【药物名称】Nateglinide, DJN-608, SDZ-DJN-608, YM-026, AY-4166, A-4166, Trazec, Fastic, Starlix, Starsis
化学结构式(Chemical Structure):
参考文献No.5189
标题:Hypoglycemic agent
作者:Toyoshima, S.; Seto, Y.; Shinkai, H.; Toi, K.; Kumashiro, I. (Ajinomoto Co., Inc.)
来源:EP 0196222; US 4816484
合成路线图解说明:

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No.98430
标题:N-(Cyclohexyl)carbonyl-D-phenylalanines and related compounds. A new class of oral hypoglycemic agents. 2
作者:Shinkai, H.; Nishikawa, M.; Sato, Y.; Toi, K.; Kumashiro, I.; Seto, Y.; Fukuma, M.; Dan, K.; Toyoshima, S.
来源:J Med Chem 1989,32(7),1436
合成路线图解说明:

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No.209238
标题:AY-4166
作者:Prous, J.; Graul, A.; Casta馿r, J.
来源:Drugs Fut 1993,18(6),503
合成路线图解说明:

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.

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