Imidazonaphthyridines

A compound of the formula II:

• 181
• wherein
• B is —NR—C(R)2—C(R)2—C(R)2—;
• —C(R)2—NR—C(R)2—C(R)2—;
• —C(R)2—C(R)2—NR—C(R)2— or —C(R)2—C(R)2—C(R)2—NR—;
• R1 is selected from the group consisting of:
• -hydrogen;
• —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20 alkyl,
• —O—(C1-20alkyl)0-1-aryl;
• —O—(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2—C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• —N3;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• and
• —C1-20 alkyl-NR3-Q-X—R or —C2-20 alkenyl-NR3—CO—X—R4 wherein Q is —CO— or —SO2—;
• X is a bond, —O— or —NR3— and R1 is aryl;
• heteroaryl;
• heterocyclyl;
• or —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20 alkyl,
• —O—(C1-20alkyl)0-1-aryl;
• —O—(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2—C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2(C1-20 alkyl)0-1-heterocyclyl;
• —N(R1)2;
• —NR3—CO—O—C1-20alkyl;
• —N3;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• or R4 is
• 182
• wherein Y is —N— or —CR—;
• R2 is selected from the group consisting of:
• -hydrogen;
• —C1-10 alkyl;
• —C2-10 alkenyl;
• -aryl;
• —C1-10 alkyl-O—C1-10-alkyl;
• —C1-10 alkyl-O—C2-10alkenyl;
• and
• —C1-10 alkyl or C2-10 alkenyl substituted by one or more substituents selected from the group consisting of:
• —OH;
• -halogen;
• —N(R3)2;
• —CO—N(R3)2;
• —CO—C10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• each R3 is independently selected from the group consisting of hydrogen and C1-10 alkyl;
• and
• each R is independently selected from the group consisting of hydrogen, C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl,
• or a pharmaceutically acceptable salt thereof.

A compound of formula

• 183
• wherein
• A is ═N—CR═CR—CR═;
• ═CR—N═CR—CR═;
• —CR—CR═N—CR═;
• or ═CR—CR═CR—N═;
• R1 is selected from the group consisting of:
• -hydrogen;
• —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20 alkyl,
• —O—(C1-20alkyl)0-1-aryl;
• —O—(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C0-20 alkoxycarbonyl;
• —S(O)0-2—C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2—(C0-20 alkyl)0-1-heteroaryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• —N3;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• and
• —C1-20 alkyl-NR3-Q-X—R4 or —C2-20 alkenyl-NR3-Q-X—R4 wherein Q is —CO— or —SO2—;
• X is a bond, —O— or —NR3— and R4 is aryl;
• heteroaryl;
• heterocyclyl;
• or —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20alkyl,
• —O—(C1-20alkyl)0-1-aryl;
• —O—(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2-C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• —NR3—CO—O—C1-20alkyl;
• —N3;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• or R4 is
• 184
• wherein Y is —N— or —CR—;
• R2 is selected from the group consisting of:
• -hydrogen;
• —C1-10 alkyl;
• —C2-10 alkenyl;
• -aryl
• —C1-10 alkyl-O—C1-10-alkyl;
• —C1-10 alkyl-O—C2-10-alkenyl;
• and
• —C1-10 alkyl or C2-10 alkenyl substituted by one or more substituents selected from the group consisting of:
• —OH;
• -halogen;
• (R3)2;
• —CO—N(R3)2;
• —CO—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• each R3 is independently selected from the group consisting of hydrogen and C1-10 alkyl;
• and
• each R is independently selected from the group consisting of hydrogen, C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof.

A compound of formula

• 185
• wherein
• R1 is selected from the group consisting of:
• -hydrogen;
• —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20 alkyl,
• —O—(C1-20 alkyl)0-1-aryl;
• —O—(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2—C1-20 alkyl;
• —S(O)0-2—(C1-20alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• —N3;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• and
• —C1-20 alkyl-NR3-Q-X-4 or —C2-20 alkenyl-NR3-Q-X—R4 wherein Q is —CO— or —SO2—;
• X is a bond, —O— or —NR3— and R4 is aryl;
• heteroaryl;
• heterocyclyl;
• or —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20 alkyl,
• —O—(C1-20alkyl)0-1-aryl;
• —O—(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2—C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• —NR—CO—O—C1-20alkyl;
• —N;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• or R4 is
• 186
• wherein Y is —N— or —CR—;
• R2 is selected from the group consisting of:
• -hydrogen;
• —C1-10 alkyl;
• —C2-10 alkenyl;
• -aryl;
• —C1-10 alkyl-O—C1-10-alkyl;
• —C1-10 alkyl-O—C2-10alkenyl;
• and
• —C1-10 alkyl or C2 to alkenyl substituted by one or more substituents selected from the group consisting of:
• —OH;
• -halogen;
• —N(R3)2;
• —CO—N(R3)2;
• —CO—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• each R3 is independently selected from the group consisting of hydrogen and C1-10 alkyl;
• and
• each R is independently selected from the group consisting of hydrogen, C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof.

A compound of formula

• 187
• wherein
• R1 is selected from the group consisting of:
• -hydrogen;
• —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20 alkyl,
• —O—(C1-20alkyl)0-1-aryl;
• —O-(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2—(C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• —N2;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• —C1-20 alkyl-;NR3-Q-X—R4 or —C2-20 alkenyl-NR3-Q-X—R4 wherein Q is —CO— or —SO2—;
• X is a bond, —O— or —NR3— and R4 is aryl;
• heteroaryl;
• heterocyclyl;
• or —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20 alkyl,
• —O-(C1-20 alkyl)0-1-aryl;
• —O—(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2—C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2-(C1-20 alkyl)0-1-heterocyclyl;
• —N(R)2;
• —NR3—CO—O—C1-20alkyl;
• —N3;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• or R4 is
• 188
• wherein Y is —N— or —CR—;
• R2 is selected from the group consisting of:
• -hydrogen;
• —C1-10 alkyl;
• —C2-10 alkenyl;
• -aryl;
• —C1-10 alkyl-O—C1-10-alkyl;
• —C1-10 alkyl-O—C2-10 alkenyl;
• and
• —C1-10 alkyl or C2-10 alkenyl substituted by one or more substituents selected from the group consisting of:
• —OH;
• -halogen;
• —N(R3)2;
• —CO—N(R3)2;
• —CO—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• each R3 is independently selected from the group consisting of hydrogen and C1-10 alkyl;
• and
• each R is independently selected from the group consisting of hydrogen, C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl,
• or a pharmaceutically acceptable salt thereof.

A compound of formula

• 189
• wherein
• A is ═N—CR═CR—CR═;
• —CR—N═CR—CR═;
• ═CR—CR═N—CR═;
• or —CR—CR═CR—N═;
• R7 is OH, halogen, or NHR1,
• R1 is selected from the group consisting of:
• -hydrogen;
• —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20alkyl,
• —O—(C1-20alkyl)0-1-aryl;
• —O—(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2—C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• —N3;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• and
• —C1-20 alkyl-NR3-Q-X—R4 or —C2-20 alkenyl-NR3-Q-X—R4 wherein Q is —CO— or —SO2—;
• X is a bond, —O— or —NR3— and R4 is aryl;
• heteroaryl;
• heterocyclyl;
• or —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20 alkyl,
• —O—(C1-20 alkyl)0-1-aryl;
• —O—(C1-20 alkyl)0-1-heteroaryl;
• —O—(C1-20 alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2—C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• —NR3—CO—O—C1-20 alkyl;
• —N3;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• or R4 is
• 190
• wherein Y is —N— or —CR—;
• R8 is H, NO2 or NH,;
• and
• each R is independently selected from the group consisting of hydrogen, C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl;
• or a pharmaceutically acceptable salt thereof.

A compound of formula

• 191
• wherein
• A is ═N—CR═CR—CR═;
• ═CR—N═CR—CR═;
• ═CR—CR═N—CR═;
• or ═CR—CR═CR—N═ and
• R9 is H or C1-10 alkyl.

A compound of formula

• 192
• wherein
• R1 is selected from the group consisting of:
• —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O-C1-20 alkyl;
• —O—(C2-20alkyl)0-1-aryl;
• —O—(C1-20alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2—C1-20alkyl;
• —S(O)0-2—(C1-20alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• —C1-20 alkyl-NR3-Q-X—R4 or —C2-20 alkenyl-NR3-Q-X—R4 wherein Q is —CO— or —SO2—;
• X is a bond, —O— or —NR3— and R4 is aryl;
• heteroaryl;
• heterocyclyl;
• or —C1-20 alkyl or C2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —O—C1-20 alkyl;
• —O—(C1-20 alkyl)0-1-aryl;
• —O—(C1-20 alkyl)0-1-heteroaryl;
• —O—(C1-20alkyl)0-1-heterocyclyl;
• —C1-20 alkoxycarbonyl;
• —S(O)0-2-C1-20 alkyl;
• —S(O)0-2—(C1-20 alkyl)0-1-aryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heteroaryl;
• —S(O)0-2—(C1-20 alkyl)0-1-heterocyclyl;
• —N(R3)2;
• —NR3—CO—O—C1-20 alkyl;
• —N3;
• oxo;
• -halogen;
• —NO2;
• —OH;
• and
• —SH;
• or R is
• 193
• wherein Y is —N— or —CR—;
• each R3 is independently selected from the group consisting of hydrogen and C1-0 alkyl;
• each R is selected from the group consisting of hydrogen, C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl;
• and
• R10 is —NO2 or NH2;
• or a pharmaceutically acceptable salt thereof.