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WO2022154772A1 - Agent antiviral utilisé dans des infections virales du tractus respiratoire supérieur et composition pharmaceutique le comprenant - Google Patents

Agent antiviral utilisé dans des infections virales du tractus respiratoire supérieur et composition pharmaceutique le comprenant Download PDF

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Publication number
WO2022154772A1
WO2022154772A1 PCT/TR2022/050007 TR2022050007W WO2022154772A1 WO 2022154772 A1 WO2022154772 A1 WO 2022154772A1 TR 2022050007 W TR2022050007 W TR 2022050007W WO 2022154772 A1 WO2022154772 A1 WO 2022154772A1
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WIPO (PCT)
Prior art keywords
extract
viral
viral agent
helichrysum
pharmaceutical composition
Prior art date
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Ceased
Application number
PCT/TR2022/050007
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English (en)
Inventor
Batuhan DEMIRCI
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.)
ALMEDIKO SAGLIK URUNLERI TURIZM GIDA SANAYI VE TICARET Ltd SIRKETI
Original Assignee
ALMEDIKO SAGLIK URUNLERI TURIZM GIDA SANAYI VE TICARET Ltd SIRKETI
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Publication of WO2022154772A1 publication Critical patent/WO2022154772A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/734—Alginic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/577—Malvaceae (Mallow family)
    • A61K36/5775—Hibiscus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
    • A61K36/738—Rosa (rose)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/46—Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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

  • This invention relates to an anti-viral agent for the treatment and prophylaxis of viral upper respiratory tract infections and pharmaceutical compositions comprising the same.
  • Rhinitis Upper respiratory tract infections are divided into sub-branches such as Rhinitis, Acute Otitis Media, Acute Rhino Sinusitis, Acute Tonsilla Pharyngitis, etc.
  • Common viruses causing these are Rhinoviruses, Coronaviruses including Covid- 19, Respiratory syncytial virus (RSV), Adenoviruses, Influenza and Parainfluenza viruses, Enteroviruses, Herpes simplex viruses, Cytomegaloviruses.
  • RSV Respiratory syncytial virus
  • Adenoviruses Influenza and Parainfluenza viruses
  • Enteroviruses Herpes simplex viruses
  • Cytomegaloviruses Cytomegaloviruses.
  • Infection is usually common in autumn and winter. Factors such as insufficient ventilation, low sunlight, and collective life facilitate the development of colds. The spread of infection occurs through direct contact with the skin or infected material or through particles carried in the air, and infected hands are the most important means of transmission.
  • Sore throat, runny nose, nasal congestion, confinement, sore throat and cough are the most common symptoms.
  • Fever is rare. Fever can be observed in young children. There may be tenderness, redness and crusting in the nose. Flu is most commonly confused with influenza and recently with Covid-19.
  • Influenza is usually caught once a year and is severe compared to the common flu. Muscle pain, headache, fever and significant weakness occur in the influenza in addition to the symptoms seen in the flu. It is accompanied by loss of smell, headache, muscle and joint pain, weakness, respiratory distress, cough, and fever in Covid-19.
  • influenza virus causes upper respiratory pain, headache, abdominal pain, chills, muscle weakness, etc.
  • the flu is caused by various types of viruses classified as A, B, and C4 groups.
  • influenza viruses often lead to similar symptoms, but are completely irrelevant antigenically, so that infection with one type does not provide any immunity against the other.
  • the virus survives in the upper respiratory tract epithelial cell for a long time ranging from 4 days to 2 weeks without entering the human body. It is not so harmful to cause pneumonia or often death, and it is a symbiotic virus that causes acute respiratory diseases such as asthma, chronic bronchitis, and allows it to reproduce easily.
  • Adenoviruses mainly cause throat diseases such as sore throat, headache and muscle pain and have virulence strong enough to cover 5 to 10% of the infant's cold and 70% of the respiratory cold in winter.
  • the RS virus causes inflammation in the infant's or children's lower respiratory tract, especially inducing pneumonia and bronchitis in infants younger than 1 year of age and occupying 50% of the origin of the disease.
  • Corona viruses cause an adult cold, which occurs between 10% and 30% in the winter, and stay asleep for 2 or 5 days, which lasts for about 1 week.
  • the injection vaccine which is known to be one of the effective therapeutic agents, can treat only about 70 to 90% of patients, but it is also not as satisfactory because there are too many antigenic -type viruses that are not treated with medication.
  • Coronavirus disease (Covid-19), which emerged in Wuhan, China in December 2019 and spread to many parts of the world in a short time, infected nearly sixty million people in a year and the number continues to increase day by day.
  • Most patients infected with Covid-19 present with asymptomatic or mild symptoms such as loss of taste, smell, sore throat, weakness, and joint pain. However, it can be severe in advanced age and patients who have to receive hypertension, diabetes, HIV, long-term immunosuppressive treatment and in cases that may reduce immunity such as pregnancy.
  • Symptomatic treatment by alleviating the cold symptom is known in the art using various antipyretics and the like, but they also do not satisfy the basic treatment.
  • Rosa canina L., Hibiscus sabdariffa, Thymbra spicata L. and Helichrysum sp. are generally presented individually in the form of oil and tea in the art. There are also teas containing Rosa canina L., Hibiscus sabdariffa.
  • a band is described in US2004071757A1 that allows for the inhalation of an anti-viral composition. It has been mentioned that the composition may comprise various essential oils, including those from various thyme genus Helichrysum spp., rosehip and Thymus. It has also been mentioned that thymol phenol found in thyme has antiviral properties.
  • a cleanser composition that may comprise anti-viral agents is described in US2005271595A1. It was stated that the composition may contain various extracts, including Hibiscus rosa-sinensis and Rosa canina, but these were used as moisturizers.
  • a topical antiviral composition that comprises an antiviral agent and excipients selected from a variety of oils, including Helichrysum and rosehip.
  • flavonoids including quercetin were investigated in the documents titled “Characteristics of flavonoids as potent MERS-CoV 3C-like protease inhibitors” (Jo S, Kim H, Kim S, Shin DH, Kim MS. Chem Biol Drug Des. 2019 Dec;94(6):2023-2030.) and “Inhibition of SARS-CoV 3CL protease by flavonoids” (Seri Jo, Suwon Kim, Dong Hae Shin & Mi-Sun Kim (2020) Journal of Enzyme Inhibition and Medicinal Chemistry, 35:1, 145- 151.)
  • compositions for the treatment and prophylaxis of viral upper respiratory tract infections are developed.
  • Compositions according to the invention affect the development of infection, especially by limiting viral activity, and also help to relieve symptoms.
  • compositions according to the invention provide relief, recover, improvement, stopping progression, and prevention of symptoms such as sore throat, runny nose, nasal congestion, sneezing, sore throat and cough in upper respiratory tract infections caused by viruses such as Rhinoviruses, Coronaviruses including Covid- 19, Respiratory syncytial virus (RSV), Adenoviruses, Influenza and Parainfluenza viruses, Enteroviruses, Herpes simplex viruses, Cytomegaloviruses and especially fever, headache, weakness, loss of taste and smell, musclejoint pain and respiratory distress, which are identified with Covid-19.
  • the composition provide prophylaxis by creating a strong barrier in the upper respiratory tract mucosa to protect against viruses.
  • Another object of the present invention is to develop pharmaceutical compositions that enable the effective use of this agent with an anti-viral agent consisting of certain proportions of flavonoid and polyphenol fractions obtained by purification of plants of Rosa Canina L., Hibiscus Sabdariffa, Thymbra Spicata L. and Helichrysum sp. in order to relieve, recover, improve, stop the progression of upper respiratory tract viral infection symptoms and provide prophylaxis to protect from viruses at the same time.
  • Another object of the invention is to provide prophylaxis by combining certain fractions of flavonoid and polyphenol obtained by purifying Rosa Canina L., Hibiscus Sabdariffa, Thymbra Spicata L. and Helichrysum sp. with sodium alginate, a natural polysaccharide product obtained from the cell wall of brown seaweed grown in cold water zones, by forming a protective barrier layer against viruses in the upper respiratory tract.
  • the anti-viral agent composition of the invention basically comprises Rosa canina L. extract, Hibiscus sabdariffa extract, Thymbra spicata L. extract, and Helichrysum sp. extract.
  • the antiviral agent of the invention prevents the virus from settling in the host cell by inducing TMPRSS2 thanks to the Thymbra spicata L. fraction it contains. Meanwhile, it provides to keep the immune system balance by protecting Thl/Th2 imbalance.
  • the anti-viral agent of the invention provides quercetin and vitamin support thanks to the strong antioxidant structure of the Rosa canina L. fraction.
  • vitamins in the fraction increase the effectiveness of Thymbra spicata L.
  • the Hibiscus sabdariffa fraction in the anti-viral agent of the invention does not remove H5N1 HPAIV when removing inactive human influenza viruses (H1N1 and H3N2) by demonstrating anti-viral activity. Therefore, it provides support for a strong anti -influenza product. In addition, the red color contained gives the product a natural color and thus, there is no need to use an additional colorant in the product.
  • the Helichrysum sp. fraction in the anti-viral agent of the invention has phenols similar to Thymbra spicata L. and supports the stability of phenols originating from Thymbra spicata L.
  • Thymbra Spicata L. The anti-viral activity of Thymbra Spicata L. was significantly increased by creating a synergistic effect with Helichrysum sp., Hibiscus sabdariffa and Rosa canina L., Thymbra Spicata L. in the anti-viral agent of the invention.
  • the said effectiveness of the anti-viral agent has been performed with pharmaceutical compositions comprising this anti-viral agent and is confirmed by the following trials.
  • the anti-viral agent of the invention preferably also comprises sodium alginate.
  • sodium alginate are composed of salts of a natural polysaccharide obtained from the cell wall of brown seaweed (Phaeophyceae) grown in cold water zones.
  • Sodium alginate prevents the adhesion of harmful agents to the superficial epithelial layers and provides prophylaxis in viral infections of the upper respiratory tract thanks to its strong barrier in the mucous membrane.
  • the anti-viral agent of the invention comprises 30 to 40% by weight, preferably 36% of Rosa canina L. extract, 30 to 40%, preferably 33% of Hibiscus sabdariffa extract, 10 to 20%, preferably 16% of Thymbra spicata L. extract, 10 to 20%, preferably 12% of Helichrysum sp. extract, and 1 to 5%, preferably 3% of sodium alginate.
  • a pharmaceutical composition according to the invention comprising the anti-viral agent in question comprises 10 to 15% by weight, preferably 12% of Rosa canina L. extract, 10 to 15%, preferably 11% of Hibiscus sabdariffa extract, 1 to 10%, preferably 5% of Thymbra spicata L. extract, 1 to 10%, preferably 4% of Helichrysum sp. extract, 1 to 5%, preferably 1% of sodium alginate, excipients, and deionized water.
  • the pharmaceutical composition comprises 10 to 20%, preferably 15% glycerol, 0.2 to 0.8%, preferably 0.4% xanthan gum, 0.10 to 0.15%, preferably 0.14% steviol glycosides, 0.01 to 0.05%, preferably 0.04% raspberry flavor, and 0.01 to 0.05%, preferably 0.02% mint flavor as excipients.
  • This example is completed in such a way that the remainder is deionized water and comprises 51.4% deionized water according to the preferred rates.
  • the anti-viral agent of the invention and the pharmaceutical composition comprising the same may comprise extracts of one or more species included in the genus Helichrysum, or in a preferred embodiment of the invention, the extract of Helichrysum arenarium L.
  • the pharmaceutical composition of the invention is mixed with 12 g of Rosa Canina L. extract, 11 g of Hibiscus Sabdariffa extract, 5 g of Thymbra Spicata L. extract, 4 g of Helichrysum sp. extract, 1 g of sodium alginate, 15 g of glycerol, 0.4 g of xanthan gum, 0.14 g of steviol glycosides, 0.04 g of raspberry flavor, 0.02 g of mint flavor and 51.4 g of deionized water in a 100 g container.
  • the production can also be performed by mixing the ready-mixed anti-viral agent, excipients, and water corresponding to the quantities.
  • the anti-viral agent of the invention and the pharmaceutical composition containing the same, the phenols originating from Thymbra spicata L. in its content, have enabled it to be applied to the patient with a certain and fixed dose in mg or mcg in the human body. In addition, complications caused by the unconscious use of essential oils have been prevented.
  • Xanthan gum contained in the pharmaceutical composition regulates the consistency of the product and also forms a barrier in the mouth and esophagus.
  • Steviol glycosides contained in the pharmaceutical composition ensure that the product becomes sweet and makes it more comfortable to drink.
  • Raspberry and mint flavors contained in the pharmaceutical composition give the product a drinkable aroma and thus make it easier to use.
  • Deionized water contained in the pharmaceutical composition helps to ensure homogeneous mixing of the solution.
  • the ready-to-use pharmaceutical composition is preferably stored and transported in a colored glass bottle or colored plastic bottle.
  • Table 2 A comparison of the days when the symptoms and PCR test were positive
  • the effectiveness of the pharmaceutical composition comprising the anti-viral agent is supported by trial results as seen above. Thanks to the anti-viral agent and the pharmaceutical composition comprising the same, the symptoms such as sore throat, runny nose, nasal congestion, sneezing, sore throat and cough, especially fever, headache, weakness, loss of taste and smell, muscle-joint pain and respiratory distress, which are identified with Covid- 19, have been relieved, eliminated, improved, and stopped progression, and at the same time, prophylaxis has been provided to protect against viruses thanks to the strong barrier created on the upper respiratory tract mucosa.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Pharmacology & Pharmacy (AREA)
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Abstract

La présente invention concerne un agent antiviral pour le traitement et la prophylaxie d'infections du tractus respiratoire supérieur provoquées par des virus (rhinovirus, coronavirus, y compris le Covid-19, le virus syncytial respiratoire (RSV), adénovirus, virus Influenza et Parainfluenza, entérovirus, virus de l'herpès simplex, cytomégalovirus, etc.) et des compositions pharmaceutiques le comprenant. Les effets de l'agent antiviral développé et des compositions pharmaceutiques le comprenant sur des symptômes ainsi que des fonctions de traitement et de prophylaxie de ceux-ci ont été expliqués. La présente composition pharmaceutique comprend un extrait de Rosa canina L., un extrait d'Hibiscus sabdariffa, un extrait de Thymbra spicata L., un extrait d'Helichrysum sp., de l'alginate de sodium, du glycérol, de la gomme xanthane, des glycosides de stéviol, un arôme de framboise, un arôme de menthe et de l'eau désionisée dans une bouteille en verre coloré ou une bouteille en plastique coloré.
PCT/TR2022/050007 2021-01-12 2022-01-05 Agent antiviral utilisé dans des infections virales du tractus respiratoire supérieur et composition pharmaceutique le comprenant Ceased WO2022154772A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2021/00436A TR202100436A2 (tr) 2021-01-12 2021-01-12 Üst solunum yollari vi̇ral enfeksi̇yonlarinda kullanilan anti̇-vi̇ral ajan ve bunu i̇çeren farmasöti̇k kompozi̇syonu
TR2021/00436 2021-01-12

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WO2022154772A1 true WO2022154772A1 (fr) 2022-07-21

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011147767A1 (fr) * 2010-05-24 2011-12-01 Indena S.P.A. Polysaccharide de graine de tamarin utilisé pour le traitement d'infections microbiennes
RU2576817C2 (ru) * 2013-05-07 2016-03-10 Акционерное общество "Красногорские лекарственные средства" Биологически активная добавка к пище

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011147767A1 (fr) * 2010-05-24 2011-12-01 Indena S.P.A. Polysaccharide de graine de tamarin utilisé pour le traitement d'infections microbiennes
RU2576817C2 (ru) * 2013-05-07 2016-03-10 Акционерное общество "Красногорские лекарственные средства" Биологически активная добавка к пище

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HAŞIM ÖTNÜ, HASAN AKAN: "Şanlıurfa’daki Eczanelerde ve Aktarlarda Fitoterapi Amaçlı Satılan Bitkiler", J. AGRIC NAT, vol. 23, no. 4, 1 January 2020 (2020-01-01), pages 947 - 965, XP055956667 *
UMAZ ADIL, UMAZ KADER: "İki Farklı Lokasyona ait Altın Otunun (Helichrysum arenarium) Uçucu Bileşenlerinin Belirlenmesi ve Karşılaştırılması", GÜMÜŞHANE ÜNIVERSITESI FEN BILIMLERI ENSTITÜSÜ DERGISI, vol. 10, no. 3, 1 January 2020 (2020-01-01), pages 592 - 600, XP055956672, ISSN: 2146-538X, DOI: 10.17714/gumusfenbil.621772 *

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