WO2008038712A1 - Agent thérapeutique/prophylactique du syndrome métabolique - Google Patents

Agent thérapeutique/prophylactique du syndrome métabolique Download PDF

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Publication number
WO2008038712A1
WO2008038712A1 PCT/JP2007/068808 JP2007068808W WO2008038712A1 WO 2008038712 A1 WO2008038712 A1 WO 2008038712A1 JP 2007068808 W JP2007068808 W JP 2007068808W WO 2008038712 A1 WO2008038712 A1 WO 2008038712A1
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WO
WIPO (PCT)
Prior art keywords
metabolic syndrome
salt
geranylgeranylacetone
agent
present
Prior art date
Application number
PCT/JP2007/068808
Other languages
English (en)
Japanese (ja)
Inventor
Eiichi Araki
Tatsuya Kondo
Kazunari Sasaki
Hironori Adachi
Hirofumi Kai
Original Assignee
Kumamoto University
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 Kumamoto University filed Critical Kumamoto University
Priority to JP2008536424A priority Critical patent/JPWO2008038712A1/ja
Publication of WO2008038712A1 publication Critical patent/WO2008038712A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/12—Ketones
    • A61K31/121—Ketones acyclic
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • 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
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to a therapeutic / preventive agent for metabolic syndrome.
  • Lifestyle-related diseases include obesity, diabetes, hypertension, and hyperlipidemia. These lifestyle-related diseases are often caused by obesity, which is not an independent disease. Often duplicates. A state in which such lifestyle-related diseases are combined is sometimes referred to as metabolic syndrome. Recently, it has been found that the causes of these lifestyle-related diseases include abnormal sugar metabolism and abnormal lipid metabolism.
  • the provisional diagnostic criteria for metabolic syndrome in Japan is that it has visceral fat type obesity, and in addition to this, it is said that it has two or more of hyperglycemia, hypertension and hyperlipidemia! .
  • GGA geranylgeranylacetone
  • Patent Document 1 Japanese Patent Laid-Open No. 53-145922
  • Patent Document 2 Japanese Patent Application Laid-Open No. 62-10013
  • Patent Document 3 Japanese Unexamined Patent Publication No. 2003-267863
  • An object of the present invention is to provide a novel therapeutic / prophylactic agent for metabolic syndrome that has few side effects!
  • the present inventors have intensively studied to solve the above-mentioned problems, and the effect of teprenone (geranyl geranylacetone) on the metabolic syndrome, body weight suppression action, blood sugar lowering action, insulin resistance improving action, and blood adiponectin The effect of increasing the amount was examined. As a result, 200 mg / kg of teprenone was orally administered to mice that induced diabetes with insulin resistance due to high-fat diet loading. 2 days of daily administration suppressed weight gain, improved insulin resistance, and glucose tolerance An improvement in performance was observed. The blood concentration of adiponectin, which improves insulin resistance, also increased. From these results, it was found that teprenone is effective as a therapeutic agent for metabolic syndrome. The present invention has been completed based on these findings.
  • a therapeutic / preventive agent for metabolic syndrome containing geranylgeranylacetone, a salt thereof, a hydrate or a solvate thereof as an active ingredient.
  • the therapeutic / prophylactic agent for metabolic syndrome of the present invention is used for suppressing weight gain, reducing blood glucose, improving insulin resistance, and / or increasing blood adiponectin level.
  • a weight gain inhibitor containing geranylgeranylacetone, a salt thereof, or a hydrate or solvate thereof as an active ingredient.
  • hypoglycemic agent comprising geranylgeranylacetone, a salt thereof, or a hydrate or solvate thereof as an active ingredient.
  • an insulin resistance ameliorating agent containing geranylgeranylacetone, a salt thereof, or a hydrate or solvate thereof as an active ingredient.
  • an agent for increasing the amount of adiponectin in blood containing geranylgeranylacetone, a salt thereof, or a hydrate or solvate thereof as an active ingredient.
  • treatment of metabolic syndrome comprising the step of administering an effective amount of geranylgeranylacetone, a salt thereof, or a hydrate or solvate thereof to a mammal including a human.
  • a method of preventing, a method of suppressing weight gain, a method of reducing blood sugar, a method of improving insulin resistance, or a method of increasing blood adiponectin level are provided.
  • a therapeutic / preventive agent for metabolic syndrome a weight gain inhibitor, a hypoglycemic agent, an insulin resistance ameliorating agent, or a blood adiponectin amount increasing agent.
  • Geranylgeranylacetone, a salt thereof, or a hydrate or solvate thereof is provided.
  • Metabolic syndrome is attracting attention as a cause of arteriosclerotic diseases, and the presence of insulin resistance due to the accumulation of visceral fat is regarded as important.
  • a novel therapeutic agent for metabolic syndrome can be provided. Since the high safety of geranylgeranylacetone used as an effective component in the present invention has already been recognized, the present invention can provide a safe therapeutic agent for metabolic syndrome with few side effects. .
  • teprenone (geranylgeranylacetone) has an insulin resistance improving action, a body weight gain inhibiting action, and a serum adiponectin level raising action. From these results, it was shown that teprenone (geranylgeranylacetone) can be an insulin resistance ameliorating agent / weight gain inhibitor.
  • metabolic syndrome has been attracting attention as a cause of arteriosclerotic diseases, and the presence of insulin resistance due to the accumulation of visceral fat is regarded as important.
  • teprenone (geranyl geranylacetone) is clinically applied as an early intervention for metabolic syndrome Is possible.
  • the therapeutic agent for metabolic syndrome according to the present invention contains geranylgeranylacetone as an active ingredient.
  • Geranyl geranyl acetone used as an active ingredient in the medicament of the present invention is represented by the following formula (I), and the compound name is 6, 10, 14, 18-tetramethyl 1, 5, 9, 13, 17-nona. Decatetraen 1 2-one compound.
  • Geranylgeranylacetone is generally called teprenone and is also abbreviated as GGA.
  • Geranylgeranylacetone has various isomers. Any isomer can be used in the present invention.
  • the 5, 9, and 13 positions may be either E-form or Z-form, and one kind of isomer may be used, or a mixture of two kinds of isomers may be used.
  • Geranylgeranylacetone is widely used as a therapeutic agent for gastric ulcer and gastritis, and a pharmaceutical grade is readily available. Moreover, the synthesis method of geranylgeranylacetone is well-known, for example, it can synthesize
  • geranylgeranylacetone may be used as a salt.
  • the salt of geranylgeranylacetone is not particularly limited as long as it is a pharmacologically acceptable salt.
  • the salt of geranylgeranylacetone is preferably a hydrohalide salt (eg hydrofluoride, hydrochloride, hydrobromide, hydroiodide, etc.), inorganic acid salt (eg sulfate, nitrate) , Perchlorate, phosphate, carbonate, bicarbonate, etc.), organic carboxylates (eg, acetate, maleate, tartrate, fumarate, kenate, etc.), organic sulfonates (For example, methanesulfonate, ethanesulfonate, benzenesulfonate, toluenesulfonate, camphorsulfonate, etc.), amino acid salts (eg aspartate, glutamate, etc.), quatern
  • the geranylgeranylacetone used in the present invention may be any of an anhydride, a hydrate, and a solvate.
  • the preparation form of the therapeutic agent for metabolic syndrome of the present invention is not particularly limited, and an appropriate form most suitable for the purpose of treatment or prevention is selected from the preparation forms for oral administration or parenteral administration.
  • Examples of the dosage form suitable for oral administration include tablets, capsules, powders, granules, fine granules, syrups, solutions, emulsions, suspensions, and tuples.
  • Suitable dosage forms for administration include, for example, transdermal forms such as injections (subcutaneous injection, intramuscular injection, intravenous injection, etc.), drops, inhalants, sprays, suppositories, gels or ointments.
  • a force S that can include an absorbent, a transmucosal absorbent, a patch or a transdermal absorbent in the form of a tape, etc., but is not limited thereto.
  • Liquid preparations suitable for oral administration include water, sorbits, sugars such as fructose, darikols such as polyethylene glycol and propylene glycol, sesame oil, olive oil, It can be manufactured using oils such as bean oil, preservatives such as p-hydroxybenzoates, and flavors such as strawberry flavor and peppermint.
  • solid preparations such as capsules, tablets, powders or granules, excipients such as lactose and mannitol, disintegrants such as starch and sodium alginate, lubricants such as magnesium stearate and talc are used.
  • Agents, binders such as polyvinyl alcohol, hydroxypropyl cellulose, and gelatin, surfactants such as fatty acid esters, and plasticizers such as glycerin can be used.
  • An injectable or infusion preparation suitable for parenteral administration preferably contains the above-mentioned substance as an active ingredient dissolved or suspended in a sterile aqueous medium isotonic with the blood of the recipient.
  • a solution can be prepared using a salt solution or an aqueous medium composed of a mixture of salt water and another solution.
  • Formulations for enteral administration can be prepared, for example, using carriers such as strength cacao butter, hydrogenated fats, or hydrogenated carboxylic acids, and are provided as suppositories.
  • the above-mentioned substances that are active ingredients can be dispersed as fine particles, without irritating the recipient's oral cavity and airway mucosa
  • a carrier that facilitates absorption of the active ingredient can be used.
  • the carrier include lactose and glycerin.
  • formulations in the form of aerosols or dry powders can be prepared. These preparations for parenteral administration include one selected from glycols, oils, flavors, preservatives, excipients, disintegrants, lubricants, binders, surfactants, plasticizers, etc. Two or more auxiliary components can also be added.
  • the dose and frequency of administration of the therapeutic agent for metabolic syndrome of the present invention are appropriately determined depending on various factors such as the type and severity of the disease, the dosage form, conditions such as the age and weight of the patient, and the presence or absence of complications.
  • the force S that can be set generally 200 mg / kg per day as the active ingredient dosage is preferred. Because it is metabolized in the liver and kidneys, it is desirable to reduce the dose in elderly people! The maximum dose is considered to be 500 mg / kg!
  • the therapeutic agent for metabolic syndrome of the present invention can be administered to any mammal including humans, and is preferably administered to humans.
  • the therapeutic agent for metabolic syndrome of the present invention can be used to suppress weight gain, decrease blood glucose, improve insulin resistance, and / or increase blood adiponectin level.
  • a weight gain inhibitor, a hypoglycemic agent, an insulin resistance improver, comprising geranylgeranylacetone, a salt thereof, or a hydrate or solvate thereof as an active ingredient is provided.
  • the therapeutic agent for metabolic syndrome of the present invention can be used as a weight gain inhibitor. Since obesity is closely related to the metabolic syndrome, the metabolic syndrome can be treated and / or prevented by suppressing weight gain using the therapeutic agent for metabolic syndrome of the present invention.
  • the therapeutic agent for metabolic syndrome of the present invention can also be used as a hypoglycemic agent.
  • diabetes is a disease based on abnormal glucose metabolism characterized by hyperglycemia, and diabetes can be treated by lowering the blood glucose level of diabetic patients using the metabolic syndrome therapeutic agent of the present invention, Diabetes can also be prevented by controlling blood glucose levels in patients suspected of having diabetes.
  • the metabolism of the present invention The therapeutic agent for cough syndrome can be widely used not only for the prevention and / or treatment of diabetes but also for the reduction of blood glucose.
  • Hyperglycemia may be clinically shown by various diseases other than diabetes, such as organic disorders of the winning tissue, chronic liver disease, endocrine disease, increased brain pressure, obesity, overeating, alcohol overdose, stomach Hyperglycemia can occur due to various factors such as dietary hyperglycemia after resection, febrile illness, carbon monoxide poisoning, and drug-induced blood glucose elevation.
  • the therapeutic agent for metabolic syndrome of the present invention may be used to reduce these hyperglycemia.
  • the therapeutic / preventive agent for metabolic syndrome of the present invention can also be used as an agent for improving insulin resistance.
  • a pathological condition with increased insulin resistance so-called insulin resistance syndrome
  • lifestyle-related diseases for example, diabetes, hypertension or obesity
  • Improving insulin resistance plays an important role.
  • the lifestyle-related diseases caused by the insulin resistance syndrome can be treated or prevented.
  • the therapeutic / preventive agent for metabolic syndrome of the present invention can also be used as a calorie increasing agent for blood adiponectin level.
  • Adiponectin is a protein produced and extracted from adipocytes, and is closely involved in sugar and lipid metabolism. In patients with cardiovascular disease, diabetes or obesity, blood adiponectin levels are generally decreased. Therefore, a decrease in blood adiponectin concentration is closely related to lifestyle-related diseases such as hypertension, diabetes or obesity, and is considered to contribute to these lifestyle-related diseases. Therefore, it is possible to treat or prevent the above lifestyle-related diseases caused by hypoadiponectinemia by increasing the blood adiponectin level using the therapeutic / preventive agent for metabolic syndrome of the present invention.
  • Adiponectin is also associated with insulin resistance.
  • insulin resistance is known to increase, and in animal models, it is known to improve adiponectin administration power S, insulin resistance life span, and improve glucose metabolism. Therefore, diabetes or diabetic complications can be treated or prevented by increasing the amount of adiponectin in the blood using the therapeutic / preventive agent for metabolic syndrome of the present invention.
  • mice Ten 11-week-old C57BL / 6 mice were prepared and divided into a control group (5 mice) and a teprenone group (5 mice).
  • the control group and the teprenone group were loaded with a high fat diet for 1 week, and their body weight and blood glucose level were measured.
  • 0.008% tocopherol dissolved in Phosphate Buffered Saline
  • 200 mg / kg of teprenone dissolved in 0.008% tocopherol was added to the teprenone group.
  • the dose was orally administered once daily.
  • body weight and blood glucose level were measured, and an insulin tolerance test (0.75 U / kg) was performed.
  • insulin tolerance test insulin (0.75 U / kg) was administered intraperitoneally, and blood glucose levels were measured from 0 to 120 minutes. Three days later, a glucose tolerance test (1 g / kg) was conducted. In the glucose tolerance test, glucose (1 g / kg) was administered intraperitoneally and blood glucose levels were measured from 0 to 120 minutes. Leptin was measured using a mouse leptin kit (Morinaga), and adiponectin was measured using a mouse / rat adiponectin ELISA kit (Otsuka Pharmaceutical).
  • Fig. 1 shows the measurement results of body weight
  • Fig. 2 shows the change in blood glucose level in the glucose tolerance test
  • Fig. 3 shows the change in blood glucose level in the insulin tolerance test
  • Fig. 4 shows the measurement results of levtin and adiponectin. .
  • control group was 118 mg / dl, while the teprenone group was 96 mg / dl. (See Figure 3: Blood glucose level at 0 minutes)
  • the present invention provides a safe therapeutic agent for metabolic syndrome with few side effects. it can.
  • FIG. 1 shows the results of measuring changes in body weight. GGA seemed to suppress weight gain.
  • FIG. 2 shows changes in blood glucose level in a glucose tolerance test. In the glucose tolerance test, glucose tolerance improved!
  • FIG. 3 shows changes in blood glucose level in an insulin tolerance test. In the insulin tolerance test, it seemed that insulin resistance improved! /.
  • FIG. 4 shows the measurement results of leptin and adiponectin. Like MET, the leptin level was not different, but the adiponectin level increased!

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Diabetes (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Child & Adolescent Psychology (AREA)
  • Epidemiology (AREA)
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Abstract

L'invention concerne un nouvel agent thérapeutique/prophylactique du syndrome métabolique qui ne présente guère d'effets secondaires indésirables. Plus précisément, l'invention concerne un agent thérapeutique/prophylactique du syndrome métabolique, qui comprend géranyle-génanyle-acétone, un sel de celui-ci, ou un hydrate ou solvat de géranyle-génanyle-acétone ou son sel comme ingrédient actif.
PCT/JP2007/068808 2006-09-27 2007-09-27 Agent thérapeutique/prophylactique du syndrome métabolique WO2008038712A1 (fr)

Priority Applications (1)

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JP2008536424A JPWO2008038712A1 (ja) 2006-09-27 2007-09-27 メタボリックシンドロームの治療・予防剤

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JP2006262190 2006-09-27
JP2006-262190 2006-09-27

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WO2008038712A1 true WO2008038712A1 (fr) 2008-04-03

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005060303A (ja) * 2003-08-12 2005-03-10 Sutaagen:Kk 不動性骨粗鬆の治療または予防剤
WO2005115366A1 (fr) * 2004-05-31 2005-12-08 Kaneka Corporation Agent pour prévenir/améliorer les maladies liées au mode de vie contenant un composant d'huile essentielle de curcuma
JP2006063012A (ja) * 2004-08-26 2006-03-09 Univ Nagoya 抗ポリグルタミン病剤
WO2006085562A1 (fr) * 2005-02-09 2006-08-17 Kaneka Corporation Préparation pour le traitement prophylactique et/ou thérapeutique du syndrome métabolique et du syndrome d'insulinorésistance
JP2006225263A (ja) * 2003-06-02 2006-08-31 Eisai Co Ltd 腎疾患予防・治療剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006225263A (ja) * 2003-06-02 2006-08-31 Eisai Co Ltd 腎疾患予防・治療剤
JP2005060303A (ja) * 2003-08-12 2005-03-10 Sutaagen:Kk 不動性骨粗鬆の治療または予防剤
WO2005115366A1 (fr) * 2004-05-31 2005-12-08 Kaneka Corporation Agent pour prévenir/améliorer les maladies liées au mode de vie contenant un composant d'huile essentielle de curcuma
JP2006063012A (ja) * 2004-08-26 2006-03-09 Univ Nagoya 抗ポリグルタミン病剤
WO2006085562A1 (fr) * 2005-02-09 2006-08-17 Kaneka Corporation Préparation pour le traitement prophylactique et/ou thérapeutique du syndrome métabolique et du syndrome d'insulinorésistance

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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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