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【结 构 式】 
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【药物名称】(S)-PD-148903 【化学名称】(-)-6(S)-(Dipropylamino)-1,2,3,4,5,6,7,8-octahydronaphthalen-1-one hydrochloride 【CA登记号】335158-94-6, 256474-06-3 (undefined isomer; free base) 【 分 子 式 】C16H28ClNO 【 分 子 量 】285.86066 |
【开发单位】Pfizer (Originator) 【药理作用】Antiparkinsonian Drugs, Chemical Delivery Systems, DRUG DELIVERY, Drug Delivery Systems, Extrapyramidal Disorders, Treatment of, NEUROLOGIC DRUGS |
合成路线1
Mannich reaction of 1,3-cyclohexanedione (I) with paraformaldehyde and dipropylamine affords intermediate (II) which, without isolation is condensed with acetone under Robinson annulation conditions, to produce the bicyclic amino ketone (III). Enamine reduction in (III) using NaBH3CN in AcOH gives a racemic amine, which is resolved via formation of the corresponding diastereoisomeric salts with (-)-ditoluyltartaric acid, and finally isolated as the hydrochloride salt.
| 【1】 Venhuis, B.J.; Wikstrom, H.V.; Rodenhuis, N.; Sundell, S.; Dijkstra, D.; A new type of prodrug of catecholamines: An opportunity to improve the treatment of Parkinson's disease. J Med Chem 2002, 45, 12, 2349. |
| 【2】 Wise, L.D.; Wikstrom, H.V.; Wustrow, D.J.; Meltzer, L.T.; Dijkstra, D.; Venhuis, B.J. (Pfizer Inc.); Method for treating Parkinson's disease by administering (-)-5-keto-2-N,N-di-N-propylamino-tetrahydrotetralin. WO 0128977 . |