Azabicycloalkane derivatives, preparation thereof and use thereof in therapy
View Patent ↗The invention relates to compounds of the general formula (I): Wherein R, m, n and o are as defined herein. The invention also relates to a method for preparing the same and to the application in therapy.
1. A compound of the formula (I):
in which:
R represents hydrogen, halogen, hydroxyl, (C 1 -C 6 )alkoxy, (C 3 -C 7 )cycloalkyl-O—, (C 3 -C 7 )cycloalkyl-(C 1 -C 3 )alkylene-O—,
or a heterocycloalkyl, aryl or heteroaryl group; wherein said group is optionally substituted by one or more groups chosen from halogen, (C 1 -C 6 )alkyl, (C 3 -C 7 )cycloalkyl, (C 3 -C 7 )cycloalkyl-(C 1 -C 3 )alkylene, (C 1 -C 6 )alkoxy, (C 3 -C 7 )cycloalkyl-O—, (C 3 -C 7 )cycloalkyl-(C 1 -C 3 )alkylene-O—, (C 1 -C 6 )fluoroalkyl, (C 1 -C 6 )fluoroalkoxy, nitro, cyano, hydroxyl, amino, (C 1 -C 6 )alkylamino, di(C 1 -C 6 )alkylamino, heterocycloalkyl, aryl, aryl-(C 1 -C 6 )alkylene, heteroaryl, heteroaryl-(C 1 -C 6 )alkylene, aryl-O— or —C(O)—(C 1 -C 6 )alkyl groups, the heterocycloalkyl group optionally being substituted by —C(O)O(CH 3 ) 3 ;
n represents 1;
m represents 1; and
o represents 1;
or a salt thereof; and
with the proviso that when n and o are 1 m is not 2; and
the following compounds are excluded:
4-(6-fluoropyridin-3-yl)-1-azabicyclo[2.2.1]heptane;
4-(6-chloropyridin-3-yl)-1-azabicyclo[2.2.1]heptane;
4-(6-bromopyridin-3-yl)-1-azabicyclo[2.2.1]heptane;
4-(pyridin-3-yl)-1-azabicyclo[2.2.1]heptane.
2. The compound of formula (I) according to claim 1 , wherein:
R represents hydrogen, halogen, hydroxyl,
or a heterocycloalkyl, aryl or heteroaryl group; wherein said group is optionally substituted by one or more groups chosen from halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )fluoroalkyl, (C 1 -C 6 )fluoroalkoxy, nitro, cyano, hydroxyl, amino, (C 1 -C 6 )alkylamino, di(C 1 -C 6 )alkylamino, heterocycloalkyl, aryl, aryl-(C 1 -C 6 )alkylene, heteroaryl, aryl-O— or —C(O)—(C 1 -C 6 )alkyl groups, the heterocycloalkyl group optionally being substituted by —C(O)O(CH 3 ) 3 ;
n represents 1;
m represents 1; and
o represents 1;
or a salt thereof.
3. The compound of formula (I) according to claim 1 , wherein:
R represents halogen, hydroxyl,
or a heterocycloalkyl group or an aryl group or a heteroaryl group; wherein said group is optionally substituted by one or more groups chosen from halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )fluoroalkyl, (C 1 -C 6 )fluoroalkoxy, di(C 1 -C 6 )alkylamino, heterocycloalkyl, aryl, aryl-(C 1 -C 6 )alkylene, heteroaryl, aryl-O— or —C(O)—(C 1 -C 6 )alkyl groups; the heterocycloalkyl group optionally being substituted by —C(O)O(CH 3 ) 3 ;
n represents 1;
m represents 1; and
o represents 1;
or a salt thereof.
4. A pharmaceutical composition comprising a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.
5. A pharmaceutical composition comprising a compound of formula (I) according to claim 2 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.
6. A pharmaceutical composition comprising a compound of formula (I) according to claim 3 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.