Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1990-12-03
1993-03-30
Griffin, Ronald W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
536103, 435280, 562401, 210632, 210634, 210635, 210636, C08B 3716, C07B 6300
Patent
active
051984296
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to substituted cyclodextrins, to a process for their production, and to a process for the separation of chiral organic compounds by chromatographic separation processes, particularly gas chromatography, using the substituted cyclodextrins as stationary phase.
Substituted cyclodextrins are known, for example, from DE-OS 37 10 569, which is no prior publication, which describes the production of ultrathin films from these cyclodextrin compounds or an inclusion compound on the basis of the cyclodextrin compounds. These ultrathin films can be used, for example, as protective film for compounds which are sensitive to light and oxygen, or as carrier in chromatography.
Triethyl-.beta.-cyclodextrin is described in Journal of Pharmaceutical Sciences (1987, 660). An alkyl-acyl-compound (R.sub.2 =R.sub.6 =methyl, R.sub.3 =benzoyl, n=7, of the following general formula) is described in J. Chem. Soc. Perkin Trans. (1987), 1323.
Single cyclodextrin derivatives were also mentioned as possible stationary phases, however, realization of this possibility was limited due to the properties of the known substances, this is described, for example, in ACS Symposium Series, 1987, vol. 342, pages 200 to 217, and in Starch/Starke, 1987, pages 357 to 358.
Up to now, the separation of enantiomeric, low-molecular chiral compounds by gas-chromatography has been conducted by using chiral low-molecular or polymeric separation phases with amide or diamide structure.
Such a separation is almost exclusively limited to enantiomers with amide, carbamate, oxime, or hydroxyl groups. In this connection, intermolecular hydrogen bridge bonds are built so that diastereomeric associates between chiral separation phase and chiral substrates are formed.
In order to improve the separation results, the enantiomers to be separated were mostly converted into derivatives with amide or carbamoyl functions.
Due to the fact that the formed derivatives are difficultly volatile, high operating temperatures of the chromatographic columns are required and thus leads to uneven courses of the base-lines of the chromatrograms and to reduced separation efficiency due to cross diffusion.
It was the object of the present invention to provide improved stationary phases for the separation of chiral compounds, particularly of enantiomers, and a process for the separation of chiral compounds.
Surprisingly,it was found that this object is achieved by substituted cyclodextrins of the general formula: ##STR2## in which: R.sup.2 and R.sup.6 mean straight-chain or branched alkyl or alkenyl groups with 1 to 8 carbon atoms or cyclo-alkyl groups with 5 to 8 carbon atoms which can be the same or different, and which can be the same or different to the residues R.sup.2 and R.sup.6, with 1 to 8 carbon atoms or a cycloalkyl group with 5 to 8 carbon atoms, or unsaturated aliphatic or cycloaliphatic or with an aromatic hydrocarbon residue with 1 to 8 carbon atoms, and
A further solution of the problem underlying the present invention is the provision of a process for the chromatographic separation of chiral compounds, particularly of enantiomers.
In this connection, compounds with
The substituted cyclodextrins according to the present invention permit a separation of enantiomers which is mainly caused by inclusion effects at the macrocyclic chiral cyclodextrins, and which--due to the separation mechanism which, compared to the separation phases according to the prior art, is completely different--can be employed even for those enantiomers not being able to form hydrogen bridges and therefore could not be separated on the chiral separating phases used until now.
For the use as separation phases in gas-chromatography the compounds according to the present invention on the one hand have the advantage of having a very high temperature stability of more than 200.degree. C., on the other hand, the separation mechanism which--compared to the separation phases known until now--is different in most cases permits the conversion into very readily volatile derivatives,
REFERENCES:
patent: 4582900 (1986-04-01), Brandt et al.
patent: 4590167 (1986-05-01), Gunther et al.
patent: 5078886 (1992-01-01), Hsu
Chemical Abstracts, vol. 109, Oct. 10, 1988 Abstract 109: 125206x.
Tetrahedron, vol. 39, No. 9, 1983 Pergamon Press Ltd. (Oxford, GB), A. P. Croft et al.: "Synthesis of Chemically Modified Cyclodextrins", pp. 1417, 1427-1433, 1472, see page 1431.
Starch/Starke, vol. 39, No. 10, Oct. 1987, VCH Verlagsgesellschaft mbH (Weinheim, DE), J. Szejtli: "Application of Cyclodextrins in the Chromatography", pp. 357-362, see page 358.
Chemical Abstracts, vol. 109, No. 15, Oct. 10, 1988 (Columbus, Ohio, US), W. A. Koenig et al.: "Modified cyclodextrin a New Highly Enantioselective Stationary Phase for Gas Chromatography", p. 331, Abstract No. 125206x of Angew. Chem. 1988, 100(7), 989-90.
Konig Wilfried
Lutz Sabine
von der Bey Eva
Wenz Gerhard
Griffin Ronald W.
Macherey-Nagel & Co.
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