Heinz Gries

Sterile pharmaceutical compositions of gadolinium chelates useful enhancing NMR imaging

Pharmaceutical compositions comprising gadolinium chelates are useful for enhancing NMR images.

Enteral contrast medium useful for nuclear magnetic resonance imaging and its preparation

An enteral contrast medium useful for proton nuclear spin tomography contains at least one physiologically compatible paramagnetic compound in combination with a physiologically compatible, osmotically active substance, as well as a physiologically compatible base/buffer or buffer mixture with a pH value of 3 to 8, and, optionally, also a viscosity-raising material, all dissolved or suspended in water. It is excellently suitable for enhancing contrast in imaging, e.g., of the gastrointestinal tract by nuclear spin tomography.

Calcium chelate and gadolinium pharmaceutical composition and methods of x-ray and nmr imaging

Improved metal complex-containing pharmaceutical agents are described which, as an additive, contain one or more complexing agents and/or one or more weak metal complex(es) or mixtures thereof.

Sterile composition comprising a chelate complex for magnetic resonance imaging

A diagnostic medium contains at least one physiologically well tolerated complex salt comprising an anion of a complexing acid and one or more central ion or ions of an element with an atomic number of 21 to 29, 42, 44 or 57 to 83 and, optionally, one or more physiologically biocompatible cation or cations of an inorganic and/or organic base or amino acid, optionally, with additives customary in galenic formulations, dissolved or suspended in an aqueous medium.

NMR imaging using paramagnetic chelates having hydroxyalkyl-substituted amide groups

Compounds of the general formula I: ##STR1## R1 signifies a COOX group or the group ##STR2## R2 and R3 are the same or different and signify a hydrogen atom, a lower straight- or branched-chain, hydrocarbon radical, a phenyl or benzyl group or either R2 or R3 signifies the group ##STR3## or R2 or R3 together signify a trimethylene or tetramethylene radical, R4 represents a straight- or branched-chain mono- or poly-hydroxyalkyl radical, R5 represents a hydrocarbon atom, a lower straight- or branched-chain, optionally mono- or poly-hydroxylated, hydrocarbon radical, Q signifies an oxygen or sulfur atom or the group ##STR4## wherein j signifies the numbers 1 to 4 and Rx signifies a hydrogen atom, a lower alkoxy group with 1 to 4 carbon atoms, a COOX group, or if j>1, also the group ##STR5## wherein k and m are the same or different and represent the numbers 0 or 2, l signifies the numbers 1 or 2 and n and w are the same or different and signify the numbers 0 or 1, wherein n and w can only represent the number 1, if k and m signify the number 2, and X represents hydrogen atoms and/or metal ion equivalents, and their salts with physiologically harmless organic bases, are valuable complexing agents, complexes and complex salts for NMR imaging.

Nitroxyl compounds, and diagnostic media based thereon useful for enhancing NmR imaging

Diagnostic media suitable for NMR diagnoses contain compounds of Formula I ##STR1## wherein is a single bond or a double bond, X is the grouping --(CH2)n -- or , if is a single bond, also the grouping --NHCO(CH2)n -- wherein n means 0 to 4, m means the numbers 0, 1, or 2, R1 is an alkyl residue substituted by hydroxy groups, acyloxy groups and/or alkylidenedioxy groups, R2 has the same meanings as R1 or is a hydrogen atom or an alkyl residue, R3 and R4 are alkyl residues, and R5 and R6 are alkyl residues optionally substituted by hydroxy groups.

Trihalogenated benzamides: structure taste relationships

ZusammenfassungAchtundvierzig 2,4,6-Trihalogen-3-carboxyalkylbenzamide und verwandte Verbindungen wurden auf süßen Geschmack untersucht; gegebenenfalls wurden die Schwellenwerte bestimmt. Das CONH2/COO−-System der Verbindungen ist als das für süßen Geschmack essentielle e/n-System anzusehen. Es ist kein genereller Zusammenhang zwischen der Hydrophobität (Verteilungskoeffizient im Systemn-Octanol/Wasser) der Carboxyalkylbenzamide und ihrem Süßschwellenwert zu erkennen, da sterische Parameter überlagert sind. Wesentlich ist der Abstand der beiden Gruppen des e/n-Systems, der bei einer der süßesten Verbindungen mitctsw ~1 μmol/l für die jeweiligen Zentralatome (N/C) bei 660–830 pm liegt und damit wesentlich größer ist als die für andere süße Verbindungen, z.B. Fructose oderα-Aminosäuren bekannten Werte um 240 pm. Für solche Verbindungen mit einem “longer range” e/n-System wird deshalb ein zweiter schematischer Süßrezeptor postuliert.SummaryThe sweet taste of 48 2,4,6-trihalogenated 3-carboxyalkylbenzamides and related compounds was assessed. The recognition thresholds were determined for all sweet compounds. It was shown that the CONH2/COO− groups form an electrophilic/nucleophilic (e/n)-system, which is essential for sweet taste. A general relation between hydrophobicity (partition coefficient in the systemn-octanol/water) and sweet threshold could not be detected because of the strong influence of steric parameters. The distance between the two groups of the e/n system is especially important. This distance is 660–830 pm measured between the central atoms of the e/n system (N/C) for one of the sweetest compounds withctsw ~1 μmol/l. The value is much larger than those of about 240 pm known for other sweet compounds, e.g. fructose orα-amino acids. A second schematic receptor is postulated for such compounds with a longer range e/n system.

Effect of structure on biological tolerance. Comparison of triiodobenzene derivatives.

Gries H, Mützel W. Effect of structure on biological tolerance: comparison of triiodobenzene derivatives. Invest Radiol 1988;23 (Suppl 1):S97‐S100. Synthesis of basic structures of contrast media is reviewed. Biological tolerance of ionic and nonionic derivatives of triiodobenzene are related to the degree of withdrawal of electrons from their aromatic systems.

Trihalogenated benzamides — a new class of artificial sweeteners

Zusammenfassung2,4;6-Tribrom-3-carboxylalkylbenzamide und 2,4,6-Tribrom-3-carboxylalkoxybenzamide sind intensiv süß. Die 3-Carboxyethyl-Verbindung gehört mit einem Erkennungsschwellenwert von 1 gmol/l zu den süßesten bekannten Verbindungen. Die Intensität des Süßgeschmacks hängt von der Struktur des Carboxyalkyl- bzw. Carboxyalkoxyrestes ab. Die Ante Toxizität der Verbindungen für Mäuse entspricht in etwa der von Saccharin (Na-Salz) und Natriumcyclamat. Die Verbindungen sind leicht und in guter Ausbeute zugänglich.Summary2,4,6-tribromo-3-carboxyalkyl-benzamides and -carboxyalkoxy-benzamides are intensely sweet. With a recognition threshold value of about 1 gmol/1 the 3-carboxyethyl compound is one of the sweetest compounds known. The intensity of the sweet taste depends upon the nature of the carboxyalkyl/carboxylalkoxy group. In respect to the acute toxicity to mice the compounds are similar to the sodium salt of saccharin and sodium cyclamate. The compounds are easily obtainable in good yield.