WO2003018080A1 - Systeme d'administration locale de medicament dans des extenseurs coronaires - Google Patents

Systeme d'administration locale de medicament dans des extenseurs coronaires Download PDF

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Publication number
WO2003018080A1
WO2003018080A1 PCT/IB2002/003480 IB0203480W WO03018080A1 WO 2003018080 A1 WO2003018080 A1 WO 2003018080A1 IB 0203480 W IB0203480 W IB 0203480W WO 03018080 A1 WO03018080 A1 WO 03018080A1
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WO
WIPO (PCT)
Prior art keywords
coating
ajoene
allicin
composition
poly
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.)
Ceased
Application number
PCT/IB2002/003480
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English (en)
Inventor
Managoli Nandkishore
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Sahajanand Biotech Pvt Ltd
Original Assignee
Sahajanand Biotech Pvt Ltd
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Filing date
Publication date
Application filed by Sahajanand Biotech Pvt Ltd filed Critical Sahajanand Biotech Pvt Ltd
Publication of WO2003018080A1 publication Critical patent/WO2003018080A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • A61L29/16—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/602—Type of release, e.g. controlled, sustained, slow
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/606—Coatings

Definitions

  • This invention relates to the field of cardiology and, more particularly, to a system for the localised delivery of a drug for use following coronary angioplasty or stenting.
  • the invention provides a stent, or other implantable medical device, which has a coating that contains ajoene and/or allicin.
  • Ajoene and allicin are derived from garlic and have been found to be effective in the prevention or inhibition of restenosis following angioplasty.
  • interventional cardiologists deal with the coronary vessels in disease, they are faced with the unenviable task of handling stenosed blood vessels with small diametric lumina, narrowed further by atherosclerotic plaques and vasospasm, leading to near- total, or total blockage of the arteries.
  • Cardiac intervention in such cases in the form of coronary angioplasty or stenting, causes endothelial damage leading to thrombosis, inflammation, proliferation and remodelling of the vasculature.
  • Such selective coagulation inhibitors or anticoagulants and antiproliferative drugs or agents have been isolated from biological sources, such as animals and plants, or have been synthesized in the laboratory in the past few years.
  • the latest advance in pharmacology namely the local drug delivery technique, where drug molecules are packaged with polymers or are bonded to the surface of a device by using biologically derived materials, such as serum, and delivered at the desired site by using a "time-release technique" (i.e. to achieve sustained release of the drug in a controlled manner over a predetermined and prolonged period of time), is nyisaged as the ideal method to locally manage the restenosis problem.
  • Stents are tubular structures that are implanted within blood vessels and other passageways within the human or animal body for the purpose of treating disease conditions such as aneurysms, occlusions and stenosis. They function to physically support and, if necessary, expand the wall of the blood vessel or other passageway into which they have been implanted. Stents can have either solid or lattice-like walls and may be either self-expandable or expanded by means of inflating a balloon positioned within them.
  • Stents and other implantable medical devices are also commonly used to carry and deliver therapeutic substances, such as anticoagulants, antiplatelet agents and cytostatic agents. These therapeutic substances are often carried in a polymer coating on the stent and then released over a period of time once it has been implanted in the blood vessel or other passageway.
  • US Patent Nos. 5994341, 5869127, 6168619, 6179817, 6203551, 6231600, 6254632, 6258121 and 6280411 describe stents and other implantable medical devices which may have a biocompatible polymeric coating that contains a therapeutic agent.
  • Garlic Allium sativum has been used in traditional medicine for thousands of years; for example, for the prevention of strokes, coronary thrombosis and atherosclerosis, as well as for the treatment of various infectious diseases and vascular disorders.
  • Some components of garlic are known to have antibiotic properties, while others are potent inhibitors of platelet aggregation (one of the initial stages of blood clot formation or thrombosis).
  • US Patent No. 4917921 teaches the combination of a component of garlic called dithiin (a monomeric organosulphur compound that has antibiotic and antithrombogenic properties) with a biocompatible polymer, and the use of the resulting composition in a method for coating polymeric articles.
  • the invention resulted from the finding that ajoene and allicin, which are two components of garlic, have antithrombotic, antibiotic, antiinflammatory and antiproliferative properties and are effective (both individually and together) for preventing or inhibiting restenosis.
  • an implantable medical device such as a stent, comprising a substrate and a biocompatible polymeric coating which covers at least a portion of the said substrate, and wherein the coating contains ajoene and/or allicin or isomers, analogues, homologues or derivatives thereof.
  • the present invention provides a composition which comprises one or more biocompatible polymers and ajoene and/or allicin or isomers, analogues, homologues or derivatives thereof and which is suitable for use in coating an implantable medical device.
  • the present invention still further provides a method of manufacturing an implantable medical device which includes the step of applying such a composition as a coating to the said device.
  • the coating of the stent or other implantable medical device typically contains a total of from 50 to 800 micrograms of the drug or active ingredient (i.e. of ajoene alone, allicin alone or ajoene and allicin in combination).
  • the composition of the coating typically comprises from 60 to 80% by weight of the polymer (preferably 70%) and from 20 to 40%) by weight of the drug (preferably 30%).
  • the invention also provides a method of manufacturing an implantable medical device which comprises applying to a substrate a coating of a composition.
  • the composition may be prepared as a solution of ajoene and/or allicin with biodegradable and biocompatible polymers selected from lactone-based polyesters or copolyesters such as polylactide, polycaprolactone-glycolide, polyorthoesters, polyanhydrides, poly-aminoacids, polysaccharides; polyphosphazenes; poly (ether-ester) copolymers, or blends thereof in a solovent selected from dichloromethane. Dimethyl formamide, dimethyl sulphoxide, hexafluoroisopropanol or acetone.
  • the polymer may be non- absorbable and biocompatible.
  • the polymers are such as polydimethylsiloxane; poly (ethylene-vinylacetate); acrylate based polymers or copolymers, poly (hydroxyethyl methylmethacrylate, polyvinyl pyrrolidone; fluorinated polymers such as polytetrafluoroethylene; cellulose esters.
  • the implantable medical devices of this invention include tubular scaffolding bodies, grafts, catheters and, in particular, endoluminal stents (including cardiovascular stents) designed for dealing with various intraluminal occlusions and contractions within the body.
  • the substrate referred to above is thus typically a stent body and which may be made of, for example, metal or a polymer composition.
  • the biocompatible polymeric coating has a composition which pennits the ajoene and/or allicin to be controllably released in a predetermined manner over a prolonged period of time. It will be appreciated that its precise composition will be chosen to produce the desired release profile.
  • the polymeric coating may be either biodegradable or non-biodegradable. It may consist of either a single biocompatible polymer or a combination of two or more such materials.
  • the coating comprises polyactides, polyglycolides, polycaprolactone, polydioxanone, polygluconate, polyanhydrides, polyphosphoesters, polyethyleneterpthalate, polyhydroxylbutyrate, polyphosphazene, polyorthoesters or polyphosphate esters, or mixtures or copolymers thereof.
  • the ajoene and/or allicin is disposed, dispersed, dissolved, embedded, micro- encapsulated or otherwise incorporated in the coating or a part of the coating.
  • the coating may comprise two or more layers and which each contain one or both of these components. It will be appreciated that its precise composition will be chosen to produce the desired release profile.
  • the ideal agent(s) for the management of coronary restenosis would have the following properties:
  • antithrombotic and antiplatelet activity to control the amount of thrombus formation and also to control the process of intimal regeneration, which will prevent restenosis
  • antilipemic and antiatherosclerotic activity which act to maintain the potency of the vascular lumen in hyperlipidemic patients and also to improve blood flow by reducing plasma viscosity (blood-thinning property);
  • antiproliferative activity to control neointimal hyperplasia
  • antiseptic activity which may be useful in taking care of any infection introduced during the invasive procedure of angioplasty or coronary stenting
  • Ajoene (from "ajo", Spanish for garlic) is a sulphur-containing natural product derived from the ubiquitous and perennial bulbous herb, Allium sativum. Garlic contains 33 sulphur compounds, the chief one being allicin (diallyl thiosulphonate) which is formed only when garlic is cut or macerated or heated. This r is the compound responsible for the offensive odour of garlic. Ajoene is formed by the combination of three molecules of allicin.
  • Ajoene is (E,Z) 4, 5, 9 - trithiadodeca -1, 6, 11 -triene-9-oxide) and has the following structural formula:-
  • E-a j oene Allicin is S-allyl-2-propenethiosulphinate and has the following structural formula:
  • Ajoene and a precursor thereof can be isolated from extracts of garlic. As the garlic is crushed, allicin in the garlic comes into contact with allinase in the cell wall to form allicin. In the presence of a polar molecule (such as a lower alcohol) or even water, allicin forms ajoene.
  • a polar molecule such as a lower alcohol
  • Antithrombotic, antiinflammatory arid antiplatelet activity This effect is achieved by interfering with cyclo-oxygenase mediated thromboxane synthesis (a potential stimulant) non-competitively and irreversibly. It inhibits prostaglandin synthetase and lipoxygenase, decreasing thromboxane synthesis and inflammatory cytokines. It also reversibly inhibits platelet aggregation. Ajoene synergistically potentiates the anti- aggregatory action of prostacyclin, indomethacin and dipyridamole. It causes fibrinolysis by inhibiting thromboxane synthesis. These effects lead to reduced thrombus formation and inflammation in the damaged vasculature.
  • Ajoene has been proved to possess antibacterial activity against gram-positive bacteria (such as Bacillus cereus, Bacillus subtilis, Mycobacterium smegmatis, Streptomyces griseus, Straphylococcus aureus and Lactobacillus plantaram) and gram-negative bacteria (like Escherichia coli, Klebsiella pneumoniae and Xanthmonas maltophilia); ajoene also inhibited yeast growth.
  • gram-positive bacteria such as Bacillus cereus, Bacillus subtilis, Mycobacterium smegmatis, Streptomyces griseus, Straphylococcus aureus and Lactobacillus plantaram
  • gram-negative bacteria like Escherichia coli, Klebsiella pneumoniae and Xanthmonas maltophilia
  • Garlic is an abundantly used herb across the globe for culinary as well as medicinal purposes. Garlic and its derivatives are on the Food and Drug Administration's Generally Recognised as Safe (GRAS) list, but it is l ⁇ iown to cause gastric irritation if taken in high doses. This effect is not expected to occur when it is administered locally at the site of endothelial injury. Chronic toxicity with garlic and its extracts is unknown. In fact it appears to protect against agents with known genotoxicity, embryotoxicity and carcinogenicity.
  • GRAS Food and Drug Administration's Generally Recognised as Safe
  • Acute and chronic complications following coronary stenting can be reduced by using the safe and multipotential garlic extract, ajoene, which has been proved by in- vitro and in-vivo studies to possess all the beneficial qualities required for countering the processes of thrombus formation, hyperlipemia, atherosclerosis, inflammation, proliferation and sepsis.
  • a coronary stent can be loaded with a drug-polymer complex of a combination of a polymer and ajoene and/or allicin and their derivatives to provide for "time-release".
  • the polymer acts as a vehicle to hold the drag and present it to the site of injury whenever required and as programmed for time-release.
  • the released drug is then able to act locally and counter the acute and chronic complications of coronary stenting which lead to restenosis.
  • Example 1 describes the preparation of a stent with a coating containing ajoene. A coating containing allicin or both ajoene and allicin would be prepared in a corresponding manner.
  • Example 2 demonstrates the time-release properties of the drag from the coating of a stent according to the present invention.
  • Pre-Treatment Received bare stents are given an ultrasonic isopropanol washing treatment for about 30 minutes to 1 hour for better adhesion of the coating material. After that the stents are washed with sterile water and then dried with a hot air drier.
  • a solution of ajoene (the drag) is prepared in a solvent such as dichloromethane, dimethyl formamide, dimethyl sulfoxide, hexafluoroisopropanol or acetone and biodegradable and biocompatible polymers, such as lactone-based polyesters or copolyesters, e.g., polylactide, polycaprolactone-glycolide, polyorthoesters, polyanhydrides; poly-aminoacids; polysaccharides; polyphosphazenes; poly (ether-ester) copolymers, e.g., PEO-PLLA, or blends thereof.
  • Non-absorbable biocompatible polymers are also suitable candidates.
  • the base coat is from 40% to 45% of the drag; about 250 micrograms of the coating.
  • the second coat can be from 25% to 30% of the drug; about 210 micrograms of the coating.
  • the third coat contains 30% to 35%> of the drug; about 240 micrograms of coating in its layer, using a broad band ultrasonic generator attached to a nozzle and medical grade nitrogen gas as the carrier.
  • the power at which the system is operated is 5.0 m Watts.
  • the flow rate is adjusted to about 0.3 ml/min.
  • the spray system is placed in a vacuum amber coloured glass box to eliminate air current and to slow down the evaporation.
  • the stents are positioned (horizontally) 1.5 to 5.0 cm distance from the nozzle and have a dwell time in the spray cloud of about 50 to 60 seconds. The interval is of 10 to 20 seconds and the stent motion is both clockwise and anticlockwise.
  • the room temperature is maintained at 20°C to 23°C.
  • the stent is then dried in ambient conditions for 12 to 16 hours at 38°C. Then the drag-coated stent is stored in a sealed container.
  • IP pH 7.5 phosphate buffer saline
  • PBS 10 mM phosphate buffered saline
  • the tubes are tumbled at 37°C and at given time intervals, centrifuged at 1500 x g for 5 mintues and the supernatant saved for analysis.
  • Drag-loaded stents are resuspended in fresh PBS (10ml) at 37°C and reincubated.
  • Drug concentrations are determined by extraction into 2 ml DCM followed by evaporation to dryness under a stream of medical grade nitrogen gas, reconstitution in 1 ml of acetonitrile in water and analysis using the HPLC method. 30%> of the drag is released initially in 2 to 3 days, 27.5%o of the drag is released within the next 7 to 10 days and the remaining 42.5% should be released in the next 35 to 40 days.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Vascular Medicine (AREA)
  • Surgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Dermatology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Materials For Medical Uses (AREA)

Abstract

Cette invention se rapporte à un dispositif médical implantable qui comprend un substrat et une revêtement polymère biocompatible couvrant au moins une partie dudit substrat. Ledit revêtement contient de l'ajoène et/ou de l'allicine ou des isomères, analogues, homologues ou dérivés de celles-ci, cette invention se rapportant également à une composition comprenant un ou des polymères biocompatibles et de l'ajoène et/ou de l'allicine en vue de servir de revêtement audit dispositif médical implantable.
PCT/IB2002/003480 2001-08-29 2002-08-28 Systeme d'administration locale de medicament dans des extenseurs coronaires Ceased WO2003018080A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0120887.5 2001-08-29
GB0120887A GB0120887D0 (en) 2001-08-29 2001-08-29 Local drug delivery system in coronary stents

Publications (1)

Publication Number Publication Date
WO2003018080A1 true WO2003018080A1 (fr) 2003-03-06

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Application Number Title Priority Date Filing Date
PCT/IN2002/000173 Ceased WO2003018082A2 (fr) 2001-08-29 2002-08-28 Systeme d'administration locale de medicament dans des endoprotheses coronaires
PCT/IB2002/003480 Ceased WO2003018080A1 (fr) 2001-08-29 2002-08-28 Systeme d'administration locale de medicament dans des extenseurs coronaires

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Application Number Title Priority Date Filing Date
PCT/IN2002/000173 Ceased WO2003018082A2 (fr) 2001-08-29 2002-08-28 Systeme d'administration locale de medicament dans des endoprotheses coronaires

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GB (1) GB0120887D0 (fr)
WO (2) WO2003018082A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119113230A (zh) * 2024-09-14 2024-12-13 广州见微医疗科技有限公司 抗菌导管及其制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2449264A (en) * 2007-05-15 2008-11-19 Chameleon Biosurfaces Ltd A coated medical device
CA2687031A1 (fr) 2007-05-15 2008-11-20 Chameleon Biosurfaces Limited Revetements polymeres sur dispositifs medicaux
ES2571998T3 (es) * 2010-12-08 2016-05-27 Univ Danmarks Tekniske Composiciones y usos médicos de derivados del ajoeno

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2061987A (en) * 1978-12-12 1981-05-20 Chinoin Gyogyszer Es Vegyeszet Cyclodextrin complexes, their preparation, and pharmaceutical compositions containing them
EP0353416A2 (fr) * 1988-06-29 1990-02-07 Gesellschaft für Biotechnologische Forschung mbH (GBF) Utilisation de l'ajoène et de ses dérivés comme agents cytostatiques
JPH04108728A (ja) * 1990-08-27 1992-04-09 Kanebo Ltd マイクロカプセル及び繊維構造物
US5824048A (en) * 1993-04-26 1998-10-20 Medtronic, Inc. Method for delivering a therapeutic substance to a body lumen
WO1999021008A1 (fr) * 1997-10-23 1999-04-29 Pharmaprint, Inc. Ail de qualite pharmaceutique
US6206916B1 (en) * 1998-04-15 2001-03-27 Joseph G. Furst Coated intraluminal graft
WO2001056545A2 (fr) * 2000-02-01 2001-08-09 Kuhrts Eric H Systeme d'administration microencapsule a liberation prolongee
US20010053356A1 (en) * 2000-03-20 2001-12-20 Ahmed Mousa Garlic ingredients and antioxidants in the prevention and treatment of vascular-related disorders and pathological angiogenesis-mediated disorders

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2061987A (en) * 1978-12-12 1981-05-20 Chinoin Gyogyszer Es Vegyeszet Cyclodextrin complexes, their preparation, and pharmaceutical compositions containing them
EP0353416A2 (fr) * 1988-06-29 1990-02-07 Gesellschaft für Biotechnologische Forschung mbH (GBF) Utilisation de l'ajoène et de ses dérivés comme agents cytostatiques
JPH04108728A (ja) * 1990-08-27 1992-04-09 Kanebo Ltd マイクロカプセル及び繊維構造物
US5824048A (en) * 1993-04-26 1998-10-20 Medtronic, Inc. Method for delivering a therapeutic substance to a body lumen
WO1999021008A1 (fr) * 1997-10-23 1999-04-29 Pharmaprint, Inc. Ail de qualite pharmaceutique
US6206916B1 (en) * 1998-04-15 2001-03-27 Joseph G. Furst Coated intraluminal graft
WO2001056545A2 (fr) * 2000-02-01 2001-08-09 Kuhrts Eric H Systeme d'administration microencapsule a liberation prolongee
US20010053356A1 (en) * 2000-03-20 2001-12-20 Ahmed Mousa Garlic ingredients and antioxidants in the prevention and treatment of vascular-related disorders and pathological angiogenesis-mediated disorders

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 199221, Derwent World Patents Index; Class A96, AN 1992-171832, XP002223085 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119113230A (zh) * 2024-09-14 2024-12-13 广州见微医疗科技有限公司 抗菌导管及其制备方法

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WO2003018082A2 (fr) 2003-03-06

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