Xamoterol fumarate, TI-31, ICI-118587, Sepan, Corwin, -Drug Synthesis Database

【结构式】

【药物名称】Xamoterol fumarate, TI-31, ICI-118587, Sepan, Corwin

【化学名称】(±)-1-(p-Hydroxyphenoxy)-3-[2-(morpholinocarbonamido)ethylamino]-2-propanol hemifumarate
　　　　　　(±)-N-[2-[[2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-4-morpholinecarboxamide (E)-2-butenedioate(2:1) (salt)

【CA登记号】90730-93-1, 69630-19-9 ((1:1) salt), 81801-12-9 (free base)

【分子式】C₂₀H₂₉N₃O₉

【分子量】455.46883

【开发单位】AstraZeneca (Originator), Stuart Pharma. (Originator), Yamanouchi (Originator)

【药理作用】CARDIOVASCULAR DRUGS, Heart Failure Therapy, beta1-Adrenoceptor Agonists

合成路线1

The reaction of 1-(p-benzyloxyphenoxy)-2,3-epoxypropane (I) with 4-[N-(2-aminoethyl)carbamoyl]morpholine (II) by means of KOH in isopropanol gives 1-(p-benzyloxyphenoxy)-3-[2-(morpholinocarbonamido)ethylamino]-2-propanol (III), which is debenzylated by treatment with H2 over Pd/C in ethanol acetic acid and treated with a solution of fumaric acid in ethanol.

参考文献中间体

【1】 Main, B.G.; Barlow, J.J. (AstraZeneca plc); Morpholine carboxamides and use thereof. FR 2391997; JP 53147038; US 4143140; US 4172150 .
【2】 Blancafort, P.; Serradell, M.N.; Thorpe, P.J.; Castaner, J.; ICI-118,587. Drugs Fut 1982, 7, 8, 571.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	23808	Fumaric acid; (E)-2-butenedioic acid	110-17-8	C₄H₄O₄	详情	详情
(I)	32152	Benzyl 4-(2-oxiranyloxy)phenyl ether; 2-[4-(Benzyloxy)phenoxy]oxirane; 1-(p-Benzyloxyphenoxy)-2,3-epoxypropane		C₁₅H₁₄O₃	详情	详情
(II)	32153	N-(2-aminoethyl)-4-morpholinecarboxamide; 4-[N-(2-Aminoethyl)carbamoyl]morpholine		C₇H₁₅N₃O₂	详情	详情
(III)	32154	N-[2-([3-[4-(Benzyloxy)phenoxy]-2-hydroxypropyl]amino)ethyl]-4-morpholinecarboxamide; 1-(p-Benzyloxyphenoxy)-3-[2-(morpholinocarbonamido)ethylamino]-2-propanol		C₂₃H₃₁N₃O₅	详情	详情

Extended Information