Novel cyclodextrin derivatives and methods for the...

C - Chemistry – Metallurgy – 08 – B

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C08B 37/16 (2006.01) A61K 39/39 (2006.01) A61K 47/48 (2006.01)

Patent

CA 2208849

The present invention relates to cyclodextrin derivatives, and methods for the preparation thereof, which cyclodextrin derivatives have at least one but no more than N-1 "higher" alkyl groups and at least one but no more than N-1 sulfate groups, wherein the total combined number of "higher" alkyl groups and sulfate groups does not exceed N, and further wherein N is the number of hydroxyl groups of the cyclodextrin from which the derivative was derived. The "higher" alkyl groups are lipids and, more particularly, aliphatic or aromatic carbon chains, especially linear carbon chains having a general structure of - O-C(=O)-(CH2)n-CH3, wherein n is between 6 and 24 and/or -OC(=O)-(CH2)m-CH=H-(CH2)m-CH3, wherein m is at least 6. The sulfate groups disclosed herein are sulfate groups having the formula -OSO3R, wherein R may be H, Na, K, Li, NH4 and/or other atoms/molecules that form monovalent cations. The CD derivatives are obtained in a two-step reaction wherein a cyclodextrin is contacted with acoylchloride followed by sulfonating SO3-complex.

On décrit des dérivés de cyclodextrines et leurs procédés de préparation. Ces dérivés comprennent au moins un, mais au plus N-1, groupes alkyles "supérieurs" et au moins un, mais au plus N-1, groupes sulfate, le nombre total combiné des groupes alkyle "supérieurs" et des groupes sulfate ne dépassant pas N, lequel correspond aussi au nombre de groupes hydroxyle de la cyclodextrine d'où sont tirés ces dérivés. Les groupes alkyle "supérieurs" sont des lipides et plus particulièrement des chaînes de carbones aliphatiques ou aromatiques, et notamment des chaînes de carbones linéaires de structure générale -O-C(=O)-(CH2)n-CH3, où n vaut de 6 à 24, et/ou -OC(=O)-(CH2)m-CH=CH-(CH2)m-CH3, où m vaut au moins 6. Les groupes sulfate décrits sont de formule -OSO3R, ou R peut représenter H, Na, K, Li, NH4 et/ou d'autres atomes ou molécules formant des cations monovalents. On obtient ces dérivés de cyclodextrines par une réaction à deux étapes où on met en contact une cyclodextrine avec un alcoylchlorure puis avec un complexe SO3 de sulfonation.

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