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US 7,459,456 B2Granted
Quinoline and quinazoline derivatives having affinity for 5HT1-type receptors
AssigneeGlaxo Group Limited
InventorsMatteo Biagetti, Alessandro Falchi, Colin Philip Leslie, Giancarlo Merlo, Domenica Antonia Pizzi, Marilisa Rinaldi, Luigi Piero Stasi, Jessica Tibasco
Life of this patent
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Abstract
Compounds of formula (I) and pharmaceutically acceptable salts thereof are provided: wherein R1, m, X, R2, n, W, p, Y, Z, R3, R4, R5 and q have the meanings as defined in the description. Methods of preparation and uses thereof in therapy, particularly for CNS disorders such as depression or anxiety, are also disclosed.
Claims12
A compound of formula (Ib):
- wherein:
- R1 is halogen, cyano, C1-6alkyl, C1-6alkoxy, haloC1-6alkoxy or haloC1-6alkyl;
- X is N or CH;
- R3 and R4 are independently hydrogen, C1-6alkyl, C1-6alkylsulfonyl, a group having the formula (IIa):
- wherein A is oxygen or sulfur, D is —(CH2)t—, —(CH2)tO— or —O(CH2)t—, wherein t is 0, 1, 2, 3 or 4;
- and E is C1-6alkyl;
- C3-7cycloalkyl, optionally substituted by one or more substituents independently selected from halogen, hydroxy, oxo, C1-6alkyl, cyano, CF3, OCF3, C1-6alkoxy and C1-6alkanoyl;
- or aryl, optionally substituted by one or more substituents independently selected from halogen, C1-6alkyl, CF3, cyano, hydroxy, C1-6alkanoyl, and C1-6alkoxy;
- or a group having formula (IIb)
- wherein A is oxygen or sulfur, D is —(CH2)t—, —(CH2)tO— or —O(CH2)t—, wherein t is 0,1, 2, 3 or 4;
- and E is C1-6alkyl;
- C3-7cycloalkyl, optionally substituted by one or more substituents independently selected from halogen, hydroxy, oxo, C1-6alkyl, cyano, CF3, OCF3, C1-6alkoxy and C1-6alkanoyl;
- or aryl optionally substituted by one or more substituents independently selected from halogen, C1-6alkyl, CF3, cyano, hydroxy, C1-6alkanoyl, and C1-6alkoxy;
- or R3 and R4, together with the nitrogen atom to which R3 and R4 are attached, combine to form a 3-7 membered monocyclic heterocyclic group or a 8-11 membered bicyclic heterocyclic group, wherein each group is optionally substituted by one or more substituents selected from halogen, oxo, C1-6alkyl, cyano, CF3, C1-6alkoxy, C1-6alkanoyl, aryl and arylC1-6alkyl, wherein the aryl and arylC1-6 are further optionally substituted by one or more halogen, oxo, C1-6alkyl, cyano, CF3, C1-6alkoxy and C1-6alkanoyl;
- or pharmaceutically acceptable salt thereof.
12 more elements
A compound which is:
- 3-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-1,3-oxazolidin-2-one;
- N-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-N′-phenylurea;
- N-[2-(methyloxy)phenyl]-N′-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)urea;
- 2,4-dimethyl-N-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-1,3-thiazole-5-carboxamide;
- 2-fluoro-N-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)benzamide;
- 1-methyl-3-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone;
- 1-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2,4-imidazolidinedione;
- 1-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-1,3-dihydro-2H-imidazol-2-one;
- 1-methyl-3-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-1,3-dihydro-2H-imidazol-2-one;
- 4,4-dimethyl-1-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone;
- or a pharmaceutically acceptable salt thereof.
8 more elements
Dependencies are inferred from the claim text.