US3867431A - Contrast agent for angiography and urography - Google Patents
Contrast agent for angiography and urography Download PDFInfo
- Publication number
- US3867431A US3867431A US274973A US27497372A US3867431A US 3867431 A US3867431 A US 3867431A US 274973 A US274973 A US 274973A US 27497372 A US27497372 A US 27497372A US 3867431 A US3867431 A US 3867431A
- Authority
- US
- United States
- Prior art keywords
- acid
- compound
- urography
- angiography
- propanediol
- 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 - Lifetime
Links
- 239000002872 contrast media Substances 0.000 title abstract description 8
- 238000007487 urography Methods 0.000 title abstract description 6
- 238000002583 angiography Methods 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 5
- 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 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- -1 N-methylxylamine Chemical compound 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
- WOMTYMDHLQTCHY-UHFFFAOYSA-N 3-methylamino-1,2-propanediol Chemical compound CNCC(O)CO WOMTYMDHLQTCHY-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 9
- 150000001340 alkali metals Chemical class 0.000 abstract description 8
- 150000001412 amines Chemical class 0.000 abstract description 6
- 210000003169 central nervous system Anatomy 0.000 abstract description 3
- 238000002585 cerebral angiography Methods 0.000 abstract description 3
- 210000003734 kidney Anatomy 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- KMJGLKDBKRNRJK-UHFFFAOYSA-N 3-(acetamidomethyl)-5-[acetyl(2,3-dihydroxypropyl)amino]-2,4,6-triiodobenzoic acid Chemical compound OC(CN(C=1C(=C(C(=O)O)C(=C(C1I)CNC(C)=O)I)I)C(C)=O)CO KMJGLKDBKRNRJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- 231100000419 toxicity Toxicity 0.000 description 10
- 230000001988 toxicity Effects 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- VVDGWALACJEJKG-UHFFFAOYSA-N iodamide Chemical compound CC(=O)NCC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I VVDGWALACJEJKG-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
- CRVYPNHLIAWRNV-UHFFFAOYSA-N 2,4,6-triiodobenzoic acid Chemical class OC(=O)C1=C(I)C=C(I)C=C1I CRVYPNHLIAWRNV-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- PGIGXJYEXSOUNZ-UHFFFAOYSA-N oxiran-2-ylmethyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OCC1CO1 PGIGXJYEXSOUNZ-UHFFFAOYSA-N 0.000 description 1
- NCGARFWFKHNMJK-UHFFFAOYSA-N oxiran-2-ylmethyl methanesulfonate Chemical compound CS(=O)(=O)OCC1CO1 NCGARFWFKHNMJK-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 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
Definitions
- the aqueous solutions employed contained 300 mg iodine per milliliter and were injected at a rate of g iodine per minute per kg of test animal weight.
- the amount of aqueous test solution was 2 ml per kg of body weight, and the concentration was varied to modify the dosage.
- All solutions used for testing intracisternal toxicity contained 280 mg iodine per milliliter. Hyphens in the Table indicate that the test was not performed.
- the free acid of Compound A is primarily useful as an intermediate in the preparation of the water-soluble salts with pharmaceutically acceptable alkali metals and amines.
- Sodium is the preferred alkali metal.
- the lithium salt may also be employed.
- the other alkali metals contribute physiological properties of their own which are not normally desirable.
- Small amounts of the calcium or magnesium salts may be employed jointly with the alkali metal salts.
- the amines employed are those commonly used in galenic pharmacy as physiologically inert, cationic moieties in salts of physiologically active acids. They include, but are not limited to N-methylglucamine, N- methylxylamine l-methylamino-l dsoxy-[D1-xylite), l-methylamino-2,3-propanediol, monoethanolamine, diethanolamine, tris-(hydroxymethyl)-aminomethane, and mixtures of such alkanolamines.
- the free acid of Compound A is prepared by alkylating 3-acetyl-amino-5-acetylaminomethyl-2,4,6- triiodobenzoic acid in strongly alkaline solution with an ester of the formulas X CH CHOH CH OH or x c21 CH ⁇ 6/CH2 wherein X is the anionic radical of a strong acid, such as a hydrogen halide (l-lCl, HB,, HI), an alkylsulfonic acid, or an arylsulfonic acid..An epoxide may replace the esters.
- the most conveniently available alkylating agents include 3-chloro-l,2-propanediol, 3-bromo-l ,2-
- the alkylation is preferably performed in alcoholic solution in the presence of an alkali metal alcoholate as an acid acceptor.
- the aqueous solutions of the salts are epichlorohydrin,
- the solutions are also employed to advantage in urography. It has been found that the two hydroxyl groups in the side chain in position 3 do not materially interfere with excretion of the compound by the kidney so that at least 60% to 70% of an intravenous dosage of 100 mg per kg body weight is discharged by the kidney. of standard laboratory test animals within three hours. A sufficient amount of the radiopaque material is thus available in the urinary system for producing X-ray pictures of good contrast. Otherwise closely related compounds having more than two hydroxyl groups in side chains of the basic triiodobenzoic acid molecule do not produce useful X-ray images of the urinary tract.
- EXAMPLE 1 50.2 g 3-Acetylamino-5-acetylaminomethyl-2,4,6- triiodobenzoic acid (0.08 mole) was dissolved in 400 ml methanol, and the solution was mixed sequentially with 128 ml 2.5-molar sodium methylate solution (0.32 mole) in methanol and 13.4 ml 3chloro-l,2- propanediol (0.16 mole). The mixture was stirred at ambient temperature (about 20C) for 24 hours. An additional 32 ml 2.5-molar sodium methylate solution (0.08 mole) and 6.7 ml 3-chloro-1,2-propanediol were admixed, and stirring was continued for 24 hours.
- the free acid is soluble in 40 times its own weight of boiling water, 7 weights of cold methanol, 3 weights of boiling methanol, 50 weights of cold ethanol, and 5 weights of boiling ethanol, but is insoluble in chloroform.
- the salts with the alkali metals and amines mentioned above are readily soluble in water, the sodium and N-methylglucamine salts dissolving at C in about their own weights of water.
- EXAMPLE 3 12.55 g 3-Acetylamino-5-acetylaminomethyl-2,4,6- triiodobenzoic acid (0.02 mole) was dissolved in ml of a 0.5 molar solution of sodium methylate in methanol, and 4 g 2,3-epoxy-1-propanol was added. The mixture was stirred for 1 hour at ambient temperature and stored thereafter for 60 hours. 1t was then worked up as in Example 1 to recover 10.5 g 3-(N-[3,ydihydroxypropyl-acetylamino)-5-acetylaminomethyl- 2,4,6-triiodobenzoic acid melting at 196 to 198C (74.7% yield).
- EXAMPLE 4 553 g 3-(N-B,y-dihydroxypropyl-acetylamino)-5- acetylaminomethyl-Z,4,6-triiodobenzoic acid, 136.7 g N-methylglucamine, and 3.6 g sodium hydroxide were added sequentially with stirring to a solution of 0.01 g disodium edetate in a small amount of bi-distilled wa ter, and adding enoughadditional water to produce 800 ml solution. The solution was adjusted to pH 7.1i0.2, subjected to ultrafiltration, distributed in glass vials in amounts of 10 and 20 ml, and sterilized.
- the injectable solutions so obtained contained 375 mg iodine per milliliter.
- a compound as set forth in claim 1 which is a salt of said acid with sodium, lithium, or an alkanolamine.
- a compound as set forth in claim 1 which is a salt of said acid with an alkanolamine selected from the group consisting of N-methylglucaminc, N- methylxylamine, 1-methylamino-2,3propanediol, monoethanolamine, diethanolamine, and tris-(hydroxymethyl )-aminomethane.
- an alkanolamine selected from the group consisting of N-methylglucaminc, N- methylxylamine, 1-methylamino-2,3propanediol, monoethanolamine, diethanolamine, and tris-(hydroxymethyl )-aminomethane.
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1256971A CH551790A (de) | 1971-08-26 | 1971-08-26 | Roentgenkontrastmittel und verfahren zu seiner herstellung. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3867431A true US3867431A (en) | 1975-02-18 |
Family
ID=4384251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US274973A Expired - Lifetime US3867431A (en) | 1971-08-26 | 1972-07-25 | Contrast agent for angiography and urography |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3867431A (cs) |
| JP (1) | JPS5217019B2 (cs) |
| AR (1) | AR192959A1 (cs) |
| AT (1) | AT313470B (cs) |
| AU (1) | AU461619B2 (cs) |
| BE (1) | BE788054A (cs) |
| BR (1) | BR7205741D0 (cs) |
| CA (1) | CA976184A (cs) |
| CH (1) | CH551790A (cs) |
| DE (1) | DE2229360A1 (cs) |
| ES (1) | ES404646A1 (cs) |
| FR (1) | FR2150805B1 (cs) |
| ZA (1) | ZA724977B (cs) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001323A (en) * | 1974-12-13 | 1977-01-04 | Savac Ag | Water-soluble, non-ionizing hydroxy-containing amide derivatives of 2,4,6-triiodo-isophthalic acid |
| JPS5321137A (en) * | 1976-06-11 | 1978-02-27 | Serukapeto | Xxray contrast medium |
| US4138589A (en) * | 1974-06-17 | 1979-02-06 | Mallinckrodt, Inc. | Substituted isophthalamic acids |
| US4285928A (en) * | 1979-01-25 | 1981-08-25 | Juro Wada | Contrast composition for angiography |
| WO1987000757A1 (en) * | 1985-08-09 | 1987-02-12 | Cook Imaging, Inc. | Non-ionic polyol contrast media from ionic contrast media |
| US4954348A (en) * | 1985-08-09 | 1990-09-04 | Cook Imaging Corporation | Non-ionic polyol contrast media from ionic contrast media |
| US5035877A (en) * | 1985-08-09 | 1991-07-30 | Cook Imaging Corporation | Non-ionic contrast media from ionic contrast media |
| US5705692A (en) * | 1996-09-27 | 1998-01-06 | Abbott Laboratories | Process for the preparation of iohexol |
| US20080206862A1 (en) * | 2007-02-28 | 2008-08-28 | Cinvention Ag | High surface cultivation system bag |
| US20080213742A1 (en) * | 2007-02-28 | 2008-09-04 | Cinvention Ag | High surface cultivation system |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602005010747D1 (de) | 2005-01-13 | 2008-12-11 | Cinv Ag | Kohlenstoffnanopartikel enthaltende verbundwerkstoffe |
| RU2287346C2 (ru) * | 2005-03-22 | 2006-11-20 | ГУ Центральный научно-исследовательский рентгено-радиологический институт МЗ РФ (ЦНИРРИ) | Рентгеноконтрастное средство |
| RU2336904C1 (ru) * | 2007-01-15 | 2008-10-27 | Федеральное государственное учреждение "Российский научный центр радиологии и хирургических технологий Федерального агентства по высокотехнологичной медицинской помощи" (ФГУ "РНЦРХТ Росмедтехнологий") | Рентгеноконтрастное средство |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3360436A (en) * | 1962-11-23 | 1967-12-26 | Eprova Ltd | Radioopaque compounds and methods of preparing the same |
| US3702866A (en) * | 1968-06-10 | 1972-11-14 | Nyegaard & Co As | Novel 3,5 - bis-acylamido - 2,4,6-triiodobenzoic acids and 5-acylamido-2,4,6-triiodoisophthalamic acids |
-
0
- BE BE788054D patent/BE788054A/xx unknown
-
1971
- 1971-08-26 CH CH1256971A patent/CH551790A/xx not_active IP Right Cessation
-
1972
- 1972-06-16 DE DE2229360A patent/DE2229360A1/de active Pending
- 1972-07-03 AT AT568472A patent/AT313470B/de not_active IP Right Cessation
- 1972-07-07 ES ES404646A patent/ES404646A1/es not_active Expired
- 1972-07-19 ZA ZA724977A patent/ZA724977B/xx unknown
- 1972-07-21 AR AR243200A patent/AR192959A1/es active
- 1972-07-21 AU AU44850/72A patent/AU461619B2/en not_active Expired
- 1972-07-25 US US274973A patent/US3867431A/en not_active Expired - Lifetime
- 1972-07-26 CA CA147,967A patent/CA976184A/en not_active Expired
- 1972-08-04 JP JP47077732A patent/JPS5217019B2/ja not_active Expired
- 1972-08-18 FR FR7229697A patent/FR2150805B1/fr not_active Expired
- 1972-08-22 BR BR5741/72A patent/BR7205741D0/pt unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3360436A (en) * | 1962-11-23 | 1967-12-26 | Eprova Ltd | Radioopaque compounds and methods of preparing the same |
| US3702866A (en) * | 1968-06-10 | 1972-11-14 | Nyegaard & Co As | Novel 3,5 - bis-acylamido - 2,4,6-triiodobenzoic acids and 5-acylamido-2,4,6-triiodoisophthalamic acids |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138589A (en) * | 1974-06-17 | 1979-02-06 | Mallinckrodt, Inc. | Substituted isophthalamic acids |
| US4001323A (en) * | 1974-12-13 | 1977-01-04 | Savac Ag | Water-soluble, non-ionizing hydroxy-containing amide derivatives of 2,4,6-triiodo-isophthalic acid |
| JPS5321137A (en) * | 1976-06-11 | 1978-02-27 | Serukapeto | Xxray contrast medium |
| US4285928A (en) * | 1979-01-25 | 1981-08-25 | Juro Wada | Contrast composition for angiography |
| WO1987000757A1 (en) * | 1985-08-09 | 1987-02-12 | Cook Imaging, Inc. | Non-ionic polyol contrast media from ionic contrast media |
| US4954348A (en) * | 1985-08-09 | 1990-09-04 | Cook Imaging Corporation | Non-ionic polyol contrast media from ionic contrast media |
| US5035877A (en) * | 1985-08-09 | 1991-07-30 | Cook Imaging Corporation | Non-ionic contrast media from ionic contrast media |
| AU650432B2 (en) * | 1985-08-09 | 1994-06-23 | Guerbet Llc | Intermediates useful in the preparation of contrast medium and methods for their preparation |
| US5705692A (en) * | 1996-09-27 | 1998-01-06 | Abbott Laboratories | Process for the preparation of iohexol |
| US20080206862A1 (en) * | 2007-02-28 | 2008-08-28 | Cinvention Ag | High surface cultivation system bag |
| US20080213742A1 (en) * | 2007-02-28 | 2008-09-04 | Cinvention Ag | High surface cultivation system |
Also Published As
| Publication number | Publication date |
|---|---|
| CA976184A (en) | 1975-10-14 |
| AR192959A1 (es) | 1973-03-21 |
| AU4485072A (en) | 1974-01-24 |
| FR2150805B1 (cs) | 1975-11-28 |
| AT313470B (de) | 1974-02-25 |
| CH551790A (de) | 1974-07-31 |
| ES404646A1 (es) | 1975-06-16 |
| BR7205741D0 (pt) | 1973-11-01 |
| AU461619B2 (en) | 1975-05-29 |
| ZA724977B (en) | 1973-07-25 |
| DE2229360A1 (de) | 1974-07-11 |
| BE788054A (fr) | 1973-02-26 |
| FR2150805A1 (cs) | 1973-04-13 |
| JPS4832840A (cs) | 1973-05-02 |
| JPS5217019B2 (cs) | 1977-05-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3867431A (en) | Contrast agent for angiography and urography | |
| US4001323A (en) | Water-soluble, non-ionizing hydroxy-containing amide derivatives of 2,4,6-triiodo-isophthalic acid | |
| CA1106401A (en) | Dicarboxylic acid bis-(3,5-dicarbamoyl-2,4,6- triiodoanilides) | |
| JPH0222066B2 (cs) | ||
| GB1569242A (en) | Bis-(triiodobenzoylamino)-oxaalkanes for use in x-ray contrast media and process for their preparation | |
| US5575986A (en) | Chelating agent, complex compound of said chelating agent and metallic atom, and diagnostic agent comprising same | |
| CS221814B2 (en) | Method of making the triamide of the acid of 2,4,6-triiodebenzen-1,3-5-tricarboxyle | |
| KR19990022943A (ko) | 비이온성 조영제로서의 포르밀 유도체 | |
| JP3249112B2 (ja) | 非イオン性化合物及び該化合物を含有する放射線造影剤組成物 | |
| US3574718A (en) | Method for producing x-ray contrast agents | |
| US3763226A (en) | 3,5-substituted 2,4,6-triiodobenzoic acids,esters and salts thereof | |
| US3804892A (en) | Novel 3,5-substituted 2,4,6-triiodobenzoic acids and salts thereof | |
| US3937733A (en) | Salts of iodomethanesulfonic acid with organic bases | |
| US2939881A (en) | Iodo-benzoic acid derivatives | |
| JPH0433786B2 (cs) | ||
| JPH01153667A (ja) | 置換ジカルボン酸−ビス（３，５，−ジカルバモイル−２，４，６，−トリヨード−アニリド）、その製法およびこの化合物を含有するレントゲン造影剤 | |
| AU665968B2 (en) | New non ionic iodized agents for X-ray contrasting, method for preparing them and galenical compositions containing them | |
| US3632738A (en) | Method for the x-ray visualization of body cavities and a preparation for carrying out the method | |
| US3334134A (en) | Iodine-containing benzoic acid derivatives | |
| CA1274547A (en) | Gem-dihalo and tetrahalo-1,12-diamino-4, 9-diaza-dodecanes | |
| US3452134A (en) | Derivatives of 2,4,6-triiodo-3-hydroxy-benzene as x-ray opacifiers | |
| US3781338A (en) | Nitrilotriacyltriimino-tris-(2,4,6-triiodobenzoic acid)compounds | |
| US3558600A (en) | Alkyl sulfate salts of 1-(p-chlorobenzhydryl)-4-methylhomopiperazines | |
| JPH0667880B2 (ja) | ｇｅｍ−ジハロ−１，８−ジアミノ−４−アザ−オクタン類 | |
| DE2245467A1 (de) | Benzoesaeurederivate |