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Chemistry of X-Ray Contrast Media

  • Chapter
Radiocontrast Agents

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 73))

Abstract

X-ray contrast media (CM) have been used since the first discovery of X-rays by Roentgen in 1895. The function of such media is to opacify an organ or portion of the body to X-rays, providing thereby greater diagnostic information to the physician. Many opaque atoms have been studied in many chemical forms; for example, bismuth, barium, tantalum, strontium, and bromine have all been used in a variety of compounds. Although many water-soluble compounds have been evaluated, by 1980 only two atoms, iodine and bromine, have been found to be of significant diagnostic use. This chapter will devote itself to iodinated organic compounds, since they are by far the most diagnostically useful, in particular, we shall discuss mainly water-soluble compounds. The pertinent literature has been surveyed through mid-1980.

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References

  1. Hoey GB, Wiegert PE, Rands RD Jr (1971) Organic iodine compounds as X-ray contrast media. In: Knoefel PK (ed) Radiocontrast agents, sect 76, vol 1. Pergamon, New York, pp 23–131

    Google Scholar 

  2. Ackerman JH (1970) Diagnostic Agents. In: Burger AA (ed) Medicinal chemistry, 3rd edn. Wiley, New York, pp 1686–1699

    Google Scholar 

  3. Doerge RF, Wilson CO (1977) Diagnostic agents. In: Wilson CO, Gisvold O, Doerge RF (eds) Textbook of organic medicinal and pharmaceutical chemistry. Lippincott, Philadelphia, p 939

    Google Scholar 

  4. Lasser C (1967) Dynamic factors in roentgen diagnosis. Williams and Wilkins, Baltimore

    Google Scholar 

  5. Miller RE, Skucas J (1977) Radiographic contrast agents. University Park Press, Baltimore, pp 329–418, 451–494

    Google Scholar 

  6. Contrast Material Symposium (1980) Invest Radiol [Suppl] 15/6

    Google Scholar 

  7. Wallingford VH (1953) The development of organic iodine compounds as X-ray contrast media. J Am Pharmacol Assoc 42:721–728

    Article  CAS  Google Scholar 

  8. See also: Wallingford VH, Becker HH, Kruty M (1952) X-ray contrast media. I. Iodinated acylaminobenzoic acids. J Am Chem Soc 74:4365

    Article  CAS  Google Scholar 

  9. Knoefel PA (1971) Binding of iodinated radiocontrast agents to plasma proteins. In: Knoefel PA (ed) Radiocontrast agents, sect 76, vol 1. Pergamon, New York, pp 133–145

    Google Scholar 

  10. Baker CE (1979/1980) Physicians desk reference for radiology and nuclear medicine. Medical Economics, Oradell, p 75

    Google Scholar 

  11. Aspelin P (1979) Effect of ionic and nonionic contrast media on red cell deformability in vitro. Acta Radiol [Diagn] (Stockh) 20:1–12

    CAS  Google Scholar 

  12. Guerbet M, Tilly G (1969) 2,4,6-Triiodo-3-(N-hydroxyethyl)carbamoyl)-5-(acetylamino) benzoic acid as an opaquing agent for radiography. French patent 6777, 21 April 1969

    Google Scholar 

  13. Grainger RD (1979) A clinical trial of a new low osmolality contrast medium. Sodium and meglumine ioxaglate (Hexabrix) compared with meglumine iothalamate (Conray) for carotid arteriography. Br J Radiol 52:781–786

    Article  PubMed  CAS  Google Scholar 

  14. Lehninger AL (1975) The molecular basis of cell structure and function. In: Biochemistry, 2nd ed. Worth, New York, p 174

    Google Scholar 

  15. Harrington C, Michie C, Lynch PR, Russel MA, Oppenheimer MJ (1966) Blood brain barrier changes associated with unilateral cerebral angiography. Invest Radiol 1:431–440

    Article  PubMed  CAS  Google Scholar 

  16. Sorensen SE (1971) Changes in vascular permeability after local application of roentgen contrast media in the hamster cheek pouch. Acta Radiol [Diagn] (Stockh) 11:274–288

    CAS  Google Scholar 

  17. Waldron RL, Bridgenbraugh RB, Dempsey EW (1974) Effect of angiographic contrast media at the cellular level in the brain: hypertonic vs. chemical action. AJR 122:469–476

    Google Scholar 

  18. Rapoport SI, Hori M, Klatzo I (1972) Testing of hypothesis for osmotic opening of the blood brain barrier. Am J Physiol 223:323–331

    PubMed  CAS  Google Scholar 

  19. Sterrett PR, Bradley IM, Kitten TG, Janssen FH, Holloway SL (1976) Cerebrovascu-lature permeability changes following experimental cerebral angiography. A light and electron microscopic study. J Neurol Sci 30:385–403

    Article  PubMed  CAS  Google Scholar 

  20. Chaplin H, Carlsson E (1961) Change in human red blood cells during in vitro exposure to several roentgenologic contrast media. AJR 86:1127–1137

    Google Scholar 

  21. Giammona ST, Lurie PR, Segar WE (1963) Hypertonicity following selective angiocardiography. Circulation 28:1096–1101

    PubMed  CAS  Google Scholar 

  22. Meyer MW, Read RC (1964) Red cell aggregation from concentrated saline and angiographic media. Radiology 82:630–635

    PubMed  CAS  Google Scholar 

  23. Friesinger GC, Schaffer J, Criley JM, Gartner RA, Ross RJ (1965) Hemodynamic consequences of the injection of radiopaque material. Circulation 31:730–740

    PubMed  CAS  Google Scholar 

  24. Cohen LS, Kokko JP, Williams WH (1969) Hemolysis and hemoglobinuria following angiography. Radiology 92:329–332

    PubMed  CAS  Google Scholar 

  25. Von Bubnoff M, Riecker G (1961) Zellosmolaritat und Zellwassergehalt. Klinische und experimentelle Untersuchungen an Erythrozyten. Klin Wochenschr 39:724–733

    Article  Google Scholar 

  26. Raininko R (1979) Role of hypertonicity in the endothelial injury caused by angiographic contrast media. Acta Radiol [Diagn] (Stockh) 20:410–416

    CAS  Google Scholar 

  27. Almen T (1971) Toxicity of radiocontrast agents. In: Knoefel PK (ed) Radiocontrast agents, vol 2. Pergamon, New York, pp 443–550

    Google Scholar 

  28. Fischer HW (1968) Hemodynamic reaction to angiographic media. A survey and commentary. Radiology 91:66–73

    PubMed  CAS  Google Scholar 

  29. Rapoport SI, Thompson HK, Bidinger JM (1974) Equi-osmolal opening of the blood brain barrier in the rabbit by different contrast media. Acta Radiol [Diagn] (Stockh) 15:21–32

    CAS  Google Scholar 

  30. Oldendorf WH (1971/1972) Blood brain barrier permeability to lactate. Eur Neurol 6:49–55

    Article  PubMed  CAS  Google Scholar 

  31. Hilal SK, Dauth GW, Hess KH, Gilman S (1978) Development and evaluation of a new water-soluble iodinated myelographic contrast medium with markedly reduced convulsive effects. Radiology 126:417–422

    PubMed  CAS  Google Scholar 

  32. Haughton V, Ho K-C, Unger GF (1977) Arachnoiditis following myelography with water-soluble agents. Radiology 125:731–733

    PubMed  CAS  Google Scholar 

  33. Rapoport SI, Levitan H (1974) Neurotoxicity of X-ray contrast media. AJR 122:186–193

    CAS  Google Scholar 

  34. Binz A (1937) History of the uroselectans. Z Urol 31:73–84

    CAS  Google Scholar 

  35. Long L Jr, Burger A (1941) Synthesis of some iodinated aromatic compounds. J Am Chem Soc 63:1586–1589

    Article  CAS  Google Scholar 

  36. Wang JY-C (1980) Deiodination kinetics of water-soluble radiopaques. J Pharm Sci 69/6:671–675

    Article  Google Scholar 

  37. Fischer H (1978) Contrast media in coronary arteriography: a review. Invest Radiol 13:450–457

    Article  PubMed  CAS  Google Scholar 

  38. Mohl MH, Rizzolo RR, Hoey GB, Gorman AD (1979) Determination of diatrizoic acid in X-ray contrast media by high performance liquid chromatography. 15th Midwest regional meeting, American Chemical Society, St. Louis, 8 November 1979

    Google Scholar 

  39. Hoey GB, Wiegert PE, Rands RD Jr (1971) Organic iodine compounds as X-ray contrast media. In: Knoefel PK (ed) Radiocontrast agents, sect 76, vol 1. Pergamon, New York, p 23

    Google Scholar 

  40. Lasser C (1967) Dynamic factors in roentgen diagnosis. Williams and Wilkins, Baltimore, pp 77–79

    Google Scholar 

  41. Kodama JK, Butler WM, Tusing TW, Hallett FP (1963) Iothalamate: a new intravascular radiopaque medium with unusual pharmacotoxic inertness. Exp Mol Pathol [Suppl] 2:65–80

    CAS  Google Scholar 

  42. Melartin E, Tuohimaa PJ, Dabb R (1970) Neurotoxicity of iothalamates and diatrizoates. I. Significance of concentration and cation. Invest Radiol 5:13–21

    PubMed  CAS  Google Scholar 

  43. Haley TJ, McCormick WG (1957) Pharmacological effects produced by intracerebral injection of drugs in the conscious mouse. Br J Pharmacol 12:12–15

    CAS  Google Scholar 

  44. Valzelli L (1964) A simple method to inject drugs intracerebrally. Med Exp 11:23–26

    PubMed  CAS  Google Scholar 

  45. Sovak M, Ranganathan R (1980) Stability of nonionic water-soluble contrast media: implications for their design. Invest Radiol 15:S323–S328

    Article  PubMed  CAS  Google Scholar 

  46. Hopkins RM, Tusing TW (1979) Preclinical pharmacology and toxicology evaluation for diagnostic X-ray contrast media. R&D Division, Mallinckrodt, St Louis

    Google Scholar 

  47. Gries H, Pfeiffer H, Speck U, Mützel W (1981) Ionic 5-C-substituted-2,4,6-triio-doisophthalic acid derivatives. German Offen 3,001,293, 16 July 1981

    Google Scholar 

  48. Gries H (1981) 3,5-Dicyano-2,4,6-triiodobenzoic acids. German Offen 3,001,294, 16 July 1981

    Google Scholar 

  49. Priewe H, Rutkowski R, Pirner K, Junkman K (1954) Derivatives of 2,4,6-triiodo-3-aminobenzoic acid. Chem Ber 87:651–658

    Article  CAS  Google Scholar 

  50. Hoey GB, Rands RD, Wiegert PE, Chapman DW, Zey RL, DeLaMater GB (1966) X-ray media. II. Synthesis of alkanoylbis(isophthalamic acids) and X-ray contrast agents. J Med Chem 9:964–966

    Article  PubMed  CAS  Google Scholar 

  51. Wiegert PE (1972) 5,5′,5′-(Nitrilotriacetamido)tris-(2,4,6-triiodobenzoic acids). German Offen 2,132,614, 17 Aug 1972

    Google Scholar 

  52. Wiegert PE (1974) (Nitrilotriacyltriimino)tris-(2,4,6-triiodobenzoic acid) compounds for X-ray contrast media. British patent 1,346,795, 13 Feb 1974

    Google Scholar 

  53. Bjork L, Erickson U, Ingelman B (1972) New type of contrast medium in selective coronary arteriography. Ups J Med Sci 77/1:19–21

    Google Scholar 

  54. Bjork L, Erickson UE, Ingelman BGA (1970) New type of contrast medium in arthrography. AJR 109/3:505–510

    Google Scholar 

  55. Bjork L (1959) X-ray contrast agent. French patent M 7251, 8 Sept 1969

    Google Scholar 

  56. Felder E, Pitre D, Fumagalli L, Lorenzotti E (1973) Radiopaque contrast media. XXIV. Synthesis and structure-activity relations of new hexaiodinated radiopaque compounds. Farmaco [Sci] 28/11:912–924

    Google Scholar 

  57. Felder E, Pitre D (1971) 3′,3″-Dicarboxy-2′,2″,4′,4″,6′,6″ hexaiodo-4,7,10,13-tetraoxohexadecane-l,16-dianilide as X-ray contrast agent. German Offen 1,937,211, 4 Feb 1971

    Google Scholar 

  58. Felder E, Pitre D (1969) Nontoxic 4,7,10-trioxatridecanebis(3-carboxy-2,4,6-triiodoanilide) for cholecystography. German Offen 1,922,578, 13 Nov 1969

    Google Scholar 

  59. Pharmacia AB (1970) Hydroxyalkylene bis(acylamino-2,4,6-triiodobenzoic acid) derivatives for use as X-ray visualization agents. British patent 1,207,974, 7 Oct 1970

    Google Scholar 

  60. Pfeiffer H, Speck U, Kolb H (1975) 3,5,9-Trioxaundecane-1, 11-dioxyl-bis(3-carboxyl-2,4,6-triiodoanilide) and its salts. German Offen 2,405,652, 21 Aug 1975

    Google Scholar 

  61. Weinmann HJ, Mützel W, Souchon R, Wegener OH (1981) Experimental water soluble contrast media for computed tomography of the liver. Excerpta Med Int Congr Ser 561:95–100

    CAS  Google Scholar 

  62. Bernstein J, Losee KA (1971) Tris(2-(2,4,6-triiodo-3-carboxy-5-acetamido-benzami-do) ethyl) amine. German Offen 2,039,214, 25 Feb 1971

    Google Scholar 

  63. Tilly G, Hardouin MJC, Lautrou J (1977) X-ray contrast media. US patent 4,014,986, 29 March 1977

    Google Scholar 

  64. Tilly G, Hardouin MJC, Lautrou J (1977) X-ray contrast media. US patent 4,065,554, 27 Dec 1977

    Google Scholar 

  65. Thomson KR, Evill CA, Fritzche J, Benness GT (1980) Comparison of iopamidol, ioxaglate and diatrizoate during coronary arteriography in dogs. Invest Radiol 15:234–241

    Article  PubMed  CAS  Google Scholar 

  66. Owman T, Hoevels J (1979) Comparison of monomer, dimer and non-ionized medium at urography with simulated compression. ROEFO 131/3:309–317

    Article  Google Scholar 

  67. Higgins CB, Sovak M, Schmidt WS, Kelley MJ, Newell JD (1980) Direct myocardial effects of intracoronary administration of new contrast material with low osmolality. Invest Radiol 15:39–46

    Article  PubMed  CAS  Google Scholar 

  68. Tilly G, Hardouin JC, Lautrou J (1974) Improvements in or relating to new X-ray contrast media. British patent 1,488,904, 31 May 1974

    Google Scholar 

  69. Tilly G, Hardouin MJG, Lautrou J (1979) New ionic polyiodo benzene derivatives useful as X-ray contrast media. British patent 2,002,583A, 19 Dec 1979

    Google Scholar 

  70. Hebky J, Polacek J (1970) Preparation of 3,5-diaminobenzyl alcohol and its iodinated derivatives. Coll Czech Chem Commun 35/2:667–674

    Google Scholar 

  71. Hebky J, First B, Polacek J, Karasek M (1970) Synthesis of iodinated benzylamine X-ray diagnosis. Coll Czech Chem Commun 35/3:867–881

    Google Scholar 

  72. Hebky J (1970) X-ray contrast agents. Pharm Ind 32/10A:938–940

    Google Scholar 

  73. Hebky J, Polacek J, Tikal I, Lupinek V, Sova M (1976) Synthesis of iodinated derivatives of 3-aminobenzylamine and 3,5-diaminobenzylamine for X-ray diagnosis. Coll Czech Chem Commun 41/10:3094–3105

    Google Scholar 

  74. Van Ootegham SP, Smith RG, Daves G Jr, Chang EM, El-Mazati A, Olsen GD, Riker WK (1976) Iodo-bis(quaternary ammonium) salts. Potential cartilage-selective X-ray contrast agents. J Med Chem 19/11:1349–1352

    Article  Google Scholar 

  75. Sovak M, Weitl FL, Lang JH, Higgins CB (1979) Development of a radiopaque cation: toxicity of the benzylammonium group. Eur J Med Chem Chim Ther 14/3:257–260

    Google Scholar 

  76. Speck U, Klieger E, Mützel W (1981) Triiodinated aminoacetamido isophthalamide X-ray contrast agents. US patent 4,283,381, 11 Aug 1981

    Google Scholar 

  77. Suter H, Zutter H (1975) Diiodofumaric acid derivatives as possible new X-ray contrast agents. Pharm Acta Helv 50/5:151–152

    Google Scholar 

  78. Carnmalm B, Gyllander J, Jonsson HA, Mikiver L (1974) Potential X-ray contrast agents. III. Synthesis of some derivatives of iodomethanesulfonic acid and tris (iodomethyl) acetic acid. Acta Pharm Suec 11/2:161–166

    Google Scholar 

  79. Suter H, Zutter H, Brunner J (1971) Tetraiodoterephthalic acid derivatives as X-ray contrast agents. Helv Chim Acta 54/7:2097–2107

    Article  Google Scholar 

  80. Bedford AJM (1973) Radiographic contrast medium. German Offen 2,136,255, 22 March 1973

    Google Scholar 

  81. Hoey GB (1970) The symposium on contrast media toxicity of the Association of University Radiologists. Invest Radiol 5/6:453

    Google Scholar 

  82. Kleiger E, Schroeder E (1975) Synthesis of N-(3-acylamino-5-alkylcarbamoyl-2,4,6-triiodobenzoyl) amino acids as X-ray contrast agents. Eur J Med Chem Chim Ther 10/1:84–88

    Google Scholar 

  83. Bjork L, Erickson U, Ingelman B (1970) Polymeric contrast media for roentgenologic examination of gastrointestinal tract. Invest Radiol 3:142–148 (and references therein)

    Article  Google Scholar 

  84. Bjork L, Erickson U, Ingelman B, Zaar B (1974) Improved polymeric contrast agents for roentgenologic examination of the gastrointestinal tract. Upsala J Med Sci 79:103–105 (and references therein)

    Article  PubMed  CAS  Google Scholar 

  85. Bjork L, Erickson U, Ingelman B (1976) Preliminary report on angiography with polymeric contrast agents in rabbits and dogs. Ups J Med Sci 81:183–187 (and references therein)

    Article  PubMed  CAS  Google Scholar 

  86. Almen T (1969) Contrast agent design. Some aspects of the synthesis of water soluble contrast agents of low osmolarity. J Theor Biol 24:216–226

    Article  PubMed  CAS  Google Scholar 

  87. Holtermann H (1973) Metrizamide, a nonionic, water soluble contrast medium. Acta Radiol [Suppl] (Stockh) 335:1–4

    CAS  Google Scholar 

  88. Kejha J, Radek O, Jelinek V, Nemecek O (1966) X-ray opaque agents. Czech patent 118,444, 15 May 1966 (cf Chem Abstr 66:55207r, 1967)

    Google Scholar 

  89. Kocourek J (1966) A method for the manufacture of 6-O-(2,4,6-triiodophenyl)-D-glucose. Czech patent 120,380, 15 Oct 1966

    Google Scholar 

  90. Almen TO, Haavaldsen J, Nordal N (1971) Nonionic iodinated X-ray contrast media. German Offen 2,031,724, 7 Jan 1971 (cf Chem Abstr 74:99662e, 1971)

    Google Scholar 

  91. Torsten HO, Almen TO, Haavaldsen J, Vegard T (1972) N-(2,4,6-triiodobenzoyl)-sugar amines. US patents 3,701,771, 31 Oct 1972 (and 4,021,481, 3 May 1977)

    Google Scholar 

  92. Suter H, Zutter H, Mueller HR (1971) Iodomethansulfonamides. German Offen 2,201,578, 23 March 1971 (cf Chem Abstr 78:3694a, 1973; see also British patent 1,359,908, 17 July 1974)

    Google Scholar 

  93. Felder E, Pitre D, Tirone P (1977) Radiopaque contrast media. XCIV. Preclinical studies with a new nonionic contrast agent. Farmaco [Sci] 32:835–844

    CAS  Google Scholar 

  94. Herskovits TT, Kelly TM (1973) Viscosity studies of aqueous solutions of alcohols, ureas, and amides. J Phys Chem 77:381–388 (and references cited therein)

    Article  CAS  Google Scholar 

  95. Rakli FB, Keely MJ (1980) A process for the preparation of a sterile injectable physiologically acceptable solution of an X-ray contrast agent and solutions of the contrast agent and a buffer. British patent 2,031,405, 23 April 1980

    Google Scholar 

  96. Weitl FL, Sovak M, Ohno M (1976) Synthesis of a potential water soluble radiographic contrast medium, 2,4,6-triiodo-3-acetamido-5-N-methylcarboxamidophenyl β-D-glucopyranoside. J Med Chem 10:353–356

    Article  Google Scholar 

  97. Weitl FL, Sovak M, Williams TM, Lang JH (1976) Studies in the design of X-ray contrast agents. Synthesis, hydrophobicity, and solubility of some iodoresorcyl bis β-glucosides. J Med Chem 10:1359–1362

    Article  Google Scholar 

  98. Sovak M (this volume) Introduction

    Google Scholar 

  99. Felder E, Vitale RS, Pitre DF (1977) Water soluble, non-ionizing hydroxy-containing amide derivates of 2,4,6-triiodo-isophthalic acid. US patent 4,001,323, 4 Jan 1977

    Google Scholar 

  100. Felder E, Pitre DE (1976) Easily water-soluble nonionic X-ray contrast agents. German Offen 2,547,789, 24 Jan 1976 (cf Chem Abstr 8s:94103r, 1976)

    Google Scholar 

  101. Pfeiffer H (1979) Method for the preparation of serinol (l,3-dihydroxy-2-amino-propane). German Auslegeschrift 2,742,981, 22 March 1979)

    Google Scholar 

  102. Pfeiffer H, Speck U (1978) New dicarboxylic acid-bis-(3,5-dicarbamoyl-2,4,6-triiodoanilides). German Offen 2,628,517, 5 Jan 1978

    Google Scholar 

  103. Sovak M, Ranganathan R, Speck U (1982) Nonionic dimer: Development and initial testing of intrathecal contrast agents. Radiology 142:115–118

    PubMed  CAS  Google Scholar 

  104. Felder E, Pitre D (1978) Water soluble, nonionic X-ray contrast agent. German Offen 2,805,928, 5 Oct 1978 (cf Chem Abstr 90:127532p, 1979)

    Google Scholar 

  105. Felder E, Vitale RS, Pitre D (1979) Water-soluble, nonionizing, radiopaque compounds and contrast compositions containing the same. US patent 4,139,605, 13 Feb 1979

    Google Scholar 

  106. Tilly G, Hardouin M, Michel JC, Lautrou J (1975) X-ray contrast medium. German Offen 2,456,685, 12 June 1975 (cf Chem Abstr 83:114021b, 1975; see also British patent 1,436,357, 19 May 1976)

    Google Scholar 

  107. Hoey GB, Murphy GP, Wiegert PE, Woods JW (1977) 3,5-Disubstituted-2,4,6-triiodoanilides of monobasic polyhydroxy acids. German Offen 2,643,841, 7 April 1977 (cf Abstr 87:136300, 1977)

    Google Scholar 

  108. Lin Y, Smith KR (1979) N-(2-Hydroxyethyl)-2,4,6-triiodo-3,5-bis-(2-keto-L-gulonamido) benzamide and radiological compositions containing same. 15th American Chemical Society Midwest Meeting, St Louis, 8 Nov 1979

    Google Scholar 

  109. Lin Y (1981) N, N′-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-keto-L-gulonamido) isophthalamide and radiological compositions. US patent 4,256,729, 17 March 1981

    Google Scholar 

  110. Tilly G, Hardouin MJC, Lautrou J (1976) X-ray contrast material. German Offen 2,624,153, 23 Dec 1976 (cf Chem Abstr 87:157183, 1977; see also US patent 4,062,934, 13 Dec 1977)

    Google Scholar 

  111. Smith KR (1977) N-Triiodobenzoylaminoacyl derivates of polyhydroxyamines. German Offen 2,710,730, 22 Sept 1977 (cf Chem Abstr 88:2337w, 1978)

    Google Scholar 

  112. Smith KR (1976) L-(3,5-Disubstituted-2,4,6-triiodophenyl)-3-(polyhydroxy-alkyl) urea compounds. German Offen 2,610,500, 25 Nov 1976 (cf Chem Abstr 86:190410e, 1977; see also US patent 4,109,081, 22 Aug 1978)

    Google Scholar 

  113. Smith KR (1976) Polyhydroxyalkyl 3,5-disubstituted-2,4,6-triiodocarbanilate. German Offen 2,541,491, 15 April 1976 (cf Chem Abstr 85:63296, 1976; see also US patent 4,125,706, 14 Nov 1978)

    Google Scholar 

  114. United States Pharmacopoeia, 20th revision. US Pharmacopoeial Convention, Rockville, p 1037 (and references therein)

    Google Scholar 

  115. Ackerman JH, Laidlaw GM, Snyder CA (1969) Restricted rotational isomers I. Hindered triiodoisophthalic acid derivatives. Tetrahedron Lett 44:3879

    Article  Google Scholar 

  116. Ackerman JH, Laidlaw GM (1969) Restricted rotational isomers II. Maleimido derivatives of the cis and trans isomers of 5-amino, 2,4,6-triiodo-N,N,N′,N′-tetra-methylisophthalimides. Tetrahedron Lett 51:4487

    Article  CAS  Google Scholar 

  117. Ackerman JH, Laidlaw GM (1970) Restricted rotational isomers III. Cis and trans 3′,5′-(dimethylcarbamoyl)-2′,4′,6′-triiodooxalanilic acid and their N-methyl derivatives. Tetrahedron Lett 27:2381

    Article  Google Scholar 

  118. Hol L, Kelly M, Salvesen S (1977) Metrizamide. In: Goldberg ME (ed) Pharmacological and biochemical properties of drug substances. American Pharmacological Association, Washington (Academy pharmacological sciences, vol 1, pp 387–412)

    Google Scholar 

  119. McCall JM (1975) Liquid-liquid partition coefficients by high pressure liquid chromatography. J Med Chem 18:549–552

    Article  PubMed  CAS  Google Scholar 

  120. Rizzolo RR, Smith KR, Hoey GB, Reed RD, Ehrhard EJ (1979) Relationship between toxicity and HPLC retention times of nonionic iodinated X-ray contrast media. 15th American Chemical Society Midwest Meeting, St Louis, 8 Nov 1979

    Google Scholar 

  121. Larmaque JL, Bruel JM, Dondelinger B, Vendrell B, Pelissier O, Rouanet JP, Michel JL, Boulet P (1979) The use of iodolipids in hepatosplenic computed tomography. J Comput Assist Tomogr 3/1:21–24

    Google Scholar 

  122. Vermess M, Chatterji BC, Doppman JL, Grimes G, Adamson RH (1979) Development and experimental evaluation of a contrast medium for computed tomographic examination of liver and spleen. J Comput Assist Tomogr 3:25–31

    Article  PubMed  CAS  Google Scholar 

  123. Vermess M, Adamson RH, Doppman JL, Rapson AS, Herdt JR (1976) Intravenous hepatospleenography. Experimental evaluation of a new contrast material. Radiology 119/1:31–37

    Google Scholar 

  124. Grimes G, Vermess M, Galielli JF, Girton M, Chatterji BD (1979) Formulation and evaluation of ethiodized oily emulsion for intravenous hepatography. J Pharm Sci 68/1:52–56

    Article  Google Scholar 

  125. Roth SL, Dumbrowski H, Heiort U, Kalbfleisch H, Ludwig J, Siefart F, Saeher A, Vielhauer E (1979) A new contrast medium emulsion for lymphography. ROFO 131/3:317–321

    Article  Google Scholar 

  126. Villemein T, Morre J, Laval-Jeantet AM, Laval Jeantet M (1973) Experimental hepatography in the rat by selective intraarterial injection of an iodolipid emulsion. Ann Radiol (Paris) 16/7–8:527–532

    Google Scholar 

  127. Arbadus BT, Ferno OB, Linderot TO (1971) X-ray contrast agent. German patent 1,617,275, 13 May 1971

    Google Scholar 

  128. Roth S (1977) X-ray contrast agent based on an emulsion of iodinated oils. German patent 2,602,907, 28 July 1977

    Google Scholar 

  129. Fritsch G, Voigt R, Lleuning M (1970) Preparation of a contrasting emulsion agent for lymphography. Pharmazie 25/4:248–252

    Google Scholar 

  130. Newton BN (1976) Iodine containing organic carbonates as investigative radiopaque compounds. J Med Chem 19/12:1362–1366

    Article  Google Scholar 

  131. Newton BN (1977) Iodine containing organic carbonates for use as radiographic agents. US patent 4,022,814, 10 May 1977

    Google Scholar 

  132. Newton BN (1978) Structure-toxicity relationships of iodinated organic carbonates and related compounds. J Pharm Sci 67/8:1154–1157

    Article  Google Scholar 

  133. Newton BN (1978) Iodinated thiolcarbonates for use as radiographic contrast agents. US patent 4,125,554, 14 Nov 1978

    Google Scholar 

  134. Deleted in production

    Google Scholar 

  135. Larsen AA (1964) Iodinated esters of substituted benzoic acids and preparations thereof. US patent 3,119,858, 20 Aug 1964

    Google Scholar 

  136. Felder E, Pitre D, Tirone P, Zingales AH (1978) Radiopaque contrast media. XLV. Experimental lymphography with crystal suspensions. Farmaco [Sci] 33/4:302–314

    Google Scholar 

  137. Felder E, Pitre E (1976) New X-ray media and methods for their preparation. German Offen 2,625,826, 23 Dec 1976

    Google Scholar 

  138. Felder E, Vitale RS, Pitre D (1977) Radiopaque esters of tetriiodoteraphthalic acid. US patent 4,044,048, 23 Aug 1977

    Google Scholar 

  139. Kaude JE, Abrams RM, Daly JW (1978) Percutaneous indirect lymphography with a new experimental contrast medium — a preliminary report. Angiology 29/2:162–168

    Article  Google Scholar 

  140. Zutter H, Brunner J (1970) New X-ray contrast media, their use and methods for their preparation. German Offen 1,958,333, 27 Aug 1970

    Google Scholar 

  141. Schic M, Povse T, Zupet T (1971) Bronchography using an iodine contrast agent substituted at the ester of 3,5-diiodo-4-pyridone in N-carboxylic acid ester. Tekhnika 26/4:158–159

    Google Scholar 

  142. Povse T, Zupet T, Japelj N (1971) Tekhnika 26/4:333–336

    Google Scholar 

  143. French Patent 2,180,568 (1974) Contrast material for radiologic examinations, 4 Jan 1974

    Google Scholar 

  144. Soulal MJ, Utting K (1974) Acetoxymethyl and peivaloyloxymethyl 5-acetamido-2,4,6-triiodo-N-methylisophthalamates. US patent 3,795,698, 3 May 1974

    Google Scholar 

  145. Soulal MJ, Utting K (1975) Derivatives of 3-acetamido-2,4,6-triiodobenzoic acid. German Offen 2,428,140, 23 Jan 1975

    Google Scholar 

  146. Hoey GB (1980) Lower alkoxymethyl esters of 2,4,6-triiodobenzoic acid derivatives. US patent 4,225,725, 30 Sept 1980

    Google Scholar 

  147. Long EM, Liu MS, Dobben GB, Scanto PF, Aranbulo AS (1976) Radiopaque applications of brominated fluorocarbon compounds in experimental animals and human subjects. Am Chem Soc Ser 28:171–189

    CAS  Google Scholar 

  148. Enzmann D, Young SY (1979) Applications of perfluorinated compounds as contrast agents in computed tomography. J Comput Assist Tomogr 3/5:622–626

    Article  Google Scholar 

  149. Brahme F, Sovak M, Powell H, Long DM (1975) Perfluorocarbon bromides as contrast media in radiography of the central nervous system. Acta Radiol [Suppl] (Stockh) 347

    Google Scholar 

  150. Felder E, Tanara CB (1976) Radiopaque contrast media. XXXIII. Oral cholecystography, a review. Farmaco [Sci] 31:283–294

    CAS  Google Scholar 

  151. Stagner WC, Guillory JK (1979) Physical characterization of solid iopanoic acid forms. J Pharm Sci 68:1005–1009

    Article  PubMed  CAS  Google Scholar 

  152. Deleted in production

    Google Scholar 

  153. Deleted in production

    Google Scholar 

  154. Deleted in production

    Google Scholar 

  155. Deleted in production

    Google Scholar 

  156. Deleted in production

    Google Scholar 

  157. Deleted in production

    Google Scholar 

  158. Deleted in production

    Google Scholar 

  159. Deleted in production

    Google Scholar 

  160. Pitre D, Felder E (1976) Radiopaque contrast media. XLII. Metabolism of iopronic acid in human. Farmaco [Sci] 31:540–546

    CAS  Google Scholar 

  161. Pitre D (1976) Radiopaque contrast media. XL. Isolation and identification of the metabolites of iopronic acid in the urine and bile of the dog. Farmaco [Sci] 31:516–528

    CAS  Google Scholar 

  162. Pitre D, Fumagalli L (1976) Radiopaque contrast media. XLI. Isolation and identification of the metabolites of iopronic acid in the rat. Farmaco [Sci] 31:529–539

    CAS  Google Scholar 

  163. Raffaeli E, Facino RM, Salmona M, Pitre D (1977) In vitro binding and metabolism of iopronic acid by rat liver microsomes. Pharmacol Res Commun 9:833–846

    Article  PubMed  CAS  Google Scholar 

  164. Pitre D, Facino RF (1976) Radiopaque contrast media. XXXIX. Metabolism of iopronic acid by rat liver microsomes: characterization and identification of the metabolites. Farmaco [Sci] 31:755–762

    CAS  Google Scholar 

  165. Felder E, Pitre D (1972) 3[ω[3-(Acylamino)-2,4,6-triiodophenoxy]alkoxy]-2-alkyl-propinoic acids. German Offen 2,128,902. 22 June 1972

    Google Scholar 

  166. Felder E, Pitre D, Fumagalli L, Lorenzotti E (1976) Radiopaque contrast media. XXXIV. Derivatives of ω-(3-amino-2,4,6-triiodophenoxy)alkoxyalkanoic acids. Farmaco [Sci] 31:349–363

    CAS  Google Scholar 

  167. Felder E, Pitre D, Frandi M (1976) Radiopaque contrast media. XXXV. Physical properties of iopronic acid, a new oral cholecystographic agent. Farmaco [Sci] 31:426–437

    CAS  Google Scholar 

  168. Felder E, Zingales MF, Tiepolo U (1976) Radiopaque contrast media. XXXVI. Iopronic acid: proposed analytical monograph. Farmaco [Prat] 31:383–396

    CAS  Google Scholar 

  169. Pitre D, Frigerio A, Maffei-Facino R (1976) Identification of some urinary metabolites of iopronic acid in human, rat and dog. Mass spectrum drug metab, Proc int symp, pp 13–30

    Google Scholar 

  170. Tirone P, Rosati G (1976) Radiopaque contrast media. XXXVII. Iopronic acid, a new contrast medium for oral chelecystography: pharmacologic investigation. Farmaco [Prat] 31:397–412

    CAS  Google Scholar 

  171. Tirone P, Rosati G (1976) Radiopaque contrast media. XXXVIII. Iopronic acid, a new contrast medium for oral cholecystography: toxicologic investigation. Farmaco [Prat] 31:437–446

    CAS  Google Scholar 

  172. Lewis TR, Archer S (1949) Preparation of some iodinated aminophenylalkanoic acids. J Am Chem Soc 71:3753–3755

    Article  CAS  Google Scholar 

  173. Priewe H, Poljak A (1960) Foramidino derivatives of β-(2,4,6-triiodo-3-aminophenyl) alkanoic acids. Chem Ber 93:2347–2352

    Article  CAS  Google Scholar 

  174. Obendorf W (1962) 3-Amino-2,4,6-triiodoaminobenzoyl compounds for use as X-ray contrast agents. German patent 1,085,048. Appl 6 Aug 1958 (ch Chem Abstr 56:5884h, 1962). US patent 3,051,745, 28 Aug 1962

    Google Scholar 

  175. Archer S, Hoppe JO (1959) Acylated triiodoaminophenylalkanoic acids. US patent 2,895,988, 21 July 1959

    Google Scholar 

  176. Almen T (1971) 2,4,6-Triiodobenzoic acid derivaties: methods for their preparation and properties as X-ray contrast media. In: Knoefel P (ed) Radiocontrast agents, vol 2. Pergamon, New York, p 688

    Google Scholar 

  177. Salvesen S, Haugen LG, Haavaldsen J, Nordal V (1971) Triiodobenzoic acid derivatives as X-ray contrast agents. Norwegian patent 122430, 28 June 1971

    Google Scholar 

  178. See also: Haugen LG, Salvesen S, Haavaldsen J, Nordal V (1969) Substituted 2,4,6-triiodobenzoic acids, X-ray contrast media. German Offen 1,928,838, 11 Dec 1969

    Google Scholar 

  179. Felder E, Pitre D, Grandi M (1977) Radiopaque contrast media. XLIII. Physico-chemical properties of iodamide. Farmaco [Sci] 32/10:755–766

    Google Scholar 

  180. Bernstein J, Losee KA (1972) 2,4,6-Triiodobenzoic acid derivatives. Methods for their preparation and properties as X-ray contrast media. German Offen 2,129,936, 27 Jan 1972

    Google Scholar 

  181. Wiegert PE (1976) 2,4,6-Triiodo-5-methoxyacetamido-N-methylisophthalamic acid compounds and their use in X-ray contrast media. German Offen 2,528,795, 12 Feb 1976

    Google Scholar 

  182. Tilly G (1971) Opaquing agents for radiography. French demande 2,074,734, 12 Nov 1971

    Google Scholar 

  183. Tilly G (1971) Iodinated radiocontrast agents. German Offen 211,750, 28 Oct 1971 (and French demande 2,085,636, 4 Feb 1972: Iodinated radiocontrast agents; also Norwegian patent 122430, 28 June 1971)

    Google Scholar 

  184. Haugen LG, Salvesen S, Haavaldsen J, Nordal V (1969) Substituted 2,4,6-triiodoben-zoic acids, X-ray contrast media. German Offen 1,928,838, 11 Dec 1969

    Google Scholar 

  185. Pfeiffer H, Zoellner G, Beich W (1972) 3-Acetamido-5-(hydroxyacetamido)-2,4,6-triiodobenzoic acid-containing contrast media. German Offen 211,829, 26 Oct 1972 (and references therein)

    Google Scholar 

  186. Wiegert PE (1978) 2,4,6-Triiodobenzoic acid derivatives. Methods of preparation and use as X-ray contrast media. German Offen 2,732,825, 23 Feb 1978

    Google Scholar 

  187. Sterling Drug Co. (1970) Iodonated imido-benzoic acids. British patent 1,191,015, 5 May 1970

    Google Scholar 

  188. Ackerman JH (1969) Triiodoaniline derivatives. German Offen 1,915,196, 20 Nov 1969

    Google Scholar 

  189. Zupet P, Povse T, Japelj M, Sehic M, Obrez I, Bulic D (KRKA Inst. Raziskave Raz-vo) (1975) Novo Mesto, Yugoslavia. Kern Ind 24/7:379–381

    Google Scholar 

  190. Wiegert PE (1976) Substituted 2,4,6-triiodoisopnthalamic acids for use in X-ray contrast media. German Offen 2,526,848, 2 Jan 1976

    Google Scholar 

  191. Kleiger E, Speck U (1978) Iodinated isophthalamic acid derivatives. German Offen 2,629,228, 5 Jan 1978 (see also Belgian patent 856,095, 27 Dec 1977)

    Google Scholar 

  192. Schering AG (1977) Iodinated isophthalamic acid derivatives. Belgian patent 856,095, 27 Dec 1977

    Google Scholar 

  193. Dagra NV (1971) X-Ray contrast medium containing a shielding component. Netherlands Appl 6,912,102, 10 Feb 1971 (CA 75:35436 (19), 1971)

    Google Scholar 

  194. Kneller MT (1978) Oxazolinylacetamidotriiodobenzoic acid X-ray contrast agents., US patent 4,066,743, 3 Jan 1978

    Google Scholar 

  195. Tilly G (1972) Triiodobenzene derivatives as X-ray contrast media. German Offen 2,216,627, 19 Oct 1972

    Google Scholar 

  196. Klieger E, Schroeder E (1973) Synthesis of N-(carbamoylalkyl)triiodoisophthalamic acids and their use as X-ray contrast media. Arch Pharm (Weinheim) 306/11:834–845

    Article  Google Scholar 

  197. Klieger E, Beich W, Schroeder E (1976) Triiodoisophthalamic acid monoamino acid amides. US patent 3,953,501, 27 April 1976

    Google Scholar 

  198. Klieger E, Beich W, Schroeder E (1973) N-3-Carbamoyl(or carboxy)-5-acetamido-2,4,6-triiodobenzoyl amino acids (or amides) for X-ray contrast media. German Offen 2,207,950, 23 Aug 1973

    Google Scholar 

  199. Bernstein J, Losee KA (1972) Substituted triiodoisophthalamic acids. US patent 3,666,800, 30 May 1972

    Google Scholar 

  200. Ackerman JH (1970) Iodinated imido-benzoic acids. British patent 1,191,015, 6 May 1970

    Google Scholar 

  201. Felder E, Pitre D, Zutter H (1974) 5-(Acetamidomethyl)-3-acetyl(2,3-dihydroxypropyl) amino-2,4,6-triiodobenzoic acid. German Offen 2,229,360, 7 Nov 1974 (see also French demande 2,150,805, 26 Aug 1971; US patent 3,360,436, 26 Dec 1967)

    Google Scholar 

  202. Felder E, Pitre D (1975) 3-Hydroxyacylaminomethyl-5-acylamino-2,4,6-triiodobenzoic acids and their use as X-ray contrast materials. German Offen 2,425,912, 20 March 1975

    Google Scholar 

  203. Felder E, Pitre D (1975) X-ray contrast medium. German Offen 2,422,718, 13 Feb 1975

    Google Scholar 

  204. Klieger E (1972) Synthesis of triiodo-phenylacetic acid derivatives and their use as X-ray contrast agents. Chim Ther 7/6:475–478

    Google Scholar 

  205. Pfeiffer H, Zoellner G, Geich W (1972) Circulation-compatible 5-hydroxy (and alkoxy) acetamido-3-(acetamidomethyl)-2,4,6-triiodobenzoic acids for X-ray contrast media. German Offen 2,124,904, 7 Dec 1972

    Google Scholar 

  206. Klieger E, Schroeder E (1976) Preparation of new hexaiodated X-ray contrast materials. Eur J Med Chem Chim Ther 11/3:283–286

    Google Scholar 

  207. Klieger E, Speck U, Schroeder E (1976) Dicarboxylic acid derivatives of triiodoisoph-thalic acid monoamino acid amides and their use as X-ray contrast media. German Offen 2,505,320, 5 Aug 1976

    Google Scholar 

  208. Ekstrand TKIV, Ronlan A, Wickberg BV, Munksgaard AH (1973) X-ray contrast agent. German Offen 2,038,263, 22 Feb 1973

    Google Scholar 

  209. Bernstein J, Loese KA (1971) N,N′-Trimethylenebis(5-(3-methylureido)-2,4,6-triiodoisophthalamic acid as X-ray contrast medium. German Offen 2,038,263, 18 Feb 1971

    Google Scholar 

  210. Bernstein J, Losee KA (1971) N,N′-Bis 5-(3-methylureido)-3-carboxy-2,4,6-triiodophenyl adipamide. German Offen 2,130,369, 23 Dec 1971

    Google Scholar 

  211. Ekstrand TKI, Munksgaard A, Ronlan A, Wickberg BV (1971) N,N′-Bis(triiodophenyl) alkylenediamines as X-ray contrast media. German Offen 2,111,127, 21 Oct 1971

    Google Scholar 

  212. Bjork L, Erickson UE, Ingelman BGA (1973) Derivative of 3,5-dialkanoylamino-2,4,6-triiodobenzoic acid and its use as X-ray contrast medium. Swedish patent 354,853, 26 March 1973

    Google Scholar 

  213. Tilly G (1975) N,N′-Dimethyliocarmic acid derivatives useful as radiography opacifies. British patent 1,385,684, 26 Feb 1975

    Google Scholar 

  214. Ingelman BGA (1969) Radiopaque iodocompounds. German Offen 1,816,844, 24 July 1969

    Google Scholar 

  215. Klieger E, Speck U, Schroeder E (1977) Triiodoisophthalamic acids, useful as X-ray contrast agents. German Offen 2,554,148, 6 Aug 1977 (see also Belgian patent 856,095, 23 Dec 1977)

    Google Scholar 

  216. Gries H, Pfeiffer H (1977) Triiodized N-methyldicarboxylic acid anilides. US patent 4,001,298, 4 Jan 1977

    Google Scholar 

  217. Gries H, Pfeiffer H (1977) Dicarbopylic acid derivatives of triiodoisophthalic acid mono-amides. Methods for their preparation and their use as X-ray contrast media. German Offen 2,554,148, 6 Aug 1977

    Google Scholar 

  218. Felder E, Pitre D (1969) Alkanedioylbis(3-acylaminomethyl-5-carboxy-2,4,6-triiodoanilides). German Offen 1,922,606, 13 Nov 1969

    Google Scholar 

  219. Felder E, Pitre D (1969) New X-ray contrast media. German Offen 1,922,613, 2 May 1969

    Google Scholar 

  220. Gries H (1972) 3-(Methylamino)-2,4,6-triiodophenyl derivatives. German Offen 2,050,217, 6 April 1972

    Google Scholar 

  221. Felder E, Pitre D (1974) 3-(Acylamino)-5-(alpha-hydroxyalkyl)-2,4,6-triiodobenzoic acids as X-ray contrast media. German Offen 2,317,535, 30 May 1974

    Google Scholar 

  222. Bernstein J, Sowinski FA (1975) 3,5-Disubstituted-2,4,6-triiodobenzoic acids. US patent 3,914,294, 21 Oct 1975

    Google Scholar 

  223. Tilly G, Hardouin MJC, Lautrou J (1975) X-ray contrast media. German Offen 2,523,567, 11 Dec 1975

    Google Scholar 

  224. Klieger E, Schroeder E (1975) Synthesis of N-(3-acylamino-5-alkylcarbamoyl-2,4,6-triiodobenzoyl)amino acids as X-ray contrast agents. Eur J Med Chem Chim Ther 10/1:84–88

    Google Scholar 

  225. Murphy GP, Hoey GB, Wiegert PE, Smith KR, Lin Y, El-Antably SM, Friedman MD, Kneller MT, Reed RD, Hopkins RM, VanDeripe DR, Adams MD, Lau DHM, Valenti A (1979) Synthesis and toxicological evaluation of nonionic iodinated X-ray contrast media. 15th Midwest American Chemical Society Meeting, St Louis, 8 Nov 1979

    Google Scholar 

  226. Sovak M, Nahlovsky B, Lang J, Lasser ES (1975) Preliminary evaluation of di-iodotriglucosyl benzene. An approach to the design of nonionic water-soluble radiographic contrast media. Radiology 117:717–719

    PubMed  CAS  Google Scholar 

  227. Sovak M, Johnson M, Ranganathan R (1979) Improved screening of acute toxicity of novel contrast media. Invest Radiol 14:378

    Google Scholar 

  228. Sovak M, Ranganathan R (1980) Stability of nonionic water-soluble contrast media. Invest Radiol [Suppl], p 3327

    Google Scholar 

  229. Nordal V, Holterman H (1977) Iodine-containing isophthalamide derivates. German Offen 2,727,196, 22 Dec 1977 (cf Chem Abstr 88:152269z, 1978; see also US patent 4,250,113, 10 Feb 1981)

    Google Scholar 

  230. Tilly G (1968) 4-[2,4,6-Triiodo-3-morpholino carbonyl)phenoxy]-butyric acid. French CAM 202, 24 June 1968 (cf Chem Abstr 72:43699p, 1970)

    Google Scholar 

  231. Speck U, Blasskiewicz P, Seidelmann D, Kleiger E (1980) New nonionic X-ray contrast media. German Offen 2,909,439, 19 Sept 1980

    Google Scholar 

  232. Gries H, Pfeiffer H, Speck U, Mützel W (1981) Nonionic 5-C-substituted 2,4,6-triiodoisophthalic acid derivates. German Offen 3,001,292, 16 July 1981

    Google Scholar 

  233. Felder E, Pitre D (1972) 2-Alkyl-3-[2-(3-carbamoyl-2,4,6-triiodophenoxylethoxy] propionic acids as X-ray contrast media. German Offen 2,212,741, 28 Dec 1972 (cf Chem Abst 78:71710c, 1973)

    Google Scholar 

  234. Bernstein J, Sowinski FA (1972) 3-[4-(3-Hydroxy-2,4,6-triiodophenoxy)phennylalanine. French demande 2,182,161, 27 April 1972 (cf Chem Abstr 80:133827y, 1974)

    Google Scholar 

  235. Felder E, Pitre D (1969) Aminotriiodophenylpropionic acids as contrast agents. Swiss patent 480,071, 15 Dec 1969 (cf Chem Abstr 72:100292b, 1970)

    Google Scholar 

  236. Pfeiffer H, Kolb KH, Harwart A, Schulze PE (1971) 3-(2,4,6-Triiodo-3-amidino-phenyl) propionic acids as X-ray contrast media. German Offen 1,956,844, 19 May 1971 (cf Chem Abstr 75:35474b, 1971)

    Google Scholar 

  237. Ackerman JH (1972) 3-(Carboxyalkanoylamino)-2,4,6-triiodohydrocinnamic acids. US patent 3,637,825, 25 Jan 1972

    Google Scholar 

  238. Ackerman JH (1968) 3-Cyclic imides of 3-amino-2,4,6-triiodohydrocinnamic acids. US patent 3,655,669, 25 March 1968

    Google Scholar 

  239. Ackerman JH (1977) 3-Acylamino-2,4,6-triiodobenzoic acids. US patent 4,031,088, 21 June 1977

    Google Scholar 

  240. Felder E, Pitre D, Fumagalli L, Lorenzotte E (1970) Radiopaque contrast media. XVIII. Derivatives of 2-(3-amino-2,4,6-triiodophenyl)alkanoic acids. J Med Chem 13:559–561

    Article  PubMed  CAS  Google Scholar 

  241. Pitre D, Fumagalli L, Lorenzotti E (1972) Radiological contrast media. XXI. Iodo derivatives of aryl [3-(N-alkylacylamino)phenoxy]acetic acid. Formaco [Sci] 27:408–418

    CAS  Google Scholar 

  242. Skulan TW (1977) Diagnostic process using sodium tyropanoate. US patent 4,002,711, 11 Jan 1977

    Google Scholar 

  243. Hoppe JO, Ackerman JH, Larsen AA (1970) Sodium tyropanoate, a new oral cholecystographic agent. J Med Chem 13:997–999

    Article  PubMed  CAS  Google Scholar 

  244. Holtermann H (1969) N-(Hydroxyalkyl)-2′,4′,6′-triiodosuccinanilic acids, cholecystographic contrast media. German Offen 1,927,557, 18 Dec 1969 (cf Chem Abstr 72:66587q, 1970)

    Google Scholar 

  245. Cassebaum H, Dierbach K (1969) Alkyl substituted-N-(2,4,6-triiodo-3-aminophenyl)-glutaramidic acids. German (East) patent 67,209, 5 June 1969 (cf Chem Abstr 72:66654j, 1970)

    Google Scholar 

  246. Cassebaum H, Dierback K, Bekker H (1972) Iodinated N-aryldicarboxylic acid monoamides as orally applied bile contrast media. Pharmazie 27:391–395

    PubMed  CAS  Google Scholar 

  247. Obendorf W, Lindner I (1969) 3-Amino-2,4,6-triiodobenzamide derivatives as X-ray contrast agents. Austrain patent 275,025, 10 Oct 1969 (cf Chem Abstr 72:78726x, 1970)

    Google Scholar 

  248. Clauss W, Speck U, Jentsch D (1976) Oral X-ray contrast medium. German Offen 2,505,218, 19 Aug 1976 (cf Chem Abstr 85:166652u, 1976)

    Google Scholar 

  249. Korver JA (1977) Radiographic contrast agents containing N-acetyl-N-(3,5-diamino-2,4,6-triiodophenyl)aminopropionic acid derivatives. French demande 2,313,917, 7 Jan 1977 (cf Chem Abstr 88:16159m, 1978)

    Google Scholar 

  250. Dagra NV (1979) Triiodophenylaminopropionic acids and their use in X-ray contrast media. Belgian patent 874,988, 16 July 1979 (cf Chem Abstr 91:175027v, 1979)

    Google Scholar 

  251. Suter H, Pitre D, Fumagalli L (1969) Amino-triiodobenzamidophenylalkanoic acids as contrast media. Swiss patent 480,070, 15 Dec 1969 (cf Chem Abstr 72:100300c, 1970)

    Google Scholar 

  252. Suter H, Pitre D, Fumagalli L (1970) Roentgen contrast media containing [(3-amino-2,4,6-triiodobenzoyl)aminophenyl]alkanoic acid as shadow imaging component. Swiss patent 490,090, 30 June 1970 (cf Chem Abstr 73:112947c, 1970)

    Google Scholar 

  253. Obendorf W, Lindner I, Schwarzinger E, Krieger J (1974) Cyclic amidines for X-ray contrast medium. German Offen 2,235,915, 7 Feb 1974 (cf Chem Abstr 80:108538p, 1974)

    Google Scholar 

  254. Obendorf W, Lindner I, Schwarzinger E, Krieger J (1974) [(Aminoalkylidene)-amino]triiodobenzamide derivatives for X-ray contrast media. German Offen 2,235,935, 7 Feb 1974 (cf Chem Abstr 80:108545x, 1974)

    Google Scholar 

  255. Obendorf W, Schwarzinger E, Krieger J, Lindner I (1974) X-ray contrast medium. Austrian patent 319,463, 27 Dec 1974 (cf Chem Abstr 82:160245e, 1975)

    Google Scholar 

  256. Obendorf W, Schwarzinger E, Krieger J, Lindner I (1974) Iodine-substituted cyclic amidines as X-ray contrast agents. Austrian patent 319,226, 10 Dec 1974 (cf Chem Abstr 83:9777e, 1975)

    Google Scholar 

  257. Obendorf W, Schwarzinger E, Krieger J, Lindner I (1975) X-ray contrast material. Austrian patent 320,139, 27 Jan 1975 (cf Chem Abstr 83:654998b, 1975)

    Google Scholar 

  258. Obendorf W, Lindner I, Schwarzinger E (1978) N-Acyl derivatives of 3-amino-2,4,6-triiodobenzoic acid. German Offen 2,732,599, 20 April 1978 (cf Chem Abstr 89:42838x, 1978)

    Google Scholar 

  259. Obendorf W, Schwarzinger E (1979) N-Acyl derivatives of 3-amino-2,4,6-triiodobenzoic acid. US patent 4,152,526, 1 May 1979

    Google Scholar 

  260. Ackerman JH (Sterling Drug Inc.) (1969) 3,3′-[Alkylenebis(carbonylimino)]bis[2,4,6-triiodobenzoic acids]. British patent 1,164,526, 17 Sept 1969 (cf Chem Abstr 71:123989c, 1969; see also US patent 3,542,861 and/or German Offen 1,618,001)

    Google Scholar 

  261. Rosenberg FJ, Ackerman JH, Nickel AR (1980) Iosulamide: A new intravenous cholangiocholecystographic medium. Invest Radiol [Suppl] S142

    Google Scholar 

  262. Sovak M, Ranganathan R, Douglass I, Gallagher I, Nagavajan G (1983) New concepts in CM synthesis: development of a new nonionic contrast medium. Invest Rad (Suppl) 19

    Google Scholar 

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Authors
  1. G. B. Hoey
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  2. K. R. Smith
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Editors and Affiliations

  1. School of Medicine, Department of Radiology, S-009, University of California in San Diego, La Jolla, CA, 92093, USA

    Milos Sovak

  2. Biophysica Foundation, 3333 Torrey Pines Ct., La Jolla, CA, 92037, USA

    Milos Sovak

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Hoey, G.B., Smith, K.R. (1984). Chemistry of X-Ray Contrast Media. In: Sovak, M. (eds) Radiocontrast Agents. Handbook of Experimental Pharmacology, vol 73. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-69515-5_2

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