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【结 构 式】 
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【药物名称】BM-567 【化学名称】2-(Cyclohexylamino)-5-nitro-N-(pentylcarbamoyl)benzenesulfonamide 【CA登记号】284464-77-3 【 分 子 式 】C18H28N4O5S 【 分 子 量 】412.51166 |
【开发单位】University of Liege(Originator), University of Namur (Originator) 【药理作用】Antiplatelet Therapy, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, Prostanoid TP (Thromboxane A2) Antagonists, Thromboxane Synthase Inhibitors |
合成路线1
Diazotization of 2-chloro-5-nitroaniline (I), followed by quenching with a solution of SO2 in HOAc in the presence of CuCl2, furnished the sulfonyl chloride (II). Treatment of (II) with aqueous ammonia gave rise to the corresponding sulfonamide (III). The chloro group of (III) was then displaced with cyclohexylamine (IV) in refluxing 3-chlorotoluene to afford the cyclohexylamino benzenesulfonamide (V). Finally, condensation of sulfonamide (V) with pentyl isocyanate (VI) produced the target sulfonylurea.
| 【1】 Delarge, J.; Masereel, B.; Dogne, J.-M. (University of Liege); Benzenic sulphonamide derivs. and their uses. WO 0042004 . |
| 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) | 43033 | 2-chloro-5-nitroaniline; 2-chloro-5-nitrophenylamine | 6283-25-6 | C6H5ClN2O2 | 详情 | 详情 |
| (II) | 43034 | 2-chloro-5-nitrobenzenesulfonyl chloride;2-Chloro-5-nitro-benzenesulfonyl chloride;2-Chloro-5-nitrophenylsulfonyl chloride;6-Chloro-3-nitrobenzenesulfonyl chloride | 4533-95-3 | C6H3Cl2NO4S | 详情 | 详情 |
| (III) | 43035 | 2-chloro-5-nitrobenzenesulfonamide | 96-72-0 | C6H5ClN2O4S | 详情 | 详情 |
| (IV) | 17966 | cyclohexanamine; cyclohexyl amine; cyclohexylamine | 108-91-8 | C6H13N | 详情 | 详情 |
| (V) | 47439 | 2-(cyclohexylamino)-5-nitrobenzenesulfonamide | C12H17N3O4S | 详情 | 详情 | |
| (VI) | 47440 | 1-isocyanatopentane; pentyl isocyanate | 3954-13-0 | C6H11NO | 详情 | 详情 |