DE2260933C3 - Verfahren zur Herstellung von durch radioaktives Halogen markierten organischen Verbindungen - Google Patents
Verfahren zur Herstellung von durch radioaktives Halogen markierten organischen VerbindungenInfo
- Publication number
- DE2260933C3 DE2260933C3 DE2260933A DE2260933A DE2260933C3 DE 2260933 C3 DE2260933 C3 DE 2260933C3 DE 2260933 A DE2260933 A DE 2260933A DE 2260933 A DE2260933 A DE 2260933A DE 2260933 C3 DE2260933 C3 DE 2260933C3
- Authority
- DE
- Germany
- Prior art keywords
- halogen
- iodine
- labeled
- exchange
- compounds
- 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
- 229910052736 halogen Inorganic materials 0.000 title claims description 23
- 150000002367 halogens Chemical class 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 17
- 150000002894 organic compounds Chemical class 0.000 title claims description 7
- 230000002285 radioactive effect Effects 0.000 title claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 239000011630 iodine Substances 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 15
- 238000002844 melting Methods 0.000 claims description 11
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 3
- 150000002896 organic halogen compounds Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000011084 recovery Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- FVAUCKIRQBBSSJ-LAIFMVDKSA-M sodium;iodine-131(1-) Chemical compound [Na+].[131I-] FVAUCKIRQBBSSJ-LAIFMVDKSA-M 0.000 description 5
- 150000002366 halogen compounds Chemical class 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- VLHRIOASVODQEX-WLDNQIQOSA-N [2-[(6s,8s,9s,10r,11s,13s,14s,16r,17s)-6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)COC(C)=O)[C@@]2(C)C[C@@H]1O VLHRIOASVODQEX-WLDNQIQOSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XUIIKFGFIJCVMT-LBPRGKRZSA-N L-thyroxine Chemical compound IC1=CC(C[C@H]([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-LBPRGKRZSA-N 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 229950008325 levothyroxine Drugs 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- PUZPDOWCWNUUKD-ULWFUOSBSA-M sodium;fluorine-18(1-) Chemical compound [18F-].[Na+] PUZPDOWCWNUUKD-ULWFUOSBSA-M 0.000 description 2
- ZVYLQUJPYVRIKE-RKIXBIESSA-N (8s,9s,10r,13s,14s,16r,17s)-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)CC2 ZVYLQUJPYVRIKE-RKIXBIESSA-N 0.000 description 1
- HXGPNAFIOIDAIU-UHFFFAOYSA-N 2,4,6-triiodo-3-(methylamino)benzoic acid Chemical compound CNC1=C(I)C=C(I)C(C(O)=O)=C1I HXGPNAFIOIDAIU-UHFFFAOYSA-N 0.000 description 1
- CRVYPNHLIAWRNV-UHFFFAOYSA-N 2,4,6-triiodobenzoic acid Chemical compound OC(=O)C1=C(I)C=C(I)C=C1I CRVYPNHLIAWRNV-UHFFFAOYSA-N 0.000 description 1
- BZEHYVFQYWQHPC-UHFFFAOYSA-N 3-acetamido-2,4,6-trichlorobenzoic acid Chemical compound CC(=O)NC1=C(Cl)C=C(Cl)C(C(O)=O)=C1Cl BZEHYVFQYWQHPC-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 1
- FFINMCNLQNTKLU-UHFFFAOYSA-N adipiodone Chemical compound OC(=O)C1=C(I)C=C(I)C(NC(=O)CCCCC(=O)NC=2C(=C(C(O)=O)C(I)=CC=2I)I)=C1I FFINMCNLQNTKLU-UHFFFAOYSA-N 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000007449 liver function test Methods 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- OXDYCJOPPBIFHS-UHFFFAOYSA-N n,n-dimethyl-1-phenylmethanesulfonamide Chemical compound CN(C)S(=O)(=O)CC1=CC=CC=C1 OXDYCJOPPBIFHS-UHFFFAOYSA-N 0.000 description 1
- WCFDSGHAIGTEKL-UHFFFAOYSA-N n,n-dimethylmethanesulfonamide Chemical compound CN(C)S(C)(=O)=O WCFDSGHAIGTEKL-UHFFFAOYSA-N 0.000 description 1
- LXZGVFCKZRHKMU-UHFFFAOYSA-N n-benzyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- FVAUCKIRQBBSSJ-FXMLPJBTSA-M sodium;iodine-125(1-) Chemical compound [Na+].[125I-] FVAUCKIRQBBSSJ-FXMLPJBTSA-M 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940056501 technetium 99m Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001685 thyroid gland Anatomy 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
- A61K51/0493—Steroids, e.g. cholesterol, testosterone
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Steroid Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2260933A DE2260933C3 (de) | 1972-12-08 | 1972-12-08 | Verfahren zur Herstellung von durch radioaktives Halogen markierten organischen Verbindungen |
| CH1652673A CH593881A5 (enExample) | 1972-12-08 | 1973-11-23 | |
| US05/421,818 US3933869A (en) | 1972-12-08 | 1973-12-05 | Preparation of organic radiohalogen compounds |
| BE138655A BE808384A (fr) | 1972-12-08 | 1973-12-07 | Procede de preparation de composes organiques de radio-halogene |
| FR7343932A FR2209584B1 (enExample) | 1972-12-08 | 1973-12-10 | |
| GB5709273A GB1458677A (en) | 1972-12-08 | 1973-12-10 | Process for the manufacture of organic radio-halogen compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2260933A DE2260933C3 (de) | 1972-12-08 | 1972-12-08 | Verfahren zur Herstellung von durch radioaktives Halogen markierten organischen Verbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2260933A1 DE2260933A1 (de) | 1974-06-12 |
| DE2260933B2 DE2260933B2 (de) | 1980-11-13 |
| DE2260933C3 true DE2260933C3 (de) | 1981-08-20 |
Family
ID=5864296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2260933A Expired DE2260933C3 (de) | 1972-12-08 | 1972-12-08 | Verfahren zur Herstellung von durch radioaktives Halogen markierten organischen Verbindungen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3933869A (enExample) |
| BE (1) | BE808384A (enExample) |
| CH (1) | CH593881A5 (enExample) |
| DE (1) | DE2260933C3 (enExample) |
| FR (1) | FR2209584B1 (enExample) |
| GB (1) | GB1458677A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4321208A (en) * | 1976-09-27 | 1982-03-23 | Velayudhan Sahadevan | Preparation of directly iodinated steroid hormones and related compounds |
| DE2914089C2 (de) * | 1979-04-07 | 1982-02-11 | Kernforschungsanlage Jülich GmbH, 5170 Jülich | Verfahren zur Herstellung von ω-↑123↑J-markierten Fettsäuren |
| US4430321A (en) * | 1982-01-15 | 1984-02-07 | Merck Frosst Canada Inc. | 6-Bromocholesterol derivatives |
| DE3424525A1 (de) * | 1984-07-04 | 1986-01-16 | Kernforschungsanlage Jülich GmbH, 5170 Jülich | Verfahren zur herstellung von (pfeil hoch)1(pfeil hoch)(pfeil hoch)8(pfeil hoch)f-alkyl- und arylverbindungen durch halogenaustausch |
| US4966999A (en) * | 1988-06-07 | 1990-10-30 | Cytogen Corporation | Radiohalogenated compounds for site specific labeling |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3728351A (en) * | 1968-05-31 | 1973-04-17 | Univ Michigan | Radioiodinated quinoline derivatives |
| US3644441A (en) * | 1969-11-17 | 1972-02-22 | Schering Ag | Method for the production of 21-fluoro-4 6-pregnadienes |
| US3784576A (en) * | 1970-09-24 | 1974-01-08 | Univ Michigan | Halogenated cholesterol |
-
1972
- 1972-12-08 DE DE2260933A patent/DE2260933C3/de not_active Expired
-
1973
- 1973-11-23 CH CH1652673A patent/CH593881A5/xx not_active IP Right Cessation
- 1973-12-05 US US05/421,818 patent/US3933869A/en not_active Expired - Lifetime
- 1973-12-07 BE BE138655A patent/BE808384A/xx unknown
- 1973-12-10 FR FR7343932A patent/FR2209584B1/fr not_active Expired
- 1973-12-10 GB GB5709273A patent/GB1458677A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE808384A (fr) | 1974-06-07 |
| CH593881A5 (enExample) | 1977-12-30 |
| DE2260933A1 (de) | 1974-06-12 |
| FR2209584A1 (enExample) | 1974-07-05 |
| FR2209584B1 (enExample) | 1977-04-15 |
| GB1458677A (en) | 1976-12-15 |
| DE2260933B2 (de) | 1980-11-13 |
| US3933869A (en) | 1976-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8330 | Complete disclaimer |