Patent EA-001734-B1 (EA)
Title: Imidazopyridazines
Inventor: ZIMMERMANN PETER
IPC: C07H15/26
Filed: 1997-12-18
Abstract: 1. A compound of the formula I   in which R1 is hydrogen, C1-C4alkyl, C1-C4alkyl substituted by radical R11, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, sulfo group(-SO3H) or a cyclic system or bicyclic system substituted by radicals R11 and R12, which is selected from the group consisting of pyrrole, furan, thiophene, pyrazole, imidazole, imidazoline, oxazole, isoxazole, thiazole, thiazoline, isothiazole, triazole, oxadiazole, thiadiazole, thiadiazole-1-oxide, tetrazole, hexopyranoses, benzene, pyridine, pyridine-N-oxide, pyridazine, pyrimidine, pyrazine, triazine, naphthalene, quinoline, quinazoline, quinoxaline, benzimidazole, benzoxazole, benzothiazole, thiazolopyridine and imidazopyridine, wherein R11 is hydrogen, C1-C4alkyl, C3-C7cycloalkyl, C1-C4alkoxy, C1-C4alkoxyC1-C4alkoxy, C1-C4alkylcarbonyl, amino-, C1-C4alkylcarbonylamino, halogen, trifluoromethyl, trifluoromethoxy, hydroxyl, carboxyl, C1-C4alkoxycarbonyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, sulfo (-SO3H), nitro, guanidino, phenyl, phenyl substituted by radical R111, pyridyl, pyridyl substituted by radical R111, imidazolyldione, thiazolyl, C1-C4alkyl substituted by radical R111, -N(R112)R113 or -CO-N(R112)R113 and R12 is hydrogen, C1-C4alkyl, C1-C4-alkoxy, halogen, amino, hydroxyl, phenyl or trifluoromethyl, wherein R111 is hydroxyl, C1-C4alkyl, C1-C4-alkoxy, carboxyl, C1-C4alkoxycarbonyl, halogen, aminosulfonyl or -N(R112)R113, R112 is hydrogen, C1-C4alkyl, formyl, C1-C4alkylcarbonyl or C1-C4alkoxycarbonyl and R113 is hydrogen or C1-C4alkyl, or where R112 and R113, together and including the nitrogen atom to which both are bonded, are a piperidino or morpholino radical, R2 is hydrogen, C1-C4alkyl or halogen, A is C2-7alkylene, X is a bonding dash, O (oxygen) or S (sulfur), Y is O (oxygen), S (sulfur) or N-C1-C4alkyl and Z is O (oxygen) or S (sulfur), or the salts of this compound and its N-oxides or the salts of the N-oxides. 2. A compound as claimed in Claim 1, of the formula I*   in which R1, R2, A, X, Y and Z have the meanings indicated in Claim 1, or the salts of this compound and its N-oxides or the salts of the N-oxides. 3. A compound of the formula I in which R1 is hydrogen, C1-C4alkyl, C1-C4alkyl substituted by radical R11, C1-C4alkylcarbonyl, sulfo group (-SO3H) or a cyclic system or bicyclic system substituted by radicals R11 and R12, which is selected from the group consisting of pyrrole, furan, thiophene, pyrazole, imidazole, imidazoline, oxazole, isoxazole, thiazole, thiazoline, isothiazole, triazole, oxadiazole, thiadiazole, thiadiazole-1-oxide, tetrazole, hexopyranoses, benzene, pyridine, pyridine-N-oxide, pyridazine, pyrimidine, pyrazine, naphthalene, quinoline, quinazoline, quinoxaline, benzimidazole, benzothiazole, thiazolopyridine and imidazopyridine, where R11 is hydrogen, C1-C4alkyl, C3-C7cycloalkyl, C1-C4alkoxy, C1-C4alkoxyC1-C4alkoxy, C1-C4alkylcarbonyl, amino-, C1-C4alkylcarbonylamino, halogen, trifluoromethyl, trifluoromethoxy, hydroxyl, carboxyl, C1-C4alkoxycarbonyl), C1-C4alkylthio, C1-C4alkylsulfonyl, nitro, phenyl, phenyl substituted by radical R111, pyridyl, pyridyl substituted by radical R111, imidazolyldione, thiazolyl, C1-C4alkyl substituted by radical R111, -N(R112)R113 or -CO-N(R112)R113 and R12 is hydrogen, C1-C4alkyl, C1-C4alkoxy, halogen, amino, hydroxyl or phenyl, where R111 is hydroxyl, C1-C4alkyl, C1-C4alkoxy, carboxyl, halogen, aminosulfonyl or -N(R112)R113, R112 is hydrogen, C1-C4alkyl, C1-C4alkylcarbonyl or C1-C4alkoxycarbonyl and R113 is hydrogen or C1-C4alkyl, R2 is hydrogen, C1-C4alkyl or halogen, A is C2-7alkylene, X is a bonding dash, O (oxygen) or S (sulfur), Y is O (oxygen), S (sulfur) or N-C1-C4alkyl and Z is O (oxygen) or S (sulfur), or the salts of this compound and its N-oxides or the salts of the N-oxides. 4. A compound of the formula I in which R1 is hydrogen, C1-C4alkyl, C1-C4alkyl substituted by radical R11, C1-C4alkylcarbonyl, sulfo group (-SO3H) or a cyclic system or bicyclic system substituted by radicals R11 and R12, which is selected from the group consisting of imidazole, tetrazole, hexopyranoses, pyridine, pyridine-N-oxide, pyrimidine, benzimidazole and thiazolopyridine, where R11 is hydrogen, C1-C4alkyl, C3-C7cycloalkyl, C1-C4alkoxy, C1-C4alkoxyC1-C4alkoxy, C1-C4alkylcarbonyl, amino, halogen, trifluoromethyl, hydroxyl, carboxyl, C1-C4alkoxycarbonyl, C1-C4alkylthio, C1-C4alkylsulfonyl, phenyl, phenyl substituted by radical R111, pyridyl, pyridyl substituted by radical R111, imidazolyldione, thiazolyl, C1-C4alkyl substituted by radical R111 or -N(R112)R113 and R12 is hydrogen, C1-C4alkyl, amino or hydroxyl, where R111 is hydroxyl, C1-C4alkyl, C1-C4alkoxy or -N(R112)R113, R112 is hydrogen, C1-C4alkyl or C1-C4alkylcarbonyl and R113 is hydrogen or C1-C4alkyl, R2 is hydrogen, C1-C4alkyl or halogen, A is C2-C5alkylene, X is a bonding dash, O (oxygen) or S (sulfur), Y is O (oxygen), S (sulfur) or N-C1-C4alkyl and Z is O (oxygen) or S (sulfur), or the salts of this compound and its N-oxides or the salts of the N-oxides. 5. A compound as claimed in Claim 1, of the formula I*   in which R1 is hydrogen, C1-C4alkyl, C1-C4alkyl substituted by radical R11, C1-C4alkylcarbonyl, sulfo group (-SO3H) or a cyclic system or bicyclic system substituted by radicals R11 and R12, which is selected from the group consisting of imidazole, tetrazole, pyridine, pyrimidine and benzimidazole, where R11 is hydrogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkoxyC1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, phenyl, phenyl substituted by radical R111, pyridyl, pyridyl substituted by radical R111 or thiazolyl R12 is hydrogen, where R111 is hydroxyl or C1-C4alkyl, R2 is C1-C4alkyl or halogen, A is C2-C4alkylene, X is a bonding dash, O (oxygen) or S (sulfur), Y is O (oxygen), S (sulfur) or N-C1-C4alkyl and Z is O (oxygen) or S (sulfur), or the salts of this compound and its N-oxides or the salts of the N-oxides. 6. A compound as claimed in Claim 1, of the formula I*   in which R1 is benzimidazol-2-yl, R2 is C1-C4alkyl or halogen, A is C2-C4alkylene, X is a bonding dash, O (oxygen) or S (sulfur), Y is O (oxygen), S (sulfur) or N-C1-C4alkyl and Z is O (oxygen) or S (sulfur), or the salts of this compound and its N-oxides or the salts of the N-oxides. 7. A compound of the formula I as claimed in Claim 1, in which X is S (sulfur), Y is S (sulfur) and Z is S (sulfur). 8. A compound of the formula I as claimed in Claim 1, in which A is C2-C4alkylen, X is S (sulfur), Y is N-C1-C4alkyl and Z is O (oxygen). 9. A medicament comprising a compound of Claim 1 together with customary pharmaceutical auxiliaries or excipients. 10. The use of compounds of Claim 1 in the control of Helicobacter bacteria.