CA1253514A - Complexing agents, complexes and complex salts - Google Patents
Complexing agents, complexes and complex saltsInfo
- Publication number
- CA1253514A CA1253514A CA000457842A CA457842A CA1253514A CA 1253514 A CA1253514 A CA 1253514A CA 000457842 A CA000457842 A CA 000457842A CA 457842 A CA457842 A CA 457842A CA 1253514 A CA1253514 A CA 1253514A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- carbamoylmethyl
- carboxymethyl
- acid
- dihydroxypropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 29
- 239000008139 complexing agent Substances 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 229910021645 metal ion Chemical group 0.000 claims abstract description 5
- 150000007530 organic bases Chemical class 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 52
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 27
- 150000002500 ions Chemical class 0.000 claims description 23
- -1 2,3-dihydroxypropyl-carbamoylmethyl Chemical group 0.000 claims description 18
- 239000011572 manganese Substances 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 238000003745 diagnosis Methods 0.000 claims description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
- VHBHDTCQRAWUAT-UHFFFAOYSA-N C(=O)(O)CN(CCN(CC(=O)O)C(C(NC)=O)CC(CO)O)CCN(CC(=O)O)C(C(NC)=O)CC(CO)O Chemical compound C(=O)(O)CN(CCN(CC(=O)O)C(C(NC)=O)CC(CO)O)CCN(CC(=O)O)C(C(NC)=O)CC(CO)O VHBHDTCQRAWUAT-UHFFFAOYSA-N 0.000 claims description 7
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 7
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 7
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052748 manganese Inorganic materials 0.000 claims description 7
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052772 Samarium Inorganic materials 0.000 claims description 4
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 3
- 229910052689 Holmium Inorganic materials 0.000 claims description 3
- 229910052771 Terbium Inorganic materials 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 3
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 3
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims description 3
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 238000003384 imaging method Methods 0.000 claims description 2
- 230000006872 improvement Effects 0.000 claims description 2
- GXQQBJUFAKMIKE-UHFFFAOYSA-N 2-[bis[2-[(1-amino-4,5-dihydroxy-1-oxopentan-2-yl)-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OCC(O)CC(C(=O)N)N(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)C(CC(O)CO)C(N)=O GXQQBJUFAKMIKE-UHFFFAOYSA-N 0.000 claims 5
- LTYNJCZECBDDEC-UHFFFAOYSA-N 2-[bis[2-[(1-amino-4,5,6-trihydroxy-1-oxohexan-2-yl)-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OCC(O)C(O)CC(C(=O)N)N(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)C(CC(O)C(O)CO)C(N)=O LTYNJCZECBDDEC-UHFFFAOYSA-N 0.000 claims 3
- HUCLENQBMAZCJJ-UHFFFAOYSA-N 2-[bis[2-[(3-carbamoyl-1,5-dihydroxypentan-3-yl)-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OCCC(C(=O)N)(CCO)N(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)C(CCO)(CCO)C(N)=O HUCLENQBMAZCJJ-UHFFFAOYSA-N 0.000 claims 3
- WPURBFHVMFIVBM-UHFFFAOYSA-N 2-[bis[2-[[1-amino-4-hydroxy-3-(hydroxymethyl)-1-oxobutan-2-yl]-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OCC(CO)C(C(=O)N)N(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)C(C(CO)CO)C(N)=O WPURBFHVMFIVBM-UHFFFAOYSA-N 0.000 claims 3
- JECGSDWATPZSJH-UHFFFAOYSA-N 2-[bis[2-[carboxymethyl-[4,5,6,7,8-pentahydroxy-1-(methylamino)-1-oxooctan-2-yl]amino]ethyl]amino]acetic acid Chemical compound C(=O)(O)CN(CCN(CC(=O)O)C(C(NC)=O)CC(C(C(C(CO)O)O)O)O)CCN(CC(=O)O)C(C(NC)=O)CC(C(C(C(CO)O)O)O)O JECGSDWATPZSJH-UHFFFAOYSA-N 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 2
- WGXDGYGKCFUHNE-UHFFFAOYSA-N 2-[2-[carboxymethyl-[4,5-dihydroxy-1-(methylamino)-1-oxopentan-2-yl]amino]ethyl-[4,5-dihydroxy-1-(methylamino)-1-oxopentan-2-yl]amino]acetic acid Chemical compound OC(CC(N(CC(=O)O)CCN(CC(=O)O)C(C(NC)=O)CC(CO)O)C(NC)=O)CO WGXDGYGKCFUHNE-UHFFFAOYSA-N 0.000 claims 2
- PEICQWVPBAJJQJ-UHFFFAOYSA-N 2-[bis[2-[[1-amino-4,5-dihydroxy-2-(hydroxymethyl)-1-oxopentan-2-yl]-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OCC(O)CC(CO)(C(=O)N)N(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)C(CO)(CC(O)CO)C(N)=O PEICQWVPBAJJQJ-UHFFFAOYSA-N 0.000 claims 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 2
- 229910052804 chromium Inorganic materials 0.000 claims 2
- 239000011651 chromium Substances 0.000 claims 2
- 150000004698 iron complex Chemical class 0.000 claims 2
- 229910052746 lanthanum Inorganic materials 0.000 claims 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- GVGXPXPGZLUONX-UHFFFAOYSA-N samarium Chemical compound [Sm][Sm][Sm][Sm][Sm][Sm][Sm][Sm][Sm][Sm][Sm][Sm][Sm][Sm] GVGXPXPGZLUONX-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- YESFHTISNYHXJX-UHFFFAOYSA-N 2-[(1-amino-4,5-dihydroxy-1-oxopentan-2-yl)-[2-[(1-amino-4,5-dihydroxy-1-oxopentan-2-yl)-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OCC(O)CC(C(=O)N)N(CC(O)=O)CCN(CC(O)=O)C(CC(O)CO)C(N)=O YESFHTISNYHXJX-UHFFFAOYSA-N 0.000 claims 1
- LWGORILFSPQNDB-UHFFFAOYSA-N 2-[(1-amino-4-hydroxy-1-oxobutan-2-yl)-[2-[(1-amino-4-hydroxy-1-oxobutan-2-yl)-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OCCC(C(=O)N)N(CC(O)=O)CCN(CC(O)=O)C(CCO)C(N)=O LWGORILFSPQNDB-UHFFFAOYSA-N 0.000 claims 1
- VUXGMZGLCJTNGF-UHFFFAOYSA-N 2-[(3-carbamoyl-1,5-dihydroxypentan-3-yl)-[2-[(3-carbamoyl-1,5-dihydroxypentan-3-yl)-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OCCC(C(=O)N)(CCO)N(CC(O)=O)CCN(CC(O)=O)C(CCO)(CCO)C(N)=O VUXGMZGLCJTNGF-UHFFFAOYSA-N 0.000 claims 1
- CNGGWQIYSLYJSH-UHFFFAOYSA-N 2-[[1-amino-4,5-dihydroxy-2-(hydroxymethyl)-1-oxopentan-2-yl]-[2-[[1-amino-4,5-dihydroxy-2-(hydroxymethyl)-1-oxopentan-2-yl]-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OC(CC(CO)(N(CC(=O)O)CCN(CC(=O)O)C(CO)(C(N)=O)CC(CO)O)C(N)=O)CO CNGGWQIYSLYJSH-UHFFFAOYSA-N 0.000 claims 1
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
- 238000002405 diagnostic procedure Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000000843 powder Substances 0.000 description 47
- 238000002844 melting Methods 0.000 description 40
- 230000008018 melting Effects 0.000 description 40
- 239000000243 solution Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000004458 analytical method Methods 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- CMIHHWBVHJVIGI-UHFFFAOYSA-N gadolinium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Gd+3].[Gd+3] CMIHHWBVHJVIGI-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000000536 complexating effect Effects 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- RJOJUSXNYCILHH-UHFFFAOYSA-N gadolinium(3+) Chemical compound [Gd+3] RJOJUSXNYCILHH-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229960000281 trometamol Drugs 0.000 description 4
- 238000002604 ultrasonography Methods 0.000 description 4
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 3
- 206010027439 Metal poisoning Diseases 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 239000000729 antidote Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- WMWLMWRWZQELOS-UHFFFAOYSA-N bismuth(III) oxide Inorganic materials O=[Bi]O[Bi]=O WMWLMWRWZQELOS-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- QZQVBEXLDFYHSR-UHFFFAOYSA-N gallium(iii) oxide Chemical compound O=[Ga]O[Ga]=O QZQVBEXLDFYHSR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- MENOBBYDZHOWLE-UHFFFAOYSA-N morpholine-2,3-dione Chemical compound O=C1NCCOC1=O MENOBBYDZHOWLE-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- MSBGPEACXKBQSX-UHFFFAOYSA-N (4-fluorophenyl) carbonochloridate Chemical compound FC1=CC=C(OC(Cl)=O)C=C1 MSBGPEACXKBQSX-UHFFFAOYSA-N 0.000 description 1
- WNIBCFTVQSCFKW-UHFFFAOYSA-N 2-[2-[2-[2-(carboxymethylamino)ethylamino]ethylamino]ethylamino]acetic acid Chemical compound OC(=O)CNCCNCCNCCNCC(O)=O WNIBCFTVQSCFKW-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- WOMTYMDHLQTCHY-UHFFFAOYSA-N 3-methylamino-1,2-propanediol Chemical compound CNCC(O)CO WOMTYMDHLQTCHY-UHFFFAOYSA-N 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 241000283014 Dama Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
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- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
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- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
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- AWSFICBXMUKWSK-UHFFFAOYSA-N ytterbium(3+) Chemical compound [Yb+3] AWSFICBXMUKWSK-UHFFFAOYSA-N 0.000 description 1
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
- A61K49/1806—Suspensions, emulsions, colloids, dispersions
- A61K49/1812—Suspensions, emulsions, colloids, dispersions liposomes, polymersomes, e.g. immunoliposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0478—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group complexes from non-cyclic ligands, e.g. EDTA, MAG3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0478—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group complexes from non-cyclic ligands, e.g. EDTA, MAG3
- A61K51/048—DTPA (diethylenetriamine tetraacetic acid)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Radiology & Medical Imaging (AREA)
- Immunology (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3324235A DE3324235A1 (de) | 1983-07-01 | 1983-07-01 | Neue komplexbildner, komplexe und komplexsalze |
| DEP3324235.6 | 1983-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1253514A true CA1253514A (en) | 1989-05-02 |
Family
ID=6203212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000457842A Expired CA1253514A (en) | 1983-07-01 | 1984-06-29 | Complexing agents, complexes and complex salts |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5316756A (enExample) |
| EP (1) | EP0130934B1 (enExample) |
| JP (1) | JPS6036452A (enExample) |
| AT (1) | ATE28745T1 (enExample) |
| CA (1) | CA1253514A (enExample) |
| DE (2) | DE3324235A1 (enExample) |
| DK (1) | DK171352B1 (enExample) |
| IE (1) | IE57929B1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5208324A (en) * | 1988-01-26 | 1993-05-04 | Nycomed Imaging As | Paramagnetic compounds |
| US5242683A (en) * | 1989-07-21 | 1993-09-07 | Nycomed Imaging As | Contrast media comprising a paramagnetic agent and an iodinated agent for x-ray and mri |
| US5494655A (en) * | 1990-03-09 | 1996-02-27 | The Regents Of The University Of California | Methods for detecting blood perfusion variations by magnetic resonance imaging |
| US5693310A (en) * | 1986-09-26 | 1997-12-02 | Schering Aktiengesellschaft | Amide complexes |
| US8669236B2 (en) | 2005-05-12 | 2014-03-11 | The General Hospital Corporation | Biotinylated compositions |
| US10532104B2 (en) | 2012-08-31 | 2020-01-14 | The General Hospital Corporation | Biotin complexes for treatment and diagnosis of Alzheimer'S disease |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8413772D0 (en) * | 1984-05-30 | 1984-07-04 | Nyegaard & Co As | Chemical compounds |
| US4687659A (en) * | 1984-11-13 | 1987-08-18 | Salutar, Inc. | Diamide-DTPA-paramagnetic contrast agents for MR imaging |
| DE3508000A1 (de) * | 1985-03-04 | 1986-09-04 | Schering AG, Berlin und Bergkamen, 1000 Berlin | Ferromagnetische partikel fuer die nmr-diagnostik |
| JPH07100666B2 (ja) * | 1986-04-07 | 1995-11-01 | フランスワ ディエトラン | 濃度断層撮影用造影剤 |
| EP0250358A3 (en) * | 1986-06-20 | 1988-10-05 | Schering Aktiengesellschaft | Novel complex compounds |
| AU608759B2 (en) * | 1986-08-04 | 1991-04-18 | Amersham Health Salutar Inc | NMR imaging with paramagnetic polyvalents metal salts of poly-(acid-alkylene-amido)-alkanes |
| DE3640708C2 (de) * | 1986-11-28 | 1995-05-18 | Schering Ag | Verbesserte metallhaltige Pharmazeutika |
| US5057302A (en) * | 1987-02-13 | 1991-10-15 | Abbott Laboratories | Bifunctional chelating agents |
| DE3710730A1 (de) * | 1987-03-31 | 1988-10-20 | Schering Ag | Substituierte komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
| GB9007965D0 (en) * | 1990-04-09 | 1990-06-06 | Nycomed As | Compounds |
| US5531978A (en) * | 1987-07-16 | 1996-07-02 | Nycomed Imaging As | Aminopolycarboxylic acids and derivatives thereof |
| HU208947B (en) * | 1987-07-16 | 1994-02-28 | Nycomed As | Diagnostical compositions and process for producing aminopolycarboxylic acids, their derivatives and metal-kelates |
| DE3724188C2 (de) * | 1987-07-17 | 1995-05-18 | Heinz Dr Gries | Metallhaltige Oligosaccharid-Polysulfate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Mittel |
| JPH01240620A (ja) * | 1988-03-16 | 1989-09-26 | Miyamoto Kogyosho:Kk | ビレット調質方法とビレット調質炉 |
| US5137711A (en) * | 1988-07-19 | 1992-08-11 | Mallickrodt Medical, Inc. | Paramagnetic dtpa and edta alkoxyalkylamide complexes as mri agents |
| DE3825040A1 (de) * | 1988-07-20 | 1990-01-25 | Schering Ag, 13353 Berlin | 5- oder 6-ring- enthaltende makrocyclische polyaza-verbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| DE4001655A1 (de) * | 1990-01-18 | 1991-07-25 | Schering Ag | 6-ring enthaltende makrocyclische tetraaza-verbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| US5314681A (en) * | 1988-12-23 | 1994-05-24 | Nycomed Innovation Ab | Composition of positive and negative contrast agents for electron spin resonance enhanced magnetic resonance imaging |
| GB8900719D0 (en) * | 1989-01-13 | 1989-03-08 | Nycomed As | Compounds |
| GB8900732D0 (en) * | 1989-01-13 | 1989-03-08 | Nycomed As | Agents |
| US5011925A (en) * | 1989-03-09 | 1991-04-30 | Mallinckrodt, Inc. | Morpholinoamido EDTA derivatives |
| US5384108A (en) * | 1989-04-24 | 1995-01-24 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents |
| US5695739A (en) * | 1989-06-30 | 1997-12-09 | Schering Aktiengesellschaft | Derivatized DTPA complexes, pharmaceutical agents containing these compounds, their use, and processes for their production |
| US6039931A (en) * | 1989-06-30 | 2000-03-21 | Schering Aktiengesellschaft | Derivatized DTPA complexes, pharmaceutical agents containing these compounds, their use, and processes for their production |
| CA2065415A1 (en) * | 1989-09-05 | 1991-03-06 | Raghavan Rajagopalan | Magnetic resonance imaging agents |
| WO1992017215A1 (en) * | 1990-03-28 | 1992-10-15 | Nycomed Salutar, Inc. | Contrast media |
| DE4011684A1 (de) | 1990-04-06 | 1991-10-10 | Schering Ag | Dtpa-monoamide, diese verbindungen enthaltende pharmazeutische mittel, ihre verwendung und verfahren zu deren herstellung |
| US5843399A (en) * | 1990-04-06 | 1998-12-01 | Schering Aktiengesellschaft | DTPA monoamides for MRI |
| GB9007967D0 (en) * | 1990-04-09 | 1990-06-06 | Nycomed As | Compounds |
| 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 |
| US5077037A (en) * | 1990-08-03 | 1991-12-31 | Mallinckrodt Medical, Inc. | Novel compositions for magnetic resonance imaging |
| US5908931A (en) * | 1990-12-14 | 1999-06-01 | Mallinckrodt Inc. | Preorganized hexadentate ligands useful in radiographic imaging agents |
| GB9027922D0 (en) * | 1990-12-21 | 1991-02-13 | Nycomed As | Compounds |
| AU660013B2 (en) * | 1991-03-27 | 1995-06-08 | Nycomed Salutar, Inc. | Contrast media |
| EP0594640A4 (en) * | 1991-05-23 | 1998-06-03 | Evan C Unger | Liposoluble compounds for magnetic resonance imaging |
| US5562894A (en) * | 1991-08-09 | 1996-10-08 | Regents Of The University Of California | Amino-acyl-type and catecholamine-type contrast agents for MRI |
| GB9208908D0 (en) * | 1992-04-24 | 1992-06-10 | Nycomed As | Contrast agents |
| US5439913A (en) | 1992-05-12 | 1995-08-08 | Schering Aktiengesellschaft | Contraception method using competitive progesterone antagonists and novel compounds useful therein |
| DE4302287A1 (de) * | 1993-01-25 | 1994-07-28 | Schering Ag | Derivatisierte DTPA-Komplexe, diese Verbindungen enthaltende pharmazeutische Mittel, ihre Verwendung und Verfahren zu deren Herstellung |
| GB9321595D0 (en) * | 1993-10-20 | 1993-12-08 | Nycomed Imaging As | Contrast agents |
| US5571498A (en) * | 1994-06-02 | 1996-11-05 | Hemagen/Pfc | Emulsions of paramagnetic contrast agents for magnetic resonance imaging (MRI). |
| US5672335A (en) * | 1994-11-30 | 1997-09-30 | Schering Aktiengesellschaft | Use of metal complexes as liver and gallbladder X-ray diagnostic agents |
| US5614170A (en) * | 1994-11-30 | 1997-03-25 | Hemagen/Pfc | Paramagnetic complexes of N-alkyl-N-hydroxylamides of organic acids and emulsions containing same for magnetic resonance imaging (MRI) |
| DE19507819A1 (de) * | 1995-02-21 | 1996-08-22 | Schering Ag | DTPA-Monoamide der zentralen Carbonsäure und deren Metallkomplexe, diese Komplexe enthaltende pharmazeutische Mittel, deren Verwendung in der Diagnostik und Therapie sowie Verfahren zur Herstellung der Komplexe und Mittel |
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| IT1297035B1 (it) | 1997-12-30 | 1999-08-03 | Bracco Spa | Derivati dell'acido 1,4,7,10-tetraazaciclododecan-1,4-diacetico |
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| DE102007058220A1 (de) | 2007-12-03 | 2009-06-04 | Bayer Schering Pharma Aktiengesellschaft | Dimere macrocyclisch substituierte Benzolderivate |
| WO2012136813A2 (en) | 2011-04-07 | 2012-10-11 | Universitetet I Oslo | Agents for medical radar diagnosis |
| HUP1500076A2 (hu) * | 2015-02-25 | 2016-09-28 | Debreceni Egyetem | Új helyettesített etilén-diamin-tetraecetsav-bisz(amid) származékok és alkalmazásuk Mn(II)-alapú MRI kontrasztanyag ligandumként |
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| US10494379B2 (en) | 2015-11-26 | 2019-12-03 | Debreceni Egyetem | 6-oxa-3,9,15-triaza-bicyclo[9.3.1]pentadeca-1(14),11(15),12-triene derivatives based compounds and their application as ligands of essential metal ion based MRI and 52MN based PET contrast agents |
| EP3380473A1 (en) | 2015-11-26 | 2018-10-03 | Debreceni Egyetem | New 2, 1 l -diaza-[3.3](2,6)pyridinophane compounds and their application as ligands of essential metal ion based mri contrast agents and 52mn based pet contrast agents |
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-
1983
- 1983-07-01 DE DE3324235A patent/DE3324235A1/de not_active Withdrawn
-
1984
- 1984-06-28 EP EP84730074A patent/EP0130934B1/de not_active Expired
- 1984-06-28 DE DE8484730074T patent/DE3465191D1/de not_active Expired
- 1984-06-28 AT AT84730074T patent/ATE28745T1/de not_active IP Right Cessation
- 1984-06-29 CA CA000457842A patent/CA1253514A/en not_active Expired
- 1984-06-29 DK DK320884A patent/DK171352B1/da not_active IP Right Cessation
- 1984-07-02 JP JP59135365A patent/JPS6036452A/ja active Granted
- 1984-07-02 IE IE1683/84A patent/IE57929B1/en not_active IP Right Cessation
-
1990
- 1990-04-13 US US07/515,761 patent/US5316756A/en not_active Expired - Lifetime
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1994
- 1994-03-28 US US08/219,339 patent/US5419894A/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693310A (en) * | 1986-09-26 | 1997-12-02 | Schering Aktiengesellschaft | Amide complexes |
| US5208324A (en) * | 1988-01-26 | 1993-05-04 | Nycomed Imaging As | Paramagnetic compounds |
| US5242683A (en) * | 1989-07-21 | 1993-09-07 | Nycomed Imaging As | Contrast media comprising a paramagnetic agent and an iodinated agent for x-ray and mri |
| US5494655A (en) * | 1990-03-09 | 1996-02-27 | The Regents Of The University Of California | Methods for detecting blood perfusion variations by magnetic resonance imaging |
| US5833947A (en) * | 1990-03-09 | 1998-11-10 | The Regents Of The University Of California | Magnetic resonance imaging |
| US8669236B2 (en) | 2005-05-12 | 2014-03-11 | The General Hospital Corporation | Biotinylated compositions |
| US10532104B2 (en) | 2012-08-31 | 2020-01-14 | The General Hospital Corporation | Biotin complexes for treatment and diagnosis of Alzheimer'S disease |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE28745T1 (de) | 1987-08-15 |
| DK320884A (da) | 1985-01-02 |
| EP0130934A1 (de) | 1985-01-09 |
| JPH0380148B2 (enExample) | 1991-12-24 |
| IE841683L (en) | 1985-01-01 |
| US5316756A (en) | 1994-05-31 |
| US5419894A (en) | 1995-05-30 |
| DK171352B1 (da) | 1996-09-16 |
| DE3465191D1 (en) | 1987-09-10 |
| EP0130934B1 (de) | 1987-08-05 |
| DE3324235A1 (de) | 1985-01-10 |
| IE57929B1 (en) | 1993-05-19 |
| DK320884D0 (da) | 1984-06-29 |
| JPS6036452A (ja) | 1985-02-25 |
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