Derivatives of 4-aminopiperidine and their use as a medicament
A subject of the present application is new derivatives of 4-aminopiperidines of formula in which R 1 , R 2 and R 3 represent various radical, and their preparation processes by synthetic methods in parallel in liquid and solid phase. These products having a good affinity with certain sub-types of somatostatin receptors, they are particularly useful for treating the pathological states or diseases in which one (or more) somatostatin receptors are involved.
1. Compounds of the general formula:
in racemic, enantiomeric form or all combinations of these forms, in which:
R 1 represents a —(CH 2 ) m —Z 12 radical in which Z 12 represents optionally substituted aryl;
R 2 represents a radical of formula —C(Y)NHX 1 , wherein X 1 represents a (CH 2 ) p Z 22 radical in which Z 22 represents aryl optionally substituted;
R 3 represents an optionally substituted alkyl;
Y represents an oxygen atom;
m is an integer from 1 to 6; and
p is an integer from 0 to 6;
or their addition salts with pharmaceutically acceptable mineral or organic acids.
2. The compound of claim 1 , wherein the aryl represented by Z 12 is substituted with one or more fluoro, chloro, bromo, iodo, alkyl, alkoxy, alkylthio, —CF 3 , —OCF 3 , phenyl, phenoxy or aminosulphonyl.
3. The compound of claim 1 , wherein the aryl represented by Z 22 is substituted with one or more fluoro, chloro, bromo, iodo, alkyl, alkenyl, alkoxy, alkylthio, CF 3 , OCF 3 , nitro, cyano, azido, aminosulphonyl, piperidinosulphonyl, mono- or di-alkylamino, —C(O)—O-alkyl, —C(O)-alkyl, optionally substituted phenyl, phenoxy, phenylthio or benzyloxy.
4. The compound of claim 1 , wherein the aryl represented by Z 12 is substituted with one or more fluoro, chloro, bromo, iodo, alkyl or alkoxy.
5. The compound of claim 1 , wherein the aryl represented by Z 22 is substituted with one or more fluoro, chloro, bromo, iodo, alkyl, alkoxy, alkylthio, CF 3 , OCF 3 , nitro, cyano, azido, piperidinosulphonyl, —C(O)—O-alkyl, —C(O)-alkyl or phenyl.
6. The compound of claim 1 , wherein R 3 is unsubstituted alkyl.
7. The compound of claim 1 , wherein R 3 is methyl.
8. The compound of claim 1 , wherein Z 12 and Z 22 are optionally substituted phenyl or naphthyl.
9. The compound of claim 1 , wherein m and p are simultaneously 1.
10. A pharmaceutical composition comprising a compound of claim 1 or an addition salt thereof with a pharmaceutically acceptable mineral or organic acid.