DE2926850C2 - Verfahren zur Herstellung einer sterilen injizierbaren physiologisch annehmbaren Lösung eines nicht ionischen m-Carboxamido-o-jodo-N-(β-hydroxyalkyl)-anilin-Röntgenkontrastmittels und Lösungen des Röntgenkontrastmittels und eines Puffers - Google Patents
Verfahren zur Herstellung einer sterilen injizierbaren physiologisch annehmbaren Lösung eines nicht ionischen m-Carboxamido-o-jodo-N-(β-hydroxyalkyl)-anilin-Röntgenkontrastmittels und Lösungen des Röntgenkontrastmittels und eines PuffersInfo
- Publication number
- DE2926850C2 DE2926850C2 DE2926850A DE2926850A DE2926850C2 DE 2926850 C2 DE2926850 C2 DE 2926850C2 DE 2926850 A DE2926850 A DE 2926850A DE 2926850 A DE2926850 A DE 2926850A DE 2926850 C2 DE2926850 C2 DE 2926850C2
- Authority
- DE
- Germany
- Prior art keywords
- ray contrast
- buffer
- physiologically acceptable
- solution
- contrast agent
- 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
- 239000000872 buffer Substances 0.000 title claims description 35
- 239000002872 contrast media Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title 2
- 239000000243 solution Substances 0.000 claims description 56
- 150000001412 amines Chemical class 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 230000007423 decrease Effects 0.000 claims description 9
- 239000007853 buffer solution Substances 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000002252 acyl group Chemical group 0.000 description 10
- 229940039231 contrast media Drugs 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- -1 hydroxy, mercapto, carboxyl Chemical group 0.000 description 8
- 230000001419 dependent effect Effects 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 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 description 5
- 125000005518 carboxamido group Chemical group 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229960003194 meglumine Drugs 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001860 citric acid derivatives Chemical class 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960002442 glucosamine Drugs 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- 101150035093 AMPD gene Proteins 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ULSIECBIWATTOD-UHFFFAOYSA-N CC(=O)N[N] Chemical group CC(=O)N[N] ULSIECBIWATTOD-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 150000008273 hexosamines Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000008278 pentosamines Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
-
- 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
- A61K49/0452—Solutions, e.g. for injection
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/90—In vivo diagnostic or in vivo test agent which contains an additional ingredient to reduce the toxicity or side effects of the active ingredient
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)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7828764 | 1978-07-04 | ||
| KR1019790002214A KR830001643B1 (ko) | 1978-07-04 | 1979-07-03 | X-선 조영제의 생리적으로 허용되는 멸균 주사용 용액을 제조하는 방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2926850A1 DE2926850A1 (de) | 1980-03-06 |
| DE2926850C2 true DE2926850C2 (de) | 1985-01-24 |
Family
ID=26268114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2926850A Expired DE2926850C2 (de) | 1978-07-04 | 1979-07-03 | Verfahren zur Herstellung einer sterilen injizierbaren physiologisch annehmbaren Lösung eines nicht ionischen m-Carboxamido-o-jodo-N-(β-hydroxyalkyl)-anilin-Röntgenkontrastmittels und Lösungen des Röntgenkontrastmittels und eines Puffers |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4278654A (https=) |
| JP (1) | JPS5531068A (https=) |
| KR (1) | KR830001643B1 (https=) |
| AR (1) | AR222337A1 (https=) |
| AT (1) | AT371998B (https=) |
| AU (1) | AU523295B2 (https=) |
| BE (1) | BE877443A (https=) |
| CA (1) | CA1132901A (https=) |
| CH (1) | CH649469A5 (https=) |
| DE (1) | DE2926850C2 (https=) |
| DK (1) | DK155714C (https=) |
| ES (1) | ES482131A0 (https=) |
| FI (1) | FI75492C (https=) |
| FR (1) | FR2435253A1 (https=) |
| HK (1) | HK59984A (https=) |
| IT (1) | IT1193761B (https=) |
| NL (1) | NL183121C (https=) |
| NZ (1) | NZ190907A (https=) |
| PT (1) | PT69869A (https=) |
| SE (1) | SE445971B (https=) |
| SG (1) | SG5784G (https=) |
| ZA (1) | ZA793313B (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3150916A1 (de) * | 1981-12-18 | 1983-06-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | N-hydroxyaethylierte 2,4,6-trijodaminoisiophthalsaeure-bis- trihydroxybutylamide, deren herstellung und diese enthaltende roentgenkontrastmittel" |
| US4396598A (en) * | 1982-01-11 | 1983-08-02 | Mallinckrodt, Inc. | Triiodoisophthalamide X-ray contrast agent |
| US5035877A (en) * | 1985-08-09 | 1991-07-30 | Cook Imaging Corporation | Non-ionic contrast media from ionic contrast media |
| HK1003564A1 (en) * | 1985-08-09 | 1998-10-30 | Cook Imaging Corporation | Non-ionic polyol contrast media from ionic contrast media |
| US4718463A (en) * | 1985-12-20 | 1988-01-12 | Mallinckrodt, Inc. | Method of producing prefilled sterile plastic syringes |
| US5847009A (en) * | 1986-01-14 | 1998-12-08 | Alliance Pharmaceutical Corp. | Prophylaxis in the parenteral administration of particulate dispersions in fluorocarbon emulsions |
| US5284645A (en) * | 1987-08-05 | 1994-02-08 | Alliance Pharmaceutical Corp. | Fluorocarbon emulsions containing amino acid based anti-inflamatory agents and buffer systems |
| US4863714A (en) * | 1987-02-05 | 1989-09-05 | Cook Imaging Corporation | Sterilization of compositions of limited stability |
| US5698739A (en) * | 1989-07-05 | 1997-12-16 | Schering Aktiengesellschaft | Carboxamide non-ionic contrast media |
| IL94718A (en) * | 1989-07-05 | 1994-10-21 | Schering Ag | Carboxamide non-ionic contrast media and method for the preparation thereof |
| US5191120A (en) * | 1989-12-13 | 1993-03-02 | Mallinckrodt Medical, Inc. | Process for preparing nonionic X-ray contrast agents |
| US5075502A (en) * | 1989-12-13 | 1991-12-24 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
| DE4111939A1 (de) * | 1991-04-12 | 1992-10-22 | Fresenius Ag | Parenteral verabreichbare, hitzesterilisierbare o/w-emulsion eines roentgenkontrastmittels |
| US5169864A (en) * | 1991-11-15 | 1992-12-08 | Baxter International Inc. | Unbuffered premixed ranitidine formulation |
| DE4316722A1 (de) * | 1993-05-19 | 1994-11-24 | Fresenius Ag | Parenteral verabreichbare, unter Hitzesterilisationsbedingungen stabile O/W-Emulsion eines Röntgenkontrastmittels |
| SK101398A3 (en) * | 1996-01-25 | 1998-12-02 | Schering Ag | Improved concentrated injection and infusion solutions for intravenous administration |
| DE19648650C2 (de) * | 1996-01-29 | 1998-07-02 | Schering Ag | Puffersysteme und deren Verwendung zur Stabilisierung pharmazeutischer Zubereitung |
| US6072069A (en) * | 1998-11-04 | 2000-06-06 | Biophysica, Inc. | Biodegradable nonionic contrast media |
| US7250153B2 (en) * | 2002-12-12 | 2007-07-31 | Biophysica Research, Inc. | Contrast media formulations having improved biological tolerance |
| KR101915821B1 (ko) * | 2010-03-23 | 2018-11-06 | 지이 헬스케어 에이에스 | 안정화된 ｘ―선 진단용 조성물의 제조 |
| EP2854531A4 (en) * | 2012-05-30 | 2016-03-23 | Verrow Pharmaceuticals Inc | STABILIZED FORMULATIONS WITH IODIC CONTRASTIVE AND CYCLODEXTRINS |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3189E (fr) * | 1904-09-30 | Jules Cesar Napoleon Fouilloy | Collier d'attache pour protecteur antidérapant de pneumatiques | |
| NL127881C (https=) * | 1963-03-25 | |||
| GB1069437A (en) * | 1963-10-23 | 1967-05-17 | Nyegaard & Co As | Injectable x-ray contrast media |
| US3733397A (en) * | 1966-12-02 | 1973-05-15 | Pharmacia Ab | Method for the x-ray visualization of body cavities and a preparation for carrying out the method |
| SE315975B (https=) * | 1967-12-28 | 1969-10-13 | Pharmacia Ab | |
| US4021481A (en) * | 1969-06-27 | 1977-05-03 | Nyegaard & Co. A/S | Amido derivatives of 2,4,6-triiodobenzoic acids containing at least one N-hydroxyalkyl and at least two hydroxyl groups |
| GB1321591A (en) * | 1969-06-27 | 1973-06-27 | Nyegaard & Co As | Non-ionic iodinated x-ray contrast agents |
| CH583562A5 (https=) * | 1973-07-17 | 1977-01-14 | Bracco Ind Chimica Spa | |
| GB1495679A (en) * | 1974-06-17 | 1977-12-21 | Mallinckrodt Inc | Substituted isophthalamic acids |
| US3953497A (en) * | 1974-07-29 | 1976-04-27 | Mallinckrodt, Inc. | 2,4,6-Triiodo-5-methoxyacetamido-N-methylisophthalamic acid and salts, acyl halides and esters thereof |
| GB1514920A (en) * | 1974-10-09 | 1978-06-21 | Reckitt & Colmann Prod Ltd | Dispensing container for medicinal foams |
| FI760068A7 (https=) * | 1975-02-03 | 1976-08-04 | Schering Ag | |
| DE2505218A1 (de) * | 1975-02-05 | 1976-08-19 | Schering Ag | Neue orale roentgenkontrastmittel und verfahren zu ihrer herstellung |
| GB1548594A (en) * | 1976-06-11 | 1979-07-18 | Nyegaard & Co As | Triiodoisophthalic acid amides |
| DE2629228C2 (de) * | 1976-06-25 | 1984-10-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | Jodierte Isophthalamsäure-Derivate Verfahren zu deren Herstellung sowie deren Verwendung |
| US4256729A (en) * | 1979-03-23 | 1981-03-17 | Mallinckrodt, Inc. | N,N'-Bis-(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-keto-L-gulonamido)isophthalamide and radiological compositions containing same |
-
1979
- 1979-07-03 AT AT0464479A patent/AT371998B/de not_active IP Right Cessation
- 1979-07-03 DE DE2926850A patent/DE2926850C2/de not_active Expired
- 1979-07-03 PT PT69869A patent/PT69869A/pt unknown
- 1979-07-03 IT IT49618/79A patent/IT1193761B/it active
- 1979-07-03 AU AU48615/79A patent/AU523295B2/en not_active Expired
- 1979-07-03 CA CA331,006A patent/CA1132901A/en not_active Expired
- 1979-07-03 ZA ZA793313A patent/ZA793313B/xx unknown
- 1979-07-03 US US06/054,440 patent/US4278654A/en not_active Expired - Lifetime
- 1979-07-03 NZ NZ190907A patent/NZ190907A/xx unknown
- 1979-07-03 ES ES482131A patent/ES482131A0/es active Granted
- 1979-07-03 JP JP8356579A patent/JPS5531068A/ja active Granted
- 1979-07-03 BE BE0/196098A patent/BE877443A/fr not_active IP Right Cessation
- 1979-07-03 NL NLAANVRAGE7905166,A patent/NL183121C/xx not_active IP Right Cessation
- 1979-07-03 SE SE7905830A patent/SE445971B/sv unknown
- 1979-07-03 AR AR277172A patent/AR222337A1/es active
- 1979-07-03 CH CH6221/79A patent/CH649469A5/de not_active IP Right Cessation
- 1979-07-03 KR KR1019790002214A patent/KR830001643B1/ko not_active Expired
- 1979-07-03 FR FR7917239A patent/FR2435253A1/fr active Granted
- 1979-07-03 FI FI792101A patent/FI75492C/fi not_active IP Right Cessation
- 1979-07-03 DK DK280979A patent/DK155714C/da not_active IP Right Cessation
-
1981
- 1981-02-10 US US06/233,137 patent/US4396597A/en not_active Expired - Lifetime
-
1984
- 1984-01-21 SG SG57/84A patent/SG5784G/en unknown
- 1984-08-02 HK HK599/84A patent/HK59984A/xx not_active IP Right Cessation
Non-Patent Citations (1)
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