US20150265568A1 - Pharmaceutical composition comprising palmitoylethanolamide and l-acetylcarnitine - Google Patents
Pharmaceutical composition comprising palmitoylethanolamide and l-acetylcarnitine Download PDFInfo
- Publication number
- US20150265568A1 US20150265568A1 US14/658,369 US201514658369A US2015265568A1 US 20150265568 A1 US20150265568 A1 US 20150265568A1 US 201514658369 A US201514658369 A US 201514658369A US 2015265568 A1 US2015265568 A1 US 2015265568A1
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- United States
- Prior art keywords
- pharmaceutical composition
- composition according
- palmitoylethanolamide
- compound
- antioxidant activity
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- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/221—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
- A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
Definitions
- neurogenic pain also referred to as inflammatory pain
- inflammatory pain can be defined as the consequence of a complex multi-factorial mechanism localized in the innervated tissues and/or in the miniaturized endoneurial compartment in which, in addition to the nociceptive nerve terminals and/or the axons composing the peripheral sensitive fibers, the endothelial cells of the microcirculation, both tissue and endoneurial mastocytes, and cells of an immunologic nature extravasated from the tissue microcirculation in cases of suffering of the peripheral nervous system and/or of the tissue it innervates are involved.
- the whole process is defined as neurogenic inflammation, and it gives rise to the phenomenon referred to as peripheral sensitization.
- neuropathic pain characteristic of neuropathies caused by traumatic, compressive, dysmetabolic, and infective injuries, is characterized by spontaneous pain, allodynia, and hyperalgesia.
- central sensitization found at the level of the dorsal horns of the spinal cord, generally as a consequence of a lesion or an alteration of the somato-sensory nervous system (Neurology 2008; 70:1630-1635), is recognized as the most important mechanism on which of chronic pain is based.
- glial cells and in particular the microglia are involved in this sensitization process.
- microglia induced, as stated, above, by an injury or dysmetabolism of neuronal systems (peripheral, spinal, supraspinal) results in a significant alteration of the synaptic plasticity induced by growth factors of protein origin released by the microglia, with a substantial modification of the neurotransmission (peptidergic, glutamatergic) dialogue between the first and second neurons.
- the neurotransmission at the level of said synaptic junction is deeply changed, passing from an essentially glutamatergic neurotransmission through NMDA-type receptors to a mixed neurotransmission, glutamatergic—in part still of an NMDA type and in part of a metabotropic type (through a series of glutamatergic receptors belonging to the mGlu family)—and peptidergic, essentially related, to the neuropeptide known as Substance P (SP).
- SP Substance P
- palmitoylethanolamide an endogenous lipid of an N-acylethanolamide nature produced on demand in the case of a cell damage
- palmitoylethanolamide is capable of modulating in an inhibitory manner both the hyperdegranulation of the mastocyte and the hyper-activation of the microglia, thus showing to be capable, when administered in such a pharmaceutical form as to ensure bioavailability at the level of the above-mentioned two target cells, of controlling the neuronal—peripheral and central—sensitization and, consequently, both the inflammatory and neuropathic pain.
- palmitoylethanolamide showed a particularly relevant effect, at the dose of 10 mg/kg, in the neuropathic pain model obtained by sciatic nerve ligation in the mouse; clinically, many studies proved the ability of palmitoylethanolamide, administered p.o. in an appropriate form—e.g., micronized and/or ultramicronized—of reducing both inflammatory pain and chronic and neuropathic pain associated with several disease conditions.
- L-Acetylcarnitine (LAC), a molecule which is typically used in the treatment of painful neuropathies, proved to be able, at a dose of 100 mg/kg, to decrease the mechanical allodynia in the neuropathic pain model obtained by sciatic nerve ligation in rodents (CCI).
- CCI sciatic nerve ligation in rodents
- the mechanism of action of such molecule is a selective over-regulation of the metabotropic receptors for glutamate, and in particular of the receptor referred to as mGlu2 at the level of the joint between the first and the second neurons, located in the posterior horns of the spinal cord.
- the inventors of the present patent have surprisingly found that the association between palmitoylethanolamide, in micronized or ultramicronized form, and L-acetylcarnitine is capable of providing a highly synergic effect between the two molecules, which effect is particularly clear on neuropathic pain.
- an object of the present invention is a pharmaceutical composition
- a pharmaceutical composition comprising palmitoylethanolamide (PEA), alternatively in non-micronized form (non-micronized PEA), or in micronized form (PEA-m), or in ultra-micronized form (PEA-um), and L-acetylcarnitine in finely pulverized form.
- PDA palmitoylethanolamide
- a further object of the invention is a pharmaceutical composition
- a pharmaceutical composition comprising palmitoylethanolamide (PEA) as defined above, L-acetylcarnitine, and antioxidative molecules of the polyphenols family (e.g., polydatin, resveratrol, luteolin, quercetin, rutin, etc.), ⁇ -lipoic acid, and/or acetylcysteine.
- PDA palmitoylethanolamide
- L-acetylcarnitine and antioxidative molecules of the polyphenols family (e.g., polydatin, resveratrol, luteolin, quercetin, rutin, etc.), ⁇ -lipoic acid, and/or acetylcysteine.
- FIG. 1 shows a Table illustrating the data regarding to a mechanical allodynia test following a sciatic nerve ligation in mouse.
- the invention relates to a pharmaceutical composition
- a pharmaceutical composition comprising palmitoylethanolamide (PEA), alternatively in non-micronized form (non-micronized PEA), or in micronized form (PEA-m), or in ultra-micronized form (PEA-um), and L-acetylcarnitine in finely pulverized form.
- PDA palmitoylethanolamide
- Palmitoylethanolamide can be synthesized as described in Example no. 25 of U.S. Pat. No. 5,990,170.
- Non-micronized PEA can be obtained by finely grounding the product from the synthesis; a product with a particle size ranging between 50.0 and 100.0 ⁇ m can be obtained.
- PEA-m can be obtained as described in the U.S. Pat. No. 6,548,550 B1 and it has a particle size ranging between 2.0 and 10.0 ⁇ m.
- PEA-um can be obtained as described in the patent application PCT issued with no. WO 2011/027373 A1 and it has a particle size ranging between 0.8 and 6.0 ⁇ m.
- L-acetylcarnitine is a commercially available product.
- the pharmaceutical composition of the invention comprises palmitoylethanolamide in weight percentages ranging between 20 and 35%, L-acetylcarnitine in weight percentages between 20 and 55%, and one or more compounds with antioxidant activity in total weight percentages ranging between 0 and 20%.
- the compound with antioxidant activity is preferably selected from the group comprising polyphenols, alpha-lipoic acid (or thioctic acid), and the L-acetylcysteine.
- the antioxidant compound is or comprises a polyphenol, it is preferably selected from polydatin, resveratrol, luteolin, quercetin and rutin.
- the molecules having an antioxidative activity may also be co-micronized with palmitoylethanolamide according to the teachings described in U.S. Pat. No. 6,548, 550 B1.
- the antioxidative compounds are commercially available products.
- the inventive composition can further contain pharmaceutically acceptable excipients and additives, selected as a function of the desired pharmaceutical form.
- the diseases which can be treated with the composition object of the present invention comprise:
- composition according to the present invention can be formulated for an oral, buccal, or rectal administration.
- the pharmaceutical compositions can be, for example, in the form of tablets or capsules prepared in a conventional manner with pharmaceutically acceptable excipients, such as binders (e.g., pre-gelatinized corn starch, polyvinylpyrrolidone, or hydroxypropyl methylcellulose); filling agents (e.g., lactose, microcrystalline cellulose or calcium hydrogen phosphate); lubricants (e.g., magnesium stearate, talc, or silica); disintegrating agents (e.g., potato starch or sodium starch glycolate); or inhibiting agents (e.g., sodium lauryl sulfate).
- binders e.g., pre-gelatinized corn starch, polyvinylpyrrolidone, or hydroxypropyl methylcellulose
- filling agents e.g., lactose, microcrystalline cellulose or calcium hydrogen phosphate
- lubricants e.g., magnesium stearate, talc, or silica
- the liquid preparations for oral administration can be, for example, in the form of solutions, syrups or suspensions, or they can be in the form of lyophilized products to be reconstituted, before their use, with water or other suitable vehicles.
- Such liquid preparations can be prepared by conventional methods with pharmaceutically acceptable additives, such as suspending agents (e.g., sorbitol syrup, cellulose derivatives, or edible hydrogenated fats); emulsifying agents (e.g., lecithin or acacia); non-aqueous vehicles (e.g., almond oil, oily esters, ethyl alcohol, or fractionated plant-based oils); and preservatives (e.g., methyl- or propyl-p-hydroxybenzoates or sorbic acid).
- the preparation may also suitably contain flavors, colorants, and sweeteners.
- the preparations for oral administration can be suitably formulated to allow the controlled release of the active ingredient.
- compositions can be in the form of tablets or lozenges formulated in a conventional manner, suitable for an absorption by the buccal mucosae.
- Typical buccal formulations are the tablets for sub-lingual administration.
- the compounds can also be formulated in rectal compositions, such as suppositories or retention enema, for example containing the base components of typical suppositories, such as cocoa butter or other glycerides.
- the compounds can also be formulated as depot preparations. Such long-acting formulations can be administered by an implant (for example, subcutaneously, transdermally, or intramuscularly) or by intramuscular injection.
- an implant for example, subcutaneously, transdermally, or intramuscularly
- intramuscular injection for example, the compounds, according to the present invention, can be formulated with suitable polymeric or hydrophobic materials (e.g., in the form of an emulsion in a suitable oil) or ionic exchange resins, or as minimally soluble derivatives, for example, as a minimally soluble salt.
- the dose of the compounds proposed for the administration to a human being ranges from 10 mg to 1 g, and preferably from 100 mg to 500 mg of the active ingredients per dose unit.
- the dose unit can be administered, for example, 1 to 4 times/day.
- the dose will depend on the selected administration route. It shall be considered that it could be necessary to continuously vary the dosage as a function of the age and weight of the patient, and also of the severity of the clinical condition to be treated. Finally, the precise dose and the administration route will be at discretion of the attending physician or veterinary.
- formulations described above can be prepared according to conventional methods, such as those described in Remington's Pharmaceutical Sciences Handbook, Mack Pub. Co., N.Y., USA.
- mice of the C57BL/6J strain with a weight ranging between 25 and 30 g; 10 animals per group were used.
- the animals were anesthetized with sodium pentobarbital (60 mg/kg, i.p.) and subjected to a surgical procedure of sciatic nerve ligation capable of inducing neuropathic pain in accordance with the method described by Bennet and Xie (1988, Pain; 33:87-107). Sham animals were used as a control.
- the products were administered p.o. with a tube, suspended in 2% CarboxymethylCellulose.
- the mechanical allodynia was measured by using the Dynamic Plantar Aesthesiometer equipment of the Company Ugo Basile—Varese, Italy.
- PEA-um at a close from 5 mg/kg in association with LAC at a dose of 10 mg/kg, causes a very high decrease of the neuropathic pain after 8 days of treatment.
- Each tablet contains:
- Each tablet contains:
- Each tablet contains:
- Each tablet contains:
- Each tablet contains:
- Each tablet contains:
- Each sachet of microgranules contains:
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/603,566 US10441559B2 (en) | 2014-03-19 | 2017-05-24 | Method of treating neuropathic pain with a synergistic pharmaceutical composition comprising palmitoylethanolamide and L-acetylcarnitine |
US16/436,143 US20190290609A1 (en) | 2014-03-19 | 2019-06-10 | Pharmaceutical composition comprising palmitoylethanolamide and l-acetylcarnitine |
US18/184,797 US20230285349A1 (en) | 2014-03-19 | 2023-03-16 | Pharmaceutical composition comprising palmitoylethanolamide and l-acetylcarnitine |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI2014A000454 | 2014-03-19 | ||
ITMI20140454 | 2014-03-19 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US15/603,566 Continuation US10441559B2 (en) | 2014-03-19 | 2017-05-24 | Method of treating neuropathic pain with a synergistic pharmaceutical composition comprising palmitoylethanolamide and L-acetylcarnitine |
Publications (1)
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US20150265568A1 true US20150265568A1 (en) | 2015-09-24 |
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ID=50733183
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US14/658,369 Abandoned US20150265568A1 (en) | 2014-03-19 | 2015-03-16 | Pharmaceutical composition comprising palmitoylethanolamide and l-acetylcarnitine |
US15/603,566 Active 2035-03-25 US10441559B2 (en) | 2014-03-19 | 2017-05-24 | Method of treating neuropathic pain with a synergistic pharmaceutical composition comprising palmitoylethanolamide and L-acetylcarnitine |
Family Applications After (1)
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US15/603,566 Active 2035-03-25 US10441559B2 (en) | 2014-03-19 | 2017-05-24 | Method of treating neuropathic pain with a synergistic pharmaceutical composition comprising palmitoylethanolamide and L-acetylcarnitine |
Country Status (5)
Country | Link |
---|---|
US (2) | US20150265568A1 (de) |
EP (1) | EP2921167B1 (de) |
CA (1) | CA2884898C (de) |
CY (1) | CY1118214T1 (de) |
ES (1) | ES2603809T3 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20190070133A1 (en) * | 2017-09-05 | 2019-03-07 | Ankit Shyam SINGH | Pharmaceutical composition for improving or preventing progression of chronic kidney disease |
US11819511B2 (en) * | 2019-08-26 | 2023-11-21 | Epitech Group S.P.A. | Composition of N-palmitoyl-ethanolamide and Rutin in co-micronized form |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3417846A1 (de) * | 2017-06-19 | 2018-12-26 | Gifar Srl | Nahrungsmittel und/oder nutrazeutische zusammensetzung |
IT201800004355A1 (it) * | 2018-04-10 | 2019-10-10 | Composizione per il trattamento delle neuropatie periferiche | |
US11523998B2 (en) | 2018-06-14 | 2022-12-13 | The Texas A&M University System | Anti-inflammatory formulations and uses thereof including a combination of palmitoylethanolamide and plant-based polyphenols |
WO2020141546A1 (en) | 2019-01-02 | 2020-07-09 | Celagenex Research (India) Pvt. Ltd. | Synergistic nutritional compositions for pain management |
EP3838346A1 (de) * | 2019-12-20 | 2021-06-23 | Chemo Research SL | Weiche gelatinekapseln mit palmitoylethanolamid und alpha-liponsäure |
GR20200100479A (el) * | 2020-08-13 | 2022-03-09 | Pharma Unimedis Ike, | Συμπληρωμα διατροφης για την προληψη και/ή τη θεραπεια του πονου και/ή νευροπαθειων |
EP4364730A1 (de) | 2022-11-02 | 2024-05-08 | Chiesi Italia S.p.A. | Pharmazeutische zusammensetzung mit l-acetylcarnitin und beta-caryophyllen |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5973004A (en) * | 1997-04-04 | 1999-10-26 | Howard; James R. | L-carnitine, acetyl-L-carnitine, and pantothenic acid or ubiquinone, combined for prevention and treatment of syndromes related to ineffective energy metabolism |
US6548550B1 (en) * | 1999-08-06 | 2003-04-15 | Innovet Italia S.R.L. | Pharmaceutical compositions containing N-palmitoylethanolamide and use thereof in the veterinary field |
US20110171313A1 (en) * | 2009-09-07 | 2011-07-14 | Francesco Della Valle | Composition containing ultra-micronized palmitoyl-ethanolamide |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1271266B (it) | 1994-12-14 | 1997-05-27 | Valle Francesco Della | Impiego terapeutico di ammidi di acidi mono e bicarbossilici con amminoalcoli,selettivamente attive sul recettore periferico dei cannabinoidi |
-
2015
- 2015-03-06 ES ES15157173.4T patent/ES2603809T3/es active Active
- 2015-03-06 EP EP15157173.4A patent/EP2921167B1/de active Active
- 2015-03-12 CA CA2884898A patent/CA2884898C/en active Active
- 2015-03-16 US US14/658,369 patent/US20150265568A1/en not_active Abandoned
-
2016
- 2016-11-07 CY CY20161101137T patent/CY1118214T1/el unknown
-
2017
- 2017-05-24 US US15/603,566 patent/US10441559B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5973004A (en) * | 1997-04-04 | 1999-10-26 | Howard; James R. | L-carnitine, acetyl-L-carnitine, and pantothenic acid or ubiquinone, combined for prevention and treatment of syndromes related to ineffective energy metabolism |
US6548550B1 (en) * | 1999-08-06 | 2003-04-15 | Innovet Italia S.R.L. | Pharmaceutical compositions containing N-palmitoylethanolamide and use thereof in the veterinary field |
US20110171313A1 (en) * | 2009-09-07 | 2011-07-14 | Francesco Della Valle | Composition containing ultra-micronized palmitoyl-ethanolamide |
US8470373B2 (en) * | 2009-09-07 | 2013-06-25 | Epitech Group S.R.L. | Composition containing ultra-micronized palmitoyl-ethanolamide |
US8663701B2 (en) * | 2009-09-07 | 2014-03-04 | Epitech Group S.R.L. | Compositions containing ultra-micronized palmitoyl-ethanolamide |
Non-Patent Citations (4)
Title |
---|
Gilron 1 (New England Journal of Medicine. 2005 Mar 31;352(13):1324-34.) * |
Gilron 2 (The Lancet. 2009 Oct 16;374(9697):1252-61) * |
Sima (Diabetes Care 28:96-101, 2005) * |
Vorobeychik (CNS Drugs December 2011, Volume 25, Issue 12, pp 1023-1034) * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20190070133A1 (en) * | 2017-09-05 | 2019-03-07 | Ankit Shyam SINGH | Pharmaceutical composition for improving or preventing progression of chronic kidney disease |
US10973782B2 (en) * | 2017-09-05 | 2021-04-13 | Frimline Private Limited | Pharmaceutical composition for improving or preventing progression of chronic kidney disease |
US11819511B2 (en) * | 2019-08-26 | 2023-11-21 | Epitech Group S.P.A. | Composition of N-palmitoyl-ethanolamide and Rutin in co-micronized form |
Also Published As
Publication number | Publication date |
---|---|
EP2921167A1 (de) | 2015-09-23 |
US10441559B2 (en) | 2019-10-15 |
EP2921167B1 (de) | 2016-08-17 |
ES2603809T3 (es) | 2017-03-01 |
CY1118214T1 (el) | 2017-06-28 |
CA2884898A1 (en) | 2015-09-19 |
CA2884898C (en) | 2022-03-08 |
US20170252314A1 (en) | 2017-09-07 |
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