EP0014957A1 - Process for separating technetium-99m from molybdenum-99 - Google Patents
Process for separating technetium-99m from molybdenum-99 Download PDFInfo
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- EP0014957A1 EP0014957A1 EP80100734A EP80100734A EP0014957A1 EP 0014957 A1 EP0014957 A1 EP 0014957A1 EP 80100734 A EP80100734 A EP 80100734A EP 80100734 A EP80100734 A EP 80100734A EP 0014957 A1 EP0014957 A1 EP 0014957A1
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- aluminum oxide
- copper
- copper salt
- technetium
- salt
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- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21G—CONVERSION OF CHEMICAL ELEMENTS; RADIOACTIVE SOURCES
- G21G1/00—Arrangements for converting chemical elements by electromagnetic radiation, corpuscular radiation or particle bombardment, e.g. producing radioactive isotopes
- G21G1/04—Arrangements for converting chemical elements by electromagnetic radiation, corpuscular radiation or particle bombardment, e.g. producing radioactive isotopes outside nuclear reactors or particle accelerators
Definitions
- the invention relates to a process for separating technetium-99m from molybdenum-99 bound to aluminum oxide with eluents from nuclide generators, characterized in that a copper salt, preferably a copper (II) salt, is added to the elution system.
- a copper salt preferably a copper (II) salt
- Salt solutions in particular physiological salt solutions such as physiological saline, and furthermore dilute mineral acids such as dilute hydrochloric acid or nitric acid, are expediently used as eluents.
- the nitrate, acetate and preferably the chloride are used as the copper (II) salt.
- a copper salt such as CuCl 2 .2H 2 O in 10 -2 to 10 -6 molar - preferably in 2 x 10 -4 to 2 ⁇ 10 -5 molar - dissolved concentration, or the copper salt is fixed on the aluminum oxide in a weight ratio of Cu salt to Al 2 0 3 between appropriately 1:10 and 1: 5000 - preferably between 1:50 and 1: 300.
- the corresponding amount of copper salt is dissolved in water and the aluminum oxide (acidic) is suspended in this solution.
- the pH is then slowly adjusted to a value between 4 and 9 - preferably between 6.5 and 7.5 - and the aluminum oxide loaded with copper salt is filtered off and at temperatures between 120 and 250 ° C., preferably at 180-220 ° C, dried.
- the generator column is advantageously produced in such a way that only 1/20 to 1/2, preferably 1/10 to 1/3, of the alumina volume at the upper end of the column where the Mo-99 is later fixed, filled with the aluminum oxide loaded with copper salt, while the remaining part of the space available in the column for the aluminum oxide is filled with untreated aluminum oxide (acidic).
- the copper ion content in the eluate is generally below 1 ppm, it being immaterial within the limits specified how much copper salt is added to the eluent or the aluminum oxide. (The normal level of copper in human serum is around 1.2 ppm.)
- the method according to the invention enables the production and the operation of technetium generators without loss of yield by radiation reduction; it is neither necessary to suck the generator column dry between the individual elutions, nor can a significant part of the yield stabilizer used get into the eluate.
- Table 1 shows that when CuCl2-2H20 is added to the eluent, the elution yield is around 80% in the expected range, whereas without this addition it drops significantly below this value after the 3rd elution.
- Table 2 shows that the addition of CuCl2 ⁇ 2H20 to aluminum oxide prevents breakdowns in yield which can occur very massively under certain circumstances without this addition.
- Table 3 shows that the addition of copper (II) chloride to aluminum oxide results in the elution yields of the expected magnitude over the entire period of use, while without this addition they are significantly lower from the 3rd elution onwards.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- High Energy & Nuclear Physics (AREA)
- Manufacture And Refinement Of Metals (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
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Abstract
Description
In der nuklearmedizinischen Diagnostik hat sich in den letzten Jahren Technetium-99m wegen seiner günstigen physikalischen Eigenschaften (keine Korpuskularstrahlung, γ-Energie von 140 keV, Halbwertszeit von 6 h) und der damit verbundenen geringen Strahlenbelastung für Patienten und Personal weitgehend durchgesetzt. Wegen der kurzen Halbwertszeit des Technetium-99m und den damit verbundenen starken Aktivitätsverlusten beim Transport wird es nur noch selten in isolierter Form versandt. Mit einem Technetium-Generator kann Tc-99m leicht von seinem Mutternuklid Mo-99 abgetrennt werden. Wegen der längeren Halbwertszeit von Mo-99 (HWZ = 66,7 h) werden die durch den Transport bedingten Aktivi tätsverluste in Grenzen gehalten. Weil nach Abtrennung des Tc-99m durch Elution aus dem noch auf der Säule vorhandenen Molybdän-99 wieder Technetium-99m nachge- bildet wird, kann ein Technetium-99m-Generator ein bis zwei Wochen lang täglich ein- bis zweimal eluiert werden.Technetium-99m has been widely used in nuclear medicine diagnostics in recent years due to its favorable physical properties (no corpuscular radiation, γ energy of 140 keV, half-life of 6 h) and the associated low radiation exposure for patients and staff. Due to the short half-life of the Technetium-99m and the associated strong loss of activity during transport, it is rarely shipped in isolated form. With a technetium generator, Tc-99m can be easily separated from its mother nuclide Mo-99. Due to the longer half-life of Mo-99 (HWZ = 66.7 h), the loss of activity due to transport is kept within limits. Because after Separation of Tc-99m by elution from the still present on the column of molybdenum-99 again technetium-99m nachg e - is forming a technetium-99m generator can be eluted a single daily for up to two weeks or twice.
Es ist bekannt, daß die berechneten Mengen an Technetium-99m vor allem bei Generatoren mit einer größeren Mo-99-Beladung oft deutlich unterschritten werden. Diese Ausbeuteeinbußen, in besonderen Fällen Ausbeutezusammenbrüche werden durch "Strahlenreduktion" verursacht. Die als ß-Strahlung des Mo-99 emittierten Elektronen reduzieren das in der Aluminiumoxid-Säule als Pertechnetat-Ion Tc04- vorliegende Technetium (Oxidationsstufe + 7) zu einer niedrigeren Oxidationsstufe. Das reduzierte Technetium ist im Gegensatz zum Pertechnetat an das Aluminiumoxid der Generatorsäule gebunden und kann nicht eluiert werden. Je größer die Strahlendosis in dem Teil der Säule ist, in dem das Tc-99m entsteht, desto mehr Pertechnetat wird reduziert. Bei Generatoren, die mit aus den Spaltprodukten des Uran-235 gewonnenem Mo-99 (sogenanntem Spaltmolybdän) hergestellt werden, ist dieser Teil der Säule wegen der hohen spezifischen Aktivität des Mo-99 bsonders klein und folglich die absorbierte Dosis besonders hoch. Deshalb ist auch das Risiko der Ausbeuteverminderung bei mit Spaltmolybdän hergestellten Generatoren besonders hoch.It is known that the calculated amounts of technetium-99m, especially in generators with a larger Mo-99 load, are often significantly undercut. This loss of yield, in particular cases collapse in yield, is caused by "radiation reduction". The electrons emitted as β-radiation from Mo-99 reduce the technetium present in the aluminum oxide column as pertechnetate ion Tc04- (oxidation level + 7) to a lower oxidation level. In contrast to the pertechnetate, the reduced technetium is bound to the aluminum oxide of the generator column and cannot be eluted. The greater the radiation dose in the part of the column in which the Tc-99m is generated, the more pertechnetate is reduced. In the case of generators which are produced using Mo-99 (so-called fission molybdenum) obtained from the fission products of uranium-235, this part of the column is particularly small because of the high specific activity of the Mo-99 and consequently the absorbed dose is particularly high. This is why the risk of reducing the yield of generators made with split molybdenum is particularly high.
Um Ausbeuteeinbußen durch Strahlenreduktion zu verhindern, sind mehrere Möglichkeiten beschrieben worden, die jedoch alle gewisse Nachteile haben.
- 1. Man kann einer als Elutionsmittel dienenden physiologischen Kochsalzlösung ein Oxidationsmittel wie H202 oder NaOCl zusetzen, das das reduzierte Technetium wieder zum Pertechnetat oxidiert. Der Nachteil dieses Verfahrens besteht darin, daß solche Oxidationsmittel vor der Verwendung der Eluate für die Markierung bestimmter organspezifischer Substanzen wieder zerstört werden muß, z.B. durch Verkochen.
- 2. Bringt man nach jeder Elution durch Trockensaugen der Säule frischen Sauerstoff in das System, so wird die Strahlenreduktion so lange verhindert, wie noch genug Sauerstoff in der Säule vorhanden ist. Der Nachteil dieser Methode ist eine umständlichere Elutionstechnik.
- 3. Aus DE-AS 22 38 503 ist bekannt, daß durch den Zusatz von Nitrat oder Nitrit zum Elutionsmittel die Reduktion des Pertechnetat-Ions verhindert werden kann. Gegen die Verwendung von Nitrat und Nitrit, die beide ins Eluat und somit in den Organismus gelangen, spricht die noch nicht geklärte Rolle, die Nitrit, das in kleinen Mengen auch aus dem Nitrat entsteht, bei der Krebsbildung spielt.
- 1. An oxidizing agent such as H 2 O 2 or NaOCl, which oxidizes the reduced technetium back to the pertechnetate, can be added to a physiological saline solution serving as an eluent. The disadvantage of this method is that such oxidizing agents are destroyed again before the eluates are used to label certain organ-specific substances must be, for example by boiling.
- 2. If fresh oxygen is brought into the system after each elution by vacuuming the column dry, the radiation reduction is prevented as long as there is still enough oxygen in the column. The disadvantage of this method is a more complicated elution technique.
- 3. From DE-AS 22 38 503 it is known that the reduction of the pertechnetate ion can be prevented by the addition of nitrate or nitrite to the eluent. The use of nitrate and nitrite, which both get into the eluate and thus into the organism, is spoken against by the as yet unexplained role of nitrite, which also arises in small quantities from the nitrate, in cancer formation.
Gegenstand der Erfindung ist ein Verfahren zur Trennung von Technetium-99m von an Aluminiumoxid gebundenem Molybdän-99 mit Elutionsmitteln aus Nuklidgeneratoren, dadurch gekennzeichnet, daß man dem Elutionssystem ein Kupfer-Salz, vorzugsweise ein Kupfer-(II)-Salz, zusetzt.The invention relates to a process for separating technetium-99m from molybdenum-99 bound to aluminum oxide with eluents from nuclide generators, characterized in that a copper salt, preferably a copper (II) salt, is added to the elution system.
Als Elutionsmittel werden zweckmäßig Salzlösungen, insbesondere physiologische Salzlösungen wie physiologische Kochsalzlösung, weiterhin verdünnte Mineralsäuren wie verdünnte Salzsäure oder Salpetersäure, verwendet.Salt solutions, in particular physiological salt solutions such as physiological saline, and furthermore dilute mineral acids such as dilute hydrochloric acid or nitric acid, are expediently used as eluents.
Als Kupfer-(II)-Salz werden insbesondere das Nitrat, Acetat und vorzugsweise das Chlorid verwendet.In particular, the nitrate, acetate and preferably the chloride are used as the copper (II) salt.
Zur Durchführung des Verfahrens wird entweder im Elutionsmittel ein Kupfer-Salz, wie CuCl2·2H2O, in 10-2 bis 10-6 molarer - vorzugsweise in 2·10-4 bis 2·10-5 molarer - Konzentration gelöst, oder das Kupfer-Salz wird auf dem Aluminiumoxid im Gewichtsverhältnis Cu-Salz zu Al203 zwischen zweckmäßig 1:10 und 1:5000 - vorzugsweise zwischen 1:50 und 1:300 - fixiert.To perform the process is either in the eluant a copper salt such as CuCl 2 .2H 2 O in 10 -2 to 10 -6 molar - preferably in 2 x 10 -4 to 2 × 10 -5 molar - dissolved concentration, or the copper salt is fixed on the aluminum oxide in a weight ratio of Cu salt to Al 2 0 3 between appropriately 1:10 and 1: 5000 - preferably between 1:50 and 1: 300.
Zur Fixierung des Kupfer-Salzes auf dem Aluminiumoxid wird die entsprechende Menge Kupfer-Salz in Wasser gelöst und das Aluminiumoxid (sauer) in dieser Lösung suspendiert. Anschließend wird der pH langsam auf einen Wert zwischen 4 und 9 - vorzugsweise zwischen 6,5 und 7,5 - eingestellt, das so mit Kupfer-Salz beladene Aluminiumoxid abfiltriert und bei Temperaturen zwischen 120 und 250°C, vorzugsweise bei 180 - 220°C, getrocknet.To fix the copper salt on the aluminum oxide, the corresponding amount of copper salt is dissolved in water and the aluminum oxide (acidic) is suspended in this solution. The pH is then slowly adjusted to a value between 4 and 9 - preferably between 6.5 and 7.5 - and the aluminum oxide loaded with copper salt is filtered off and at temperatures between 120 and 250 ° C., preferably at 180-220 ° C, dried.
Um den Gehalt an Kupferionen im Eluat niedrig zu halten, wird in diesem Fall die Generatorsäule vorteilhaft so hergestellt, daß nur 1/20 bis 1/2, vorzugsweise 1/10 bis 1/3, des Aluminiumoxid-Volumens am oberen Ende der Säule, wo später das Mo-99 fixiert wird, mit dem mit Kupfer-Salz beladenen Aluminiumoxid gefüllt wird, während der verbleibende Teil des in der Säule für das Aluminiumoxid zur Verfügung stehenden Raums mit unbehandeltem Aluminiumoxid (sauer) gefüllt wird.In this case, in order to keep the copper ion content in the eluate low, the generator column is advantageously produced in such a way that only 1/20 to 1/2, preferably 1/10 to 1/3, of the alumina volume at the upper end of the column where the Mo-99 is later fixed, filled with the aluminum oxide loaded with copper salt, while the remaining part of the space available in the column for the aluminum oxide is filled with untreated aluminum oxide (acidic).
Bei beiden Verfahrensweisen liegt der Gehalt an Kupferionen im Eluat in der Regel unter 1 ppm, wobei es in den angegebenen Grenzen gleichgültig ist, wieviel Kupfer-Salz dem Elutionsmittel bzw. dem Aluminiumoxid zugesetzt wird. (Der normale Gehalt an Kupfer im menschlichen Serum liegt bei etwa 1,2 ppm.)In both procedures, the copper ion content in the eluate is generally below 1 ppm, it being immaterial within the limits specified how much copper salt is added to the eluent or the aluminum oxide. (The normal level of copper in human serum is around 1.2 ppm.)
Das Verfahren gemäß der Erfindung ermöglicht die Herstellung und den Betrieb von Technetiumgeneratoren ohne Ausbeuteeinbuße durch Strahlenreduktion; dabei ist es weder erforderlich, zwischen den einzelnen Elutionen die Generatorsäule trockenzusaugen, noch kann ein nennenswerter Teil des verwendeten Ausbeutestabilisators ins Eluat gelangen.The method according to the invention enables the production and the operation of technetium generators without loss of yield by radiation reduction; it is neither necessary to suck the generator column dry between the individual elutions, nor can a significant part of the yield stabilizer used get into the eluate.
Es werden mehrere Generatorsäulen, die je 1,4 g Aluminiumoxid S, sauer, superaktiv; Fa. Riedel de Haen, Best.-Nr. 31183 enthalten, mit einer Spaltmolybdän-Lösung beladen und arbeitstäglich eluiert, wobei als Elutionsmittel physiologische Kochsalzlösung verwendet wird, der unterschiedliche Mengen an CuCl2·2H2O zugesetzt wurde. In Tabelle 1 sind die Elutionsausbeuten in % bezogen auf die vorhandene Mo-99-Aktivität angegeben.
Aus Tabelle 1 geht hervor, daß bei Zusatz von CuCl2-2H20 zum Elutionsmittel die Elutionsausbeute mit etwa 80% im zu erwartenden Bereich liegt, während sie ohne diesen Zusatz ab der 3. Elution deutlich unter diesem Wert sinkt.Table 1 shows that when CuCl2-2H20 is added to the eluent, the elution yield is around 80% in the expected range, whereas without this addition it drops significantly below this value after the 3rd elution.
10 g CuCl2·2H2O werden in 400 ml bidest. Wasser gelöst. Dann werden unter kräftigem Rühren 200 g Al2O3 (sauer) langsam.zugegeben. Anschließend werden 10 ml 20%ige Natronlauge zugesetzt und solange gerührt (15 - 20 min.), bis sich der pH-Wert stabilisiert hat (er beträgt dann etwa 8,5). Danach wird der pH-Wert mit konz. Salzsäure (ca. 0,5 ml) etwa auf pH 7 gebracht. Wenn sich der pH-Wert stabilisiert hat, wird dekantiert, mit bidest. Wasser aufgeschlämmt, erneut dekantiert und 15 Stunden bei 200°C getrocknet.10 g of CuCl 2 .2H 2 O are redistilled in 400 ml. Water dissolved. Then 200 g of Al 2 O 3 (acidic) are slowly added with vigorous stirring. 10 ml of 20% sodium hydroxide solution are then added and the mixture is stirred (15-20 min.) Until the pH has stabilized (it is then about 8.5). Then the pH value with conc. Hydrochloric acid (approx. 0.5 ml) brought to about pH 7. When the pH has stabilized, decant with bidist. water slurried, decanted again and dried at 200 ° C for 15 hours.
In eine Glassäule werden 1 g unbehandeltes Aluminiumoxid (sauer) und darüber 150 mg eines wie oben beschriebenen mit Kupfer-(II)-Ionen beladenen Aluminiumoxids eingefüllt. Diese Säule wird mit Mo-99 beladen und arbeitstäglich eluiert. Als Elutionsmittel diente eine physiologische Kochsalzlösung, die mit üblicherweise zur Verpackung dienender PVC-Folie zusammen im Autoklaven erhitzt wurde. Es ist bekannt, daß dabei ein Teil des Weichmachers der Folie in das Elutionsmittel gelangt, und daß durch solche organischen Verunreinigungen starke Ausbeuteverminderungen auftreten. Zum Vergleich wurde eine Säule untersucht, die nur unbehandeltes Aluminiumoxid enthielt.1 g of untreated aluminum oxide (acidic) and 150 mg of an aluminum oxide loaded with copper (II) ions as described above are introduced into a glass column. This column is loaded with Mo-99 and eluted every working day. A physiological saline solution was used as the eluent, which was heated together in an autoclave with PVC film that is usually used for packaging. It is known that part of the plasticizer of the film gets into the eluent and that such organic impurities reduce yields considerably. For comparison, a column was examined which only contained untreated aluminum oxide.
Die Elutionsausbeuten sind in Tabelle 2 angegeben:
Tabelle 2 zeigt, daß durch den Zusatz von CuCl2·2H20 zu Aluminiumoxid Ausbeutezusammenbrüche verhindert werden, die ohne diesen Zusatz unter bestimmten Umständen sehr massiv auftreten können.Table 2 shows that the addition of CuCl2 · 2H20 to aluminum oxide prevents breakdowns in yield which can occur very massively under certain circumstances without this addition.
Entsprechend dem in Beispiel 2 angegebenen Verfahren wurden Säulen mit 10, 20, 30, 40 und 50 mg CuCl2·2H2O pro g Al203 hergestellt und arbeitstäglich eluiert. Die Elutionsausbeuten sind in Tabelle 3 angegeben:
Tabelle 3 zeigt, daß durch den Zusatz von Kupfer-(II)-chlorid zu Aluminiumoxid die Elutionsausbeuten über den gesamten Verwendungszeitraum in der erwarteten Größenordnung liegen, während sie ohne diesen Zusatz ab der 3. Elution deutlich niedriger sind.Table 3 shows that the addition of copper (II) chloride to aluminum oxide results in the elution yields of the expected magnitude over the entire period of use, while without this addition they are significantly lower from the 3rd elution onwards.
Entsprechend dem in Beispiel 2 angegebenen Verfahren wurden Säulen mit 15 mg Kupfer-(I)-chlorid pro g Al2O3 hergestellt und arbeitstäglich eluiert. Die Ausbeuten sind in Tabelle 4 angegeben:
(bei den mi + gekennzeichneten Werten lag die Regenerationszeit zwischen den Elutionen statt der normalerweise üblichen 24 Stunden bei 72 Stunden).(For the mi + marked values, the regeneration time between elutions was 72 hours instead of the usual 24 hours).
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT80100734T ATE4024T1 (en) | 1979-02-20 | 1980-02-14 | PROCESS FOR SEPARATION OF TECHNETIUM-99M FROM MOLYBDENUM-99. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792906439 DE2906439A1 (en) | 1979-02-20 | 1979-02-20 | METHOD FOR SEPARATING TECHNETIUM-99M FROM MOLYBAEN-99 |
DE2906439 | 1979-02-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0014957A1 true EP0014957A1 (en) | 1980-09-03 |
EP0014957B1 EP0014957B1 (en) | 1983-07-06 |
Family
ID=6063381
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80100734A Expired EP0014957B1 (en) | 1979-02-20 | 1980-02-14 | Process for separating technetium-99m from molybdenum-99 |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0014957B1 (en) |
JP (1) | JPS55113628A (en) |
AT (1) | ATE4024T1 (en) |
DE (2) | DE2906439A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0213589A2 (en) * | 1985-09-03 | 1987-03-11 | Hoechst Aktiengesellschaft | Generator of technecium-99m, its preparation and use |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4229327A1 (en) * | 1992-09-02 | 1994-03-03 | Rossendorf Forschzent | Technetium recovery for use in nuclear medical diagnostics from eluate - obtd. from per:technetate generator by redn. to hydroxide, adsorption, re-oxidation and elution, suitable for clinical field |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1929067A1 (en) * | 1968-07-03 | 1970-01-15 | Squibb & Sons Inc | Eluent for radioisotope generators |
FR2148456A1 (en) * | 1971-08-06 | 1973-03-23 | Radiochemical Centre Ltd |
-
1979
- 1979-02-20 DE DE19792906439 patent/DE2906439A1/en not_active Withdrawn
-
1980
- 1980-02-14 AT AT80100734T patent/ATE4024T1/en not_active IP Right Cessation
- 1980-02-14 EP EP80100734A patent/EP0014957B1/en not_active Expired
- 1980-02-14 DE DE8080100734T patent/DE3064003D1/en not_active Expired
- 1980-02-20 JP JP1928180A patent/JPS55113628A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1929067A1 (en) * | 1968-07-03 | 1970-01-15 | Squibb & Sons Inc | Eluent for radioisotope generators |
FR2148456A1 (en) * | 1971-08-06 | 1973-03-23 | Radiochemical Centre Ltd |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0213589A2 (en) * | 1985-09-03 | 1987-03-11 | Hoechst Aktiengesellschaft | Generator of technecium-99m, its preparation and use |
DE3531355A1 (en) * | 1985-09-03 | 1987-03-12 | Hoechst Ag | TECHNETIUM 99M GENERATOR, ITS PRODUCTION AND USE |
EP0213589A3 (en) * | 1985-09-03 | 1988-03-16 | Hoechst Aktiengesellschaft | Generator of technecium-99m, its preparation and use |
US4837110A (en) * | 1985-09-03 | 1989-06-06 | Hoechst Aktiengesellschaft | Technetium-99m generator, its preparation and its use |
Also Published As
Publication number | Publication date |
---|---|
DE3064003D1 (en) | 1983-08-11 |
JPH0149647B2 (en) | 1989-10-25 |
EP0014957B1 (en) | 1983-07-06 |
JPS55113628A (en) | 1980-09-02 |
DE2906439A1 (en) | 1980-09-04 |
ATE4024T1 (en) | 1983-07-15 |
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