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药物详细合成路线

Name Tazarotene;AGN-190168;Avage;Suretin;Tazorac;Zorac
Chemical Name 6-[2-(4,4-Dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylic acid ethyl ester
CAS 118292-40-3
Related CAS
Formula C21H21NO2S
Structure
Formula Weight 351.47102
Stage 上市-1996
Company Allergan (Originator), Bioglan (Licensee), 3M Pharmaceuticals (Comarketer)
Activity/Mechanism Acne Therapy, Antipsoriatics, Dermatologic Drugs, ONCOLYTIC DRUGS, Ornithine Decarboxylase Inhibitors, Retinoid RARbeta Agonists, Retinoid RARgamma Agonists, Retinoids
Syn. Route 1
Route 1
the condensation of thiophenol (ii) with 3-methyl-2-butenyl bromide (i) by means of naoh in refluxing acetone gives 3-methyl-2-butenyl(phenyl)sulfide (iii), which is cyclized by means of p2o5 and h3po4 in refluxing benzene to yield 4,4-dimethyl-3,4-dihydro-1h-1-benzothiopyran (iv). the acylation of (iv) with acetyl chloride catalyzed by sncl4 in benzene affords the corresponding 6-acetyl derivative (v), which by dehydration with lithium diisopropylamide and diethyl chlorophosphate in thf is converted into 6-ethynyl-4,4-dimethyl-3,4-dihydro-2h-1-benzothiopyran (vi). finally, this compound is condensed with ethyl 6-chloropyridine-3-carboxylate (vii) by means of butyllithium in thf.the ester (vii) is obtained by esterification of the corresponding acid (viii) with ethanol by means of dicyclohexylcarbodiimide (dcc) and dimethylaminopyridine (dmap).
List of intermediates No.
2-[(2r)-2-(2-chlorobenzyl)-3,6-dioxo-4-(3-phenylpropyl)piperazinyl]acetic acid (ii)
phenyl (2s)-2-[[chloro(phenoxy)phosphoryl]amino]propanoate (i)
benzyl (2s)-2-[[chloro(phenoxy)phosphoryl]amino]propanoate (iii)
3,5-dibromo-2,2,6,6-tetramethyl-4-piperidinone (iv)
n-(3-aminopropyl)-2,2,5,5-tetramethyl-2,5-dihydro-1h-pyrrole-3-carboxamide (v)
2-[[(3-[[(2,2,5,5-tetramethyl-2,5-dihydro-1h-pyrrol-3-yl)carbonyl]amino]propyl)amino]carbonyl]benzoic acid (vi)
n-[3-(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)propyl]-2,2,5,5-tetramethyl-2,5-dihydro-1h-pyrrole-3-carboxamide (vii)
3-hydroxyacetophenone; 1-(3-hydroxyphenyl)-1-ethanone (viii)
Reference 1:
    ngo, j.; leeson, p.a.; castaner, j.; tazarotene. drugs fut 1997, 22, 3, 249.
Reference 2:
    chandraratna, r.a.s. (allergan, inc.); disubstd. acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity. ep 0284288; jp 88255277; jp 95324085 .
Reference 3:
    chandraratna, r.a.s. (allergan, inc.); disubstd. acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity. us 5089509 .
Reference 4:
    chandraratna, r.a. (allergan, inc.); disubstd. acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity. wo 9611686 .

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他扎罗汀;英文名Tazarotene;AGN-190168;Avage;Suretin;Tazorac;Zorac;CAS[118292-40-3]

 
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