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【结 构 式】 
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【药物名称】R-755 【化学名称】N-(2,6-Diethylphenyl)-N'-[3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]thiophen-2-yl]urea 【CA登记号】159387-63-0 【 分 子 式 】C29H30N2OS 【 分 子 量 】454.63925 |
【开发单位】Nihon Nohyaku (Originator) 【药理作用】Atherosclerosis Therapy, CARDIOVASCULAR DRUGS, Lipoprotein Disorders, Treatment of , METABOLIC DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, ACAT Inhibitors, Triglyceride Lowering Agents |
合成路线1
The required benzothiophenecarboxylic acid precursor (IV) was prepared by Friedel-Crafts acylation of 5-(methylthio)indan (I) with 2-methylbenzoyl chloride (II) followed by condensation of the resulting mercapto ketone (III) with hot chloroacetic acid. Curtius rearrangement of carboxylic acid (IV) using diphenylphosphoryl azide produced isocyanate (V), which was subsequently condensed with 2,6-diethylaniline (VI) to yield the title urea.
| 【1】 Nagamine, M.; Yamamoto, K.; Matsui, Y.; Horiuchi, K.; Yoshida, M. (Nihon Nohyaku Co., Ltd.); N-Heteroaryl-N'-phenylurea derivs., their production and use. CA 2116286; EP 0613894; JP 1994340647; US 5464863 . |
| 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) | 50709 | 2,3-dihydro-1H-inden-5-yl methyl sulfide; 5-(methylsulfanyl)indane | C10H12S | 详情 | 详情 | |
| (II) | 14770 | 2-methylbenzoyl chloride; o-Toluoyl chloride | 933-88-0 | C8H7ClO | 详情 | 详情 |
| (III) | 50710 | (2-methylphenyl)[6-(methylsulfanyl)-2,3-dihydro-1H-inden-5-yl]methanone | C18H18OS | 详情 | 详情 | |
| (IV) | 50711 | 3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]thiophene-2-carboxylic acid | C19H16O2S | 详情 | 详情 | |
| (V) | 50712 | 3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]thiophen-2-yl isocyanate; 2-isocyanato-3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]thiophene | C19H15NOS | 详情 | 详情 | |
| (VI) | 35058 | 2,6-diethylphenylamine; 2,6-diethylaniline | 579-66-8 | C10H15N | 详情 | 详情 |