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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US7968562B2 (en) 2011-06-28
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