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药物详细合成路线

Name Cefotiam hydrochloride;SCE-963;CGP-14221/E;Abbott-48999;Pansporin;Halospor
Chemical Name 7beta-[2-(2-Imino-4-thiazolin-4-yl)acetamido]-3-[1-[2-(N,N-dimethylamino)ethyl]-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid dihydrochloride;(6R,7R)-7-[2-(2-Amino-4-thiazolyl)acetamido]-3-[[[1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydrochloride
CAS 66309-69-1
Related CAS 61622-34-2 (free acid)
Formula C18H25Cl2N9O4S3
Structure
Formula Weight 598.55585
Stage 上市-1981
Company Novartis (Originator), Takeda (Originator)
Activity/Mechanism Antibiotics, ANTIINFECTIVE THERAPY, Cephalosporins
Syn. Route 2
Route 1
the reaction of 7-beta-(d-5-phthalimido-5-carboxylvaleramido)-3-hydroxy-methyl-3-cephem-4-carboxylic acid (i) with diketene in ch2cl2 gives the 3-(3-oxobutyryloxy)methyl derivative (ii), which is treated with triethylamine-n,n-dimethylaniline, dimethyldichlososilane and pcl5 to obtain 7-beta-amino-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid (iii).the acylation of (iii) with 4-chloro-3-oxobutyryl chloride (a) and triethylamine in ch2cl2 affords the amide (iv), which is condensed with thiourea (b) by means of nahco3 in acetone yielding the thiazole derivative (v). finally, this compound is condensed with 5-mercapto-1-[2-(n,n-dimethylamino)ethyl-1h-tetrazole (vi) by means of nahco3 in hot water.
List of intermediates No.
methyl (1s,3as,4s,5s,7as)-4-(cyanomethyl)-7a-methyl-5-[(1r,3r,6r)-3-methyl-2-oxo-7-oxabicyclo[4.1.0]hept-3-yl]octahydro-1h-indene-1-carboxylate (b)
(3bs,4ar,5ar,6as,7as,7br,8ar,8bs)-6a-isopropyl-8b-methyl-3b,4,4a,7a,7b,8b,9,10-octahydrotrioxireno[2,3:6,7:2,3:8a,9:2,3:4b,5]phenanthro[1,2-c]furan-1,6(3h,6ah)-dione (a)
tert-butyl (1s,3s)-1-formyl-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentylcarbamate (iii)
benzyl 2-[3-(dimethylamino)phenoxy]acetate (i)
2-[3-(dimethylamino)phenoxy]acetic acid (ii)
(iv)
n-methoxy-n,6-dimethylnicotinamide (v)
diphenyl anilino(6-methyl-3-pyridinyl)methylphosphonate (vi)
Reference 1:
    tsushima, s.; et al. (takeda chemical industries, ltd.); novel 3-acyloxymethyl-cephem compounds useful as intermediates for preparing cephalosporin antibiotics. de 2607064; es 459261; fr 2301528; gb 1544103; us 4245088 .
Reference 2:
    blancafort, p.; serradell, m.n.; castaner, j.; roberts, p.j.; cefotiam. drugs fut 1979, 4, 6, 400.

Route 2
the condensation of 7-acetoacetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid (vii) with the mercaptane (vi) by means of nahco3 in hot water gives 7-beta-amino-3-[1-[2-(n,n-dimethylamino)ethyl]-1h-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (viii), which is then condensed with 2-aminothiazol-4-ylacetic acid (ix) by means of n-hydroxysuccinimide and dicyclohexylcarbodiimide in thf.the free amino group of (viii) is acylated with cl2 and diketene giving the 4-chloro-3-oxobutyramido derivative (x), which is finally cyclized with thiourea (b) by means of nahco3 in acetone.
List of intermediates No.
methyl (1s,3as,4s,5s,7as)-4-(cyanomethyl)-7a-methyl-5-[(1r,3r,6r)-3-methyl-2-oxo-7-oxabicyclo[4.1.0]hept-3-yl]octahydro-1h-indene-1-carboxylate (b)
diphenyl anilino(6-methyl-3-pyridinyl)methylphosphonate (vi)
chloro[4-(methylsulfanyl)benzyl]magnesium (vii)
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfanyl)phenyl]-1-ethanone (viii)
ethyl 2-[4-(methylsulfonyl)phenyl]acetate (x)
n-[(e)-1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethenyl]-n-phenylamine; n-[(e)-1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethenyl]aniline (ix)
Reference 1:
    numata, m.; et al. (takeda chemical industries, ltd.); 7-alpha-(2-aminothiazole)acetamidocephalosporins. de 2461478; fr 2255077; gb 1491018; nl 7416609; us 4080498; us 4421912; us 4517361 .
Reference 2:
    blancafort, p.; serradell, m.n.; castaner, j.; roberts, p.j.; cefotiam. drugs fut 1979, 4, 6, 400.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名头孢替安盐酸盐;英文名Cefotiam hydrochloride;SCE-963;CGP-14221/E;Abbott-48999;Pansporin;Halospor;CAS[66309-69-1]

 
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