Imiquimod, MTD-39, DZ-2636, R-837, S-26308, Zartra, Aldara

咪喹莫特Chemical Name: 1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-amine; 1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
CAS No. 99011-02-6, 99011-78-6 (mono HCl salt)
项目整合开发状态: Launched-1997
项目研究机构: 3M Pharmaceuticals (Originator), Daiichi Pharmaceutical (Licensee), Mochida (Licensee)
合成路线:The condensation of 4-chloro-3-nitroquinoline (I) with isobutylamine in refluxing THF gives 4-(isobutylamino)-3-nitroquinoline (II),which by reduction with H2 over Pt/C in ethanol is converted to 3-amino-4-(isobutylamino)quinoline (III).The cyclization of (III) with triethyl orthoformate in refluxing formic acid affords 1-isobutyl-1H-imidazo[4,5-c]quinoline (IV),which is oxidized with 30% H2O2 in hot acetic acid yielding 1-isobutyl-1H-imidazo[4,5-c]quinolin-5-oxide (V).The reaction of (V) with refluxing POCl3 affords 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline (VI),which is finally treated with concentrated aqueous NH4OH at 150 C in a pressure vessel.