NO305126B1 - Kompleksert forbindelse omfattende aminokarboksylatligander med substituerte aromatiske amidrester - Google Patents

Kompleksert forbindelse omfattende aminokarboksylatligander med substituerte aromatiske amidrester Download PDF

Info

Publication number: NO305126B1
Authority: NO; Norway
Prior art keywords: alkyl; phenyl; hydroxy; solution; amino
Prior art date: 1991-08-01

Application number

NO923038A

Other languages

English (en)

Norwegian (no)

Other versions

NO923038L (no

NO923038D0 (no

Inventor

Radhakrishna Pillai

Edmund R Marinelli

Ramachandran S Ranganathan

Michael F Tweedle

Sang-Ihn Kang

Original Assignee

Bracco Int Bv

Priority date (The priority date 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 date listed.)

1991-08-01

Filing date

1992-07-31

Publication date

1999-04-06

1992-07-31 Application filed by Bracco Int Bv filed Critical Bracco Int Bv

1992-07-31 Publication of NO923038D0 publication Critical patent/NO923038D0/no

1993-02-02 Publication of NO923038L publication Critical patent/NO923038L/no

1999-04-06 Publication of NO305126B1 publication Critical patent/NO305126B1/no

Links

239000003446 ligand Substances 0.000 title claims abstract description 50
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title claims abstract description 11
150000001875 compounds Chemical class 0.000 title claims description 94
150000008430 aromatic amides Chemical group 0.000 title abstract description 5
229910052751 metal Inorganic materials 0.000 claims description 40
239000002184 metal Substances 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000002738 chelating agent Substances 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 22
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
-1 4,1-phenylene Chemical group 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
230000005298 paramagnetic effect Effects 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
HHLZCENAOIROSL-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound OC(=O)CN1CCNCCN(CC(O)=O)CCN(CC(O)=O)CC1 HHLZCENAOIROSL-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000007983 Tris buffer Substances 0.000 claims description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
XTZCTOAYMHMTLA-UHFFFAOYSA-N 2-[4-[2-[3,5-bis(2,3-dihydroxypropylcarbamoyl)anilino]-2-oxoethyl]-7,10-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical group OCC(O)CNC(=O)C1=CC(C(=O)NCC(O)CO)=CC(NC(=O)CN2CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC2)=C1 XTZCTOAYMHMTLA-UHFFFAOYSA-N 0.000 claims description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
IPUVYPTUQAIICH-UHFFFAOYSA-N 2-[7-[n-acetyl-4-(methylcarbamothioylamino)anilino]-4,10-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound C1=CC(NC(=S)NC)=CC=C1N(C(C)=O)N1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 IPUVYPTUQAIICH-UHFFFAOYSA-N 0.000 claims description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 claims description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
239000013522 chelant Substances 0.000 abstract description 25
239000000243 solution Substances 0.000 description 112
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 80
229910001868 water Inorganic materials 0.000 description 69
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
235000019439 ethyl acetate Nutrition 0.000 description 32
239000002904 solvent Substances 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
239000007787 solid Substances 0.000 description 23
239000000047 product Substances 0.000 description 22
238000000921 elemental analysis Methods 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
238000003384 imaging method Methods 0.000 description 17
239000000460 chlorine Substances 0.000 description 16
UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
239000003054 catalyst Substances 0.000 description 15
238000002595 magnetic resonance imaging Methods 0.000 description 15
150000003839 salts Chemical class 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
230000001588 bifunctional effect Effects 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 13
239000002872 contrast media Substances 0.000 description 13
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
239000012071 phase Substances 0.000 description 12
239000011347 resin Substances 0.000 description 12
229920005989 resin Polymers 0.000 description 12
229940126062 Compound A Drugs 0.000 description 11
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 11
229910021645 metal ion Inorganic materials 0.000 description 11
102000004169 proteins and genes Human genes 0.000 description 11
108090000623 proteins and genes Proteins 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 7
125000004429 atom Chemical group 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
239000012043 crude product Substances 0.000 description 7
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 7
230000002285 radioactive effect Effects 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 6
229910052688 Gadolinium Inorganic materials 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
150000002540 isothiocyanates Chemical class 0.000 description 6
230000005291 magnetic effect Effects 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
238000000746 purification Methods 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
239000003814 drug Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
125000002768 hydroxyalkyl group Chemical group 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000012217 radiopharmaceutical Substances 0.000 description 5
229940121896 radiopharmaceutical Drugs 0.000 description 5
230000002799 radiopharmaceutical effect Effects 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
150000000921 Gadolinium Chemical class 0.000 description 4
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 4
239000000908 ammonium hydroxide Substances 0.000 description 4
238000005349 anion exchange Methods 0.000 description 4
239000012267 brine Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000012634 fragment Substances 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
PYPPUPWJXZHVIR-UHFFFAOYSA-N 2-[7-(n-acetyl-4-aminoanilino)-4,10-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound C=1C=C(N)C=CC=1N(C(=O)C)N1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 PYPPUPWJXZHVIR-UHFFFAOYSA-N 0.000 description 3
FILDXHVNMMHPQD-UHFFFAOYSA-N 2-[7-(n-acetyl-4-nitroanilino)-4,10-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(C(=O)C)N1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 FILDXHVNMMHPQD-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
229910004373 HOAc Inorganic materials 0.000 description 3
241000282412 Homo Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
239000002585 base Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000000872 buffer Substances 0.000 description 3
150000004697 chelate complex Chemical class 0.000 description 3
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
GGTSJKFPGKFLCZ-UHFFFAOYSA-N dimethyl 5-nitrobenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC([N+]([O-])=O)=C1 GGTSJKFPGKFLCZ-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
230000029142 excretion Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
229940127121 immunoconjugate Drugs 0.000 description 3
229910052747 lanthanoid Inorganic materials 0.000 description 3
150000002602 lanthanoids Chemical class 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000001959 radiotherapy Methods 0.000 description 3
239000000523 sample Substances 0.000 description 3
238000012800 visualization Methods 0.000 description 3
QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 description 2
RKPJXEFGHGVLCC-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-10-[2-[2-(4-nitrophenyl)ethylamino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CCN1CC(=O)NCCC1=CC=C([N+]([O-])=O)C=C1 RKPJXEFGHGVLCC-UHFFFAOYSA-N 0.000 description 2
JEBBXAOUTGQBPF-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-10-[2-[4-(2,3-dihydroxypropylcarbamoyl)anilino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound C1=CC(C(=O)NCC(O)CO)=CC=C1NC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 JEBBXAOUTGQBPF-UHFFFAOYSA-N 0.000 description 2
SUBSNADZBBVYJO-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-10-[2-[n-methyl-3,5-bis(2-methylbutylcarbamoyl)anilino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound CCC(C)CNC(=O)C1=CC(C(=O)NCC(C)CC)=CC(N(C)C(=O)CN2CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC2)=C1 SUBSNADZBBVYJO-UHFFFAOYSA-N 0.000 description 2
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-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
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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 description 2
229920005654 Sephadex Polymers 0.000 description 2
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230000003213 activating effect Effects 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
238000005571 anion exchange chromatography Methods 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
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229910052801 chlorine Inorganic materials 0.000 description 2
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239000012954 diazonium Substances 0.000 description 2
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201000010099 disease Diseases 0.000 description 2
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150000004665 fatty acids Chemical class 0.000 description 2
RJOJUSXNYCILHH-UHFFFAOYSA-N gadolinium(3+) Chemical compound [Gd+3] RJOJUSXNYCILHH-UHFFFAOYSA-N 0.000 description 2
230000005283 ground state Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
238000002372 labelling Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
102000004196 processed proteins & peptides Human genes 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
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230000035484 reaction time Effects 0.000 description 2
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239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
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235000010755 mineral Nutrition 0.000 description 1
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150000002825 nitriles Chemical class 0.000 description 1
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239000011734 sodium Substances 0.000 description 1
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239000012279 sodium borohydride Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
XJPKDRJZNZMJQM-UHFFFAOYSA-N tetrakis(prop-2-enyl)stannane Chemical compound C=CC[Sn](CC=C)(CC=C)CC=C XJPKDRJZNZMJQM-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
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QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
GRTBAGCGDOYUBE-UHFFFAOYSA-N yttrium(3+) Chemical compound [Y+3] GRTBAGCGDOYUBE-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- 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
- A61K51/0482—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 chelates from cyclic ligands, e.g. DOTA
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Radiology & Medical Imaging (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Hydrogenated Pyridines (AREA)

NO923038A 1991-08-01 1992-07-31 Kompleksert forbindelse omfattende aminokarboksylatligander med substituerte aromatiske amidrester NO305126B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US73899891A	1991-08-01	1991-08-01

Publications (3)

Publication Number	Publication Date
NO923038D0 NO923038D0 (no)	1992-07-31
NO923038L NO923038L (no)	1993-02-02
NO305126B1 true NO305126B1 (no)	1999-04-06

Family

ID=24970389

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO923038A NO305126B1 (no)	1991-08-01	1992-07-31	Kompleksert forbindelse omfattende aminokarboksylatligander med substituerte aromatiske amidrester

Country Status (17)

Country	Link
EP (1)	EP0543482B1 (hu)
JP (1)	JP2538165B2 (hu)
KR (1)	KR930003911A (hu)
CN (1)	CN1069027A (hu)
AT (1)	ATE212861T1 (hu)
AU (1)	AU2061592A (hu)
CA (1)	CA2074867A1 (hu)
DE (1)	DE69232408T2 (hu)
ES (1)	ES2173862T3 (hu)
FI (1)	FI923470A (hu)
HU (1)	HUT62906A (hu)
IL (1)	IL102570A0 (hu)
MX (1)	MX9204434A (hu)
NO (1)	NO305126B1 (hu)
PL (1)	PL295490A1 (hu)
TW (1)	TW213864B (hu)
ZA (1)	ZA925521B (hu)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5310535A (en) *	1992-04-24	1994-05-10	The Dow Chemical Company	Carboxamide modified polyamine chelators and radioactive complexes thereof for conjugation to antibodies
WO1995027705A1 (en) *	1994-04-08	1995-10-19	Bracco International B.V.	Aromatic amide compounds and metal chelates thereof
TW319763B (hu)	1995-02-01	1997-11-11	Epix Medical Inc
CA2371816C (en) *	1999-02-18	2010-04-27	The Regents Of The University Of California	Phthalamide-lanthanide complexes for use as luminescent markers
FR2802928B1 (fr) *	1999-12-22	2003-01-31	Air Liquide	Polyazacycloalcanes eventuellement greffes sur une matrice solide, complexes organometalliques les incorporant comme ligands. utilisation desdits composes a l'extraction de metaux lourds
ATE271396T1 (de) *	2000-05-12	2004-08-15	Univ Hospital	Prochelators von radiometall markierten molekülen
FR2827515B1 (fr) *	2001-07-20	2005-06-03	Oreal	Composition moussante a base de silice et de polymere cationique
JP2009517465A (ja) *	2005-12-02	2009-04-30	ジーイー・ヘルスケア・アクスイェ・セルスカプ	多量体の磁気共鳴造影剤
EP2774611A4 (en) *	2011-10-06	2015-03-04	Ihi Corp	MAGNETIC COMPOSITION AND METHOD FOR THE PRODUCTION THEREOF
CN103073667B (zh) *	2013-01-25	2016-05-11	南京大学	一种双伯胺基螯合树脂及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH03203282A (ja) *	1989-12-29	1991-09-04	Nec Kansai Ltd	半導体レーザダイオード
JP2776953B2 (ja) *	1990-04-10	1998-07-16	日本メジフィジックス株式会社	多官能性金属キレート化合物とその用途
DE4035760A1 (de) *	1990-11-08	1992-05-14	Schering Ag	Mono-n-substituierte 1,4,7,10-tetraazacyclododecan-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel
JP2807852B2 (ja) *	1991-07-18	1998-10-08	株式会社ミドリ十字	新規キレート化剤、該キレート化剤と金属原子との錯化合物及びそれを含む診断剤

1992
- 1992-07-18 TW TW081105703A patent/TW213864B/zh active
- 1992-07-21 IL IL102570A patent/IL102570A0/xx unknown
- 1992-07-22 ZA ZA925521A patent/ZA925521B/xx unknown
- 1992-07-29 CA CA002074867A patent/CA2074867A1/en not_active Abandoned
- 1992-07-29 AU AU20615/92A patent/AU2061592A/en not_active Abandoned
- 1992-07-30 MX MX9204434A patent/MX9204434A/es unknown
- 1992-07-31 FI FI923470A patent/FI923470A/fi unknown
- 1992-07-31 KR KR1019920013787A patent/KR930003911A/ko not_active Application Discontinuation
- 1992-07-31 HU HU9202513A patent/HUT62906A/hu unknown
- 1992-07-31 NO NO923038A patent/NO305126B1/no unknown
- 1992-07-31 PL PL29549092A patent/PL295490A1/xx unknown
- 1992-07-31 JP JP4205097A patent/JP2538165B2/ja not_active Expired - Fee Related
- 1992-08-01 CN CN92109214A patent/CN1069027A/zh active Pending
- 1992-08-03 EP EP92307091A patent/EP0543482B1/en not_active Expired - Lifetime
- 1992-08-03 AT AT92307091T patent/ATE212861T1/de not_active IP Right Cessation
- 1992-08-03 DE DE69232408T patent/DE69232408T2/de not_active Expired - Fee Related
- 1992-08-03 ES ES92307091T patent/ES2173862T3/es not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO923038L (no)	1993-02-02
EP0543482B1 (en)	2002-02-06
ES2173862T3 (es)	2002-11-01
MX9204434A (es)	1994-06-30
HUT62906A (en)	1993-06-28
AU2061592A (en)	1993-02-04
JPH05208920A (ja)	1993-08-20
DE69232408T2 (de)	2002-09-19
IL102570A0 (en)	1993-01-14
HU9202513D0 (en)	1992-10-28
DE69232408D1 (de)	2002-03-21
CA2074867A1 (en)	1993-02-02
NO923038D0 (no)	1992-07-31
PL295490A1 (en)	1993-05-31
EP0543482A1 (en)	1993-05-26
TW213864B (hu)	1993-10-01
ATE212861T1 (de)	2002-02-15
CN1069027A (zh)	1993-02-17
FI923470A0 (fi)	1992-07-31
KR930003911A (ko)	1993-03-22
ZA925521B (en)	1993-04-28
JP2538165B2 (ja)	1996-09-25
FI923470A (fi)	1993-02-02

Publication	Publication Date	Title
US4885363A (en)	1989-12-05	1-substituted-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs
US5474756A (en)	1995-12-12	Method for imaging mammalian tissue using 1-substituted-1,4,7-tricarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs
US6875864B2 (en)	2005-04-05	Aminocarboxylate ligands having substituted aromatic amide moieties
US6056939A (en)	2000-05-02	Self-assembling heteropolymetallic chelates as imaging agents and radiopharmaceuticals
US5573752A (en)	1996-11-12	Aromatic amide compounds and metal chelates thereof
JP2833766B2 (ja)	1998-12-09	アミノポリカルボン酸およびその誘導体
US5417960A (en)	1995-05-23	Nitrogen-containing cyclic ligands, metallic complexes formed by these ligands, diagnostic compositions containing these complexes and process for the preparation of the ligands
CA1341176C (en)	2001-01-30	Macrocylic compounds
RU2743167C2 (ru)	2021-02-15	Контрастные агенты
CA2487908C (en)	2013-02-12	Scorpionate-like pendant macrocyclic ligands, complexes and compositions thereof, and methods of using same
JPH05112567A (ja)	1993-05-07	６員環を有する巨大環式テトラアザ化合物、その製法及びこれを含有する薬剤
CA2615434A1 (en)	2007-01-25	Perfluoroalkyl-containing complexes, process for their production as well as their use
JP7145156B2 (ja)	2022-09-30	二量体造影剤
AU663572B2 (en)	1995-10-12	Tetraazacyclododecane derivative and its use
NO305126B1 (no)	1999-04-06	Kompleksert forbindelse omfattende aminokarboksylatligander med substituerte aromatiske amidrester
KR20080043762A (ko)	2008-05-19	퍼플루오로알킬 함유 착물, 그의 제조 방법 및 용도
AU625529B2 (en)	1992-07-16	10-(2'-hydroxy-3'-alkoxy-1,4,7-triscarboxymethyl-1,4,7,10- tetraazacyclododecanes
US5695737A (en)	1997-12-09	Dimeric DTPA derivatives, their metal complexes and pharmaceutical agents containing these complexes
IE904318A1 (en)	1991-07-03	10-(2'-hydroxy-3'-alkoxy-1,4,7-triscarboxymethyl-1,4,7,10,¹-tetraazacyclododecanes
KR101451446B1 (ko)	2014-10-16	퍼플루오르화 ｐｅｇ기를 갖는 금속 킬레이트, 그의 제조 방법, 및 그의 용도
KR0153501B1 (ko)	1998-12-01	오르토 결합 작용기를 갖는 킬란트 및 그의 착물
JP2538165C (hu)	1998-11-05
AU637052B2 (en)	1993-05-20	Macrocyclic polyaza compounds containing 5 or 6 rings, process for producing them and pharmaceutical media containing them
JPH0656802A (ja)	1994-03-01	テトラアザシクロドデカン誘導体およびその用途