DE3324235A1 - Neue komplexbildner, komplexe und komplexsalze - Google Patents
Neue komplexbildner, komplexe und komplexsalzeInfo
- Publication number
- DE3324235A1 DE3324235A1 DE3324235A DE3324235A DE3324235A1 DE 3324235 A1 DE3324235 A1 DE 3324235A1 DE 3324235 A DE3324235 A DE 3324235A DE 3324235 A DE3324235 A DE 3324235A DE 3324235 A1 DE3324235 A1 DE 3324235A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- carboxymethyl
- carbamoylmethyl
- acid
- group
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 229910021645 metal ion Chemical group 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 207
- 239000002253 acid Substances 0.000 claims description 44
- -1 1-carbamoylmethyl Chemical group 0.000 claims description 37
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 25
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 19
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 19
- 239000008139 complexing agent Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 8
- 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 7
- 238000002360 preparation method Methods 0.000 claims description 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-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
- 239000011651 chromium Substances 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- 229910052797 bismuth Inorganic materials 0.000 claims description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229910052689 Holmium Inorganic materials 0.000 claims description 3
- 229910052771 Terbium Inorganic materials 0.000 claims description 3
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229910052746 lanthanum Inorganic materials 0.000 claims description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- LYJBWDPBXNGCAJ-UHFFFAOYSA-N 2-cyclohexyl-4,5-dihydroxy-n-methylpentanamide Chemical compound OCC(O)CC(C(=O)NC)C1CCCCC1 LYJBWDPBXNGCAJ-UHFFFAOYSA-N 0.000 claims description 2
- WIGVHSVSKMPGFH-UHFFFAOYSA-N 2-cyclohexyl-4,5-dihydroxypentanamide Chemical compound OC(CC(C(N)=O)C1CCCCC1)CO WIGVHSVSKMPGFH-UHFFFAOYSA-N 0.000 claims description 2
- FSIFWKYZYKQISV-UHFFFAOYSA-N 2-cyclohexyl-4-hydroxy-3-(hydroxymethyl)butanamide Chemical compound OCC(CO)C(C(N)=O)C1CCCCC1 FSIFWKYZYKQISV-UHFFFAOYSA-N 0.000 claims description 2
- GGOUDNMXRLWZFL-UHFFFAOYSA-N 2-cyclohexyl-4-hydroxybutanamide Chemical compound OCCC(C(N)=O)C1CCCCC1 GGOUDNMXRLWZFL-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- CPIJFVRBBPQLLZ-UHFFFAOYSA-N OC(CC(CO)(C(N)=O)C(C(=O)O)NCCNCCNCC(=O)O)CO Chemical compound OC(CC(CO)(C(N)=O)C(C(=O)O)NCCNCCNCC(=O)O)CO CPIJFVRBBPQLLZ-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 229910052713 technetium Inorganic materials 0.000 claims description 2
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 150000001414 amino alcohols Chemical class 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- BYXQCSLXXWQKIF-UHFFFAOYSA-N 2-[2-[2-(carboxymethylamino)ethylamino]ethylamino]-4-(1,3-dihydroxypropan-2-ylamino)-4-oxobutanoic acid Chemical compound OCC(CO)NC(=O)CC(C(O)=O)NCCNCCNCC(O)=O BYXQCSLXXWQKIF-UHFFFAOYSA-N 0.000 claims 1
- 229910052692 Dysprosium Inorganic materials 0.000 claims 1
- 150000000921 Gadolinium Chemical class 0.000 claims 1
- FXBLLWUBOLHZRY-UHFFFAOYSA-N OC(CC(N(CC(=O)O)CCNCCN(CC(=O)O)C(C(N)=O)CC(CO)O)C(N)=O)CO Chemical compound OC(CC(N(CC(=O)O)CCNCCN(CC(=O)O)C(C(N)=O)CC(CO)O)C(N)=O)CO FXBLLWUBOLHZRY-UHFFFAOYSA-N 0.000 claims 1
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229940039227 diagnostic agent Drugs 0.000 claims 1
- 239000000032 diagnostic agent Substances 0.000 claims 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000004698 iron complex Chemical class 0.000 claims 1
- 150000002696 manganese Chemical class 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- 239000000843 powder Substances 0.000 description 46
- 238000002844 melting Methods 0.000 description 45
- 230000008018 melting Effects 0.000 description 45
- 239000000243 solution Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 239000011572 manganese Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229910052748 manganese Inorganic materials 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- FEUUSTBYWDAUFK-UHFFFAOYSA-N 2-[2-[2-(carboxymethylamino)ethylamino]ethylamino]-5,6-dihydroxy-3-(methylcarbamoyl)hexanoic acid Chemical compound OCC(O)CC(C(=O)NC)C(C(O)=O)NCCNCCNCC(O)=O FEUUSTBYWDAUFK-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- 229960000281 trometamol Drugs 0.000 description 5
- 238000002604 ultrasonography Methods 0.000 description 5
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000729 antidote Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010027439 Metal poisoning Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- IJSMDZFKMKEIRX-UHFFFAOYSA-N morpholine-2,6-dione Chemical compound O=C1CNCC(=O)O1 IJSMDZFKMKEIRX-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 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
- DDJXXYZGKAHNMH-UHFFFAOYSA-N 2-[2-[2-(carboxymethylamino)ethylamino]ethylamino]acetic acid Chemical compound OC(=O)CNCCNCCNCC(O)=O DDJXXYZGKAHNMH-UHFFFAOYSA-N 0.000 description 2
- FGWDLOHDNKIXTH-UHFFFAOYSA-N 2-[2-[carboxymethyl-[2-[carboxymethyl-[4,5-dihydroxy-1-(methylamino)-1-oxopentan-2-yl]amino]ethyl]amino]ethyl-[2-[carboxymethyl-[4,5-dihydroxy-1-(methylamino)-1-oxopentan-2-yl]amino]ethyl]amino]acetic acid Chemical compound OCC(O)CC(C(=O)NC)N(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)C(CC(O)CO)C(=O)NC FGWDLOHDNKIXTH-UHFFFAOYSA-N 0.000 description 2
- RAZLJUXJEOEYAM-UHFFFAOYSA-N 2-[bis[2-(2,6-dioxomorpholin-4-yl)ethyl]azaniumyl]acetate Chemical compound C1C(=O)OC(=O)CN1CCN(CC(=O)O)CCN1CC(=O)OC(=O)C1 RAZLJUXJEOEYAM-UHFFFAOYSA-N 0.000 description 2
- WOMTYMDHLQTCHY-UHFFFAOYSA-N 3-methylamino-1,2-propanediol Chemical compound CNCC(O)CO WOMTYMDHLQTCHY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 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
- 238000007792 addition Methods 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- IOIFRTZBJMZZFO-UHFFFAOYSA-N dysprosium(3+) Chemical compound [Dy+3] IOIFRTZBJMZZFO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000011656 manganese carbonate Substances 0.000 description 2
- 235000006748 manganese carbonate Nutrition 0.000 description 2
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 2
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 2
- 230000005298 paramagnetic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000008259 solid foam 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
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- MKDRHMDHWIBVRH-UHFFFAOYSA-N 2-amino-1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol Chemical compound CC1(C)OCC(C(O)CN)O1 MKDRHMDHWIBVRH-UHFFFAOYSA-N 0.000 description 1
- KEFKCKFIEUCATP-UHFFFAOYSA-N 2-cyclohexyl-n,n-bis(2-hydroxyethyl)acetamide Chemical compound OCCN(CCO)C(=O)CC1CCCCC1 KEFKCKFIEUCATP-UHFFFAOYSA-N 0.000 description 1
- RSHPXJWPCWGGSQ-UHFFFAOYSA-N 2-cyclohexyl-n-(1,3-dihydroxypropan-2-yl)acetamide Chemical class OCC(CO)NC(=O)CC1CCCCC1 RSHPXJWPCWGGSQ-UHFFFAOYSA-N 0.000 description 1
- YIWSLEJNZQRTGM-UHFFFAOYSA-N 3-carbamoyl-2-[2-[2-(carboxymethylamino)ethylamino]ethylamino]-5,6,7-trihydroxyheptanoic acid Chemical compound OC(CC(C(N)=O)C(C(=O)O)NCCNCCNCC(=O)O)C(CO)O YIWSLEJNZQRTGM-UHFFFAOYSA-N 0.000 description 1
- QZRGIEUTAVNVQN-UHFFFAOYSA-N 3-carbamoyl-2-[2-[2-(carboxymethylamino)ethylamino]ethylamino]-5-hydroxy-4-(hydroxymethyl)pentanoic acid Chemical compound OCC(CO)C(C(=O)N)C(C(O)=O)NCCNCCNCC(O)=O QZRGIEUTAVNVQN-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- XRTUVZSUJMNJOF-NXEZZACHSA-N 4-[(1r,2r)-2-(2,6-dioxomorpholin-4-yl)cyclohexyl]morpholine-2,6-dione Chemical compound C1C(=O)OC(=O)CN1[C@H]1[C@H](N2CC(=O)OC(=O)C2)CCCC1 XRTUVZSUJMNJOF-NXEZZACHSA-N 0.000 description 1
- IRIRHXXUSZTSTF-UHFFFAOYSA-N 6-amino-2,2-dimethyl-1,3-dioxepin-5-ol Chemical compound CC1(C)OC=C(N)C(O)=CO1 IRIRHXXUSZTSTF-UHFFFAOYSA-N 0.000 description 1
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- DAOANAATJZWTSJ-UHFFFAOYSA-N N-Decanoylmorpholine Chemical compound CCCCCCCCCC(=O)N1CCOCC1 DAOANAATJZWTSJ-UHFFFAOYSA-N 0.000 description 1
- PVDDRVWOUYMZRY-UHFFFAOYSA-N OC(CC(C(NC)=O)N(CCNCCN(CC(=O)O)C(CC(CO)O)C(NC)=O)CC(=O)O)CO Chemical compound OC(CC(C(NC)=O)N(CCNCCN(CC(=O)O)C(CC(CO)O)C(NC)=O)CC(=O)O)CO PVDDRVWOUYMZRY-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229940075522 antidotes Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
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- 229940075613 gadolinium oxide Drugs 0.000 description 1
- 229910001938 gadolinium oxide Inorganic materials 0.000 description 1
- CMIHHWBVHJVIGI-UHFFFAOYSA-N gadolinium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Gd+3].[Gd+3] CMIHHWBVHJVIGI-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 229940021223 hypertonic solution Drugs 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 230000005291 magnetic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
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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
-
- 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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3324235A DE3324235A1 (de) | 1983-07-01 | 1983-07-01 | Neue komplexbildner, komplexe und komplexsalze |
| DE8484730074T DE3465191D1 (en) | 1983-07-01 | 1984-06-28 | Complexing agents, complexes and complex salts |
| AT84730074T ATE28745T1 (de) | 1983-07-01 | 1984-06-28 | Neue komplexbildner, komplexe und komplexsalze. |
| EP84730074A EP0130934B1 (de) | 1983-07-01 | 1984-06-28 | Neue Komplexbildner, Komplexe und Komplexsalze |
| CA000457842A CA1253514A (en) | 1983-07-01 | 1984-06-29 | Complexing agents, complexes and complex salts |
| DK320884A DK171352B1 (da) | 1983-07-01 | 1984-06-29 | Metalkomplekser og salte deraf, fremgangsmåde til fremstilling af sådanne forbindelser samt diagnostiske midler og farmaceutiske præparater indeholdende forbindelserne |
| IE1683/84A IE57929B1 (en) | 1983-07-01 | 1984-07-02 | New complexing agents,complexes and complex salts |
| JP59135365A JPS6036452A (ja) | 1983-07-01 | 1984-07-02 | 新規錯化剤及び錯化合物、その製法及び該錯化合物を含有するｎｍｒ診断剤及びｎｍｒ診断用医薬組成物 |
| US07/515,761 US5316756A (en) | 1983-07-01 | 1990-04-13 | NMR imaging using paramagnetic chelates having hydroxyalkyl-substituted amide groups |
| US08/219,339 US5419894A (en) | 1983-07-01 | 1994-03-28 | Complexing agents, complexes and complex salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3324235A DE3324235A1 (de) | 1983-07-01 | 1983-07-01 | Neue komplexbildner, komplexe und komplexsalze |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3324235A1 true DE3324235A1 (de) | 1985-01-10 |
Family
ID=6203212
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3324235A Withdrawn DE3324235A1 (de) | 1983-07-01 | 1983-07-01 | Neue komplexbildner, komplexe und komplexsalze |
| DE8484730074T Expired DE3465191D1 (en) | 1983-07-01 | 1984-06-28 | Complexing agents, complexes and complex salts |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484730074T Expired DE3465191D1 (en) | 1983-07-01 | 1984-06-28 | 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 (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3710730A1 (de) * | 1987-03-31 | 1988-10-20 | Schering Ag | Substituierte komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
| US5077037A (en) * | 1990-08-03 | 1991-12-31 | Mallinckrodt Medical, Inc. | Novel compositions for magnetic resonance imaging |
| US5137711A (en) * | 1988-07-19 | 1992-08-11 | Mallickrodt Medical, Inc. | Paramagnetic dtpa and edta alkoxyalkylamide complexes as mri agents |
| 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 |
| US5376357A (en) * | 1989-03-09 | 1994-12-27 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents |
| US5384108A (en) * | 1989-04-24 | 1995-01-24 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents |
| US5693310A (en) * | 1986-09-26 | 1997-12-02 | Schering Aktiengesellschaft | Amide complexes |
| DE102023001815A1 (de) * | 2023-05-05 | 2024-11-07 | Siempelkamp Maschinen- Und Anlagenbau Gmbh | Verfahren und Vorrichtung (Anlage) zur Herstellung einer Werkstoffplatte, Werkstoffplatte, sowie Verwendung einer Werkstoffplatte |
Families Citing this family (57)
| 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 |
| 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 |
| GB8801646D0 (en) * | 1988-01-26 | 1988-02-24 | Nycomed As | Chemical compounds |
| 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 |
| 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 |
| GB8900719D0 (en) * | 1989-01-13 | 1989-03-08 | Nycomed As | Compounds |
| GB8900732D0 (en) * | 1989-01-13 | 1989-03-08 | Nycomed As | 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 |
| GB8916781D0 (en) * | 1989-07-21 | 1989-09-06 | Nycomed As | Compositions |
| CA2065415A1 (en) * | 1989-09-05 | 1991-03-06 | Raghavan Rajagopalan | Magnetic resonance imaging agents |
| 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 |
| 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 |
| 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 |
| DE19507820A1 (de) * | 1995-02-21 | 1996-08-22 | Schering Ag | Neuartig substituierte DTPA-Derivate, deren Metallkomplexe, diese Komplexe enthaltende pharmazeutische Mittel, deren Verwendung in der Diagnostik, sowie Verfahren zur Herstellung der Komplexe und Mittel |
| DE19507822B4 (de) * | 1995-02-21 | 2006-07-20 | Schering Ag | Substituierte 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 |
| IT1297035B1 (it) | 1997-12-30 | 1999-08-03 | Bracco Spa | Derivati dell'acido 1,4,7,10-tetraazaciclododecan-1,4-diacetico |
| ATE384120T1 (de) * | 1999-08-27 | 2008-02-15 | Invitrogen Corp | Metallbindende verbindungen und deren verwendung in zusammensetzungen für zellkulturmedien |
| US6767741B1 (en) * | 1999-08-27 | 2004-07-27 | Invitrogen Corporation | Metal binding compounds and their use in cell culture medium compositions |
| US20030203879A1 (en) * | 1999-09-09 | 2003-10-30 | Schering Ag | Calcium complex of [[(4R)-4-[bis[(carboxy-.kappa.O)methyl]amino-.kappa.n]-6,9-bis[(carboxy.kappa.O)methyl]-1-[(4,4-diphenylcyclohexy)oxy]-1-hydroxy-2-oxa-6,9-diaza-1-phosphaundecan-11-ylic-acid-.kappa.N6,.Kappa.N9,.Kappa 011]1-oxidato(6-)]-, hexahydrogen, its salts, pharmaceutical agents that contain these complexes, their use in treatment and as additives in diagnosis, as well as processes for the production of the complexes and agents |
| US6525234B1 (en) * | 2000-11-21 | 2003-02-25 | Exxonmobil Oil Corporation | Process for liquid phase aromatics alkylation comprising in-situ catalyst reactivation with polar compounds |
| US8669236B2 (en) | 2005-05-12 | 2014-03-11 | The General Hospital Corporation | Biotinylated compositions |
| FI20065030L (fi) * | 2006-01-17 | 2007-07-18 | Wallac Oy | Neutraaliset leimausreagenssit ja niistä johdetut konjugaatit |
| 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 |
| EP2890788A1 (en) | 2012-08-31 | 2015-07-08 | The General Hospital Corporation | Biotin complexes for treatment and diagnosis of alzheimer's disease |
| 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 |
| US10568976B2 (en) | 2015-11-26 | 2020-02-25 | Debreceni Egyetem | 3,6,9, 15-tetraaza-bicyclo [9.3.1 ]pentadeca-1(14), 11(15), 12-triene based compounds and their application as ligands of essential metal ion based MRI and 52MN based PET contrast agents |
| 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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| US2673213A (en) * | 1952-06-03 | 1954-03-23 | Frederick C Bersworth | Polyalkylene polyamino acids |
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| US2954458A (en) * | 1958-07-17 | 1960-09-27 | Mankouski Charles | Holder for welding rods |
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| US3994966A (en) * | 1972-09-28 | 1976-11-30 | The Board Of Trustees Of The Leland Stanford Junior University | Chelating agents |
| GB1471894A (en) * | 1973-12-12 | 1977-04-27 | Wilkinson Sword Ltd | Compositions for application to or consumption by the body and containing a compound having a physiological cooling effect |
| US4022420A (en) * | 1975-11-06 | 1977-05-10 | Anacleto Pace | Formwork and connecting means apparatus for casting reinforced concrete |
| DE2650966A1 (de) * | 1975-11-14 | 1977-05-26 | Ciba Geigy Ag | Gegebenenfalls veraetherte basische methylolverbindungen und deren salze |
| US4352751A (en) * | 1979-09-10 | 1982-10-05 | Analytical Radiation Corporation | Species-linked diamine triacetic acids and their chelates |
| US4308249A (en) * | 1979-12-13 | 1981-12-29 | G. D. Searle & Co. | Radiopharmaceutical complexes of N-(tri-substituted alkyl)-iminodiacetic acids |
| US4339426A (en) * | 1980-03-18 | 1982-07-13 | Regents Of The University Of California | Bleomycin analog |
| US4647447A (en) * | 1981-07-24 | 1987-03-03 | Schering Aktiengesellschaft | Diagnostic media |
| DE3129906C3 (de) * | 1981-07-24 | 1996-12-19 | Schering Ag | Paramagnetische Komplexsalze, deren Herstellung und Mittel zur Verwendung bei der NMR-Diagnostik |
| US4454106A (en) * | 1982-06-07 | 1984-06-12 | Gansow Otto A | Use of metal chelate conjugated monoclonal antibodies |
| US4472509A (en) * | 1982-06-07 | 1984-09-18 | Gansow Otto A | Metal chelate conjugated monoclonal antibodies |
| NL194579C (nl) * | 1983-01-21 | 2002-08-05 | Schering Ag | Diagnostisch middel. |
| US4652519A (en) * | 1983-02-03 | 1987-03-24 | Yeda Research And Development Company Limited | Bifunctional chelating agents and process for their production |
| US4687659A (en) * | 1984-11-13 | 1987-08-18 | Salutar, Inc. | Diamide-DTPA-paramagnetic contrast agents for MR imaging |
| US4859451A (en) * | 1984-10-04 | 1989-08-22 | Salutar, Inc. | Paramagnetic contrast agents for MR imaging |
| US4687658A (en) * | 1984-10-04 | 1987-08-18 | Salutar, Inc. | Metal chelates of diethylenetriaminepentaacetic acid partial esters for NMR imaging |
| SE465907B (sv) * | 1984-11-01 | 1991-11-18 | Nyegaard & Co As | Diagnosticeringsmedel innehaallande en paramagnetisk metall |
| US4826673A (en) * | 1985-01-09 | 1989-05-02 | Mallinckrodt, Inc. | Methods and compositions for enhancing magnetic resonance imaging |
| US4933441A (en) * | 1987-01-27 | 1990-06-12 | Gibby Wendell A | Contrast enhancing agents for magnetic resonance images |
| US5078986A (en) * | 1989-02-15 | 1992-01-07 | Mallinckrodt Medical, Inc. | Method for enhancing magnetic resonance imaging using an image altering agent containing an excess of chelating agent |
-
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
-
1994
- 1994-03-28 US US08/219,339 patent/US5419894A/en not_active Expired - Lifetime
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693310A (en) * | 1986-09-26 | 1997-12-02 | Schering Aktiengesellschaft | Amide complexes |
| DE3710730A1 (de) * | 1987-03-31 | 1988-10-20 | Schering Ag | Substituierte komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
| US5137711A (en) * | 1988-07-19 | 1992-08-11 | Mallickrodt Medical, Inc. | Paramagnetic dtpa and edta alkoxyalkylamide complexes as mri agents |
| EP0425571B2 (en) † | 1988-07-19 | 2000-09-20 | Mallinckrodt Medical, Inc. | Novel magnetic resonance imaging agents |
| 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 |
| US5376357A (en) * | 1989-03-09 | 1994-12-27 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents |
| US5376358A (en) * | 1989-03-09 | 1994-12-27 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents |
| US5384108A (en) * | 1989-04-24 | 1995-01-24 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents |
| US5554357A (en) * | 1989-04-24 | 1996-09-10 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents containing hydrazide moieties |
| US5077037A (en) * | 1990-08-03 | 1991-12-31 | Mallinckrodt Medical, Inc. | Novel compositions for magnetic resonance imaging |
| DE102023001815A1 (de) * | 2023-05-05 | 2024-11-07 | Siempelkamp Maschinen- Und Anlagenbau Gmbh | Verfahren und Vorrichtung (Anlage) zur Herstellung einer Werkstoffplatte, Werkstoffplatte, sowie Verwendung einer Werkstoffplatte |
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 |
| IE57929B1 (en) | 1993-05-19 |
| CA1253514A (en) | 1989-05-02 |
| DK320884D0 (da) | 1984-06-29 |
| JPS6036452A (ja) | 1985-02-25 |
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