US20030199538A1 - Pharmaceutical formulation comprising an immune response modifier - Google Patents

Pharmaceutical formulation comprising an immune response modifier Download PDF

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Publication number
US20030199538A1
US20030199538A1 US10/306,019 US30601902A US2003199538A1 US 20030199538 A1 US20030199538 A1 US 20030199538A1 US 30601902 A US30601902 A US 30601902A US 2003199538 A1 US2003199538 A1 US 2003199538A1
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Prior art keywords
imidazo
amine
formulation
quinolin
amines
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Raymond Skwierczynski
Terri Busch
Amy Gust-Heiting
Mary Fretland
Matthew Scholz
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3M Innovative Properties Co
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3M Innovative Properties Co
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Priority to US10/306,019 priority Critical patent/US20030199538A1/en
Assigned to 3M INNOVATIVE PROPERTIES COMPANY reassignment 3M INNOVATIVE PROPERTIES COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BUSCH, TERRI F., FRETLAND, MARY, GUST-HEITING, AMY L., SCHOLZ, MATTHEW T., SKWIERCZYNSKI, RAYMOND D.
Publication of US20030199538A1 publication Critical patent/US20030199538A1/en
Priority to US12/172,712 priority patent/US7968562B2/en
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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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4355—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • 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
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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
    • A61P37/02—Immunomodulators

Definitions

  • the present invention is directed to pharmaceutical formulations comprising at least one immune response modifier chosen from imidazoquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, 1,2-bridged imidazoquinoline amines, thiazoloquinoline amines, oxazoloquinoline amines, thiazolopyridine amines, oxazolopyridine amines, imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines.
  • Embodiments of the present invention are directed to topical formulations for application to the skin of a mammal.
  • Other embodiments of the present invention are directed to methods for treating dermal diseases.
  • IRM immune response modifier
  • IRM interferon- ⁇ cytokines
  • IFN interferon
  • TNF tumor necrosis factor
  • IL-1 Interleukin-1
  • IL-6 Interleukin-6
  • the present invention is directed to a pharmaceutical formulation comprising an immune response modifier selected from imidazoquinoline amines, imidazotetrahydroquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, 1,2-bridged imidazoquinoline amines, thiazoloquinoline amines, oxazoloquinoline amines, thiazolopyridine amines, oxazolopyridine amines, imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines; a fatty acid; a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms; and a hydrophilic viscosity enhancing agent selected from cellulose ethers and carbo
  • the pharmaceutical formulation comprises an immune response modifier selected from imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines; a fatty acid; and a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms.
  • an immune response modifier selected from imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines
  • a fatty acid and a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms.
  • the formulation can further comprise one or more of a preservative system, an emulsifier, and water.
  • the present invention is directed to a method of treatment of a dermal associated condition comprising applying to skin a topical formulation comprising an immune response modifier selected from imidazoquinoline amines, imidazotetrahydroquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, 1,2-bridged imidazoquinoline amines, thiazoloquinoline amines, oxazoloquinoline amines, thiazolopyridine amines, oxazolopyridine amines, imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines; a fatty acid; a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms; and a hydrophil
  • the method of treatment of a dermal associated condition comprises applying to skin a formulation comprising an immune response modifier selected from imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines; a fatty acid; and a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms.
  • an immune response modifier selected from imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines
  • a fatty acid and a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms.
  • the method of treatment of a dermal associated condition comprises applying to skin a formulation comprising an immune response modifier selected from imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines; a fatty acid; a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms; and further comprising one or more of a preservative system, an emulsifier, and water.
  • an immune response modifier selected from imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines
  • a fatty acid a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms
  • the dermal associated condition is selected from actinic keratosis, postsurgical scars, basal cell carcinoma, atopic dermatitis, and warts.
  • the present invention is directed to a method for delivering an immune response modifier to a dermal surface, the method comprising the steps of selecting a formulation comprising a compound selected from imidazoquinoline amines, imidazotetrahydroquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, 1,2-bridged imidazoquinoline amines, thiazoloquinoline amines, oxazolo-quinoline amines, thiazolopyridine amines, oxazolopyridine amines, imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines; a fatty acid; a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms;
  • the selected formulation comprises an immune response modifier selected from imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines; a fatty acid; and a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms.
  • an immune response modifier selected from imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines
  • a fatty acid and a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms.
  • the present invention is directed to a formulation comprising an immune response modifier compound selected from imidazoquinoline amines, imidazotetrahydroquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, 1,2-bridged imidazoquinoline amines, thiazoloquinoline amines, oxazoloquinoline amines, thiazolopyridine amines, oxazolopyridine amines, imidazonaphthyridine amines, imidazotetrahydronaphthyridine amines, and thiazolonaphthyridine amines; a fatty acid; a hydrophobic, aprotic component miscible with the fatty acid and comprising a hydrocarbyl group of 7 or more carbon atoms, and a hydrophilic viscosity enhancing agent selected from cellulose ethers and carbo
  • an immune response modifier compound
  • the IRM compound can be chosen from imidazoquinoline amines, for example, 1H-imidazo[4,5-c]quinolin-4-amines defined by one of Formulas I-V below:
  • R 11 is chosen from alkyl of one to ten carbon atoms, hydroxyalkyl of one to six carbon atoms, acyloxyalkyl wherein the acyloxy moiety is alkanoyloxy of two to four carbon atoms or benzoyloxy, and the alkyl moiety contains one to six carbon atoms, benzyl, (phenyl)ethyl and phenyl, said benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently chosen from alkyl of one to four carbon atoms, alkoxy of one to four carbon atoms and halogen, with the proviso that if said benzene ring is substituted by two of said moieties, then said moieties together contain no more than six carbon atoms;
  • R 21 is chosen from hydrogen, alkyl of one to eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently chosen from alkyl of one to four carbon atoms, alkoxy of one to four carbon atoms and halogen, with the proviso that when the benzene ring is substituted by two of said moieties, then the moieties together contain no more than six carbon atoms; and
  • each R 1 is independently chosen from alkoxy of one to four carbon atoms, halogen, and alkyl of one to four carbon atoms, and n is an integer from 0 to 2, with the proviso that if n is 2, then said R 1 groups together contain no more than six carbon atoms;
  • R 12 is chosen from straight chain or branched chain alkenyl containing two to ten carbon atoms and substituted straight chain or branched chain alkenyl containing two to ten carbon atoms, wherein the substituent is chosen from straight chain or branched chain alkyl containing one to four carbon atoms and cycloalkyl containing three to six carbon atoms; and cycloalkyl containing three to six carbon atoms substituted by straight chain or branched chain alkyl containing one to four carbon atoms; and
  • R 22 is chosen from hydrogen, straight chain or branched chain alkyl containing one to eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently chosen from straight chain or branched chain alkyl containing one to four carbon atoms, straight chain or branched chain alkoxy containing one to four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than six carbon atoms; and
  • each R 2 is independently chosen from straight chain or branched chain alkoxy containing one to four carbon atoms, halogen, and straight chain or branched chain alkyl containing one to four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R 2 groups together contain no more than six carbon atoms;
  • R 23 is chosen from hydrogen, straight chain or branched chain alkyl of one to eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently chosen from straight chain or branched chain alkyl of one to four carbon atoms, straight chain or branched chain alkoxy of one to four carbon atoms, and halogen, with the proviso that when the benzene ring is substituted by two such moieties, then the moieties together contain no more than six carbon atoms; and
  • each R 3 is independently chosen from straight chain or branched chain alkoxy of one to four carbon atoms, halogen, and straight chain or branched chain alkyl of one to four carbon atoms, and n is an integer from zero to 2, with the proviso that if n is 2, then said R 3 groups together contain no more than six carbon atoms;
  • R 14 is —CHR x R y wherein R y is hydrogen or a carbon-carbon bond, with the proviso that when R y is hydrogen R x is alkoxy of one to four carbon atoms, hydroxyalkoxy of one to four carbon atoms, 1-alkynyl of two to ten carbon atoms, tetrahydropyranyl, alkoxyalkyl wherein the alkoxy moiety contains one to four carbon atoms and the alkyl moiety contains one to four carbon atoms, or 2-, 3-, or 4-pyridyl, and with the further proviso that when R y is a carbon-carbon bond R y and R x together form a tetrahydrofuranyl group optionally substituted with one or more substituents independently chosen from hydroxy and hydroxyalkyl of one to four carbon atoms;
  • R 24 is chosen from hydrogen, alkyl of one to four carbon atoms, phenyl, and substituted phenyl wherein the substituent is chosen from alkyl of one to four carbon atoms, alkoxy of one to four carbon atoms, and halogen; and
  • R 4 is chosen from hydrogen, straight chain or branched chain alkoxy containing one to four carbon atoms, halogen, and straight chain or branched chain alkyl containing one to four carbon atoms;
  • R 15 is chosen from: hydrogen; straight chain or branched chain alkyl containing one to ten carbon atoms and substituted straight chain or branched chain alkyl containing one to ten carbon atoms, wherein the substituent is chosen from cycloalkyl containing three to six carbon atoms and cycloalkyl containing three to six carbon atoms substituted by straight chain or branched chain alkyl containing one to four carbon atoms; straight chain or branched chain alkenyl containing two to ten carbon atoms and substituted straight chain or branched chain alkenyl containing two to ten carbon atoms, wherein the substituent is chosen from cycloalkyl containing three to six carbon atoms and cycloalkyl containing three to six carbon atoms substituted by straight chain or branched chain alkyl containing one to four carbon atoms; hydroxyalkyl of one to six carbon atoms; alkoxyalkyl wherein the alkoxy moiety contains
  • R 25 is
  • R S and R T are independently chosen from hydrogen, alkyl of one to four carbon atoms, phenyl, and substituted phenyl wherein the substituent is chosen from alkyl of one to four carbon atoms, alkoxy of one to four carbon atoms, and halogen;
  • X is chosen from alkoxy containing one to four carbon atoms, alkoxyalkyl wherein the alkoxy moiety contains one to four carbon atoms and the alkyl moiety contains one to four carbon atoms, hydroxyalkyl of one to four carbon atoms, haloalkyl of one to four carbon atoms, alkylamido wherein the alkyl group contains one to four carbon atoms, amino, substituted amino wherein the substituent is alkyl or hydroxyalkyl of one to four carbon atoms, azido, chloro, hydroxy, 1-morpholino, 1-pyrrolidino, alkylthio of one to four carbon atoms; and
  • R 5 is chosen from hydrogen, straight chain or branched chain alkoxy containing one to four carbon atoms, halogen, and straight chain or branched chain alkyl containing one to four carbon atoms;
  • the IRM compound can also be chosen from 6,7 fused cycloalkylimidazopyridine amines defined by Formula VI below:
  • R 16 is chosen from hydrogen; cyclic alkyl of three, four, or five carbon atoms; straight chain or branched chain alkyl containing one to ten carbon atoms and substituted straight chain or branched chain alkyl containing one to ten carbon atoms, wherein the substituent is chosen from cycloalkyl containing three to six carbon atoms and cycloalkyl containing three to six carbon atoms substituted by straight chain or branched chain alkyl containing one to four carbon atoms; fluoro- or chloroalkyl containing from one to ten carbon atoms and one or more fluorine or chlorine atoms; straight chain or branched chain alkenyl containing two to ten carbon atoms and substituted straight chain or branched chain alkenyl containing two to ten carbon atoms, wherein the substituent is chosen from cycloalkyl containing three to six carbon atoms and cycloalkyl containing three to six carbon atoms substitute
  • R y is hydrogen or a carbon-carbon bond, with the proviso that when R y is hydrogen R x is alkoxy of one to four carbon atoms, hydroxyalkoxy of one to four carbon atoms, 1-alkynyl of two to ten carbon atoms, tetrahydropyranyl, alkoxyalkyl wherein the alkoxy moiety contains one to four carbon atoms and the alkyl moiety contains one to four carbon atoms, or 2-, 3-, or 4-pyridyl, and with the further proviso that when R y is a carbon-carbon bond R y and R x together form a tetrahydrofuranyl group optionally substituted with one or more substituents independently chosen from hydroxy and hydroxyalkyl of one to four carbon atoms,
  • R 26 is chosen from hydrogen, straight chain or branched chain alkyl containing one to eight carbon atoms, straight chain or branched chain hydroxyalkyl containing one to six carbon atoms, morpholinoalkyl, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by a moiety chosen from methyl, methoxy, and halogen; and
  • R S and R T are independently chosen from hydrogen, alkyl of one to four carbon atoms, phenyl, and substituted phenyl wherein the substituent is chosen from alkyl of one to four carbon atoms, alkoxy of one to four carbon atoms, and halogen;
  • X is chosen from alkoxy containing one to four carbon atoms, alkoxyalkyl wherein the alkoxy moiety contains one to four carbon atoms and the alkyl moiety contains one to four carbon atoms, haloalkyl of one to four carbon atoms, alkylamido wherein the alkyl group contains one to four carbon atoms, amino, substituted amino wherein the substituent is alkyl or hydroxyalkyl of one to four carbon atoms, azido, alkylthio of one to four carbon atoms, and morpholinoalkyl wherein the alkyl moiety contains one to four carbon atoms, and
  • R 6 is chosen from hydrogen, fluoro, chloro, straight chain or branched chain alkyl containing one to four carbon atoms, and straight chain or branched chain fluoro- or chloroalkyl containing one to four carbon atoms and at least one fluorine or chlorine atom; and pharmaceutically acceptable salts thereof.
  • the IRM compound can be chosen from imidazopyridine amines defined by Formula VII below:
  • R 17 is chosen from hydrogen; —CH 2 R W wherein R W is chosen from straight chain, branched chain, or cyclic alkyl containing one to ten carbon atoms, straight chain or branched chain alkenyl containing two to ten carbon atoms, straight chain or branched chain hydroxyalkyl containing one to six carbon atoms, alkoxyalkyl wherein the alkoxy moiety contains one to four carbon atoms and the alkyl moiety contains one to six carbon atoms, and phenylethyl; and —CH ⁇ CR Z R Z wherein each R Z is independently straight chain, branched chain, or cyclic alkyl of one to six carbon atoms;
  • R 27 is chosen from hydrogen; straight chain or branched chain alkyl containing one to eight carbon atoms; straight chain or branched chain hydroxyalkyl containing one to six carbon atoms; alkoxyalkyl wherein the alkoxy moiety contains one to four carbon atoms and the alkyl moiety contains one to six carbon atoms; benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl oand phenyl being optionally substituted on the benzene ring by a moiety chosen from methyl, methoxy, and halogen; and morpholinoalkyl wherein the alkyl moiety contains one to four carbon atoms;
  • R 67 and R 77 are independently chosen from hydrogen and alkyl of one to five carbon atoms, with the proviso that R 67 and R 77 taken together contain no more than six carbon atoms, and with the further proviso that when R 77 is hydrogen then R 67 is other than hydrogen and R 27 is other than hydrogen or morpholinoalkyl, and with the further proviso that when R 67 is hydrogen then R 77 and R 27 are other than hydrogen;
  • the IRM compound can be chosen from 1,2-bridged imidazoquinoline amines defined by Formula VIII below:
  • Z is chosen from:
  • R 8 is chosen from alkyl of one to four carbon atoms, alkoxy of one to four carbon atoms, and halogen
  • the IRM compound can be chosen from thiazoloquinoline amines, oxazoloquinoline amines, thiazolonaphthyridine amines, thiazolopyridine amines, and oxazolopyridine amines of Formula IX:
  • R 19 is chosen from oxygen, sulfur and selenium
  • R 29 is chosen from
  • R 39 and R 49 are each independently:
  • R 39 and R 49 form a fused aromatic, heteroaromatic, cycloalkyl or heterocyclic ring;
  • X is chosen from —O—, —S—, —NR 59 —, —C(O)—, —C(O)O—, —OC(O)—, and a bond;
  • each R 59 is independently H or C 1-8 alkyl
  • the IRM compound can be chosen from imidazonaphthyridine amines and imidazotetrahydronaphthyridine amines of Formulae X and XI below:
  • A is ⁇ N—CR ⁇ CR—CR ⁇ ; ⁇ CR—N ⁇ CR—CR—; ⁇ CR—CR ⁇ N—CR ⁇ ; or ⁇ CR—CR ⁇ CR—N ⁇ ;
  • R 110 is chosen from:
  • R 210 is chosen from:
  • each R 310 is independently chosen from hydrogen and C 1-10 alkyl
  • each R is independently chosen from hydrogen, C 1-10 alkyl, C 1-10 alkoxy, halogen and trifluoromethyl,
  • B is —NR—C(R) 2 —C(R) 2 —C(R) 2 —; —C(R) 2 —NR—C(R) 2 —C(R) 2 —; —C(R) 2 —C(R) 2 —NR—C(R) 2 — or —C(R) 2 —C(R) 2 —C(R) 2 —NR—;
  • R 111 is chosen from:
  • R 211 is chosen from:
  • each R 311 is independently chosen from hydrogen and C 1-10 alkyl
  • each R is independently chosen from hydrogen, C 1-10 alkyl, C 1-10 alkoxy, halogen and trifluoromethyl,
  • the IRM compound can be chosen from imidazoquinoline amines and imidazotetrahydroquinoline amines, for example, 1H-imidazo[4,5-c]quinolin-4-amines and tetrahydro-1H-imidazo[4,5-c]quinolin-4-amines defined by Formulas XII, XIII and XIV below:
  • R 112 is -alkyl-NR 312 —CO—R 412 or -alkenyl-NR 312 —CO—R 412 wherein R 412 is aryl, heteroaryl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents chosen from:
  • R 512 is an aryl, (substituted aryl), heteroaryl, (substituted heteroaryl), heterocyclyl or (substituted heterocyclyl) group;
  • R 212 is chosen from:
  • each R 312 is independently chosen from hydrogen; C 1-10 alkyl-heteroaryl; C 1-10 alkyl-(substituted heteroaryl); C 1-10 alkyl-aryl; C 1-10 alkyl-(substituted aryl) and C 1-10 alkyl;
  • v is 0 to 4.
  • each R 12 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, halogen and trifluoromethyl;
  • R 113 is -alkyl-NR 313 —SO 2 —X—R 413 or -alkenyl-NR 313 —SO 2 —X—R 413 ;
  • X is a bond or —NR 513 —;
  • R 413 is aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents chosen from:
  • R 413 is alkyl, alkenyl, or heterocyclyl, oxo;
  • R 213 is chosen from:
  • each R 313 is independently chosen from hydrogen, C 1-10 alkyl, and when X is a bond R 313 and R 413 can combine to form a 3 to 7 membered heterocyclic or substituted heterocyclic ring;
  • R 513 is chosen from hydrogen, C 1-10 alkyl, and R 413 and R 513 can combine to form a 3 to 7 membered heterocyclic or substituted heterocyclic ring;
  • v is 0 to 4 and each R 13 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, halogen and trifluoromethyl;
  • R 114 is -alkyl-NR 314 —CY—NR 514 —X—R 414 or -alkenyl-NR 314 —CY—NR 514 —X—R 414
  • Y is ⁇ O or ⁇ S
  • X is a bond, —CO— or —SO 2 —;
  • R 414 is aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents chosen from:
  • R 414 is alkyl, alkenyl or heterocyclyl, oxo; with the proviso that when X is a bond R 414 can additionally be hydrogen;
  • R 214 is chosen from:
  • each R 314 is independently chosen from hydrogen and C 1-10 alkyl
  • R 514 is chosen from hydrogen, C 1-10 alkyl, and R 414 and R 514 can combine to form a 3 to 7 membered heterocyclic or substituted heterocyclic ring;
  • v is 0 to 4 and each R 14 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, halogen and trifluoromethyl,
  • the IRM compound can be chosen from imidazoquinoline amines and imidazotetrahydroquinoline amines, for example, 1H-imidazo[4,5-c]quinolin-4-amines and tetrahydro-1H-imidazo[4,5-c]quinolin-4-amines defined by Formulas XV, XVI, XVII, XVIII, XIX, XX, XXI, XXIII, XXIV, XXV, and XXVI below
  • X is —CHR 515 —, —CHR 515 -alkyl-, or —CHR 515 -alkenyl-;
  • R 115 is chosen from:
  • Z is —NR 515 —, —O—, or —S—;
  • R 215 is chosen from:
  • R 315 is ⁇ O or ⁇ S
  • R 415 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
  • each R 515 is independently H or C 1-10 alkyl
  • R 615 is a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
  • R 715 is H, C 1-10 alkyl, arylalkyl, or R 415 and R 715 can join together to form a 5 to 7 membered heterocylcic ring;
  • R 815 is H, C 1-10 alkyl, or R 715 and R 815 can join together to form a 5 to 7 membered heterocyclic ring;
  • Y is —O— or —S(O) 0-2 —;
  • v is 0 to 4.
  • each R 15 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
  • X is —CHR 516 —, —CHR 516 -alkyl-, or —CHR 516 -alkenyl-;
  • R 116 is chosen from:
  • Z is —NR 516 —, —O—, or —S—;
  • R 216 is chosen from:
  • R 316 is ⁇ O or ⁇ S
  • R 416 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
  • each R 516 is independently H or C 1-10 alkyl
  • R 616 is a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
  • R 716 is H, C 1-10 alkyl, arylalkyl, or R 416 and R 716 can join together to form a 5 to 7 membered hetercyclic ring;
  • R 816 is H or C 1-10 alkyl; or R 716 and R 816 can join together to form a 5 to 7 membered heterocyclic ring;
  • Y is —O— or —S(O) 0-2 —;
  • v is 0 to 4.
  • each R 16 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen, and trifluoromethyl;
  • X is —CHR 317 —, —CHR 317 -alkyl-, or —CHR 317 -alkenyl-;
  • R 117 is chosen from:
  • R 217 is chosen from:
  • R 417 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
  • each R 317 is independently H or C 1-10 alkyl
  • each Y is independently —O— or —S(O) 0-2 —;
  • v is 0 to 4.
  • each R 17 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
  • X is —CHR 318 —, —CHR 318 -alkyl-, or —CHR 318 -alkenyl-;
  • R 118 is chosen from:
  • R 218 is chosen from:
  • R 418 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
  • each R 318 is independently H or C 1-10 alkyl
  • each Y is independently —O— or —S(O) 0-2 —;
  • v is 0 to 4.
  • each R 18 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
  • X is —CHR 319 —, —CHR 319 -alkyl-, or —CHR 319 -alkenyl-;
  • R 119 is chosen from:
  • R 219 is chosen from:
  • R 419 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
  • each R 319 is independently H or C 1-10 alkyl
  • each Y is independently —O— or —S(O) 0-2 —;
  • v is 0 to 4.
  • each R 19 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
  • X is —CHR 320 —, —CHR 320 -alkyl-, or —CHR 320 -alkenyl-;
  • R 120 is chosen from:
  • R 220 is chosen from:
  • R 420 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
  • each R 320 is independently H or C 1-10 alkyl
  • each Y is independently —O— or —S(O) 0-2 —;
  • v is 0 to 4.
  • each R 20 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
  • X is —CHR 521 —, —CHR 521 -alkyl-, or —CHR 521 -alkenyl-;
  • R 121 is chosen from:
  • R 221 is chosen from:
  • Y is —O— or —S(O) 0-2 —;
  • R 321 is H, C 1-10 alkyl, or arylalkyl
  • each R 421 is independently alkyl or alkenyl, which may be interrupted by one or more —O— groups, or R 321 and R 421 can join together to form a 5 to 7 membered heterocyclic ring;
  • each R 521 is independently H, C 1-10 alkyl, or C 2-10 alkenyl;
  • R 621 is a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
  • R 721 is C 1-10 alkyl, or R 321 and R 721 can join together to form a 5 to 7 membered heterocyclic ring;
  • v is 0 to 4.
  • each R 21 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
  • X is —CHR 522 —, —CHR 522 -alkyl-, or —CHR 522 -alkenyl-;
  • R 122 is chosen from:
  • R 222 is chosen from:
  • Y is —O— or —S(O) 0-2 —;
  • R 322 is H, C 1-10 alkyl, or arylalkyl
  • each R 422 is independently alkyl or alkenyl, which may be interrupted by one or more —O— groups, or R 322 and R 422 can join together to form a 5 to 7 membered heterocyclic ring;
  • each R 522 is independently H, C 1-10 alkyl, or C 2-10 alkenyl;
  • R 622 is a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
  • R 722 is C 1-10 alkyl, or R 322 and R 722 can join together to form a 5 to 7 membered heterocyclic ring;
  • v is 0 to 4.
  • each R 22 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen, and trifluoromethyl;
  • X is —CHR 323 —, —CHR 323 -alkyl-, or —CHR 323 -alkenyl-;
  • Z is —S—, —SO—, or —SO 2 —;
  • R 123 is chosen from:
  • R 223 is chosen from:
  • each R 323 is independently H or C 1-10 alkyl
  • each R 423 is independently alkyl or alkenyl
  • each Y is independently —O— or —S(O) 0-2 —;
  • v is 0 to 4.
  • each R 23 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
  • X is —CHR 324 —, —CHR 324 -alkyl-, or —CHR 324 -alkenyl-;
  • Z is —S—, —SO—, or —SO 2 —;
  • R 124 is chosen from:
  • R 224 is chosen from:
  • each R 324 is independently H or C 1-10 alkyl
  • each R 424 is independently alkyl or alkenyl
  • each Y is independently —O— or —S(O) 0-2 —;
  • v is 0 to 4.
  • each R 24 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
  • X is —CHR 525 —, —CHR 525 -alkyl-, or —CHR 525 -alkenyl-;
  • R 125 is chosen from:
  • R 225 is chosen from:
  • each R 325 is ⁇ O or ⁇ S
  • each R 425 is independently alkyl or alkenyl, which may be interrupted by one or more —O— groups;
  • each R 525 is independently H or C 1-10 alkyl
  • R 625 is a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
  • R 725 is H, C 1-10 alkyl which may be interrupted by a hetero atom, or R 725 can join with R 525 to form a 5 to 7 membered heterocyclic ring;
  • R 825 is H, C 1-10 alkyl, arylalkyl, or R 425 and R 825 can join together to form a 5 to 7 membered heterocyclic ring;
  • R 925 is C 1-10 alkyl which can join together with R 825 to form a 5 to 7 membered heterocyclic ring;
  • each Y is independently —O— or —S(O) 0-2 —;
  • Z is a bond, —CO—, or —SO 2 —;
  • v is 0 to 4.
  • each R 25 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
  • X is —CHR 526 —, —CHR 526 -alkyl-, or —CHR 526 -alkenyl-;
  • R 126 is chosen from:
  • R 226 is chosen from:
  • each R 326 is ⁇ O or ⁇ S
  • each R 426 is independently alkyl or alkenyl, which may be interrupted by one or more —O— groups;
  • each R 526 is independently H or C 1-10 alkyl
  • R 626 is a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
  • R 726 is H, C 1-10 alkyl which may be interrupted by a hetero atom, or R 726 can join with R 526 to form a 5 to 7 membered heterocyclic ring;
  • R 826 is H, C 1-10 alkyl, arylalkyl, or R 426 and R 826 can join together to form a 5 to 7 membered heterocyclic ring;
  • R 926 is C 1-10 alkyl which can join together with R 826 to form a 5 to 7 membered heterocyclic ring;
  • each Y is independently —O— or —S(O) 0-2 —;
  • Z is a bond, —CO—, or —SO 2 —;
  • v is 0 to 4.
  • each R 26 present is independently chosen from C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen, and trifluoromethyl;
  • the IRM compound can be chosen from 1H-imidazo[4,5-c]pyridin-4-amines compounds defined by Formula XXVII
  • X is alkylene or alkenylene
  • Y is —CO—, —CS—, or —SO 2 —;
  • Z is a bond, —O—, —S—, or —NR 527 —;
  • R 127 is aryl, heteroaryl, heterocyclyl, C 1-20 alkyl or C 2-20 alkenyl, each of which may be unsubstituted or substituted by one or more substituents independently chosen from:
  • R 227 is chosen from:

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US20010004853A1 (en) * 1999-12-28 2001-06-28 Yasunari Kato Accelerator with attachment of pedal arm
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US20040157879A1 (en) * 2000-12-08 2004-08-12 3M Innovative Properties Company Urea substituted imidazopyridines
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US20040265351A1 (en) * 2003-04-10 2004-12-30 Miller Richard L. Methods and compositions for enhancing immune response
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US20070292456A1 (en) * 2003-08-05 2007-12-20 3M Innovative Properties Company Formulations Containing an Immune Response Modifier
US20080015271A1 (en) * 2006-07-14 2008-01-17 Stiefel Research Austrialia Pty Ltd Fatty acid pharmaceutical foam
US20080015184A1 (en) * 2004-06-14 2008-01-17 3M Innovative Properties Company Urea Substituted Imidazopyridines, Imidazoquinolines, and Imidazonaphthyridines
US20080114019A1 (en) * 2003-08-12 2008-05-15 Coley Pharmaceutical Group, Inc. Hydroxylamine Substituted Imidazoquinolines
WO2008082381A1 (en) * 2006-12-29 2008-07-10 3M Innovative Properties Company Immune response modifier formulations containing oleic acid and methods
WO2008082382A1 (en) * 2006-12-29 2008-07-10 Graceway Pharmaceuticals, Inc. Packaging for 1-(2-methylpropyl)-1h-imidazo[4,5-c]quinolin-4-amine containing formulation
US20080188513A1 (en) * 2004-12-30 2008-08-07 Taked Pharmaceutical Company Limited 1-(2-Methylpropyl)-1H-Imidazo[4,5-C](1,5]Naphthyridin-4-Amine Ethanesulfonate and 1-(2-Methylpropyl)-1H-Imidazo[4,5-C](1,5]Naphthyridin-4-Amine Methanesulfonate
US20080306266A1 (en) * 2004-12-30 2008-12-11 3M Innovative Properties Company Process for Preparing 2-Methyl-1-(2-Methylpropyl)-1H-Imidazo[4,5-C][1,5]Naphthyridin-4-Amine
US20090005376A1 (en) * 2004-09-02 2009-01-01 3M Innovative Properties Company 1-Alkoxy 1H-Imidazo Ring Systems and Methods
US20090023722A1 (en) * 1999-06-10 2009-01-22 Coleman Patrick L Amide substituted imidazoquinolines
US20090035323A1 (en) * 2006-02-22 2009-02-05 Doris Stoermer Immune response modifier conjugates
US20090042925A1 (en) * 2003-11-14 2009-02-12 Coley Pharmaceutical Group, Inc. Oxime substituted imidazoquinolines
WO2009118296A2 (en) * 2008-03-24 2009-10-01 4Sc Ag Novel substituted imidazoquinolines
US20100092401A1 (en) * 2006-07-18 2010-04-15 Graceway Pharmaceuticals, Llc Immune response modifier formulations
US20100096287A1 (en) * 2006-07-31 2010-04-22 Stoesz James D Immune Response Modifier Compositions and Methods
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Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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Citations (36)

* 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
US4595586A (en) * 1985-08-30 1986-06-17 Eli Lilly And Company Moisturizing lotion
US4689338A (en) * 1983-11-18 1987-08-25 Riker Laboratories, Inc. 1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use
US4698348A (en) * 1983-11-18 1987-10-06 Riker Laboratories, Inc. 1H-imidazo[4,5-c]quinolines and their use as bronchodilating agents
US4800076A (en) * 1987-03-13 1989-01-24 Johnson & Johnson Consumer Products, Inc. Skin care compositions
US4929624A (en) * 1989-03-23 1990-05-29 Minnesota Mining And Manufacturing Company Olefinic 1H-imidazo(4,5-c)quinolin-4-amines
US4973468A (en) * 1989-03-22 1990-11-27 Cygnus Research Corporation Skin permeation enhancer compositions
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
US4996193A (en) * 1989-03-03 1991-02-26 The Regents Of The University Of California Combined topical and systemic method of administration of cyclosporine
US5037986A (en) * 1989-03-23 1991-08-06 Minnesota Mining And Manufacturing Company Olefinic 1H-imidazo[4,5-c]quinolin-4-amines
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
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
US5266575A (en) * 1991-11-06 1993-11-30 Minnesota Mining And Manufacturing Company 2-ethyl 1H-imidazo[4,5-ciquinolin-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
US5352784A (en) * 1993-07-15 1994-10-04 Minnesota Mining And Manufacturing Company Fused cycloalkylimidazopyridines
US5367076A (en) * 1990-10-05 1994-11-22 Minnesota Mining And Manufacturing Company Process for imidazo[4,5-C]quinolin-4-amines
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
US5395937A (en) * 1993-01-29 1995-03-07 Minnesota Mining And Manufacturing Company Process for preparing quinoline amines
US5446153A (en) * 1993-07-15 1995-08-29 Minnesota Mining And Manufacturing Company Intermediates for imidazo[4,5-c]pyridin-4-amines
US5482936A (en) * 1995-01-12 1996-01-09 Minnesota Mining And Manufacturing Company Imidazo[4,5-C]quinoline amines
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
US5756747A (en) * 1989-02-27 1998-05-26 Riker Laboratories, Inc. 1H-imidazo 4,5-c!quinolin-4-amines
US5939080A (en) * 1997-01-10 1999-08-17 The Procter & Gamble Company Hydrophobic agents and non-polymeric surfactants use in oral care products
US6039969A (en) * 1996-10-25 2000-03-21 3M Innovative Properties Company Immune response modifier compounds for treatment of TH2 mediated and related diseases
US6069149A (en) * 1997-01-09 2000-05-30 Terumo Kabushiki Kaisha Amide derivatives and intermediates for the synthesis thereof
US6083505A (en) * 1992-04-16 2000-07-04 3M Innovative Properties Company 1H-imidazo[4,5-C]quinolin-4-amines as vaccine adjuvants
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
US6194425B1 (en) * 1997-12-11 2001-02-27 3M Innovative Properties Company Imidazonaphthyridines
US6245776B1 (en) * 1999-01-08 2001-06-12 3M Innovative Properties Company Formulations and methods for treatment of mucosal associated conditions with an immune response modifier
US6331539B1 (en) * 1999-06-10 2001-12-18 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines
US6376669B1 (en) * 1999-11-05 2002-04-23 3M Innovative Properties Company Dye labeled imidazoquinoline compounds
US20020055517A1 (en) * 2000-09-15 2002-05-09 3M Innovative Properties Company Methods for delaying recurrence of herpes virus symptoms
US20020058674A1 (en) * 1999-01-08 2002-05-16 Hedenstrom John C. Systems and methods for treating a mucosal surface
US6451810B1 (en) * 1999-06-10 2002-09-17 3M Innovative Properties Company Amide substituted imidazoquinolines
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

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4722941A (en) * 1978-06-07 1988-02-02 Kali-Chemie Pharma Gmbh Readily absorbable pharmaceutical compositions of per se poorly absorbable pharmacologically active agents and preparation thereof
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
JPH09208584A (ja) 1996-01-29 1997-08-12 Terumo Corp アミド誘導体、およびそれを含有する医薬製剤、および合成中間体
US5728732A (en) * 1996-11-27 1998-03-17 Elizabeth Arden Company, Division Of Conopco, Inc. Skin treatment with salicylic acid esters and retinoids
US5939090A (en) * 1996-12-03 1999-08-17 3M Innovative Properties Company Gel formulations for topical drug delivery
TW450810B (en) 1997-02-20 2001-08-21 Fujisawa Pharmaceutical Co Macrolides antibiotic pharmaceutical composition for preventing and treating skin diseases
US6248763B1 (en) * 1998-05-19 2001-06-19 Scivoletto Rosemarie Composition for treating skin conditions
US6372234B1 (en) * 1997-05-27 2002-04-16 Sembiosys Genetics Inc. Products for topical applications comprising oil bodies
JPH11222432A (ja) 1998-02-03 1999-08-17 Terumo Corp インターフェロンを誘起するアミド誘導体を含有する外用剤
JPH11255926A (ja) 1998-03-13 1999-09-21 Toray Ind Inc シリコーン成型品およびその製造方法
JP2000119271A (ja) 1998-08-12 2000-04-25 Hokuriku Seiyaku Co Ltd １ｈ―イミダゾピリジン誘導体
CA2349698A1 (en) 1998-11-03 2000-05-11 Bristol-Myers Squibb Company Skin moisturizer compositions containing a sebum control agent
US6558951B1 (en) 1999-02-11 2003-05-06 3M Innovative Properties Company Maturation of dendritic cells with immune response modifying compounds
JP2000247884A (ja) 1999-03-01 2000-09-12 Sumitomo Pharmaceut Co Ltd アラキドン酸誘発皮膚疾患治療剤
US6541485B1 (en) 1999-06-10 2003-04-01 3M Innovative Properties Company Urea substituted imidazoquinolines
JP4521899B2 (ja) 1999-08-27 2010-08-11 エーザイ・アール・アンド・ディー・マネジメント株式会社 クロタミトン含有皮膚外用液剤
US6894060B2 (en) 2000-03-30 2005-05-17 3M Innovative Properties Company Method for the treatment of dermal lesions caused by envenomation
JP2002145777A (ja) 2000-11-06 2002-05-22 Sumitomo Pharmaceut Co Ltd アラキドン酸誘発皮膚疾患治療剤
UA74593C2 (en) 2000-12-08 2006-01-16 3M Innovative Properties Co Substituted imidazopyridines
AU3249802A (en) 2000-12-08 2002-06-18 3M Innovative Properties Co Screening method for identifying compounds that selectively induce interferon alpha
UA74852C2 (en) 2000-12-08 2006-02-15 3M Innovative Properties Co Urea-substituted imidazoquinoline ethers
CA2449754A1 (en) 2001-06-15 2002-12-27 3M Innovative Properties Company Immune response modifiers for the treatment of periodontal disease

Patent Citations (37)

* 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
US4689338A (en) * 1983-11-18 1987-08-25 Riker Laboratories, Inc. 1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use
US4698348A (en) * 1983-11-18 1987-10-06 Riker Laboratories, Inc. 1H-imidazo[4,5-c]quinolines and their use as bronchodilating agents
US4595586A (en) * 1985-08-30 1986-06-17 Eli Lilly And Company Moisturizing lotion
US4800076A (en) * 1987-03-13 1989-01-24 Johnson & Johnson Consumer Products, Inc. Skin care compositions
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
US4996193A (en) * 1989-03-03 1991-02-26 The Regents Of The University Of California Combined topical and systemic method of administration of cyclosporine
US4973468A (en) * 1989-03-22 1990-11-27 Cygnus Research Corporation Skin permeation enhancer compositions
US5037986A (en) * 1989-03-23 1991-08-06 Minnesota Mining And Manufacturing Company Olefinic 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
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
US5367076A (en) * 1990-10-05 1994-11-22 Minnesota Mining And Manufacturing Company Process for imidazo[4,5-C]quinolin-4-amines
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
US5346905A (en) * 1991-09-04 1994-09-13 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
US6083505A (en) * 1992-04-16 2000-07-04 3M Innovative Properties Company 1H-imidazo[4,5-C]quinolin-4-amines as vaccine adjuvants
US5395937A (en) * 1993-01-29 1995-03-07 Minnesota Mining And Manufacturing Company Process for preparing quinoline amines
US5352784A (en) * 1993-07-15 1994-10-04 Minnesota Mining And Manufacturing Company Fused cycloalkylimidazopyridines
US5446153A (en) * 1993-07-15 1995-08-29 Minnesota Mining And Manufacturing Company Intermediates for imidazo[4,5-c]pyridin-4-amines
US5482936A (en) * 1995-01-12 1996-01-09 Minnesota Mining And Manufacturing Company Imidazo[4,5-C]quinoline amines
US5741908A (en) * 1996-06-21 1998-04-21 Minnesota Mining And Manufacturing Company Process for reparing imidazoquinolinamines
US5693811A (en) * 1996-06-21 1997-12-02 Minnesota Mining And Manufacturing Company Process for preparing tetrahdroimidazoquinolinamines
US6039969A (en) * 1996-10-25 2000-03-21 3M Innovative Properties Company Immune response modifier compounds for treatment of TH2 mediated and related diseases
US6069149A (en) * 1997-01-09 2000-05-30 Terumo Kabushiki Kaisha Amide derivatives and intermediates for the synthesis thereof
US5939080A (en) * 1997-01-10 1999-08-17 The Procter & Gamble Company Hydrophobic agents and non-polymeric surfactants use in oral care products
US6194425B1 (en) * 1997-12-11 2001-02-27 3M Innovative Properties Company Imidazonaphthyridines
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
US6245776B1 (en) * 1999-01-08 2001-06-12 3M Innovative Properties Company Formulations and methods for treatment of mucosal associated conditions with an immune response modifier
US20020058674A1 (en) * 1999-01-08 2002-05-16 Hedenstrom John C. Systems and methods for treating a mucosal surface
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
US6331539B1 (en) * 1999-06-10 2001-12-18 3M Innovative Properties Company Sulfonamide and sulfamide 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
US20020055517A1 (en) * 2000-09-15 2002-05-09 3M Innovative Properties Company Methods for delaying recurrence of herpes virus symptoms

Cited By (232)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080091010A1 (en) * 1997-12-11 2008-04-17 Graceway Pharmaceuticals, Llc Intermediates for imidazonaphthyridines
US20060128674A1 (en) * 1997-12-11 2006-06-15 3M Innovative Properties Company Intermediates for imidazonaphthyridines
US7038051B2 (en) 1997-12-11 2006-05-02 3M Innovative Properties Company Imidazonaphthyridines
US20050288320A1 (en) * 1997-12-11 2005-12-29 3M Innovative Properties Company Imidazonaphthyridines
US7678918B2 (en) 1997-12-11 2010-03-16 3M Innovative Properties Company Intermediates for imidazonaphthyridines
US7335773B2 (en) 1997-12-11 2008-02-26 Graceway Pharmaceuticals, Llc Intermediates for imidazonaphthyridines
US20040167154A1 (en) * 1999-06-10 2004-08-26 3M Innovative Properties Company Urea substituted imidazoquinolines
US7157453B2 (en) 1999-06-10 2007-01-02 3M Innovation Properties Company Urea substituted imidazoquinolines
US20060106052A1 (en) * 1999-06-10 2006-05-18 3M Innovative Properties Company Method of using sulfonamide substituted imidazoquinolines
US6897221B2 (en) 1999-06-10 2005-05-24 3M Innovative Properties Company Urea substituted imidazoquinolines
US20090023722A1 (en) * 1999-06-10 2009-01-22 Coleman Patrick L Amide substituted imidazoquinolines
US20010004853A1 (en) * 1999-12-28 2001-06-28 Yasunari Kato Accelerator with attachment of pedal arm
US20050234088A1 (en) * 2000-12-08 2005-10-20 3M Innovative Properties Company Urea substituted imidazoquinoline ethers
US7132429B2 (en) 2000-12-08 2006-11-07 3M Innovative Properties Company Sulfonamido ether substituted imidazoquinolines
US20060142202A1 (en) * 2000-12-08 2006-06-29 3M Innovative Properties Company Compositions and methods for targeted delivery of immune response modifiers
US20040157879A1 (en) * 2000-12-08 2004-08-12 3M Innovative Properties Company Urea substituted imidazopyridines
US7288550B2 (en) 2000-12-08 2007-10-30 3M Innovative Properties Company Thioether substituted imidazoquinolines
US6878719B2 (en) 2000-12-08 2005-04-12 3M Innovative Properties Company Sulfonamido substituted imidazopyridines
US7098221B2 (en) 2000-12-08 2006-08-29 3M Innovative Properties Company Amide substituted imidazopyridines
US7276515B2 (en) 2000-12-08 2007-10-02 Coley Pharmaceutical Group, Inc. Thioether substituted imidazoquinolines
US7115622B2 (en) 2000-12-08 2006-10-03 3M Innovative Properties Company Amido ether substituted imidazoquinolines
US6903113B2 (en) 2000-12-08 2005-06-07 3M Innovative Properties Company Urea substituted imidazopyridines
US6969722B2 (en) 2000-12-08 2005-11-29 3M Innovative Properties Company Amide substituted imidazopyridines
US7612083B2 (en) 2000-12-08 2009-11-03 Coley Pharmaceutical Group, Inc. Urea substituted imidazoquinoline ethers
US7214675B2 (en) 2000-12-08 2007-05-08 3M Innovative Properties Company Urea substituted imidazoquinoline ethers
US20050209268A1 (en) * 2000-12-08 2005-09-22 3M Innovative Properties Company Thioether substituted imidazoquinolines
US20050209267A1 (en) * 2000-12-08 2005-09-22 3M Innovative Properties Company Thioether substituted imidazoquinolines
US20050215581A1 (en) * 2000-12-08 2005-09-29 3M Innovative Properties Company Urea substituted imidazoquinoline ethers
US20040235881A1 (en) * 2001-06-15 2004-11-25 Mitra Sumita B. Immune response modifiers for the treatment of periodontal disease
US7226928B2 (en) 2001-06-15 2007-06-05 3M Innovative Properties Company Methods for the treatment of periodontal disease
US7199131B2 (en) 2001-12-21 2007-04-03 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines
US20050197358A1 (en) * 2001-12-21 2005-09-08 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines
US6888000B2 (en) 2001-12-21 2005-05-03 3M Innovative Properties Company Sulfonamide and sulfamide substituted imidazoquinolines
US20030161797A1 (en) * 2002-02-22 2003-08-28 3M Innovative Properties Company Method of reducing and treating UVB-induced immunosuppression
US7030129B2 (en) * 2002-02-22 2006-04-18 3M Innovative Properties Company Method of reducing and treating UVB-induced immunosuppression
US7220758B2 (en) 2002-06-07 2007-05-22 3M Innovative Properties Company Ether substituted imidazopyridines
US7091214B2 (en) 2002-12-20 2006-08-15 3M Innovative Properties Co. Aryl substituted Imidazoquinolines
US7598382B2 (en) 2002-12-20 2009-10-06 Coley Pharmaceutical Group, Inc. Aryl substituted imidazoquinolines
US8110582B2 (en) * 2003-03-04 2012-02-07 3M Innovative Properties Company Prophylactic treatment of UV-induced epidermal neoplasia
US20040175336A1 (en) * 2003-03-04 2004-09-09 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
US20050054640A1 (en) * 2003-03-07 2005-03-10 Griesgraber George W. 1-Amino 1H-imidazoquinolines
US7163947B2 (en) 2003-03-07 2007-01-16 3M Innovative Properties Company 1-Amino 1H-imidazoquinolines
US8426457B2 (en) 2003-03-13 2013-04-23 Medicis Pharmaceutical Corporation Methods of improving skin quality
US20040181130A1 (en) * 2003-03-13 2004-09-16 3M Innovative Properties Company Methods for diagnosing skin lesions
US20040180919A1 (en) * 2003-03-13 2004-09-16 3M Innovative Properties Company Methods of improving skin quality
US7699057B2 (en) 2003-03-13 2010-04-20 3M Innovative Properties Company Methods for treating skin lesions
US20100180902A1 (en) * 2003-03-13 2010-07-22 3M Innovative Properties Company Methods for diagnosing skin lesions
WO2004080430A3 (en) * 2003-03-13 2006-02-23 3M Innovative Properties Co Methods of improving skin quality
US20050165043A1 (en) * 2003-03-13 2005-07-28 3M Innovative Properties Company Method of treating scarring
US20040191833A1 (en) * 2003-03-25 2004-09-30 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
US20040202720A1 (en) * 2003-04-10 2004-10-14 3M Innovative Properties Company Delivery of immune response modifier compounds using metal-containing particulate support materials
US20070105856A1 (en) * 2003-04-23 2007-05-10 Pfizer Inc Cannabinoid receptor ligands and uses thereof
US20050032829A1 (en) * 2003-06-06 2005-02-10 3M Innovative Properties Company Process for imidazo[4,5-c]pyridin-4-amines
US7038053B2 (en) 2003-06-06 2006-05-02 3M Innovative Properties Company Process for imidazo[4,5-c]pyridin-4-amines
US20050245516A1 (en) * 2003-06-06 2005-11-03 3M Innovative Properties Company Process for imidazo[4,5-c]pyridin-4-amines
US20080312434A1 (en) * 2003-06-06 2008-12-18 Coley Pharmaceutical Group, Inc. Process for imidazo [4,5-c] pyridin-4-amines
US20040248929A1 (en) * 2003-06-06 2004-12-09 3M Innovative Properties Company Process for imidazo[4,5-c]pyridin-4-amines
US20070292456A1 (en) * 2003-08-05 2007-12-20 3M Innovative Properties Company Formulations Containing an Immune Response Modifier
US8211906B1 (en) 2003-08-05 2012-07-03 Scherrer Lawrence C Method of inhibiting growth of neoplastic cells and inhibiting infection by administering an immune enhancer drug
US8221771B2 (en) 2003-08-05 2012-07-17 3M Innovative Properties Company Formulations containing an immune response modifier
US20080114019A1 (en) * 2003-08-12 2008-05-15 Coley Pharmaceutical Group, Inc. Hydroxylamine Substituted Imidazoquinolines
US8673932B2 (en) 2003-08-12 2014-03-18 3M Innovative Properties Company Oxime substituted imidazo-containing compounds
US7648997B2 (en) * 2003-08-12 2010-01-19 Coley Pharmaceutical Group, Inc. Hydroxylamine substituted imidazoquinolines
US7799800B2 (en) 2003-08-14 2010-09-21 3M Innovative Properties Company Lipid-modified immune response modifiers
US20060189644A1 (en) * 2003-08-14 2006-08-24 Wightman Paul D Lipid-modified immune response modifiers
US20050048072A1 (en) * 2003-08-25 2005-03-03 3M Innovative Properties Company Immunostimulatory combinations and treatments
US8961477B2 (en) 2003-08-25 2015-02-24 3M Innovative Properties Company Delivery of immune response modifier compounds
US7897597B2 (en) 2003-08-27 2011-03-01 3M Innovative Properties Company Aryloxy and arylalkyleneoxy substituted imidazoquinolines
US20060216333A1 (en) * 2003-09-02 2006-09-28 Miller Richard L Methods related to the treatment of mucosal associated conditions
US7923429B2 (en) 2003-09-05 2011-04-12 3M Innovative Properties Company Treatment for CD5+ B cell lymphoma
US20050059072A1 (en) * 2003-09-17 2005-03-17 3M Innovative Properties Company Selective modulation of TLR gene expression
US20060100229A1 (en) * 2003-10-03 2006-05-11 Hays David S Pyrazolopyridines and analogs thereof
US8871782B2 (en) 2003-10-03 2014-10-28 3M Innovative Properties Company Alkoxy substituted imidazoquinolines
US7879849B2 (en) 2003-10-03 2011-02-01 3M Innovative Properties Company Pyrazolopyridines and analogs thereof
US7544697B2 (en) 2003-10-03 2009-06-09 Coley Pharmaceutical Group, Inc. Pyrazolopyridines and analogs thereof
US20050096259A1 (en) * 2003-10-31 2005-05-05 3M Innovative Properties Company Neutrophil activation by immune response modifier compounds
US7897767B2 (en) 2003-11-14 2011-03-01 3M Innovative Properties Company Oxime substituted imidazoquinolines
US20090042925A1 (en) * 2003-11-14 2009-02-12 Coley Pharmaceutical Group, Inc. Oxime substituted imidazoquinolines
US8598192B2 (en) 2003-11-14 2013-12-03 3M Innovative Properties Company Hydroxylamine substituted imidazoquinolines
US8691837B2 (en) 2003-11-25 2014-04-08 3M Innovative Properties Company Substituted imidazo ring systems and methods
US8778963B2 (en) 2003-11-25 2014-07-15 3M Innovative Properties Company Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines
US20070099901A1 (en) * 2003-11-25 2007-05-03 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
US20050171072A1 (en) * 2003-12-02 2005-08-04 Tomai Mark A. Therapeutic combinations and methods including IRM compounds
US8940755B2 (en) 2003-12-02 2015-01-27 3M Innovative Properties Company Therapeutic combinations and methods including IRM compounds
US7939526B2 (en) 2003-12-04 2011-05-10 3M Innovative Properties Company Sulfone substituted imidazo ring ethers
US7888349B2 (en) 2003-12-29 2011-02-15 3M Innovative Properties Company Piperazine, [1,4]Diazepane, [1,4]Diazocane, and [1,5]Diazocane fused imidazo ring compounds
US20070167476A1 (en) * 2003-12-29 2007-07-19 Kshirsagar Tushar A Piperazine, [1,4]Diazepane, [1,4]Diazocane, and [1,5]Diazocane fused imidazo ring compounds
US8802853B2 (en) 2003-12-29 2014-08-12 3M Innovative Properties Company Arylalkenyl and arylalkynyl substituted imidazoquinolines
US8735421B2 (en) 2003-12-30 2014-05-27 3M Innovative Properties Company Imidazoquinolinyl sulfonamides
US20050239735A1 (en) * 2003-12-30 2005-10-27 3M Innovative Properties Company Enhancement of immune responses
WO2005089317A2 (en) 2004-03-15 2005-09-29 3M Innovative Properties Company Immune response modifier formulations and methods
US20070167479A1 (en) * 2004-03-15 2007-07-19 Busch Terri F Immune response modifier formulations and methods
US8697873B2 (en) 2004-03-24 2014-04-15 3M Innovative Properties Company Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines
US20060051374A1 (en) * 2004-04-28 2006-03-09 3M Innovative Properties Company Compositions and methods for mucosal vaccination
US20050267145A1 (en) * 2004-05-28 2005-12-01 Merrill Bryon A Treatment for lung cancer
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
US8026366B2 (en) 2004-06-18 2011-09-27 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
US20070287724A1 (en) * 2004-06-18 2007-12-13 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
US7897609B2 (en) 2004-06-18 2011-03-01 3M Innovative Properties Company Aryl substituted imidazonaphthyridines
US20060045886A1 (en) * 2004-08-27 2006-03-02 Kedl Ross M HIV immunostimulatory compositions
US8143270B2 (en) 2004-09-02 2012-03-27 3M Innovative Properties Company 2-amino 1H-in-imidazo ring systems and methods
US20090005376A1 (en) * 2004-09-02 2009-01-01 3M Innovative Properties Company 1-Alkoxy 1H-Imidazo Ring Systems and Methods
US7579359B2 (en) 2004-09-02 2009-08-25 3M Innovative Properties Company 1-alkoxy 1H-imidazo ring systems and methods
US20070243215A1 (en) * 2004-10-08 2007-10-18 Miller Richard L Adjuvant for Dna Vaccines
US7928116B2 (en) 2004-12-17 2011-04-19 3M Innovative Properties Company Method of treating actinic keratosis
US7928117B2 (en) 2004-12-17 2011-04-19 3M Innovative Properties Company Method of inducing cytokine biosynthesis
US20100120824A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company Method of preparing a pharmaceutical cream and minimizing imiquimod impurity formation
US20100120827A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company X-fold less imiquimod impurities at two months between refined and compendial
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US20100120831A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company Methods for improving imiquimod availability at two months, four months and six months between refined and compendial
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US20100120820A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company Method of treating actinic keratosis
US20100130531A1 (en) * 2004-12-17 2010-05-27 3M Innovative Properties Company Pharmaceutical creams with reduced imiquimod impurities
US20100130529A1 (en) * 2004-12-17 2010-05-27 3M Innovative Properties Company Method of stabilizing imiquimod
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US20100130533A1 (en) * 2004-12-17 2010-05-27 3M Innovative Properties Company Pharmaceutical creams with refined oleic acid
US20100130536A1 (en) * 2004-12-17 2010-05-27 3M Innovative Properties Company Methods for controlling formation of imiquimod impurities for two months, four months, and six months
US20100130534A1 (en) * 2004-12-17 2010-05-27 3M Innovative Properties Company Methods for reducing imiquimod impurities for two months, four months, and six months
US20070123558A1 (en) * 2004-12-17 2007-05-31 Statham Alexis S Immune response modifier formulations containing oleic acid and methods
US7655672B2 (en) 2004-12-17 2010-02-02 3M Innovative Properties Company Immune response modifier formulations containing oleic acid and methods
US20100120823A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company Method of treating basal cell carcinoma
US8557838B2 (en) 2004-12-17 2013-10-15 Medicis Pharmaceutical Corporation Immune response modifier formulations containing oleic acid and methods
US20100120832A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company Method of preparing a pharmaceutical cream and minimizing imiquimod impurity formation (at least four months storage)
US8080560B2 (en) 2004-12-17 2011-12-20 3M Innovative Properties Company Immune response modifier formulations containing oleic acid and methods
US20100120829A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company X-fold less imiquimod impurities at six months between refined and compendial
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US20100120819A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company Method of reducing imiquimod impurity formation
US20100120826A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company Method of inducing cytokine biosynthesis
US7902213B2 (en) 2004-12-17 2011-03-08 3M Innovative Properties Company Pharmaceutical cream with reduced imiquimod impurities at four months using refined oleic acid
US7902246B2 (en) 2004-12-17 2011-03-08 3M Innovative Properties Company Methods for controlling formation of imiquimod impurities for two months, four months, and six months
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US20100120821A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company Method of treating genital or peri-anal warts
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US20100120828A1 (en) * 2004-12-17 2010-05-13 3M Innovative Properties Company Method of inducing interferon biosynthesis
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US20080306266A1 (en) * 2004-12-30 2008-12-11 3M Innovative Properties Company Process for Preparing 2-Methyl-1-(2-Methylpropyl)-1H-Imidazo[4,5-C][1,5]Naphthyridin-4-Amine
US20100056557A1 (en) * 2004-12-30 2010-03-04 Bernd Benninghoff Treatment for cutaneous metastases
WO2006071997A2 (en) 2004-12-30 2006-07-06 3M Innovative Properties Company Treatment for cutaneous metastases
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
US20080188513A1 (en) * 2004-12-30 2008-08-07 Taked Pharmaceutical Company Limited 1-(2-Methylpropyl)-1H-Imidazo[4,5-C](1,5]Naphthyridin-4-Amine Ethanesulfonate and 1-(2-Methylpropyl)-1H-Imidazo[4,5-C](1,5]Naphthyridin-4-Amine Methanesulfonate
EP2394650A1 (en) 2004-12-30 2011-12-14 3M Innovative Properties Co. Use of resiquimod for the treatment of cutaneous metastases
US8034938B2 (en) 2004-12-30 2011-10-11 3M Innovative Properties Company Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds
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US8461174B2 (en) 2004-12-30 2013-06-11 3M Innovative Properties Company Treatment for cutaneous metastases
US20090124652A1 (en) * 2004-12-30 2009-05-14 Takeda Pharmaceutical Company Limited Polymorphs of 1-(2-Methylpropyl)-1H-Imidazo[4,5-C][1,5]Naphthyridin-4-Amine Ethane-Sulfonate
US9248127B2 (en) 2005-02-04 2016-02-02 3M Innovative Properties Company Aqueous gel formulations containing immune response modifiers
WO2006084073A3 (en) * 2005-02-04 2007-06-28 3M Innovative Properties Co Aqueous gel formulations containing 1-(2-methylpropyl)-1h-imidazo[4,5-c][1,5]naphthyridin-4-amine
US10071156B2 (en) 2005-02-04 2018-09-11 3M Innovative Properties Company Aqueous gel formulations containing immune response modifiers
WO2006084073A2 (en) * 2005-02-04 2006-08-10 Takeda Pharmaceutical Company Limited Aqueous gel formulations containing 1-(2-methylpropyl)-1h-imidazo[4,5-c][1,5]naphthyridin-4-amine
US7968563B2 (en) 2005-02-11 2011-06-28 3M Innovative Properties Company Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods
US20080262022A1 (en) * 2005-03-14 2008-10-23 Graceway Phamaceuticals Llc Method of Treating Actinic Keratosis
WO2006099275A3 (en) * 2005-03-14 2007-10-25 3M Innovative Properties Co Method of treating actinic keratosis
US8354424B2 (en) * 2005-03-14 2013-01-15 Medicis Pharmaceutical Corporation Method of treating actinic keratosis
US7943610B2 (en) 2005-04-01 2011-05-17 3M Innovative Properties Company Pyrazolopyridine-1,4-diamines and analogs thereof
US7943636B2 (en) 2005-04-01 2011-05-17 3M Innovative Properties Company 1-substituted pyrazolo (3,4-C) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases
WO2006116475A2 (en) 2005-04-25 2006-11-02 3M Innovative Properties Company Immunostimulatory compositions
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
US20070123559A1 (en) * 2005-09-15 2007-05-31 3M Innovative Properties Company PACKAGING FOR 1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-c] QUINOLIN-4-AMINE-CONTAINING FORMULATION
EP3085373A1 (en) 2006-02-22 2016-10-26 3M Innovative Properties Company Immune response modifier conjugates
US8951528B2 (en) 2006-02-22 2015-02-10 3M Innovative Properties Company Immune response modifier conjugates
US20090035323A1 (en) * 2006-02-22 2009-02-05 Doris Stoermer Immune response modifier conjugates
US7906506B2 (en) 2006-07-12 2011-03-15 3M Innovative Properties Company Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods
US9827195B2 (en) 2006-07-14 2017-11-28 Stiefel Research Australia Pty Ltd Fatty acid pharmaceutical foam
US20080015271A1 (en) * 2006-07-14 2008-01-17 Stiefel Research Austrialia Pty Ltd Fatty acid pharmaceutical foam
US9023863B2 (en) 2006-07-14 2015-05-05 Stiefel Research Australia Pty Ltd Fatty acid pharmaceutical foam
EP2046121A4 (en) * 2006-07-14 2010-10-20 Stiefel Res Australia Pty Ltd PHARMACEUTICAL FOAM WITH FATTY ACID
EP2046121A2 (en) * 2006-07-14 2009-04-15 Stiefel Research Australia Pty Ltd Fatty acid pharmaceutical foam
US20100092401A1 (en) * 2006-07-18 2010-04-15 Graceway Pharmaceuticals, Llc Immune response modifier formulations
RU2481108C2 (ru) * 2006-07-18 2013-05-10 Меда Аб Пенный состав модификатора иммунного ответа, способ получения лекарственного средства на его основе (варианты) и лекарственный набор, содержащий указанный состав
US20100096287A1 (en) * 2006-07-31 2010-04-22 Stoesz James D Immune Response Modifier Compositions and Methods
US8124096B2 (en) 2006-07-31 2012-02-28 3M Innovative Properties Company Immune response modifier compositions and methods
US10144735B2 (en) 2006-12-22 2018-12-04 3M Innovative Properties Company Immune response modifier compositions and methods
US10005772B2 (en) 2006-12-22 2018-06-26 3M Innovative Properties Company Immune response modifier compositions and methods
WO2008082382A1 (en) * 2006-12-29 2008-07-10 Graceway Pharmaceuticals, Inc. Packaging for 1-(2-methylpropyl)-1h-imidazo[4,5-c]quinolin-4-amine containing formulation
WO2008082381A1 (en) * 2006-12-29 2008-07-10 3M Innovative Properties Company Immune response modifier formulations containing oleic acid and methods
WO2009118296A2 (en) * 2008-03-24 2009-10-01 4Sc Ag Novel substituted imidazoquinolines
EA023556B1 (ru) * 2008-03-24 2016-06-30 4ЭсЦэ АГ 1,2-дизамещенные-4-аминоимидазохинолины
US9908880B2 (en) 2008-03-24 2018-03-06 4Sc Ag Substituted imidazoquinolines
US9073913B2 (en) 2008-03-24 2015-07-07 4Sc Ag Substituted imidazoquinolines
WO2009118296A3 (en) * 2008-03-24 2009-12-03 4Sc Ag Novel substituted imidazoquinolines
US9446040B2 (en) 2008-03-24 2016-09-20 4Sc Ag Substituted imidazoquinolines
US20100160368A1 (en) * 2008-08-18 2010-06-24 Gregory Jefferson J Methods of Treating Dermatological Disorders and Inducing Interferon Biosynthesis With Shorter Durations of Imiquimod Therapy
US8598196B2 (en) 2008-08-18 2013-12-03 Medicis Pharmaceutical Corporation Methods of treating dermatological disorders and inducing interferon biosynthesis with shorter durations of imiquimod therapy
US9271973B2 (en) 2008-08-18 2016-03-01 Medicis Pharmaceutical Corporation Methods of treating dermatological disorders and inducing interferon biosynthesis with shorter durations of imiquimod therapy
US20110207765A1 (en) * 2008-10-31 2011-08-25 Moberg Derma Ab Topical composition comprising a combination of at least two penetration enhancing agents
US20130202650A1 (en) * 2008-10-31 2013-08-08 Moberg Derma Ab Topical composition comprising a combination of at least two penetration enhancing agents
US8236816B2 (en) 2008-12-19 2012-08-07 Medicis Pharmaceutical Corporation 2×2×2 week dosing regimen for treating actinic keratosis with pharmaceutical compositions formulated with 3.75 % imiquimod
US20110021555A1 (en) * 2008-12-19 2011-01-27 Graceway Pharmaceuticals, Llc Lower dosage strength imiquimod formulations and shorter dosing regimens for treating actinic keratoses
US8222270B2 (en) 2008-12-19 2012-07-17 Medicis Pharmaceutical Corporation 2×2×2 week treatment regimen for treating actinic keratosis with pharmaceutical compositions formulated with 2.5% imiquimod
US11318130B2 (en) 2008-12-19 2022-05-03 Medicis Pharmaceutical Corporation 2x2x2 week dosing regimen for treating actinic keratosis with pharmaceutical compositions formulated with 3.75% imiquimod
US10238644B2 (en) 2008-12-19 2019-03-26 Medicis Pharmaceutical Corporation 2×2×2 week dosing regimen for treating acting keratosis with pharmaceutical compositions formulated with 3.75% imiquimod
US8299109B2 (en) 2008-12-19 2012-10-30 Medicis Pharmaceutical Corporation Method of treating actinic keratosis with 3.75% imiquimod cream
US9370509B2 (en) 2008-12-19 2016-06-21 Medicis Pharmaceutical Corporation 2×2×2 week dosing regimen for treating actinic keratosis with pharmaceutical compositions formulated with 3.75 % imiquimod
US20110207766A1 (en) * 2009-07-13 2011-08-25 Graceway Pharmaceuticals, Llc. Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts
US9980955B2 (en) 2009-07-13 2018-05-29 Medicis Pharmaceutical Corporation Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts
US8642616B2 (en) 2009-07-13 2014-02-04 Medicis Pharmaceutical Corporation Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts
US9078889B2 (en) 2009-07-13 2015-07-14 Medicis Pharmaceutical Corporation Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts
US10238645B2 (en) 2009-07-13 2019-03-26 Medicis Pharmaceutical Corporation Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts
US10918635B2 (en) 2009-07-13 2021-02-16 Medicis Pharmaceutical Corporation Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts
US11850245B2 (en) 2009-07-13 2023-12-26 Medicis Pharmaceutical Corporation Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts
EP3222621A1 (en) 2010-08-17 2017-09-27 3M Innovative Properties Company Lipidated immune response modifier compound and its medical use
US11020486B2 (en) * 2013-11-05 2021-06-01 3M Innovative Properties Company Sesame oil based injection formulations
US9962453B2 (en) 2013-12-02 2018-05-08 Altimmune Uk Limited Immunogenic compound
US10434183B2 (en) 2013-12-02 2019-10-08 Altimmune UK Ltd. Immunogenic compound
US10849984B2 (en) 2013-12-02 2020-12-01 Altimmune Uk Limited Immunogenic compound

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