Biodegradable proline-based polymers

C - Chemistry – Metallurgy – 08 – L

Patent

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Details

C08L 77/12 (2006.01) A61K 9/51 (2006.01) A61K 47/34 (2006.01) C08G 69/44 (2006.01)

Patent

CA 2736393

The invention provides sequential poly(ester amide)s derived from Proline and that are synthesized by a two-step method, involving a final thermal polyesterification reaction. Molecular weights of polymers prepared by this method are from 14,000 Da to about 77,000Da.1 When invention proline-based PEAs were thermally characterized,, their glass transition temperatures were lower than other alpha-amino acid based poly(ester amides) due to lack of internal hydrogen bonding. These Proline-based PEAs assemble as nano-particles in aqueous solutions and form complexes with various cations and biologies, including hydrophobic small molecule drugs and biologies. Therefore the invention Proline- based PEAs are useful for drug delivery applications requiring a polymer with a molecular weight in the range from 14,000 Da to about 77,000Da and for fabrication of nanoparticles for delivery of hydrophobic drugs.

L'invention porte sur des poly(ester amides) séquentiels qui sont issus de la proline et qui sont synthétisés par un procédé à deux étapes, impliquant une réaction de polyestérification thermique finale. Les masses moléculaires de polymères préparés par ce procédé vont de 14 000 Da à environ 77 000 Da. Lorsque les PEA à base de proline de l'invention ont été thermiquement caractérisés, leurs températures de transition vitreuse étaient inférieures à celles d'autres poly(ester amides) à base d'acide alpha-aminé en raison d'un manque de liaisons hydrogène internes. Ces PEA à base de proline s'assemblent sous la forme de nanoparticules dans des solutions aqueuses et forment des complexes avec divers cations et agents biologiques, comprenant des médicaments et agents biologiques à petites molécules hydrophobes. Par conséquent, les PEA à base de proline de l'invention sont utiles pour des applications d'administration de médicaments nécessitant un polymère ayant une masse moléculaire dans la plage de 14 000 Da à environ 77 000 Da et pour la fabrication de nanoparticules pour l'administration de médicaments hydrophobes.

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