IL90409A - Acrylic Acids 2 Aralkyl - 1, 4, 7, 01 Tetraazacyclododecane - 'N, "N,"' N, "" N Tetraacetic acid, their preparation and medical use - Google Patents

Acrylic Acids 2 Aralkyl - 1, 4, 7, 01 Tetraazacyclododecane - 'N, "N,"' N, "" N Tetraacetic acid, their preparation and medical use

Info

Publication number: IL90409A
Authority: IL; Israel
Prior art keywords: chelate; group; member selected; conjugate; ncs
Prior art date: 1988-05-25

Application number

IL9040989A

Other languages

English (en)

Hebrew (he)

Other versions

IL90409A0 (en

Original Assignee

Us Commerce

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.)

1988-05-25

Filing date

1989-05-25

Publication date

1996-09-12

1989-05-25 Application filed by Us Commerce filed Critical Us Commerce

1989-05-25 Priority to IL11306889A priority Critical patent/IL113068A/en

1990-01-18 Publication of IL90409A0 publication Critical patent/IL90409A0/xx

1996-09-12 Publication of IL90409A publication Critical patent/IL90409A/en

Links

238000002360 preparation method Methods 0.000 title claims description 4
239000013522 chelant Substances 0.000 claims abstract description 58
229910021645 metal ion Inorganic materials 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 28
229910052797 bismuth Inorganic materials 0.000 claims abstract description 19
239000003446 ligand Substances 0.000 claims abstract description 15
229910052727 yttrium Inorganic materials 0.000 claims abstract description 12
229910052745 lead Inorganic materials 0.000 claims abstract description 11
230000001413 cellular effect Effects 0.000 claims abstract description 10
229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 10
150000002602 lanthanoids Chemical class 0.000 claims abstract description 10
238000002405 diagnostic procedure Methods 0.000 claims abstract description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
102000004169 proteins and genes Human genes 0.000 claims description 23
108090000623 proteins and genes Proteins 0.000 claims description 23
229910052751 metal Inorganic materials 0.000 claims description 21
239000002184 metal Substances 0.000 claims description 21
230000008569 process Effects 0.000 claims description 15
229910052688 Gadolinium Inorganic materials 0.000 claims description 10
239000005556 hormone Substances 0.000 claims description 10
229940088597 hormone Drugs 0.000 claims description 10
150000003431 steroids Chemical class 0.000 claims description 9
102000004190 Enzymes Human genes 0.000 claims description 8
108090000790 Enzymes Proteins 0.000 claims description 8
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 8
229910052767 actinium Inorganic materials 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 6
229910052771 Terbium Inorganic materials 0.000 claims description 6
229910052693 Europium Inorganic materials 0.000 claims description 5
229910052802 copper Inorganic materials 0.000 claims description 5
239000002245 particle Substances 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 3
238000000338 in vitro Methods 0.000 claims description 3
238000012360 testing method Methods 0.000 claims 2
150000001875 compounds Chemical class 0.000 abstract description 51
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
229910052776 Thorium Inorganic materials 0.000 abstract description 3
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract description 2
229910052793 cadmium Inorganic materials 0.000 abstract description 2
229910001431 copper ion Inorganic materials 0.000 abstract description 2
229910052712 strontium Inorganic materials 0.000 abstract description 2
235000018102 proteins Nutrition 0.000 description 21
-1 2-substituted 1, 4, 7, 10-Tetraaza cyclododecane - Chemical class 0.000 description 16
WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 description 11
150000002678 macrocyclic compounds Chemical class 0.000 description 11
150000002148 esters Chemical class 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
206010028980 Neoplasm Diseases 0.000 description 9
125000003277 amino group Chemical group 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
230000005855 radiation Effects 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000010949 copper Substances 0.000 description 7
238000003384 imaging method Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 6
150000002540 isothiocyanates Chemical class 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
229940125773 compound 10 Drugs 0.000 description 4
229940125797 compound 12 Drugs 0.000 description 4
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 4
229920002521 macromolecule Polymers 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000037361 pathway Effects 0.000 description 4
238000004611 spectroscopical analysis Methods 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
238000003556 assay Methods 0.000 description 3
230000001588 bifunctional effect Effects 0.000 description 3
229910000085 borane Inorganic materials 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000002738 chelating agent Substances 0.000 description 3
230000009920 chelation Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229940126214 compound 3 Drugs 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000000717 retained effect Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
210000004881 tumor cell Anatomy 0.000 description 3
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
SQWOBSHRAUJBNP-UHFFFAOYSA-N 2-[4,7,10-tris(carboxymethyl)-6-[(4-nitrophenyl)methyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound C1N(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CCN(CC(O)=O)C1CC1=CC=C([N+]([O-])=O)C=C1 SQWOBSHRAUJBNP-UHFFFAOYSA-N 0.000 description 2
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
102000003886 Glycoproteins Human genes 0.000 description 2
108090000288 Glycoproteins Proteins 0.000 description 2
208000000389 T-cell leukemia Diseases 0.000 description 2
208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000427 antigen Substances 0.000 description 2
102000036639 antigens Human genes 0.000 description 2
108091007433 antigens Proteins 0.000 description 2
JCXGWMGPZLAOME-AKLPVKDBSA-N bismuth-212 Chemical compound [212Bi] JCXGWMGPZLAOME-AKLPVKDBSA-N 0.000 description 2
210000001124 body fluid Anatomy 0.000 description 2
239000010839 body fluid Substances 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
150000004696 coordination complex Chemical class 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
125000005647 linker group Chemical group 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
230000002285 radioactive effect Effects 0.000 description 2
238000001959 radiotherapy Methods 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 2
ZUZPOSNHFCUOMQ-UHFFFAOYSA-N thiolan-2-amine Chemical compound NC1CCCS1 ZUZPOSNHFCUOMQ-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
NKIJBSVPDYIEAT-UHFFFAOYSA-N 1,4,7,10-tetrazacyclododec-10-ene Chemical compound C1CNCCN=CCNCCN1 NKIJBSVPDYIEAT-UHFFFAOYSA-N 0.000 description 1
150000007545 14-membered macrocycles Chemical class 0.000 description 1
RFLCXBQMQJSWCK-UHFFFAOYSA-N 2-(2-amino-4-nitrophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C([N+]([O-])=O)C=C1N RFLCXBQMQJSWCK-UHFFFAOYSA-N 0.000 description 1
WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 description 1
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
BSVMPWANOMFSPR-UHFFFAOYSA-N 2-iodoacetyl chloride Chemical compound ClC(=O)CI BSVMPWANOMFSPR-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
GTVVZTAFGPQSPC-UHFFFAOYSA-N 4-nitrophenylalanine Chemical compound OC(=O)C(N)CC1=CC=C([N+]([O-])=O)C=C1 GTVVZTAFGPQSPC-UHFFFAOYSA-N 0.000 description 1
BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
101100287595 Caenorhabditis elegans kin-2 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
206010056740 Genital discharge Diseases 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
102000000588 Interleukin-2 Human genes 0.000 description 1
108010002350 Interleukin-2 Proteins 0.000 description 1
102000010789 Interleukin-2 Receptors Human genes 0.000 description 1
108010038453 Interleukin-2 Receptors Proteins 0.000 description 1
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
QQINRWTZWGJFDB-UHFFFAOYSA-N actinium atom Chemical compound [Ac] QQINRWTZWGJFDB-UHFFFAOYSA-N 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
150000004705 aldimines Chemical class 0.000 description 1
OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000002981 blocking agent Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical group OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
150000004697 chelate complex Chemical class 0.000 description 1
125000003636 chemical group Chemical group 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
201000010099 disease Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
229940127121 immunoconjugate Drugs 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
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
238000002372 labelling Methods 0.000 description 1
229910021644 lanthanide ion Inorganic materials 0.000 description 1
RLJMLMKIBZAXJO-UHFFFAOYSA-N lead nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000004807 localization Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical group COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000011275 oncology therapy Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000047 product Substances 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
238000011362 radionuclide therapy Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000012475 sodium chloride buffer Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
238000001685 time-resolved fluorescence spectroscopy Methods 0.000 description 1
238000003325 tomography Methods 0.000 description 1
KOECRLKKXSXCPB-UHFFFAOYSA-K triiodobismuthane Chemical compound I[Bi](I)I KOECRLKKXSXCPB-UHFFFAOYSA-K 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
JUWHRRAPBUAYTA-UHFFFAOYSA-K yttrium(3+);triacetate Chemical class [Y+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JUWHRRAPBUAYTA-UHFFFAOYSA-K 0.000 description 1

Classifications

- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/534—Production of labelled immunochemicals with radioactive label
- 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
- 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
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/10—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody
- A61K51/1093—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody conjugates with carriers being antibodies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
- 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)
Chemical & Material Sciences (AREA)
Immunology (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Physics & Mathematics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Optics & Photonics (AREA)
Molecular Biology (AREA)
Biomedical Technology (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Cell Biology (AREA)
Pathology (AREA)
Biotechnology (AREA)
Food Science & Technology (AREA)
Analytical Chemistry (AREA)
Biochemistry (AREA)
General Physics & Mathematics (AREA)
Microbiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL9040989A 1988-05-25 1989-05-25 Acrylic Acids 2 Aralkyl - 1, 4, 7, 01 Tetraazacyclododecane - 'N, "N,"' N, "" N Tetraacetic acid, their preparation and medical use IL90409A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
IL11306889A IL113068A (en)	1988-05-25	1989-05-25	Acid Ligand-Haftan Acids of 1,4,7,01-Tetraazacyclododecane - N, (N,) N-Tetratic (

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US19853888A	1988-05-25	1988-05-25

Publications (2)

Publication Number	Publication Date
IL90409A0 IL90409A0 (en)	1990-01-18
IL90409A true IL90409A (en)	1996-09-12

Family

ID=22733797

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9040989A IL90409A (en)	1988-05-25	1989-05-25	Acrylic Acids 2 Aralkyl - 1, 4, 7, 01 Tetraazacyclododecane - 'N, "N,"' N, "" N Tetraacetic acid, their preparation and medical use

Country Status (9)

Country	Link
US (1)	US5428154A (ja)
EP (1)	EP0416033B1 (ja)
JP (2)	JPH0720989B2 (ja)
AT (1)	ATE134999T1 (ja)
AU (2)	AU630362B2 (ja)
CA (1)	CA1339015C (ja)
DE (1)	DE68925904T2 (ja)
IL (1)	IL90409A (ja)
WO (1)	WO1989011475A1 (ja)

Families Citing this family (66)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8719042D0 (en) *	1987-08-12	1987-09-16	Parker D	Conjugate compounds
CA1341373C (en) *	1988-06-24	2002-07-02	Roberta C. Cheng	Macrocyclic bifunctional chelants, complexes thereof and their antibody conjugates
GB9111199D0 (en) *	1991-05-23	1991-07-17	Sandoz Ltd	Improvements in or relating to organic compounds
US6139603A (en) *	1989-02-22	2000-10-31	L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude	Process for recovering oxygen
US5292868A (en) *	1989-05-26	1994-03-08	Akzo N.V.	Chelating agents for attaching metal ions to proteins
JPH04154729A (ja) *	1990-10-16	1992-05-27	Nippon Mejifuijitsukusu Kk	磁気共鳴造影剤
US6403771B1 (en)	1991-02-19	2002-06-11	Actinium Pharmaceuticals, Limited	Method and means for site directed therapy
JP2962883B2 (ja)	1991-07-02	1999-10-12	帝人株式会社	新規大環状キレート配位子およびその金属錯体
US6022966A (en) *	1993-11-22	2000-02-08	Neorx Corporation	Pretargeting methods and compounds
US5541287A (en) *	1992-06-09	1996-07-30	Neorx Corporation	Pretargeting methods and compounds
CA2100709C (en) *	1992-07-27	2004-03-16	Maurits W. Geerlings	Method and means for site directed therapy
DE69327760T2 (de) *	1992-07-31	2000-09-07	Australian Nuclear Science And Technology Organisation, Lucas Heights	Hydroxyaryl enthaltenden aminocarboxylsäure-chelatbildnern
US5807535A (en) *	1992-07-31	1998-09-15	Australian Nuclear Science & Technology Organisation	Metal complexes of hydroxyaryl containing aminocarboxylic acid chelating agents
US5650134A (en) *	1993-01-12	1997-07-22	Novartis Ag (Formerly Sandoz Ltd.)	Peptides
WO1995001346A1 (en) *	1993-06-30	1995-01-12	Akzo Nobel N.V.	Chelating compounds
CA2179990A1 (en) *	1994-01-12	1995-07-20	Gary Robert Bower	Biological targeting agents
US6693190B1 (en)	1994-05-11	2004-02-17	Bracco International B.V.	Enhanced relaxivity monomeric and multimeric compounds
GB9417873D0 (en) *	1994-09-06	1994-10-26	Sandoz Ltd	Organic compounds
US6770261B2 (en) *	1995-06-02	2004-08-03	Research Corporation Technologies	Magnetic resonance imaging agents for the detection of physiological agents
US5814521A (en) *	1995-10-06	1998-09-29	Bayer Corporation	Metal ion determination by sandwich aggregation assay
US7632651B2 (en)	1997-09-15	2009-12-15	Mds Analytical Technologies (Us) Inc.	Molecular modification assays
US6713046B1 (en) *	1997-10-27	2004-03-30	Research Corporation Technologies	Magnetic resonance imaging agents for the delivery of therapeutic agents
EP1032430A2 (en)	1997-11-17	2000-09-06	Research Corporation Technologies, Inc.	Magnetic resonance imaging agents for the detection of physiological agents
US6372187B1 (en)	1998-12-07	2002-04-16	Mcdermott Technology, Inc.	Alkaline sorbent injection for mercury control
US20020102208A1 (en)	1999-03-01	2002-08-01	Paul Chinn	Radiolabeling kit and binding assay
MY133346A (en)	1999-03-01	2007-11-30	Biogen Inc	Kit for radiolabeling ligands with yttrium-90
US6855859B2 (en) *	1999-03-31	2005-02-15	The Babcock & Wilcox Company	Method for controlling elemental mercury emissions
US6284199B1 (en) *	1999-03-31	2001-09-04	Mcdermott Technology, Inc.	Apparatus for control of mercury
US6328939B1 (en)	1999-03-31	2001-12-11	Mcdermott Technology, Inc.	Mercury removal in utility wet scrubber using a chelating agent
RU2260217C2 (ru)	1999-11-30	2005-09-10	Скотт ШЕНТЕР	Способ получения актиния-225 и его дочерних элементов
AU4906901A (en) *	2000-02-25	2001-09-17	Dangshe Ma	Actinium-225 complexes and conjugates for radioimmunotherapy
LU90544B1 (en) *	2000-03-14	2001-09-17	Europ Economic Community	Bifunctional chelating agent
US6565828B2 (en)	2000-04-07	2003-05-20	Bristol-Myers Squibb Company	Macrocyclic chelants for metallopharmaceuticals
US6683162B2 (en) *	2000-09-15	2004-01-27	Sloan Kettering Institute Of Cancer Research	Targeted alpha particle therapy using actinium-255 conjugates
US6517814B2 (en)	2001-01-09	2003-02-11	Bristol-Myers Squibb Pharma Company	Macrocyclic chelants useful for metallopharmaceuticals
AU2002254000A1 (en) *	2001-02-23	2002-09-12	Bristol-Myers Squibb Pharma Company	Labeled macrophage scavenger receptor antagonists for imaging atherosclerosis and vulnerable plaque
US20030004236A1 (en) *	2001-04-20	2003-01-02	Meade Thomas J.	Magnetic resonance imaging agents for detection and delivery of therapeutic agents and detection of physiological substances
US20030135108A1 (en) *	2001-05-02	2003-07-17	Silva Robin M.	High throughput screening methods using magnetic resonance imaging agents
WO2002087632A1 (en) *	2001-05-02	2002-11-07	Metaprobe, Inc.	High throughput screening methods using magnetic resonance imaging agents
AU2002350991A1 (en) *	2001-06-25	2003-01-08	The Government Of The United States Of America As Represented By The Secretary Of The Department Of	Macromolecular imaging agents for liver imaging
US20030198597A1 (en) *	2002-04-22	2003-10-23	Meade Thomas J.	Novel macrocyclic activatible magnetic resonance imaging contrast agents
US20030086868A1 (en) *	2002-08-12	2003-05-08	Dangshe Ma	Actinium-225 complexes and conjugates for radioimmunotherapy
CA2495442C (en)	2002-09-06	2013-12-10	Martin W. Brechbiel	Backbone-substituted bifunctional dota ligands, complexes and compositions thereof, and methods of using same
ES2581781T3 (es)	2002-09-24	2016-09-07	The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services	Método por imágenes para administración mejorada por convección de agentes terapéuticos
GB0308731D0 (en) *	2003-04-15	2003-05-21	Anticancer Therapeutic Inv Sa	Method of radiotherapy
ATE407176T1 (de)	2003-12-30	2008-09-15	Univ California Office Of The	Aromatische triamid-lanthanid-komplexe
US20050171424A1 (en) *	2004-01-13	2005-08-04	The Gov. Of The Usa As Rep. By The Secretary Of The Dept. Of Health And Human Services	Methods for imaging the lymphatic system using dendrimer-based contrast agents
WO2006039505A2 (en) *	2004-09-30	2006-04-13	Molecular Devices Corporation	Luminescent lanthanide complexes
US20060204443A1 (en) *	2005-03-11	2006-09-14	The Government Of The Usa As Represented By The Secretary Of The Dept. Of Health & Human Services	Methods for tumor treatment using dendrimer conjugates
US20070025910A1 (en)	2005-07-29	2007-02-01	Norenberg Jeffrey P	Anticancer therapy
US8557601B2 (en)	2006-07-10	2013-10-15	The Regents Of The University Of California	Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides
US8173800B2 (en) *	2006-08-15	2012-05-08	The Regents Of The University Of California	Luminescent macrocyclic lanthanide complexes
US8388936B2 (en) *	2008-02-22	2013-03-05	Mcw Research Foundation, Inc.	In vivo mitochondrial labeling using positively-charged nitroxide enhanced and gadolinium chelate enhanced magnetic resonance imaging
US8388931B2 (en)	2008-02-29	2013-03-05	Marcos Lopez	99m Tc-labeled triphenylphosphonium derivative contrasting agents and molecular probes for early detection and imaging of breast tumors
WO2010014179A1 (en)	2008-07-31	2010-02-04	Duke University	Photolabile caged transition metal complexes and methods of using the same
CN104710504B (zh)	2009-07-22	2019-09-13	锕医药股份有限公司	用于制备放射性免疫缀合物的方法
WO2011025790A1 (en)	2009-08-24	2011-03-03	Lumiphore, Inc.	Macrocyclic hopo chelators
GB201002508D0 (en)	2010-02-12	2010-03-31	Algeta As	Product
KR101253100B1 (ko) *	2010-02-16	2013-04-10	경북대학교 산학협력단	폴리아자마크로사이클릭 화합물, 그 제조 방법 및 생의학적 적용
US11453652B2 (en)	2013-03-15	2022-09-27	Lumiphore, Inc.	Di-macrocycles
FR3006688B1 (fr) *	2013-06-06	2015-08-14	Centre Nat Rech Scient	Chelates du plomb (ii) et du bismuth (iii) a base de tetraazacycloalcanes trans-di-n-picolinates
SG11201706849SA (en) *	2015-02-26	2017-09-28	Sciencons AS	Radiopharmaceutical solutions with advantageous properties
CN105807055B (zh) *	2016-03-15	2017-10-10	中国烟草总公司郑州烟草研究院	一种检测二氯喹啉酸的试纸条及其制备方法和应用
EP3409297A1 (en)	2017-05-30	2018-12-05	AlfaRim Medial Holding B.V.	The optimal 225actinium--213bismuth generator for alpha-particle radioimmunotherapy
WO2019057598A1 (en)	2017-09-20	2019-03-28	Alfarim Medical Holding B.V.	OPTIMAL 225ACTINIUM - 213BISMUTH GENERATOR FOR ALPHA PARTICLE RADIO IMMUNOTHERAPY
KR20230173150A (ko)	2021-04-20	2023-12-26	테라파워, 엘엘씨	Ac-225 생성용 티타니아 기반 발생기

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2186464A (en) *	1939-10-18	1940-01-09	Alframine Corp	Condensation product and method of preparing same
US3860576A (en) *	1972-04-26	1975-01-14	Dow Chemical Co	N-substituted-tetra-azacyclotetradecanes
US3936445A (en) *	1973-07-04	1976-02-03	Badische Anilin- & Soda-Fabrik Aktiengesellschaft	Process for the production of iron complexes of tetraazaannulenes
US3979379A (en) *	1975-04-25	1976-09-07	The United States Of America As Represented By The Secretary Of The Army	Process for producing 1,3,5,7-tetraalkanoyl-1,3,5,7-octahydrotetrazocines
DE2803528C2 (de) *	1977-03-09	1984-10-18	Tabushi, Iwao, Kyoto	Schwermetallionen-Adsorbens und dessen Verwendung zum Adsorbieren von Schwermetallionen
JPS53144592A (en) *	1977-05-19	1978-12-15	Tabuse Iwao	122alkyll147*100tetrazacyclotridecane
GB1529150A (en) *	1977-05-17	1978-10-18	Tabushi I	Alkyl substituted cyclic alkyltetramines
US4543213A (en) *	1978-07-24	1985-09-24	The United States Of America As Represented By The United States Department Of Energy	Process for preparing 2,3-dihydroxybenzoic acid amides of tetraazaalkanes and cycloalkanes
US4578517A (en) *	1983-09-16	1986-03-25	Air Products And Chemicals, Inc.	Polyalkylene polyamines from alkanolamine and ammonia or amines using group IIIB metal acid phosphate catalysts
JPS61226751A (ja) *	1985-03-30	1986-10-08	Konishiroku Photo Ind Co Ltd	ハロゲン化銀写真感光材料用処理液及びその処理方法
US4678667A (en) *	1985-07-02	1987-07-07	501 Regents of the University of California	Macrocyclic bifunctional chelating agents
US4885363A (en) *	1987-04-24	1989-12-05	E. R. Squibb & Sons, Inc.	1-substituted-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs
GB8603537D0 (en) *	1986-02-13	1986-03-19	Parker D	Conjugate compound
DE3625417C2 (de) *	1986-07-28	1998-10-08	Schering Ag	Tetraazacyclododecan-Derivate
US5132409A (en) *	1987-01-12	1992-07-21	Bracco Industria Chimica S.P.A.	Macrocyclic chelating agents and chelates thereof
US5049667A (en) *	1987-04-14	1991-09-17	Guerbet S.A.	Nitrogen-containing cyclic ligands
DE3713842A1 (de) *	1987-04-22	1988-11-17	Schering Ag	Substituierte cyclische komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel
US5064956A (en) *	1987-06-24	1991-11-12	The Dow Chemical Company	Process for preparing mono-n-alkylated polyazamacrocycles
GB8719042D0 (en) *	1987-08-12	1987-09-16	Parker D	Conjugate compounds
US4923985A (en) *	1988-05-25	1990-05-08	The United States Of America As Represented By The Department Of Health & Human Services	Process for synthesizing macrocyclic chelates
US4987227A (en) *	1988-10-21	1991-01-22	The Research Foundation Of State University Of New York	Polyazamacrocycles and their metal complexes
US5053503A (en) *	1989-02-17	1991-10-01	Centocor	Chelating agents

1989
- 1989-05-24 JP JP1507105A patent/JPH0720989B2/ja not_active Expired - Fee Related
- 1989-05-24 AU AU38428/89A patent/AU630362B2/en not_active Ceased
- 1989-05-24 DE DE68925904T patent/DE68925904T2/de not_active Expired - Fee Related
- 1989-05-24 EP EP89907438A patent/EP0416033B1/en not_active Expired - Lifetime
- 1989-05-24 AT AT89907438T patent/ATE134999T1/de not_active IP Right Cessation
- 1989-05-24 WO PCT/US1989/002201 patent/WO1989011475A1/en not_active Ceased
- 1989-05-25 CA CA000600714A patent/CA1339015C/en not_active Expired - Fee Related
- 1989-05-25 IL IL9040989A patent/IL90409A/en active IP Right Grant
1993
- 1993-01-28 AU AU32108/93A patent/AU655704B2/en not_active Ceased
- 1993-10-22 US US08/140,714 patent/US5428154A/en not_active Expired - Lifetime
1994
- 1994-07-11 JP JP6181867A patent/JP2582341B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US5428154A (en)	1995-06-27
JPH07258281A (ja)	1995-10-09
AU3842889A (en)	1989-12-12
WO1989011475A1 (en)	1989-11-30
AU3210893A (en)	1993-04-01
JP2582341B2 (ja)	1997-02-19
IL90409A0 (en)	1990-01-18
CA1339015C (en)	1997-03-25
DE68925904T2 (de)	1996-10-31
EP0416033B1 (en)	1996-03-06
EP0416033A4 (en)	1991-04-17
JPH0720989B2 (ja)	1995-03-08
AU630362B2 (en)	1992-10-29
EP0416033A1 (en)	1991-03-13
JPH03503531A (ja)	1991-08-08
DE68925904D1 (de)	1996-04-11
ATE134999T1 (de)	1996-03-15
AU655704B2 (en)	1995-01-05

Legal Events

Date	Code	Title
1997-02-18	FF	Patent granted
1997-11-20	KB	Patent renewed
1999-11-30	KB	Patent renewed
2003-07-31	KB	Patent renewed
2007-08-19	KB	Patent renewed

Publication	Publication Date	Title
US5428154A (en)	1995-06-27	Complexes of functionalized tetraazacyclododecane chelates with bismuth, lead, ytriium, actinium, or lanthanide metal ions
US5583219A (en)	1996-12-10	Macrocyclic chelating agent
JP3292301B2 (ja)	2002-06-17	治療用及び診断用撮像組成物及び方法において役立つ錯化剤及びターゲティング放射性免疫試薬
CA2487908C (en)	2013-02-12	Scorpionate-like pendant macrocyclic ligands, complexes and compositions thereof, and methods of using same
JPH07504661A (ja)	1995-05-25	放射免疫イメージング及び放射免疫療法に関するビオチン及びデフェロキサミンのコンジュゲート
CA2495442C (en)	2013-12-10	Backbone-substituted bifunctional dota ligands, complexes and compositions thereof, and methods of using same
AU625529B2 (en)	1992-07-16	10-(2'-hydroxy-3'-alkoxy-1,4,7-triscarboxymethyl-1,4,7,10- tetraazacyclododecanes
AU638757B2 (en)	1993-07-08	Chelating agents for attaching metal ions to proteins
CA2079206A1 (en)	1991-09-27	Fonctionalized complexand
IL113068A (en)	1996-11-14	Acid Ligand-Haftan Acids of 1,4,7,01-Tetraazacyclododecane - N, (N,) N-Tetratic (
JPH06505795A (ja)	1994-06-30	キレート化剤
JPH05320147A (ja)	1993-12-03	ペンダント型二官能性大環状キレート配位子、その製造法および金属錯体
DE69327760T2 (de)	2000-09-07	Hydroxyaryl enthaltenden aminocarboxylsäure-chelatbildnern
JP2962883B2 (ja)	1999-10-12	新規大環状キレート配位子およびその金属錯体
EP0354543A1 (en)	1990-02-14	Photochemical attachment of chelating groups to biomolecules
JPH09507488A (ja)	1997-07-29	新規なポリアミノカルボキシレートキレート化剤