|
【结 构 式】 
|
【药物名称】NCX-530 【化学名称】2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 3-(nitrooxymethyl)phenyl ester 【CA登记号】204268-63-3 【 分 子 式 】C26H21ClN2O7 【 分 子 量 】508.91947 |
【开发单位】NicOx (Originator), Kyoto Pharmaceutical University (Codevelopment) 【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Nitric Oxide Donors |
合成路线1
The title compound was synthesized by two procedures. Indomethacin (I) was coupled with 3-hydroxybenzyl nitrate (II) using DCC to yield the title ester.
| 【1】 Del Soldato, P.; Sannicolo', F. (NicOx SA); Nitric ester derivs. and their use in urinary incontinence and other diseases. JP 2000517332; WO 9809948 . |
合成路线2
In a related procedure, indomethacin chloride (III) was coupled with 3-hydroxybenzaldehyde (IV) to yield ester (V). Catalytic hydrogenation of the formyl group of (V) over Pd/C produced alcohol (VI), which was further converted to chloride (VII) upon treatment with SOCl2. The chloride group of (VII) was finally displaced with silver nitrate to furnish the corresponding nitrate ester.
| 【1】 Garufi, M.; Del Soldato, P. (NicOx SA); Synthesis method of nitroxymethylphenyl esters of aspirin derivs.. WO 0044705 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 24047 | 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl chloride | C19H15Cl2NO3 | 详情 | 详情 | |
| (IV) | 28537 | 3-hydroxybenzaldehyde | 100-83-4 | C7H6O2 | 详情 | 详情 |
| (V) | 48379 | 3-formylphenyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate | C26H20ClNO5 | 详情 | 详情 | |
| (VI) | 48380 | 3-(hydroxymethyl)phenyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate | C26H22ClNO5 | 详情 | 详情 | |
| (VII) | 48381 | 3-(chloromethyl)phenyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate | C26H21Cl2NO4 | 详情 | 详情 |