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【结 构 式】 
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【药物名称】ML-10375 【化学名称】cis-4-Amino-2-methoxy-5-chlorobenzoic acid 2-(3,5-dimethylpiperidin-1-yl)ethyl ester 【CA登记号】174008-52-7, 174008-51-6 (trans-isomer), 174008-53-8 (undefined isomer), 174008-54-9 (undefined isomer, monoHCl salt) 【 分 子 式 】C17H25ClN2O3 【 分 子 量 】340.8534 |
【开发单位】Sanofi-synthélabo (Originator) 【药理作用】Anxiolytics, GASTROINTESTINAL DRUGS, Irritable Bowel Syndrome, Agents for, Pharmacological Tools, PSYCHOPHARMACOLOGIC DRUGS, 5-HT4 Antagonists |
合成路线1
Reaction of 4-amino-5-chloro-2-methoxybenzoic acid (I) with 1,2-dibromoethane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene afforded bromoethyl ester (II). This was then condensed with a mixture of cis and trans 3,5-dimethylpiperidines (III), and the resulting mixture of amines was finally separated by column chromatogaphy to provide the target cis compound.
| 【1】 Sicsic, S.; Soulier, J.-L.; Yang, D.; et al.; New esters of 4-amino-5-chloro-2-methoxybenzoic acid as potent agonists and antagonists for 5-HT4 receptors. J Med Chem 1997, 40, 4, 608. |
| 【2】 Langlois, M.; Guzzi, U.; Cecchi, R.; Croci, T. (Midy SpA); Esters of 4-amino-5-chloro-2-methoxybenzoic acid, process for their preparation and pharmaceutical compsns. containing them. EP 0683161 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10252 | 1,2-Dibromoethane; Ethylene dibromide | 106-93-4 | C2H4Br2 | 详情 | 详情 | |
| (I) | 12419 | 4-Amino-5-chloro-2-methoxybenzoic acid | 7206-70-4 | C8H8ClNO3 | 详情 | 详情 |
| (II) | 26533 | 2-bromoethyl 4-amino-5-chloro-2-methoxybenzoate | C10H11BrClNO3 | 详情 | 详情 | |
| (III) | 26534 | 3,5-dimethylpiperidine | 35794-11-7 | C7H15N | 详情 | 详情 |