WO2007021061A1 - Composition comprising oleic acid and the use thereof - Google Patents
Composition comprising oleic acid and the use thereof Download PDFInfo
- Publication number
- WO2007021061A1 WO2007021061A1 PCT/KR2006/000082 KR2006000082W WO2007021061A1 WO 2007021061 A1 WO2007021061 A1 WO 2007021061A1 KR 2006000082 W KR2006000082 W KR 2006000082W WO 2007021061 A1 WO2007021061 A1 WO 2007021061A1
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- WIPO (PCT)
- Prior art keywords
- oleic acid
- disease
- present
- brain
- pharmaceutical composition
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 210000001044 sensory neuron Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 208000023516 stroke disease Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- 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
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Definitions
- the present invention relates to a composition comprising oleic acid having neuronal cell-protective activity
- Brain stroke is one of the major public health problem in degenerative disease and the mortality rate from stroke is surpassed only by that of heart.
- the two major categories of stroke are cerebral ischemia and hemorrhage. The former is caused by reduction of blood flow and the latter is caused by bleeding from brain vessels. Reduction of blood flow is occurred by an occlusion in a blood vessel by a blood clot or other things. Ischemic stroke accounts for 80% of all stroke
- t-PA tissue-plasminogen activator
- FDA tissue-plasminogen activator
- the inventors of the present invention have intensively carried out the scientific investigation concerning pharmacological effects and its mechanism of action of oleic acid. As a result of the investigation, the inventors have discovered that it shows novel pharmacological effects, especially, its preventing or treating activity for functional disorder of sensory neuron and they have finally completed the present invention.
- a pharmaceutical composition comprising oleic acid as an active ingredient in an amount effective to protect neuronal cell and to treat or prevent human or mammal suffering from brain diseases such as brain stroke and degenerative brain diseases, together with a pharmaceutically acceptable carrier.
- the present invention provides a pharmaceutical composition comprising oleic acid, as an active ingredient in an effective amount to protect neuronal cell.
- the oleic acid of the present invention is C/s-9-octadecenoic acid expressed by following chemical structure 1. [20] Chemistry Figure 1
- degenerative brain diseases disclosed herein comprise brain stroke, cerebral ischemia, Huntington's disease, Creutzfeld- Jakob disease, Alzheimer's disease (AD), Parkinson's disease (PD), senile dementia and the like.
- oleic acid can be obtained by the procedures as follows: oil material derived from plant or animal oil is pulverized to extract therefrom; the powder is extracted with hexane or chloroform solvent and the extract is concentrated to obtain concentrated non-polar solvent extract; the extract is subjected to silica gel column chromatography with solvent mixture (acetone: hexane) as a mobile phase to isolate purposed oleic acid.
- the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising oleic acid prepared by the above-described method, as an active ingredient in an effective amount to protect neuronal cell and to treat or prevent human or mammal suffering from degenerative brain diseases such as brain stroke and cerebral ischemia, together with a pharmaceutically acceptable carrier.
- the present invention also provides a use of oleic acid for the preparation of the medicament to prevent or treat degenerative brain disease such as brain stroke and cerebral ischemia of mammal or human.
- the present invention also provide a method of treating or preventing brain disease such as brain stroke and cerebral ischemia in a mammal comprising administrating to said mammal an effective amount of above described extract, together with a pharmaceutically acceptable carrier thereof.
- composition according to the present invention can be provided as a pharmaceutical composition containing pharmaceutically acceptable carriers, adjuvants or diluents, e.g., lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starches, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, polyvinyl pyrrolidone, water, methylhydroxy benzoate, propylhydroxy benzoate, talc, magnesium stearate and mineral oil.
- pharmaceutically acceptable carriers e.g., lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starches, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, polyvinyl
- the formulations may additionally include fillers, anti-agglutinating agents, lubricating agents, wetting agents, flavoring agents, emulsifiers, preservatives and the like.
- the compositions of the present invention may be formulated so as to provide quick, sustained or delayed release of the active ingredient after their administration to a patient by employing any of the procedures well known in the art.
- compositions of the present invention can be dissolved in oils, propylene glycol or other solvents that are commonly used to produce an injection.
- suitable examples of the carriers include physiological saline, polyethylene glycol, ethanol, vegetable oils, isopropyl myristate, etc., but are not limited to them.
- the extract of the present invention can be formulated in the form of ointments and creams.
- compositions containing present composition may be prepared in any form, such as oral dosage form (powder, tablet, capsule, soft capsule, aqueous medicine, syrup, elixirs pill, powder, sachet, granule), or topical preparation (cream, ointment, lotion, gel, balm, patch, paste, spray solution, aerosol and the like), or injectable preparation (solution, suspension, emulsion).
- oral dosage form prowder, tablet, capsule, soft capsule, aqueous medicine, syrup, elixirs pill, powder, sachet, granule
- topical preparation cream, ointment, lotion, gel, balm, patch, paste, spray solution, aerosol and the like
- injectable preparation solution, suspension, emulsion
- composition of the present invention in pharmaceutical dosage forms may be used in the form of their pharmaceutically acceptable salts, and also may be used alone or in appropriate association, as well as in combination with other pharmaceutically active compounds.
- the desirable dose of the inventive extract of the present invention varies depending on the condition and the weight of the subject, severity, drug form, route and period of administration, and may be chosen by those skilled in the art. However, in order to obtain desirable effects, it is generally recommended to administer at the amount ranging 0.01-lOg/kg, preferably, 1 to 5g/kg by weight/day of the inventive extract.
- the dose may be administered in single or divided into several times per day.
- the composition should be present between 0.01 to 80% by weight, preferably 0.5 to 50% by weight based on the total weight of the composition.
- composition of present invention can be administered to a subject animal such as mammals (rat, mouse, domestic animals or human) via various routes. All modes of administration are contemplated, for example, administration can be made orally, rectally or by intravenous, intramuscular, subcutaneous,intracutaneous, intrathecal, epidural or intracerebroventricular injection.
- present inventors demonstrated that present composition comprising above described mulberry extract of the present invention have preventing or treating activity of brain stroke by accomplishing in vivo experiment already well known in the art, e.g., middle cerebral artery occlusion model test which is consisted of following step i.e., nylon filament is inserted into internal carotid artery to occlude middle cerebral artery and 120 minutes after, the filament is removed again to allow the reperfusion of the artery.
- middle cerebral artery occlusion model test which is consisted of following step i.e., nylon filament is inserted into internal carotid artery to occlude middle cerebral artery and 120 minutes after, the filament is removed again to allow the reperfusion of the artery.
- a health care food comprising the above-described oleic acid of the present invention prepared by above processes and a sitologically acceptable additive to protect neuronal cell and to prevent or improve brain diseases such as brain stroke and cerebral ischemia.
- composition therein can be added to food, additive or beverage for prevention of brain diseases such as brain stroke and cerebral ischemia as a form of tablet, capsule, pill or beverage type.
- the amount of above described compound of the present invention in food or beverage may generally range from about 0.1 to 15 w/w %, preferably 1 to 10 w/w % of total weight of food for the health food composition and 1 to 30 g, preferably 3 to 10 g on the ratio of IOOD of the health beverage composition.
- the health beverage composition of present invention contains above described compound as an essential component in the indicated ratio
- the other component can be various deodorant or natural carbohydrate etc such as conventional beverage.
- natural carbohydrate are monosaccharide such as glucose, fructose etc; disaccharide such as maltose, sucrose etc; conventional sugar such as dextrin, cyclodextrin; and sugar alcohol such as xylitol, and erythritol etc.
- natural deodorant such as taumatin, stevia extract such as levaudioside A, glycyrrhizin et al., and synthetic deodorant such as saccharin, aspartam et al.
- the amount of above described natural carbohydrate is generally ranges from about 1 to 20 g, preferably 5 to 12 g in the ratio of IOOD of present beverage composition.
- the other components rather than aforementioned composition are various nutrients, a vitamin, a mineral or an electrolyte, synthetic flavoring agent, a coloring agent and improving agent in case of cheese chocolate et al., pectic acid and the salt thereof, alginic acid and the salt thereof, organic acid, protective colloidal adhesive, pH controlling agent, stabilizer, a preservative, glycerin, alcohol, carbonizing agent used in carbonate beverage etc.
- the other component rather than aforementioned ones may be fruit juice for preparing natural fruit juice, fruit juice beverage and vegetable beverage, wherein the component can be used independently or in combination.
- the ratio of the components is not so important but is generally range from about 0 to 20 w/w % per 100 w/w % present composition.
- composition comprising oleic acid according to the present invention shows protective effect of neuronal cell and preventing or treating effect of brain stroke and cerebral ischemia. Therefore, it is useful in the prevention or treatment of degenerative brain diseases in human or mammal.
- Fig. 1 shows the protective effect of various concentration of oleic acid on the injury of brain tissue using by TTC staining method
- Fig. 2 represents the comparison of the effect of control using 5% Tween 20 and test group on brain tissue section of brain injury model
- Fig. 3 presents the recovery activity of various concentration of oleic acid on the neuronal behavior.
- the rat was orally anesthetized with 5% isoflurane gas (mixed gas with the gas mixture consisting of 70% N O and 30% O gas and 5% isoflurane) and maintained with 5% isoflurane gas during experiment.
- 5% isoflurane gas mixed gas with the gas mixture consisting of 70% N O and 30% O gas and 5% isoflurane
- ECA was ligated at the point that about 20 mm of coated probe was inserted to reach at 20mm or the less from the inserting point and the resistance was felt.
- the probe was fixed at the same time preventing regurgitation.
- the skin excision area was sealed again and the rat was restored from anesthetized status naturally. Since inserted probe obstruct the blood flow of MCA, the regional ischemia was induced and the rat was re-anesthetized to remove the probe restoring carotid blood flow after 2 hour. 24 hours after reperfusion, the rat was killed to cervical dislocation to deliver brain and the brain tissue was examined by microscope sectioned 2mm thickness then stained by 2% TTC solution.
- the volume of cerebral infarction region was calculated by the OPTIMAS program (Media Cybernetics Co., 6.51 version) and analyzed by image analysis system. To determine the exact volume of cerebral infarction region of right hemisphere excluding edema volume (A), the real volume of cerebral infarction (B) was calculated by following Empirical Formula 1 and 2.
- the infract volume ⁇ %) correlated infarct volume (mm ⁇ / total volume (mi ' ) of none damaged hemisphere (WI) x 100
- test group treated with various oleic acid (B: lmg/kg, C: 10mg/kg, D:
- Fig. 1 100mg/kg showed smaller staining area with TTC (white) due to little damage of neuronal cell than control group as can be seen in Fig. 1.
- Fig.2 the volume percentage of total infarct hemisphere tissue of control group showed 37.1 4.34%.
- the test group C and D showed more potent protective effect on neuronal cell death than control group by 32.9% (20.9 3.48 %) and 64.9% (13.0 2.79 % ) respectively in a dose-dependent manner.
- the recovery score was counted by following standard in case the white rat was lifted to about 50 cm higher from the bottom: the fore-rat paw were directed toward the bottom (score 5): the injured rat paw were bounded and without other symptom (score 4); the paw were completely bounded (score 3); the paw were twitched to the left (score 2); and the rat was turned to the left (score 1).
- the final neurological score of respective group was calculated by summing up total score of respective group in accordance with the above-described evaluation method as shown in Fig. 3.
- the test group intraperitoneally treated with 100mg/kg of oleic acid showed higher score (3.95 0.15 %; p ⁇ 0.001) than control group (2.86 0.21).
- Dawley rats 300+1Og, Jung-Ang Lab Animal Inc. were performed using the oleic acid of the Example 1.
- Four group consisting of 10 mice or rats was administrated orally with 100mg/kg, 250mg/kg, 500mg/kg and 1000mg/kg of test sample or solvents (0.2 D, i.p.) respectively and observed for 2 weeks.
- mice and rats were administered intraperitoneally with 25mg/kg, 50mg/kg, 100mg/kg and 200mg/kg of test sample or solvents (0.2 D, i.p.), respectively and observed for 24 hours.
- composition comprising oleic acid according to the present invention shows protective effect of neuronal cell and preventing or treating effect of brain stroke and cerebral ischemia. Therefore, it is useful in the prevention or treatment of degenerative brain diseases in human or mammal.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
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- Urology & Nephrology (AREA)
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- Hospice & Palliative Care (AREA)
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008526859A JP4993515B2 (en) | 2005-08-19 | 2006-01-09 | Oleic acid-containing composition and use thereof |
US12/064,134 US8193245B2 (en) | 2005-08-19 | 2006-01-09 | Composition comprising oleic acid and the use thereof |
CN2006800302217A CN101242823B (en) | 2005-08-19 | 2006-01-09 | Composition comprising oleic acid and the use thereof |
EP06700089.3A EP1915142B1 (en) | 2005-08-19 | 2006-01-09 | Oleic acid for the treatment of brain stroke or cerebral ischemia |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020050076324A KR100756890B1 (en) | 2005-08-19 | 2005-08-19 | Composition comprising oleic acid having neuronal cell-protecting activity for preventing and treating the degenerative brain disease |
KR10-2005-0076324 | 2005-08-19 |
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Publication Number | Publication Date |
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WO2007021061A1 true WO2007021061A1 (en) | 2007-02-22 |
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PCT/KR2006/000082 WO2007021061A1 (en) | 2005-08-19 | 2006-01-09 | Composition comprising oleic acid and the use thereof |
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US (1) | US8193245B2 (en) |
EP (1) | EP1915142B1 (en) |
JP (1) | JP4993515B2 (en) |
KR (1) | KR100756890B1 (en) |
CN (1) | CN101242823B (en) |
WO (1) | WO2007021061A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITMI20111284A1 (en) * | 2011-07-11 | 2013-01-12 | Giovanni Nusca | PHARMACEUTICAL COMPOSITION. |
EP2842556A3 (en) * | 2008-12-09 | 2015-08-05 | Universitat de les Illes Balears | Alpha-derivatives of cis-monounsaturated fatty acids for use as medicines |
EP2987493A4 (en) * | 2013-04-17 | 2016-12-21 | Univ-Industry Coop Group Of Kyung Hee Univ | Composition for preventing or treating stroke or degenerative brain disease |
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CN109125311A (en) * | 2018-06-26 | 2019-01-04 | 东南大学 | The pharmaceutical composition and its application of prevention or treatment Alzheimer's disease |
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JP2900580B2 (en) * | 1990-10-29 | 1999-06-02 | 日本油脂株式会社 | Reactive oxygen disorder protective agent |
JPH10215787A (en) * | 1997-02-10 | 1998-08-18 | Sagami Chem Res Center | Production method for oleic acid reinforced animal food and oleic acid reinforced animal food |
US7025984B1 (en) * | 2000-06-26 | 2006-04-11 | The Procter & Gamble Company | Compositions and methods for body weight management |
GB2368521B (en) * | 2000-10-31 | 2004-12-08 | Jasali Ltd | Pharmaceutical or dietary composition containing a vegetable oil in particular olive oil and sitosterol |
KR100502835B1 (en) * | 2001-05-23 | 2005-07-20 | 전길자 | Compositions comprising extract of ganoderma lucidum, oleamide and its structural analogue as an effective component for preventing or treating dementia |
JP4388322B2 (en) * | 2003-07-31 | 2009-12-24 | 花王株式会社 | Apolipoprotein D degradation inhibitor |
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EP2842556A3 (en) * | 2008-12-09 | 2015-08-05 | Universitat de les Illes Balears | Alpha-derivatives of cis-monounsaturated fatty acids for use as medicines |
US10588883B2 (en) | 2008-12-09 | 2020-03-17 | Universitat De Les Illes Balears | Alpha-derivatives of cis-monounsaturated fatty acids for use as medicines |
ITMI20111284A1 (en) * | 2011-07-11 | 2013-01-12 | Giovanni Nusca | PHARMACEUTICAL COMPOSITION. |
EP2987493A4 (en) * | 2013-04-17 | 2016-12-21 | Univ-Industry Coop Group Of Kyung Hee Univ | Composition for preventing or treating stroke or degenerative brain disease |
US11617774B2 (en) | 2013-04-17 | 2023-04-04 | University-Industry Cooperation Group Of Kyung Hee University | Composition for preventing or treating stroke or degenerative brain disease |
Also Published As
Publication number | Publication date |
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US20080227860A1 (en) | 2008-09-18 |
CN101242823A (en) | 2008-08-13 |
KR100756890B1 (en) | 2007-09-07 |
EP1915142A1 (en) | 2008-04-30 |
JP4993515B2 (en) | 2012-08-08 |
JP2009504725A (en) | 2009-02-05 |
EP1915142B1 (en) | 2017-01-25 |
CN101242823B (en) | 2012-01-25 |
US8193245B2 (en) | 2012-06-05 |
EP1915142A4 (en) | 2009-12-16 |
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