Substituted 3-(1,2,4-Oxadiazol-5-yl)-5-Phenylpiperidines
The invention relates to novel substituted piperidines, to processes for preparation thereof, to the use thereof for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially of cardiovascular disorders and tumour disorders.
1 . A compound of the formula
in which
R 1 is trifluoromethyl, trifluoromethoxy or ethyl,
R 2 is 2-methoxyeth-1-yl, 2-ethoxyeth-1-yl or cyclopropyl,
R 3 is a group of the formula
where
* is the point of attachment to the carbonyl group,
or one of its salts, its solvates or the solvates of its salts.
2 . A compound according to claim 1 , wherein
R 1 is trifluoromethyl or ethyl,
R 2 is 2-methoxyeth-1-yl or cyclopropyl,
R 3 is a group of the formula
where
* is the point of attachment to the carbonyl group,
or one of its salts, its solvates or the solvates of its salts.
3 . A compound according to claim 1 , wherein
R 1 is trifluoromethoxy or ethyl,
R 2 is 2-ethoxyeth-1-yl,
R 3 is a group of the formula
where
* is the point of attachment to the carbonyl group,
or one of its salts, its solvates or the solvates of its salts.
4 . A compound according to claim 1 , wherein the phenyl substituent and the 1,2,4-oxadiazol-5-yl substituent bonded to the piperidine ring, are in cis positions to one another.
5 . A process for preparing a compound of the formula (I) or one of its salts, its solvates or the solvates of its salts according to claim 1 , wherein either
[A] a compound of the formula
in which
R 1 and R 2 are each as defined in claim 1
is reacted with a compound of the formula
in which
R 3 is as defined in claim 1 and
X 1 is halogen, preferably bromine or chlorine, or hydroxyl,
or
[B] a compound of the formula (II) is reacted in the first stage with 4-nitrophenyl chloroformate and in the second stage with a compound of the formula
R 3 —H (IV)
in which
R 3 is as defined in claim 1 ,
or
[C] a compound of the formula
in which
R 1 and R 3 are each as defined in claim 1 ,
is reacted with a compound of the formula
in which
R 2 is as defined in claim 1 .
6 . (canceled)
7 . (canceled)
8 . (canceled)
9 . (canceled)
10 . A pharmaceutical composition comprising a compound according to claim 1 in combination with an inert, non-toxic, pharmaceutically acceptable excipient.
11 . A pharmaceutical composition comprising a compound according to claim 1 in combination with a further active ingredient.
12 . (canceled)
13 . A method for the treatment and/or prophylaxis of a thromboembolic disorder comprising administering to a human or animal in need thereof an anticoagulatory amount of a compound according to claim 1 .
14 . A method for the prevention of blood coagulation in vitro, comprising adding to blood ex vivo an anticoagulatory amount of a compound according to claim 1 .
15 . A method for the treatment and/or prophylaxis of a cardiovascular disorder comprising administering to a human or animal in need thereof an effective amount of a compound according to claim 1 .
16 . A method for the treatment and/or prophylaxis of a tumour disorder comprising administering to a human or animal in need thereof an effective amount of a compound according to claim 1 .
17 . A method for the treatment and/or prophylaxis of a thromboembolic disorder comprising administering to a human or animal in need thereof an anticoagulatory amount of a pharmaceutical composition according to claim 10 .
18 . A method for the treatment and/or prophylaxis of a cardiovascular disorder comprising administering to a human or animal in need thereof an anticoagulatory amount of a pharmaceutical composition according to claim 10 .
19 . A method for the treatment and/or prophylaxis of a tumour disorder comprising administering to a human or animal in need thereof an anticoagulatory amount of a pharmaceutical composition according to claim 10 .