WO2026027997A1 - Compositions analgésiques comprenant une combinaison synergique de principes actifs - Google Patents

Compositions analgésiques comprenant une combinaison synergique de principes actifs

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Publication number
WO2026027997A1
WO2026027997A1 PCT/IB2025/057238 IB2025057238W WO2026027997A1 WO 2026027997 A1 WO2026027997 A1 WO 2026027997A1 IB 2025057238 W IB2025057238 W IB 2025057238W WO 2026027997 A1 WO2026027997 A1 WO 2026027997A1
Authority
WO
WIPO (PCT)
Prior art keywords
vitamin
spilanthol
compositions according
pea
palmitoylethanolamide
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.)
Pending
Application number
PCT/IB2025/057238
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English (en)
Inventor
Fabio Pietro TERRUZZI
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.)
GIELLEPI SpA
Original Assignee
GIELLEPI SpA
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Filing date
Publication date
Application filed by GIELLEPI SpA filed Critical GIELLEPI SpA
Publication of WO2026027997A1 publication Critical patent/WO2026027997A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • 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
    • 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
    • A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
    • 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
    • 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
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—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
    • A61K9/4858—Organic compounds
    • 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

Definitions

  • the invention relates to a pharmaceutical, veterinary or nutraceutical composition
  • a pharmaceutical, veterinary or nutraceutical composition comprising an association of spilanthol with acylethanolamides and/or vitamin K2.
  • the Acmella oleracea (formerly known as Spilanthes acmella) also known as toothache plant, paracress, and Jambu, is an annual herbaceous plant belonging to the Asteraceae family traditionally used by the indigenous populations of South America as a remedy to reduce toothache.
  • the Acmella oleracea is native to the tropical and subtropical regions of South America, in particular Brazil and Peru, where it is identified with the common name of Jambu. Thanks to its ease of cultivation and adaptability, the plant has spread to other parts of the world. It is often cultivated for ornamental purposes and used in local traditional medicine for its many benefits.
  • the Acmella oleracea extract most commonly used in phytotherapy and nutraceuticals is a hydroalcoholic extract of aerial parts, especially flowers and leaves, rich in biologically active secondary metabolites, including alkamides or N-alkylamides (spilanthol), flavonoids, polyphenols and tannins.
  • Spilanthol is an alkamide, responsible for the biological properties attributable to the extract, in particular anti-inflammatory properties, modulating the inflammatory response and reducing the production of pro-inflammatory cytokines (Rondanelli et al Phytotherapy 2020, Volume 140, 104419; Yien et al., Natural Product Research 2023, Volume 37, 18, 2023, 3136- 31442022; Jayashan et al. Appl. Sci. 2024, 14, 3755), as well as for its antioxidant, analgesic (Rondanelli et al Phytotherapy 2020 Volume 140, 2020, 104419) and antimicrobial effects (Spinozzi et al., Plants 2022, 11, 2721).
  • the hydroalcoholic extract of A. oleracea is therefore used in food supplements, herbal preparations and cosmetics.
  • the dosage forms most commonly used as a supplement are capsules or tablets containing standardized extracts of the plant's active ingredients.
  • Acmella oleracea is used to relieve pain, both of inflammatory and neuropathic origin.
  • Acylethanolamides such as anandamide, palmitoylethanolamide, oleoyl ethanol ami de, and prostamides, are natural compounds that play physiological roles as lipid and autacoid neurotransmitters .
  • PDA palmitoylethanolamide
  • PEA acts primarily through modulation of cannabinoid and non-cannabinoid receptors, such as the proliferator-activated peroxisome receptor alpha (PPAR-a). This mechanism helps reduce inflammation and pain without the psychotropic effects associated with traditional cannabinoids.
  • PPAR-a proliferator-activated peroxisome receptor alpha
  • PEA has been proposed for the treatment of chronic pain, neuropathic pain, pain associated with chronic inflammatory diseases, rheumatoid arthritis, intestinal inflammation, neurodegenerative diseases (Gabrielsson, L. et al. Br J Clin Pharmacol. 2016, 8 2(4):932-42; Skaper, S. D. et al. Inflammopharmacology 2014; 22(2):79-94).
  • vitamin K refers to a group of fat-soluble molecules comprising several isoforms or subtypes: vitamin KI (phylloquinone) and vitamin K2 (menaquinone); there is also a synthetic form known as vitamin K3 (menadion) which is not biologically active in humans.
  • vitamin K has a common central structure consisting of a naphthoquinone ring with an isoprenoid side chain which, in the case of vitamin K2, can be of variable length (due to the number of repeated isoprenoid units) and for this reason it is often referred to as "MK-n” or “vitK2-n” where "n” indicates the number of isoprenoid units.
  • Vitamin KI is mainly present in green leafy vegetables and is involved in the process of photosynthesis.
  • Vitamin K2 mainly present in foods of animal origin, (especially in the form of menaquinone-7, or MK-7 or vitamin K2-7) has shown potential benefits in the treatment of peripheral neuropathies, in particular associated with vitamin B12 deficiency, diabetes and iatrogenic conditions from oncological treatment. Preliminary studies suggest that vitamin K2- 7 may improve neuropathy symptoms, such as pain, tingling, and cramps, by acting through several biological mechanisms.
  • the MK-7 form of vitamin K2 has a longer half-life in the body than other forms of K2.
  • the Italian patent IT 202000024217 describes combinations of spilanthol with cannabidiol and/or boswellic acid useful for the treatment of pain, in particular neuropathic pain.
  • EP 3 417 846 discloses lipocomplexes in the form of microparticles comprising an emulsifier, an endocannabinoid such as PEA and a cannabinoid.
  • an endocannabinoid such as PEA
  • a cannabinoid a cannabinoid
  • the invention therefore relates to an oral or nutraceutical pharmaceutical composition
  • an oral or nutraceutical pharmaceutical composition comprising as active ingredients spilanthol in association with an acyl ethanol ami de and/or with vitamin K2 in combination with compatible carriers or excipients.
  • compositions comprise an association of spilanthol and an acylethanolamide.
  • compositions comprise spilanthol, an acylethanolamide and vitamin K2.
  • compositions comprise spilanthol and vitamin K2.
  • the spilanthol may be used in substantially pure or isolated form.
  • the spilanthol is present in an extract of Acmella oleracea. preferably an extract of aerial parts (flowers and/or leaves) or of other species of the same genus (such as A. paniculata, A. uliginosa, A. ciliata, A. radicans, A. caulirhiza, A. bellidioides or A. decumbens).
  • the acylethanolamides are preferably chosen from oleoyl ethanol ami de and palmitoylethanolamide. Palmitoylethanolamide is very particularly preferred.
  • compositions of the invention are suitable for oral administration, for example in the form of tablets, capsules, granules or liquid formulations, prepared in a conventional manner with pharmaceutically acceptable excipients.
  • suitable excipients comprise binding agents, bulking agents, lubricants, disintegrants and other conventionally used excipients or vehicles.
  • the tablets can be single- or multi-layered and can have a coating to allow the controlled release of the active ingredients.
  • Liquid preparations may be in the form of solutions, emulsions, syrups or suspensions or in the form of lyophilisates to be reconstituted, before use, with water or other vehicles.
  • Such liquid preparations can be prepared by conventional methods.
  • the unit dosage of spilanthol in the compositions of the invention is typically from 0.01 to 40 mg, preferably from 0.05 to 10 mg.
  • acylethanolamide is between 150 and 1200 mg, preferably between 500 and 800 mg in the case of palmitoylethanolamide (preferably used in non-micronized form). In the case of oleoylethanolamide, the dosage is between 100 and 250 mg.
  • the dosage of vitamin K2 is between 10 and 300 mcg.
  • compositions of the invention are useful for the treatment of pain in general, in particular pain related to inflammatory states or neuropathic pain, in human or veterinary medicine.
  • the frequency of administration may vary from 1 to 3-4 times per day.
  • the dose administered may vary depending on the age and weight of the patient and also the severity of the clinical condition being treated, at the discretion of the physician or veterinarian.
  • composition for capsule (0 size)
  • Vit. K2-7 (Powder Tit. 0.2%) 100 mg (Eq. 200 mcg Vit. K2-7)
  • Microcrystalline cellulose 500 mg
  • Citric acid 300 mg
  • Natural flavour e.g. lemon
  • Natural flavour 75 mg
  • Vitamin K2-7 (titer.1%) 5 mg (Eq. 50 mcg Vit.K2-7)
  • Vitamin K2-7 in sunflower oil (Tit. 0.15%) 67 mg (Eq. 100 mcg Vit. K2-7)
  • Vitamin K2-7 0.2% ,50mg (Equivalent to 100 mcg of Vit. K2-7)
  • BV-2 cells a cell line widely used for neuroinflammation studies.
  • BV-2s are immortalized cells that share morphological and functional characteristics with macrophages from other body districts with regard to their antigenic profile, their phagocytic capacity and antimicrobial activity.
  • BV-2 cells are also able to release pro-inflammatory cytokines when appropriately stimulated with pro-inflammatory cytokines and/or oxidative stress.
  • Such stimuli are among the main triggers capable of triggering neurodegenerative disorders such as Alzheimer's and Parkinson's disease, so BV-2 is widely used as an alternative in vitro experimental model to primary microglia cells.
  • BV-2 cells were cultured in vitro, under standard experimental conditions (37°C, 5% CO2 and controlled humidity) using RPMI 1640 culture medium supplemented with specific growth factors and 10% FCS (foetal calf serum), according to known protocols (Borgonetti, V., et al., Phytomedicine 2020; 68, 153143.).
  • BV-2 cells were cultured in 24-well plates at a density of 10 5 cells per well and allowed to adhere for 24 hours.
  • the cells were treated with the substances of interest: PEA, Acmella oleracea (AC) dry extract Vitamin K2 and their AC -PEA combinations, AC -PEA+ Vitamin K2 and AC+ Vitamin K2 while cells treated only with the culture medium were used as a control. All samples were stimulated with LPS (250 ng/ml) for two hours in order to induce inflammatory stimulation and express TNF-a whose expression was evaluated by ELISA kit according to the instructions provided by the manufacturer (Invitrogen).
  • TNF-a expression was quantified by spectrophotometer reading at the primary wavelength of 450 nm.
  • ROS reactive oxygen species
  • Cells were treated with the substances of interest or their combination for 4 hours and stimulated with LPS (250 ng/ml) for a further 2 hours in order to induce a condition of oxidative stress. Then the cells were incubated with a H2DCF-DA solution for 45 minutes at 37°C. In the presence of ROS, the reagent H2DCF-DA is converted into a fluorescent product, dichlorofluorescein (DCF) whose fluorescence is measured with a plate reader at a wavelength of 485/535 nm. Fluorescence is directly proportional to ROS levels.
  • DCF dichlorofluorescein
  • Results are expressed as mean values of three independent experiments ⁇ standard deviations and are shown in Figure 2 (**p ⁇ 0.01 vs control; * **p ⁇ 0.001 vs control; #p ⁇ 0.05 vs PEA, Acmella and Vitamin K2 (single treatment).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Botany (AREA)
  • Medical Informatics (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne des compositions ayant une activité analgésique comprenant comme principes actifs du spilanthol ou un extrait le contenant en association synergique avec un acyléthanolamide et/ou la vitamine K2.
PCT/IB2025/057238 2024-07-31 2025-07-17 Compositions analgésiques comprenant une combinaison synergique de principes actifs Pending WO2026027997A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IT202400017791 2024-07-31
IT102024000017791 2024-07-31
IT102024000022138 2024-10-04
IT202400022138 2024-10-04

Publications (1)

Publication Number Publication Date
WO2026027997A1 true WO2026027997A1 (fr) 2026-02-05

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PCT/IB2025/057238 Pending WO2026027997A1 (fr) 2024-07-31 2025-07-17 Compositions analgésiques comprenant une combinaison synergique de principes actifs

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3417846A1 (fr) 2017-06-19 2018-12-26 Gifar Srl Aliment et/ou composition nutraceutique
WO2019049142A1 (fr) * 2017-09-08 2019-03-14 Scicann Therapeutics Inc. Compositions comprenant un cannabinoïde et du spilanthol
IT202000024217A1 (it) 2020-10-14 2022-04-14 Sanitas Laboratorio Chimico Farm S R L Composizione farmaceutica ad effetto analgesico a base di acmella olearacea ed altri principi attivi

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3417846A1 (fr) 2017-06-19 2018-12-26 Gifar Srl Aliment et/ou composition nutraceutique
WO2019049142A1 (fr) * 2017-09-08 2019-03-14 Scicann Therapeutics Inc. Compositions comprenant un cannabinoïde et du spilanthol
IT202000024217A1 (it) 2020-10-14 2022-04-14 Sanitas Laboratorio Chimico Farm S R L Composizione farmaceutica ad effetto analgesico a base di acmella olearacea ed altri principi attivi

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
ANONYMUS: "Mitidol Zingiber and Acmella standardized extracts combination", 6 January 2020 (2020-01-06), pages 1 - 1, XP055861610, Retrieved from the Internet <URL:https://www.indena.com/indena_files/2019/12/mitidol_ss_int-1.pdf> [retrieved on 20211115] *
BORGONETTI, V ET AL., PHYTOMEDICINE, vol. 68, 2020, pages 153143
BORGONETTI, V. ET AL., PHYTOTHERAPY RESEARCH, vol. 36, 2022, pages 2246 - 2263
GABRIELSSON, L. ET AL., BR J CLIN PHARMACOL., vol. 82, no. 4, 2016, pages 932 - 42
JAYASHAN ET AL., APPL. SCI., vol. 14, 2024, pages 3755
LUONGO LIVIO ET AL: "Palmitoylethanolamide Reduces Formalin-Induced Neuropathic-Like Behaviour Through Spinal Glial/Microglial Phenotypical Changes in Mice", CNS & NEUROLOGICAL DISORDERS, vol. 12, no. 1, 1 March 2013 (2013-03-01), NL, pages 45 - 54, XP093252199, ISSN: 1871-5273, DOI: 10.2174/1871527311312010009 *
RONDANELLI ET AL., FITOTERAPIA, vol. 140, 2020, pages 104419
SERENA BOCCELLA ET AL: "Synergistic effects of Boswellia serrata and Acmella oleracea extract combination for treating neuropathic pain in a preclinical model of spared nerve injury", PHYSIOTHERAPY RESEARCH, JOHN WILEY & SONS LTD. CHICHESTER, GB, vol. 38, no. 4, 4 September 2023 (2023-09-04), pages 1731 - 1734, XP072616312, ISSN: 0951-418X, DOI: 10.1002/PTR.8001 *
SKAPER, S. D. ET AL., INFLAMMOPHARMACOLOGY, vol. 22, no. 2, 2014, pages 79 - 94
SPINOZZI ET AL., PLANTS, vol. 11, 2022, pages 2721
VIKAS SHARMA ET AL: "ethanolic flower extract: LCMS alkylamide profiling and its effects on sexual behavior in male rats", PHYTOMEDICINE, vol. 18, no. 13, 15 July 2011 (2011-07-15), pages 1161 - 1169, XP028308902, ISSN: 0944-7113, [retrieved on 20110615], DOI: 10.1016/J.PHYMED.2011.06.001 *
YIEN ET AL., NATURAL PRODUCT RESEARCH, vol. 37, no. 18, 2023, pages 3136 - 31442022

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