Vinzolidine sulfate, LY-104208, -Drug Synthesis Database

【结构式】

【药物名称】Vinzolidine sulfate, LY-104208

【化学名称】Methyl (3R,5S,7R,9S)-9-[3'-(2-chloroethyl)-6,7-didehydro-4beta-hydroxy-16-methoxy-1-methyl-2',4'-dioxo-2beta,3beta,5alpha,12beta,19alpha-spiro[aspidospermidine-3,5'oxazolidin]-15-yl]-5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-2H-3,7-methanoazacycloundecino[5,4-b]indole-9-carboxylate 4'-acetate (ester) sulfate (1:1) (salt)
　　　　　　[5S-(5R*,7S*,9S*)]-9-[(2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(Acetyloxy)-3'-(2-chloroethyl)-6,7-didehydro-16-methoxy-1-methyl-2',4'-dioxospiro[aspidospermidine-3,5'-oxazolidin]-15-yl]-5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-2H-3,7-methanoazacycloundecino[5,4-b]indole-9-carboxylic acid methyl ester sulfate (1:1) (salt)

【CA登记号】67699-41-6, 67699-40-5 (free base)

【分子式】C₄₈H₆₀ClN₅O₁₃S

【分子量】982.5561

【开发单位】Lilly (Originator)

【药理作用】ONCOLYTIC DRUGS, Alkaloids

合成路线1

The reaction of vinblastine (I) with 2-chloroethyl isocyanate (II) in refluxing benzene gives the corresponding N-(2-chloroethyl)carbamate (III), which is cyclized by continuous refluxing in the same solvent.

参考文献中间体

【1】 Miller, J.C.; Gutowski, G.E.; Oxazolidinedione derivatives of Vinca alkaloids. FR 2372839; GB 1590649; JP 53071100; US 4096148 .
【2】 Hopkins, S.J.; Vinzolidine Sulfate. Drugs Fut 1984, 9, 12, 913.

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)	10346	methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetoxy)-3a-ethyl-9-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0(4,12).0(5,10)]nonadeca-4(12),5,7,9-tetraen-13-yl]-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate	446-86-6	C₄₆H₅₈N₄O₉	详情	详情
(II)	11237	1-Chloro-2-isocyanatoethane; 2-Chloroethyl isocyanate	1943-83-5	C₃H₄ClNO	详情	详情
(III)	34248			C₄₉H₆₂ClN₅O₁₀	详情	详情

Extended Information