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【结 构 式】 
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【药物名称】NO-Mesalamine, NO-5-ASA, NCX-456 【化学名称】5-Amino-2-hydroxybenzoic acid 4-(nitrooxy)butyl ester 【CA登记号】256499-26-0 【 分 子 式 】C11H14N2O6 【 分 子 量 】270.24403 |
【开发单位】NicOx (Originator) 【药理作用】GASTROINTESTINAL DRUGS, Inflammatory Bowel Disease, Agents for, Nitric Oxide Donors |
合成路线1
5-Amino-2-hydroxybenzoic acid (I) was protected as the N-Boc derivative (II) by treatment with di-tert-butyl dicarbonate and Et3N. Reaction with triphenylphosphine and carbon tetrabromide in tetrahydrofuran generated the bromobutyl ester (III). After conversion of (III) to the nitroxybutyl ester (IV) by reaction with AgNO3 in refluxing acetonitrile, acid deprotection of the Boc group furnished the title compound.
| 【1】 Del Soldato, P. (NicOx SA); Medicine nitrate salts. WO 0006585 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 41419 | tetrahydrofuran | 109-99-9 | C4H8O | 详情 | 详情 | |
| (I) | 29932 | 5-amino-2-hydroxybenzoic acid | 89-57-6 | C7H7NO3 | 详情 | 详情 |
| (II) | 41418 | 5-[(tert-butoxycarbonyl)amino]-2-hydroxybenzoic acid | C12H15NO5 | 详情 | 详情 | |
| (III) | 41420 | 4-bromobutyl 5-[(tert-butoxycarbonyl)amino]-2-hydroxybenzoate | C16H22BrNO5 | 详情 | 详情 | |
| (IV) | 41421 | 4-(nitrooxy)butyl 5-[(tert-butoxycarbonyl)amino]-2-hydroxybenzoate | C16H22N2O8 | 详情 | 详情 |
Extended Information