|
【结 构 式】 
|
【药物名称】Y-27632 【化学名称】(+)-trans-4-[1(R)-Aminoethyl]-N-(4-pyridyl)cyclohexane-1-carboxamide 【CA登记号】146986-50-7, 138381-45-0 (undefined isomer, diHCl salt) 【 分 子 式 】C14H21N3O 【 分 子 量 】247.34297 |
【开发单位】Mitsubishi Pharma (Originator), Calbiochem-Novabiochem (Bulk Supplier) 【药理作用】Antiglaucoma Agents, CARDIOVASCULAR DRUGS, Heart Failure Therapy, OCULAR MEDICATIONS, ONCOLYTIC DRUGS, Ophthalmic Drugs, RENAL-UROLOGIC DRUGS, Treatment of Erectile Dysfunction, Treatment of Male Sexual Dysfunction, Calcium Sensitizers, Rho Kinase Inhibitors |
合成路线1
Racemic trans-4-(1-benzyloxycarbonylaminoethyl)cyclohexanecarboxylic acid (I) was resolved using D-(+)-alpha-phenethylamine. The desired (R)-isomer (II) was activated as the corresponding acid chloride (III), which was further coupled with 4-aminopyridine (IV), yielding amide (V). The benzyloxycarbonyl protecting group of (V) was finally removed by treatment with HBr in HOAc.
| 【1】 Muro, T.; Seki, T.; Abe, M.; Inui, J.; Sato, H. (Mitsubishi Pharma Corp.); Trans-4-amino(alkyl)-1-pyridylcarbamoylcyclohexane cpds. and pharmaceutical use thereof. EP 0370498; JP 1990509475; US 4997834; WO 9005723 . |
| 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) | 52952 | 4-(1-{[(benzyloxy)carbonyl]amino}ethyl)cyclohexanecarboxylic acid | n/a | C17H23NO4 | 详情 | 详情 |
| (II) | 52953 | 4-((1R)-1-{[(benzyloxy)carbonyl]amino}ethyl)cyclohexanecarboxylic acid | C17H23NO4 | 详情 | 详情 | |
| (III) | 52954 | benzyl (1R)-1-[4-(chlorocarbonyl)cyclohexyl]ethylcarbamate | n/a | C17H22ClNO3 | 详情 | 详情 |
| (IV) | 25661 | 4-pyridinamine; 4-aminopyridine | 5044-74-5 | C5H6N2 | 详情 | 详情 |
| (V) | 52955 | benzyl (1R)-1-{4-[(4-pyridinylamino)carbonyl]cyclohexyl}ethylcarbamate | n/a | C22H27N3O3 | 详情 | 详情 |