WO2023068287A1 - Nouveau produit pharmaceutique - Google Patents

Nouveau produit pharmaceutique Download PDF

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Publication number
WO2023068287A1
WO2023068287A1 PCT/JP2022/038872 JP2022038872W WO2023068287A1 WO 2023068287 A1 WO2023068287 A1 WO 2023068287A1 JP 2022038872 W JP2022038872 W JP 2022038872W WO 2023068287 A1 WO2023068287 A1 WO 2023068287A1
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WO
WIPO (PCT)
Prior art keywords
ivermectin
molnupiravir
covid
cov
sars
Prior art date
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PCT/JP2022/038872
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English (en)
Japanese (ja)
Inventor
浩一 白石
睦男 奥村
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興和株式会社
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Application filed by 興和株式会社 filed Critical 興和株式会社
Publication of WO2023068287A1 publication Critical patent/WO2023068287A1/fr

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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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to preventive and/or therapeutic agents for diseases based on SARS-CoV-2 infection.
  • COVID-19 Japanese name: novel coronavirus infectious disease
  • SARS-CoV-2 2019 novel coronavirus
  • COVID-19 is an infectious disease that was confirmed to occur in Wuhan, People's Republic of China in November 2019 and was reported to WHO in December of the same year, and has spread worldwide since then.
  • Symptoms include fever, dry cough, fatigue, sputum production, shortness of breath, sore throat, headache, muscle pain, joint pain, dysosmia, and dysgeusia. is taken.
  • there are still unknown points such as its infectivity and the rate of severe disease when contracted, and because it is a new type, effective treatment methods are still being sought, causing anxiety around the world.
  • Non-Patent Document 1 ivermectin is expected as a therapeutic drug for COVID-19, a disease based on SARS-CoV-2 infection.
  • Molnupiravir is known to exhibit antiviral effects by causing replication errors during viral RNA replication, and is expected to be a therapeutic drug for COVID-19, a disease caused by SARS-CoV-2 infection.
  • An object of the present invention is to provide a new drug for the prevention and/or treatment of COVID-19, a disease based on SARS-CoV-2 infection.
  • it is intended to provide a medicament for the prevention and/or treatment of mild or moderate COVID-19.
  • Ivermectin has already been used in Japan as a treatment for intestinal strongyloidiasis and scabies in tablet form. It is also expected as an orally administrable drug for treatment.
  • Molnupiravir exhibits antiviral activity, it is expected as an orally administrable therapeutic agent for COVID-19, a disease based on SARS-CoV-2 infection.
  • the inventors have focused on combining ivermectin and mornupiravir for the suppression of CoV-2 infection or the prevention and/or treatment of COVID-19, leading to the present invention.
  • the present invention provides the following inventions [1] to [9].
  • a pharmaceutical comprising a combination of ivermectin and mornupiravir.
  • a prophylactic and/or therapeutic agent for SARS-CoV-2 infection which is a combination of ivermectin and molnupiravir.
  • a preventive and/or therapeutic agent for COVID-19 which is a combination of ivermectin and molnupiravir.
  • Use of ivermectin and molnupiravir for prophylactic and/or therapeutic drug production for SARS-CoV-2 infection.
  • a method for preventing and/or treating COVID-19 which comprises administering ivermectin and molnupiravir.
  • the medicament obtained by combining ivermectin and molnupiravir of the present invention is effective in suppressing SARS-CoV-2 infection or preventing and / or treating COVID-19, that is, symptoms of COVID-19 (fever, cough, Shortness of breath, muscle pain, nasal discharge, sore throat, headache, nausea, vomiting, abdominal pain, diarrhea, dysosmia, dysgeusia) are improved or eliminated.
  • both ivermectin and molnupiravir are drugs that exert their effects when administered orally. It is possible to prescribe and administer drugs at any clinic.
  • the mechanism of antiviral action of ivermectin and the mechanism of antiviral action of mornupiravir are different, it is expected that the antiviral action will be enhanced by their combined use.
  • the medicament obtained by combining ivermectin and molnupiravir of the present invention is effective in suppressing SARS-CoV-2 infection or preventing and/or treating COVID-19.
  • the ivermectin used in the present invention may contain at least either ivermectin B1a or ivermectin B1b as ivermectin.
  • a mixture containing both ivermectin B1a and ivermectin B1b is preferable, and 90% or more of ivermectin B1a and ivermectin Mixtures containing less than 10% B 1b are more preferred.
  • ivermectin is a known chemical substance, and can be obtained by purchasing a commercial product or by producing avermectin by selective catalytic hydrogenation followed by removal of the catalyst.
  • the administration route of the ivermectin-containing medicament of the present invention is not particularly limited, and may be oral administration or parenteral administration.
  • a drug containing ivermectin When a drug containing ivermectin is administered orally, the dosage varies depending on the patient's body weight, age, sex, symptoms, etc., but the usual dose for adults is 0.1 to 1 mg/kg body weight per day as ivermectin. 0.15 to 0.5 mg/kg body weight, more preferably 0.2 to 0.4 mg/kg body weight. Assuming that the body weight of an adult is 60 kg, the daily dose is usually 6 to 60 mg, preferably 12 to 24 mg. The daily dose can be divided and administered about 1 to 4 times.
  • oral administration formulations examples include capsules, pills, granules, fine granules, powders, tablets, liquid formulations, syrups, jellies, lozenges, etc.
  • Oral administration formulations containing these ivermectins are known. It can be manufactured by the method of As the dosage form of oral administration preparations, solid preparations are preferable, and capsules, pills, granules, fine granules, powders, and tablets are particularly preferable.
  • the ivermectin content per dosage unit of these oral administration preparations is preferably 3 mg and 6 mg in consideration of the dosage amount.
  • a tablet containing 3 mg of ivermectin is on the market, and if ivermectin is approved for the suppression of SARS-CoV-2 infection or the prevention and / or treatment of COVID-19, it should be used. can also be possible.
  • molnupiravir has the IUPAC name ((2R,3S,4R,5R)-3,4-dihydroxy-5-(4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H) -yl) tetrahydrofuran-2-yl) methyl isobutylate, which is a known chemical substance, can be obtained by purchasing a commercially available product or by producing it by a known method.
  • the administration route of the medicament containing molnupiravir of the present invention is not particularly limited, and may be oral administration or parenteral administration.
  • a drug containing molnupiravir is administered orally, the dosage varies depending on the patient's body weight, age, sex, symptoms, etc., but the usual daily dose of molnupiravir for adults is 10 to 5000 mg. Well, it is preferably 100-3200 mg, more preferably 200-1600 mg.
  • the daily dose can be divided and administered about 1 to 4 times.
  • oral administration formulations examples include capsules, pills, granules, fine granules, powders, tablets, liquid formulations, syrups, jellies, lozenges, etc.
  • Oral administration formulations containing these molnupiravir are known. It can be manufactured by the method of As the dosage form of oral administration preparations, solid preparations are preferable, and capsules, pills, granules, fine granules, powders, and tablets are particularly preferable.
  • the content of molnupiravir per dosage unit of these oral administration preparations is preferably 100 mg and 200 mg in consideration of the dosage amount.
  • a dosage form such as an inhalant that can be directly applied to the lower respiratory tract as a site of SARS-CoV-2 infection can be administered unlike an injection. is convenient, it can be cited as a preferred dosage form among parenteral administration.
  • the particle size is preferably 0.5 to 10 ⁇ m from the viewpoint of accessibility to the lower respiratory tract. 0.5 to 8 ⁇ m, more preferably 0.5 to 6 ⁇ m.
  • the mass median aerodynamic diameter of ivermectin and molnupiravir is preferably 0.5 to 10 ⁇ m, more preferably 0.5 to 8 ⁇ m, and more preferably 0.5 to 6 ⁇ m. is more preferred.
  • the particle size of ivermectin and molnupiravir is the particle size of the ivermectin-containing powder or molnupiravir-containing powder in the case of a powder, and the particle size of the ivermectin-containing atomized droplets or molnupiravir-containing atomized droplets in the case of a liquid formulation.
  • the particle size can be adjusted by pulverization, sieving, etc. during powder production.
  • inhalants include inhalation powders, inhalation liquids, and inhalation aerosols, but are not particularly limited.
  • a suitable device or device for administration by inhalation may be used, or a container combined with a device for inhalation may be filled.
  • the inhalable powder preparation is a preparation for inhalation as an aerosol of ivermectin-containing powder or molnupiravir-containing powder prepared so that the inhalation amount is constant. More preferably, it may be prepared as a powder having a particle size of 0.5 to 8 ⁇ m, more preferably 0.5 to 6 ⁇ m, specifically, preferably 0.5 to 10 ⁇ m, more preferably 0.5 to 8 ⁇ m. and more preferably as a powder having a mass median aerodynamic diameter of 0.5 to 6 ⁇ m.
  • Sugar or sugar alcohol can be used as an additive for the ivermectin-containing powder or molnupiravir-containing powder.
  • sugars include lactose hydrate, sucrose, and glucose
  • sugar alcohols include erythritol, isomalt, lactitol, maltitol, mannitol, sorbitol, and xylitol.
  • ivermectin-containing powder a freeze-dried product containing ivermectin and a lactic acid/glycolic acid copolymer described in JP-A-2019-69906 can also be mentioned.
  • DPI dry powder inhaler
  • Devices commonly used as DPIs can be used for the inhalable powder formulation of the present invention.
  • devices using capsules include Monohaler, Handyhaler, Breezhaler, Flowcaps and the like.
  • Other examples include Dischaler, Discus, and Ellipta, which use aluminum blisters.
  • Turbuhaler, Crickhaler, Swinghaler, Twisthaler and the like are examples of reservoir-type devices in which a powder is filled in a container.
  • An inhalation solution is a liquid inhalation preparation that is inhaled using a nebulizer or the like.
  • Ivermectin or molnupiravir may be dissolved or suspended in a suitable solvent to prepare a solution or suspension.
  • An isotonizing agent, a pH adjusting agent, and the like can be added during preparation.
  • the droplet size of the inhalation solution is preferably 0.5 to 10 ⁇ m, more preferably 0.5 to 8 ⁇ m, still more preferably 0.5 to 10 ⁇ m, depending on the form of the nebulizer (jet type, ultrasonic wave type, mesh type, etc.). It may be adjusted to a droplet of 6 ⁇ m. Adjust to drops.
  • Devices that are commonly used as nebulizers can be used for the inhalation liquid of the present invention.
  • a type that uses compressed air to atomize the chemical liquid jet type
  • a type that uses the vibration of an ultrasonic transducer to atomize the chemical liquid jet type
  • a type that pushes the chemical liquid through the holes of the mesh by vibration etc. to atomize it type (mesh type) and the like.
  • An inhalation aerosol is a metered dose inhaler that can nebulize a fixed amount of ivermectin or molnupiravir together with a container filled with propellant.
  • Spray droplets to be sprayed by an inhalation aerosol are composed of ivermectin (including lyophilized products containing ivermectin and lactic acid/glycolic acid copolymer) or molnupiravir solution or suspension, filling propellant and container material.
  • ivermectin including lyophilized products containing ivermectin and lactic acid/glycolic acid copolymer
  • molnupiravir solution or suspension filling propellant and container material.
  • the droplets should preferably have a mass median diameter of 0.5 to 10 ⁇ m, more preferably 0.5 to 8 ⁇ m, still more preferably 0.5 to 6 ⁇ m.
  • ivermectin lyophilized product containing ivermectin and lactic acid/glycolic acid copolymer
  • molnupiravir is dissolved or suspended in an appropriate solvent to prepare a solution or suspension, and a liquid propellant is prepared. It can be manufactured by filling a pressure-resistant container together with it and attaching a metering valve. Dispersants, stabilizers, and the like can be added when preparing solutions or suspensions.
  • a specific example of the inhalation aerosol is a pressurized metered dose inhaler.
  • ivermectin and mornupiravir can be administered at the same time or at different times. It is also possible to use those formulated in the same dosage form. In addition, it is also possible to prepare a so-called combination drug or combination drug in which ivermectin and molnupiravir are formulated together.
  • ivermectin and mornupiravir are formulated in the same dosage form, or when a combination drug containing ivermectin and mornupiravir is formulated, it is preferable to use an oral administration formulation or an inhalant as described above. In addition, it is preferable to set the doses as described above even in the formulations and combination drugs having the same dosage form.
  • both ivermectin and mornupiravir have antiviral effects and viral growth-inhibitory effects, but their growth-inhibitory mechanisms are different from each other. Therefore, it can be expected that the antiviral action will be enhanced by the combined use of these.
  • the action of the drug of the present invention is to suppress the proliferation of viruses, it is desirable to administer it as soon as possible after SARS-CoV-2 infection is confirmed.
  • Ivermectin was pulverized with a jet mill to obtain a pulverized material.
  • the average particle size D50 of the pulverized material obtained was 2.0 ⁇ m.
  • the pulverized product and lactose hydrate were mixed with lactose hydrate so that the concentration of ivermectin was 10% to obtain an inhalable powder.
  • the formulation is shown in Table 1. Also, 0.03 g of the obtained powder was filled into a capsule to produce an inhalation powder-filled capsule.
  • Control example 1 Unpulverized ivermectin and lactose hydrate were mixed with lactose hydrate so that the concentration of ivermectin was 10% to obtain an inhalable powder.
  • the formulation is shown in Table 1. Also, 0.03 g of the obtained powder was filled into a capsule to produce an inhalation powder-filled capsule.
  • Test example 1 In order to evaluate the aerodynamic properties of the inhalable powders obtained in Example 1 and Comparative Example 1 using a device for inhalation, the fine particle content (FPF) (%) and the aerodynamic mass Dimensional diameter was measured.
  • the fine particle content (FPF) (%) and the mass median aerodynamic diameter were measured in accordance with the aerodynamic particle size measurement method for inhalants in the Japanese Pharmacopoeia 17th Edition Supplement 1, and the multi-stage Evaluated using a liquid impinger.
  • the inhalable powder of Example 1 using pulverized ivermectin had a fine particle content (FPF) (%) of 29.9% and a mass median aerodynamic diameter of 2.8 ⁇ m.
  • the inhalation powder of Comparative Example 1 using unmilled ivermectin had a fine particle content (FPF) (%) of 3.5% and a mass median aerodynamic diameter of more than 10 ⁇ m, indicating that It was considered difficult to deliver ivermectin to the deep lung.
  • the inhalation powder of Comparative Example 1 using unmilled ivermectin had a fine particle content (FPF) (%) of 3.5% and a mass median aerodynamic diameter of more than 10 ⁇ m, indicating that It was considered difficult to deliver ivermectin to
  • Example 2 Ivermectin was dissolved in ethyl alcohol, and phosphate buffer and water were added to adjust the final concentration of ivermectin to 0.5% to prepare an inhalation solution.
  • Test example 2 For the inhalation liquid obtained in Example 2, a nebulizer was used as a device to visually confirm whether the drug was sprayed in the form of mist. Further, the atomized drug was collected and the particle size was confirmed with a microscope. It was confirmed that the liquid agent of Example 2 was atomized and had a particle size of 2 to 6 ⁇ m. Therefore, it was determined that the drug solution of Example 2 is suitable as an inhalation solution.
  • Example 1 Attempts to combine treatment with tablets containing ivermectin and capsules containing mornupiravir in patients infected with SARS-CoV-2 infection and developing mild COVID-19 may reduce the risk of COVID-19.
  • Symptoms fever, cough, shortness of breath, muscle pain, nasal discharge, sore throat, headache, nausea, vomiting, abdominal pain, diarrhea, abnormal smell and abnormal taste) show improvement or disappearance.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un nouveau produit pharmaceutique utilisé comme médicament thérapeutique contre la COVID-19.　La présente invention concerne un produit pharmaceutique obtenu en associant l'ivermectine et le molnupiravir, un médicament thérapeutique destiné à la prévention et/ou au traitement d'une infection par le SARS-CoV-2 obtenue en associant l'ivermectine et le vernupiravir, et un médicament thérapeutique destiné à la prévention et/ou au traitement de la COVID-19 obtenu en associant l'ivermectine et le vernupiravir.
PCT/JP2022/038872 2021-10-19 2022-10-19 Nouveau produit pharmaceutique WO2023068287A1 (fr)

Applications Claiming Priority (2)

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JP2021-171116 2021-10-19
JP2021171116 2021-10-19

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WO2023068287A1 true WO2023068287A1 (fr) 2023-04-27

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019113462A1 (fr) * 2017-12-07 2019-06-13 Emory University N4-hydroxycytidine et dérivés et leurs utilisations anti-virales

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019113462A1 (fr) * 2017-12-07 2019-06-13 Emory University N4-hydroxycytidine et dérivés et leurs utilisations anti-virales

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
ABD‐ELSALAM SHERIEF, NOOR RASHA A., BADAWI REHAB, KHALAF MAI, ESMAIL ESLAM S., SOLIMAN SHAIMAA, ABD EL GHAFAR MOHAMED S., ELBAHNAS: "Clinical study evaluating the efficacy of ivermectin in COVID‐19 treatment: A randomized controlled study", JOURNAL OF MEDICAL VIROLOGY, JOHN WILEY & SONS, INC., US, vol. 93, no. 10, 1 October 2021 (2021-10-01), US , pages 5833 - 5838, XP093059008, ISSN: 0146-6615, DOI: 10.1002/jmv.27122 *
AJAYI AAL: "Drugs Shown to Inhibit SARS-CoV-2 in COVID-19 Disease: Comparative Basic and Clinical Pharmacology of Molnupiravir and Ivermectin", AUSTIN J PHARMACOL THER, vol. 9, no. 5, 1 August 2021 (2021-08-01), pages 1149, XP093059006 *
COX ROBERT M.; WOLF JOSEF D.; PLEMPER RICHARD K.: "Therapeutically administered ribonucleoside analogue MK-4482/EIDD-2801 blocks SARS-CoV-2 transmission in ferrets", NATURE MICROBIOLOGY, NATURE PUBLISHING GROUP UK, LONDON, vol. 6, no. 1, 1 January 1900 (1900-01-01), London , pages 11 - 18, XP037319215, DOI: 10.1038/s41564-020-00835-2 *
ERRECALDE JORGE, LIFSCHITZ ADRIAN, VECCHIOLI GRACIELA, CEBALLOS LAURA, ERRECALDE FRANCISCO, BALLENT MARIANA, MARÍN GUSTAVO, DANIEL: "Safety and Pharmacokinetic Assessments of a Novel Ivermectin Nasal Spray Formulation in a Pig Model", JOURNAL OF PHARMACEUTICAL SCIENCES, AMERICAN CHEMICAL SOCIETY AND AMERICAN PHARMACEUTICAL ASSOCIATION, US, vol. 110, no. 6, 23 January 2021 (2021-01-23), US , pages 2501 - 2507, XP055963463, ISSN: 0022-3549, DOI: 10.1016/j.xphs.2021.01.017 *
IMRAN MOHD., KUMAR ARORA MANDEEP, ASDAQ SYED MOHAMMED BASHEERUDDIN, KHAN SHAH ALAM, ALAQEL SALEH I., ALSHAMMARI MOHAMMED KANAN, AL: "Discovery, Development, and Patent Trends on Molnupiravir: A Prospective Oral Treatment for COVID-19", MOLECULES, vol. 26, no. 19, 24 September 2021 (2021-09-24), pages 5795 - 599577945, XP055923049, DOI: 10.3390/molecules26195795 *
M. MANSOUR SUZAN; N. SHAMMA REHAB; A. AHMED KAWKAB; A. SABRY NIRMEEN; ESMAT GAMAL; A. MAHMOUD AZZA; MAGED AMR: "Safety of inhaled ivermectin as a repurposed direct drug for treatment of COVID-19: A preclinical tolerance study", INTERNATIONAL IMMUNOPHARMACOLOGY, ELSEVIER, AMSTERDAM, NL, vol. 99, 23 July 2021 (2021-07-23), NL , XP086760350, ISSN: 1567-5769, DOI: 10.1016/j.intimp.2021.108004 *

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