New bicyclic imidazole derivatives are dipeptidylpeptidase-IV inhibitors useful to treat e.g. arthritis, obesity, allograft transplantation and calcitonin-induced osteoporosis

摘要

Bicyclic imidazole derivatives (I) and their salts, tautomers, enantiomers and/or diastereomers are new. Bicyclic imidazole derivatives (I) and their salts, tautomers, enantiomers and/or diastereomers are new. R 1>(phenyl)pyridinyl, (pyridinylphenyl)carbonyl, (phenyl)quinolinyl, (phenyl)isoquinolinyl or phenanthridinyl (substituted by R 10>-R 12>) (where N atom is substituted by an O atom); R 10>H, F, Cl, Br, I, 1-4C alkyl, OH, 1-4C alkyloxy, NO 2, NH 2, 1-3C alkylamino, di-(1-3C alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl or morpholin-4-yl, 1-3C alkyl-carbonylamino, N-(1-3C alkyl)-1-3C alkyl-carbonylamino, 1-3C alkylsulfonylamino, N-(1-3C alkyl)-1-3C alkyl-sulfonylamino group, 1-3C alkyl-carbonyl, CN, aminocarbonyl, (1-3C alkylamino)carbonyl, [di-(1-3C alkyl)-amino]carbonyl, pyrrolidin-1-ylcarbonyl, piperidin-1-ylcarbonyl, morpholin-4-ylcarbonyl, CH 3, OCH 3 (substituted by 1-3F), 1-3C alkylsulfanyl, 1-3C alkylsulfinyl or 1-3C alkylsulfonyl, 2-4C alkenyl, 2-4C alkynyl, 3-4C alkenyloxy, 3-4C alkynyloxy, 3-6C cycloalkyl, 3-6C cycloalkyloxy, 3-6C cycloalkyl-1-3C alkyl, 3-6C cycloalkyl-1-3C alkyloxy, aryl, aryloxy, aryl-1-3C alkyl or aryl-1-3C alkyloxy; R 11>, R 12>H, F, Cl or Br or CH 3, difluoromethyl, CF 3, OCH 3, difluoromethoxy, OCF 3, CN, a pyridazinyl, phenylpyridazinyl, (pyridazinylphenyl-)carbonyl, (phenyl)pyrimidinyl, (pyrimidinylphenyl)carbonyl, (phenyl)pyrazinyl, (pyrazinylphenyl)carbonyl, (phenyl)quinolinyl, (phenyl)quinazolinyl, (phenyl)phthalazinyl, (phenyl)quinoxalinyl or (phenyl)naphthyridinyl (substituted by R 10>-R 12>), (one N atom is substituted by an O atom); R 2>2-methyl-2-propen-1-yl, 2-chloro-2-propen-1-yl or 3-bromo-2-propen-1-yl; 1-buten-1-yl, 3-methyl-1-buten-1-yl, 3-methyl-2-buten-1-yl, 2-buten-1-yl, 2-methyl-2-buten-1-yl or 2,3-dimethyl-2-buten-1-yl, 2-butyn-1-yl, 1-cyclopenten-1-ylmethyl group or benzyl, 2-fluorobenzyl, 2-chlorobenzyl, 2-bromobenzyl or 2-cyanobenzyl; R 3>3-aminopiperidin-1-yl, 3-amino-azepan-1yl, piperazin-1-yl or [1,4]-diazepan-1-yl or NH 2 (substituted by R 4> and R 5>); R 4>CH 3 or ethyl; R 5>2-aminoethyl (ethyl moiety of the 2-aminoethyl optionally substituted by 1-2 CH 3); A : CO-N(R 6>) (N atom is linked to the imidazo ring of (I)); R 6>H, 1-4C alkyl, 3-6C cycloalkyl, aryl, CH=CH (substituted by R 6>) or (R 7>)=N (N atom is linked to the imidazo ring of (I)); and R 7>H, 1-4C alkyl, 3-6C cycloalkyl, arylor N=C(R 7>) (C atom is linked to the imidazo ring of (I). Independent claims are also included for preparations of (I). [Image] ACTIVITY : Antidiabetic; Antiarthritic; Anorectic; Immunosuppressive; Osteopathic. MECHANISM OF ACTION : Dipeptidylpeptidase-IV inhibitor.