Calixpyrroles, calixpyridinopyrroles and calixpyridines

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 487/22 (2006.01) A61K 47/22 (2006.01) A61M 1/14 (2006.01) B01J 45/00 (2006.01) C07D 471/22 (2006.01) C07D 495/22 (2006.01) C07D 498/22 (2006.01) C07D 519/00 (2006.01) C07F 9/6561 (2006.01) C07F 17/02 (2006.01) C07H 13/04 (2006.01) C07J 43/00 (2006.01) C12Q 1/68 (2006.01) G01N 27/30 (2006.01) G01N 27/327 (2006.01) G01N 27/447 (2006.01) G01N 30/88 (2006.01) G21F 9/06 (2006.01) G21F 9/12 (2006.01) G21F 9/30 (2006.01) G01N 30/02 (2006.01)

Patent

CA 2251072

The present invention provides calixpyrrole, calixpyridinopyrrole, and calixpyridine macrocycles, having 4, 5, 6, 7, or 8 heterocyclic rings, as well as syntheses, derivatives, conjugates, multimers, and solid supports thereof. Such macrocycles have proved to be effective and selective ion- and neutral molecule-binding agents forming supramolecular ensembles, and ion- and neutral molecule-separation agents. The macrocycles are fully meso-non-hydrogen- substituted porphyrinogens, a few molecules of which were previously known but not recognized as possessing anion- or molecule-binding properties. The binding mode is noncovalent, primarily that of hydrogen-bonding, thereby providing a new mode for liquid chromatography, that of Hydrogen Bonding Liquid Chromatography. Further useful applications of the macrocycles provided herein include environmental remediation by removal of undesired ions or neutral molecules, and removal of phosphate for kidney dialysis.

L'invention concerne des macrocycles calixpyrroles, calixpyridinopyrroles et calixpyridines, possédant 4, 5, 6, 7 ou 8 noyaux hétérocycliques, ainsi que leurs synthèses, dérivés, conjugués, multimères et supports solides. Ces macrocycles se sont avérés être des agents de liaison des ions et des molécules neutres efficaces et sélectifs, formant des ensembles supramoléculaires, ainsi que des agents de séparation des ions et des molécules neutres. Ils constituent des porphyrinogènes totalement méso, sans substituant hydrogène dont certaines molécules étaient déjà connues, mais pas les propriétés de liaison anionique ou moléculaire de celles-ci. Le mode de liaison, non covalent, est à l'origine une liaison hydrogène, ce qui donne un nouveau procédé de chromatographie en phase liquide, la chromatographie en phase liquide par liaison hydrogène. Parmi les autres applications utiles des macrocycles cités ici, on trouve le traitement de l'environnement par élimination des ions ou des molécules neutres indésirables, et l'élimination des phosphates en dialyse rénale.

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