W-1807, BAY-W-1807
Chemical Name: (-)-4(S)-(2-Chlorophenyl)-1-ethyl-2-methyl-1,4-dihydropyridine-3,5,6-tricarboxylic acid 3- isopropyl ester disodium salt
CAS No. 252721-95-2 (free acid)
项目整合开发状态: Preclinical
项目研究机构: Bayer (Originator)
合成路线:The title compound was prepared by N-alkylation of the known dihydropyridine (I) with ethyl iodide in the presence of LDA.
合成路线:The intermediate hydroxy lactone (IV) was prepared by two alternative procedures: Compound (II) was prepared by N-alkylation of the known dihydropyridine (I) with ethyl iodide in the presence of LDA (1).Bromination of the lithium derivative of (II) at -78 C followed by aqueous hydrolysis provided hydroxy lactone (IV).This intermediate was also prepared by basic treatment of formyl ester (III).Hydroxy lactone (IV) was oxidized to cyclic anhydride (V) by treatment with trifluoroacetic anhydride in DMSO.Then,basic hydrolysis of anhydride (V) provided the title disodium dicarboxylate salt.
📌 参考资料/链接：
参考文献标题:1-Alkyl-substd.1,4-dihydropyridine lactones,process for their preparation and their use in pharmaceuticals
文献作者:Puls,W.; Bossert,F.; Petzinna,D.; Schlossmann,K.; Goldmann,S.; Bischoff,H.(Bayer AG)
参考来源:DE 3410645; EP 0158138; ES 8607309; ES 8702413; ES 8702414; ES 8702415; ES 8702416; ES 8702417; ES 8702418; ES 8704173; ES 8704174; US 5026714
📄 详细内容
合成路线:The intermediate hydroxy lactone (IV) was prepared by two alternative procedures: Compound (II) was prepared by N-alkylation of the known dihydropyridine (I) with ethyl iodide in the presence of LDA (1).Bromination of the lithium derivative of (II) at -78 C followed by aqueous hydrolysis provided hydroxy lactone (IV).This intermediate was also prepared by basic treatment of formyl ester (III).Hydroxy lactone (IV) was oxidized to cyclic anhydride (V) by treatment with trifluoroacetic anhydride in DMSO.Then,basic hydrolysis of anhydride (V) provided the title disodium dicarboxylate salt.
参考文献标题:Dihydropyridine derivs.
文献作者:Goldmann,S.; Ahr,H.-J.; Puls,W.; Bischoff,H.; Petzinna,D.; Schlossmann,K.; Bender,J.(Bayer AG)
参考来源:AU 8777695; DE 3629545; EP 0258729; JP 1988072674