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【结 构 式】 
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【药物名称】BN-80933 【化学名称】N1-[4-[4-[6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2(S)-ylcarbonyl]piperazin-1-yl]phenyl]thiophene-2-carboxamidine 【CA登记号】214348-10-4, 214124-18-2 (undefined isomer) 【 分 子 式 】C29H34N4O3S 【 分 子 量 】518.68333 |
【开发单位】Ipsen (Originator) 【药理作用】Cerebrovascular Diseases, Treatment of, Ischemic Stroke, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, Free Radical Scavengers, Neuronal Nitric Oxide Synthase Inhibitors |
合成路线1
(S)-6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (I) was coupled to N-(4-nitrophenyl)piperazine (II) via activation with 1,1'-carbonyldiimidazole to furnish the corresponding amide (III). Subsequent hydrogenation of the nitro group of (III) over Pd/C provided aniline (IV). This was finally condensed with S-methyl-2-thiophenethiocarboxamide (V) to yield the title amidine.
| 【1】 Chabrier de Lassauniere, P.-E.; Auguet, M.; Auvin, S.; Bigg, D. (SCRAS (Societé de Conseils de Recherches et d'Applications Scientifiques)); Novel 2-(iminomethyl)amino-phenyl derivs., preparation, application as medicines and pharmaceutical compsns. containing same. EP 0973763; WO 9842696 . |
| 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) | 34833 | (2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylic acid | C14H18O4 | 详情 | 详情 | |
| (II) | 20299 | 1-(4-nitrophenyl)piperazine | 6269-89-2 | C10H13N3O2 | 详情 | 详情 |
| (III) | 34834 | [(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl][4-(4-nitrophenyl)-1-piperazinyl]methanone | C24H29N3O5 | 详情 | 详情 | |
| (IV) | 34835 | [4-(4-aminophenyl)-1-piperazinyl][(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methanone | C24H31N3O3 | 详情 | 详情 | |
| (V) | 34836 | methyl 2-thiophenecarbimidothioate | C6H7NS2 | 详情 | 详情 |
合成路线2
2-thiophenecarbonitrile (VI) was converted into imidate (VII) and then coupled with aniline (IV) in refluxing MeOH to give the title compound.
| 【1】 Chabrier de Lassauniere, P.-E.; Auguet, M.; Auvin, S.; Bigg, D. (SCRAS (Societé de Conseils de Recherches et d'Applications Scientifiques)); Novel 2-(iminomethyl)amino-phenyl derivs., preparation, application as medicines and pharmaceutical compsns. containing same. EP 0973763; WO 9842696 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 34835 | [4-(4-aminophenyl)-1-piperazinyl][(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methanone | C24H31N3O3 | 详情 | 详情 | |
| (VI) | 34025 | Thiophene-2-carbonitrile; 2-thiophenecarbonitrile | 1003-31-2 | C5H3NS | 详情 | 详情 |
| (VII) | 34837 | methyl 2-thiophenecarboximidoate | C6H7NOS | 详情 | 详情 |