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药物详细合成路线

Name Seratrodast;ABT-001;A-73001;Abbott-73001;AA-2414;Bronica
Chemical Name (±)-7-Phenyl-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)heptanoic acid
CAS 112665-43-7
Related CAS 103187-09-3 (R-isomer), 103196-89-0 (S-isomer), 103186-19-2 (undefined stereoch.)
Formula C22H26O4
Structure
Formula Weight 354.45012
Stage 上市-1995
Company Takeda (Originator), Abbott (Licensee), TAP (Licensee), Grelan (Comarketer)
Activity/Mechanism Asthma Therapy, Chronic Obstructive Pulmonary Diseases (COPD), Treatment of, RESPIRATORY DRUGS, Prostanoid TP (Thromboxane A2) Antagonists
Syn. Route 1
Route 1
the reaction of pimelic acid monoester (i) with refluxing socl2 gives the corresponding acid chloride (ii), which by a friedel-crafts condensation with benzene (alcl3 as catalyst) is converted into 6-benzoylhexanoic acid ethyl ester (iii). the reduction of (iii) with nabh4 in methanol affords 7-hydroxy-7-phenylheptanoic acid ethyl ester (iv), which is hydrolyzed with naoh in hot thf - water to yield the corresponding free acid (v). finally, this compound is condensed with trimethylhydroquinone (vi) by means of boron trifluoride ethearate in hot toluene.
List of intermediates No.
ethyl 2-[(1s,2s,13s,21r)-16-(benzyloxy)-22-(cyclopropylmethyl)-2-hydroxy-14-oxa-22-azaheptacyclo[13.9.1.0(1,13).0(2,21).0(4,12).0(5,10).0(19,25)]pentacosa-4(12),5,7,9,15(25),16,18-heptaen-11-yl]acetate (a)
benzyl (1r)-2-(benzylamino)-1-(methoxymethyl)-2-oxoethylcarbamate (vi)
(1s)-1-[(2r,3s,4r)-3-(acetoxy)-2-(hydroxymethyl)-4-methyl-5-oxopyrrolidinyl]-2-methylpropyl acetate (i)
(2r,3s,4r)-3-(acetoxy)-2-[(1s)-1-(acetoxy)-2-methylpropyl]-4-methyl-5-oxo-2-pyrrolidinecarboxylic acid (ii)
(1r)-1-[(3ar,6r,6ar)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,2-ethanediol (iii)
(1r)-1-[(3ar,6r,6ar)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(benzyloxy)-1-ethanol (iv)
1-[(3ar,6r,6ar)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(benzyloxy)-1-ethanone (v)
Reference 1:
    terao, s.; maki, y. (takeda chemical industries, ltd.); quinone amides, their production and use. ep 0232089; jp 1987246545 .
Reference 2:
    terao, s.; maki, y. (takeda chemical industries, ltd.); quinone derivs., their production and use. au 8545615; ep 0171251; es 8704870; jp 1986044840; jp 1991072444; jp 1991081248; jp 1991086841; us 5180742; wo 8600887; wo 8604058 .
Reference 3:
    shiraishi, m.; kato, k.; terao, s.; ashida, y.; terashita, z.-i.; kito, g.; quinones. 4. novel eicosanoid antagonists: synthesis and pharmacological evaluation. j med chem 1989, 32, 9, 2214-21.
Reference 4:
    terao, s.; quinone derivatives: synthesis and structure-activity relations of a novel class of eicosanoid antagonists, aa-2414 and its analogs. advances in prostaglandin, thromboxane and leukotriene research 1989, 19, 651-654.
Reference 5:
    prous, j.; castaner, j.; aa-2414. drugs fut 1990, 15, 8, 783.

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塞曲司特;英文名Seratrodast;ABT-001;A-73001;Abbott-73001;AA-2414;Bronica;CAS[112665-43-7]

 
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