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HETEROCYCLIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE SEROTONIN 5HT6 RECEPTOR

  • US 20100048582A1
  • Filed: 04/18/2007
  • Published: 02/25/2010
  • Est. Priority Date: 04/19/2006
  • Status: Active Grant
First Claim
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1. A compound of the formula (I) whereinD is a group of the formula B or C n is or 2;

  • G is CH2 or CHR3;

    R1 is H, C1-C6-alkyl, C1-C6-alkyl substituted by C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, fluorinated C1-C6-alkyl, C3-C6-cycloalkyl, fluorinated C3-C6-cycloalkyl, C3-C6-alkenyl, fluorinated C3-C6-alkenyl, formyl, acetyl, propionyl or benzyl;

    R2, R2′

    , R3, R4 and R4′

    are, independently of each other, H, methyl, fluoromethyl, difluoromethyl, or trifluoromethyl;

    A is 2,4-pyridylene, 3,5-pyridylene or 2,6-pyridylene, which is optionally substituted by one, two or three substituents selected from halogen, C1-C4-alkyl, C1-C4-alkoxy, fluorinated C1-C4-alkyl and fluorinated C1-C4-alkoxy;

    E is NR7 or CH2, wherein R7 is H or C1-C3-alkyl;

    Ar is a cyclic radical selected from the group consisting of phenyl, a 5- or 6-membered heteroaromatic radical comprising as ring members 1, 2 or 3 heteroatoms selected from N, O and S and a phenyl ring fused to a saturated or unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, where the heterocyclic ring comprises as ring members 1, 2 or 3 heteroatoms selected from N, O and S and/or 1, 2 or 3 heteroatom-containing groups each independently selected from NR6, where R8 is H, C1-C4-alkyl, fluorinated C1-C4-alkyl, C1-C4-alkylcarbonyl or fluorinated C1-C4-alkylcarbonyl, and where the cyclic radical Ar may carry 1, 2 or 3 substituents Ra;

    each R1 is independently halogen, hydroxyl, C1-C6-alkyl, fluorinated C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, fluorinated C2-C6-alkenyl, C3-C6-cycloalkyl, fluorinated C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-hydroxyalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, fluorinated C1-C6-alkoxy, C1-C6-alkylthio, fluorinated C1-C6-alkylthio, C1-C6-alkylsulfinyl, fluorinated C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, fluorinated C1-C6-alkylsulfonyl, phenylsulfonyl, pyridylsulfonyl, benzyloxy, phenoxy, phenyl, where the phenyl and the pyridyl radical in the 5 last-mentioned radicals may be unsubstituted or may carry 1 to 3 substituents selected from C1-C4-alkyl, fluorinated C1-C4-alkyl and halogen, CN, nitro, C1-C6-alkylcarbonyl, fluorinated C1-C6-alkylcarbonyl, C1-C6-alkylcarbonylamino, fluorinated C1-C6-alkylcarbonylamino, carboxy, NH—

    C(O)—

    NR6R7, NR6R7, NR6R7

    C1-C6-alkylene, O—

    NR6R7, where R6 and R7 are, independently of each other, H, C1-C4-alkyl, fluorinated C1-C4-alkyl or C1-C4-alkoxy or may form, together with N, a 4-, 5- or 6-membered saturated or unsaturated ring, R10

    CO—

    NR6

    C1-C6-alkylene, where R6 is as defined above and R10 is C1-C4-alkyl or phenyl, where the phenyl radical may be unsubstituted or may carry 1 to 3 substituents selected from C1-C4-alkyl, fluorinated C1-C4-alkyl and halogen, CH2-pyridyl, where the pyridyl radical may be unsubstituted or may carry 1 to 3 substituents selected from C1-C4-alkyl, fluorinated C1-C4-alkyl and halogen, or is a saturated or unsaturated aromatic or non-aromatic 3- to 7-membered heterocyclic ring comprising as ring members 1, 2, 3 or 4 heteroatoms selected from N, O and S and/or 1, 2 or 3 heteroatom-containing groups selected from NR9, where R9 has one of the meanings given for R8, SO, SO2 and CO, and where the heterocyclic ring may carry 1, 2 or 3 substituents selected from hydroxy, halogen, C1-C6-alkyl, fluorinated C1-C6-alkyl, C1-C6-alkoxy, fluorinated C1-C6-alkoxy, C1-C6-alkylthio, fluorinated C1-C6-alkylthio, NR6R7

    C1-C6-alkylene, where R6 and R7 are as defined above, carboxyl and C1-C4-alkoxycarbonyl;

    and physiologically tolerated acid addition salts thereof.

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