WO2019074235A1 - Composition contenant alpha-asarone pour la prévention ou le traitement de lésion de la moelle épinière - Google Patents

Composition contenant alpha-asarone pour la prévention ou le traitement de lésion de la moelle épinière Download PDF

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Publication number
WO2019074235A1
WO2019074235A1 PCT/KR2018/011715 KR2018011715W WO2019074235A1 WO 2019074235 A1 WO2019074235 A1 WO 2019074235A1 KR 2018011715 W KR2018011715 W KR 2018011715W WO 2019074235 A1 WO2019074235 A1 WO 2019074235A1
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WIPO (PCT)
Prior art keywords
spinal cord
cord injury
asarone
alpha
pharmaceutical composition
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Ceased
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English (en)
Korean (ko)
Inventor
한인보
조민재
최혜민
쿠마헤먼트
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Industry Academic Cooperation Foundation of College of Medicine Pochon CHA University
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Industry Academic Cooperation Foundation of College of Medicine Pochon CHA University
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Publication of WO2019074235A1 publication Critical patent/WO2019074235A1/fr
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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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/30—Foods, ingredients or supplements having a functional effect on health

Definitions

  • Alpha asarone and a composition for preventing or treating spinal cord injury.
  • Damage to the spinal cord is a secondary regression that leads to mechanical damage and consequent loss of tissue progression.
  • the pathologic phenomenon that occurs after spinal cord injury is classified into two stages, primary damage and secondary damage, over time.
  • Primary injury occurs within minutes after traumatic injury, and necrosis of cell death occurs mainly in wound area.
  • the cause of this reaction is mediated inflammatory reaction induced mainly by pro-inflammatory cytokine.
  • Secondary damage following primary damage progresses slowly from hours to days and not only the cells in the wound but also the surrounding neurons gradually undergo apoptosis.
  • Inflammatory responses from primary damage are a major mechanism of these secondary injuries and are involved in causing neuropathies of chronic spinal cord injury. As the inflammatory reaction continues, apoptosis gradually enlarges and the damaged area inside the spinal cord becomes wider, resulting in a permanent loss of function.
  • the direction of spinal cord injury treatment is to minimize the damage of the secondary spinal cord and restore the neurological function to its maximum extent.
  • a spinal cord injury occurs, there is a method of preventing cell necrosis due to the inflammation reaction of neurons using a high-dose steroid drug while eliminating the fragment or dislocation that compresses the spinal cord through surgical treatment.
  • administration of steroid drugs to patients at high doses has limited clinical efficacy because of the enormous side effects of sepsis, gastrointestinal bleeding, and pneumonia. Because of the above reasons, there is no stable therapeutic agent that can restore the damaged spinal nerve. That is, there is a need for a therapeutic agent capable of treating spinal cord injury, having potent anti-inflammatory activity without side effects.
  • One aspect is to provide a pharmaceutical composition for preventing or treating spinal cord injury comprising alpha-asarone or a pharmaceutically acceptable salt thereof as an active ingredient.
  • Another aspect is to provide a health functional food for preventing or ameliorating spinal cord injury comprising alpha-asarone as an active ingredient.
  • One aspect provides a pharmaceutical composition for preventing or treating spinal cord injury comprising an essential oil component of Acorus gramineus , for example, alpha-asarone or a pharmaceutically acceptable salt thereof as an active ingredient.
  • alpha-asarone or a pharmaceutically acceptable salt thereof for use in the manufacture of a pharmaceutical composition or preparation for preventing or treating spinal cord injury.
  • alpha-asarone or a pharmaceutically acceptable salt thereof for use in the manufacture of a medicament for the prevention or treatment of disease, for example, spinal cord injury.
  • Another aspect provides a method of preventing or treating a disease, e. G., Spinal cord injury, comprising administering to a subject in need thereof an alpha asarone or a pharmaceutically acceptable salt thereof of an active ingredient.
  • a disease e. G., Spinal cord injury
  • the term "seokchangpo" is the scientific name Acorus It is a gramineus , a perennial plant with green leaves of the genus Agate .
  • the rootstock is thick and hard, has many nodes, and is attached to the same spot as a rock gap by taking out roots. Leaves grow from roots to base layers overlapping each other. Narrow strips are brittle and shiny. The tip of the leaf is pointed like a knife, the edge is plain and always smells good. Flowers blend in the shape of a round stick in the middle of the flower-like peduncle. The length of the stick is 5cm and the color is yellowish blue. It is also called white whitish, iris, stony grass and gypsum, and it contains 0.5 ⁇ 0.8% essential oil in rootstock. Essential oils are Asarone, Palmitinsaure and Phenol.
  • alpha asarone may be mixed with “ asarone ", and may be a compound represented by the following formula (1).
  • Alpha-asarone inhibits neuroinflammation through inhibition of various inflammatory factors such as TNF- ⁇ , IL-1 ⁇ , and IL-6, as well as neuroprotection through antioxidant and nitric oxide production inhibition in various parts of the brain The effect can be shown. Since the initial mechanism of spinal cord injury is so fast that it is difficult to treat it as a pharmacologic treatment, the pharmacological strategies dealing with the secondary mechanism are an important part of the development of therapeutic agents. In this regard, up to now, steroids, antioxidants, glutamate receptor inhibitors, Various potential pharmacological treatments have been attempted, including inhibitors, gangliosides, antibodies to axon regeneration inhibitors, antiinflammatory agents, and neurotrophins.
  • the pharmaceutical composition for preventing or treating spinal cord injury according to the present invention is useful as an anti-inflammatory, M2 polarization and anti- It was confirmed whether or not the effect of angiogenesis could be shown.
  • the pharmaceutical composition according to the present invention can be used not only as a spinal cord injury due to trauma, but also as a spinal cord injury-related acute transverse myelitis, , Hereditary diseases, non-Hodgkin's lymphoma, hydrocephalus, hereditary ataxia, neurosyphilis, Minamata disease, Lou Gehrig's disease, multiple sclerosis and the like.
  • the alpha asarone may be included in the composition as a pharmaceutically acceptable salt thereof.
  • the salt may be an acid addition salt or a base addition salt.
  • the acid addition salt includes a salt with an inorganic acid or an organic acid. Examples of the inorganic acid salt include salts with hydrochloric acid, hydrobromic acid, phosphoric acid or sulfuric acid.
  • organic acid salt examples include acetic acid, trifluoroacetic acid, propionic acid, maleic acid, fumaric acid, malic acid, citric acid, , Benzoic acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid or naphthalenedisulfonic acid, but is not limited thereto.
  • the base addition salts include, for example, alkali metal salts such as sodium or potassium salts, alkaline earth metal salts such as calcium or magnesium salts, or ammonia salts or organic amine salts such as diethylamine, triethylamine, ethyl And salts with diisopropylamine, procaine, dibenzylamine, N-methylmorpholine, or dihydroabiethylamine.
  • alkali metal salts such as sodium or potassium salts
  • alkaline earth metal salts such as calcium or magnesium salts
  • ammonia salts or organic amine salts such as diethylamine, triethylamine, ethyl And salts with diisopropylamine, procaine, dibenzylamine, N-methylmorpholine, or dihydroabiethylamine.
  • alpha asanone or a pharmaceutically acceptable salt thereof is to be interpreted to be in any form selected from the group consisting of any of its crystalline forms and amorphous forms, and hydrates, solvates, and co-crystals thereof.
  • the pharmaceutical composition according to the present invention may be an oral or parenteral dosage form.
  • the pharmaceutical preparations may be formulated for oral administration, such as tablets, hard or soft capsules, liquids, suspensions, etc. These pharmaceutical preparations may contain conventional pharmaceutically acceptable carriers, for example, excipients, binders , A disintegrant, a lubricant, a solubilizing agent, a suspending agent, a preservative or an extender, and the like.
  • the pharmaceutical composition may be used as a preparation for parenteral administration such as cream, gel, patch, spray, ointment, warning agent, lotion and the like.
  • the pharmaceutical composition may further contain commonly used excipients, disintegrants, sweeteners, lubricants, flavors and the like, and may be formulated into tablets, capsules, powders, granules, suspensions, emulsions, syrups, Other liquid formulations may be formulated.
  • Binders such as lactose, saccharose, sorbitol, mannitol, starch, amylopectin, celluloses or gelatin, excipients such as dicalcium phosphate, disintegrants such as corn starch or sweet potato starch, and disintegrants such as stearic acid Magnesium stearate, calcium stearate, sodium stearyl fumarate, or polyethylene glycol wax.
  • a liquid carrier such as fatty oil is contained.
  • the pharmaceutical composition of the present invention can be administered orally or parenterally.
  • parenteral administration subcutaneous injection, intravenous injection, intramuscular injection, or intramuscular injection can be selected.
  • parenteral administration formulations the bile acid or the salt thereof of the present invention is mixed with water or a stabilizer or buffer to prepare a suspension, which is then formulated into a unit dosage form of ampoule or vial.
  • administering means introducing the pharmaceutical composition of the present invention into an inflammatory disease or a suspect member of spinal cord injury by any appropriate method, and the administration route may be either oral or parenteral May be administered via various routes of administration.
  • Administration of the pharmaceutical composition is applicable to any animal, and the animal includes not only humans and primates but also livestock such as cows, pigs, sheep, horses, dogs, rats, rats and cats.
  • compositions herein may be administered in a pharmaceutically effective amount.
  • the term " pharmaceutically effective amount" means an amount sufficient to treat a disease at a reasonable benefit / risk ratio applicable to medical treatment and the effective dose level will vary depending on the species and severity, age, sex, The type of drug, the activity of the drug, the sensitivity to the drug, the time of administration, the route of administration and the rate of release, the duration of the treatment, factors including co-administered drugs, and other factors well known in the medical arts.
  • the composition of the present invention may be administered as an individual therapeutic agent or in combination with other therapeutic agents, and may be administered sequentially or simultaneously with conventional therapeutic agents. And can be administered singly or multiply.
  • the dosage of the pharmaceutical composition of the present invention may be determined by a specialist depending on various factors such as the condition of the patient, age, sex, and complications, but is generally from 0.1 mg to 10 g per kg of the adult, or from 10 mg to 5 g Dose. ≪ / RTI > Also, the daily dosage of the pharmaceutical composition per unit dosage form, or a half, 1/3, or 1/4 dose thereof, may be contained, and may be administered 1 to 6 times per day.
  • the amount may be less than the above range, and the active ingredient may be used in an amount in the above-mentioned range because there is no problem in terms of safety.
  • the alpha asarone may be one that causes M2 polarization.
  • the alpha asarone may be one that inhibits the expression of inflammatory cytokine genes and proteins.
  • the inflammatory cytokine may be at least one selected from the group consisting of TNF-a, IL-1 alpha, IL-1 beta, and IL-6.
  • the alpha asarone may be one that enhances the motor function of the spinal cord injured entity, or promotes repair of damaged spinal cord tissue.
  • alpha asarone or a pharmaceutically acceptable salt thereof may be usefully employed in compositions for the prevention, amelioration, or treatment of inflammatory diseases or spinal cord injury.
  • Another aspect provides a health functional food for preventing or ameliorating spinal cord injury comprising alpha-asarone as an active ingredient.
  • the food may be, but is not limited to, a health supplement food, a health functional food, a functional food, and the like, and includes the addition of the compound of the present invention to natural foods, processed foods, patient foods, and general food ingredients.
  • the food composition according to the present invention can be used as it is, or can be used in combination with other food or food compositions, and can be suitably used according to conventional methods.
  • the amount of the active ingredient to be mixed can be suitably determined according to its intended use (prevention, improvement, or therapeutic treatment).
  • the effective dose of the alpha-asarone or its salt may be used according to the effective dose of the pharmaceutical composition, but may be less than the above-mentioned range for the purpose of health and hygiene or long-term intake for the purpose of health control,
  • the above components can be used in an amount exceeding the above range because there is no problem in terms of safety.
  • the food composition may be used in the form of tablets, hard or soft capsules, liquids, suspensions, and the like, which may contain conventional excipients, such as excipients in the case of oral preparations, Binders, disintegrators, lubricants, solubilizers, suspending agents, preservatives or extenders.
  • Examples of the food include dairy products including meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen and other noodles, gums and ice cream, soups, drinks, tea, drinks, , And other nutrients, but are not limited to these kinds of foods.
  • Alpha-asarone according to one embodiment has an effect of enhancing motor function or recovery of injured spinal cord when administered to spinal cord injured individuals, and thus may be useful for preventing, improving or treating inflammatory diseases and spinal cord injuries.
  • Alpha Asarone is a registered herb medicine ingredient in the Korea Food and Drug Administration and has a low risk of adverse effects. Therefore, it is easy to carry out clinical trials because it is exempted from the nonclinical toxicity and pharmacological test results when obtaining the approval of the drug product.
  • FIG. 1 is a schematic diagram showing development of a mouse spinal cord injury model using a weight.
  • FIG. 2 is a graph showing the results of a BBB score test for measuring the locomotor function of a spinal cord injured subject to which the pharmaceutical composition according to the present invention was administered. As shown in FIG. 2, Of the patients were significantly higher than those of the control group.
  • FIG. 3 shows a cut-off histological analysis of the injured area of the group administered with the pharmaceutical composition according to the present invention on days 1, 3, 7 and 14 after spinal cord injury and the control group
  • FIG. 3a shows the results of hematoxylin eosin
  • FIG. 3B is a photograph showing the results of H & E staining
  • FIG. 3B is a result of GFAP immunohistological staining
  • FIG. 3C is a photograph of CD68, CD86 and Arg1 staining
  • FIG. 3D is a photograph of DAPI and GEAP immunohistochemical staining.
  • FIG. 4 is a graph showing the ratios of arg1, iNOS and CD68 immunohistocytic staining (FIG. 4A) and arg1, iNOS, and CD68 of the control group and the group administered with the pharmaceutical composition according to the present invention on days 7 and 14 after spinal cord injury (Fig. 4B), and the graph shows the results of the difference between the upper two of 7 days and the lower 2 of 14 days.
  • FIG. 5 is a graph (FIG. 5A) showing the Ang1 and VEGFR immunohistochemical staining images (FIG. 5A) and intensity of the control group (FIG. 5B) of the group administered with the pharmaceutical composition according to the present invention at 14 days after injury of the spinal cord.
  • Example 1 alpha-asarone (alpha- asarone ) As an active ingredient in the manufacture of a pharmaceutical composition for preventing or treating spinal cord injury
  • Alpha asarone was purchased and prepared by stirring 1% carboxymethylcellulose solution and 1% Tween 80.
  • composition for preventing or treating spinal cord injury comprising alpha asarone according to the present invention was prepared, and the effect of treating spinal cord injury using Example 1 was confirmed in the following experimental examples.
  • the spinal cord injury was applied using a fall-fall method.
  • the weight and weights of 20g, 35g, and 50g were used to construct a laryngeal laminectomy at the T10 site to remove the vertebral bone plate.
  • An impactor, which is further coupled to the support rod, causes spinal cord injury. Weights may be used in different weights, and a schematic diagram thereof is shown in Fig.
  • the body weight was first measured, and the epilator was used to epilate in a circle having a radius of about 4 cm around the 10th thoracic vertebra region.
  • the epilating area was sterilized with 70% alcohol.
  • the surgical site was disinfected with povidone and 70% alcohol.
  • the epidermis was incised by a surgical knife about 5 cm.
  • the muscle layer exposed after the incision was incised by about 2 cm in the 10th thoracic region using a surgical knife.
  • the extensor was removed using an Offset Bone Nipper (FST, Germany) and the spinal bone plate (lamina) was exposed to the posterior spinal cord without damage to the dura meter.
  • the 8th thoracic and 11th thoracic spiral surgeries were fixed with Allis Forceps to expose the posterior spinal cord without damaging the dura. Then, the spinal cord was squeezed at 10th thoracic position for 5 minutes by using weights (20g, 35g, and 50g) to produce a spinal cord compression model.
  • composition prepared in Example 1 was orally administered at 1 mg / kg of the above 1.3.
  • the BBB score test was performed to measure the motor function of the spinal cord trauma mice administered with the drug.
  • the BBB score test is a test method that can evaluate various exercise functions in a complex manner. The score is divided from the minimum score of 0 to 21 points when the hind legs can not be used at all according to the 21 items. Which means improved functionality.
  • the spinal cord of the asarone group (the spinal cord injured population treated with the pharmaceutical composition according to the present invention) and the Injury group (control group) were placed in 4% PFA on days 1, 3, 7 and 14 after spinal cord injury, Cut 1cm from the damaged area and make a paraffin block as a longitudinal section.
  • the blocks were cut to a thickness of 5 ⁇ m and then treated with hematoxylin eosin through a deparaffinization process.
  • the spinal cord of the asarone group (the spinal cord injured population treated with the pharmaceutical composition according to the present invention) and the Injury group (control group) were placed in 4% PFA on days 1, 3, 7 and 14 after spinal cord injury, A 1-cm section was cut from the damaged area and a paraffin block was made as a longitudinal section. Blocks were cut to a thickness of 5 ⁇ m and subjected to immunofluorescent staining.
  • FIG. 3B shows the results of GFAP immunohistochemical staining of 1 cm of the damaged area of the group administered with the pharmaceutical composition according to the present invention on days 1, 3, 7, and 14 after spinal cord injury
  • FIG. 3c shows the results of CD68, CD86
  • Fig. 3 is a photograph of DAPI and GEAP immunohistochemical staining.
  • FIG. 4 is a graph showing the ratios of arg1, iNOS and CD68 immunohistocytic staining (FIG. 4A) and arg1, iNOS, and CD68 of the control group and the group administered with the pharmaceutical composition according to the present invention on days 7 and 14 after spinal cord injury (Fig. 4B), and the graph shows the results of the difference between the upper two of 7 days and the lower 2 of 14 days.
  • FIG. 5 is a graph (FIG. 5A) showing the Ang1 and VEGFR immunohistochemical staining images (FIG. 5A) and intensity of the control group (FIG. 5B) of the group administered with the pharmaceutical composition according to the present invention at 14 days after injury of the spinal cord.

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  • Polymers & Plastics (AREA)
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Abstract

La présente invention concerne une composition contenant alpha-asarone pour la prévention ou le traitement de lésion de la moelle épinière. L'alpha-asarone selon un aspect a pour effet d'améliorer les fonctions motrices ou de favoriser la restauration de la moelle épinière lésée lorsqu'il est administré à un sujet souffrant d'une lésion de la moelle épinière, et peut ainsi être favorablement utilisé dans la prévention, le soulagement ou le traitement d'une maladie inflammatoire ou d'une lésion de la moelle épinière. De plus, alpha-asarone est un composant médicinal présent dans des plantes enregistré au Ministère de l'Alimentation et de l'Innocuité des Médicaments en Corée, qui présente un faible risque d'effets secondaires, et est exempté d'être soumis à des résultats non cliniques de tests pharmacologiques et de toxicité lors de l'acquisition d'une approbation des médicaments pharmaceutiques, et, par conséquent, des tests cliniques peuvent être effectués facilement.
PCT/KR2018/011715 2017-10-10 2018-10-04 Composition contenant alpha-asarone pour la prévention ou le traitement de lésion de la moelle épinière Ceased WO2019074235A1 (fr)

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KR1020170129118A KR101986832B1 (ko) 2017-10-10 2017-10-10 알파 아사론을 포함하는 척수 손상 예방 또는 치료용 조성물

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Cited By (1)

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CN110934828A (zh) * 2019-12-25 2020-03-31 桂林南药股份有限公司 一种细辛脑口服乳剂及其制备方法

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KR102320780B1 (ko) * 2021-01-29 2021-11-02 정성삼 척추 통증 완화 및 척추 유연성 개선을 위한 조성물 및 이의 제조방법

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110934828A (zh) * 2019-12-25 2020-03-31 桂林南药股份有限公司 一种细辛脑口服乳剂及其制备方法

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