WO2008032980A1 - Nouveau dérivé de stigmastérol ou sel pharmaceutiquement acceptable correspondant, procédé de production, et composition contenant ce produit pour lutter contre l'obésité ou prévenir et traiter l'hyperlipidémie - Google Patents

Nouveau dérivé de stigmastérol ou sel pharmaceutiquement acceptable correspondant, procédé de production, et composition contenant ce produit pour lutter contre l'obésité ou prévenir et traiter l'hyperlipidémie Download PDF

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Publication number
WO2008032980A1
WO2008032980A1 PCT/KR2007/004395 KR2007004395W WO2008032980A1 WO 2008032980 A1 WO2008032980 A1 WO 2008032980A1 KR 2007004395 W KR2007004395 W KR 2007004395W WO 2008032980 A1 WO2008032980 A1 WO 2008032980A1
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WO
WIPO (PCT)
Prior art keywords
compound
formula
obesity
cholesterol
stigmasterol
Prior art date
Application number
PCT/KR2007/004395
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English (en)
Inventor
Chung-Oh Kong
Original Assignee
Cns Pharm Korea Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cns Pharm Korea Co., Ltd. filed Critical Cns Pharm Korea Co., Ltd.
Publication of WO2008032980A1 publication Critical patent/WO2008032980A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class

Definitions

  • the present invention relates to a novel stigmasterol derivative or a pharmaceutically acceptable salt thereof, a method of producing the same, and a composition containing the same to inhibit obesity or to prevent and treat hyperlipidemia.
  • the excess body weight has a body mass index (BMI, an index of obesity that is obtained by dividing weight by the square of height) in the range of 25 or more and less than 30.
  • BMI body mass index
  • the obesity means that the body mass index is in the range of 30 or more.
  • Obesity means that fat is excessively accumulated in the body and the ratio of fat to body weight is relatively high. Obesity is classified into simple obesity and secondary obesity (symptomatic obesity).
  • sample obesity may be caused by overeating, insufficient exercise, and a reduced basal metabolic rate. Most of the cases that are clinically diagnosed are simple obesity. If simple obesity continues over a long period of time, various types of disorders may occur.
  • Secondary obesity is caused by certain basis diseases and examples thereof may include endocrine obesity, hypothalamus obesity, hereditary obesity, or obesity resulting from medicine.
  • the main cause of obesity is due to the excessive growth of adipocytes, and the excessive growth of adipocytes is caused by the lack of hormone, which is called leptin that is secreted by the order of the brain.
  • the lack of leptin hormone is caused by overeating, reduced metabolism in the living body due to aging, and animal cholesterol that is excessively accumulated in the body, with the exception of the case of the hereditary leptin hormone deficiency.
  • Cholesterol includes small spherical lipoprotein particles in the blood. Lipoprotein is classified into various types. Lipoprotein that carries cholesterol from the liver to the other tissues is called low density lipoprotein (LDL), and lipoprotein that carries cholesterol from the other tissues to the liver is called high density lipoprotein (HDL). Particularly, HDL-cholesterol functions to clean the blood vessel to reduce arteriosclerosis. Thus, in the case when the content of HDL-cholesterol is low, the occurrence of arteriosclerosis is increased similar to the case when the content of LDL- cholesterol is high, which is considered to be unhealthy.
  • LDL low density lipoprotein
  • HDL high density lipoprotein
  • Obesity incurs diseases such as hyperlipidemia, hypertension, cardiovascular disease, pseudotumor cerebri, sleep apnea, cancer, pulmonary hypertension, cholecystitis, and osteoarthritis, or reduces movement. Furthermore, obesity may be a complication resulting from various types of diseases.
  • obesity occurs when ingestion energy continues while being more than consumption energy. Some obese patients make an effort to reduce body weight and cholesterol by diet therapy and exercise therapy for the purpose of treating obesity. Additionally, patients are subjected to behavioral treatment, psychotherapy, drug treatment, or bariatric surgery (a surgical operation such as gastric banding).
  • Det therapy is a method of controlling the total energy intake.
  • diet therapy is problematic in that since a metabolic rate is reduced during rest, it is difficult to ensure a sufficient weight reduction.
  • weight other than fat weight is reduced, such that physical and mental pains such as malnutrition disorder, hunger, or stress occur.
  • Behavioral treatment or psychotherapy is used as an auxiliary means of diet therapy or exercise therapy, and not considered as a main treatment to obtain the desired effect.
  • the obese person do a low-impact exercise such as swimming.
  • medicine that has a low side effect and activation of energy metabolism may be used while the patient does a low-impact exercise such as swimming to increase muscle mass and promote consumption of energy due to an increase in basal metabolism, thereby reducing the possibility of obesity.
  • stigmasterol is phytosterol that is contained in soybean milk and has a structure similar to that of animal cholesterol.
  • stigmasterol is absorbed in the guts while competing with animal cholesterol to reduce the concentration of cholesterol in the body and suppress the excessive growth of adipocytes.
  • calcium phosphate is accumulated in the joints or muscles and muscular atrophy occurs.
  • Glucosamine is one of natural amino sugars that constitute the joints and the cartilages and its molecular formula is C H NO .
  • Glucosamine has 6 carbon atoms,
  • glucosamine and galactosamine are generically known as hexosamine.
  • Glucosamine is a strong basic material that has colorless needle crystals, and is decomposed at 11O 0 C and dissolved in water.
  • Natural glucosamine is present in a chitin form or a polysaccharide form such as mucopolysaccharides constituting the cell walls of bacteria or the cartilages or skins of animals.
  • a large amount of proteins that are bonded to glucosamine are contained in blood or mucus of humans, and glycolipid that is bonded to glucosamine is present in the cell membrane of a red blood cell.
  • chitin may be decomposed using a hydrochloric acid to produce glucosamine.
  • glucosamine prevents acetate from being provided into the cell to suppress formation of acetyl GoA. As a result, the synthesis of fats and cholesterol is obstructed.
  • Snce glucosamine is known as a material that helps make the joint and the cartilage strong, it is extensively used in medicines for degenerative arthritis, cosmetic compositions, foods, and the like.
  • the present inventors have conducted studies on a compound capable of reducing the amount of cholesterol and preventing adipocytes from growing in the body, which has resulted in the finding of a novel stigmasterol derivative produced by the present inventors that reduces the contents of triglyceride, total cholesterol, and LDL-cholesterol in the blood, increases the content of HDL- cholesterol, and prevents body weight from being increased, thereby accomplishing the present invention.
  • the present invention provides a novel stigmasterol derivative or a pharmaceutically acceptable salt thereof, a method of producing the same, and a composition containing the same to inhibit obesity or to prevent and treat hyperlipidemia. Best Mode for Carrying Out the Invention
  • a novel stigmasterol derivative represented by the following Formula 1 or a pharmaceutically acceptable salt thereof is provided.
  • the compound of the present invention may be used m the form of a pharmaceutically acceptable salt and a solvate according to the conventional method m the related art.
  • acid addition salts produced with free acids are preferred.
  • the acid addition salts are produced by the conventional method, for example, a method comprising the steps of dissolving a compound in an excessive amount of acid aqueous solution, and precipitating the salt using water-miscible organic solvents such as methanol, ethanol, acetone or acetomtrile.
  • Acid or alcohol for example, glycol monomethyl ether
  • the free acids organic acids and inorganic acids may be used.
  • Examples of the inorganic acids include hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, and tartaric acid
  • examples of the organic acids include methanesulfonic acid, p-toluenesulfonic acid, acetic acid, trifluoroacetic acid, citric acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, mandelic acid, propionic acid, lactic acid, glycollic acid, gluconic acid, galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, vanillic acid, and hydroiodic acid, but are not limited thereto.
  • a pharmaceutically acceptable metal salt can be produced using a base.
  • An alkali metal salt and alkaline earth metal salt can be obtained by a method, in which a compound is dissolved in an excessive amount of alkali metal hydroxide or alkaline earth metal hydroxide solution, filtered the undissolved salt, and then the filtrate is evaporated and dried.
  • metal salts it is preferable that sodium, potassium, or calcium salt is pharmaceutically preferable, and the corresponding silver salt is obtained by reacting alkali metal salt or alkaline earth metal salt with a suitable silver salt (e.g. silver nitrate).
  • a pharmaceutically acceptable salt of the compound represented by Formula 1 includes salts of acidic or basic groups, which can be present in the compound of Formula 1 unless otherwise specified.
  • the pharmaceutically acceptable salt includes sodium salt, calcium salt, potassium salt of a hydroxy group
  • other pharmaceutically acceptable salt of an amino group includes hydrochloride, hy- drobromide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, acetate, succinate, citrate, tartrate, lactate, mandelate, methanesulfonate (mesylate), and p-toluenesulfonate (tosylate).
  • the salts can be produced by a known method for producing a salt or a production process in the related art.
  • an intermediate compound of the stigmasterol derivative represented by the following Formula 3 or 4 or a pharmaceutically acceptable salt thereof is provided.
  • the method of producing the stigmasterol derivative of the present invention comprises the steps of: [40] 1) producing the compound of Formula 3 by reacting stigmasterol and the compound of Formula 2, [41] 2) producing the compound of Formula 4 by reacting the compound of Formula 3 produced in step 1) and an ammonia aqueous solution, and [42] 3) producing the compound of Formula 1 by reacting the compound of Formula 4 produced in step 2) and palladium hydroxide [Pd(OH) ]. [43] [Reaction Scheme 1]
  • the compound of Formula 2 as a starting material can be produced by the method described in Chemical. Reviews 1993, Vol. 93, No. 4, p. 1511 or the like or the similar method thereto, and used.
  • step 1) stigmasterol and the compound of Formula 2 are dissolved in an organic solvent, and then BF OEt was added thereto. The mixture is subjected to reaction at normal temperature for 10-20 hours to produce the compound of Formula 3.
  • the organic solvent is preferably selected from the group consisting of dimethyl ether, tetrahydrofuran, methylene chloride, methanol, cyclohexene, acetonitrile, dimethylformamide, and dimethyl sulfoxide, but is not limited thereto.
  • step 2) the compound of Formula 3 produced in step 1) is dissolved in an organic solvent, and reacted with the ammonia aqueous solution in a water bath at 30 ⁇ 50°C for 10-20 hours to produce the compound of Formula 4.
  • the organic solvent can be selected from the organic solvents used in step 1).
  • the base is preferably selected from the group consisting of sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, potassium bicarbonate, tri- ethylamme, pyridine, DBU, and ammonium hydroxide, but is not limited thereto.
  • step 3 the compound of Formula 4 produced in step 2) is dissolved in an organic solvent and distilled water, and reacted with palladium hydroxide [Pd(OH) ] to produce the compound of Formula 1.
  • the organic solvent used herein can be selected from the organic solvents used in step 1).
  • composition containing the stigmasterol derivative represented by Formula 1 or the pharmaceutically acceptable salt thereof to inhibit obesity or to prevent and treat hyper- lipidemia is provided.
  • the stigmasterol derivative according to the present invention has the excellent effects of decreasing blood levels of triglyceride, total cholesterol, and LDL cholesterol, increasing blood level of HDL-cholesterol, and inhibiting body weight gain.
  • toxicity test was performed by orally administering the stigmasterol derivative according to the invention to a mouse, resulting in a Lethal Ebse 50 (LD )
  • the stigmasterol derivative according to the present invention can be used as a medicine and as health food useful for inhibiting obesity or for preventing and treating hyperlipidemia.
  • composition of the invention may contain at least one kind of active ingredient known in the art, which has the effect of inhibiting obesity or preventing or treating hyperlipidemia, in addition to the compound of Formula 1.
  • the composition of the invention can include at least one pharmaceutically acceptable carrier, in addition to the active ingredients as described above.
  • the pharmaceutically acceptable carrier include saline solution, sterile water, Ringer's solution, buffered saline solution, dextrose solution, maltodextrin solution, glycerol, ethanol and a mixture of one or more thereof.
  • the composition may also contain other conventional additives such as antioxidants, buffers, and bacteriostatic agents.
  • the composition may additionally contain diluents, dispersants, surfactants, binders, and lubricants in order to formulate it into injectable formulations such as aqueous solution, suspension, and emulsion, pills, capsules, granules, and tablets.
  • injectable formulations such as aqueous solution, suspension, and emulsion, pills, capsules, granules, and tablets.
  • the composition may preferably be formulated depending on particular diseases and its components, using the method described in Remington's Pharmaceutical Science (latest edition), Mack Publishing Cbmpany, Easton PA, which is a suitable method in the relevant field of art.
  • composition of the invention may be administered orally or parenterally (for example, intravein, subcutaneous, intraperitoneal, or topical application).
  • the dosage of the composition of the invention can vary depending on various factors, including the patient's weight, age, sex, health condition, and diet, and administration time, administration route, secretion rate, disease severity, etc.
  • the compound of Formula 1 is administered at a daily dosage of about 5-30 mg/kg, preferably 10-25 mg/kg one time or several times.
  • composition of the invention may be used alone or in combination with surgical operations, hormone therapies, chemical therapies, and other methods using biological reaction regulators, in order to inhibit obesity or to prevent or treat hyperlipidemia.
  • the composition of the present invention can be added to a health food for the purpose of improving the diseases caused by obesity or hyperlipidemia.
  • the compound of Formula 1 of the invention can be added as it is or with other foods or food ingredients, and suitably used according to the conventional method.
  • the mixed amount of active ingredient can be suitably determined depending on its purpose (prevention, health, or treatment).
  • the compound of Formula 1 of the invention is added 15% by weight or less, preferably 10% by weight or less, based on a raw material.
  • the amount may be less than the above range. Snce there is no problem in safety, the active ingredient may be used in an amount more than the above range.
  • the kind of food is not particularly limited.
  • Examples of the food, to which the substance can be added include meat, sausage, bread, chocolate, candy, snack, cookie, pizza, instant noodle, other noodles, chewing gum, dairy products including icecream, various kinds of soup, beverage, tea, drink, alcoholic beverages and vitamin complex, and includes all kinds of typical health foods.
  • the health beverage composition of the present invention may contain various flavors, natural carbohydrates or the like as an additional ingredient, similarly to a conventional beverage.
  • natural carbohydrates include monosaccharides such as glucose, fructose, disaccharides such as maltose, sucrose, polysaccharides such as dextrin and cyclodextrin, sugaralcohols such as xylitol, sorbitol, erythritol.
  • sweeteners include natural sweeteners such as thaumatin and stevioside, and artificial sweeteners such as saccharin and aspartame.
  • the content of the natural carbohydrate is generally about 0.01-0.04 g, preferably about 0.02-O.03 g, based on 100 m£ of the composition of the present invention.
  • the composition of the invention may contain various nutrients, vitamins, minerals, flavoring agent, coloring agent, pectic acid and a salt thereof, alginic acid and a salt thereof, organic acid, protective colloid thickener, pH control agent, stabilizer, preservative, glycerin, alcohol, carbonating agent used in carbonated beverages or the like, in addition to the above-mentioned. Further, the composition of the invention may contain fruit fleshes for production of natural fruit juice, fruit juice beverage, and vegetable beverage. The above ingredients can be used alone or in combination therewith. Generally, the content of the additives is, but not considered significant, 0.01-O.l parts by weight, based on 100 parts by weight of the composition of the present invention. Mode for the Invention
  • LDL-cholesterol [Total cholesterol - HDL-cholesterol - (triglyceride / 5)]
  • mice Sx-week-old ICR mice were used as test animals. The mice were allowed to freely ingest solid feed and water at the temperature of 23+1 0 C and the humidity of 60+5% before the test was performed. The test animals were divided into groups, and six mice were included in each group. The compound 1 that was produced in Example 1 was suspended in a 0.5% methyl cellulose solution and then orally administered in the amount of 1 g/kg/15 mH once. After the test material was administered, mice were observed for 14 days in views of appearance and death. The dead mice were subjected to an autopsy and observed in terms of grosslesions. The LD value was obtained by using the Richfield- Wilcoxon method.
  • the compound of the present invention does not incur a change in toxicity until the amount is increased to 3000 mg/kg in respects to all the mice. Additionally, the compound is evaluated as a safe substance having the oral administration lethal dose 50 (LD ) of 3000 mg/kg or more.
  • LD lethal dose 50
  • PREPARATION EXAMPLE 2 Production of foods [133] Foods that contain the compound of Formula 1 according to the present invention were produced by using the following methods. [ 134] 1. Production of seasonings [135] 20-95 % by weight of compound of Formula 1 was used to produce seasonings that were healthy.
  • Sde materials such as fructose liquid (0.5%), oligosaccharide (2%), sugar (2%), common salt (0.5%), and water (75%) and the compound of Formula 1 were homogeneously mixed with each other and instantaneously sterilized.
  • the sterilized mixture was packed by using small-sized vessels such as glass bottles and pet bottles to produce beverages that were healthy.
  • the stigmasterol derivative according to the present invention is advantageous in that the stigmasterol derivative reduces the contents of triglyceride, total cholesterol, and LDL-cholesterol in blood, increases the content of HDL-cholesterol, and suppresses an increase in body weight. Accordingly, it is possible to use the stigmasterol derivative according to the present invention as medicines and health foods that are useful to suppress obesity or to prevent and treat hyperlipidemia.

Abstract

Nouveau dérivé de stigmastérol ou sel pharmaceutiquement acceptable correspondant, procédé de production, et composition contenant ce produit pour lutter contre l'obésité ou prévenir et traiter l'hyperlipidémie. Ledit dérivé a l'avantage de réduire le taux de triglycérides, le taux de cholestérol total, et le taux de cholestérol-LDL dans le sang, d'augmenter le taux de cholestérol HDL, et d'endiguer la prise de poids. On peut donc utiliser ce dérivé comme médicament et produit diététique utile pour enrayer l'obésité ou prévenir et traiter l'hyperlipidémie.
PCT/KR2007/004395 2006-09-12 2007-09-11 Nouveau dérivé de stigmastérol ou sel pharmaceutiquement acceptable correspondant, procédé de production, et composition contenant ce produit pour lutter contre l'obésité ou prévenir et traiter l'hyperlipidémie WO2008032980A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20060087875 2006-09-12
KR10-2006-0087875 2006-09-12
KR10-2007-0091861 2007-09-11
KR1020070091861A KR100886466B1 (ko) 2006-09-12 2007-09-11 신규한 스티그마스테롤 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법, 및 이를 포함하는 비만억제 또는 고지혈증 예방 및 치료용 조성물

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009021740A2 (fr) 2007-08-15 2009-02-19 Sanofis-Aventis Nouvelles tétrahydronaphtalines substituées, leurs procédés de préparation et leur utilisation comme médicaments
WO2011157827A1 (fr) 2010-06-18 2011-12-22 Sanofi Dérivés d'azolopyridin-3-one en tant qu'inhibiteurs de lipases et de phospholipases
EP2567959A1 (fr) 2011-09-12 2013-03-13 Sanofi Dérivés d'amide d'acide 6-(4-Hydroxy-phényl)-3-styryl-1H-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000052029A1 (fr) * 1999-03-04 2000-09-08 Eugene Science Inc. Derive de sterol hydrosoluble inhibant l'absorption de cholesterol et procede d'elaboration
KR20020081834A (ko) * 2001-04-20 2002-10-30 주식회사 유엘바이오텍 식물성 스테롤의 유도체를 이용한 혈중 콜레스테롤저하제의 제조방법 및 이에 의해 제조된 혈중 콜레스테롤저하제
WO2005005453A2 (fr) * 2003-07-09 2005-01-20 Forbes Medi-Tech Inc. Nouveaux composes et compositions comprenant des sterols et/ou des stanols et des inhibiteurs de biosynthese du cholesterol et utilisation associees pour le traitement et la prevention de maladies et d'etats divers

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000052029A1 (fr) * 1999-03-04 2000-09-08 Eugene Science Inc. Derive de sterol hydrosoluble inhibant l'absorption de cholesterol et procede d'elaboration
KR20020081834A (ko) * 2001-04-20 2002-10-30 주식회사 유엘바이오텍 식물성 스테롤의 유도체를 이용한 혈중 콜레스테롤저하제의 제조방법 및 이에 의해 제조된 혈중 콜레스테롤저하제
WO2005005453A2 (fr) * 2003-07-09 2005-01-20 Forbes Medi-Tech Inc. Nouveaux composes et compositions comprenant des sterols et/ou des stanols et des inhibiteurs de biosynthese du cholesterol et utilisation associees pour le traitement et la prevention de maladies et d'etats divers

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Title
KAZUNOBU TOSHIMA ET AL.: "Recent Progress in O-Glycosylation Methods and Its Application to Natural Products Synthesis", CHEMICAL REVIEWS, vol. 93, no. 4, June 1993 (1993-06-01), pages 1503 - 1531 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009021740A2 (fr) 2007-08-15 2009-02-19 Sanofis-Aventis Nouvelles tétrahydronaphtalines substituées, leurs procédés de préparation et leur utilisation comme médicaments
WO2011157827A1 (fr) 2010-06-18 2011-12-22 Sanofi Dérivés d'azolopyridin-3-one en tant qu'inhibiteurs de lipases et de phospholipases
EP2567959A1 (fr) 2011-09-12 2013-03-13 Sanofi Dérivés d'amide d'acide 6-(4-Hydroxy-phényl)-3-styryl-1H-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs

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KR20080024075A (ko) 2008-03-17

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