WO2021177660A1 - Weight loss composition comprising oenothein b analogues as active ingredient - Google Patents
Weight loss composition comprising oenothein b analogues as active ingredient Download PDFInfo
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- WO2021177660A1 WO2021177660A1 PCT/KR2021/002392 KR2021002392W WO2021177660A1 WO 2021177660 A1 WO2021177660 A1 WO 2021177660A1 KR 2021002392 W KR2021002392 W KR 2021002392W WO 2021177660 A1 WO2021177660 A1 WO 2021177660A1
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- obesity
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Images
Classifications
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/163—Sugars; Polysaccharides
-
- 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
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- 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
- A61K31/7024—Esters of saccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A23V2200/332—Promoters of weight control and weight loss
Definitions
- the present invention relates to a composition
- a composition comprising an oenotein B analogue as an active ingredient, which has an effect on anti-obesity or weight loss, more preferably, body fat loss, and a use thereof.
- Obesity refers to a state of excessive accumulation of adipose tissue, but excessive accumulation of adipose tissue increases the risk of metabolic syndrome such as hypertension and diabetes, and is also associated with the occurrence of cardiovascular diseases.
- oriental medicine clinics treat not only general obesity but also partial obesity through prescription-based herbal medicine therapy, acupuncture treatment, acupuncture electrostimulation therapy, and medicinal acupuncture treatment. .
- the effect of obesity treatment can be reliably obtained without side effects, and obesity treatment methods or novel anti-obesity methods that can be conveniently applied without special effort.
- An object of the present invention is to provide a pharmaceutical composition for treating or preventing obesity, complications of obesity, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof as an active ingredient.
- Another object to be solved by the present invention is to provide a food composition for improving obesity, weight loss, or weight loss, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
- Another object to be solved by the present invention is to provide an animal feed composition for alleviating or preventing obesity, obesity complications, or both, including an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
- Another object to be solved by the present invention is to provide a low-fat-containing livestock feed composition comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
- the present invention provides a pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof as an active ingredient.
- the pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both may be to reduce the amount of body fat.
- the composition may reduce the amount of one or more fats selected from abdominal fat, visceral fat, intramuscular fat, and blood fat.
- the present invention provides a food composition for improving obesity, weight loss, or reducing body fat, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
- the food composition may be a health functional food, but is not limited thereto.
- the present invention provides an animal feed composition for alleviating or preventing obesity, obesity complications, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
- the animal may be one or more animals selected from mammals and birds.
- the present invention provides a low-fat-containing livestock feed composition
- a low-fat-containing livestock feed composition comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
- composition comprising an oenotein B analogue compound or a pharmaceutically acceptable salt thereof according to the present invention exhibited an effective weight loss effect in normal or obese animal models, and the weight loss can reduce fat without loss of muscle mass. Since it did not show side effects such as dehydration symptoms, stress, decreased physical strength or toxicity even after weight loss, it is used for weight loss, body fat loss, obesity treatment, improvement or prevention for pharmaceutical compositions, food compositions, feed compositions, etc. can be usefully applied.
- the composition comprising the oenotein B analogue compound or a pharmaceutically acceptable salt thereof according to the present invention is applied to the livestock industry, the fat content can be reduced in edible livestock such as broilers in which the fat layer accumulated in the muscle is a problem, useful as
- the present invention confirmed the pharmacological effect of an oenotein B analogue compound or a pharmaceutically acceptable salt thereof on anti-obesity. was completed.
- the present invention provides a pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof as an active ingredient.
- the term "obesity complications” refers to various diseases having a prevalence due to excessive accumulation of fat, and the complications include metabolic syndromes such as hypertension, diabetes, and hyperlipidemia. Also included are herniated discs, osteoarthritis (eg, osteoarthritis of the ankle, knee joint, hip joint, etc.). Also included are gastroesophageal reflux disease, hernia, and stress incontinence due to abdominal obesity. Also included are sleep apnea and nonalcoholic fatty liver disease, which is caused by a decrease in the space in the throat due to obesity. Also included are cardiovascular diseases such as angina pectoris, myocardial infarction, and heart failure. Also included are cerebrovascular diseases such as stroke and cerebral infarction.
- a decrease in neurological function due to an increase in oxidative stress is included.
- various diseases such as early onset of menstruation, ovulation disorder, luteal phase defect, postmenopausal health, precocious puberty, menstrual irregularity, infertility, polycystic ovary syndrome and female hormone-dependent cancer caused by an increase in female hormones due to excessive body fat in women Included.
- the obesity complication is hypertension; diabetes; hyperlipidemia;
- the oenotein of the present invention has four benzoic acids attached to glucose as a basic monomer, and oenoteins A, B, C, D, F, and G exist, which are structurally very similar and In the present invention, it is included in the term “oenotein B analog” (Phytochemistry 40:555-561, 1995).
- Oenotein B (CAS# 104987-36-2) is a dimeric ellagitannin composed of C68H48O44 having a molecular weight of 1569.08. It was first discovered in the leaves of Oenothera erythrosepala (J. Chem. Soc. Perkin Trans. 1, 2735-2743, 1990), may be represented by the following formula (3).
- the oenotein B analog is a monomer or dimer compound of a compound represented by the following formula (1); or a pharmaceutically acceptable salt thereof:
- R 2 is (CH 2 ) n , where n is an integer from 1 to 6,
- R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,
- R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano to the furnace, halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, phenylmethoxy, etc. Any one selected from the group consisting of,
- R 7 and R 8 are —OH.
- R 7 and R 8 are condensed with R 4 , respectively.
- R 7 and R 8 and R 4 and each condensation may be connected to any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) p -, where p is an integer from 1 to 6.
- dimer compound of the compound of Formula 1 it may be a compound represented by the following Formula 2 or a pharmaceutically acceptable salt thereof:
- R 2 is (CH 2 ) n , where n is an integer from 1 to 6,
- R 3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,
- R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano to the furnace, halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, phenylmethoxy, etc. Any one selected from the group consisting of, and
- R 7 ' and R 8 ' are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6.
- the compound according to the present invention may be a compound represented by the following formula (3) or a pharmaceutically acceptable salt thereof:
- pharmaceutically acceptable salts refer to salts commonly used in the pharmaceutical industry, for example, inorganic ionic salts prepared from calcium, potassium, sodium and magnesium, hydrochloric acid, nitric acid, phosphoric acid, hydrobromic acid, and iodine.
- Inorganic acid perchloric acid, tartaric acid and sulfuric acid, acetic acid, trifluoroacetic acid, citric acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, manderic acid, propionic acid, citric acid, lactic acid, glycolic acid, gluconic acid , galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, carbonic acid, vanillic acid, hydroiodic acid, etc.
- organic acid salts methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p -There are sulfonic acid salts prepared from toluenesulfonic acid and naphthalenesulfonic acid, amino acid salts prepared from glycine, arginine, lysine, etc., and amine salts prepared from trimethylamine, triethylamine, ammonia, pyridine, picoline, etc. The types of salts in the present invention are not limited by these listed salts.
- the composition may be to treat or prevent obesity by reducing the amount of body fat.
- the composition may treat or prevent obesity, obesity complications, or both by reducing the amount of one or more fats selected from abdominal fat, visceral fat, intramuscular fat, and blood fat.
- Abdominal obesity or visceral obesity is a symptom of the accumulation of fat in the subcutaneous or internal organs of the abdomen and is known to accompany various complications.
- the composition according to the present invention can also be used for the treatment or prevention of the above-mentioned complications of obesity.
- composition according to the present invention can selectively reduce fat without loss of muscle mass, and has very low cytotoxicity, so it is effective in treating or preventing obesity, obesity complications, or both.
- composition according to the present invention has excellent effects in that it reduces the content of neutral triglycerides and lipids without toxicity in the human body, and exhibits a weight loss effect and an effect on reducing abdominal fat.
- the term "treatment” refers to both the action of alleviating the symptoms caused by obesity and obesity complications by administering the composition, and the disease, the symptoms of the disease, the secondary disease of the disease or disease, or To a subject (human or animal) having a disease, a symptom of a disease, a secondary disease of the disease or disorder, or a predisposition thereto, for the purpose of treating, alleviating, alleviating, remedying, or ameliorating the predisposition It is defined as the application or administration of the composition.
- the pharmaceutical composition of the present invention may contain 0.01 to 95% by weight, preferably 1 to 80% by weight of the oenotein B analog compound or a pharmaceutically acceptable salt thereof, based on the total weight of the composition.
- the oenotein B analog compound or a pharmaceutically acceptable salt thereof is mixed with a conventional carrier, adjuvant or diluent and formulated in a conventional formulation method for oral or parenteral administration. It can be prepared in any suitable form.
- the carrier, adjuvant or diluent may include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, poly vinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.
- conventional fillers, extenders, binders, wetting agents, disintegrants, surfactants, etc. may be further included, and lubricants such as magnesium stearate and talc may be further added.
- oral administration it may be prepared in the form of tablets, capsules, solutions, syrups, suspensions, etc.
- parenteral administration it is suitable for intravenous, intrauterine, intraperitoneal, subcutaneous, intramuscular, transdermal and intracerebrovascular injection. It can be prepared in the form of an injection for
- the pharmaceutical composition of the present invention is an amount of an active ingredient or pharmaceutical composition that induces a biological or medical response in a tissue system, animal or human as considered by a researcher, veterinarian, physician or other clinician, that is, the amount of the symptom of the disease or disorder being treated. It can be administered in a therapeutically effective amount, which is an amount that induces remission. It is apparent to those skilled in the art that the therapeutically effective dosage and frequency of administration for the pharmaceutical composition of the present invention will vary depending on the desired effect.
- the optimal dosage to be administered can be easily determined by those skilled in the art, and the type of disease, the severity of the disease, the content of active ingredients and other ingredients contained in the composition, the type of formulation, the age, weight, and general health of the patient , sex and diet, administration time, administration route and secretion rate of the composition, treatment period, and various factors including concurrently used drugs.
- the pharmaceutical composition of the present invention may be administered to an individual by various routes. For example, intravenous, intraperitoneal, intramuscular, intraarterial, buccal, intracardiac, intramedullary, intrathecal, transdermal, enteral, subcutaneous, sublingual or topical administration may be administered, but not limited thereto.
- the pharmaceutical composition of the present invention may be administered in an amount of 1 to 10,000 mg/kg/day, preferably 1 to 200 mg/kg/day, and may be administered once a day or divided into several administrations .
- Another object to be solved by the present invention is to provide a food composition for improving obesity, weight loss or body fat loss, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
- the present invention provides a food composition for improving obesity or reducing body fat containing oenotein B.
- the food composition of the present invention can be used as a health functional food.
- health functional food means a food manufactured and processed using raw materials or ingredients useful for the human body in accordance with the Health Functional Food Act, and "functionality” refers to the structure and function of the human body. It refers to ingestion for the purpose of obtaining useful effects for health purposes such as regulating nutrients or physiological effects.
- the food composition of the present invention may contain conventional food additives, and the suitability as the "food additive” is determined according to the general rules and general test methods of food additives approved by the Ministry of Food and Drug Safety, unless otherwise specified. It is judged according to the standards and standards related to the item.
- Food Additives Code include, for example, chemical compounds such as ketones, glycine, potassium citrate, nicotinic acid, and cinnamic acid; Mixed preparations such as sodium L-glutamate preparation, noodle-added alkali agent, preservative agent, and tar color agent can be mentioned.
- the food composition of the present invention may contain 0.01 to 95% by weight, preferably 1 to 80% by weight of the oenotein B analog compound or a pharmaceutically acceptable salt thereof, based on the total weight of the composition.
- the food composition of the present invention can be manufactured and processed in the form of tablets, capsules, powders, granules, liquids, pills, etc. for the purpose of improving obesity, weight loss or body fat loss.
- the health functional food in the form of tablets is granulated with a mixture of oenotein B analogs, excipients, binders, disintegrants, and other additives in a conventional manner, and then compression-molded by adding a lubricant, etc.;
- the mixture can be directly compression molded.
- the health functional food in the form of tablets may contain a mating agent, etc., if necessary, and may be coated with a suitable skinning agent if necessary.
- hard capsules can be prepared by filling conventional hard capsules with a mixture of oenotein B analogues and additives such as excipients, or granules thereof or coated granules. can be prepared by filling a mixture of an oenotein B analogue and an additive such as an excipient into a capsule base such as gelatin.
- the soft capsule formulation may contain a plasticizer such as glycerin or sorbitol, a colorant, a preservative, and the like, if necessary.
- a health functional food in the form of a ring can be prepared by molding a mixture of oenotein B analogues, excipients, binders, disintegrants, etc. in an appropriate way, and if necessary, the skin is coated with sucrose or other suitable skinning agent, or starch, talc, or You can also dress the gown with a suitable material.
- a health functional food in granular form may be prepared in a granular form by a suitable method of a mixture of oenotein B analogues, excipients, binders, disintegrants, etc., and may contain flavoring agents, flavoring agents, etc. as needed.
- For health functional foods in granular form use No. 12 (1680 ⁇ m), No. 14 (1410 ⁇ m) and No. 45 (350 ⁇ m) sieves to pass all the sieves No. 12 and the remaining in No. 14 sieves in the next particle size test. 5.0% or less and passing through No. 45 may be less than 15.0% of the total amount.
- Examples of foods to which the oenotein B analogue of the present invention can be added include beverages, gums, vitamin complexes, drinks, and the like, and include all health functional foods in a conventional sense.
- the food composition may contain food supplement additives, and the food products include, for example, beverages, gum, tea, vitamin complexes, health supplements, etc., capsules, tablets, powders, granules, liquids, pills, slices, pastes. It can be used in the form of phases, syrups, gels, beverages, jellies or vines.
- the content of the oenotein B analogue may be contained in an amount of 0.01 to 15% by weight based on the total weight of the health functional food, and in the case of a health beverage composition, 0.02 to 10 g, preferably 0.3 to 1, based on a total of 100 g g may contain.
- the food supplement additives include food additives conventional in the art, for example, flavoring agents, flavoring agents, coloring agents, fillers, stabilizers, and the like.
- the health drink composition is an essential ingredient in the indicated ratio, and there is no particular limitation on the ingredients added other than the oenotein B analog, and it can contain various flavoring agents or natural carbohydrates as additional ingredients like conventional beverages.
- the natural carbohydrate include monosaccharides such as glucose, fructose and the like; disaccharides such as maltose, sucrose and the like; polysaccharides such as dextrins, cyclodextrins; and sugar alcohols such as xylitol, sorbitol, and erythritol.
- natural flavoring agents taumatin, stevia extract (eg rebaudioside A, glycyrrhizin, etc.)
- synthetic flavoring agents sacharin, aspartame, etc.
- food compositions, diet supplements, or health functional foods containing an oenotein B analogue compound or a pharmaceutically acceptable salt thereof include various nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors. Flavoring, coloring and thickening agents (cheese, chocolate, etc.), pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, carbonates used in carbonated beverages It may contain topics and the like.
- the present invention provides an animal feed composition for improving or preventing obesity and obesity complications, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
- the animal may be one or more selected from mammals and birds, and preferably, the wild habits defined in Article 2, No. 1 of the Livestock Livestock Act and Article 2 of the Enforcement Rule of the same Act, and are suitable for breeding. And it can be a livestock that can contribute to the income increase of the farmhouse.
- the livestock may be cattle, horses, mules, donkeys, goats, goats, sheep, deer, pigs, rabbits, poultry, etc., and poultry includes chickens, turkeys, ducks, ostriches, geese, quails, etc., preferably chickens, If it is suitable for breeding and obtaining livestock products, it is not limited thereto.
- livestock products are meat, milk, eggs, honey and their processed products, raw hides (including raw fur), raw wool, and other livestock products, which are defined by Article 2, 3 of the Livestock Act, as determined by the Ordinance of the Ministry of Agriculture and Forestry. means that In addition, it may be a dog, a cat, etc., including companion animals, but is not limited thereto.
- feed in the present invention means any natural or artificial diet, meal, etc., or a component of said meal, intended for or suitable for being eaten, consumed, and digested by an animal.
- the composition for feed containing the oenotein B analog compound of the present invention or a pharmaceutically acceptable salt thereof may include a concentrated feed, forage and/or special feed.
- seed fruits containing grains such as wheat, oats, and corn, bran containing rice bran, bran, barley bran, etc.
- Fish-soluble, meat powder which is a condensed product of fish meal, fish waste, and fresh liquid obtained from fish meal, fish waste, fish meal, fish meal , animal feed such as dried whey, yeast, chlorella, seaweed, etc., blood meal, feather meal, skim milk powder, cheese from milk, and whey, which is the remainder of the production of casein from skim milk.
- silage which is a stored feed fermented with lactic acid after being filled, wild grasses, hay obtained by cutting and drying grass, straw for breeding crops, and leaves from legumes.
- Special feed includes mineral feed such as oyster shells and rock salt, urea feed such as urea or its derivative diureide isobutane, supplementing ingredients that are easily lacking when only natural feed ingredients are blended, or added to formulated feed to increase feed storage.
- feed additives which are substances added in trace amounts.
- the present invention provides a low-fat-containing livestock feed composition
- a low-fat-containing livestock feed composition comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
- the oenotein B analog can be usefully applied as an additive to a low-fat-containing livestock fattening feed composition because it reduces the body fat content without loss of muscle mass.
- the present invention provides the use of an oenotein B analog compound represented by Formula 1 or Formula 2, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment of obesity, obesity complications, or both.
- the present invention relates to obesity, obesity complications, Methods for preventing or treating all of these are provided.
- the term "subject" may refer to all animals, including humans, that have or are likely to develop obesity or obesity complications.
- the animal may be a mammal, such as a cow, a horse, a sheep, a pig, a goat, a camel, an antelope, a dog, or a cat, in need of treatment for symptoms similar to those of humans as well as humans. It may also refer to animals other than humans, but is not limited thereto.
- the prevention or treatment method of the present invention may include administering the composition in a pharmaceutically effective amount to an individual who has developed or is at risk of developing obesity or obesity complications.
- the present invention provides a composition comprising an oenotein B analogue compound represented by Formula 1 or Formula 2 or a pharmaceutically acceptable salt thereof for use in the treatment of obesity, obesity complications, or both.
- the definition of the oenotein B analog compound represented by Formula 1 or Formula 2, a pharmaceutically acceptable salt thereof, obesity or obesity complications is as described above.
- reagents and solvents mentioned below were purchased from Sigma-Aldrich, TCI or Alfa aesar, unless otherwise specified, and HPLC grade was used.
- Test Example 1 Weight loss effect of oenotein B in a normal-weight animal model
- Oenotein B was dissolved in sterile distilled water to prepare a solution of 20 mg/mL. After diluting the prepared solution 20-fold with saline, 200 ⁇ L of oenotein B (1 mg/mL) was injected into the abdominal cavity of C57BL6/J mice with an average age of 13 weeks using a 1cc syringe on days 1 and 3 of the experiment. The injections were made at intervals of time, and body weight changes were measured daily for 5 days after injection, starting one day before the injection of oenotein B solution. Distilled water was used as a control, and normal feed and water with a fat content of 15% were provided during the experiment.
- FIG. 1 shows a graph showing the weight loss effect of oenotein B.
- Arrows indicate the time of injection of oenotein B. After the first injection of oenotein B, a weight loss effect was observed, and 1.5 to 8.5% of body weight was lost after the first injection, and 1.5 to 6% of body weight was lost after the second injection.
- Test Example 2 Weight loss effect of oenotein B in obese animal model
- the weight loss effect of oenotein B in an obese animal model was confirmed using overweight-induced mice.
- C57BL/6J mice with an average age of 12 weeks were fed after changing the normal diet (fat content 15%) to a high-fat diet containing 45% fat, and the change in body weight was measured daily.
- 200 ⁇ L of oenotein B (1 mg/mL) was injected into the abdominal cavity of the mice, and body weight changes were measured every day until the 27th day, and the control group was injected with distilled water.
- Test Example 3 Weight loss effect of oenotein B in obese animal model
- mice administered oenotein B compared to the control group, it was confirmed that the average abdominal fat was reduced by about 44%.
- Oil red O is a dye used to stain neutral triglycerides and lipids.
- A549 cells a cell line obtained from human lung cancer tissue, were mixed with 10% fetal bovine serum in RPMI-1640 medium and cultured at 37° C. and 5% CO 2 conditions.
- lactate dehydrogenase (LDH) release assay was performed to quantitatively measure cytotoxicity, and the results are shown in FIG. 5 .
- Hydrogen peroxide was used as a positive control, and phosphate-buffered saline was used as a negative control.
- the composition comprising the oenotein B analog according to the present invention is a pharmaceutical composition, a food composition for weight loss, treatment, prevention or improvement of obesity and obesity complications, in particular, health for weight loss or body fat loss It can be usefully applied as a functional food, a feed composition, and further can be usefully used as a feed composition for fattening livestock containing low fat.
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Abstract
The present invention relates to a pharmaceutical composition for treating or preventing obesity and/or obesity complications, and a food composition or a feed composition for obesity prevention, weight loss, or fat loss, all of which comprise oenothein B analogues.
Description
본 발명은 오에노테인 B 유사체를 유효성분으로 포함하는 항비만 또는 체중 감량, 보다 바람직하게는 체지방 감량에 효과를 나타내는 조성물 및 이의 용도에 관한 것이다.The present invention relates to a composition comprising an oenotein B analogue as an active ingredient, which has an effect on anti-obesity or weight loss, more preferably, body fat loss, and a use thereof.
전 세계적으로 고지방, 고열량 식이의 증가 및 비활동적인 생활양식으로 인해 과체중과 비만이 급속히 증가하고 있으며, 이러한 과체중과 비만은 유병률과 사망률을 높이는 위험 인자로 작용하고 있다. 비만은 지방 조직의 과잉 축적 상태를 의미하지만, 지방 조직의 과잉 축적은 고혈압, 당뇨병 등의 대사 증후군의 발생 위험을 높이고, 심혈관 질환의 발생과도 관련이 있다. Overweight and obesity are rapidly increasing worldwide due to an increase in high-fat, high-calorie diets and inactive lifestyles, and these overweight and obesity are risk factors that increase morbidity and mortality. Obesity refers to a state of excessive accumulation of adipose tissue, but excessive accumulation of adipose tissue increases the risk of metabolic syndrome such as hypertension and diabetes, and is also associated with the occurrence of cardiovascular diseases.
최근, 이러한 대사 장애뿐 아니라 산화 스트레스의 증가가 신경학적인 기능 저하와 종양 발생의 위험도를 높이는 것이 알려졌다. 특히, 여성의 체지방 과다는 혈중 고안드로겐 상태를 유도하고, 여성 호르몬 증가는 초경의 이른 개시, 배란 장애, 황체기 결함, 폐경 후 건강도에 영향을 주며, 성 조숙증, 생리불순, 불임, 다낭성난소증후군 및 여성 호르몬 의존성 암등 다양한 질환의 위험성을 높일 수 있다.Recently, it has been known that an increase in oxidative stress as well as these metabolic disorders increases the risk of neurological dysfunction and tumor development. In particular, excess body fat in women induces high androgen levels in the blood, and increase in female hormones affects early onset of menstruation, ovulation disorders, luteal phase defects, postmenopausal health, and precocious puberty, menstrual irregularities, infertility, and polycystic ovary syndrome. And it can increase the risk of various diseases such as female hormone-dependent cancer.
비만에 대한 관심이 높아지면서 비만을 치료하기 위한 다양한 운동요법, 식이요법, 약물요법, 수술요법 등이 제안되었다. 운동을 통한 체중 감소는 부작용이 없는 가장 효과적인 방법으로 알려져 있으나 바쁜 현대 생활에서 비만 치료에 충분한 정도의 운동을 규칙적으로 장기간 행하는 것은 매우 어려운 일이다. 각종 식품을 주의 깊게 선택하여 준비하여야 하는 식이요법을 이용한 비만의 치료 또한 최소 몇 달에 걸친 장기간 복용을 인내심을 가지고 행하기가 어렵다는 단점이 있다. 다른 방법으로는 약물요법이 있는데, 이 또한 장기간에 걸쳐 투여해야 효과가 약간 나타나거나 약물에 따라서는 약제 내성이 생겨 비만치료에 적합하지 않은 경우도 있다. 한편, 한방병의원에서는 처방을 위주로 하는 한약요법, 침치료, 침 전기자극요법 및 약침 치료 등을 통해 전신 비만 뿐만 아니라, 부분 비만 치료를 시술하기도 하나, 침치료에 대해 두려움 또는 거부감을 느끼는 경우도 있다. 비만 치료에 사용되는 종래의 방법들의 단점 또는 어려움을 고려할 때, 부작용이 없이 비만치료의 효과를 확실하게 얻을 수 있으며, 특단의 노력을 기울일 필요 없이 간편하게 적용할 수 있는 비만 치료 방법 또는 신규한 항비만 활성성분의 개발이 필요한 실정이다.As interest in obesity increases, various exercise therapy, diet, drug therapy, and surgery therapy have been proposed to treat obesity. Weight loss through exercise is known to be the most effective method without side effects, but it is very difficult to regularly and long-term exercise sufficient to treat obesity in a busy modern life. The treatment of obesity using a diet that requires careful selection and preparation of various foods also has a disadvantage in that it is difficult to carry out long-term use for at least several months with patience. Another method is drug therapy, which also needs to be administered for a long period of time to have some effect or, depending on the drug, drug resistance may develop, which is not suitable for obesity treatment. On the other hand, oriental medicine clinics treat not only general obesity but also partial obesity through prescription-based herbal medicine therapy, acupuncture treatment, acupuncture electrostimulation therapy, and medicinal acupuncture treatment. . Considering the disadvantages or difficulties of conventional methods used to treat obesity, the effect of obesity treatment can be reliably obtained without side effects, and obesity treatment methods or novel anti-obesity methods that can be conveniently applied without special effort There is a need to develop active ingredients.
[선행기술문헌][Prior art literature]
[특허문헌][Patent Literature]
KR 10-2014-0021401KR 10-2014-0021401
KR 10-2018-7001716KR 10-2018-7001716
본 발명이 해결하고자 하는 과제는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 유효성분으로 포함하는 비만, 비만 합병증 또는 이들 모두의 치료 또는 예방용 약학적 조성물을 제공하는 것이다. SUMMARY OF THE INVENTION An object of the present invention is to provide a pharmaceutical composition for treating or preventing obesity, complications of obesity, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof as an active ingredient.
본 발명이 해결하고자 하는 다른 과제는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만 개선, 체중 감량 또는 체지방 감량용 식품 조성물을 제공하는 것이다.Another object to be solved by the present invention is to provide a food composition for improving obesity, weight loss, or weight loss, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
본 발명이 해결하고자 하는 또 다른 과제는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만, 비만 합병증 또는 이들 모두의 개선 또는 예방용 동물 사료 조성물을 제공하는 것이다.Another object to be solved by the present invention is to provide an animal feed composition for alleviating or preventing obesity, obesity complications, or both, including an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
본 발명이 해결하고자 하는 또 다른 과제는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 저지방 함유 가축 비육용 사료 조성물을 제공하는 것이다.Another object to be solved by the present invention is to provide a low-fat-containing livestock feed composition comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
상기한 과제를 해결하기 위해 본 발명은 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 유효성분으로 포함하는 비만, 비만 합병증 또는 이들 모두의 치료 또는 예방용 약학적 조성물을 제공한다. In order to solve the above problems, the present invention provides a pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof as an active ingredient.
본 발명에 있어서, 상기 비만, 비만 합병증 또는 이들 모두의 치료 또는 예방용 약학적 조성물은 체내 지방량을 감소시키는 것일 수 있다. In the present invention, the pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both may be to reduce the amount of body fat.
본 발명에 있어서, 상기 조성물은 복부 지방, 내장 지방, 근육 내 지방 및 혈중 지방 중에서 선택되는 하나 이상의 지방량을 감소시키는 것일 수 있다. In the present invention, the composition may reduce the amount of one or more fats selected from abdominal fat, visceral fat, intramuscular fat, and blood fat.
또한, 본 발명은 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만 개선, 체중 감량 또는 체지방 감량용 식품 조성물을 제공한다. In addition, the present invention provides a food composition for improving obesity, weight loss, or reducing body fat, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
본 발명에 있어서, 상기 식품 조성물은 건강기능식품일 수 있으나 이에 한정되는 것은 아니다.In the present invention, the food composition may be a health functional food, but is not limited thereto.
또한, 본 발명은 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만, 비만 합병증 또는 이들 모두의 개선 또는 예방용 동물 사료 조성물을 제공한다. In addition, the present invention provides an animal feed composition for alleviating or preventing obesity, obesity complications, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
본 발명에 있어서, 상기 동물은 포유동물 및 조류 중에서 선택되는 하나 이상의 동물일 수 있다. In the present invention, the animal may be one or more animals selected from mammals and birds.
또한, 본 발명은 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 저지방 함유 가축 비육용 사료 조성물을 제공한다.In addition, the present invention provides a low-fat-containing livestock feed composition comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
본 발명에 따른 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 조성물은 정상 또는 비만 동물 모델에서 효과적인 체중감량 효과를 나타내었으며, 상기 체중감량은 근육량의 손실 없이, 지방을 감소시킬 수 있고, 체중 감량 후에도 탈수 증상, 스트레스, 체력 저하 또는 독성 등의 부작용을 나타내지 않았으므로, 체중 감량, 체지방 감량, 비만 치료, 개선 또는 예방을 위한 약학적 조성물, 식품조성물, 사료조성물 등의 용도로 유용하게 적용될 수 있다. 본 발명에 따른 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 조성물을 축산업에 적용시, 근육 내 축적된 지방층이 문제가 되는 육계 등의 식용 가축에서 지방 함량을 줄일 수 있어 산업적으로 유용하다.The composition comprising an oenotein B analogue compound or a pharmaceutically acceptable salt thereof according to the present invention exhibited an effective weight loss effect in normal or obese animal models, and the weight loss can reduce fat without loss of muscle mass. Since it did not show side effects such as dehydration symptoms, stress, decreased physical strength or toxicity even after weight loss, it is used for weight loss, body fat loss, obesity treatment, improvement or prevention for pharmaceutical compositions, food compositions, feed compositions, etc. can be usefully applied. When the composition comprising the oenotein B analogue compound or a pharmaceutically acceptable salt thereof according to the present invention is applied to the livestock industry, the fat content can be reduced in edible livestock such as broilers in which the fat layer accumulated in the muscle is a problem, useful as
도 1은 정상 체중 동물 모델에서 오에노테인 B 처리에 따른 체중 변화를 확인한 실험 결과이다. 1 is an experimental result confirming the change in body weight according to Oenotein B treatment in a normal-weight animal model.
도 2는 비만 동물 모델에서 오에노테인 B 처리에 따른 체중 변화를 확인한 실험 결과이다. 2 is an experimental result confirming the change in body weight according to Oenotein B treatment in an obese animal model.
도 3은 비만 동물 모델에서 오에노테인 B 처리에 따른 복부지방량 변화를 확인한 실험 결과이다. 3 is an experimental result confirming the change in abdominal fat mass according to Oenotein B treatment in an obese animal model.
도 4는 오에노테인 B 처리에 따른 지방감소를 여부를 검증하기 위해,
in vitro에서 3T3-L1 지방전구세포를 지방세포로 분화시킨 후, 다양한 농도의 오에노테인 B로 처리하고, Oil Red O로 염색하여 중성 트리글리세리드와 지질 함량 변화를 측정한 결과이다.4 shows 3T3-L1 preadipocytes in vitro differentiated into adipocytes, treated with various concentrations of Oenotein B, and Oil Red O It is the result of measuring the change in neutral triglyceride and lipid content by staining with
도 5는 오에노테인 B의 세포 독성 유무를 확인한 결과를 나타낸다.5 shows the results of confirming the presence or absence of cytotoxicity of oenotein B.
본 발명은 비만, 특히 체지방을 감량할 수 있는 신규한 천연물 유래 물질을 찾기 위해 예의 연구한 결과, 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염의 항비만에 대한 약리 효과를 확인함으로써 본 발명을 완성하게 되었다. As a result of intensive research to find a novel natural substance-derived substance capable of reducing obesity, particularly body fat, the present invention confirmed the pharmacological effect of an oenotein B analogue compound or a pharmaceutically acceptable salt thereof on anti-obesity. was completed.
이하, 본 발명을 보다 상세하게 설명한다. Hereinafter, the present invention will be described in more detail.
본 발명은 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 유효성분으로 포함하는 비만, 비만 합병증 또는 이들 모두의 치료 또는 예방용 약학적 조성물을 제공한다. The present invention provides a pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof as an active ingredient.
본 발명에 있어서, 용어 "비만 합병증"은 지방의 과잉 축적에 의해 유병률이 나타나는 다양한 질환을 의미하는 것으로, 상기 합병증에는 고혈압, 당뇨병, 고지혈증 등의 대사 증후군이 포함된다. 또한, 허리 디스크, 퇴행성 관절염(예컨대, 발목, 무릎 관절, 고관절 등에 대한 퇴행성 관절염)이 포함된다. 또한, 복부비만에 의한 역류성식도염, 탈장, 스트레스 요실금이 포함된다. 또한, 비만으로 목 안의 공간이 줄어들어 생기는 수면무호흡증이나 비알코올성지방간이 포함된다. 또한, 협심증, 심근경색, 심부전 등의 심혈관 질환이 포함된다. 또한, 뇌졸중, 뇌경색 등의 뇌혈관 질환이 포함된다. 또한, 산화 스트레스 증가에 따른 신경학적인 기능 저하가 포함된다. 또한, 여성의 체지방 과다에 의한 여성 호르몬 증가로 초래되는 초경의 이른 개시, 배란 장애, 황체기 결함, 폐경 후 건강도, 성 조숙증, 생리불순, 불임, 다낭성난소증후군 및 여성 호르몬 의존성 암 등 다양한 질환이 포함된다. 상기와 같이 비만이 원인이 되어 나타나는 다양한 합병증이 있으나, 이에 제한되는 것은 아니다.In the present invention, the term "obesity complications" refers to various diseases having a prevalence due to excessive accumulation of fat, and the complications include metabolic syndromes such as hypertension, diabetes, and hyperlipidemia. Also included are herniated discs, osteoarthritis (eg, osteoarthritis of the ankle, knee joint, hip joint, etc.). Also included are gastroesophageal reflux disease, hernia, and stress incontinence due to abdominal obesity. Also included are sleep apnea and nonalcoholic fatty liver disease, which is caused by a decrease in the space in the throat due to obesity. Also included are cardiovascular diseases such as angina pectoris, myocardial infarction, and heart failure. Also included are cerebrovascular diseases such as stroke and cerebral infarction. In addition, a decrease in neurological function due to an increase in oxidative stress is included. In addition, various diseases such as early onset of menstruation, ovulation disorder, luteal phase defect, postmenopausal health, precocious puberty, menstrual irregularity, infertility, polycystic ovary syndrome and female hormone-dependent cancer caused by an increase in female hormones due to excessive body fat in women Included. As described above, there are various complications appearing due to obesity, but is not limited thereto.
바람직하게 상기 비만 합병증은 고혈압; 당뇨병; 고지혈증; Preferably, the obesity complication is hypertension; diabetes; hyperlipidemia;
허리 디스크; 퇴행성 관절염; Herniated disc; degenerative arthritis;
복부 비만에 의한 역류성식도염, 탈장 또는 스트레스 요실금; reflux esophagitis, hernia or stress incontinence due to abdominal obesity;
수면무호흡증; 비알코올성지방간;sleep apnea; nonalcoholic fatty liver;
협심증; 심근경색; 심부전;angina pectoris; myocardial infarction; heart failure;
뇌졸중; 뇌경색;stroke; cerebral infarction;
여성의 체지방 과다에 의한 여성 호르몬 증가로 초래되는 이른 초경; 배란 장애; 성조숙증; 생리불순; 불임; 다낭성난소증후군 등을 포함할 수 있다. Early menarche caused by increased female hormones due to excess body fat in women; ovulation disorders; precocious puberty; irregular menstruation; sterility; polycystic ovary syndrome and the like.
본 발명의 오에노테인는 글루코스(glucose)에 안식향산(shikimic acid) 네 개가 붙은 것을 기본 monomer로 하며, 오에노테인 A, B, C, D, F, G가 존재하는데, 이들은 구조적으로 매우 유사하며 본 발명에 있어서, 용어 “오에노테인 B 유사체”에 포함된다(Phytochemistry 40:555-561, 1995). 오에노테인 B(CAS# 104987-36-2)는 1569.08의 분자량을 가지는 C68H48O44로 구성된 이량체 엘라지타닌(dimeric ellagitannin)으로 Oenothera erythrosepala의 잎에서 처음 발견되었으며(J. Chem. Soc. Perkin Trans. 1, 2735-2743, 1990), 하기 화학식 3으로 표기될 수 있다. 이후 Oenothera 속(Phytochem Anal. 23(6):582-587, 2012)이나 Epilobii angustifolli herba (J Chromatogr A. 1173(1-2):146-150, 2007)나 Eucalyptus globulus (Phytochem Anal. 24(2):162-170, 2013) 등의 여러 식물에서도 발견되었다. The oenotein of the present invention has four benzoic acids attached to glucose as a basic monomer, and oenoteins A, B, C, D, F, and G exist, which are structurally very similar and In the present invention, it is included in the term “oenotein B analog” (Phytochemistry 40:555-561, 1995). Oenotein B (CAS# 104987-36-2) is a dimeric ellagitannin composed of C68H48O44 having a molecular weight of 1569.08. It was first discovered in the leaves of Oenothera erythrosepala (J. Chem. Soc. Perkin Trans. 1, 2735-2743, 1990), may be represented by the following formula (3). Subsequently, the genus Oenothera (Phytochem Anal. 23(6):582-587, 2012) or Epilobii angustifolli herba (J Chromatogr A. 1173(1-2):146-150, 2007) or Eucalyptus globulus (Phytochem Anal. 24(2) ):162-170, 2013) were also found in several plants.
본 발명에 의하면, 오에노테인 B 유사체는 하기 화학식 1로 표시되는 화합물의 모노머 또는 다이머 화합물; 또는 이의 약제학적으로 허용가능한 염일 수 있다:According to the present invention, the oenotein B analog is a monomer or dimer compound of a compound represented by the following formula (1); or a pharmaceutically acceptable salt thereof:
[화학식 1][Formula 1]
R
1은 OH, CH
3, COOH, CHO, =O, NH
2 등으로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O, NH 2 and the like,
R
2는 (CH
2)
n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,
R3은 -O-, -CH
2- 및 -O(CH
2)
m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,
R
4, R
4', R
5 및 R
6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C
l-3)알킬, (C
l-
3)알케닐, (C
l-
3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C
l-
3)알콕시, (C
2-
4)아실옥시, (C
l-
3)카복사미노, 페녹시, 페닐메톡시 등으로 이루어진 군으로부터 선택되는 어느 하나이고, R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano to the furnace, halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, phenylmethoxy, etc. Any one selected from the group consisting of,
모노머인 경우 R
7 및 R
8은 -OH이다.In the case of a monomer, R 7 and R 8 are —OH.
본 발명에 의하면, 오에노테인 B 유사체가 상기 화학식 1로 표시되는 화합물의 다이머이면, R
7 및 R
8이 R
4와 각각 축합된다. 이러한 축합에 있어서, R
7 및 R
8이 R
4와 각각 축합은 -O-, -CH
2- 및 -O(CH
2)
p-로 이루어진 군으로부터 선택되는 어느 하나로 연결되는 것일 수 있고, 여기서 p는 1 내지 6의 정수이다. According to the present invention, if the oenotein B analogue is a dimer of the compound represented by the above formula (1), R 7 and R 8 are condensed with R 4 , respectively. In this condensation, R 7 and R 8 and R 4 and each condensation may be connected to any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) p -, where p is an integer from 1 to 6.
상기 화학식 1의 화합물의 다이머 화합물의 경우 하기 화학식 2로 표시되는 화합물 또는 이의 약제학적으로 허용가능한 염일 수 있다 : In the case of the dimer compound of the compound of Formula 1, it may be a compound represented by the following Formula 2 or a pharmaceutically acceptable salt thereof:
[화학식 2][Formula 2]
식 중에서,In the formula,
R
1은 OH, CH
3, COOH, CHO, =O, NH
2 등으로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O, NH 2 and the like,
R
2는 (CH
2)
n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,
R
3은 -O-, -CH
2- 및 -O(CH
2)
m-로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R 3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,
R
4, R
4', R
5 및 R
6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C
l-3)알킬, (C
l-
3)알케닐, (C
l-
3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C
l-
3)알콕시, (C
2-
4)아실옥시, (C
l-
3)카복사미노, 페녹시, 페닐메톡시등으로 이루어진 군으로부터 선택되는 어느 하나이고, 및 R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano to the furnace, halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, phenylmethoxy, etc. Any one selected from the group consisting of, and
R
7’ 및 R
8’는 각각 독립적으로 -O-, -CH
2- 및 -O(CH
2)
p-로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 p는 1 내지 6의 정수이다. R 7 ' and R 8 ' are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6.
본 발명에 따른 화합물은 하기 화학식 3으로 표시되는 화합물 또는 이의 약제학적으로 허용가능한 염일 수 있다: The compound according to the present invention may be a compound represented by the following formula (3) or a pharmaceutically acceptable salt thereof:
[화학식 3][Formula 3]
본 발명에서 약제학적으로 허용가능한 염은 의약업계에서 통상적으로 사용되는 염을 의미하며, 예를 들어 칼슘, 칼륨, 나트륨 및 마그네슘 등으로 제조된 무기이온염, 염산, 질산, 인산, 브롬산, 요오드산, 과염소산, 주석산 및 황산 등으로 제조된 무기산염, 아세트산, 트리플루오로아세트산, 시트르산, 말레인산, 숙신산, 옥살산, 벤조산, 타르타르산, 푸마르산, 만데르산, 프로피온산, 구연산, 젖산, 글리콜산, 글루콘산, 갈락투론산, 글루탐산, 글루타르산, 글루쿠론산, 아스파르트산, 아스코르브산, 카본산, 바닐릭산, 하이드로 아이오딕산 등으로 제조된 유기산염, 메탄설폰산, 에탄설폰산, 벤젠설폰산, p-톨루엔설폰산 및 나프탈렌설폰산 등으로 제조된 설폰산염, 글리신, 아르기닌, 라이신 등으로 제조된 아미노산염 및 트리메틸아민, 트라이에틸아민, 암모니아, 피리딘, 피콜린 등으로 제조된 아민염 등이 있으나, 열거된 이들 염에 의해 본 발명에서 의미하는 염의 종류가 한정되는 것은 아니다.In the present invention, pharmaceutically acceptable salts refer to salts commonly used in the pharmaceutical industry, for example, inorganic ionic salts prepared from calcium, potassium, sodium and magnesium, hydrochloric acid, nitric acid, phosphoric acid, hydrobromic acid, and iodine. Inorganic acid, perchloric acid, tartaric acid and sulfuric acid, acetic acid, trifluoroacetic acid, citric acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, manderic acid, propionic acid, citric acid, lactic acid, glycolic acid, gluconic acid , galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, carbonic acid, vanillic acid, hydroiodic acid, etc. organic acid salts, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p -There are sulfonic acid salts prepared from toluenesulfonic acid and naphthalenesulfonic acid, amino acid salts prepared from glycine, arginine, lysine, etc., and amine salts prepared from trimethylamine, triethylamine, ammonia, pyridine, picoline, etc. The types of salts in the present invention are not limited by these listed salts.
본 발명에 의하면, 상기 조성물은 체내 지방량을 감소시킴으로써 비만을 치료 또는 예방하는 것일 수 있다. According to the present invention, the composition may be to treat or prevent obesity by reducing the amount of body fat.
본 발명에 의하면, 상기 조성물은 복부 지방, 내장 지방, 근육 내 지방 및 혈중 지방 중에서 선택되는 하나 이상의 지방량을 감소시킴으로써 비만, 비만 합병증 또는 이들 모두를 치료 또는 예방하는 것일 수 있다. According to the present invention, the composition may treat or prevent obesity, obesity complications, or both by reducing the amount of one or more fats selected from abdominal fat, visceral fat, intramuscular fat, and blood fat.
복부비만 또는 내장비만은 복부 피하 또는 내장에 지방이 축적되는 증상으로 다양한 합병증을 동반하는 것으로 알려져 있다. 본 발명에 따른 조성물은 상기 언급된 비만 합병증의 치료 또는 예방에도 사용될 수 있다. Abdominal obesity or visceral obesity is a symptom of the accumulation of fat in the subcutaneous or internal organs of the abdomen and is known to accompany various complications. The composition according to the present invention can also be used for the treatment or prevention of the above-mentioned complications of obesity.
본 발명에 따른 조성물은 근육량의 손실 없이, 지방을 선택적으로 감량할 수 있으며, 세포독성이 매우 낮으므로 비만, 비만 합병증 또는 이들 모두를 치료 또는 예방하는데 효과적이다.The composition according to the present invention can selectively reduce fat without loss of muscle mass, and has very low cytotoxicity, so it is effective in treating or preventing obesity, obesity complications, or both.
또한, 본 발명에 따른 조성물은 인체 내 독성 없이 중성 트리글리세리드와 지질 함량을 감소시키고 체중 감량 효과 및 복부 지방 감소 효과를 나타내는 점에서 우수한 효과를 가진다.In addition, the composition according to the present invention has excellent effects in that it reduces the content of neutral triglycerides and lipids without toxicity in the human body, and exhibits a weight loss effect and an effect on reducing abdominal fat.
본 발명에 있어서, 용어 "치료"는 상기 조성물의 투여에 의해 비만 및 비만 합병증으로 인한 증상을 낫게 하는 행위를 모두 의미하는 것으로, 질환, 질환의 증상, 질병 또는 질환의 2차 질환, 또는 이에 대한 소인(predisposition)을 치료, 경감, 완화, 요법(remedy), 또는 향상하기 위한 목적과 함께 질환, 질환의 증상, 질병 또는 질환의 2차 질환, 또는 이에 대한 소인을 갖는 피험자(인간 또는 동물)에게 상기 조성물의 적용 또는 투여로 정의된다.In the present invention, the term "treatment" refers to both the action of alleviating the symptoms caused by obesity and obesity complications by administering the composition, and the disease, the symptoms of the disease, the secondary disease of the disease or disease, or To a subject (human or animal) having a disease, a symptom of a disease, a secondary disease of the disease or disorder, or a predisposition thereto, for the purpose of treating, alleviating, alleviating, remedying, or ameliorating the predisposition It is defined as the application or administration of the composition.
본 발명의 약학적 조성물은 조성물 총 중량에 대하여 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 0.01 내지 95 중량%, 바람직하게는 1 내지 80 중량%로 포함할 수 있다.The pharmaceutical composition of the present invention may contain 0.01 to 95% by weight, preferably 1 to 80% by weight of the oenotein B analog compound or a pharmaceutically acceptable salt thereof, based on the total weight of the composition.
본 발명의 일 실시예에 의하면, 상기 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염은 통상적인 담체, 보조제 또는 희석제와 혼합하여 통상의 제제화 방법으로 제형화하여 경구투여 또는 비경구투여에 적합한 형태로 제조될 수 있다.According to one embodiment of the present invention, the oenotein B analog compound or a pharmaceutically acceptable salt thereof is mixed with a conventional carrier, adjuvant or diluent and formulated in a conventional formulation method for oral or parenteral administration. It can be prepared in any suitable form.
상기 담체, 보조제 또는 희석제로는 락토즈, 덱스트로즈, 수크로스, 솔비톨, 만니톨, 자일리톨, 에리스리톨, 말티톨, 전분, 알지네이트, 젤라틴, 칼슘 포스페이트, 칼슘 실리케이트, 셀룰로즈, 메틸 셀룰로즈, 미정질 셀룰로스, 폴리비닐 피롤리돈, 물, 메틸히드록시벤조에이트, 프로필히드록시벤조에이트, 탈크, 마그네슘 스테아레이트 및 광물유를 들 수 있다.The carrier, adjuvant or diluent may include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, poly vinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.
또한, 제제화할 경우에는 통상의 충진제, 증량제, 결합제, 습윤제, 붕해제, 계면활성제 등을 더 포함할 수도 있으며, 마그네슘 스티레이트, 탈크 같은 윤활제를 더 첨가할 수도 있다. In addition, in the case of formulation, conventional fillers, extenders, binders, wetting agents, disintegrants, surfactants, etc. may be further included, and lubricants such as magnesium stearate and talc may be further added.
경구투여의 경우에는 정제, 캡슐제, 용액, 시럽제, 현탁제 등의 형태로 제조될 수 있고, 비경구투여의 경우에는 정맥, 자궁내 경막, 복강, 피하, 근육, 경피 및 뇌혈관 내 주사에 대한 주사제의 형태로 제조될 수 있다.In the case of oral administration, it may be prepared in the form of tablets, capsules, solutions, syrups, suspensions, etc., and in the case of parenteral administration, it is suitable for intravenous, intrauterine, intraperitoneal, subcutaneous, intramuscular, transdermal and intracerebrovascular injection. It can be prepared in the form of an injection for
본 발명의 약학적 조성물은 연구자, 수의사, 의사 또는 기타 임상에 의해 생각되는 조직계, 동물 또는 인간에서 생물학적 또는 의학적 반응을 유도하는 유효 성분 또는 약학적 조성물의 양, 즉 치료되는 질환 또는 장애의 증상의 완화를 유도하는 양인 치료상 유효량으로 투여할 수 있다. 본 발명의 약학 조성물에 대한 치료상 유효 투여량 및 투여횟수는 원하는 효과에 따라 변화될 것임은 당업자에게 자명하다. 그러므로, 투여될 최적의 투여량은 당업자에 의해 쉽게 결정될 수 있으며, 질환의 종류, 질환의 중증도, 조성물에 함유된 유효성분 및 다른 성분의 함량, 제형의 종류, 환자의 연령, 체중, 일반 건강 상태, 성별 및 식이, 투여시간, 투여 경로 및 조성물의 분비율, 치료기간, 동시 사용되는 약물을 비롯한 다양한 인자 등에 따라 조절될 수 있다. 본 발명의 약학 조성물은 개체에게 다양한 경로로 투여될 수 있다. 예를 들어, 정맥내, 복강내, 근육내, 동맥내, 구강, 심장내, 골수내, 경막내, 경피, 장관, 피하, 설하 또는 국소 투여할 수 있으나, 이에 제한되지 않는다.The pharmaceutical composition of the present invention is an amount of an active ingredient or pharmaceutical composition that induces a biological or medical response in a tissue system, animal or human as considered by a researcher, veterinarian, physician or other clinician, that is, the amount of the symptom of the disease or disorder being treated. It can be administered in a therapeutically effective amount, which is an amount that induces remission. It is apparent to those skilled in the art that the therapeutically effective dosage and frequency of administration for the pharmaceutical composition of the present invention will vary depending on the desired effect. Therefore, the optimal dosage to be administered can be easily determined by those skilled in the art, and the type of disease, the severity of the disease, the content of active ingredients and other ingredients contained in the composition, the type of formulation, the age, weight, and general health of the patient , sex and diet, administration time, administration route and secretion rate of the composition, treatment period, and various factors including concurrently used drugs. The pharmaceutical composition of the present invention may be administered to an individual by various routes. For example, intravenous, intraperitoneal, intramuscular, intraarterial, buccal, intracardiac, intramedullary, intrathecal, transdermal, enteral, subcutaneous, sublingual or topical administration may be administered, but not limited thereto.
본 발명의 약학 조성물은 1 내지 10,000㎎/㎏/일, 바람직하게는 1 내지 200㎎/㎏/일의 양으로 투여할 수 있으며, 하루에 한번 투여할 수도 있고, 수 회에 나누어 투여할 수도 있다. The pharmaceutical composition of the present invention may be administered in an amount of 1 to 10,000 mg/kg/day, preferably 1 to 200 mg/kg/day, and may be administered once a day or divided into several administrations .
또한, 본 발명이 해결하고자 하는 다른 과제는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만 개선, 체중 감량 또는 체지방 감량용 식품 조성물을 제공한다. In addition, another object to be solved by the present invention is to provide a food composition for improving obesity, weight loss or body fat loss, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
또한, 본 발명은 오에노테인 B를 포함하는 비만 개선 또는 체지방 감량용 식품 조성물을 제공한다. In addition, the present invention provides a food composition for improving obesity or reducing body fat containing oenotein B.
본 발명의 식품 조성물은 건강기능식품으로서 사용될 수 있다. 상기 "건강기능식품"이라 함은 건강기능식품에 관한 법률에 따른 인체에 유용한 기능성을 가진 원료나 성분을 사용하여 제조 및 가공한 식품을 의미하며, "기능성"이라 함은 인체의 구조 및 기능에 대하여 영양소를 조절하거나 생리학적 작용 등과 같은 보건 용도에 유용한 효과를 얻을 목적으로 섭취하는 것을 의미한다.The food composition of the present invention can be used as a health functional food. The term "health functional food" means a food manufactured and processed using raw materials or ingredients useful for the human body in accordance with the Health Functional Food Act, and "functionality" refers to the structure and function of the human body. It refers to ingestion for the purpose of obtaining useful effects for health purposes such as regulating nutrients or physiological effects.
본 발명의 식품 조성물은 통상의 식품 첨가물을 포함할 수 있으며, 상기 "식품 첨가물"로서의 적합 여부는 다른 규정이 없는 한, 식품의약품안전처에 승인된 식품 첨가물 공전의 총칙 및 일반시험법 등에 따라 해당 품목에 관한 규격 및 기준에 의하여 판정한다.The food composition of the present invention may contain conventional food additives, and the suitability as the "food additive" is determined according to the general rules and general test methods of food additives approved by the Ministry of Food and Drug Safety, unless otherwise specified. It is judged according to the standards and standards related to the item.
상기 "식품 첨가물 공전"에 수재된 품목으로는 예를 들어, 케톤류, 글리신, 구연산칼륨, 니코틴산, 계피산 등의 화학적 합성물, 감색소, 감초추출물, 결정셀룰로오스, 고량색소, 구아검 등의 천연첨가물, L-글루타민산나트륨 제제, 면류첨가알칼리제, 보존료제제, 타르색소제제 등의 혼합제제류들을 들 수 있다.The items listed in the "Food Additives Code" include, for example, chemical compounds such as ketones, glycine, potassium citrate, nicotinic acid, and cinnamic acid; Mixed preparations such as sodium L-glutamate preparation, noodle-added alkali agent, preservative agent, and tar color agent can be mentioned.
본 발명의 식품 조성물은 조성물 총 중량에 대하여 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 0.01 내지 95 중량%, 바람직하게는 1 내지 80 중량%로 포함할 수 있다.The food composition of the present invention may contain 0.01 to 95% by weight, preferably 1 to 80% by weight of the oenotein B analog compound or a pharmaceutically acceptable salt thereof, based on the total weight of the composition.
또한, 본 발명의 식품 조성물은 비만 개선, 체중 감량 또는 체지방 감량을 목적으로 정제, 캡슐, 분말, 과립, 액상, 환 등의 형태로 제조 및 가공할 수 있다.In addition, the food composition of the present invention can be manufactured and processed in the form of tablets, capsules, powders, granules, liquids, pills, etc. for the purpose of improving obesity, weight loss or body fat loss.
예를 들어, 상기 정제 형태의 건강기능식품은 오에노테인 B 유사체, 부형제, 결합제, 붕해제, 및 다른 첨가제와의 혼합물을 통상의 방법으로 과립화한 다음, 활택제 등을 넣어 압축성형하거나, 상기 혼합물을 직접 압축성형할 수 있다. 또한, 상기 정제 형태의 건강기능식품은 필요에 따라 교미제 등을 함유할 수 있으며, 필요에 따라 적당한 제피제로 제피할 수도 있다.For example, the health functional food in the form of tablets is granulated with a mixture of oenotein B analogs, excipients, binders, disintegrants, and other additives in a conventional manner, and then compression-molded by adding a lubricant, etc.; The mixture can be directly compression molded. In addition, the health functional food in the form of tablets may contain a mating agent, etc., if necessary, and may be coated with a suitable skinning agent if necessary.
캡슐 형태의 건강기능식품 중 경질캡슐제는 통상의 경질캡슐에 오에노테인 B 유사체, 및 부형제 등의 첨가제와의 혼합물 또는 그의 입상물 또는 제피한 입상물을 충진하여 제조할 수 있으며, 연질캡슐제는 오에노테인 B 유사체 및 부형제 등의 첨가제와의 혼합물을 젤라틴 등 캡슐기제에 충진하여 제조할 수 있다. 상기 연질캡슐제는 필요에 따라 글리세린 또는 소르비톨 등의 가소제, 착색제, 보존제 등을 함유할 수 있다.Among health functional foods in the form of capsules, hard capsules can be prepared by filling conventional hard capsules with a mixture of oenotein B analogues and additives such as excipients, or granules thereof or coated granules. can be prepared by filling a mixture of an oenotein B analogue and an additive such as an excipient into a capsule base such as gelatin. The soft capsule formulation may contain a plasticizer such as glycerin or sorbitol, a colorant, a preservative, and the like, if necessary.
환 형태의 건강기능식품은 오에노테인 B 유사체, 부형제, 결합제, 붕해제 등의 혼합물을 적당한 방법으로 성형하여 조제할 수 있으며, 필요에 따라 백당이나 다른 적당한 제피제로 제피를, 또는 전분, 탈크 또는 적당한 물질로 환의를 입힐 수도 있다.A health functional food in the form of a ring can be prepared by molding a mixture of oenotein B analogues, excipients, binders, disintegrants, etc. in an appropriate way, and if necessary, the skin is coated with sucrose or other suitable skinning agent, or starch, talc, or You can also dress the gown with a suitable material.
과립형태의 건강기능식품은 오에노테인 B 유사체, 부형제, 결합제, 붕해제 등의 혼합물을 적당한 방법으로 입상으로 제조할 수 있으며, 필요에 따라 착향제, 교미제 등을 함유할 수 있다. 과립형태의 건강기능식품은 12호 (1680 μm), 14호 (1410 μm) 및 45호 (350 μm) 체를 써서 다음 입도시험을 할 때에 12호체를 전량 통과하고 14호체에 남는 것이 전체량의 5.0 %이하이고 또 45호체를 통과하는 것은 전체량의 15.0 %이하일 수 있다.A health functional food in granular form may be prepared in a granular form by a suitable method of a mixture of oenotein B analogues, excipients, binders, disintegrants, etc., and may contain flavoring agents, flavoring agents, etc. as needed. For health functional foods in granular form, use No. 12 (1680 μm), No. 14 (1410 μm) and No. 45 (350 μm) sieves to pass all the sieves No. 12 and the remaining in No. 14 sieves in the next particle size test. 5.0% or less and passing through No. 45 may be less than 15.0% of the total amount.
상기 부형제, 결합제, 붕해제, 활택제, 교미제, 착향제 등에 대한 용어 정의는 당업계에 공지된 문헌에 기재된 것으로 그 기능 등이 동일 내지 유사한 것들을 포함한다 (대한약전 해설편, 문성사, 한국약학대학협의회, 제 5 개정판, p33-48, 1989).The term definitions for the excipients, binders, disintegrants, lubricants, flavoring agents, flavoring agents, etc. are described in documents known in the art and include those having the same or similar functions (Explanation of the Korean Pharmacopoeia, Moonseongsa, Korea) Association of Colleges of Pharmacy, 5th ed., p33-48, 1989).
상기 식품의 종류에는 특별한 제한이 없다. 본 발명의 오에노테인 B 유사체를 첨가할 수 있는 식품의 예로는 음료, 껌, 비타민 복합제, 드링크제 등이 있으며, 통상적인 의미에서의 건강기능식품을 모두 포함한다.There is no particular limitation on the type of the food. Examples of foods to which the oenotein B analogue of the present invention can be added include beverages, gums, vitamin complexes, drinks, and the like, and include all health functional foods in a conventional sense.
상기 식품 조성물은 식품보조첨가제를 포함할 수 있으며, 식품류는 예를 들어, 음료, 껌, 차, 비타민 복합제, 건강보조 식품류 등이 있으며, 캡슐, 정제, 분말, 과립, 액상, 환, 편상, 페이스트상, 시럽, 겔, 음료, 젤리 또는 바인 형태로 사용할 수 있다. The food composition may contain food supplement additives, and the food products include, for example, beverages, gum, tea, vitamin complexes, health supplements, etc., capsules, tablets, powders, granules, liquids, pills, slices, pastes. It can be used in the form of phases, syrups, gels, beverages, jellies or vines.
오에노테인 B 유사체의 함량은 건강기능식품 총 중량을 기준으로 0.01 내지 15 중량%로 함유할 수 있으며, 건강음료 조성물의 경우에는 총 100 g을 기준으로 0.02 내지 10 g, 바람직하게는 0.3 내지 1 g으로 함유할 수 있다.The content of the oenotein B analogue may be contained in an amount of 0.01 to 15% by weight based on the total weight of the health functional food, and in the case of a health beverage composition, 0.02 to 10 g, preferably 0.3 to 1, based on a total of 100 g g may contain.
상기 식품보조첨가제는 당업계에 통상적인 식품첨가제, 예를 들어 향미제, 풍미제, 착색제, 충진제, 안정화제 등을 포함한다. 또한, 상기 건강음료조성물은 지시된 비율로 필수 성분으로서, 상기 오에노테인 B 유사체 외에 첨가되는 성분에 특별한 제한은 없으며 통상의 음료와 같이 여러 가지 향미제 또는 천연 탄수화물 등을 추가 성분으로서 함유할 수 있다. 상기 천연 탄수화물의 예로는 모노사카라이드, 예를 들어, 포도당, 과당 등; 디사카라이드, 예를 들어 말토스, 슈크로스 등; 폴리사카라이드, 예를 들어 덱스트린, 시클로덱스트린; 등과 같은 통상적인 당 및 자일리톨, 소르비톨, 에리트리톨 등의 당알콜이다. 상술한 것 이외의 향미제로서 천연 향미제 (타우마틴, 스테비아 추출물 (예를 들어 레바우디오시드 A, 글리시르히진 등)) 및 합성 향미제 (사카린, 아스파르탐 등)를 유리하게 사용할 수 있다. The food supplement additives include food additives conventional in the art, for example, flavoring agents, flavoring agents, coloring agents, fillers, stabilizers, and the like. In addition, the health drink composition is an essential ingredient in the indicated ratio, and there is no particular limitation on the ingredients added other than the oenotein B analog, and it can contain various flavoring agents or natural carbohydrates as additional ingredients like conventional beverages. have. Examples of the natural carbohydrate include monosaccharides such as glucose, fructose and the like; disaccharides such as maltose, sucrose and the like; polysaccharides such as dextrins, cyclodextrins; and sugar alcohols such as xylitol, sorbitol, and erythritol. As flavoring agents other than those described above, natural flavoring agents (taumatin, stevia extract (eg rebaudioside A, glycyrrhizin, etc.)) and synthetic flavoring agents (saccharin, aspartame, etc.) can be advantageously used. have.
상기 외, 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 식품 조성물, 다이어트 보조제 또는 건강기능식품은 여러 가지 영양제, 비타민, 광물 (전해질), 합성 풍미제 및 천연 풍미제 등의 풍미제, 착색제 및 중진제 (치즈, 초콜릿 등), 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알코올, 탄산 음료에 사용되는 탄산화제 등을 함유할 수 있다.In addition to the above, food compositions, diet supplements, or health functional foods containing an oenotein B analogue compound or a pharmaceutically acceptable salt thereof include various nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors. Flavoring, coloring and thickening agents (cheese, chocolate, etc.), pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, carbonates used in carbonated beverages It may contain topics and the like.
또한, 본 발명은 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만 및 비만 합병증 개선 또는 예방용 동물 사료 조성물을 제공한다. In addition, the present invention provides an animal feed composition for improving or preventing obesity and obesity complications, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
본 발명에 있어서 동물은 포유동물 및 조류 중에서 선택되는 하나 이상일 수 있으며, 바람직하게, 축산법 제2조 제1호 및 동법 시행규칙 제2조 각호에서 정의하고 있는, 야생습성이 순화되어 사육하기에 적합하며 농가의 소득증대에 기여할 수 있는 가축일 수 있다. 상기 가축에는 소, 말, 노새, 당나귀, 염소, 산양, 면양, 사슴, 돼지, 토끼, 가금류 등 일수 있으며, 가금류에는 닭, 칠면조, 오리, 타조, 거위, 메추리 등, 바람직하게는 닭 일수 있으나, 사육하여 축산물을 얻기에 적합한 것이라면 이에 제한되는 것은 아니다. 상기 "축산물"은 축산법 제2조 3호의 정의인, 가축에서 생산된 고기, 젖, 알, 꿀과 이들의 가공품, 원피 (원모피를 포함한다), 원모, 기타 가축의 생산물로서 농림부령이 정하는 것을 의미한다. 또한 반려동물을 포함하여 개, 고양이 등 일 수 있으나, 이에 제한되는 것은 아니다.In the present invention, the animal may be one or more selected from mammals and birds, and preferably, the wild habits defined in Article 2, No. 1 of the Livestock Livestock Act and Article 2 of the Enforcement Rule of the same Act, and are suitable for breeding. And it can be a livestock that can contribute to the income increase of the farmhouse. The livestock may be cattle, horses, mules, donkeys, goats, goats, sheep, deer, pigs, rabbits, poultry, etc., and poultry includes chickens, turkeys, ducks, ostriches, geese, quails, etc., preferably chickens, If it is suitable for breeding and obtaining livestock products, it is not limited thereto. The above "livestock products" are meat, milk, eggs, honey and their processed products, raw hides (including raw fur), raw wool, and other livestock products, which are defined by Article 2, 3 of the Livestock Act, as determined by the Ordinance of the Ministry of Agriculture and Forestry. means that In addition, it may be a dog, a cat, etc., including companion animals, but is not limited thereto.
발명의 용어 "사료"는 동물이 먹고, 섭취하며, 소화시키기 위한 또는 이에 적당한 임의의 천연 또는 인공 규정식, 한끼식 등 또는 상기 한끼식의 성분을 의미한다. 일 양태로, 본 발명의 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 함유하는 사료용 조성물에는 농후사료, 조사료 및/또는 특수사료가 포함될 수 있다.The term "feed" in the present invention means any natural or artificial diet, meal, etc., or a component of said meal, intended for or suitable for being eaten, consumed, and digested by an animal. In one embodiment, the composition for feed containing the oenotein B analog compound of the present invention or a pharmaceutically acceptable salt thereof may include a concentrated feed, forage and/or special feed.
농후사료에는 밀, 귀리, 옥수수 등의 곡류를 포함하는 종자열매류, 곡물을 정제하고 얻는 부산물로서 쌀겨, 밀기울, 보릿겨 등을 포함하는 겨류, 콩, 유체, 깨, 아마인, 코코야자 등을 채유하고 얻는 부산물인 깻묵류와 고구마, 감자 등에서 녹말을 뺀 나머지인 녹말찌꺼기의 주성분인 잔존녹말질류 등의 찌꺼기류, 어분, 물고기찌꺼기, 어류에서 얻은 신선한 액상물을 농축시킨 것인 피시솔루블, 육분, 혈분, 우모분, 탈지분유, 우유에서 치즈, 탈지유에서 카제인을 제조할 때의 잔액인 훼이(whey)를 건조한 건조훼이 등의 동물질사료, 효모, 클로렐라, 해조류 등이 있다.In the enriched feed, seed fruits containing grains such as wheat, oats, and corn, bran containing rice bran, bran, barley bran, etc. Fish-soluble, meat powder, which is a condensed product of fish meal, fish waste, and fresh liquid obtained from fish meal, fish waste, fish meal, fish meal , animal feed such as dried whey, yeast, chlorella, seaweed, etc., blood meal, feather meal, skim milk powder, cheese from milk, and whey, which is the remainder of the production of casein from skim milk.
조사료에는 야초, 목초, 풋베기 등의 생초(生草)사료, 사료용 순무, 사료용 비트, 순무의 일종인 루터베어거 등의 뿌리채소류, 생초, 풋베기작물, 곡실(穀實)등을 사일로에 채워 놓고 젖산발효시킨 저장사료인 사일리지(silage), 야초, 목초를 베어 건조시킨 건초, 종축용(種畜用) 작물의 짚, 콩과 식물의 나뭇잎 등이 있다. 특수 사료에는 굴껍테기, 암염 등의 미네랄 사료, 요소나 그 유도체인 디우레이드이소부탄 등의 요소사료, 천연사료 원료만을 배합했을 때 부족하기 쉬운 성분을 보충하거나, 사료의 저장성을 높이기 위해서 배합사료에 미량으로 첨가하는 물질인 사료첨가물 등이 있다.For roughage, raw grass feed such as wild grasses, grasses and green cuttings, turnips for feed, beets for feed, root vegetables such as luther bearger, a type of turnip, raw herbs, green crops, and grains are placed in a silo. There are silage, which is a stored feed fermented with lactic acid after being filled, wild grasses, hay obtained by cutting and drying grass, straw for breeding crops, and leaves from legumes. Special feed includes mineral feed such as oyster shells and rock salt, urea feed such as urea or its derivative diureide isobutane, supplementing ingredients that are easily lacking when only natural feed ingredients are blended, or added to formulated feed to increase feed storage. There are feed additives, which are substances added in trace amounts.
또한, 본 발명은 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 저지방 함유 가축 비육용 사료 조성물을 제공한다. In addition, the present invention provides a low-fat-containing livestock feed composition comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
본 발명에 따르면, 오에노테인 B 유사체는 근육량의 손실 없이, 체내 지방의 함량을 감량시키므로 저지방 함유 가축 비육용 사료 조성물의 첨가제로 유용하게 적용될 수 있다. According to the present invention, the oenotein B analog can be usefully applied as an additive to a low-fat-containing livestock fattening feed composition because it reduces the body fat content without loss of muscle mass.
또한, 본 발명은 비만, 비만 합병증 또는 이들 모두의 치료를 위한 약제의 제조에서 상기 화학식 1 또는 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염의 용도를 제공한다. In addition, the present invention provides the use of an oenotein B analog compound represented by Formula 1 or Formula 2, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment of obesity, obesity complications, or both.
또한, 본 발명은 상기 화학식 1 또는 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염의 약제학적으로 유효한 양을 이를 필요로 하는 대상에게 투여하는 것을 포함하는 비만, 비만 합병증 또는 이들 모두의 예방 또는 치료 방법을 제공한다. In addition, the present invention relates to obesity, obesity complications, Methods for preventing or treating all of these are provided.
본 발명에서 사용되는 용어, "대상"이란, 비만 또는 비만 합병증이 발병되었거나 발병할 가능성이 있는 인간을 포함한 모든 동물을 의미할 수 있다. 상기 동물은 인간뿐만 아니라 이와 유사한 증상의 치료를 필요로 하는 소, 말, 양, 돼지, 염소, 낙타, 영양, 개, 고양이 등의 포유동물일 수 있다. 또한 인간을 제외한 동물을 의미할 수 있으나, 이에 제한되지는 않는다.As used herein, the term "subject" may refer to all animals, including humans, that have or are likely to develop obesity or obesity complications. The animal may be a mammal, such as a cow, a horse, a sheep, a pig, a goat, a camel, an antelope, a dog, or a cat, in need of treatment for symptoms similar to those of humans as well as humans. It may also refer to animals other than humans, but is not limited thereto.
본 발명의 상기 예방 또는 치료 방법은 구체적으로, 비만 또는 비만 합병증이 발병하였거나 발병할 위험이 있는 개체에 상기 조성물을 약학적으로 유효한 양으로 투여하는 단계를 포함할 수 있다.Specifically, the prevention or treatment method of the present invention may include administering the composition in a pharmaceutically effective amount to an individual who has developed or is at risk of developing obesity or obesity complications.
또한, 본 발명은 비만, 비만 합병증 또는 이들 모두의 치료에 사용하기 위한, 상기 화학식 1 또는 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 조성물In addition, the present invention provides a composition comprising an oenotein B analogue compound represented by Formula 1 or Formula 2 or a pharmaceutically acceptable salt thereof for use in the treatment of obesity, obesity complications, or both.
본 발명에서, 상기 화학식 1 또는 화학식 2로 표시되는 오에노테인 B 유사체 화합물, 이의 약제학적으로 허용가능한 염, 비만 또는 비만 합병증의 정의는 상기에서 설명한 바와 같다. In the present invention, the definition of the oenotein B analog compound represented by Formula 1 or Formula 2, a pharmaceutically acceptable salt thereof, obesity or obesity complications is as described above.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범주 및 기술사상 범위 내에서 다양한 변경 및 수정이 가능함은 당업자에게 있어서 명백한 것이며, 이러한 변형 및 수정이 첨부된 특허청구범위에 속하는 것도 당연한 것이다.Hereinafter, preferred examples are presented to aid the understanding of the present invention, but the following examples are merely illustrative of the present invention and it will be apparent to those skilled in the art that various changes and modifications are possible within the scope and spirit of the present invention, It goes without saying that such variations and modifications fall within the scope of the appended claims.
실시예Example
시약reagent
이하에서 언급된 시약 및 용매는 특별한 언급이 없는 한, Sigma-Aldrich, TCI 또는 Alfa aesar 로부터 구입한 것이며, HPLC 급을 사용하였다. The reagents and solvents mentioned below were purchased from Sigma-Aldrich, TCI or Alfa aesar, unless otherwise specified, and HPLC grade was used.
시험예 1. 정상 체중 동물모델에서의 오에노테인 B의 체중 감량 효과Test Example 1. Weight loss effect of oenotein B in a normal-weight animal model
오에노테인 B를 멸균 증류수에 녹여 20 mg/mL의 용액으로 제조하였다. 제조된 용액을 식염수를 사용하여 20배로 희석한 후, 1cc 주사기를 사용하여 평균 13 주령의 C57BL6/J 마우스의 복강에 200μL의 오에노테인 B(1 mg/mL)를 실험 1일과 3일에 48시간 간격을 두고 주사하였으며, 오에노테인 B 용액을 주사하기 하루 전을 시작으로 주사 후 5일 동안 체중변화를 매일 측정하였다. 증류수를 대조군으로 사용하였으며, 실험 동안 지방함량이 15%인 일반 사료와 물을 제공하였다. Oenotein B was dissolved in sterile distilled water to prepare a solution of 20 mg/mL. After diluting the prepared solution 20-fold with saline, 200 μL of oenotein B (1 mg/mL) was injected into the abdominal cavity of C57BL6/J mice with an average age of 13 weeks using a 1cc syringe on days 1 and 3 of the experiment. The injections were made at intervals of time, and body weight changes were measured daily for 5 days after injection, starting one day before the injection of oenotein B solution. Distilled water was used as a control, and normal feed and water with a fat content of 15% were provided during the experiment.
도 1은 오에노테인 B의 체중 감량 효과 결과 그래프를 보여준다. 화살표는 오에노테인 B의 주사 시점을 나타낸다. 오에노테인 B 주사 후 1일 차부터 체중 감량 효과가 나타났으며, 첫 번째 주사 후 1.5~8.5% 체중이 감량되었고, 두 번째 주사 후 1.5 내지 6% 체중이 감량되었다. 이러한 결과는 오에노테인 B가 단기간에 우수한 체중 감량 효과를 나타내었으며, 감량된 체중이 유지되고 있음을 시사한다. 1 shows a graph showing the weight loss effect of oenotein B. Arrows indicate the time of injection of oenotein B. After the first injection of oenotein B, a weight loss effect was observed, and 1.5 to 8.5% of body weight was lost after the first injection, and 1.5 to 6% of body weight was lost after the second injection. These results suggest that oenotein B exhibited an excellent weight loss effect in a short period of time, and that the weight loss was maintained.
시험예 2. 비만 동물모델에서의 오에노테인 B의 체중 감량 효과Test Example 2. Weight loss effect of oenotein B in obese animal model
과체중 유도된 마우스를 사용하여 비만 동물 모델에서의 오에노테인 B의 체중 감량 효과를 확인하였다. 평균 12 주령의 C57BL/6J 마우스에게 일반사료 (지방 함량 15%)를 지방 함량이 45%인 고지방 사료로 바꾼 후 급여하였으며 매일 체중 변화를 측정하였다. 고지방 사료 급여 후, 21, 23, 25일에 200μL의 오에노테인 B(1 mg/mL)를 마우스의 복강에 주사한 후 27일 차까지 매일 체중 변화를 측정하였으며, 대조군은 증류수를 주사하였다. The weight loss effect of oenotein B in an obese animal model was confirmed using overweight-induced mice. C57BL/6J mice with an average age of 12 weeks were fed after changing the normal diet (fat content 15%) to a high-fat diet containing 45% fat, and the change in body weight was measured daily. After feeding the high-fat feed, on the 21st, 23rd, and 25th days, 200 μL of oenotein B (1 mg/mL) was injected into the abdominal cavity of the mice, and body weight changes were measured every day until the 27th day, and the control group was injected with distilled water.
도 2에 나타낸 바와 같이, 고지방 사료를 3주간 제공받은 마우스의 체중은 평균 약 16.3% 증가하는 것으로 확인되었다. 체중이 증가된 마우스에 200μL의 오에노테인 B(1 mg/mL)를 48 시간 간격으로 3회 복강 주사한 결과, 대조군은 체중 변화가 크게 없었으나, 오에노테인 B를 주사한 마우스의 체중은 지속적으로 감소하여 주사 후 6일차에 약 12.9%의 체중이 감량되었다. 또한, 투여한지 만 72시간만에 9% 의 체중이 감량되는 것으로 관찰되었으며, 체중 감량 후에도 식욕이 감소하거나 탈수 증세를 보이거나 스트레스, 체력저하 등이 관찰되지 않았고, 독성 등의 부작용도 관찰되지 않았다. As shown in FIG. 2 , it was confirmed that the body weight of the mice receiving the high-fat feed for 3 weeks increased by about 16.3% on average. As a result of intraperitoneal injection of 200 μL of oenotein B (1 mg/mL) three times at 48 hour intervals to mice with increased body weight, there was no significant change in body weight in the control group, but the body weight of mice injected with oenotein B was It continued to decrease, and about 12.9% of the body weight was lost on the 6th day after injection. In addition, 9% of weight loss was observed within 72 hours of administration. After weight loss, there was no decrease in appetite, no signs of dehydration, stress, deterioration of physical strength, and no side effects such as toxicity. .
시험예 3. 비만 동물모델에서의 오에노테인 B의 체중 감량 효과Test Example 3. Weight loss effect of oenotein B in obese animal model
과체중이 유도된 마우스에서 오에노테인 B에 의한 체중 감량이 지방 감소에 의한 것인지 확인하기 위하여 시험예 2에서 사용된 동일한 마우스를 이용하여 복부 지방의 무게를 측정하였으며, 그 결과를 도 3에 나타내었다.In order to determine whether the weight loss by oenotein B in the overweight-induced mouse was due to the reduction in fat, the weight of abdominal fat was measured using the same mouse used in Test Example 2, and the results are shown in FIG. .
오에노테인 B가 투여된 마우스의 경우, 대조군과 비교하여평균 약 44%의 복부 지방이 감소한 것이 확인되었다. 이러한 결과는 오에노테인 B의 투여에 의한 체중 감소가 지방량의 감소에 따른 것임을 보여준다. In the case of mice administered oenotein B, compared to the control group, it was confirmed that the average abdominal fat was reduced by about 44%. These results show that the weight loss by the administration of oenotein B is due to the decrease in fat mass.
시험예 4. oil red O staining Test Example 4. oil red O staining
Oil red O는 중성 트리글리세리드와 지질을 염색하는데 사용되는 염료이다. 3T3-L1 지방전구세포를 지방세포로 분화시킨 후 오에노테인 B를 20 및 40 μg/ml의 농도로 4번에 걸쳐 처리하여 지방감소 정도를 조사하였으며, 이를 도 4에 나타내었다. Oil red O is a dye used to stain neutral triglycerides and lipids. After 3T3-L1 preadipocytes were differentiated into adipocytes, the degree of fat reduction was investigated by treatment with oenotein B at concentrations of 20 and 40 μg/ml 4 times, and this is shown in FIG. 4 .
도 4는 염색 결과를 나타낸 것이다. 대조군과 달리 오에노테인 B를 처리한 군에서는 염색된 지방의 양이 최대 50 % 감소하는 것이 확인되었다. 4 shows the staining results. Unlike the control group, it was confirmed that the amount of stained fat was reduced by up to 50% in the group treated with oenotein B.
시험예 5. 세포독성 평가 Test Example 5. Cytotoxicity evaluation
사람의 폐암 조직에서 얻은 세포주인 A549 세포를 RPMI-1640 배지에 10% fetal bovine serum을 섞어 37℃, 5% CO
2의 조건에서 배양하였다. 다음으로 오에노테인 B를 A549 세포에 처리한 후, lactate dehydrogenase (LDH) release assay를 실시하여 세포독성을 정량적으로 측정하였으며, 그 결과를 도 5에 나타내었다. 양성 대조군(positive)으로 과산화수소를 사용하였고, 음성 대조군(negative)으로 식염수(phosphate-buffered saline)를 사용하였다.A549 cells, a cell line obtained from human lung cancer tissue, were mixed with 10% fetal bovine serum in RPMI-1640 medium and cultured at 37° C. and 5% CO 2 conditions. Next, after treating A549 cells with oenotein B, lactate dehydrogenase (LDH) release assay was performed to quantitatively measure cytotoxicity, and the results are shown in FIG. 5 . Hydrogen peroxide was used as a positive control, and phosphate-buffered saline was used as a negative control.
도 5에 나타낸 바와 같이, 오에노테인 B의 독성은 음성 대조군 수준만큼 낮은 것이 확인되었다. As shown in FIG. 5 , it was confirmed that the toxicity of oenotein B was as low as the level of the negative control.
상기와 같은 결과는 본원 발명에 따른 오에노테인 B 유사체가 세포 독성과 같은 부작용이 없이 단기간에 체내 지방을 감소시킴으로써 체중 감량을 유도하고, 감량된 체중을 장기간 유지할 수 있음을 보여준다. 이러한 결과를 바탕으로 본 발명에 따른 오에노테인 B 유사체를 포함하는 조성물은 체중 감량, 비만 및 비만 합병증의 치료, 예방 또는 개선을 위한 약학적 조성물, 식품 조성물, 특히 체중 감량용 또는 체지방 감량용 건강기능식품, 사료 조성물로 유용하게 적용이 가능하며, 나아가 저지방 함유 가축 비육을 위한 사료 조성물로도 유용하게 사용될 수 있다. The above results show that the oenotein B analogue according to the present invention can induce weight loss by reducing body fat in a short period of time without side effects such as cytotoxicity, and can maintain the weight loss for a long time. Based on these results, the composition comprising the oenotein B analog according to the present invention is a pharmaceutical composition, a food composition for weight loss, treatment, prevention or improvement of obesity and obesity complications, in particular, health for weight loss or body fat loss It can be usefully applied as a functional food, a feed composition, and further can be usefully used as a feed composition for fattening livestock containing low fat.
Claims (21)
- 하기 화학식 1로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 유효성분으로 포함하는 비만, 비만 합병증 또는 이들 모두의 치료 또는 예방용 약학적 조성물:A pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both, comprising an oenotein B analog compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient:[화학식 1][Formula 1]
식 중에서, In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy Any one selected from the group,R 7 및 R 8은 -OH이다.R 7 and R 8 are —OH. - 하기 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 유효성분으로 포함하는 비만, 비만 합병증 또는 이들 모두의 치료 또는 예방용 약학적 조성물:A pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both, comprising an oenotein B analog compound represented by the following formula (2) or a pharmaceutically acceptable salt thereof as an active ingredient:[화학식 2][Formula 2]
식 중에서,In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, 및 R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy any one selected from the group, andR 7’ 및 R 8’는 각각 독립적으로 -O-, -CH 2- 및 -O(CH 2) p-로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 p는 1 내지 6의 정수이다. R 7 ' and R 8 ' are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6. - 제2항에 있어서, 상기 화학식 2의 화합물은 하기 화학식 3으로 표시되는 화합물인 약학적 조성물:The pharmaceutical composition according to claim 2, wherein the compound of Formula 2 is a compound represented by Formula 3 below:[화학식 3][Formula 3]
- 제1항 내지 제3항 중 어느 한 항에 있어서, 4. The method according to any one of claims 1 to 3,상기 오에노테인 B 유사체는 복부 지방, 내장 지방, 근육내 지방 및 혈중 지방 중에서 선택되는 하나 이상의 체내 지방량을 감소시키는 것인, 약학적 조성물.The oenotein B analog reduces the amount of body fat at least one selected from abdominal fat, visceral fat, intramuscular fat and blood fat.
- 제1항 내지 제3항 중 어느 한 항에 있어서, 상기 비만 합병증은 고혈압; 당뇨병; 고지혈증; The method according to any one of claims 1 to 3, wherein the obesity complication is hypertension; diabetes; hyperlipidemia;허리 디스크; 퇴행성 관절염; Herniated disc; degenerative arthritis;복부 비만에 의한 역류성식도염, 탈장 또는 스트레스 요실금; reflux esophagitis, hernia or stress incontinence due to abdominal obesity;수면무호흡증; 비알코올성지방간;sleep apnea; nonalcoholic fatty liver;협심증; 심근경색; 심부전; angina pectoris; myocardial infarction; heart failure;뇌졸중; 뇌경색; stroke; cerebral infarction;여성의 체지방 과다에 의한 여성 호르몬 증가로 초래되는 이른 초경; 배란 장애; 성조숙증; 생리불순; 불임; 다낭성난소증후군으로 이루어진 군으로부터 선택되는 어느 하나의 질환인, 약학적 조성물. Early menarche caused by increased female hormones due to excess body fat in women; ovulation disorders; precocious puberty; irregular menstruation; sterility; Any one disease selected from the group consisting of polycystic ovary syndrome, a pharmaceutical composition.
- 하기 화학식 1로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만 개선, 체중 감량 또는 체지방 감량용 식품 조성물:A food composition for improving obesity, weight loss or body fat reduction, comprising an oenotein B analog compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof:[화학식 1][Formula 1]
식 중에서, In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy Any one selected from the group,R 7 및 R 8은 -OH이다.R 7 and R 8 are —OH. - 하기 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만 개선, 체중 감량 또는 체지방 감량용 식품 조성물:A food composition for improving obesity, weight loss, or reducing body fat, comprising an oenotein B analog compound represented by the following formula (2) or a pharmaceutically acceptable salt thereof:[화학식 2][Formula 2]
식 중에서,In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, 및 R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy any one selected from the group, andR 7’ 및 R 8’는 각각 독립적으로 -O-, -CH 2- 및 -O(CH 2) p-로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 p는 1 내지 6의 정수이다. R 7 ' and R 8 ' are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6. - 제7항에 있어서, 상기 화학식 2의 화합물은 하기 화학식 3으로 표시되는 화합물인 식품 조성물:The food composition according to claim 7, wherein the compound of Formula 2 is a compound represented by Formula 3 below:[화학식 3][Formula 3].
. - 제6항 내지 제8항 중 어느 한 항에 있어서, 상기 식품 조성물은 건강기능식품인, 식품 조성물.The food composition according to any one of claims 6 to 8, wherein the food composition is a health functional food.
- 하기 화학식 1로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만, 비만 합병증 또는 이들 모두의 개선 또는 예방용 동물 사료 조성물:An animal feed composition for alleviating or preventing obesity, obesity complications, or both, comprising an oenotein B analog compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof:[화학식 1][Formula 1]
식 중에서, In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy Any one selected from the group,R 7 및 R 8은 -OH이다.R 7 and R 8 are —OH. - 하기 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 비만, 비만 합병증 또는 이들 모두의 개선 또는 예방용 동물 사료 조성물:An animal feed composition for alleviating or preventing obesity, obesity complications, or both, comprising an oenotein B analog compound represented by the following formula (2) or a pharmaceutically acceptable salt thereof:[화학식 2][Formula 2]
식 중에서,In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, 및 R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy any one selected from the group, andR 7’ 및 R 8’는 각각 독립적으로 -O-, -CH 2- 및 -O(CH 2) p-로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 p는 1 내지 6의 정수이다. R 7 ' and R 8 ' are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6. - 제11항에 있어서, 상기 화학식 2의 화합물은 하기 화학식 3으로 표시되는 화합물인 동물 사료 조성물:The animal feed composition according to claim 11, wherein the compound of Formula 2 is a compound represented by Formula 3 below:[화학식 3][Formula 3]
- 하기 화학식 1로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 저지방 함유 가축 비육용 사료 조성물:A low-fat-containing livestock fattening feed composition comprising an oenotein B analog compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof:[화학식 1][Formula 1]
식 중에서, In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy Any one selected from the group,R 7 및 R 8은 -OH이다.R 7 and R 8 are —OH. - 하기 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 저지방 함유 가축 비육용 사료 조성물:A low-fat-containing livestock fattening feed composition comprising an oenotein B analog compound represented by the following formula (2) or a pharmaceutically acceptable salt thereof:[화학식 2][Formula 2]
식 중에서,In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, 및 R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy any one selected from the group, andR 7’ 및 R 8’는 각각 독립적으로 -O-, -CH 2- 및 -O(CH 2) p-로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 p는 1 내지 6의 정수이다. R 7 ' and R 8 ' are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6. - 제14항에 있어서, 상기 화학식 2의 화합물은 하기 화학식 3으로 표시되는 화합물인 저지방 함유 가축 비육용 사료 조성물:15. The low fat-containing livestock fattening feed composition according to claim 14, wherein the compound of Formula 2 is a compound represented by Formula 3 below:[화학식 3][Formula 3]
- 비만, 비만 합병증 또는 이들 모두의 치료를 위한 약제의 제조에서 하기 화학식 1 또는 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염의 용도:Use of an oenotein B analog compound represented by the following formula (1) or formula (2) or a pharmaceutically acceptable salt thereof in the manufacture of a medicament for the treatment of obesity, obesity complications, or both:[화학식 1][Formula 1]
[화학식 2][Formula 2]
식 중에서, In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R 3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R 3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy Any one selected from the group,R 7 및 R 8은 -OH이고, 및R 7 and R 8 are —OH, andR 7’ 및 R 8’는 각각 독립적으로 -O-, -CH 2- 및 -O(CH 2) p-로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 p는 1 내지 6의 정수이다. R 7 ' and R 8 ' are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6. - 제16항에 있어서, 17. The method of claim 16,상기 비만 합병증은 고혈압; 당뇨병; 고지혈증; The obesity complications include hypertension; diabetes; hyperlipidemia;허리 디스크; 퇴행성 관절염; Herniated disc; degenerative arthritis;복부 비만에 의한 역류성식도염, 탈장 또는 스트레스 요실금; reflux esophagitis, hernia or stress incontinence due to abdominal obesity;수면무호흡증; 비알코올성지방간;sleep apnea; nonalcoholic fatty liver;협심증; 심근경색; 심부전; angina pectoris; myocardial infarction; heart failure;뇌졸중; 뇌경색; stroke; cerebral infarction;여성의 체지방 과다에 의한 여성 호르몬 증가로 초래되는 이른 초경; 배란 장애; 성조숙증; 생리불순; 불임; 다낭성난소증후군으로 이루어진 군으로부터 선택되는 어느 하나의 질환인, 용도. Early menarche caused by increased female hormones due to excess body fat in women; ovulation disorders; precocious puberty; irregular menstruation; sterility; Any one disease selected from the group consisting of polycystic ovary syndrome, use.
- 하기 화학식 1 또는 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염의 약제학적으로 유효한 양을 이를 필요로 하는 대상에게 투여하는 것을 포함하는 비만, 비만 합병증 또는 이들 모두의 예방 또는 치료 방법:Prevention of obesity, obesity complications, or both, comprising administering to a subject in need thereof a pharmaceutically effective amount of an oenotein B analogue compound represented by the following Chemical Formula 1 or Chemical Formula 2 or a pharmaceutically acceptable salt thereof Treatment method:[화학식 1][Formula 1]
[화학식 2][Formula 2]
식 중에서, In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R 3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R 3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy Any one selected from the group,R 7 및 R 8은 -OH이고, 및R 7 and R 8 are —OH, andR 7’ 및 R 8’는 각각 독립적으로 -O-, -CH 2- 및 -O(CH 2) p-로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 p는 1 내지 6의 정수이다. R 7 ' and R 8 ' are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6. - 제18항에 있어서, 19. The method of claim 18,상기 비만 합병증은 고혈압; 당뇨병; 고지혈증; The obesity complications include hypertension; diabetes; hyperlipidemia;허리 디스크; 퇴행성 관절염; Herniated disc; degenerative arthritis;복부 비만에 의한 역류성식도염, 탈장 또는 스트레스 요실금; reflux esophagitis, hernia or stress incontinence due to abdominal obesity;수면무호흡증; 비알코올성지방간;sleep apnea; nonalcoholic fatty liver;협심증; 심근경색; 심부전; angina pectoris; myocardial infarction; heart failure;뇌졸중; 뇌경색; stroke; cerebral infarction;여성의 체지방 과다에 의한 여성 호르몬 증가로 초래되는 이른 초경; 배란 장애; 성조숙증; 생리불순; 불임; 다낭성난소증후군으로 이루어진 군으로부터 선택되는 어느 하나의 질환인, 비만, 비만 합병증 또는 이들 모두의 예방 또는 치료 방법.Early menarche caused by increased female hormones due to excess body fat in women; ovulation disorders; precocious puberty; irregular menstruation; sterility; Any one disease selected from the group consisting of polycystic ovary syndrome, obesity, obesity complications, or a method for preventing or treating both.
- 비만, 비만 합병증 또는 이들 모두의 치료에 사용하기 위한, 하기 화학식 1 또는 화학식 2로 표시되는 오에노테인 B 유사체 화합물 또는 이의 약제학적으로 허용가능한 염을 포함하는 조성물:A composition comprising an oenotein B analogue compound represented by the following Chemical Formula 1 or Chemical Formula 2 or a pharmaceutically acceptable salt thereof for use in the treatment of obesity, obesity complications, or both:[화학식 1][Formula 1]
[화학식 2][Formula 2]
식 중에서, In the formula,R 1은 OH, CH 3, COOH, CHO, =O 및 NH 2로 이루어진 군으로부터 선택되는 어느 하나이며, R 1 is any one selected from the group consisting of OH, CH 3 , COOH, CHO, =O and NH 2 ,R 2는 (CH 2) n이고, 여기서 n은 1 내지 6의 정수이고,R 2 is (CH 2 ) n , where n is an integer from 1 to 6,R 3은 -O-, -CH 2- 및 -O(CH 2) m-으로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 m은 1 내지 6의 정수이고,R 3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,R 4, R 4', R 5 및 R 6은 서로 동일하거나 또는 상이하고, 각각 독립적으로 H, (C l-3)알킬, (C l- 3)알케닐, (C l- 3)알키닐, 시아노, 할로, 니트로, 티오, 페닐, 히드록실, (C l- 3)알콕시, (C 2- 4)아실옥시, (C l- 3)카복사미노, 페녹시 및 페닐메톡시로 이루어진 군으로부터 선택되는 어느 하나이고, R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano, consisting of halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, and phenylmethoxy Any one selected from the group,R 7 및 R 8은 -OH이고, 및R 7 and R 8 are —OH, andR 7’ 및 R 8’는 각각 독립적으로 -O-, -CH 2- 및 -O(CH 2) p-로 이루어진 군으로부터 선택되는 어느 하나이고, 여기서 p는 1 내지 6의 정수이다. R 7 ′ and R 8 ′ are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6. - 제20항에 있어서, 21. The method of claim 20,상기 비만 합병증은 고혈압; 당뇨병; 고지혈증; The obesity complications include hypertension; diabetes; hyperlipidemia;허리 디스크; 퇴행성 관절염; Herniated disc; degenerative arthritis;복부 비만에 의한 역류성식도염, 탈장 또는 스트레스 요실금; reflux esophagitis, hernia or stress incontinence due to abdominal obesity;수면무호흡증; 비알코올성지방간;sleep apnea; nonalcoholic fatty liver;협심증; 심근경색; 심부전; angina pectoris; myocardial infarction; heart failure;뇌졸중; 뇌경색; stroke; cerebral infarction;여성의 체지방 과다에 의한 여성 호르몬 증가로 초래되는 이른 초경; 배란 장애; 성조숙증; 생리불순; 불임; 다낭성난소증후군으로 이루어진 군으로부터 선택되는 어느 하나의 질환인, 조성물.Early menarche caused by increased female hormones due to excess body fat in women; ovulation disorders; precocious puberty; irregular menstruation; sterility; Any one disease selected from the group consisting of polycystic ovary syndrome, the composition.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07188275A (en) * | 1993-11-16 | 1995-07-25 | Roussel Uclaf | Ewoseine b for obtaining remedy for disease associated with hyperandrogenism, pharmaceutical composition containingsame, and production of same from eperobium.parubifuroram |
| US20030004131A1 (en) * | 1999-09-10 | 2003-01-02 | Warren Steck | Oenothein medicaments |
| JP2009102288A (en) * | 2007-10-19 | 2009-05-14 | Harunire Bio Kenkyusho:Kk | Fat accumulation inhibitor |
| US20130030007A1 (en) * | 2010-01-07 | 2013-01-31 | Akron Molecules Gmbh | Obesity Small Molecules |
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| KR20140021401A (en) | 2012-08-10 | 2014-02-20 | 코웨이 주식회사 | Apparatus for inspecting water purifier and method for inspecting water purifier |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07188275A (en) * | 1993-11-16 | 1995-07-25 | Roussel Uclaf | Ewoseine b for obtaining remedy for disease associated with hyperandrogenism, pharmaceutical composition containingsame, and production of same from eperobium.parubifuroram |
| US20030004131A1 (en) * | 1999-09-10 | 2003-01-02 | Warren Steck | Oenothein medicaments |
| JP2009102288A (en) * | 2007-10-19 | 2009-05-14 | Harunire Bio Kenkyusho:Kk | Fat accumulation inhibitor |
| US20130030007A1 (en) * | 2010-01-07 | 2013-01-31 | Akron Molecules Gmbh | Obesity Small Molecules |
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| YOSHIDA TAKASHI, YOSHIMURA MORIO, AMAKURA YOSHIAKI: "Chemical and Biological Significance of Oenothein B and Related Ellagitannin Oligomers with Macrocyclic Structure", MOLECULES, vol. 23, no. 3, pages 552, XP055847346, DOI: 10.3390/molecules23030552 * |
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