Quinoline and isoquinoline derivatives, a process for their production and their use as inflammation inhibitors
The invention relates to quinoline and isoquinoline derivatives of general formula I and a process for their production, and their use as inflammation inhibitors.
1. A compound of formula I
wherein
A stands for an aryl group, a benzyl group or a phenethyl group, optionally substituted by:
one or more radicals of C 1 -C 5 -alkyl, C 1 -C 5 -alkoxy, C 1 -C 5 -alkylthio, C 1 -C 5 -perfluoroalkyl, halogen, hydroxy, cyano, or nitro; or
—O—(CH 2 ) n —O—, —O—(CH 2 ) n —CH 2 —, —O—CH═CH—, or —(CH 2 ) n+2 —, wherein n=1 or 2, and wherein the two terminal atoms in these groups are linked with directly adjacent ring-carbon atoms of the aryl, benzyl or phenethyl group to form a fused ring; or
NR 4 R 5 , wherein R 4 and R 5 , independently of one another, are hydrogen, C 1 -C 5 -alkyl or (CO)—C 1 -C 5 -alkyl,
R 1 and R 2 , independently of one another, are a hydrogen atom, a methyl or an ethyl group or together with the carbon atom of the chain form a C 3 -C 6 -cycloalkyl ring,
R 3 means a C 1 -C 3 -alkyl group or a C 1 -C 3 -alkyl group optionally partially or completely fluorinated,
B means a carbonyl group or a methylene group that is optionally substituted by a methyl, or an ethyl, group, and
Q means a quinolinyl group or an isoquinolinyl group that is linked via any position and that optionally can be substituted by one or more radicals from the group C 1 -C 5 -alkyl, wherein C 1 -C 5 -alkyl is optionally substituted by 1-3 hydroxy groups and/or 1-3 COOR 6 groups; C 1 -C 5 -alkoxy; C 1 -C 5 -alkylthio; C 1 -C 5 -perfluoroalkyl; halogen; hydroxy; a carbonyl-oxygen atom; cyano; nitro; or NR 4 R 5 ,
wherein R 4 and R 5 , independently of one another, are hydrogen, C 1 -C 5 -alkyl or (CO)—C 1 -C 5 -alkyl;
COOR 6 , wherein R 6 means hydrogen or a C 1 -C 5 -alkyl group;
(CO)NR 7 R 8 , wherein R 7 and R 8 , independently of one another, mean hydrogen or a C 1 -C 5 -alkyl group;
or a (C 1 -C 5 -alkylene)-O—(CO)—(C 1 -C 5 )alkyl group;
or a racemate, a separately present stereoisomer, or a physiologically compatible salt thereof.
2. A compound according to claim 1 , wherein Q means a quinolinyl group or an isoquinolinyl group that is linked via any position and that optionally can be substituted by one or more radicals from the group C 1 -C 5 -alkyl, a carbonyl-oxygen atom, COOR 6 , wherein R 6 means hydrogen or a C 1 -C 5 -alkyl group, (CO)NR 7 R 8 , wherein R 7 and R 8 , independently of one another, mean hydrogen or a C 1 -C 5 -alkyl group, or a (C 1 -C 5 -alkylene)-O—(CO)—(C 1 -C 5 )alkyl group.
3. A compound according to claim 2 , wherein A is an aryl radical.
4. A compound according to claim 3 , wherein A is a phenyl radical that is substituted by a hydroxy group, a methoxy group, and a halogen atom.