CA2376305A1 - Sulfonamide and sulfamide substituted imidazoquinolines - Google Patents
Sulfonamide and sulfamide substituted imidazoquinolines Download PDFInfo
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- CA2376305A1 CA2376305A1 CA002376305A CA2376305A CA2376305A1 CA 2376305 A1 CA2376305 A1 CA 2376305A1 CA 002376305 A CA002376305 A CA 002376305A CA 2376305 A CA2376305 A CA 2376305A CA 2376305 A1 CA2376305 A1 CA 2376305A1
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- alkyl
- butyl
- amino
- quinolin
- imidazo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0063—Periodont
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
Imidazoquinoline and tetrahydroimidazoquinoline compounds that contain sulfonamide or sulfonamide functionality at the 1-position are useful as immune response modifiers. The compounds and compositions of the invention can induce the biosynthesis of various cytokines and are useful in the treatment of a variety of conditions including viral diseases and neoplastic diseases.
Claims (37)
- WHAT IS CLAIMED IS:
A compound of the formula (I):
wherein R1 is -alkyl-NR3- SO2 -X-R4 or -alkenyl-NR3- SO2 -X-R4 ;
X is a bond or -NR5-;
R4 is aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents selected from the group consisting of:
-alkyl;
-alkenyl;
-aryl -heteroaryl;
-heterocyclyl;
-substituted cycloalkyl;
-substituted aryl;
-substituted heteroaryl;
-substituted heterocyclyl;
-O-alkyl;
-O-(alkyl)0-1-aryl;
-O-(alkyl)0-1-substituted aryl;
-O-(alkyl)0-1-heteroaryl;
-O-(alkyl)0-1-substituted heteroaryl;
-O-(alkyl)0-1-heterocyclyl;
-O-(alkyl)0-1-substituted heterocyclyl;
-COOH;
-CO-O-alkyl;
-CO-alkyl;
-S(O)0-2-alkyl;
-S (O)0-2-(alkyl)0-1-aryl;
-S(O)0-2-(alkyl)0-1-substituted aryl;
-S(O)0-2-(alkyl)0-1-heteroaryl;
-S(O)0-2-(alkyl)0-1-substituted heteroaryl;
-S(O)0-2-(alkyl)0-1-heterocyclyl;
-S(O)0-2-(alkyl)0-1-substituted heterocyclyl;
-(alkyl)0-1-NR3R3;
-(alkyl)0-1-NR3-CO-O-alkyl;
-(alkyl)0-1-NR3-CO-alkyl;
-(alkyl)0-1-NR3-CO-aryl;
-(alkyl)0-1-NR3-CO-substituted aryl;
-(alkyl)0-1-NR3-CO-heteroaryl;
-(alkyl)0-1-NR3-CO-substituted heteroaryl;
-N3;
-halogen;
-haloalkyl;
-haloalkoxy;
-CO-haloalkyl;
-CO-haloalkoxy;
-NO2;
-CN;
-OH;
-SH; and in the case of alkyl, alkenyl, or heterocyclyl, oxo;
R2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
- alkyl-alkyl;
- alkyl-O- alkenyl; and - alkyl or 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;
-CO-O-C1-10 alkyl;
-N3;
-aryl -substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-heterocyclyl;
-substituted heterocyclyl;
-CO-aryl;
-CO-(substituted aryl);
-CO-heteroaryl; and -CO-(substituted heteroaryl);
each R3 is independently selected from the group consisting of hydrogen and C1-alkyl;
R5 is selected from the group consisting of hydrogen and C1-10 alkyl, or R4 and R5 can combine to form a 3 to 7 membered heterocyclic or substituted heterocyclic ring;
n is 0 to 4 and each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof. - 2. A compound of claim 1 wherein X is a bond.
- 3. A compound of claim 2 wherein n is 0.
- 4. A compound of claim 2 wherein each R3 is hydrogen.
- 5. A compound of claim 2 wherein R1 is -(CH2)2-4- NR3- SO2 -R4.
- 6. A compound of claim 2 wherein R4 is selected from the group consisting of alkyl, aryl and heteroaryl that may be unsubstituted or substituted by one or more substituents selected from the group consisting of:
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-substituted aryl;
-substituted heteroaryl;
-substituted heterocyclyl;
-O-alkyl;
-O-(alkyl)0-1-aryl;
-O-(alkyl)0-1-substituted aryl;
-O-(alkyl)0-1-heteroaryl;
-O-(alkyl)0-1-substituted heteroaryl;
-O-(alkyl)0-1-heterocyclyl;
-O-(alkyl)0-1-substituted heterocyclyl;
-COOH;
-CO-O-alkyl;
-CO-alkyl;
-S(O)0-2-alkyl;
-S(O)0-2-(alkyl)0-1-aryl;
-S(O)0-2-(alkyl)0-1-substituted aryl;
-S(O)0-2-(alkyl)0-1-heteroaryl;
-S(O)0-2-(alkyl)0-1-substituted heteroaryl;
-S(O)0-2-(alkyl)0-1-heterocyclyl;
-S(O)0-2-(alkyl)0-1-substituted heterocyclyl;
-(alkyl)0-1-NR3R3;
-(alkyl)0-1-NR3-CO-O-alkyl;
-(alkyl)0-1-NR3-CO-alkyl;
-(alkyl)0-1-NR3-CO-aryl;
-(alkyl)0-1-NR3-CO-substituted aryl;
-(alkyl)0-1-NR3-CO-heteroaryl;
-(alkyl)0-1-NR3-CO-heteroaryl;
-(alkyl)0-1-NR3-CO-substituted heteroaryl;
-N3;
-halogen;
-haloalkyl;
-haloalkoxy;
-CO-haloalkoxy;
-NO2;
-CN;
-OH;
-SH; and in the case of alkyl, oxo. - 7. A compound of claim 2 wherein R2 is selected from the group consisting of hydrogen; alkyl; alkyl-O-alkyl; (alkyl)0-1 aryl, (alkyl)0-1-(substituted aryl); (alkyl)0-1-heteroaryl; and (alkyl)0-1-(substituted heteroaryl).
- 8. A compound of claim 2 wherein R2 is selected from the group consisting of hydrogen, C1-4alkyl, and C1-4alkyl-O- C1-4alkyl.
- 9. A compound of claim 2 wherein the dashed bonds are absent.
- 10. A compound of claim 1 wherein X is -NR5-.
- 11. A compound of claim 10 wherein n is 0.
- 12. A compound of claim 10 wherein R1 is -(CH2)2-4- NR3- SO2 -NR5 -R4.
- 13. A compound of claim 10 wherein R2 is selected from the group consisting of hydrogen; alkyl; alkyl-O-alkyl; (alkyl)0-1 aryl, (alkyl)0-1-(substituted aryl); (alkyl)0-1-heteroaryl; and (alkyl)0-1-(substituted heteroaryl).
- 14. A compound of claim 10 wherein R2 is selected from the group consisting of hydrogen, C1-4alkyl, and C1-4alkyl-O- C1-4alkyl.
- 15. A compound of claim 10 wherein R4 and R5 join to form a 3 to 7 membered heterocyclic or substituted heterocyclic ring.
- 16. A compound of claim 10 wherein R4 and R5 join to form a substituted or unsubstituted pyrrolidine, morpholine, thiomorpholine, piperidine, or piperazine ring.
- 17. A compound of claim 16 wherein R3 is hydrogen.
- 18. A compound of claim 15 wherein R2 is selected from the group consisting of hydrogen; alkyl; alkyl-O-alkyl; (alkyl)0-1 aryl, (alkyl)0-1-(substituted aryl); (alkyl)0-1-heteroaryl; and (alkyl)0-1-(substituted heteroaryl).
- 19. A compound of claim 16 wherein R2 is selected from the group consisting of hydrogen, C1-4alkyl, and C1-4alkyl-O- C1-4alkyl.
- 20. A compound of claim 10 wherein R4 and R5 are alkyl.
- 21. A compound of claim 20 wherein R3 is hydrogen.
- 22. A compound of claim 20 wherein R2 is selected from the group consisting of hydrogen; alkyl; alkyl-O-alkyl; (alkyl)0-1, aryl, (alkyl)0-1-(substituted aryl); (alkyl)0-1-heteroaryl; and (alkyl)0-1-(substituted heteroaryl).
- 23. A compound of claim 10 wherein R3 is hydrogen.
- 24. A compound selected from the group consisting of:
N2-[2-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-2-thiophenesulfonamide;
N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-1-benzenesulfonamide;
N8-[2-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-8-quinolinesulfonamide;
N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-5-(dimethylamino)-1-naphthalenesulfonamide;
N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide;
N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-benzenesulfonamide;
N8-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-8-quinolinesulfonamide;
N2-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-thiophenesulfonamide;
N2-[4-(4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-thiophenesulfonamide;
N1-[4-(4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-benzenesulfonamide;
N8-[4-(4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-8-quinolinesulfonamide;
N1-[4-(4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(dimethylamino)-1-naphthalenesulfonamide;
N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-fluoro-1-benzenesulfonamide;
N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c] quinolin-1-yl)butyl]-3-fluoro-1-benzenesulfonamide;
N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}methanesulfonamide;
N2-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-2-thiophenesulfonamide;
N1-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-5-(dimethylamino)-1-naphthalenesulfonamide;
N1-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}methanesulfonamide;
N2-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-2-thiophenesulfonamide;
N1-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-5-(dimethylamino)-1-naphthalenesulfonamide;
N1-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-4-fluoro-1-benzenesulfonamide;
N1-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-3-fluoro-1-benzenesulfonamide;
N1-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-1-benzenesulfonamide;
N8-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-8-quinolinesulfonamide;
N2-{4-[4-amino-2-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-2-thiophenesulfonamide;
N-[4-(4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide;
N2-[4-(4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-thiophenesulfonamide;
N1-[4-(4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(dimethylamino)-1-naphthalenesulfonamide;
N1{-4-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-1-benzenesulfonamide;
N1-{4-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo [4,5-c]quinolin-1-yl]butyl}-5-(dimethylamino)-1-naphthalenesulfonamide;
N'-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N,N-dimethylsulfamide;
N'-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-N,N-dimethylsulfamide;
N'-{4-[4-amino-2-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-N,N-dimethylsulfamide;
N'-[4-(4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N,N-dimethylsulfamide;
N'-{4-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-N,N-dimethylsulfamide;
N4-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-4-thiomorpholinesulfonamide;
N1-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-1-pyrrolidinesulfonamide;
N1-[4-(4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-fluoro-1-benzenesulfonamide;
N-[4-(4-Amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide; and N-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}phenyl-methanesulfonamide. - 25. A compound selected from the group consisting of:
N1-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(dimethylamino)-1-naphthalenesulfonamide;
N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(dimethylamino)-1-naphthalenesulfonamide;
N2-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-thiophenesulfonamide;
N-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-phenylmethanesulfonamide;
N1-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-benzenesulfonamide;
N-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]
Methanesulfonamide;
N1-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-3-nitro-1-benzenesulfonamide;
N1-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-3-amino-1-benzenesulfonamide;
N1-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-nitro-1-benzenesulfonamide;
N5-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-amino-1-benzenesulfonamide;
N5-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-isoquinolinesulfonamide N-[4-(4-Amino-2-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl]-methanesulfonamide;
N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-y)butyl]-1-butanesulfonamide;
N1-{4-[4-Amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-4-fluoro-1-benzenesulfonamide;
N1-[4-(4-Amino-2-phenyl-1H-imidazo [4,5-c]quinolin-1-yl)butyl]-4-fluoro-1-benzenesulfonamide; and N-[4-(4-Amino-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]
methanesulfonamide. - 26. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
- 27. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 2 and a pharmaceutically acceptable carrier.
- 28. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 10 and a pharmaceutically acceptable carrier.
- 29. A method of inducing cytokine biosynthesis in an animal comprising administering an effective amount of a compound of claim 1 to the animal.
- 30. A method of treating a viral disease in an animal comprising administering an effective amount of a compound of claim 1 to the animal.
- 31. A method of treating a neoplastic disease in an animal comprising administering an effective amount of a compound of claim 1 to the animal.
- 32. A method of inducing cytokine biosynthesis in an animal comprising administering an effective amount of a compound of claim 2 to the animal.
- 33. A method of treating a viral disease in an animal comprising administering an effective amount of a compound of claim 2 to the animal.
- 34. A method of treating a neoplastic disease in an animal comprising administering an effective amount of a compound of claim 2 to the animal.
- 35. A method of inducing cytokine biosynthesis in an animal comprising administering an effective amount of a compound of claim 10 to the animal.
- 36. A method of treating a viral disease in an animal comprising administering an effective amount of a compound of claim 10 to the animal.
- 37. A method of treating a neoplastic disease in an animal comprising administering an effective amount of a compound of claim 10 to the animal.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13836599P | 1999-06-10 | 1999-06-10 | |
US60/138,365 | 1999-06-10 | ||
US09/589,216 | 2000-06-07 | ||
US09/589,216 US6331539B1 (en) | 1999-06-10 | 2000-06-07 | Sulfonamide and sulfamide substituted imidazoquinolines |
PCT/US2000/015722 WO2000076519A1 (en) | 1999-06-10 | 2000-06-08 | Sulfonamide and sulfamide substituted imidazoquinolines |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2376305A1 true CA2376305A1 (en) | 2000-12-21 |
CA2376305C CA2376305C (en) | 2010-10-12 |
Family
ID=26836139
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2376305A Expired - Fee Related CA2376305C (en) | 1999-06-10 | 2000-06-08 | Sulfonamide and sulfamide substituted imidazoquinolines |
Country Status (29)
Country | Link |
---|---|
US (5) | US6331539B1 (en) |
EP (1) | EP1198233B1 (en) |
JP (1) | JP4833466B2 (en) |
KR (1) | KR100781428B1 (en) |
CN (1) | CN1249061C (en) |
AT (1) | ATE336249T1 (en) |
AU (1) | AU772179B2 (en) |
BR (1) | BR0011433B1 (en) |
CA (1) | CA2376305C (en) |
CY (1) | CY1108536T1 (en) |
CZ (1) | CZ303287B6 (en) |
DE (1) | DE60030126T2 (en) |
DK (1) | DK1198233T3 (en) |
EE (1) | EE05074B1 (en) |
ES (1) | ES2270840T3 (en) |
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