CH338274A - Use as radiopaque agents of polyiodinated phenoxy fatty acids - Google Patents
Use as radiopaque agents of polyiodinated phenoxy fatty acidsInfo
- Publication number
- CH338274A CH338274A CH338274DA CH338274A CH 338274 A CH338274 A CH 338274A CH 338274D A CH338274D A CH 338274DA CH 338274 A CH338274 A CH 338274A
- Authority
- CH
- Switzerland
- Prior art keywords
- fatty acids
- polyiodinated
- radiopaque agents
- phenoxy fatty
- triiodophenoxy
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
Description
Utilisation comme agents radio-opaques de phénoxy-acides gras potyiodés
L'invention se rapporte à l'utilisation, comme agents radio-opaques, de phénoxy-acides gras de formule générale :
EMI1.1
dans laquelle R est un groupe alcoyle inférieur,
R'est un atome d'hydrogène ou un groupe alcoyle inférieur ou alcoxy-alcoyle, R et R'contenant ensemble 1 à 4 atomes de carbone, et Y est un atome d'hydrogène ou d'iode, ou un groupe hydroxy, amino ou acylamino carboxylique aliphatique inférieur, de mme que de leurs sels métalliques non toxiques et de leurs sels d'amines non toxiques.
Ces agents se sont avérés avoir une sélectivité définie pour faire apparaître la vésicule biliaire et sont résorbables pratiquement complètement à travers l'appareil digestif, si bien qu'on a un minimum d'ombres interférentes.
On peut utiliser comme sels métalliques non toxiques les sels alcalins et alcalino-terreux, notamment les sels de potassium, calcium, magnésium, mais de préférence les sels de sodium.
On peut utiliser comme sels d'amines non toxiques les sels d'alcoylamines inférieures et d'alcoylolamines inférieures, par exemple les sels de diéthyl- amine, monoéthanolamine, diéthanolamine, dipropanolamine et triéthanolamine.
Si R et R'étaient tous deux de l'hydrogène, les composés seraient très toxiques et donneraient une image médiocre ou n'en donneraient pas du tout, tandis que si R et R'contenaient ensemble plus de 4 atomes de carbone, les propriétés cholécysto- graphiques de la substance ne seraient pas satisfaisantes. En revanche, lorsque R et R'contiennent ensemble 1 à 4 atomes de carbone, de préférence 2 à 3 atomes de carbone, les composés présentent des propriétés cholécystographiques hautement sélectives avec une toxicité générale nulle ou minime et se prtent facilement aux applications roentgengraphiques.
Les composés suivants peuvent tre utilisés pour exécuter la présente invention : acide alpha- (2, 4,6-triiodophénoxy)-butyrique ; acide alpha- (2, 4,6-triiodophénoxy)-propionique ; acide alpha- (2, 4,6-triiodophénoxy)-isovalérique ; acide alpha- (3-amino-2, 4,6-triiodophénoxy)-butyrique ; acide alpha- (2, 4,6-triiodophénoxy)-isobutyrique ; acide alpha- (2,4,6-triiodophenoxy)-beta-methoxy-propionique ; acide alpha- (2,4,6-triiodophenoxy)-beta-ethoxy-propionique ; acide alpha- (3-hydroxy-2, 4,6-triiodophenoxy)-bta-méthoxy-propionique ; acide alpha- (3-acétylamino-2, 4,6-triiodophénoxy)-bta-méthoxypropionique.
On peut administrer ces composés en tablettes en utilisant des supports ou liants inertes tels que l'amidon, les gommes, le sucre, etc., ou à l'état de poudre dans des capsules, ou en combinaison avec des émulsifiants comestibles dans 1'emploi sous la forme d'émulsion, ou encore sous la forme d'élixirs avec des mélanges alcooliques aqueux aromatisés.
On peut également les réduire en poudre et les dissoudre ou les mettre en suspension dans du lait, de l'eau, du jus d'orange ou autres liquides potables ; on peut mettre les acides libres en ampoules de 15 cm3, en suspension dans de l'eau contenant de la pectine, de la méthyl-cellulose, du kaolin ou autres agents de suspension et antiacides. Avec une dose moyenne d'environ 3 g, on peut obtenir une image satisfaisante aux rayons X au bout d'environ 10 à 16 heures.
Use as radiopaque agents of potyiodinated phenoxy fatty acids
The invention relates to the use, as radiopaque agents, of phenoxy-fatty acids of general formula:
EMI1.1
in which R is a lower alkyl group,
R ′ is a hydrogen atom or a lower alkyl or alkoxy-alkyl group, R and R ′ together containing 1 to 4 carbon atoms, and Y is a hydrogen or iodine atom, or a hydroxy or amino group or lower aliphatic carboxylic acylamino, as well as their non-toxic metal salts and their non-toxic amine salts.
These agents have been shown to have a definite selectivity to show the gallbladder and are absorbable almost completely through the digestive tract, so that there is a minimum of interfering shadows.
Alkali and alkaline-earth metal salts can be used as non-toxic metal salts, in particular potassium, calcium and magnesium salts, but preferably sodium salts.
The salts of lower alkylamines and lower alkylolamines, for example the salts of diethylamine, monoethanolamine, diethanolamine, dipropanolamine and triethanolamine, can be used as salts of non-toxic amines.
If R and R 'were both hydrogen, the compounds would be very toxic and either look poor or not at all, while if R and R' together contained more than 4 carbon atoms, the properties cholecystographs of the substance would not be satisfactory. On the other hand, when R and R 'together contain 1 to 4 carbon atoms, preferably 2 to 3 carbon atoms, the compounds exhibit highly selective cholecystographic properties with zero or minimal general toxicity and lend themselves easily to roentgraphic applications.
The following compounds can be used to carry out the present invention: alpha- (2, 4,6-triiodophenoxy) -butyric acid; alpha- (2, 4,6-triiodophenoxy) -propionic acid; alpha- (2, 4,6-triiodophenoxy) -isovaleric acid; alpha- (3-amino-2, 4,6-triiodophenoxy) -butyric acid; alpha- (2, 4,6-triiodophenoxy) -isobutyric acid; alpha- (2,4,6-triiodophenoxy) -beta-methoxy-propionic acid; alpha- (2,4,6-triiodophenoxy) -beta-ethoxy-propionic acid; alpha- (3-hydroxy-2, 4,6-triiodophenoxy) -bta-methoxy-propionic acid; alpha- (3-acetylamino-2, 4,6-triiodophenoxy) -bta-methoxypropionic acid.
These compounds can be administered in tablets using inert carriers or binders such as starch, gums, sugar, etc., or as a powder in capsules, or in combination with edible emulsifiers in the liquid. use in the form of an emulsion, or alternatively in the form of elixirs with flavored aqueous alcoholic mixtures.
They can also be powdered and dissolved or suspended in milk, water, orange juice or other drinkable liquids; the free acids can be put in 15 cm3 ampoules, suspended in water containing pectin, methyl cellulose, kaolin or other suspending and antacid agents. With an average dose of about 3 g, a satisfactory x-ray image can be obtained after about 10 to 16 hours.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US338274XA | 1954-01-08 | 1954-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH338274A true CH338274A (en) | 1959-05-15 |
Family
ID=21872674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH338274D CH338274A (en) | 1954-01-08 | 1954-12-28 | Use as radiopaque agents of polyiodinated phenoxy fatty acids |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH338274A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1179336B (en) * | 1960-06-21 | 1964-10-08 | Bracco Ind Chimica Spa | X-ray contrast media |
| US3435066A (en) * | 1964-12-23 | 1969-03-25 | Eprova Ltd | Radiopaque esters of triiodophenoxy-alkanoic acids |
| EP0609587A2 (en) * | 1993-02-02 | 1994-08-10 | Nycomed Imaging As | Compositions of iodophenoxy alkanes and iodophenyl ethers in film-forming materials for visualization of the gastrointestinal tract |
| EP0609586A2 (en) * | 1993-02-02 | 1994-08-10 | Nycomed Imaging As | Compositions of iodophenoxy alkanes and iodophenyl ethers for visualization of the gastrointestinal tract |
| WO1995022995A1 (en) * | 1994-02-25 | 1995-08-31 | Nycomed Imaging A/S | X-ray contrast compositions containing cellulose derivatives |
| WO1995028969A1 (en) * | 1994-04-21 | 1995-11-02 | Nycomed Imaging As | X-ray contrast compositions containing pharmaceutically acceptable clays |
-
1954
- 1954-12-28 CH CH338274D patent/CH338274A/en unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1179336B (en) * | 1960-06-21 | 1964-10-08 | Bracco Ind Chimica Spa | X-ray contrast media |
| US3435066A (en) * | 1964-12-23 | 1969-03-25 | Eprova Ltd | Radiopaque esters of triiodophenoxy-alkanoic acids |
| EP0609587A2 (en) * | 1993-02-02 | 1994-08-10 | Nycomed Imaging As | Compositions of iodophenoxy alkanes and iodophenyl ethers in film-forming materials for visualization of the gastrointestinal tract |
| EP0609586A2 (en) * | 1993-02-02 | 1994-08-10 | Nycomed Imaging As | Compositions of iodophenoxy alkanes and iodophenyl ethers for visualization of the gastrointestinal tract |
| EP0609587A3 (en) * | 1993-02-02 | 1995-09-06 | Sterling Winthrop Inc | Compositions of iodophenoxy alkanes and iodophenyl ethers in film-forming materials for visualization of the gastrointestinal tract. |
| EP0609586A3 (en) * | 1993-02-02 | 1995-09-06 | Sterling Winthrop Inc | Compositions of iodophenoxy alkanes and iodophenyl ethers for visualization of the gastrointestinal tract. |
| US5531979A (en) * | 1993-02-02 | 1996-07-02 | Sterling Winthrop Inc. | Compositions of iodophenoxy alkanes and iodophenyl ethers and pharmaceutically acceptable clays for visualization of the gastrointestinal tract |
| US5607660A (en) * | 1993-02-02 | 1997-03-04 | Sterling Winthrop Inc. | Compositions of iodophenoxy alkanes and iodophenyl ethers in combination with cellulose derivatives for visualization of the gastrointestinal tract |
| US5620677A (en) * | 1993-02-02 | 1997-04-15 | Sterling Winthrop Inc. | Compositions of iodophenoxy alkanes and iodophenyl ethers for visualization of the gastrointestinal tract |
| WO1995022995A1 (en) * | 1994-02-25 | 1995-08-31 | Nycomed Imaging A/S | X-ray contrast compositions containing cellulose derivatives |
| WO1995028969A1 (en) * | 1994-04-21 | 1995-11-02 | Nycomed Imaging As | X-ray contrast compositions containing pharmaceutically acceptable clays |
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