Patent US4593091A successfully refreshed from Google Patents.
US4593091A
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Method for preparing ganglioside derivatives and use thereof in pharmaceutical compositions
Assignee: Fidia SpA
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Filing: 1982-09-28
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Granted: 1986-06-03
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Expires: 2002-09-28
Abstract
Abstract The present invention relates to a method for preparing inner ester derivatives of gangliosides and pharmaceutical compositions containing such derivatives to be used in treating disorders of the nervous system. The pharmaceutical compositions of the present invention promote nerve regeneration by stimulating nerve sprouting.
Inventors
- 👤 Francesco Della Valle
- 👤 Aurelio Romeo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 16:15
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/01
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
187 words
A method for preparing inner ester ganglioside derivatives, said derivatives comprising: (a) a carbohydrate portion, at least one ceramide and at least one sialic acid moiety; (b) said carbohydrate portion including at least one N-acetylgalactosamine or N-acetylglucosamine moiety and at least one glucose or galactose moiety; (c) said acid moiety including at least one N-acetylneuraminic acid or N-glycolylneuraminic acid; and (d) the carboxyl group of at least one of said acid moieties being ester bonded to a hydroxy group of one of said carbohydrates or one of said acid moieties to form a lactonic ring; said method for preparing inner ester ganglioside derivatives comprising converting the carboxylate groups in a ganglioside or a mixture of gangliosides to carboxyl groups or to a salt thereof by means of ion exchange; and reacting, in a non-aqueous organic solvent, the converted ganglioside or a mixture of gangliosides or a salt of such ganglioside or mixture of gangliosides with a lactonization reagent to form at least one lactonic bond in said inner ester ganglioside derivatives, with the proviso that said solvent and lactonization reagent are not acetic acid or trichloroacetic acid.
Claim 2
Independent Claim
187 words
A method for preparing inner ester ganglioside derivatives, said derivatives comprising: (a) a carbohydrate portion, at least one ceramide and at least one sialic acid moiety; (b) said carbohydrate portion including at least one N-acetylgalactosamine or N-acetylglucosamine moiety and at least one glucose or galactose moiety; (c) said acid moiety including at least one N-acetylneuraminic acid or N-glycolylneuraminic acid; and (d) the carboxyl group of at least one of said acid moieties being ester bonded to a hydroxy group of one of said carbohydrates or one of said acid moieties to form a lactonic ring; said method for preparing inner ester ganglioside derivatives comprising converting the carboxylate groups in a ganglioside or a mixture of gangliosides to carboxyl groups or to a salt thereof by means of ion exchange; and reacting, in a non-aqueous organic solvent, the converted ganglioside or a mixture of gangliosides or a salt of such ganglioside or mixture of gangliosides with a lactonization reagent to form at least one lactonic bond in said inner ester ganglioside derivatives, with the proviso that said solvent and lactonization reagent are not acetic acid or trichloroacetic acid.
Claim 3
Dependent Claim
17 words
the method of claim 1, wherein the ganglioside or mixture of gangliosides is extracted from bovine brains.
Claim 4
Dependent Claim
24 words
The method of claim 1, wherein said organic solvent is selected from the group consisting of dimethyl sulfoxide, dimethylformamide, sulfolane, tetrahydrofuran, dimethoxyethane and pyridine.
Claim 5
Dependent Claim
26 words
The method of claim 1, wherein said lactonization reagent is selected from the group consisting of carbodiimides soluble in organic solvents, 2-chloro-1-methyl-pyridinium salts, ethoxyacetylene and N-ethyl-5-phenylisoxazolium-3'-sulfonate.
Claim 6
Dependent Claim
13 words
The method of claim 4, wherein the carbodiimide is dicyclohexylcarbodiimide, benzylisopropylcarbodiimide or benzylethylcarbodiimide.
Claim 7
Dependent Claim
24 words
The method of claim 1, wherein said inner ester ganglioside derivatives are obtained by precipitation with acetone after said reaction with a lactonization reagent.
Claim 8
Independent Claim
92 words
A method for preparing inner ester ganglioside derivatives which comprises: (a) dissolving a ganglioside or mixture of gangliosides obtained from a mammal in a non-aqueous aprotic solvent; (b) adding an ion exchange resin to said ganglioside or mixture of gangliosides whereby the carboxylate groups of said gangliosides are converted to carboxyl groups; and (c) treating said ganglioside or mixture with a lactonization reagent to form at least one lactonic bond in said inner ester ganglioside derivative, with the proviso that said solvent and lactonization reagent are not acetic acid or trichloroacetic acid.
Claim 9
Independent Claim
92 words
A method for preparing inner ester ganglioside derivatives which comprises: (a) dissolving a ganglioside or mixture of gangliosides obtained from a mammal in a non-aqueous aprotic solvent; (b) adding an ion exchange resin to said ganglioside or mixture of gangliosides whereby the carboxylate groups of said gangliosides are converted to carboxyl groups; and (c) treating said ganglioside or mixture with a lactonization reagent to form at least one lactonic bond in said inner ester ganglioside derivative, with the proviso that said solvent and lactonization reagent are not acetic acid or trichloroacetic acid.
Claim 10
Dependent Claim
16 words
The method of claim 7, wherein said gangliosides of step (a) are extracted from bovine brains.
Claim 11
Dependent Claim
21 words
The method of claim 7, wherein said aprotic solvent is selected from the group consisting of dimethyl sulfoxide, dimethylformamide and sulfolane.
Claim 12
Dependent Claim
22 words
The method of claim 7, wherein said ion exchange resin is removed from said mixture after step (b) and before step (c).
Claim 13
Dependent Claim
19 words
The method of claim 7, wherein said inner ester ganglioside derivative obtained in step (c) is precipitated with acetone.
Claim 14
Dependent Claim
26 words
The method of claim 7, wherein said lactonization reagent is selected from the group consisting of carbodiimides soluble in organic solvents, 2-chloro-1-methyl-pyridinium salts, ethoxyacetylene and N-ethyl-5-phenylisoxazolium-3'-sulfonate.
Claim 15
Dependent Claim
13 words
The method of claim 12, wherein said carbodiimide is dicyclohexylcarbodiimide, benzylisopropylcarbodiimide, or benzylethylcarbodiimide.
Claim 16
Dependent Claim
10 words
The method of claim 13, wherein said carbodiimide is dicyclohexylcarbodiimide.
References Cited (Backward Citations)
US4415733A
Cited
EP0072722A2
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-06-02 | 1989-12-02 | 1990-06-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-06-02 | 1993-12-02 | 1994-06-03 | $3760.00 | Window Closed / Lapsed |
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