AU2010336403B2 - Radiopharmaceutical complexes - Google Patents
Radiopharmaceutical complexes Download PDFInfo
- Publication number
- AU2010336403B2 AU2010336403B2 AU2010336403A AU2010336403A AU2010336403B2 AU 2010336403 B2 AU2010336403 B2 AU 2010336403B2 AU 2010336403 A AU2010336403 A AU 2010336403A AU 2010336403 A AU2010336403 A AU 2010336403A AU 2010336403 B2 AU2010336403 B2 AU 2010336403B2
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- Australia
- Prior art keywords
- substituted
- unsubstituted
- complex
- alkyl
- linker
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000012217 radiopharmaceutical Substances 0.000 title description 3
- 229940121896 radiopharmaceutical Drugs 0.000 title description 3
- 230000002799 radiopharmaceutical effect Effects 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 126
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 230000008685 targeting Effects 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 125000000524 functional group Chemical group 0.000 claims description 37
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- 108091034117 Oligonucleotide Proteins 0.000 claims description 7
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 102000008394 Immunoglobulin Fragments Human genes 0.000 claims description 5
- 108010021625 Immunoglobulin Fragments Proteins 0.000 claims description 5
- 229910052776 Thorium Inorganic materials 0.000 claims description 5
- 108020004707 nucleic acids Proteins 0.000 claims description 4
- 150000007523 nucleic acids Chemical class 0.000 claims description 4
- 102000039446 nucleic acids Human genes 0.000 claims description 4
- 229920001184 polypeptide Polymers 0.000 claims description 4
- 239000005556 hormone Substances 0.000 claims description 3
- 229940088597 hormone Drugs 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 150000003384 small molecules Chemical class 0.000 claims description 3
- 229910052767 actinium Inorganic materials 0.000 claims description 2
- 229940125666 actinium-225 Drugs 0.000 claims description 2
- 230000001668 ameliorated effect Effects 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 239000002738 chelating agent Substances 0.000 abstract description 75
- 150000001875 compounds Chemical class 0.000 abstract description 63
- 229910021645 metal ion Inorganic materials 0.000 abstract description 20
- 230000001225 therapeutic effect Effects 0.000 abstract description 8
- 125000005647 linker group Chemical group 0.000 description 98
- -1 terephthalamidyl Chemical class 0.000 description 78
- 239000000243 solution Substances 0.000 description 56
- 238000006243 chemical reaction Methods 0.000 description 46
- 239000003446 ligand Substances 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 26
- 239000002184 metal Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 125000005842 heteroatom Chemical group 0.000 description 23
- 125000001424 substituent group Chemical group 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 150000001768 cations Chemical class 0.000 description 22
- 108090000623 proteins and genes Proteins 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 102000004169 proteins and genes Human genes 0.000 description 19
- 235000018102 proteins Nutrition 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000011324 bead Substances 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 125000003396 thiol group Chemical group [H]S* 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000007792 addition Methods 0.000 description 10
- 125000001188 haloalkyl group Chemical group 0.000 description 10
- 238000004949 mass spectrometry Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 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 9
- 239000002585 base Substances 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052768 actinide Inorganic materials 0.000 description 8
- 239000013522 chelant Substances 0.000 description 8
- 238000013461 design Methods 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- GQZXNSPRSGFJLY-UHFFFAOYSA-N hydroxyphosphanone Chemical group OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- WLRWZFFZBGHMBU-UHFFFAOYSA-N 48,49,63,64-tetramethoxy-1,4,7,15,18,21,24,32,37,45,52,60-dodecazaheptacyclo[19.13.13.134,18.19,13.126,30.139,43.154,58]tetrahexaconta-9(63),10,12,26,28,30(49),39(48),40,42,54,56,58(64)-dodecaene-8,14,25,31,38,44,53,59-octone Chemical compound COC1=C(C(NCCN(CCNC2=O)CCN3CCNC(=O)C=4C=CC=C(C=4OC)C(=O)NCCN(CCNC(=O)C=4C=CC=C(C=4OC)C(=O)NCC3)CC3)=O)C=CC=C1C(=O)NCCN3CCNC(=O)C1=CC=CC2=C1OC WLRWZFFZBGHMBU-UHFFFAOYSA-N 0.000 description 7
- 108020004414 DNA Proteins 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000010668 complexation reaction Methods 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 150000003141 primary amines Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 238000010494 dissociation reaction Methods 0.000 description 6
- 230000005593 dissociations Effects 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 150000002463 imidates Chemical class 0.000 description 6
- 229910052747 lanthanoid Inorganic materials 0.000 description 6
- 150000002602 lanthanoids Chemical class 0.000 description 6
- 238000006303 photolysis reaction Methods 0.000 description 6
- 230000015843 photosynthesis, light reaction Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 150000001255 actinides Chemical class 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000001502 gel electrophoresis Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- KUWKQASGHNTJAT-UHFFFAOYSA-N 1-hydroxy-n-[3-[(1-hydroxy-6-oxopyridine-2-carbonyl)-[4-[(1-hydroxy-6-oxopyridine-2-carbonyl)-[3-[(1-hydroxy-6-oxopyridine-2-carbonyl)amino]propyl]amino]butyl]amino]propyl]-6-oxopyridine-2-carboxamide Chemical compound C1=CC(=O)N(O)C(C(=O)NCCCN(CCCCN(CCCNC(=O)C=2N(C(=O)C=CC=2)O)C(=O)C=2N(C(=O)C=CC=2)O)C(=O)C=2N(C(=O)C=CC=2)O)=C1 KUWKQASGHNTJAT-UHFFFAOYSA-N 0.000 description 4
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical compound SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000001268 conjugating effect Effects 0.000 description 4
- 150000002019 disulfides Chemical class 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 230000000269 nucleophilic effect Effects 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
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- 241000894007 species Species 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- 210000000988 bone and bone Anatomy 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
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- 150000002170 ethers Chemical class 0.000 description 3
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
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- ICGQLNMKJVHCIR-UHFFFAOYSA-N 1,3,2-dioxazetidin-4-one Chemical compound O=C1ONO1 ICGQLNMKJVHCIR-UHFFFAOYSA-N 0.000 description 2
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- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
- PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 description 2
- ASFLKOQYRQNIKJ-UHFFFAOYSA-N 5-acetyloxy-1-hydroxy-6-oxopyridine-2-carboxylic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)N(O)C1=O ASFLKOQYRQNIKJ-UHFFFAOYSA-N 0.000 description 2
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- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
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- 238000003556 assay Methods 0.000 description 2
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 230000009920 chelation Effects 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nuclear Medicine (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29015509P | 2009-12-24 | 2009-12-24 | |
| US61/290,155 | 2009-12-24 | ||
| PCT/US2010/062048 WO2011079291A1 (en) | 2009-12-24 | 2010-12-23 | Radiopharmaceutical complexes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2010336403A1 AU2010336403A1 (en) | 2012-06-28 |
| AU2010336403B2 true AU2010336403B2 (en) | 2016-04-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010336403A Active AU2010336403B2 (en) | 2009-12-24 | 2010-12-23 | Radiopharmaceutical complexes |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US20110189088A1 (cg-RX-API-DMAC7.html) |
| EP (2) | EP2516407A4 (cg-RX-API-DMAC7.html) |
| JP (4) | JP2013515744A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2010336403B2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011079291A1 (cg-RX-API-DMAC7.html) |
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| EP2511266B1 (en) | 2006-07-10 | 2019-09-04 | The Regents of The University of California | Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides |
| US9273059B2 (en) | 2009-08-24 | 2016-03-01 | Lumiphore, Inc. | Macrocyclic HOPO chelators |
| GB201002508D0 (en) * | 2010-02-12 | 2010-03-31 | Algeta As | Product |
| GB201208309D0 (en) * | 2012-05-11 | 2012-06-27 | Algeta As | Complexes |
| AU2013344514B2 (en) * | 2012-11-16 | 2017-09-14 | Lumiphore, Inc. | Di-Macrocycles |
| US11453652B2 (en) | 2013-03-15 | 2022-09-27 | Lumiphore, Inc. | Di-macrocycles |
| CA2945034C (en) * | 2014-04-09 | 2024-03-05 | Lumiphore, Inc. | Macrocycles with chelating moieties for diagnostic and therapeutic use |
| EP3237429A4 (en) * | 2014-12-22 | 2018-08-15 | Lumiphore, Inc. | Functionalized linear ligands and complexes thereof |
| CN109689115A (zh) * | 2016-06-10 | 2019-04-26 | 拜耳制药股份公司 | 放射性药物配合物 |
| US11235076B2 (en) | 2016-08-29 | 2022-02-01 | Fred Hutchinson Cancer Research Center | Chelating platform for delivery of radionuclides |
| WO2018130988A1 (en) * | 2017-01-12 | 2018-07-19 | Nestec S.A. | Cryptate derivatives and their use as luminescent lanthanide complexes |
| WO2019246311A1 (en) * | 2018-06-19 | 2019-12-26 | Lumiphore, Inc. | Macrocycle conjugates |
| WO2020086629A1 (en) * | 2018-10-22 | 2020-04-30 | The General Hospital Corporation | Complexes and ligands |
| JP2024045789A (ja) * | 2021-02-19 | 2024-04-03 | 住友化学株式会社 | 化合物及び金属錯体 |
| JP2024060110A (ja) * | 2021-02-19 | 2024-05-02 | 住友化学株式会社 | 放射性金属錯体及びその製造方法 |
| CN117180277A (zh) * | 2023-08-04 | 2023-12-08 | 中国辐射防护研究院 | 一种核素标记的靶向探针及其制备方法和应用 |
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| JP2013515744A (ja) | 2013-05-09 |
| EP2516407A1 (en) | 2012-10-31 |
| US20110189088A1 (en) | 2011-08-04 |
| JP2021006542A (ja) | 2021-01-21 |
| EP3263562A1 (en) | 2018-01-03 |
| AU2010336403A1 (en) | 2012-06-28 |
| JP2017119705A (ja) | 2017-07-06 |
| WO2011079291A1 (en) | 2011-06-30 |
| EP2516407A4 (en) | 2013-06-12 |
| JP2019052164A (ja) | 2019-04-04 |
| US20200024234A1 (en) | 2020-01-23 |
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