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【结 构 式】 
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【药物名称】CVT-313 【化学名称】N2,N2-Bis(2-hydroxyethyl)-9-isopropyl-N6-(4-methoxybenzyl)purine-2,6-diamine 【CA登记号】199986-75-9 【 分 子 式 】C20H28N6O3 【 分 子 量 】400.48456 |
【开发单位】CV Therapeutics (Originator) 【药理作用】Angina pectoris, Treatment of, CARDIOVASCULAR DRUGS, Restenosis Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, CDK2 Inhibitors |
合成路线1
The condensation of 2,6-dichloropurine (I) with 4-methoxybenzylamine (II) in butanol at 120 C gives 2-chloro-6-(4-methoxybenzylamino)purine (II), which is treated with isopropyl iodide (IV) and NaH in DMF yielding 2-chloro-9-isopropyl-6-(4-methoxybenzylamino)purine (V). Finally, this compound is condensed with diethanolamine (VI) in DMSO at 160 C.
| 【1】 Schow, S.R.; et al.; Synthesis and activity of 2,6,9-trisubstituted purines. Bioorg Med Chem Lett 1997, 7, 21, 2697. |
| 【2】 Lum, R.T.; Blum, C.L.; Mackman, R.; Wick, M.M.; Schow, S.R. (CV Therapeutics, Inc.); Purine inhibitors of cyclin dependent kinase 2 and IkappaB-alpha. EP 1021186; US 5866702; WO 9805335 . |
| 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) | 25254 | 2,6-dichloro-9H-purine | 5451-40-1 | C5H2Cl2N4 | 详情 | 详情 |
| (II) | 15098 | 4-Methoxybenzylamine; (4-Methoxyphenyl)methanamine | 2393-23-9 | C8H11NO | 详情 | 详情 |
| (III) | 38022 | N-(2-chloro-9H-purin-6-yl)-N-(4-methoxybenzyl)amine; 2-chloro-N-(4-methoxybenzyl)-9H-purin-6-amine | C13H12ClN5O | 详情 | 详情 | |
| (IV) | 19369 | 2-iodopropane | 75-30-9 | C3H7I | 详情 | 详情 |
| (V) | 38023 | 2-chloro-9-isopropyl-N-(4-methoxybenzyl)-9H-purin-6-amine; N-(2-chloro-9-isopropyl-9H-purin-6-yl)-N-(4-methoxybenzyl)amine | C16H18ClN5O | 详情 | 详情 | |
| (VI) | 24273 | 2-[(2-hydroxyethyl)amino]-1-ethanol | 111-42-2 | C4H11NO2 | 详情 | 详情 |