Polysubstituted imidazopyridines as gastric secretion inhibitors

A compound of the formula 1

• 10
• in which
• R1 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxycarbonyl, 2-4C-alkenyl, 2-4C-alkynyl, fluoro-1-4C-alkyl or hydroxy-1-4C-alkyl,
• R2 is hydrogen, 1-4C-alkyl, aryl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkoxycarbonyl, hydroxy-1-4C-alkyl, halogen, 2-4C-alkenyl, 2-4C-alkynyl, fluoro-1-4C-alkyl or cyanomethyl,
• R3a is hydrogen, halogen, fluoro-1-4C-alkyl, 1-4C-alkyl, 2-4C-alkenyl, 2-4C-alkynyl, carboxyl, —CO— 1-4C-alkoxy, hydroxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkoxy-1-4C-alkyl, fluoro-1-4C-alkoxy-1-4C-alkyl or the radical —CO—NR31R32,
• R3b is hydrogen, halogen, fluoro-1-4C-alkyl, 1-4C-alkyl, 2-4C-alkenyl, 2-4C-alkynyl, carboxy, —CO— 1-4C-alkoxy, hydroxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkoxy-1-4C-alkyl, fluoro-1-4C-alkoxy-1-4C-alkyl or the radical —CO—NR31R32, where
• R31 is hydrogen, 1-7C-alkyl, hydroxy-1-4C-alkyl or 1-4C-alkoxy-1-4C-alkyl and
• R32 is hydrogen, 1-7C-alkyl, hydroxy-1-4C-alkyl or 1-4C-alkoxy-1-4C-alkyl, or where
• R31 and R32 together, including the nitrogen atom to which both are bonded, are a pyrrolidino, piperidino or morpholino radical,
• one of the substituents R4a and R4b is hydrogen, 1-7C-alkyl, 2-7C-alkenyl, phenyl or phen-1-4C-alkyl and the other is hydroxyl, 1-4C-alkoxy, oxo-substituted 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkyl-1-4C-alkoxy, hydroxy-1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 3-7C-cycloalkoxy-1-4C-alkoxy, 3-7C-cycloalkyl-1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkylcarbonyloxy, wholly or mainly halogen-substituted 1-4C-alkoxy, the radical R41 or the radical R42, or in which R4a and R4b together are O (oxygen) or are 1-7C-alkylidene, where
• R41 is a radical from which a hydroxy group is formed under physiological conditions, and where
• R42 is —O—(CH2)m—S(O)n—R6, —S(O)n—(CH2)m—OH, —S(O)n—(CH2)m—O—R6, —S(O)n—(CH2)m—S(O)p—R6, —O-Alk1-S(O)n—R6, —S(O)n—R6, —S(O)n-Alk1-OH, —S(O)n-Alk1-O—R6 or —S(O)n-Alk1-S(O)p—R6, in which
• R6 is 1-7C-alkyl, halo-1-4C-alkyl, hydroxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, carboxy-1-4C-alkyl, 1-4C-alkoxycarbonyl-1-4C-alkyl or di-1-4C-alkylamino-1-4C-alkyl, Ar or Ar-1-4C-alkyl, where Ar is phenyl or substituted phenyl having one, two or three identical or different substituents selected from the group consisting of 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkylcarbonyl, 1-4C-alkoxycarbonyl, halogen, trifluoromethyl, difluoromethoxy, trifluoromethoxy, amino, 1-4C-alkoxycarbonylamino, 1-4C-alkoxy-1-4C-alkoxycarbonylamino and nitro,
• Alk1 is substituted 2-7C-alkylene or 3-4C-alkenylene by 1-4C-alkyl, hydroxyl, oxo, carboxyl, halogen, amino, 1-4C-alkoxycarbonylamino or phenyl,
• m is an integer from 2 to 7,
• n is the number 0, 1 or 2 and
• p is the number 0, 1 or 2,
• one of the substituents R5a and R5b is hydrogen, 1-7C-alkyl, 2-7C-alkenyl, phenyl or phen-1-4C-alkyl and the other is hydrogen, hydroxyl, 1-4C-alkoxy, oxo-substituted 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkyl-1-4C-alkoxy, hydroxy-1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy-1-4C-alkoxy, 3-7C-cycloalkoxy-1-4C-alkoxy, 3-7C-cycloalkyl-1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkylcarbonyloxy, wholly or mainly halogen-substituted 1-4C-alkoxy, the radical R51 or the radical R52, or in which R5a and R5b together are O (oxygen) or are 1-7C-alkylidene, where
• R51 is a radical from which a hydroxy group is formed under physiological conditions, and where
• R52 is —O—(CH2)q—S(O)r—R7, —S(O)r—(CH2)q—OH, —S(O)—(CH2)q—O—R7, —(O)r—(CH2)q—S(O)t—R7, —O-Alk2-S(O)r—R7, —S(O)r—R7, —S(O)r-Alk2-OH, —S(O)r-Alk2-O—R7 or —S(O)r-Alk2-S(O)t—R7, in which
• R7 is 1-7C-alkyl, halo-1-4C-alkyl, hydroxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, carboxy-1-4C-alkyl, 1-4C-alkoxycarbonyl-1-4C-alkyl or di-1-4C-alkylamino-1-4C-alkyl, Ar or Ar-1-4C-alkyl, where Ar is phenyl or substituted phenyl having one, two or three identical or different substituents selected from the group consisting of 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkylcarbonyl, 1-4C-alkoxycarbonyl, halogen, trifluoromethyl, difluoromethoxy, trifluoromethoxy, amino, 1-4C-alkoxycarbonylamino, 1-4C-alkoxy-1-4C-alkoxycarbonylamino and nitro,
• Alk2 is 2-7C-alkylene or 3-4C-alkenylene substituted by 1-4C-alkyl, hydroxyl, oxo, carboxyl, halogen, amino, 1-4C-alkoxycarbonylamino or phenyl,
• q is an integer from 2 to 7,
• r is the number 0, 1 or 2 and
• t is the number 0, 1 or 2,
• 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, 1-7C-alkyl, 2-7C-alkenyl, phenyl or phen-1-4C-alkyl, and the other substituents in each case together form a 1-4C-alkylenedioxy radical, which if desired, is wholly or partially halogen-substituted,
• Arom is a mono- or bicyclic aromatic radical substituted by R8, R9, R10 and R11, which is selected from the group consisting of phenyl, naphthyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, indolyl, benzimidazolyl, furanyl (furyl), benzofuranyl (benzofuryl), thiophenyl (thienyl), benzothiophenyl (benzothienyl), thiazolyl, isoxazolyl, pyridinyl, pyrimidinyl, quinolinyl and isoquinolinyl, where
• R8 is hydrogen, 1-4C-alkyl, hydroxy-1-4C-alkyl, 1-4C-alkoxy, 2-4C-alkenyloxy, 1-4C-alkylcarbonyl, carboxyl, 1-4C-alkoxycarbonyl, carboxy-1-4C-alkyl, 1-4C-alkoxycarbonyl-1-4C-alkyl, halogen, hydroxyl, aryl, aryl-1-4C-alkyl, aryloxy, aryl-1-4C-alkoxy, trifluoromethyl, nitro, amino, mono- or di-1-4C-alkylamino, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonylamino, 1-4C-alkoxy-1-4C-alkoxycarbonylamino or sulfonyl,
• R9 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl, halogen, trifluoromethyl or hydroxyl,
• R10 is hydrogen, 1-4C-alkyl or halogen and
• R11 is hydrogen, 1-4C-alkyl or halogen, where
• Aryl is phenyl or substituted phenyl having one, two or three identical or different substituents from the group consisting of 1-4C-alkyl, 1-4C-alkoxy, carboxyl, 1-4C-alkoxycarbonyl, halogen, trifluoromethyl, nitro, trifluoromethoxy, hydroxyl and cyano,
• X is O (oxygen) or NH,
• or a salt thereof,
• where the following are excluded
• (a) compounds of the formula 1, in which
• R1 is 1-4C-alkyl,
• R2 is 1-4C-alkyl or hydroxy-1-4C-alkyl,
• R3a is hydrogen or halogen,
• R3b is hydrogen or halogen,
• one of the substituents R4a and R4b is hydrogen and the other is hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy or 1-4C-alkylcarbonyloxy, 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, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy or 1-4C-alkylcarbonyloxy, or in which R5a and R5b 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 1-4C-alkylenedioxy radical,
• Arom is phenyl substituted by R8, R9, R10 and R11, where
• R8 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy, halogen, trifluoromethyl, 1-4C-alkoxycarbonylamino or 1-4C-alkoxy-1-4C-alkoxycarbonylamino,
• R9 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy or halogen,
• R10 is hydrogen and
• R11 is hydrogen,
• X is O (oxygen) or NH,
• and their salts,
• (b) compounds of the formula 1, in which
• R1 is 1-4C-alkyl,
• R2 is 1-4C-alkyl or hydroxy-1-4C-alkyl,
• R3a is hydrogen or halogen,
• R3b is hydrogen or halogen,
• one of the substituents R4a and R4b is hydrogen and the other is hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkylcarbonyloxy or the radical R42, or in which R4a and R4b together are O (oxygen), where
• R42 has the meanings indicated above,
• one of the substituents R5a and R5b is hydrogen and the other is hydrogen, hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkylcarbonyloxy or the radical R52, or in which R5a and R5b together are O (oxygen), where
• R52 has the meanings indicated above,
• Arom is phenyl substituted by R8, R9, R10 and R11, where
• R8 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy, halogen, trifluoromethyl, 1-4C-alkoxycarbonylamino or 1-4C-alkoxy-1-4C-alkoxycarbonylamino,
• R9 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy or halogen,
• R10 is hydrogen and
• R11 is hydrogen,
• X is NH,
• and their salts,
• (c) compounds of the formula 1, in which
• R1 is hydrogen, 1-4C-alkyl or hydroxy-1-4C-alkyl,
• R2 is hydrogen, 1-4C-alkyl, hydroxy-1-4C-alkyl, halogen, 2-4C-alkenyl or 2-4C-alkynyl,
• R3a is hydrogen, halogen, fluoro-1-4C-alkyl, 1-4C-alkyl, 2-4C-alkenyl or 2-4C-alkynyl,
• R3b is hydrogen, halogen, fluoro-1-4C-alkyl, 1-4C-alkyl, 2-4C-alkenyl or 2-4C-alkynyl,
• one of the substituents R4a and R4b is hydrogen and the other is hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkylcarbonyloxy or wholly or mainly halogen-substituted 1-4C-alkoxy, 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, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkylcarbonyloxy or wholly or mainly halogen-substituted 1-4C-alkoxy, or in which R5a and R5b together are O (oxygen), with the proviso that at least one of the substituents R4a, R4b, R5a and R5b is wholly or mainly halogen-substituted alkoxy,
• 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 wholly or partially halogen-substituted 1-4C-alkylenedioxy radical,
• Arom is phenyl substituted by R8, R9, R10 and R11, where
• R8 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy, halogen, trifluoromethyl, 1-4C-alkoxycarbonylamino or 1-4C-alkoxy-1-4C-alkoxycarbonylamino,
• R9 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy or halogen,
• R10 is hydrogen and
• R11 is hydrogen,
• X is NH,
• and their salts,
• (d) compounds of the formula 1, in which
• R1 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl or hydroxy-1-4C-alkyl,
• R2 is hydrogen, 1-4C-alkyl, hydroxy-1-4C-alkyl, halogen, 2-4C-alkenyl or 2-4C-alkynyl,
• R3a is hydrogen,
• R3b is hydrogen, halogen, fluoro-1-4C-alkyl, 1-4C-alkyl, 2-4C-alkenyl, 2-4C-alkynyl, carboxyl, —CO— 1-4C-alkoxy, hydroxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, fluoro-1-4C-alkoxy-1-4C-alkyl or the radical —CO—NR31R32, where
• R31 is hydrogen, 1-7C-alkyl, hydroxy-1-4C-alkyl or 1-4C-alkoxy-1-4C-alkyl and
• R32 is hydrogen, 1-7C-alkyl, hydroxy-1-4C-alkyl or 1-4C-alkoxy-1-4C-alkyl, or where
• R31 and R32 together, including the nitrogen atom to which both are bonded, are a pyrrolidino, piperidino or morpholino radical,
• one of the substituents R4a and R4b is hydrogen, 1-7C-alkyl, 2-7C-alkenyl, phenyl or phen-1-4C-alkyl and the other is hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkylcarbonyloxy or the radical R41, or in which R4a and R4b together are O (oxygen) or are 1-7C-alkylidene, where
• R41 is a radical from which a hydroxy group is formed under physiological conditions,
• one of the substituents R5a and R5b is hydrogen, 1-7C-alkyl, 2-7C-alkenyl, phenyl or phen-1-4C-alkyl and the other is hydrogen, hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkyl-carbonyloxy or the radical R51, or in which R5a and R5b together are O (oxygen) or are 1-7C-alkylidene, where
• R51 is a radical from which a hydroxy group is formed under physiological conditions,
• 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, 1-7C-alkyl, 2-7C-alkenyl, phenyl or phen-1-4C-alkyl, and the other substituents in each case together form a 1-4C-alkylenedioxy radical,
• where one of the substituents R4a and R4b must have the meaning R41 and/or one of the substituents R5a and R5b must have the meaning R51 and/or where at least one of the substituents R4a, R4b, R5a and R5b must have the meaning 1-7C-alkyl, 2-7C-alkenyl, phenyl or phen-1-4C-alkyl and/or where either R4a and R4b or R5a and R5b together must be 1-7C-alkylidene,
• Arom is phenyl substituted by R8, R9, R10 and R11, where
• R8 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy, halogen, trifluoromethyl, 1-4C-alkoxycarbonylamino or 1-4C-alkoxy-1-4C-alkoxycarbonylamino,
• R9 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy or halogen,
• R10 is hydrogen and
• R11 is hydrogen,
• X is O (oxygen) or NH,
• and their salts, and also
• (e) compounds of the formula 1, in which
• R1 is methyl,
• R2 is methyl or hydroxymethyl,
• R3a is hydrogen,
• R3b is halogen, carboxyl, —CO-1-4C-alkoxy, hydroxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkoxy-1-4C-alkyl, fluoro-1-4C-alkoxy-1-4C-alkyl or the radical —CO—NR31R32, where
• R31 is hydrogen, 1-7C-alkyl, hydroxy-1-4C-alkyl or 1-4C-alkoxy-1-4C-alkyl and
• R32 is hydrogen, 1-7C-alkyl, hydroxy-1-4C-alkyl or 1-4C-alkoxy-1-4C-alkyl, or where
• R31 and R32 together, including the nitrogen atom to which both are bonded, are a pyrrolidino, piperidino or morpholino radical,
• one of the substituents R4a and R4b is hydrogen and the other is hydroxyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, methoxyethoxy or methoxypropoxy,
• one of the substituents R5a and R5b is hydrogen and the other is hydrogen, hydroxyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, methoxyethoxy or methoxypropoxy,
• Arom is a phenyl radical,
• X is O (oxygen) or NH,
• and their salts.