IL94818A - History of diethylenetriaminepentathetic acid couplings and pharmaceuticals and diagnostic preparations containing them - Google Patents
History of diethylenetriaminepentathetic acid couplings and pharmaceuticals and diagnostic preparations containing themInfo
- Publication number
- IL94818A IL94818A IL9481890A IL9481890A IL94818A IL 94818 A IL94818 A IL 94818A IL 9481890 A IL9481890 A IL 9481890A IL 9481890 A IL9481890 A IL 9481890A IL 94818 A IL94818 A IL 94818A
- Authority
- IL
- Israel
- Prior art keywords
- triaza
- tris
- complex
- acid
- hydrogen atom
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title description 27
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical class OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 150000001413 amino acids Chemical class 0.000 claims abstract description 18
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 150000007530 organic bases Chemical class 0.000 claims abstract description 11
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 239000008177 pharmaceutical agent Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 29
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 27
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 229910052693 Europium Inorganic materials 0.000 claims description 11
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 11
- 239000007983 Tris buffer Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052751 metal Chemical class 0.000 claims description 7
- 239000002184 metal Chemical class 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 6
- 150000004698 iron complex Chemical class 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- AQOXEJNYXXLRQQ-UHFFFAOYSA-N 2-[[2-[bis(carboxymethyl)amino]-3-(4-ethoxyphenyl)propyl]-[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound CCOC1=CC=C(CC(CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 AQOXEJNYXXLRQQ-UHFFFAOYSA-N 0.000 claims description 5
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 5
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- QRTXNZQKIDAKNB-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[bis(carboxymethyl)amino]-3-(4-phenylmethoxyphenyl)propyl]amino]acetic acid Chemical compound C1=CC(CC(CN(CCN(CC(O)=O)CC(O)=O)CC(=O)O)N(CC(O)=O)CC(O)=O)=CC=C1OCC1=CC=CC=C1 QRTXNZQKIDAKNB-UHFFFAOYSA-N 0.000 claims description 4
- UWTSAVIFSBWYKP-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[bis(carboxymethyl)amino]-3-phenylmethoxypropyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CC(N(CC(O)=O)CC(O)=O)COCC1=CC=CC=C1 UWTSAVIFSBWYKP-UHFFFAOYSA-N 0.000 claims description 4
- QAWHECZOIIEXPW-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[bis(carboxymethyl)amino]-3-phenylpropyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CC(N(CC(O)=O)CC(O)=O)CC1=CC=CC=C1 QAWHECZOIIEXPW-UHFFFAOYSA-N 0.000 claims description 4
- OYEFFRLHKMBAKH-UHFFFAOYSA-N 2-[[2-[bis(carboxymethyl)amino]-3-(4-butoxyphenyl)propyl]-[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound CCCCOC1=CC=C(CC(CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 OYEFFRLHKMBAKH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- OBICCQMGNNKVAW-UHFFFAOYSA-N 2-[[2-[bis(carboxymethyl)amino]-3-[4-(carboxymethoxy)phenyl]propyl]-[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OC(=O)COC1=CC=C(CC(CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 OBICCQMGNNKVAW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 239000002504 physiological saline solution Substances 0.000 claims description 3
- 238000001959 radiotherapy Methods 0.000 claims description 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 claims 2
- 101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 claims 1
- 239000012460 protein solution Substances 0.000 claims 1
- 101150068774 thyX gene Proteins 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- -1 ytterbium(III) ions Chemical class 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000011734 sodium Substances 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 239000002872 contrast media Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 239000002585 base Substances 0.000 description 9
- 230000000536 complexating effect Effects 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 210000002784 stomach Anatomy 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229940039231 contrast media Drugs 0.000 description 7
- 210000004185 liver Anatomy 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 230000008030 elimination Effects 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- LGMLJQFQKXPRGA-VPVMAENOSA-K gadopentetate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O LGMLJQFQKXPRGA-VPVMAENOSA-K 0.000 description 5
- 238000003384 imaging method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- YZKSKMHOCZJNBI-UHFFFAOYSA-N 2-[2-[[2-[carboxymethyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)propyl]-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]acetic acid Chemical compound CC(C)(C)OC(=O)CN(CC(O)=O)CCN(CC(=O)OC(C)(C)C)CC(N(CC(O)=O)CC(=O)OC(C)(C)C)CC1=CC=C(O)C=C1 YZKSKMHOCZJNBI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910001940 europium oxide Inorganic materials 0.000 description 3
- AEBZCFFCDTZXHP-UHFFFAOYSA-N europium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Eu+3].[Eu+3] AEBZCFFCDTZXHP-UHFFFAOYSA-N 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- FPMUIQZYMZYBKU-UHFFFAOYSA-N tert-butyl 2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)propyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)CC1=CC=C(O)C=C1 FPMUIQZYMZYBKU-UHFFFAOYSA-N 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NFDYZDYFHGOTGM-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[bis(carboxymethyl)amino]-3-(4-methoxyphenyl)propyl]amino]acetic acid Chemical compound COC1=CC=C(CC(CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 NFDYZDYFHGOTGM-UHFFFAOYSA-N 0.000 description 2
- UPEJSCBQXHRZHS-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[bis(carboxymethyl)amino]-3-[4-[(4-methoxyphenyl)methoxy]phenyl]propyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(CC(CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 UPEJSCBQXHRZHS-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 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 2
- 206010061218 Inflammation Diseases 0.000 description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001767 cationic compounds Chemical class 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 238000002405 diagnostic procedure Methods 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 2
- ILXZMTJXXHNZJS-UHFFFAOYSA-N diethyl hydrogen phosphate;hydrochloride Chemical compound Cl.CCOP(O)(=O)OCC ILXZMTJXXHNZJS-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- RJOJUSXNYCILHH-UHFFFAOYSA-N gadolinium(3+) Chemical compound [Gd+3] RJOJUSXNYCILHH-UHFFFAOYSA-N 0.000 description 2
- 210000000232 gallbladder Anatomy 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960003104 ornithine Drugs 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 229960003330 pentetic acid Drugs 0.000 description 2
- 238000003408 phase transfer catalysis Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 229940069575 rompun Drugs 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
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- FERIWWYTZDKQDK-UHFFFAOYSA-N tert-butyl 2-[2-[[1-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-(4-methoxyphenyl)propan-2-yl]-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]acetate Chemical compound COC1=CC=C(CC(CN(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)N(CCN(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C=C1 FERIWWYTZDKQDK-UHFFFAOYSA-N 0.000 description 1
- QZZIPKDDFWHAQH-UHFFFAOYSA-N tert-butyl 2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-[4-[(4-methoxyphenyl)methoxy]phenyl]propyl]amino]acetate Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(CC(CN(CCN(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C=C1 QZZIPKDDFWHAQH-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- ORZHVTYKPFFVMG-UHFFFAOYSA-N xylenol orange Chemical compound OC(=O)CN(CC(O)=O)CC1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C=C(CN(CC(O)=O)CC(O)=O)C(O)=C(C)C=2)=C1 ORZHVTYKPFFVMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Radiology & Medical Imaging (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Analysing Materials By The Use Of Radiation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3922005A DE3922005A1 (de) | 1989-06-30 | 1989-06-30 | Derivatisierte dtpa-komplexe, diese verbindungen enthaltende pharmazeutische mittel, ihre verwendung und verfahren zu deren herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL94818A0 IL94818A0 (en) | 1991-04-15 |
| IL94818A true IL94818A (en) | 1996-05-14 |
Family
ID=6384290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9481890A IL94818A (en) | 1989-06-30 | 1990-06-21 | History of diethylenetriaminepentathetic acid couplings and pharmaceuticals and diagnostic preparations containing them |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0405704B1 (sv) |
| JP (1) | JP2603357B2 (sv) |
| KR (1) | KR100190808B1 (sv) |
| AT (1) | ATE115546T1 (sv) |
| AU (1) | AU637111B2 (sv) |
| CA (1) | CA2020142C (sv) |
| CZ (1) | CZ277926B6 (sv) |
| DD (1) | DD296276B5 (sv) |
| DE (3) | DE3922005A1 (sv) |
| DK (1) | DK0405704T3 (sv) |
| ES (1) | ES2066113T3 (sv) |
| FI (1) | FI102168B (sv) |
| HK (1) | HK1002810A1 (sv) |
| HU (1) | HU210208B (sv) |
| IE (1) | IE65676B1 (sv) |
| IL (1) | IL94818A (sv) |
| NL (1) | NL300182I2 (sv) |
| NO (2) | NO179203C (sv) |
| NZ (1) | NZ234295A (sv) |
| PT (1) | PT94541B (sv) |
| RU (1) | RU2086554C1 (sv) |
| TW (1) | TW219356B (sv) |
| UA (1) | UA27275C2 (sv) |
| ZA (1) | ZA905129B (sv) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4011684A1 (de) | 1990-04-06 | 1991-10-10 | Schering Ag | Dtpa-monoamide, diese verbindungen enthaltende pharmazeutische mittel, ihre verwendung und verfahren zu deren herstellung |
| DE4302289A1 (de) * | 1993-01-25 | 1994-07-28 | Schering Ag | Verfahren zur Herstellung C-substituierter Diethylentriamine |
| 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 |
| DE4341724A1 (de) * | 1993-12-03 | 1995-06-08 | Schering Ag | Halogenaryl-substituierte Metallkomplexe enthaltende pharmazeutische Mittel, deren Verwendung in der Diagnostik, sowie Verfahren zur Herstellung der Komplexe und Mittel |
| US5582814A (en) * | 1994-04-15 | 1996-12-10 | Metasyn, Inc. | 1-(p-n-butylbenzyl) DTPA for magnetic resonance imaging |
| CA2206558A1 (en) * | 1994-11-30 | 1996-06-06 | Schering Aktiengesellschaft | Use of metal complexes as x-ray diagnostic agents for the liver and gallbladder |
| US5672335A (en) * | 1994-11-30 | 1997-09-30 | Schering Aktiengesellschaft | Use of metal complexes as liver and gallbladder X-ray diagnostic agents |
| TW319763B (sv) | 1995-02-01 | 1997-11-11 | Epix Medical Inc | |
| DE19606326A1 (de) * | 1995-02-09 | 1996-08-22 | Schering Ag | Kontrastmittelhaltige Liposomenformulierung sowie deren Verwendung für die In-vivo-Diagnostik, insbesondere für die Darstellung des Intravasalraumes |
| 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 |
| JP2759627B2 (ja) * | 1995-07-21 | 1998-05-28 | 東北大学長 | 非エステル結合性ｄｔｐａ誘導体およびその製造方法 |
| DE19641197C2 (de) * | 1996-09-24 | 1999-02-18 | Schering Ag | Ionenpaare und ihre Verwendung als Kontrastmittel |
| DE19646762B4 (de) * | 1996-11-04 | 2004-05-13 | Schering Ag | Verwendung von Metallverbindungen zur Herstellung von Mitteln zur Strahlentherapie von Tumoren |
| DE19712012A1 (de) * | 1997-03-13 | 1998-09-24 | Schering Ag | Verfahren zur Herstellung kristalliner 3,6,9-Triaza-3,6-9-tris(carboxymethyl)-4-(4- ethoxybenzyl)-undecandisäure |
| DE19744004C1 (de) * | 1997-09-26 | 1999-07-22 | Schering Ag | Lipophile Metall-Komplexe für Nekrose und Infarkt-Imaging |
| US6495118B1 (en) | 1997-09-26 | 2002-12-17 | Schering Aktiengesellschaft | Lipophilic metal complexes for necrosis and infarction imaging |
| US6534040B2 (en) * | 1999-12-23 | 2003-03-18 | Health Research, Inc. | Chlorin and bacteriochlorin-based aminophenyl DTPA and N2S2 conjugates for MR contrast media and radiopharmaceuticals |
| FR2867473B1 (fr) | 2004-03-12 | 2006-06-23 | Guerbet Sa | Compose de porphyrines et utilisation a haut champ en irm |
| KR100749087B1 (ko) * | 2006-06-02 | 2007-08-14 | 경북대학교 산학협력단 | 신규한 ｄｔｐａ-비스-아미드 리간드들 및 이들이 결합된가돌리늄 착물 |
| SE533165C2 (sv) * | 2008-06-13 | 2010-07-13 | Chemseq Internat Ab | Kemikalie och förfarande för komplexbindning av metalljoner, som är minst tvåvärda |
| EP2338874A1 (en) * | 2009-12-16 | 2011-06-29 | Bracco Imaging S.p.A | Process for the preparation of chelated compounds |
| EP2580184A2 (de) | 2010-06-11 | 2013-04-17 | Bayer Intellectual Property GmbH | Verfahren zur herstellung kristalliner 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxybenzyl)-undecandisäure und die verwendung zur herstellung von primovist® |
| DE102010023890A1 (de) | 2010-06-11 | 2011-12-15 | Bayer Schering Pharma Aktiengesellschaft | Verfahren zur Herstellung kristalliner 3,6,9-Triaza-3,6,9-tris(carboxymethyl)-4-(ethoxybenzyl)-undecandinsäure und die Verwendung zur Herstellung von Primovist |
| CN104761461A (zh) * | 2014-09-09 | 2015-07-08 | 山东富创医药科技有限公司 | 一种新的钆塞酸二钠中间体的制备方法 |
| US11149041B2 (en) * | 2016-05-30 | 2021-10-19 | Biophore India Pharmaceuticals Pvt. Ltd. | Process for the preparation of gadolinium complex of (4S)-4-(4-ethoxybenzyl)-3,6,9-tris(carboxylatomethyl)-3,6,9-triazaundecanedioic acid disodium (Gadoxetate disodium) |
| JP6867639B2 (ja) * | 2016-10-11 | 2021-05-12 | 学校法人 聖マリアンナ医科大学 | 非イオン性ヨード造影剤の結合体 |
| EP4059925A1 (en) | 2021-03-15 | 2022-09-21 | Bayer Aktiengesellschaft | New contrast agent for use in magnetic resonance imaging |
| EP4335840A1 (en) | 2022-09-09 | 2024-03-13 | Bayer Aktiengesellschaft | New contrast agents for use in diagnostic imaging |
| EP4335462A1 (en) | 2022-09-09 | 2024-03-13 | Bayer AG | Contrast agents for use in diagnostic computed tomography imaging |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL194579C (nl) * | 1983-01-21 | 2002-08-05 | Schering Ag | Diagnostisch middel. |
| US4672028A (en) * | 1984-05-23 | 1987-06-09 | Icn Micromedic Systems, Inc. | Compositions and method for simultaneous multiple array of analytes using radioisotope chelate labels |
| US4824986A (en) * | 1985-04-26 | 1989-04-25 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Metal chelate protein conjugate |
| IL83966A (en) * | 1986-09-26 | 1992-03-29 | Schering Ag | Amides of aminopolycarboxylic acids and pharmaceutical compositions containing them |
| DE3710730A1 (de) * | 1987-03-31 | 1988-10-20 | Schering Ag | Substituierte komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
| WO1989000557A1 (en) * | 1987-07-16 | 1989-01-26 | Cockbain, Julian, Roderick, Michaelson | Aminopolycarboxylic acids and derivatives thereof |
| AU617338B2 (en) * | 1987-07-16 | 1991-11-28 | Nycomed As | Aminopolycarboxylic acids and derivatives thereof |
| DE3728525A1 (de) * | 1987-08-24 | 1989-03-16 | Schering Ag | Mehrkernige substituierte komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
-
1989
- 1989-06-30 DE DE3922005A patent/DE3922005A1/de not_active Withdrawn
-
1990
- 1990-06-21 IL IL9481890A patent/IL94818A/en active IP Right Grant
- 1990-06-26 CZ CS903174A patent/CZ277926B6/cs not_active IP Right Cessation
- 1990-06-26 IE IE229990A patent/IE65676B1/en not_active IP Right Cessation
- 1990-06-27 AT AT90250165T patent/ATE115546T1/de active
- 1990-06-27 KR KR1019900009529A patent/KR100190808B1/ko not_active IP Right Cessation
- 1990-06-27 DK DK90250165.9T patent/DK0405704T3/da active
- 1990-06-27 ES ES90250165T patent/ES2066113T3/es not_active Expired - Lifetime
- 1990-06-27 EP EP90250165A patent/EP0405704B1/de not_active Expired - Lifetime
- 1990-06-27 DE DE200412000051 patent/DE122004000051I2/de active Active
- 1990-06-27 DE DE59007987T patent/DE59007987D1/de not_active Expired - Lifetime
- 1990-06-28 NZ NZ234295A patent/NZ234295A/xx unknown
- 1990-06-29 ZA ZA905129A patent/ZA905129B/xx unknown
- 1990-06-29 CA CA002020142A patent/CA2020142C/en not_active Expired - Lifetime
- 1990-06-29 FI FI903295A patent/FI102168B/sv active Protection Beyond IP Right Term
- 1990-06-29 HU HU904040A patent/HU210208B/hu unknown
- 1990-06-29 JP JP2170372A patent/JP2603357B2/ja not_active Expired - Lifetime
- 1990-06-29 DD DD34235090A patent/DD296276B5/de active IP Right Maintenance
- 1990-06-29 PT PT94541A patent/PT94541B/pt not_active IP Right Cessation
- 1990-06-29 RU SU904830458A patent/RU2086554C1/ru active Protection Beyond IP Right Term
- 1990-06-29 NO NO902925A patent/NO179203C/no not_active IP Right Cessation
- 1990-06-29 UA UA4830458A patent/UA27275C2/uk unknown
- 1990-06-29 AU AU58024/90A patent/AU637111B2/en not_active Expired
- 1990-11-10 TW TW079109532A patent/TW219356B/zh active
-
1998
- 1998-03-10 HK HK98101936A patent/HK1002810A1/xx not_active IP Right Cessation
-
2005
- 2005-03-18 NL NL300182C patent/NL300182I2/nl unknown
- 2005-05-23 NO NO2005013C patent/NO2005013I2/no unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed |