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【结 构 式】

【药物名称】AVE-0991

【化学名称】N-Ethyl-N'-[3-[4-(5-formyl-4-methoxy-2-phenyl-1H-imidazol-1-ylmethyl)phenyl]-5-isobutylthien-2-ylsulfonyl]urea

【CA登记号】304462-19-9, 306288-04-0 (monosodium salt)

【 分 子 式 】C29H32N4O5S2

【 分 子 量 】580.73019

【开发单位】Aventis Pharma (Originator)

【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Angiotensin Receptor Agonists

合成路线1

4-Chloro-5-formyl-2-phenylimidazole (I) is alkylated with 4-bromobenzyl bromide (II) in the presence of K2CO3 in DMF to produce the N-bromobenzyl imidazole (III). Subsequent Suzuki coupling between aryl bromide (III) and 5-isobutyl-2-[(N-tert-butyl)sulfonamido]thiophene-3-boronic acid (IV) affords the thienylphenyl derivative (V). The N-tert-butyl group is then removed by treatment with trifluoroacetic acid in the presence of anisole, yielding sulfonamide (VI). Displacement of the chloro substituent of (VI) with MeOH/NaOH furnishes the 4-methoxy imidazole (VII). Finally, condensation of sulfonamide (VII) with ethyl isocyanate gives rise to the target N-sulfonyl urea compound.

1 Wiemer, G.; Heitsch, H. (Aventis Pharma Deutschland GmbH); 1-(p-Thienylbenzyl)-imidazoles as angiotensin-(1-7) receptor agonists, method for the production and the utilization thereof and pharmaceutical preparations containing said cpds.. EP 1185527; JP 2002544130; US 6235766; US 6429222; WO 0068226 .
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) 63250 4-chloro-2-phenyl-1H-imidazole-5-carbaldehyde C10H7ClN2O 详情 详情
(II) 16109 1-bromo-4-(bromomethyl)benzene; 4-Bromobenzyl bromide 589-15-1 C7H6Br2 详情 详情
(III) 63251 1-(4-bromobenzyl)-4-chloro-2-phenyl-1H-imidazole-5-carbaldehyde C17H12BrClN2O 详情 详情
(IV) 63252 2-[(tert-butylamino)sulfonyl]-5-isobutyl-3-thienylboronic acid C12H22BNO4S2 详情 详情
(V) 63253 N-(tert-butyl)-3-{4-[(4-chloro-5-formyl-2-phenyl-1H-imidazol-1-yl)methyl]phenyl}-5-isobutyl-2-thiophenesulfonamide C29H32ClN3O3S2 详情 详情
(VI) 63254 3-{4-[(4-chloro-5-formyl-2-phenyl-1H-imidazol-1-yl)methyl]phenyl}-5-isobutyl-2-thiophenesulfonamide C25H24ClN3O3S2 详情 详情
(VII) 63255 3-{4-[(5-formyl-4-methoxy-2-phenyl-1H-imidazol-1-yl)methyl]phenyl}-5-isobutyl-2-thiophenesulfonamide C26H27N3O4S2 详情 详情
Extended Information