C - Chemistry – Metallurgy – 07 – H
Patent
C - Chemistry, Metallurgy
07
H
260/230.58
C07H 5/04 (2006.01) C07H 15/10 (2006.01)
Patent
CA 1230596
ABSTRACT OF THE DISCLOSURE Processes are provided herein for preparing either partial or fully lactonized inner ester derivatives of gangliosides. The inner ester ganglioside comprises: (i) a carbohydrate portion, at least one ceramide and at least one acid moiety; (ii) the carbohydrate portion including at least one N-acetylgalactosamine or N-acetylglucosamine moiety and at least one glucose or galactose moiety; and (iii) the acid moiety including at least one N-acetylneuraminic acid or N-glycolyneuraminic acid. The processes each include reacting, in a non-aqueous organic solvent, (a) a ganglioside in which the carboxylate groups are in carboxyl form, or (b) a mixture of gangliosides in which the carboxylate groups are in carboxyl form, or (c) a salt of a ganglioside with a tertiary nitrogen base, or (d) a salt of a mixture of gangliosides with a tertiary nitrogen base, with a sufficient amount of a lactonization reagent, to form at least one lactonic bond in the inner ester ganglioside derivatives, with the proviso that the solvent and lactonization reagent are not acetic acid or trichloroacetic acid. Generally, the carboxyl group of at least one of the acid moieties is ester bonded to a hydroxy group or to one of the carbohydrates of one of the moieties to form a lactonic ring. The inner ester ganglioside derivatives co formed can be used in the treatment of peripheral nervous system disorders due to traumatic, compressive, degenerative or toxic-infectious causes where the stimulation of Abstract continued, page 2 nerve degeneration and recovery of neuromuscular function is necessary, and in central nervous system disorders due to traumatic, anoxic degenerative or toxic-infectious causes where the stimulation of neuronal sprouting is necessary for functional recovery. The inner ester derivatives of gangliosides have much greater activity than that of the gangliosides themselves.
408559
Della Valle Francesco
Romeo Aurelio
Borden Ladner Gervais Llp
Fidia S.p.a.
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