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藥物詳細合成路線

Name Gestodene;SH-546;SHB-331
Chemical Name 13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,15-dien-20-yn-3-one
CAS 60282-87-3
Related CAS
Formula C21H26O2
Structure
Formula Weight 310.44017
Stage III 期臨床
Company Schering AG (Originator)
Activity/Mechanism Bone Diseases, Treatment of, ENDOCRINE DRUGS, Gynecological Disorders, Treatment of , Hormone Replacement Therapy, METABOLIC DRUGS, Prevention of Osteoporosis, Progestogens
Syn. Route 3
Route 1
18-methyl-4-oestrene-3,17-dione (i) is hydroxylated by fermentation with penicillium raistrickii giving the 15alpha-hydroxy compound (ii), which is ketalized with 2,2-dimethylpropanediol (a), triethyl orthoformate and p-toluenesulfonic acid in ch2cl2 giving a mixture of the delta(5-6) and delta(5-10)-ketals (iiia-b). these ketals are mesylated witn methanesulfonyl chloride in pyridine yielding the mesyl ester (iva-b), which is treated with sodium acetate in dmf to afford the oestradiene ketal (va-b). finally, this compound is treated with ethynylmagnesium bromide (b) and refluxed with oxalic acid (c) in methanol.
List of intermediates No.
l-glutamine (a)
18-(4-iodophenyl)-1-octadecanol (c)
3-(3-iodopropyl)phenyl phenyl ether; 1-(3-iodopropyl)-3-phenoxybenzene (b)
n,n-diethyl-1-ethanamine; n,n,n-triethylamine; triethylamine (i)
methyl 7-[(3r)-3-hydroxy-5-oxo-1-cyclopenten-1-yl]heptanoate (ii)
methyl 7-((3r)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-oxo-1-cyclopenten-1-yl)heptanoate (iiia)
methyl 7-((1r,2r,3r)-2-(3-butenyl)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-oxocyclopentyl)heptanoate (iiib)
methyl 7-((1r,2r,3r,5s)-2-(3-butenyl)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-hydroxycyclopentyl)heptanoate (iva)
methyl 7-((1r,2r,3r,5s)-2-(3-butenyl)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclopentyl)heptanoate (ivb)
methyl 7-[(1r,2r,3r,5s)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(3-oxopropyl)cyclopentyl]heptanoate (va)
1-benzothiophen-2-yllithium (vb)
Reference 1:
    hofmeister, h.; wiechert, r.; annen, k.; laurent, h.; steinbeck, h.; steroids and pharmaceutical compositions thereof. be 0847090; fr 2326927; gb 1569135; jp 52046060; us 4081537 .
Reference 2:
    castaner, j.; blancafort, p.; gestodene. drugs fut 1977, 2, 12, 805.

Route 2
ketals (iiia-b) can also be treated with trimethylsilyl chloride in pyridine to give the trimethylsilyl derivative (via-b), which is then treated with ethynylmagnesium bromide (b) and oxalic acid (c) in methanol.
List of intermediates No.
18-(4-iodophenyl)-1-octadecanol (c)
3-(3-iodopropyl)phenyl phenyl ether; 1-(3-iodopropyl)-3-phenoxybenzene (b)
methyl 7-((3r)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-oxo-1-cyclopenten-1-yl)heptanoate (iiia)
methyl 7-((1r,2r,3r)-2-(3-butenyl)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-oxocyclopentyl)heptanoate (iiib)
methyl 7-((1r,2r,3r,5s)-2-[3-(1-benzothiophen-2-yl)-3-hydroxypropyl]-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclopentyl)heptanoate (via)
methyl 7-[(1r,2r,3r,5s)-2-[3-(1-benzothiophen-2-yl)-3-hydroxypropyl]-3,5-dihydroxycyclopentyl]heptanoate (vib)
Reference 1:
    hofmeister, h.; wiechert, r.; annen, k.; laurent, h.; steinbeck, h.; steroids and pharmaceutical compositions thereof. be 0847090; fr 2326927; gb 1569135; jp 52046060; us 4081537 .
Reference 2:
    castaner, j.; blancafort, p.; gestodene. drugs fut 1977, 2, 12, 805.

Route 3
ketals (iiia-b) can also be acetylated with acetic anhydride in pyridine to the acetate (viia-b), which is then treated with ethynylmagnesium bromide (b) and oxalic acid (c) in methanol.
List of intermediates No.
18-(4-iodophenyl)-1-octadecanol (c)
3-(3-iodopropyl)phenyl phenyl ether; 1-(3-iodopropyl)-3-phenoxybenzene (b)
methyl 7-((3r)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-oxo-1-cyclopenten-1-yl)heptanoate (iiia)
methyl 7-((1r,2r,3r)-2-(3-butenyl)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-oxocyclopentyl)heptanoate (iiib)
2-([(4-methylphenyl)sulfonyl][2-[[(4-methylphenyl)sulfonyl](2-[[(4-methylphenyl)sulfonyl]oxy]ethyl)amino]ethyl]amino)ethyl 4-methylbenzenesulfonate (viia)
4-methyl-n-[2-[[(4-methylphenyl)sulfonyl](2-[[(4-methylphenyl)sulfonyl]amino]ethyl)amino]ethyl]benzenesulfonamide (viib)
Reference 1:
    hofmeister, h.; wiechert, r.; annen, k.; laurent, h.; steinbeck, h.; steroids and pharmaceutical compositions thereof. be 0847090; fr 2326927; gb 1569135; jp 52046060; us 4081537 .
Reference 2:
    castaner, j.; blancafort, p.; gestodene. drugs fut 1977, 2, 12, 805.

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孕二烯酮;英文名Gestodene;SH-546;SHB-331;CAS[60282-87-3]

 
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