AU778078B2 - Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives - Google Patents
Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives Download PDFInfo
- Publication number
- AU778078B2 AU778078B2 AU26354/00A AU2635400A AU778078B2 AU 778078 B2 AU778078 B2 AU 778078B2 AU 26354/00 A AU26354/00 A AU 26354/00A AU 2635400 A AU2635400 A AU 2635400A AU 778078 B2 AU778078 B2 AU 778078B2
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- Australia
- Prior art keywords
- composition
- alkyl
- cyanoacrylate
- hydroquinone
- present
- 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.)
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- HRKWOOHVRHBXHJ-UHFFFAOYSA-N hexan-2-yl prop-2-enoate Chemical compound CCCCC(C)OC(=O)C=C HRKWOOHVRHBXHJ-UHFFFAOYSA-N 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002697 interventional radiology Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000002981 neuropathic effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000000541 pulsatile effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005549 size reduction Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003106 tissue adhesive Substances 0.000 description 1
- 229940075469 tissue adhesives Drugs 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000001177 vas deferen Anatomy 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 210000002073 venous valve Anatomy 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
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
- 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
- A61L31/04—Macromolecular materials
- A61L31/048—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Chemistry (AREA)
- Vascular Medicine (AREA)
- Materials For Medical Uses (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Sealing Material Composition (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/241368 | 1999-01-29 | ||
| US09/241,368 US6476069B2 (en) | 1997-09-11 | 1999-01-29 | Compositions for creating embolic agents and uses thereof |
| PCT/US2000/002262 WO2000044287A1 (en) | 1999-01-29 | 2000-01-28 | Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005200245A Division AU2005200245A1 (en) | 1999-01-29 | 2005-01-21 | Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2635400A AU2635400A (en) | 2000-08-18 |
| AU778078B2 true AU778078B2 (en) | 2004-11-11 |
Family
ID=22910444
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU26354/00A Ceased AU778078B2 (en) | 1999-01-29 | 2000-01-28 | Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives |
| AU2005200245A Abandoned AU2005200245A1 (en) | 1999-01-29 | 2005-01-21 | Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005200245A Abandoned AU2005200245A1 (en) | 1999-01-29 | 2005-01-21 | Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6476069B2 (https=) |
| EP (1) | EP1154723B1 (https=) |
| JP (2) | JP4317663B2 (https=) |
| AT (1) | ATE381290T1 (https=) |
| AU (2) | AU778078B2 (https=) |
| CA (1) | CA2360533C (https=) |
| DE (1) | DE60037500T2 (https=) |
| ES (1) | ES2296607T3 (https=) |
| WO (1) | WO2000044287A1 (https=) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6538026B1 (en) * | 1997-09-11 | 2003-03-25 | 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 |
| US7687053B2 (en) * | 2001-08-20 | 2010-03-30 | Boston Scientific Scimed, Inc. | Embolic compositions with non-cyanoacrylate rheology modifying agents |
| US7060023B2 (en) | 2001-09-25 | 2006-06-13 | The Foundry Inc. | Pericardium reinforcing devices and methods of using them |
| US6695769B2 (en) | 2001-09-25 | 2004-02-24 | The Foundry, Inc. | Passive ventricular support devices and methods of using them |
| US7131997B2 (en) | 2002-03-29 | 2006-11-07 | Scimed Life Systems, Inc. | Tissue treatment |
| US7094369B2 (en) | 2002-03-29 | 2006-08-22 | Scimed Life Systems, Inc. | Processes for manufacturing polymeric microspheres |
| US7462366B2 (en) | 2002-03-29 | 2008-12-09 | Boston Scientific Scimed, Inc. | Drug delivery particle |
| US7053134B2 (en) | 2002-04-04 | 2006-05-30 | Scimed Life Systems, Inc. | Forming a chemically cross-linked particle of a desired shape and diameter |
| US7341716B2 (en) * | 2002-04-12 | 2008-03-11 | Boston Scientific Scimed, Inc. | Occlusive composition |
| US7449236B2 (en) | 2002-08-09 | 2008-11-11 | Boston Scientific Scimed, Inc. | Porous polymeric particle comprising polyvinyl alcohol and having interior to surface porosity-gradient |
| US7842377B2 (en) * | 2003-08-08 | 2010-11-30 | Boston Scientific Scimed, Inc. | Porous polymeric particle comprising polyvinyl alcohol and having interior to surface porosity-gradient |
| US8012454B2 (en) | 2002-08-30 | 2011-09-06 | Boston Scientific Scimed, Inc. | Embolization |
| US7588825B2 (en) | 2002-10-23 | 2009-09-15 | Boston Scientific Scimed, Inc. | Embolic compositions |
| US7883490B2 (en) | 2002-10-23 | 2011-02-08 | Boston Scientific Scimed, Inc. | Mixing and delivery of therapeutic compositions |
| WO2005006991A2 (en) * | 2003-07-18 | 2005-01-27 | Chiroxia Limited | Device and method for fallopian tube occlusion |
| US7976823B2 (en) | 2003-08-29 | 2011-07-12 | Boston Scientific Scimed, Inc. | Ferromagnetic particles and methods |
| US20050090804A1 (en) * | 2003-10-22 | 2005-04-28 | Trivascular, Inc. | Endoluminal prosthesis endoleak management |
| US7901770B2 (en) | 2003-11-04 | 2011-03-08 | Boston Scientific Scimed, Inc. | Embolic compositions |
| US8052669B2 (en) | 2004-02-25 | 2011-11-08 | Femasys Inc. | Methods and devices for delivery of compositions to conduits |
| US8048101B2 (en) | 2004-02-25 | 2011-11-01 | Femasys Inc. | Methods and devices for conduit occlusion |
| US9238127B2 (en) | 2004-02-25 | 2016-01-19 | Femasys Inc. | Methods and devices for delivering to conduit |
| US8048086B2 (en) | 2004-02-25 | 2011-11-01 | Femasys Inc. | Methods and devices for conduit occlusion |
| US7736671B2 (en) | 2004-03-02 | 2010-06-15 | Boston Scientific Scimed, Inc. | Embolization |
| US20050197421A1 (en) * | 2004-03-03 | 2005-09-08 | Loomis Gary L. | Process for preparation of cyanoacrylate compositions |
| US20050228433A1 (en) * | 2004-03-16 | 2005-10-13 | Weenna Bucay-Couto | In situ implant and method of forming same |
| US8173176B2 (en) | 2004-03-30 | 2012-05-08 | Boston Scientific Scimed, Inc. | Embolization |
| US7311861B2 (en) | 2004-06-01 | 2007-12-25 | Boston Scientific Scimed, Inc. | Embolization |
| US20050287216A1 (en) * | 2004-06-29 | 2005-12-29 | Loomis Gary L | Medical imaging agents for injectable compositions |
| US8425550B2 (en) | 2004-12-01 | 2013-04-23 | Boston Scientific Scimed, Inc. | Embolic coils |
| US7727555B2 (en) | 2005-03-02 | 2010-06-01 | Boston Scientific Scimed, Inc. | Particles |
| US7858183B2 (en) | 2005-03-02 | 2010-12-28 | Boston Scientific Scimed, Inc. | Particles |
| US7963287B2 (en) | 2005-04-28 | 2011-06-21 | Boston Scientific Scimed, Inc. | Tissue-treatment methods |
| US9463426B2 (en) | 2005-06-24 | 2016-10-11 | Boston Scientific Scimed, Inc. | Methods and systems for coating particles |
| CN1318099C (zh) * | 2005-07-29 | 2007-05-30 | 商菁华 | 一种粘合剂的用途 |
| US20070078207A1 (en) * | 2005-09-30 | 2007-04-05 | Jonn Jerry Y | Stabilizer cyanoacrylate formulations |
| JP2007126632A (ja) * | 2005-10-06 | 2007-05-24 | Taoka Chem Co Ltd | 2−シアノアクリレート系接着剤組成物 |
| US8007509B2 (en) | 2005-10-12 | 2011-08-30 | Boston Scientific Scimed, Inc. | Coil assemblies, components and methods |
| US8101197B2 (en) | 2005-12-19 | 2012-01-24 | Stryker Corporation | Forming coils |
| US8152839B2 (en) | 2005-12-19 | 2012-04-10 | Boston Scientific Scimed, Inc. | Embolic coils |
| US7501179B2 (en) | 2005-12-21 | 2009-03-10 | Boston Scientific Scimed, Inc. | Block copolymer particles |
| US7947368B2 (en) | 2005-12-21 | 2011-05-24 | Boston Scientific Scimed, Inc. | Block copolymer particles |
| US8092819B2 (en) * | 2006-01-27 | 2012-01-10 | Cook Medical Technologies LLC. | Implantable medical device coated with a bioactive agent |
| US20070185229A1 (en) | 2006-02-08 | 2007-08-09 | Bristol-Myers Squibb Company | Formulation for improving skin adhesive effectiveness |
| JP5242551B2 (ja) * | 2006-04-06 | 2013-07-24 | レヴァ メディカル、 インコーポレイテッド | 血管性動脈瘤の治療用塞栓プロテーゼ |
| US8603138B2 (en) * | 2006-10-04 | 2013-12-10 | Ethicon Endo-Surgery, Inc. | Use of an adhesive to treat intraluminal bleeding |
| US8414927B2 (en) | 2006-11-03 | 2013-04-09 | Boston Scientific Scimed, Inc. | Cross-linked polymer particles |
| CN101917927A (zh) * | 2007-11-12 | 2010-12-15 | 维勒医学有限公司 | 医用级氰基丙烯酸酯的单瓶制剂 |
| US20090137981A1 (en) * | 2007-11-26 | 2009-05-28 | Valor Medical | Methods of treating a blood vessel |
| US20090246262A1 (en) * | 2008-03-28 | 2009-10-01 | Valor Medical, Inc. | Easily applied field dressing for wounds |
| EP2326255B1 (en) | 2008-05-19 | 2020-05-06 | Anaesthetic Care Limited | Varicose vein treatment |
| WO2010028300A1 (en) | 2008-09-04 | 2010-03-11 | Curaseal Inc. | Inflatable device for enteric fistula treatment |
| US20100080791A1 (en) * | 2008-09-26 | 2010-04-01 | Rousseau Robert A | Composition and Method For Treating Tissue Defects |
| US9554826B2 (en) | 2008-10-03 | 2017-01-31 | Femasys, Inc. | Contrast agent injection system for sonographic imaging |
| US10070888B2 (en) | 2008-10-03 | 2018-09-11 | Femasys, Inc. | Methods and devices for sonographic imaging |
| US12171463B2 (en) | 2008-10-03 | 2024-12-24 | Femasys Inc. | Contrast agent generation and injection system for sonographic imaging |
| DE102009012187A1 (de) * | 2009-02-26 | 2010-09-02 | Aesculap Aktiengesellschaft | Medizinische Klebstoffzusammensetzung |
| JP6122424B2 (ja) | 2011-06-16 | 2017-04-26 | キュラシール インコーポレイテッド | 瘻孔処置用デバイス及びその関連方法 |
| JP6127042B2 (ja) | 2011-06-17 | 2017-05-10 | キュラシール インコーポレイテッド | 瘻孔処置用デバイスと方法 |
| US12402885B2 (en) | 2017-09-23 | 2025-09-02 | Universität Zürich | Medical occlusion device |
| EP3459469A1 (en) | 2017-09-23 | 2019-03-27 | Universität Zürich | Medical occluder device |
| CN110964131B (zh) | 2018-09-29 | 2022-11-22 | 诺维新材有限公司 | 含有多羟基的聚合物及其制备方法和用途 |
| IT201900010053A1 (it) * | 2019-06-25 | 2020-12-25 | Permabond Eng Adhesives Ltd | Composizioni di adesivi cianoacrilici con resistenza migliorata alle alte temperature |
| CN114641242B (zh) | 2019-09-26 | 2025-11-18 | 苏黎世大学 | 左心耳闭塞装置 |
| US12564408B2 (en) | 2020-03-25 | 2026-03-03 | Universitat Zurich | Medical occluder delivery systems |
| KR102530540B1 (ko) * | 2020-08-19 | 2023-05-09 | 서울대학교산학협력단 | 신규 시안화아크릴레이트 유도체 및 이를 포함하는 색전 물질용 조성물 |
| US20250382506A1 (en) * | 2022-06-29 | 2025-12-18 | University Of Kansas | Shelf stable adhesive compositions |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313865A (en) * | 1979-09-28 | 1982-02-02 | Japan Synthetic Rubber Co., Ltd. | Instant-setting adhesive composition |
| US5695480A (en) * | 1996-07-29 | 1997-12-09 | Micro Therapeutics, Inc. | Embolizing compositions |
| WO1999042535A1 (en) * | 1998-02-18 | 1999-08-26 | Closure Medical Corporation | Cyanoacrylate compositions with terminal vinyl group in the alcohol part |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3559652A (en) | 1968-08-05 | 1971-02-02 | Minnesota Mining & Mfg | Method of adhesively repairing body tissue with alkoxyalkyl 2-cyanoacrylate |
| US3692752A (en) | 1968-10-31 | 1972-09-19 | Matsumoto Seiyaku Kogyo Kk | Adhesive composition containing {60 -cyanoacrylate as its main ingredient |
| US3728375A (en) | 1971-05-12 | 1973-04-17 | Eastman Kodak Co | Cyanoacrylate adhesive compositions |
| US3995641A (en) | 1975-04-23 | 1976-12-07 | Ethicon, Inc. | Surgical adhesives |
| US4182823A (en) | 1978-08-18 | 1980-01-08 | National Starch And Chemical Corporation | Anionic polymerization inhibitor for cyanoacrylate adhesives |
| US4328170A (en) | 1978-11-02 | 1982-05-04 | Matsumoto Seiyaku Kogyo Kabushiki Kaisha | Process for preparing an α-cyanoacrylate |
| JPS5853676B2 (ja) | 1979-12-24 | 1983-11-30 | 東亞合成株式会社 | 接着剤組成物 |
| 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 |
| US5403591A (en) | 1993-06-25 | 1995-04-04 | Medlogic Global Corporation | Methods for inhibiting skin ulceration by use of cyanoacrylate adhesives |
| US5759194A (en) | 1993-09-28 | 1998-06-02 | Hemodynamics, Inc. | Vascular patch applicator |
| TW359683B (en) | 1993-12-23 | 1999-06-01 | Loctite Ireland Ltd | Sterilized cyanoacrylate adhesive composition, and a method of making such composition |
| US5795331A (en) | 1994-01-24 | 1998-08-18 | Micro Therapeutics, Inc. | Balloon catheter for occluding aneurysms of branch vessels |
| US5703267A (en) | 1995-03-27 | 1997-12-30 | Toagosei Co., Ltd. | Process for producing 2-cyanoacrylic acid |
| US5981621A (en) * | 1996-02-29 | 1999-11-09 | Closure Medical Corporation | Monomeric compositions effective as wound closure devices |
| US5888546A (en) | 1995-08-28 | 1999-03-30 | The Regents Of The University Of California | Embolic material for endovascular occlusion of abnormal vasculature and method for using the same |
| US5702361A (en) | 1996-01-31 | 1997-12-30 | Micro Therapeutics, Inc. | Method for embolizing blood vessels |
| US6037366A (en) * | 1997-09-11 | 2000-03-14 | Prohold Medical Technologies, Inc. | Composition for creating vascular occlusions |
-
1999
- 1999-01-29 US US09/241,368 patent/US6476069B2/en not_active Expired - Lifetime
-
2000
- 2000-01-28 EP EP00904626A patent/EP1154723B1/en not_active Expired - Lifetime
- 2000-01-28 AU AU26354/00A patent/AU778078B2/en not_active Ceased
- 2000-01-28 AT AT00904626T patent/ATE381290T1/de not_active IP Right Cessation
- 2000-01-28 DE DE60037500T patent/DE60037500T2/de not_active Expired - Lifetime
- 2000-01-28 CA CA002360533A patent/CA2360533C/en not_active Expired - Fee Related
- 2000-01-28 WO PCT/US2000/002262 patent/WO2000044287A1/en not_active Ceased
- 2000-01-28 ES ES00904626T patent/ES2296607T3/es not_active Expired - Lifetime
- 2000-01-28 JP JP2000595594A patent/JP4317663B2/ja not_active Expired - Fee Related
-
2005
- 2005-01-21 AU AU2005200245A patent/AU2005200245A1/en not_active Abandoned
-
2009
- 2009-04-06 JP JP2009092509A patent/JP2009148627A/ja not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313865A (en) * | 1979-09-28 | 1982-02-02 | Japan Synthetic Rubber Co., Ltd. | Instant-setting adhesive composition |
| US5695480A (en) * | 1996-07-29 | 1997-12-09 | Micro Therapeutics, Inc. | Embolizing compositions |
| WO1999042535A1 (en) * | 1998-02-18 | 1999-08-26 | Closure Medical Corporation | Cyanoacrylate compositions with terminal vinyl group in the alcohol part |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4317663B2 (ja) | 2009-08-19 |
| US20020098150A1 (en) | 2002-07-25 |
| ES2296607T3 (es) | 2008-05-01 |
| JP2002535065A (ja) | 2002-10-22 |
| EP1154723B1 (en) | 2007-12-19 |
| ATE381290T1 (de) | 2008-01-15 |
| WO2000044287A1 (en) | 2000-08-03 |
| JP2009148627A (ja) | 2009-07-09 |
| CA2360533A1 (en) | 2000-08-03 |
| AU2635400A (en) | 2000-08-18 |
| DE60037500T2 (de) | 2008-12-24 |
| CA2360533C (en) | 2009-04-14 |
| US6476069B2 (en) | 2002-11-05 |
| EP1154723A1 (en) | 2001-11-21 |
| DE60037500D1 (de) | 2008-01-31 |
| AU2005200245A1 (en) | 2005-03-17 |
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