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WO2004035065A1 - Substances hypoglycemiques contenant du zinc - Google Patents

Substances hypoglycemiques contenant du zinc Download PDF

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Publication number
WO2004035065A1
WO2004035065A1 PCT/JP2003/012741 JP0312741W WO2004035065A1 WO 2004035065 A1 WO2004035065 A1 WO 2004035065A1 JP 0312741 W JP0312741 W JP 0312741W WO 2004035065 A1 WO2004035065 A1 WO 2004035065A1
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WO
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Prior art keywords
zinc
complex
group
aspirin
administration
Prior art date
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Ceased
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PCT/JP2003/012741
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English (en)
Japanese (ja)
Inventor
Yoshitane Kojima
Yutaka Yoshikawa
Naemi Kajiwara
Hiromu Sakurai
Hiroshi Taniguchi
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Priority to AU2003271098A priority Critical patent/AU2003271098A1/en
Publication of WO2004035065A1 publication Critical patent/WO2004035065A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4425—Pyridinium derivatives, e.g. pralidoxime, pyridostigmine
    • 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
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
    • 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
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A61K31/612—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid
    • A61K31/616—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid by carboxylic acids, e.g. acetylsalicylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

Definitions

  • the present invention provides a hypoglycemic effect comprising a zinc (II) organic complex containing as a ligand a compound consisting of salicylic acid having a benzene ring, trigonelline having a pyridi-dimethyl ring, and a derivative thereof, and ⁇ -darkosida light.
  • the present invention relates to a pharmaceutical preparation and a prophylactic agent having an inhibitory action, an anti-inflammatory action, an analgesic action, an anticancer action, an inhibitory action on platelet aggregation, an inhibitory action on blood coagulation, and an antithrombotic action.
  • salicylic acid used as a ligand is contained in willow leaves and bark, and has been used as an analgesic and antipyretic since ancient times.
  • Salicylic acid which has been isolated and confirmed, has become widely used as an analgesic.
  • aspirin acetylsalicylic acid
  • aspirin has been shown to have anti-inflammatory, analgesic, anti-cancer, anti-platelet aggregation, anti-thrombotic effects, and anticoagulant effects that can cause heart attacks and strokes.
  • Aspirin which has been taken for 100 years, is said to contribute to the recovery of patients' health and also to prevent diseases.
  • some organic compounds and natural products have been developed as anti-diabetic drugs, anti-obesity drugs, anti-triglyceride drugs, and used as drugs.
  • type 1 diabetes which depends only on subcutaneous injection of insulin, and there is a need for the development of a therapeutic drug that can be orally administered instead of insulin. It also comes from stress, obesity, lack of exercise, aging, etc. 2
  • Non-insulin dependent Although some therapeutics have been developed and used clinically for type 2 diabetes, they are not universal and often have side-effect problems.
  • vanadyl sulfate is already being used in clinical trials in the United States and elsewhere.
  • zinc (II) ion which is known to be less toxic than vanadium, It has been known from around the time that it has insulin-like activity (see Non-Patent Documents 1-3).
  • Panadyl sulphate (zinc) ion (zinc sulphate and zinc salt) is an inorganic salt, so it is difficult for it to pass through biological membranes and is hardly taken into the living body.
  • Non-Patent Document 1 L. Coulston and P. Dandona, Insulin-like effects of Zn on adipocytes, Diabetes, 29, 665-7 (1980)
  • Non-patent Literature Document 2 J.M. May and C.S.Contoreggi, The mechanism of the insulin-like effects of on oral ionic zinc, J. Biol.Chem., 257, 4362-8 (1982)
  • Non-Patent Document 3 Shisheva, D. Gefel and Y. Shecliter, Insulinlike effects of zinc ion in vitro and in vivo (Zn 2 + is the first agent other than vanadate that administration is able to restore tissue ability to metabolism glucose), .
  • Non-Patent Document 4 E. Ueda, Y. Yoshikawa, Y. Isliino, H. Sakurai, and Y. Kojima, Potential insulino-mimetic agents of zinc (II) complexes with picolinamide.
  • Patent Document 1 Kojima, Sakurai, Zinc (II) Organic Complex Hypoglycemic Agent, PCT: WO 01/39769 A1
  • Patent Document 2 Kojima, Sakurai, Yoshikawa, hypoglycemic agent, PCT: WO 02/060432 A1
  • Patent Document 3 Kojima, Sakurai, Yoshikawa, zinc-containing food, PCT: WO 02/089606 A1 Since zinc (II) ions (zinc sulfate, zinc chloride, etc.) are inorganic salts, they are difficult to pass through living organisms. It is difficult to be taken into the living body. In addition, dispirin salicylate, which has anti-inflammatory, analgesic, anti-cancer, anti-platelet aggregation, anti-thrombotic effects, and anticoagulant effect of causing heart attacks and strokes, etc. There are side effects. (Disclosure of the Invention)
  • the present invention provides a prophylactic / therapeutic treatment comprising a zinc (II) complex having a lower toxicity than zinc (II) ions, a moderate stability, and a moderate lipophilicity.
  • the purpose is to provide drugs.
  • Many zinc (II) complexes with hypoglycemic activity have been developed by the applicants, but complexes that can prevent and treat multiple health problems have not been developed so far.
  • the present invention relates to a drug which can be safely prevented and treated as an anti-inflammatory action, an analgesic action, a pile cancer action, a platelet aggregation inhibitory action, a thrombotic preventive action, and a blood coagulation inhibitory action that causes heart attack and stroke.
  • An object of the present invention is to provide a zinc (II) complex having aspirin and an analog thereof as a ligand.
  • the problem to be solved by the present invention is a pharmaceutical composition containing a zinc (II) complex as an active ingredient, which causes diabetes, hypertension, inflammation, pain, carcinogenesis, and heart attack and stroke.
  • the present invention relates to a pharmaceutical composition for treating blood coagulation and thrombus.
  • the pharmaceutical composition of the present invention is preferably a pharmaceutical composition comprising a pharmaceutically acceptable simple substance and a mixture thereof in addition to the above-mentioned zinc (II) complex.
  • the present invention relates to an agent comprising an organic compound capable of forming a complex with zinc and a zinc source.
  • organic compound capable of forming a complex with zinc include, but are not limited to, organic compounds having a benzene ring and a pyridinium ring in addition to the general formulas (1) to (2). It is not done.
  • any zinc source suitable for administration to humans and / or other animals may be used.
  • a zinc mineral salt or a zinc organic complex is preferable.
  • Examples of zinc mineral salts include zinc acetate, zinc chloride, zinc sulfate, and zinc nitrate. I can do it.
  • the pH adjuster may be, for example, a basic aqueous solution such as potassium hydroxide, sodium hydroxide, lithium hydroxide, barium hydroxide, or the like.
  • a buffer such as a citrate buffer or a phosphate buffer may be used in combination.
  • Preferred examples of the zinc organic complex include a zinc organic complex having, as a ligand, a compound selected from the group consisting of salicylic acids, trigonelins, and derivatives thereof.
  • the shape of the drug according to the present invention may be any of powder, granule, fatigue type, capsule, liquid, gel, and the like.
  • FIG. 1 shows a full chart of infrared absorption starch (IR) of a bis (salicylic acid) Z zinc (II) complex according to the present invention.
  • FIG. 1 shows the infrared absorption spectrum (IR) of bis (trigonelline) nozinc (II) complex.
  • FIG. 3 shows the change in blood glucose level when the bis (aspirin) Z zinc ( ⁇ ) complex, [Zn (asp) 2 (H 20 ) 2 ], was intraperitoneally administered once a day.
  • FIG. 4 shows changes in body weight when the bis (aspirin) / zinc ( II ) complex, [Zn (asp) 2 (H 20 ) 2 ], was intraperitoneally administered once a day.
  • Figure 5 represents 14 days, bis (aspirin) / zinc (II) complex, after administration [Zn (asp) 2 (H 2 0) 2], and the transition of the blood glucose level when performing the glucose tolerance test ing.
  • the complex non-administration group (violent) and the [Zn (asp) 2 (H 2 0) 2 ] complex administration group ( ⁇ ) are plotted.
  • * indicates the group of p 0.05 and the complex non-administered group.
  • Figure 6 shows the results of the sucrose tolerance test (OSTT) after administration of the bis (aspirin) / zinc ( II ) complex, [Zn (asp) 2 (H 2 0) 2 ], aspirin and water. Changes in blood sugar levels.
  • FIG. 7 shows changes in the HbAlc value before and after administration of the bis (aspirin) / zinc (II) complex, [Zn (asp) 2 (H 20 ) 2 ], and the administration.
  • * indicates p ⁇ 0.05 vs before KK_A y mouse
  • FIG. 8 is a graph showing the relationship between the bis (salicylic acid) / zinc (II) complex concentration () and the ⁇ -dalcosidase inhibition rate (%) in Experimental Example 4.
  • FIG. 9 is a graph showing the relationship between the bis (aspirin) zinc (II) complex concentration (mM) and the ⁇ - darcosidase inhibition rate (%) in Experimental Example 4.
  • Non-Patent Document 5 K. Singla and H. Wadhwa, Int.J. Phamaseutics, 108, 173-185 (1994)
  • BSA bovine serum albumin
  • KRB buffer 1 O
  • Table 1 to Table the IC 5 o values for each zinc (II) complex relative to the VOS0 4 values (IC 5 o 1.00).
  • KK- Ay mice of type 2 diabetes model animals were used.
  • the blood glucose level in the abdominal cavity is 250 mg IdL or more.
  • the complex was administered to give 1.5 mg Zn / kg body weight.
  • changes in body weight were also monitored.
  • the animals were fasted for 16 hours, and glucose was administered to give 1 g glucose I kg body weight, and a glucose tolerance test was performed.
  • HbAlc was measured before and after administration, and biochemical serum parameters were measured using blood obtained from orbital blood collection after administration.
  • KK- Ay mice were used for the oral sucrose tolerance test (0STT). Water was orally administered to 9-week-old KK- Ay mice for 3 days. Thereafter, fasted about 1 6 hours, empty stomach in the early morning, Zn (asp) 2 (H 2 0) 2 complex (5 nig Zn / kg body weight), aspirin (Zn (asp) 2 (H 2 0) 2 complex throw The amount corresponding to aspirin at the time of administration) and pre-administered water. 60 minutes after the pre-administration, sucrose was administered to give a weight of 2 g / kg body weight, and a sucrose tolerance test was performed. Blood glucose was measured at 60 minutes before administration, at 0 minutes after administration of sucrose, at 15 minutes, 30 minutes, 60 minutes, 90 minutes, and 120 minutes after administration of sucrose. This was performed a total of seven times (Figure 6).
  • 0.1 M substrate maltose and sucrose dissolved in 0.15 M HEPES buffer pH 6.8) or 4% starch solution (0.15 M HEPES buffer pH 6.8) 0 0.1 ml of the test substance solution and 0.1 ml of the enzyme solution were added to 1 ml, reacted at 37 ° C for 60 minutes, and then boiled to stop the reaction.
  • the amount of generated glucose was measured by a glucose oxidase method (glucose CII test Co., Ltd.).
  • a control the absorbance Ac when a solvent was added instead of the test substance was measured, and ⁇ -gnorecosidase inhibitory activity was measured by the following equation (FIGS. 8 and 9).
  • a-Darcosidase inhibitory activity (%) [(Ac— As) / Ac] X 100
  • the blood glucose level began to decrease after administration of the complex, and at the end of the 14-day administration, decreased by about 150 rag IdL as compared to before administration.
  • the zinc complex-administered group as a pretreatment tended to suppress an increase in blood glucose level after sucrose loading as compared to the groups administered aspirin or water.
  • the blood glucose peak time was 30 minutes after sucrose loading in the zinc complex administration group, but peaked after 15 minutes in the other groups (Fig. 6). ).
  • Figure 7 shows the change in HbAlc values before and after administration of the bis (aspirin) Z zinc (II) complex.
  • the HbAlc value before administration was 7.2, 0.5. /.
  • the value of HbAlc after administration decreased to 0.2% in 6.6 soils, which was significantly lower than the value before administration.
  • an agent comprising an organic compound capable of forming a complex with zinc and a zinc source is
  • zinc (II) ion It is less toxic than zinc (II) ion, has good stability, has good fat solubility, hypoglycemic action, ⁇ -darcosidase inhibitory action, anti-inflammatory action, analgesic action, anti-cancer action, It is expected to be a promising agent containing a zinc (II) complex that has platelet aggregation inhibitory action, thrombus preventive action, and blood coagulation inhibitory action that causes heart attack and stroke.
  • hyperlipidemia a drug that is effective in the prevention and treatment of cerebral disorders, atherosclerosis, cardiovascular disease, hyperglycemia, angina, hypertension, congestive heart failure, diabetic complications, or taste disorders. , Is what is expected.
  • the complex of the present invention is safe without substantial side effects even during long-term ingestion.

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  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Hematology (AREA)
  • Pain & Pain Management (AREA)
  • Obesity (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Emergency Medicine (AREA)
  • Rheumatology (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention a pour but de développer des médicaments ayant un effet hypoglycémique, inhibiteur d'α-glucosidase, anti-inflammatoire, analgésique, anticancéreux, antiplaquettaire et antithrombotique, ainsi qu'un effet inhibiteur de la coagulation sanguine, cause d'infarctus du myocarde et d'apoplexie, ceci en utilisant des complexes de zinc (II) contenant de l'acide salicylique, de l'aspirine, de la trigonelline et des dérivés de ces produits, conjointement avec une source de zinc. L'invention concerne en conséquence des préparations médicamenteuses et préventives ayant un effet hypoglycémique, inhibiteur d'α-glucosidase, anti-inflammatoire, analgésique, anti-cancéreux, antiplaquettaire et antithrombotique, ainsi qu'un effet inhibiteur de la coagulation sanguine, cause d'infarctus du myocarde et d'apoplexie, et comprenant des complexes organiques de zinc (II) contenant, comme ligand, un composé sélectionné à partir d'acide salicylique ayant un noyau benzénique, de trigonelline ayant un noyau pyridinium et de dérivés de ces produits.
PCT/JP2003/012741 2002-10-18 2003-10-03 Substances hypoglycemiques contenant du zinc Ceased WO2004035065A1 (fr)

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AU2003271098A AU2003271098A1 (en) 2002-10-18 2003-10-03 Hypoglycemic substances containing zinc

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JP2002304751 2002-10-18
JP2002-304751 2002-10-18
JP2003-315857 2003-09-08
JP2003315857A JP2004155766A (ja) 2002-10-18 2003-09-08 血糖降下作用を有する亜鉛含有物

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004105771A1 (fr) * 2003-05-28 2004-12-09 Bayer Healthcare Ag Association d'acide acetylsalicylique et d'inhibiteurs de l'alpha-glucosidase
FR2901274A1 (fr) * 2006-05-19 2007-11-23 Coordination De Rech S Therape Nouveaux complexes metalliques, procede pour leur preparation et leur utilisation therapeutique
US7736676B2 (en) * 2003-05-14 2010-06-15 Indus Biotech Pvt. Ltd. Synergistic composition for the treatment of diabetes mellitus
CN110776420A (zh) * 2019-11-18 2020-02-11 山东省化工研究院 一种卡巴匹林钙的合成工艺
CN116063356A (zh) * 2023-01-18 2023-05-05 广东电网有限责任公司 一种烷基水杨酸异质金属衍生物及其制备方法与应用

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5759175B2 (ja) * 2008-09-29 2015-08-05 日本碍子株式会社 ガス吸着材料、その前駆体及びガス吸着材料の製造方法
WO2010055170A1 (fr) * 2008-11-17 2010-05-20 Technische Universität München Dérivés de pyrimidine à utiliser dans le traitement ou la prévention du diabète
EP4076431B1 (fr) * 2019-12-20 2024-01-31 Vector Vitale IP LLC Composition et procédé pour la prévention et le traitement du diabète de type 2

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Publication number Priority date Publication date Assignee Title
GB1553749A (en) * 1976-03-31 1979-09-26 Egyt Gyogyszervegyeszeti Gyar Oligo- and polygalacturonic acid complexes formed with essential metal ions
WO1987001281A1 (fr) * 1985-08-27 1987-03-12 Glyzinc Pharmaceuticals Limited Complexe de glycerolate de zinc et produits d'addition pour applications pharmaceutiques
WO2001039769A1 (fr) * 1999-11-30 2001-06-07 Japan Science And Technology Corporation Hypoglycemiants a base de complexes de zinc (ii) organiques
WO2002060432A1 (fr) * 2001-01-31 2002-08-08 Japan Science And Technology Corporation Agent hypoglycemique
JP2003199532A (ja) * 2001-12-28 2003-07-15 Junichi Arita 亜鉛有機組成物からなる食品
JP2003319760A (ja) * 2002-02-26 2003-11-11 Junichi Arita 抗肥満作用を有する亜鉛含有物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1553749A (en) * 1976-03-31 1979-09-26 Egyt Gyogyszervegyeszeti Gyar Oligo- and polygalacturonic acid complexes formed with essential metal ions
WO1987001281A1 (fr) * 1985-08-27 1987-03-12 Glyzinc Pharmaceuticals Limited Complexe de glycerolate de zinc et produits d'addition pour applications pharmaceutiques
WO2001039769A1 (fr) * 1999-11-30 2001-06-07 Japan Science And Technology Corporation Hypoglycemiants a base de complexes de zinc (ii) organiques
WO2002060432A1 (fr) * 2001-01-31 2002-08-08 Japan Science And Technology Corporation Agent hypoglycemique
JP2003199532A (ja) * 2001-12-28 2003-07-15 Junichi Arita 亜鉛有機組成物からなる食品
JP2003319760A (ja) * 2002-02-26 2003-11-11 Junichi Arita 抗肥満作用を有する亜鉛含有物

Non-Patent Citations (2)

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Title
MASLENNIKOVA, I.S. ET AL: "Use of Infrared spectroscopy for determining the nature of coordination in some transition metal complexes", ZHURNAL FIZICHESKOI KHIMII, vol. 44, no. 10, 1970, pages 2509 - 2511, XP002975870 *
YOSHIKAWA, Y ET AL: "Studies on the development of organic zink (II) complexes with blood glucose lowering effect", BIOMED. RES. TRACE ELEMENTS, vol. 12, no. 1, 2001, pages 104 - 109, XP002975871 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7736676B2 (en) * 2003-05-14 2010-06-15 Indus Biotech Pvt. Ltd. Synergistic composition for the treatment of diabetes mellitus
WO2004105771A1 (fr) * 2003-05-28 2004-12-09 Bayer Healthcare Ag Association d'acide acetylsalicylique et d'inhibiteurs de l'alpha-glucosidase
FR2901274A1 (fr) * 2006-05-19 2007-11-23 Coordination De Rech S Therape Nouveaux complexes metalliques, procede pour leur preparation et leur utilisation therapeutique
CN110776420A (zh) * 2019-11-18 2020-02-11 山东省化工研究院 一种卡巴匹林钙的合成工艺
CN110776420B (zh) * 2019-11-18 2022-04-26 山东省化工研究院 一种卡巴匹林钙的合成工艺
CN116063356A (zh) * 2023-01-18 2023-05-05 广东电网有限责任公司 一种烷基水杨酸异质金属衍生物及其制备方法与应用

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