Back to results
US 2017/0247378 A1Published application
Imidazo[4,5-c]pyridine and pyrrolo[2,3-c]pyridine derivatives as ssao inhibitors
AssigneeProximagen Limited
InventorsMax Espensen, Lee Patient, David Evans, Iain Simpson, Edward Savory
Life of this patent
Estimating the term…
Abstract
The compounds of formula (I) are inhibitors of SSAO activity wherein V, W, X, Y, Z, R1 and R2 are as defined in the claims.
Claims21
A compound of formula (I) or a pharmaceutically acceptable salt, or N-oxide thereof:
- Wherein:
- Y is selected from hydrogen, hydroxyl, —NH2, —NH—C1-4-alkyl, —NH-halo-C1-4-alkyl, or —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, or —NHhalo-C1-4-alkyl;
- R1 is a phenyl ring, or a 5 or 6-membered heteroaryl ring, either 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;
- wherein
- R4A, R4B R5 and R6 are each independently selected from hydrogen, C1-4-alkyl or 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, —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, either 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)—, or —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 or a 3-7 membered heterocyclic ring or 3-7 membered cycloalkyl ring, or 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-C6alkyl, —(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.
19 more elements
A compound of formula (I) or a pharmaceutically acceptable salt, or N-oxide thereof:
- Wherein:
- Y is selected from hydrogen, hydroxyl, —NH2, —NH—C1-4-alkyl, —NH-halo-C1-4-alkyl, or —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, or —NHhalo-C1-4-alkyl;
- R1 is a phenyl ring, or a 5 or 6-membered heteroaryl ring, either ring being optionally substituted with one or more substituents selected from halogen, cyano, C1-4-alkyl, halo-C1-4-alkyl, cyano-C1-4-alkyl, —OR5, —NR6C(O)OR5, —NR6C(O)R5, —NR6C(O)NR4AR4B, —C(O)NR4AR4B, —C(O)R5, —C(O)OR5, and —NR6S(O)2R5;
- wherein
- R4A, R4B R5 and R6 are each independently selected from hydrogen, C1-4-alkyl or 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, —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, C(O)NR4AR4B, —C(O)R5, —C(O)OR5, —SO2R5, —SO2NR4AR4B and —NR6S(O)2R5;
- W is a phenyl ring or a 5 or 6-membered heteroaryl ring, either ring being optionally substituted with one or more substituents selected from halogen, cyano, C1-4-alkyl, halo-C1-4-alkyl, cyano-C1-4-alkyl, —OR5, —NR7AR7B, —NR6C(O)OR5, —NR6C(O)R5, —NR6C(O)NR7AR7B, —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)—, or —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 hydrogen, or a 3-7 membered heterocyclic ring, or 3-7 membered cycloalkyl ring selected from cyclopropyl, cyclopentyl or cyclohexyl, or 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 when —R3 is H, R1 is not a phenyl ring substituted with one —OCH3.
12 more elements
Dependencies are inferred from the claim text.