SUN-C8257
Chemical Name: 2-Amino-4-(7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-3-ylsulfonyl)benzoic acid
CAS No. 259536-74-8, 259536-75-9 (Na salt)
项目整合开发状态: Preclinical
项目研究机构: Daiichi Suntory Pharma (Originator)
合成路线:Benzyl 4-chloroanthranilate (I) is treated with phenyl chloroformate in hot dioxane to produce carbamate (II).Condensation between the phenyl carbamate (II) and sulfonamide (III) in the presence of DBU yields the sulfonyl urea (IV).The benzyl ester and N-benzyloxycarbonyl groups of (IV) are then removed by catalytic hydrogenolysis to furnish acid (V).Cyclization of (V) by means of CDI leads to the quinazolinedione (VI).Finally,the tert-butyl ester group of (VI) is cleaved by treatment with trifluoroacetic acid to provide the title compound
📌 参考资料/链接：
参考文献标题:Quinazoline derivs.and pharmaceutical application thereof
文献作者:Ito,A.; Fukami,H.; Imajo,S.(Suntory Ltd.)
参考来源:EP 1114035; JP 2002523404; WO 0010982
📄 详细内容
合成路线:Benzyl 4-chloroanthranilate (I) is treated with phenyl chloroformate in hot dioxane to produce carbamate (II).Condensation between the phenyl carbamate (II) and sulfonamide (III) in the presence of DBU yields the sulfonyl urea (IV).The benzyl ester and N-benzyloxycarbonyl groups of (IV) are then removed by catalytic hydrogenolysis to furnish acid (V).Cyclization of (V) by means of CDI leads to the quinazolinedione (VI).Finally,the tert-butyl ester group of (VI) is cleaved by treatment with trifluoroacetic acid to provide the title compound
参考文献标题:Substituted 3-phenylsulfonylquinazoline-2,4-dione derivatives as novel nonpeptide inhibitors of human heart chymase
文献作者:Fukami,H.; Imajo,S.; Ito,A.; Kakutani,S.; Shibata,H.; Sumida,M.; Tanaka,T.; Niwata,S.; Saitoh,M.; Kiso,Y.; Miyazaki,M.; Okunishi,H.; Urata,H.; Arakawa,K.
参考来源:Drug Des Discov 2000,17(1),69