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Pyridazinyl derivatives as SMO inhibitors

  • US 9,409,871 B2
  • Filed: 05/30/2013
  • Issued: 08/09/2016
  • Est. Priority Date: 07/18/2008
  • Status: Active Grant
First Claim
Patent Images

1. A compound, or a pharmaceutically acceptable salt thereof, selected from:

  • (R)-4-(4,5-Dimethyl-6-phenoxy-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic methyl ester;

    (R)-4-(4,5-Dimethyl-6-phenylamino-pyridazin-3-yl)-2-methyl-3,4,5,6-tetra-hydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid methyl ester;

    (R)-4-(4,5-Dimethyl-6-phenylamino-pyridazin-3-yl)-2-methyl-3,4,5,6-tetra-hydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid phenylamide;

    2-[(R)-4-(4,5-Dimethyl-6-phenylamino-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -yl]-propan-2-ol;

    (R)-4-[6-(4-fluoro-phenyl)-4,5-dimethyl-pyridazin-3-yl]-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid methyl ester;

    (R)-4-[6-(4-trifluoromethyl-phenyl)-4,5-dimethyl-pyridazin-3-yl]-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5 ‘

    -carboxylic acid methyl ester;

    (R)-4-[6-(4-trifluoromethyl-phenyl)-4,5-dimethyl-pyridazin-3-yl]-2-methyl-3,4,5,6-tetrahydro-2H-[1,2’

    ]bipyrazinyl-5′

    -carboxylic acid;

    (R)-4-[6-(4-fluoro-phenyl)-4,5-dimethyl-pyridazin-3-yl]-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid;

    Methyl 5-(4-(6-benzyl-4,5-dimethylpyridazin-3-yl)piperidin-1-yl)pyrazine-2-carboxylate;

    2-{5-[4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-piperidin-1-yl]-pyrazin-2-yl}-propan-2-ol;

    3-Benzyl-6-{1-[5-(1-methoxy-1-methyl-ethyl)-pyrazin-2-yl]-piperidin-4-yl}-4,5-dimethyl-pyridazine;

    3-Benzyl-6-{1-[5-(trifluoromethyl)pyridin-2-yl]-piperidin-4-yl}-4,5-dimethyl-pyridazine;

    (R)-4-(6-Benzoyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid methyl ester;

    (6-{(R)-4-[4-(1-Hydroxy-1-methyl-ethyl)-phenyl]-3-methyl-piperazin-1-yl}-4,5-dimethyl-pyridazin-3-yl)-phenyl-methanone;

    (R)-4[6-(hydroxyl-phenyl-methyl)-4,5-dimethyl-pyridazin-3-yl]-2-methyl-3,4,5,6-tetrahydro-2H-[1,2]bipyrazinyl-5′

    -carboxylic acid methyl ester;

    (R)-4-(4,5-Dimethyl-6-pyridin-4-ylmethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid methyl ester;

    (R)-4-(4,5-Dimethyl-6-pyridin-3-ylmethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid methyl ester;

    2-[(R)-4-(4,5-Dimethyl-6-pyridin-3-ylmethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -yl]-propan-2-ol;

    (R)-4-(4,5-Dimethyl-6-pyridin-2-ylmethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid methyl ester;

    2-{(R)-4-[6-(Difluoro-phenyl-methyl)-4,5-dimethyl-pyridazin-3-yl]-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -yl}-propan-2-ol;

    3-Benzyl-6-[4-(5-chloro-1H-imidazol-2-yl)-piperidin-1-yl]-4,5-dimethyl-pyridazine;

    1′

    -(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-5-(1-hydroxy-1-methyl-ethyl)-2′

    ,3′

    ,5′

    ,6′

    -tetrahydro-1′

    H-[2,4′

    ]bipyridinyl-4′

    -carbonitrile;

    3-Benzyl-4,5-dimethyl-6-[4-(4-trifluoromethyl-1H-imidazol-2-yl)-piperidin-1-yl]-pyridazine;

    1′

    -(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-5-(1-hydroxy-1-methyl-ethyl)-2′

    ,3′

    ,5′

    ,6′

    -tetrahydro-1′

    H-[2,4′

    ]bipyridinyl-4′

    -ol;

    2-[1′

    -(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-4′

    -fluoro-1′

    ,2′

    ,3′

    ,4′

    ,5′

    ,6′

    -hexahydro-[2,4′

    ]bipyridinyl-5-yl]-propan-2-ol;

    2-(6-{(S)-4-[4-(2-Chloro-benzyl)-6,7-dihydro-5H-cyclopenta[d]pyridazin-1-yl]-3-methyl-piperazin-1-yl}-pyridin-3-yl)-propan-2-ol;

    (R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid methyl ester;

    3-Benzyl-4,5-dimethyl-6-[(R)-3-methyl-4-(4-trifluoro-methanesulfonylphenyl)-piperazin-1-yl]-pyridazine;

    2-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -yl]-2,2-dimethoxy-ethanol;

    1-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -yl]-ethanol;

    1-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -yl)-2-hydroxy-ethanone;

    1-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -yl)-ethane-1,2-diol;

    (R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid;

    (R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -carboxylic acid methoxy-methyl-amide;

    (R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-5′

    -isopropenyl-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl;

    4,5-Dimethyl-3-(5-methyl-[1,2,4]oxadiazol-3-yl-methyl)-6-[4-(5-trifluoro-methyl-pyridin-2-yl)-piperazin-1-yl]-pyridazine;

    4,5-Dimethyl-3-(1-methyl-1H-tetrazol-5-ylmethyl)-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazine;

    4,5-Dimethyl-3-(2-methyl-2H-tetrazol-5-ylmethyl)-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazine;

    4,5-Dimethyl-3-(5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazine;

    2-[(R)-4-(6-Benzyl-5-hydroxymethyl-4-methyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -yl]-propan-2-ol; and

    2-[(R)-4-(6-Benzyl-4-hydroxymethyl-5-methyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′

    ]bipyrazinyl-5′

    -yl]-propan-2-ol.

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