EP2202232A1 — 1,2,4-oxadiazole derivatives and their therapeutic use

USPTO Abstract

New derivatives of general formula (I), or pharmaceutically acceptable salts or N-oxides thereof wherein, A is selected from the group consisting of -N-, -O- and -S-; B and C are independently selected from the group consisting of-N- and -O-, with the proviso that at least two of A, B and C are nitrogen atoms; G 1 is selected from the group consisting of -CH 2 -, -NH- and -O-; G 2 is selected from the group consisting of -NR 4 - and -O-; R 1 represents: ➢ a 8 to 10 membered bicyclic N-containing heteroaryl group optionally substituted with a C 1-4 carboxyalkyl group or a C 1-4 aminoalkyl group, ➢ a pyridyl group optionally substituted with one or more substituents selected from hydroxy groups, C 1-4 alkyl groups, C 1-4 carboxyalkyl groups, C 1-4 haloalkyl groups, C 1-4 alkoxy groups, amino groups, C 1-4 aminoalkyl groups and C 1-4 aminoalkoxy groups, ➢ a pyridone group substituted with one or more C 1-4 alkyl groups; C 1-4 haloalkyl groups or C 1-4 aminoalkyl groups, or ➢ a group of formula: wherein: • R a represents a hydrogen atom, a halogen atom, a C 1-4 alkyl group, C 3-4 cycloalkyl group or a -CF 3 group; • R b represents a hydrogen atom, a halogen atom, a C 14 alkyl group, a -CF 3 group or a C 1-4 alkoxy group; • R d represents a hydrogen atom, a C 1-4 alkyl group or a C 1-4 alkoxy group; • R c represents: ○ a hydrogen atom, a C 1-4 hydroxyalkyl group, a C 1-4 aminoalkyl group which is optionally substituted with one or more substituents selected from halogen atoms, hydroxy groups and -CF 3 groups; ○ a 4 to 6-membered saturated N-containing heterocyclic ring optionally substituted with a C 1-2 carboxyalkyl group; ○ -(CH 2 ) (0-4) -C(O)OR', -(CH 2 ) (0-4) -C(O)NR'R", -(CH 2 ) (0-4) -NHC(O)R", -S(O) 2 NR'R", -O-(CH 2 ) (2-4) NR'R", -O-(CH 2 ) (1-4) C(O)OR", -O-(CH 2 ) (1-4) -C(O)NR'R", -(CH 2 ) (0-4) -NR'R", -(CH 2 ) (0-4) -CONHS(O) 2 R', -(CH 2 ) (0-4) -NHS(O) 2 R' or -(CH 2 ) (0-3) -N H-(CH 2 ) (1-3) -(NH) (0-1) S(O) 2 R' wherein, ■ R' represents a hydrogen atom or a C 1-4 alkyl group, ■ R" represents a hydrogen atom, a C 1-4 alkyl group, a C 3-4 cycloalkyl group, a C 1-4 carboxyalkyl group, a C 1-4 haloalkyl group, a C 1-4 hydroxyalkyl group or a 6 membered, saturated N-containing heterocyclic ring, or ■ R' and R" together with the nitrogen atom to which they are attached from a 4 to 6 membered heterocyclic group which contains, as heteroatoms, one N atom and, optionally, one further atom selected from N and O, and which is optionally substituted with a carboxy or a C 1-4 carboxyalkyl group, or R c together with R d form a C 5-6 cycloalkyl group optionally substituted by a -NHR f group, wherein R f is selected from the group consisting of a hydrogen atom and a carboxymethyl group; R 2 and R 3 are independently selected from the group consisting of hydrogen atoms, halogen atoms and C 1-4 alkyl groups; and R 4 is selected from the group consisting of a hydrogen atom, a phenyl group, a C 3-4 cycloalkyl-C 1-4 alkyl group, C 1-4 aminoalkyl group, C 1-4 haloalkyl group and a linear or branched C 1-4 alkyl group which is optionally substituted by a phenyl or a pyridyl group.