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US 2006/0052418 A1Published application
Viral polymerase inhibitors
AssigneeBoehringer Ingelheim International GmbH
InventorsPierre Beaulieu, Christian Brochu, Stephen Kawai, Jean Rancourt, Timothy Stammers, Bounkham Thavonekham, Youla Tsantrizos
Life of this patent
Estimating the term…
Abstract
A compound, represented by formula (I): wherein A, B, R1, R2, R3, R5, R6, R7, R9, and R10 are as defined herein, or an enantiomer, diastereoisomer or tautomer thereof, including a salt, ester or derivative thereof, as an inhibitor of HCV NS5B polymerase.
Claims33
A compound of formula (I):
- wherein:
- either A or B is N and the other B or A is C, wherein ----- between two C-atoms represents a double bond and ----- between a C-atom and a N-atom represents a single bond;
- R1 is H or (C1-6)alkyl;
- R2 is (C1-6)alkyl, (C2-6)alkynyl, —C(═O)—(C1-6)alkyl, aryl or Het;
- the aryl and Het being optionally substituted with R21;
- wherein R21 is one, two or three substituents each independently selected from (C1-6)alkyl, (C3-7)cycloalkyl, Het, —CN, —NH2, —NH(C1-6)alkyl, —N((C1)alkyl)2, halo, —O—(C1-6)alkyl, —S—(C1-6)alkyl, —SO—(C1-6)alkyl and —SO2—(C1-6)alkyl;
- wherein the (C1-6)alkyl, —O—(C1-6)alkyl, —S—(C1-6)alkyl, —SO—(C1-1)alkyl and —SO2—(C1-6)alkyl are each optionally substituted with one, two or three halo substituents;
- R3 is (C5-6)cycloalkyl, optionally substituted with from one to four halo substituents;
- R5 is selected from H, (C1-6)alkyl, (C2-6)alkenyl, (C2-6)alkynyl, (C3-7)cycloalkyl, (C3-7)cycloalkyl-(C1-6)alkyl-, Het and Het-(C1-6)alkyl-;
- wherein the (C1-6)alkyl is optionally substituted with from one to three substituents each independently selected from halo, cyano, (C1-6)alkoxy, —NH(C1-6)alkyl, —N((C1-6)alkyl)2 and —NHSO2(C1-6)alkyl;
- and
- wherein each of the Het and the Het portion of the Het-(C1-6)alkyl- is optionally substituted with (C1)alkyl;
- and
- R6 is selected from H, (C1-6)alkyl and halo;
- or
- R5 and R6 are linked such that the group of the subformula
- is a group of formula
- wherein n is 0, 1 or 2;
- and wherein R50 is selected independently in each instance from H, halo, cyano, (C1-6)alkoxy, (C1-)alkyl, (C2-6)alkenyl, (C2-6)alkynyl, (C3-7)cycloalkyl, (C3-7)cycloalkyl-(C1-6)alkyl-, Het and Het-(C1-6)alkyl-;
- wherein the (C1-6)alkyl is optionally substituted with from one to three substituents each independently selected from halo, cyano, (C1-6)alkoxy, —NH(C1-6)alkyl, —N((C1-6)alkyl)2 and —NHSO2(C1-6)alkyl;
- and wherein each of the Het and the Het portion of the Het-(C1-6)alkyl- is optionally substituted with (C1-6)alkyl;
- R7 is selected from H, (C1-)alkyl, (C1-6)alkoxy, (C1-6)alkylthio, —NH2, —NH(C1-6)alkyl, —N((C1-6)alkyl)2 and halo;
- R9 and R10 are each independently selected from (C1-6)alkyl;
- or R9 and R10 are covalently bonded together to form (C3-7)cycloalkyl, (C5-7)cycloalkenyl or a 4-, 5- or 6-membered heterocycle having from 1 to 3 heteroatoms each independently selected from O, N, and S;
- wherein the cycloalkyl, cycloalkenyl or heterocycle is optionally substituted with (C1-4)alkyl;
- wherein Het is defined as a 4- to 7-membered heterocycle having 1 to 4 heteroatoms each independently selected from O, N and S, which may be saturated, unsaturated or aromatic, and which is optionally fused to at least one other cycle to form a 7 to 14-membered heteropolycycle having wherever possible 1 to 5 heteroatoms, each independently selected from O, N and S, the heteropolycycle being saturated, unsaturated or aromatic;
- or an enantiomer, diastereoisomer or tautomer thereof, including a salt, ester or derivative thereof.
24 more elements
A compound of formula (I):
- wherein:
- either A or B is N and the other B or A is C, wherein ----- between two C-atoms represents a double bond and ----- between a C-atom and a N-atom represents a single bond;
- R1 is H or (C1-6)alkyl;
- R2 is (C2-6)alkynyl, —C(═O)—(C1-6)alkyl, aryl or Het;
- the aryl and Het being optionally substituted with R21;
- wherein R21 is one, two or three substituents each independently selected from (C1-6)alkyl, (C3-7)cycloalkyl, Het, —CN, —NH2, —NH(C1-6)alkyl, —N((C1-6)alkyl)2, halo, —O—(C1-6)alkyl, —S—(C1-6)alkyl, —SO—(C1-6)alkyl and —SO2—(C1l6)alkyl;
- wherein the (C1-6)alkyl, —O—(C1-6)alkyl, —S—(C1-6)alkyl, —SO—(C1-6)alkyl and —SO2—(C1-6)alkyl are each optionally substituted with one, two or three halo substituents;
- R3 is (C5-6)cycloalkyl, optionally substituted with from one to four halo substituents;
- R5 is selected from H, (C1-6)alkyl, (C2-6)alkenyl, (C2-6)alkynyl, (C3-7)cycloalkyl, and (C3-7)cycloalkyl-(C1-6)alkyl-;
- wherein the (C1-6)alkyl is optionally substituted with from one to three substituents each independently selected from halo, cyano and (C1-6)alkoxy;
- and
- R6 is selected from H, (C1-6)alkyl and halo;
- or
- R5 and R0 are linked, together with the atoms to which they are attached, to form a 5-, 6- or 7-membered ring;
- R7 is selected from H, (C1-6)alkyl, (C1-6)alkoxy, (C1-6)alkylthio, —NH2, —NH(C1-6)alkyl, —N((C1-6)alkyl)2 and halo;
- R9 and R10 are each independently selected from (C1-6)alkyl;
- or R9 and R10 are covalently bonded together to form (C3-7)cycloalkyl, (C5-7)cycloalkenyl or a 4-, 5- or 6-membered heterocycle having from 1 to 3 heteroatoms each independently selected from O, N, and S;
- wherein the cycloalkyl, cycloalkenyl or heterocycle are each optionally substituted with (C1-4)alkyl;
- wherein Het is defined as a 3- to 7-membered heterocycle having 1 to 4 heteroatoms each independently selected from O, N and S, which may be saturated, unsaturated or aromatic, and which is optionally fused to at least one other cycle to form a 4- to 14-membered heteropolycycle having wherever possible 1 to 5 heteroatoms, each independently selected from O, N and S, the heteropolycycle being saturated, unsaturated or aromatic;
- or an enantiomer, diastereoisomer or tautomer thereof, including a salt thereof.
17 more elements
Dependencies are inferred from the claim text.