[go: up one dir, main page]

WO2012060820A1 - Sulfonyl semicarbazides, semicarbazides et urées, compositions pharmaceutiques à base de ceux-ci, et procédés de traitement des virus responsables des fièvres hémorragiques, comprenant des infections associées à des arénavirus - Google Patents

Sulfonyl semicarbazides, semicarbazides et urées, compositions pharmaceutiques à base de ceux-ci, et procédés de traitement des virus responsables des fièvres hémorragiques, comprenant des infections associées à des arénavirus Download PDF

Info

Publication number
WO2012060820A1
WO2012060820A1 PCT/US2010/055086 US2010055086W WO2012060820A1 WO 2012060820 A1 WO2012060820 A1 WO 2012060820A1 US 2010055086 W US2010055086 W US 2010055086W WO 2012060820 A1 WO2012060820 A1 WO 2012060820A1
Authority
WO
WIPO (PCT)
Prior art keywords
urea
bis
propyl
trifluoromethyl
substituted
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.)
Ceased
Application number
PCT/US2010/055086
Other languages
English (en)
Inventor
Dongcheng Dai
Tove Bolken
Sean M. Amberg
Dennis E. Hruby
Thomas R. Bailey
Jack H. Nunberg
Celestine Johnson Thomas
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.)
Siga Technologies Inc
Original Assignee
Siga Technologies 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 Siga Technologies Inc filed Critical Siga Technologies Inc
Priority to PCT/US2010/055086 priority Critical patent/WO2012060820A1/fr
Publication of WO2012060820A1 publication Critical patent/WO2012060820A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/433—Thidiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4866—Organic macromolecular compounds
    • 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

  • the instant invention further provides for methods of treating Arenavirus infection, comprising administering in a therapeutically effective amount to a mammal in need thereof, a compound of formula I below:
  • Ri is selected from the group consisting of H and alky l;
  • Cycloalkyl refers to cyclic alkyl groups of from 3 to 8 carbon atoms having a single cyclic ring including, by way of example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like. Excluded from this definition are multi-ring alkyl groups such as adamantanyl, etc.
  • Salts derived from inorganic bases include by way of example only, sodium, potassium, lithium, ammonium, calcium and magnesium salts.
  • Salts derived from organic bases include, but are not limited to, salts of primary, secondary and tertiary amines, such as alkyl amines, dialkyl amines, trialkyl amines, substituted alkyl amines, di(substituted alkyl) amines, tri(substituted alkyl) amines, alkenyl amines, dialkenyl amines, trialkenyl amines, substituted alkenyl amines, di(substituted alkenyl) amines, tri (substituted alkenyl) amines, cycloalkyl amines, di(cycloalkyl) amines, tri(cycloalkyl) amines, substituted cycloalkyl amines, disubstituted cycloalkyl amine,
  • a “therapeutically effective amount” means the amount of a compound or antibody that, when administered to a mammal for treating a disease, is sufficient to effect such treatment for the disease.
  • the “therapeutically effective amount” will vary depending on the compound, the disease and its severity and the age, weight, etc., of the mammal to be treated.
  • sustained-release preparations include semipermeable matrices of solid hydrophobic polymers containing the protein, which matrices are in the form of shaped articles, e.g., films, or microcapsules.
  • sustained-release matrices include polyesters, hydrogels (e.g., poly(2-hydroxyethyl-methacrylate) as described by Langer et ah, J. Biomed. Mater. Res. 15: 167-277 (1981) and Langer, Chem. Tech. 12: 98-105 (1982) or poly(vinyl alcohol)), polylactides (U.S. Patent No.
  • the compounds of this invention can be administered in a sustained release form, for example a depot injection, implant preparation, or osmotic pump, which can be formulated in such a manner as to permit a sustained release of the active ingredient.
  • Implants for sustained release formulations are well-known in the art. Implants may be formulated as, including but not limited to, microspheres, slabs, with biodegradable or non-biodegradable polymers. For example, polymers of lactic acid and/or glycolic acid form an erodible polymer that is well-tolerated by the host.
  • Magnesium stearate 5.0 [000128] The above ingredients are mixed and filled into hard gelatin capsules in 340 mg quantities.
  • Suspensions each containing 50 mg of medicament per 5.0 ml dose are made as follows:
  • Isotonic saline 1000 ml Therapeutic compound compositions generally are placed into a container having a sterile access port, for example, an intravenous solution bag or vial having a stopper pierceable by a hypodermic injection needle or similar sharp instrument.
  • transdermal delivery devices Such transdermal patches may be used to provide continuous or discontinuous infusion of the compounds of the present invention in controlled amounts.
  • the construction and use of transdermal patches for the delivery of pharmaceutical agents is well known in the art. See, e.g., U.S. Patent No. 5,023,252, issued June 1 1 , 1991, herein incorporated by reference. Such patches may be constructed for continuous, pulsatile, or on demand delivery of pharmaceutical agents.
  • Direct or indirect placement techniques may be used when it is desirable or necessary to introduce the pharmaceutical composition to the brain.
  • the compounds may be encapsulated, introduced into the lumen of liposomes, prepared as a colloid, or other conventional techniques may be employed which provide an extended serum half life of the compounds.
  • a variety of methods are available for preparing liposomes, as described in, e.g., Szoka, et ah, U.S. Patent Nos. 4,235,871 ,
  • the chiral product can be obtained via purification techniques which separates enantiomers from a R, S mixture to provide for one or the other stereoisomer. Such techniques are known in the art.
  • the compounds can be provided as prodrugs which convert (e.g., hydrolyze, metabolize, etc.) in vivo to a compound of Formula I above.
  • the carboxylic acid group of the compound of Formula I is modified into a group which, in vivo, will convert to a carboxylic acid group (including salts thereof).
  • the inhibitory activity of each compound was calculated by subtracting from the OD570 of test compound well from the average OD570 of virus-infected cell wells, then dividing by the average OD570 of mock-infected cell wells. The result represents the percent protection against Tacaribe virus CPE activity conferred by the compound. "Hits" in this assay were defined as compounds that inhibited virus-induced CPE by greater than 50% at the test concentration (5 (J.M). Of the approximately 400,000 compounds screened in the Tacaribe virus HT S campaign, 2,347 hits were identified (0.58% hit rate). [000174] Quality hits are defined as inhibitor compounds (hits) that exhibit acceptable chemical structures, antiviral potency and selectivity, and spectrum of antiviral activity.
  • MRC-5 cells human normal lung fibroblast; ATCC #CCL-171 were cultured in MEM containing 10% heat-inactivated FBS, 1% penicillin/streptomycin, 1% L- glutamine (Invitrogen 25030-081), 1 % Non-Essential Amino Acids (Invitrogen #1 1 140-050), 1% sodium pyruvate (Invitrogen #1 1360-070), and 2% sodium bicarbonate.
  • reference agents when available, were included on each assay plate (gancyclovir for HSV-1 and CMV, Sigma #G2536; ribavirin for LCMV and RSV, Sigma #R9644; and rifampicin for vaccinia virus, Sigma #R3501). Plates were incubated at 37 ° C and 5% CO 2 for either 3 days (HSV-1 , Rotavirus, LCMV, Vaccinia virus) or 4 days (Tacaribe virus, Amapari virus, Candid 1 virus, SARS-CoV, RSV, and CMV).
  • Genotoxicity An exploratory bacterial mutagenicity assay (Ames test) was used to assess the potential of the compound genotoxicity. T his assay utilized S. typhimurium tester strains TA7007 and TA7006 (single base pair mutations) and TA98 (frame shift mutation) with and without metabolic activation (Arochlor-induced rat liver S9) as described previously. 32
  • PK Pharmacokinetic
  • IP intraperitoneal ly
  • a 50 ⁇ aliquot of plasma was combined with 150 ⁇ of 100% acetonitrile containing an internal standard (100 ng/ml tolbutamide) in a 1.5 ml centrifuge tube. Samples were vortexed and centrifiiged at 13,000 rpm for ten minutes. An 80 ⁇ aliquot of the resulting supernatant was then transferred to an HPLC for vial analysis. Plasma levels of each compound were determined by LC/MS/MS, and pharmacokinetic parameters were determined using WinNolin software.
  • ST-336 DR ST-336 drug resistant variants
  • RNA viruses Sixteen ST -336 DR isolates from four independent wild type Tacaribe virus stocks were isolated and plaque purified three times. All ST-336 DR isolates were tested for their ability to grow in the presence of ST-336. The growth of ST-336 DR isolates was unaffected by the presence of ST-336 at concentrations that completely inhibited wild type Tacaribe virus replication (data not shown). The isolation and confirmation of drug resistant virus variants strongly suggest that ST-336 acts as a direct antiviral inhibitor.
  • Luciferase activity was measured 2-3 days post-infection using standard luciferin- based bioluminescence detection methods, such as Promega's Luciferase Assay System. Each compound dilution was tested in triplicate wells, and luciferase activity was converted to a percentage of infectivity based on positive (no compound) and negative (no virus) controls on the same plate.
  • baculoviruses were generated using the Invitrogen Bac-to-BacTM system. Coding regions corresponding to SSP and the G 1 G2 precursor of GPC from the pathogenic MC2 strain of JUNV (GenBank accession number D 10072) 43 ' 53 were inserted downstream of the baculovirus p 10 and polyhedrin protein promoters in the pFastBac-Dual vector (Invitrogen), respectively. The G1G2 precursor was expressed using the conventional signal peptide from human CD4 43 .
  • the lysate was stirred for 2 hr, clarified (100,000 x g for 1 hr), and the supernatant was incubated with M2 anti-FLAG MAb immobilized to agarose beads (Sigma) for 2 hr with slight agitation.
  • the beads were then loaded onto a column, washed with DDM-containing lysis buffer to remove non-specifically bound proteins, and icd-GPC was eluted with 5 ⁇ of 3xFLAG peptide (Sigma). T he eluate was dialyzed to remove the peptide and subjected to size-exclusion chromatography using a Superdex-200/G-75 tandem column (GE Healthcare).

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Otolaryngology (AREA)
  • Pulmonology (AREA)
  • Dispersion Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention porte sur des composés, des procédés et des compositions pharmaceutiques pour le traitement d'infections virales, par administration de certains nouveaux semicarbazides, sulfonyl carbazides, urées et composés apparentés dans des quantités thérapeutiquement efficaces. L'invention porte également sur des procédés de préparation des composés et sur des procédés d'utilisation des composés et des compositions pharmaceutiques à base de ceux-ci. En particulier, l'invention porte sur le traitement et la prophylaxie d'infections virales, telles que celles provoquées par les virus responsables des fièvres hémorragiques, c'est-à-dire, comprenant, mais sans y être limités, les Arenaviridae (Junin, Machupo, Guanavito, Sabia et Lassa), les Filoviridae (virus d'ébola et de Marburg), les Flaviviridae (virus de la fièvre jaune, de la fièvre hémorragique omsk et de la maladie de la forêt de Kyasanur) et les Bunyaviridae (virus de la vallée du Rift).
PCT/US2010/055086 2010-11-02 2010-11-02 Sulfonyl semicarbazides, semicarbazides et urées, compositions pharmaceutiques à base de ceux-ci, et procédés de traitement des virus responsables des fièvres hémorragiques, comprenant des infections associées à des arénavirus Ceased WO2012060820A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US2010/055086 WO2012060820A1 (fr) 2010-11-02 2010-11-02 Sulfonyl semicarbazides, semicarbazides et urées, compositions pharmaceutiques à base de ceux-ci, et procédés de traitement des virus responsables des fièvres hémorragiques, comprenant des infections associées à des arénavirus

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2010/055086 WO2012060820A1 (fr) 2010-11-02 2010-11-02 Sulfonyl semicarbazides, semicarbazides et urées, compositions pharmaceutiques à base de ceux-ci, et procédés de traitement des virus responsables des fièvres hémorragiques, comprenant des infections associées à des arénavirus

Publications (1)

Publication Number Publication Date
WO2012060820A1 true WO2012060820A1 (fr) 2012-05-10

Family

ID=46024731

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/055086 Ceased WO2012060820A1 (fr) 2010-11-02 2010-11-02 Sulfonyl semicarbazides, semicarbazides et urées, compositions pharmaceutiques à base de ceux-ci, et procédés de traitement des virus responsables des fièvres hémorragiques, comprenant des infections associées à des arénavirus

Country Status (1)

Country Link
WO (1) WO2012060820A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8410149B2 (en) 2004-12-06 2013-04-02 Siga Technologies Inc. Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses
US8642596B2 (en) 2004-12-06 2014-02-04 Siga Technologies, Inc. Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arena viruses
US8658697B2 (en) 2004-12-06 2014-02-25 Siga Technologies, Inc. Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6077661A (en) * 1994-06-10 2000-06-20 Georgetown University Internally controlled virion nucleic acid amplification reaction for quantitation of virion and virion nucleic acid
US20090203675A1 (en) * 2004-12-06 2009-08-13 Siga Technologies, Inc. Sulfonyl Semicarbazides, Semicarbazides and Ureas, Pharmaceutical Compositions Thereof, and Methods for Treating Hemorrhagic Fever Viruses, Including Infections Associated with Arena Viruses

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6077661A (en) * 1994-06-10 2000-06-20 Georgetown University Internally controlled virion nucleic acid amplification reaction for quantitation of virion and virion nucleic acid
US20090203675A1 (en) * 2004-12-06 2009-08-13 Siga Technologies, Inc. Sulfonyl Semicarbazides, Semicarbazides and Ureas, Pharmaceutical Compositions Thereof, and Methods for Treating Hemorrhagic Fever Viruses, Including Infections Associated with Arena Viruses

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8410149B2 (en) 2004-12-06 2013-04-02 Siga Technologies Inc. Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses
US8642596B2 (en) 2004-12-06 2014-02-04 Siga Technologies, Inc. Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arena viruses
US8658697B2 (en) 2004-12-06 2014-02-25 Siga Technologies, Inc. Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses
US8664274B2 (en) 2004-12-06 2014-03-04 Siga Technologies, Inc. Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arena viruses
US9067873B2 (en) 2004-12-06 2015-06-30 Kineta Four, LLC Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses
US9115065B2 (en) 2004-12-06 2015-08-25 Kineta, Inc. Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with Arenaviruses

Similar Documents

Publication Publication Date Title
US8664274B2 (en) Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arena viruses
US9067873B2 (en) Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses
US7977365B2 (en) Antiviral drugs for treatment of arenavirus infection
US20110172281A1 (en) Anti-Viral Drugs for Treatment of Arenavirus Infection
US9199920B2 (en) Antiviral drugs for treatment of arenavirus infection
US20130096138A1 (en) Novel thiourea or urea derivative, preparation method thereof, and pharmaceutical composition for preventing or treating aids, containing same as active ingredient
WO2012037119A2 (fr) Inhibiteurs d&#39;entrée virale dans des cellules de mammifères
US20160052870A1 (en) 3-amidobenzamides and uses thereof for increasing cellular levels of a3g and other a3 family members
WO2012060820A1 (fr) Sulfonyl semicarbazides, semicarbazides et urées, compositions pharmaceutiques à base de ceux-ci, et procédés de traitement des virus responsables des fièvres hémorragiques, comprenant des infections associées à des arénavirus
US9115065B2 (en) Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with Arenaviruses
KR101241370B1 (ko) 신규한 티오우레아 또는 우레아 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 ａｉｄｓ 예방 또는 치료용 약학 조성물

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10859358

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10859358

Country of ref document: EP

Kind code of ref document: A1