BIIE-0246

Chemical Name: N-[1-[2-[4-(6-Oxo-6,11-dihydro-5H-dibenz[b,e]azepin-11-yl)-1-piperazinyl]cyclopentyl]acetyl]-L-arginine N-[2-(3,5-dioxo-1,2-diphenyl-1,2,3,4-tetrahydro-1,2,4-triazol-4-yl]ethylamide
CAS No. 246146-55-4, 246146-31-6 (diHCl), 246146-32-7 (monoHCl)
项目整合开发状态: Preclinical
项目研究机构: Boehringer Ingelheim (Originator)
合成路线:The condensation of ethyl allophanate (I) with diphenylhydrazine (II) produced 1,2-diphenylurazole (III).Alkylation of (III) with N-(2-bromoethyl)phthalimide (IV) in the presence of potassium tert-butoxide afforded the 4-(2-phthalimidoethyl)urazole (V),and the subsequent hydrazinolysis of the phthalimide group of (V) yielded the amino derivative (VI).Then,coupling of (VI) with N-(benzyloxycarbonyl)arginine (VII) via activation with 1,1'-carbonyldiimidazole (CDI) furnished amide (VIII).Deprotection of the N-benzyloxycarbonyl group of (VIII) to give (IX) was effected by catalytic hydrogenation over Pd/C.

合成路线:Condensation of piperazinyl dibenzoazepinone (X) with 3,3-tetramethyleneglutaric anhydride (XI) produced piperazide (XII).Further condensation of (XII) with arginine derivative (IX) using CDI yielded the title compound.