Condensed imidazole derivatives as aldosterone synthase inhibitors

1. A compound of the formula

in which

R is deuterium, halogen, or hydrogen;

R 1 is aryl-C 0 -C 4 -alkyl or heterocyclyl-C 0 -C 4 -alkyl, which radicals are unsubstituted or substituted by 1-4 C 1 -C 8 alkoxy, C 1 -C 8 alkoxycarbonyl, C 1 -C 8 alkyl, C 0 -C 8 alkylcarbonyl, C 1 -C 8 alkylsulphonyl, unsubstituted or substituted aryl, aryl-C 0 -C 4 alkoxycarbonyl, cyano, halogen, unsubstituted or substituted heterocyclyl, hydroxy, nitro, oxide, oxo, tri-C 1 -C 4 alkylsilyl, trifluoromethoxy or trifluoromethyl;

R 2 is a) deuterium, halogen, hydroxy, cyano or hydrogen; or

is b) C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 alkoxy, C 1 -C 4 alkoxycarbonyl-C 1 -C 4 alkyl, C 1 -C 8 alkyl, C 0 -C 4 alkylcarbonyl, aryl-C 0 -C 4 alkyl, carboxy-C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl or heterocyclyl-C 0 -C 4 alkyl, which radicals are unsubstituted or substituted by 1-4 C 1 -C 8 alkoxy, C 1 -C 8 alkoxycarbonyl, C 1 -C 8 alkyl, C 0 -C 8 alkylcarbonyl, C 1 -C 8 alkylsulphonyl, unsubstituted or substituted aryl, aryl-C 0 -C 4 alkoxycarbonyl, cyano, halogen, unsubstituted or substituted heterocyclyl, hydroxy, nitro, oxide, oxo, tri-C 1 -C 4 alkylsilyl, trifluoromethoxy or trifluoromethyl;

R 3 is C 1 -C 8 alkyl;

Q is sulphur;

m is a number 0, 1 or 2;

n is a number 1;

or a pharmaceutically acceptable salt thereof

where

R 1 is not C 1 -C 8 alkyl-substituted aryl if R 2 is hydrogen; and heterocyclyl in heterocyclyl-C 0 -C 4 -alkyl stands for a saturated, partially saturated or unsaturated, 4-8 membered monocylic ring system, a saturated, partially saturated or unsaturated 7-12 membered bicyclic ring system, or a partially saturated or unsaturated 9-12 membered tricyclic ring system.

2. A compound according to claim 1 , which corresponds to the formula

or a pharmaceutically acceptable salt thereof, where the meanings of the substituents R, R 1 , R 2 , R 3 , Q, m and n are as indicated for compounds of the formula (I) according to claim 1 , and * designates an asymmetric carbon atom and which compound shows an aldosterone synthase and/or 11-β-hydroxylase inhibitory activity at least 10 times higher, than the compound of the formula (Ia) with the opposite configuration around the asymmetric carbon atom labelled “*”.

3. A compound according to claim 2 , and which compound shows an aldosterone synthase and/or 11-β-hydroxylase inhibitory activity at least 20 times higher than the compound of the formula (Ia) with the opposite configuration around the asymmetric carbon atom labelled “*”.

4. A compound according to claim 3 , and which compound shows an aldosterone synthase and/or 11-β-hydroxylase inhibitory activity at least 40 times higher than the compound of the formula (Ia) with the opposite configuration around the asymmetric carbon atom labelled “*”.

5. A compound according to claim 1 , where R is deuterium or hydrogen.

6. A compound according to claim 2 , where R is deuterium or hydrogen.

7. A compound according to claim 1 , where R 1 is unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, benzofuranyl, benzo[b]thiophenyl, benzoimidazolyl, benzo[d]isothiazolyl, benzo[d]isoxazolyl, benzo[b]thiophenyl, imidazolyl, indazolyl, oxazolyl, pyridyl, pyrrolyl, thiazolyl or thiophenyl.

8. A compound according to claim 2 , where R 1 is unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, benzofuranyl, benzo[b]thiophenyl, benzoimidazolyl, benzo[d]isothiazolyl, benzo[d]isoxazolyl, benzo[b]thiophenyl, imidazolyl, indazolyl, oxazolyl, pyridyl, pyrrolyl, thiazolyl or thiophenyl.

9. A compound according to claim 1 , where R 2 is C 1 -C 8 alkoxy, hydroxy, C 1 -C 8 alkyl, substituted or substituted aryl-C 0 -C 4 alkyl, deuterium, halogen, cyano or hydrogen.

10. A compound according to claim 2 , where R 2 is C 1 -C 8 alkoxy, hydroxy, C 1 -C 8 alkyl, unsubstituted or substituted aryl-C 0 -C 4 alkyl, deuterium, halogen, cyano or hydrogen.

11. A method for delaying the progression or for the treatment of hypertension in a patient, which comprises administering a therapeutically effective amount of a compound of the formula (I) or a pharmaceutically acceptable salt thereof according to claim 1 to the patient.

12. A method for delaying the progression or for the treatment of hypertension in a patient, which comprises administering a therapeutically effective amount of a compound of the formula (Ia) or a pharmaceutically acceptable salt thereof according to claim 2 to the patient.

13. A method for delaying the progression or for the treatment of Cushing's Syndrome in a patient, which comprises administering a therapeutically effective amount of a compound of the formula (I) or a pharmaceutically acceptable salt thereof according to claim 1 to the patient.

14. A method for delaying the progression or for the treatment of Cushing's Syndrome in a patient, which comprises administering a therapeutically effective amount of a compound of the formula (Ia) or a pharmaceutically acceptable salt thereof according to claim 2 to the patient.

15. A pharmaceutical composition comprising a compound of the formula (I) or a pharmaceutically acceptable salt thereof according to claim 1 , and conventional excipients a conventional excipient.

16. A pharmaceutical composition comprising a compound of the formula (Ia) or a pharmaceutically acceptable salt thereof according to claim 2 , and conventional a conventional excipient.

17. A pharmaceutical composition in the form of a product or of a kit comprising individual components consisting a) of a compound of the formula (I) or a pharmaceutically acceptable salt thereof according to claim 1 , and b) at least one pharmaceutical form whose active ingredient has a blood pressure-lowering, an inotropic, a metabolic or a lipid-lowering effect.

18. A pharmaceutical composition in the form of a product or of a kit comprising individual components consisting a) of a compound of the formula (Ia) or a pharmaceutically acceptable salt thereof according to claim 2 , and b) at least one pharmaceutical form whose active ingredient has a blood pressure-lowering, an inotropic, a metabolic or a lipid-lowering effect.