Patent EA-002402-B1 (EA)
Title: Tetrahydropyrido compounds
Inventor: SIMON WOLFGANG-ALEXANDER
IPC: C07D471/14
Filed: 1998-03-19
Abstract: 1. A compound of the formula I   in which R1 is C1-C4alkyl, R2 is C1-C4alkyl or hydroxy- C1-C4alkyl, R3 is hydrogen one of the substituents R4a and R4b is hydrogen and the other is hydrogen, hydroxyl, C1-C4alkoxy-, C1-C4alkoxy-C1-C4alkoxy- or in which R4a and R4b together are O (oxygen), or in which one of the substituents R4a and R4b on the one hand and one of the substituents R5a and R5b on the other hand is in each case hydrogen, and the other substituents in each case together form a methylenedioxy radical (-O-CH2-O-) or an ethylenedioxy radical (-O-CH2-CH2-O-), where R4a, R4b, R5a and R5b are not simultaneously hydrogen, R6 is hydrogen or halogentrifluoromethyl, R7 is hydrogen or halogen or its salts. preferably this compound may have a chemical name (7R,8R,9R)-7,8-isopropylidenedioxy-2, 3-dimethyl-9-phenyl-7, 8, 9, 10-tetrahydroimidazo[1,2-h][1, 7]naphthyridine, or a salt thereof. 2. The compound of the formula I as claimed in claim 1, in which R1 is I-4C-alkyl, R2 is C1-C4alkyl or hydroxy-C1-C4 alkyl, R3 is hydrogen, one of the substituents R4a and R4b is hydrogen and the other is hydrogen, hydroxyl or C1-C4alkoxy, or in which R4a and R4b together are O (oxygen), one of the substituents R5a and R5b is hydrogen and the other is hydrogen, hydroxyl or C1-C4alkoxy or in which R5a and R5b together are O (oxygen), where R4a, R4b, R5a and R5b are not simultaneously hydrogen, R6 is hydrogen, halogen or trifluoromethyl and R7 is hydrogen or halogen or its salts. 3. The compound as claimed in claim 1, which has the formula l*   in which R1 is C1-C4 alkyl, R2 is C1-C4 alkyl, R3 is hydrogen, one of the substituents R4a and R4b is hydrogen and the other is hydrogen, hydroxyl or C1-C4 alkoxy, one of the substituents R5a and R5b is hydrogen and the other is hydrogen, hydroxyl or C1-C4 alkoxy, where R4a, R4b, R5a and R5b are not simultaneously hydrogen, R6 is hydrogen, halogen or trifluoromethyl and R7 is hydrogen or halogen, or its salts. 4. The compound of the formula l* as claimed in claim 3, in which R1 is C1-C4 alkyl, R2 is C1-C4 alkyl, R3 is hydrogen, R4a is hydrogen,  R4b is hydroxyl or C1-C4 alkoxy, R5a is hydrogen, hydroxyl or C1-C4 alkoxy, R5b is hydrogen, R6 is hydrogen, halogen or trifluoromethyl and R7 is hydrogen or halogen, or its salts. 5. The compound of the formula l* as claimed in claim 3, in which R1 is C1-C4 alkyl, R2 is C1-C4 alkyl,  R3 is hydrogen, R4a is hydrogen, R4b is hydroxyl, R5a is hydroxyl, R5b is hydrogen, R6 is hydrogen, halogen or trifluoromethyl and R7 is hydrogen or halogen, and its salts. 6. The compound as claimed in claim 1, selected from the group consisting of 7,8-dihydroxy-2, 3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1 ,2-h][1 ,7]naphthyridine, 2,3-dimethyl-9-phenyl-7,8,9, 10-tetrahydroimidazo[1 ,2-h][1 ,7]naphthyridin-7-one, 9-(2-chlorophenyl)-2, 3-dimethyl-7,8,9, 10-tetrahydroimidazo[1 ,2h][1 ,7]naphthyridin-7-one, 9-(2,6-dichlorophenyl)-2, 3-dimethyl-7, 8,9,10-tetrahydroimidazo[1 ,2-h][1 ,7]naphthyridin-7-one, 9-(2-trifluoromethylphenyl)-2, 3-dimethyl-7,8,9,10-tetrahydroimidazo[1 ,2-h][1 ,7]naphthyridin-7one, 7-hydroxy-2,3-dimethyl-9-phenyl-7, 8,9,10-tetrahydroimidazo[1 ,2-h][1 ,7]naphthyridine, 9-(2-chlorophenyl)-7-hydroxy-2,3-dimethyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine, 9-(2, 6-dichlorophenyl)-7-hydroxy-2,3-dimethyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine, 9-(2-trifluoromethylphenyl)-7-hydroxy-2, 3-dimethyl-7,8 9,10-tetrahydroimidazo[I .2- h][1 ,7]naphthyridine, 8-hydroxy-2,3-dimethyl-9-phenyl-7,8,9, 10-tetrahydroimidazo[1 ,2-h][1 ,7]naphthyridin-7-one, (7S,8R,9R)-2,3-dimethyl-7,8-dihydroxy-9-phenyl-7,8,9, 1 0-tetrahydroimidazo[1 ,2h][1 ,7]naphthyridine, (8R,9R)-3-Formyl-8-hydroxy-2-methyl-7-oxo-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2h][1 ,7]naphthyridine, (7R,8R,9R)-3-hydroxymethyl-7,8-dihydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydro- imidazo[I ,2-h][1 , 7]naphthyridine or a salt thereof. 7. The compound as claimed in claim 6 with 9R-configuration, or a salt thereof. 8. The compound as claimed in claim 1 having the chemical name (7R,8R,9R)-7,8dihydroxy-2, 3-dimethyl-9-phenyl-7, 8,9,10-tetrahydroimidazo[1 ,2-h][1 ,7]naphthyridine, or a salt thereof. 9. A medicament comprising a compound as claimed in claim 1 and/or a pharmacologically tolerable salt thereof together with customary pharmaceutical auxiliaries and/or excipients. 10. The use of compounds as claimed in claim 1 and their pharmacologically tolerable salts for the production of medicaments for the prevention and treatment of gastrointestinal diseases caused by an increased secretion of digestive juices.