CA1187897A - Acides iminodiacetiques substitues en n - Google Patents
Acides iminodiacetiques substitues en nInfo
- Publication number
- CA1187897A CA1187897A CA000392015A CA392015A CA1187897A CA 1187897 A CA1187897 A CA 1187897A CA 000392015 A CA000392015 A CA 000392015A CA 392015 A CA392015 A CA 392015A CA 1187897 A CA1187897 A CA 1187897A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- prepared
- methyl
- water soluble
- soluble salt
- 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
Links
- -1 N-substituted iminodiacetic acids Chemical class 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 239000011630 iodine Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 41
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- MHPZZZZLAQGTHT-UHFFFAOYSA-N mebrofenin Chemical compound CC1=CC(C)=C(NC(=O)CN(CC(O)=O)CC(O)=O)C(C)=C1Br MHPZZZZLAQGTHT-UHFFFAOYSA-N 0.000 claims description 3
- SFPXBXKUJFHQQY-UHFFFAOYSA-N 2-[carboxymethyl-[2-(3-iodo-4-methylanilino)-2-oxoethyl]amino]acetic acid Chemical compound CC1=CC=C(NC(=O)CN(CC(O)=O)CC(O)=O)C=C1I SFPXBXKUJFHQQY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims 36
- 235000013350 formula milk Nutrition 0.000 claims 7
- UDLJWHHLPYMPPJ-UHFFFAOYSA-N 2-[[2-(3-bromo-2,6-diethyl-4-methylanilino)-2-oxoethyl]-(carboxymethyl)amino]acetic acid Chemical compound CCC1=CC(C)=C(Br)C(CC)=C1NC(=O)CN(CC(O)=O)CC(O)=O UDLJWHHLPYMPPJ-UHFFFAOYSA-N 0.000 claims 2
- YGEKFHNXRSQDJR-UHFFFAOYSA-N 2-[[2-(3-bromo-4-methylanilino)-2-oxoethyl]-(carboxymethyl)amino]acetic acid Chemical compound CC1=CC=C(NC(=O)CN(CC(O)=O)CC(O)=O)C=C1Br YGEKFHNXRSQDJR-UHFFFAOYSA-N 0.000 claims 2
- IZEFTTLLQCXMCW-UHFFFAOYSA-N 2-[[2-(4-bromo-3-methylanilino)-2-oxoethyl]-(carboxymethyl)amino]acetic acid Chemical compound CC1=CC(NC(=O)CN(CC(O)=O)CC(O)=O)=CC=C1Br IZEFTTLLQCXMCW-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 abstract description 14
- 229940056501 technetium 99m Drugs 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 8
- 239000003638 chemical reducing agent Substances 0.000 abstract description 7
- 238000003384 imaging method Methods 0.000 abstract description 6
- 150000007513 acids Chemical class 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 210000004185 liver Anatomy 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000002002 slurry Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 4
- 229960002799 stannous fluoride Drugs 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 229910014033 C-OH Inorganic materials 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910014570 C—OH Inorganic materials 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 210000000941 bile Anatomy 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 210000001865 kupffer cell Anatomy 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- DJQJFMSHHYAZJD-UHFFFAOYSA-N lidofenin Chemical class CC1=CC=CC(C)=C1NC(=O)CN(CC(O)=O)CC(O)=O DJQJFMSHHYAZJD-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000009206 nuclear medicine Methods 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 229960003330 pentetic acid Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000012217 radiopharmaceutical Substances 0.000 description 2
- 229940121896 radiopharmaceutical Drugs 0.000 description 2
- 230000002799 radiopharmaceutical effect Effects 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 229930187593 rose bengal Natural products 0.000 description 2
- 229940081623 rose bengal Drugs 0.000 description 2
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 2
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 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
- 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 1
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
- PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 description 1
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
- MLMHOTOHNNVYHN-UHFFFAOYSA-N 2-[carboxymethyl-[2-oxo-2-(2-phenylethylamino)ethyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(=O)NCCC1=CC=CC=C1 MLMHOTOHNNVYHN-UHFFFAOYSA-N 0.000 description 1
- MVLMPTBHZPYDBZ-UHFFFAOYSA-N 3-bromo-2,4,6-trimethylaniline Chemical compound CC1=CC(C)=C(Br)C(C)=C1N MVLMPTBHZPYDBZ-UHFFFAOYSA-N 0.000 description 1
- GRXMMIBZRMKADT-UHFFFAOYSA-N 3-bromo-4-methylaniline Chemical compound CC1=CC=C(N)C=C1Br GRXMMIBZRMKADT-UHFFFAOYSA-N 0.000 description 1
- RRUDMHNAMZFNEK-UHFFFAOYSA-N 3-iodo-4-methylaniline Chemical compound CC1=CC=C(N)C=C1I RRUDMHNAMZFNEK-UHFFFAOYSA-N 0.000 description 1
- MMEGELSFOYDPQW-UHFFFAOYSA-N 4-bromo-3-methylaniline Chemical compound CC1=CC(N)=CC=C1Br MMEGELSFOYDPQW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- ZOKXTWBITQBERF-AKLPVKDBSA-N Molybdenum Mo-99 Chemical compound [99Mo] ZOKXTWBITQBERF-AKLPVKDBSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052925 anhydrite Inorganic materials 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 210000003445 biliary tract Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- GHAFORRTMVIXHS-UHFFFAOYSA-L bromosulfophthalein sodium Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(O)=CC=C1C1(C=2C=C(C(O)=CC=2)S([O-])(=O)=O)C(C(Br)=C(Br)C(Br)=C2Br)=C2C(=O)O1 GHAFORRTMVIXHS-UHFFFAOYSA-L 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical class OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229950009740 molybdenum mo-99 Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- FJTPHHNWVXNMEK-IEOVAKBOSA-N octathiocane;technetium-99 Chemical compound [99Tc].S1SSSSSSS1 FJTPHHNWVXNMEK-IEOVAKBOSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 229960001734 sulfobromophthalein Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 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
- A61K51/0478—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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22115580A | 1980-12-29 | 1980-12-29 | |
| US221,155 | 1988-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1187897A true CA1187897A (fr) | 1985-05-28 |
Family
ID=22826582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000392015A Expired CA1187897A (fr) | 1980-12-29 | 1981-12-10 | Acides iminodiacetiques substitues en n |
Country Status (15)
| Country | Link |
|---|---|
| JP (2) | JPS58948A (fr) |
| AT (1) | AT377975B (fr) |
| AU (1) | AU539726B2 (fr) |
| BE (1) | BE891534A (fr) |
| CA (1) | CA1187897A (fr) |
| CH (1) | CH649761A5 (fr) |
| DE (1) | DE3151686A1 (fr) |
| FR (1) | FR2497197B1 (fr) |
| GB (1) | GB2090252B (fr) |
| IE (1) | IE52900B1 (fr) |
| IT (1) | IT1140400B (fr) |
| LU (1) | LU83856A1 (fr) |
| NL (1) | NL193318C (fr) |
| SE (2) | SE461015B (fr) |
| ZA (1) | ZA818943B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4454107A (en) * | 1982-08-30 | 1984-06-12 | Merck & Co., Inc. | Tc99m-Phenida, radioscintigraphic agent for diagnosis of hepatoniliary disease |
| GB8413772D0 (en) * | 1984-05-30 | 1984-07-04 | Nyegaard & Co As | Chemical compounds |
| JPH0331486Y2 (fr) * | 1985-06-24 | 1991-07-04 | ||
| JPH01143751A (ja) * | 1987-11-18 | 1989-06-06 | Corns & Co Ltd | 低圧鋳造装置とその鋳造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725295A (en) * | 1971-07-20 | 1973-04-03 | Atomic Energy Commission | Technetium labeling |
| US4017596A (en) * | 1975-03-03 | 1977-04-12 | Research Corporation | Radiopharmaceutical chelates and method of external imaging |
| CA1070695A (fr) * | 1975-09-02 | 1980-01-29 | Michael D. Loberg | Produit pharmaceutique a base d'acide iminodiacetique |
| CH607920A5 (fr) * | 1976-05-31 | 1978-12-15 | Solco Basel Ag | |
| PL115524B1 (en) * | 1978-04-10 | 1981-04-30 | Uniwersytet Warszawski | Process for manufacturing scintigraphic agent |
| DE2855334A1 (de) * | 1978-12-21 | 1980-07-10 | Hoechst Ag | Technetium-99m-markiertes (2,4,5-trimethylacetanilido)-iminodiacetat zur leberfunktionsdiagnostik und verfahren zur herstellung |
| DE2920174A1 (de) * | 1979-05-18 | 1980-11-20 | Hoechst Ag | Technetium-99m-markierte acetanilidoiminodiacetate zur leberfunktionsdiagnostik |
-
1981
- 1981-12-10 CA CA000392015A patent/CA1187897A/fr not_active Expired
- 1981-12-17 GB GB8138054A patent/GB2090252B/en not_active Expired
- 1981-12-18 BE BE0/206879A patent/BE891534A/fr not_active IP Right Cessation
- 1981-12-18 IE IE3110/81A patent/IE52900B1/en not_active IP Right Cessation
- 1981-12-21 FR FR8123803A patent/FR2497197B1/fr not_active Expired
- 1981-12-22 CH CH8210/81A patent/CH649761A5/fr not_active IP Right Cessation
- 1981-12-23 JP JP56216075A patent/JPS58948A/ja active Granted
- 1981-12-23 AU AU78808/81A patent/AU539726B2/en not_active Expired
- 1981-12-24 LU LU83856A patent/LU83856A1/fr unknown
- 1981-12-24 NL NL8105845A patent/NL193318C/nl not_active IP Right Cessation
- 1981-12-28 SE SE8107806A patent/SE461015B/sv not_active IP Right Cessation
- 1981-12-28 DE DE19813151686 patent/DE3151686A1/de active Granted
- 1981-12-28 ZA ZA818943A patent/ZA818943B/xx unknown
- 1981-12-28 IT IT25861/81A patent/IT1140400B/it active
- 1981-12-29 AT AT0561381A patent/AT377975B/de active
-
1987
- 1987-09-18 SE SE8703623A patent/SE466788B/sv not_active IP Right Cessation
-
1989
- 1989-09-28 JP JP1256895A patent/JPH02160727A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE8703623D0 (sv) | 1987-09-18 |
| DE3151686A1 (de) | 1982-07-08 |
| SE466788B (sv) | 1992-04-06 |
| ZA818943B (en) | 1982-11-24 |
| IT1140400B (it) | 1986-09-24 |
| SE8703623L (sv) | 1987-09-18 |
| BE891534A (fr) | 1982-04-16 |
| ATA561381A (de) | 1984-10-15 |
| SE461015B (sv) | 1989-12-18 |
| IE813110L (en) | 1982-06-29 |
| JPH0237345B2 (fr) | 1990-08-23 |
| DE3151686C2 (fr) | 1990-12-20 |
| SE8107806L (sv) | 1982-06-30 |
| IT8125861A0 (it) | 1981-12-28 |
| AT377975B (de) | 1985-05-28 |
| JPH02160727A (ja) | 1990-06-20 |
| GB2090252B (en) | 1985-01-03 |
| NL8105845A (nl) | 1982-07-16 |
| FR2497197B1 (fr) | 1986-04-11 |
| JPH0316327B2 (fr) | 1991-03-05 |
| NL193318B (nl) | 1999-02-01 |
| CH649761A5 (fr) | 1985-06-14 |
| AU7880881A (en) | 1982-07-08 |
| GB2090252A (en) | 1982-07-07 |
| NL193318C (nl) | 1999-06-02 |
| FR2497197A1 (fr) | 1982-07-02 |
| JPS58948A (ja) | 1983-01-06 |
| LU83856A1 (fr) | 1982-07-07 |
| IE52900B1 (en) | 1988-04-13 |
| AU539726B2 (en) | 1984-10-11 |
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| MKEX | Expiry | ||
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Effective date: 20020528 |