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【结 构 式】 
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【药物名称】Gestrinone, A-46745, Ru-2323, R-2323, Dimetrose, Nemestran, Dimetriose 【化学名称】(17alpha)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one 【CA登记号】16320-04-0 【 分 子 式 】C21H24O2 【 分 子 量 】308.42423 |
【开发单位】Aventis Pharma (Originator), Pfizer (Licensee) 【药理作用】ENDOCRINE DRUGS, Endometriosis Therapy, Gynecological Disorders, Treatment of , Progesterone Receptor Antagonists |
合成路线1
Compound can be prepared in two different ways: 1) By dehydration of 13beta-ethyl-11beta,17beta-dihydroxy-17alpha-ethynyl-gona-4,9-diene-3-one (IV) with 60% formic acid at 100 C or with perchloric acid in methylene chloride containing acetonitrile. 2) The ketalization of 13beta-ethyl-gona-4,9,11-triene-3,17-dione (I) by means of glycol (A) and oxalic acid in dichloroethane affords 3-ethylenedioxy-13beta-ethyl-gona-4,9,11-trien-17-one (II), which is then treated with methylmagnesium bromide (B) and acetylene (C) in THF to yield 3-ethylenedioxy-13beta-ethyl-17beta-hydroxy-17alpha-ethynyl-gona-4,9,11-triene (III). Finally, this compound is hydrolyzed in an acidic medium.
| 【1】 Bertin, D.; Pierdet, A.; 19-Nor-delta(4,9,11)-gonatriene-3-ones. DE 1618810; FR 1503984; GB 1128787; US 3484462 . |
| 【2】 Bertin, D.; Pierdet, A; Process for the preparation of unsaturated 19-nor steroids. DE 1618815; FR 1479352; GB 1128788; US 3478067 . |
| 【3】 Nomine, G.; et al.; New Steroid compounds, compositions incorporating them and processes for their preparation. GB 1069709 . |
| 【4】 Nomine, G.; et al.; Novel 13beta-alkyl-4,9,11-gonatriene-3-ones. DE 1291337; DE 1593307; FR 1426077; FR 1453214; FR 1492782; NL 6607609; US 3248294; US 3257278 . |
| 【5】 Castaner, J.; Thorpe, P.; R-2323. Drugs Fut 1977, 2, 2, 131. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 11295 | Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol | 107-21-1 | C2H6O2 | 详情 | 详情 |
| (B) | 33623 | bromo(methyl)magnesium | 75-16-1 | CH3BrMg | 详情 | 详情 |
| (I) | 33619 | (8S,13R,14S)-13-ethyl-7,8,13,14,15,16-hexahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione | C19H22O2 | 详情 | 详情 | |
| (II) | 33620 | C21H26O3 | 详情 | 详情 | ||
| (III) | 33621 | C23H28O3 | 详情 | 详情 | ||
| (IV) | 33622 | (8S,11S,13S,14S,17R)-13-ethyl-17-ethynyl-11,17-dihydroxy-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | C21H26O3 | 详情 | 详情 | |
| (C) | 23634 | acetylene | 74-86-2 | C2H2 | 详情 | 详情 |