Imidazo[4,5-c]pyridine and pyrrolo[2,3-c]pyridine derivatives as SSAO inhibitors

A process for the preparation of a compound of formula (I) or a pharmaceutically acceptable salt, or N-oxide thereof

• comprising reacting a compound of formula (IIIb) with a compound of formula (IX) to form the compound of formula (I)
• wherein:
• Y is selected from hydrogen, hydroxyl, —NH2, —NH—C1-4-alkyl, —NH-halo-C1-4-alkyl, and —C1-4-alkoxy;
• Z is selected from hydrogen, halogen, hydroxyl, cyano, C1-4-alkyl, halo-C1-4-alkyl, C1-4-alkoxy, halo-C1-4-alkoxy, —CONH2, —SO2NH2, —NH2, —NHC1-4-alkyl, and —NHhalo-C1-4-alkyl;
• R1 is a phenyl ring, or a 5 or 6-membered heteroaryl ring, the ring being optionally substituted with one or more substituents selected from halogen, cyano, C1-4-alkyl, halo-C1-4-alkyl, cyano-C1-4-alkyl, a 3-7 membered cycloalkyl ring, —OR5, —NR6C(O)OR5, —NR6C(O)R5, —NR6C(O)NR4AR4B, —C(O)NR4AR4B, —C(O)R5, —C(O)OR5, and —NR6S(O)2R5;
• R4A, R4B, R5, and R6 are each independently selected from hydrogen, C1-4-alkyl, and halo-C1-4-alkyl, or
• R4A and R4B together with the nitrogen to which they are attached form a 3-7 membered cyclic amino group, optionally substituted by one or more substituents selected from halogen, hydroxyl, cyano, C1-4-alkyl, halo-C1-4-alkyl, C1-4-alkoxy, halo-C1-4-alkoxy, —CONH2, —SO2NH2, —NH2, —NHC1-4-alkyl, and —NHhalo-C1-4-alkyl;
• X is —C(R2)═;
• R2 is selected from hydrogen, halogen, cyano, C1-4-alkyl, halo-C1-4-alkyl, cyano-C1-4-alkyl, —OR5, —NR4AR4B, —NR6C(O)OR5, —NR6C(O)R5, —NR6C(O)NR4AR4B, —SO2R5, —SO2NR4AR4B and —NR6S(O)2R5;
• W is a phenyl ring or a 5 or 6-membered heteroaryl ring, the ring being optionally substituted with one or more substituents selected from halogen, cyano, oxo C1-4-alkyl, halo-C1-4-alkyl, cyano-C1-4-alkyl, —OR5, —NR7AR7B, —NR6C(O)OR5, —NR6C(O)R5, —NR6C(O)NR7AR7B, —C(O)NR7AR7B, —C(O)R5, —C(O)OR5, —SO2R5, —SO2NR7AR7B, and —NR6S(O)2R5;
• R7A and R7B are independently hydrogen, C1-4-alkyl, or halo-C1-4-alkyl;
• V is selected from a bond, —O—, —N(R6)—, —(C═O)—, —CONR6—, —NR6C(O)—, and —C1-4-alkylene-, wherein the C1-4-alkylene group is optionally substituted by halogen, and wherein any one of the carbon atoms of the C1-4-alkylene group may be replaced by —O— or —N(R6)—;
• R3 is selected from hydrogen, —C1-4-alkyl, —C1-4-alkyl-C1-4-alkoxy, a 3-7 membered heterocyclic ring, a 3-7 membered cycloalkyl ring, and a 5 or 6-membered heteroaryl ring, any one of the rings being optionally substituted with one or more substituents selected from halogen, oxo, hydroxyl, cyano, C1-4-alkyl, halo-C1-4-alkyl, cyano-C1-4-alkyl, —OR5, —NR4AR4B, —NR6C(O)OR5, —NR6C(O)R5, —NR6C(O)NR4AR4B, —C(O)NR4AR4B, —C(O)R5, —C(O)OR5, —SO2R5, —SO2NR4AR4B, and —NR6S(O)2R5;
• provided that groups —WVR3 and/or R1 are not:
• wherein:
• n is 0, 1, or 2;
• R′ and R″ are independently selected from the group consisting of H, —C1-C6 alkyl, —(C═O)—C1-C6 alkyl, and —(C═O)OC(CH3)3;
• and
• R′″ is H, OH, or C1-C6 alkyl;
• and
• further provided that when —R3 is H, R1 is not a phenyl ring substituted with one —OCH3.