UA75364C2 - Perfluoroalkyl-containing complexes with remainders of sugars, a method for obtaining and use thereof - Google Patents
Perfluoroalkyl-containing complexes with remainders of sugars, a method for obtaining and use thereof Download PDFInfo
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- UA75364C2 UA75364C2 UA2003032069A UA2003032069A UA75364C2 UA 75364 C2 UA75364 C2 UA 75364C2 UA 2003032069 A UA2003032069 A UA 2003032069A UA 2003032069 A UA2003032069 A UA 2003032069A UA 75364 C2 UA75364 C2 UA 75364C2
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- 235000000346 sugar Nutrition 0.000 title claims abstract description 14
- 125000005010 perfluoroalkyl group Chemical group 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 55
- 150000008163 sugars Chemical class 0.000 title claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 238000001990 intravenous administration Methods 0.000 claims abstract description 15
- 206010028851 Necrosis Diseases 0.000 claims abstract description 14
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 14
- 230000017074 necrotic cell death Effects 0.000 claims abstract description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 206010061216 Infarction Diseases 0.000 claims abstract description 8
- 230000007574 infarction Effects 0.000 claims abstract description 8
- 238000003745 diagnosis Methods 0.000 claims abstract description 7
- 150000002772 monosaccharides Chemical group 0.000 claims abstract description 6
- 150000002482 oligosaccharides Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 324
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- 239000002872 contrast media Substances 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 230000035699 permeability Effects 0.000 claims description 30
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 28
- 150000001412 amines Chemical class 0.000 claims description 26
- 229910021645 metal ion Inorganic materials 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 230000003993 interaction Effects 0.000 claims description 20
- 238000012800 visualization Methods 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 150000001413 amino acids Chemical class 0.000 claims description 15
- 150000001735 carboxylic acids Chemical class 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 239000008177 pharmaceutical agent Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- 238000001959 radiotherapy Methods 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 8
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 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 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 238000003776 cleavage reaction Methods 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 230000007017 scission Effects 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 125000004429 atom Chemical group 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229930182830 galactose Natural products 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
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- 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 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 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 3
- 210000004324 lymphatic system Anatomy 0.000 claims description 3
- 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
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000005304 joining Methods 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
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 9
- 241000256844 Apis mellifera Species 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 210000005056 cell body Anatomy 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 238000003384 imaging method Methods 0.000 abstract description 9
- 125000005647 linker group Chemical group 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 310
- 239000000243 solution Substances 0.000 description 293
- 238000000921 elemental analysis Methods 0.000 description 160
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 128
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 117
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 112
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 112
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 108
- 235000019441 ethanol Nutrition 0.000 description 105
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 105
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 98
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 97
- 239000003480 eluent Substances 0.000 description 97
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- 238000006243 chemical reaction Methods 0.000 description 84
- 239000000203 mixture Substances 0.000 description 80
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- 229910002027 silica gel Inorganic materials 0.000 description 78
- 239000003054 catalyst Substances 0.000 description 76
- 239000000126 substance Substances 0.000 description 71
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
- 239000003921 oil Substances 0.000 description 68
- 239000007787 solid Substances 0.000 description 67
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 66
- 150000001408 amides Chemical class 0.000 description 63
- 239000000706 filtrate Substances 0.000 description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- 238000003756 stirring Methods 0.000 description 59
- 238000003828 vacuum filtration Methods 0.000 description 56
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
- 239000007983 Tris buffer Substances 0.000 description 43
- 238000001514 detection method Methods 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 37
- 238000000108 ultra-filtration Methods 0.000 description 37
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- 239000012230 colorless oil Substances 0.000 description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 35
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- -1 (Ce) Chemical compound 0.000 description 24
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 24
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 24
- 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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- 210000001165 lymph node Anatomy 0.000 description 23
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000010521 absorption reaction Methods 0.000 description 21
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- 235000002639 sodium chloride Nutrition 0.000 description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 19
- 239000004202 carbamide Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 17
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 17
- 239000012298 atmosphere Substances 0.000 description 17
- WTNMWCJVEAIMLV-UHFFFAOYSA-N 2-[2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]propanoylamino]acetic acid Chemical compound OC(=O)CNC(=O)C(C)N1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WTNMWCJVEAIMLV-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 229910052763 palladium Inorganic materials 0.000 description 16
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
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- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 14
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- 206010027476 Metastases Diseases 0.000 description 9
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
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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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000012285 ultrasound imaging Methods 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75364C2 true UA75364C2 (en) | 2006-04-17 |
Family
ID=7652861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003032069A UA75364C2 (en) | 2000-08-11 | 2001-07-23 | Perfluoroalkyl-containing complexes with remainders of sugars, a method for obtaining and use thereof |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP1307446B1 (xx) |
| JP (1) | JP2004506631A (xx) |
| KR (1) | KR100820387B1 (xx) |
| CN (1) | CN1249058C (xx) |
| AR (1) | AR035579A1 (xx) |
| AT (1) | ATE293623T1 (xx) |
| AU (2) | AU2001289729B2 (xx) |
| BG (1) | BG107540A (xx) |
| BR (1) | BR0113192A (xx) |
| CA (1) | CA2418790A1 (xx) |
| CZ (1) | CZ2003340A3 (xx) |
| DE (2) | DE10040381C1 (xx) |
| DK (1) | DK1307446T3 (xx) |
| EE (1) | EE200300059A (xx) |
| ES (1) | ES2240517T3 (xx) |
| HK (1) | HK1062016A1 (xx) |
| HR (1) | HRP20030172A2 (xx) |
| HU (1) | HUP0300744A3 (xx) |
| IL (1) | IL154328A0 (xx) |
| MX (1) | MXPA03001285A (xx) |
| NO (1) | NO20030648L (xx) |
| NZ (1) | NZ524079A (xx) |
| PL (1) | PL360359A1 (xx) |
| PT (1) | PT1307446E (xx) |
| RU (1) | RU2280644C2 (xx) |
| SK (1) | SK1542003A3 (xx) |
| TW (1) | TWI243170B (xx) |
| UA (1) | UA75364C2 (xx) |
| WO (1) | WO2002014309A1 (xx) |
| YU (1) | YU10403A (xx) |
| ZA (1) | ZA200301948B (xx) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2009509915A (ja) * | 2005-07-15 | 2009-03-12 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | ペルフルオロアルキル含有錯体、ならびにｎｍｒ、ｘ線および放射線診断、さらに放射線治療のための造影剤としてのその使用法 |
| DE102006049821A1 (de) | 2006-10-18 | 2008-04-24 | Bayer Schering Pharma Aktiengesellschaft | Metallchelate mit perfluoriertem PEG-Rest, Verfahren zu deren Herstellung, sowie deren Verwendung |
| US20100215581A1 (en) * | 2006-10-25 | 2010-08-26 | Koninklijke Philips Electronics N.V. | Contrast agents for detecting prostate cancer |
| 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 |
| CA3044877A1 (en) | 2016-11-28 | 2018-05-31 | Bayer Pharma Aktiengesellschaft | High relaxivity gadolinium chelate compounds for use in magnetic resonance imaging |
| EP3883613A1 (en) | 2018-11-23 | 2021-09-29 | Bayer Aktiengesellschaft | Formulation of contrast media and process of preparation thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CA2069886A1 (en) * | 1989-10-23 | 1991-04-24 | David Love | Multi-site metal chelating agents |
| US5330743A (en) * | 1992-11-12 | 1994-07-19 | Magnetic Research, Inc. | Aminosaccharide contrast agents for magnetic resonance images |
| IL115670A (en) * | 1994-10-21 | 1999-11-30 | Nihon Mediphysics Co Ltd | 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 |
-
2000
- 2000-08-11 DE DE10040381A patent/DE10040381C1/de not_active Expired - Fee Related
-
2001
- 2001-07-23 HU HU0300744A patent/HUP0300744A3/hu unknown
- 2001-07-23 ES ES01969481T patent/ES2240517T3/es not_active Expired - Lifetime
- 2001-07-23 PL PL01360359A patent/PL360359A1/xx not_active Application Discontinuation
- 2001-07-23 WO PCT/EP2001/008499 patent/WO2002014309A1/de active IP Right Grant
- 2001-07-23 MX MXPA03001285A patent/MXPA03001285A/es active IP Right Grant
- 2001-07-23 IL IL15432801A patent/IL154328A0/xx unknown
- 2001-07-23 CN CNB018171109A patent/CN1249058C/zh not_active Expired - Fee Related
- 2001-07-23 BR BR0113192-3A patent/BR0113192A/pt not_active IP Right Cessation
- 2001-07-23 UA UA2003032069A patent/UA75364C2/uk unknown
- 2001-07-23 NZ NZ524079A patent/NZ524079A/en unknown
- 2001-07-23 AT AT01969481T patent/ATE293623T1/de not_active IP Right Cessation
- 2001-07-23 RU RU2003105815/04A patent/RU2280644C2/ru not_active IP Right Cessation
- 2001-07-23 DE DE50105965T patent/DE50105965D1/de not_active Expired - Fee Related
- 2001-07-23 YU YU10403A patent/YU10403A/sh unknown
- 2001-07-23 CA CA002418790A patent/CA2418790A1/en not_active Abandoned
- 2001-07-23 EE EEP200300059A patent/EE200300059A/xx unknown
- 2001-07-23 DK DK01969481T patent/DK1307446T3/da active
- 2001-07-23 KR KR1020037002021A patent/KR100820387B1/ko not_active IP Right Cessation
- 2001-07-23 AU AU2001289729A patent/AU2001289729B2/en not_active Ceased
- 2001-07-23 PT PT01969481T patent/PT1307446E/pt unknown
- 2001-07-23 EP EP01969481A patent/EP1307446B1/de not_active Expired - Lifetime
- 2001-07-23 CZ CZ2003340A patent/CZ2003340A3/cs unknown
- 2001-07-23 AU AU8972901A patent/AU8972901A/xx active Pending
- 2001-07-23 JP JP2002519449A patent/JP2004506631A/ja active Pending
- 2001-07-23 SK SK154-2003A patent/SK1542003A3/sk unknown
- 2001-08-10 TW TW090119623A patent/TWI243170B/zh not_active IP Right Cessation
- 2001-08-10 AR ARP010103831A patent/AR035579A1/es unknown
-
2003
- 2003-02-07 BG BG107540A patent/BG107540A/bg unknown
- 2003-02-10 NO NO20030648A patent/NO20030648L/no not_active Application Discontinuation
- 2003-03-10 ZA ZA200301948A patent/ZA200301948B/en unknown
- 2003-03-10 HR HR20030172A patent/HRP20030172A2/hr not_active Application Discontinuation
-
2004
- 2004-07-13 HK HK04105095A patent/HK1062016A1/xx not_active IP Right Cessation
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