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【结 构 式】 
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【药物名称】NCX-2111 【化学名称】2(S)-Acetamido-3-[2-(4-isobutylphenyl)propionylsulfanyl]propionic acid 4-(nitrooxy)butyl ester 【CA登记号】302543-76-6 【 分 子 式 】C22H32N2O7S 【 分 子 量 】468.57354 |
【开发单位】NicOx (Originator) 【药理作用】RENAL-UROLOGIC DRUGS, Urinary Incontinence Therapy, Cyclooxygenase-1 Inhibitors, Cyclooxygenase-2 Inhibitors, Nitric Oxide Donors |
合成路线1
Coupling of ibuprofen (I) with N-acetylcysteine (II) via activation with carbonyl diimidazole produced the thioester adduct (III). Reaction of the free carboxyl group of (III) with tetrahydrofuran in the presence of triphenylphosphine and carbon tetrabromide gave rise to the bromobutyl ester (IV). The bromide group of (IV) was finally displaced with silver nitrate to produce the title nitrate ester.
| 【1】 Del Soldato, P. (NicOx SA); Pharmaceutical cpds.. EP 1169294; WO 0061537 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 52312 | 2-(4-Isobutylphenyl)propionic acid; Ibuprofen | 15687-27-1 | C13H18O2 | 详情 | 详情 |
| (II) | 39365 | (2S)-2-(acetamido)-3-sulfanylpropionic acid | 616-91-1 | C5H9NO3S | 详情 | 详情 |
| (III) | 52313 | N-acetyl{2-[4-(2-methylpropyl)phenyl]propanoyl}cysteine | C18H25NO4S | 详情 | 详情 | |
| (IV) | 52314 | 4-bromobutyl 2-(acetylamino)-3-({2-[4-(2-methylpropyl)phenyl]propanoyl}sulfanyl)propanoate | C22H32BrNO4S | 详情 | 详情 |