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项目整合精选>>>Nateglinide, DJN-608, SDZ-DJN-608, YM-026, AY-4166, A-4166, Trazec, Fastic, Starlix, Starsis
Nateglinide, DJN-608, SDZ-DJN-608, YM-026, AY-4166, A-4166, Trazec, Fastic, Starlix, Starsis
那格列奈Chemical Name: (-)-N-(trans-4-Isopropylcyclohexyl-1-carbonyl)-D-phenylalanine
CAS No. 105816-04-4
项目整合开发状态: Launched-1999
项目研究机构: Ajinomoto (Originator), Aventis Pharma (Marketer), Novartis (Licensee), Yamanouchi (Codevelopment)
合成路线:The hydrogenation of 4-isopropylbenzoic acid (I) with H2 over PtO2 in acetic acid gives 4-isopropylcyclohexanecarboxylic acid as a mixture of cis- and trans-isomers (II).This mixture is esterified with methanol to the corresponding mixture of methyl esters (III),which is isomerized with NaH at 150 C without solvent,affording the trans-methyl ester (IV).Hydrolysis of (IV) with NaOH in methanol - water gives the free acid (V),which is finally condensed with D-phenylalanine (VI) by means of N-hydroxysuccinimide and dicyclohexylcarbodiimide in chloroform.
📌 参考资料/链接：
参考文献标题:Hypoglycemic agent
文献作者:Toyoshima,S.; Seto,Y.; Shinkai,H.; Toi,K.; Kumashiro,I.(Ajinomoto Co.,Inc.)
参考来源:EP 0196222; US 4816484
📄 详细内容
合成路线:The hydrogenation of 4-isopropylbenzoic acid (I) with H2 over PtO2 in acetic acid gives 4-isopropylcyclohexanecarboxylic acid as a mixture of cis- and trans-isomers (II).This mixture is esterified with methanol to the corresponding mixture of methyl esters (III),which is isomerized with NaH at 150 C without solvent,affording the trans-methyl ester (IV).Hydrolysis of (IV) with NaOH in methanol - water gives the free acid (V),which is finally condensed with D-phenylalanine (VI) by means of N-hydroxysuccinimide and dicyclohexylcarbodiimide in chloroform.
参考文献标题:N-(Cyclohexyl)carbonyl-D-phenylalanines and related compounds.A new class of oral hypoglycemic agents.2
文献作者:Shinkai,H.; Nishikawa,M.; Sato,Y.; Toi,K.; Kumashiro,I.; Seto,Y.; Fukuma,M.; Dan,K.; Toyoshima,S.
参考来源:J Med Chem 1989,32(7),1436
合成路线:The hydrogenation of 4-isopropylbenzoic acid (I) with H2 over PtO2 in acetic acid gives 4-isopropylcyclohexanecarboxylic acid as a mixture of cis- and trans-isomers (II).This mixture is esterified with methanol to the corresponding mixture of methyl esters (III),which is isomerized with NaH at 150 C without solvent,affording the trans-methyl ester (IV).Hydrolysis of (IV) with NaOH in methanol - water gives the free acid (V),which is finally condensed with D-phenylalanine (VI) by means of N-hydroxysuccinimide and dicyclohexylcarbodiimide in chloroform.
参考文献标题:AY-4166
文献作者:Prous,J.; Graul,A.; Castar,J.
参考来源:Drugs Fut 1993,18(6),503
产品链接: CAS No. 105816-04-4››