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藥物詳細合成路線

Name Guanfacine hydrochloride;SPD-503;BS-100-141;Estulic;Tenex
Chemical Name N-Amidino-2,6-dichlorobenzeneacetamide monohydrochloride
CAS 29110-48-3
Related CAS 29110-47-2 (free base)
Formula C9H10Cl3N3O
Structure
Formula Weight 282.55855
Stage 上市-1979
Company Novartis (Originator), Wyeth Consumer Healthcare (Originator), Egis (Licensee), Shire Pharmaceuticals (Formulation)
Activity/Mechanism Attention Deficit Hyperactivity Disorder (ADHD), Treatment of, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, alpha2-Adrenoceptor Agonists
Syn. Route 2
Route 1
1) by methanolysis of 2,6-dichlorophenylacetonitrile (i) by means of h2so4 to methyl 2,6-dichlorophenylacetate (ii), which is then condensed with guanidine (a) in isopropanol.2) by condensation of s-methylisothiourea (v) with 2,6-dichlorophenylacetyl chloride (vi) in acetone to afford s-methyl-n-(2,6-dichlorophenylacetyl)isothiourea (vii); this product is then treated with ammonia in isopropanol.3) by condensation of 2,6-dichlorophenylacetic acid (viii) with guanidine (a) in toluene.
List of intermediates No.
ethyl 2-[(z)-(6-amino-9h-purin-9-yl)methylidene]cyclopropanecarboxylate (v)
allyl 4,4-dimethyl-3-oxopentanoate (a)
2-(dimethylamino)ethanethioamide (i)
isopropyl (z)-7-[(1r,2r,3r,5s)-5-hydroxy-2-[(e)-4-[2-iodo-5-(trifluoromethyl)phenoxy]-3-(tetrahydro-2h-pyran-2-yloxy)-1-butenyl]-3-(tetrahydro-2h-pyran-2-yloxy)cyclopentyl]-5-heptenoate (ii)
isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-{(e,3r)-3-hydroxy-4-[2-iodo-5-(trifluoromethyl)phenoxy]-1-butenyl}cyclopentyl)-5-heptenoate (viii)
hexanedioyl dichloride; adipoyl chloride (vi)
benzyl (2r)-1-(6-{(2r)-2-[(benzyloxy)carbonyl]pyrrolidinyl}-6-oxohexanoyl)-2-pyrrolidinecarboxylate; benzyl 1-[6-[2(r)-carboxy-1-pyrrolidinyl]-6-oxohexanoyl]pyrrolidine-2(r)-carboxylate (vii)
Reference 1:
    arrigoni-martelli, e.; castaner, j.; bs 100-141. drugs fut 1976, 1, 4, 167.
Reference 2:
    bream, j.b.; et al.; substituted phenylacetylguanidines: a new class of antihypertensive agents. arzneim-forsch drug res 1975, 25, 10, 1477.
Reference 3:
    bream, j.b.; et al. (novartis ag); substituted phenylacethyl derivatives of guanidine, o-alkylisoureas, s-alkylisothioureas and p-benzylalkylisothioureas. de 179348; fr 1584670; gb 1235723; us 3632645 .

Route 2
4) by reaction of the nitrile (i) with ethyl formate (b) by means of naoet in ethanol to give alpha-formyl-2,6-dichlorophenylacetonitrile (iii), which is condensed with guanidine hydrochloride (a) by means of naoet in ethanol to yield alpha-(guanidinomethylene)-2,6-dichlorophenylacetonitrile (iv); this product is finally hydrolyzed and rearranged by means of hcl.
List of intermediates No.
allyl 4,4-dimethyl-3-oxopentanoate (a)
n-(3,4-dimethoxy-9-phenanthryl)acetamide (b)
2-(dimethylamino)ethanethioamide (i)
benzyl (2r)-2-pyrrolidinecarboxylate; d-proline-benzylester hydrochloride (iii)
(19s,20s)-20-(2-carboxyethyl)-2-(carboxymethyl)-9-ethyl-5,10,15,19-tetramethyl-14-vinyl-21,22,23,24-tetraazapentacyclo[16.2.1.1~3,6~.1~8,11~.1~13,16~]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21)-decaene-4-carboxylic acid (iv)
Reference 1:
    arrigoni-martelli, e.; castaner, j.; bs 100-141. drugs fut 1976, 1, 4, 167.
Reference 2:
    bream, j.b.; et al.; verfahren zur herstellung von acylguanidinen. ch 511816 .
Reference 3:
    bream, j.b.; et al.; verfahren zur herstellung von acylguanidinen. ch 518910 .

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鹽酸胍法辛;英文名Guanfacine hydrochloride;SPD-503;BS-100-141;Estulic;Tenex;CAS[29110-48-3]

 
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