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US 2004/0006098 A1Published application
Imidazonaphthyridines
Assignee3M Innovative Properties Company
InventorsJohn F. Gerster, Kyle J. Lindstrom, Stephen L. Crooks, Philip D. Heppner, Gregory J. Marszalek, Peter V. Maye, Bryon A. Merrill, John W. Mickelson, Michael J. Rice
Life of this patent
Estimating the term…
Abstract
Imidazonaphthyridine and tetrahydroimidazonaphthyridine compounds induce the biosynthesis of cytokines such as interferon and tumor necrosis factor. The compounds exhibit antiviral and antitumor properties. Methods of preparing the compounds and intermediates useful in the preparation of the compounds are also disclosed.
Claims26
A compound of the formula I:
- 178
- 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;
- —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 consisiting 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 alkyl0-1-heterocyclyl;
- —N(R3)2;
- —NR3—CO—O—C1-20alkyl;
- —N3;
- oxo;
- -halogen;
- —NO2;
- —OH;
- and
- —SH;
- or R4 is
- 179
- 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.
81 more elements
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—R4 or —C2-20 alkenyl-NR3—CO—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—C11-20 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
- 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—C2-10 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.
80 more elements
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;
- —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—(C1-20alkyl)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;
- —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.
81 more elements
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—(C1-20alkyl)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 consiting 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;
- —NR3—CO—O—C1-20alkyl;
- —N3;
- 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—C2-10 alkenyl;
- and
- —C1-10 alkyl or C2-10 alkenyl substituted by one or more substituents selected from the group consiting 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
76 more elements
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;
- —N3;
- 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—C1-20alkyl,
- —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
- 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.
76 more elements
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—C1-20 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—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—(C1-20alkyl)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
- 190
- wherein Y is —N— or —CR—;
- R8 is H, NO2 or NH2;
- 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.
61 more elements
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.
4 more elements
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—(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;
- —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—(C1-20alkyl)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
- 193
- wherein Y is —N— or —CR—;
- each R3 is independently selected from the group consisting of hydrogen and C1-10 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
55 more elements
Dependencies are inferred from the claim text.