2-heteroaryl-pyrrolo[3,4-c]pyrrole derivatives and their use as SCD inhibitors

1. A compound of formula I,

wherein:

R is hydrogen, (C 1 -C 16 )-alkyl, (C 1 -C 5 )-alkyloxy, (C 1 -C 5 )-alkylthio, (C 1 -C 5 )-alkylamino, di-(C 2 -C 8 -alkylamino, (C 0 -C 4 )-alkylene-(C 6 -C 10 )-aryl, (C 0 -C 4 )-alkylene-(C 5 -C 12 )-heteroaryl, (C 0 -C 4 )-alkylene-(C 3 -C 12 )-heterocyclyl, (C 0 -C 4 )-alkylene-(C 3 -C 12 )-cycloalkyl, or a bicyclic (C 8 -C 14 ) ring system,

wherein the aryl, heteroaryl, heterocyclyl, cycloalkyl or bicyclic (C 8 -C 14 ) ring system may be mono- or polysubstituted by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyloxy, hydroxyl, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 -alkylaminocarbonyl, di-(C 2 -C 6 -alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 -alkylcarbonyl, cyano, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

R1 is hydrogen, (C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyloxy, amino, mono-(C 1 -C 10 )-alkylamino, or di-(C 2 -C 12 )-alkylamino,

wherein the alkyl may be substituted by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyloxy, hydroxyl, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, -(C 6 -C 10 )-aryl, —(C 5 -C 12 )-heteroaryl, —(C 3 -C 12 )-heterocyclyl or —(C 3 -C 12 )-cycloalkyl,

wherein the aryl, heteroaryl, heterocyclyl or cycloalkyl may be mono- or polysubstituted by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyloxy, hydroxyl, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, or di-(C 2 -C 12 )-alkylamino;

R2 is hydrogen, (C 1 -C 16 )-alkyl, or (C 0 -C 4 )-alkylene-(C 6 -C 10 )-aryl;

R3 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyloxy, hydroxyl, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, cyano, (C 1 -C 6 )-alkylcarbonyl, halogen, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl;

A is S;

B is C(R3);

D is N;

n is 1;

L is a bond, —C(═O)—, —C(═S)—, —C(═O)—N(R2)—, —C(═O)—O—, —S(O) 0-2 —, —S(O) 0-2 —N(R2)—, or a mono- or bicyclic ring system in which one or more ring members may be N(R3), O, S or —C(═O)—; and

M is —C(═O)—N(R2)—, —N(R2)—C(═O)—, —S(O) 0-2 —, —S(O) 0-2 —N(R2)—, —N(R2)—S(O)—O—, or —O—C(═)—;

or a physiologically compatible salt thereof.

2. The compound according to claim 1 , wherein

R1 is (C 1 -C 10 -alkyl, (C 1 -C 10 )-alkyloxy, amino, mono-(C 1 -C 10 )-alkylamino, or di-(C 2 -C 12 )-alkylamino,

wherein the alkyl may be substituted by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyloxy, hydroxyl, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, —(C 6 -C 10 )-aryl, —(C 5 -C 12 )-heteroaryl, —(C 3 -C 12 )-heterocyclyl or —(C 3 -C 12 )-cycloalkyl,

wherein the aryl, heteroaryl, heterocyclyl or cycloalkyl may be mono- or polysubstituted by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyloxy, hydroxyl, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, or di-(C 2 -C 12 )-alkylamino;

M is —C(═O)—N(R2)—, —N(R2)—C(═O)—, —S(O) 0-2 —, —S(O) 0-2 —N(R2)—, —N(R2)—S(O) 0-2 —, or —O—C(═O)—;

or a physiologically compatible salt thereof.

3. The compound according to claim 1 , wherein

R is (C 1 -C 16 )-alkyl, (C 1 -C 5 )-alkyloxy, (C 0 -C 4 )-alkylene-(C 6 -C 10 )-aryl, or a bicyclic (C 8 -C 14 ) ring system,

wherein the aryl or bicyclic (C 8 -C 14 ) ring system may be mono- or polysubstituted by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyloxy, hydroxyl, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

R1 is (C 1 -C 10 -alkyl, (C 1 -C 10 )-alkyloxy, amino, mono-(C 1 -C 10 )-alkylamino, or di-(C 2 -C 12 )-alkylamino,

wherein the alkyl may be substituted by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyloxy, hydroxyl, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, —(C 6 -C 10 )-aryl, —(C 5 -C 12 )-heteroaryl, —(C 3 -C 12 )-heterocyclyl or —(C 3 -C 12 )-cycloalkyl,

wherein the aryl, heteroaryl, heterocyclyl or cycloalkyl may each optionally be mono- or polysubstituted by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyloxy, hydroxyl, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, or di-(C 2 -C 12 )-alkylamino;

L is a bond, or —C(═O)—; and

M is —C(═O)—N(R2)—, or —O—C(═O)—;

or a physiologically compatible salt thereof.

4. The compound according to claim 1 , which is:

Ethyl 2-[5-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl]thiazole-5-carboxylate;

N-(2-Cyclopropylethyl)-2-[5-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo-[3,4-c]pyrrol-2-yl]thiazole-5-carboxamide;

N-(3-Methylbutyl)-2-[5-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]-pyrrol-2-yl]thiazole-5-carboxamide;

N-(cyclopropylmethyl)-2-[5-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl]thiazole-5-carboxamide;

N-(3-methylbutyl)-2-(5-quinazolin-4-yl-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl)-thiazole-5-carboxamide;

N-(Cyclopropylmethyl)-2-(5-quinazolin-4-yl-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl)thiazole-5-carboxamide;

tert-Butyl 5-[5-(3-phenylpropylcarbamoyl)thiazol-2-yl]-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]-pyrrole-2-carboxylate;

N-(3-Phenylpropyl)-2-(5-quinazolin-4-yl-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl)-thiazole-5-carboxamide;

N-(3-Phenylpropyl)-2-[5-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]-pyrrol-2-yl]thiazole-5-carboxamide;

N-(3-Methylbutyl)-2-[5-(2-bromo-5-methoxybenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]-pyrrol-2-yl]thiazole-5-carboxamide;

N-(3-Phenylpropyl)-2-[5-(2-bromo-5-methoxybenzoyl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]-pyrrol-2-yl]thiazole-5-carboxamide;

or a physiologically compatible salt thereof.

5. A pharmaceutical composition comprising the compound according to claim 1 or a physiologically compatible salt thereof, in combination of a pharmacologically compatible carrier.

6. A pharmaceutical composition comprising the compound according to claim 2 or a physiologically compatible salt thereof, in combination of a pharmacologically compatible carrier.

7. A pharmaceutical composition comprising the compound according to claim 3 or a physiologically compatible salt thereof, in combination of a pharmacologically compatible carrier.

8. A pharmaceutical composition comprising the compound according to claim 4 or a physiologically compatible salt thereof, in combination of a pharmacologically compatible carrier.

9. A process for preparing a pharmaceutical composition comprising the compound according to claim 1 or a physiologically compatible salt thereof, in combination of a pharmacologically compatible carrier, which comprises mixing the compound according to claim 1 or the physiologically compatible salt thereof, with the pharmacologically compatible carrier and bringing this mixture into a form suitable for administration.