Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1991-12-06
1993-08-31
Nutter, Nathan M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 46, 536103, 127 32, C08B 3716
Patent
active
052410595
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to cyclodextrin derivatives, more particularly to cyclodextrin derivatives having extremely high water solubility.
BACKGROUND ART
Chemicals such as pharmaceuticals and agrichemicals are generally required to have water solubility because of the nature of their use. One of the means of improving the water solubility of those chemicals that have been proposed in recent years is by including them in cyclodextrin.
However, because of the limited solubility of cyclodextrin in water, the cyclodextrin inclusion compounds have had the problem that their water solubility is still insufficient for practical applications. Under these circumstances, efforts have been made to improve the solubility of cyclodextrin in water by various methods such as methylating, hydroxyethylating or hydroxypropylating cyclodextrin, or synthesizing polymers crosslinked with epichlorohydrin, but no satisfactory results have yet been achieved.
Therefore, an object of the present invention is to provide cyclodextrin derivatives having extremely high solubility in water.
DISCLOSURE OF INVENTION
The present inventor conducted intensive studies in order to achieve the above-stated object and found that it could be attained by providing a cyclodextrin derivative having at least one group selected from among a sulfonic acid group, a sulfonic acid salt group, an ammonium salt group, a phosphoric acid group, a carboxyl group, a carboxylic acid salt group and a hydroxyl group.
The present invention is described below in greater detail.
In accordance with the present invention, the water solubility of cyclodextrin (hereunder abbreviated as CD) is improved significantly by positively introducing a sulfonic acid group (--SO.sub.3 H), a sulfonic acid salt group (--SO.sub.3 M), an ammonium salt group, preferably NH.sub.4.sup.+ X.sup.- group (X is a halogen atom), a phosphoric acid group (--PO(OH).sub.2), a carboxyl group (--COOH), a carboxylic acid salt group (--COOM) or a hydroxyl group into the molecule of CD. Specific examples of the CD derivative of the present invention these obtained include: those having a sulfonic acid group such as monosulfonic acid-.beta.-CD, heptasulfonic acid-.beta.-CD, disulfonic acid .beta.-CD, tetradecasulfonic acid .beta.-CD and heneicosasulfonic acid .beta.-CD; those having an ammonium salt group such as monotrimethylammonium (chloride) .beta.-CD, ditrimethylammonium (chloride) .beta.-CD and heptatrimethylammonium (chloride) .beta.-CD; those having a phosphoric acid group such as monophosphoric acid .beta.-CD, diphosphoric acid .beta.-CD and heptaphosphoric acid .beta.-CD; and those having a carboxyl group such as monocarboxylic acid .beta.-CD, dicarboxylic acid .beta.-CD, heptacarboxylic acid .beta.-CD and biscarboxylic acid .beta.-CD.
Useful sulfonic acid salt groups and carboxylic acid salt groups include alkali metal (e.g. K or Na) salts of a sulfonic acid group or a carboxyl group and CD derivatives having those groups may be used as the CD derivatives of the present invention.
The CD to be used in the present invention may be of any type such as .alpha.-CD, .beta.-CD or .gamma.-CD.
Shown below are exemplary reaction schemes for the synthesis of CD derivatives having at least one sulfonic acid group in accordance with the present invention, with the illustrated CD derivatives being monosulfonic acid .beta.-CD, disulfonic acid .beta.-CD, heptasulfonic acid .beta.-CD, tetradecasulfonic acid .beta.-CD and heneicosasulfonic acid .beta.-CD.
(1) Synthesis of monosulfonic acid .beta.-CD ##STR1##
(2) Synthesis of heptasulfonic acid .beta.-CD ##STR2##
(3) Synthesis of disulfonic acid .beta.-CD ##STR3##
(4) Synthesis of tetradecasulfonic acid .beta.-CD ##STR4##
(5) Synthesis of heneicosasulfonic acid .beta.-CD ##STR5##
The above-listed monosulfonic acid .beta.-CD, disulfonic acid .beta.-CD, heptasulfonic acid .beta.-CD, tetradecasulfonic acid .beta.-CD and heneicosasulfonic acid .beta.-CD can specifically be synthesized by the following schemes.
(1) Synthesis scheme for monosulf
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Nutter Nathan M.
Toppan Printing Co. Ltd.
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