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【结 构 式】 
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【药物名称】Setastine hydrochloride, EGYT-2062, EGIS-2062, Loderix 【化学名称】1-[2-[1-(4-Chlorophenyl)-1-phenylethoxy]ethyl]hexahydro-1H-azepine hydrochloride 【CA登记号】59767-13-4, 64294-95-7 (free base) 【 分 子 式 】C22H29Cl2NO 【 分 子 量 】394.38853 |
【开发单位】Egis (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, Drugs for Allergic Rhinitis, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders, Histamine H1 Antagonists |
合成路线1
4-Chloro-alpha-methylbenzhydrol (I) is alkylated with N-(2-chloroethyl)hexamethyleneimine (II) in benzene in the presence of sodium amide to give setastine. The starting products are obtained as follows; Caprolactame (III) is O-alkylated with dimethyl sulfate to yield the lactimether (IV), which is reduced with sodium borohydride to hexamethyleneimine (II). Friedel Cratts acylation of chlorobenzene (V) with benzoyl chloride (VI) affords the benzophenone (VII), to which methylmagnesium bromide is added to give the carbinol (I).
| 【1】 Rakoczi, J.; Bolla, K.; Beck, I.; Porszasz, K. (Egis Pharmaceuticals Ltd.); New benzhydryloxy-alkylamine derivs. and process f. DE 2528194; GB 1463038 . |
| 【2】 Nogradi, M.; Setastine hydrochloride. Drugs Fut 1987, 12, 4, 357. |
| 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) | 22917 | 1-(4-chlorophenyl)-1-phenyl-1-ethanol | C14H13ClO | 详情 | 详情 | |
| (II) | 22918 | 1-(2-chloroethyl)azepane | C8H16ClN | 详情 | 详情 | |
| (III) | 22919 | 2-azepanone | 105-60-2 | C6H11NO | 详情 | 详情 |
| (IV) | 22920 | 7-methoxy-3,4,5,6-tetrahydro-2H-azepine; methyl 3,4,5,6-tetrahydro-2H-azepin-7-yl ether | 2525-16-8 | C7H13NO | 详情 | 详情 |
| (V) | 10190 | 1-Chlorobenzene | 108-90-7 | C6H5Cl | 详情 | 详情 |
| (VI) | 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 |
| (VII) | 22923 | (4-chlorophenyl)(phenyl)methanone; 4-Chlorobenzophenone | 134-85-0 | C13H9ClO | 详情 | 详情 |