CA2311456A1 - Imidazonaphthyridines and their use in inducing cytokine biosynthesis - Google Patents

Imidazonaphthyridines and their use in inducing cytokine biosynthesis Download PDF

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CA2311456A1
CA2311456A1 CA002311456A CA2311456A CA2311456A1 CA 2311456 A1 CA2311456 A1 CA 2311456A1 CA 002311456 A CA002311456 A CA 002311456A CA 2311456 A CA2311456 A CA 2311456A CA 2311456 A1 CA2311456 A1 CA 2311456A1
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alkyl
aryl
heteroaryl
heterocyclyl
group
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CA2311456C (en
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Kyle J. Lindstrom
John F. Gerster
Stephen L. Crooks
Philip D. Heppner
Gregory J. Marszalek
Peter V. Maye
Bryon A. Merrill
John W. Mickelson
Michael J. Rice
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Takeda Pharmaceutical Co Ltd
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    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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Abstract

Imidazonaphthyridine (I) and tetrahydroimidazonaphthyridine (II) 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. R1 and R2 and A
are as defined in the application.

Claims (26)

1. A compound of the formula I:

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 alkyl)0-1-heterocyclyl;
-N(R3)2 -NR3-CO-O-C1-20alkyl;
-N3;
oxo;
-halogen;
-NO2;
-OH; and -SH; or R4 is wherein Y is -N- or -CR-;
R2 is selected from the group consisting of:
-hydrogen;
-C1-10 alkyl;
-C2-20 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-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-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.
2. A compound according to Claim 1 wherein R1 is selected from the group consisting of C1-6 alkyl and C1-6 hydroxyalkyl.
3. A compound according to Claim 2 wherein R1 is selected from the group consisting of n-butyl, 2-hydroxy-2-methylpropyl, and 2-methylpropyl.
4. A compound according to Claim 1 wherein R2 is selected from the group consisting of C1-6 straight chain alkyl and alkoxyalkyl wherein the alkoxy moiety and the alkyl moiety each independently contain 1 to 4 carbon atoms.
5. A compound according to Claim 4 wherein R2 is selected from the group consisting of methyl, n-butyl, benzyl, ethoxymethyl, and methoxyethyl.
6. A compound according to Claim 1 wherein each R is hydrogen.
7. A compound according to Claim 1 wherein R1 is -C1-20 alkyl-NR3-Q-X-R4.
8. A compound according to Claim 7 wherein R4 is
9. A compound according to Claim 1 wherein A is =CH-CH=CH-N=.
10. A compound of the formula II:

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-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 wherein Y is -N- or -CR-;

R1 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-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.
11. A compound according to Claim 10 wherein R1 is selected from the group consisting of C1-6 alkyl and C1-6 hydroxyalkyl.
12. A compound according to Claim 11 wherein R1 is selected from the group consisting of n-butyl, 2-hydroxy-2-methylpropyl, and 2-methylpropyl.
13. A compound according to Claim 10 wherein R2 is selected from the group consisting of methyl, n-butyl, benzyl, ethoxymethyl, and methoxyethyl.
14. A compound according to Claim 10 wherein each R is hydrogen.
15. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound according to Claim 1 and a pharmaceutically acceptable carrier.
16. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound according to Claim 10 and a pharmaceutically acceptable carrier.
17. A method of inducing cytokine biosynthesis in an animal comprising administering an effective amount of a compound according to Claim 1 to the animal.
18. A method of inducing cytokine biosynthesis in an animal comprising administering an effective amount of a compound according to Claim 10 to the animal.
19. A method of treating a viral infection in an animal comprising admistering an effective amount of a compound according to claim 1 to the animal.
20. A method of treating a viral infection man animal comprising administering an effective amount of a compounds according to claim 10 to the aminal.
21. A compound of formula 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(RO3)2;
-N>;
oxo;
-halogen;

-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 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-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.
22. A compound of formula 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 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-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.
23. A compound of formula 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-C1-20 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 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-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.
24. A compound of Formula 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)02-(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 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.
25. A compound of formula 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.
26. A compound of formula 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;

-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 C2-20o 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 wherein Y is -N- or -CR-;
each R3 is independently selected from the group consisting of hydrogen and C1-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.
CA2311456A 1997-12-11 1998-12-11 Imidazonaphthyridines and their use in inducing cytokine biosynthesis Expired - Lifetime CA2311456C (en)

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