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药物详细合成路线

Name Zolpidem tartrate;SL-80-0750-23N;Myslee;Stilnoct;Ivadal;Ambien;Bikalm;Niotal;Stilnox
Chemical Name N,N,6-Trimethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetamide L-(+)-tartrate (2:1)
CAS 99294-93-6
Related CAS 82626-48-0 (free base)
Formula C23H27N3O7
Structure
Formula Weight 457.48754
Stage 上市-1988
Company Sanofi-synthélabo (Originator), Altana Pharma (Licensee), Fujisawa (Licensee), Lorex (Licensee), Biovail (Formulation)
Activity/Mechanism PSYCHOPHARMACOLOGIC DRUGS, Sedative/Hypnotics, Sleep Disorders, Treatment of, Benzodiazepines, GABA(A) BZ Site Receptor Agonists
Syn. Route 2
Route 1
a new and industrially viable synthesis of zolpidem has been described:the cyclization of 2-amino-5-methylpyridine (i) with 4-methylphenacyl bromide (ii) gives 6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine (iii), which is condensed with n,n-dimethylglyoxylamide (iv) to yield 2-hydroxy-n,n-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyri din-3-yl]acetamide (v). the reaction of (v) with socl2 affords the corresponding chloroacetamide (vi), which is finally reduced to give zolpidem. this product is then converted into the hemitartrate salt. via this synthesis, zolpidem is obtained in excellent yield and quality on an industrial scale.
List of intermediates No.
1-(7-amino-2-methyl-1-benzofuran-3-yl)-1-ethanone (i)
2,6-dichlorobenzoyl chloride (ii)
n-(3-acetyl-2-methyl-1-benzofuran-7-yl)-2,6-dichlorobenzamide (iii)
ethyl 2-(2-sulfanyl-1,3-thiazol-4-yl)acetate (iv)
2-(2-sulfanyl-1,3-thiazol-4-yl)acetamide (v)
benzhydryl (6r,7r)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (vi)
Reference 1:
    allen, j.; george, p.; wick, a.; mompon, b.; depoortere, h.; rossey, g.; imidazopyridines: towards novel hypnotic and anxiolytic drugs. farmaco 1991, 46, 1, suppl., 277-88.

Route 2
n,n-dimethyl-4-(4-methylphenyl)-4-oxobutyramide (i) with br2 in hoac gives the 3-bromo derivative (ii), which is cyclized with 5-methylpyridine-2-amine (iii) in either hot acetonitrile or 1,3-dimethyl-2-imidazolidinone to afford the imidazo-pyridine derivative (iv). finally, the semitartrate salt is obtained by treatment of (iv) with tartaric acid in meoh.alternatively, the conversion of n,n-dimethyl-4-(4-methylphenyl)-4-oxobutyramide (i) into the imidazo-pyridine derivative (iv) can be directly performed by first refluxing of (i) with hbr in dichloromethane, followed by reaction with br2 and final treatment with a solution of 5-methylpyridine-2-amine (iii) in acetonitrile.
List of intermediates No.
1-(7-amino-2-methyl-1-benzofuran-3-yl)-1-ethanone (iii)
Reference 1:
    wohlleben, w.; sauter, m. (boehringer ingelheim pharma kg); method for the production of zolpidem. de 10121638; wo 0290356 .

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酒石酸唑吡坦;英文名Zolpidem tartrate;SL-80-0750-23N;Myslee;Stilnoct;Ivadal;Ambien;Bikalm;Niotal;Stilnox;CAS[99294-93-6]

 
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