PAT-5A
Chemical Name: (E)-5-[4-[1-(2-Pyridyl)pyrrolidin-2(S)-ylmethoxy]benzylidene]thiazolidine-2,4-dione maleate
CAS No. 199117-51-6, 199117-46-9 (free base), 199117-53-8 (monoHCl), 199117-54-9 (monoNa salt)
项目整合开发状态: Preclinical
项目研究机构: Dr. Reddy's Research Foundation (Originator)
合成路线:2-Chloropyridine (I) was condensed with (S)-prolinol (II) to furnish the pyridinylpyrrolidine (III).Subsequent alkylation of the hydroxyl group of (III) with 4-fluorobenzaldehyde (IV) using NaH in hot DMF gave ether (V).Knoevenagel condensation of (V) with 2,4-thiazolidinedione (VI) in the presence of benzoic acid and piperidine afforded the required benzylidene thiazolidine,which was finally treated with maleic acid in acetone to yield the title maleate salt.
📌 参考资料/链接：
参考文献标题:Heterocyclic cpds.having antidiabetic,hypolipidaemic,antihypertensive properties,process for their preparation and pharmaceutical compsns.containing them
文献作者:Rao,P.B.; Ramanujam,R.; Alla,S.R.; Lohray,V.B.; Chakrabarti,R.; Lohray,B.B.(Dr.Reddy's Research Foundation)
参考来源:US 5919782
📄 详细内容
合成路线:2-Chloropyridine (I) was condensed with (S)-prolinol (II) to furnish the pyridinylpyrrolidine (III).Subsequent alkylation of the hydroxyl group of (III) with 4-fluorobenzaldehyde (IV) using NaH in hot DMF gave ether (V).Knoevenagel condensation of (V) with 2,4-thiazolidinedione (VI) in the presence of benzoic acid and piperidine afforded the required benzylidene thiazolidine,which was finally treated with maleic acid in acetone to yield the title maleate salt.
参考文献标题:Thiazolidinedione cpds.having antidiabetic,hypolipidaemic,antihypertensive properties,process for their preparation and pharmaceutical compsns.thereof
文献作者:Ramanujam,R.; Lohray,B.B.; Alla,S.R.; Chakrabarti,R.; Paraselli,R.B.; Lohray,V.B.(Dr.Reddy's Research Foundation)
参考来源:WO 9741120
合成路线:2-Chloropyridine (I) was condensed with (S)-prolinol (II) to furnish the pyridinylpyrrolidine (III).Subsequent alkylation of the hydroxyl group of (III) with 4-fluorobenzaldehyde (IV) using NaH in hot DMF gave ether (V).Knoevenagel condensation of (V) with 2,4-thiazolidinedione (VI) in the presence of benzoic acid and piperidine afforded the required benzylidene thiazolidine,which was finally treated with maleic acid in acetone to yield the title maleate salt.
参考文献标题:Novel euglycemic and hypolipidemic agents.4.Pyridyl- and quinolinyl-containing thiazolidinediones
文献作者:Lohray,B.B.; Bhushan,V.; Reddy,A.S.; Rao,P.B.; Reddy,N.J.; Harikishore,P.; Haritha,N.; Vikramadityan,R.K.; Chakrabarti,R.; Rajagopalan,R.; Katneni,K.
参考来源:J Med Chem 1999,42(14),2569