Bicyclic N-arylamides
View Patent ↗This application relates to bicyclic N-aryl amides of the formula R 1 is a 1 -aza-bicyclo[ 3.2.1 ]octyl group, a 1 -aza-bicyclo[ 2.2.2 ]oct- 3 -yl; R 2 is an optionally sustituted 8 - to 10 - membered heteroaryl, naphthyl, or azulenyl group; and R 3 is H or (C 1 C 6 )alkyl; or a salt, solvate, or solvate of a salt of these compounds. A process for preparing these compounds, medicaments containing them, and methods for using them in treatment are also disclosed and claimed.
1. A compound of the general formula (I)
in which
R 1 is a 1-aza-bicyclo[3.2.1]octyl, 1-aza-bicyclo[3.3.1]nonyl, or 1-aza-bicyclo[2.2.2]oct-3-yl, wherein the bicycloalkyl radical is optionally substituted by (C 1 –C 6 )-alkyl,
R 2 is 8- to 10-membered heteroaryl, naphthyl or azulenyl, where the rings are optionally substituted by 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,
and
R 3 hydrogen or (C 1 –C 6 )-alkyl,
or their salts, solvates and solvates of the salts.
2. The compound of claim 1 , where
R 1 is 1-azabicyclo[2.2.2]oct-3-yl,
and R 2 and R 3 have the meaning indicated in claim 1 .
3. The compound of claim 1 or 2 , where
R 1 is 1-azabicyclo[2.2.2]oct-3-yl,
R 2 is benzotriazolyl, benzothiophenyl, quinolinyl, benzopyrazinyl or naphthyl, where the rings are optionally substituted by 1 to 3 radicals selected from the group of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, (C 1 –C 4 )-alkyl, (C 1 –C 4 )-alkoxy, (C 1 –C 4 -alkylthio,
and
R 3 is hydrogen.
4. A process for preparing compounds of the general formula (I) as claimed in claim 1 , characterized in that compounds of the general formula (II)
R 1 —CO—X (II)
in which
R 1 has the meaning indicated in claim 1 , and
X is hydroxyl or a suitable leaving group,
are reacted with a compound of the general formula (III)
HNR 1 R 2 (III)
in which
R 2 and R 3 have the meaning indicated in claim 1 ,
in an inert solvent, where appropriate in the presence of a condensing agent and where appropriate
in the presence of a base.
5. Medicament comprising at least one compound according to claim 1 mixed with at least one pharmaceutically acceptable, essentially nontoxic carrier or excipient.
6. A method for the treatment and/or prophylaxis of impairments of perception, concentration, learning and/or memory comprising administering to a subject an effective amount of a compound of claim 1 .
7. A method for the treatment and/or prophylaxis of impairments of perception, concentration, learning and/or memory comprising administering to a subject an effective amount of a compound of claim 5 .