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N-benzyl-3,4-dihyroxypyridine-2-carboxamide and n-benzyl-2,3-dihydroxypyridine-4- carboxamide compounds useful as hiv integrase inhibitors

  • US 20070155744A1
  • Filed: 01/26/2005
  • Published: 07/05/2007
  • Est. Priority Date: 01/30/2004
  • Status: Abandoned Application
First Claim
Patent Images

1. A compound of Formula I, or a pharmaceutically acceptable salt thereof:

  • embedded image wherein;

    Q is;

    embedded image T is;

    embedded image X1, X2 and X3 are each independently selected from the group consisting of —

    H, halo, —

    C1-4 alkyl, —

    O—

    C1-4 alkyl, —

    C1-4 fluoroalkyl, —

    SO2

    C1-4 alkyl, —

    C(═

    O)—

    NH(—

    C1-4 alkyl), —

    C(═

    O)—

    N(—

    C1-4 alkyl)2, and HetA Y1 is —

    H, halo, —

    C1-4 alkyl, or —

    C1-4 fluoroalkyl;

    R1 is;

    (1) —

    C1-6 fluoroalkyl, (2) —

    C1-6 alkyl-N(Ra)Rb, (3) —

    C1-6 alkyl-N(Ra)—

    C(═

    O)—

    Rb, (4) —

    C(═

    O)—

    Ra, (5) —

    C(═

    O)ORa, (6) —

    C(═

    O)—

    N(Ra)Rb, (7) —

    C(═

    O)—

    N(Ra)—

    C1-6 alkyl-aryl, (8) —

    HetB, (9) —

    C(═

    O)—

    N(Ra)—

    C1-6 alkyl—

    HetB, (10) —

    C1-6 alkyl-HetC, (11) —

    C(═

    O)—

    HetC. (12) —

    C(═

    O)-aryl, or (13) —

    C(═

    O)—

    HetB;

    each HetA is independently a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein the heteroaromatic ring is optionally substituted with 1 or 2 substituents each of which is independently a —

    C1-4 alkyl;

    HetB is;

    (A) a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S;

    wherein the heteroaromatic ring is attached to the rest of the compound via a carbon atom in the ring, and wherein the heteroaromatic ring is;

    (i) optionally substituted with 1 or 2 substituents each of which is independently a —

    C1-4 alkyl; and

    (ii) optionally substituted with aryl or —

    C1-4 alkyl-aryl;

    or (B) a 9- or 10-membered aromatic heterobicyclic fused ring system containing from 1 to 4 heteroatoms independently selected from N, O and S;

    wherein the fused ring system consists of a 6-membered ring fused with either a 5-membered ring or another 6-membered ring, either ring of which is attached to the rest of the compound via a carbon atom;

    wherein the ring of the fused ring system attached to the rest of the compound via the carbon atom contains at least one of the heteroatoms; and

    wherein the fused ring system is;

    (i) optionally substituted with 1 or 2 substituents each of which is independently a —

    C1-4 alkyl; and

    (ii) optionally substituted with aryl or —

    C1-4 alkyl-aryl;

    HetC is a 4- to 7-membered saturated heterocyclic ring containing at least one carbon atom and a total of from 1 to 4 heteroatoms independently selected from 1 to 4 N atoms, from 0 to 2 O atoms, and from 0 to 2 S atoms, wherein any ring S atom is optionally oxidized to SO or SO2, and wherein the heterocyclic ring is optionally fused with a benzene ring, and wherein the heterocyclic ring is attached to the rest of the compound via a N atom in the ring, and wherein the heterocyclic ring is;

    (i) optionally substituted with 1 or 2 substituents each of which is independently a —

    C1-4 alkyl, —

    C1-4 alkyl-N(Ra)Rb, or —

    C(═

    O)ORa; and

    (ii) optionally substituted with aryl, —

    C1-4 alkyl-aryl, HetD, or —

    C1-4 alkyl-HetD;

    wherein HetD is (i) a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S or (ii) a 4- to 7-membered saturated heterocyclic ring containing at least one carbon atom and from 1 to 4 heteroatoms independently selected from N, O and S;

    R2 is —

    C1-6 alkyl or —

    C1-6 alkyl-aryl;

    aryl is phenyl or naphthyl;

    each Ra is independently H or C1-6 alkyl; and

    each Rb is independently H or C1-6 alkyl.

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