DE646116C - Contrast media for the roentgenological visualization of hollow systems of the body - Google Patents
Contrast media for the roentgenological visualization of hollow systems of the bodyInfo
- Publication number
- DE646116C DE646116C DE1930646116D DE646116DD DE646116C DE 646116 C DE646116 C DE 646116C DE 1930646116 D DE1930646116 D DE 1930646116D DE 646116D D DE646116D D DE 646116DD DE 646116 C DE646116 C DE 646116C
- Authority
- DE
- Germany
- Prior art keywords
- contrast media
- visualization
- roentgenological
- diiodo
- pyridone
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Es ist bekannt, daß halogenhaltige Stoffe, insbesondere Jodverbindungen, vielfach Röntgenkontrastmittel sind, die für die röntgenographische Darstellung von Organen, besonders auch der Harnwege, von Bedeutung sind. Das Bestreben der Technik geht nun dahin, durch Steigerung der Halogenkonzentration eine Vertiefung des Röntgenschattens zu erzielen. Man hat deshalb schon 2-PyridoneIt is known that halogen-containing substances, in particular iodine compounds, often use X-ray contrast media that are important for the radiographic representation of organs, especially the urinary tract. The endeavors of the technology now go by increasing the halogen concentration to achieve a deepening of the X-ray shadow. So you already have 2-pyridones
ίο mit hohem Jodgehalt dargestellt. Derartige Verbindungen zeigten aber als Röntgenkontrastmittel gegenüber den mono jodsubstituierten 2-Pyridonen keine Vorzüge, da die Einführung eines zweiten Jodatoms die Löslichkeit außerordentlich herabsetzt, so daß die intravenöse Darreichung sich als unmöglich erwies. ίο shown with high iodine content. Such connections but showed no advantages as an X-ray contrast medium compared to the mono-iodine-substituted 2-pyridones, since the introduction of a second iodine atom extremely lowers the solubility, so that the intravenous Administration proved impossible.
Es wurde nun gefunden, daß die 3, 5-D1-halogen-4-pyridone, die am Stickstoff löslichmachende Gruppen tragen, insbesondere die Brom- und Jodverbindungen, im Gegensatz zu den entsprechenden 2-Pyridonen infolge ihrer bedeutend größeren Wasserlöslichkeit und infolge ihrer physiologischen Indifferenz ohne weiteres für die röntgenographische Darstellung z. B. der Harnwege verwendbar sind, zumal sie sich durch ihre bemerkenswerte Ungiftigkeit auszeichnen. Als löslichmachende Substituenten am Stickstoff kommen z. B. die Reste organischer Carbonsäuren und Sulfonsäuren sowie Alkyl- und Alkylaminoalkylreste in Frage.It has now been found that the 3, 5-D1-halogen-4-pyridones, which carry solubilizing groups on the nitrogen, in particular the Bromine and iodine compounds, in contrast to the corresponding 2-pyridones as a result their significantly greater water solubility and as a result of their physiological indifference easily for the radiographic representation z. B. the urinary tract can be used especially since they are distinguished by their remarkable non-toxicity. As a solubilizing agent Substituents on nitrogen come, for. B. the radicals of organic carboxylic acids and sulfonic acids and alkyl and alkylaminoalkyl radicals in question.
Die Anwendung der neuen Verbindungen erfolgt z. B. in der folgenden Weise:The application of the new connections takes place z. B. in the following way:
Einem Hunde von 26 kg werden 10 g 3, 5"dijod-4-pyridon-N-essigsaures Natrium intravenös verabreicht. Der Harn des Tieres enthält dann von der ersten bis zur fünften Stunde nach der Injektion etwa 5,3 °/o organisch gebundenes Jod gegenüber einem maximalen Gehalt von etwa 2,5 °/0 nach Verabreichung der entsprechenden Monojodverbindung. Infolgedessen ist die erzielte Röntgenkontrastwirkung etwa doppelt so stark, so daß sich sehr gute Röntgenbilder von den Harnwegen auf diese Weise herstellen lassen.10 g of 3.5 "diiodo-4-pyridone-N-acetic acid sodium are administered intravenously to a dog weighing 26 kg. The urine of the animal then contains about 5.3% organically bound from the first to the fifth hour after the injection iodine compared to a maximum content of about 2.5 ° / 0 after administration of the corresponding Monojodverbindung. Consequently, the X-ray contrast effect achieved is about twice as strong, so that blank excellent X-ray images of the urinary tract in this way produce.
Anstatt durch intravenöse Injektion kann man das Kontrastmittel z. B. auch durch Uretherenkatheter dem Organismus einverleiben.Instead of intravenous injection, you can use the contrast agent z. B. also by ureter catheter incorporate into the organism.
Ähnliche Ergebnisse wie das 3, 5-dijod-4-pyridon-N-essigsaure Natrium liefern z. B. Salze des N-Diäthylaminäthyl-3, 5-dijod-4-pyridons, das N-Methyl-3, 5-dijod-4-pyridon (F. 2070), das 3,5-Dijod-4-pyridon-N-acetamid (F. 275°), das N-(/?, y-Dioxypropyl)-3, 5-dijod-4-pyridon (F. i6i°), dasResults similar to those of 3, 5-diiodo-4-pyridone-N-acetic acid sodium are obtained, for. B. Salts of N-diethylamine ethyl-3, 5-diiodo-4-pyridone, N-methyl-3, 5-diiodo-4-pyridone (F. 207 0 ), 3,5-diiodo-4-pyridone N-acetamide (m.p. 275 °), the N - (/ ?, γ-dioxypropyl) -3, 5-diiodo-4-pyridone (m.p. 16 °), the
*) Von dem Patentsucher sind als die Erfinder angegeben worden:*) The patent seeker indicated the following as the inventors:
Dr. Joachim Reitmann und Dr. Gerhard Hecht in Wnppertal-Vohwinkel.Dr. Joachim Reitmann and Dr. Gerhard Hecht in Wnppertal-Vohwinkel.
N - Methyl-^-,N - methyl - ^ -,
X-(/?-oxyäthyl)-3,5-dijod-4-pyridon(F.20o=),
ferner Salze der 3, s-Dijod-j.-pyridon-X-äthansulfosäure
(F. i8o°j und der
3, 5-dijodchelidamsäure.X - (/? - oxyethyl) -3,5-diiodo-4-pyridone (F.20o =), also salts of 3, s-diiodo-j.-pyridone-X-ethanesulfonic acid (F. 18o ° j and der
3, 5-diiodochelidamic acid.
Auch bei der Anwendung am Mensche? haben die neuen Kontrastmittel eine her^ogjj ragende Kontrastwirkung gezeigt. ^ Also when used on people? the new contrast media have shown an excellent contrast effect. ^
Claims (1)
Kontrastmittel zur röntgenologischen Sichtbarmachung von Hohlsystemen des »Körpers, bestehend aus 3, 5-Dijod- oder *''3, 5-Dibrom-4-pyridonen, die am Stickstoff durch löslichmachende Gruppen substituiert sind.Claim:
Contrast media for the radiological visualization of hollow systems of the »body, consisting of 3, 5-diiodo- or * '' 3, 5-dibromo-4-pyridones, which are substituted on the nitrogen by solubilizing groups.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE646116T | 1930-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE646116C true DE646116C (en) | 1937-06-08 |
Family
ID=6580819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930646116D Expired DE646116C (en) | 1930-12-21 | 1930-12-21 | Contrast media for the roentgenological visualization of hollow systems of the body |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE646116C (en) |
-
1930
- 1930-12-21 DE DE1930646116D patent/DE646116C/en not_active Expired
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