Heteroaryl carboxylic acid amides
View Patent ↗The invention relates to novel heteroaryl carboxamides, a process for their preparation, and pharmaceutical compositions containing them. These materials are useful for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning and/or memory.
1. A compound of the formula (I)
in which
R 1 is an azabicyclo[m.n.o]alkyl radical having 7 to 11 ring atoms, in which m, n and o are identical or different and are 0, 1, 2 or 3,
and where the radical is optionally substituted by (C 1 -C 6 )-alkyl,
the ring A is pyrimido, or
is optionally benzo-fused pyrido, pyridazo or pyridazino,
and
R 2 and R 3 are identical or different and are radicals selected from the group of hydrogen, halogen, formyl, carbamoyl, cyano, trifluoromethyl, trifluoromethoxy, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio, (C 3 -C 8 )-cycloalkyl, 4- to 8-membered heterocyclyl, phenyl or 5- to 6-membered heteroaryl, where phenyl and heteroaryl are optionally substituted by halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, amino, mono- or di-(C 1 -C 4 )-alkylamino, (C 1 -C 4 )-alkanoylamino or (C 1 -C 4 )-alkanesulfonylamino,
or a salt thereof.
2. A compound as claimed in claim 1 , where
R 1 has the meaning indicated in claim 1 ,
the ring A together with the fused-on benzene residue is quinolin-5-yl or quinolin-6-yl,
and
R 2 and R 3 are identical or different and are radicals selected from the group of hydrogen, halogen, cyano, trifluoromethyl, methyl and ethyl,
or a salt thereof.
3. A compound as claimed in claim 1 or 2 , where
R 1 is 1-azabicyclo[2.2.2]oct-3-yl,
and ring A, R 2 and R 3 have the meaning indicated in claim 1 or 2 ,
or a salt thereof.
4. A process for preparing compounds of the formula (I) as claimed in claim 1 , characterized in that
compounds of the general formula (II)
R 1 —NH 2 (II)
in which R 1 has the meaning indicated in claim 1 ,
are reacted with a compound of the general formula (III)
in which
the ring A, R 2 and R 3 have the meaning indicated in claim 1 , and
X is hydroxyl or a suitable leaving group,
in an inert solvent, where appropriate in the presence of a condensing agent, and where appropriate in the presence of a base.
5. A pharmaceutical composition comprising at least one compound as claimed in any of claims 1 to 3 in combination with at least one pharmaceutically acceptable, essentially nontoxic carrier or excipient.