Methyl pyrrolidinone chitosan, production process and uses there

Details Methyl pyrrolidinone chitosan, production process and uses there Methyl pyrrolidinone chitosan, production process and uses there

1992-07-27

1995-01-03

Page, Thurman K.

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Web, sheet or filament bases; compositions of bandages; or...

424 1836, 424402, 424464, 424489, 536 20, 536 31, A61K 970, L08B 3708

Patent

active

053784723

DESCRIPTION:

BRIEF SUMMARY
SUMMARY OF THE INVENTION

It is an object of the present invention to provide a novel class of water-soluble, modified polysaccharides derived from chitosans, here indicated as 5-methylpyrrolidinone chitosans, where the glucan chains carry, at position 2,5-methylpyrrolidinone pendant groups. An essential characteristic property of 5-methylpyrrolidinone chitosans is their high susceptibility to depolymerization by lyozyze. When 5-methylpyrrolidinone chitosans are applied in vivo to a wound, this characteristic provides an efficient way to stimulate macrophages and spleen cells, and to favor the ordered deposition of collagen, while providing glucosamine and N-acetylglucosamine monomers no the biosynthetic route of hyaluronic acid and glycosaminoglycans. This exceptionally favorable biochemical significance enables 5-methylpyrrolidinone chitosans to heal wounds in connective tissues otherwise difficult or impossible to heal, such as bone and meniscal cartilage. Thus, a further object of the present invention is to provide medical items made of 5-methylpyrrolidinone chitosans, exerting excellent therapeutic effects on human tissues.
Due to the mentioned characteristics, 5-methylpyrrolidinone chitosans are exceptionally useful in cosmetical applications as well. Thus, a further object of the present invention is to provide cosmetical items made of or containing 5-methylpyrrolidinone chitosans.


BACKGROUND OF THE PRESENT INVENTION

The current use of wound dressing materials is based mostly on empirical knowledge rather than on real scientific understanding of the healing process. A certain number of characteristic properties of materials suitable for wound dressing has been clarified. They are: capacity to facilitate removal of exudates and toxic compounds, capacity to maintain humidity at the interface wound tissue/dressing, capacity to permit gas exchange and thermal insulation, protection against secondary infections, easy removal from the wound without damaging the newly formed tissue.
In the course of the last few years, polysaccharide based materials have been made available for wound treatment and general medications; they possess most of the characteristics indicated above while retaining specific properties. Important commercial products are: cross-linked dextran (Debrisan.RTM., Pharmacia), polyacrylamid agar (Geliperm.RTM., Geistlich), carboxymethyl cellulose (Comfeel.RTM.), hyaluronic acid (Connettivina.RTM., Fidia). Very little is known at the histological level about the effects of these polysaccharide based remedies, whilst the clinical data are abundant and the physico-chemical informations are well known. For no one of these dressings, however, a real biological significance is shown. As far as chitin-based wound dressings are concerned, in Japan one product is commercially available (Beschitin.RTM., Unitika), which is a non-woven fabric manufactured from chitin filaments. So far, no commercial exploitation, has been made of chitosan-based medical items and very limited research has been done in such field.


Previous research on chitin-based wound dressings

Balassa [DE 1,906,155 and DE 1,906,159 (1969); GB 1,252,373 (1971)] showed that pulverized chitin aids wound healing based on observations relating to mechanical resistance of the scar tissue. The same author [U.S. Pat. No. 3,632,754 (1972)] claimed "a process for facilitating wound healing" indicating chitin as "a wound healing accelerator" [also U.S. Pat. No. 3,914,413 (1975)]. In a previous work [Am. J. Surgery, 119, 560-564 (1970)] he indicated that chit in is "physiologically soluble" as a consequence of the effect of lysozyme; even in the absence of histological data, it was suggested that N-acetylglucosamine is important for the orientation and cross-linking of collagen, and that uridine diphosphate N-acetylglucosamine is a key compound in the biosynthesis of hyaluronic acid.
Widra [EP 0,089,152 (1983)] and Miyata et al. [Jpn. Kokai Tokkyo Koho JP 86,141,373 (1986)] described associations of chitosan and keratin or collagen to be a

REFERENCES:
patent: 5116824 (1992-05-01), Miyata et al.

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