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US 9,212,177 B2Granted
Antiviral compounds and methods of making and using thereof
AssigneeVersitech Limited
InventorsYi Tsun Richard Kao, Dan Yang, Kwok-Yung Yuen
Life of this patent
Estimating the term…
Abstract
Compounds which exhibit antiviral activity, particularly against influenza virus, and methods of making and using thereof are described herein. In one embodiment, the compounds are heterocyclic amides containing piperazine and isozazole rings and optionally substituted with one or more substituents. The compounds can be formulated with one or more pharmaceutically acceptable excipients to form compositions suitable for enteral or parenteral administration. The compounds are preferably used to treat or prevent Influenza A infections, such as H1N1, H2N2, H3N2, H5N1, H7N7, H1N2, H9N2, H7N2, H7N3, and H10N7.
Claims19
A compound of formula VI:
- X, Y, and Z are independently absent or selected from the group consisting of —C(═O)—, —S(═O)—, —SO2—, —N(R12)—, —C(R13)═C(R14)—, and —C(R15R16)n—;
- n, g, and m are independently 0 to 6;
- A and D are independently selected from nitrogen or CR17;
- wherein R1, R2, R4, R5, R6 and R10-R17 are independently selected from hydrogen;
- halo;
- hydroxyl;
- substituted or unsubstituted, linear or branched C1-C6 alkyl;
- substituted or unsubstituted, linear or branched C1-C6 alkenyl;
- substituted or unsubstituted, linear or branched C1-C6 alkynyl;
- or substituted or unsubstituted, linear or branched C1-C6 alkoxy;
- amino;
- azide;
- cyano;
- nitro;
- nitrile;
- isonitrile;
- amide;
- carboxylate;
- urea;
- guanidine;
- isocyanate;
- isothiocyanate;
- and thioether, and
- R7 is selected from halo;
- hydroxyl;
- substituted or unsubstituted, linear or branched C1-C6 alkyl;
- substituted or unsubstituted, linear or branched C1-C6 alkenyl;
- substituted or unsubstituted, linear or branched C1-C6 alkynyl;
- or substituted or unsubstituted, linear or branched C1-C6 alkoxy;
- amino;
- azide;
- cyano;
- nitro;
- nitrile;
- isonitrile;
- amide;
- carboxylate;
- urea;
- guanidine;
- isocyanate;
- isothiocyanate;
- and thioether.
39 more elements
A compound of selected from the group consisting of:
- [4-(2-chloro-4-nitro-phenyl)-piperazin1-yl]-[3-(4-hydroxy-phenyl)-5-methylisoxazol-4-yl]-methanone;
- [4-(2-chloro-4-nitro-phenyl)-piperazin-1-yl]-[3-phenyl-5-methyl-isoxazol-4-yl]-methanone;
- [4-(2-chloro-4-nitro-phenyl)-piperazin-1-yl]-[3-(4-amino-phenyl)-methylisoxazol-4-yl]-methanone;
- [4-(2-chloro-4-nitro-phenyl)-piperazin-1-yl]-[3-(4-azido-phenyl)-5-methylisoxazol-4-yl]-methanone;
- [4-(2-chloro-4-nitro-phenyl)-piperazin-1-yl]-[3-(2-chloro-phenyl)-5-methylisoxazol-4-yl]-methanone;
- [4-(2-chloro-4-nitro-phenyl)-2-methyl-piperazin-1-yl]-[3-(2-chloro-phenyl)-5-methyl-isoxazol-4-yl]-methanone;
- [4-(2-chloro-4-nitro-phenyl)-2-methyl-piperazin-1-yl]-[3-phenyl-5-methylisoxazol-4-yl]-methanone;
- [4-(4-nitro-pheny1)-piperazin-1-yl]-[3-(2-chloro-phenyl)-5-methyl-isoxazol-4-yl]-methanone;
- and [4-(4-nitro-pheny1)-piperazin-1-yl]-[3-(2,6-dichloro-phenyl)-5-methyl-isoxazol-4-yl]-methanone.
6 more elements
A compound of formula (III):
- wherein T, Q, and R are independently selected from C(R8R9), nitrogen, oxygen, phosphorous, silicon, sulfur, and arsenic;
- wherein R4 and R8-R9 are independently selected from hydrogen;
- halo;
- hydroxyl;
- substituted or unsubstituted, linear or branched C1-C6 alkyl;
- substituted or unsubstituted, linear or branched C1-C6 alkenyl;
- substituted or unsubstituted, linear or branched C1-C6 alkynyl;
- or substituted or unsubstituted, linear or branched C1-C6 alkoxy;
- amino;
- azide;
- cyano;
- nitro;
- nitrile;
- isonitrile;
- amide;
- carboxylate;
- urea;
- guanidine;
- isocyanate;
- isothiocyanate;
- and thioether;
- wherein Ar1 and Ara are each independently substituted or unsubstituted aryl or heteroaryl groups;
- X, Y, and Z are independently absent or selected from the group consisting of —C(═O)—, —S(═O)—, —SO2—, —N(R12)—, —C(R13)═C(R14)—, and —C(R15R16)n—;
- n, g and m are independently 0 to 6;
- A and D are independently selected from nitrogen or CR17;
- wherein when Ar3 is phenyl, and the phenyl group is substituted at the para position, the substituent is selected from the group consisting of halo;
- hydroxyl;
- substituted or unsubstituted, linear or branched C1-C6 alkyl;
- substituted or unsubstituted, linear or branched C1-C6 alkenyl;
- substituted or unsubstituted, linear or branched C1-C6 alkynyl;
- or substituted or unsubstituted, linear or branched C1-C6 alkoxy;
- amino;
- azide;
- cyano;
- nitro;
- nitrile;
- isonitrile;
- amide;
- carboxylate;
- urea;
- guanidine;
- isocyanate;
- isothiocyanate;
- and thioether, or the phenyl group comprises a nitro group,
- R12-R17 are independently selected from hydrogen;
- halo;
- hydroxyl;
- substituted or unsubstituted, linear or branched C1-C6 alkyl;
- substituted or unsubstituted, linear or branched C1-C6 alkenyl;
- substituted or unsubstituted, linear or branched C1-C6 alkynyl;
- or substituted or unsubstituted, linear or branched C1-C6 alkoxy;
- amino;
- azide;
- cyano;
- nitro;
- nitrile;
- isonitrile;
- amide;
- carboxylate;
- urea;
- guanidine;
- isocyanate;
- isothiocyanate;
- and thioether;
- and
- R10 is independently selected from hydrogen;
- halo;
- hydroxyl;
- substituted or unsubstituted, linear or branched C1-C6 alkyl;
- substituted or unsubstituted, linear or branched C1-C6 alkenyl;
- substituted or unsubstituted, linear or branched C1-C6 alkynyl;
- or substituted or unsubstituted, linear or branched C1-C6 alkoxy;
- amino;
- azide;
- cyano;
- nitro;
- nitrite;
- isonitrile;
- amide;
- carboxylate;
- urea;
- guanidine;
- isocyanate;
- isothiocyanate;
- and thioether.
82 more elements
Dependencies are inferred from the claim text.