WO2012108794A2 - Dérivés de l'acide 1,2,4-triazol-з-yl-thioglycolique destinés à s'utiliser en thérapie - Google Patents

Dérivés de l'acide 1,2,4-triazol-з-yl-thioglycolique destinés à s'utiliser en thérapie Download PDF

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Publication number
WO2012108794A2
WO2012108794A2 PCT/RU2012/000085 RU2012000085W WO2012108794A2 WO 2012108794 A2 WO2012108794 A2 WO 2012108794A2 RU 2012000085 W RU2012000085 W RU 2012000085W WO 2012108794 A2 WO2012108794 A2 WO 2012108794A2
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Prior art keywords
acid
ylthioglycolic
pharmaceutical composition
chlorophenyl
triazol
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Russian (ru)
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WO2012108794A3 (fr
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Андрей Александрович ВИННИК
Петр Олегович ФЕДИЧЕВ
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • 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
    • 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

Definitions

  • influenza and other acute respiratory viral infections are very relevant in human viral pathology. This is due to the fact that according to the World Health Organization, these are the most common diseases that cause enormous damage to the health of the world's population and the economies of all countries. Most often, influenza and viral infections affect children: children under the age of one year are 3 times more likely than other preschool children and 5 times more likely than adults. The elderly are also very vulnerable. These infections contribute to the formation of chronic respiratory diseases, are one of the causes of pneumonia, aggravate the course of other diseases, contributing to their adverse outcome. Even in the inter-epidemic time, influenza and acute respiratory viral infections account for up to 40% of all diseases registered in medical institutions of the Russian Federation among adults and more than 60% among children. However, to prevent these diseases there are no guaranteed specific vaccines, and in their treatment are used, in mainly pathogenetic and symptomatic agents, since the arsenal of etiotropic antiviral drugs is small.
  • Amantadine and remantadine are widely used for the treatment of influenza in medical practice, as antiviral prophylactic and therapeutic agents that have antiviral activity against influenza virus strains [Am. J. Med. - 1997. - V.102 (3A) - N17. - P.55-60], [Watts J. “Asian nations step up action to curb spread of avian influenza” // Lancet. - 2004. - V.363 - N 9406. - P. 373].
  • the antiviral drug Remantadine has spread. It is used to treat and prevent infection caused by type A influenza viruses. A pronounced therapeutic effect, the drug showed against the influenza virus subtype H3N2.
  • the mechanism of action on the virus is associated with blocking the function of the viral protein within the membrane. Inhibition of viral activity occurs at the stages of receptor-mediated endocytosis, decapsidation in the phagolysosome, as well as the assembly and budding of viral particles [Vestnik RAMS // 1993. - N 3. - P.10-15].
  • remantadine as a representative of the adamantane group, has limitations in its use. At high doses, side effects from the central nervous system occur, in particular, it can cause convulsive effects. It also has an adverse effect on the liver and kidneys, which makes it unlikely to be used in people with diseases of these organs.
  • oseltamivir phosphate oseltamivir
  • zanamivir zanamivir
  • Oseltamivir the trade name Tamiflu®
  • zanamivir the trade name Relenza®
  • Relenza® are considered one of the most effective antiviral drugs.
  • oseltamivir and zanamivir there are currently reported cases of resistance to oseltamivir and zanamivir [Menno D. de Jong, Tran Tan Thanh, Truong Huu Khanh et al. Oseltamivir Resistance during Treatment of Influenza A (H5N1) Infection // N. Engi. J. Med. - 2005. - N 353. - P.2667-2572]
  • neuraminidase inhibitors have pronounced CNS side effects. So, the experts of the British Health Protection Agency gave recommendations to the British government that oseltamivir, or Tamiflu, should not be prescribed to children for the prevention of A / H1N1 flu due to the large number of undesirable side effects.
  • the aim of this invention is the development of new approaches to treatment by using previously unused compounds in therapy that are derivatives of 1,2,4-triazol-3-ylthioglycolic acid, including their use for the treatment of viral diseases, including influenza (including influenza A and influenza B), new methods of treating influenza, new ways of using these substances.
  • viral diseases including influenza (including influenza A and influenza B)
  • influenza including influenza A and influenza B
  • new methods of treating influenza new ways of using these substances.
  • no publications, studies and / or reports on the use of this class of organic compounds in therapy and the presence of antiviral activity have been found.
  • the scope of the invention relates to the use of patentable compounds, their pharmacologically acceptable salts, salt adducts or solvates and pharmaceutical compositions based on them for use in therapy, including for the treatment of diseases caused by various viral infections.
  • each of R1 and R2 is independently selected from hydrogen, Cl-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-6-cycloalkyl, aryl, heteroaryl, optionally substituted with one or more substituents independently selected from halogen, aryl, heteroaryl, Cl-6-alkyl, Cl-6-alkenyl, C2-6-alkynyl, OC1-6-alkyl, and a dialkyl group;
  • R3 is selected from hydrogen, Cl-6-alkyl, aryl
  • R4 is selected from hydrogen, Cl-6-alkyl
  • each of R5 and R6 is independently selected from hydrogen, Cl-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-6-cycloalkyl, aryl, heteroaryl, optionally substituted with one or more substituents independently selected from halogen, aryl, heteroaryl, Cl-6-alkyl, Cl-6-alkenyl, C2-6-alkynyl, heterocyclyl, OC 1-6-alkyl, OC1-6-alkenyl, OC2-6-alkynyl, ⁇ 02 ⁇ , ⁇ , OCH2Ph and dialkylamino groups .
  • the present invention relates to the use of derivatives of 1,2,4-triazol-3-ylthioglycolic acid of formula (I) in therapy.
  • the present invention relates to the use of derivatives of 1,2,4-triazol-3-ylthioglycolic acid of the formula (I) in the treatment of humans and / or animals.
  • the present invention relates to the use of derivatives of 1,2,4-triazol-3-ylthioglycolic acid of formula (I) in the treatment of viral disease.
  • the present invention relates to the use of derivatives of 1, 2,4-triazol-3-ylthioglycolic acid of formula (I) in therapy for the prevention and / or treatment of influenza.
  • the present invention relates to the use of derivatives of 1,2,4-triazol-3-ylthioglycolic acid of formula (I) in therapy for prophylaxis and / or treating type A flu
  • the present invention relates to the use of derivatives of 1,2,4-triazol-3-ylthioglycolic acid of formula (I) in therapy for the prevention and / or treatment of type B influenza.
  • compositions comprising, as a therapeutically active agent, at least one 1,2,4-triazol-3-ylthioglycolic acid derivative of the formula (I) or a prodrug thereof.
  • the present invention relates to a method for producing pharmaceutical compositions containing, as a therapeutically active agent, at least one 1,2,4-triazol-3-ylthioglycolic acid derivative of the formula (I) or a prodrug thereof, by mixing at least at least one therapeutically active agent with a pharmaceutically acceptable carrier.
  • the present invention relates to dosage forms for the prevention and / or treatment of viral diseases, containing as a therapeutically active agent, at least one derivative of 1,2,4-triazol-3-ylthioglycolic acid of the formula (I) or a prodrug thereof .
  • the present invention relates to a method for treating a viral disease of a human and / or animal by administering a pharmaceutical composition containing, as a therapeutically active agent, at least one 1,2,4-triazol-3-ylthioglycolic acid derivative of the formula (I ) or a prodrug thereof in a therapeutically effective amount.
  • the present invention relates to a method for treating a human and / or animal viral disease caused by an influenza virus by administering a pharmaceutical composition comprising, as a therapeutically active agent, at least one 1,2,4-triazol-3-ylthioglycolic derivative an acid of formula (I) or a prodrug thereof in a therapeutically effective amount.
  • the present invention relates to a method for treating a human and / or animal viral disease caused by influenza A virus by administering a pharmaceutical composition containing as a therapeutically active an agent, at least one 1,2,4-triazol-3-ylthioglycolic acid derivative of the formula (I) or a prodrug thereof in a therapeutically effective amount.
  • the present invention relates to a method for treating a human and / or animal viral disease caused by influenza B virus by administering a pharmaceutical composition comprising, as a therapeutically active agent, at least one derivative of 1, 2,4-triazole-3- ilthioglycolic acid of formula (I) or a prodrug thereof in a therapeutically effective amount.
  • a compound comprising a 1,2,4-triazol-3-ylthioglycolic acid derivative of the general formula (I) or a pharmaceutically acceptable salt, salt adduct or solvate thereof
  • each of R1 and R2 is independently selected from hydrogen, C1 -6 -alkyl, C 2-6 - alkenyl, C 2-6 -alkynyl, C 3-6 -cycloalkyl, aryl, heteroaryl, optionally substituted with one or more substituents, independently selected from halogen, aryl, heteroaryl, C] -6 alkyl, C ⁇ b-alkenyl, C 2-6 alkynyl, OC1. 6- alkyl and dialkylamino groups;
  • R3 is selected from hydrogen, Ci-b. Alkyl, aryl;
  • R4 is selected from hydrogen, C ⁇ b. Alkyl
  • each of R5 and R6 is independently selected from hydrogen, C 2-6 -alkenyl, C 2-6 - alkynyl, C 3-6 cycloalkyl, aryl, heteroaryl, optionally substituted with one or more substituents independently selected from halogen, aryl, heteroaryl, C 1-6 - alkyl, Ci- b-alkenyl, C 2-6 alkynyl, heterocyclyl, OC] -6 alkyl, OC ] -6 alkenyl, OC 2 b-alkynyl, C0 2 CH 3 , OCOCH 3 , OCH 2 Ph and dialkylamino groups,
  • the compound according to claim 1 characterized in that it is used in the treatment of humans and / or animals.
  • a pharmaceutical composition comprising, as a therapeutically active agent, at least one compound according to claim 1 or a prodrug thereof.
  • composition according to claim 19 for the treatment of a viral disease.
  • composition according to claim 19 for the prevention of viral disease.
  • composition according to any one of claims 19-24 containing 5- (4-tert-butylphenyl) -4-phenyl-1,2,4-triazole-3 as therapeutically active agent (3-benzyloxyphenyl) methylidenehydrazide - ilthioglycolic acid.
  • composition according to any one of claims 19-24 containing (3,4,5-trimethoxyphenyl) methylidenehydrazide 5- (4-chlorophenyl) -4- (4-methylphenyl) -1, 2 as therapeutically active agent , 4-triazole-Z - ylthioglycolic acid.
  • alkyl means a monovalent saturated hydrocarbon group, which may be linear or branched, or may be a combination thereof.
  • Representative alkyl groups include, as examples, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butip, pgret-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n nonyl, n-decyl, etc.
  • a certain number of carbon atoms is meant in the case of the particular term used here, the number of carbon atoms is indicated before the term itself.
  • C ] -6 alkyl means an alkyl group having from 1 to 6 carbon atoms.
  • alkenyl means a monovalent unsaturated hydrocarbon group that contains at least one carbon-carbon double bond, usually 1 or 2 carbon-carbon double bonds and which may be linear or branched or may be a combination thereof.
  • alkenyl groups include, as examples, vinyl, allyl, isopropenyl, but-2-enyl, n-pent-2-enyl, n-hex-2-enyl, n-hept-2-enyl, n-oct -2-enyl, c-non-2-enyl, n-dec-4-enyl, n-dec-2,4-dienyl, etc.
  • alkynyl means a monovalent unsaturated hydrocarbon group that contains at least one carbon-carbon triple bond, usually 1 carbon-carbon triple bond, and which may be linear or branched or may be a combination thereof.
  • Representative alkynyl groups include, as examples, ethynyl, propargyl, but-2-ynyl, etc.
  • cycloalkyl means a monovalent saturated carbocyclic group, which may be monocyclic or multicyclic.
  • Representative cycloalkynyl groups include, as examples, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.
  • aryl means a monovalent aromatic hydrocarbon having a single ring (i.e., phenyl) or fused rings (i.e., naphthyl). Unless otherwise indicated, such aryl groups typically contain from 6 to 10 ring carbon atoms. Representative aryl groups include, as examples, phenyl and naphthalen-1-yl, naphthalen-2-yl, etc.
  • heteroaryl means a monovalent aromatic group having a single ring or two fused rings and containing at least one heteroatom in this ring (usually 1 to 3 heteroatoms) selected from nitrogen, oxygen and sulfur. Unless otherwise indicated, such heteroaryl groups typically contain from 5 to 10 total ring atoms.
  • heteroaryl groups include, by way of example, pyrroyl, isoxazolyl, isothiazolyl, pyrazolyl, pyridyl (or, equivalently, pyridinyl), oxazolyl, oxadiazolyl, thiadiazolyl, thiazolyl, imidazolyl, triazolyl, tetrazolyl, thyryl, furyl pyridazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, quinolyl, indolyl, isoquinolyl, etc., where the point of attachment is any available ring carbon or nitrogen atom.
  • heterocyclyl or heterocyclic ring means a monovalent saturated or partially unsaturated cyclic non-aromatic group, which may be monocyclic or multicyclic (for example, fused or bridged) and which contains at least one heteroatom (usually from 1 to 3 heteroatoms) selected from nitrogen, oxygen and sulfur. Unless otherwise indicated, such heterocyclyl groups typically contain from 5 to 10 total ring atoms.
  • heterocyclic groups include, by way of example, pyrrolidinyl, piperidinyl, piperazinyl, imidazolidinyl, morpholinyl, indolyl-3-yl, 2-imidazolinyl, 1,2,3,4-tetrahydroisoquinolin-2-yl, quinuclidinyl and the like.
  • halogen means fluoro, chloro, bromo or iodo.
  • terapéuticaally effective amount means an amount sufficient for effective treatment when administered to a patient, if treatment is necessary.
  • pharmaceutically acceptable salt means a salt derived from a base or acid that is acceptable for administration to a patient, a human or an animal. Such salts may be prepared from pharmaceutically acceptable inorganic or organic bases and from pharmaceutically acceptable inorganic or organic acids.
  • Salts derived from pharmaceutically acceptable acids include, but are not limited to, salts of acetic, benzenesulfonic, benzoic, camphosulfonic, citric, ethanesulfonic, fumaric, gluconic, glutamic, hydrobromic, hydrochloric, lactic, maleic, malic, mandelic, almond nitric, pantothenic, phosphoric, succinic, sulfuric, tartaric, and-toluenesulfonic acids and others.
  • salts derived from fumaric, hydrobromic, hydrochloric, acetic, sulfuric, methanesulfonic, citric and tartaric acids are especially preferred.
  • Salts derived from pharmaceutically acceptable inorganic bases include aluminum, ammonium, calcium, copper, iron (III), iron (II), lithium, magnesium, manganese III), manganese (II), potassium, sodium, zinc and etc. Particularly preferred are salts of ammonium, calcium, magnesium, potassium and sodium.
  • Salts derived from pharmaceutically acceptable organic bases include salts of primary, secondary and tertiary amines, including substituted amines, cyclic amines, naturally occurring amines, etc., such as arginine, betaine, caffeine, choline, ⁇ , ⁇ '-dibenzylethylenediamine , diethylamine, 2-diethylaminoethanol, 2-dimethylaminoethanol, ethanolamine, ethylenediamine, ⁇ -ethylmorpholine, ⁇ -ethylpiperidine, glucamine, glucosamine, histidine, hydrabamine, isopropylamine, lysine, methylglucamine, morpholine, piperine, piperine, piperine, piperine , Theobromine, triethylamine, trimethylamine, tripropylamine, tromethamine, and so forth.
  • arginine betaine
  • caffeine choline
  • solvate means a complex or aggregate formed by one or more molecules of a solute, i.e. a compound according to the invention or a pharmaceutically acceptable salt thereof and one or more solvent molecules. Such solvates are typical solid crystals having a substantially fixed molar ratio of solute to solvent. Representative solvents include, but are not limited to, water, ethanol, isopropanol, acetic acid, etc. When the solvent is water, the solvate formed is a hydrate.
  • acylhydrazines 1.1 interact with thioisocyanates of various nature 1.2 with the formation of acylthiosemicarbazides 1.3, which, under the action of alkalis, cyclize to form 5-mercapto-1,2,4-triazoles 1.4.
  • S-alkylation with various derivatives of chloroacetic acid hydrazide 1.9 leads to the target compounds 1.5.
  • the synthesis of chloro derivatives of 1.9 was carried out using ethyl chloroacetate and its homologues 1.6, hydrazine or its derivative 1.7, aldehydes or ketones 1.8.
  • the precipitate formed is filtered off, washed with water, dried and, if necessary, crystallized from aqueous ethanol.
  • Intermedia TM 1.9 is synthesized according to the methods: Helvetica Chim. Acta, 47, 2449 and Bull. Chem. Soc. Jpn., 43, 1970, 2257.
  • Target products 1.5.01-1.5.11 were synthesized according to the method: J. Med. Chem., 1984,
  • 20 animals are used. 20 further include control animals for toxicity compound as its maximum dose used, 20 animals (herd control -. Saline) and 20 animals (untreated infected group). To control antiviral activity, a group treated with Tamiflu — 20 animals is used.
  • mice 120 mice (6 groups of 20 animals each) are required.
  • a virus-containing suspension is injected into both nostrils of white mice under light ether anesthesia in a volume of 50 ⁇ l.
  • the infectious dose is 10 - 30 LD 5 of influenza virus A / Aichi / 2/68 (H3N2) for 20 mice in each group. Observation of animals is carried out within 14 days from the moment of infection, recording their death.
  • the invention also includes derivatives of substances described in this application (including so-called prodrugs).
  • Prodrugs as a rule (but not always), have less activity on the target protein than those substances into which they are converted. Prodrugs are particularly useful when the reception of the desired active compound is difficult or ineffective, e.g., because of low solubility or other problems of the active substance.
  • prodrug may be found in Stella, V. J. et al., "Prodrugs", Drug Delivery Systems, 1985, pp. 112-176, and Drugs, 1985.29, pp. 455-473.
  • the present invention may also include all possible forms of the substances described in this application, including, but not limited to, complex salts of salts, salt adducts of stereoisomeric forms of substances, as biologically active substances.
  • the present invention also relates to any pharmacologically acceptable carrier that assists in the delivery as an active substance to any of the substances described in this application, any of its forms or prodrugs.
  • compositions of the dosage forms any examples of compositions and / or dosage forms commonly used for systemically used drugs can be given.
  • compositions for the purpose of making a variant of the pharmaceutical composition of the present invention, but not limited to these examples, an effective amount of a substance from the class described or covered by this application or its salt can be taken. It is also possible in a mixture (composition) with a pharmaceutically acceptable carrier (vehicle), where the carriers can be a wide variety of forms and substances depending on the composition that is supposed to be administered to the patient. It is more convenient that these pharmaceutical compositions be in standardized doses, for example, for oral administration or parenteral administration.
  • the carrier may be sterile water, saline, or other ingredients, for example, substances that improve solubility.
  • the solutions for injection for example, the carrier may comprise a physiological saline solution or glucose solution, or a mixture of saline and glucose solution, buffer.
  • suspension for injection can also be produced in a suitable in each particular case or cases the number of representative or representatives of liquid carriers, dispersing agents and similar substances and compositions.
  • Also in the present invention include a therapeutically active agent as described herein or covered it, in the form of powder which is assumed shortly prior to receiving transfer in liquid form.
  • the pharmaceutical composition may also contain various other ingredients known from the prior art, such as stabilizing agents, a lubricant, a buffer, an emulsifier, a viscosity and / or tackifier, a surfactant, a preservative, an antioxidant, a dye, other additives and things like that.
  • stabilizing agents such as stabilizing agents, a lubricant, a buffer, an emulsifier, a viscosity and / or tackifier, a surfactant, a preservative, an antioxidant, a dye, other additives and things like that.
  • the pharmaceutical composition described above in the form of a dosage (unit dosage form).
  • the dosage in the description is used as a physically separate part, used for a single application. Such a portion contains a certain amount of the active ingredient necessary to obtain a therapeutic effect together with an acceptable pharmaceutical carrier.
  • Examples of such dosages are tablets of various shapes and appearance, capsules, powder sachets, lozenges, plates, suppositories, suppositories, injection solutions and so on, as well as various combinations of the above.
  • composition mg per tablet:
  • Hydroxypropylmethyl cellulose 20 When creating a solid dosage form in the form of tablets of the claimed medicinal product, starch in an amount of 1 mg to 10 mg per tablet was used as a filler to give better flowability and compressibility of the active substance. Potato and / or modified starch may be used.
  • stearic acid As lubricants and glidants, stearic acid, aerosil or collidone are used. These materials provide good flowability and uniform supply tabletiruemyh mass from the hopper into the matrix, and consequently provides a higher accuracy and constancy of the dosage of the drug substance. Contribute to the easier ejection of tablets from the matrix, preventing the formation of scratches on their faces.
  • lactose In order to give acceptable organoleptic properties to the composition, up to 60 mg lactose may be administered.
  • the result is a mixture of substances having good technological properties in the process of granulation and tableting.
  • the manufactured tablets have properties that meet the requirements of a pharmaceutical agent. They have a marketable appearance without chips and cracks, with the necessary strength and disintegration, and are stored for at least 2 years.
  • the new pharmaceutical formulation is in the form of a solid dosage form, preferably, but not necessarily, coated in the form of a tablet.
  • the presence of the shell of the claimed composition gives, firstly, the stability of the composition during storage, and secondly, improves its appearance and organoleptic properties.

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Abstract

L'invention concerne des dérivés de l'acide 1,2,4-triazol-З-yl-thioglycolique, leurs pharmaceutiquement acceptables, des additifs à base de sel ou des solvates ainsi que des compositions pharmaceutiques, destinés à s'utiliser en thérapie.
PCT/RU2012/000085 2011-02-10 2012-02-10 Dérivés de l'acide 1,2,4-triazol-з-yl-thioglycolique destinés à s'utiliser en thérapie Ceased WO2012108794A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2011104686 2011-02-10
RU2011104686/04A RU2011104686A (ru) 2011-02-10 2011-02-10 Производные 1,2,4-триазол-3-илтиогликолевой кислоты для применения в терапии

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WO2012108794A2 true WO2012108794A2 (fr) 2012-08-16
WO2012108794A3 WO2012108794A3 (fr) 2012-10-26

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2626003C2 (ru) * 2014-04-28 2017-07-21 Общество с ограниченной ответственностью "Квантум Фармасьютикалс" Амид 1,2,4-триазол-3-илтиогликолевой кислоты, обладающий противовирусной активностью, или его фармацевтически приемлемые соли, фармацевтические композиции и их применение для лечения и профилактики гриппа

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3238903A1 (de) * 1982-10-21 1984-04-26 Bayer Ag, 5090 Leverkusen Antivirales mittel

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2626003C2 (ru) * 2014-04-28 2017-07-21 Общество с ограниченной ответственностью "Квантум Фармасьютикалс" Амид 1,2,4-триазол-3-илтиогликолевой кислоты, обладающий противовирусной активностью, или его фармацевтически приемлемые соли, фармацевтические композиции и их применение для лечения и профилактики гриппа

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