WO2007117241A1 - Intramuscular antiviral treatments - Google Patents
Intramuscular antiviral treatments Download PDFInfo
- Publication number
- WO2007117241A1 WO2007117241A1 PCT/US2006/013535 US2006013535W WO2007117241A1 WO 2007117241 A1 WO2007117241 A1 WO 2007117241A1 US 2006013535 W US2006013535 W US 2006013535W WO 2007117241 A1 WO2007117241 A1 WO 2007117241A1
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- WO
- WIPO (PCT)
- Prior art keywords
- compound
- formula
- pharmaceutically acceptable
- acceptable salt
- iii
- Prior art date
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- 0 CCCC(CCC)C(*)C(CC(C1)C(O)=O)C1NC(N)=N Chemical compound CCCC(CCC)C(*)C(CC(C1)C(O)=O)C1NC(N)=N 0.000 description 2
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
Definitions
- influenza virus neuraminidase inhibitor peraniivir 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 et ah, Antimicrobial Agents and Chemotherapy, 45(3), 743- 748 (2001)).
- peramivir showed an undesirably low inhibitory effect on influenza 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, ⁇ , IE, or lV:
- a viral infection e.g., an influenza infection
- administering an effective anti- viral amount of a compound of formula I, ⁇ , IE, or lV:
- 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 intramuscular route .
- the invention also provides a unit dosage form that is suitable for intramuscular administration to a human comprising up to about 500 mgs (e.g., about 150 mg) of a compound of formula I, II, III, 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 intramuscular route.
- the invention also provides the use of a compound of formula I, ⁇ , IE, or FV, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for intramuscular injection for increasing life expectancy and/or • reducing mortality in a group of mammals, e.g., humans, exposed to a source of an influenza virus, by intramuscular injection of a dose, e.g. , an effective antiviral dose, of the medicament into each member of the group presenting clinical symptoms of infection.
- a dose e.g. , an effective antiviral dose
- the invention also provides the use of a compound of formula I, II, III, or rV, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for intramuscular injection for increasing life expectancy or reducing mortality in a group of mammals, e.g., humans, exposed to a source of an influenza virus, by intramuscular injection of a dose of the medicament into each member of the group.
- 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)). Unfortunately, clinical trials using this drug showed an inadequate inhibitory effect on influenza in humans. It has been discovered that a single intramuscular injection of peramivir significantly reduces weight loss and mortality in mice infected with influenza A/H1N1. A single intramuscular injection of peramivir can thus be used to treat influenza infections and to provide an alternate option to oseltamivir during an influenza outbreak. Peramivir was tested as a single intramuscular injection in the mouse influenza model and was found to be active when administered intramuscularly.
- a single intramuscular injection of oseltamivir carboxylate in mice showed a similar effect as the single intramuscular injection of oseltamivir.
- the IC 50 S of peramivir and oseltamivir carboxylate are subnanomolar against HlNl at 0.11 and 0.69nM (Bantia et ah, Antimicrob. Agents Chemother. 45, 1162-1167 (2001)) and H3N2 at 0.59 and 0.55 nM, respectively.
- a single intramuscular injection of oseltamivir (carboxylate) is not effective.
- peramivir as a single intramuscular injection is superior to oseltamivir (carboxylate) given as single intramuscular injections.
- carboxylate carboxylate
- peramivir is a potent inhibitor of neuraminidase activity.
- peramivir is effective as a single intramuscular injection and can be used in the treatment of human influenza virus infections.
- 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 intramuscular administration.
- the effective amount is administered in a single intramuscular administration.
- the methods of the invention provide for high patient compliance as they involve a low dose of the effective agent.
- the effective inhibitory amount of the compound of formula I, II, III, or IV is up to about 500 mg (e.g., from about
- the effective inhibitory amount of the compound of formula I 5 II, III, or IV is up to about 150 mg. In one embodiment of the invention, the effective inhibitory amount of the compound of formula I, II, III, or IV is about 150 mg.
- the compound of formula I, II, III, or IV is administered once to a human intramuscularly, hi another embodiment of the invention, a neuraminidase inhibitor is also administered to the human orally, hi one embodiment of the invention, 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, or a pharmaceutically acceptable salt thereof, hi one embodiment of the invention, the neuraminidase inhibitor that is administered orally is a compound of formula Ia, Ha, Ilia, or FVa:
- the neuraminidase inhibitor that is administered orally is a compound of formula Ia, or a pharmaceutically acceptable salt thereof.
- the compound of formula I, II, IH, 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 intramuscular 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.
- a specific compound of formula I, II, HI, or IV is a compound of formula Ia, Ha, Ilia, or IVa:
- a specific compound of formula I, II, m, or IV is (lS,2S,3R,4R)-3-Q-- Acetamido-2-ethylbutyl)-4-guanidino-2-hydroxycyclopentane-carboxylic acid; (lS,2S,3R,4R)-3-(l -Acetamido-2-propylpentyl)-4-guanidino-2- hydroxycyclopentanecarboxylic acid; (li?,3i?,4i-)-3-(l-Acetamido-2- propylpentyl)-4-guanidinocyclopentanecarboxylic acid; or (li?,3i?,4i?)-3-(l- 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 pharmaceutical
- optically active and racemic forms may exist in and be isolated in optically active and racemic forms. Some compounds may exhibit polymorphism. It is to be understood that the present invention encompasses the use of any racemic, optically-active, polymorphic, or stereoisomeric form, or mixtures thereof, of a compound of formula I, II, III, and/or IV, which possess the useful properties described herein, it being well known in the art how to prepare optically active forms (for example, by resolution of the racemic form by recrystallization techniques, by synthesis from optically-active starting materials, by chiral synthesis, or by chromatographic separation using a chiral stationary phase) and how to determine anti-viral (e.g. anti-influenza) activity using the standard tests described herein, or using other similar tests which are well known in the art.
- anti-viral e.g. anti-influenza
- salts are organic acid addition salts formed with acids which form a physiological acceptable anion, for example, tosylate, methanesulfonate, acetate, citrate, malonate, tartarate, succinate, benzoate, ascorbate, ⁇ -ketoglutarate, and ⁇ -glycerophosphate.
- Suitable inorganic salts may also be formed, including hydrochloride, sulfate, nitrate, phosphate, bicarbonate, and carbonate salts.
- 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.
- a sufficiently basic compound such as an amine
- 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, III, and IV can be formulated as pharmaceutical .compositions and administered to a mammalian host, such as a human patient, by intramuscular 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 compounds of formula I, II, III, and/or IV are formulated with a buffer, e.g., a citrate, e.g., sodium citrate.
- 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, hi many cases, it will be preferable to include isotonic agents, for example, sugars, buffers (e.g., sodium citrate) 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, e.g., 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 intramuscular formulation containing a specific amount of a drug (e.g., from about 10 mg to about 500 mg, e.g., about 150 mg), 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.
- a specific amount of a drug e.g., from about 10 mg to about 500 mg, e.g., about 150 mg
- Peramivir was also administered at 2, 10, and 20 mg/kg as a single intramuscular injection 4 hours before viral infection with the HlNl virus. Complete protection against lethality was observed at all doses. However, none of the five saline-treated control mice survived. By comparison, complete protection against lethality was also observed in the mice treated orally with oseltamivir at both 2 and 10 mg/kg/day (q.d.x5 days). No signs of drug-related toxicity were observed when peramivir was administered intramuscular at the highest dose (20 mg/kg).
- Peramivir and oseltamivir showed a dose response relationship when the weight loss of infected mice over time was followed.
- the maximum mean weight loss in the 2, 10, and 20 mg/kg peramivir-treated groups were 3.3, 0.98, and 0 g, respectively.
- oseltamivir provided a similar effect with the greatest mean weight loss of 1.34 and 0 g occurring at day 8 for the 2 and 10 mg/kg groups, respectively.
- Day 5 weight loss shows a similar trend, hi general, a lower dose resulted in greater weight loss when compared with a higher dose.
- influenza A viruses used in this study were obtained from American Type Culture Collection, Manassas, VA, USA (A/NWS/33;H1N1) and Dr. Robert Sidwell, Utah State University, Logan, UT, USA (A/Victoria/3/75 ;H3N2) and were mouse adapted. Purified N9 crystals from A/H1N9 (NWS/G70) avian virus were obtained from Dr. Graeme Laver, Australian National University, Canberra, Australia.
- mice Specific pathogen-free female BALB/c mice (10-19 g) were obtained from Charles Rivers Laboratories (Raleigh, NC, USA). They were quarantined for 24 hours prior to infection and maintained on rodent diet from Harlan Teklad and tap water.
- Peramivir, oseltamivir, oseltamivir carboxylate and zanamivir were synthesized by BioCryst Pharmaceuticals, Inc. (Birmingham, AL, USA). Each compound was prepared in sterile 0.9% sodium chloride for in vivo experiments. A mixture of 5% isoflurane/95% oxygen was administered as anesthesia. A standard fluorimetric assay was used to measure influenza virus neuraminidase activity (Potier et al., Anal. Biochem., 94, 287-296 (1979)).
- the substrate (2'-(4-methylumbelliferyl)- ⁇ -D-acetymeuraminic acid, MuNANA) is cleaved by neuraminidase to yield a fluorescent product that can be quantified.
- the assay mixture contained inhibitor at various concentrations and neuraminidase enzyme in 32.5mM MES (2-(7V-morpholino)- ethanesulfonic acid) buffer, 4mMcalcium chloride at pH6.5 and incubated for 10-30 min. The reaction was started by the addition of the substrate. After incubation for 30-120 min fluorescence was recorded (excitation: 360 nm and emission: 450 nm) and substrate blanks were subtracted from the sample readings. The IC 5O was calculated by plotting percent inhibition of neuraminidase activity versus the inhibitor concentration. The results are reported as the average of three experiments.
- mice were anesthetized with isoflurane and exposed to lOO ⁇ L of virus by intranasal instillation.
- drug was administered 1 or 4 hours before viral infection; in the treatment model, drug was given at times indicated after the viral infection.
- Each infected, drug and saline-treated group contained 5-10 mice. All mice were observed daily for changes in weight and for any deaths. Parameters for evaluation of antiviral activity included weight loss, reduction in mortality and/or increase in mean days to death determined through 16 or 21 days.
- Mice were infected intranasally with an approximately 70—90% lethal dose of the A/NWS/33(H1N1) or A/Victoria/3/75 (H3N2) influenza virus.
- Oral treatment with peramivir or oseltamivir began 1 or 4 hours before virus exposure (prophylaxis model) and continued once daily for 5 days unless indicated.
- a single intramuscular treatment was administered 1 or 4 hours before virus exposure or at times indicated (treatment model).
- Normal and saline-treated control mice were included in the same treatment schedule. Parameters studied were reduction in mortality and/or increase in mean days to death. The data was analyzed by Sigma Plot (Windows Version 4.01, SPSS,
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Abstract
Description
Claims
Priority Applications (34)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009505338A JP2009533428A (en) | 2006-04-12 | 2006-04-12 | Intramuscular antiviral treatment |
PCT/US2006/013535 WO2007117241A1 (en) | 2006-04-12 | 2006-04-12 | Intramuscular antiviral treatments |
AU2006341592A AU2006341592A1 (en) | 2006-04-12 | 2006-04-12 | Intramuscular antiviral treatments |
MX2008013140A MX2008013140A (en) | 2006-04-12 | 2006-04-12 | Intramuscular antiviral treatments. |
CA002649090A CA2649090A1 (en) | 2006-04-12 | 2006-04-12 | Intramuscular antiviral treatments |
BRPI0621552-1A BRPI0621552A2 (en) | 2006-04-12 | 2006-04-12 | intramuscular antiviral treatments |
EA200870430A EA200870430A1 (en) | 2006-04-12 | 2006-04-12 | INTRAMUSCULAR ANTIVIRUS METHODS OF TREATMENT |
US11/476,401 US20070244193A1 (en) | 2006-04-12 | 2006-06-28 | Intramuscular antiviral treatments |
KR20147030611A KR20140132778A (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
EA200870263A EA025483B1 (en) | 2006-02-13 | 2007-02-12 | Intravenous method for treating a seasonal influenza |
CA2642260A CA2642260C (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
PCT/US2007/003755 WO2007095218A1 (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
EP07750583A EP1986626A1 (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
KR1020227042429A KR20230003248A (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
AU2007215156A AU2007215156A1 (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
CN201510115375.7A CN104784166A (en) | 2006-02-13 | 2007-02-12 | Antiviral compound, dosage form including same, and uses thereof |
MX2020002008A MX2020002008A (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments. |
KR1020187005451A KR101992585B1 (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
KR1020087022406A KR20080096829A (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
BRPI0707769-6A BRPI0707769A2 (en) | 2006-02-13 | 2007-02-12 | intravenous antiviral treatments |
KR1020217035812A KR102475176B1 (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
KR1020197017311A KR102194015B1 (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
KR1020207036259A KR102267754B1 (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
JP2008554421A JP2009538822A (en) | 2006-02-13 | 2007-02-12 | Treatment of viruses in veins |
MX2008010394A MX2008010394A (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments. |
KR1020167030296A KR20160129105A (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
KR1020217018500A KR102323339B1 (en) | 2006-02-13 | 2007-02-12 | Intravenous antiviral treatments |
MYPI20083086A MY166063A (en) | 2006-02-13 | 2008-08-13 | Intravenous antiviral treatments |
US12/749,030 US20110015264A1 (en) | 2006-04-12 | 2010-03-29 | Intramuscular antiviral treatments |
AU2013216632A AU2013216632B2 (en) | 2006-02-13 | 2013-08-14 | Intravenous antiviral treatments |
JP2013174479A JP6073202B2 (en) | 2006-02-13 | 2013-08-26 | Treatment of viruses in veins |
JP2015137495A JP2015180695A (en) | 2006-02-13 | 2015-07-09 | Intravenous antiviral treatment |
HK16100369.5A HK1212250A1 (en) | 2006-02-13 | 2016-01-14 | Antiviral compounds, unit dosage form comprising said compounds and use thereof |
AU2016262644A AU2016262644B2 (en) | 2006-02-13 | 2016-11-21 | Intravenous antiviral treatments |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2006/013535 WO2007117241A1 (en) | 2006-04-12 | 2006-04-12 | Intramuscular antiviral treatments |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/476,401 Continuation US20070244193A1 (en) | 2006-04-12 | 2006-06-28 | Intramuscular antiviral treatments |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007117241A1 true WO2007117241A1 (en) | 2007-10-18 |
Family
ID=37671157
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2006/013535 WO2007117241A1 (en) | 2006-02-13 | 2006-04-12 | Intramuscular antiviral treatments |
Country Status (8)
Country | Link |
---|---|
JP (1) | JP2009533428A (en) |
CN (1) | CN104784166A (en) |
AU (1) | AU2006341592A1 (en) |
BR (1) | BRPI0621552A2 (en) |
CA (1) | CA2649090A1 (en) |
EA (1) | EA200870430A1 (en) |
MX (1) | MX2008013140A (en) |
WO (1) | WO2007117241A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011083317A1 (en) * | 2010-01-08 | 2011-07-14 | Varleigh Immuno Pharmaceuticals Limited | Ev576 for use in the treatment of viral infections of the respiratory tract |
CN102584637A (en) * | 2011-01-17 | 2012-07-18 | 天津药物研究院 | Peramivir hydrate crystal, preparation method, medical compound and usage thereof |
US9192648B2 (en) | 2005-09-09 | 2015-11-24 | Volution Immuno Pharmaceuticals Sa | Method of treating myasthenia gravis |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101367750B (en) * | 2007-08-14 | 2012-05-23 | 中国人民解放军军事医学科学院毒物药物研究所 | (1S,2S,3S,4R)-3-[(1S)-1-acet-ammonia-2-ethyl-butyl]-4- guanidino-2-hydroxyl-cyclopentyl-1-carboxylic acid aqua compound and medical uses thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUP0100142A3 (en) * | 1997-12-17 | 2002-01-28 | Biocryst Pharmaceuticals Inc B | Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors |
GB0015324D0 (en) * | 2000-06-22 | 2000-08-16 | Biota Scient Management | Medicaments |
-
2006
- 2006-04-12 MX MX2008013140A patent/MX2008013140A/en not_active Application Discontinuation
- 2006-04-12 BR BRPI0621552-1A patent/BRPI0621552A2/en not_active IP Right Cessation
- 2006-04-12 WO PCT/US2006/013535 patent/WO2007117241A1/en active Application Filing
- 2006-04-12 CA CA002649090A patent/CA2649090A1/en not_active Abandoned
- 2006-04-12 AU AU2006341592A patent/AU2006341592A1/en not_active Abandoned
- 2006-04-12 JP JP2009505338A patent/JP2009533428A/en active Pending
- 2006-04-12 EA EA200870430A patent/EA200870430A1/en unknown
-
2007
- 2007-02-12 CN CN201510115375.7A patent/CN104784166A/en active Pending
Non-Patent Citations (1)
Title |
---|
BANTIA ET AL: "Anti-influenza virus activity of peramivir in mice with single intramuscular injection", ANTIVIRAL RESEARCH, ELSEVIER SCIENCE BV., AMSTERDAM, NL, vol. 69, no. 1, January 2006 (2006-01-01), pages 39 - 45, XP005212462, ISSN: 0166-3542 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9192648B2 (en) | 2005-09-09 | 2015-11-24 | Volution Immuno Pharmaceuticals Sa | Method of treating myasthenia gravis |
WO2011083317A1 (en) * | 2010-01-08 | 2011-07-14 | Varleigh Immuno Pharmaceuticals Limited | Ev576 for use in the treatment of viral infections of the respiratory tract |
US9522171B2 (en) | 2010-01-08 | 2016-12-20 | Volution Immuno Pharmaceuticals Sa | EV576 for use in the treatment of viral infections of the respiratory tract |
CN102584637A (en) * | 2011-01-17 | 2012-07-18 | 天津药物研究院 | Peramivir hydrate crystal, preparation method, medical compound and usage thereof |
Also Published As
Publication number | Publication date |
---|---|
JP2009533428A (en) | 2009-09-17 |
BRPI0621552A2 (en) | 2011-12-13 |
EA200870430A1 (en) | 2009-06-30 |
MX2008013140A (en) | 2009-02-12 |
AU2006341592A1 (en) | 2007-10-18 |
CA2649090A1 (en) | 2007-10-18 |
CN104784166A (en) | 2015-07-22 |
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