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【结 构 式】 
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【药物名称】QAB-205, NVP-QAB-205, NVP-QAB-205-AA 【化学名称】N-[4-[6-(Cyclobutylamino)-9H-purin-2-ylamino]phenyl]-N-methylacetamide 【CA登记号】325165-07-9 (hydrochloride) 【 分 子 式 】C18H21N7O 【 分 子 量 】351.41437 |
【开发单位】Novartis (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, Chronic Obstructive Pulmonary Diseases (COPD), Treatment of, Respiratory Distress Syndrome, Agents for, RESPIRATORY DRUGS, Syk Kinase Inhibitors |
合成路线1
2,6-Dichloropurine (I) is condensed with cyclobutylamine (II) in the presence of diisopropylethylamine in hot butanol to produce the 6-cyclobutylamino purine (III). The 2-chloro group of purine (III) is then displaced with 4-amino-N-methylacetanilide (IV) in N-methylpyrrolidone at 145 C to furnish the target diamino purine derivative.
| 【1】 Bammerlin, H.; Le Grand, D.; Hayler, J.; et al.; Novel 2,6-disubstituted purines - The synthesis of potent and selective inhibitors of the protein tyrosine kinase Syk. Drugs Fut 2002, 27, Suppl. A. |
| 【2】 Menear, K.A.; Mattes, H.; Collingwood, S.P.; Walker, C.V.; Hayler, J.; Le Grand, D.M.; Cockcroft, X.-L. (Novartis AG; Novartis-Erfindungen VmbH); Purine derivs. inhibitors of tyrosine protein kinase syk. EP 1200435; WO 0109134 . |
| 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) | 58377 | cyclobutylamine; cyclobutanamine; Aminocyclobutane | 2516-34-9 | C4H9N | 详情 | 详情 |
| (III) | 58378 | 2-chloro-N-cyclobutyl-9H-purin-6-amine; N-(2-chloro-9H-purin-6-yl)-N-cyclobutylamine | C9H10ClN5 | 详情 | 详情 | |
| (IV) | 58379 | N-(4-aminophenyl)-N-methylacetamide; 4'-amino-N-methylacetanilide | C9H12N2O | 详情 | 详情 |