EP2268277A1 - Verwendung von flavonoidverbindungen für die propyhylaxe und therapie ischämischer oder entzündlicher herz- und kreislauferkrankungen - Google Patents
Verwendung von flavonoidverbindungen für die propyhylaxe und therapie ischämischer oder entzündlicher herz- und kreislauferkrankungenInfo
- Publication number
- EP2268277A1 EP2268277A1 EP09718237A EP09718237A EP2268277A1 EP 2268277 A1 EP2268277 A1 EP 2268277A1 EP 09718237 A EP09718237 A EP 09718237A EP 09718237 A EP09718237 A EP 09718237A EP 2268277 A1 EP2268277 A1 EP 2268277A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- glucuronide
- quercetin
- compounds
- heart
- extract
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- 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
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- 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
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/87—Vitaceae or Ampelidaceae (Vine or Grape family), e.g. wine grapes, muscadine or peppervine
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Definitions
- the present invention relates to the use of flavonoid compounds, in particular of flavonol glucosides and flavonol glucuronides, especially of quercetin-3-O- ⁇ -D-glucoside, kaempferol-3-O- ⁇ -D-glucoside and the corresponding glucuronides, quercetin-3-O - ⁇ -D-glucuronide and kaempferol-3-O- ⁇ -D-glucuronide, for the prevention of diseases of the heart and circulatory system.
- certain vegetable extracts e.g. made from endive, celery or extract of red vine leaves.
- polyphenols have been proposed as an important factor.
- the class of polyphenols includes a wide range of subgroups, such as catechins, flavonoids, procyanidins or isoflavones. All of these subgroups have been found to be diverse, cell or organ protective due to in vitro studies Attributed effects.
- appropriate plant material rich in polyphenols and extracted from the plant is placed in direct contact with cell or organ systems.
- the target organs do not come into contact with the substances in the same way.
- Quercetin is one of the most widely studied flavonols, both in vitro and after parenteral administration to animals (Formica et al., Fd Chem. Toxic 1995; 12: 1061-1080). However, quercetin is only slightly absorbed (Manach et al., J Clin Nutr 2005; 81 (1 Suppl): 230S-242S). Quercetin occurs naturally in the form of glycosides and glucuronides (McAnlis et al., Eur J Clin Nutr 1999; 53 (2): 92-96; Graefe et al., Journal of Clinical Pharmacology 2001; 41 (5): 492 -499).
- flavonoids especially flavonol glucuronides, in particular quercetin-3-0-.beta.-D-glucuronide and Kamp fero 1-3 -0-.beta.-D-glucuronide
- flavonol glucuronides are poorly absorbed in the gastrointestinal tract. Therefore, in previous medical applications (eg in the therapy of CVI) their corresponding glucosides are used as prodrugs. Extract of red vine leaves is especially rich in quercetin glucoside and camphor glucoside.
- the present invention therefore also encompasses an intra-arterial administration and use of quercetin-3-O-.beta.-D-glucuronide prepared purely neat and / or MUSTero 1-3-O-ß- D-glucuronide for reducing the risk of functional organ failure, with the latter being able to adapt under analogous conditions to all organs and not to the heart alone.
- quercetin-3-O-.beta.-D-glucuronide prepared purely neat and / or
- MUSTero 1-3-O-ß- D-glucuronide for reducing the risk of functional organ failure, with the latter being able to adapt under analogous conditions to all organs and not to the heart alone.
- the use of Quercetinglucosid and / or Kamp fero lglucoside alone or as an extract of red vine leaves which has a high concentration of both compounds claimed as a prodrug for peroral administration.
- flavonol compounds are substances having a 3-hydroxyflavone structure, in particular those having free hydroxyl groups.
- Preferred flavonols are derivatives of quercetin and camphor oil.
- preferred flavonol compounds in the context of the present invention are quercetin glucuronide and Kampfero lglucuronide, in particular quercetin 3-O- ⁇ -D-glucuronide and kaempferol-3-O- ⁇ -D-glucuronide.
- flavonoid compounds preferably quercetin-3-O-.beta.-D-glucuronide and
- Mattero 1-3 -O-.beta.-D-glucuronide intravascularly, can also be administered intraarterially. This would also circumvent the problem of low absorption by the digestive tract.
- such an intravascular application is only conditionally suitable for routine preventive measures.
- the flavonol compounds can also be administered perorally.
- the flavonol compounds in addition to the corresponding pure glucosides, which are then metabolized as "prodrugs" as described above to the corresponding glucuronides, it is above all plant extracts which are rich in flavonoids that are particularly advantageous
- This extract is particularly rich in quercetin-3-O-.beta.-D Glucoside and kaempferol-3-O-.beta.-D-glucoside and can be administered either as a drop or as a capsule or tablet
- the extract mentioned in EP 1 225 810 contains 2 to 20% flavonoids, the aqueous extract being obtainable from red grape leaves is by a process comprising the following steps:
- This extract is suitable for oral administration, in particular in a solid dosage form, ie a capsule or tablet consisting of 20 to 60% of an aqueous extract of red grape leaves with a high content of flavonoids of 2-15%.
- a solid dosage form ie a capsule or tablet consisting of 20 to 60% of an aqueous extract of red grape leaves with a high content of flavonoids of 2-15%.
- Another preferred dosage form consists of drops containing 3 to 90% of the extract.
- Other suitable forms of administration may include coated tablets, syrups or the like.
- the extract is characterized by a high content of 2 to 20% and preferably 2 to 10% of biologically active flavonoids.
- Carriers or excipients may be added during drying to facilitate further processing of the extract. Such excipients or excipients may be silica, maltodextrin, glucose syrup, cellulose and the like.
- Preferred dosage forms are tablets, including coated tablets or capsules.
- liquid preparations preferably drops, can also be selected.
- a preferred embodiment for an orally administrable preparation according to the present invention is a film-coated tablet, in particular as proposed in EP 1 581 195.
- the film-coated tablet disclosed therein contains 50 to 70% of a dry vine leaf extract with a flavonoid content of 2-15%, which was prepared by the aqueous extraction method described above.
- the film-coated tablet contains auxiliaries in the core of the tablet.
- the weight ratio of extract to the excipients is from 1: 1 to 2: 1, preferably from 1.1: 1 to 1.8: 1, preferably from 1.25: 1 to 1.75: 1.
- An exemplary film-coated tablet contains
- the excipients (b) consist of
- Binder means an adjuvant that binds ingredients together.
- Preferred binders are: cellulose powder, microcrystalline cellulose, sorbitol, starch, povidone, copolymers of vinylpyrrolidone with other derivatives (copovidones), cellulose derivatives, especially methylhydroxypropylcellulose, eg Methocel A 15 LV, and mixtures thereof.
- the preferred binders are cellulose powder, microcrystalline cellulose and / or povidone.
- the abovementioned binders are used in a range of 15-45% by weight, preferably 25-40% by weight, preferably 33% by weight, based on the total weight of the tablet.
- the tablet according to the invention also contains disintegrants in addition to the aforementioned ingredients. These are preferably selected from sodium starch glycolate, crospovidone, croscarmellose sodium salt (sodium salt of cellulose C arboxymethyl ether, crosslinked), sodium carboxymethyl cellulose, dried corn starch, colloidal anhydrous silica and mixtures thereof.
- disintegrants are used in a range from 0.5 to 10% by weight, preferably from 1.5 to 7.5% by weight, based on the total weight of the tablet.
- the tablet according to the invention also comprises a filler which is described as an inert, inorganic metal oxide or phosphate or hydrogen phosphate.
- a filler which is described as an inert, inorganic metal oxide or phosphate or hydrogen phosphate.
- Calcium hydrogen phosphate is the preferred filler.
- the abovementioned fillers are used in a range from 1 to 10% by weight, preferably from 2 to 8% by weight, based on the total weight of the tablet.
- the tablet according to the invention also contains flow agents and / or lubricants in addition to the aforementioned ingredients. These include silica, talc, stearic acid, sodium stearyl fumarate, magnesium stearate and glycerol tribehenates.
- the aforementioned flow and lubricants are used in a range of 0.1 to 10 wt .-%, preferably from 0.6 and 1.5 wt .-%, measured on the total weight of the tablet.
- flavonols are vegetable extracts, e.g. from endive, celery and the like
- mice Female guinea pigs (250-33Og) were used as heart donors. After decapitating the animals, their hearts were explanted and placed in a Langendorff apparatus (self-construction). The perfusion under normal conditions was retrograde via the aorta under a constant pressure of 60 mm Hg for 3 min (mode 1). For perfusion, 37 ° C-warm Krebs-Henseleit bicarbonate buffer (KHM) was used without the addition of quercetiglucuronide (QG), which was fumigated with carbogen before use. After cannulation of the left atrium was switched to the working mode (mode 2) with a preload of lOmmHg and an afterload of 60mmHg.
- KHM 37 ° C-warm Krebs-Henseleit bicarbonate buffer
- QG quercetiglucuronide
- the baseline functions were registered, in particular: aortic flow, coronary flow, ejection output, heart rate, systolic pressure maximum, mean arterial pressure, and the product of heart rate and systolic pressure maximum.
- Histological sections are made from the frozen tissue and arterioles or venules in the myocardial tissue are identified on the basis of their typical marker enzymes (alkaline phosphatase or dipeptidylamino peptidase).
- PMN are immunohistochemically identified with monoclonal anti-PMN antibody (MBL, Japan), T with monoclonal anti-CD61, and counted under the microscope.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Botany (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mycology (AREA)
- Cardiology (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Heart & Thoracic Surgery (AREA)
- Medical Informatics (AREA)
- Nutrition Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008012909A DE102008012909A1 (de) | 2008-03-06 | 2008-03-06 | Verwendung von Flavonoidverbindungen für die Prophylaxe und Therapie ischämischer oder entzündlicher Herz- und Kreislauferkrankungen |
PCT/EP2009/052502 WO2009109573A1 (de) | 2008-03-06 | 2009-03-03 | Verwendung von flavonoidverbindungen für die propyhylaxe und therapie ischämischer oder entzündlicher herz- und kreislauferkrankungen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2268277A1 true EP2268277A1 (de) | 2011-01-05 |
Family
ID=40600026
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP09718237A Withdrawn EP2268277A1 (de) | 2008-03-06 | 2009-03-03 | Verwendung von flavonoidverbindungen für die propyhylaxe und therapie ischämischer oder entzündlicher herz- und kreislauferkrankungen |
Country Status (6)
Country | Link |
---|---|
US (2) | US20110053874A1 (ja) |
EP (1) | EP2268277A1 (ja) |
JP (1) | JP2011527984A (ja) |
CA (1) | CA2717012A1 (ja) |
DE (1) | DE102008012909A1 (ja) |
WO (1) | WO2009109573A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011512320A (ja) * | 2007-08-31 | 2011-04-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 赤ブドウの葉の抽出物を含む噴霧可能な組成物 |
DE102008012908A1 (de) * | 2008-03-06 | 2009-09-10 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Methode zum anti-inflammatorischen und anti-ödematösen Schutz von explantiertem biologischen Material bis zu seiner Transplantation in Patienten |
US10316053B2 (en) | 2012-10-11 | 2019-06-11 | Armaron Bio Pty Ltd | Flavonoid compounds and uses thereof |
CN113398114B (zh) * | 2021-05-28 | 2022-11-01 | 浙江大学智能创新药物研究院 | 3,7,8,4′-四羟基黄酮在制备抗心血管疾病药物中的应用 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1124561B1 (en) * | 1998-10-29 | 2004-07-21 | MERCK PATENT GmbH | Compositions comprising a mixture of bioflavonols |
JP2001122791A (ja) * | 1999-10-20 | 2001-05-08 | Boehringer Ingelheim Internatl Gmbh | 下肢の慢性静脈不全の軽減および予防のための赤色ブドウ樹葉の水性抽出物よりなる食事補強剤 |
PT1317272E (pt) * | 2000-05-25 | 2006-06-30 | Boehringer Ingelheim Int | Composicao para melhoramento da proteccao celular compreendendo um antioxidante lipofilo e um antioxidante hidrofilo |
CN1197567C (zh) * | 2002-10-21 | 2005-04-20 | 中国人民解放军第二军医大学 | 山奈酚衍生物用于制备防治脑血管疾病药物的用途 |
JP4989071B2 (ja) | 2002-12-31 | 2012-08-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 赤ブドウ葉抽出物を含むフィルムコート錠 |
-
2008
- 2008-03-06 DE DE102008012909A patent/DE102008012909A1/de not_active Withdrawn
-
2009
- 2009-03-03 WO PCT/EP2009/052502 patent/WO2009109573A1/de active Application Filing
- 2009-03-03 US US12/919,561 patent/US20110053874A1/en not_active Abandoned
- 2009-03-03 JP JP2010549125A patent/JP2011527984A/ja active Pending
- 2009-03-03 EP EP09718237A patent/EP2268277A1/de not_active Withdrawn
- 2009-03-03 CA CA2717012A patent/CA2717012A1/en not_active Abandoned
-
2012
- 2012-12-11 US US13/710,799 patent/US20130109641A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
JP2011527984A (ja) | 2011-11-10 |
CA2717012A1 (en) | 2009-09-11 |
US20130109641A1 (en) | 2013-05-02 |
WO2009109573A1 (de) | 2009-09-11 |
DE102008012909A1 (de) | 2009-09-10 |
US20110053874A1 (en) | 2011-03-03 |
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