Method for producing glyco-conjugates of 20(s)-camptothecin

Details Method for producing glyco-conjugates of 20(s)-camptothecin Method for producing glyco-conjugates of 20(s)-camptothecin

C - Chemistry, Metallurgy

07

H

C07H 15/203 (2006.01) C07D 491/22 (2006.01) C07H 15/26 (2006.01) C07K 5/062 (2006.01) C07K 9/00 (2006.01) A61K 31/706 (2006.01) C07B 53/00 (2006.01)

Patent

CA 2366632

The invention relates to a method for producing glyco-conjugates of 20(S)- camptothecin in which a 3-O-methylated .beta.-L-fucose building block is linked to the 20 hydroxyl group of a camptothecin derivative via thiourea- modified peptide spacers, whereby the decisive step exists in the linking of the building block (II) with the building block (V) in the presence of a particular coupling reagent such as N-[(dimethylamino)-1H-1,2,3-triazolo[4,5- b]pyridin-1-yl-methylene]-N-methylmethane-aminium hexafluorophosphate-N-oxide (HATU).

La présente invention concerne un procédé de production de glycoconjugués de 20(S)-camptothécine, dans lesquels un composant beta -L-fucose est lié, par l'intermédiaire d'un espaceur peptidique modifié par thiourée, au groupe 20-hydroxyle, l'étape décisive étant la liaison du composant (II) au composant (V), en présence d'un réactif de couplage particulier, tel que le N-[diméthylamino]-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-méthylène]-N-méthylméthanaminium hexafluorophosphate-N-oxyde (HATU).

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