NO861962L - Radioaktivt halogenerte smaa molykyler for proteinmerking. - Google Patents

Radioaktivt halogenerte smaa molykyler for proteinmerking.

Info

Publication number: NO861962L
Authority: NO; Norway
Prior art keywords: protein; functional group; radioactive; compound; group
Prior art date: 1985-05-17

Application number

NO861962A

Other languages

English (en)

Norwegian (no)

Inventor

Daniel Scott Wilbur

Alan Richard Fritzberg

David Schuster Jones

Original Assignee

Neorx Corp

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.)

1985-05-17

Filing date

1986-05-16

Publication date

1986-11-18

1986-05-16 Application filed by Neorx Corp filed Critical Neorx Corp

1986-11-18 Publication of NO861962L publication Critical patent/NO861962L/no

Links

102000004169 proteins and genes Human genes 0.000 title claims abstract description 68
108090000623 proteins and genes Proteins 0.000 title claims abstract description 68
230000002285 radioactive effect Effects 0.000 title claims description 104
238000002372 labelling Methods 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims abstract description 38
125000000524 functional group Chemical group 0.000 claims abstract description 36
125000003118 aryl group Chemical group 0.000 claims abstract description 28
125000002524 organometallic group Chemical group 0.000 claims abstract description 19
125000001424 substituent group Chemical group 0.000 claims abstract description 19
150000003384 small molecules Chemical class 0.000 claims abstract description 16
230000021615 conjugation Effects 0.000 claims abstract description 15
239000002243 precursor Substances 0.000 claims abstract description 15
229910052794 bromium Inorganic materials 0.000 claims abstract description 14
230000004071 biological effect Effects 0.000 claims abstract description 11
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims description 37
150000002367 halogens Chemical class 0.000 claims description 36
-1 imide ester Chemical class 0.000 claims description 28
238000000034 method Methods 0.000 claims description 27
230000015572 biosynthetic process Effects 0.000 claims description 21
238000003786 synthesis reaction Methods 0.000 claims description 21
239000000047 product Substances 0.000 claims description 15
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 12
238000005658 halogenation reaction Methods 0.000 claims description 11
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 claims description 11
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
230000026030 halogenation Effects 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
229910052789 astatine Inorganic materials 0.000 claims description 8
RYXHOMYVWAEKHL-UHFFFAOYSA-N astatine atom Chemical compound [At] RYXHOMYVWAEKHL-UHFFFAOYSA-N 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
238000006467 substitution reaction Methods 0.000 claims description 8
150000003573 thiols Chemical class 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
239000000427 antigen Substances 0.000 claims description 5
102000036639 antigens Human genes 0.000 claims description 5
108091007433 antigens Proteins 0.000 claims description 5
238000006478 transmetalation reaction Methods 0.000 claims description 5
KRHYYFGTRYWZRS-BJUDXGSMSA-N ac1l2y5h Chemical compound [18FH] KRHYYFGTRYWZRS-BJUDXGSMSA-N 0.000 claims description 4
150000001299 aldehydes Chemical class 0.000 claims description 4
150000001413 amino acids Chemical class 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
150000002540 isothiocyanates Chemical class 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
210000004881 tumor cell Anatomy 0.000 claims description 4
150000003923 2,5-pyrrolediones Chemical class 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
150000002429 hydrazines Chemical class 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
150000003949 imides Chemical class 0.000 claims description 3
229920000642 polymer Polymers 0.000 claims description 3
102000004506 Blood Proteins Human genes 0.000 claims description 2
108010017384 Blood Proteins Proteins 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
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 claims description 2
239000012634 fragment Substances 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
239000000813 peptide hormone Substances 0.000 claims description 2
150000002989 phenols Chemical class 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
150000008049 diazo compounds Chemical class 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
150000001298 alcohols Chemical class 0.000 claims 1
239000012736 aqueous medium Substances 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
150000002902 organometallic compounds Chemical class 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 28
238000002560 therapeutic procedure Methods 0.000 abstract description 9
238000003745 diagnosis Methods 0.000 abstract description 4
238000007324 demetalation reaction Methods 0.000 abstract description 2
125000003106 haloaryl group Chemical group 0.000 abstract description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
239000003921 oil Substances 0.000 description 12
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
229910052740 iodine Inorganic materials 0.000 description 10
239000011630 iodine Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 9
238000001727 in vivo Methods 0.000 description 8
238000000746 purification Methods 0.000 description 8
239000007787 solid Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 5
239000012267 brine Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000003384 imaging method Methods 0.000 description 5
230000026045 iodination Effects 0.000 description 5
238000006192 iodination reaction Methods 0.000 description 5
239000003550 marker Substances 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
KIZBJMBDBYDTEX-UHFFFAOYSA-N 2-[(4-tributylstannylbenzoyl)amino]acetic acid Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(C(=O)NCC(O)=O)C=C1 KIZBJMBDBYDTEX-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 4
206010028980 Neoplasm Diseases 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 4
150000004820 halides Chemical group 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
150000002463 imidates Chemical class 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
210000003734 kidney Anatomy 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
210000001685 thyroid gland Anatomy 0.000 description 4
229960001479 tosylchloramide sodium Drugs 0.000 description 4
LOYKOFHWTNBVBE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-tributylstannylbenzoate Chemical compound C1=CC([Sn](CCCC)(CCCC)CCCC)=CC=C1C(=O)ON1C(=O)CCC1=O LOYKOFHWTNBVBE-UHFFFAOYSA-N 0.000 description 3
PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
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HLEWKZFDAZECQR-UHFFFAOYSA-N methyl 4-bromobenzenecarboximidate Chemical compound COC(=N)C1=CC=C(Br)C=C1 HLEWKZFDAZECQR-UHFFFAOYSA-N 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
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125000006850 spacer group Chemical group 0.000 description 3
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YCDZJPNCKSFWPT-UHFFFAOYSA-M tributylstannyl 4-tributylstannylbenzoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C1=CC=C([Sn](CCCC)(CCCC)CCCC)C=C1 YCDZJPNCKSFWPT-UHFFFAOYSA-M 0.000 description 3
KYRUKRFVOACELK-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(4-hydroxyphenyl)propanoate Chemical compound C1=CC(O)=CC=C1CCC(=O)ON1C(=O)CCC1=O KYRUKRFVOACELK-UHFFFAOYSA-N 0.000 description 2
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DLFRSGUCZXYGAN-UHFFFAOYSA-N 3-(4-tributylstannylphenyl)propanoic acid Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(CCC(O)=O)C=C1 DLFRSGUCZXYGAN-UHFFFAOYSA-N 0.000 description 2
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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239000004133 Sodium thiosulphate Substances 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
102000011923 Thyrotropin Human genes 0.000 description 1
108010061174 Thyrotropin Proteins 0.000 description 1
GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
LUGNZZHPWPZWQF-UHFFFAOYSA-N [(4-hydroxyphenyl)-methoxymethylidene]azanium;chloride Chemical compound Cl.COC(=N)C1=CC=C(O)C=C1 LUGNZZHPWPZWQF-UHFFFAOYSA-N 0.000 description 1
PNDPGZBMCMUPRI-XXSWNUTMSA-N [125I][125I] Chemical compound [125I][125I] PNDPGZBMCMUPRI-XXSWNUTMSA-N 0.000 description 1
CPELXLSAUQHCOX-AHCXROLUSA-N ac1l4zwb Chemical compound [76BrH] CPELXLSAUQHCOX-AHCXROLUSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
RYXHOMYVWAEKHL-OUBTZVSYSA-N astatine-211 Chemical compound [211At] RYXHOMYVWAEKHL-OUBTZVSYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
CPELXLSAUQHCOX-FTXFMUIASA-N bromine-75 Chemical compound [75BrH] CPELXLSAUQHCOX-FTXFMUIASA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000837 carbohydrate group Chemical group 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003759 clinical diagnosis Methods 0.000 description 1
238000011281 clinical therapy Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000007336 electrophilic substitution reaction Methods 0.000 description 1
230000007515 enzymatic degradation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
229940012952 fibrinogen Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000002240 furans Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
125000004404 heteroalkyl group Chemical group 0.000 description 1
230000013632 homeostatic process Effects 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical class N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
229940127121 immunoconjugate Drugs 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011503 in vivo imaging Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
108091005979 iodinated proteins Proteins 0.000 description 1
229940044173 iodine-125 Drugs 0.000 description 1
AMZMQXJQIYKBJU-UHFFFAOYSA-N iodo benzoate Chemical compound IOC(=O)C1=CC=CC=C1 AMZMQXJQIYKBJU-UHFFFAOYSA-N 0.000 description 1
229940069341 iodohippurate Drugs 0.000 description 1
125000006303 iodophenyl group Chemical group 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
SGRIHFNQTZNXAQ-UHFFFAOYSA-N methyl 2-[(4-tributylstannylbenzoyl)amino]ethanimidate Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(C(=O)NCC(=N)OC)C=C1 SGRIHFNQTZNXAQ-UHFFFAOYSA-N 0.000 description 1
ZOGZMBNITFOYBJ-UHFFFAOYSA-N methyl 3-(4-tributylstannylphenyl)propanimidate Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(CCC(=N)OC)C=C1 ZOGZMBNITFOYBJ-UHFFFAOYSA-N 0.000 description 1
DYQNRMCKBFOWKH-UHFFFAOYSA-N methyl 4-hydroxybenzenecarboximidate Chemical compound COC(=N)C1=CC=C(O)C=C1 DYQNRMCKBFOWKH-UHFFFAOYSA-N 0.000 description 1
SHPFEEXMJCKBOH-UHFFFAOYSA-N methyl 4-tributylstannylbenzenecarboximidate Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(C(=N)OC)C=C1 SHPFEEXMJCKBOH-UHFFFAOYSA-N 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
VKDKSZQYQGYWCZ-UHFFFAOYSA-N n-(cyanomethyl)-4-tributylstannylbenzamide Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(C(=O)NCC#N)C=C1 VKDKSZQYQGYWCZ-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical compound OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
238000007344 nucleophilic reaction Methods 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000037081 physical activity Effects 0.000 description 1
230000001817 pituitary effect Effects 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000000700 radioactive tracer Substances 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000007420 reactivation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
VXKVZCJLLIJKAK-UHFFFAOYSA-N sodium;trimethyltin Chemical compound C[Sn](C)(C)[Na] VXKVZCJLLIJKAK-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003577 thiophenes Chemical group 0.000 description 1
239000005495 thyroid hormone Substances 0.000 description 1
229940036555 thyroid hormone Drugs 0.000 description 1
229940034208 thyroxine Drugs 0.000 description 1
XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
238000003325 tomography Methods 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
PXRQBNYPWHRFPD-UHFFFAOYSA-M tributylstannyl 3-(4-tributylstannylphenyl)propanoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)CCC1=CC=C([Sn](CCCC)(CCCC)CCCC)C=C1 PXRQBNYPWHRFPD-UHFFFAOYSA-M 0.000 description 1
REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 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
238000005199 ultracentrifugation Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/12—Aromatic substances containing mercury
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Peptides Or Proteins (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Investigating Or Analysing Biological Materials (AREA)

NO861962A 1985-05-17 1986-05-16 Radioaktivt halogenerte smaa molykyler for proteinmerking. NO861962L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US73539285A	1985-05-17	1985-05-17
US85274086A	1986-04-21	1986-04-21

Publications (1)

Publication Number	Publication Date
NO861962L true NO861962L (no)	1986-11-18

Family

ID=27112875

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO861962A NO861962L (no)	1985-05-17	1986-05-16	Radioaktivt halogenerte smaa molykyler for proteinmerking.

Country Status (5)

Country	Link
EP (1)	EP0203764B1 (de)
AT (1)	ATE87290T1 (de)
DE (1)	DE3688103T2 (de)
DK (1)	DK226986A (de)
NO (1)	NO861962L (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4812577A (en) *	1987-04-28	1989-03-14	The United States Of America As Represented By The United States Department Of Energy	Mercuric acetate phenyl maleimide useful for preparing radiohalogenated maleimides
US4977288A (en) *	1988-01-29	1990-12-11	President And Fellows Of Harvard College	M-aminophenyltrialkylstannane
US5059541A (en) *	1988-04-29	1991-10-22	Neorx Corporation	Minimal derivatization of proteins
US4966999A (en) *	1988-06-07	1990-10-30	Cytogen Corporation	Radiohalogenated compounds for site specific labeling
DE68924783T2 (de) *	1988-09-30	1996-03-28	Neorx Corp	Wässrige additivsysteme, verfahren und polymerteilchen.
US5066789A (en) *	1988-09-30	1991-11-19	Neorx Corporation	Targeting substance-diagnostic/therapeutic agent conjugates having Schiff base linkages
US5102651A (en) *	1989-12-29	1992-04-07	Neorx Corporation	Process for isolation and radiolabeling of pharmaceuticals with isotopes of astatine
US5463080A (en) *	1992-08-27	1995-10-31	Bracco International B.V.	2,4,6-triiodo-1,3-benzenedicarboxylic acid compounds used as radiolabelling reagents
GB0206750D0 (en)	2002-03-22	2002-05-01	Amersham Plc	Radiofluorination methods
DK3157577T3 (da)	2014-06-18	2021-01-18	Alpha Therapy Solutions Ab	Automatisk procesplatform til fremstilling af astatin-211 [at-211]-radiofarmaka

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3979506A (en) *	1974-10-11	1976-09-07	Pierce Chemical Company	Radioactive compounds for labeling proteins
JPS5932457B2 (ja)	1978-11-29	1984-08-09	エフ・ホフマン−ラ・ロシユ・ウント・コンパニ−・アクチエンゲゼルシヤフト	放射性ヨウ素化アミン
DE2947500C2 (de)	1979-11-24	1984-05-10	Dutschka, Klaus, 4300 Essen	Radiojodierte ω -Phenylfettsäuren, ihre Herstellung und deren Verwendung zur szintigraphischen Untersuchung des Herzmuskels und der Leber

1986
- 1986-05-16 EP EP86303757A patent/EP0203764B1/de not_active Expired - Lifetime
- 1986-05-16 AT AT86303757T patent/ATE87290T1/de not_active IP Right Cessation
- 1986-05-16 NO NO861962A patent/NO861962L/no unknown
- 1986-05-16 DK DK226986A patent/DK226986A/da unknown
- 1986-05-16 DE DE8686303757T patent/DE3688103T2/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE3688103D1 (de)	1993-04-29
EP0203764A3 (en)	1990-03-28
DE3688103T2 (de)	1993-07-15
DK226986A (da)	1986-11-18
EP0203764A2 (de)	1986-12-03
EP0203764B1 (de)	1993-03-24
ATE87290T1 (de)	1993-04-15
DK226986D0 (da)	1986-05-16

Publication	Publication Date	Title
US4885153A (en)	1989-12-05	Radiohalogenated for proteins
CA1328147C (en)	1994-03-29	Metal-radionuclide-labeled proteins and glycoproteins for diagnosis and therapy
CA1305160C (en)	1992-07-14	Ether isonitriles and radiolabeled complexes thereof
US4735792A (en)	1988-04-05	Radioiodinated maleimides and use as agents for radiolabeling antibodies
US5616692A (en)	1997-04-01	Metal-radionuclide-labeled proteins and glycoproteins for diagnosis and therapy
NO861962L (no)	1986-11-18	Radioaktivt halogenerte smaa molykyler for proteinmerking.
JPH0647560B2 (ja)	1994-06-22	放射性標識された抗体断片用のカツプリング剤
EP0420934B1 (de)	1994-09-21	Bifunktionelle kuppler und daraus hergestellte mit radionukleid markierte zusammensetzungen
EP0005834A1 (de)	1979-12-12	Vitamin B12 Derivate, Verfahren zu deren Herstellung und ihre Verwendung bei Radioimmun-Testen
US20240018110A1 (en)	2024-01-18	Radiolabeled compounds targeting the prostate-specific membrane antigen
Knapp Jr et al.	1984	Effect of tellurium position on the myocardial uptake of radioiodinated 18-iodotellura-17-octadecenoic acid analogs
KR101315152B1 (ko)	2013-10-07	신규 유기화합물 및 상기 화합물을 이용한 방사성 할로겐표식 유기화합물의 제조 방법
Toscano et al.	2024	13Cβ‐Valine and 13Cγ‐Leucine Methine Labeling To Probe Protein Ligand Interaction
JPH09194406A (ja)	1997-07-29	蛋白質標識のための放射性ハロゲン化化合物
EP0289187A2 (de)	1988-11-02	Vinyl-substituierte Radiohalogen-Konjugate zur Markierung von Proteinen
Kasina et al.	1998	Simplified preformed chelate protein radiolabeling with technetium-99m mercaptoacetamidoadipoylglycylglycine (N3S-adipate)
US4870188A (en)	1989-09-26	Vinyl substituted radiohalogen conjugates for protein labeling
Mamat et al.	2015	Preparation of 4-halobenzoate-containing phosphane-based building blocks for labeling reactions using the traceless Staudinger ligation
US6334995B1 (en)	2002-01-01	Process for the preparation of technetium-99m diethylene triamine penta-acetic acid diester
US20230002293A1 (en)	2023-01-05	Radiohalogen prosthetic moieties and radiolabeled biomolecules
AU599603B2 (en)	1990-07-26	Process for preparation of antigens using radio active stilbene derivatives labelled with iodine and the antigens obtained
US5290937A (en)	1994-03-01	Radiolabeling of proteins using alkoxyphenol derivatives
Goodman et al.	1984	Synthesis and evaluation of radioiodinated terminal‐substituted 5‐iodo‐(2‐thienyl) fatty acids as new myocardial imaging agents
KR20120066550A (ko)	2012-06-22	사멸세포의 양전자방출 단층촬영술을 위한 Ｆ?１８ 표지 ＡｐｏＰｅｐ?１ 화합물， 이의 제조방법 및 응용
JPH06505975A (ja)	1994-07-07	環状リガンド