US20060252791A1 - Imidazo[4,5-c]pyridine compound and method of antiviral treatment - Google Patents

Imidazo[4,5-c]pyridine compound and method of antiviral treatment Download PDF

Info

Publication number
US20060252791A1
US20060252791A1 US11/316,050 US31605005A US2006252791A1 US 20060252791 A1 US20060252791 A1 US 20060252791A1 US 31605005 A US31605005 A US 31605005A US 2006252791 A1 US2006252791 A1 US 2006252791A1
Authority
US
United States
Prior art keywords
compound
imidazo
agents
acid
salts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US11/316,050
Other languages
English (en)
Inventor
Steven Bondy
David Oare
Winston Tse
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Katholieke Universiteit Leuven
Original Assignee
Gilead Sciences Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc
Priority to US11/316,050 priority Critical patent/US20060252791A1/en
Publication of US20060252791A1 publication Critical patent/US20060252791A1/en
Assigned to GILEAD SCIENCES, INC. reassignment GILEAD SCIENCES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BONDY, STEVEN S., TSE, WINSTON C., OARE, DAVID A.
Priority to US12/022,557 priority patent/US7795276B2/en
Assigned to K.U. LEUVEN RESEARCH & DEVELOPMENT, GILEAD SCIENCES, INC., PUERSTINGER, GERHARD reassignment K.U. LEUVEN RESEARCH & DEVELOPMENT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GILEAD SCIENCES, INC.
Assigned to K.U. LEUVEN RESEARCH & DEVELOPMENT reassignment K.U. LEUVEN RESEARCH & DEVELOPMENT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GILEAD SCIENCES, INC.
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses

Definitions

  • the present invention relates to compounds useful in the treatment or prophylaxis of viral infections, particularly those by the Flaviviridae and Picornaviridae families including hepatitis C virus (HCV).
  • HCV hepatitis C virus
  • the Flaviviridae family consists of 3 genera, the pestiviruses, the flaviviruses and the hepaciviruses. It also contains the hepatitis G virus (HGV/GBV-C), which has not yet been assigned to a genus. Pestiviruses such as the Classical Swine Fever Virus (CSFV), the Bovine Viral Diarrhea Virus (BVDV) and the Border Disease Virus (BDV) cause infections of domestic livestock (respectively pigs, cattle and sheep) and are responsible for significant economic losses world-wide.
  • CSFV Classical Swine Fever Virus
  • BVDV Bovine Viral Diarrhea Virus
  • BDV Border Disease Virus
  • BVDV the prototypic representative of the pestivirus genus, is ubiquitous and causes a range of clinical manifestations, including abortion, teratogenesis, respiratory problems, chronic wasting disease, immune system dysfunction, and predisposition to secondary viral and bacterial infections.
  • Vaccines are used in some countries with varying degrees of success to control pestivirus disease. In other countries, animal culling and slaughter are used to contain pestivirus disease outbreaks.
  • the World Health Organization estimates that world-wide 170 million people (3% of the world's population) are chronically infected with HCV. These chronic carriers are at risk of developing cirrhosis and/or liver cancer. In studies with a 10 to 20 year follow-up, cirrhosis developed in 20-30% of the patients, 1 to 5% of whom may develop liver cancer during the next ten years.
  • the only treatment option available today is the use of interferon ⁇ -2 (or its pegylated from) either alone or combined with ribavirin. However, sustained response is only observed in about 40% of the patients and treatment is associated with serious adverse effects. There is thus an urgent need for potent and selective inhibitors of HCV.
  • Coxsackie viruses belong to the enteroviruses of the Picornaviridae family. They cause a heterogeneous group of infections including herpangina, aseptic meningitis, a common-cold-like syndrome, a non-paralytic poliomyelitis-like syndrome, epidemic pleurodynia (an acute, febrile, infectious disease generally occurring in epidemics), hand-foot-mouth syndrome, pediatric and adult pancreatitis and serious myocarditis.
  • the novel compound 5-((3-(2,4-trifluoromethyphenyl)isoxazol-5-yl)methyl)-2-(2-fluorophenyl)-5H-imidazo[4,5-c]pyridine and its salts and solvates.
  • compositions comprising the compound of this invention together with pharmaceutically acceptable carriers, as well as the use of such compositions in the treatment or prophylaxis of viral, especially HCV, infections.
  • the compound of this invention is employed for the treatment or prophylaxis of flaviviral or picornaviral infections, in particular HCV and BVDV.
  • the therapeutic compound of this invention is administered to a subject mammal (including a human) by any means well known in the art, i.e. orally, intranasally, subcutaneously, intramuscularly, intradermally, intravenously, intra-arterially, parenterally or by catheterization in a therapeutically effective amount, i.e., a flaviviral or picornaviral growth inhibiting amount or a flaviviral or picornaviral replication inhibiting amount.
  • a therapeutically effective amount i.e., a flaviviral or picornaviral growth inhibiting amount or a flaviviral or picornaviral replication inhibiting amount.
  • This amount is believed to be an amount that ensures a plasma level of between about 1 ⁇ g/ml and 100 mg/ml, optionally of 10 mg/ml.
  • Dosages of 1, 3, 6, 10, 20, 30 and 60 mg/kg are suitable for conducting toxicity studies in dogs and for extrapolating to suitable doses in humans.
  • the optimal dosage of the compound of this invention will depend upon many factors known to the artisan, including bioavailability of the compound, its metabolism and distribution in the subject, its toxicity and its potency, among others. Proper dosing typically is determined in the preclinical and clinical settings, and is well within the skill of the ordinary artisan.
  • the therapeutically effective amount of the compound of this invention optionally is divided into several sub-units per day or is administered daily or in more than one day intervals, depending upon the nature of the infection, the patient's general condition and the nature of the compound of this invention. Generally, the compound is administered daily.
  • the compound of this invention is employed in concert with other agents effective against Picornaviral or Flaviviral infections.
  • agents include, for instance, interferon alpha, ribavirin, and/or compounds falling within the disclosures of EP1162196, WO 03/010141, WO 03/007945 WO 00/204425 and/or WO 03/010140 (and other filings within their patent families).
  • Such other agents are used in conventional amounts, although if the efficacy of the compound of this invention and the other compound is additive then the amounts of each active agent optionally are commensurately reduced, and more so if the agents act synergistically. In general, however, the agents are used in their ordinary active amounts in the compositions.
  • Co-administered agents generally are formulated into unitary compositions with the compound of this invention so long as they are chemically compatible and are intended to be administered by the same route. If not, then they optionally are provided in the form of a medical kit or package containing the two agents in separate repositories or compartments.
  • the present invention further provides veterinary compositions comprising at least one compound of this invention together with a veterinary carrier therefor, for example in the treatment of BVDV.
  • Veterinary carriers are materials useful for the purpose of administering the composition and are excipients which are otherwise inert or acceptable in the veterinary art and are compatible with the compound of this invention. These veterinary compositions are administered orally, parenterally or by any other desired route.
  • the compound of this invention is provided as the free base or as a salt.
  • Salts typically are prepared by acid addition of certain organic and inorganic acids to the free base. Examples include (1) inorganic acids such as hydrohalogen acids, e.g. hydrochloric or hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and sulfamic acids; or (2) organic acids such as acetic, propanoic, hydroxyacetic, benzoic, 2-hydroxypropanoic, 2-oxopropanoic, lactic, fumaric, tartaric, pyruvic, maleic, malonic, malic, salicylic (e.g.
  • 2-hydroxybenzoic p-aminosalicylic, isethionic, lactobionic, succinic, oxalic and citric acids; organic sulfonic acids, such as methanesulfonic, ethanesulfonic, benzenesulfonic, p-toluenesulfonic, C1-C6 alkylsulfonic, benzenesulfonic, p-toluenesulfonic, and cyclohexanesulfamic acids. Also included within the scope of this invention are the salts of the compound of this invention with one or more amino acids, typically naturally-occuring amino acids such as one of the amino acids found in proteins.
  • the acidic counterion desirably is physiologically innocuous and non-toxic or otherwise pharmaceutically acceptable, unless the salt is being used as an intermediate in preparation of the compounds whereupon toxicity is not relevant. While the free base is preferred, suitable salts include mesylate (methanesulfonic acid) and HCl.
  • the compound of this invention includes the solvates formed with the compound of this invention or their salts, such as for example hydrates, alcoholates and the like.
  • the compound of this invention optionally is formulated with conventional pharmaceutical carriers and excipients, which will be selected in accord with ordinary practice. Tablets will contain excipients, glidants, fillers, binders and the like. Aqueous formulations are prepared in sterile form, and when intended for delivery by other than oral administration generally will be isotonic. Formulations optionally contain excipients such as those set forth in the “Handbook of Pharmaceutical Excipients” (1986) and include ascorbic acid and other antioxidants, chelating agents such as EDTA, carbohydrates such as dextrin, hydroxyalkylcellulose, hydroxyalkylmethylcellulose and stearic acid.
  • pharmaceutically acceptable carrier means any material or substance with which the active ingredient is formulated in order to facilitate its preparation and/or its application or dissemination to the site to be treated.
  • Suitable pharmaceutical carriers for use in the compositions of this invention are well known to those skilled in the art. They include additives such as wetting agents, dispersing agents, adhesives, emulsifying agents, solvents, glidants, coatings, antibacterial and antifungal agents (for example phenol, sorbic acid, chlorobutanol), isotonic agents (such as sugars or sodium chloride), provided that the same are consistent with pharmaceutical practice, i.e. they are not toxic to mammals.
  • compositions of the present invention are prepared in any known manner, for instance by homogeneously mixing, coating and/or grinding the active ingredients in a one-step or multi-step procedure, with the selected carrier material and, where appropriate, other additives such as surface-active agents.
  • Compositions containing the compound of this invention formulated into microspheres are useful as controlled or sustained release formulations.
  • Suitable surface-active agents also known as emulgents or emulsifiers, are useful in the pharmaceutical compositions of the present invention. They are non-ionic, cationic and/or anionic materials having suitable emulsifying, dispersing and/or wetting properties.
  • Suitable anionic surfactants include both water-soluble soaps and water-soluble synthetic surface-active agents.
  • Suitable soaps are alkaline or alkaline-earth metal salts, unsubstituted or substituted ammonium salts of higher fatty acids (C 10 -C 22 ), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures obtainable from coconut oil or tallow oil.
  • Synthetic surfactants include sodium or calcium salts of polyacrylic acids; fatty sulphonates and sulphates; sulphonated benzimidazole derivatives and alkylarylsulphonates.
  • Fatty sulphonates or sulphates are usually in the form of alkaline or alkaline-earth metal salts, unsubstituted ammonium salts or ammonium salts substituted with an alkyl or acyl radical having from 8 to 22 carbon atoms, e.g.
  • Suitable sulphonated benzimidazole derivatives preferably contain 8 to 22 carbon atoms.
  • alkylarylsulphonates are the sodium, calcium or alcoholamine salts of dodecylbenzene sulphonic acid or dibutyl-naphthalenesulphonic acid or a naphthalene-sulphonic acid/formaldehyde condensation product.
  • corresponding phosphates e.g. salts of phosphoric acid ester and an adduct of p-nonylphenol with ethylene and/or propylene oxide, or phospholipids.
  • Suitable phospholipids for this purpose are the natural (originating from animal or plant cells) or synthetic phospholipids of the cephalin or lecithin type such as e.g.
  • phosphatidylethanolamine phosphatidylserine, phosphatidylglycerine, lysolecithin, cardiolipin, dioctanylphosphatidyl-choline, dipalmitoylphoshatidyl-choline and their mixtures.
  • Suitable non-ionic surfactants include polyethoxylated and polypropoxylated derivatives of alkylphenols, fatty alcohols, fatty acids, aliphatic amines or amides containing at least 12 carbon atoms in the molecule, alkylarenesulphonates and dialkylsulphosuccinates, such as polyglycol ether derivatives of aliphatic and cycloaliphatic alcohols, saturated and unsaturated fatty acids and alkylphenols, said derivatives preferably containing 3 to 10 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenol.
  • non-ionic surfactants are water-soluble adducts of polyethylene oxide with poylypropylene glycol, ethylenediaminopolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethyleneglycol ether groups and/or 10 to 100 propyleneglycol ether groups.
  • Such compounds usually contain from I to 5 ethyleneglycol units per propyleneglycol unit.
  • non-ionic surfactants are nonylphenol-polyethoxyethanol, castor oil polyglycolic ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethyleneglycol and octylphenoxypolyethoxyethanol.
  • Fatty acid esters of polyethylene sorbitan such as polyoxyethylene sorbitan trioleate
  • glycerol glycerol
  • sorbitan sucrose and pentaerythritol are also suitable non-ionic surfactants.
  • Suitable cationic surfactants include quaternary ammonium salts, particularly halides, having 4 hydrocarbon radicals optionally substituted with halo, phenyl, substituted phenyl or hydroxy; for instance quaternary ammonium salts containing as N-substituent at least one C8C22 alkyl radical (e.g. cetyl, lauryl, palmityl, myristyl and oleyl) and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl and/or hydroxy-lower alkyl radicals.
  • C8C22 alkyl radical e.g. cetyl, lauryl, palmityl, myristyl and oleyl
  • the compound of this invention is administered by any route appropriate to the condition to be treated, such as oral, rectal, nasal, topical (including ocular, buccal and sublingual), vaginal and parenteral (including subcutaneous, intramuscular, intravenous, intradermal, intrathecal and epidural).
  • routes appropriate to the condition to be treated such as oral, rectal, nasal, topical (including ocular, buccal and sublingual), vaginal and parenteral (including subcutaneous, intramuscular, intravenous, intradermal, intrathecal and epidural).
  • the preferred route of administration may vary with for example the condition of the recipient, but is generally oral.
  • Formulations of the compound of this invention for oral administration usually are presented as discrete units such as capsules, cachets or tablets each containing a predetermined amount of the active ingredient; as a powder or granular form; as a solution or suspension in an aqueous liquid or a non-aqueous liquid; or as an oil-in-water liquid emulsion or a water-in-oil liquid emulsion.
  • the compound of this invention optionally is presented as a bolus, electuary or paste.
  • a tablet is made by compression or molding, optionally with one or more accessory ingredients.
  • Compressed tablets are prepared by compressing in a suitable machine the compound of the invention in a free-flowing form such as a powder or granules, optionally mixed with a binder, lubricant, inert diluent, preservative, surface active and/or dispersing agent.
  • Molded tablets typically are made by molding in a suitable machine a mixture of the powdered compound moistened with an inert liquid diluent.
  • the tablets may optionally be coated or scored and may be formulated so as to provide slow or controlled release of the active ingredient therein.
  • the formulations are optionally applied as a topical ointment or cream containing the active ingredient(s) in an amount of, for example, 0.075 to 20% w/w (including active ingredient(s) in a range between 0.1% and 20% in increments of 0.1% w/w such as 0.6% w/w, 0.7% w/w, etc), preferably 0.2 to 15% w/w and most preferably 0.5 to 10% w/w.
  • the compound is employed with a paraffinic or a water-miscible ointment base.
  • the compound is formulated in a cream with an oil-in-water cream base.
  • the aqueous phase of the cream base may include, for example, at least 30% w/w of a polyhydric alcohol, i.e. an alcohol having two or more hydroxyl groups such as propylene glycol, butane 1,3-diol, mannitol, sorbitol, glycerol and polyethylene glycol (including PEG400) and mixtures thereof.
  • the topical formulations may desirably include a compound which enhances absorption or penetration of the active ingredient through the skin or other affected areas. Examples of such dermal penetration enhancers include dimethylsulfoxide and related analogs.
  • the oily phase of the emulsions of this invention is constituted from known ingredients in a known manner. While this phase may comprise merely an emulsifier (otherwise known as an emulgent), it desirably comprises a mixture of at least one emulsifier with a fat or an oil or with both a fat and an oil. Optionally, a hydrophilic emulsifier is included together with a lipophilic emulsifier which acts as a stabilizer. It is also preferred to include both an oil and a fat.
  • the emulsifier(s) with or without stabilizer(s) make up the so-called emulsifying wax
  • the wax together with the oil and fat make up the so-called emulsifying ointment base which forms the oily dispersed phase of the cream formulations.
  • suitable oils or fats for the formulation is based on achieving the desired cosmetic properties.
  • the cream should optionally be a non-greasy, non-staining and washable product with suitable consistency to avoid leakage from tubes or other containers.
  • Straight or branched chain, mono- or dibasic alkyl esters such as di-isoadipate, isocetyl stearate, propylene glycol diester of coconut fatty acids, isopropyl myristate, decyl oleate, isopropyl palmitate, butyl stearate, 2-ethylhexyl palmitate or a blend of branched chain esters known as Crodamol CAP may be used, the last three being preferred esters.
  • Crodamol CAP may be used, the last three being preferred esters.
  • high melting point lipids such as white soft paraffin and/or liquid paraffin or other mineral oils can be used.
  • Formulations suitable for topical administration to the eye also include eye drops wherein the active ingredient is dissolved or suspended in a suitable carrier, especially an aqueous solvent for the active ingredient.
  • a suitable carrier especially an aqueous solvent for the active ingredient.
  • the active ingredient is optionally present in such formulations in a concentration of 0.5 to 20%, advantageously 0.5 to 10% particularly about 1.5% w/w.
  • Formulations suitable for topical administration in the mouth include lozenges comprising the active ingredient in a flavored basis, usually sucrose and acacia or tragacanth; pastilles comprising the active ingredient in an inert basis such as gelatin and glycerin, or sucrose and acacia; and mouthwashes comprising the active ingredient in a suitable liquid carrier.
  • Formulations for rectal administration may be presented as a suppository with a suitable base comprising for example cocoa butter or a salicylate.
  • Formulations suitable for nasal administration wherein the carrier is a solid include a coarse powder having a particle size for example in the range 20 to 500 microns (including particle sizes in a range between 20 and 500 microns in increments of 5 microns such as 30 microns, 35 microns, etc), which is administered by aerosol or powder inhalers, of which numerous examples are available.
  • Suitable formulations wherein the carrier is a liquid, for administration as for example a nasal spray or as nasal drops include aqueous or oily solutions of the active ingredient.
  • Formulations suitable for vaginal administration may be presented as pessaries, tampons, creams, gels, pastes, foams or spray formulations containing in addition to the active ingredient such carriers as are known in the art to be appropriate.
  • Formulations suitable for parenteral administration include aqueous and non-aqueous sterile injection solutions which may contain anti-oxidants, buffers, bacteriostats and solutes which render the formulation isotonic with the blood of the intended recipient; and aqueous and non-aqueous sterile suspensions which may include suspending agents and thickening agents.
  • the formulations are presented in unit-dose or multi-dose containers, for example sealed ampoules and vials, and may be stored in a freeze-dried (lyophilized) condition requiring only the addition of the sterile liquid carrier, for example water for injections, immediately prior to use.
  • Extemporaneous injection solutions and suspensions may be prepared from sterile powders, granules and tablets of the kind previously described.
  • the compound of this invention is formulated into controlled release compositions in which the release of the compound is controlled and regulated to allow less frequency dosing or to improve the pharmacokinetic or toxicity profile of the invention compound.
  • Controlled release compositions are prepared in accord with known methods, many of which involve formulating the active compound with one or more polymer carriers such a polyester, polyamino acid, polyvinyl pyrrolidone, ethylene-vinyl acetate copolymer, methylcellulose, carboxymethylcellulose and/or protamine sulfate.
  • the rate of drug release and duration of action optionally is controlled by incorporating the active ingredient into particles, e.g.
  • microcapsules of a polymeric substance such as hydrogels, polylactic acid, hydroxymethylcellulose, polymethyl methacrylate and the other above-described polymers.
  • a polymeric substance such as hydrogels, polylactic acid, hydroxymethylcellulose, polymethyl methacrylate and the other above-described polymers.
  • colloid drug delivery systems such as liposomes, microspheres, microemulsions, nanoparticles, nanocapsules and so on.
  • the pharmaceutical composition e.g., tablets, may require protective coatings.
  • 2,4-(bis-trifluoromethyl)benzaldoxime (9.75 g, 0.038 mol) was suspended in CH 2 Cl 2 (45 mL, 0.85 M) and cooled to 4° C.
  • Propargyl chloride (2.72 mL, 0.038 mol) was added to the reaction solution followed by dropwise addition of NaOCl (10-13% free chlorine, 37.6 mL, 0.061 mol).
  • the reaction mixture was stirred at 4° C. for 15 min then heated to reflux for 3 h. After cooling to room temperature, the reaction was partitioned between CH 2 Cl 2 and H 2 O. The organic layer was separated, washed with saturated aqueous NaCl, and dried over sodium sulfate. After removal of solvent, the crude product chloromethylisoxazole was purified by column chromatography on silica (10% CH 2 Cl 2 /hexanes)(6.5 g ,0.020 mol).

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Molecular Biology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
US11/316,050 2004-12-21 2005-12-21 Imidazo[4,5-c]pyridine compound and method of antiviral treatment Abandoned US20060252791A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US11/316,050 US20060252791A1 (en) 2004-12-21 2005-12-21 Imidazo[4,5-c]pyridine compound and method of antiviral treatment
US12/022,557 US7795276B2 (en) 2004-12-21 2008-01-30 Imiadazo[4,5-c] pyridine compound and method of antiviral treatment

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US63821504P 2004-12-21 2004-12-21
US11/316,050 US20060252791A1 (en) 2004-12-21 2005-12-21 Imidazo[4,5-c]pyridine compound and method of antiviral treatment

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/022,557 Continuation US7795276B2 (en) 2004-12-21 2008-01-30 Imiadazo[4,5-c] pyridine compound and method of antiviral treatment

Publications (1)

Publication Number Publication Date
US20060252791A1 true US20060252791A1 (en) 2006-11-09

Family

ID=36481451

Family Applications (2)

Application Number Title Priority Date Filing Date
US11/316,050 Abandoned US20060252791A1 (en) 2004-12-21 2005-12-21 Imidazo[4,5-c]pyridine compound and method of antiviral treatment
US12/022,557 Expired - Fee Related US7795276B2 (en) 2004-12-21 2008-01-30 Imiadazo[4,5-c] pyridine compound and method of antiviral treatment

Family Applications After (1)

Application Number Title Priority Date Filing Date
US12/022,557 Expired - Fee Related US7795276B2 (en) 2004-12-21 2008-01-30 Imiadazo[4,5-c] pyridine compound and method of antiviral treatment

Country Status (16)

Country Link
US (2) US20060252791A1 (xx)
EP (1) EP1841765B1 (xx)
JP (2) JP2008524335A (xx)
AT (1) ATE426601T1 (xx)
AU (1) AU2005319167B2 (xx)
CA (1) CA2592388C (xx)
CY (1) CY1109087T1 (xx)
DE (1) DE602005013580D1 (xx)
DK (1) DK1841765T5 (xx)
ES (1) ES2324794T3 (xx)
HK (1) HK1113570A1 (xx)
NZ (1) NZ556624A (xx)
PL (1) PL1841765T3 (xx)
PT (1) PT1841765E (xx)
SI (1) SI1841765T1 (xx)
WO (1) WO2006069193A2 (xx)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050239821A1 (en) * 2002-07-03 2005-10-27 Johan Neyts Viral inhibitors
US20070244148A1 (en) * 2003-12-22 2007-10-18 Bondy Steven S Imidazo 4,5-C Pyridine Compounds and Methods of Antiviral Treatment
US20080199427A1 (en) * 2006-07-07 2008-08-21 Bondy Steven S Novel pyridazine compound and use thereof
US20090036460A1 (en) * 2007-07-06 2009-02-05 Gilead Sciences, Inc. Crystalline pyridazine compound
US8815858B2 (en) 2010-05-21 2014-08-26 Gilead Sciences, Inc. Heterocyclic flaviviridae virus inhibitors

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK2094702T3 (en) 2006-12-14 2015-12-07 Gilead Sciences Inc viral inhibitors
TW200920372A (en) * 2007-07-13 2009-05-16 Genelabs Tech Inc Anti-viral compounds, compositions, and methods of use
HRP20211456T1 (hr) 2014-12-26 2021-12-24 Emory University Protuvirusni derivati n4-hidroksicitidina
KR102248165B1 (ko) 2017-12-07 2021-05-06 에모리 유니버시티 N4-하이드록시사이티딘 및 유도체 및 이와 관련된 항-바이러스 용도

Citations (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3985891A (en) * 1973-02-03 1976-10-12 Boehringer Ingelheim Gmbh 2-Phenyl-imidazo (4,5-b)pyridines and salts thereof
US4565816A (en) * 1982-05-28 1986-01-21 Sandoz Ltd. Piperazine derivatives and pharmaceutical composition containing them
US4692443A (en) * 1983-10-17 1987-09-08 Eli Lilly And Company 3-bicyclicpyridinium-methyl cephalosporins
US4804658A (en) * 1986-09-15 1989-02-14 G. D. Searle & Co. Imidazopyridine derivatives and pharmaceutical compositions
US4914108A (en) * 1988-03-14 1990-04-03 G. D. Searle & Co. 5-substituted(4,5-c)imidazopyridine compounds which have useful platelet activating factor antagonistic activity
US4988707A (en) * 1989-09-13 1991-01-29 G. D. Searle & Co. Pharmacologically active phenylalkanoyl substituted imidazo (4,5-C) pyridines
US4990518A (en) * 1989-09-13 1991-02-05 G. D. Searle & Co. Pharmacologically active heteroaryl substituted imidazo (4,5-c) pyridines
US5011832A (en) * 1990-06-26 1991-04-30 Merck & Co., Inc. 2-biphenyl-carbapenem antibacterial agents
US5019581A (en) * 1988-03-14 1991-05-28 G. D. Searle & Co. 5-substituted (4,5-c) imidazopyridine compounds which have useful platelet activating factor antagonistic activity
US5057517A (en) * 1987-07-20 1991-10-15 Merck & Co., Inc. Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents
US5137896A (en) * 1981-10-01 1992-08-11 Janssen Pharmaceutica N.V. N-(3-hydroxy-4-piperidinyl)benzamide derivatives
US5208242A (en) * 1992-08-26 1993-05-04 G. D. Searle & Co. 5-substituted-4-phenyl-5H-imidazo[4,5-c]pyridine derivatives
US5227384A (en) * 1988-03-14 1993-07-13 G. D. Searle & Co. 5-substituted [4,5-c] imidazopyridines and pharmaceutical use thereof
US5302601A (en) * 1988-03-14 1994-04-12 G. D. Searle & Co. 5-substituted imidazo[4,5-c]pyridines
US5332744A (en) * 1989-05-30 1994-07-26 Merck & Co., Inc. Substituted imidazo-fused 6-membered heterocycles as angiotensin II antagonists
US5374638A (en) * 1993-03-19 1994-12-20 Merck & Co., Inc. Six membered ring fused imidazoles substituted with phenoxyphenylacetic acid derivatives used to treat asthma
US5405964A (en) * 1992-10-24 1995-04-11 Merck Patent Gesellschaft Mit Beschrankter Haftung Imidazopyridines
US5438063A (en) * 1993-06-07 1995-08-01 Merck Patent Gesellschaft Mit Beschrankter Haftung Imidazopyridines as angiotensin II antagonists
US5446032A (en) * 1991-07-24 1995-08-29 British Biotech Pharmaceuticals Limited Imidazo (4,5-C) pyridine derivatives as PAF antagonists
US5486525A (en) * 1993-12-16 1996-01-23 Abbott Laboratories Platelet activating factor antagonists: imidazopyridine indoles
US5585492A (en) * 1994-10-11 1996-12-17 G. D. Searle & Co. LTA4 Hydrolase inhibitors
US5587372A (en) * 1991-12-12 1996-12-24 Roussel Uclaf Cephalosporins
US5607944A (en) * 1993-07-22 1997-03-04 Karl Thomae Gmbh Bicyclic heterocyclic compounds, pharmaceutical preparations containing these compounds and processes for their preparations
US6329381B1 (en) * 1997-11-28 2001-12-11 Sumitomo Pharmaceuticals Company, Limited Heterocyclic compounds
US6479508B1 (en) * 2000-07-06 2002-11-12 Boehringer Ingelheim (Canada) Ltd. Viral polymerase inhibitors
US6492384B1 (en) * 1998-10-01 2002-12-10 Merck Patent Gmbh Imidazo (4,5-C) pyridine-4-one derivatives with factor XA inhibiting effect
US20030108862A1 (en) * 2001-08-07 2003-06-12 Boehringer Ingelheim (Canada) Ltd. Direct binding assay for identifying inhibitors of HCV polymerase
US20040082635A1 (en) * 2001-06-26 2004-04-29 Hiromasa Hashimoto Fused cyclic compounds and medicinal use thereof
US20040097574A1 (en) * 2002-08-29 2004-05-20 Boehringer Ingelheim Pharmaceuticals, Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
US20040097438A1 (en) * 1999-12-27 2004-05-20 Japan Tobacco Inc. Fused-ring compounds and use thereof as drugs
US20050222198A1 (en) * 2003-12-22 2005-10-06 K.U. Leuven Research & Development, Gerhard Puerstinger And Gilead Sciences, Inc. Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment
US7112600B1 (en) * 1999-12-27 2006-09-26 Japan Tobacco Inc. Fused-ring compounds and use thereof as drugs

Family Cites Families (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2191978A (en) * 1935-10-10 1940-02-27 Ig Farbenindustrie Ag Quaternary nitrogen compounds and process of preparing them
US2411662A (en) * 1943-05-13 1946-11-26 Geigy Ag J R Imino-di-fatty acid amide
US2548863A (en) * 1946-05-29 1951-04-17 Wyeth Corp Substituted glycinamides
US2516674A (en) * 1948-10-29 1950-07-25 Wyeth Corp Substituted glycinamide
SU813921A1 (ru) 1979-10-26 1986-12-23 Институт физико-органической химии и углехимии АН УССР Стирильные производные имидазо(4,5- @ )пиридиний иодида,обладающие фунгицидной активностью
SU851940A1 (ru) 1980-03-20 1988-04-30 Институт физико-органической химии и углехимии АН УССР Четвертичные соли имидазо @ 4,5-с @ пиридини ,обладающие антимикробной и фунгистатической активностью
SU1048742A1 (ru) 1981-03-30 1986-12-23 Институт физико-органической химии и углехимии АН УССР 2,4-Дистирилпроизводные имидазо-(4,5- @ )пиридини ,обладающие бактериостатической и фунгистатической активностью
US4358387A (en) * 1981-08-10 1982-11-09 Texaco Inc. Cylinder lubricating oil composition
CA1183847A (en) 1981-10-01 1985-03-12 Georges Van Daele N-(3-hydroxy-4-piperidinyl)benzamide derivatives
EP0138552A3 (en) 1983-10-17 1986-03-19 Eli Lilly And Company Improvements on or relating to 3-bicyclicpyridinium-methyl cephalosporins
GB8501542D0 (en) 1985-01-22 1985-02-20 Erba Farmitalia 4 5 6 7-tetrahydro-imidazo(4 5-clpyridine derivatives
GB8530602D0 (en) 1985-12-12 1986-01-22 Fujisawa Pharmaceutical Co Heterocyclic compounds
DE3781173T2 (de) 1986-02-03 1992-12-17 Janssen Pharmaceutica Nv N-heterozyklische-4-piperidinamine enthaltende anti-histaminische zusammensetzungen.
US4968707A (en) * 1987-06-10 1990-11-06 Pfizer Inc. Oxazolidin-2-one derivatives as hypoglycemic agents
NZ225447A (en) 1987-07-20 1991-12-23 Merck & Co Inc Piperazinyl derivatives of purine and purine isosteres and pharmaceutical compositions
FR2663332B1 (fr) 1990-06-15 1997-11-07 Roussel Uclaf Nouvelles cephalosporines comportant en position 3 un radical propenyle substitue par un ammonium quaternaire, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus.
JPH04327587A (ja) 1991-04-26 1992-11-17 Asahi Chem Ind Co Ltd ６’−ｃ−アルキル−３−デアザネプラノシンａ誘導体、その製造法およびその用途
GB9202792D0 (en) 1992-02-11 1992-03-25 British Bio Technology Compounds
DE4211474A1 (de) 1992-04-06 1993-10-07 Merck Patent Gmbh Imidazopyridine
DE4230464A1 (de) 1992-09-11 1994-03-17 Merck Patent Gmbh Imidazolderivate
JP3115455B2 (ja) 1992-12-18 2000-12-04 明治製菓株式会社 新規セファロスポリン誘導体
DE4309969A1 (de) 1993-03-26 1994-09-29 Bayer Ag Substituierte heteroanellierte Imidazole
US5563143A (en) 1994-09-21 1996-10-08 Pfizer Inc. Catechol diether compounds as inhibitors of TNF release
US6506876B1 (en) * 1994-10-11 2003-01-14 G.D. Searle & Co. LTA4 hydrolase inhibitor pharmaceutical compositions and methods of use
US5939557A (en) * 1996-04-03 1999-08-17 Merck & Co., Inc. Inhibitors of farnesyl-protein transferase
US5854265A (en) * 1996-04-03 1998-12-29 Merck & Co., Inc. Biheteroaryl inhibitors of farnesyl-protein transferase
US5872136A (en) * 1996-04-03 1999-02-16 Merck & Co., Inc. Arylheteroaryl inhibitors of farnesyl-protein transferase
US5883105A (en) * 1996-04-03 1999-03-16 Merck & Co., Inc. Inhibitors of farnesyl-protein transferase
US6080870A (en) * 1996-04-03 2000-06-27 Merck & Co., Inc. Biaryl substituted imidazole compounds useful as farnesyl-protein transferase inhibitors
US5874452A (en) * 1996-04-03 1999-02-23 Merck & Co., Inc. Biheteroaryl inhibitors of farnesyl-protein transferase
US5880140A (en) * 1996-04-03 1999-03-09 Merck & Co., Inc. Biheteroaryl inhibitors of farnesyl-protein transferase
US6063930A (en) * 1996-04-03 2000-05-16 Merck & Co., Inc. Substituted imidazole compounds useful as farnesyl-protein transferase inhibitors
US5859035A (en) * 1996-04-03 1999-01-12 Merck & Co., Inc. Arylheteroaryl inhibitors of farnesyl-protein transferase
DE19900471A1 (de) 1999-01-08 2000-07-13 Merck Patent Gmbh Imidazo[4,5c]-pyridin-4-on-derivate
JP4055363B2 (ja) * 1999-01-08 2008-03-05 チッソ株式会社 ボラン誘導体および有機電界発光素子
CA2373073A1 (en) * 1999-05-07 2000-11-16 Takeda Chemical Industries, Ltd. Cyclic compounds and uses thereof
US6844367B1 (en) * 1999-09-17 2005-01-18 Millennium Pharmaceuticals, Inc. Benzamides and related inhibitors of factor Xa
DK1259485T3 (da) * 2000-02-29 2006-04-10 Millennium Pharm Inc Benzamider og beslægtede inhibitorer for faktor Xa
EP1132381A1 (en) 2000-03-08 2001-09-12 Cermol S.A. Ester derivatives of dimethylpropionic acid and pharmaceutical compositions containing them
JP4331944B2 (ja) 2001-04-17 2009-09-16 大日本住友製薬株式会社 新規アデニン誘導体
US20030073836A1 (en) * 2001-07-05 2003-04-17 Boehringer Ingelheim Pharma Kg Heteroarylcarboxylic acid amides, the preparation thereof and their use as pharmaceutical compositions
DE10140246A1 (de) * 2001-08-09 2003-03-06 Forsch Pigmente Und Lacke E V Verfahren zur Behandlung von Oberflächen von Substraten
EP1429759A4 (en) * 2001-09-26 2004-12-15 Bristol Myers Squibb Co COMPOUNDS FOR TREATING HEPATITIS C VIRUS
JP2005525309A (ja) 2002-01-10 2005-08-25 ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト 医薬品としての使用のためのＭＴＰインヒビター又はａｐｏＢ分泌インヒビターとフィブレートの組み合わせ
GB0215293D0 (en) * 2002-07-03 2002-08-14 Rega Foundation Viral inhibitors
CA2496249C (en) 2002-08-21 2012-01-24 Boehringer Ingelheim Pharma Gmbh & Co. Kg 8-[3-amino-piperidin-1-yl]-xanthines, the production thereof and the use of the same as medicaments
WO2004054974A2 (en) * 2002-12-13 2004-07-01 Smithkline Beecham Corporation Piperidine derivatives as ccr5 antagonists
US7223785B2 (en) * 2003-01-22 2007-05-29 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
US7098231B2 (en) * 2003-01-22 2006-08-29 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
US20040242613A1 (en) 2003-01-30 2004-12-02 Boehringer Ingelheim Pharmaceuticals, Inc. Pyrimidine derivatives useful as inhibitors of PKC-theta
US7566707B2 (en) * 2003-06-18 2009-07-28 Boehringer Ingelheim International Gmbh Imidazopyridazinone and imidazopyridone derivatives, the preparation thereof and their use as pharmaceutical compositions
MXPA06004641A (es) * 2003-11-05 2006-06-27 Hoffmann La Roche Derivados de fenilo como agonistas para.
KR101238430B1 (ko) * 2004-07-27 2013-02-28 길리애드 사이언시즈, 인코포레이티드 이미다조［4,5-ｄ］피리미딘, 그들의 용도 및 제조방법
EP1791932A1 (en) 2004-09-13 2007-06-06 Ciba Specialty Chemicals Holding Inc. Alkylaminoacetamide lubricant additives
ES2339298T3 (es) * 2006-07-07 2010-05-18 Gilead Sciences, Inc. Compuesto de piridazina novedoso y uso del mismo.
UA99466C2 (xx) 2007-07-06 2012-08-27 Гилиад Сайенсиз, Инк. Кристалічна сполука піридазину$кристаллическое соединение пиридазина

Patent Citations (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3985891A (en) * 1973-02-03 1976-10-12 Boehringer Ingelheim Gmbh 2-Phenyl-imidazo (4,5-b)pyridines and salts thereof
US5137896A (en) * 1981-10-01 1992-08-11 Janssen Pharmaceutica N.V. N-(3-hydroxy-4-piperidinyl)benzamide derivatives
US4565816A (en) * 1982-05-28 1986-01-21 Sandoz Ltd. Piperazine derivatives and pharmaceutical composition containing them
US4692443A (en) * 1983-10-17 1987-09-08 Eli Lilly And Company 3-bicyclicpyridinium-methyl cephalosporins
US4804658A (en) * 1986-09-15 1989-02-14 G. D. Searle & Co. Imidazopyridine derivatives and pharmaceutical compositions
US5057517A (en) * 1987-07-20 1991-10-15 Merck & Co., Inc. Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents
US5019581A (en) * 1988-03-14 1991-05-28 G. D. Searle & Co. 5-substituted (4,5-c) imidazopyridine compounds which have useful platelet activating factor antagonistic activity
US5227384A (en) * 1988-03-14 1993-07-13 G. D. Searle & Co. 5-substituted [4,5-c] imidazopyridines and pharmaceutical use thereof
US5302601A (en) * 1988-03-14 1994-04-12 G. D. Searle & Co. 5-substituted imidazo[4,5-c]pyridines
US4914108A (en) * 1988-03-14 1990-04-03 G. D. Searle & Co. 5-substituted(4,5-c)imidazopyridine compounds which have useful platelet activating factor antagonistic activity
US5332744A (en) * 1989-05-30 1994-07-26 Merck & Co., Inc. Substituted imidazo-fused 6-membered heterocycles as angiotensin II antagonists
US4990518A (en) * 1989-09-13 1991-02-05 G. D. Searle & Co. Pharmacologically active heteroaryl substituted imidazo (4,5-c) pyridines
US4988707A (en) * 1989-09-13 1991-01-29 G. D. Searle & Co. Pharmacologically active phenylalkanoyl substituted imidazo (4,5-C) pyridines
US5011832A (en) * 1990-06-26 1991-04-30 Merck & Co., Inc. 2-biphenyl-carbapenem antibacterial agents
US5446032A (en) * 1991-07-24 1995-08-29 British Biotech Pharmaceuticals Limited Imidazo (4,5-C) pyridine derivatives as PAF antagonists
US5587372A (en) * 1991-12-12 1996-12-24 Roussel Uclaf Cephalosporins
US5208242A (en) * 1992-08-26 1993-05-04 G. D. Searle & Co. 5-substituted-4-phenyl-5H-imidazo[4,5-c]pyridine derivatives
US5405964A (en) * 1992-10-24 1995-04-11 Merck Patent Gesellschaft Mit Beschrankter Haftung Imidazopyridines
US5374638A (en) * 1993-03-19 1994-12-20 Merck & Co., Inc. Six membered ring fused imidazoles substituted with phenoxyphenylacetic acid derivatives used to treat asthma
US5438063A (en) * 1993-06-07 1995-08-01 Merck Patent Gesellschaft Mit Beschrankter Haftung Imidazopyridines as angiotensin II antagonists
US5607944A (en) * 1993-07-22 1997-03-04 Karl Thomae Gmbh Bicyclic heterocyclic compounds, pharmaceutical preparations containing these compounds and processes for their preparations
US5486525A (en) * 1993-12-16 1996-01-23 Abbott Laboratories Platelet activating factor antagonists: imidazopyridine indoles
US5585492A (en) * 1994-10-11 1996-12-17 G. D. Searle & Co. LTA4 Hydrolase inhibitors
US6329381B1 (en) * 1997-11-28 2001-12-11 Sumitomo Pharmaceuticals Company, Limited Heterocyclic compounds
US6492384B1 (en) * 1998-10-01 2002-12-10 Merck Patent Gmbh Imidazo (4,5-C) pyridine-4-one derivatives with factor XA inhibiting effect
US20040097438A1 (en) * 1999-12-27 2004-05-20 Japan Tobacco Inc. Fused-ring compounds and use thereof as drugs
US7112600B1 (en) * 1999-12-27 2006-09-26 Japan Tobacco Inc. Fused-ring compounds and use thereof as drugs
US6770666B2 (en) * 1999-12-27 2004-08-03 Japan Tobacco Inc. Fused-ring compounds and use thereof as drugs
US6479508B1 (en) * 2000-07-06 2002-11-12 Boehringer Ingelheim (Canada) Ltd. Viral polymerase inhibitors
US20040082635A1 (en) * 2001-06-26 2004-04-29 Hiromasa Hashimoto Fused cyclic compounds and medicinal use thereof
US20030108862A1 (en) * 2001-08-07 2003-06-12 Boehringer Ingelheim (Canada) Ltd. Direct binding assay for identifying inhibitors of HCV polymerase
US20040097574A1 (en) * 2002-08-29 2004-05-20 Boehringer Ingelheim Pharmaceuticals, Inc. Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
US20050222198A1 (en) * 2003-12-22 2005-10-06 K.U. Leuven Research & Development, Gerhard Puerstinger And Gilead Sciences, Inc. Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7737162B2 (en) 2002-07-03 2010-06-15 Gilead Sciences, Inc. Viral inhibitors
US8779141B2 (en) 2002-07-03 2014-07-15 Gilead Sciences, Inc. Viral inhibitors
US20050239821A1 (en) * 2002-07-03 2005-10-27 Johan Neyts Viral inhibitors
US8329727B2 (en) 2003-12-22 2012-12-11 Gilead Sciences, Inc. Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment
US7648998B2 (en) * 2003-12-22 2010-01-19 K.U. Leuven Research & Development Imidazo 4,5-c pyridine compounds and methods of antiviral treatment
US20100028301A1 (en) * 2003-12-22 2010-02-04 Bondy Steven S IMIDAZO[4,5-c]PYRIDINE COMPOUNDS AND METHODS OF ANTIVIRAL TREATMENT
US20070244148A1 (en) * 2003-12-22 2007-10-18 Bondy Steven S Imidazo 4,5-C Pyridine Compounds and Methods of Antiviral Treatment
US8569487B2 (en) 2006-07-07 2013-10-29 Gilead Sciences, Inc. Pyridazine compound and use thereof
US20100152444A1 (en) * 2006-07-07 2010-06-17 Gilead Sciences, Inc. Novel pyridazine compound and use thereof
US7754720B2 (en) 2006-07-07 2010-07-13 Gilead Sciences, Inc. Pyridazine compound and use thereof
US7956184B2 (en) 2006-07-07 2011-06-07 Gilead Sciences, Inc. Pyridazine compound and use thereof
US20080199427A1 (en) * 2006-07-07 2008-08-21 Bondy Steven S Novel pyridazine compound and use thereof
US20100063059A1 (en) * 2006-07-07 2010-03-11 Gerhard Puerstinger Novel pyridazine compound and use thereof
US8106054B2 (en) 2007-07-06 2012-01-31 Gilead Sciences, Inc. Crystalline pyridazine compound
US20090036460A1 (en) * 2007-07-06 2009-02-05 Gilead Sciences, Inc. Crystalline pyridazine compound
US8569488B2 (en) 2007-07-06 2013-10-29 Gilead Sciences, Inc. Crystalline pyridazine compound
US8815858B2 (en) 2010-05-21 2014-08-26 Gilead Sciences, Inc. Heterocyclic flaviviridae virus inhibitors

Also Published As

Publication number Publication date
EP1841765A2 (en) 2007-10-10
PT1841765E (pt) 2009-05-14
EP1841765B1 (en) 2009-03-25
US20080188516A1 (en) 2008-08-07
DE602005013580D1 (de) 2009-05-07
DK1841765T5 (da) 2009-12-21
JP2008524335A (ja) 2008-07-10
ES2324794T3 (es) 2009-08-14
WO2006069193A2 (en) 2006-06-29
JP2012184265A (ja) 2012-09-27
CA2592388C (en) 2013-04-02
NZ556624A (en) 2010-06-25
AU2005319167A1 (en) 2006-06-29
WO2006069193A3 (en) 2006-08-10
US7795276B2 (en) 2010-09-14
AU2005319167B2 (en) 2011-09-29
PL1841765T3 (pl) 2009-08-31
HK1113570A1 (en) 2008-10-10
SI1841765T1 (sl) 2009-08-31
CA2592388A1 (en) 2006-06-29
ATE426601T1 (de) 2009-04-15
DK1841765T3 (da) 2009-06-02
CY1109087T1 (el) 2014-07-02

Similar Documents

Publication Publication Date Title
US7795276B2 (en) Imiadazo[4,5-c] pyridine compound and method of antiviral treatment
US8569487B2 (en) Pyridazine compound and use thereof
DK2161273T3 (en) Imidazo [4,5-C] pyridine compounds and methods for antiviral therapy
KR101184032B1 (ko) 바이러스 억제제
US8569488B2 (en) Crystalline pyridazine compound
AU2011253901B2 (en) Novel pyridazine compound and use thereof

Legal Events

Date Code Title Description
AS Assignment

Owner name: GILEAD SCIENCES, INC., CALIFORNIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:BONDY, STEVEN S.;OARE, DAVID A.;TSE, WINSTON C.;REEL/FRAME:019876/0581;SIGNING DATES FROM 20060501 TO 20060504

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO PAY ISSUE FEE

AS Assignment

Owner name: PUERSTINGER, GERHARD, AUSTRIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:GILEAD SCIENCES, INC.;REEL/FRAME:020772/0582

Effective date: 20080401

Owner name: K.U. LEUVEN RESEARCH & DEVELOPMENT, BELGIUM

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:GILEAD SCIENCES, INC.;REEL/FRAME:020772/0582

Effective date: 20080401

Owner name: GILEAD SCIENCES, INC., CALIFORNIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:GILEAD SCIENCES, INC.;REEL/FRAME:020772/0582

Effective date: 20080401

AS Assignment

Owner name: K.U. LEUVEN RESEARCH & DEVELOPMENT, BELGIUM

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:GILEAD SCIENCES, INC.;REEL/FRAME:036495/0004

Effective date: 20150314