HRP20030172A2 - Perfluoroalkyl-containing complexes comprising sugar residues, method for producing the same and usethereof - Google Patents
Perfluoroalkyl-containing complexes comprising sugar residues, method for producing the same and usethereof Download PDFInfo
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- HRP20030172A2 HRP20030172A2 HR20030172A HRP20030172A HRP20030172A2 HR P20030172 A2 HRP20030172 A2 HR P20030172A2 HR 20030172 A HR20030172 A HR 20030172A HR P20030172 A HRP20030172 A HR P20030172A HR P20030172 A2 HRP20030172 A2 HR P20030172A2
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- 238000004519 manufacturing process Methods 0.000 title claims description 22
- 235000000346 sugar Nutrition 0.000 title claims description 11
- 125000005010 perfluoroalkyl group Chemical group 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 327
- 238000006243 chemical reaction Methods 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 239000002872 contrast media Substances 0.000 claims description 42
- 229910052751 metal Inorganic materials 0.000 claims description 36
- 239000002184 metal Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 229910021645 metal ion Inorganic materials 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 150000004696 coordination complex Chemical class 0.000 claims description 18
- 206010028980 Neoplasm Diseases 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 16
- 206010061216 Infarction Diseases 0.000 claims description 15
- 150000001413 amino acids Chemical class 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- 230000007574 infarction Effects 0.000 claims description 15
- 206010028851 Necrosis Diseases 0.000 claims description 14
- 230000017074 necrotic cell death Effects 0.000 claims description 14
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- 238000003776 cleavage reaction Methods 0.000 claims description 11
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- 238000003745 diagnosis Methods 0.000 claims description 7
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- 150000007530 organic bases Chemical class 0.000 claims description 7
- 238000001959 radiotherapy Methods 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
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- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
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- 239000008177 pharmaceutical agent Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 230000004856 capillary permeability Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 210000004324 lymphatic system Anatomy 0.000 claims description 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 311
- 239000000243 solution Substances 0.000 description 178
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 147
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 125
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 120
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 117
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 114
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 112
- 238000004458 analytical method Methods 0.000 description 105
- 239000000203 mixture Substances 0.000 description 100
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- 239000002904 solvent Substances 0.000 description 92
- 239000000126 substance Substances 0.000 description 89
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 74
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 74
- 239000000741 silica gel Substances 0.000 description 74
- 229910002027 silica gel Inorganic materials 0.000 description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 68
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- 239000003921 oil Substances 0.000 description 62
- 239000007787 solid Substances 0.000 description 61
- 239000003054 catalyst Substances 0.000 description 57
- 238000000921 elemental analysis Methods 0.000 description 54
- 238000003756 stirring Methods 0.000 description 54
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 54
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- 239000011541 reaction mixture Substances 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 44
- 239000012230 colorless oil Substances 0.000 description 44
- 239000000706 filtrate Substances 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000007983 Tris buffer Substances 0.000 description 41
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 36
- -1 gadolinium ions Chemical class 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 33
- 239000003480 eluent Substances 0.000 description 31
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
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- 229910052763 palladium Inorganic materials 0.000 description 21
- 239000011734 sodium Substances 0.000 description 21
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- 238000012545 processing Methods 0.000 description 20
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 19
- 238000001556 precipitation Methods 0.000 description 19
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 15
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- 125000004494 ethyl ester group Chemical group 0.000 description 14
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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- 235000006748 manganese carbonate Nutrition 0.000 description 1
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- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
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- 229910052761 rare earth metal Inorganic materials 0.000 description 1
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- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- HKCRVXUAKWXBLE-UHFFFAOYSA-N terbium(3+) Chemical compound [Tb+3] HKCRVXUAKWXBLE-UHFFFAOYSA-N 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
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- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical class NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10040381A DE10040381C1 (de) | 2000-08-11 | 2000-08-11 | Perfluoralkylhaltige Komplexe mit Zuckerresten, Verfahren zu deren Herstellung und ihre Verwendung |
| PCT/EP2001/008499 WO2002014309A1 (de) | 2000-08-11 | 2001-07-23 | Perfluoralkylhaltige komplexe mit zuckerresten, verfahren zu deren herstellung und ihre verwendung |
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| HRP20030172A2 true HRP20030172A2 (en) | 2005-04-30 |
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| HR20030172A HRP20030172A2 (en) | 2000-08-11 | 2003-03-10 | Perfluoroalkyl-containing complexes comprising sugar residues, method for producing the same and usethereof |
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| EP (1) | EP1307446B1 (da) |
| JP (1) | JP2004506631A (da) |
| KR (1) | KR100820387B1 (da) |
| CN (1) | CN1249058C (da) |
| AR (1) | AR035579A1 (da) |
| AT (1) | ATE293623T1 (da) |
| AU (2) | AU8972901A (da) |
| BG (1) | BG107540A (da) |
| BR (1) | BR0113192A (da) |
| CA (1) | CA2418790A1 (da) |
| CZ (1) | CZ2003340A3 (da) |
| DE (2) | DE10040381C1 (da) |
| DK (1) | DK1307446T3 (da) |
| EE (1) | EE200300059A (da) |
| ES (1) | ES2240517T3 (da) |
| HK (1) | HK1062016A1 (da) |
| HR (1) | HRP20030172A2 (da) |
| HU (1) | HUP0300744A3 (da) |
| IL (1) | IL154328A0 (da) |
| MX (1) | MXPA03001285A (da) |
| NO (1) | NO20030648L (da) |
| NZ (1) | NZ524079A (da) |
| PL (1) | PL360359A1 (da) |
| PT (1) | PT1307446E (da) |
| RU (1) | RU2280644C2 (da) |
| SK (1) | SK1542003A3 (da) |
| TW (1) | TWI243170B (da) |
| UA (1) | UA75364C2 (da) |
| WO (1) | WO2002014309A1 (da) |
| YU (1) | YU10403A (da) |
| ZA (1) | ZA200301948B (da) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE19948651B4 (de) * | 1999-09-29 | 2006-10-05 | Schering Ag | Para- und diamagnetische perfluorhaltige Verbindungen enthaltende galenische Formulierungen, deren Herstellung und Verwendung |
| US7344704B2 (en) | 2002-07-10 | 2008-03-18 | Schering Ag | Use of perfluoroalkyl-containing metal complexes as contrast media in MR-imaging for visualization of intravascular thrombi |
| DE10231799B4 (de) * | 2002-07-10 | 2006-10-05 | Schering Ag | Verwendung von perfluoralkylhaltigen Metallkomplexen als Kontrastmittel im MR-Imaging zur Darstellung von Intravasalen Thromben |
| DE10260372B4 (de) | 2002-12-13 | 2007-01-04 | Schering Ag | Kernspintomographievorrichtung und Verfahren zur ortsaufgelösten Bilddarstellung |
| EP1904462A2 (de) * | 2005-07-15 | 2008-04-02 | Bayer Schering Pharma Aktiengesellschaft | Perfluoralkylhaltige komplexe, verfahren zu deren herstellung, sowie deren verwendung |
| DE102006049821A1 (de) | 2006-10-18 | 2008-04-24 | Bayer Schering Pharma Aktiengesellschaft | Metallchelate mit perfluoriertem PEG-Rest, Verfahren zu deren Herstellung, sowie deren Verwendung |
| JP2010507645A (ja) * | 2006-10-25 | 2010-03-11 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | 前立腺癌を検出するための造影剤 |
| DE102008024976A1 (de) | 2008-05-23 | 2009-12-17 | Marvis Technologies Gmbh | Medizinisches Instrument |
| JP2011190183A (ja) * | 2010-03-11 | 2011-09-29 | Noguchi Institute | フルオラス化糖結合型クラウンエーテル誘導体 |
| EP2450067A1 (en) | 2010-10-18 | 2012-05-09 | MaRVis Technologies GmbH | Medical device |
| EP2484388A1 (en) | 2011-02-05 | 2012-08-08 | MaRVis Technologies GmbH | Implantable or insertable MRI-detectable medical device having a coating comprising paramagnetic ions and a process for preparing it |
| EP2692365A1 (en) | 2012-08-03 | 2014-02-05 | MaRVis Medical GmbH | Implantable or insertable MRI-detectable medical device having a coating comprising paramagnetic ions and a process for preparing it |
| EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
| CN110035996B (zh) | 2016-11-28 | 2022-08-09 | 拜耳医药股份公司 | 用于磁共振成像的新型高弛豫性钆螯合物 |
| KR20210095168A (ko) | 2018-11-23 | 2021-07-30 | 바이엘 악티엔게젤샤프트 | 조영 매체의 제형 및 그의 제조 방법 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5707604A (en) * | 1986-11-18 | 1998-01-13 | Access Pharmaceuticals, Inc. | Vivo agents comprising metal-ion chelates with acidic saccharides and glycosaminoglycans, giving improved site-selective localization, uptake mechanism, sensitivity and kinetic-spatial profiles |
| AU623901B2 (en) * | 1988-01-26 | 1992-05-28 | Nycomed As | Paramagnetic compounds comprising chelating moiety, linker group macro molecule and paramagnetic metal |
| ES2116291T3 (es) * | 1989-10-23 | 1998-07-16 | Nycomed Salutar Inc | Agentes quelantes de metales en sitios multiples. |
| US5330743A (en) * | 1992-11-12 | 1994-07-19 | Magnetic Research, Inc. | Aminosaccharide contrast agents for magnetic resonance images |
| CA2160819A1 (en) * | 1994-10-21 | 1996-04-22 | Yuji Hashiguchi | Diagnostic imaging agent |
| DE19603033A1 (de) * | 1996-01-19 | 1997-07-24 | Schering Ag | Perfluoralkylhaltige Metallkomplexe, Verfahren zu deren Herstellung und ihre Verwendung in der NMR-Diagnostik |
| DE19728954C1 (de) * | 1997-06-30 | 1999-04-22 | Schering Ag | Saccharid-Konjugate, diese enthaltende pharmazeutische Mittel, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19729013A1 (de) * | 1997-07-03 | 1999-02-04 | Schering Ag | Oligomere, perfluoralkylhaltige Verbindungen, Verfahren zu deren Herstellung und ihre Verwendung in der NMR-Diagnostik |
| DE19744004C1 (de) * | 1997-09-26 | 1999-07-22 | Schering Ag | Lipophile Metall-Komplexe für Nekrose und Infarkt-Imaging |
| DE19758105A1 (de) * | 1997-12-18 | 1999-06-24 | Schering Ag | Dendritische Polymer-Saccharid-Konjugate, diese enthaltende pharmazeutische Mittel, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19914101C1 (de) * | 1999-03-22 | 2000-10-12 | Schering Ag | Perfluoralkylamide, ihre Herstellung und ihre Verwendung in der Diagnostik |
| DE19948651B4 (de) * | 1999-09-29 | 2006-10-05 | Schering Ag | Para- und diamagnetische perfluorhaltige Verbindungen enthaltende galenische Formulierungen, deren Herstellung und Verwendung |
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2000
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2001
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- 2001-07-23 UA UA2003032069A patent/UA75364C2/uk unknown
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- 2001-07-23 KR KR1020037002021A patent/KR100820387B1/ko not_active IP Right Cessation
- 2001-07-23 PL PL01360359A patent/PL360359A1/xx not_active Application Discontinuation
- 2001-07-23 EP EP01969481A patent/EP1307446B1/de not_active Expired - Lifetime
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2003
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