Chemical apparatus and process disinfecting – deodorizing – preser – Analyzer – structured indicator – or manipulative laboratory... – Means for analyzing liquid or solid sample
Reexamination Certificate
2002-02-19
2003-11-04
Dawson, Robert (Department: 1712)
Chemical apparatus and process disinfecting, deodorizing, preser
Analyzer, structured indicator, or manipulative laboratory...
Means for analyzing liquid or solid sample
C210S635000, C436S161000, C544S192000, C549S541000, C549S542000, C528S418000
Reexamination Certificate
active
06641784
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an optically active gent comprising optically active tris-(2,3-epoxypropyl)isocyanurate or an optically active derivative of tris-(2,3-epoxypropyl)isocyanurate, which may be supported on surface-modified carrier to form an optical resolver suitable for high-performance liquid chromatography.
BACKGROUND ART
In recent years, development of functional polymers intended for recognizing molecules, has been remarkable, and functional polymers capable of recognizing objective ions, organic low molecules and polymer compounds by their sizes, shapes, electric charges, etc., have been researched and developed. On the other hand, in the field of pharmaceuticals, many cases have been known in which pharmacological effects are different among optical isomers. For example, with respect to thalidomide, it is known that only (S)-(−) isomer has teratogenicity. Like this, with pharmaceuticals, it is not rare that only one of optical isomers of the compound to be used, brings about a strong side effect.
For such a reason, also in the field of recognizing molecules, an attention has been drawn particularly to a functional polymer having an asymmetry-recognizing ability. With respect to such a functional polymer having an asymmetry-recognizing ability, some technologies are known, and possible applications to a packing for an optical resolution chromatography column, a membrane for optical resolution or a host for a host-guest method, have been researched, studied and developed. Among them, an application to a packing for an optical resolution chromatography column has been active. The optical resolution chromatography is known to be very effective as a means for an optical resolution, since an optically active substance can be easily and simply analyzed and separated. Asymmetry-recognizing polymers so far researched and developed as packings for optical resolution chromatography columns include, polysaccharides such as cellulose triacetate (JP-A-59-166502, etc.), cellulose benzoate (JP-A-60-40952, etc.), cellulose carbamate (JP-A-60-108751, etc.) and amylose carbamate (JP-A-60-226831, etc.), synthetic polymers, for example, proteins such as bovine serum albumin (J. Chromatogr., 264(1983), 63-68, etc.), &agr;1-acid glycoprotein (J. Chromatogr., 269(1983), 71-80, etc.) and ovomucoid (JP-A-4-187646, etc.), a poly(meth)acrylic acid amide (JP-A-51-81891, etc.), and a poly(meth)acrylic acid ester (JP-A-56-142216, etc.).
On the other hand, Inoue et al. have reported on molecular design and utilization of novel optically active isocyanurates at 1998 Annual Meeting of Chemical Society of Japan (Report No. 1G414, 1G415) and at 1999 Annual Meeting of Chemical Society of Japan (Report No. 1D244, 1D245). In these reports, a discussion is made with respect to asymmetry-recognition, but no discussion is made on optical resolution.
These asymmetry-recognizing polymers have strong and weak points for optical resolution depending upon the objective compounds, whereby the respective ranges of the objective compounds for optical resolution have been limited.
It is an object of the present invention to provide a novel optical resolver employing an optically active tris-(2,3-epoxypropyl)isocyanurate or its derivative, or an optically active derivative of tris-(2,3-epoxypropyl)isocyanurate, in order to broaden the range of objective compounds for optical resolution.
The present inventors have conducted an extensive study to invent a novel optically active compound as a novel optical resolver, whereby they have found that an optically active compound employing tris-(2,3-epoxypropyl)isocyanurate as the starting material, is useful as an optical resolver and have accomplished the present invention.
DISCLOSURE OF THE INVENTION
The first aspect of the present invention is an optical resolver comprising an optically active tris-(epoxyalkyl)isocyanurate or its derivative.
The second aspect is the optical resolver according to the first aspect, wherein the optically active tris-(epoxyalkyl)isocyanurate is optically active tris-(2,3-epoxypropyl)isocyanurate.
The third aspect is an optical resolver comprising an optically active derivative of a tris-(epoxyalkyl)isocyanurate.
The fourth aspect is the optical resolver according to the third aspect, wherein the optically active derivative of a tris-(epoxyalkyl)isocyanurate is an optically active derivative of tris-(2,3-epoxypropyl)isocyanurate.
The fifth aspect is the optical resolver according to the fourth aspect, wherein the optically active derivative of tris-(2,3-epoxypropyl)isocyanurate is one obtained by a reaction of tris-(2,3-epoxypropyl)isocyanurate with an optically active compound.
The sixth aspect is an optical resolver having an optically active tris-(epoxyalkyl)isocyanurate or its derivative, or an optically active derivative of a tris-(epoxyalkyl)isocyanurate, supported on a carrier.
The seventh aspect is an optical resolver having optically active tris-(2,3-epoxypropyl)isocyanurate or its derivative, or an optically active derivative of tris-(2,3-epoxypropyl)isocyanurate, supported on a carrier.
BEST MODE FOR CARRYING OUT THE INVENTION
The optical resolver in the present invention is an optically active compound employing, as a starting material, an epoxy compound having an isocyanurate ring. Namely, it is required to have an isocyanurate ring, an asymmetric center based on an epoxy group and an optical activity. For example, when optically active tris-(2,3-epoxypropyl)isocyanurate is used, it has a tris-(propyl)isocyanurate structure having an optically active asymmetric center at the 2-position. When racemic tris-(2,3-epoxypropyl)isocyanurate is used, it has a tris-(propyl)isocyanurate structure having an asymmetric center at the 2-position and an optically active point derived from an optically active compound which is present in the vicinity thereof. Namely, the present invention can not be accomplished when a tris-(propyl)isocyanurate structure having no asymmetric center is used in a case where no epoxy compound is used as the starting material, or when a racemic tris-(2,3-epoxypropyl)isocyanurate is used alone.
In a first embodiment, the present invention provides an optical resolver comprising an optically active tris-(epoxyalkyl)isocyanurate or its derivative. The optically active tris-(epoxyalkyl)isocyanurate may be one wherein the alkyl part is an alkyl group having from 2 to 6 carbon atoms, and it may, for example, be optically active tris-(2,3-epoxypropyl)isocyanurate or optically active tris-(2,3-epoxy-2-methylpropyl)isocyanurate. However, optically active tris-(2,3-epoxypropyl)isocyanurate is preferably employed.
The optically active tris-(epoxyalkyl)isocyanurate itself, preferably the optically active tris-(2,3-epoxypropyl)isocyanurate itself, may be used as it is. However, when it is to be used as a packing for high performance liquid chromatography, it is preferably used as fixed on a carrier by physical adsorption or chemical reaction. In a case where it is to be chemically fixed, the carrier surface is modified with a compound having a reactive functional group (A), and by permitting the reactive functional group (A) and the epoxy group of an optically active tris-(2,3-epoxypropyl)isocyanurate to react, an optical resolver having the optically active tris-(2,3-epoxypropyl)isocyanurate derivative supported thereon, can be obtained. Here, it is preferred to react at least one functional group of the reactive functional group (A) to one molecule of the optically active tris-(2,3-epoxypropyl)isocyanurate. This is intended to prevent flowing out of the tris-(2,3-epoxypropyl)isocyanurate from the column by dissolution under an influence of an eluent used or by being detached by a physical force when the tris-(2,3-epoxypropyl)isocyanurate itself is used as a packing for e.g. high performance liquid chromatography to carry out optical resolution by using it as an optical resolver, whereby deterioration of the separation ability can be prevented, and a preferred packing useful for a long period of t
Hidaka Motohiko
Okamoto Yoshio
Aylward D.
Dawson Robert
Nissan Chemical Industries Ltd.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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