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【结 构 式】 
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【药物名称】Ranitidine Bismutrex, Ranitidine bismuth citrate, GR-122311-X, Tritec, Pylorid 【化学名称】N-[2-[5-(Dimethylaminomethyl)furan-2-ylmethylsulfanyl]ethyl]-N'-methyl-2-nitroethene-1,1-diamine 2-hydroxypropane-1,2,3-tricarboxylate bismuth(3+) complex (1:1:1) 【CA登记号】128345-62-0, 139638-15-6 (deleted CAS) 【 分 子 式 】C19H27BiN4O10S 【 分 子 量 】712.49184 |
【开发单位】GlaxoSmithKline (Originator) 【药理作用】Anti-Helicobacter Pylori Agents, Antiulcer Drugs, Gastric Antisecretory Drugs, GASTROINTESTINAL DRUGS, Histamine H2 Receptor Antagonists |
合成路线1
The reaction of 2-furan-methanol (I) with dimethylamine and formaldehyde gives 5-(dimethylaminomethyl)furan-2-methanol (II), which is condensed with 2-sulfanylethylamine (III) yielding 2-[5-(dimethylaminomethyl)furan-2-ylsulfanyl]ethylamine (IV). The condensation of (IV) with 1-(methylamino)-1-(methylsulfanyl)-2-nitroethylene (V), obtained from 1,1,-bis(methylsulfanyl)-2-nitroethylene (VI) and methylamine, in hot acetone, or by heating at 100-120 C affords N-[2-[5-(dimethylaminomethyl)furan-2-ylmethylsulfanyl]ethyl]- N'-methyl-2-nitroethylene-1,1-diamine (VII) , which is finally complexed with bismuth (+3) citrate (VIII), obtained by reaction of NO3BiO with citric acid (IX) in hot water.
| 【1】 Castaner, J.; Rabasseda, X.; Mealy, N.; Ranitidine Bismuth Citrate. Drugs Fut 1995, 20, 5, 480. |
| 【2】 Clitherow, J.W. (Glaxo Wellcome plc); Ranitidine derivs. BE 1003254; CH 679582; GB 2220937; JP 1990117684; US 5008256 . |
| 【3】 Bradshaw, J.; Price, B.J.; Clitherow, J.W.; Aminoalkyl furan derivs. GB 1565966 . |
| 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) | 13848 | 2-Furylmethanol; Furfuryl Alcohol | 98-00-0 | C5H6O2 | 详情 | 详情 |
| (II) | 13849 | [5-[(dimethylamino)methyl]-2-furyl]methanol | C8H13NO2 | 详情 | 详情 | |
| (III) | 13186 | 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine | 60-23-1 | C2H7NS | 详情 | 详情 |
| (IV) | 13851 | 2-[([5-[(Dimethylamino)methyl]-2-furyl]methyl)sulfanyl]-1-ethanamine; N-[(5-[[(2-Aminoethyl)sulfanyl]methyl]-2-furyl)methyl]-N,N-dimethylamine | C10H18N2OS | 详情 | 详情 | |
| (V) | 13852 | N-Methyl-N-[(E)-1-(methylsulfanyl)-2-nitroethenyl]amine; (E)-N-Methyl-1-(methylsulfanyl)-2-nitro-1-ethenamine; (E)-1-Methylthio-1-methylamino-2-nitroethylene | 61832-41-5 | C4H8N2O2S | 详情 | 详情 |
| (VI) | 13853 | Methyl 1-(methylsulfanyl)-2-nitrovinyl sulfide; 1,1-Bis(methylthio)-2-nitroethylene; 1,1-Bis(methylsulfanyl)-2-nitroethylene | 13623-94-4 | C4H7NO2S2 | 详情 | 详情 |
| (VII) | 13854 | N-[2-[([5-[(Dimethylamino)methyl]-2-furyl]methyl)sulfanyl]ethyl]-N-[(E)-1-(methylamino)-2-nitroethenyl]amine; (E)-N(1)-[2-[([5-[(Dimethylamino)methyl]-2-furyl]methyl)sulfanyl]ethyl]-N(1)-methyl-2-nitro-1,1-ethenediamine; Ranitidine | 66357-35-5 | C13H22N4O3S | 详情 | 详情 |
| (VIII) | 13855 | bismuth(3+) 2-hydroxy-1,2,3-propanetricarboxylate; Bismuth Citrate | 813-93-4 | C6H5BiO7 | 详情 | 详情 |
| (IX) | 13856 | 2-Hydroxy-1,2,3-propanetricarboxylic acid; Citric acid | 77-92-9 | C6H8O7 | 详情 | 详情 |