CA2376305A1 - Sulfonamide and sulfamide substituted imidazoquinolines - Google Patents

Sulfonamide and sulfamide substituted imidazoquinolines Download PDF

Info

Publication number
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
Authority
CA
Canada
Prior art keywords
alkyl
butyl
amino
quinolin
imidazo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002376305A
Other languages
French (fr)
Other versions
CA2376305C (en
Inventor
Stephen L. Crooks
Kyle J. Lindstrom
Bryon A. Merrill
Michael J. Rice
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties Company
Stephen L. Crooks
Kyle J. Lindstrom
Bryon A. Merrill
Michael J. Rice
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 3M Innovative Properties Company, Stephen L. Crooks, Kyle J. Lindstrom, Bryon A. Merrill, Michael J. Rice filed Critical 3M Innovative Properties Company
Publication of CA2376305A1 publication Critical patent/CA2376305A1/en
Application granted granted Critical
Publication of CA2376305C publication Critical patent/CA2376305C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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)

  1. 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. 2. A compound of claim 1 wherein X is a bond.
  3. 3. A compound of claim 2 wherein n is 0.
  4. 4. A compound of claim 2 wherein each R3 is hydrogen.
  5. 5. A compound of claim 2 wherein R1 is -(CH2)2-4- NR3- SO2 -R4.
  6. 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. 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. 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. 9. A compound of claim 2 wherein the dashed bonds are absent.
  10. 10. A compound of claim 1 wherein X is -NR5-.
  11. 11. A compound of claim 10 wherein n is 0.
  12. 12. A compound of claim 10 wherein R1 is -(CH2)2-4- NR3- SO2 -NR5 -R4.
  13. 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. 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. 15. A compound of claim 10 wherein R4 and R5 join to form a 3 to 7 membered heterocyclic or substituted heterocyclic ring.
  16. 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. 17. A compound of claim 16 wherein R3 is hydrogen.
  18. 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. 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. 20. A compound of claim 10 wherein R4 and R5 are alkyl.
  21. 21. A compound of claim 20 wherein R3 is hydrogen.
  22. 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. 23. A compound of claim 10 wherein R3 is hydrogen.
  24. 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. 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. 26. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
  27. 27. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 2 and a pharmaceutically acceptable carrier.
  28. 28. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 10 and a pharmaceutically acceptable carrier.
  29. 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. 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. 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. 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. 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. 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. 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. 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. 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.
CA2376305A 1999-06-10 2000-06-08 Sulfonamide and sulfamide substituted imidazoquinolines Expired - Fee Related CA2376305C (en)

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)
HK (1) HK1086762A1 (en)
HR (1) HRP20010890B1 (en)
HU (1) HU229928B1 (en)
IL (2) IL146486A0 (en)
MX (1) MXPA01012547A (en)
NO (1) NO320747B1 (en)
NZ (1) NZ515967A (en)
PL (1) PL211009B1 (en)
PT (1) PT1198233E (en)
RU (1) RU2248975C2 (en)
SK (1) SK286418B6 (en)
TR (1) TR200103575T2 (en)
UA (1) UA73503C2 (en)
WO (1) WO2000076519A1 (en)

Families Citing this family (250)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5741908A (en) 1996-06-21 1998-04-21 Minnesota Mining And Manufacturing Company Process for reparing imidazoquinolinamines
UA67760C2 (en) 1997-12-11 2004-07-15 Міннесота Майнінг Енд Мануфакчурінг Компані Imidazonaphthyridines and use thereof to induce the biosynthesis of cytokines
US6518280B2 (en) 1998-12-11 2003-02-11 3M Innovative Properties Company Imidazonaphthyridines
US20020058674A1 (en) 1999-01-08 2002-05-16 Hedenstrom John C. Systems and methods for treating a mucosal surface
US6558951B1 (en) * 1999-02-11 2003-05-06 3M Innovative Properties Company Maturation of dendritic cells with immune response modifying compounds
US6331539B1 (en) * 1999-06-10 2001-12-18 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines
US6756382B2 (en) 1999-06-10 2004-06-29 3M Innovative Properties Company Amide substituted imidazoquinolines
US6541485B1 (en) 1999-06-10 2003-04-01 3M Innovative Properties Company Urea substituted imidazoquinolines
US6573273B1 (en) 1999-06-10 2003-06-03 3M Innovative Properties Company Urea substituted imidazoquinolines
US6916925B1 (en) 1999-11-05 2005-07-12 3M Innovative Properties Co. Dye labeled imidazoquinoline compounds
US6376669B1 (en) 1999-11-05 2002-04-23 3M Innovative Properties Company Dye labeled imidazoquinoline compounds
JP3436512B2 (en) * 1999-12-28 2003-08-11 株式会社デンソー Accelerator device
US6664260B2 (en) 2000-12-08 2003-12-16 3M Innovative Properties Company Heterocyclic ether substituted imidazoquinolines
US6545016B1 (en) 2000-12-08 2003-04-08 3M Innovative Properties Company Amide substituted imidazopyridines
US6664264B2 (en) 2000-12-08 2003-12-16 3M Innovative Properties Company Thioether substituted imidazoquinolines
UA75622C2 (en) * 2000-12-08 2006-05-15 3M Innovative Properties Co Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon
UA74593C2 (en) * 2000-12-08 2006-01-16 3M Innovative Properties Co Substituted imidazopyridines
US20020107262A1 (en) * 2000-12-08 2002-08-08 3M Innovative Properties Company Substituted imidazopyridines
US6677348B2 (en) 2000-12-08 2004-01-13 3M Innovative Properties Company Aryl ether substituted imidazoquinolines
AU3249802A (en) * 2000-12-08 2002-06-18 3M Innovative Properties Co Screening method for identifying compounds that selectively induce interferon alpha
JP2008531580A (en) * 2000-12-08 2008-08-14 スリーエム イノベイティブ プロパティズ カンパニー Compositions and methods for targeted delivery of immune response modifiers
US6525064B1 (en) 2000-12-08 2003-02-25 3M Innovative Properties Company Sulfonamido substituted imidazopyridines
US6660735B2 (en) * 2000-12-08 2003-12-09 3M Innovative Properties Company Urea substituted imidazoquinoline ethers
US6664265B2 (en) * 2000-12-08 2003-12-16 3M Innovative Properties Company Amido ether substituted imidazoquinolines
US6667312B2 (en) * 2000-12-08 2003-12-23 3M Innovative Properties Company Thioether substituted imidazoquinolines
US6677347B2 (en) 2000-12-08 2004-01-13 3M Innovative Properties Company Sulfonamido ether substituted imidazoquinolines
US6660747B2 (en) * 2000-12-08 2003-12-09 3M Innovative Properties Company Amido ether substituted imidazoquinolines
US6545017B1 (en) 2000-12-08 2003-04-08 3M Innovative Properties Company Urea substituted imidazopyridines
US7226928B2 (en) * 2001-06-15 2007-06-05 3M Innovative Properties Company Methods for the treatment of periodontal disease
CA2458876A1 (en) * 2001-08-30 2003-03-13 3M Innovative Properties Company Methods of maturing plasmacytoid dendritic cells using immune response modifier molecules
ATE416771T1 (en) * 2001-11-16 2008-12-15 3M Innovative Properties Co N-Ä4-(4-AMINO-2-ETHYL-1H-IMIDAZOÄ4,5-CUCHINOLINE 1-YL)BUTYLUMETHANESULFONAMIDE, PHARMACEUTICAL COMPOSITION CONTAINING SAME AND USE THEREOF
ES2312659T3 (en) * 2001-11-29 2009-03-01 3M Innovative Properties Company PHARMACEUTICAL FORMULATIONS THAT INCLUDE A MODIFIER OF THE IMMUNE RESPONSE.
CA2365732A1 (en) * 2001-12-20 2003-06-20 Ibm Canada Limited-Ibm Canada Limitee Testing measurements
US6677349B1 (en) * 2001-12-21 2004-01-13 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines
JP2005518433A (en) 2002-02-22 2005-06-23 スリーエム イノベイティブ プロパティズ カンパニー Methods for reducing and treating UVB-induced immunosuppression
CA2484049A1 (en) * 2002-03-19 2003-10-02 Powdermed Limited Imidazoquinoline adjuvants for vaccines
JP2005533752A (en) * 2002-03-19 2005-11-10 パウダーメド リミテッド Imidazoquinolinamine as an adjuvant in HIV DNA vaccination
DE50308334D1 (en) * 2002-05-07 2007-11-22 Schott Ag Lighting device for buttons
GB0211649D0 (en) 2002-05-21 2002-07-03 Novartis Ag Organic compounds
JP2005538057A (en) 2002-06-07 2005-12-15 スリーエム イノベイティブ プロパティズ カンパニー Ether-substituted imidazopyridine
AU2003299863B2 (en) 2002-08-15 2009-09-24 3M Innovative Properties Company Immunostimulatory compositions and methods of stimulating an immune response
US6818650B2 (en) * 2002-09-26 2004-11-16 3M Innovative Properties Company 1H-imidazo dimers
CN1738797A (en) * 2002-11-19 2006-02-22 阿基里昂药品公司 Substituted aryl thioureas and related compounds, inhibitors of viral replication
AU2003287316A1 (en) * 2002-12-11 2004-06-30 3M Innovative Properties Company Assays relating to toll-like receptor activity
WO2004053057A2 (en) * 2002-12-11 2004-06-24 3M Innovative Properties Company Gene expression systems and recombinant cell lines
CA2510375A1 (en) 2002-12-20 2004-07-15 3M Innovative Properties Company Aryl / hetaryl substituted imidazoquinolines
WO2004060319A2 (en) * 2002-12-30 2004-07-22 3M Innovative Properties Company Immunostimulatory combinations
WO2004071459A2 (en) * 2003-02-13 2004-08-26 3M Innovative Properties Company Methods and compositions related to irm compounds and toll-like receptor 8
JP2006519020A (en) * 2003-02-27 2006-08-24 スリーエム イノベイティブ プロパティズ カンパニー Selective regulation of TLR-mediated biological activity
WO2004078138A2 (en) 2003-03-04 2004-09-16 3M Innovative Properties Company Prophylactic treatment of uv-induced epidermal neoplasia
US7163947B2 (en) * 2003-03-07 2007-01-16 3M Innovative Properties Company 1-Amino 1H-imidazoquinolines
US20040176367A1 (en) * 2003-03-07 2004-09-09 3M Innovative Properties Company 1-Amino 1H-imidazoquinolines
US7699057B2 (en) * 2003-03-13 2010-04-20 3M Innovative Properties Company Methods for treating skin lesions
EP1603476A4 (en) 2003-03-13 2010-01-13 3M Innovative Properties Co Method of tattoo removal
JP4891066B2 (en) * 2003-03-13 2012-03-07 スリーエム イノベイティブ プロパティズ カンパニー How to improve skin quality
US20040192585A1 (en) * 2003-03-25 2004-09-30 3M Innovative Properties Company Treatment for basal cell carcinoma
EP1613956A2 (en) * 2003-03-25 2006-01-11 3M Innovative Properties Company Selective activation of cellular activities mediated through a common toll-like receptor
US20040265351A1 (en) * 2003-04-10 2004-12-30 Miller Richard L. Methods and compositions for enhancing immune response
WO2004108072A2 (en) * 2003-04-10 2004-12-16 3M Innovative Properties Company Delivery of immune response modifier compounds using metal-containing particulate support materials
US20050032829A1 (en) * 2003-06-06 2005-02-10 3M Innovative Properties Company Process for imidazo[4,5-c]pyridin-4-amines
US6943255B2 (en) * 2003-06-06 2005-09-13 3M Innovative Properties Company Process for imidazo[4,5-c]pyridin-4-amines
MY157827A (en) * 2003-06-27 2016-07-29 3M Innovative Properties Co Sulfonamide substituted imidazoquinolines
AU2004261987A1 (en) * 2003-07-31 2005-02-10 3M Innovative Properties Company Compositions for encapsulation and controlled release
WO2005016273A2 (en) * 2003-08-05 2005-02-24 3M Innovative Properties Company Infection prophylaxis using immune response modifier compounds
WO2005018556A2 (en) * 2003-08-12 2005-03-03 3M Innovative Properties Company Hydroxylamine substituted imidazo-containing compounds
EP1653959B1 (en) * 2003-08-14 2015-05-27 3M Innovative Properties Company Lipid-modified immune response modifiers
JP4913593B2 (en) * 2003-08-14 2012-04-11 スリーエム イノベイティブ プロパティズ カンパニー Lipid-modified immune response modifier
WO2005020912A2 (en) 2003-08-25 2005-03-10 3M Innovative Properties Company Delivery of immune response modifier compounds
CA2551075A1 (en) * 2003-08-25 2005-03-03 3M Innovative Properties Company Immunostimulatory combinations and treatments
RU2006105101A (en) * 2003-08-27 2007-10-10 3М Инновейтив Пропертиз Компани (US) Aryloxy and arylalkylene-substituted substituted imidazoquinolines
AU2004268665A1 (en) * 2003-09-02 2005-03-10 3M Innovative Properties Company Methods related to the treatment of mucosal associated conditions
AU2004270201A1 (en) 2003-09-05 2005-03-17 3M Innovative Properties Company Treatment for CD5+ B cell lymphoma
EP1664342A4 (en) * 2003-09-17 2007-12-26 3M Innovative Properties Co Selective modulation of tlr gene expression
AU2004315876B2 (en) 2003-10-03 2011-05-26 3M Innovative Properties Company Pyrazolopyridines and analogs thereof
US7544697B2 (en) 2003-10-03 2009-06-09 Coley Pharmaceutical Group, Inc. Pyrazolopyridines and analogs thereof
KR101154101B1 (en) 2003-10-03 2012-06-11 쓰리엠 이노베이티브 프로퍼티즈 컴파니 Alkoxy substituted imidazoquinolines
US20050096259A1 (en) * 2003-10-31 2005-05-05 3M Innovative Properties Company Neutrophil activation by immune response modifier compounds
JP2007511527A (en) * 2003-11-14 2007-05-10 スリーエム イノベイティブ プロパティズ カンパニー Oxime-substituted imidazo ring compounds
CN1906192A (en) 2003-11-14 2007-01-31 3M创新有限公司 Hydroxylamine substituted imidazo ring compounds
BRPI0416801A (en) * 2003-11-21 2007-01-09 Novartis Ag 1h-imidazoquinoline derivatives as protein synase inhibitors
AR046845A1 (en) * 2003-11-21 2005-12-28 Novartis Ag DERIVATIVES OF 1H-IMIDAZO [4,5-C] QUINOLINE FOR THE TREATMENT OF PROTEIN-KINASE DEPENDENT DISEASES
NZ547467A (en) 2003-11-25 2010-06-25 3M Innovative Properties Co Substituted imidazo ring system and methods
AU2004293096A1 (en) * 2003-11-25 2005-06-09 3M Innovative Properties Company Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines
US20050226878A1 (en) * 2003-12-02 2005-10-13 3M Innovative Properties Company Therapeutic combinations and methods including IRM compounds
EP1689361A4 (en) * 2003-12-02 2009-06-17 3M Innovative Properties Co Therapeutic combinations and methods including irm compounds
AR048289A1 (en) * 2003-12-04 2006-04-19 3M Innovative Properties Co ETERES OF RING IMIDAZO SULFONA REPLACED.
EP1701955A1 (en) 2003-12-29 2006-09-20 3M Innovative Properties Company Arylalkenyl and arylalkynyl substituted imidazoquinolines
AU2004312510A1 (en) * 2003-12-29 2005-07-21 3M Innovative Properties Company Piperazine, [1,4]diazepane, [1,4]diazocane, and [1,5]diazocane fused imidazo ring compounds
WO2005065678A1 (en) * 2003-12-30 2005-07-21 3M Innovative Properties Company Immunomodulatory combinations
EP1699788A2 (en) * 2003-12-30 2006-09-13 3M Innovative Properties Company Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides
JP4991520B2 (en) 2004-03-15 2012-08-01 スリーエム イノベイティブ プロパティズ カンパニー Immune response modulator formulation and method
US8697873B2 (en) 2004-03-24 2014-04-15 3M Innovative Properties Company Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines
CN1938307B (en) 2004-03-26 2010-06-16 大日本住友制药株式会社 9-substituted 8-oxoadenine compound
JP2007532572A (en) * 2004-04-09 2007-11-15 スリーエム イノベイティブ プロパティズ カンパニー Methods, compositions and preparations for delivering immune response modifiers
EP1755665A4 (en) * 2004-04-28 2010-03-03 3M Innovative Properties Co Compositions and methods for mucosal vaccination
TW200600492A (en) * 2004-05-18 2006-01-01 Achillion Pharmaceuticals Inc Substituted aryl acylthioureas and related compounds; inhibitors of viral replication
US20080015184A1 (en) * 2004-06-14 2008-01-17 3M Innovative Properties Company Urea Substituted Imidazopyridines, Imidazoquinolines, and Imidazonaphthyridines
US8017779B2 (en) 2004-06-15 2011-09-13 3M Innovative Properties Company Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
WO2006009826A1 (en) 2004-06-18 2006-01-26 3M Innovative Properties Company Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines
US7884207B2 (en) * 2004-06-18 2011-02-08 3M Innovative Properties Company Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines
US7915281B2 (en) 2004-06-18 2011-03-29 3M Innovative Properties Company Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method
WO2006009832A1 (en) * 2004-06-18 2006-01-26 3M Innovative Properties Company Substituted imidazo ring systems and methods
US7897609B2 (en) 2004-06-18 2011-03-01 3M Innovative Properties Company Aryl substituted imidazonaphthyridines
US8541438B2 (en) 2004-06-18 2013-09-24 3M Innovative Properties Company Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines
US20060045886A1 (en) * 2004-08-27 2006-03-02 Kedl Ross M HIV immunostimulatory compositions
WO2006028962A2 (en) * 2004-09-02 2006-03-16 3M Innovative Properties Company 1-alkoxy 1h-imidazo ring systems and methods
WO2006029115A2 (en) 2004-09-02 2006-03-16 3M Innovative Properties Company 2-amino 1h imidazo ring systems and methods
US20080193468A1 (en) * 2004-09-08 2008-08-14 Children's Medical Center Corporation Method for Stimulating the Immune Response of Newborns
WO2006042254A2 (en) * 2004-10-08 2006-04-20 3M Innovative Properties Company Adjuvant for dna vaccines
US8080560B2 (en) * 2004-12-17 2011-12-20 3M Innovative Properties Company Immune response modifier formulations containing oleic acid and methods
AR052447A1 (en) * 2004-12-30 2007-03-21 3M Innovative Properties Co 1- (2-METIPROPIL) ETANSULFONATE -1H-IMIDAZO [4,5-C] [1,5] NAFTIRIDIN-4- AMINA AND 1- (2- METIPROPIL) -1H-IMIDAZO [4,5-C ] [1,5] NAFTIRIDIN-4-AMINA
US8436176B2 (en) * 2004-12-30 2013-05-07 Medicis Pharmaceutical Corporation Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine
EP1830876B1 (en) 2004-12-30 2015-04-08 Meda AB Use of imiquimod for the treatment of cutaneous metastases derived from a breast cancer tumor
AU2005326708C1 (en) 2004-12-30 2012-08-30 3M Innovative Properties Company Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds
JP5543068B2 (en) 2004-12-30 2014-07-09 スリーエム イノベイティブ プロパティズ カンパニー Chiral fused [1,2] imidazo [4,5-c] cyclic compound
US20080119508A1 (en) * 2004-12-30 2008-05-22 3M Innovative Properties Company Multi-Route Administration Of Immune Response Modifier Compounds
WO2006084251A2 (en) 2005-02-04 2006-08-10 Coley Pharmaceutical Group, Inc. Aqueous gel formulations containing immune reponse modifiers
AU2006338521A1 (en) 2005-02-09 2007-10-11 Coley Pharmaceutical Group, Inc. Oxime and hydroxylamine substituted thiazolo(4,5-c) ring compounds and methods
WO2006086449A2 (en) * 2005-02-09 2006-08-17 Coley Pharmaceutical Group, Inc. Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines
US7968563B2 (en) 2005-02-11 2011-06-28 3M Innovative Properties Company Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods
WO2006091394A2 (en) 2005-02-11 2006-08-31 Coley Pharmaceutical Group, Inc. Substituted imidazoquinolines and imidazonaphthyridines
AU2006216844B2 (en) 2005-02-18 2012-11-08 Novartis Vaccines And Diagnostics S.R.L. Immunogens from uropathogenic escherichia coli
EP1858920B1 (en) 2005-02-18 2016-02-03 GlaxoSmithKline Biologicals SA Proteins and nucleic acids from meningitis/sepsis-associated escherichia coli
CA2598639A1 (en) 2005-02-23 2006-08-31 Coley Pharmaceutical Group, Inc. Hydroxyalkyl substituted imidazonaphthyridines
US8846710B2 (en) 2005-02-23 2014-09-30 3M Innovative Properties Company Method of preferentially inducing the biosynthesis of interferon
AU2006216798A1 (en) 2005-02-23 2006-08-31 Coley Pharmaceutical Group, Inc. Hydroxyalkyl substituted imidazoquinoline compounds and methods
AU2006223634A1 (en) 2005-02-23 2006-09-21 Coley Pharmaceutical Group, Inc. Hydroxyalkyl substituted imidazoquinolines
WO2006099275A2 (en) 2005-03-14 2006-09-21 3M Innovative Properties Company Method of treating actinic keratosis
EP1863814A1 (en) 2005-04-01 2007-12-12 Coley Pharmaceutical Group, Inc. 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases
WO2006107853A2 (en) 2005-04-01 2006-10-12 Coley Pharmaceutical Group, Inc. Pyrazolopyridine-1,4-diamines and analogs thereof
AU2006241166A1 (en) * 2005-04-25 2006-11-02 3M Innovative Properties Company Immunostimulatory compositions
CA2615626A1 (en) 2005-07-18 2007-01-25 Novartis Ag Small animal model for hcv replication
ZA200803029B (en) 2005-09-09 2009-02-25 Coley Pharm Group Inc Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods
AU2006287270A1 (en) 2005-09-09 2007-03-15 Coley Pharmaceutical Group, Inc. Amide and carbamate derivatives of N-{2-[4-amino-2- (ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods
US8889154B2 (en) 2005-09-15 2014-11-18 Medicis Pharmaceutical Corporation Packaging for 1-(2-methylpropyl)-1H-imidazo[4,5-c] quinolin-4-amine-containing formulation
TW200801003A (en) * 2005-09-16 2008-01-01 Astrazeneca Ab Novel compounds
KR20080083270A (en) 2005-11-04 2008-09-17 콜레이 파마시티컬 그룹, 인코포레이티드 Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods
EP1951299B1 (en) 2005-11-04 2012-01-04 Novartis Vaccines and Diagnostics S.r.l. Influenza vaccines including combinations of particulate adjuvants and immunopotentiators
US20090304742A1 (en) 2005-11-04 2009-12-10 Novartis Vaccines And Diagnostics Srl Influenza vaccines with reduced amount of emulsion adjuvant
JP2009514838A (en) 2005-11-04 2009-04-09 ノバルティス ヴァクシンズ アンド ダイアグノスティクス エスアールエル Adjuvant vaccine containing non-virion antigen prepared from influenza virus grown in cell culture
JP2009514839A (en) 2005-11-04 2009-04-09 ノバルティス ヴァクシンズ アンド ダイアグノスティクス エスアールエル Adjuvant influenza vaccine containing cytokine inducer
WO2007079203A2 (en) * 2005-12-28 2007-07-12 3M Innovative Properties Company Treatment for cutaneous t cell lymphoma
KR20110110853A (en) 2006-01-27 2011-10-07 노파르티스 파르마 아게 Influenza vaccines containing hemagglutinin and matrix proteins
EP3085373A1 (en) 2006-02-22 2016-10-26 3M Innovative Properties Company Immune response modifier conjugates
WO2007106854A2 (en) 2006-03-15 2007-09-20 Coley Pharmaceutical Group, Inc. Hydroxy and alkoxy substituted 1h-imidazonaphthyridines and methods
EP2295411A1 (en) * 2006-03-22 2011-03-16 F. Hoffmann-La Roche AG Pyrazoles as 11-beta-hsd-1
EP2357184B1 (en) 2006-03-23 2015-02-25 Novartis AG Imidazoquinoxaline compounds as immunomodulators
US8063063B2 (en) * 2006-03-23 2011-11-22 Novartis Ag Immunopotentiating compounds
WO2007109810A2 (en) * 2006-03-23 2007-09-27 Novartis Ag Methods for the preparation of imidazole-containing compounds
CA2646349A1 (en) 2006-03-24 2007-10-04 Novartis Vaccines And Diagnostics Gmbh & Co Kg Storage of influenza vaccines without refrigeration
WO2007126825A2 (en) 2006-03-31 2007-11-08 Novartis Ag Combined mucosal and parenteral immunization against hiv
WO2008020335A2 (en) 2006-06-09 2008-02-21 Novartis Ag Immunogenic compositions for streptococcus agalactiae
WO2007147529A2 (en) * 2006-06-20 2007-12-27 Transgene S.A. Recombinant viral vaccine
EP2041135A4 (en) 2006-07-05 2010-12-01 Astrazeneca Ab 8-oxoadenine derivatives acting as modulators of tlr7
WO2008008432A2 (en) 2006-07-12 2008-01-17 Coley Pharmaceutical Group, Inc. Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods
GB0614460D0 (en) 2006-07-20 2006-08-30 Novartis Ag Vaccines
JP2010500399A (en) 2006-08-16 2010-01-07 ノバルティス アーゲー Immunogen from Urinary Pathogenic Escherichia coli
US8178539B2 (en) 2006-09-06 2012-05-15 3M Innovative Properties Company Substituted 3,4,6,7-tetrahydro-5H-1,2a,4a,8-tetraazacyclopenta[cd]phenalenes and methods
AU2007297178B2 (en) 2006-09-11 2014-07-24 Novartis Ag Making influenza virus vaccines without using eggs
AU2007327807A1 (en) * 2006-12-05 2008-06-12 Transgene S.A. Means and method for raising improved immune response
AU2007330494B2 (en) 2006-12-06 2014-03-13 Seqirus UK Limited Vaccines including antigen from four strains of influenza virus
TW200831105A (en) 2006-12-14 2008-08-01 Astrazeneca Ab Novel compounds
US20080149123A1 (en) 2006-12-22 2008-06-26 Mckay William D Particulate material dispensing hairbrush with combination bristles
DK2102192T3 (en) 2006-12-29 2013-03-04 Il Yang Pharmaceutical Company Ltd Racemic ilaprazole in solid form
GB0700562D0 (en) 2007-01-11 2007-02-21 Novartis Vaccines & Diagnostic Modified Saccharides
US8063051B2 (en) 2007-03-19 2011-11-22 Astrazeneca Ab 9-substituted-8-oxo-adenine compounds as toll-like receptor (TLR7) modulators
EP2132209B8 (en) 2007-03-19 2014-04-16 AstraZeneca AB 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7 ) modulators
WO2008114819A1 (en) 2007-03-20 2008-09-25 Dainippon Sumitomo Pharma Co., Ltd. Novel adenine compound
PE20081887A1 (en) * 2007-03-20 2009-01-16 Dainippon Sumitomo Pharma Co NEW ADENINE COMPOUND
RU2475487C2 (en) * 2007-05-08 2013-02-20 Астразенека Аб Imidazochinolines with immunomodulating properties
NZ582595A (en) 2007-06-27 2012-07-27 Novartis Ag Low-additive influenza vaccines
GB0714963D0 (en) 2007-08-01 2007-09-12 Novartis Ag Compositions comprising antigens
GB0810305D0 (en) 2008-06-05 2008-07-09 Novartis Ag Influenza vaccination
UY31531A1 (en) 2007-12-17 2009-08-03 SALTS DERIVED FROM 8-OXOADENINE PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND THEIR USE IN THERAPY AS TOLL TYPE RECEIVER MODULATORS (TLR)
GB0818453D0 (en) 2008-10-08 2008-11-12 Novartis Ag Fermentation processes for cultivating streptococci and purification processes for obtaining cps therefrom
EP2268309B1 (en) 2008-03-18 2015-01-21 Novartis AG Improvements in preparation of influenza virus vaccine antigens
BRPI1006901A2 (en) 2009-01-20 2016-02-16 Transgène S A ex vivo method and kit for testing if a patient will respond therapeutically to a treatment method, and use of sicam-1 levels in a blood sample
CN102438650A (en) 2009-03-06 2012-05-02 诺华有限公司 Chlamydia antigens
SG174507A1 (en) 2009-03-24 2011-10-28 Transgene Sa Biomarker for monitoring patients
KR101856462B1 (en) 2009-03-25 2018-05-10 보드 오브 리전츠, 더 유니버시티 오브 텍사스 시스템 Compositions for stimulation of mammalian innate immune resistance to pathogens
WO2010119343A2 (en) 2009-04-14 2010-10-21 Novartis Ag Compositions for immunising against staphylococcus aureus
WO2010119003A1 (en) 2009-04-17 2010-10-21 Transgene Sa Biomarker for monitoring patients
USH2284H1 (en) 2009-04-27 2013-09-03 Novartis Ag Vaccines for protecting against influenza
DK2452194T3 (en) 2009-07-10 2015-11-30 Transgene Sa Biomarker PATIENT SELECTION AND RELATED PRACTICES
HRP20220756T1 (en) 2009-07-15 2022-09-02 Glaxosmithkline Biologicals S.A. Rsv f protein compositions and methods for making same
MX2012000734A (en) 2009-07-16 2012-01-27 Novartis Ag Detoxified escherichia coli immunogens.
US20110033515A1 (en) * 2009-08-04 2011-02-10 Rst Implanted Cell Technology Tissue contacting material
GB0918392D0 (en) 2009-10-20 2009-12-02 Novartis Ag Diagnostic and therapeutic methods
GB0919690D0 (en) 2009-11-10 2009-12-23 Guy S And St Thomas S Nhs Foun compositions for immunising against staphylococcus aureus
JP2013512859A (en) * 2009-12-03 2013-04-18 大日本住友製薬株式会社 Imidazoquinoline acting through a toll-like receptor (TLR)
KR20180099900A (en) 2010-05-26 2018-09-05 셀렉타 바이오사이언시즈, 인크. Dose selection of adjuvanted synthetic nanocarriers
GB201009861D0 (en) 2010-06-11 2010-07-21 Novartis Ag OMV vaccines
EP3222621B1 (en) 2010-08-17 2023-03-08 3M Innovative Properties Company Lipidated immune response modifier compound and its medical use
US9994443B2 (en) 2010-11-05 2018-06-12 Selecta Biosciences, Inc. Modified nicotinic compounds and related methods
ES2575688T3 (en) 2010-12-16 2016-06-30 Sumitomo Dainippon Pharma Co., Ltd. Imidazo [4,5-c] quinolin-1-yl derivative useful in therapy
US8895570B2 (en) 2010-12-17 2014-11-25 Astrazeneca Ab Purine derivatives
EP4159232A1 (en) 2011-01-26 2023-04-05 GlaxoSmithKline Biologicals S.A. Rsv immunization regimen
HUE034673T2 (en) 2011-05-13 2018-02-28 Glaxosmithkline Biologicals Sa Pre-fusion rsv f antigens
US8728486B2 (en) 2011-05-18 2014-05-20 University Of Kansas Toll-like receptor-7 and -8 modulatory 1H imidazoquinoline derived compounds
AU2012261959B2 (en) 2011-06-03 2015-12-03 Solventum Intellectual Properties Company Hydrazino 1H-imidazoquinolin-4-amines and conjugates made therefrom
WO2012167088A1 (en) 2011-06-03 2012-12-06 3M Innovative Properties Company Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom
WO2012174549A2 (en) * 2011-06-16 2012-12-20 Children's Hospital Medical Center Blockade of eosinophil production by toll-like receptors
US20130023736A1 (en) 2011-07-21 2013-01-24 Stanley Dale Harpstead Systems for drug delivery and monitoring
JP6170932B2 (en) 2011-11-07 2017-07-26 ノバルティス アーゲー Carrier molecule comprising spr0096 antigen and spr2021 antigen
WO2013108272A2 (en) 2012-01-20 2013-07-25 International Centre For Genetic Engineering And Biotechnology Blood stage malaria vaccine
SI2844282T1 (en) 2012-05-04 2019-08-30 Pfizer Inc. Prostate-associated antigens and vaccine-based immunotherapy regimens
CN112587671A (en) 2012-07-18 2021-04-02 博笛生物科技有限公司 Targeted immunotherapy for cancer
RU2669941C2 (en) 2013-01-07 2018-10-17 Дзе Трастиз Оф Дзе Юниверсити Оф Пенсильвания Compositions and methods for treating cutaneous t-cell lymphoma
US9919029B2 (en) 2013-07-26 2018-03-20 Inserm (Institut National De La Sante Et De La Recherche Medicale) Methods and pharmaceutical compositions for the treatment of bacterial infections
AU2014347059B2 (en) 2013-11-05 2017-09-07 Solventum Intellectual Properties Company Sesame oil based injection formulations
EP2870974A1 (en) 2013-11-08 2015-05-13 Novartis AG Salmonella conjugate vaccines
EP3092254A4 (en) 2014-01-10 2017-09-20 Birdie Biopharmaceuticals Inc. Compounds and compositions for treating her2 positive tumors
PL3122378T3 (en) 2014-03-26 2020-06-01 Glaxosmithkline Biologicals S.A. Mutant staphylococcal antigens
CN112546230A (en) 2014-07-09 2021-03-26 博笛生物科技有限公司 Combination therapeutic compositions and combination therapeutic methods for treating cancer
CA2954446A1 (en) 2014-07-09 2016-01-14 Shanghai Birdie Biotech, Inc. Anti-pd-l1 combinations for treating tumors
CN112587672A (en) 2014-09-01 2021-04-02 博笛生物科技有限公司 anti-PD-L1 conjugates for the treatment of tumors
WO2016044839A2 (en) 2014-09-19 2016-03-24 The Board Of Regents Of The University Of Texas System Compositions and methods for treating viral infections through stimulated innate immunity in combination with antiviral compounds
WO2016180852A1 (en) 2015-05-12 2016-11-17 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods for preparing antigen-specific t cells from an umbilical cord blood sample
WO2016187459A1 (en) 2015-05-20 2016-11-24 The Regents Of The University Of California Method for generating human dendritic cells for immunotherapy
JP6956071B2 (en) 2015-08-31 2021-10-27 スリーエム イノベイティブ プロパティズ カンパニー Imidazo [4,5-c] cyclic compound containing a substituted guanidine group
WO2017040233A1 (en) 2015-08-31 2017-03-09 3M Innovative Properties Company GUANIDINE SUBSTITUTED IMIDAZO[4,5-c] RING COMPOUNDS
WO2017059280A1 (en) 2015-10-02 2017-04-06 The University Of North Carolina At Chapel Hill Novel pan-tam inhibitors and mer/axl dual inhibitors
TWI812584B (en) 2015-10-30 2023-08-21 美國加利福尼亞大學董事會 Methods of generating t-cells from stem cells and immunotherapeutic methods using the t-cells
CN115554406A (en) 2016-01-07 2023-01-03 博笛生物科技有限公司 anti-CD 20 combinations for the treatment of tumors
CN106943597A (en) 2016-01-07 2017-07-14 博笛生物科技（北京）有限公司 Anti-EGFR for treating tumour is combined
CN106943598A (en) 2016-01-07 2017-07-14 博笛生物科技（北京）有限公司 Anti- HER2 for treating tumour is combined
EP4059570A1 (en) 2016-01-13 2022-09-21 Children's Hospital Medical Center Compositions and methods for treating allergic inflammatory conditions
KR102590454B1 (en) 2016-07-07 2023-10-17 더 보드 어브 트러스티스 어브 더 리랜드 스탠포드 주니어 유니버시티 Antibody-Adjuvant Conjugate
EP3504215B1 (en) 2016-08-26 2022-04-06 3M Innovative Properties Company Fused [1,2]imidazo[4,5-c]ring compounds substituted with guanidino groups
CN110234401B (en) 2016-11-09 2024-03-01 德克萨斯大学系统董事会 Methods and compositions for adaptive immunomodulation
US10766896B2 (en) 2017-03-01 2020-09-08 3M Innovative Properties Company Imidazo[4,5-c] ring compounds containing guanidine substituted benzamide groups
CN108794467A (en) 2017-04-27 2018-11-13 博笛生物科技有限公司 2- amino-quinoline derivatives
WO2018232725A1 (en) 2017-06-23 2018-12-27 Birdie Biopharmaceuticals, Inc. Pharmaceutical compositions
EP3728255B1 (en) 2017-12-20 2022-01-26 3M Innovative Properties Company Amide substituted imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier
US11859250B1 (en) 2018-02-23 2024-01-02 Children's Hospital Medical Center Methods for treating eosinophilic esophagitis
CN111788202B (en) 2018-02-28 2024-03-01 3M创新有限公司 Substituted imidazo [4,5-c ] quinoline compounds with N-1 branched groups
RU2020128440A (en) 2018-02-28 2022-03-28 Пфайзер Инк. IL-15 OPTIONS AND THEIR APPLICATIONS
US11525010B2 (en) 2018-05-23 2022-12-13 Pfizer Inc. Antibodies specific for GUCY2c and uses thereof
PE20210127A1 (en) 2018-05-23 2021-01-19 Pfizer CD3 SPECIFIC ANTIBODIES AND THEIR USES
CN112218864B (en) 2018-05-24 2023-09-08 3M创新有限公司 N-1 branched cycloalkyl substituted imidazo [4,5-c ] quinoline compounds, compositions and methods
EP3887369A1 (en) 2018-11-26 2021-10-06 3M Innovative Properties Company N-1 branched alkyl ether substituted imidazo[4,5-c]quinoline compounds, compositions, and methods
WO2020128893A1 (en) 2018-12-21 2020-06-25 Pfizer Inc. Combination treatments of cancer comprising a tlr agonist
CA3128081A1 (en) 2019-02-12 2020-08-20 Ambrx, Inc. Compositions containing, methods and uses of antibody-tlr agonist conjugates
CA3130794A1 (en) 2019-03-15 2020-09-24 Bolt Biotherapeutics, Inc. Immunoconjugates targeting her2
US20220177471A1 (en) 2019-06-06 2022-06-09 3M Innovative Properties Company N-1 branched alkyl substituted imidazo[4,5-c]quinoline compounds, compositions, and methods
WO2020250089A1 (en) 2019-06-12 2020-12-17 3M Innovative Properties Company Phenethyl substituted imidazo[4,5-c]quinoline compounds with an n-1 branched group
WO2021116420A1 (en) 2019-12-13 2021-06-17 INSERM (Institut National de la Santé et de la Recherche Médicale) Use of tlr7 and/or tlr8 agonists for the treatment of leptospirosis
KR20220114049A (en) 2019-12-17 2022-08-17 화이자 인코포레이티드 Antibodies specific for CD47, PD-L1, and uses thereof
PE20231565A1 (en) 2020-07-17 2023-10-04 Pfizer THERAPEUTIC ANTIBODIES AND THEIR USES
AU2021327396A1 (en) 2020-08-20 2023-03-23 Ambrx, Inc. Antibody-TLR agonist conjugates, methods and uses thereof

Family Cites Families (104)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3314941A (en) 1964-06-23 1967-04-18 American Cyanamid Co Novel substituted pyridodiazepins
US3692907A (en) * 1970-10-27 1972-09-19 Richardson Merrell Inc Treating viral infections with bis-basic ethers and thioethers of fluorenone and fluorene and pharmaceutical compositons of the same
US3917624A (en) 1972-09-27 1975-11-04 Pfizer Process for producing 2-amino-nicotinonitrile intermediates
IL73534A (en) 1983-11-18 1990-12-23 Riker Laboratories Inc 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds
ZA848968B (en) 1983-11-18 1986-06-25 Riker Laboratories Inc 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines
US4775674A (en) 1986-05-23 1988-10-04 Bristol-Myers Company Imidazoquinolinylether derivatives useful as phosphodiesterase and blood aggregation inhibitors
US5500228A (en) * 1987-05-26 1996-03-19 American Cyanamid Company Phase separation-microencapsulated pharmaceuticals compositions useful for alleviating dental disease
US5238944A (en) * 1988-12-15 1993-08-24 Riker Laboratories, Inc. Topical formulations and transdermal delivery systems containing 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
US5756747A (en) * 1989-02-27 1998-05-26 Riker Laboratories, Inc. 1H-imidazo 4,5-c!quinolin-4-amines
US4929624A (en) 1989-03-23 1990-05-29 Minnesota Mining And Manufacturing Company Olefinic 1H-imidazo(4,5-c)quinolin-4-amines
US5037986A (en) 1989-03-23 1991-08-06 Minnesota Mining And Manufacturing Company Olefinic 1H-imidazo[4,5-c]quinolin-4-amines
NZ232740A (en) 1989-04-20 1992-06-25 Riker Laboratories Inc Solution for parenteral administration comprising a 1h-imidazo(4,5-c) quinolin-4-amine derivative, an acid and a tonicity adjuster
US4988815A (en) * 1989-10-26 1991-01-29 Riker Laboratories, Inc. 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines
US5750134A (en) * 1989-11-03 1998-05-12 Riker Laboratories, Inc. Bioadhesive composition and patch
WO1992006093A1 (en) * 1990-10-05 1992-04-16 Minnesota Mining And Manufacturing Company Process for the preparation of imidazo[4,5-c]quinolin-4-amines
US5977306A (en) 1991-02-12 1999-11-02 Heska Corporation Parasitic helminth P39 proteins, and uses thereof
US5175296A (en) * 1991-03-01 1992-12-29 Minnesota Mining And Manufacturing Company Imidazo[4,5-c]quinolin-4-amines and processes for their preparation
US5389640A (en) 1991-03-01 1995-02-14 Minnesota Mining And Manufacturing Company 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines
US5268376A (en) * 1991-09-04 1993-12-07 Minnesota Mining And Manufacturing Company 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines
US5266575A (en) 1991-11-06 1993-11-30 Minnesota Mining And Manufacturing Company 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines
IL105325A (en) * 1992-04-16 1996-11-14 Minnesota Mining & Mfg Immunogen/vaccine adjuvant composition
WO1993023011A1 (en) * 1992-05-18 1993-11-25 Minnesota Mining And Manufacturing Company Transmucosal drug delivery device
US5395937A (en) * 1993-01-29 1995-03-07 Minnesota Mining And Manufacturing Company Process for preparing quinoline amines
KR100341341B1 (en) 1993-07-15 2002-11-25 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 IMIDAZO[4,5-c]PYRIDIN-4-AMINES
US5352784A (en) 1993-07-15 1994-10-04 Minnesota Mining And Manufacturing Company Fused cycloalkylimidazopyridines
US5648516A (en) 1994-07-20 1997-07-15 Minnesota Mining And Manufacturing Company Fused cycloalkylimidazopyridines
US5644063A (en) 1994-09-08 1997-07-01 Minnesota Mining And Manufacturing Company Imidazo[4,5-c]pyridin-4-amine intermediates
GB9420168D0 (en) * 1994-10-06 1994-11-23 Boots Co Plc Therapeutic agents
US5482936A (en) 1995-01-12 1996-01-09 Minnesota Mining And Manufacturing Company Imidazo[4,5-C]quinoline amines
US5585612A (en) 1995-03-20 1996-12-17 Harp Enterprises, Inc. Method and apparatus for voting
JPH09208584A (en) 1996-01-29 1997-08-12 Terumo Corp Amide derivative, pharmaceutical preparation containing the same, and intermediate for synthesizing the same
JPH09255926A (en) 1996-03-26 1997-09-30 Diatex Co Ltd Pressure-sensitive tape
US5939047A (en) * 1996-04-16 1999-08-17 Jernberg; Gary R. Local delivery of chemotherapeutic agents for treatment of periodontal disease
US5693811A (en) * 1996-06-21 1997-12-02 Minnesota Mining And Manufacturing Company Process for preparing tetrahdroimidazoquinolinamines
US5741908A (en) * 1996-06-21 1998-04-21 Minnesota Mining And Manufacturing Company Process for reparing imidazoquinolinamines
JP4391592B2 (en) * 1996-10-25 2009-12-24 スリーエム カンパニー Immune response modifying compounds for the treatment of TH2-mediated and related diseases
US5939090A (en) 1996-12-03 1999-08-17 3M Innovative Properties Company Gel formulations for topical drug delivery
US6069149A (en) 1997-01-09 2000-05-30 Terumo Kabushiki Kaisha Amide derivatives and intermediates for the synthesis thereof
JPH10298181A (en) 1997-04-25 1998-11-10 Sumitomo Pharmaceut Co Ltd Type 2 helper t cell selective immune response inhibitor
US6123957A (en) * 1997-07-16 2000-09-26 Jernberg; Gary R. Delivery of agents and method for regeneration of periodontal tissues
JPH1180156A (en) * 1997-09-04 1999-03-26 Hokuriku Seiyaku Co Ltd 1-(substitutedaryl)alkyl-1h-imidazopyridin-4-amine derivative
JPH11108156A (en) 1997-10-09 1999-04-20 Tochigi Fuji Ind Co Ltd Differential device
UA67760C2 (en) * 1997-12-11 2004-07-15 Міннесота Майнінг Енд Мануфакчурінг Компані Imidazonaphthyridines and use thereof to induce the biosynthesis of cytokines
JPH11222432A (en) 1998-02-03 1999-08-17 Terumo Corp Preparation for external use containing amide derivative inducing interferon
US6182186B1 (en) 1998-06-30 2001-01-30 Sun Microsystems, Inc. Method and apparatus that utilizes lock states to lock resources
US6110929A (en) * 1998-07-28 2000-08-29 3M Innovative Properties Company Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof
JP2000119271A (en) 1998-08-12 2000-04-25 Hokuriku Seiyaku Co Ltd 1h-imidazopyridine derivative
CZ20011188A3 (en) 1998-10-02 2001-08-15 3M Innovative Properties Company Mucosal originated drug delivery systems and animal applications
US6486168B1 (en) * 1999-01-08 2002-11-26 3M Innovative Properties Company Formulations and methods for treatment of mucosal associated conditions with an immune response modifier
EP1140091B1 (en) * 1999-01-08 2005-09-21 3M Innovative Properties Company Formulations comprising imiquimod or other immune response modifiers for treating cervical dysplasia
US20020058674A1 (en) * 1999-01-08 2002-05-16 Hedenstrom John C. Systems and methods for treating a mucosal surface
US6558951B1 (en) 1999-02-11 2003-05-06 3M Innovative Properties Company Maturation of dendritic cells with immune response modifying compounds
JP2000247884A (en) 1999-03-01 2000-09-12 Sumitomo Pharmaceut Co Ltd Arachidonic acid-induced skin disease-treating agent
US6541485B1 (en) 1999-06-10 2003-04-01 3M Innovative Properties Company Urea substituted imidazoquinolines
US6331539B1 (en) * 1999-06-10 2001-12-18 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines
US6756382B2 (en) * 1999-06-10 2004-06-29 3M Innovative Properties Company Amide substituted imidazoquinolines
US6573273B1 (en) * 1999-06-10 2003-06-03 3M Innovative Properties Company Urea substituted imidazoquinolines
US6451810B1 (en) * 1999-06-10 2002-09-17 3M Innovative Properties Company Amide substituted imidazoquinolines
US6376669B1 (en) * 1999-11-05 2002-04-23 3M Innovative Properties Company Dye labeled imidazoquinoline compounds
US6894060B2 (en) 2000-03-30 2005-05-17 3M Innovative Properties Company Method for the treatment of dermal lesions caused by envenomation
DE10029580C1 (en) * 2000-06-15 2002-01-10 Ferton Holding Sa Device for removing body stones with an intracorporeal lithotripter
US6610716B2 (en) 2000-07-13 2003-08-26 Alteon Incorporated Cyanomethyl substituted thiazoliums and imidazoliums and treatments of disorders associated with protein aging
US20020055517A1 (en) * 2000-09-15 2002-05-09 3M Innovative Properties Company Methods for delaying recurrence of herpes virus symptoms
JP2002145777A (en) 2000-11-06 2002-05-22 Sumitomo Pharmaceut Co Ltd Therapeutic agent for arachidonic acid-induced dermatosis
DE60126136T8 (en) * 2000-12-07 2008-04-10 Aoyama Seisakusho Co., Ltd., Nagoya METHOD FOR THE THERMAL HEATING OF STEEL PARTS
UA74593C2 (en) 2000-12-08 2006-01-16 3M Innovative Properties Co Substituted imidazopyridines
US6545017B1 (en) * 2000-12-08 2003-04-08 3M Innovative Properties Company Urea substituted imidazopyridines
US6545016B1 (en) * 2000-12-08 2003-04-08 3M Innovative Properties Company Amide substituted imidazopyridines
US6525064B1 (en) * 2000-12-08 2003-02-25 3M Innovative Properties Company Sulfonamido substituted imidazopyridines
US6660747B2 (en) * 2000-12-08 2003-12-09 3M Innovative Properties Company Amido ether substituted imidazoquinolines
AU3249802A (en) * 2000-12-08 2002-06-18 3M Innovative Properties Co Screening method for identifying compounds that selectively induce interferon alpha
UA75622C2 (en) 2000-12-08 2006-05-15 3M Innovative Properties Co Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon
US6660735B2 (en) * 2000-12-08 2003-12-09 3M Innovative Properties Company Urea substituted imidazoquinoline ethers
US6677348B2 (en) * 2000-12-08 2004-01-13 3M Innovative Properties Company Aryl ether substituted imidazoquinolines
JP2002247884A (en) 2001-02-19 2002-08-30 Hitachi Ltd Operation controller for fan motor
CA2458876A1 (en) * 2001-08-30 2003-03-13 3M Innovative Properties Company Methods of maturing plasmacytoid dendritic cells using immune response modifier molecules
US20030139364A1 (en) * 2001-10-12 2003-07-24 University Of Iowa Research Foundation Methods and products for enhancing immune responses using imidazoquinoline compounds
ATE416771T1 (en) * 2001-11-16 2008-12-15 3M Innovative Properties Co N-Ä4-(4-AMINO-2-ETHYL-1H-IMIDAZOÄ4,5-CUCHINOLINE 1-YL)BUTYLUMETHANESULFONAMIDE, PHARMACEUTICAL COMPOSITION CONTAINING SAME AND USE THEREOF
ES2312659T3 (en) * 2001-11-29 2009-03-01 3M Innovative Properties Company PHARMACEUTICAL FORMULATIONS THAT INCLUDE A MODIFIER OF THE IMMUNE RESPONSE.
US6677349B1 (en) * 2001-12-21 2004-01-13 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines
JP2005518433A (en) * 2002-02-22 2005-06-23 スリーエム イノベイティブ プロパティズ カンパニー Methods for reducing and treating UVB-induced immunosuppression
AU2003233519A1 (en) * 2002-05-29 2003-12-19 3M Innovative Properties Company Process for imidazo(4,5-c)pyridin-4-amines
JP2005538057A (en) * 2002-06-07 2005-12-15 スリーエム イノベイティブ プロパティズ カンパニー Ether-substituted imidazopyridine
AU2003299863B2 (en) * 2002-08-15 2009-09-24 3M Innovative Properties Company Immunostimulatory compositions and methods of stimulating an immune response
US6818650B2 (en) * 2002-09-26 2004-11-16 3M Innovative Properties Company 1H-imidazo dimers
AU2003287316A1 (en) * 2002-12-11 2004-06-30 3M Innovative Properties Company Assays relating to toll-like receptor activity
WO2004053057A2 (en) * 2002-12-11 2004-06-24 3M Innovative Properties Company Gene expression systems and recombinant cell lines
CA2510375A1 (en) * 2002-12-20 2004-07-15 3M Innovative Properties Company Aryl / hetaryl substituted imidazoquinolines
WO2004060319A2 (en) * 2002-12-30 2004-07-22 3M Innovative Properties Company Immunostimulatory combinations
WO2004071459A2 (en) * 2003-02-13 2004-08-26 3M Innovative Properties Company Methods and compositions related to irm compounds and toll-like receptor 8
JP2006519020A (en) * 2003-02-27 2006-08-24 スリーエム イノベイティブ プロパティズ カンパニー Selective regulation of TLR-mediated biological activity
WO2004078138A2 (en) * 2003-03-04 2004-09-16 3M Innovative Properties Company Prophylactic treatment of uv-induced epidermal neoplasia
US20040176367A1 (en) * 2003-03-07 2004-09-09 3M Innovative Properties Company 1-Amino 1H-imidazoquinolines
JP4891066B2 (en) * 2003-03-13 2012-03-07 スリーエム イノベイティブ プロパティズ カンパニー How to improve skin quality
EP1603476A4 (en) * 2003-03-13 2010-01-13 3M Innovative Properties Co Method of tattoo removal
US7699057B2 (en) * 2003-03-13 2010-04-20 3M Innovative Properties Company Methods for treating skin lesions
EP1613956A2 (en) * 2003-03-25 2006-01-11 3M Innovative Properties Company Selective activation of cellular activities mediated through a common toll-like receptor
JP2004302671A (en) * 2003-03-28 2004-10-28 Hitachi Software Eng Co Ltd Database search path designating method
WO2004108072A2 (en) * 2003-04-10 2004-12-16 3M Innovative Properties Company Delivery of immune response modifier compounds using metal-containing particulate support materials
US20040214851A1 (en) * 2003-04-28 2004-10-28 3M Innovative Properties Company Compositions and methods for induction of opioid receptors
WO2005016273A2 (en) * 2003-08-05 2005-02-24 3M Innovative Properties Company Infection prophylaxis using immune response modifier compounds
NZ545536A (en) * 2003-09-05 2010-04-30 Anadys Pharmaceuticals Inc TLR7 ligands for the treatment of hepatitis C
US20050226878A1 (en) * 2003-12-02 2005-10-13 3M Innovative Properties Company Therapeutic combinations and methods including IRM compounds
EP1699398A4 (en) * 2003-12-30 2007-10-17 3M Innovative Properties Co Enhancement of immune responses

Also Published As

Publication number Publication date
EP1198233A4 (en) 2002-07-24
CZ303287B6 (en) 2012-07-18
EE200100669A (en) 2003-02-17
CY1108536T1 (en) 2014-04-09
HRP20010890B1 (en) 2011-03-31
TR200103575T2 (en) 2002-06-21
PL352554A1 (en) 2003-08-25
US6800624B2 (en) 2004-10-05
US7030131B2 (en) 2006-04-18
US20040204438A1 (en) 2004-10-14
AU772179B2 (en) 2004-04-08
CN1354663A (en) 2002-06-19
NZ515967A (en) 2003-10-31
BR0011433B1 (en) 2013-10-22
US20060106052A1 (en) 2006-05-18
DE60030126D1 (en) 2006-09-28
CZ20014363A3 (en) 2002-03-13
MXPA01012547A (en) 2003-10-14
US20030130299A1 (en) 2003-07-10
KR100781428B1 (en) 2007-12-03
KR20020010701A (en) 2002-02-04
JP4833466B2 (en) 2011-12-07
CN1249061C (en) 2006-04-05
BR0011433A (en) 2002-03-05
DK1198233T3 (en) 2006-12-04
PL211009B1 (en) 2012-03-30
NO20015502D0 (en) 2001-11-09
UA73503C2 (en) 2005-08-15
EE05074B1 (en) 2008-10-15
NO20015502L (en) 2002-02-07
NO320747B1 (en) 2006-01-23
SK17922001A3 (en) 2002-04-04
HRP20010890A2 (en) 2003-08-31
PT1198233E (en) 2007-01-31
ES2270840T3 (en) 2007-04-16
ATE336249T1 (en) 2006-09-15
DE60030126T2 (en) 2007-03-15
CA2376305C (en) 2010-10-12
SK286418B6 (en) 2008-09-05
US6825350B2 (en) 2004-11-30
EP1198233A1 (en) 2002-04-24
HU229928B1 (en) 2015-01-28
AU5328400A (en) 2001-01-02
RU2248975C2 (en) 2005-03-27
HUP0201431A3 (en) 2002-12-28
HUP0201431A2 (en) 2002-08-28
US6331539B1 (en) 2001-12-18
JP2003501474A (en) 2003-01-14
IL146486A0 (en) 2002-07-25
EP1198233B1 (en) 2006-08-16
US20040029877A1 (en) 2004-02-12
HK1086762A1 (en) 2006-09-29
IL146486A (en) 2010-05-31
WO2000076519A1 (en) 2000-12-21

Similar Documents

Publication Publication Date Title
CA2376305A1 (en) Sulfonamide and sulfamide substituted imidazoquinolines
RU2001132139A (en) Imidazoquinolines with sulfonamide or sulfamide substitution
CA2436846A1 (en) Thioether substituted imidazoquinolines
RU2001132570A (en) Urea-substituted imidazoquinolines
CA2376304A1 (en) Amide substituted imidazoquinolines
RU2003116648A (en) SUBSTITUTED IMIDAZOPYRIDINES
RU2007107189A (en) ARILPYRIDINE DERIVATIVES
RU2007130144A (en) HETEROCYCLIC COMPOUNDS AS CCCR2B ANTAGONISTS
JP2005511745A5 (en)
RU2003134544A (en) AMRIDES OF ANTRANILIC ACID, METHODS FOR PRODUCING THEM, THEIR APPLICATION AS ANTIARRHYTHMIC MEDICINES, AND ALSO CONTAINING THEIR PHARMACEUTICAL COMPOSITIONS
RU2011103741A (en) COMPOSITIONS AND METHODS FOR TREATING RETAIL DISEASES
RU99105567A (en) PROPIONIC ACID DERIVATIVES AND THEIR USE
RU2006130000A (en) ORGANIC COMPOUNDS
EP0382687A3 (en) Benzofused-n-containing heterocycle derivatives
DE3852085D1 (en) Substituted N- (1-alkyl-3-hydroxy-4-piperidinyl) benzamides.
RU2002100058A (en) 1-Methylcarbapenem Crystal Derivatives
RU2004119963A (en) HIV INTEGRAS INHIBITORS
ATE361918T1 (en) 4-(4-METHOXYBENZYL)-N'-(5-NITRO-1,3-THIAZOL-2-YL)UREA AND ITS USE IN THE TREATMENT OF GLYCOGEN SYNTHASE KINASE-3 (GSK3)-ASSOCIATED CONDITIONS
HUP0203884A2 (en) Crystals of an oxyiminoalkanoic acid derivative and their use as antidiabetics and pharmaceutical compositions containing them
RU2003130644A (en) RARCARBOLINE DERIVATIVES AND THEIR PHARMACEUTICAL USE AGAINST DIPRESSION AND FEAR
RU2001126547A (en) Biphenyl derivatives
JP2005522492A5 (en)
ES2203889T3 (en) TREATMENT OF PROTOZO INFECTIONS.
GB1289240A (en)
FI872930A0 (en) Analogous method for the preparation of anti-diarrheal 4- (benzoylamino) piperidinebutanamide derivatives

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20190610