|
【结 构 式】 
|
【药物名称】AM-682 【化学名称】2-[(4-Carboxybenzoyl)amino]-4-[(1-oxopropyl)amino]benzoic acid 1-ethyl ester sodium salt 【CA登记号】73625-86-2 (free acid) 【 分 子 式 】C20H19N2NaO6 【 分 子 量 】406.37403 |
【开发单位】Chugai (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS |
合成路线1
4-Nitroanthranilic acid (I) is combined with terephthalic acid by reaction with the half ester chloride, followed by hydrolysis, to give the nitro diacid (II), which is catalytically hydrogenated to the amino diacid (III). Amidation and selective half-esterification of the amino diacid (III) is believed to occur through an oxazinone-type intermediate (IV), which is opened by alcoholysis under basic conditions to afford AM-682 free acid (V).
| 【1】 Tasaka, K.; AM-682. Drugs Fut 1989, 14, 8, 738. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 25029 | p-Phthalic acid monomethyl ester chloride; Terephthalic acid monomethyl ester chloride; Methyl 4-chlorocarbonylbenzoate | 7377-26-6 | C9H7ClO3 | 详情 | 详情 |
| (I) | 21205 | 2-amino-4-nitrobenzoic acid | 619-17-0 | C7H6N2O4 | 详情 | 详情 |
| (II) | 21206 | 2-[(4-carboxybenzoyl)amino]-4-nitrobenzoic acid | C15H10N2O7 | 详情 | 详情 | |
| (III) | 21207 | 4-amino-2-[(4-carboxybenzoyl)amino]benzoic acid | C15H12N2O5 | 详情 | 详情 | |
| (IV) | 21208 | 4-[4-oxo-7-(propionylamino)-4H-3,1-benzoxazin-2-yl]benzoic acid | C18H14N2O5 | 详情 | 详情 | |
| (V) | 21209 | 4-[[2-(ethoxycarbonyl)-5-(propionylamino)anilino]carbonyl]benzoic acid | C20H20N2O6 | 详情 | 详情 |