporins

合成路线1

The condensation of 7-amino-3-bromomethyl-3-cephem-4-carboxylic acid tert-butyl ester 1-oxide (I) with 2-(2-tritylamino-4-thiazolyl)-2-[2-(tert-butoxycarbonyl)-2-propyloxyimino]acetic acid (II) by means of dicyclohexylcarbodiimide in CH2Cl2 gives the corresponding amide (III), which is treated with N-allyl-pyridine-2-thione (IV) in dimethylacetamide yielding the pyridinium salt (V). Finally, this compound is deprotected by a treatment with HCl in formic acid. The thione (IV) is prepared as follows: The reaction of 2-bromopyridine (VI) with allyl bromide (VII) in acetone gives N-allyl-2-bromopyridinium bromide (VIII), which is then treated with potassium hydrosulfide in water.

1 Labeeuw, B.; Salhi, A. (Sanofi-Synthelabo); Derivatives of pyridinium thiomethyl cephalosporins. EP 0088853; FR 2516515; JP 58090590; US 4593022 .
2 Serradell, M.N.; Matthews, R.; Castaner, J.; Burnie, J.; CM-40874. Drugs Fut 1985, 10, 3, 193.
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) 29048 tert-butyl 7-amino-3-(bromomethyl)-5,8-dioxo-5lambda(4)-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C12H17BrN2O4S 详情 详情
(II) 29047 2-[[2-(tert-butoxy)-1,1-dimethyl-2-oxoethoxy]imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid C32H33N3O5S 详情 详情
(III) 29049 tert-butyl 3-(bromomethyl)-7-([2-[[2-(tert-butoxy)-1,1-dimethyl-2-oxoethoxy]imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-5,8-dioxo-5lambda(4)-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C44H48BrN5O8S2 详情 详情
(IV) 29050 1-allyl-2(1H)-pyridinethione C8H9NS 详情 详情
(V) 29051 1-allyl-2-([[2-(tert-butoxycarbonyl)-7-([2-[[2-(tert-butoxy)-1,1-dimethyl-2-oxoethoxy]imino]-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-5,8-dioxo-5lambda(4)-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]sulfanyl)pyridinium bromide C52H57BrN6O8S3 详情 详情
(VI) 29052 2-Bromopyridine;α-bromopyridine;α-bromoazine 109-04-6 C5H4BrN 详情 详情
(VII) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(VIII) 29053 1-allyl-2-bromopyridinium bromide C8H9Br2N 详情 详情
Extended Information