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Piperazinyl 5-HT1 agonists and antagonists

  • US 6,277,852 B1
  • Filed: 04/14/1999
  • Issued: 08/21/2001
  • Est. Priority Date: 04/15/1998
  • Status: Expired due to Fees
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Assignment
First Claim
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1. A compound of the formula or the pharmaceutically acceptable salt thereof;

  • whereinZ is oxygen, S(O)m wherein m is 0, 1 or 2;

    or NQ wherein Q is hydrogen, (C1-C6)alkyl or phenyl;

    X is hydrogen, chloro, fluoro, bromo, iodo, hydroxy, nitro, cyano, (C1-C6)alkyl, trifluoromethyl, (C1-C6)alkoxy, (C1-C6)alkyl S(O)a wherein a is 0, 1 or 2;

    or phenyl wherein the phenyl group is optionally substituted by hydrogen, halo, hydroxy, nitro, cyano, (C1-C6)alkyl, trifluoromethyl, (C1-C6)alkoxy, or (C1-C6)alkyl S(O)b wherein b is 0, 1 or 2;

    Y is wherein M is oxygen or sulfur;

    X2 is hydrogen, fluoro, chloro, trifluoromethyl, (C1-C6)alkyl, (C1-C6)alkoxy or (C1-C6)alkyl S(O)c wherein c is 0, 1 or 2;

    R1 is selected from whereinR6 in G1 is selected from the group consisting of hydrogen, (C1-C6)alkyl optionally substituted with (C1-C6)alkoxy or one to three fluorine atoms, or [(C1-C4)alkyl]aryl wherein the aryl moiety is phenyl, naphthyl, or heteroaryl-(CH2)q—

    , wherein the heteroaryl moiety is selected from the group consisting of pyridyl, pyrimidyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl and benzisothiazolyl and q is zero, one, two, three or four, and wherein said aryl and heteroaryl moieties may optionally be substituted with one or more substituents independently selected from the group consisting of chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, trifluoromethyl, cyano and (C1-C6)alkylS(O)e, wherein e is 0, 1 or 2;

    and wherein R6 in G5 together with R7 form a 2 carbon chain;

    R9 is hydrogen or (C1-C6)alkyl;

    R10 is hydrogen or (C1-C6)alkyl;

    R2 is hydrogen, (C1-C4)alkyl, phenyl or naphthyl, wherein said phenyl or naphthyl may optionally be substituted with one or more substituents independently selected from chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, trifluoromethyl, cyano and (C1-C6)alkyl S(O)g wherein g is 0, 1 or 2; and

    R3 is —

    (CH2)tB, wherein t is zero, one, two or three and B is hydrogen, phenyl, naphthyl or a 5 or 6 membered heteroaryl group containing from one to four heteroatoms in the ring, and wherein each of the foregoing phenyl, naphthyl and heteroaryl groups may optionally be substituted with one or more substituents independently selected from chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6) alkoxy-(C1C6)alkyl-, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, COOH and (C1-C6)alkyl S(O)h wherein h is 0, 1 or 2.

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