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【结 构 式】

【药物名称】Olanexidine hydrochloride, OPB-2045

【化学名称】1-(3,4-Dichlorobenzyl)-5-octylbiguanide hydrochloride

【CA登记号】146509-94-6, 146510-36-3 (free base), 218282-71-4 (hemihydrate)

【 分 子 式 】C17H28Cl3N5

【 分 子 量 】408.80521

【开发单位】Otsuka (Originator)

【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY

合成路线1

OPB-2045 can be obtained by several related ways: 1) The addition of 3,4-dichlorobenzylamine hydrochloride (I) to sodium dicyanamide (II) in refluxing acetonitrile gives 1-(3,4-dichlorobenzyl)-3-cyanoguanidine (III), which is then condensed with octylamine hydrochloride (IV) in refluxing mesitylene. 2) The treatment of S,S'-dimethyl(cyanoimino)dithiocarbonate (V) with aqueous ammonia and further reaction with 3,4-dichlorobenzylamine hydrochloride (I) yields intermediate (III), which is then condensed with (IV) as before. 3) By condensation of 3,4-dichlorobenzylamine hydrochloride (I) with 1-cyano-3-octylguanidine (VI) in refluxing mesitylene.

1 Kikuchi, M.; Ishikawa, H.; Yasumura, K.; Ohguro, K.; Tsubouchi, H.; Synthesis and structure-activity relationships of novel antiseptics. Bioorg Med Chem Lett 1997, 7, 13, 1721.
2 Yasumura, K.; Kikuchi, M.; Ishikawa, H.; Ohguro, K.; Tsubouchi, H.; Synthesis and structure-activity relationships of new disinfectants. Symp Med Chem 1996, Abst 2-P-3.
3 Sorbera, L.A.; Castañer, J.; OPB-2045. Drugs Fut 1999, 24, 2, 151.
4 Ishikawa, H.; Yasumura, K.; Tsubouchi, H.; Higuchi, Y.; Tamaoka, H. (Otsuka Pharmaceutical Co., Ltd.); Biguanide derivs., manufacturing method thereof, and disinfectants containing the derivs.. EP 0507317 .
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) 21140 (3,4-dichlorophenyl)methanamine hydrochloride C7H8Cl3N 详情 详情
(II) 21141 sodium dicyanimide C2N3Na 详情 详情
(III) 21142 N-cyano-N'-(3,4-dichlorobenzyl)guanidine C9H8Cl2N4 详情 详情
(IV) 21143 1-octanamine hydrochloride 142-95-0 C8H20ClN 详情 详情
(V) 18174 [[bis(methylsulfanyl)methylene]amino](nitrilo)methane 10191-60-3 C4H6N2S2 详情 详情
(VI) 21145 N-cyano-N'-octylguanidine C10H20N4 详情 详情
Extended Information