Sulfate of n-acetylneuraminic acid homopolymer and processes for

Details Sulfate of n-acetylneuraminic acid homopolymer and processes for Sulfate of n-acetylneuraminic acid homopolymer and processes for

1994-12-27

1997-06-10

Nutter, Nathan M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536122, 5361231, C07H 1100, C07H 1312

Patent

active

056376901

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The invention relates to a sulfate ester of N-acetylneuraminic acid homopolymer, a method for producing the same, a medicament effective for treating human immunodeficiency virus (HIV) comprising the sulfate ester as an active ingredient (anti-HIV agent), a method for treating AIDS using the sulfate ester, the sulfate ester for use to treat AIDS and use of the sulfate ester to produce the medicament.


BACKGROUND ART

Although the number of patient of Acquired Immune Deficiency Syndrome (AIDS) caused by HIV is rapidly increasing, an effective method for treating AIDS has not been established yet. Because of high mortality thereof after crisis, there is an urgent demand for searching an anti-HIV agent.
Azidothymidine and like reverse transcriptase inhibitors, and heparin and like sulfated polysaccharides capable of suppressing infection of HIV to a target cell are exemplified as a known anti-HIV agent (see, Japanese unexamined patent publication Nos. 215529/1987; 7577/1990; and 91027/1992).
Although azidothymidine and like reverse transcriptase inhibitors inhibit increase of HIV, the inhibitors have a strong side effect because of an action thereof on a nucleic acid synthesis. A long-term administration is, therefore, difficult. In contrast, heparin and like sulfated polysaccharides having been used as an anticoagulant have a strong anticoagulant activity relative to an anti-HIV activity. The sulfated polysaccharides have a very strong anticoagulant activity at a concentration where the polysaccharides exhibit an anti-HIV activity. Development of the sulfated polysaccharides as an anti-HIV agent is difficult due to the side effect thereof (anticoagulant activity).
It is an object of the present invention to provide a medicament having an excellent anti-HIV activity and being free of a side effect.


DISCLOSURE OF THE INVENTION

The inventors conducted extensive research in considering the problems of the prior art, and found that a novel sulfate ester of N-acetylneuraminic acid homopolymer is very weak in side effects, such as an anticoagulant activity, at a dose of exhibiting an anti-HIV activity.
Thus, the invention provides a sulfate ester of N-acetylneuraminic acid homopolymer represented by the following formula (I): ##STR2## [wherein R represents, the same or different, a hydrogen atom or SO.sub.3 H, n is an integer of 5 to 1,000, provided that the number of SO.sub.3 H residue per 1 molecule of N-acetylneuraminic acid residue is 0.1 to 3.] and a pharmaceutically acceptable salt thereof.
Further, the invention provides a method for producing a sulfate ester of N-acetylneuraminic acid homopolymer represented by the following formula (I): ##STR3## [wherein R and n are as defined above provided that the number of SO.sub.3 H residue per 1 molecule of N-acetylneuraminic acid residue is 0.1 to 3.] and a pharmaceutically acceptable salt thereof characterised in that 1 part by weight of N-acetylneuraminic acid homopolymer is reacted with 0.5 to 200 parts by weight of a catalyst and 0.2 to 30 parts by weight of a sulfating agent in the presence or absence of a solvent.
Further, the invention provides an anti-HIV agent comprising a sulfate ester of N-acetylneuraminic acid homopolymer represented by the following formula (I): ##STR4## [wherein R and n are as defined above provided that the number of SO.sub.3 H residue per 1 molecule of N-acetylneuraminic acid residue is 0.1 to 3.] or a pharmaceutically acceptable salt thereof combined with an additive.
Furthermore, the invention provides a method for treating AIDS characterised in that the method comprises administering a sulfate ester of N-acetylneuraminic acid homopolymer represented by the following formula (I): ##STR5## [wherein R and n are as defined above provided that the number of SO.sub.3 H residue per 1 molecule of N-acetylneuraminic acid residue is 0.1 to 3.] or a pharmaceutically acceptable salt thereof to a patient.
Furthermore, the invention provides a sulfate ester of N-acetylneuraminic acid homopolymer represented by the fo

REFERENCES:
patent: 5273892 (1993-12-01), Okutani
patent: 5447919 (1995-09-01), Hosang et al.

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