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Isbogrel, A-66900, CV-4151

伊波格雷Chemical Name: (E)-7-Phenyl-7-(3-pyridyl)-6-heptenoic acid
CAS No. 89667-40-3
项目整合开发状态: Phase III
项目研究机构: Takeda (Originator), TAP (Licensee)
合成路线:The condensation of 6-bromohexanoic acid (I) with triphenylphosphine in refluxing acetonitrile gives the corresponding phosphonium salt (III),which is submitted to a Wittig condensation with phenyl 3-pyridyl ketone (IV) by means of NaH in DMSO,yielding a mixture of the title product and its (Z)-isomer (V).This mixture of isomers is separated by fractional crystallization or HPLC and the isomeric compound (V) is treated with refluxing aqueous 25% HBr to perform its isomerization to CV-415.
📌 参考资料/链接:
参考文献标题:Substituted vinylcarboxylic acid derivative and its preparation
文献作者:Terao,S.; et al.(Takeda Chemical Industries,Ltd.)
参考来源:JP 58219162

📄 详细内容


合成路线:The condensation of 6-bromohexanoic acid (I) with triphenylphosphine in refluxing acetonitrile gives the corresponding phosphonium salt (III),which is submitted to a Wittig condensation with phenyl 3-pyridyl ketone (IV) by means of NaH in DMSO,yielding a mixture of the title product and its (Z)-isomer (V).This mixture of isomers is separated by fractional crystallization or HPLC and the isomeric compound (V) is treated with refluxing aqueous 25% HBr to perform its isomerization to CV-415.

参考文献标题:CV-4151
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1986,11(3),183


合成路线:The condensation of 6-bromohexanoic acid (I) with triphenylphosphine in refluxing acetonitrile gives the corresponding phosphonium salt (III),which is submitted to a Wittig condensation with phenyl 3-pyridyl ketone (IV) by means of NaH in DMSO,yielding a mixture of the title product and its (Z)-isomer (V).This mixture of isomers is separated by fractional crystallization or HPLC and the isomeric compound (V) is treated with refluxing aqueous 25% HBr to perform its isomerization to CV-415.
参考文献标题:Thromboxane synthetase inhibitors (TXSI).Design,synthesis,and evaluation of a novel series of omega-pyridilalkenoic acids
文献作者:Kato,K.; Ohkawa,S.; Terao,S.; Terashita,Z.; Nishikawa,K.
参考来源:J Med Chem 1985,28(3),287-294


产品链接: CAS No. 89667-40-3››