4-(1-piperazinyl) benzoic acid derivatives, process for preparing them and their therapeutic applications

A compound of the formula (I):

• in which:
• Ar is selected from
• a mono-, bi- or tricyclic aryl group having from 6 to 14 carbon atoms,
• a heteroaromatic group selected from the pyridyl, pyrimidyl, pyrrolyl, furyl, thienyl, quinolyl, indolyl, benzothienyl, benzofuryl, benzopyrranyl, benzothiopyrannyl, dibenzofuryl, carbazolyl and benzothiazinyl groups,
• optionally, the Ar group carrying 1 to 3 substituents selected from C1-C8 alkyl, (C3-C8)cyclo-alkyl (C1-C6)alkyl, C1-C8 alkoxy, (C3-C8)cycloalkyloxy (C1-C6)alkyl, (C3-C8)cycloalkyl (C1-C6)alkoxy (C1-C6)alkyl, (C3-C8)cycloalkyloxy, (C3-C8)cycloalkyl (C1-C6)alkoxy, (C1-C6)alkoxy (C1-C6)alkyl, C6-C14 aryl, C6-C14 heteroaryl, (C6-C14)heteroaryl (C1-C6)alkyl, (C6-C14)aryl (C1-C6)alkyl, (C6-C14)aryl (C1-C6)alkyl (C6-C14)aryl, (C6-C14)aryloxy, (C6-C14)aryloxy, (C1-C6)aryloxy (C1-C6)alkyl, (C6-C4)aryl (C1-C6)alkyloxy or (C6-C14)aryl (C1-C6)alkyloxy (C1-C6)alkyl groups, a halogen, a trifluoromethyl, trifluoromethoxy, cyano, hydroxyl, nitro, amino, carboxyl, (C1-C6)alkoxycarbonyl, carbamoyl, (C1-C8)alkylthio, (C1-C8)alkylsulphinyl, (C1-C8)alkylsulphonyl, sulphoamino, (C1-C8)alkylsulphonylamino, sulphamoyl or (C1-C8) alkylcarbonylamino group, or two substituents together forming a methylenedioxy group;
• R1, R2 and R3 are selected, independently of each other, from:
• a hydrogen atom,
• a C1-C8 alkyl or (C1-C6)alkoxy(C1-C6)alkyl group,
• a cycloalkyl group containing from 3 to 8 carbon atoms, a (C3-C8)cycloalkyl(C1-C6) alkyl group, a (C3-C8)cycloalkyloxy(C1-C6)alkyl or (C3-C8)cycloalkyl(C1-C6)-alkoxy(C1-C6)alkyl group,
• a C6-C14aryl, C6-C14heteroaryl, (C6-C14)heteroaryl (C1-C6)alkyl, (C6-C14)aryl (C1-C6)alkyl (C6-C14)aryl (C1-C6)alkyl (C6-C14)aryl (C6-C14)aryl, (C1-C6)alkoxy (C1-C6)alkyl or (C6-C14)aryloxy (C1-C6)alkyl group,
• or alternatively R1 forms with the nitrogen atom to which R1 is attached and the Ar group a ring selected from indolinyl, quinolyl, indolyl and tetrahydroquinolyl;
• and
• R4, R5, R6 are selected, independently of each other, from:
• a hydrogen atom,
• a C1-C8alkyl, (C3-C8)cycloalkyl (C1-C6)alkyl, C1-C8 alkoxy, (C3-C8)cycloalkyloxy (C6-C6)alkyl, (C3-C8)cycloalkyl (C1-C6)alkoxy (C1-C6)alkyl, (C3-C8)cycloalkyloxy, (C3-C8)cycloalkyl (C1-C6)alkoxy, (C1-C6)alkoxy (C1-C6)alkyl, C6-C14 aryl, C6-C14 heteroaryl, (C6-C14)heteroaryl (C1-C6)alkyl, (C6-C14)aryl (C1-C6)alkyl, (C6-C14)aryl (C1-C6)alkyl (C6-C14)aryl, (C6-C14)aryloxy, (C6-C14)aryloxy (C1-C6)alkyl, (C6-C14)aryl (C1-C6)alkyloxy or (C6-C14)aryl (C1-C6)alkyloxy (C1-C6)alkyl groups, a halogen, a trifluoromethyl, trifluoromethoxy, cyano, hydroxyl, nitro, amino, (C1-C6)alkoxycarbonyl, carbamoyl, (C1-C8)alkylthio, (C1-C8)alkylsulphinyl, (C1-C8)alkylsulphonyl, sulphoamino, (C1-C8)alkylsulphonylamino, sulphamoyl or (C1-C8)alkylcarbonylamino group,
• optionally two of the R4, R5 and R6 groups together form a methylenedioxy group, and
• optionally, each aryl group being substituted with 1 to 3 substituents selected from a C1-C8 alkyl or C1-C8 alkoxy group, a halogen, a trifluoromethyl, trifluoromethoxy, hydroxyl, nitro and amino group,
• wherein heteroaryl in each case is selected from the pyridyl, pyrimidyl, pyrrolyl, furyl, thienyl, quinolyl, indolyl, benzothienyl, benzofuryl, benzopyrranyl, benzothiopyrannyl, dibenzofuryl, carbazolyl and benzothiazinyl groups;
• solvates thereof and pharmaceutically acceptable salts thereof.