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【结 构 式】 
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【药物名称】A-278637 【化学名称】(-)-9(S)-(3-Bromo-4-fluorophenyl)-2,3,4,5,6,7,8,9-octahydrothieno[3,2- b]quinoline-8-one 1,1-dioxide 【CA登记号】 【 分 子 式 】C17H15BrFNO3S 【 分 子 量 】412.2804 |
【开发单位】Abbott (Originator) 【药理作用】RENAL-UROLOGIC DRUGS, Urinary Incontinence Therapy, K(ATP) Channel Activators |
合成路线1
The Hantzsch reaction between 3-oxotetrahydrothiophene-1,1-dioxide (I), 3-bromo-4-fluorobenzaldehyde (II) and 3-amino-2-cyclohexen-1-one (III) in refluxing EtOH yielded the hydroxy tetrahydropyridine derivative (IV). Dehydration of the cyclic hemiaminal function of (IV) was carried out in refluxing toluene to produce the racemic dihydropyridine, which was resolved into the individual enantiomers by chiral HPLC.
| 【1】 Drizin, I.; et al.; Novel sulfonyldihydropyridine potassium channel openers with potential utility in the treatment of overactive bladder (OAB). 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 197. |
| 【2】 Drizin, I.; Holladay, M.W.; Carroll, W.A.; Zhang, H.Q.; Sullivan, J.P. (Abbott Laboratories Inc.); Potassium channel openers. EP 1040097; US 6265417; WO 9931059 . |
| 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) | 51549 | 3-Oxosulfolane | C4H6O3S | 详情 | 详情 | |
| (II) | 51550 | 3-Bromo-4-fluorobenzaldehyde | 77771-02-9 | C7H4BrFO | 详情 | 详情 |
| (III) | 31475 | 3-amino-2-cyclohexen-1-one | 5220-49-5 | C6H9NO | 详情 | 详情 |
| (IV) | 51551 | 9-(3-bromo-4-fluorophenyl)-3a-hydroxy-2,3,3a,5,6,7,9,9a-octahydro-1H-2H-thieno[3,2-b]quinoline-1,1,8(4H)-trione | C17H17BrFNO4S | 详情 | 详情 |
Extended Information