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AZEPINE INHIBITORS OF JANUS KINASES

  • US 20090197869A1
  • Filed: 04/03/2009
  • Published: 08/06/2009
  • Est. Priority Date: 09/22/2005
  • Status: Abandoned Application
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Assignment
First Claim
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1. A compound of Formula Ia, Ib, or Ic:

  • or pharmaceutically acceptable salt thereof, wherein;

    D1, D2, D3, D4, D5, D6 and D7 are, independently, CR1 or N;

    E is O, S, SO, SO2, or NR2a;

    G is N or CR2b;

    Q1 and Q2 are each, independently, N or CR2c;

    W1 is absent, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, O, S, NR3, CO, COO, CONR3, SO, SO2, SONR3, SO2NR3, or NR3CONR4, wherein said C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl is optionally substituted by 1, 2 or 3 substituents independently selected from halo, OH, C1-4 alkoxy, C1-4 haloalkoxy, amino, C1-4 alkylamino and C2-8 dialkylamino;

    W2 is absent, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, cycloalkyl, heteroaryl or heterocycloalkyl, wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, cycloalkyl, heteroaryl or heterocycloalkyl is optionally substituted by 1, 2, or 3 substituents independently selected from halo, CN, NO2, OH, ═

    NH, ═

    NOH, ═

    NO—

    (C1-4 alkyl), —

    NR3C(O)O—

    (C1-4 alkyl), NR3C(O)—

    (C1-4 alkyl), —

    C(O)O—

    (C1-4 alkyl), C1-4 haloalkyl, C1-4 cyanoalkyl, pentahalosulfanyl, C1-4 hydroxylalkyl, C1-4 alkylthio, C1-4 haloalkylthio, C1-4 alkoxy, C1-4 haloalkoxy, amino, C1-4 alkylamino and C2-8 dialkylamino;

    W3 is absent, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, O, S, NR3, ═

    N—

    , ═

    N—

    O—

    , ═

    N—

    O—

    (C1-4 alkyl)-, O—

    (C1-4 alkyl), S—

    (C1-4 alkyl), NR3—

    (C1-4 alkyl), (C1-4 alkyl)-O—

    (C1-4 alkyl), (C1-4 alkyl)-S—

    (C1-4 alkyl), (C1-4 alkyl)-NR3—

    (C1-4 alkyl), CO, COO, C(O)—

    (C1-4 alkyl), C(O)O—

    (C1-4 alkyl), C(O)—

    (C1-4 alkyl)-C(O), NR3C(O)—

    (C1-4 alkyl), C(O)NR3—

    (C1-4 alkyl), NR3C(O)O—

    (C1-4 alkyl), NR3C(O)O, CONR3, SO, SO2, SONR3, SO2NR3, or NR3CONR4, wherein said C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl is optionally substituted by 1, 2 or 3 substituents independently selected from halo, OH, CN, C1-4 alkoxy, C1-4 haloalkoxy, amino, C1-4 alkylamino and C2-8 dialkylamino;

    W4 is H, NR3R4, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, cycloalkyl, heteroaryl or heterocycloalkyl, wherein each of said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, cycloalkyl, heteroaryl or heterocycloalkyl is optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from halo, OH, CN, C1-4 alkoxy, ═

    NH, ═

    NOH, ═

    NO—

    (C1-4 alkyl), C1-4 haloalkyl, C1-4 haloalkoxy, pentahalosulfanyl, COOH, CONH2, COO—

    (C1-4 alkyl), amino, C1-4 alkylamino and C2-8 dialkylamino;

    R1 is, independently, H, halo, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 haloalkyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, CN, NO2, ORa, SRa, C(O)Rb, C(O)NRcRd, NRcC(O)NRcRd, C(O)ORa, OC(O)Rb, OC(O)NRcRd, NRcRd, NRcC(O)Rd, NRcC(O)ORa, S(O)Rb, S(O)NRcRd, NRcS(O)NRcRd, pentahalosulfanyl, S(O)2Rb, or S(O)2NRcRd;

    R2a is H, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, OH, C1-4 alkoxy, C(O)Rb, C(O)NRcRd, S(O)Rb, S(O)NRcRd, S(O)2Rb, or S(O)2NRcRd;

    R2b and R2c are each, independently, H, halo, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 haloalkyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, CN, NO2, ORa, SRa, C(O)Rb, C(O)NRcRd, C(O)ORa, OC(O)Rb, OC(O)NRcRd, NRcC(O)NRcRd, NRcRd, NRcC(O)Rd, NRcC(O)ORa, S(O)Rb, S(O)NRcRd, NRcS(O)NRcRd, S(O)2Rb, or S(O)2NRcRd;

    R3 and R4 are each, independently, H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, cycloalkyl, arylalkyl, cycloalkylalkyl, COORa′

    , CORb′

    , SORb′

    , or SO2Rb′

     wherein each of said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, cycloalkyl, arylalkyl, or cycloalkylalkyl is optionally substituted by 1, 2 or 3 substituents selected from halo, C1-4 alkyl, C1-4 haloalkyl, OH, C1-4 alkoxy, C1-4 haloalkoxy, amino, C1-4 alkylamino, C2-8 dialkylamino, aminocarbonyl, C1-4 alkylaminocarbonyl, C2-8 dialkylaminocarbonyl, CN and NO2;

    or R3 and R4 together with the N atom to which they are attached form a heterocycloalkyl group optionally substituted by 1, 2 or 3 substituents selected from halo, C1-4 alkyl, C1-4 haloalkyl, OH, C1-4 alkoxy, C1-4 haloalkoxy, amino, C1-4 alkylamino, C2-8 dialkylamino, aminocarbonyl, C1-4 alkylaminocarbonyl, and C2-8 dialkylaminocarbonyl;

    Ra and Ra′

     are each, independently, H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, cycloalkyl, heteroaryl or heterocycloalkyl;

    Rb and Rb′

     are each, independently, H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, cycloalkyl, heteroaryl or heterocycloalkyl; and

    Rc and Rd are each, independently, H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, cycloalkyl, arylalkyl, or cycloalkylalkyl;

    or Re and Rd together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

    provided that when D7 is N, E is O or S, and G is N;

    then —

    W1—

    W2—

    W3—

    W4 is other than H.

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