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药物详细合成路线

Name Ciloprost;Iloprost;E-1030;SH-401;ZK-36374;Ventavis;Endoprost;Ilom?ine;Ilomedin
Chemical Name 5(E)-[(1S,5S,6R,7R)-7-Hydroxy-6-[(3S,4RS)-3-hydroxy-4-methyl-1(E)-octen-6-ynyl]bicyclo[3.3.0]octan-3-ylidene]pentanoic acid
CAS 73873-87-7
Related CAS
Formula C22H32O4
Structure
Formula Weight 360.49794
Stage 上市-1992
Company Schering AG (Orphan Drug), Berlex (Originator), Schering AG (Originator), CoTherix (Licensee), Eisai (Licensee), Italfarmaco (Licensee)
Activity/Mechanism CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Peripheral Vascular Disease, Treatment of, Pulmonary Hypertension, Treatment of, Raynauds Phenomenon, Treatment for , Treatment of Peripheral Obstructive Vascular Disease, Prostacyclin Analogs
Syn. Route 1
Route 1
reaction of the lactone (i) with lithium ethyl acetate followed by acid catalyzed dehydration and hydrolysis of the ester group with k2co3 in methanol affords the hydroxy compound (ii), which gives after collins oxidation, treatment with 1,5-diazabicyclo[4.3.0]non-5-ene (dbn) and reduction with nabh4, the ketoester (iii). dealkoxy carbonylation with dabco in toluene, benzoylation and removal of the silyl group with acetic acid in thf-water yield the ketone (iv). ketalization of the ketone (iv) with ethylene glycol, collins oxidation and condensation of the resulting aldehyde with the sodium salt of the phosphonate (v) afford the enone (vi). reduction of (vi) with nabh4 in methanol, cleavage of the ketal function with acetic acid-h2o and subsequent tetrahydropyranylation lead to the ketone (vii). wittig condensation of the ketone (vii) with (viii) and nah in dmso affords after chromatographic separation the acid (ix), which is finally deprotected to (x) (zk-36374) by treatment with acetic acid in thf-water mixture.
List of intermediates No.
(1r,4as,10ar)-7-isopropyl-1,4a-dimethyl-6-sulfo-1,2,3,4,4a,9,10,10a-octahydro-1-phenanthrenecarboxylic acid (a)
1-(6-phenyl-3-pyridinyl)-1-ethanone oxime (v)
5-bromo-2-methyl-1-benzofuran-4,7-dione (viii)
[(2r)-4-benzyl-2-(1h-indol-3-ylmethyl)piperazinyl][3,5-bis(trifluoromethyl)phenyl]methanone (i)
[3,5-bis(trifluoromethyl)phenyl][(2r)-2-(1h-indol-3-ylmethyl)piperazinyl]methanone (ii)
tert-butyl 4-methyl-1h-indol-7-ylcarbamate (iiia)
benzyl 2-[(3r)-4-[3,5-bis(trifluoromethyl)benzoyl]-3-(1h-indol-3-ylmethyl)piperazinyl]acetate (iiib)
2-[(3r)-4-[3,5-bis(trifluoromethyl)benzoyl]-3-(1h-indol-3-ylmethyl)piperazinyl]acetic acid (iv)
tert-butyl 3-formyl-4-methyl-1h-indol-7-ylcarbamate (via)
4-(1-cyclohexen-1-yl)morpholine (vib)
tert-butyl 3-cyano-4-methyl-1h-indol-7-ylcarbamate (viia)
ethyl 4-[2-(4-morpholinyl)-1-cyclohexen-1-yl]-4-oxobutanoate (viib)
diethyl aminomalonate; diethyl 2-aminomalonate (ixa)
ethyl 3-(3-ethoxy-3-oxopropyl)-4,5,6,7-tetrahydro-1h-indole-2-carboxylate (ixb)
Reference 1:
    skuballa, w.; raduechel, b.; vorbrueggen, h.; mannesmann, g.; losert, w.; casals, j. (schering ag); novel prostacyclin derivatives and a process for the preparation thereof.. de 2845770; es 485199; us 4692464 .
Reference 2:
    vorbruggen, h.; schillinger, e.; ciloprost. drugs fut 1981, 6, 11, 676.

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伊洛前列素;英文名Ciloprost;Iloprost;E-1030;SH-401;ZK-36374;Ventavis;Endoprost;Ilom?ine;Ilomedin;CAS[73873-87-7]

 
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