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【结 构 式】 
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【药物名称】Camostat mesilate, Camostat mesylate, FOY-305, Foipan 【化学名称】p-Guanidinobenzoic acid,ester with (p-hydroxyphenyl)acetic acid,ester with N,N-dimethylglycolamide mesylate 【CA登记号】59721-29-8, 59721-28-7 (free base) 【 分 子 式 】C21H26N4O8S 【 分 子 量 】494.52737 |
【开发单位】Ono (Originator), Il Sung (Licensee) 【药理作用】Esophageal Diseases, Treatment of, Gastroesophageal Reflux Disease, Agents for, GASTROINTESTINAL DRUGS, Pancreatic Disorders, Treatment of, Protease Inhibitors, Trypsin Inhibitors |
合成路线1
The reaction of p-hydrophenylacetic acid (I) with N,N-dimethylbromoacetamide (II) by means of triethylamine in reftuxing acetonitrile gives N,N-dimethylcarbamoylmethyl-p-hydroxyphenylacetate (III), which is then condensed with p-guanidinobenzoyl chloride (IV) [obtained from the corresponding acid p-guanidinobenzoic acid (V) and thionyl chloride] in pyridine.
| 【1】 Fujii, S.; Uegai, Y.; Watanabe, T.; Kayama, N. (Ono Pharmaceutical Co., Ltd.); Guanidinobenzoic acid derivatives. DE 2548886; FR 2289181; GB 1472700; JP 76054530; US 4021472 . |
| 【2】 Fujii, S.; et al. (Ono Pharmaceutical Co., Ltd.); Guanidinobenzoic acid derivatives and antiplasmin agents and remedies for pancreas diseases containing the said guanidinobensolc acid derivatives. JP 52089640 . |
| 【3】 Castaner, J.; Serradell, M.N.; Hashimoto, K.; Camostat Mesylate. Drugs Fut 1985, 10, 11, 897. |
| 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) | 18430 | 2-(4-Hydroxyphenyl)acetic acid; 4-Hydroxyphenylacetic acid | 156-38-7 | C8H8O3 | 详情 | 详情 |
| (II) | 29753 | 2-bromo-N,N-dimethylacetamide | C4H8BrNO | 详情 | 详情 | |
| (III) | 29754 | 2-(dimethylamino)-2-oxoethyl 2-(4-hydroxyphenyl)acetate | C12H15NO4 | 详情 | 详情 | |
| (IV) | 29755 | 4-[[amino(imino)methyl]amino]benzoic acid | C8H9N3O2 | 详情 | 详情 | |
| (V) | 22548 | 4-[[amino(imino)methyl]amino]benzoyl chloride | C8H8ClN3O | 详情 | 详情 |
合成路线2
By reaction of N,N-dimethylcarbamoylmethyl-p-(p-aminobenzoyloxy)phenylacetate (VI) with cyanamide (VII).
| 【1】 Fujii, S.; et al. (Ono Pharmaceutical Co., Ltd.); Preparation of guanidinobenzoic acid derivatives. JP 54052052 . |
| 【2】 Castaner, J.; Serradell, M.N.; Hashimoto, K.; Camostat Mesylate. Drugs Fut 1985, 10, 11, 897. |