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【结 构 式】 
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【药物名称】YM-17551 【化学名称】4-[5-(4-Acetyl-3-hydroxy-2-propylbenzylthio)-1,3,4-thiadiazol-2-ylthiomethyl]benzoic acid 【CA登记号】107859-85-8 【 分 子 式 】C22H22N2O4S3 【 分 子 量 】474.62364 |
【开发单位】Yamanouchi (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Antiinflammatory Drugs, Leukotriene Antagonists |
合成路线1
The reaction of 4-acetyl-3-hydroxy-2-propylbenzyl chloride (I) with 2,5-dimercapto-1,3,4-thiadiazole (II) in 2-butanone gives 2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-5-mercapto-1,3,4-thiadiazole (III), which is condensed with alpha-bromo-p-toluic acid (IV) in 2-butanone.
| 【1】 Mase, T.; Murase, K.; Tsuzuki, R.; Tomioka, K.; Hara, H. (Yamanouchi Pharmaceutical Co., Ltd.); (Substd. benzyl)thio heterocyclic cpds. having leukotriene-antagonist activity. EP 0214732; US 4803211; US 4933348; US 5180730 . |
| 【2】 Yamada, T.; Tomioka, K.; Mase, T.; YM-17551. Drugs Fut 1990, 15, 9, 905. |
| 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) | 11926 | 1-[4-(Chloromethyl)-2-hydroxy-3-propylphenyl]-1-ethanone | C12H15ClO2 | 详情 | 详情 | |
| (II) | 11927 | 5-Sulfanyl-1,3,4-thiadiazol-2-ylhydrosulfide; 1,3,4-Thiadiazole-2,5-dithiol | 1072-71-5 | C2H2N2S3 | 详情 | 详情 |
| (III) | 11928 | 1-(2-Hydroxy-3-propyl-4-[[(5-sulfanyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]phenyl)-1-ethanone | C14H16N2O2S3 | 详情 | 详情 | |
| (IV) | 11929 | 4-(Bromomethyl)benzoic acid; alpha-Bromo-p-toluic acid | 6232-88-8 | C8H7BrO2 | 详情 | 详情 |
Extended Information