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【结 构 式】 
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【药物名称】CP-320626 【化学名称】5-Chloro-N-[1(S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-1H-indole-2-carboxamide 【CA登记号】186430-23-9 【 分 子 式 】C23H23ClFN3O3 【 分 子 量 】443.90946 |
【开发单位】Pfizer (Originator) 【药理作用】Antidiabetic Drugs, ENDOCRINE DRUGS, Lipoprotein Disorders, Treatment of , METABOLIC DRUGS, Glycogen Phosphorylase Inhibitors, Lanosterol 14alpha-demethylase Inhibitors |
合成路线1
The reaction of N-(tert-butoxycarbonyl)-L-4-fluorophenylalanine (I) with 4-hydroxypiperidine (II) by means of triethylamine, EDC and HOBT in dichloromethane gives the expected piperidide (III), which is deprotected with with HCl in dioxane to afford (IV) with a free amino group that is condensed with 5-chloro-1H-indole-2-carboxylic acid (V) by means of triethylamine, EDC and HOBT as before.
| 【1】 Hoover, D.J.; et al.; Indole-2-carboxamide inhibitors of human liver glycogen phosphorylase. J Med Chem 1998, 41, 16, 2934. |
| 【2】 Hulin, B.; Hoover, D.J.; Treadway, J.L.; Martin, W.H.; Phillips, D. (Pfizer Inc.); Substd. N-(indole-2-carbonyl)-glycinamides and derivs. as glycogen phosphorylase inhibitors. EP 0832065; WO 9639384 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 25929 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-fluorophenyl)propionic acid | C14H18FNO4 | 详情 | 详情 | |
| (II) | 12076 | 4-Piperidinol; 4-Hydroxypiperidine | 5382-16-1 | C5H11NO | 详情 | 详情 |
| (III) | 25930 | tert-butyl (1S)-1-(4-fluorobenzyl)-2-(4-hydroxy-1-piperidinyl)-2-oxoethylcarbamate | C19H27FN2O4 | 详情 | 详情 | |
| (IV) | 25931 | (2S)-2-amino-3-(4-fluorophenyl)-1-(4-hydroxy-1-piperidinyl)-1-propanone | C14H19FN2O2 | 详情 | 详情 | |
| (V) | 25932 | 5-Chloroindole-2-carboxylic acid; 5-Chloro-1H-indole-2-carboxylic acid | 10517-21-2 | C9H6ClNO2 | 详情 | 详情 |