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药物详细合成路线

Name Tauroursodeoxycholic acid;Ursodeoxycholyltaurine;UR-906
Chemical Name N-(3alpha,7beta-Dihydroxy-5beta-cholan-24-oyl)taurine
CAS 14605-22-2
Related CAS
Formula C26H45NO6S
Structure
Formula Weight 499.71565
Stage II 期临床
Company Mitsubishi Pharma (Originator), Childrens Hosp. Med. Center, Cincinnati (Codevelopment)
Activity/Mechanism GASTROINTESTINAL DRUGS, Hepatoprotectants, Liver and Biliary Tract Disorders, Treatment of
Syn. Route 3
Route 1
ursodeoxycholic acid (i) was activated as the mixed anhydride (ii) with ethyl chloroformate and triethylamine, and subsequently coupled with the triethylamine salt of taurine (iii) to produce the title conjugated bile acid. optionally, the mixed anhydride (ii) was previously converted to the active phenol ester (v) by treatment with p-hydroxypropiophenone (iv), and subsequently condensed with taurine (iii). alternatively, ursodeoxycholic acid (i) was directly coupled to taurine (iii) employing as the coupling reagents 2-isobutyl-n-isobutyloxycarbonyl-1,2-dihydroquinoline (iidq), diethylphosphorocyanidate (depc), or 2-ethoxy-n-ethoxycarbonyl-1,2-dihydroquinoline (eedq) under microwave irradiation.
List of intermediates No.
methyl (2s)-2-amino-2-[(2r,3s,4r,5r)-5-[2,4-dioxo-3,4-dihydro-1,3,5-triazin-1(2h)-yl]-3,4-dihydroxytetrahydro-2-furanyl]ethanoate (iii)
(1s,2s,3e)-1-{(e)-3-[(4r,6r)-4,6-dimethyl-1,3-dioxan-2-yl]-2-propenyl}-2-(methoxymethoxy)-4-[(2s)-4-methyl-3,6-dihydro-2h-pyran-2-yl]-3-butenyl (z)-4-((2r,6s)-6-{(2s)-2-methyl-4-[(trimethylsilyl)methyl]-4-pentenyl}-5,6-dihydro-2h-pyran-2-yl)-2-buten (i)
Reference 1:
    momose, t.; et al.; an improved synthesis of taurine- and glycine-conjugated bile acids. lipids 1997, 32, 7, 775.
Reference 2:
    dayal, b.; et al.; microwave-induced rapid synthesis of bile acid conjugates. synlett 1997, 8, 861.
Reference 3:
    bonadi, a.; molinari, e.; process for the preparation of taurine-conjugated bile acids. ep 0582891 .
Reference 4:
    reiner, a. (skyepharma ag); process for preparing ursodeoxycholic acid derivates and their inorganic and organic salts having therapeutic activity. ep 0272462 .

Route 2
in a related method, ursodeoxycholic acid (i) was activated as either the mixed anhydrides (vi) or (vii) with pivaloyl chloride or benzoyl chloride, respectively. subsequent coupling with taurine (iii) produced the title conjugated bile acid.
List of intermediates No.
methyl (2s)-2-amino-2-[(2r,3s,4r,5r)-5-[2,4-dioxo-3,4-dihydro-1,3,5-triazin-1(2h)-yl]-3,4-dihydroxytetrahydro-2-furanyl]ethanoate (iii)
(1s,2s,3e)-1-{(e)-3-[(4r,6r)-4,6-dimethyl-1,3-dioxan-2-yl]-2-propenyl}-2-(methoxymethoxy)-4-[(2s)-4-methyl-3,6-dihydro-2h-pyran-2-yl]-3-butenyl (z)-4-((2r,6s)-6-{(2s)-2-methyl-4-[(trimethylsilyl)methyl]-4-pentenyl}-5,6-dihydro-2h-pyran-2-yl)-2-buten (i)
Reference 1:
    rossetti, v.; arosio, r. (sanofi-synthelabo); process for the preparation of taurocholic acids. ep 0629634 .

Route 3
a further method was based on the microbial hydroxylation of taurolithocholic acid (viii) by the action of a microorganism belonging to the mortierella genus.
List of intermediates No.
Reference 1:
    sawada, h.; watanuki, m. (yakult honsha co., ltd.); procuding conjugated ursodeoxycholic acids. ep 0119040 .

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牛磺熊去氧胆酸;英文名Tauroursodeoxycholic acid;Ursodeoxycholyltaurine;UR-906;CAS[14605-22-2]

 
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