Patent NZ-602141-A (NZ)
Title: Inhibitors of semicarabazide-sensitive amine oxidase
Inventor: EVANS DAVID
IPC: A61K31/407
Filed: 2011-03-14
Abstract: Disclosed are 1-(aryl and heteroaryl)-1H-pyrrolo[2,3-c]pyridine derivatives as represented by the general formula (I), wherein R1 is optionally substituted phenyl or optionally substituted 6-membered heteroaryl; R2 is -B-Q-[R3]n or -B-R3; wherein n = 1, 2, 3, or 4; B is a bond, O, or C1-3-alkylene; Q is selected from: (i) a saturated or partially unsaturated monocyclic 3-7 membered heterocyclic ring or a C3-7-cycloalkyl ring, or (ii) a bridged heterocyclic or cycloalkyl ring selected from homomorpholine, tetrahydrofuranyl, tetrahydropyranyl, piperidinyl, piperazinyl, morpholinyl, cyclohexyl wherein the bridge is formed by an ethylene or propylene radical; Y is selected from hydrogen, hydroxyl, amino, -NHR6 or -OCH3; Z is selected from hydrogen, fluorine, hydroxyl, alkoxy, amino, -NHR6; W is selected from H, alkyl or haloalkyl; and wherein the remaining substituents are as defined herein. Representative compounds include 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-1,2,3,6-tetrahydropyridine, tert-butyl 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]piperidine-1-carboxylate, 1-(4-chlorophenyl)-3-piperidin-4-yl-1H-pyrrolo[5 2,3-c]pyridine, tert-butyl N-{ 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]cyclohexyl} carbamate, 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]cyclohexan-1-amine, 4-[1-(4-chloro-2-methylphenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]cyclohexan-1-amine, 1-{ 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl} -2-(dimethylamino)ethan-1-one, 1-{ 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridine-3-yl]piperidin-1-yl} -2-hydroxyethan-1-one, 2-amino-1-{ 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl} ethan-1-one, 3-amino-1-{ 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl} propan-1-one, 2-{ 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl} ethan-1-ol, 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-1-(1H-pyrazol-3-ylmethyl)piperidine, 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-1-[(1-methyl-1H-pyrazol-4-yl)-methyl]piperidine, 3-{ 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridine-3-yl]piperidin-1-yl} propanenitrile, 4-{ 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl} butanenitrile, [1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methanol, 1-{ [1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methyl} -4-methylpiperazine, tert-butyl 4-{ [1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methyl} piperazine-1-carboxylate, 1-{ [1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methyl} piperazine, 2-(1-{ [1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methyl} piperidin-4-yl)ethan-1-ol, (1-{ [1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methyl} piperidin-4-yl)methanol, 4-{ [1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methyl} morpholine, 1-{ [1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methyl} piperidin-4-ol, 2-({ [1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methyl} amino)ethan-1-ol, 1-(4-chlorophenyl)-3-(oxan-4-yl)-1H-pyrrolo[2,3-c]pyridine, 1-(4-methylphenyl)-3-(oxan-4-yl)-1H-pyrrolo[2,3-c]pyridine, 5-chloro-2-[3-(oxan-4-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl]pyridine, 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]morpholine, 4-amino-1-{ 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl} butan-1-one, 2-aminoethyl 4-[1-(4-chlorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]piperidine-1-carboxylate and 3-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-1-(4-methylphenyl)-1H-pyrrolo[2,3-c]pyridine and their pharmaceutically acceptable salts or N-oxides thereof. Also disclosed is a pharmaceutical composition for the treatment of inflammation, an inflammatory disease, an immune or an autoimmune disorder, or inhibition of tumour growth, the composition comprising a compound as defined above, together with one or more pharmaceutically acceptable carriers and/or excipients.