Substituted benzoylureidopyridylpiperidine-and-pyrrolidinecarboxylic acid derivatives, processes for preparing them and their use
The invention relates to compounds of the formula I where the radicals are as defined, and their physiologically tolerated salts. The compounds are suitable, for example, as medicaments for preventing and treating type 2 diabetes.
1. A compound of the formula I
wherein
R1, R2 are each independently H, F, Cl, Br, (C 1 -C 6 )-alkyl, CF 3 , OCF 3 , NO 2 , CN, O—(C 1 C 6 )-alkyl, COO(C 1 -C 6 )-alkyl, COOH, CO—(C 1 -C 6 )-alkyl, (C 0 -C 6 )-alkyl-COOH, (C 0 C 6 )-alkyl -COO(C 1 C 6 )-alkyl or SO 2 -(C 1 -C 6 )-alkyl;
R3 is OH, (C 1 -C 6 )-alkyl, (C 0 -C 6 )-alkyl-aryl, O—(C 1 -C 6 )-alkyl, O—(C 2 -C 6 )-alkenyl or O—(C 2 -C 6 )-alkynyl, wherein said (C 1 -C 6 )-alkyl, (C 0 -C 6 )-alkyl-aryl, O—(C 1 -C 6 )-alkyl, O—(C 2 -C 6 )-alkenyl and O—(C 2 -C 6 )-alkynyl radicals are optionally mono- or polysubstituted by F, Cl or Br;
X is OH, O—(C 1 -C 6 )-alkyl, NH 2 , NH(C 1 -C 6 )-alkyl or N((C 1 -C 6 )-alkyl) 2 ;
A is N;
B, D and E are CH;
m is 2;
or a pharmaceutically acceptable salt thereof.
2. The compound of claim 1 wherein:
R1, R2 are each independently H, F, Cl, Br, (C1-C 6 )-alkyl, CF 3 , OCF 3 , NO 2 , CN, O—(C 1 -C 6 )-alkyl, COO(C 1 -C 6 )-alkyl, COOH, CO—(C 1 -C 6 )-alkyl, (C 0 -C 6 )-alkyl-COOH, (C 0 -C 6 )-alkyl-COO(C 1 -C 6 )-alkyl or SO 2 —(C 1 -C 6 )-alkyl;
R3 is OH, (C 1 -C 6 )-alkyl, (C 0 -C 6 )-alkyl-aryl, O—(C 1 -C 6 )-alkyl, O—(C 2 -C 6 )-alkenyl or O—(C 2 -C 6 )-alkynyl, wherein said (C 1 -C 6 )-alkyl, (C 0 -C 6 )-alkyl-aryl, O—(C 1 C 6 )-alkyl, O—(C 2 -C 6 )-alkenyl and O—(C 2 -C 6 )-alkynyl radicals are optionally mono- or polysubstituted by F, Cl or Br;
X is OH, O—(C 1 -C 6 )-alkyl, NH 2 , NH(C 1 -C 6 )-alkyl or N((C 1 -C 6 )-alkyl) 2 ;
A is N;
B, D and E are CH;
m is 2;
or a pharmaceutically acceptable salt thereof.
3. The compound of claim 2 wherein:
R1 is H or F;
R2 is each independently H, F, Cl, Br, (C 1 C 6 )-alkyl, CF 3 , OCF 3 , O—(C 1 -C 6 )-alkyl, COO(C 1 -C 6 )-alkyl, COOH, CO—(C 1 C 6 )-alkyl, (C 0 -C 6 )-alkyl-COOH, (C 0 -C 6 )-alkyl-COO(C 1 -C 6 )-alkyl or SO 2 —(C 1 -C 6 )-alkyl;
R3 is OH, (C 1 ,-C 6 )-alkyl, (C 0 -C 6 )-alkyl-aryl, O—(C 1 -C 6 )-alkyl, O—(C 2 -C 6 )-alkenyl or O—(C 2 -C 6 )-alkynyl, wherein said (C 1 -C 6 )-alkyl, (C 0 -C 6 )-alkyl-aryl, O—(C 1 -C 6 )-alkyl, O—(C 2 -C 6 )-alkenyl and O—(C 2 -C 6 )-alkynyl radicals are optionally mono- or polysubstituted by F, Cl or Br;
X is OH, O—(C 1 -C 6 )-alkyl, NH 2 , NH(C 1 -C 6 )-alkyl or N((C 1 -C 6 )-alkyl) 2 ;
A is N;
B, D, E are each CH;
m is 2;
or a pharmaceutically acceptable salt thereof.
4. The compound of claim 3 wherein:
R1 is H or F;
R2 is H, Cl, (C 1 -C 6 )-alkyl, CF 3 , COO(C 1 -C 6 )-alkyl or COOH,
R3 is H or phenyl;
X is OH, O—(C 1 -C 6 )-alkyl, NH 2 , NH(C 1 -C 6 )-alkyl or N((C 1 -C 6 )-alkyl) 2 ;
A is N;
B, D, E are each CH;
m is 2;
or a pharmaceutically acceptable salt thereof.
5. A pharmaceutical composition comprising one or more compounds of claim 1 and a pharmaceutically acceptable carrier.