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PYRAZOLE DERIVATIVES AS MODULATORS OF THE 5-HT2A SEROTONIN RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO

  • US 20100004264A1
  • Filed: 10/02/2007
  • Published: 01/07/2010
  • Est. Priority Date: 10/03/2006
  • Status: Active Grant
First Claim
Patent Images

1. A compound of Formula (Ia):

  • or a pharmaceutically acceptable salt, solvate or hydrate thereof;

    wherein;

    R1 and R2 are each independently selected from the group consisting of H, C1-C6 alkyl, C1-C6 alkylaryl, aryl, C3-C7 cycloalkyl, C1-C6 haloalkyl, halogen, heteroaryl, and nitro; and

    wherein C1-C6 alkyl, aryl and heteroaryl are optionally substituted with 1, 2, 3, 4 or 5 substituents selected independently from the group consisting of C1-C6 acyl, C1-C6 acyloxy, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarboxamide, C1-C6 alkylsulfonamide, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylthio, C1-C6 alkylureyl, C1-C6 alkylamino, C2-C6 alkynyl, amino, carbo-C1-C6-alkoxy, carboxamide, carboxy, cyano, C3-C7 cycloalkyl, C2-C6 dialkylamino, C2-C6 dialkylcarboxamide, C2-C6 dialkylsulfonamide, C1-C6 haloalkoxy, C1-C6 haloalkyl, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 haloalkylthio, halogen, hydroxyl, nitro, sulfonamide and thiol;

    orR1 and R2 together with the carbon atoms to which they are bonded form a C3-C7 carbocyclyl or a C3-C7 heterocyclyl group each optionally substituted with 1, 2, 3, 4 or 5 substituents selected independently from the group consisting of C1-C6 acyl, C1-C6 acyloxy, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarboxamide, C1-C6 alkylsulfonamide, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylthio, C1-C6 alkylureyl, C1-C6 alkylamino, C2-C6 alkynyl, amino, carbo-C1-C6-alkoxy, carboxamide, carboxy, cyano, C3-C7 cycloalkyl, C2-C6 dialkylamino, C2-C6 dialkylcarboxamide, C2-C6 dialkylsulfonamide, C1-C6 haloalkoxy, C1-C6 haloalkyl, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 haloalkylthio, halogen, hydroxyl, nitro, oxo, sulfonamide and thiol;

    R3 is selected from the group consisting of H, C1-C6 alkyl and aryl; and

    wherein aryl is optionally substituted with 1, 2, 3, 4 or 5 substituents selected independently from the group consisting of C1-C6 acyl, C1-C6 acyloxy, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarboxamide, C1-C6 alkylsulfonamide, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylthio, C1-C6 alkylureyl, C1-C6 alkylamino, C2-C6 alkynyl, amino, carbo-C1-C6-alkoxy, carboxamide, carboxy, cyano, C3-C7 cycloalkyl, C2-C6 dialkylamino, C2-C6 dialkylcarboxamide, C2-C6 dialkylsulfonamide, C1-C6 haloalkoxy, C1-C6 haloalkyl, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 haloalkylthio, halogen, hydroxyl, nitro, sulfonamide and thiol;

    A and X are each —

    CH2CH2

    , each optionally substituted with 1, 2, 3 or 4 substituents selected independently from the group consisting of C1-C4 alkoxy, C1-C3 alkyl, carboxy, cyano, C1-C3 haloalkyl, halogen, hydroxyl and oxo;

    J is —

    CH2CH2

    or —

    C(═

    NOMe)CH2

    each optionally substituted with 1, 2, 3 or 4 substituents selected independently from the group consisting of C1-C4 alkoxy, C1-C3 alkyl, carboxy, cyano, C1-C3 haloalkyl, halogen, hydroxyl and oxo; and

    Ar is aryl or heteroaryl each optionally substituted with 1, 2, 3, 4 or 5 substituents selected independently from the group consisting of C1-C6 acyl, C1-C6 acyloxy, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarboxamide, C1-C6 alkylsulfonamide, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylthio, C1-C6 alkylureyl, C1-C6 alkylamino, C2-C6 alkynyl, amino, carbo-C1-C6-alkoxy, carboxamide, carboxy, cyano, C3-C7 cycloalkyl, C2-C6 dialkylamino, C2-C6 dialkylcarboxamide, C2-C6 dialkylsulfonamide, C1-C6 haloalkoxy, C1-C6 haloalkyl, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 haloalkylthio, halogen, C3-C7 heterocyclyl, hydroxyl, nitro, sulfonamide and thiol;

    provided that said compound is other than;

    1-(4-(1H-pyrazole-3-carbonyl)piperazin-1-yl)-2-(4-fluoro-1H-indol-3-yl)ethane-1,2-dione.

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