DE2541491A1 - Polyhydroxy-alkyl-3,5-disubst.-2, 4,6-trijodcarbanilate, verfahren zu ihrer herstellung und mittel, worin sie enthalten sind - Google Patents
Polyhydroxy-alkyl-3,5-disubst.-2, 4,6-trijodcarbanilate, verfahren zu ihrer herstellung und mittel, worin sie enthalten sindInfo
- Publication number
- DE2541491A1 DE2541491A1 DE19752541491 DE2541491A DE2541491A1 DE 2541491 A1 DE2541491 A1 DE 2541491A1 DE 19752541491 DE19752541491 DE 19752541491 DE 2541491 A DE2541491 A DE 2541491A DE 2541491 A1 DE2541491 A1 DE 2541491A1
- Authority
- DE
- Germany
- Prior art keywords
- acylamino
- alkyl
- alkoxy
- carbamyl
- hydroxy
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 2,4,6-triiodophenyl Chemical group 0.000 claims description 62
- 229920005862 polyol Polymers 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 53
- 150000003077 polyols Chemical class 0.000 claims description 44
- 150000001241 acetals Chemical class 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 125000004442 acylamino group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 18
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 231100000053 low toxicity Toxicity 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical group NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229930182470 glycoside Natural products 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 16
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- 239000000047 product Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- OYEVGJFBPABVBN-UHFFFAOYSA-N 5-amino-2,4,6-triiodo-1-n,3-n,3-n-trimethylbenzene-1,3-dicarboxamide Chemical compound CNC(=O)C1=C(I)C(N)=C(I)C(C(=O)N(C)C)=C1I OYEVGJFBPABVBN-UHFFFAOYSA-N 0.000 description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000906446 Theraps Species 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
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- 231100000041 toxicology testing Toxicity 0.000 description 3
- 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 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
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- 241000699666 Mus <mouse, genus> Species 0.000 description 2
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- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- 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 1
- SZKGLHFDOIYOSN-UHFFFAOYSA-N N=C=O.NC(Cl)=O Chemical compound N=C=O.NC(Cl)=O SZKGLHFDOIYOSN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001304 aldoheptoses Chemical class 0.000 description 1
- 150000001312 aldohexoses Chemical class 0.000 description 1
- 150000001320 aldopentoses Chemical class 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 150000001330 aldotetroses Chemical class 0.000 description 1
- 150000001333 aldotrioses Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- HXFDFZSGILIIMP-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetrol Chemical class OC1C(O)C(O)C1O HXFDFZSGILIIMP-UHFFFAOYSA-N 0.000 description 1
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-UHFFFAOYSA-N 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- XNAUSUVBDKISHM-UHFFFAOYSA-N cyclopentane-1,2,3,4,5-pentol Chemical compound OC1C(O)C(O)C(O)C1O XNAUSUVBDKISHM-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940120503 dihydroxyacetone Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 229960003082 galactose Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000002566 ketoheptoses Chemical class 0.000 description 1
- 150000002574 ketohexoses Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002581 ketopentoses Chemical class 0.000 description 1
- 150000002584 ketoses Chemical class 0.000 description 1
- 150000002586 ketotetroses Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- HOVAGTYPODGVJG-VOQCIKJUSA-N methyl beta-D-galactoside Chemical compound CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-VOQCIKJUSA-N 0.000 description 1
- HOVAGTYPODGVJG-XUUWZHRGSA-N methyl beta-D-glucopyranoside Chemical compound CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-XUUWZHRGSA-N 0.000 description 1
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000009608 myelography Methods 0.000 description 1
- CZZXMMGYJKBXAP-UHFFFAOYSA-N n-(2,3,4,5-tetrahydroxycyclopentyl)acetamide Chemical compound CC(=O)NC1C(O)C(O)C(O)C1O CZZXMMGYJKBXAP-UHFFFAOYSA-N 0.000 description 1
- OTVWCQCGAPTVLW-NTSWFWBYSA-N n-[(2r,3s)-3,4-dihydroxy-1-oxobutan-2-yl]acetamide Chemical compound CC(=O)N[C@@H](C=O)[C@H](O)CO OTVWCQCGAPTVLW-NTSWFWBYSA-N 0.000 description 1
- GUCKZVCYFJZLCB-XVMARJQXSA-N n-[(2r,3s,4r)-3,4,5-trihydroxy-1-oxopentan-2-yl]acetamide Chemical compound CC(=O)N[C@@H](C=O)[C@H](O)[C@H](O)CO GUCKZVCYFJZLCB-XVMARJQXSA-N 0.000 description 1
- RKDQPJFPCQYUFU-IYSWYEEDSA-N n-[(2s,3r)-1,2,5-trihydroxy-4-oxopentan-3-yl]acetamide Chemical compound CC(=O)N[C@H]([C@H](O)CO)C(=O)CO RKDQPJFPCQYUFU-IYSWYEEDSA-N 0.000 description 1
- ASXCJONOVQSZRF-LXGUWJNJSA-N n-[(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl]acetamide Chemical compound CC(=O)NC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO ASXCJONOVQSZRF-LXGUWJNJSA-N 0.000 description 1
- PWODVNIZOOSARV-CSMHCCOUSA-N n-[(3r,4r,5r)-1,4,5,6-tetrahydroxy-2-oxohexan-3-yl]acetamide Chemical compound CC(=O)N[C@@H](C(=O)CO)[C@@H](O)[C@H](O)CO PWODVNIZOOSARV-CSMHCCOUSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000005527 organic iodine compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000007487 urography Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
-
- 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
- A61K49/0438—Organic X-ray contrast-enhancing agent comprising an iodinated group or an iodine atom, e.g. iopamidol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/512,004 US4125709A (en) | 1974-10-04 | 1974-10-04 | Polyhydroxy-alkyl-3,5-disubstituted-2,4,6-triiodocarbanilates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2541491A1 true DE2541491A1 (de) | 1976-04-15 |
Family
ID=24037296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752541491 Withdrawn DE2541491A1 (de) | 1974-10-04 | 1975-09-17 | Polyhydroxy-alkyl-3,5-disubst.-2, 4,6-trijodcarbanilate, verfahren zu ihrer herstellung und mittel, worin sie enthalten sind |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4125709A (enExample) |
| JP (1) | JPS5159837A (enExample) |
| AU (1) | AU497120B2 (enExample) |
| BE (1) | BE834162A (enExample) |
| CA (1) | CA1099262A (enExample) |
| DE (1) | DE2541491A1 (enExample) |
| FR (1) | FR2286643A1 (enExample) |
| GB (1) | GB1479397A (enExample) |
| IT (1) | IT1047304B (enExample) |
| NL (1) | NL7510912A (enExample) |
| SE (1) | SE7511131L (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4109081A (en) * | 1975-05-15 | 1978-08-22 | Mallinckrodt, Inc. | 1-(3,5-disubstituted-2,4,6-triiodophenyl)-3-(polyhydroxy-alkyl)urea compounds |
| US4321368A (en) * | 1975-10-20 | 1982-03-23 | Mallinckrodt, Inc. | Glycosyl triidobenzoic acid derivatives |
| US4230845A (en) * | 1978-08-31 | 1980-10-28 | Mallinckrodt, Inc. | Polyhydroxy-alkyl-3,5-disubstituted-2,4,6-triiodocarbanilates |
| US4263427A (en) * | 1978-11-29 | 1981-04-21 | Hoffmann-La Roche Inc. | Monensin urethane derivatives |
| US4243653A (en) * | 1979-04-27 | 1981-01-06 | The Regents Of The University Of California | Non-ionic polyiodo sugar substituted anilines |
| CA1248944A (en) * | 1982-09-28 | 1989-01-17 | Gareth J. Thomas | Anthracycline glycosides |
| US5143715A (en) * | 1990-03-28 | 1992-09-01 | Molecular Biosystems, Inc. | Organic contrast agent analog and method of making same |
| US5250283A (en) * | 1990-03-28 | 1993-10-05 | Molecular Biosystems, Inc. | Organic contrast agent analog and method of making same |
| US5324503A (en) * | 1992-02-06 | 1994-06-28 | Mallinckrodt Medical, Inc. | Iodo-phenylated chelates for x-ray contrast |
| EP4148059A4 (en) * | 2020-04-10 | 2024-02-21 | St. Marianna University School of Medicine | COMPOUND, CONTRAST AGENT AND METHOD FOR PRODUCING COMPOUND |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2855436A (en) * | 1954-07-26 | 1958-10-07 | Koninklijke Pharma Fab Nv | Production of substituted acrylic acid amides |
| US3144479A (en) * | 1958-08-07 | 1964-08-11 | Chemie Linz Ag | New iodine-containing benzoic acid esters |
| DE1251755B (de) * | 1960-10-17 | 1967-10-12 | Smith Kline &. French Laboratories, Philadelphia, Pa (V St A) | Verfahren zur Herstellung von 2 Phenyl-cyclopropyl carbaminsaurederivaten |
| US3198784A (en) * | 1962-07-25 | 1965-08-03 | Veisicol Chemical Corp | Process of producing sucrose benzoates |
| GB974134A (en) * | 1963-03-28 | 1964-11-04 | Science Union Et Compagnie Soc | Oxazolidinone derivatives |
| FR2053037B1 (enExample) * | 1969-06-27 | 1974-08-09 | Nyegaard & Co As | |
| BE757107A (fr) * | 1969-10-06 | 1971-04-06 | Basf Ag | Procede de preparation de derives d'alpha-n-formylamino- acides |
| GB1436357A (en) * | 1973-12-07 | 1976-05-19 | Laboraoires Andre Guerbet | Tri-iodo benzene derivatives and their use as x-ray contrast |
-
1974
- 1974-10-04 US US05/512,004 patent/US4125709A/en not_active Expired - Lifetime
-
1975
- 1975-09-10 CA CA235,140A patent/CA1099262A/en not_active Expired
- 1975-09-15 AU AU84836/75A patent/AU497120B2/en not_active Expired
- 1975-09-17 DE DE19752541491 patent/DE2541491A1/de not_active Withdrawn
- 1975-09-17 NL NL7510912A patent/NL7510912A/xx not_active Application Discontinuation
- 1975-09-23 FR FR7529120A patent/FR2286643A1/fr active Granted
- 1975-09-24 IT IT69371/75A patent/IT1047304B/it active
- 1975-10-01 GB GB40134/75A patent/GB1479397A/en not_active Expired
- 1975-10-03 BE BE160659A patent/BE834162A/xx unknown
- 1975-10-03 SE SE7511131A patent/SE7511131L/xx not_active Application Discontinuation
- 1975-10-03 JP JP50118988A patent/JPS5159837A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1099262A (en) | 1981-04-14 |
| JPS5159837A (en) | 1976-05-25 |
| US4125709A (en) | 1978-11-14 |
| FR2286643B1 (enExample) | 1979-09-14 |
| SE7511131L (sv) | 1976-04-05 |
| NL7510912A (nl) | 1976-04-06 |
| FR2286643A1 (fr) | 1976-04-30 |
| AU8483675A (en) | 1977-03-24 |
| GB1479397A (en) | 1977-07-13 |
| IT1047304B (it) | 1980-09-10 |
| BE834162A (fr) | 1976-02-02 |
| AU497120B2 (en) | 1978-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |