Bimatoprost, AGN-192024, Lumigan, -Drug Synthesis Database

【结构式】

【药物名称】Bimatoprost, AGN-192024, Lumigan

【化学名称】(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-N-ethyl-5-heptenamide
　　　　　　17-Phenyl-18,19,20-trinorprostaglandin F2alpha ethylamide
　　　　　　(5Z,9alpha,11alpha,13E,15S)-9,11,15-Trihydroxy-17-phenyl-18,19,20-trinorprosta-5,13-dienoic acid ethylamide

【CA登记号】155206-00-1

【分子式】C₂₅H₃₇NO₄

【分子量】415.57794

【开发单位】Allergan (Originator)

【药理作用】Antiglaucoma Agents, OCULAR MEDICATIONS, Ophthalmic Drugs, Prostaglandins

合成路线1

The esterification of 17-phenyl-18,19,20-trinorprostaglandin F2alpha (I) with methyl iodide and DBU in acetone gives the corresponding methyl ester (II), which is finally treated with ethylamine in methanol at 80-5 C.

参考文献中间体

【1】 Rabasseda, X.; Castaner, J.; Sorbera, L.A.; Leeson, P.A.; Bimatoprost. Drugs Fut 2001, 26, 5, 433.
【2】 Woodward, D.F.; Andrews, S.W.; Burk, R.M.; Garst, M.E. (Allergan, Inc.); Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivs. as therapeutic agents. EP 0660716; JP 1996501310; US 5352708; WO 9406433 .
【3】 Andrews, S.W.; Burk, R.M.; Garst, M.E.; Woodward, D.F. (Allergan, Inc.); Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivs. as therapeutic agents. US 5607978 .

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)	43188	(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoic acid	38344-08-0	C₂₃H₃₂O₅	详情	详情
(II)	46719	methyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate		C₂₄H₃₄O₅	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)