Tetomilast, OPC-6535
6-(2-(3,4-二乙氧基苯基)噻唑-4-基)甲酸吡啶Chemical Name: 6-[2-(3,4-Diethoxyphenyl)thiazol-4-yl]pyridine-2-carboxylic acid
CAS No. 145739-56-6
项目整合开发状态: Phase III
项目研究机构: Otsuka (Originator)
合成路线:Bromination of 6-acetylpyridine-2-carboxylic acid (I) in hot AcOH generated the alpha-bromoketone (II),which was subsequently esterified to (III) upon refluxing in MeOH.Thioamide (VI) was prepared by treatment of 3,4-diethoxybenzonitrile (IV) with thioacetamide (V) in the presence of HCl.The thiazole derivative (VII) was then obtained by condensation of bromoketone (III) with thioamide (VI) in refluxing MeOH.Finally,basic hydrolysis of the methyl ester function of (VII) provided the title carboxylic acid
📌 参考资料/链接：
参考文献标题:Cytokine production inhibitors and adhesion inhibitors
文献作者:Chihiro,M.; Matsuzaki,T.; Nagamoto,T.; Toda,G.; Sueyoshi,S.; Mori,T.; Kitano,K.; Takemura,I.; Yamashita,H.; Kurimura,M.; Tabusa,F.(Otsuka Pharmaceutical Co.,Ltd.)
参考来源:JP 1998152437; US 2002013469; US 6583163; WO 9814191
📄 详细内容
合成路线:Bromination of 6-acetylpyridine-2-carboxylic acid (I) in hot AcOH generated the alpha-bromoketone (II),which was subsequently esterified to (III) upon refluxing in MeOH.Thioamide (VI) was prepared by treatment of 3,4-diethoxybenzonitrile (IV) with thioacetamide (V) in the presence of HCl.The thiazole derivative (VII) was then obtained by condensation of bromoketone (III) with thioamide (VI) in refluxing MeOH.Finally,basic hydrolysis of the methyl ester function of (VII) provided the title carboxylic acid
参考文献标题:Novel thiazole derivatives as inhibitors of superoxide production by human neutrophils: Synthesis and structure-activity relationships
文献作者:Chihiro,M.; Nagamoto,H.; Takemura,I.; Kitano,K.; Komatsu,H.; Sekiguchi,K.; Tabusa,F.; Mori,T.; Tominaga,M.; Yabuuchi,Y.
参考来源:J Med Chem 1995,38(2),353
产品链接: CAS No. 145739-56-6››