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    • 1. 发明公开
    • Heteroaryl sulfonamides and CCR2
    • Heteroarylsulfonamides和CCR2
    • EP2474532A1
    • 2012-07-11
    • EP12162572.7
    • 2006-01-13
    • ChemoCentryx, Inc.
    • Ungashe, SolomonPennell, Andrew M. K.Punna, SreenivasWei, ZhengWright, John JessenZeng, YibinBadak, ArindrajitCharvat, Trevor T.Dairaghi, DanielHanson, DerekJin, JeffMoore, Jimmie
    • C07D213/02
    • C07C311/21C07D213/48C07D213/61C07D213/643C07D213/70C07D213/73C07D213/76C07D213/79C07D213/81C07D213/89C07D241/22C07D263/32C07D401/04C07D405/04C07D409/12C07D413/06C07D413/10C07D417/12C07D471/04
    • A compound of the formula (I), or a salt thereof:

      where
      Ar is selected from the group consisting of substituted or unsubstituted C 6-10 aryl and substituted or unsubstituted 5- to 10-membered heteroaryl;
      R 1 is selected from the group consisting of hydrogen, unsubstituted C 1 alkyl, substituted or unsubstituted C 3-8 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, and substituted or unsubstituted 3- to 10-membered heterocyclyl;
      Y 1 is selected from the group consisting of -CR 2a -, -N-, and -N + (O) - -;
      Y 2 is selected from the group consisting of -CR 2b -, -N-, and -N + (O) - -;
      Y 3 is selected from the group consisting of -CR 2c -, -N-, and -N + (O) - -;
      R 2a , R 2b , and R 2c are each independently selected from the group consisting of hydrogen, halogen, -CN, -C(O)R 3 , -CO 2 R 3 , -C(O)NR 3 R 4 , -OR 3 , - OC(O)R 3 , -OC(O)NR 3 R 4 , -SR 3 , -S(O)R 3 , -S(O) 2 R 3 , -S(O) 2 NR 3 R 4 , -NO 2 , -NR 3 R 4 , -NR 3 C(O)R 4 , -NR 3 C(O)OR 4 , -NR 3 S(O) 2 R 4 , -NR 3 C(O)NR 4 R 5 , substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-8 alkenyl, substituted or unsubstituted C 2-8 alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10 aryl, and substituted or unsubstituted 5- to 10-membered heteroaryl;
      R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-8 alkenyl, substituted or unsubstituted C 2-8 alkynyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, and substituted or unsubstituted 3- to 10-membered heterocyclyl;
      R 3 and R 4 , R 4 and R 5 or R 3 and R 5 may, together with the atoms to which they are attached, form a substituted or unsubstituted 5-, 6-, or 7-membered ring;
      Y 4 is selected from the group consisting of -N- and -N + (O) - -;
      L is selected from the group consisting of a bond, -O-, -S-, -S(O)-, S(O) 2 -, - CR 6 R 7 -, -NR 8 -, -C(O)- and -NR 8 C(O)-;
      R 6 and R 7 are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, -CN, -OR 9 , -NR 10 R 11 , -S(O)R 9 , and -S(O) 2 R 9 ;
      R 6 and R 7 may, together with the carbon atom to which they are attached, form substituted or unsubstituted C 3-8 cycloalkyl or substituted or unsubstituted 3-to 10-membered heterocyclic ring;
      R 9 is selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-8 alkenyl, substituted or unsubstituted C 2-8 alkynyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, and substituted or unsubstituted 3- to 10-membered heterocyclyl;
      R 10 and R 11 are each independently selected from the group consisting of substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted C 2-8 alkenyl, and substituted or unsubstituted C 2-8 alkynyl;
      R 10 and R 11 of -NR 10 R 11 may, together with the nitrogen, form a substituted or unsubstituted C 3-8 cycloalkyl or substituted or unsubstituted 3- to 10-membered heterocyclyl;
      R 8 is selected from the group consisting of hydrogen, C(O)R 12 , S(O) 2 R 12 , CO 2 R 12 , substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 2-6 alkenyl, and substituted or unsubstituted C 2-6 alkynyl;
      R 12 is selected from the group consisting of substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10 aryl, and substituted or unsubstituted 5- to 10-membered heteroaryl;
      Z 1 is selected from the group consisting of substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted 3- to 10-membered heterocyclyl, and -NR 13 R 14 ;
      R 13 and R 14 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-8 alkenyl, substituted or unsubstituted C 2-8 alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted (C 1-4 alkyl)-(C 6-10 aryl), and substituted or unsubstituted (C 1-4 alkyl)-(5- to 10-membered heteroaryl);
      R 13 and R 14 may, together with the nitrogen, form a substituted or unsubstituted 4-, 5-, 6-, or 7-membered heterocyclyl
      with the proviso that compounds of formula CC are excluded:

      where
      X 14 is selected from the group consisting of -Cl, -NO 2 , -OCH 3 , -CH 3 , - NHC(O)CH 3 , and -CH 2 CH 2 -(phenyl);
      R 65 is selected from the group consisting of hydrogen, substituted or unsubstituted C 1-4 alkyl, and substituted or unsubstituted -SO 2 (phenyl); and
      R 60 is selected from the group consisting of -NR 61 CH 2 CH 2 OR 62 , - NR 61 CH 2 CH 2 NR 63 R 64 , -NR 61 CH 2 CH 2 SR 62 ,

      where R 61 is selected from the group consisting of hydrogen and substituted or unsubstituted phenyl;
      R 62 is selected from the group consisting of substituted or unsubstituted phenyl, and substituted or unsubstituted C 1-4 alkyl; and
      R 63 and R 64 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted -SO 2 (phenyl), - C(O)CH 3 , -C(O)C(O)OH, and -C(O) 2 C(CH 3 ) 3 .
    • 3. 发明公开
    • Heteroaryl sulfonamides and CCR2
    • Heteroarylsulfonamides和CCR2
    • EP2354126A1
    • 2011-08-10
    • EP11002389.2
    • 2006-01-13
    • ChemoCentryx, Inc.
    • Ungashe, SolomonWright, John JessenZeng, YibinBadak, ArindrajitCharvat, Trevor T.Dairaghi, DanielHansen, DerekJin, JeffMoore, JimmiePennell, Andrew M.K.Punna, SreenivasWei, Zheng
    • C07D213/02C07D401/02A61K31/44
    • C07C311/21C07D213/48C07D213/61C07D213/643C07D213/70C07D213/73C07D213/76C07D213/79C07D213/81C07D213/89C07D241/22C07D263/32C07D401/04C07D405/04C07D409/12C07D413/06C07D413/10C07D417/12C07D471/04
    • A compound of the formula (I), or a salt thereof:

      where
      Ar is selected from the group consisting of substituted or unsubstituted C 6-10 aryl and substituted or unsubstituted 5- to 10-membered heteroaryl;
      R 1 is selected from the group consisting of hydrogen, unsubstituted C 1 alkyl, substituted or unsubstituted C 3-8 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, and substituted or unsubstituted 3- to 10-membered heterocyclyl;
      Y 1 is selected from the group consisting of -CR 2a -, -N-, and -N + (O) - -;
      Y 2 is selected from the group consisting of -CR 2b -, -N-, and -N + (O) - -;
      Y 3 is selected from the group consisting of -CR 2c -, -N-, and -N + (O) - -;
      R 2a , R 2b , and R 2c are each independently selected from the group consisting of hydrogen, halogen, -CN, -C(O)R 3 , -CO 2 R, -C(O)NR 3 R 4 , -OR 3 , -OC(O)R 3 , -OC(O)NR 3 R 4 , -SR 3 , -S(O)R 3 , -S(O) 2 R 3 , -S(O) 2 NR 3 R 4 , -NO 2 , -NR 3 R 4 , -NR 3 C(O)R 4 , -NR 3 C(O)OR 4 , - NR 3 S(O) 2 R 4 , -NR 3 C(O)NR 4 R 5 , substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-8 alkenyl, substituted or unsubstituted C 2-8 alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10 aryl, and substituted or unsubstituted 5- to 10-membered heteroaryl;
      R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-8 alkenyl, substituted or unsubstituted C 2-8 alkynyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, and substituted or unsubstituted 3- to 10-membered heterocyclyl;
      R 3 and R 4 , R 4 and R 5 or R 3 and R 5 may, together with the atoms to which

      they are attached, form a substituted or unsubstituted 5-, 6-, or 7-membered ring;

      Y 4 is selected from the group consisting of -N- and -N + (O) - -;
      L is selected from the group consisting of a bond, -O-, -S-, -S(O)-, S(O) 2 -, -CR 6 R 7 -, - NR 8 -, -C(O)- and -NR 8 C(O)-;
      R 6 and R 7 are each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, -CN, -OR 9 , -NR 10 R 11 , -S(O)R 9 , and -S(O) 2 R 9 ;
      R 6 and R 7 may, together with the carbon atom to which they are attached, form substituted or unsubstituted C 3-8 cycloalkyl or substituted or unsubstituted 3- to 10-membered heterocyclic ring;
      R 9 is selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-8 alkenyl, substituted or unsubstituted C 2-8 alkynyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, and substituted or unsubstituted 3- to 10-membered heterocyclyl;
      R 10 and R 11 are each independently selected from the group consisting of substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted C 2-8 alkenyl, and substituted or unsubstituted C 2-8 alkynyl;
      R 10 and R 11 of -NR 10 R 11 may, together with the nitrogen, form a substituted or unsubstituted C 3-8 cycloalkyl or substituted or unsubstituted 3- to 10-membered heterocyclyl;

      R 8 is selected from the group consisting of hydrogen, C(O)R 12 , S(O) 2 R 12 , CO 2 R 12 , substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 2-6 alkenyl, and substituted or unsubstituted C 2-6 alkynyl;
      R 12 is selected from the group consisting of substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-6 alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted 3- to 1 0-membered heterocyclyl, substituted or unsubstituted C 6-10 aryl, and substituted or unsubstituted 5- to 10-membered heteroaryl;

      Z 1 is selected from the group consisting of substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted 3- to 10-membered heterocyclyl, and -NR 13 R 14 ;
      R 13 and R 14 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted C 2-8 alkenyl, substituted or unsubstituted C 2-8 alkynyl, substituted or unsubstituted 3- to 10-membered heterocyclyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl, substituted or unsubstituted (6 1-4 alkyl)-(C 6-10 aryl), and substituted or unsubstituted (C 1-4 alkyl)-(5- to 10-membered heteroaryl);
      R 13 and R 14 may, together with the nitrogen, form a substituted or unsubstituted 4-, 5-, 6-, or 7-membered heterocyclyl
      with the proviso that compounds of formula CC are excluded:


      where
      X 14 is selected from the group consisting of -Cl, -NO 2 , -OCH 3 , -CH 3 , -NHC(O)CH 3, and -CH 2 CH 2 -(phenyl);
      R 65 is selected from the group consisting of hydrogen, substituted or unsubstituted C 1-4 alkyl, and substituted or unsubstituted -SO 2 (phenyl); and
      R 60 is selected from the group consisting of -NR 61 CH 2 CH 2 OR 62 , - NR 61 CH 2 CH 2 NR 63 R 64 , -NR 61 CH 2 CH 2 SR 62 ,

      where R 61 is selected from the group consisting of hydrogen and substituted or unsubstituted phenyl;
      R 62 is selected from the group consisting of substituted or unsubstituted phenyl, and substituted or unsubstituted C 1-4 alkyl; and
      R 63 and R 64 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted -SO 2 (phenyl), -C(O)CH 3 , -C(O)C(O)OH, and -C(O) 2 C(CH 3 ) 3 .