Anionic polysaccharides functionalized by a hydrophobic acid derivative
Inventors
Charvet, Richard • Soula, Remi • Soula, Olivier
Assignees
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Publication Number
US-9493583-B2
Publication Date
2016-11-15
Expiration Date
Abstract
A novel anionic polysaccharides functionalized by at least one hydrophobic acid derivative. These novel anionic polysaccharides including hydrophobic groups have good biocompatibility and their hydrophobicity can be easily adjusted without detrimentally affecting the biocompatibility or the stability. A method of synthesis which makes it possible to produce them and to pharmaceutical compositions including them.
Core Innovation
The invention relates to anionic polysaccharides that are monofunctionalized with a hydrophobic function -M-Ach according to Formula I, where n is between 0.01 and 0.7. The hydrophobic part Ach is a hydrophobic radical composed of a chain having between 4 and 50 carbons, optionally branched and/or unsaturated, and optionally comprising heteroatoms and/or saturated, unsaturated or aromatic rings or heterocycles. Unfunctionalized carboxyl functions of the anionic polysaccharide are in salt form.
The invention defines how the connecting arm and the hydrophobic radical are coupled to the polysaccharide, with M being either -F1-R1-G or -F2-R2-G. F1 is an amide function, an ester function or a thioester function, while F2 is a carbamate function. R1 and R2 are divalent radicals, each comprising a chain of 1 to 15 carbons and optionally branched and/or unsaturated, optionally comprising heteroatoms and/or saturated, unsaturated or aromatic rings or heterocycles, and G is an amide function, an ester function or a thioester function, forming the bond with Ach.
The problem addressed is producing an anionic polysaccharide that combines carboxyl functions with a hydrophobic function while ensuring monofunctionalization and controlled functionalization degree, as expressed by the range n between 0.01 and 0.7. Embodiments include natural carboxyl-functional polysaccharides and conversion of hydroxyl functions to carboxylates prior to functionalization, and the hydrophobic acid derivative is selected from categories such as fatty acids and bile acids and derivatives.
Claims Coverage
The provided claims include two independent claims and refinement dependent claims for each. Across these independent claims, the inventive coverage centers on a monofunctionalized anionic polysaccharide/polysaccharide framework according to Formula I, with specified bounds for n and structural definitions for Ach, M, F1/F2, R1/R2, and G, including salt-form unfunctionalized carboxyl functions.
Monofunctionalized anionic polysaccharide with hydrophobic radical -M-Ach
An anionic polysaccharide comprising saccharide units including carboxyl functions and being monofunctionalized with a hydrophobic function -M-Ach according to Formula I, wherein n is between 0.01 and 0.7, Ach is a hydrophobic radical composed of a chain comprising between 4 and 50 carbons and optionally branched and/or unsaturated and optionally comprises heteroatoms and/or saturated, unsaturated or aromatic rings or heterocycles, and M is either -F1-R1-G or -F2-R2-G with F1 being an amide, ester or thioester function, F2 being a carbamate function, R1 and R2 being divalent radicals each with a chain comprising 1 to 15 carbons and optionally branched and/or unsaturated and optionally comprising heteroatoms and/or rings or heterocycles, and G being an amide, ester or thioester function; unfunctionalized carboxyl functions are in salt form.
Polysaccharide monofunctionalized with hydrophobic function -M-Ach and salt-form carboxyls
A polysaccharide comprising saccharide units including carboxyl functions and being monofunctionalized with a hydrophobic function -M-Ach according to Formula I, wherein n is between 0.01 and 0.7, Ach is a hydrophobic radical composed of a chain comprising between 4 and 50 carbons and optionally branched and/or unsaturated and optionally comprises heteroatoms and/or saturated, unsaturated or aromatic rings or heterocycles, M is either -F1-R1-G or -F2-R2-G, F1 is an amide, ester or thioester function resulting from functionalization of a carboxyl function, F2 is a carbamate function resulting from functionalization of a hydroxyl group, R1 and R2 are divalent radicals each with a chain comprising between 1 and 15 carbons and optionally branched and/or unsaturated and optionally comprising heteroatoms and/or rings or heterocycles, and G is an amide, ester or thioester function that forms a bond with Ach; unfunctionalized carboxyl functions are in salt form.
The independent claims define a monofunctionalized polysaccharide scaffold in which carboxyl-containing saccharide units are functionalized with a hydrophobic radical -M-Ach under Formula I, with n constrained to 0.01–0.7 and with detailed structural boundaries for Ach, connecting arms R1/R2, and the bond-forming/functional groups F1/F2/G and salt-form carboxyls.
Stated Advantages
Documented Applications
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