RU2003105810A - APPLICATION OF PERFluoroalkyl-containing metal complexes as contrast agents in magnetic resonance imaging for visualization of plaques, tumors and necrosis - Google Patents
APPLICATION OF PERFluoroalkyl-containing metal complexes as contrast agents in magnetic resonance imaging for visualization of plaques, tumors and necrosisInfo
- Publication number
- RU2003105810A RU2003105810A RU2003105810/15A RU2003105810A RU2003105810A RU 2003105810 A RU2003105810 A RU 2003105810A RU 2003105810/15 A RU2003105810/15 A RU 2003105810/15A RU 2003105810 A RU2003105810 A RU 2003105810A RU 2003105810 A RU2003105810 A RU 2003105810A
- Authority
- RU
- Russia
- Prior art keywords
- groups
- denotes
- group
- general formula
- residue
- Prior art date
Links
- 229910052751 metal Inorganic materials 0.000 title claims 27
- 239000002184 metal Substances 0.000 title claims 27
- 239000002872 contrast media Substances 0.000 title claims 5
- 238000002595 magnetic resonance imaging Methods 0.000 title claims 5
- 206010028980 Neoplasm Diseases 0.000 title claims 2
- 230000022534 cell killing Effects 0.000 title claims 2
- 230000009089 cytolysis Effects 0.000 title claims 2
- 230000017074 necrotic cell death Effects 0.000 title claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 34
- -1 perfluorooctylsulfonyl Chemical group 0.000 claims 25
- 239000008139 complexing agent Substances 0.000 claims 17
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 17
- UIWYJDYFSGRHKR-UHFFFAOYSA-N Gadolinium Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims 15
- 229910052688 Gadolinium Inorganic materials 0.000 claims 15
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 14
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 13
- 150000004696 coordination complex Chemical class 0.000 claims 11
- 229910052731 fluorine Inorganic materials 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 239000007983 Tris buffer Substances 0.000 claims 10
- 150000001413 amino acids Chemical class 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 150000002500 ions Chemical class 0.000 claims 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 125000004432 carbon atoms Chemical group C* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 125000004429 atoms Chemical group 0.000 claims 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 6
- 239000011630 iodine Substances 0.000 claims 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 6
- 229910052740 iodine Inorganic materials 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 150000007529 inorganic bases Chemical class 0.000 claims 5
- 125000005647 linker group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 150000007530 organic bases Chemical class 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011780 sodium chloride Substances 0.000 claims 5
- 125000004434 sulfur atoms Chemical group 0.000 claims 5
- 230000005292 diamagnetic Effects 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000003827 glycol group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 239000000693 micelle Substances 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- 238000003384 imaging method Methods 0.000 claims 3
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 2
- 229920000858 Cyclodextrin Polymers 0.000 claims 2
- 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 2
- 239000004472 Lysine Substances 0.000 claims 2
- 210000002381 Plasma Anatomy 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 210000002356 Skeleton Anatomy 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 125000003929 folic acid group Chemical group 0.000 claims 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 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 150000002772 monosaccharides Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 1
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- PAQQLEOTIPQUQO-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-10-[3-[6-[ethyl(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylsulfonyl)amino]hexanoylamino]-2-hydroxypropyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)N(CC)CCCCCC(=O)NCC(O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 PAQQLEOTIPQUQO-UHFFFAOYSA-N 0.000 claims 1
- PGIVNKJNVKROAZ-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-10-[3-[[2-[ethyl(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylsulfonyl)amino]acetyl]amino]-2-hydroxypropyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)N(CC)CC(=O)NCC(O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 PGIVNKJNVKROAZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- GZCGUPFRVQAUEE-KCDKBNATSA-N D-(+)-Galactose Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-KCDKBNATSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N Dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical group NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N Isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- 210000001165 Lymph Nodes Anatomy 0.000 claims 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating Effects 0.000 claims 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 229960004853 betadex Drugs 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000003901 ceryl 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])C([H])([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])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 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000001338 necrotic Effects 0.000 claims 1
- 150000002482 oligosaccharides Chemical group 0.000 claims 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000005298 paramagnetic Effects 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 229940081066 picolinic acid Drugs 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229920000151 polyglycol Polymers 0.000 claims 1
- 239000010695 polyglycol Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 125000001174 sulfone group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 1
- 125000000464 thioxo group Chemical group S=* 0.000 claims 1
- 210000001519 tissues Anatomy 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N α-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 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N α-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-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 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N β-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims 1
- GDSRMADSINPKSL-HSEONFRVSA-N γ-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims 1
- 0 CC(C(*(CO)CO)=N)N*(CC*(CO)CO)CN Chemical compound CC(C(*(CO)CO)=N)N*(CC*(CO)CO)CN 0.000 description 5
Claims (50)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10040380.8 | 2000-08-11 | ||
DE10040380A DE10040380B4 (en) | 2000-08-11 | 2000-08-11 | MRI contrast agent for visualization of plaque, lymph nodes, infarcted and necrotic tissue or both necrosis and tumors, comprising perfluoroalkylated metal complex having specific micelle forming properties |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2003105810A true RU2003105810A (en) | 2004-09-10 |
RU2290206C2 RU2290206C2 (en) | 2006-12-27 |
Family
ID=7652860
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2003105810/15A RU2290206C2 (en) | 2000-08-11 | 2001-07-23 | Using perfluoroalkyl-containing metal complexes as contrasting substances in magnetic-resonance tomography in visualization of patches, tumors and necrosis |
Country Status (26)
Country | Link |
---|---|
EP (1) | EP1307236A2 (en) |
JP (1) | JP2004506025A (en) |
KR (1) | KR20030022387A (en) |
CN (1) | CN1469757A (en) |
AR (1) | AR034139A1 (en) |
AU (2) | AU2001277549B2 (en) |
BG (1) | BG107542A (en) |
BR (1) | BR0113188A (en) |
CA (1) | CA2419223A1 (en) |
CZ (1) | CZ2003392A3 (en) |
DE (1) | DE10066210B4 (en) |
EE (1) | EE200300061A (en) |
HR (1) | HRP20030173A2 (en) |
HU (1) | HUP0300736A3 (en) |
IL (1) | IL154385A0 (en) |
MX (1) | MXPA03001287A (en) |
NO (1) | NO20030604L (en) |
NZ (1) | NZ523932A (en) |
PL (1) | PL365596A1 (en) |
RU (1) | RU2290206C2 (en) |
SK (1) | SK1572003A3 (en) |
TW (1) | TWI296931B (en) |
UA (1) | UA82642C2 (en) |
WO (1) | WO2002013874A2 (en) |
YU (1) | YU10603A (en) |
ZA (1) | ZA200301949B (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10231799B4 (en) * | 2002-07-10 | 2006-10-05 | Schering Ag | Use of perfluoroalkyl-containing metal complexes as contrast agents in MR imaging for the presentation of intravascular thrombi |
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 |
DE102005008309A1 (en) * | 2005-02-17 | 2006-08-24 | Schering Ag | Pharmaceutical agents containing fluoroalkyl-containing metal complexes and epothilones |
DE102006021495A1 (en) * | 2006-05-09 | 2007-11-15 | Bayer Schering Pharma Ag | Use of metal chelate containing perfluorinated alkyl-residue, chelator-residue and metal ion equivalent to the atomic number, for the production of diagnostic agent for representation of amyloid-containing plaques |
US7887835B2 (en) * | 2006-09-19 | 2011-02-15 | Fujifilm Corporation | Compound comprising a fluorine-substituted alkyl group and a liposome contrast medium comprising the compound |
DE102006049821A1 (en) | 2006-10-18 | 2008-04-24 | Bayer Schering Pharma Aktiengesellschaft | New, well tolerated metal chelates, for use as radiodiagnostic, radiotherapeutic or NMR and X-ray diagnostic agents, contain chelator and perfluorinated polyethylene glycol residues |
DE102007015598A1 (en) * | 2007-03-29 | 2008-10-02 | Heinrich-Heine-Universität Düsseldorf | Use of fluorochemical compounds for diagnostic purposes using imaging techniques |
JP2011190183A (en) * | 2010-03-11 | 2011-09-29 | Noguchi Institute | Fluorous sugar-bonded crown ether derivative |
US9976072B2 (en) | 2014-03-26 | 2018-05-22 | Chevron U.S.A. Inc. | Multicarboxylate compositions and method of making the same |
EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
JP7037069B2 (en) * | 2016-09-14 | 2022-03-16 | ダイキン工業株式会社 | Branched fluorine-containing compound |
ES2814555T3 (en) | 2016-11-28 | 2021-03-29 | Bayer Pharma AG | Gadolinium chelate compounds with high relaxivity for use in magnetic resonance imaging |
AU2019382881A1 (en) | 2018-11-23 | 2021-05-20 | Bayer Aktiengesellschaft | Formulation of contrast media and process of preparation thereof |
CN109867635A (en) * | 2019-02-14 | 2019-06-11 | 华东师范大学 | A kind of T1 type micella magnetic resonance imaging contrast and preparation method thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19603033A1 (en) * | 1996-01-19 | 1997-07-24 | Schering Ag | Perfluoroalkyl-containing metal complexes, processes for their preparation and their use in NMR diagnostics |
JPH10112939A (en) * | 1996-10-07 | 1998-04-28 | Nec Corp | Power switching circuit |
DE19729013A1 (en) * | 1997-07-03 | 1999-02-04 | Schering Ag | Oligomeric, perfluoroalkyl-containing compounds, processes for their preparation and their use in NMR diagnostics |
US6019959A (en) * | 1997-07-31 | 2000-02-01 | Schering Aktiengesellschaft | Oligomeric compounds that contain perfluoroalkyl, process for their production, and their use in NMR diagnosis |
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2000
- 2000-08-11 DE DE10066210A patent/DE10066210B4/en not_active Expired - Fee Related
-
2001
- 2001-07-23 RU RU2003105810/15A patent/RU2290206C2/en not_active IP Right Cessation
- 2001-07-23 CA CA002419223A patent/CA2419223A1/en not_active Abandoned
- 2001-07-23 AU AU2001277549A patent/AU2001277549B2/en not_active Ceased
- 2001-07-23 WO PCT/EP2001/008498 patent/WO2002013874A2/en not_active Application Discontinuation
- 2001-07-23 NZ NZ523932A patent/NZ523932A/en unknown
- 2001-07-23 HU HU0300736A patent/HUP0300736A3/en unknown
- 2001-07-23 EE EEP200300061A patent/EE200300061A/en unknown
- 2001-07-23 YU YU10603A patent/YU10603A/en unknown
- 2001-07-23 MX MXPA03001287A patent/MXPA03001287A/en active IP Right Grant
- 2001-07-23 AU AU7754901A patent/AU7754901A/en active Pending
- 2001-07-23 EP EP01955366A patent/EP1307236A2/en not_active Withdrawn
- 2001-07-23 IL IL15438501A patent/IL154385A0/en unknown
- 2001-07-23 CN CNA018172717A patent/CN1469757A/en active Pending
- 2001-07-23 SK SK157-2003A patent/SK1572003A3/en not_active Application Discontinuation
- 2001-07-23 BR BR0113188-5A patent/BR0113188A/en not_active IP Right Cessation
- 2001-07-23 KR KR10-2003-7002023A patent/KR20030022387A/en not_active IP Right Cessation
- 2001-07-23 CZ CZ2003392A patent/CZ2003392A3/en unknown
- 2001-07-23 UA UA2003032067A patent/UA82642C2/en unknown
- 2001-07-23 PL PL01365596A patent/PL365596A1/en not_active Application Discontinuation
- 2001-07-23 JP JP2002519012A patent/JP2004506025A/en active Pending
- 2001-08-10 AR ARP010103833A patent/AR034139A1/en unknown
- 2001-08-10 TW TW090119643A patent/TWI296931B/en active
-
2003
- 2003-02-07 BG BG107542A patent/BG107542A/en unknown
- 2003-02-07 NO NO20030604A patent/NO20030604L/en not_active Application Discontinuation
- 2003-03-10 ZA ZA200301949A patent/ZA200301949B/en unknown
- 2003-03-10 HR HR20030173A patent/HRP20030173A2/en not_active Application Discontinuation
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