|
【结 构 式】 
|
【药物名称】 【化学名称】N-[6-Methyl-1-(3-methylbutyl)piperidin-2-ylcarbonyl]-4-O-(benzyl)-L-tyrosine tert-butyl ester 【CA登记号】 【 分 子 式 】C32H46N2O4 【 分 子 量 】522.73442 |
【开发单位】Elan (Originator), Pfizer (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Cerebrovascular Diseases, Treatment of, NEUROLOGIC DRUGS, Non-Opioid Analgesics, Stroke, Treatment of, Calcium Channel Blockers |
合成路线1
Hydrogenation of 6-methylpyridine-2-carboxylic acid (I) over Pd/C in aqueous ammonia afforded the corresponding piperidine (II). Subsequent condensation of (II) with isovaleraldehyde (III), followed by catalytic hydrogenation with Pd/C provided the N-isopentyl piperidine (IV), which was finally coupled with O-benzyltyrosine tert-butyl ester (V) in the presence of benzotriazolyl tetramethyluronium hexafluorophosphate (HBTU) to furnish the target amide.
| 【1】 Szoke, B.G.; Hu, L.-Y.; Millerman, E.; Nikam, S.S.; Rafferty, M.F.; Ryder, T.R.; Synthesis and biological evaluation of substituted 4-(OBz)phenylalanine derivatives as novel N-type calcium channel blockers. Bioorg Med Chem Lett 1999, 9, 8, 1121. |
| 【2】 Hu, L.-Y.; et al.; PD 151307 analogs: Synthesis and biological evaluation of substituted 4-(OBz)phenylalanine derivatives as novel N-type calcium channel blockers. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 119. |
| 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) | 30380 | 6-methyl-2-pyridinecarboxylic acid | 934-60-1 | C7H7NO2 | 详情 | 详情 |
| (II) | 30381 | 6-methyl-2-piperidinecarboxylic acid | C7H13NO2 | 详情 | 详情 | |
| (III) | 26052 | 3-methylbutanal | 590-86-3 | C5H10O | 详情 | 详情 |
| (IV) | 30382 | 1-isopentyl-6-methyl-2-piperidinecarboxylic acid | C12H23NO2 | 详情 | 详情 | |
| (V) | 26717 | tert-butyl (2S)-2-amino-3-[4-(benzyloxy)phenyl]propanoate | C20H25NO3 | 详情 | 详情 |