Substituted 2 amino imidazoles, method for their manufacture and their use as a drug or diagnostic and drug containing them

摘要

2-Anilinoimidazoles (I) are new. 2-Anilinoimidazoles of formula (I) and their salts are new: [Image] R 1, R 2H, 1-4C (fluoro)alkyl, CN or phenyl or form a 5- to 8-membered carbocyclic ring with 1-2 double bonds, optionally substituted with 1-12 F atoms or with 1-2 of OH, NR 8R 9, 1-4C alkyl, CN, CF 3or 1-4C alkoxy, provided that R 1and R 2are not both H; R 9, R 10H or 1-4C alkyl; R 3-R 7H, halo, 1-4C (fluoro)alkyl or 1-4C (fluoro)alkoxy, provided than R 3and R 7are not both H; R 8H, 1-4C (fluoro)alkyl or 3-5C (fluoro)cycloalkyl; provided that R1 and R2 are not both Me when R 3is Cl and R 4-R 8are H. An independent claim is also included for production of alpha -amino ketals of formula (V) by reacting an alpha -halo ketone or aldehyde of formula (VI) with an azide, reacting the resulting alpha -azido ketone or aldehyde with a mono- or dihydric alcohol to form a ketal or acetal of formula (VIII) and reducing this to (V). [Image] R 1, R 2H, 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 3-6C cycloalkyl, 4-6C cycloalkenyl or phenyl, where phenyl is optionally substituted with 1-2 of halo, NR 11R 12, 1-4C alkyl, CN, CF 3or 1-4C alkoxy and carbon chains are optionally substituted with 1-9 F atoms or 1-2 of NR 11R 12, 1-4C alkyl, CN, CF 3or 1-4C alkoxy, or R 1+R 2forms a 5- to 8-membered carbocyclic ring with 1-2 double bonds, optionally substituted with 1-12 F atoms or with 1-2 of OH, NR 11R 12, 1-4C alkyl, CN, CF 3or 1-4C alkoxy; R 11, R 121-4C alkyl, benzyl or 4-methoxybenzyl; E : 1-4C alkyl or E+E is 2-4C alkylene. ACTIVITY : Nephrotropic; Laxative; Hypotensive; Anticonvulsant; Tranquilizer; Antidepressant; Neuroleptic; Cerebroprotective; Vasotropic; Antiarteriosclerotic; Antilipemic; Anticoagulant; Antiparasitic; Protozoacide; Antidiabetic; Cytostatic. MECHANISM OF ACTION : Sodium/hydrogen exchanger inhibitor. N-(2,6-dichorophenyl)-N-(4-methyl-1H-imidazol-2-yl)amine hydrochloride had an IC 50of 1.7 MicroM against intracellular pH restoration by recombinant sodium/hydrogen exchanger 3 in LAP1 fibroblasts.