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【结 构 式】 
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【药物名称】VUF-K-9015 【化学名称】7-[3-[1-(2-Ethoxyethyl)-1H-benzimidazol-2-ylmethoxy]benzyloxy]-3,4-dihydro-2H-1,4-benzothiazin-3-one 【CA登记号】198012-83-8 【 分 子 式 】C27H27N3O4S 【 分 子 量 】489.59794 |
【开发单位】Kowa (Originator), Vrije Universiteit (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Histamine H1 Antagonists, Leukotriene CysLT1 (LTD4) Antagonists |
合成路线1
Alkylation of 3-hydroxybenzyl alcohol (II) with benzimidazolylmethyl chloride (I) in the presence of K2CO3 and tetrabutylammonium bromide provided ether (III). The hydroxyl group of (III) was converted to chloride (IV) by treatment with thionyl chloride. Finally, alkylation of hydroxybenzothiazinone (V) with chloride (IV) yielded the title compound.
| 【1】 Tamura, M.; Tohma, T.; Onogi, K.; et al.; VUF-K-8707 and analogs, non-acidic leukotriene D4 receptor antagonists. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.226. |
| 【2】 Timmerman, H.; Zhang, M.; Onogi, K.; Tamura, M.; Toma, T.; Wada, Y. (Kowa Co., Ltd.); Heteroaryl substd. phenylene derivs., their preparation and their use a leukotriene receptor antagonists. EP 0799826; JP 1997323975; US 5756518; US 5885987; US 6011033 . |
| 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) | 28288 | 2-(chloromethyl)-1-(2-ethoxyethyl)-1H-benzimidazole | C12H15ClN2O | 详情 | 详情 | |
| (II) | 17296 | 3-Hydroxybenzyl alcohol; 3-(hydroxymethyl)phenol | 620-24-6 | C7H8O2 | 详情 | 详情 |
| (III) | 28289 | (3-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]methoxy]phenyl)methanol | C19H22N2O3 | 详情 | 详情 | |
| (IV) | 28291 | 2-[[3-(chloromethyl)phenoxy]methyl]-1-(2-ethoxyethyl)-1H-benzimidazole | C19H21ClN2O2 | 详情 | 详情 | |
| (V) | 28290 | 7-hydroxy-2H-1,4-benzothiazin-3(4H)-one | C8H7NO2S | 详情 | 详情 |
Extended Information