WO1980001244A1 - X-ray contrast media solutions - Google Patents
X-ray contrast media solutions Download PDFInfo
- Publication number
- WO1980001244A1 WO1980001244A1 PCT/EP1979/000100 EP7900100W WO8001244A1 WO 1980001244 A1 WO1980001244 A1 WO 1980001244A1 EP 7900100 W EP7900100 W EP 7900100W WO 8001244 A1 WO8001244 A1 WO 8001244A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- contrast media
- ray contrast
- media solutions
- solutions according
- active agent
- Prior art date
Links
- 239000002872 contrast media Substances 0.000 title claims abstract description 51
- 229940039231 contrast media Drugs 0.000 title claims abstract description 45
- 239000004094 surface-active agent Substances 0.000 claims abstract description 43
- 210000004369 blood Anatomy 0.000 claims description 10
- 239000008280 blood Substances 0.000 claims description 10
- -1 polyoxyethylene Polymers 0.000 claims description 8
- 210000001124 body fluid Anatomy 0.000 claims description 7
- 239000010839 body fluid Substances 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 235000010445 lecithin Nutrition 0.000 claims description 5
- 239000000787 lecithin Substances 0.000 claims description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- OLAOYPRJVHUHCF-UHFFFAOYSA-N iooxitalamic acid Chemical compound CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(=O)NCCO)=C1I OLAOYPRJVHUHCF-UHFFFAOYSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 3
- 229940067606 lecithin Drugs 0.000 claims description 3
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 3
- OBFSQMXGZIYMMN-UHFFFAOYSA-N 3-chloro-2-hexadecylpyridine Chemical compound CCCCCCCCCCCCCCCCC1=NC=CC=C1Cl OBFSQMXGZIYMMN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000002604 ultrasonography Methods 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- 230000000254 damaging effect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 17
- 210000003038 endothelium Anatomy 0.000 description 13
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 5
- 230000001815 facial effect Effects 0.000 description 5
- 210000000709 aorta Anatomy 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LJLXDSVJKWDEQX-UHFFFAOYSA-N 1,6-diacetyl-3,5-diamino-2,4,6-triiodocyclohexa-2,4-diene-1-carboxylic acid Chemical compound C(C)(=O)C1(C(C(=O)O)(C(=C(C(=C1N)I)N)I)C(C)=O)I LJLXDSVJKWDEQX-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 206010018910 Haemolysis Diseases 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008588 hemolysis Effects 0.000 description 2
- 150000002497 iodine compounds Chemical class 0.000 description 2
- 229960001707 ioxaglic acid Drugs 0.000 description 2
- 229960003781 ioxitalamic acid Drugs 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 230000003204 osmotic effect Effects 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 210000004291 uterus Anatomy 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- IFTFXKNYTWAOGK-WZTVWXICSA-N 3-acetamido-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodobenzoic acid;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(=O)NCCO)=C1I IFTFXKNYTWAOGK-WZTVWXICSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BAQCROVBDNBEEB-UBYUBLNFSA-N Metrizamide Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(=O)N[C@@H]2[C@H]([C@H](O)[C@@H](CO)OC2O)O)=C1I BAQCROVBDNBEEB-UBYUBLNFSA-N 0.000 description 1
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 1
- 229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 description 1
- 229920002700 Polyoxyl 60 hydrogenated castor oil Polymers 0.000 description 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 206010046996 Varicose vein Diseases 0.000 description 1
- ATNOAWAQFYGAOY-GPTZEZBUSA-J [Na+].[Na+].[Na+].[Na+].Cc1cc(ccc1\N=N\c1ccc2c(cc(c(N)c2c1O)S([O-])(=O)=O)S([O-])(=O)=O)-c1ccc(\N=N\c2ccc3c(cc(c(N)c3c2O)S([O-])(=O)=O)S([O-])(=O)=O)c(C)c1 Chemical compound [Na+].[Na+].[Na+].[Na+].Cc1cc(ccc1\N=N\c1ccc2c(cc(c(N)c2c1O)S([O-])(=O)=O)S([O-])(=O)=O)-c1ccc(\N=N\c2ccc3c(cc(c(N)c3c2O)S([O-])(=O)=O)S([O-])(=O)=O)c(C)c1 ATNOAWAQFYGAOY-GPTZEZBUSA-J 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000000819 hypertonic solution Substances 0.000 description 1
- 229940021223 hypertonic solution Drugs 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- TYYBFXNZMFNZJT-UHFFFAOYSA-N ioxaglic acid Chemical compound CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I TYYBFXNZMFNZJT-UHFFFAOYSA-N 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229960000554 metrizamide Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 208000027185 varicose disease Diseases 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
Definitions
- the invention relates to aqueous X-raycontrast media solutions which are to be introduced intravasally and are miscible with body fluids.
- the inner lining of human and animal blood vessels is an i portant structure; when damaged, formation of thro bae can occur. Minor lesions can lead to per eability disorders and thus to an increased escape of fluids into the tissue.
- aqueous solutions of iodine-contain- ing compounds are injected in to produce an increased absorption of X-rays in the vessels.
- X-ray contrast media are hypertonic solutions which as a rule cause clearly detectable damage to the endothelium.
- the hypertonic properties of the contrast media Solutions for example by using non-ionic iodine compounds, such as etrizamide, or by using iodine compounds with a relatively high molecular weight, such as.-ioxaglic acid, it has been possible in normal cases to keep the damage to healthy endothelium of blood vessels with normal circulation within acceptable limits.
- non-ionic iodine compounds such as etrizamide
- iodine compounds with a relatively high molecular weight such as.-ioxaglic acid
- the damaging effect of X-ray contrast media on the endothelium is known and can be determined se iquantitatively by the method of Gottlob and Zinner, Wien.Klin.Wschr. 77, 149 [1965] (Silver coloration of the aortas of surviving rats after the action of contrast media, - Examination of the aorta endothelia on mounted preparations, fro the surfaces, - "en face preparations" method). The percentage of damaged area of the aortas investigated can be indicated by this method.
- endothelium damage caused by X-ray contrast media can be detected by the fact that after contact with the contrast medium, the endothelium can be stained to a greater extent with dyestuffs, such as Evan's Blue or Trypan Blue. This is to be evaluated as an indication of a per eability disorder (Gottlob, R. Amipaque-Workshop, 25th May 1978, Berlin, Excerpta Medica, Amsterdam-Oxford, 1978, p. 124-132).
- dyestuffs such as Evan's Blue or Trypan Blue
- the invention is thus based on the object of improving X-ray contrast media which are to be introduced intravasally to the extent that the danger of damage to the endothelium is significantly reduced.
- Swiss Patent Specification 373,866 showing the addition of non-ionic surface-active agents to X-ray contrast media in the form of aqueous suspensions, whereupon greater adhesion of these suspensions to the sur ⁇ face of the bronchial system or of the uterus is said to be achieved.
- aqueous Solutions of iodated derivatives of pyridone are known, which ' contain a viscosity increasing agent and optionally a wetting agent, which shall enhance the adhesion of the Solutions to the surface of the Uterus or of the bronchial system, ie for a nonintravasal use.
- M. Guerbet the literature reference M. Guerbet,
- the invention thus relates to aqueous X-ray contrast media solutions which are miscible with body fluids and are characterized by the addition of pharmacologically acceptable surface-active agents.
- Body fluids are to be understood as blood.
- X-ray contrast media Solutions according to this invention are to be understood as those which are to be introduced intravasally, that is for arteriographic and phlebographic application.
- the invention thus preferably relates to aqueous X-ray contrast media Solutions which are miscible with body fluids and are characterized by the addition of pharmacologically acceptable surface-active agents in an amount such that the interfacial tension with respect to the walls of the vessels in the body is approximately reduced to the interfacial tenion which prevails between the blood and the vessel walls.
- Some X-ray contrast media which do not dissociate into ions and thus have a Tower (but in comparison with blood still increased) osmotic pressure such as, for example, metrizamide (2- (3-acetamido-5-N-methyl- acetamide-2,4,6-triiodobenzamido) -2-deoxy-D-glucose), cause damage to the vessel wall, which can be detected by an increased . ability to be stained and is possibly a result of a certain lipophilicity.
- metrizamide 3- (3-acetamido-5-N-methyl- acetamide-2,4,6-triiodobenzamido) -2-deoxy-D-glucose
- the establishment, according to the invention, of the interfacial tension can be assisted by a suitable mixture of X-ray contrast media, so that the amount of surface-active agents required for reducing the interfacial tension to the desired value can be minimized.
- the interfacial tension of conventional X-ray contrast media solutions with respect to the vessel wall is as a rule between 18 and 20.10 -5 N / cm.
- a good endothelium toleration is achieved, in particular, by lowering this interfacial tension to values of below 16.10 -5 N / cm by adding surface-active agents.
- the corresponding inter ⁇ facial tension values for blood are in the order of size from 8 to 15.10 N / cm, and are usually about 12.10 -5 N / cm.
- vveesssseell ⁇ wall is reduced to at least 16.10 N / cm by the surface-active agents.
- HLB number An essential criterion of the usefulness of a surface-active agent is given by the so-called HLB number.
- This nu ber represents the "hydrophilic / lipophilic balance" and a high numerical value corresponds to a pro- nounced hydrophilic character while a low numerical value represents pro ⁇ nounced lipophilic character.
- the lipophilic character is preferably reduced to an HLB number of greater than 15, preferably between 25 and 35, in particular about 29, by the addition of suitable surface-active agents, and, above all, block copolycondensates of propylene glycol and poly - ethylene glycol have proved suitable for this.
- Suitable surface-active agents are, above all, the lecithins with poly- unsaturated fatty acids, which are well tolerated biologically. With such surface-active agents, the concentration can be adjusted to a relatively high value, in particular to a concentration of about 0.1 to 1 g / 100 ml, preferably of about 0.5 g / 100 ml.
- Another suitable surface-active agent is polyoxyethylene sorbitan mono-oleates. The amount required in each case depends on the chosen surface- active agent, but is also influenced by the chosen X-ray contrast medium.
- Customary X-ray contrast media for angiography are substituted triiodobenzoic acids, and examples which should be mentioned specifically are "the methylglucamine salt of diacetyl-3,5-diamino-2,4,6-triiodobenzoic acid, the methylglucamine salt, onoethanola ine salt and sodium salt of 5-acetamido-N- (2-hydroxy-ethyl) -2,4,6-triiodoisophthalamic acid and ioxaglic acid.
- Non-ionic surface-active agents which are preferably used according to the inven ⁇ tion are the non-ionic surface-active agents, such as, for example, naturally occuring lecithins, polyethoxy-sorbitane fatty acid esters (commer cially available, for example, under the tradename Tween®), polyethoxy-castor oil acid glycerol esters (commercially available, for example, under the tradename Cremophor EL, RH 40 and RH 60®) and polyoxyethylene / polyoxypropylene ' polymers (commercially available, for example, under the tradename Pluronics®).
- non-ionic surface-active agents such as, for example, naturally occuring lecithins, polyethoxy-sorbitane fatty acid esters (commer cially available, for example, under the tradename Tween®), polyethoxy-castor oil acid glycerol esters (commercially available, for example, under the tradename Cremophor EL, RH
- Ampoules (30 ml) containing 19.8 g meglumine-ioxitalamate, batch size 300 ml are prepared as follows: 1.5 kg of EPL US are dissolved in 100 1 of doubly distilled water of 80 ° C, while stirring with a highspeed stirrer. Thereafter 151.98 kg of ioxitalamic acid are suspended and 46.02 kg of methylglucamine are added slowly. The clear solution is cooled to about 40 ° C. After addition of 0.03 kg sodium bisulfite the pH-value is brought to 7.0 t 0.5 by adding ioxitalamic acid or methylglucamine. The batch is filtrated under sterile conditions and is made up to 300 1 with doubly distilled water. The solution is filled into 30 ml ampoules and these are sterilized in an autoclave at 120 ° C for 20 minutes.
- the invention also relates to the use of pharmacologically acceptable surface-active agents as admixture to aqueous X-ray contrast media solutions which are to be introduced intravasally.
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT907678 | 1978-12-19 | ||
| AT9076/78 | 1978-12-19 | ||
| EP19790105091 EP0012926B1 (de) | 1978-12-19 | 1979-12-11 | Röntgenkontrastmittellösungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1980001244A1 true WO1980001244A1 (en) | 1980-06-26 |
Family
ID=25605277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1979/000100 WO1980001244A1 (en) | 1978-12-19 | 1979-12-17 | X-ray contrast media solutions |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS55501057A (enrdf_load_stackoverflow) |
| WO (1) | WO1980001244A1 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997030736A3 (en) * | 1996-02-20 | 1997-12-18 | Nycomed Imaging As | Contrast medium |
| WO2000021577A3 (en) * | 1998-10-09 | 2000-07-27 | Nycomed Imaging As | Compositions |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH273245A (de) * | 1948-10-14 | 1951-01-31 | Cilag Ag | Lösung für die röntgenographische Darstellung von Körperhöhlen. |
| DE919908C (de) * | 1952-05-24 | 1954-11-08 | Schering Ag | Roentgenkontrastmittel zur Bronchographie und Hysterosalpingographie |
| GB834517A (en) * | 1958-09-15 | 1960-05-11 | Sterling Drug Inc | Radiopaque compositions |
| CH373866A (de) * | 1957-09-11 | 1963-12-15 | Bayer Ag | Röntgenkontrastmittel |
| CH375841A (de) * | 1958-10-24 | 1964-03-15 | Leo Ab | Röntgenkontrastmittel zur Besichtigung der Gallengänge |
| FR3658M (fr) * | 1964-02-18 | 1965-11-02 | Michel Marie Andre Guerbet | Composition huileuse pour l'injection intravasculaire. |
| FR5986M (enrdf_load_stackoverflow) * | 1966-11-22 | 1968-06-21 | ||
| FR6777M (enrdf_load_stackoverflow) * | 1967-07-10 | 1969-03-10 |
-
1979
- 1979-12-17 JP JP50012479A patent/JPS55501057A/ja active Pending
- 1979-12-17 WO PCT/EP1979/000100 patent/WO1980001244A1/de unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH273245A (de) * | 1948-10-14 | 1951-01-31 | Cilag Ag | Lösung für die röntgenographische Darstellung von Körperhöhlen. |
| DE919908C (de) * | 1952-05-24 | 1954-11-08 | Schering Ag | Roentgenkontrastmittel zur Bronchographie und Hysterosalpingographie |
| CH373866A (de) * | 1957-09-11 | 1963-12-15 | Bayer Ag | Röntgenkontrastmittel |
| GB834517A (en) * | 1958-09-15 | 1960-05-11 | Sterling Drug Inc | Radiopaque compositions |
| CH375841A (de) * | 1958-10-24 | 1964-03-15 | Leo Ab | Röntgenkontrastmittel zur Besichtigung der Gallengänge |
| FR3658M (fr) * | 1964-02-18 | 1965-11-02 | Michel Marie Andre Guerbet | Composition huileuse pour l'injection intravasculaire. |
| FR5986M (enrdf_load_stackoverflow) * | 1966-11-22 | 1968-06-21 | ||
| FR6777M (enrdf_load_stackoverflow) * | 1967-07-10 | 1969-03-10 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997030736A3 (en) * | 1996-02-20 | 1997-12-18 | Nycomed Imaging As | Contrast medium |
| WO2000021577A3 (en) * | 1998-10-09 | 2000-07-27 | Nycomed Imaging As | Compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55501057A (enrdf_load_stackoverflow) | 1980-12-04 |
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