DE69101708T2 - Verfahren zur herstellung von übergangsmetallnitridkomplexen. - Google Patents
Verfahren zur herstellung von übergangsmetallnitridkomplexen.Info
- Publication number
- DE69101708T2 DE69101708T2 DE69101708T DE69101708T DE69101708T2 DE 69101708 T2 DE69101708 T2 DE 69101708T2 DE 69101708 T DE69101708 T DE 69101708T DE 69101708 T DE69101708 T DE 69101708T DE 69101708 T2 DE69101708 T2 DE 69101708T2
- Authority
- DE
- Germany
- Prior art keywords
- process according
- ligand
- radical
- ammonium
- tin
- 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.)
- Expired - Fee Related
Links
- -1 TRANSITION METAL NITRIDE Chemical class 0.000 title claims description 70
- 229910052723 transition metal Inorganic materials 0.000 title claims description 40
- 238000004519 manufacturing process Methods 0.000 title description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 88
- 239000003446 ligand Substances 0.000 claims description 88
- 238000000034 method Methods 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 239000003638 chemical reducing agent Substances 0.000 claims description 41
- 229910052751 metal Inorganic materials 0.000 claims description 41
- 239000002184 metal Substances 0.000 claims description 41
- 230000008569 process Effects 0.000 claims description 41
- 239000000243 solution Substances 0.000 claims description 33
- 150000003624 transition metals Chemical class 0.000 claims description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 26
- 150000002927 oxygen compounds Chemical class 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 239000008139 complexing agent Substances 0.000 claims description 19
- 150000003254 radicals Chemical group 0.000 claims description 17
- 229910052713 technetium Inorganic materials 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 15
- 102000008394 Immunoglobulin Fragments Human genes 0.000 claims description 14
- 108010021625 Immunoglobulin Fragments Proteins 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 125000000962 organic group Chemical group 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical group [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims description 12
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 150000005840 aryl radicals Chemical class 0.000 claims description 10
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 10
- 102000004169 proteins and genes Human genes 0.000 claims description 10
- 108090000623 proteins and genes Proteins 0.000 claims description 10
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 9
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 claims description 8
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 8
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 8
- 239000013110 organic ligand Substances 0.000 claims description 8
- 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 claims description 7
- 235000011150 stannous chloride Nutrition 0.000 claims description 7
- FCMYSEXCLRFWBP-UHFFFAOYSA-N [NH4+].[NH4+].[O-]S(=O)S([O-])=O Chemical compound [NH4+].[NH4+].[O-]S(=O)S([O-])=O FCMYSEXCLRFWBP-UHFFFAOYSA-N 0.000 claims description 6
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical group [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 235000011180 diphosphates Nutrition 0.000 claims description 5
- 229950004394 ditiocarb Drugs 0.000 claims description 5
- 239000001294 propane Substances 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 229910052702 rhenium Chemical group 0.000 claims description 4
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical group [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 3
- IRZFQKXEKAODTJ-UHFFFAOYSA-M sodium;propan-2-yloxymethanedithioate Chemical compound [Na+].CC(C)OC([S-])=S IRZFQKXEKAODTJ-UHFFFAOYSA-M 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 101100422771 Caenorhabditis elegans sup-9 gene Proteins 0.000 claims description 2
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 claims description 2
- DWMBIXBKXXRQHQ-UHFFFAOYSA-N OC1OP(=O)OP(=O)O1 Chemical class OC1OP(=O)OP(=O)O1 DWMBIXBKXXRQHQ-UHFFFAOYSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- 125000005612 glucoheptonate group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- KGKSGSIXIHHTHE-UHFFFAOYSA-M sodium;propanedithioate Chemical compound [Na+].CCC([S-])=S KGKSGSIXIHHTHE-UHFFFAOYSA-M 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- DCGAZEUEQCRILY-UHFFFAOYSA-N (2-oxo-1,3,2lambda5-dioxaphosphetan-2-yl) dihydrogen phosphate Chemical class OP(O)(=O)OP1(=O)OCO1 DCGAZEUEQCRILY-UHFFFAOYSA-N 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- YXTDAZMTQFUZHK-UHFFFAOYSA-L 5,6-dihydroxy-1,3,2$l^{2}-dioxastannepane-4,7-dione Chemical group [Sn+2].[O-]C(=O)C(O)C(O)C([O-])=O YXTDAZMTQFUZHK-UHFFFAOYSA-L 0.000 claims 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 36
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 19
- 239000012217 radiopharmaceutical Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000654 additive Substances 0.000 description 15
- 230000000996 additive effect Effects 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 229940121896 radiopharmaceutical Drugs 0.000 description 13
- 230000002799 radiopharmaceutical effect Effects 0.000 description 13
- 239000008363 phosphate buffer Substances 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 229940116901 diethyldithiocarbamate Drugs 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 150000004767 nitrides Chemical class 0.000 description 6
- 229940056501 technetium 99m Drugs 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical class [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 238000003745 diagnosis Methods 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
- 230000010415 tropism Effects 0.000 description 4
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000009206 nuclear medicine Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 3
- 229940048086 sodium pyrophosphate Drugs 0.000 description 3
- 239000008174 sterile solution Substances 0.000 description 3
- 150000003495 technetium Chemical class 0.000 description 3
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 3
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 3
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 2
- RSOOXPFMVKSKNN-UHFFFAOYSA-N 2-acetyloxyethyl acetate;amino acetate Chemical class CC(=O)ON.CC(=O)ON.CC(=O)OCCOC(C)=O RSOOXPFMVKSKNN-UHFFFAOYSA-N 0.000 description 2
- HWZUDASOMGNLSM-UHFFFAOYSA-N O=P1OCOP(=O)O1 Chemical compound O=P1OCOP(=O)O1 HWZUDASOMGNLSM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229940050410 gluconate Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229960001639 penicillamine Drugs 0.000 description 2
- 229940048084 pyrophosphate Drugs 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- XJHRGQUGDYHYNH-UHFFFAOYSA-M sodium;diethyl-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CCP([S-])(=S)CC XJHRGQUGDYHYNH-UHFFFAOYSA-M 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 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 1
- YXTDAZMTQFUZHK-ZVGUSBNCSA-L (2r,3r)-2,3-dihydroxybutanedioate;tin(2+) Chemical compound [Sn+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O YXTDAZMTQFUZHK-ZVGUSBNCSA-L 0.000 description 1
- ZQXIMYREBUZLPM-UHFFFAOYSA-N 1-aminoethanethiol Chemical compound CC(N)S ZQXIMYREBUZLPM-UHFFFAOYSA-N 0.000 description 1
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 1
- HPHBOJANXDKUQD-UHFFFAOYSA-N 2-cyanoacetohydrazide Chemical compound NNC(=O)CC#N HPHBOJANXDKUQD-UHFFFAOYSA-N 0.000 description 1
- NDXLVXDHVHWYFR-UHFFFAOYSA-N 2-pyridin-1-ium-1-ylacetohydrazide;chloride Chemical compound [Cl-].NNC(=O)C[N+]1=CC=CC=C1 NDXLVXDHVHWYFR-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 101100208721 Mus musculus Usp5 gene Proteins 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- FYWDGJCLLYSXFJ-UHFFFAOYSA-M P(=O)([O-])(O)O.S(=O)(O)S(=O)O.[Na+] Chemical compound P(=O)([O-])(O)O.S(=O)(O)S(=O)O.[Na+] FYWDGJCLLYSXFJ-UHFFFAOYSA-M 0.000 description 1
- 239000007990 PIPES buffer Substances 0.000 description 1
- HEFUQMVMXLNCKZ-UHFFFAOYSA-N PP(=O)=O Chemical class PP(=O)=O HEFUQMVMXLNCKZ-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FMQNKVGDYIXYDI-UHFFFAOYSA-N [Na].C=C.C=C Chemical group [Na].C=C.C=C FMQNKVGDYIXYDI-UHFFFAOYSA-N 0.000 description 1
- IPYIMQWJGKCLPM-UHFFFAOYSA-N [Na].CCSC=S Chemical compound [Na].CCSC=S IPYIMQWJGKCLPM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- ZKLHYLQJFBULTC-UHFFFAOYSA-N amino(methyl)carbamodithioic acid Chemical compound CN(N)C(S)=S ZKLHYLQJFBULTC-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- HCOMFAYPHBFMKU-UHFFFAOYSA-N butanedihydrazide Chemical compound NNC(=O)CCC(=O)NN HCOMFAYPHBFMKU-UHFFFAOYSA-N 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- GYQBBRRVRKFJRG-UHFFFAOYSA-L disodium pyrophosphate Chemical compound [Na+].[Na+].OP([O-])(=O)OP(O)([O-])=O GYQBBRRVRKFJRG-UHFFFAOYSA-L 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229950003499 fibrin Drugs 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 1
- 229940102859 methylene diphosphonate Drugs 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 229960004230 oxidronic acid Drugs 0.000 description 1
- HJZKOAYDRQLPME-UHFFFAOYSA-N oxidronic acid Chemical compound OP(=O)(O)C(O)P(O)(O)=O HJZKOAYDRQLPME-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 230000002285 radioactive effect Effects 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
- 150000003281 rhenium Chemical class 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 229940033078 sodium pertechnetate tc 99m Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- NEUOBESLMIKJSB-UHFFFAOYSA-J tetrasodium;tetraacetate Chemical compound [Na+].[Na+].[Na+].[Na+].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O NEUOBESLMIKJSB-UHFFFAOYSA-J 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- FAKFSJNVVCGEEI-UHFFFAOYSA-J tin(4+);disulfate Chemical compound [Sn+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FAKFSJNVVCGEEI-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- FYGHSUNMUKGBRK-UHFFFAOYSA-N trimethylbenzene Natural products CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 1
- ABBFTEOOAGLOID-UHFFFAOYSA-J tris(carbamothioylsulfanyl)stannyl carbamodithioate Chemical compound [Sn+4].NC([S-])=S.NC([S-])=S.NC([S-])=S.NC([S-])=S ABBFTEOOAGLOID-UHFFFAOYSA-J 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000012800 visualization 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
- 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
- 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
- A61K51/0476—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group complexes from monodendate ligands, e.g. sestamibi
-
- 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
- A61K51/12—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/004—Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium
-
- 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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Physics & Mathematics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dispersion Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9008473A FR2664166A1 (fr) | 1990-07-04 | 1990-07-04 | Procede de preparation de complexes nitruro de metaux de transition utilisables comme produits radiopharmaceutiques ou pour la synthese de nouveaux produits radiopharmaceutiques. |
| PCT/FR1991/000536 WO1992000982A1 (fr) | 1990-07-04 | 1991-07-03 | Procede de preparation de complexes nitruro de metaux de transition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69101708D1 DE69101708D1 (de) | 1994-05-19 |
| DE69101708T2 true DE69101708T2 (de) | 1994-10-27 |
Family
ID=9398344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69101708T Expired - Fee Related DE69101708T2 (de) | 1990-07-04 | 1991-07-03 | Verfahren zur herstellung von übergangsmetallnitridkomplexen. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5399339A ( ) |
| EP (1) | EP0537242B1 ( ) |
| JP (1) | JP3097755B2 ( ) |
| AU (1) | AU8105491A ( ) |
| CA (1) | CA2086426C ( ) |
| DE (1) | DE69101708T2 ( ) |
| ES (1) | ES2053330T3 ( ) |
| FR (1) | FR2664166A1 ( ) |
| WO (1) | WO1992000982A1 ( ) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2679452B1 (fr) * | 1991-07-22 | 1993-11-12 | Cis Bio International | Produit radiopharmaceutique ayant notamment un tropisme cerebral, comportant un complexe nitruro d'un metal de transition, et son procede de preparation. |
| US5744120A (en) * | 1993-03-30 | 1998-04-28 | The Dupont Merick Pharmaceutical Company | Ternary radiopharmaceutical complexes |
| US5750088A (en) * | 1993-03-30 | 1998-05-12 | The Dupont Merck Pharmaceutical Company | Stable hydrazones linked to a peptide moiety as reagents for the preparation of radiopharmaceuticals |
| AU6493894A (en) * | 1993-03-31 | 1994-10-24 | Mallinckrodt Medical, Inc. | Radiopharmaceutical formulations having non-stannous reductants |
| US5414620A (en) * | 1993-08-09 | 1995-05-09 | Honeywell Inc. | Synthetic friction algorithm for a hand control element |
| US5751629A (en) | 1995-04-25 | 1998-05-12 | Irori | Remotely programmable matrices with memories |
| US6331273B1 (en) | 1995-04-25 | 2001-12-18 | Discovery Partners International | Remotely programmable matrices with memories |
| US6329139B1 (en) | 1995-04-25 | 2001-12-11 | Discovery Partners International | Automated sorting system for matrices with memory |
| US5874214A (en) | 1995-04-25 | 1999-02-23 | Irori | Remotely programmable matrices with memories |
| US6416714B1 (en) | 1995-04-25 | 2002-07-09 | Discovery Partners International, Inc. | Remotely programmable matrices with memories |
| US6017496A (en) | 1995-06-07 | 2000-01-25 | Irori | Matrices with memories and uses thereof |
| FR2736834B1 (fr) * | 1995-07-17 | 1997-08-29 | Cis Bio Int | Produits radiopharmaceutiques a tropisme cardiaque comportant un complexe nitruro d'un metal de transition et ayant une clairance myocardique rapide |
| KR100554563B1 (ko) * | 1996-12-18 | 2006-03-03 | 니혼 메디피직스 가부시키가이샤 | 방사성 전이 금속 질화물 헤테로-착물 |
| KR100501534B1 (ko) * | 1997-12-23 | 2005-10-26 | 정재민 | 방사성 동위원소 치료를 위한 방사성 레늄주석콜로이드 및 그 제법 |
| CA2417392C (en) * | 2000-07-28 | 2007-09-11 | Nihon Medi-Physics Co., Ltd. | Radiopharmaceutical for diagnostic imaging containing a technetium-99m nitride heterocomplex |
| US8182789B2 (en) | 2006-01-20 | 2012-05-22 | Nihon Medi-Physics Co., Ltd. | Intermediate compound of technetium nitride complex for radiodiagnostic imaging |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0166746B1 (en) * | 1983-12-29 | 1991-04-24 | The Commonwealth Of Australia | Preparation of ?99m tc radiopharmaceuticals |
| US5279811A (en) * | 1987-02-18 | 1994-01-18 | The Du Pont Merck Pharmaceutical Company | Ester-substituted diaminedithiols and radiolabeled complexes thereof |
| ATE85619T1 (de) * | 1988-03-09 | 1993-02-15 | Cis Bio Int | Herstellung von als radiopharmazeutische produkte verwendbare nitruroverbindungen. |
| DE68909245T2 (de) * | 1988-11-25 | 1994-03-17 | Cis Bio International Saclay | Übergangsmetall-stickstoffkomplex enthaltendes radiopharmazeutisches produkt mit einer neigung zum herzgewebe. |
-
1990
- 1990-07-04 FR FR9008473A patent/FR2664166A1/fr active Granted
-
1991
- 1991-07-03 CA CA002086426A patent/CA2086426C/fr not_active Expired - Fee Related
- 1991-07-03 AU AU81054/91A patent/AU8105491A/en not_active Abandoned
- 1991-07-03 ES ES91912410T patent/ES2053330T3/es not_active Expired - Lifetime
- 1991-07-03 JP JP03511871A patent/JP3097755B2/ja not_active Expired - Fee Related
- 1991-07-03 DE DE69101708T patent/DE69101708T2/de not_active Expired - Fee Related
- 1991-07-03 US US07/965,250 patent/US5399339A/en not_active Expired - Lifetime
- 1991-07-03 WO PCT/FR1991/000536 patent/WO1992000982A1/fr active IP Right Grant
- 1991-07-03 EP EP91912410A patent/EP0537242B1/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5399339A (en) | 1995-03-21 |
| FR2664166B1 ( ) | 1994-12-16 |
| ES2053330T3 (es) | 1994-07-16 |
| JP3097755B2 (ja) | 2000-10-10 |
| CA2086426A1 (fr) | 1992-01-05 |
| FR2664166A1 (fr) | 1992-01-10 |
| WO1992000982A1 (fr) | 1992-01-23 |
| JPH05508842A (ja) | 1993-12-09 |
| EP0537242B1 (fr) | 1994-04-13 |
| EP0537242A1 (fr) | 1993-04-21 |
| DE69101708D1 (de) | 1994-05-19 |
| CA2086426C (fr) | 2004-06-15 |
| AU8105491A (en) | 1992-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |