Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1995-04-26
1997-10-14
Fonda, Kathleen K.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
530322, 536 172, 536 173, 536 174, 536 175, 536 176, 536 179, 536 184, 536 187, 536 53, 536 54, 536 55, 514 8, 514 24, 514 27, 514 32, 514 35, A61K 3170, A61K 3816, A61K 3814, C07H 1500
Patent
active
056772858
DESCRIPTION:
BRIEF SUMMARY
This is the U.S. national stage entry of PCT/US93/07307, filed Aug. 3, 1993.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to new derivatives of neuraminic acid, especially carboxylic amides of the following formula, ##STR2## where Ac represents an acyl residue of a carboxylic acid of the aliphatic, araliphatic, aromatic, alicyclic or heterocyclic series, comprising the carboxylic amides, their 2-hydrocarbyl-glycosides, and their peracylated derivatives at the hydroxy groups of both these series of amides.
These compounds have interesting pharmacological properties, especially a protective effect against the neurotoxicity induced by excitatory amino acids of the of glutamic acid type, and can therefore be used in therapies of the central nervous system, such as those following cerebral degenerations or lesions, e.g., ischemia, hypoxia, epilepsy, trauma or compressions, metabolic dysfunctions, aging, toxic-infective and chronic neurodegenerative diseases, like Alzheimer's, Parkinson's, and Huntington's diseases.
The carboxylic amides and their derivatives of formula I according the present invention are new.
2. Description of Related Art
In the literature, there is a description of the non-substituted amide of N-acetyl-neuraminic acid, prepared as an intermediate in the synthesis of tetrazolyl-2-decarboxy-N-acetyl-neuraminic acid (see Ann. 1986, 2104-11).
In an article published in Hoppe Seyler's Physiol. Chemie, 1983, 364 (109) 1411-17, there is a description of the amides obtainable through the reaction of the benzylketoside of N-acetyl-neuraminic acid with L-glycine, L-glutamic acid, and L-phenylalanine, followed by the elimination of the benzyl group through catalytic hydrogenation; no pharmacological action is described for these derivatives.
SUMMARY OF THE INVENTION
In addition to providing new derivatives of neuraminic acid, the present invention also provides pharmacological preparations containing the aforesaid derivatives for therapeutic use.
A third object of the present invention concerns the therapeutic use of these preparations.
A final object of the present invention concerns procedures for the production of these new derivatives.
Further scope of the applicability of the present invention will become apparent from the detailed description provided below. However, it should be understood that the detailed description and specific examples, while indicating preferred embodiments of the invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.
DETAILED DESCRIPTION OF THE INVENTION
The following detailed description of the invention is provided to aid those skilled in the art in practicing the present invention. Even so, the following detailed description should not be construed to unduly limit the present invention, as modifications and variations in the embodiments herein discussed may be made by those of ordinary skill in the art without departing from the spirit or scope of the present inventive discovery.
The contents of each of the references cited herein are incorporated by reference in their entirety.
The amides and their derivatives according to the present invention can derive from both possible anomeric forms in position 2 of neuraminic acid, and therefore all the new compounds can be of either type at that position. The steric configuration of the other carbon atoms of the neuraminic residue is the same as that of the natural acid.
The acyl group Ac on the nitrogen of the neuraminic acid residue in the aforesaid formula has at least 4 and not more than 24 carbon atoms, and derives from non-substituted or substituted acids, preferably from 1 to 3 functions selected from the group consisting of halogen atoms; free, esterified, or etherified hydroxylic or mercapto groups; free or esterified carboxylic or sulfonic groups, or such groups transformed into amides; and free hydrocarbylic gr
REFERENCES:
Olney Annu. Rev. Pharmacol. Toxicol. 1990, 30, 47-71.
Schmid et al. Liebigs Ann. Chem. 1986, 2104-2111.
Holmquist Acta Chemica Scandinavica B 1974, 28(9), 1065-1068.
Eschenfelder et al. Hoppe-Seyler's Z. Physiol, Chem. 1983, 364, 1411-1417.
von Itzstein et al. Nature (Jun. 1993) Rational design of potent sialidase-based inhibitors of influenza virus replication, pp. 418-423.
Kirschner Gunter
Manev Hari
Romeo Aurelio
Toffano Gino
Trimarco Martino
FIDIA S.p.A.
Fonda Kathleen K.
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