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1. WO2014110066 - MACROCYCLIC BENZOFURAN AND AZABENZOFURAN COMPOUNDS FOR THE TREATMENT OF HEPATITIS C

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[ EN ]

CLAIMS

We claim:

1. 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 R 12 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)2Rn 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 1 1-24 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, COOR11, CONR12R13, S(O)2R11, S(O)2NR12R13, and NR14CONR12R13.

2. A compound of claim 1 wherein n and m are each 1.

3. A compound of claim 2 wherein R2 is phenyl substituted with halo.

4. A compound of claim 3 wherein halo is fluoro.

5. A compound of claim 1 wherein R3, R4, R6 and R7 are each hydrogen.

6. A compound of claim 1 wherein X and Y are each NR33.

7. A compound of claim 6 wherein R33 is hydrogen or S(O)2CH3.

8. A compound of claim 1 wherein A is at least a 12-member ring.

9. A compound of claim 8 wherein A is at least a 15-member ring.

10. A compound of claim 9 wherein A is at least a 17-member ring.

11. A compound of claim 10 wherein A is at least a 19-member ring.

12. A compound, including pharmaceutically acceptable salts thereof, which is selected from the group of:


,
,


,
,


,
,


,
,


,
,
,
,


,
, and


.

13. A composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

14. A composition comprising a compound of claim 12 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

15. A method of treating hepatitis C infection comprising administering a therapeutically effective amount of a compound of claim 1 to a patient.