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US 9,434,738 B2Granted
Macrocyclic benzofuran and azabenzofuran compounds for the treatment of hepatitis C
AssigneeBristol-Myers Squibb Company
InventorsTao Wang, Zhongxing Zhang, John F. Kadow
Life of this patent
Estimating the term…
Abstract
Compounds of formula I, including their salts, as well as compositions and methods of using the compounds are set forth. The compounds have activity against hepatitis C virus (HCV) and may be useful in treating those infected with HCV.
Claims15
A compound of formula I, including pharmaceutically acceptable salts thereof:
- wherein
- n, m are independently 0 or 1;
- R1 is methyl;
- R2 is phenyl that is independently substituted with 0-2 halo or methoxy or is para substituted with W—Ar1;
- W is —O— or —NH—;
- Ar1 is phenyl or para-halophenyl;
- R3 is hydrogen, halo, or alkyl;
- R4, R5, R6 are independently selected from hydrogen, halo, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkoxy, hydroxyalkyloxy, alkoxyalkyloxy, COOR11 and CON(R12)(R13);
- R11 is hydrogen, alkyl or cycloalkyl with 0-3 substituents selected from halo, hydroxyl, alkoxy, and haloalkoxy;
- R12, R13 are each independently hydrogen, alkyl or cycloalkyl with 0-3 substituents selected from halo, hydroxyl, alkoxy, and haloalkoxy;
- or
- R12 and R13 can form a ring by joining two atoms, one from each of R12 and R13;
- R14 is hydrogen, alkyl or cycloalkyl with 0-3 substituents selected from halo, hydroxyl, alkoxy, and haloalkoxy;
- R7 is hydrogen, alkyl, halo, N(R21)(R22), or alkylsulfonyl;
- R21 and R22 are independently hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, alkylsulfonyl, or alkylsulfonylalkyl;
- or N(R21)(R22) taken together is azetidinyl, pyrrolidinyl, piperidinyl, or piperazinyl, and is substituted with 0-2 substituents selected from alkyl, hydroxyalkyl, and hydroxy;
- X, Y are independently selected from CR31R32, CO, O, NR33, NCN, S, SO, and S(O)2;
- R31, R32 are each independently alkyl or cycloalkyl, further substituted with 0-3 substituents;
- or
- R31 and R32 can form a ring by joining two atoms, one from each of R31 and R32;
- R33 is hydrogen, alkyl, cycloalkyl, or S(O)2R11 with 0-3 substituents selected from halo, haloalkoxy, OR11, NR12R13, COOR11, CONR12R13, S(O)2R11, S(O)2NR12R13, and NR14CONR12R13;
- Z is an alkylene or alkenylene chain containing 0-12 groups selected from the group consisting of O, NR41, S, S(O), S(O)2, C(O), C(O)O, C(O)NR41, C(S)NR41, O—C(O)NR41, NR41C(O)NR42, and Ar2, provided that any O or S atom does not directly bond to another O or S atom, such that ring A is 11-24 membered;
- and further wherein the alkylene or alkenylene chain is substituted with 0-6 substituents selected from alkyl, cycloalkyl, halo, alkoxy, haloalkyl, OH, OR11, haloalkoxy, NH2, NR12R13, COOR11, CONR12R13, S(O)2R11, S(O)2NR12R13, NR14CONR12R13, and Ar3;
- R41, R42 is hydrogen, alkyl or cycloalkyl with 0-3 substituents selected from halo, haloalkoxy, OR11, NR12R13, COOR11, CONR12R13, S(O)2R11, S(O)2NR12R13, and NR14CONR12R13;
- Ar2 is phenyl, 5-membered heteroaryl or 6-membered heteroaryl, and is substituted with 0-3 substituents selected from cyano, halo, alkyl, cycloalkyl, haloalkyl, OH, OR11, haloalkoxy, NH2, NR12R13, COOR11, CONR12R13, S(O)2R11, S(O)2NR12R13, and NR14CONR12R13;
- Ar3 is phenyl, 5-membered heteroaryl or 6-membered heteroaryl, and is substituted with 0-3 substituents selected from cyano, halo, alkyl, cycloalkyl, haloalkyl, OH, OR11, haloalkoxy, NH2, NR12R13, COOR11CONR12R13, S(O)2R11, S(O)2NR12R13, and NR14CONR12R13.
23 more elements
A compound, including pharmaceutically acceptable salts thereof, which is selected from the group of:
Dependencies are inferred from the claim text.