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【结 构 式】 
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【药物名称】NK-5807 【化学名称】(-)-N-[4-(10-Acetamido-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridin-2-yl)-2(S)-(3,4-dichlorophenyl)butyl]-N-methylbenzamide maleate 【CA登记号】219536-57-9 (free base), 219536-58-0 (fumarate salt (1:1)) 【 分 子 式 】C36H36Cl2N4O6 【 分 子 量 】691.61752 |
【开发单位】Nippon Kayaku (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, Chronic Obstructive Pulmonary Diseases (COPD), Treatment of, GASTROINTESTINAL DRUGS, Irritable Bowel Syndrome, Agents for, RENAL-UROLOGIC DRUGS, RESPIRATORY DRUGS, Urinary Incontinence Therapy, Tachykinin NK2 Antagonists |
合成路线1
The benzonaphthyridine system (III) was prepared by condensation of 1-Boc-4-piperidone (I) with 2-aminobenzonitrile (II) in the presence of ZnCl2. After acetylation of the 10-amino group of (III) with Ac2O in pyridine to afford (IV), the N-Boc protecting group was removed by treatment with HCl in dioxan-methanol, yielding 10-acetylamino-1,2,3,4-tetrahydrobenzo[b][1,6]-naphthyridine (V). The tricyclic amine (V) was then alkylated with the chiral sulfonate (VI), and the target compound was finally converted to the corresponding fumarate salt.
| 【1】 Honda, M.; Sato, Y.; Oka, H.; Iida, M. (Nippon Kayaku Co., Ltd.); Novel naphthyridine derivs. or salts thereof. EP 0997462; JP 2000038386; US 6294547; WO 9900388 . |
| 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) | 18620 | tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone | 79099-07-3 | C10H17NO3 | 详情 | 详情 |
| (II) | 19493 | 2-aminobenzonitrile | 1885-29-6 | C7H6N2 | 详情 | 详情 |
| (III) | 49140 | tert-butyl 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridine-2(1H)-carboxylate | C17H21N3O2 | 详情 | 详情 | |
| (IV) | 49141 | tert-butyl 10-(acetamido)-3,4-dihydrobenzo[b][1,6]naphthyridine-2(1H)-carboxylate | C19H23N3O3 | 详情 | 详情 | |
| (V) | 49142 | N-(1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridin-10-yl)acetamide | C14H15N3O | 详情 | 详情 | |
| (VI) | 49143 | (3S)-4-[benzoyl(methyl)amino]-3-(3,4-dichlorophenyl)butyl benzenesulfonate | C24H23Cl2NO4S | 详情 | 详情 |