BG99072A - Контрастно средство и метод за получаването му - Google Patents
Контрастно средство и метод за получаването му Download PDFInfo
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- BG99072A BG99072A BG99072A BG9907294A BG99072A BG 99072 A BG99072 A BG 99072A BG 99072 A BG99072 A BG 99072A BG 9907294 A BG9907294 A BG 9907294A BG 99072 A BG99072 A BG 99072A
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
- A61K49/1818—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
- A61K49/1821—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
- A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
- A61K49/223—Microbubbles, hollow microspheres, free gas bubbles, gas microspheres
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB929204918A GB9204918D0 (en) | 1992-03-06 | 1992-03-06 | Chemical compounds |
GB929204920A GB9204920D0 (en) | 1992-03-06 | 1992-03-06 | Improvements in or relating to contrast agents |
PCT/GB1993/000470 WO1993017718A1 (fr) | 1992-03-06 | 1993-03-05 | Perfectionnements apportes aux agents de contraste |
Publications (1)
Publication Number | Publication Date |
---|---|
BG99072A true BG99072A (bg) | 1995-09-29 |
Family
ID=26300446
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG99072A BG99072A (bg) | 1992-03-06 | 1994-09-28 | Контрастно средство и метод за получаването му |
Country Status (25)
Country | Link |
---|---|
US (1) | US5795562A (fr) |
EP (1) | EP0627942B1 (fr) |
JP (1) | JP3650393B2 (fr) |
CN (1) | CN1084410A (fr) |
AT (1) | ATE184491T1 (fr) |
AU (1) | AU676467B2 (fr) |
BG (1) | BG99072A (fr) |
BR (1) | BR9306044A (fr) |
CA (1) | CA2130670A1 (fr) |
CZ (1) | CZ284844B6 (fr) |
DE (1) | DE69326447T2 (fr) |
EE (1) | EE03079B1 (fr) |
ES (1) | ES2135466T3 (fr) |
FI (1) | FI944077A0 (fr) |
HU (1) | HUT68612A (fr) |
IL (1) | IL104963A (fr) |
LV (1) | LV10396B (fr) |
NO (1) | NO943272D0 (fr) |
NZ (1) | NZ249548A (fr) |
OA (1) | OA10096A (fr) |
PL (1) | PL174114B1 (fr) |
RU (1) | RU2122432C1 (fr) |
SG (1) | SG44668A1 (fr) |
SK (1) | SK106694A3 (fr) |
WO (1) | WO1993017718A1 (fr) |
Families Citing this family (76)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5922304A (en) * | 1989-12-22 | 1999-07-13 | Imarx Pharmaceutical Corp. | Gaseous precursor filled microspheres as magnetic resonance imaging contrast agents |
IN172208B (fr) * | 1990-04-02 | 1993-05-01 | Sint Sa | |
GB9106686D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
US5205290A (en) * | 1991-04-05 | 1993-04-27 | Unger Evan C | Low density microspheres and their use as contrast agents for computed tomography |
MX9205298A (es) * | 1991-09-17 | 1993-05-01 | Steven Carl Quay | Medios gaseosos de contraste de ultrasonido y metodo para seleccionar gases para usarse como medios de contraste de ultrasonido |
US5409688A (en) * | 1991-09-17 | 1995-04-25 | Sonus Pharmaceuticals, Inc. | Gaseous ultrasound contrast media |
US6383470B1 (en) | 1992-09-26 | 2002-05-07 | Thomas Fritzsch | Microparticle preparations made of biodegradable copolymers |
IL108416A (en) | 1993-01-25 | 1998-10-30 | Sonus Pharma Inc | Colloids with phase difference as contrast ultrasound agents |
US5558855A (en) * | 1993-01-25 | 1996-09-24 | Sonus Pharmaceuticals | Phase shift colloids as ultrasound contrast agents |
CZ191695A3 (en) * | 1993-01-25 | 1996-05-15 | Sonus Pharma Inc | Biologically compatible contrast agent, process of its preparation and representation method by ultrasound |
GB9305351D0 (en) * | 1993-03-16 | 1993-05-05 | Nycomed Imaging As | Improvements in or relating to contrast agents |
GB9318288D0 (en) * | 1993-09-03 | 1993-10-20 | Nycomed Imaging As | Improvements in or relating to contrast agents |
HU225495B1 (en) | 1993-12-15 | 2007-01-29 | Bracco Research Sa | Gas mixtures useful as ultrasound contrast media |
GB9402867D0 (en) * | 1994-02-15 | 1994-04-06 | Nycomed Imaging As | Improvements in or relating to contrast agents |
GB9417941D0 (en) * | 1994-09-06 | 1994-10-26 | Nycomed Imaging As | Improvements in or relating to contrast agents |
GB9622711D0 (en) * | 1996-10-31 | 1997-01-08 | British Tech Group | Instrument having enhanced ultrasound visibility |
US20020159951A1 (en) * | 1997-05-06 | 2002-10-31 | Unger Evan C. | Novel targeted compositions for diagnostic and therapeutic use |
US7637948B2 (en) | 1997-10-10 | 2009-12-29 | Senorx, Inc. | Tissue marking implant |
US8668737B2 (en) | 1997-10-10 | 2014-03-11 | Senorx, Inc. | Tissue marking implant |
US20010003580A1 (en) | 1998-01-14 | 2001-06-14 | Poh K. Hui | Preparation of a lipid blend and a phospholipid suspension containing the lipid blend |
US6347241B2 (en) | 1999-02-02 | 2002-02-12 | Senorx, Inc. | Ultrasonic and x-ray detectable biopsy site marker and apparatus for applying it |
US6725083B1 (en) | 1999-02-02 | 2004-04-20 | Senorx, Inc. | Tissue site markers for in VIVO imaging |
US8498693B2 (en) | 1999-02-02 | 2013-07-30 | Senorx, Inc. | Intracorporeal marker and marker delivery device |
US6862470B2 (en) | 1999-02-02 | 2005-03-01 | Senorx, Inc. | Cavity-filling biopsy site markers |
US7983734B2 (en) | 2003-05-23 | 2011-07-19 | Senorx, Inc. | Fibrous marker and intracorporeal delivery thereof |
US20090030309A1 (en) | 2007-07-26 | 2009-01-29 | Senorx, Inc. | Deployment of polysaccharide markers |
US7651505B2 (en) | 2002-06-17 | 2010-01-26 | Senorx, Inc. | Plugged tip delivery for marker placement |
US8361082B2 (en) | 1999-02-02 | 2013-01-29 | Senorx, Inc. | Marker delivery device with releasable plug |
US9820824B2 (en) | 1999-02-02 | 2017-11-21 | Senorx, Inc. | Deployment of polysaccharide markers for treating a site within a patent |
US6575991B1 (en) | 1999-06-17 | 2003-06-10 | Inrad, Inc. | Apparatus for the percutaneous marking of a lesion |
US7311893B2 (en) * | 2000-07-25 | 2007-12-25 | Neurochem (International) Limited | Amyloid targeting imaging agents and uses thereof |
EP2319449B1 (fr) | 2000-11-20 | 2016-03-09 | Senorx, Inc. | Marqueurs de sites tissulaires pour l' imagerie in vivo |
GB0128052D0 (en) | 2001-11-22 | 2002-01-16 | Drug Discovery Lab As | Compounds |
AUPR951501A0 (en) * | 2001-12-14 | 2002-01-24 | Smart Drug Systems Inc | Modified sustained release pharmaceutical system |
US7462366B2 (en) | 2002-03-29 | 2008-12-09 | Boston Scientific Scimed, Inc. | Drug delivery particle |
DE10224352A1 (de) * | 2002-06-01 | 2003-12-11 | Mueller Schulte Detlef | Thermosensitive Polymerträger mit veränderbarer physikalischer Struktur für die biochemische Analytik, Diagnostik und Therapie |
WO2003105917A2 (fr) | 2002-06-12 | 2003-12-24 | Scimed Life Systems, Inc. | Agents gonflants |
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 |
US7883490B2 (en) | 2002-10-23 | 2011-02-08 | Boston Scientific Scimed, Inc. | Mixing and delivery of therapeutic compositions |
US20060036158A1 (en) | 2003-11-17 | 2006-02-16 | Inrad, Inc. | Self-contained, self-piercing, side-expelling marking apparatus |
US7877133B2 (en) | 2003-05-23 | 2011-01-25 | Senorx, Inc. | Marker or filler forming fluid |
US7976823B2 (en) | 2003-08-29 | 2011-07-12 | Boston Scientific Scimed, Inc. | Ferromagnetic particles and methods |
US20050273002A1 (en) | 2004-06-04 | 2005-12-08 | Goosen Ryan L | Multi-mode imaging marker |
WO2005061088A1 (fr) * | 2003-12-22 | 2005-07-07 | Finlay Warren H | Fomation de poudre par lyophilisation par vaporisation atmospherique |
US7025726B2 (en) | 2004-01-22 | 2006-04-11 | The Regents Of The University Of Nebraska | Detection of endothelial dysfunction by ultrasonic imaging |
US7736671B2 (en) | 2004-03-02 | 2010-06-15 | Boston Scientific Scimed, Inc. | Embolization |
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 |
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 |
US10357328B2 (en) | 2005-04-20 | 2019-07-23 | Bard Peripheral Vascular, Inc. and Bard Shannon Limited | Marking device with retractable cannula |
US7963287B2 (en) | 2005-04-28 | 2011-06-21 | Boston Scientific Scimed, Inc. | Tissue-treatment methods |
JP2006327986A (ja) * | 2005-05-26 | 2006-12-07 | Nitto Denko Corp | カーボネート基含有(メタ)アクリル酸エステルモノマーとその製造方法 |
US8123693B2 (en) | 2005-06-20 | 2012-02-28 | Conceptus, Inc. | Methods and devices for determining lumen occlusion |
US9463426B2 (en) | 2005-06-24 | 2016-10-11 | Boston Scientific Scimed, Inc. | Methods and systems for coating particles |
US8052658B2 (en) | 2005-10-07 | 2011-11-08 | Bard Peripheral Vascular, Inc. | Drug-eluting tissue marker |
US8007509B2 (en) | 2005-10-12 | 2011-08-30 | Boston Scientific Scimed, Inc. | Coil assemblies, components and methods |
US8152839B2 (en) | 2005-12-19 | 2012-04-10 | Boston Scientific Scimed, Inc. | Embolic coils |
US8101197B2 (en) | 2005-12-19 | 2012-01-24 | Stryker Corporation | Forming coils |
US7947368B2 (en) | 2005-12-21 | 2011-05-24 | Boston Scientific Scimed, Inc. | Block copolymer particles |
EP2079385B1 (fr) | 2006-10-23 | 2013-11-20 | C.R.Bard, Inc. | Marqueur mammaire |
US8414927B2 (en) | 2006-11-03 | 2013-04-09 | Boston Scientific Scimed, Inc. | Cross-linked polymer particles |
EP2109409B1 (fr) | 2006-12-12 | 2018-09-05 | C.R.Bard, Inc. | Marqueur tissulaire pour mode d'imagerie multiple |
US8401622B2 (en) | 2006-12-18 | 2013-03-19 | C. R. Bard, Inc. | Biopsy marker with in situ-generated imaging properties |
WO2009099767A2 (fr) | 2008-01-31 | 2009-08-13 | C.R. Bard, Inc. | Marqueur de tissu pour biopsie |
US9327061B2 (en) | 2008-09-23 | 2016-05-03 | Senorx, Inc. | Porous bioabsorbable implant |
US8670818B2 (en) | 2008-12-30 | 2014-03-11 | C. R. Bard, Inc. | Marker delivery device for tissue marker placement |
US8585616B2 (en) | 2009-10-09 | 2013-11-19 | Conceptus, Inc. | Methods and apparatus for determining fallopian tube occlusion |
USD715942S1 (en) | 2013-09-24 | 2014-10-21 | C. R. Bard, Inc. | Tissue marker for intracorporeal site identification |
USD716450S1 (en) | 2013-09-24 | 2014-10-28 | C. R. Bard, Inc. | Tissue marker for intracorporeal site identification |
USD716451S1 (en) | 2013-09-24 | 2014-10-28 | C. R. Bard, Inc. | Tissue marker for intracorporeal site identification |
USD715442S1 (en) | 2013-09-24 | 2014-10-14 | C. R. Bard, Inc. | Tissue marker for intracorporeal site identification |
CN104817662B (zh) * | 2015-04-09 | 2017-07-14 | 清华大学 | 同时用于ct和核磁成像的含碘、含氟氨基磷酸酯类高分子造影剂及其制备方法与应用 |
JP7115914B2 (ja) | 2017-06-23 | 2022-08-09 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU636481B2 (en) * | 1990-05-18 | 1993-04-29 | Bracco International B.V. | Polymeric gas or air filled microballoons usable as suspensions in liquid carriers for ultrasonic echography |
PH31064A (en) * | 1990-09-07 | 1998-02-05 | Nycomed As Of Nycoveten | Polymers containing diester units. |
GB9106686D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
GB9106673D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
US5558857A (en) * | 1991-06-03 | 1996-09-24 | Nycomed Imaging As | Contrast agents |
-
1993
- 1993-03-05 HU HU9402565A patent/HUT68612A/hu unknown
- 1993-03-05 AT AT93905527T patent/ATE184491T1/de active
- 1993-03-05 CZ CZ942148A patent/CZ284844B6/cs not_active IP Right Cessation
- 1993-03-05 EP EP93905527A patent/EP0627942B1/fr not_active Expired - Lifetime
- 1993-03-05 IL IL104963A patent/IL104963A/xx not_active IP Right Cessation
- 1993-03-05 SG SG1996005321A patent/SG44668A1/en unknown
- 1993-03-05 CA CA002130670A patent/CA2130670A1/fr not_active Abandoned
- 1993-03-05 BR BR9306044A patent/BR9306044A/pt not_active Application Discontinuation
- 1993-03-05 SK SK1066-94A patent/SK106694A3/sk unknown
- 1993-03-05 WO PCT/GB1993/000470 patent/WO1993017718A1/fr active IP Right Grant
- 1993-03-05 RU RU94045927A patent/RU2122432C1/ru active
- 1993-03-05 AU AU36424/93A patent/AU676467B2/en not_active Ceased
- 1993-03-05 PL PL93305025A patent/PL174114B1/pl unknown
- 1993-03-05 CN CN93104052A patent/CN1084410A/zh active Pending
- 1993-03-05 DE DE69326447T patent/DE69326447T2/de not_active Expired - Fee Related
- 1993-03-05 LV LVP-93-171A patent/LV10396B/en unknown
- 1993-03-05 JP JP51546493A patent/JP3650393B2/ja not_active Expired - Fee Related
- 1993-03-05 ES ES93905527T patent/ES2135466T3/es not_active Expired - Lifetime
- 1993-03-05 NZ NZ249548A patent/NZ249548A/en unknown
- 1993-03-05 US US08/284,464 patent/US5795562A/en not_active Expired - Fee Related
-
1994
- 1994-05-23 EE EE9400024A patent/EE03079B1/xx unknown
- 1994-08-24 OA OA60556A patent/OA10096A/en unknown
- 1994-09-05 FI FI944077A patent/FI944077A0/fi unknown
- 1994-09-05 NO NO943272A patent/NO943272D0/no not_active Application Discontinuation
- 1994-09-28 BG BG99072A patent/BG99072A/bg unknown
Also Published As
Publication number | Publication date |
---|---|
CN1084410A (zh) | 1994-03-30 |
EP0627942B1 (fr) | 1999-09-15 |
WO1993017718A1 (fr) | 1993-09-16 |
EP0627942A1 (fr) | 1994-12-14 |
IL104963A0 (en) | 1993-07-08 |
JPH07505148A (ja) | 1995-06-08 |
CZ284844B6 (cs) | 1999-03-17 |
RU2122432C1 (ru) | 1998-11-27 |
HUT68612A (en) | 1995-07-28 |
DE69326447D1 (de) | 1999-10-21 |
SG44668A1 (en) | 1997-12-19 |
BR9306044A (pt) | 1997-11-18 |
AU676467B2 (en) | 1997-03-13 |
OA10096A (en) | 1996-12-18 |
LV10396B (en) | 1996-02-20 |
EE03079B1 (et) | 1998-04-15 |
CZ214894A3 (en) | 1995-04-12 |
IL104963A (en) | 1997-09-30 |
HU9402565D0 (en) | 1994-11-28 |
NO943272L (no) | 1994-09-05 |
JP3650393B2 (ja) | 2005-05-18 |
NZ249548A (en) | 1996-08-27 |
NO943272D0 (no) | 1994-09-05 |
SK106694A3 (en) | 1995-08-09 |
PL174114B1 (pl) | 1998-06-30 |
US5795562A (en) | 1998-08-18 |
ES2135466T3 (es) | 1999-11-01 |
FI944077A (fi) | 1994-09-05 |
RU94045927A (ru) | 1996-11-10 |
DE69326447T2 (de) | 2000-05-18 |
LV10396A (lv) | 1995-02-20 |
CA2130670A1 (fr) | 1993-09-07 |
ATE184491T1 (de) | 1999-10-15 |
AU3642493A (en) | 1993-10-05 |
FI944077A0 (fi) | 1994-09-05 |
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