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藥物詳細合成路線

Name Salbutamol sulfate;Albuterol sulfate;AH-3365;Pediavent;Ventoline;Ventolin;Proventil-HFA;Proventil;Volmax;Ventolin easy-breathe;Salbutamol Diskus;Proventil Repetabs;Ventolin Nebules;Buventol Easyhaler;Accuvent;Pulvinal salbutamol;Sultanol;
Chemical Name alpha1-[(tert-Butylamino)methyl]-4-hydroxy-m-xylene-alpha,alpha-diol sulfate (2:1)
      alpha1-(1,1-Dimethylethylaminomethyl)-4-hydroxy-1,3-benzenedimethanol sulfate (2:1)
CAS 51022-70-9
Related CAS 18559-94-9 (free base)
Formula C26H44N2O10S
Structure
Formula Weight 576.71198
Stage 上市-1968
Company GlaxoSmithKline (Originator), 3M Pharmaceuticals (Not Determined), Ascent (Not Determined), Dey (Not Determined), Orion Corp. (Not Determined), Schering-Plough (Not Determined), Trinity Pharmaceuticals (Not Determined), Zambon (Not Determined), Ivax (Form
Activity/Mechanism Asthma Therapy, Bronchodilators, Chronic Obstructive Pulmonary Diseases (COPD), Treatment of, RESPIRATORY DRUGS, beta2-Adrenoceptor Agonists
Syn. Route 2
Route 1
the reaction of methyl 5-bromoacetylsalicylate (i) with benzyl tert-butylamine (ii) in methyl ethyl ketone gives methyl 5-(n-benzyl-n-tert-butyl-gycyl)salicylate (iii), which is reduced with lialh4 in refluxing thf yielding alpha-(n-benzyl-n-tert-butylami-nomethyl)-4-hydroxy-m-xylene-alpha,alpha-diol (iv). finally, this compound is debenzylated by hydrogenation with h2 over pd/c in ethanol-water.
List of intermediates No.
ethyl 7-hydroxy-4-oxo-8-propyl-4h-chromene-2-carboxylate (ii)
1,1-dimethyl-2-propynyl 2-oxo-2-phenylacetate (i)
(1r,4r,6r)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (iii)
(1r,2s,4s,6r)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-ol (iv)
Reference 1:
    castaner, j.; blancafort, p.; serradell, m.n.; hopkins, s.j.; albuterol. drugs fut 1979, 4, 9, 629.
Reference 2:
    lunts, l.h.c.; et al.; gb 1200886 .

Route 2
the chloromethylation of 4-hydroxyacetophenone (v) with formaldehyde and hcl in hot water gives 3-chloromethyl-4-hydroxyacetophenone (vi), which is treated with acetic anhydride-sodium acetate in refluxing acetic acid to afford 3-acetoxymethyl-4-acetoxyacetophenone (vii). the bromination of (vii) with br2 in chloroform yields after hydrolysis 3-hydroxymethyl-4-hydroxyphenacyl bromide (viii), which is condensed with benzyl tert-butylamine (ii) in refluxing benzene giving alpha-(n-benzyl-n-tert-butylamino)-4-hydroxy-3-hydroxymethylacetophenone (ix). finally, this compound is hydrogenated with h2 over pd/c in ethanol.an alternative method of hydrogenation of (ix) is its reduction with nabh4 - ethanol, to afford the previously obtained product (iv), which is reduced with h2 over pd/c in ethanol.
List of intermediates No.
4-[(e)-3,3-dimethyl-1-triazenyl]benzoic acid (v)
ethyl 7-hydroxy-4-oxo-8-propyl-4h-chromene-2-carboxylate (ii)
(1r,2s,4s,6r)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-ol (iv)
(1r,3s,5s,6s)-5-hydroxy-6-methyl-7-oxabicyclo[4.1.0]hept-3-yl acetate (vi)
(1s,2s,4s,6r)-1-methyl-7-oxabicyclo[4.1.0]heptane-2,4-diol (vii)
tert-butyl[((1r,2s,4r,6r)-4-[[tert-butyl(dimethyl)silyl]oxy]-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl)oxy]dimethylsilane; tert-butyl(dimethyl)silyl (1r,2s,4r,6r)-4-[[tert-butyl(dimethyl)silyl]oxy]-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl ether (viii)
(3s,5s)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-oxoheptanal (ix)
Reference 1:
    lunts, l.h.c.; et al.; gb 1200886 .
Reference 2:
    castaner, j.; blancafort, p.; serradell, m.n.; hopkins, s.j.; albuterol. drugs fut 1979, 4, 9, 629.
Reference 3:
    collin, d.t.; et al.; saligenin analogs of sympathomimetic catecholamines. j med chem 1970, 13, 4, 674-680.

來源:藥化網

作者:藥化小編

摘要:本文合成路線介紹的是藥物中文名硫酸沙丁胺醇;英文名Salbutamol sulfate;Albuterol sulfate;AH-3365;Pediavent;Ventoline;Ventolin;Proventil-HFA;Proventil;Volmax;Ventolin easy-breathe;Salbutamol Diskus;Proventil Repetabs;Ventolin Nebules;Buventol Easyhaler;Accuvent;Pulvinal salbutamol;Sultanol;;CAS[51022-70-9]

 
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