Classifications

• • 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
  • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
  • A61K31/19—Carboxylic acids, e.g. valproic acid
  • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
  • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
• • 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
  • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
  • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
  • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

• influenza virus neuraminidase inhibitor peramivir has marked activity against the influenza virus in vitro and in experimentally infected mice (Govorkova et ah, Antimicrobial Agents and Chemotherapy, 45(10), 2723-2732 (2001); and Smee el al., Antimicrobial Agents and Chemotherapy, 45(3), 743- 748 (2001)).
• Clinical trials using this drug showed a suboptimal therapeutic effect on influenza infection in humans following oral administration over a period of days.
• the invention provides a method for ⁇ treating a viral infection ⁇ e.g., an influenza infection) in a human comprising administering an effective anti-viral amount of a compound of formula I, II, III, or IV:
• the invention also provides a method for inhibiting a neuraminidase in a human comprising administering an effective inhibitory amount of a compound of formula I, II, III, or IV, or a pharmaceutically acceptable salt thereof, to the human by an intravenous route.
• the invention also provides a unit dosage form that is suitable for intravenous administration to a human comprising up to about 400 mg of a compound of formula I 5 II, III, or IV, or a pharmaceutically acceptable salt thereof.
• the invention also provides a unit dosage form that is suitable for intravenous administration to a human comprising up to about 1,000 mg (e.g., up to about 800, 600, 500, 400, 300, 200, 150, 100, or 75 mg) of a compound of formula I, II, in, or IV, or a pharmaceutically acceptable salt thereof.
• a unit dosage form that is suitable for intravenous administration to a human comprising up to about 1,000 mg (e.g., up to about 800, 600, 500, 400, 300, 200, 150, 100, or 75 mg) of a compound of formula I, II, in, or IV, or a pharmaceutically acceptable salt thereof.
• the invention also provides a kit comprising packaging materials, a compound of formula I, II, III, or IV, or a pharmaceutically acceptable salt thereof, and instructions for administering the compound to a human by an intravenous route.
• the invention also provides the use of a compound of formula I, II, IH, or IV, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for intravenous injection for increasing life expectancy or reducing mortality in a group of mammals exposed to a source of an influenza virus, by intravenous injection of a dose of the medicament into each member of the group presenting clinical symptoms of infection.
• the invention also provides the use of a compound of formula I, ⁇ , HI, or IV, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for intravenous injection for increasing life expectancy or reducing mortality in a group of mammals exposed to a source of an influenza virus, by intravenous injection of a dose of the medicament into each member of the group.
• Figure 1 depicts plasma peramivir concentration time curves after 15 minute intravenous infusions of peramivir to healthy human volunteers.
• Figure 2 depicts plasma peramivir concentration time curves after intramuscular injections of peramivir to healthy human volunteers. Detailed Description
• influenza virus neuraminidase inhibitor peramivir has been previously shown to have marked activity against influenza virus in vitro and in experimentally infected mice (Govorkova et ah, (2001); and Smee et ah, (2001)).
• This drug showed an inadequate inhibitory effect on influenza in humans. This effect was attributed to a poor adsorption of the drug when administered once daily orally in patients.
• certain embodiments of the present invention provide a method for treating a viral infection in a human comprising administering an effective anti-viral amount of a compound of formula I, II, III, or IV:
• the compound of formula I, II, III, or IV is a compound of formula Ia 5 Ila, Ilia, or IVa:
• the viral infection is an influenza infection.
• the viral infection is an influenza type A or type B infection.
• the viral infection is caused by a strain of virus represented by the formula H x Ny wherein X is an integer from 1-16 and Y is an integer from 1-9.
• the influenza is an H3N2, HlNl, H5N1, avian, or seasonal influenza.
• the effective anti-viral amount is up to about 800 mg. In certain embodiments, the effective anti-viral amount is up to about 400 mg. In certain embodiments, the effective anti -viral amount is up to about 300 mg. In certain embodiments, the effective anti-viral amount is up to about 200 mg.
• the entire effective dose is administered in one intravenous administration. In certain embodiments, the entire effective dose is administered in multiple intravenous administrations.
• a compound or formula Ia, or a pharmaceutically acceptable salt thereof is administered.
• the plasma concentration of the compound is higher than the ICso of the virus causing the viral infection 12 hours following administration of the compound.
• Certain embodiments of the present invention provide a method for inhibiting a neuraminidase in a human comprising administering an effective inhibitory amount of a compound of formula I, ⁇ , IE, or IV:
• the compound of formula I, II, HI, or FV is a compound of formula Ia, Ha, Ilia, or IVa:
• the effective inhibitory amount is up to about 800 mg. In certain embodiments, the effective inhibitory amount is up to about 400 mg. In certain embodiments, the effective inhibitory amount is up to about 300 mg. In certain embodiments, the effective inhibitory amount is up to about 200 mg.
• the entire effective inhibitory dose is administered in one intravenous administration. In certain embodiments, the entire effective inhibitory dose is administered in multiple intravenous administrations.
• a compound of formula Ia, or a pharmaceutically acceptable salt thereof is administered.
• the methods may further comprise orally administering a neuraminidase inhibitor to the human.
• the neuraminidase inhibitor that is administered orally is oseltamivir carboxylate.
• the neuraminidase inhibitor that is administered orally is a compound of formula ⁇ , ⁇ , III, or IV:
• the neuraminidase inhibitor that is administered orally is a compound of formula Ia, Ha, DIa, or IVa:
• the neuraminidase inhibitor that is administered orally is a compound of formula Ia, or a pharmaceutically acceptable salt thereof. In certain embodiments, the neuraminidase inhibitor that is administered orally is administered for up to 20 days. In certain embodiments, the neuraminidase inhibitor that is administered orally is administered for up to 10 days. In certain embodiments, the neuraminidase inhibitor that is administered orally is administered for up to 5 days.
• Certain embodiments of the present invention provide a unit dosage form that is suitable for intravenous administration to a human, comprising up to about 800 mg of a compound of formula I 5 ⁇ , III, or IV:
• the compound of formula I, II, III, or IV is a compound of formula Ia, Ha, Ilia, or TVa:
• the unit dosage form comprises up to about 400 mg of the compound or salt. In certain embodiments, the unit dosage form comprises up to about 300 mg of the compound or salt. In certain embodiments, the unit dosage form comprises up to about 200 mg of the compound or salt.
• kits comprising packaging materials, a compound of formula I, II, III, or IV:
• the compound is provided in a formulation suitable for intravenous administration.
• the kit comprises up to about 800 mg of the compound or salt. In certain embodiments, the kit comprises up to about 400 mg of the compound or salt. In certain embodiments, the kit comprises up to about 300 mg of the compound or salt. In certain embodiments, the kit comprises up to about 200 mg of the compound or salt.
• kits comprising packaging materials, a unit dosage form as described herein, and instructions for administering the compound to a human by an intravenous route.
• Certain embodiments of the present invention provide a use of a compound of formula I, II, III, or IV:
• the compound of formula I 5 II, IU, or IV is a compound of formula Ia, ITa, Ilia, or IVa:
• influenza virus is an avian influenza virus.
• influenza virus is an influenza type A or type B virus.
• influenza virus is H5N1, or a mutant strain thereof.
• influenza virus is a strain of virus represented by the formula H x Ny wherein X is an integer from 1-16 and Y is an integer from 1-9.
• the influenza virus is an H3N2, HlNl, H5N1, avian, or seasonal influenza virus.
• each member of the group presenting symptoms of infection receives only one intravenous dose of the medicament. In certain embodiments, each member of the group presenting symptoms of infection receives multiple intravenous doses of the medicament.
• the members of the group presenting clinical symptoms of infection are treated orally with a neuraminidase inhibitor.
• the neuraminidase inhibitor is oseltamivir carboxylate.
• the neuraminidase inhibitor is a compound of formula I, II, m, or rV:
• the neuraminidase inhibitor is a compound of formula Ia, Ila, Ilia, or IVa:
• the neuraminidase inhibitor is a compound of formula Ia 5 or a pharmaceutically acceptable salt thereof.
• the source of the virus is an infected bird. In certain embodiments, the source of the virus is a mammal presenting symptoms of infection.
• the use is for reducing mortality.
• Certain embodiments of the present invention provide a use of a compound of formula I, II, III, or IV:
• a medicament for intravenous injection for increasing life expectancy or reducing mortality in a group of mammals exposed to a source of an influenza virus, by intravenous injection of a dose of the medicament into each member of the group.
• the compound of formula I, II, III, or IV is a compound of formula Ia, Ila, IHa, or IVa:
• influenza virus is an avian influenza virus.
• the avian influenza virus is H5N1, or a mutant strain thereof.
• the influenza virus is a strain of virus represented by the formula H x N y wherein X is an integer from 1-16 and Y is an integer from 1-9.
• the influenza virus is an influenza type A or type B virus.
• the influenza virus is an H3N2, HlNl, H5N1, avian, or seasonal influenza virus.
• each member of the group receives only one intravenous dose of the medicament. In certain embodiments, each member of the group receives multiple intravenous doses of the medicament.
• the members of the group are treated orally with a neuraminidase inhibitor.
• the neuraminidase inhibitor is oseltamivir carboxylate.
• the neuraminidase inhibitor is a compound of formula I, II, III, or IV:
• the neuraminidase inhibitor is a compound of formula Ia, Ha, Ilia, or IVa:
• the neuraminidase inhibitor is a compound of formula Ia, or a pharmaceutically acceptable salt thereof.
• the source of the virus is an infected bird. In certain embodiments, the source of the virus is a mammal presenting symptoms of infection.
• the use is for reducing mortality.
• Certain embodiments of the present invention provide a use of a compound of formula I, II, III, or IV:
• a medicament for intravenous injection for achieving a plasma concentration in a human of the compound that is effective to treat a virus by intravenous injection of a dose of the medicament into the human.
• Certain embodiments of the present invention provide a use of a compound of formula I 5 II, III, or IV:
• a specific compound of formula I 5 II, IE, or IV is (lS,2S,3R,4R)-3-(l -
• Acetamido-2-ethylbutyl)-4-guanidino-2-hydroxycyclopentane-carboxylic acid (15.2S',3i?,4i?)-3-(l-Acetamido-2-propylpentyl)-4-guanidino-2- hydroxycyclopentanecarboxylic acid; (l ⁇ ,3i?,4./?)-3-(l-Acetamido-2 ⁇ propylpentyl)-4-guanidinocyclopentanecarboxylic acid; or (lR,3R,4R)-3-( ⁇ - Acetamido-2-ethylbutyl)-4-guanidinocyclopentanecarboxylic acid; or a pharmaceutically acceptable salt thereof.
• a specific compound of formula I is a compound of formula Ia, or a pharmaceutically acceptable salt thereof.
• the plasma concentration of the compound is higher than the IC50 of the virus 12 hours following injection of the compound.
• mice infected with influenza A/Duck/MN/1525/81 (H5N1) virus were treated a single time Lv. 1 hour pre-virus exposure with peramivir at doses of 20, 10 and 3 mg/kg.
• Peramivir was significantly protective to the mice at the two highest dosages used, as seen by prevention of deaths, lessening of lung consolidation, and inhibition of lung virus titers.
• the 3 mg/kg dose was moderately inhibitory to lung parameters.
• a specific compound of formula I, ⁇ , HI, or IV is a compound of formula Ia, Ila, Ilia, or IVa:
• Suitable inorganic salts may also be formed, including hydrochloride, sulfate, nitrate, phosphate, bicarbonate, and carbonate salts.
• Pharmaceutically acceptable salts may be obtained using standard procedures well known in the art, for example by reacting a sufficiently basic • compound such as an amine with a suitable acid affording a physiologically acceptable anion.
• Alkali metal (for example, sodium, potassium or lithium) or alkaline earth metal (for example calcium) salts of carboxylic acids can also be made.
• the compounds of formula I, II, IH, and IV can be formulated as pharmaceutical compositions and administered to a mammalian host, such as a human patient, by intravenous routes.
• Solutions of the active compound or its salts can be prepared in water, optionally mixed with a nontoxic surfactant.
• Dispersions can also be prepared in glycerol, liquid polyethylene glycols, triacetin, and mixtures thereof and in oils. Under ordinary conditions of storage and use, these preparations contain a preservative to prevent the growth of microorganisms.
• the pharmaceutical dosage forms suitable for injection or infusion can include sterile aqueous solutions or dispersions or sterile powders comprising the active ingredient(s) which are adapted for the extemporaneous preparation of sterile injectable or infusible solutions or dispersions, optionally encapsulated in liposomes.
• the ultimate dosage form should be sterile, fluid and stable under the conditions of manufacture and storage.
• the liquid carrier or vehicle can be a solvent or liquid dispersion medium comprising, for example, water, ethanol, a polyol (for example, glycerol, propylene glycol, liquid polyethylene glycols, and the like), vegetable oils, nontoxic glyceryl esters, and suitable mixtures thereof.
• the proper fluidity can be maintained, for example, by the formation of liposomes, by the maintenance of the required particle size in the case of dispersions or by the use of surfactants.
• the prevention of the action of microorganisms can be brought about by various antibacterial and antifungal agents, for example, parabens, chlorobutanol, phenol, sorbic acid, thimerosal, ' and the like. In many cases, it will be preferable to include isotonic agents, for example, sugars, buffers or sodium chloride. Prolonged absorption of the injectable compositions can be brought about by the use in the compositions of agents delaying absorption, for example, aluminum monostearate and gelatin.
• Sterile injectable solutions can be prepared by incorporating the active compound(s) into an appropriate solvent with the other optional ingredients enumerated above, optionally followed by filter sterilization.
• the preferred methods of preparation are vacuum drying and the freeze drying techniques, which yield a powder of the active ingredient plus any additional desired ingredient present in the previously sterile-filtered solutions.
• the terms “treat”, “treating” and “treatment” include administering a compound prior to the onset of clinical symptoms of a disease state/condition so as to prevent the development of any symptom, as well as administering a compound after the onset of one or more clinical symptoms of a disease state/condition so as to reduce or eliminate any such symptom, aspect or characteristic of the disease state/condition. Such treating need not be absolute to be useful.
• the active compounds can be administered prior to exposure to the virus.
• the agents can also be administered subsequent ⁇ e.g., within 1, 2, 3, 4, or 5 days) to exposure to the virus.
• unit dosage form relates to an intravenous formulation containing a specific amount of a drug, the whole of which is intended to be administered as a single dose. It is distinguished from a supply of an indefinite amount of a medicament, e.g., a bottle of medicine, from which a dose has to be measured out.
• the invention provides a method for treating a viral infection in a human comprising administering an effective amount of a compound of formula I, II, III, or IV, or a pharmaceutically acceptable salt thereof, to the human by intravenous administration.
• the effective amount is administered in a single intravenous administration.
• the effective amount is administered in multiple administrations. Accordingly, the methods of the invention provide for high patient compliance and they require a low dose of the effective agent.
• the effective inhibitory amount of the compound of formula I, ⁇ , III, or IV is up to about I 5 OOO mg. • In one embodiment of the invention, the effective inhibitory amount of the compound of formula I, II, III, or IV is up to about 800 mg.
• the effective inhibitory amount of the compound of formula I, II, III, or IV is up to about 600 mg.
• the effective inhibitory, amount of the compound of formula I, ⁇ , HI, or IV is up to about 500 mg.
• the effective inhibitory amount of the compound of formula I, II, III, or IV is up to about 400 mg.
• the effective inhibitory amount of the compound of formula I, II, III, or IV is up to about 300 mg. In one embodiment of the invention, the effective inhibitory amount of the compound of formula I, II, III, or IV is up to about 200 mg.
• the effective inhibitory amount of the compound of formula I, II, III, or IV is up to about 150 mg.
• the effective inhibitory amount of the compound of formula I, II, III, or IV is up to about 75 mg.
• a compound of formula I, II, • III, or rv is administered to a human intravenously.
• the compound of formula I, ⁇ , III, or IV is administered once to a human intravenously.
• a neuraminidase inhibitor is also administered to the human orally.
• the neuraminidase inhibitor that is administered orally is oseltamivir carboxylate.
• the neuraminidase inhibitor ⁇ that is administered orally is a compound of formula I, II, III, or IV:
• the neuraminidase inhibitor that is administered orally is a compound of formula Ia 5 Ila. IHa, or IVa:
• the neuraminidase inhibitor that is administered orally is a compound of formula Ia, or a pharmaceutically acceptable salt thereof.
• the compound of formula I 5 EL, III, or IV, or a pharmaceutically acceptable salt thereof can also be administered in combination with one or more additional therapeutic agents, such as anti-viral agents (e.g., agents active against influenza) or antibiotics.
• additional therapeutic agents such as anti-viral agents (e.g., agents active against influenza) or antibiotics.
• the intravenous formulations of the invention can also comprise one or more additional therapeutic agents, such as anti-viral agents (e.g., agents active against influenza) and antibiotics.
• intravenous administration of peramivir to treat a viral infection is described herein.
• Intramuscular administration of peramivir to treat a viral infection is also described herein (see, e.g., Example 2), which further exemplifies intramuscular administration of peramivir to treat a viral infection, as is described in International Application No. PCT/US2006/013535, filed April 12, 2006, the disclosure of which is incorporated by reference.
• intravenous and intramuscular injections of peramivir to humans provides high plasma concentrations of peramivir with an extended plasma half-life.
• the compounds described herein can be used to treat a virus, e.g., an influenza virus.
• a virus e.g., an influenza virus.
• the compounds can be used to treat any one or combination of the following strains.
• H stands for a type of hemagglutinin
• N stands for a type of neuraminidase.
• H x Ny wherein X is an integer from 1-16 and Y is an integer from 1-9, can also be used to describe the combinations presented in the table.
• the virus may be, for example, an avian virus or a humanized avian virus.
• avian virus includes both avian forms of the virus and humanized forms of the avian virus.
• Certain embodiments of the present invention provide the use of a compound of formula I, II, IE, or IV:
• a medicament for intravenous injection for achieving a plasma concentration in a human of the compound that is effective to treat a virus by intravenous injection of a dose of the medicament into the human.
• Certain embodiments of the present invention also provide the use of a compound of formula I 3 ⁇ , DI 5 or IV:
• a medicament for intramuscular injection for achieving a plasma concentration in a human of the compound that is effective to treat a virus by intramuscular injection of a dose of the medicament into the human.
• compositions comprising peramivix formulated for intravenous administration to a human.
• Certain embodiments of the invention also provide compositions comprising peramivir fo ⁇ nulated for intravenous administration for use in treating a virus by achieving a plasma concentration in a human of peramivir that is effective to treat the virus.
• compositions comprising peramivir formulated for intramuscular administration to a human.
• Certain embodiments of the invention also provide compositions comprising peramivir formulated for intramuscular administration for use in treating a virus by achieving a plasma concentration in a human of peramivir that is effective to treat the virus.
• the plasma concentration of the compound is higher than the IC 50 of the virus at least about 12 hours following the injection.
• the plasma concentration of the compound is higher than the IC50 of the virus at least about 24 hours following the injection.
• the plasma concentration of the compound is higher than the IC5 0 of the virus at least about 36 hours following the injection.
• the plasma concentration of the compound is higher than the IC50 of the virus at least about 48 hours following the injection.
• the plasma concentration of the compound is higher than the IC50 of the virus at least about 60 hours following the injection. ⁇ In certain embodiments of the invention, the plasma concentration of the compound is higher than the IC50 of the virus at least about 72 hours. following the injection.
• the virus is an influenza virus. In certain embodiments of the invention, the virus is an avian influenza virus. In certain embodiments of the invention, the virus is H5N1, or a mutant strain thereof.
• influenza virus In certain embodiments of the invention, the virus is an influenza virus. In certain embodiments of the invention, the virus is an avian influenza virus. In certain embodiments of the invention, the virus is H5N1, or a mutant strain thereof.
• mice were infected i.n. with a dose thought to be the LDlOO of influenza virus.
• Groups of 10 mice were treated i.v. with peramivir at dosages of 20, 10 and 3 mg/kg a single time 1 hour pre-virus exposure.
• Placebo sterile saline
• Drug-treated infected mice and placebo-treated controls were observed daily for death through 21 days.
• As toxicity controls 3 uninfected mice were treated with the highest dose of the compounds in parallel to the infected animals. All toxicity controls were observed for death through 21 days and were weighed immediately prior to the initial treatment and 18 h after the final treatment. Five normal controls were weighed.
• mice The infection induced in this experiment was lethal to 55% of the mice (Table I) 5 with a mean day to death of 9.1 days.
• Peramivir was studied in a placebo-controlled phase I clinical study in healthy human volunteers to evaluate safety and pharmacokinetic parameters using intravenous and intramuscular administrations. Blood samples were ⁇ collected from the subjects at different time points after drug administration to determine the concentration of the drug in plasma. The time course plots are shown in Figure 1 and Figure 2 for intravenous and intramuscular administrations respectively. In the intravenous study, peramivir concentrations followed linear kinetics with an unusually extended plasma half life of greater than 12 hours. At doses of 2 mg/kg and above, the level of peramivir in plasma at 48 hours post- dose is greater than the IC50 for all strains of influenza virus tested, including H5 virus types. For doses greater than 4 mg/kg, even at 72 hours, the levels of the drug are greater than the IC 50 values.
• peramivir concentrations also followed linear kinetics with an unusually extended plasma half life. Even at 72 hours post- dosing, the levels of peramivir are higher than the IC 5 0 values for all the influenza virus strains tested.
• the long plasma half-life and the high levels of peramivir in human volunteers are unusual and unexpected findings and indicate that intravenous and intramuscular administrations of peramivir are beneficial in the treatment of ⁇ influenza in humans.

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