Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1997-09-02
2000-01-04
Kunz, Gary L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536124, 5361231, 536110, 536 56, C07H 100, C07H 300, C08B 300, C08B 1510
Patent
active
060111496
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of International Application PCT/EP 96/00773, filed Feb. 24, 1996.
The invention relates to substantially photochemically cross-linked polysaccharide derivatives that are used as supports in the chromatographic separation of enantiomers.
DE-A-2 422 365 describes polymers that are suitable for photopolymerisation, having anhydride-containing groups, that are converted by means of mechanically active light into resistant substances that are suitable as protective printing compositions or also for the manufacture of protective printing screens for printing plates.
N. R. Bertoniere et al. describe in J. Appl. Polymer Sci., Vol. 15, (1971) 1743 woven cotton fabrics having as substituents cinnamic acid esters (cinnamoyl radicals) which when irradiated with light of a specific wavelength (2573 .ANG.) first isomerise and then dimerise to truxillic and truxinic acid derivatives, the photochemical reaction taking place mainly on the surface of the fabric.
The two U.S. Pat. Nos. 2,682,481 and 2,682,482 describe methods by which soluble carbohydrates, especially cellulose derivatives, that carry unsaturated functional groups are converted by heating with peroxide catalysts and dimerisation or further cross-linking into shaped articles having an insoluble surface.
E. Yashima et al. describe in J. Chromatography A, 677(1994), 11-19 3,5-dimethylphenylcarbamates of cellulose and amylose that are bonded at specifically selected sites to silica gel and are used as a chiral stationary phase for HPL chromatography (high-pressure liquid chromatography). The 3,5-dimethylphenylcarbamates of cellulose and amylose are bonded to the 3-aminopropyl silica gel via 4,4'-diphenylmethane isocyanate as intermediate members. Since those chemically bonded phases are not damaged by polar solvents, such as CHCl.sub.3 (chloroform), a small amount of CHCl.sub.3 can be added to the eluant for effective separation of racemates and of enantiomers.
Y. Okamoto et al. describe in J. Liquid Chromatography 10, 1613-1698 (1987), cellulose-tris(3,5-dimethylphenylcarbamates) and -tris(3,5-dichlorophenylcarbamates) that are chemically bonded to 3-aminopropyl silica gel via 4,4'-diphenylmethane isocyanate.
As the first process step for the preparation, first the cellulose is bonded via the diisocyanate to the 3-aminopropyl silica gel. The reaction product is then treated with a large excess of 3,5-dimethylphenyl isocyanate or 3,5-dichlorophenyl isocyanate to produce the corresponding carbamates of cellulose.
The optical separating power of the chiral stationary phase is compared to that obtained by coating silica gel with cellulose triphenyl carbamates, it being possible to vary the chiral separating capacity of the stationary phase by heat treatment.
In a poster exhibited at the 5th Intern. Symposium "On Chiral Discrimination" in Stockholm in October, 1994, L. Oliveros et al. describe stationary phases consisting of 3,5-dimethylphenylcarbamate cellulose that have been immobilised on a support. It is not clear from the data given on the poster whether the chiral material has been immobilised and has any particular advantages over known materials from the prior art.
The present invention relates to photochemically cross-linked polysaccharide derivatives of the general formulae IA and IB ##STR2## wherein R is a polysaccharide radical in which the OH groups have been esterified as OR' groups or converted into a carbamate (urethane), substituted aryl,
The invention relates especially to photochemically cross-linked polysaccharide derivatives of the general formulae IA and IB, wherein esterified as OR' groups or converted into a carbamate (urethane), unsubstituted or substituted phenyl and
Of very special importance are photochemically cross-linked polysaccharide derivatives of the general formulae IA and IB, wherein groups or converted into a carbamate (urethane),
The invention relates to the compounds of formulae 1A and 1B characterised in the Examples.
Hereinbefore and hereinafter, lower radicals and compounds are to be understood, for example,
REFERENCES:
patent: 3960685 (1976-06-01), Sano et al.
patent: 4107174 (1978-08-01), Baumann et al.
patent: 4861872 (1989-08-01), Okamoto et al.
L. Oliveros, et al., Journal of Liquid Chromatography, vol. 18, No. 8, 1995, pp. 1521-1532.
Kalinchak Stephen G.
Kunz Gary L.
Lopez Gabriel
Novartis AG
LandOfFree
Photochemically cross-linked polysaccharide derivatives as suppo does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Photochemically cross-linked polysaccharide derivatives as suppo, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Photochemically cross-linked polysaccharide derivatives as suppo will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1073579