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WO2025155109A1 - Composition pour le traitement d'un dysfonctionnement cognitif - Google Patents

Composition pour le traitement d'un dysfonctionnement cognitif

Info

Publication number
WO2025155109A1
WO2025155109A1 PCT/KR2025/000936 KR2025000936W WO2025155109A1 WO 2025155109 A1 WO2025155109 A1 WO 2025155109A1 KR 2025000936 W KR2025000936 W KR 2025000936W WO 2025155109 A1 WO2025155109 A1 WO 2025155109A1
Authority
WO
WIPO (PCT)
Prior art keywords
day
cognitive dysfunction
control group
test
administration
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/KR2025/000936
Other languages
English (en)
Korean (ko)
Inventor
제강훈
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.)
Neurolmed Co Ltd
Original Assignee
Neurolmed Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Neurolmed Co Ltd filed Critical Neurolmed Co Ltd
Publication of WO2025155109A1 publication Critical patent/WO2025155109A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia

Definitions

  • the present invention relates to a composition for treating cognitive dysfunction.
  • scopolamine is a nonspecific muscarinic anticholinergic drug that is known to decrease learning and cognitive abilities by interacting with cholinergic probes and is known to cause amnesia by interfering with long-term potentiation in the hippocampus and other areas.
  • sobrerol compound improves cognitive dysfunction such as amnesia in a scopolamine-induced amnesia mouse model.
  • Figure 9 shows the number of neuronal cell bodies in the cornu ammonis 1 (CA1), cornu ammonis 3 (CA3), and dentate gyrus (DG) regions of the hippocampus using Nissl stain.
  • Figure 10 shows the results of quantitative analysis of p-Tau in the CA1, CA3, and DG regions of the hippocampus using immunohistochemical staining, in relative ratios, relative to the negative control group (G2).
  • the present invention provides a pharmaceutical composition for treating or preventing cognitive dysfunction, comprising a compound represented by chemical formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
  • the compound represented by the chemical formula 1 is sobrerol (5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-ol), which is one of the terpene alcohols having the chemical formula 1 of C 10 H 18 O 2 .
  • an increase in avoidance time in a passive avoidance test, a decrease in movement time and movement distance in a Morris water maze test, and an increase in cross number were observed by administration of 80 and 100 mg/kg/day of the compound represented by the chemical formula 1.
  • a decrease in blood amyloid- ⁇ 1-40 and 1-42 an increase in brain acetylcholine and a decrease in acetylcholine hydrolase, an increase in hippocampal neurons in the brain, and a decrease in p-Tau were observed, confirming an effect of improving memory.
  • cogntive function of the present invention refers to various intellectual abilities such as attention, perception, memory, language ability, and executive ability.
  • cognitive function may be used interchangeably with “cognitive ability” or “cognitive ability.”
  • memory or “memory ability” used in the present invention refers to the ability to acquire new information, learned experiences, or knowledge obtained from the surrounding environment, encode and store them in a specific part of the brain, and recall them.
  • memory disorder used in the present invention refers to a disease in which the ability to retain and recognize information, experiences, and stimuli is lost or impaired, including amnesia or memory loss. Memory disorder can occur even if any one of the three processes of memory inscription, maintenance, and reproduction is impaired.
  • composition of the present invention may have a therapeutic or preventive effect on cognitive dysfunction due to cognitive decline induced by scopolamine.
  • the cognitive dysfunction of the present invention can be caused by cholinergic neuronal decline
  • the composition of the present invention can improve cholinergic neuronal decline, and has the effect of improving cognitive functions such as memory caused by cholinergic neuronal decline by increasing acetylcholine in brain tissue, decreasing acetylcholine hydrolase, increasing neurons in the hippocampal region of the brain, and decreasing p-Tau.
  • the "scopolamine” of the present invention is a competitive antagonist that blocks muscarinic receptors (mAChR), one of the subtypes of cholinergic neurons, and prevents acetylcholine from binding to the receptor in the synaptic gap without changing the amount of acetylcholine, which causes memory impairment similar to the phenomenon caused by damage to cholinergic neurons in the central nervous system.
  • mAChR muscarinic receptors
  • composition of the present invention can protect nerve cells by reducing the expression of amyloid protein (Amyloid ⁇ , A ⁇ ) and tau protein, thereby treating or preventing cognitive dysfunction.
  • amyloid protein Amyloid ⁇ , A ⁇
  • tau protein tau protein
  • amyloid protein refers to a 36-43 amino acid peptide that is a major component of amyloid plaques found in the brains of Alzheimer's patients and is critically involved in Alzheimer's disease. It is known that nerve cells die throughout the brain due to extracellular beta-amyloid deposition and intracellular hyperphosphorylated tau protein.
  • the pharmaceutical composition contains a compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient, may additionally contain a pharmaceutically acceptable carrier, and may be formulated in the form of oral formulations such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols, external preparations, and sterile injection solutions according to conventional methods.
  • active ingredient means an ingredient that exhibits the desired activity alone or can exhibit the activity together with a carrier that is inactive on its own.
  • composition of the present invention may include diluents or excipients such as fillers, bulking agents, binders, wetting agents, disintegrants, surfactants, and other pharmaceutically acceptable additives.
  • oral administration refers to a method of injecting a drug into the mouth to improve pathological symptoms (periodontal disease)
  • parenteral administration refers to a method of administering subcutaneously, intramuscularly, intravenously, or intraperitoneally using a tube, excluding oral administration.
  • Solid preparations for oral administration include powders, granules, tablets, capsules, soft capsules, and pills.
  • Liquid preparations for oral administration include suspensions, solutions, emulsions, syrups, and aerosols.
  • various excipients such as wetting agents, sweeteners, flavoring agents, and preservatives may be included.
  • Preparations for parenteral administration can be formulated and used in the form of external preparations such as sterilized aqueous solutions, liquids, non-aqueous solvents, suspensions, emulsions, eye drops, eye ointments, syrups, suppositories, aerosols, etc. and sterile injection preparations according to conventional methods, and preferably, pharmaceutical compositions of creams, gels, patches, sprays, ointments, warnings, lotions, liniments, eye ointments, eye drops, patches, or cataplasmas can be prepared and used, but are not limited thereto.
  • Compositions for topical administration can be anhydrous or aqueous depending on the clinical prescription.
  • Non-aqueous solvents and suspensions can include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate.
  • Suppository bases that can be used include witepsol, macrogol, Tween 61, cocoa butter, laurin butter, and glycerogelatin.
  • Diluents or excipients such as fillers, bulking agents, binders, wetting agents, disintegrants, surfactants, and other pharmaceutically acceptable additives according to the present invention may be included in an amount of 0.1 to 99.9 wt% of the composition, specifically, 0.1 to 50 wt%, but is not limited thereto.
  • the pharmaceutical composition of the present invention is administered in a pharmaceutically effective amount.
  • pharmaceutically effective amount means an amount sufficient to treat a disease at a reasonable benefit/risk ratio applicable to medical treatment, and the effective dosage level can be determined based on factors including the type and severity of the individual, age, sex, activity of the drug, sensitivity to the drug, time of administration, route of administration and excretion rate, duration of treatment, concurrently used drugs, and other factors well known in the medical field.
  • the compound represented by the chemical formula 1 may be administered at a total daily dosage of 20 to 100 mg/kg/day on an animal basis. Specifically, when administered to mice, the total daily dosage may be orally administered at a total daily dosage of 60 to 100 mg/kg/day, and more specifically, the total daily dosage may be orally administered at a total daily dosage of 80 to 100 mg/kg/day.
  • the cognitive function impairment improvement effect was excellent when administered at 60 to 100 mg/kg/day.
  • the compound represented by the chemical formula 1 was administered to mice at 60 to 100 mg/kg/day, cognitive function impairment was improved to a level equivalent to or higher than that of the positive control group, Aricept.
  • Km refers to the body surface area-based coefficient. It represents the metabolic rate relative to the body surface area between animals and humans, and is used to convert the drug dose from animals to humans.
  • the above Km is based on the proportional relationship between body surface area and body weight, and reflects the physiological differences between animals and humans.
  • Km body weight (kg) / body surface area (m2)
  • the compound represented by the chemical formula 1 can be administered at 10 to 1500 mg/day for an adult weighing 60 kg, and when the total daily dose is 80 to 100 mg/kg/day orally administered to a mouse, the amount can be orally administered at 300 to 900 mg/day for an adult.
  • HED animal-human equivalent dose
  • the above administration may be administered once a day or divided into several times.
  • the cognitive dysfunction may be selected from the group consisting of dementia, learning disorder, agnosia, amnesia, aphasia, apraxia, delirium, mild cognitive impairment, depression, Alzheimer's disease, vascular dementia, and Binswanger disease.
  • the compound represented by the chemical formula 1 or a food-wise acceptable salt thereof may be added to the food composition, and the types thereof are not particularly limited.
  • various herbal extracts, food-wise acceptable food additives, or natural carbohydrates may be contained as additional ingredients, but are not limited thereto.
  • the term "food supplement additive” means a component that can be added to food as an auxiliary, and can be appropriately selected and used by those skilled in the art as something added in the manufacture of food of each formulation.
  • food supplement additives include various nutrients, vitamins, minerals (electrolytes), flavoring agents such as synthetic flavoring agents and natural flavoring agents, coloring agents and fillers, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloid thickeners, pH regulators, stabilizers, preservatives, glycerin, alcohol, carbonating agents used in carbonated beverages, and the like, but the types of food supplement additives of the present invention are not limited by the above examples.
  • natural carbohydrates examples include monosaccharides such as glucose and fructose; disaccharides such as maltose and sucrose; and polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol and erythritol.
  • natural flavoring agents thaumatin, etc.
  • stevia extracts rebaudioside A, glycyrrhizin, etc.
  • synthetic flavoring agents sacharin, aspartame, etc.
  • the food composition of the present invention may include a health functional food.
  • the term "health functional food” refers to a food manufactured and processed in the form of tablets, capsules, powders, granules, liquids, and pills using raw materials or ingredients having functionality useful to the human body.
  • functionality means obtaining a useful effect for health purposes such as regulating nutrients for the structure and function of the human body or physiological effects.
  • the health functional food of the present invention can be manufactured by a method commonly used in the art, and can be manufactured by adding raw materials and ingredients commonly added in the art during the manufacturing process.
  • unlike general drugs it has the advantage of not having side effects that may occur when taken for a long period of time, and can be highly portable.
  • the compound represented by the chemical formula 1 may be included in the food composition so that the total daily dosage is 20 to 100 mg/kg/day based on an animal. Specifically, when administered to a mouse, the compound may be included in the food composition so that the total daily dosage is 60 to 100 mg/kg/day, and more specifically, the compound may be included in the food composition so that the total daily dosage is 80 to 100 mg/kg/day, and may be included in a health functional food, which is an example of the food composition.
  • HED human equivalent dose
  • HED Animal Dose (mg/kg) ⁇ (Animal Km/Human Km) ⁇ Human Body Weight (kg)
  • Km refers to the body surface area-based coefficient. It represents the metabolic rate relative to the body surface area between animals and humans, and is used to convert the drug dose from animals to humans.
  • the above Km is based on the proportional relationship between body surface area and body weight, and reflects the physiological differences between animals and humans.
  • Km body weight (kg) / body surface area (m2)
  • the administration may be once a day or divided into several times.
  • the amount of the active ingredient included in the above food composition can be appropriately determined depending on the purpose of use (prevention, health or therapeutic treatment). Generally, when manufacturing a food, the active ingredient of the present invention can be added in an amount of 0.01 to 50 wt%, preferably 0.1 to 10 wt%, of the raw material composition, but is not limited thereto. However, in the case of long-term intake for the purpose of health and hygiene or health control, the amount can be used below the above range.
  • the present invention provides a method for preventing or treating cognitive dysfunction, comprising administering to a subject a compound represented by the chemical formula 1 or a pharmaceutically acceptable salt thereof.
  • Scopolamine (Sigma-aldrich, Cat no. S1875) was prepared at a concentration of 1 mg/10 mL in saline solution. Scopolamine was administered intraperitoneally at a dose of 1 mg/kg once/day on the 7th day (Y-maze test)4), 14-15 days (passive avoidance test), 24-28 days (Morris water maze test), and 29th day (day of autopsy) after test substance administration. Scopolamine was administered 30 minutes after test substance administration.
  • Figure 1 shows the results of measuring the body weight of experimental animals.
  • the negative control group (G2) showed a statistically significant weight loss on DAY 29 (P ⁇ 0.05) compared to the normal control group (G1). No statistically significant weight changes were observed during the other observation periods.
  • the test substance administration groups (G3-G6) and the positive control group (G7) showed no statistically significant weight changes during all observation periods compared to the negative control group (G2).
  • the light was turned off and the guillotine door was opened to allow the animal to come and go freely.
  • the light was turned on again and the animal was allowed to come and go freely for 120 seconds.
  • the guillotine door was closed and a 0.20 mA scrambled shock was applied for 2 seconds.
  • the test substance On the 15th day after the test substance administration, which is 24 hours later, the test substance was administered first, then scopolamine was administered 30 minutes later. 30 minutes after the scopolamine administration, the animals were placed in a lighted area and the guillotine door was opened, and the time taken to move to the shaded area was measured (retention trial).
  • the avoidance time measurement results showed that the negative control group (G2) showed an increase of 57.41% in avoidance time on DAY 14 compared to the normal control group (G1), although this was not statistically significant.
  • the test substance administration groups (G3-G6) and the positive control group (G7) did not show any statistically significant changes on DAY 14 compared to the negative control group (G2).
  • the avoidance time was measured, and the negative control group (G2) showed a statistically significant decrease in avoidance time on DAY 15 compared to the normal control group (G1) (P ⁇ 0.01).
  • the 20, 40, and 80 mg/kg/day NRM-331 administration groups (G3-G5) did not show a statistically significant difference in avoidance time compared to the negative control group (G2), but the 80 mg/kg/day NRM-331 administration group (G5) showed a 26.97% increase in avoidance time, although this was not statistically significant.
  • the 100 mg/kg/day NRM-331 administration group (G6) and the positive control group (G7) showed a statistically significant increase in avoidance time compared to the negative control group (G2) (P ⁇ 0.01).
  • the Morris water maze test was conducted on days 22-28 after the administration of the test substance.
  • a platform was placed in the pool of one of the four designated release points in the tank (diameter: 1 m), and the animals were allowed to find it for 60 seconds. After finding the platform, the animals were allowed to rest on it for approximately 30 seconds. If the animals could not find the platform within 60 seconds, the animals were placed on the platform and allowed to rest for approximately 30 seconds. After completing one trial with five animals per group, the next trial began, and two trials were conducted per day. However, the release points were randomly selected so that they did not overlap. This method was repeated for 7 days, and the time until the platform was found was measured (training: 2 days, behavioral experiment: 4 days, probe trial: 1 day). On the final 7th day, the platform was removed, and a probe trial was conducted for 60 seconds to measure the number of crosses at the location where the platform was.
  • Figure 4 shows the movement time required to find the platform using the Morris water maze test.
  • the negative control group (G2) showed a statistically significant increase in the movement time on DAY 24, 25, 26, and 27 compared to the normal control group (G1) (P ⁇ 0.01).
  • the 20 mg/kg/day administration group (G3) of NRM-331 a decrease in the movement time of 14.59%, 19.90%, 16.36%, and 22.50% on DAY 24, 25, 26, and 27, respectively, was observed compared to the negative control group (G2), although the difference was not statistically significant.
  • the 40, 80, 100 mg/kg/day NRM-331 administration groups (G4-G6) and the positive control group (G7) showed a statistically significant decrease in transit time on DAY 24, 25, 26, and 27 compared to the negative control group (G2) (P ⁇ 0.01), and the 100 mg/kg/day NRM-331 administration group (G6) showed a 13.84% decrease in transit time on DAY 24 compared to the positive control group (G7), although this was not statistically significant.
  • Figure 5 shows the distance traveled to find the platform using the Morris water maze test.
  • the negative control group (G2) showed a statistically significant increase in the moving distance on DAY 24, 25, 26, and 27 compared to the normal control group (G1) (P ⁇ 0.01).
  • the 20 mg/kg/day NRM-331 administration group (G3) showed a statistically significant decrease in the moving distance on DAY 25 and 27 compared to the negative control group (G2) (P ⁇ 0.05 or P ⁇ 0.01), and a statistically insignificant 17.47% decrease in the moving distance on DAY 26.
  • the 40, 80, and 100 mg/kg/day NRM-331 groups (G4-G6) and the positive control group (G7) showed a statistically significant decrease in moving distance compared to the negative control group (G2) (P ⁇ 0.01), and the 100 mg/kg/day NRM-331 group (G6) showed a 15.07% decrease in moving distance on DAY 24 compared to the positive control group (G7), although this was not statistically significant.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Neurology (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Hospice & Palliative Care (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne : une composition pharmaceutique pour le traitement ou la prévention d'un dysfonctionnement cognitif, comprenant un composé représenté par la formule chimique 1 ou un sel pharmaceutiquement acceptable de celui-ci ; et une composition alimentaire pour prévenir ou soulager un dysfonctionnement cognitif. Le composé a pour effet de traiter ou de soulager un dysfonctionnement cognitif, et peut ainsi être utilisé en tant que principe actif d'une composition pharmaceutique et d'une composition alimentaire pour le traitement d'un dysfonctionnement cognitif.
PCT/KR2025/000936 2024-01-17 2025-01-16 Composition pour le traitement d'un dysfonctionnement cognitif Pending WO2025155109A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2024-0007302 2024-01-17
KR1020240007302A KR102804780B1 (ko) 2024-01-17 2024-01-17 인지기능 장애의 치료용 조성물

Publications (1)

Publication Number Publication Date
WO2025155109A1 true WO2025155109A1 (fr) 2025-07-24

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PCT/KR2025/000936 Pending WO2025155109A1 (fr) 2024-01-17 2025-01-16 Composition pour le traitement d'un dysfonctionnement cognitif

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KR (1) KR102804780B1 (fr)
WO (1) WO2025155109A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639469A (en) * 1970-04-17 1987-01-27 Corvi Mora Camillo Method of preparing sobrerol and the pharmaceutical application of the sobrerol thus obtained
WO1992003128A1 (fr) * 1990-08-22 1992-03-05 Riace Establishment Compositions pharmaceutiques a activite mucolytique et antitussive contenant du (-)-trans-sobrerol
KR20170030448A (ko) * 2015-09-09 2017-03-17 한국생명공학연구원 소브레롤을 포함하는 근력 약화 관련 질환의 예방 또는 치료용 조성물
US20190000776A1 (en) * 2017-06-30 2019-01-03 Industrial Technology Research Institute Method for treating an autoimmune neurological disease and/or neurodegenerative disease and pharmaceutical formulations for a liquid dosage form and a controlled release dosage form
KR20220026806A (ko) * 2020-08-26 2022-03-07 주식회사 뉴롤메드 소브레롤을 유효성분으로 함유하는 허혈성 뇌졸중 예방 또는 치료용 조성물

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101694913B1 (ko) 2015-01-15 2017-01-10 경상대학교산학협력단 양파 추출물 또는 이의 분획물을 유효성분으로 함유하는 인지기능 또는 기억능력 개선용 조성물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639469A (en) * 1970-04-17 1987-01-27 Corvi Mora Camillo Method of preparing sobrerol and the pharmaceutical application of the sobrerol thus obtained
WO1992003128A1 (fr) * 1990-08-22 1992-03-05 Riace Establishment Compositions pharmaceutiques a activite mucolytique et antitussive contenant du (-)-trans-sobrerol
KR20170030448A (ko) * 2015-09-09 2017-03-17 한국생명공학연구원 소브레롤을 포함하는 근력 약화 관련 질환의 예방 또는 치료용 조성물
US20190000776A1 (en) * 2017-06-30 2019-01-03 Industrial Technology Research Institute Method for treating an autoimmune neurological disease and/or neurodegenerative disease and pharmaceutical formulations for a liquid dosage form and a controlled release dosage form
KR20220026806A (ko) * 2020-08-26 2022-03-07 주식회사 뉴롤메드 소브레롤을 유효성분으로 함유하는 허혈성 뇌졸중 예방 또는 치료용 조성물

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