• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】YM17E

【化学名称】1,3-Bis[1-cycloheptyl-3-[4-(dimethylamino)phenyl]ureidomethyl]benzene dihydrochloride
      1,1'-(1,3-Phenylene)bismethylenebis[1-cycloheptyl-3-[4-(dimethylamino)phenyl]urea] dihydrochloride

【CA登记号】124884-99-7, 124900-72-7 (free base)

【 分 子 式 】C40H58Cl2N6O2

【 分 子 量 】725.85326

【开发单位】Yamanouchi (Originator)

【药理作用】Lipoprotein Disorders, Treatment of , METABOLIC DRUGS, ACAT Inhibitors

合成路线1

Reaction of isophthaloyl dichloride (I) with cycloheptylamine (II) in the presence of triethylamine in dichloromethane gives N,N'-dicycloheptylisophthalimide (III), which is reduced with sodium bis(2-methoxyethoxy)aluminum hydride in toluene to yield 1,3-bis(cycloheptylaminomethyl)benzene (IV). Compound (IV) is treated with p-nitrophenylisocyanate (V) to afford 1,3-bis[1-cycloheptyl-3-(4-nitrophenyl)ureidomethyl]benzene (VI), which is reduced with hydrogen in the presence of palladium over charcoal to give 1,3-bis[1-cycloheptyl-3-(4-aminophenyl)ureidomethyl]benzene (VII). Finally, compound (VII) is treated with aqueous formaldehyde and hydrogen in the presence of platinum oxide in ethanol, followed by addition of hydrochloric acid in ethanol.

1 Ito, N.; Yasunaga, T.; Iizumi, Y.; Araki, T. (Yamanouchi Pharmaceutical Co., Ltd.); Diurea derivatives useful as medicaments and processes for the preparation thereof. AU 8928669; EP 0325397; JP 1990117651; US 5091419; US 5166429; US 5384425 .
2 Yasunaga, T.; Araki, T.; Iwaoka, K.; Iizumi, Y.; Ohata, I.; Matsuda, K.; Ito, N.; Synthesis and activity of a novel phenylenediurea derivative with hypolipidemic and antiatherosclerotic activity. 111th Annu Meet Pharmaceut Soc Jpn (March 28-30, Tokyo) 1991, Abst 29V 3-040..
3 Graul, A.; Castaner, J.; Prous, J.; YM17E. Drugs Fut 1993, 18, 9, 813.
4 Iizumi, Y.; Ohhata, I.; Iwaoka, K.; Matsuda, K.; Ito, N.; Yasunaga, T.; Araki, T.; Synthesis and hypocholesterolemic activity of phenylene and pyridylene diurea derivatives as ACAT inhibitors. 202nd ACS Natl Meet (Aug 25-30, New York) 1991, Abst MEDI 109.
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) 12501 Isophthaloyl dichloride 99-63-8 C8H4Cl2O2 详情 详情
(II) 11926 1-[4-(Chloromethyl)-2-hydroxy-3-propylphenyl]-1-ethanone C12H15ClO2 详情 详情
(III) 14907 N(1),N(3)-dicycloheptylisophthalamide C22H32N2O2 详情 详情
(IV) 14908 N-cycloheptyl-N-[3-[(cycloheptylamino)methyl]benzyl]amine; N-[3-[(cycloheptylamino)methyl]benzyl]cycloheptanamine C22H36N2 详情 详情
(V) 14909 1-isocyanato-4-nitrobenzene; 4-Nitrophenyl isocyanate 100-28-7 C7H4N2O3 详情 详情
(VI) 14910 N-cycloheptyl-N-[3-([cycloheptyl[(4-nitroanilino)carbonyl]amino]methyl)benzyl]-N'-(4-nitrophenyl)urea C36H44N6O6 详情 详情
(VII) 14911 N-(3-[[[(4-aminoanilino)carbonyl](cycloheptyl)amino]methyl]benzyl)-N'-(4-aminophenyl)-N-cycloheptylurea C36H48N6O2 详情 详情
Extended Information