DK168920B1 - Boronsyreaddukter af technetium-99m-dioxim-komplekser samt sæt anvendeligt til addukternes fremstilling - Google Patents
Boronsyreaddukter af technetium-99m-dioxim-komplekser samt sæt anvendeligt til addukternes fremstilling Download PDFInfo
- Publication number
- DK168920B1 DK168920B1 DK169086A DK169086A DK168920B1 DK 168920 B1 DK168920 B1 DK 168920B1 DK 169086 A DK169086 A DK 169086A DK 169086 A DK169086 A DK 169086A DK 168920 B1 DK168920 B1 DK 168920B1
- Authority
- DK
- Denmark
- Prior art keywords
- boronic acid
- 99mtc
- dimethylglyoxime
- dioxime
- chlorine
- Prior art date
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- 150000001642 boronic acid derivatives Chemical class 0.000 title claims abstract description 16
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 title abstract description 9
- 229940056501 technetium 99m Drugs 0.000 title abstract description 8
- PGBQRWOYUWEHBV-UHFFFAOYSA-N CC(C(=NO)C)=NO.[Cl] Chemical compound CC(C(=NO)C)=NO.[Cl] PGBQRWOYUWEHBV-UHFFFAOYSA-N 0.000 claims description 47
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical group O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 claims description 34
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 30
- CUNNCKOPAWXYDX-SFECMWDFSA-N (NZ)-N-[(2Z)-2-hydroxyiminocyclohexylidene]hydroxylamine Chemical group O\N=C/1\CCCC\C\1=N\O CUNNCKOPAWXYDX-SFECMWDFSA-N 0.000 claims description 29
- -1 halogen anion Chemical group 0.000 claims description 29
- 229910052796 boron Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- LJHFIVQEAFAURQ-UHFFFAOYSA-N glyoxime Chemical group ON=CC=NO LJHFIVQEAFAURQ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- RBOZTFPIXJBLPK-WGDLNXRISA-N (NZ)-N-[(2Z)-1,2-bis(furan-2-yl)-2-hydroxyiminoethylidene]hydroxylamine Chemical group O\N=C(\C(=N\O)\c1ccco1)/c1ccco1 RBOZTFPIXJBLPK-WGDLNXRISA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical compound [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- OYVWGNWQQULBOK-UHFFFAOYSA-N N-(2-hydroxyimino-3-methylcyclopentylidene)hydroxylamine Chemical compound CC1CCC(=NO)C1=NO OYVWGNWQQULBOK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- 150000001805 chlorine compounds Chemical group 0.000 claims 2
- IPCKGVFARIEVOF-UHFFFAOYSA-N (3-hydroxyiminobutan-2-ylideneamino) hypochlorite Chemical compound ClON=C(C(=NO)C)C IPCKGVFARIEVOF-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000003384 imaging method Methods 0.000 abstract description 3
- 210000004369 blood Anatomy 0.000 abstract description 2
- 239000008280 blood Substances 0.000 abstract description 2
- 210000004556 brain Anatomy 0.000 abstract description 2
- 210000004165 myocardium Anatomy 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 65
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 30
- 239000004327 boric acid Substances 0.000 description 30
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 17
- 239000002504 physiological saline solution Substances 0.000 description 17
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 17
- 229910052708 sodium Inorganic materials 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- FVYCCDTZIKBWFR-UHFFFAOYSA-N Cl.OBO.CCCN1CCCCC1 Chemical compound Cl.OBO.CCCN1CCCCC1 FVYCCDTZIKBWFR-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 210000002966 serum Anatomy 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- KTMKRRPZPWUYKK-UHFFFAOYSA-N methylboronic acid Chemical group CB(O)O KTMKRRPZPWUYKK-UHFFFAOYSA-N 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 7
- QPKFVRWIISEVCW-UHFFFAOYSA-N 1-butane boronic acid Chemical compound CCCCB(O)O QPKFVRWIISEVCW-UHFFFAOYSA-N 0.000 description 6
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 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 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
- WNDZGSZAABWBMU-UHFFFAOYSA-N hydroxyboron Chemical compound O[B] WNDZGSZAABWBMU-UHFFFAOYSA-N 0.000 description 5
- PLFLRQISROSEIJ-UHFFFAOYSA-N methylborane Chemical compound CB PLFLRQISROSEIJ-UHFFFAOYSA-N 0.000 description 5
- 229960003330 pentetic acid Drugs 0.000 description 5
- 239000001119 stannous chloride Substances 0.000 description 5
- 235000011150 stannous chloride Nutrition 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000008139 complexing agent Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PDNOURKEZJZJNZ-UHFFFAOYSA-N [4-(bromomethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(CBr)C=C1 PDNOURKEZJZJNZ-UHFFFAOYSA-N 0.000 description 3
- RKLSGKOUKYOIRM-UHFFFAOYSA-N butylboron Chemical compound [B]CCCC RKLSGKOUKYOIRM-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000002872 contrast media Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RZCPLOMUUCFPQA-UHFFFAOYSA-N (4-ethylphenyl)boronic acid Chemical compound CCC1=CC=C(B(O)O)C=C1 RZCPLOMUUCFPQA-UHFFFAOYSA-N 0.000 description 2
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 2
- FFNOLGPNGDYELU-UHFFFAOYSA-N 3-piperidin-1-ylpropylboron Chemical compound [B]CCCN1CCCCC1 FFNOLGPNGDYELU-UHFFFAOYSA-N 0.000 description 2
- GMBWGWDCLCOUCC-UHFFFAOYSA-N 3-piperidin-1-ylpropylboronic acid;hydrochloride Chemical compound Cl.OB(O)CCCN1CCCCC1 GMBWGWDCLCOUCC-UHFFFAOYSA-N 0.000 description 2
- NQNWUOIKNUCRIO-UHFFFAOYSA-N Cl.B(O)O.C1(=CC=CC=C1)C1CCN(CC1)CCC Chemical compound Cl.B(O)O.C1(=CC=CC=C1)C1CCN(CC1)CCC NQNWUOIKNUCRIO-UHFFFAOYSA-N 0.000 description 2
- TUMDVIICFOJWFI-UHFFFAOYSA-N Cl.B(O)O.N1(CCOCC1)CCC Chemical compound Cl.B(O)O.N1(CCOCC1)CCC TUMDVIICFOJWFI-UHFFFAOYSA-N 0.000 description 2
- MCGDKLYFOKQSHW-UHFFFAOYSA-N Cl.OBO.CCN(CC)CC1=CC=CC=C1 Chemical group Cl.OBO.CCN(CC)CC1=CC=CC=C1 MCGDKLYFOKQSHW-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- ZTBIQJONGXVDJZ-UHFFFAOYSA-N N-(2-hydroxyiminocyclopentylidene)hydroxylamine Chemical compound ON=C1CCCC1=NO ZTBIQJONGXVDJZ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical group CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- HLTGMLMEOOAYKB-UHFFFAOYSA-N [3-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]phenyl]boron Chemical compound [B]C1=CC=CC(NS(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)=C1 HLTGMLMEOOAYKB-UHFFFAOYSA-N 0.000 description 2
- DPRMFUAMSRXGDE-UHFFFAOYSA-N ac1o530g Chemical compound NCCN.NCCN DPRMFUAMSRXGDE-UHFFFAOYSA-N 0.000 description 2
- UADDLHRDLMMBQG-UHFFFAOYSA-N butoxyboron Chemical compound [B]OCCCC UADDLHRDLMMBQG-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000002059 diagnostic imaging Methods 0.000 description 2
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- IXNQLZLJLCEBTF-UHFFFAOYSA-N heptylboron Chemical compound [B]CCCCCCC IXNQLZLJLCEBTF-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical group CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000012216 imaging agent Substances 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- BZXQRXJJJUZZAJ-UHFFFAOYSA-N (2,4,6-trimethylphenyl)boronic acid Chemical compound CC1=CC(C)=C(B(O)O)C(C)=C1 BZXQRXJJJUZZAJ-UHFFFAOYSA-N 0.000 description 1
- TYONHSPZXLFWKI-UHFFFAOYSA-N (2,4-dimethylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C(C)=C1 TYONHSPZXLFWKI-UHFFFAOYSA-N 0.000 description 1
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- BFYQWGBTSXFZLY-UHFFFAOYSA-N (3-aminophenyl)boron Chemical compound [B]C1=CC=CC(N)=C1 BFYQWGBTSXFZLY-UHFFFAOYSA-N 0.000 description 1
- NBMYFZIWNCAUJL-UHFFFAOYSA-N (3-hydroxyiminobutan-2-ylideneamino) hypofluorite Chemical compound FON=C(C(=NO)C)C NBMYFZIWNCAUJL-UHFFFAOYSA-N 0.000 description 1
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 1
- YXOMVJFDRYZYNZ-UHFFFAOYSA-N 10-boronodecanoic acid Chemical compound OB(O)CCCCCCCCCC(O)=O YXOMVJFDRYZYNZ-UHFFFAOYSA-N 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- JQPFYXFVUKHERX-UHFFFAOYSA-N 2-hydroxy-2-cyclohexen-1-one Natural products OC1=CCCCC1=O JQPFYXFVUKHERX-UHFFFAOYSA-N 0.000 description 1
- ZAZPDOYUCVFPOI-UHFFFAOYSA-N 2-methylpropylboronic acid Chemical compound CC(C)CB(O)O ZAZPDOYUCVFPOI-UHFFFAOYSA-N 0.000 description 1
- UGPDFTILZFNUMH-UHFFFAOYSA-N 3-(4-benzylpiperidin-1-yl)propylboron Chemical compound C1CN(CCC[B])CCC1CC1=CC=CC=C1 UGPDFTILZFNUMH-UHFFFAOYSA-N 0.000 description 1
- FHKSQHHISLPSSG-UHFFFAOYSA-N 3-[methyl(2-phenylethyl)amino]propylboron Chemical compound [B]CCCN(C)CCC1=CC=CC=C1 FHKSQHHISLPSSG-UHFFFAOYSA-N 0.000 description 1
- XSUJWDLJOMBWKI-UHFFFAOYSA-N 4-hydroxybut-1-enylboronic acid Chemical compound OCCC=CB(O)O XSUJWDLJOMBWKI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XMYPZYMWZHRLSU-UHFFFAOYSA-N 9-carboxynonylboron Chemical compound [B]CCCCCCCCCC(O)=O XMYPZYMWZHRLSU-UHFFFAOYSA-N 0.000 description 1
- CCFHMBKOKCJAOQ-UHFFFAOYSA-N C1CC(CC1)[B].CC(C(=NO)C)=NO.[Cl] Chemical compound C1CC(CC1)[B].CC(C(=NO)C)=NO.[Cl] CCFHMBKOKCJAOQ-UHFFFAOYSA-N 0.000 description 1
- ALCGNBWZCDFSAG-UHFFFAOYSA-N CC(C(=NO)C)=NO.[Br] Chemical compound CC(C(=NO)C)=NO.[Br] ALCGNBWZCDFSAG-UHFFFAOYSA-N 0.000 description 1
- HSTUZNTUPWCCSW-UHFFFAOYSA-N CC(C(=NO)C)=NO.[I] Chemical compound CC(C(=NO)C)=NO.[I] HSTUZNTUPWCCSW-UHFFFAOYSA-N 0.000 description 1
- MWLBFFTXFBHHFD-UHFFFAOYSA-N CCCO[B].CC(C(=NO)C)=NO.[Cl] Chemical compound CCCO[B].CC(C(=NO)C)=NO.[Cl] MWLBFFTXFBHHFD-UHFFFAOYSA-N 0.000 description 1
- WRAOHUDMTNSCMP-UHFFFAOYSA-N Cl.B(O)O.C(C)(C)N(C(C)C)CC1=CC=CC=C1 Chemical compound Cl.B(O)O.C(C)(C)N(C(C)C)CC1=CC=CC=C1 WRAOHUDMTNSCMP-UHFFFAOYSA-N 0.000 description 1
- USNAOQJTAQRJJN-UHFFFAOYSA-N Cl.B(O)O.C(C)(C)NCC1=CC=CC=C1 Chemical compound Cl.B(O)O.C(C)(C)NCC1=CC=CC=C1 USNAOQJTAQRJJN-UHFFFAOYSA-N 0.000 description 1
- QOPODYGDMJBGAO-UHFFFAOYSA-N Cl.B(O)O.C1=CC=CC=C1 Chemical compound Cl.B(O)O.C1=CC=CC=C1 QOPODYGDMJBGAO-UHFFFAOYSA-N 0.000 description 1
- ZTVHNYDNRYRGHJ-UHFFFAOYSA-N Cl.B(O)O.CCC Chemical compound Cl.B(O)O.CCC ZTVHNYDNRYRGHJ-UHFFFAOYSA-N 0.000 description 1
- YYTSDGFZRKPZBX-UHFFFAOYSA-N Cl.B(O)O.CN(CCC1=CC=CC=C1)CC1=CC=CC=C1 Chemical compound Cl.B(O)O.CN(CCC1=CC=CC=C1)CC1=CC=CC=C1 YYTSDGFZRKPZBX-UHFFFAOYSA-N 0.000 description 1
- WUYSVDMKPDGYBM-UHFFFAOYSA-N Cl.OBO.C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC1=CC=CC=C1 Chemical compound Cl.OBO.C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC1=CC=CC=C1 WUYSVDMKPDGYBM-UHFFFAOYSA-N 0.000 description 1
- GYSSUQGFQJWJRS-UHFFFAOYSA-N Cl.OBO.CCCN1CCC(C)CC1 Chemical compound Cl.OBO.CCCN1CCC(C)CC1 GYSSUQGFQJWJRS-UHFFFAOYSA-N 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- LJIRXNPXTVQOEU-UHFFFAOYSA-N N-(2-hydroxyiminocycloheptylidene)hydroxylamine Chemical compound ON=C1CCCCCC1=NO LJIRXNPXTVQOEU-UHFFFAOYSA-N 0.000 description 1
- NYAPJROFUGTEBD-UHFFFAOYSA-N OBO.C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC1=CC=CC=C1 Chemical compound OBO.C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC1=CC=CC=C1 NYAPJROFUGTEBD-UHFFFAOYSA-N 0.000 description 1
- XPZWXOHCSBVZLP-UHFFFAOYSA-N OBO.CC(C)N(C(C)C)C(C)C1=CC=CC=C1 Chemical compound OBO.CC(C)N(C(C)C)C(C)C1=CC=CC=C1 XPZWXOHCSBVZLP-UHFFFAOYSA-N 0.000 description 1
- IFUPJCWLBCASMC-UHFFFAOYSA-N OBO.CCCC Chemical compound OBO.CCCC IFUPJCWLBCASMC-UHFFFAOYSA-N 0.000 description 1
- FZJLWFWBAWPGRI-UHFFFAOYSA-N OBO.CCCN(C)CCC1=CC=CC=C1 Chemical compound OBO.CCCN(C)CCC1=CC=CC=C1 FZJLWFWBAWPGRI-UHFFFAOYSA-N 0.000 description 1
- QVHSOQPTLWLLSG-UHFFFAOYSA-N [4-(butoxymethyl)phenyl]boron Chemical compound [B]C1=CC=C(COCCCC)C=C1 QVHSOQPTLWLLSG-UHFFFAOYSA-N 0.000 description 1
- XQIKVOZXVZVDFM-UHFFFAOYSA-N [4-(diethylaminomethyl)phenyl]boronic acid;hydrochloride Chemical compound Cl.CCN(CC)CC1=CC=C(B(O)O)C=C1 XQIKVOZXVZVDFM-UHFFFAOYSA-N 0.000 description 1
- PBSZNYXNKQJGRY-UHFFFAOYSA-N [4-(methoxymethyl)phenyl]boron Chemical compound [B]C1=CC=C(COC)C=C1 PBSZNYXNKQJGRY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- ZUVQXWUBMQNMGL-UHFFFAOYSA-N butan-2-ylboron Chemical compound [B]C(C)CC ZUVQXWUBMQNMGL-UHFFFAOYSA-N 0.000 description 1
- MACOIFNUPFKZEI-UHFFFAOYSA-N butan-2-ylboronic acid Chemical compound CCC(C)B(O)O MACOIFNUPFKZEI-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- VTTDFSNKIMAQTB-UHFFFAOYSA-N cyclopentylboronic acid Chemical compound OB(O)C1CCCC1 VTTDFSNKIMAQTB-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- MXWVIHZQMUONMP-UHFFFAOYSA-N ethoxyboron Chemical compound [B]OCC MXWVIHZQMUONMP-UHFFFAOYSA-N 0.000 description 1
- FUUMXQXWOPLYQU-UHFFFAOYSA-N ethyl(phenyl)boron Chemical compound CC[B]C1=CC=CC=C1 FUUMXQXWOPLYQU-UHFFFAOYSA-N 0.000 description 1
- VABNKPWLESVOJG-UHFFFAOYSA-N ethylboron Chemical compound [B]CC VABNKPWLESVOJG-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- NLVUJNFGANISEC-UHFFFAOYSA-N hexadecylboron Chemical compound [B]CCCCCCCCCCCCCCCC NLVUJNFGANISEC-UHFFFAOYSA-N 0.000 description 1
- XQIYHMNEFXWVAX-UHFFFAOYSA-N hexadecylboronic acid Chemical compound CCCCCCCCCCCCCCCCB(O)O XQIYHMNEFXWVAX-UHFFFAOYSA-N 0.000 description 1
- PNLSQMMDWXZWHO-UHFFFAOYSA-N hexoxyboron Chemical compound [B]OCCCCCC PNLSQMMDWXZWHO-UHFFFAOYSA-N 0.000 description 1
- UYKVDYQGRZIDGN-UHFFFAOYSA-N hexylboron Chemical compound [B]CCCCCC UYKVDYQGRZIDGN-UHFFFAOYSA-N 0.000 description 1
- CXSYDLCMCLCOCA-UHFFFAOYSA-N hexylboronic acid Chemical compound CCCCCCB(O)O CXSYDLCMCLCOCA-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- UCSAWCKVELENHI-UHFFFAOYSA-N methoxy(phenyl)boron Chemical compound CO[B]C1=CC=CC=C1 UCSAWCKVELENHI-UHFFFAOYSA-N 0.000 description 1
- ZQJCTSOMGUURGX-UHFFFAOYSA-N methoxyboron Chemical compound [B]OC ZQJCTSOMGUURGX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ABWPXVJNCQKYDR-UHFFFAOYSA-N pentylboronic acid Chemical compound CCCCCB(O)O ABWPXVJNCQKYDR-UHFFFAOYSA-N 0.000 description 1
- VPRUMANMDWQMNF-UHFFFAOYSA-N phenylethane boronic acid Chemical compound OB(O)CCC1=CC=CC=C1 VPRUMANMDWQMNF-UHFFFAOYSA-N 0.000 description 1
- PMBLYMFPRDUCBQ-UHFFFAOYSA-N propoxyboron Chemical compound [B]OCCC PMBLYMFPRDUCBQ-UHFFFAOYSA-N 0.000 description 1
- UGANMOORMVBLJP-UHFFFAOYSA-N propylboron Chemical compound [B]CCC UGANMOORMVBLJP-UHFFFAOYSA-N 0.000 description 1
- JAQOMSTTXPGKTN-UHFFFAOYSA-N propylboronic acid Chemical compound CCCB(O)O JAQOMSTTXPGKTN-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003495 technetium Chemical class 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- 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)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Absorbent Articles And Supports Therefor (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/723,601 US4705849A (en) | 1985-04-15 | 1985-04-15 | Boronic acid adducts of technetium-99m dioxime complexes |
| US72360185 | 1985-04-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK169086D0 DK169086D0 (da) | 1986-04-14 |
| DK169086A DK169086A (da) | 1986-10-16 |
| DK168920B1 true DK168920B1 (da) | 1994-07-11 |
Family
ID=24906933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK169086A DK168920B1 (da) | 1985-04-15 | 1986-04-14 | Boronsyreaddukter af technetium-99m-dioxim-komplekser samt sæt anvendeligt til addukternes fremstilling |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4705849A (de) |
| EP (1) | EP0199260B1 (de) |
| JP (2) | JPS61238794A (de) |
| AT (1) | ATE48429T1 (de) |
| AU (1) | AU583101B2 (de) |
| CA (1) | CA1257288A (de) |
| DE (1) | DE3667290D1 (de) |
| DK (1) | DK168920B1 (de) |
| IE (1) | IE58944B1 (de) |
| NZ (1) | NZ215513A (de) |
| ZA (1) | ZA862057B (de) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4714605A (en) * | 1986-10-14 | 1987-12-22 | E. R. Squibb & Sons, Inc. | Technetium-99m labeled dioxime complexes |
| AU1966188A (en) * | 1987-08-07 | 1989-03-09 | Mallinckrodt, Inc. | Diagnostic or radiotherapeutic composition comprising a hydrogen containing compound |
| US4871836A (en) * | 1987-10-13 | 1989-10-03 | E. R. Squibb & Sons, Inc. | Boronic acid adducts of rhenium and radioactive isotopes of rhenium dioxime complexes |
| US5262175A (en) * | 1989-05-10 | 1993-11-16 | Solanki Kishor K | Stabilization of radiopharmaceutical compositions |
| US5039795A (en) * | 1989-06-21 | 1991-08-13 | E. R. Squibb & Sons, Inc. | Preparation of boronic acid derivatives |
| US5069900A (en) * | 1989-08-28 | 1991-12-03 | E. R. Squibb & Sons, Inc. | Boronic acid adducts of technetium-99m dioxime-imine complexes |
| US5118797A (en) * | 1989-08-28 | 1992-06-02 | E. R. Squibb & Sons, Inc. | Rhenium tris dioxime complexes |
| US5377681A (en) * | 1989-11-13 | 1995-01-03 | University Of Florida | Method of diagnosing impaired blood flow |
| US5080884A (en) * | 1989-12-12 | 1992-01-14 | Medi-Physics, Inc. | Hydrocarbylphenyl diaminodithiol radionuclide complexes and their use in imaging |
| US5026913A (en) * | 1989-12-12 | 1991-06-25 | Medi-Physics, Inc. | Hydrocarbylphenyl diaminodithiol derivatives |
| CA2034042C (en) | 1990-01-18 | 1999-08-17 | Adrian D. Nunn | Boronic acid adducts of rhenium dioxime and technetium-99m dioxime complexes containing a biochemically active group |
| US5183653A (en) * | 1990-04-13 | 1993-02-02 | E. R. Squibb & Sons, Inc. | Boronic acid adducts of metal dioxime complexes useful in labelling proteins and other amine-containing compounds |
| US5256394A (en) * | 1991-10-23 | 1993-10-26 | Boron Biologicals, Inc. | Radiological imaging method, and contrast media reagents therefor |
| US5545397A (en) * | 1991-10-23 | 1996-08-13 | Boron Biologicals, Inc. | Contrast agents and compositions for radiological imaging, and radiological imaging method utilizing same |
| US5808091A (en) | 1991-10-29 | 1998-09-15 | Bracco International B.V. | Rhenium and technetium complexes containing a hypoxia localizing moiety |
| US6409987B1 (en) | 1999-04-07 | 2002-06-25 | Intimax Corporation | Targeted agents useful for diagnostic and therapeutic applications |
| US6056941A (en) * | 1999-07-28 | 2000-05-02 | Bracco Research Usa | Kit for the preparation of technetium TC 99m teboroxime myocardial perfusion agent |
| US7026415B2 (en) * | 2004-02-17 | 2006-04-11 | Equistar Chemicals, Lp | Clathrochelates as olefin polymerization catalyst components |
| CN107674098B (zh) * | 2017-06-26 | 2021-12-07 | 中国医学科学院阜外医院 | 一类含芳基硼酸的99mTc配合物及其药盒配方和应用 |
| CN111377968B (zh) * | 2020-03-09 | 2023-07-25 | 中国医学科学院阜外医院 | 一类含芳基硼酸的99mTc(Ⅲ)配合物及其药盒配方和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4387087A (en) * | 1980-04-18 | 1983-06-07 | Research Corporation | Cationic lipophilic complexes of 99m Tc and their use for myocardial and hepatobiliary imaging |
| US4615876A (en) * | 1983-04-25 | 1986-10-07 | Curators Of The University Of Missouri | Macrocyclic complexes of technetium-99m for use as diagnostic radionuclides |
-
1985
- 1985-04-15 US US06/723,601 patent/US4705849A/en not_active Expired - Lifetime
-
1986
- 1986-03-18 NZ NZ215513A patent/NZ215513A/xx unknown
- 1986-03-19 ZA ZA862057A patent/ZA862057B/xx unknown
- 1986-03-20 AU AU54927/86A patent/AU583101B2/en not_active Ceased
- 1986-03-24 IE IE75486A patent/IE58944B1/en not_active IP Right Cessation
- 1986-03-24 CA CA000504793A patent/CA1257288A/en not_active Expired
- 1986-04-14 DK DK169086A patent/DK168920B1/da not_active IP Right Cessation
- 1986-04-15 JP JP61087851A patent/JPS61238794A/ja active Granted
- 1986-04-15 AT AT86105172T patent/ATE48429T1/de not_active IP Right Cessation
- 1986-04-15 DE DE8686105172T patent/DE3667290D1/de not_active Expired - Lifetime
- 1986-04-15 EP EP86105172A patent/EP0199260B1/de not_active Expired
-
1991
- 1991-01-31 JP JP3056255A patent/JPH0714888B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0199260A2 (de) | 1986-10-29 |
| US4705849A (en) | 1987-11-10 |
| DK169086A (da) | 1986-10-16 |
| AU583101B2 (en) | 1989-04-20 |
| ZA862057B (en) | 1986-11-26 |
| JPH0714888B2 (ja) | 1995-02-22 |
| AU5492786A (en) | 1986-10-23 |
| IE860754L (en) | 1986-10-15 |
| JPH0411553B2 (de) | 1992-02-28 |
| JPS61238794A (ja) | 1986-10-24 |
| DE3667290D1 (de) | 1990-01-11 |
| ATE48429T1 (de) | 1989-12-15 |
| CA1257288A (en) | 1989-07-11 |
| DK169086D0 (da) | 1986-04-14 |
| EP0199260A3 (en) | 1987-04-15 |
| IE58944B1 (en) | 1993-12-01 |
| EP0199260B1 (de) | 1989-12-06 |
| NZ215513A (en) | 1988-10-28 |
| JPH061725A (ja) | 1994-01-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |