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【结 构 式】 
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【药物名称】SSR-69071 【化学名称】2-(4-Isopropyl-6-methoxy-1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-ylmethoxy)-9-[2-(1-piperidinyl)ethoxy]-4H-pyrido[1,2-a]pyrimidin-4-one 【CA登记号】344930-95-6, 344930-98-9 (benzoate), 344930-99-0 (citrate), 344930-97-8 (fumarate), 344930-96-7 (hydrochloride), 344931-13-1 (ta 【 分 子 式 】C27H32N4O7S 【 分 子 量 】556.64269 |
【开发单位】Sanofi-synthélabo (Originator), Chinoin (Codevelopment) 【药理作用】Chronic Obstructive Pulmonary Diseases (COPD), Treatment of, Respiratory Distress Syndrome, Agents for, RESPIRATORY DRUGS, Leukocyte Elastase Inhibitors |
合成路线1
2-Amino-3-hydroxypyridine (I) is alkylated with N-(2-chloroethyl)piperidine (II) under phase transfer conditions to provide ether (III). Subsequent cyclization of aminopyridine (III) with bis-trichlorophenyl malonate (IV) in refluxing acetone leads to the pyridopyrimidine (V). This is finally condensed with the N-(bromomethyl)saccharin derivative (VI) to furnish the title compound.
| 【1】 Hermecz, I.; Kapui, Z.; Arányi, P.; Bátori, S.; Varga, M.; Dessilla, S.; Lévai, F.; Mikus, E.; Pascal, M.; Simonot, B.; Urbán Szabó, K.; Vasváriné Debreczy, L.; T. Nagy, L. (Sanofi-Synthélabo); Saccharin derivs. as orally active elastase inhibitors. WO 0144245 . |
| 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) | 37086 | 2-amino-3-pyridinol; 2-Amino-3-hydroxypyridine | 16867-03-1 | C5H6N2O | 详情 | 详情 |
| (II) | 10117 | 1-(2-Chloroethyl)piperidine; N-(2-Chloroethyl)piperidine | 1932-03-2 | C7H14ClN | 详情 | 详情 |
| (III) | 62082 | 3-[2-(1-piperidinyl)ethoxy]-2-pyridinamine; 3-[2-(1-piperidinyl)ethoxy]-2-pyridinylamine | C12H19N3O | 详情 | 详情 | |
| (IV) | 12956 | bis(2,4,6-trichlorophenyl) malonate | C15H6Cl6O4 | 详情 | 详情 | |
| (V) | 62083 | 2-hydroxy-9-[2-(1-piperidinyl)ethoxy]-4H-pyrido[1,2-a]pyrimidin-4-one | C15H19N3O3 | 详情 | 详情 | |
| (VI) | 62084 | 2-(bromomethyl)-4-isopropyl-6-methoxy-1H-1,2-benzisothiazole-1,1,3(2H)-trione | C12H14BrNO4S | 详情 | 详情 |