FI105332B - Förfarande för framställning av isotiocyanatfunktionaliserade metallkomplex - Google Patents
Förfarande för framställning av isotiocyanatfunktionaliserade metallkomplex Download PDFInfo
- Publication number
- FI105332B FI105332B FI896248A FI896248A FI105332B FI 105332 B FI105332 B FI 105332B FI 896248 A FI896248 A FI 896248A FI 896248 A FI896248 A FI 896248A FI 105332 B FI105332 B FI 105332B
- Authority
- FI
- Finland
- Prior art keywords
- isothiocyanate
- methyl
- preparation
- aminophenyl
- thiophosgene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 21
- 229910052751 metal Inorganic materials 0.000 title claims description 16
- 239000002184 metal Substances 0.000 title claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 46
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 239000013522 chelant Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000010948 rhodium Substances 0.000 claims description 7
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- LXXWJPGQPFKXIY-UHFFFAOYSA-N n,n'-bis(2-aminoethyl)-2-[(4-aminophenyl)methyl]propane-1,3-diamine Chemical group NCCNCC(CNCCN)CC1=CC=C(N)C=C1 LXXWJPGQPFKXIY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- NYVLCFJZDGEXMU-UHFFFAOYSA-N 4-(1,4,8,11-tetrazacyclotetradec-6-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CC1CNCCNCCCNCCNC1 NYVLCFJZDGEXMU-UHFFFAOYSA-N 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- XSXMSSQVUIRVDE-UHFFFAOYSA-N 1-n-(2-aminoethyl)-2-n-(3-aminopropyl)pentane-1,2,5-triamine Chemical compound NCCCNC(CCCN)CNCCN XSXMSSQVUIRVDE-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000003446 ligand Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000002738 chelating agent Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- KZUNJOHGWZRPMI-AKLPVKDBSA-N samarium-153 Chemical compound [153Sm] KZUNJOHGWZRPMI-AKLPVKDBSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000002285 radioactive effect Effects 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007995 HEPES buffer Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- -1 lanthanide macrocycles Chemical class 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 3
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000009920 chelation Effects 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UWMHHZFHBCYGCV-UHFFFAOYSA-N 2,3,2-tetramine Chemical compound NCCNCCCNCCN UWMHHZFHBCYGCV-UHFFFAOYSA-N 0.000 description 1
- XAFVLCLQGAHLKY-UHFFFAOYSA-N 3-(4-aminophenyl)-2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]propanoic acid Chemical compound C1=CC(N)=CC=C1CC(C(O)=O)N1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 XAFVLCLQGAHLKY-UHFFFAOYSA-N 0.000 description 1
- HQHVHMQCHASIHT-UHFFFAOYSA-N 4-(4-aminophenyl)-2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]butanoic acid Chemical compound C1=CC(N)=CC=C1CCC(C(O)=O)N1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 HQHVHMQCHASIHT-UHFFFAOYSA-N 0.000 description 1
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- 101001068640 Nicotiana tabacum Basic form of pathogenesis-related protein 1 Proteins 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 1
- WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005277 cation exchange chromatography Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 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
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010265 fast atom bombardment Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- OHSVLFRHMCKCQY-NJFSPNSNSA-N lutetium-177 Chemical compound [177Lu] OHSVLFRHMCKCQY-NJFSPNSNSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- DOSGOCSVHPUUIA-UHFFFAOYSA-N samarium(3+) Chemical compound [Sm+3] DOSGOCSVHPUUIA-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-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
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0482—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group chelates from cyclic ligands, e.g. DOTA
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—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
- A61K51/0478—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 non-cyclic ligands, e.g. EDTA, MAG3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
-
- 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
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
-
- 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
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
- C07F19/005—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00 without metal-C linkages
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (8)
1. Förfarande för framställning av isotiocyanat-funktionaliserade metallkomplex, kännetecknat 5 av att ett aminofunktionaliserat polyazakelat omsätts med tiofosgen, vilket kelat innehäller endast primära och/el-! ler sekundära aminer, varvid kelatmetallen är rodium, och närvarande är ett polärt lösningsmedel eller en blandning av polära lösningsmedel, varvid dock lösningsmedlet är ett 10 annat än enbart vatten, när kelatet är 6-[(4-aminofenyl)metyl)-1,4,8,11-tetraazaundekan.
2. Förfarande enligt patentkrav l, k ä n n e - ' tecknatav att lösningsmedelsblandningen är en H blandning av vatten och acetonitril eller kloroform. 15
3. Förfarande enligt patentkrav l, känne tecknat av att det polära lösningsmedlet är vatten eller acetonitril.
4. Förfarande enligt patentkrav 1, kännetecknat av att reaktionens pH är 2 - 10. 20
5. Förfarande enligt patentkrav 1, känne tecknat av att temperaturen är 0 - 50 °C.
6. Förfarande enligt patentkrav 1, kännetecknat av att polyazakelateringsmedlet är nägot av föl jande .· . 25 3 -[(4-aminofenyl)metyl]-1,5,8,12 -tetraazacyklotet- radekan ; 6-[(4-aminofenyl)metyl]-1,4,8,11-tetraazaundekan; 1,4,7,10 -tetraaza-1-[(4-aminofenyl)metyl]cyklodo-dekan; eller 30 6-(3-aminopropyl)-1,4,7,11-tetraazaundekan.
7. Förfarande enligt patentkrav 1 för framställning av [105Rh(6- [ (4-isotiocyanatfenyl)metyl] -1,4,8,11-tetraazaundekan) Cl2] * kännetecknat av att * m 1S 105332 [105Rh (6 - [(4 - amino fenyl )metyl]-1,4,8, 11 - tetraa zaunde -kan)Cl2]* fkr reagera med tiofosgen i vatten/acetonitril * vid rumstemperatur.
8. Förfarande enligt patentkrav 1 för framställning 5 av [105Rh (6-[ (4-isotiocyanatfenyl-metyl]-1,4,8,11-tetraaz-aundekan) Cl2] * kännetecknat av att [105Rh (6 - [ (4 -am i no fenyl) me tyl] -1, 4 , 8, 11 - tetraa zaunde -kan)Cl2]* fär reagera med tiofosgen i vatten/acetonitril vid rumstemperatur och lösningsmedlen avlägsnas genom att 10 avdunsta och med tillhjälp av en kväveströmning. w
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28917288A | 1988-12-23 | 1988-12-23 | |
US28917288 | 1988-12-23 | ||
US38310389 | 1989-07-20 | ||
US07/383,103 US5006643A (en) | 1987-06-24 | 1989-07-20 | Process for preparing isothiocyanato functionalized metal complexes |
Publications (2)
Publication Number | Publication Date |
---|---|
FI896248A0 FI896248A0 (fi) | 1989-12-22 |
FI105332B true FI105332B (sv) | 2000-07-31 |
Family
ID=26965479
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI896248A FI105332B (sv) | 1988-12-23 | 1989-12-22 | Förfarande för framställning av isotiocyanatfunktionaliserade metallkomplex |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0374947B1 (sv) |
JP (1) | JP2930708B2 (sv) |
KR (1) | KR0163758B1 (sv) |
CN (1) | CN1025735C (sv) |
BR (1) | BR8907282A (sv) |
CA (1) | CA2006372C (sv) |
DE (1) | DE68921582T2 (sv) |
DK (1) | DK665589A (sv) |
ES (1) | ES2068881T3 (sv) |
FI (1) | FI105332B (sv) |
GR (1) | GR3015661T3 (sv) |
HK (1) | HK123196A (sv) |
HU (1) | HU209459B (sv) |
IL (1) | IL92860A (sv) |
MX (1) | MX166369B (sv) |
NO (1) | NO895236L (sv) |
PT (1) | PT92670B (sv) |
WO (1) | WO1990007342A1 (sv) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0489869B1 (en) * | 1989-08-28 | 1998-11-11 | The General Hospital Corporation | Hydroxy-aryl metal chelates for diagnostic nmr imaging |
US5410043A (en) * | 1991-12-06 | 1995-04-25 | Schering Aktiengesellschaft | Process for the production of mono-N-substituted tetraaza macrocycles |
WO1993020852A2 (en) * | 1992-04-13 | 1993-10-28 | The Dow Chemical Company | Macrocyclic chelating agents, chelates and conjugates thereof |
US5310535A (en) * | 1992-04-24 | 1994-05-10 | The Dow Chemical Company | Carboxamide modified polyamine chelators and radioactive complexes thereof for conjugation to antibodies |
DE4218744C2 (de) * | 1992-06-04 | 1997-11-06 | Schering Ag | Verfahren zur Herstellung von N-ß-Hxdroxyalkyl-tri-N-carboxylalkyl-1,4,7,10-tetraazacyclododecan- und N-ß-Hydroxyalkyl-tri-N-carboxyalkyl-1,4,8,11-tetraazacyclotetradecan-Derivaten und deren Metallkomplexe |
US5505931A (en) * | 1993-03-04 | 1996-04-09 | The Dow Chemical Company | Acid cleavable compounds, their preparation and use as bifunctional acid-labile crosslinking agents |
EP0588229A3 (en) * | 1992-09-12 | 1994-06-15 | Hoechst Ag | Macrocyclic chelating agents for the preparation of technetium or rhenium complexes |
WO1995001346A1 (en) * | 1993-06-30 | 1995-01-12 | Akzo Nobel N.V. | Chelating compounds |
US5582814A (en) * | 1994-04-15 | 1996-12-10 | Metasyn, Inc. | 1-(p-n-butylbenzyl) DTPA for magnetic resonance imaging |
US6693190B1 (en) | 1994-05-11 | 2004-02-17 | Bracco International B.V. | Enhanced relaxivity monomeric and multimeric compounds |
TW319763B (sv) | 1995-02-01 | 1997-11-11 | Epix Medical Inc | |
FR2830253B1 (fr) * | 2001-09-28 | 2005-02-04 | Air Liquide | Nouveau procede de preparation de macrocycles azotes c-fonctionnalises et nouveaux intermediaires obtenus |
CN1329432C (zh) * | 2004-12-03 | 2007-08-01 | 宁波大学 | 一种水溶性螯合树脂和其合成方法及其应用 |
JP2009215238A (ja) * | 2008-03-11 | 2009-09-24 | Osaka Univ | 希土類発光プローブ |
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GB1054328A (sv) * | 1963-10-28 | |||
US3972910A (en) * | 1970-07-09 | 1976-08-03 | Bayer Aktiengesellschaft | Preparation of a chlorinated diisocyanate |
US3994966A (en) * | 1972-09-28 | 1976-11-30 | The Board Of Trustees Of The Leland Stanford Junior University | Chelating agents |
US3931201A (en) * | 1974-01-22 | 1976-01-06 | The Dow Chemical Company | Substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives |
CA1178951A (en) * | 1980-03-18 | 1984-12-04 | Claude F. Meares | Chelating agents and method |
US4622420A (en) * | 1980-03-18 | 1986-11-11 | The Regents Of The University Of California | Chelating agents and method |
JPS57167023A (en) * | 1981-04-08 | 1982-10-14 | Fuji Photo Film Co Ltd | Developing method for color photographic sensitive material |
US4647447A (en) * | 1981-07-24 | 1987-03-03 | Schering Aktiengesellschaft | Diagnostic media |
SE8301395L (sv) * | 1983-03-15 | 1984-09-16 | Wallac Oy | Kelatiserande foreningar med funktionella grupper vilka tillater kovalent koppling till bio-organiska molekyler |
US4824986A (en) * | 1985-04-26 | 1989-04-25 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Metal chelate protein conjugate |
US4885363A (en) * | 1987-04-24 | 1989-12-05 | E. R. Squibb & Sons, Inc. | 1-substituted-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs |
US4994560A (en) * | 1987-06-24 | 1991-02-19 | The Dow Chemical Company | Functionalized polyamine chelants and radioactive rhodium complexes thereof for conjugation to antibodies |
EP0420942A1 (en) * | 1988-06-24 | 1991-04-10 | The Dow Chemical Company | Macrocyclic bifunctional chelants, complexes thereof and their antibody conjugates |
-
1989
- 1989-12-15 BR BR898907282A patent/BR8907282A/pt not_active Application Discontinuation
- 1989-12-15 JP JP2501909A patent/JP2930708B2/ja not_active Expired - Lifetime
- 1989-12-15 WO PCT/US1989/005785 patent/WO1990007342A1/en unknown
- 1989-12-21 PT PT92670A patent/PT92670B/pt active IP Right Grant
- 1989-12-21 CA CA002006372A patent/CA2006372C/en not_active Expired - Fee Related
- 1989-12-22 MX MX018868A patent/MX166369B/es unknown
- 1989-12-22 IL IL9286089A patent/IL92860A/en not_active IP Right Cessation
- 1989-12-22 DK DK665589A patent/DK665589A/da not_active Application Discontinuation
- 1989-12-22 CN CN89109820A patent/CN1025735C/zh not_active Expired - Lifetime
- 1989-12-22 FI FI896248A patent/FI105332B/sv not_active IP Right Cessation
- 1989-12-22 HU HU896768A patent/HU209459B/hu not_active IP Right Cessation
- 1989-12-22 DE DE68921582T patent/DE68921582T2/de not_active Expired - Lifetime
- 1989-12-22 KR KR1019890019262A patent/KR0163758B1/ko not_active IP Right Cessation
- 1989-12-22 ES ES89123768T patent/ES2068881T3/es not_active Expired - Lifetime
- 1989-12-22 EP EP89123768A patent/EP0374947B1/en not_active Expired - Lifetime
- 1989-12-22 NO NO89895236A patent/NO895236L/no unknown
-
1995
- 1995-04-03 GR GR950400805T patent/GR3015661T3/el unknown
-
1996
- 1996-07-11 HK HK123196A patent/HK123196A/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
HU896768D0 (en) | 1990-03-28 |
MX166369B (es) | 1993-01-05 |
PT92670B (pt) | 1995-09-12 |
JP2930708B2 (ja) | 1999-08-03 |
HU209459B (en) | 1994-06-28 |
DK665589A (da) | 1990-06-24 |
PT92670A (pt) | 1990-06-29 |
DK665589D0 (da) | 1989-12-22 |
DE68921582T2 (de) | 1995-07-06 |
KR0163758B1 (ko) | 1999-01-15 |
IL92860A (en) | 1995-08-31 |
NO895236L (no) | 1990-06-25 |
CN1044461A (zh) | 1990-08-08 |
HK123196A (en) | 1996-07-19 |
CA2006372A1 (en) | 1990-06-23 |
WO1990007342A1 (en) | 1990-07-12 |
JPH03502937A (ja) | 1991-07-04 |
BR8907282A (pt) | 1991-03-12 |
EP0374947A1 (en) | 1990-06-27 |
IL92860A0 (en) | 1990-09-17 |
KR900009565A (ko) | 1990-07-04 |
NO895236D0 (no) | 1989-12-22 |
CA2006372C (en) | 2002-07-02 |
ES2068881T3 (es) | 1995-05-01 |
GR3015661T3 (en) | 1995-07-31 |
EP0374947B1 (en) | 1995-03-08 |
FI896248A0 (fi) | 1989-12-22 |
DE68921582D1 (de) | 1995-04-27 |
CN1025735C (zh) | 1994-08-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FG | Patent granted |
Owner name: THE DOW CHEMICAL COMPANY |
|
MA | Patent expired |