Quinupristin mesilate, RP-57669, -Drug Synthesis Database

【结构式】

【药物名称】Quinupristin mesilate, RP-57669

【化学名称】N-(3-Hydroxy-2-pyridylcarbonyl)-(S)-threonyl-(R)-(alpha-aminobutyryl)-(S)-prolyl-[N-methyl-4-(dimethylamino)-(S)-phenylalanyl]-[4-oxo-5(R)-[quinuclidin-3(S)-ylthiomethyl]-(S)-homoprolyl]-(S)-phenylglycine C-1.6-O-3.1-lactone methanesulfonate
　　　　　　5(R)delta-[3(S)-Quinuclidinylthiomethyl]pristinamycin IA methanesulfonate
　　　　　　(15aS,24aS)-18(R)-[1-Azabicyclo[2.2.2]oct-3(S)-ylthiomethyl]-22(S)-[4-(dimethylamino)benzyl]-6(R)-ethyl-9(S)-(3-hydroxypyridin-2-ylcarboxamido)-10(R),23-dimethyl-13(S)-phenyldocosahydro-12H-pyrido[2,1-f]pyrrolo[2,1-b][1,4,7,10,13,16]oxapentaazacyclononadecine-5,8,12,15,17,21,24-heptaone methanesulfonate
　　　　　　N-[(6R,9S,10R,13S,15aS,18R,22S,24aS)-22-[p-(dimethylamino)benzyl]-6-ethyldocosahydro-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyl-18-[[(3S)-3-quinuclidinylthio]methyl]-12H-pyrido[2,1-f]pyrrolo[2,1-l][1,4,7,10,13,16]oxapentaazacyclononadecin-9-yl]-3-hydroxypicolinamide

【CA登记号】120138-50-3 (free base)

【分子式】C₅₄H₇₁N₉O₁₃S₂

【分子量】1118.34847

【开发单位】Aventis Pharma (Originator)

【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Macrolides

合成路线1

The condensation of the cyclopeptide analogue (I) with morpholine (II) and formaldehyde by means of MsOH in hot methanol gives the 4-morpholinylmethyl derivative (III), which by a treatment with NaOAc in hot acetic acid yields the methylene derivative (IV). Finally this compound is condensed with quinuclidine-3(S)-thiol in hot acetone.

参考文献中间体

【1】 Bastart, J.P.; Paris, J.M.; Radisson, X. (Aventis SA); Pristinaymcin IA or viginiamycin derivs. and their preparation. EP 0432029 .
【2】 Barriere, J.C.; Paris, J.M.; RP 59500 and related semisynthetic streptogramins. Drugs Fut 1993, 18, 9, 833.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IIIa)	41286			C₅₀H₆₃N₉O₁₁	详情	详情
(IIIb)	41287			C₅₀H₆₃N₉O₁₁	详情	详情
(I)	41285	N-[(6R,9S,10R,13S,15aS,22S,24aS)-22-[4-(dimethylamino)benzyl]-6-ethyl-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyldocosahydro-12H-pyrido[2,1-f]pyrrolo[2,1-l][1,4,7,10,13,16]oxapentaazacyclononadecin-9-yl]-3-hydroxy-2-pyridinecarboxamide		C₄₅H₅₄N₈O₁₀	详情	详情
(II)	10388	Morpholine	110-91-8	C₄H₉NO	详情	详情
(IV)	41288			C₄₆H₅₄N₈O₁₀	详情	详情
(V)	41289	(3S)-1-azabicyclo[2.2.2]octane-3-thiol; (3S)-1-azabicyclo[2.2.2]oct-3-ylhydrosulfide	4595-82-8	C₇H₁₃NS	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)