USRE42377E1 - Composition for creating vascular occlusions - Google Patents
Composition for creating vascular occlusions Download PDFInfo
- Publication number
- USRE42377E1 USRE42377E1 US11/827,668 US82766807A USRE42377E US RE42377 E1 USRE42377 E1 US RE42377E1 US 82766807 A US82766807 A US 82766807A US RE42377 E USRE42377 E US RE42377E
- Authority
- US
- United States
- Prior art keywords
- cyanoacrylate
- composition
- ppm
- methoxyphenol
- hydroquinone
- 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.)
- Expired - Lifetime
Links
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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
-
- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
-
- 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
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/242—Gold; Compounds thereof
-
- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/36—Materials or treatment for tissue regeneration for embolization or occlusion, e.g. vaso-occlusive compositions or devices
Definitions
- This invention relates to a composition used to treat arteriovenous malformations (“AVMs”) and other vascular abnormalities.
- the composition includes a cyanoacrylate liquid monomer and gold in a prepolymerized polymer of cyanoacrylate.
- the composition is placed into the body lumen via standard catheter procedures or directly percutaneously.
- AVMs and vascular tumors are exceedingly difficult to treat. These growths may occur all over the body, but are especially difficult to treat when in the brain or brain stem.
- the composition of the invention is especially useful in treating neurological AVMs, but may also be used to treat tumors anywhere in the body.
- Cyanoacrylate adhesives have been used surgically but are limited in their usefulness by cytotoxicity and heat generation. The brain is unusually sensitive to cytotoxicity and heat.
- the invention provides a composition that may be placed in a body lumen including veins and arteries by super selective catheterization or direct puncture using standard tools of the interventional angiographer.
- the composition of the invention has been successfully tested in simulated models of the AVMs and tumors under fluoroscopy and in systems that closely resembles the neurological condition of the human body. Further studies have been done in the pig rete.
- the rete is a body of fine arteries that allows the blood to flow into the pig brain which closely resembles normal human AVMs.
- the composition is a cyanoacrylate which involves mixing two separate containers of the material immediately prior to administration of the material into the AVM by catheter.
- the composition may contain seven ingredients which are divided into two parts prior to mixture and use. It furnishes properties that are useful for closing neurological AVMs.
- the product can also be used to close any growth resembling an AVM in any part of the body. Because of the sensitive nature of the tissues in the brain, the general sensitivity of the product must be controlled. In less sensitive areas, the product will work equally as well.
- Part I consists of a cyanoacrylate liquid monomer containing pure phosphoric acid (250 ppm) hydroquinone (100 ppm) and P-methoxyphenol (1200 ppm). This composition is stable and unchanging we believe for over two years.
- the container in which Part I is stored requires cleaning and preparation before such stability can be achieved.
- the liquid monomer of choice for this usage is 2-hexyl cyanoacrylate.
- Part II consists of pure powdered gold (5 ⁇ 3 microns), a small amount of prepolymerized polymer of the same cyanoacrylate and ethyl myristate. Any of the large chain fatty acid esters will work to replace ethyl myristate so long as they are liquids.
- the pre-polymerized polymers of cyanoacrylate are unstable and change their structures and properties even in the solid state.
- the change is exponential and therefore the polymer must be used within a limited amount of time before deterioration occurs.
- the polymer is prepared by addition of part 1 to a rapidly stirring weak bicarbonate-water solution. The addition must be added drop-wise to avoid unpolymerized masses from forming.
- the solid polymer is washed thoroughly with pure water to remove any traces of bicarbonate, then washed thoroughly with pure methanol to remove the water. Methanol dries rapidly and when the polymer is further dried at a high reduced pressure for 16–18 hours, it is considered dry.
- the polymer must be used in the next step within 24 hours to obtain consistent results in the final product. This mixture must be sterilized within 72 hours from the time of preparation.
- Part II is sterilized with ethylene oxide gas with the stopper held in an open position.
- Ethylene oxide is an alkylating agent and after sterilization the prepolymerized polymer is stable. Hence, the stability and sterilization of part 2 are carried out simultaneously.
- the sterilized samples of Part II are capped in a clean room under sterile handling conditions.
- the pre-polymerized polymer can be stabled by treatment with any of the strong alkylating agents, like ethylene oxide, ketene, etc.
- composition of matter has good cohesion as well as adequate adhesion to function well for AVMs and other similar uses within the vascular tree.
- the cohesion keeps the material together during the time required for it to polymerize.
- the adhesion makes it stick to the artery walls.
- the polymerized device will cause a modest but desirable inflammatory response in the treated tissues.
- Part I 2-Hexyl Cyanoacrylate 999,550 ppm Hydroquinone 100 ppm p-Methoxyphenol 100 ppm Pure Phosphoric Acid 250 ppm
- Part II (M2) Pure Gold 1.0000 g Pure Ethyl Myristate 0.5000 g FMS* 0.0200 g *FMS is a specially prepared polymer of 2-hexyl cyanoacrylate and must be used within 24 hours of preparation or will change and be unusable. Further, it must be sterilized within 72 hours.
- This cyanoacrylate homolog was chosen because it biodegrades very slowly in blood or any living tissue.
- the secondary alcohol will biodegrade several thousand times slower than its primary derivative. This very slow degradation rate also lowers greatly the histotoxicity.
- Tantalum, platinum and gold are all radiopaque. Gold was best for us because it could be suspended colloidally in the mixture. One gram of gold is used per device.
- Subbicates are useful for fastening the polymers of the cyanoacrylates. They also will stabilize the pre-formed polymers of the cyanoacrylates so that they may be used as thickeners.
- ethyl myristate an esterified, biocompatible fatty acid because of the convenience of purification and analysis and because is works well to give the formulation the desirable properties.
- FMS is the polymer of 2-hexyl cyanoacrylate formed in a weak, aqueous sodium bicarbonate solutions.
- the polymer differs in structure and size depending on how it is formed. This polymer will remain stable until M2 can be formulated. The polymer must be formed and dried completely before use. The final formulation of M2 must occur within 24 hours because the ethyl myristate stabilized FMS until sterilization can be performed. After sterilization the product is stable for several years.
- M1 and M2 are mixed immediately before use.
- the mixture should be used within 4 hours after mixing. If there is a delay, the syringe should be turned over several times a minute to resuspend the gold which will be settled.
Abstract
Description
-
- The product has a very slow rate of biodegradation.
- Both liquid and solid forms should have excellent cohesion.
- The delivered product should have medium adhesion
- The delivered product must be radiopaque.
- The solid polymer should be soft and pliable.
- The delivered product must have a very low or negligible histotoxicity.
- The deposited product must have no long term negative properties such as carcinogenicity, teratogenicity, systemic toxicity or other unpredictable biological and medical effects.
- The products must be sterile.
- The delivered product must have good flow characteristics for selective catheterization.
- The product must be stable on storage for an extended period of time.
- The formulation should be made from pure products and be reproducible for simple manufacturing procedures.
The product formulation is:
Part I (M1) |
2-Hexyl Cyanoacrylate | 999,550 | ppm | |
Hydroquinone | 100 | ppm | |
p-Methoxyphenol | 100 | ppm | |
Pure Phosphoric Acid | 250 | ppm |
Part II (M2) |
Pure Gold | 1.0000 | g | |
Pure Ethyl Myristate | 0.5000 | g | |
FMS* | 0.0200 | g | |
*FMS is a specially prepared polymer of 2-hexyl cyanoacrylate and must be used within 24 hours of preparation or will change and be unusable. Further, it must be sterilized within 72 hours. |
Claims (16)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/827,668 USRE42377E1 (en) | 1997-09-11 | 2007-07-12 | Composition for creating vascular occlusions |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5851097P | 1997-09-11 | 1997-09-11 | |
US09/151,621 US6037366A (en) | 1997-09-11 | 1998-09-11 | Composition for creating vascular occlusions |
US09/823,775 USRE39150E1 (en) | 1997-09-11 | 2001-03-30 | Composition for creating vascular occlusions |
US87341304A | 2004-06-22 | 2004-06-22 | |
US11/827,668 USRE42377E1 (en) | 1997-09-11 | 2007-07-12 | Composition for creating vascular occlusions |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/151,621 Reissue US6037366A (en) | 1997-09-11 | 1998-09-11 | Composition for creating vascular occlusions |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE42377E1 true USRE42377E1 (en) | 2011-05-17 |
Family
ID=26737696
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/151,621 Ceased US6037366A (en) | 1997-09-11 | 1998-09-11 | Composition for creating vascular occlusions |
US09/823,775 Expired - Lifetime USRE39150E1 (en) | 1997-09-11 | 2001-03-30 | Composition for creating vascular occlusions |
US11/827,668 Expired - Lifetime USRE42377E1 (en) | 1997-09-11 | 2007-07-12 | Composition for creating vascular occlusions |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/151,621 Ceased US6037366A (en) | 1997-09-11 | 1998-09-11 | Composition for creating vascular occlusions |
US09/823,775 Expired - Lifetime USRE39150E1 (en) | 1997-09-11 | 2001-03-30 | Composition for creating vascular occlusions |
Country Status (1)
Country | Link |
---|---|
US (3) | US6037366A (en) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6476070B2 (en) * | 1997-09-11 | 2002-11-05 | Provasis Therapeutics Inc. | Compositions useful for remodeling body spaces |
US6037366A (en) | 1997-09-11 | 2000-03-14 | Prohold Medical Technologies, Inc. | Composition for creating vascular occlusions |
US6538026B1 (en) * | 1997-09-11 | 2003-03-25 | Provasis Therapeutics, Inc. | Compositions useful for remodeling body spaces |
US6476069B2 (en) * | 1997-09-11 | 2002-11-05 | Provasis Therapeutics Inc. | Compositions for creating embolic agents and uses thereof |
US6676971B2 (en) | 2000-03-13 | 2004-01-13 | Biocure, Inc. | Embolic compositions |
US6652883B2 (en) | 2000-03-13 | 2003-11-25 | Biocure, Inc. | Tissue bulking and coating compositions |
US7687053B2 (en) * | 2001-08-20 | 2010-03-30 | Boston Scientific Scimed, Inc. | Embolic compositions with non-cyanoacrylate rheology modifying agents |
US6695769B2 (en) | 2001-09-25 | 2004-02-24 | The Foundry, Inc. | Passive ventricular support devices and methods of using them |
US7060023B2 (en) | 2001-09-25 | 2006-06-13 | The Foundry Inc. | Pericardium reinforcing devices and methods of using them |
US7341716B2 (en) * | 2002-04-12 | 2008-03-11 | Boston Scientific Scimed, Inc. | Occlusive composition |
DE10235602B4 (en) * | 2002-08-02 | 2010-01-14 | Universität Duisburg-Essen | Metal cluster nanocompounds for the treatment of tumor diseases |
HUP0203719A2 (en) * | 2002-10-31 | 2007-09-28 | Stepan Dr Gudak | Polyuretan composition for fillin blood vessels and method of aplication of it |
US7471784B2 (en) * | 2004-07-29 | 2008-12-30 | International Business Machines Corporation | Dialed number service routing in a telephone network by reference to a database |
US20060083762A1 (en) * | 2004-10-13 | 2006-04-20 | Gaelle Brun | Uses of compositions comprising electrophilic monomers and micro-particles or nanoparticles |
BRPI0504500A (en) * | 2004-10-13 | 2006-05-23 | Oreal | use of a composition, cosmetic composition, process of treatment of keratin materials and kit |
ATE438377T1 (en) * | 2004-10-13 | 2009-08-15 | Oreal | ANHYDROUS COSMETIC COMPOSITION CONTAINING ELECTROPHILIC MONOMERS AND ACID AND THE USE THEREOF FOR THE COSMETIC TREATMENT OF HAIR |
US20060085924A1 (en) * | 2004-10-13 | 2006-04-27 | Gaelle Brun | Coloring composition comprising at least one pigment and at least one electrophilic cyanoacrylate monomer |
US20070078207A1 (en) * | 2005-09-30 | 2007-04-05 | Jonn Jerry Y | Stabilizer cyanoacrylate formulations |
US20080241249A1 (en) * | 2007-03-30 | 2008-10-02 | Closure Medical Corporation | Cyanoacrylate composite |
JP2011503108A (en) * | 2007-11-12 | 2011-01-27 | ヴァロー メディカル、 インク. | Single vial formulation of medical grade cyanoacrylate |
US20090137981A1 (en) * | 2007-11-26 | 2009-05-28 | Valor Medical | Methods of treating a blood vessel |
US9232805B2 (en) | 2010-06-29 | 2016-01-12 | Biocure, Inc. | In-situ forming hydrogel wound dressings containing antimicrobial agents |
BR112014031223B1 (en) | 2012-06-14 | 2023-03-14 | Microvention, Inc | POLYMER TREATMENT COMPOSITIONS |
US9078950B2 (en) | 2012-10-15 | 2015-07-14 | Microvention, Inc. | Polymeric treatment compositions |
US10111904B2 (en) | 2013-01-09 | 2018-10-30 | Berlock Aps | Micron-sized gold, kit comprising said gold and its use as a non-toxic immune suppressor |
EP3091904A1 (en) * | 2014-01-07 | 2016-11-16 | Covidien LP | Cyanoacrylate compositions including non-agglomerating radiopaque nanoparticles |
US10368874B2 (en) | 2016-08-26 | 2019-08-06 | Microvention, Inc. | Embolic compositions |
CN111200976B (en) | 2017-10-09 | 2023-07-07 | 微仙美国有限公司 | Radioactive liquid embolism |
Citations (18)
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US4359454A (en) | 1980-12-16 | 1982-11-16 | World Health Organization | Method and composition containing MCA for female sterilization |
US4713235A (en) | 1981-05-26 | 1987-12-15 | Crx Medical, Inc. | Radiopaque cyanoacrylates |
US4740534A (en) | 1985-08-30 | 1988-04-26 | Sanyo Chemical Industries, Ltd. | Surgical adhesive |
US5328687A (en) | 1993-03-31 | 1994-07-12 | Tri-Point Medical L.P. | Biocompatible monomer and polymer compositions |
EP0664104A2 (en) | 1994-01-24 | 1995-07-26 | Micro Therapeutics, Inc. | Balloon catheter for occluding aneurysms or branch vessels |
US5525334A (en) | 1994-06-03 | 1996-06-11 | Japan As Represented By Director General Of Agency Of Industrial Science And Technology | Method for vascular embolization |
US5624685A (en) | 1991-10-16 | 1997-04-29 | Terumo Kabushiki Kaisha | High polymer gel and vascular lesion embolizing material comprising the same |
US5695480A (en) | 1996-07-29 | 1997-12-09 | Micro Therapeutics, Inc. | Embolizing compositions |
US5702361A (en) | 1996-01-31 | 1997-12-30 | Micro Therapeutics, Inc. | Method for embolizing blood vessels |
US5759194A (en) | 1993-09-28 | 1998-06-02 | Hemodynamics, Inc. | Vascular patch applicator |
WO1999042535A1 (en) | 1998-02-18 | 1999-08-26 | Closure Medical Corporation | Cyanoacrylate compositions with terminal vinyl group in the alcohol part |
US5981621A (en) | 1996-02-29 | 1999-11-09 | Closure Medical Corporation | Monomeric compositions effective as wound closure devices |
US6037366A (en) | 1997-09-11 | 2000-03-14 | Prohold Medical Technologies, Inc. | Composition for creating vascular occlusions |
WO2000044287A1 (en) | 1999-01-29 | 2000-08-03 | Prohold Medical Technologies, Inc. | Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives |
US6143352A (en) | 1994-06-28 | 2000-11-07 | Closure Medical Corporation | pH-modified biocompatible monomer and polymer compositions |
US20020018752A1 (en) | 2000-05-23 | 2002-02-14 | Krall Robert E. | Polymerizable compositions and methods of use |
US6476070B2 (en) | 1997-09-11 | 2002-11-05 | Provasis Therapeutics Inc. | Compositions useful for remodeling body spaces |
US20030194389A1 (en) | 2002-04-12 | 2003-10-16 | Porter Stephen C. | Occlusive composition |
-
1998
- 1998-09-11 US US09/151,621 patent/US6037366A/en not_active Ceased
-
2001
- 2001-03-30 US US09/823,775 patent/USRE39150E1/en not_active Expired - Lifetime
-
2007
- 2007-07-12 US US11/827,668 patent/USRE42377E1/en not_active Expired - Lifetime
Patent Citations (22)
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US4359454A (en) | 1980-12-16 | 1982-11-16 | World Health Organization | Method and composition containing MCA for female sterilization |
US4713235A (en) | 1981-05-26 | 1987-12-15 | Crx Medical, Inc. | Radiopaque cyanoacrylates |
US4740534A (en) | 1985-08-30 | 1988-04-26 | Sanyo Chemical Industries, Ltd. | Surgical adhesive |
US5624685A (en) | 1991-10-16 | 1997-04-29 | Terumo Kabushiki Kaisha | High polymer gel and vascular lesion embolizing material comprising the same |
US5328687A (en) | 1993-03-31 | 1994-07-12 | Tri-Point Medical L.P. | Biocompatible monomer and polymer compositions |
US5759194A (en) | 1993-09-28 | 1998-06-02 | Hemodynamics, Inc. | Vascular patch applicator |
EP0664104A2 (en) | 1994-01-24 | 1995-07-26 | Micro Therapeutics, Inc. | Balloon catheter for occluding aneurysms or branch vessels |
US5795331A (en) | 1994-01-24 | 1998-08-18 | Micro Therapeutics, Inc. | Balloon catheter for occluding aneurysms of branch vessels |
US5525334A (en) | 1994-06-03 | 1996-06-11 | Japan As Represented By Director General Of Agency Of Industrial Science And Technology | Method for vascular embolization |
US6143352A (en) | 1994-06-28 | 2000-11-07 | Closure Medical Corporation | pH-modified biocompatible monomer and polymer compositions |
US5702361A (en) | 1996-01-31 | 1997-12-30 | Micro Therapeutics, Inc. | Method for embolizing blood vessels |
US5981621A (en) | 1996-02-29 | 1999-11-09 | Closure Medical Corporation | Monomeric compositions effective as wound closure devices |
US5695480A (en) | 1996-07-29 | 1997-12-09 | Micro Therapeutics, Inc. | Embolizing compositions |
US6037366A (en) | 1997-09-11 | 2000-03-14 | Prohold Medical Technologies, Inc. | Composition for creating vascular occlusions |
US6476069B2 (en) | 1997-09-11 | 2002-11-05 | Provasis Therapeutics Inc. | Compositions for creating embolic agents and uses thereof |
US6476070B2 (en) | 1997-09-11 | 2002-11-05 | Provasis Therapeutics Inc. | Compositions useful for remodeling body spaces |
USRE39150E1 (en) * | 1997-09-11 | 2006-06-27 | Prohold Technologies, Inc. | Composition for creating vascular occlusions |
WO1999042535A1 (en) | 1998-02-18 | 1999-08-26 | Closure Medical Corporation | Cyanoacrylate compositions with terminal vinyl group in the alcohol part |
US6174919B1 (en) | 1998-02-18 | 2001-01-16 | Closure Medical Corporation | Cyanoacrylate compositions with vinyl terminated ester groups |
WO2000044287A1 (en) | 1999-01-29 | 2000-08-03 | Prohold Medical Technologies, Inc. | Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives |
US20020018752A1 (en) | 2000-05-23 | 2002-02-14 | Krall Robert E. | Polymerizable compositions and methods of use |
US20030194389A1 (en) | 2002-04-12 | 2003-10-16 | Porter Stephen C. | Occlusive composition |
Non-Patent Citations (22)
Also Published As
Publication number | Publication date |
---|---|
US6037366A (en) | 2000-03-14 |
USRE39150E1 (en) | 2006-06-27 |
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