NO314127B1 - Injiserbare NMR-billeddannende sammensetninger, fremgangsmåter for fremstilling og anvendelse av disse - Google Patents
Injiserbare NMR-billeddannende sammensetninger, fremgangsmåter for fremstilling og anvendelse av disse Download PDFInfo
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- NO314127B1 NO314127B1 NO19970665A NO970665A NO314127B1 NO 314127 B1 NO314127 B1 NO 314127B1 NO 19970665 A NO19970665 A NO 19970665A NO 970665 A NO970665 A NO 970665A NO 314127 B1 NO314127 B1 NO 314127B1
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- composition according
- acid
- imaging
- surfactant
- physiologically acceptable
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- RAZLJUXJEOEYAM-UHFFFAOYSA-N 2-[bis[2-(2,6-dioxomorpholin-4-yl)ethyl]azaniumyl]acetate Chemical compound C1C(=O)OC(=O)CN1CCN(CC(=O)O)CCN1CC(=O)OC(=O)C1 RAZLJUXJEOEYAM-UHFFFAOYSA-N 0.000 description 2
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- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
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- IZOOGPBRAOKZFK-UHFFFAOYSA-K gadopentetate Chemical compound [Gd+3].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O IZOOGPBRAOKZFK-UHFFFAOYSA-K 0.000 description 1
- GFSTXYOTEVLASN-UHFFFAOYSA-K gadoteric acid Chemical compound [Gd+3].OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 GFSTXYOTEVLASN-UHFFFAOYSA-K 0.000 description 1
- DPNNNPAKRZOSMO-UHFFFAOYSA-K gadoteridol Chemical compound [Gd+3].CC(O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 DPNNNPAKRZOSMO-UHFFFAOYSA-K 0.000 description 1
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- 229920002521 macromolecule Polymers 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000014207 opsonization Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- BMBWFDPPCSTUSZ-MGDILKBHSA-M sodium;[(2r)-2,3-di(hexadecanoyloxy)propyl] hydrogen phosphate Chemical compound [Na+].CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)([O-])=O)OC(=O)CCCCCCCCCCCCCCC BMBWFDPPCSTUSZ-MGDILKBHSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
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- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
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- ORZHVTYKPFFVMG-UHFFFAOYSA-N xylenol orange Chemical compound OC(=O)CN(CC(O)=O)CC1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C=C(CN(CC(O)=O)CC(O)=O)C(O)=C(C)C=2)=C1 ORZHVTYKPFFVMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
-
- 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
- A61K49/1806—Suspensions, emulsions, colloids, dispersions
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Radiology & Medical Imaging (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dispersion Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95810403 | 1995-06-15 | ||
| PCT/IB1996/000577 WO1997000087A1 (en) | 1995-06-15 | 1996-06-14 | Blood-pool imaging compositions use and method |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO970665D0 NO970665D0 (no) | 1997-02-13 |
| NO970665L NO970665L (no) | 1997-04-03 |
| NO314127B1 true NO314127B1 (no) | 2003-02-03 |
Family
ID=8221760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19970665A NO314127B1 (no) | 1995-06-15 | 1997-02-13 | Injiserbare NMR-billeddannende sammensetninger, fremgangsmåter for fremstilling og anvendelse av disse |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5833948A (de) |
| EP (1) | EP0804251B1 (de) |
| JP (1) | JP4335976B2 (de) |
| KR (1) | KR100399712B1 (de) |
| AT (1) | ATE224737T1 (de) |
| AU (1) | AU708328B2 (de) |
| CA (1) | CA2195633C (de) |
| DE (1) | DE69623929T2 (de) |
| ES (1) | ES2180784T3 (de) |
| NO (1) | NO314127B1 (de) |
| PT (1) | PT804251E (de) |
| WO (1) | WO1997000087A1 (de) |
| ZA (1) | ZA965101B (de) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1297034B1 (it) * | 1997-12-30 | 1999-08-03 | Bracco Spa | Acido 1,4,7,10-tetraazaciclododecan-1,4-diacetico |
| IT1297035B1 (it) * | 1997-12-30 | 1999-08-03 | Bracco Spa | Derivati dell'acido 1,4,7,10-tetraazaciclododecan-1,4-diacetico |
| US6342598B1 (en) | 1998-11-26 | 2002-01-29 | Bracco International B.V. | Amphipatic polycarboxylic chelates and complexes with paramagnetic metals as MRI contrast agents |
| EP2286843A3 (de) | 2000-06-02 | 2011-08-03 | Bracco Suisse SA | Arzneimitteln zur Zielgerichtung von Endothelzellen |
| US6984395B2 (en) * | 2001-04-11 | 2006-01-10 | Qlt, Inc. | Drug delivery system for hydrophobic drugs |
| US6506413B1 (en) * | 2001-04-30 | 2003-01-14 | Joseph C. Ramaekers | Compositions for treating animal diseases and syndromes |
| US20070128253A1 (en) * | 2005-04-13 | 2007-06-07 | Ramaekers Joseph C | Encapsulated transfer factor compositions and methods of use |
| US20060073197A1 (en) * | 2004-05-20 | 2006-04-06 | Ramaekers Joseph C | Encapsulated transfer factor compositions and methods of use |
| US6803046B2 (en) | 2002-08-16 | 2004-10-12 | Bracco International B.V. | Sincalide formulations |
| US20050130892A1 (en) * | 2003-03-07 | 2005-06-16 | Xencor, Inc. | BAFF variants and methods thereof |
| US20050221443A1 (en) * | 2003-01-06 | 2005-10-06 | Xencor, Inc. | Tumor necrosis factor super family agonists |
| US20060014248A1 (en) * | 2003-01-06 | 2006-01-19 | Xencor, Inc. | TNF super family members with altered immunogenicity |
| US7553930B2 (en) * | 2003-01-06 | 2009-06-30 | Xencor, Inc. | BAFF variants and methods thereof |
| EP1590006B1 (de) | 2003-02-04 | 2010-09-08 | Bracco Suisse SA | Ultraschall kontrastmittel und verfahren zur erstellung |
| EP2327723A3 (de) | 2003-10-10 | 2012-06-27 | Xencor, Inc. | Proteinbasierte TNF-alpha-Varianten zur Behandlung von mit TNF-alpha zusammenhängenden Erkrankungen |
| CA2547024C (en) | 2003-12-22 | 2013-12-17 | Bracco Research Sa | Gas-filled microvesicle assembly for contrast imaging |
| US20050152842A1 (en) * | 2003-12-24 | 2005-07-14 | Chun Li | Poly (L-glutamic acid) paramagnetic material complex and use as a biodegradable MRI contrast agent |
| CN1960707B (zh) * | 2004-06-03 | 2012-11-14 | 博莱科瑞士股份有限公司 | 用于治疗和/或诊断用途的脂质集合体 |
| WO2006018433A1 (en) | 2004-08-18 | 2006-02-23 | Bracco Research Sa | Gas-filled microvesicles composition for contrast imaging |
| FR2883562B1 (fr) | 2005-03-24 | 2009-02-27 | Guerbet Sa | Chelates lipophiles et leur utilisation en imagerie |
| KR20080009682A (ko) * | 2005-04-01 | 2008-01-29 | 더 보드 오브 리전츠 오브 더 유니버시티 오브 텍사스 시스템 | 킬레이트제인 폴리(펩티드): 제조 방법과 용도 |
| EP1898958A2 (de) * | 2005-05-31 | 2008-03-19 | INBIOS S.r.l. | Supramolekulare aggregate mit cheliermitteln und bioaktiven peptiden als effektive und selektive abgabewerkzeuge für arzneimittel und kontrastmittel bei mrt oder in der nuklearmedizin |
| US20090053197A1 (en) * | 2006-06-14 | 2009-02-26 | Ramaekers Joseph C | Transfer Factor Compositions and Methods |
| US9125874B2 (en) | 2007-11-30 | 2015-09-08 | The Ramaekers Family Trust | Administration of transfer factor for improving reproductive health |
| US9446156B2 (en) | 2006-09-05 | 2016-09-20 | Bracco Suisse S.A. | Gas-filled microvesicles with polymer-modified lipids |
| GB0623838D0 (en) * | 2006-11-29 | 2007-01-10 | Malvern Cosmeceutics Ltd | Novel compositions |
| US20090074751A1 (en) * | 2007-09-18 | 2009-03-19 | Ramaekers Nutrition, Inc. | Growth factor fraction compositions and methods |
| KR101401217B1 (ko) * | 2007-11-07 | 2014-05-28 | 충남대학교산학협력단 | Ｐｅ－ｄｔｐａ의 새로운 용도 |
| US8946148B2 (en) | 2007-11-20 | 2015-02-03 | Ambrx, Inc. | Modified insulin polypeptides and their uses |
| EP2278984A4 (de) * | 2007-11-30 | 2013-02-27 | Ramaekers Family Trust | Zusammensetzungen und verfahren zur verbesserung der fertilität |
| SG10201906494PA (en) | 2008-01-30 | 2019-09-27 | Histogen Inc | Extracellular matrix compositions |
| CN102341126A (zh) * | 2009-02-13 | 2012-02-01 | 华盛顿大学 | 用于磁共振成像的钆表现脂质纳米颗粒 |
| WO2010139003A1 (en) * | 2009-06-01 | 2010-12-09 | Commonwealth Scientific And Industrial Research Organisation | Chelating amphiphiles |
| SG10201506443TA (en) | 2010-08-17 | 2015-10-29 | Ambrx Inc | Modified relaxin polypeptides and their uses |
| EP2639227A1 (de) | 2012-03-14 | 2013-09-18 | Bracco Imaging S.p.A | Neue Klasse von Diazepinderivatchelatbildnern und Komplexe mit paramagnetischen Metallen als MRI-Kontrastmittel |
| US10039843B2 (en) | 2012-09-07 | 2018-08-07 | Bracco Imaging S.P.A. | Paramagnetic solid lipid nanoparticles (pSLNs) containing metal amphiphilic complexes for MRI |
| US11365229B2 (en) | 2012-09-10 | 2022-06-21 | Xencor, Inc. | Methods of treating neurological diseases |
| JP6313329B2 (ja) | 2012-12-21 | 2018-04-18 | ブラッコ・スイス・ソシエテ・アノニムＢｒａｃｃｏ Ｓｕｉｓｓｅ ＳＡ | ガス封入マイクロベシクル |
| WO2015119642A1 (en) | 2014-02-10 | 2015-08-13 | The Johns Hopkins University | Low oxygen tension enhances endothelial fate of human pluripotent stem cells |
| US10519207B2 (en) | 2015-06-12 | 2019-12-31 | Georgia State University Research Foundation, Inc. | Compositions and methods for treating opioid tolerance |
| US11110063B2 (en) | 2017-08-25 | 2021-09-07 | MAIA Pharmaceuticals, Inc. | Storage stable sincalide formulations |
| US12077780B2 (en) | 2020-02-14 | 2024-09-03 | Allergan Sales, Llc | Conditioned medium from cells cultured under hypoxic conditions and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5387410A (en) * | 1983-03-18 | 1995-02-07 | Mallinckrodt, Inc. | Method for enhancing magnetic resonance with compositions containing paramagnetic elements carried by liposomes |
| US4728575A (en) * | 1984-04-27 | 1988-03-01 | Vestar, Inc. | Contrast agents for NMR imaging |
| US5215680A (en) * | 1990-07-10 | 1993-06-01 | Cavitation-Control Technology, Inc. | Method for the production of medical-grade lipid-coated microbubbles, paramagnetic labeling of such microbubbles and therapeutic uses of microbubbles |
| WO1992021017A1 (en) * | 1991-05-23 | 1992-11-26 | Unger Evan C | Liposoluble compounds for magnetic resonance imaging |
| US5464696A (en) * | 1992-08-13 | 1995-11-07 | Bracco International B.V. | Particles for NMR imaging |
| US5534241A (en) * | 1993-07-23 | 1996-07-09 | Torchilin; Vladimir P. | Amphipathic polychelating compounds and methods of use |
| US5567410A (en) * | 1994-06-24 | 1996-10-22 | The General Hospital Corporation | Composotions and methods for radiographic imaging |
-
1996
- 1996-06-13 US US08/663,545 patent/US5833948A/en not_active Expired - Lifetime
- 1996-06-14 ES ES96919971T patent/ES2180784T3/es not_active Expired - Lifetime
- 1996-06-14 AU AU58431/96A patent/AU708328B2/en not_active Ceased
- 1996-06-14 AT AT96919971T patent/ATE224737T1/de not_active IP Right Cessation
- 1996-06-14 JP JP50285697A patent/JP4335976B2/ja not_active Expired - Fee Related
- 1996-06-14 WO PCT/IB1996/000577 patent/WO1997000087A1/en active IP Right Grant
- 1996-06-14 KR KR1019970700923A patent/KR100399712B1/ko not_active IP Right Cessation
- 1996-06-14 EP EP96919971A patent/EP0804251B1/de not_active Expired - Lifetime
- 1996-06-14 DE DE69623929T patent/DE69623929T2/de not_active Expired - Lifetime
- 1996-06-14 ZA ZA965101A patent/ZA965101B/xx unknown
- 1996-06-14 CA CA002195633A patent/CA2195633C/en not_active Expired - Fee Related
- 1996-06-14 PT PT96919971T patent/PT804251E/pt unknown
-
1997
- 1997-02-13 NO NO19970665A patent/NO314127B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR970704477A (ko) | 1997-09-06 |
| JP4335976B2 (ja) | 2009-09-30 |
| WO1997000087A1 (en) | 1997-01-03 |
| CA2195633C (en) | 2008-09-16 |
| PT804251E (pt) | 2003-01-31 |
| US5833948A (en) | 1998-11-10 |
| EP0804251A1 (de) | 1997-11-05 |
| ES2180784T3 (es) | 2003-02-16 |
| AU708328B2 (en) | 1999-08-05 |
| DE69623929D1 (de) | 2002-10-31 |
| DE69623929T2 (de) | 2003-05-15 |
| JPH10504044A (ja) | 1998-04-14 |
| KR100399712B1 (ko) | 2004-02-18 |
| NO970665L (no) | 1997-04-03 |
| AU5843196A (en) | 1997-01-15 |
| ATE224737T1 (de) | 2002-10-15 |
| EP0804251B1 (de) | 2002-09-25 |
| ZA965101B (en) | 1997-01-22 |
| NO970665D0 (no) | 1997-02-13 |
| CA2195633A1 (en) | 1997-01-03 |
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