FR2354316A1 - Nouveaux agents de contraste iodes non-ioniques - Google Patents

Nouveaux agents de contraste iodes non-ioniques

Info

Publication number
FR2354316A1
FR2354316A1 FR7717904A FR7717904A FR2354316A1 FR 2354316 A1 FR2354316 A1 FR 2354316A1 FR 7717904 A FR7717904 A FR 7717904A FR 7717904 A FR7717904 A FR 7717904A FR 2354316 A1 FR2354316 A1 FR 2354316A1
Authority
FR
France
Prior art keywords
contrast agents
new non
iodine contrast
ionic iodine
ionic
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.)
Granted
Application number
FR7717904A
Other languages
English (en)
French (fr)
Other versions
FR2354316B1 (US20100292554A1-20101118-C00004.png
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nyegaard and Co AS
Original Assignee
Nyegaard and Co AS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nyegaard and Co AS filed Critical Nyegaard and Co AS
Publication of FR2354316A1 publication Critical patent/FR2354316A1/fr
Application granted granted Critical
Publication of FR2354316B1 publication Critical patent/FR2354316B1/fr
Granted legal-status Critical Current

Links

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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)
FR7717904A 1976-06-11 1977-06-10 Nouveaux agents de contraste iodes non-ioniques Granted FR2354316A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB24338/76A GB1548594A (en) 1976-06-11 1976-06-11 Triiodoisophthalic acid amides

Publications (2)

Publication Number Publication Date
FR2354316A1 true FR2354316A1 (fr) 1978-01-06
FR2354316B1 FR2354316B1 (US20100292554A1-20101118-C00004.png) 1982-11-12

Family

ID=10210154

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7717904A Granted FR2354316A1 (fr) 1976-06-11 1977-06-10 Nouveaux agents de contraste iodes non-ioniques

Country Status (11)

Country Link
US (1) US4250113A (US20100292554A1-20101118-C00004.png)
JP (1) JPS5321137A (US20100292554A1-20101118-C00004.png)
BE (1) BE855580A (US20100292554A1-20101118-C00004.png)
CH (1) CH630064A5 (US20100292554A1-20101118-C00004.png)
DE (1) DE2726196C2 (US20100292554A1-20101118-C00004.png)
DK (1) DK150504C (US20100292554A1-20101118-C00004.png)
FR (1) FR2354316A1 (US20100292554A1-20101118-C00004.png)
GB (1) GB1548594A (US20100292554A1-20101118-C00004.png)
HK (1) HK56683A (US20100292554A1-20101118-C00004.png)
NL (1) NL175814C (US20100292554A1-20101118-C00004.png)
SE (1) SE441181B (US20100292554A1-20101118-C00004.png)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0015867A1 (de) * 1979-03-08 1980-09-17 Schering Aktiengesellschaft Trijodierte Isophthalsäurediamide, deren Herstellung und diese enthaltende Röntgenkontrastmittel
EP0032387A1 (de) * 1980-01-11 1981-07-22 Schering Aktiengesellschaft Nichtionische 5-C-substituierte 2,4,6-Trijodisophthalsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Röntgenkontrastmittel
EP0082803A1 (de) * 1981-12-18 1983-06-29 Schering Aktiengesellschaft N-Hydroxyäthylierte 2,4,6-trijodaminoisophthalsäure-bis-trihydroxybutylamide, deren Herstellung und diese enthaltende Röntgenkontrastmittel
EP0083964A1 (en) * 1982-01-11 1983-07-20 Mallinckrodt, Inc. (a Delaware corporation) Compounds suitable for X-ray visualisation methods
EP0108638A1 (en) * 1982-11-08 1984-05-16 NYEGAARD & CO. A/S X-ray contrast agents
WO1998052909A1 (en) * 1997-05-23 1998-11-26 Nycomed Imaging As Preparation of tri-iodo benzene compounds
US6137006A (en) * 1997-05-23 2000-10-24 Nycomed Imaging As Preparation of tri-iodo benzene compounds

Families Citing this family (95)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1132901A (en) * 1978-07-04 1982-10-05 Fridtjov B. Rakli Aniline x-ray agent and buffer whose ph decreases with temperature
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
DE2928417A1 (de) * 1979-07-12 1981-01-29 Schering Ag Trijodierte basen
IT1193211B (it) * 1979-08-09 1988-06-15 Bracco Ind Chimica Spa Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono
IT1207226B (it) * 1979-08-09 1989-05-17 Bracco Ind Chimica Spa Derivati dell'acido 2,4,6-triiodo-isoftalico, metodo per la loro preparazione e mezzi di contrasto che li contengono.
DE3038853A1 (de) 1980-10-10 1982-05-27 Schering Ag, 1000 Berlin Und 4619 Bergkamen Neue n-hydroxy-alkylierte dicarbonsaeure-bis-(3,5-dicarbamoyl-2,4,6-trijodanilide), deren herstellung und diese enthaltende roentgenkonstrastmittel (ii)
JPS58102200A (ja) * 1981-12-14 1983-06-17 日本原子力事業株式会社 沈降分離槽
DK162045C (da) * 1982-10-01 1992-02-10 Nyegaard & Co As Trijodbenzenderivater, fremgangsmaade til fremstilling deraf og radiologiske praeparater indeholdende saadanne forbindelser
US5204086A (en) * 1982-10-01 1993-04-20 Nycomed Imaging As X-ray contrast agent
US5191119A (en) * 1983-10-20 1993-03-02 Cook Imaging Corp. Process for producing non-ionic radiographic contrast media utilizing N-allylation
US4584401A (en) * 1983-10-20 1986-04-22 Biophysica Foundation Methods and compositions involving polyhydroxylated polyiodo non-ionic contrast media
JPS6091807U (ja) * 1983-11-30 1985-06-22 松下電器産業株式会社 テ−ブル
JPS634809Y2 (US20100292554A1-20101118-C00004.png) * 1984-10-04 1988-02-08
US4954348A (en) * 1985-08-09 1990-09-04 Cook Imaging Corporation Non-ionic polyol contrast media from ionic contrast media
DE3689330T2 (de) * 1985-08-09 1994-05-19 Cook Imaging Corp Nichtionische polyolkontrastmittel aus ionischen kontrastmitteln.
US5035877A (en) * 1985-08-09 1991-07-30 Cook Imaging Corporation Non-ionic contrast media from ionic contrast media
JPH0637447B2 (ja) * 1987-10-31 1994-05-18 東洋紡績株式会社 新規アミド化合物
US5698739A (en) * 1989-07-05 1997-12-16 Schering Aktiengesellschaft Carboxamide non-ionic contrast media
GB8919929D0 (en) * 1989-09-04 1989-10-18 Nycomed As Compositions
US5232685A (en) * 1989-11-03 1993-08-03 Schering Aktiengesellschaft Nonionic x-ray contrast medium with high iodine content
DE3937118A1 (de) * 1989-11-03 1991-05-08 Schering Ag Nichtionische roentgenkontrastmittel mit hohem jodgehalt
US5614638A (en) * 1989-11-29 1997-03-25 Bracco International B.V. Nonionic radiographic contrast agents
CA2029830A1 (en) * 1989-11-29 1991-05-30 Ramachandran S. Ranganathan Nonionic radiographic contrast agents
US5869024A (en) * 1989-11-29 1999-02-09 Bracco International B.V. Methods and compositions for using non-ionic contrast agents to reduce the risk of clot formation in diagnostic procedures
US5191120A (en) * 1989-12-13 1993-03-02 Mallinckrodt Medical, Inc. Process for preparing nonionic X-ray contrast agents
US4997983A (en) * 1990-01-31 1991-03-05 Mallinckrodt, Inc. Process for production of ioversol
US5527926A (en) * 1990-11-26 1996-06-18 Bracco International B.V. Methods and compositions for using non-ionic contrast agents to reduce the risk of clot formation in diagnostic procedures
US5356613A (en) * 1991-03-18 1994-10-18 Mallinckrodt Medical, Inc. X-ray contrast agents, compositions and methods
DE4109169A1 (de) * 1991-03-20 1992-09-24 Koehler Chemie Dr Franz Wasserloesliche nicht ionische roentgenkontrastmittel sowie mittel und verfahren zu ihrer herstellung
US5169864A (en) * 1991-11-15 1992-12-08 Baxter International Inc. Unbuffered premixed ranitidine formulation
JPH07501809A (ja) * 1991-12-03 1995-02-23 マリンクロッド・メディカル・インコーポレイテッド 非イオン性ｘ線造影剤組成物およびその製造方法
US5278311A (en) * 1992-06-05 1994-01-11 E. R. Squibb & Sons, Inc. Nonionic radiographic contrast agents
WO1994005337A1 (en) * 1992-09-02 1994-03-17 Mallinckrodt Medical, Inc. Nonionic x-ray contrast agents, compositions and methods
IL110391A (en) * 1993-07-30 1998-12-06 Zambon Spa Process for the formation of infamidol
US5665331A (en) * 1995-01-10 1997-09-09 Nanosystems L.L.C. Co-microprecipitation of nanoparticulate pharmaceutical agents with crystal growth modifiers
US5662883A (en) * 1995-01-10 1997-09-02 Nanosystems L.L.C. Microprecipitation of micro-nanoparticulate pharmaceutical agents
US5716642A (en) * 1995-01-10 1998-02-10 Nano Systems L.L.C. Microprecipitation of nanoparticulate pharmaceutical agents using surface active material derived from similar pharmaceutical agents
US5560932A (en) * 1995-01-10 1996-10-01 Nano Systems L.L.C. Microprecipitation of nanoparticulate pharmaceutical agents
US5543133A (en) * 1995-02-14 1996-08-06 Nanosystems L.L.C. Process of preparing x-ray contrast compositions containing nanoparticles
DE19510864A1 (de) * 1995-03-16 1996-09-19 Schering Ag Röntgenkontrastmittel für die Computertomographie und Urographie
IT1275429B (it) * 1995-05-18 1997-08-07 Zambon Spa Processo per la preparazione di un intermedio utile nella sintesi di composti organici
CN1078201C (zh) * 1995-11-20 2002-01-23 江苏省原子医学研究所 一种碘海醇的制备方法
GB9618055D0 (en) * 1996-08-29 1996-10-09 Nycomed Imaging As Process
US5840967A (en) 1996-08-29 1998-11-24 Nycomed Imaging As Process for the preparation of contrast agents
GB9618056D0 (en) * 1996-08-29 1996-10-09 Nycomed Imaging As Process
US5705692A (en) * 1996-09-27 1998-01-06 Abbott Laboratories Process for the preparation of iohexol
PT101919B (pt) * 1996-09-30 2000-01-31 Hovione Sociedade Quimica Sa Um processo para a purificacao de tohexol
US5861140A (en) * 1996-11-20 1999-01-19 Hoechst Celanese Corp. Tripodal paramagnetic contrast agents for MR imaging
US5861138A (en) * 1996-11-20 1999-01-19 Hoechst Celanese Corp. Ligands for MRI contrast agent
US5824821A (en) * 1997-02-07 1998-10-20 Nycomed Imaging As Process for the preparation of iodinated contrast agents and intermediates therefor
US5847212A (en) * 1997-04-21 1998-12-08 Abbott Laboratories Process for the preparation of iohexol
GB9710726D0 (en) * 1997-05-23 1997-07-16 Nycomed Imaging As Compound
GB9710725D0 (en) 1997-05-23 1997-07-16 Nycomed Imaging As Process
IT1292037B1 (it) * 1997-05-30 1999-01-25 Bracco Spa Processo per la preparazione di 5-(acetil 62,3-diidrossipropil)- ammino)-n,n'-bis(2,3-diidrossipropil)-2,4,6-triiodo-1,3-benzen-
US5820851A (en) * 1997-08-21 1998-10-13 Hoechst Celanese Corporation Tripodal pyridine ligands as MRI contrast agents
US5869025A (en) * 1997-08-21 1999-02-09 Hoechst Celanese Corporation Tripodal aromatic heterocycle carboxamide MRI contrast agents
US5824288A (en) * 1997-08-21 1998-10-20 Hoechst Celanese Corporation Thio-substituted pyridines as MRI ligand precursors
US5869026A (en) * 1997-08-21 1999-02-09 Hoechst Celanese Corp. Tripodal carboxamide ligands for MRI contrast agents
US5858329A (en) * 1997-08-21 1999-01-12 Hoechst Celanese Corporation MRI diagnostic procedures using tripodal pyridinyl metal complexes
GB9720969D0 (en) * 1997-10-02 1997-12-03 Nycomed Imaging As Process
GB9725010D0 (en) * 1997-11-26 1998-01-28 Nycomed Imaging As Process
US20040170561A1 (en) * 1998-09-08 2004-09-02 Jesse Salb Functional radiographic imaging methods and agents
US6751290B2 (en) 1998-09-08 2004-06-15 Veritas Pharmaceuticals, Inc. Radiographic assessment of tissue after exposure to a compound
US6226352B1 (en) 1998-09-08 2001-05-01 Veritas Pharmaceuticals, Inc. System and method for radiographic imaging of tissue
US6723746B2 (en) * 1998-09-08 2004-04-20 Veritas Pharmaceuticals, Inc. Functional radiographic imaging methods and agents
GB9825095D0 (en) * 1998-11-16 1999-01-13 Nycomed Imaging As Chemical process
EP1263324B1 (en) 2000-03-16 2009-12-02 Veritas Pharmaceuticals Radiographic assessment of tissue response to compounds
AU2002245169A1 (en) 2000-11-10 2002-07-08 Wm. Marsh Rice University Fullerene (c60)-based x-ray contrast agent for diagnostic imaging
IT1319670B1 (it) 2000-12-01 2003-10-23 Bracco Spa Processo per la preparazione di 5-ammino-n,n'-bis(2-idrossi-1-(idrossimetil)etil))-1,3-benzendicarbossammide (i) e 5-ammino-n,n'-
ITMI20010773A1 (it) * 2001-04-11 2002-10-11 Chemi Spa Processo per la produzione di ioexolo ad elevata purezza
KR20030032185A (ko) * 2001-10-16 2003-04-26 동국제약 주식회사 Ｎ,ｎ'-비스[2,3-디히드록시프로필]-2,4,6-트리요오드-5-아세틸아미도 이소 프탈아미드의 결정화방법
EA011516B1 (ru) 2005-01-13 2009-04-28 Синвеншен Аг Композиционный материал и способ его изготовления
JP4801661B2 (ja) * 2005-03-18 2011-10-26 マナック株式会社 ５−アミノ−２，４，６−トリヨードイソフタル酸誘導体のアセチル化方法
PT103391B (pt) 2005-11-24 2008-10-30 Hovione Farmaciencia S A Processo para fabrico de lohexol
CN100344606C (zh) * 2005-12-28 2007-10-24 江苏省原子医学研究所 一种碘昔兰的制备方法
EP2093206A1 (en) 2008-02-20 2009-08-26 BRACCO IMAGING S.p.A. Process for the iodination of aromatic compounds
US20110256068A1 (en) 2009-01-09 2011-10-20 Wistand Lars-Goeran Contrast media compositions
DK2451994T3 (da) 2009-07-07 2014-01-20 Bracco Imaging Spa Fremgangsmåde til fremstilling af et ioderende middel
EP2277859A1 (en) * 2009-07-21 2011-01-26 GE Healthcare AS Acetylation using reduced concentration of acetic acid anhydride for synthesizing non-ionic X-ray contrast agents
EP2277851A1 (en) * 2009-07-21 2011-01-26 GE Healthcare AS Acetylation using reduced volume of acetic acid anhydride for synthesizing non-ionic X-ray contrast agents
US20110021821A1 (en) * 2009-07-21 2011-01-27 Ge Healthcare As Continuous acetylation process in synthesis of non-ionic x-ray contrast agents
KR101585751B1 (ko) * 2010-07-12 2016-01-14 지이 헬스케어 에이에스 저농도의 조영제 및/또는 저방사선량의 x-선 영상화
CN102249948B (zh) * 2011-05-23 2014-01-29 苏州昊帆生物科技有限公司 5-乙酰氨基-n,n’-双-(2,3-二羟基丙基)-2,4,6-三碘间苯二甲酰胺的合成方法
EP2606912A1 (en) * 2011-12-23 2013-06-26 Central Medical Service Co., Ltd. Contrast medium composition with contrast enhancement effect by comprising highly concentrated agent
WO2015082720A1 (en) 2013-12-06 2015-06-11 Ge Healthcare As Alternative process for the purification of an intermediate in the synthesis of non-ionic x-ray contrast agents
EP3077366B1 (en) * 2013-12-06 2017-08-09 GE Healthcare AS Alternative acetylation process in the synthesis of non-ionic xray contrast agents
WO2015082718A1 (en) * 2013-12-06 2015-06-11 Ge Healthcare As Alternative process for the purification of an intermediate in the synthesis of non-ionic x-ray contrast agents
RU2711501C2 (ru) 2014-03-04 2020-01-17 Оцука Фармасьютикал Ко., Лтд. Порошок йогексола и способ его применения
PT108524B (pt) * 2015-06-02 2017-12-15 Hovione Farmaciência S A Processo para a preparação de intermediários úteis na preparação de agentes de contraste não-iónicos
CN107778191A (zh) * 2016-08-26 2018-03-09 正大天晴药业集团股份有限公司 一种碘普罗胺及其中间体的制备方法
RU2655619C1 (ru) * 2017-06-13 2018-05-29 Алексей Георгиевич Александров Способ получения фармацевтической субстанции на основе йогексола
CN107857714B (zh) * 2017-11-29 2020-11-13 上海司太立制药有限公司 一种碘海醇中间体杂质的制备方法和用途
CN108191690A (zh) * 2017-12-11 2018-06-22 天津河清化学工业有限公司 碘海醇节能环保的连续化制备方法
CN108191689A (zh) * 2017-12-11 2018-06-22 天津河清化学工业有限公司 一种新型碘海醇节能环保的连续化制备方法
EP4001261A1 (en) 2020-11-23 2022-05-25 Justesa Imagen S.A.U Procedure for obtaining high purity iohexol

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2053037A1 (US20100292554A1-20101118-C00004.png) * 1969-06-27 1971-04-16 Nyegaard & Co As
BE836355A (fr) * 1974-12-13 1976-06-08 Agents de constraste radiographique non ioniques facilement solubles dans l'eau et procede pour les preparer

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GB1321591A (en) 1969-06-27 1973-06-27 Nyegaard & Co As Non-ionic iodinated x-ray contrast agents
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
BE788054A (fr) * 1971-08-26 1973-02-26 Bracco Ind Chimica Spa Nouvel agent de contraste radiographique et procede pour le preparer

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
FR2053037A1 (US20100292554A1-20101118-C00004.png) * 1969-06-27 1971-04-16 Nyegaard & Co As
BE836355A (fr) * 1974-12-13 1976-06-08 Agents de constraste radiographique non ioniques facilement solubles dans l'eau et procede pour les preparer

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0015867A1 (de) * 1979-03-08 1980-09-17 Schering Aktiengesellschaft Trijodierte Isophthalsäurediamide, deren Herstellung und diese enthaltende Röntgenkontrastmittel
EP0032387A1 (de) * 1980-01-11 1981-07-22 Schering Aktiengesellschaft Nichtionische 5-C-substituierte 2,4,6-Trijodisophthalsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Röntgenkontrastmittel
EP0082803A1 (de) * 1981-12-18 1983-06-29 Schering Aktiengesellschaft N-Hydroxyäthylierte 2,4,6-trijodaminoisophthalsäure-bis-trihydroxybutylamide, deren Herstellung und diese enthaltende Röntgenkontrastmittel
EP0083964A1 (en) * 1982-01-11 1983-07-20 Mallinckrodt, Inc. (a Delaware corporation) Compounds suitable for X-ray visualisation methods
EP0108638A1 (en) * 1982-11-08 1984-05-16 NYEGAARD & CO. A/S X-ray contrast agents
WO1998052909A1 (en) * 1997-05-23 1998-11-26 Nycomed Imaging As Preparation of tri-iodo benzene compounds
US6137006A (en) * 1997-05-23 2000-10-24 Nycomed Imaging As Preparation of tri-iodo benzene compounds

Also Published As

Publication number Publication date
US4250113A (en) 1981-02-10
JPS5654310B2 (US20100292554A1-20101118-C00004.png) 1981-12-24
DK150504C (da) 1988-01-11
FR2354316B1 (US20100292554A1-20101118-C00004.png) 1982-11-12
SE7706792L (sv) 1977-12-12
GB1548594A (en) 1979-07-18
DE2726196A1 (de) 1977-12-22
SE441181B (sv) 1985-09-16
DE2726196C2 (de) 1983-12-29
BE855580A (fr) 1977-12-12
CH630064A5 (de) 1982-05-28
NL175814C (nl) 1985-01-02
DK150504B (da) 1987-03-16
JPS5321137A (en) 1978-02-27
HK56683A (en) 1983-11-25
NL7706385A (nl) 1977-12-13
DK258477A (da) 1977-12-12

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