US20100140172A1 - Optical-Isomer-Separating Agent - Google Patents

Optical-Isomer-Separating Agent Download PDF

Info

Publication number
US20100140172A1
US20100140172A1 US11/884,417 US88441706A US2010140172A1 US 20100140172 A1 US20100140172 A1 US 20100140172A1 US 88441706 A US88441706 A US 88441706A US 2010140172 A1 US2010140172 A1 US 2010140172A1
Authority
US
United States
Prior art keywords
separating agent
enantiomeric
enantiomeric isomer
organic solvent
isomer separating
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US11/884,417
Other languages
English (en)
Inventor
Yasuhiro Kagamihara
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daicel Corp
Original Assignee
Daicel Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daicel Chemical Industries Ltd filed Critical Daicel Chemical Industries Ltd
Assigned to DAICEL CHEMICAL INDUSTRIES, LTD. reassignment DAICEL CHEMICAL INDUSTRIES, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KAGAMIHARA, YASUHIRO
Publication of US20100140172A1 publication Critical patent/US20100140172A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/29—Chiral phases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
    • B01D15/3833—Chiral chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3268—Macromolecular compounds
    • B01J20/3272—Polymers obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3268—Macromolecular compounds
    • B01J20/328—Polymers on the carrier being further modified
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/50—Conditioning of the sorbent material or stationary liquid
    • G01N30/56—Packing methods or coating methods
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N2030/022—Column chromatography characterised by the kind of separation mechanism
    • G01N2030/027—Liquid chromatography
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/50—Conditioning of the sorbent material or stationary liquid
    • G01N30/56—Packing methods or coating methods
    • G01N2030/562—Packing methods or coating methods packing
    • G01N2030/565—Packing methods or coating methods packing slurry packing

Definitions

  • the present invention relates to an enantiomeric isomer separating agent and a method of producing the agent.
  • a separating agent obtained by carrying a polysaccharide derivative on silica gel has been generally used as, for example, an enantiomeric resolution agent for high performance liquid chromatography.
  • the manners in each of which silica gel supports the polysaccharide derivative are classified into the case where silica gel is caused to support the polysaccharide derivative physically (physical support type separating agent) and the case where silica gel is caused to support the polysaccharide derivative by chemical bonding (chemical support type separating agent). See JP-B-2751004 or JP-A-8-5623.
  • the chemical support type separating agent has a smaller amount of eluted component originating from the polysaccharide derivative than that of the physical support type separating agent even when an organic solvent in which the polysaccharide derivative is soluble is used.
  • an unreacted polysaccharide derivative is present even in the chemical support type separating agent, so an eluent contains eluted component originating from the polysaccharide derivative.
  • JP-A 7-260762 discloses a coating type separating agent having a small amount of eluted component.
  • a low-molecular-weight polysaccharide derivative is eluted in such physical support type separating agent. This is because the molecular weight distribution of a polysaccharide to be used varies.
  • the present invention provides an enantiomeric isomer separating agent improved in the separating performance when it is used for a separating agent of high performance liquid chromatography and a method of producing the agent.
  • the present invention provides an enantiomeric isomer separating agent, which includes a polysaccharide derivative supported on particles of a support by chemical bonding, and has a concentration of eluted component (in terms of mass proportion) as determined through a liquid passing test under the following conditions of 20 ppm or lower:
  • the enantiomeric isomer separating agent is packed into a column having a diameter of 1 cm and a length of 25 cm by a slurry method
  • a method of producing the above-mentioned enantiomeric isomer separating agent including the steps of: washing an unwashed enantiomeric isomer separating agent with an organic solvent in which the polysaccharide derivative is soluble once or multiple times; and drying the washed enantiomeric isomer separating agent.
  • a method of separating enantiomeric isomers including bringing the enantiomeric isomers into contact with the above-mentioned enantiomeric isomer separating agent, or use of the above enantiomeric isomer separating agent for separating enantiomeric isomers.
  • unwashed enantiomeric isomer separating agent refers to an enantiomeric isomer separating agent that does not satisfy the following requirement: the concentration of eluted component (in terms of mass proportion) upon performance of a liquid passing test under the above-mentioned conditions is 20 ppm or lower.
  • An enantiomeric isomer separating agent of the present invention has good separating performance, and can increase the purity of a fractionated enantiomeric isomer.
  • the agent is suitable for high performance liquid chromatography.
  • the enantiomeric isomer separating agent of the present invention has a concentration of eluted component (in terms of mass proportion) as determined through the following liquid passing test of 20 ppm or lower, preferably 15 ppm or lower, or more preferably 10 ppm or lower.
  • the enantiomeric isomer separating agent is packed into a column having a diameter of 1 cm and a length of 25 cm by a slurry method
  • a chemical support type separating agent is produced by chemically bonding a polysaccharide derivative to a support.
  • a polysaccharide derivative to be used in the present invention is well known, and can be produced by applying, for example, Examples 1 to 5 of JP-A-2004-3935, a method described in Synthesis Example 1 of JP-A-7-260762, or a method described in Production Method 3 of paragraph 43 of JP-B-2751004.
  • An enantiomeric isomer separating agent obtained by causing a support to support the polysaccharide derivative to be used in the present invention is well known, and can be produced by applying, for example, a method described in Example 1 of JP-B-2751004.
  • a porous organic support or a porous inorganic support can be used as the support, and a porous inorganic support is preferable.
  • a polymeric substance composed of, for example, polystyrene, polyacrylamide, or polyacrylate can be suitably used in a porous organic support.
  • Silica, alumina, magnesia, glass, kaolin, titanium oxide, a silicate, hydroxyapatite, or the like can be suitably used in a porous inorganic support; silica gel is particularly preferable.
  • silica gel when silica gel is used, silica gel is desirably subjected to a surface treatment such as a silanization treatment (silanization treatment with an aminoalkylsilane) or a plasma treatment in order that an influence of silanol remaining on the surface of silica gel may be eliminated, and the affinity of silica gel for an enantiomerically active polymer compound may be improved.
  • a surface treatment such as a silanization treatment (silanization treatment with an aminoalkylsilane) or a plasma treatment in order that an influence of silanol remaining on the surface of silica gel may be eliminated, and the affinity of silica gel for an enantiomerically active polymer compound may be improved.
  • a surface treatment such as a silanization treatment (silanization treatment with an aminoalkylsilane) or a plasma treatment in order that an influence of silanol remaining on the surface of silica gel may be eliminated, and the affinity of silica gel for
  • a porous support in particular, silica gel has a particle diameter of preferably 1 to 300 ⁇ m, more preferably 15 to 100 ⁇ m, or still more preferably 20 to 50 ⁇ m, and has an average pore diameter of preferably 200 to 8,000 ⁇ , more preferably 200 to 4,000 ⁇ , or still more preferably 300 to 2,000 ⁇ . It should be noted that the particle diameter of the porous support is substantially the particle diameter of the separating agent.
  • the average pore diameter of the porous support preferably falls within the range because a solution of an enantiomerically active polymer compound is sufficiently infiltrated into the pores of the porous support, and the enantiomerically active polymer compound can easily adhere to the inner wall of each of the pores in a uniform fashion. Further, the pressure loss of the separating agent can be maintained at a low level because the pores are prevented from clogging.
  • polysaccharide conveying polysaccharide derivative examples include any of a synthetic polysaccharide, a natural polysaccharide, and a natural products-modified polysaccharide as long as the polysaccharide or the derivative thereof is enantiomerically active.
  • the polysaccharide or the derivative thereof preferably has a high regularity in bonding manner.
  • polysaccharide examples include: ⁇ -1,4-glucan (cellulose); ⁇ -1,4-glucan (amylose or amylopectin); ⁇ -1,6-glucan (dextran); ⁇ -1,6-glucan (pustulan); ⁇ -1,3-glucan (such as curdlan or schizophyllan); ⁇ -1,3-glucan; ⁇ -1,2-glucan (a Crown Gall polysaccharide); ⁇ -1,4-galactan; ⁇ -1,4-mannan; ⁇ -1,6-mannan; ⁇ -1,2-fructan (inulin); ⁇ -2,6-fructan (levan); ⁇ -1,4-xylan; ⁇ -1,3-xylan; ⁇ -1,4-chitosan; ⁇ -1,4-N-acetylchitosan (chitin); pullulan; agarose; and alginic acid. Starch containing amylose is also included.
  • cellulose, amylose, ⁇ -1,4-xylan, ⁇ -1,4-chitosan, chitin, ⁇ -1,4-mannan, inulin, curdlan, and the like are preferred because they easily enables highly pure polysaccharides to be obtained.
  • Cellulose and amylose are particularly preferred.
  • the number average degree of polymerization of the polysaccharide is preferably 5 or more, or more preferably 10 or more, and has no particular upper limit.
  • the number average degree of polymerization is preferably 1,000 or less in terms of the easiness for handling, and is more preferably 5 to 1,000, still more preferably 10 to 1,000, or particularly preferably 10 to 500.
  • a product obtained by bonding a compound having a functional group capable of reacting with a hydroxyl group to some or all of the hydroxyl groups of the above-mentioned polysaccharide by, for example, ester bonding, urethane bonding or ether bonding can be used as the polysaccharide derivative.
  • Examples of functional group-containing compounds that can react with a hydroxyl group include isocyanate derivatives, carboxylic acids, esters, acid halides, acid amide compounds, halides compounds, aldehydes, alcohols or other elimination group-containing compounds; and their aliphatic, alicyclic, aromatic, and heteroaromatic compounds.
  • Examples of a particularly preferable polysaccharide derivative include a polysaccharide ester derivative and a polysaccharide carbamate derivative.
  • eluted component refers to, for example, a reaction by-product such as an isocyanic acid derivative or carboxylic acid derivative originating from a compound having a functional group capable of reacting with a hydroxyl group, or a polysaccharide derivative that has not been chemically bonded to the support.
  • a reaction by-product such as an isocyanic acid derivative or carboxylic acid derivative originating from a compound having a functional group capable of reacting with a hydroxyl group, or a polysaccharide derivative that has not been chemically bonded to the support.
  • the enantiomeric isomer separating agent obtained by chemically bonding the polysaccharide derivative to the support is washed with an organic solvent in which the polysaccharide derivative is soluble.
  • the washing can be performed once or multiple times (for example, two to ten times).
  • a method of washing the unwashed separating agent may be any method with which the unwashed separating agent and the organic solvent can be sufficiently brought into contact with each other, and a column mode, a batch mode, a method involving pouring the organic solvent into a residue after filtration to wash the unwashed separating agent, a heating reflux method, or the like is applicable.
  • organic solvent used for washing can be any solvent selected from tetrahydrofuran (THF), acetone, ethyl acetate, chloroform, methylene chloride, dimethyl acetoamide, dimethylformamide (DMF), and methanol.
  • THF tetrahydrofuran
  • acetone acetone
  • ethyl acetate chloroform
  • methylene chloride dimethyl acetoamide
  • dimethylformamide DMF
  • methanol methanol
  • the total used amount of the organic solvent is preferably 5 to 100 ml, more preferably 10 to 70 ml, or still more preferably 20 to 40 ml with respect to 1 g of the polysaccharide derivative in the unwashed separating agent.
  • the temperature of the organic solvent is lower than the boiling point of the solvent or not lower than the boiling point can be chosen depending on the washing method, and the temperature of the organic solvent is preferably 50 to 150° C., more preferably 60 to 120° C., or still more preferably 70 to 100° C.
  • the time needed for washing the unwashed separating agent may be any time required to reduce the amount of eluted component to a predetermined amount or less, and is generally about 1 to 100 hours, or preferably about 1 to 50 hours.
  • a filler after the washing can be recovered by, for example, filtration.
  • the temperature at which the filler is filtrated is typically 10 to 150° C., or preferably 20 to 100° C.
  • the separating agent after the washing is dried.
  • a method of drying the separating agent is not particularly limited, and is appropriately selected in consideration of the time period for which the separating agent is subjected to a drying treatment, and a cost for the treatment.
  • the separating agent is preferably subjected to a drying treatment under reduced pressure at room temperature to 100° C. for 2 to 24 hours.
  • An enantiomeric isomer separating agent obtained by the production method of the present invention has a concentration of eluted component in the above-mentioned liquid passing test of a predetermined value or lower.
  • Amylose derivative-bonded silica gel thus obtained was washed with 2.4 L of DMF at 75° C. (24 ml with respect to 1 g of an amylose derivative), whereby a target enantiomeric isomer separating agent was obtained.
  • Silica gel the surface of which had been treated with a silane treatment agent having an amino group at any one of its terminals was caused to support cellulose tris(3,5-dimethylphenylcarbamate) produced by a known method (Example 1 of JP-B 2669554) by physical adsorption.
  • a predetermined liquid passing test was performed by using the enantiomeric isomer separating agent of the present invention and tetrahydrofuran as a solvent to determine the concentration of eluted component (ppm).
  • the M 1 was 416.18 g
  • the M 2 was 2.7 mg
  • the ratio M 2 /M 1 was 6.5 ppm.
  • An unwashed chemical support type enantiomeric isomer separating agent was obtained in the same manner as in Example 1. 100 g of the resultant separating agent were washed by a general washing method. That is, the separating agent was filtrated through a glass filter at room temperature, and was washed with 2.4 L of methanol.
  • a liquid passing test of the present invention was performed by using the resultant enantiomeric isomer separating agent and ethyl acetate as a solvent to determine the concentration of eluted component.
  • the M 1 was 416.15 g
  • the M 2 was 85 mg
  • the ratio M 2 /M 1 was 204 ppm.
  • An unwashed chemical support type enantiomeric isomer separating agent was obtained in the same manner as in Example 2. 100 g of the resultant separating agent were washed by a general washing method. That is, the separating agent was filtrated through a glass filter at room temperature, and was washed with 2.4 L of methanol.
  • a liquid passing test of the present invention was performed by using the resultant enantiomeric isomer separating agent and THF as a solvent to determine the concentration of eluted component.
  • the M 1 was 416.23 g
  • the M 2 was 203 mg
  • the ratio M 2 /M 1 was 488 ppm.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
US11/884,417 2005-03-31 2006-03-30 Optical-Isomer-Separating Agent Abandoned US20100140172A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2005101846 2005-03-31
JP2005-101846 2005-03-31
PCT/JP2006/307259 WO2006107081A1 (fr) 2005-03-31 2006-03-30 Agent de separation d’isomeres optiques

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2006/307259 A-371-Of-International WO2006107081A1 (fr) 2005-03-31 2006-03-30 Agent de separation d’isomeres optiques

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/199,249 Continuation US8679346B2 (en) 2005-03-31 2011-08-24 Optical-isomer-separating agent

Publications (1)

Publication Number Publication Date
US20100140172A1 true US20100140172A1 (en) 2010-06-10

Family

ID=37073616

Family Applications (2)

Application Number Title Priority Date Filing Date
US11/884,417 Abandoned US20100140172A1 (en) 2005-03-31 2006-03-30 Optical-Isomer-Separating Agent
US13/199,249 Expired - Fee Related US8679346B2 (en) 2005-03-31 2011-08-24 Optical-isomer-separating agent

Family Applications After (1)

Application Number Title Priority Date Filing Date
US13/199,249 Expired - Fee Related US8679346B2 (en) 2005-03-31 2011-08-24 Optical-isomer-separating agent

Country Status (5)

Country Link
US (2) US20100140172A1 (fr)
EP (1) EP1865313B8 (fr)
JP (1) JP4871861B2 (fr)
CN (1) CN101151529B (fr)
WO (1) WO2006107081A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111366538B (zh) * 2020-03-17 2023-06-23 江苏道宁药业有限公司 一种精确检测含葡萄糖基团的多糖中旋光异构体比例的方法及装置
CN115792064A (zh) * 2022-11-30 2023-03-14 东北大学 一种在线分离与检测对映体的木质色谱柱及制备和使用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5679572A (en) * 1993-09-22 1997-10-21 Daicel Chemical Industries, Ltd. Separation of chiral compounds on polysaccharide supports
US5736259A (en) * 1994-03-17 1998-04-07 Daicel Chemical Industries, Ltd. Packing material for high-performance liquid chromatography and process for producing the same
US20030192829A1 (en) * 2002-04-12 2003-10-16 Atsushi Ohnishi Filler for separation of enantiomeric isomers in simulated moving bed chromatography

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2669554B2 (ja) * 1989-01-20 1997-10-29 ダイセル化学工業株式会社 新規な多糖誘導体及び分離剤
WO1992015616A1 (fr) * 1991-02-28 1992-09-17 Daicel Chemical Industries, Ltd. Nouveau derive de polysaccharide et agent separateur
JPH05255129A (ja) * 1992-03-12 1993-10-05 Nakano Vinegar Co Ltd 分離剤
US5496937A (en) * 1993-05-14 1996-03-05 Nakano Vinegar Co., Ltd. Polysaccharide substances, process for producing them and use of them
JP3190206B2 (ja) * 1993-06-22 2001-07-23 ダイセル化学工業株式会社 光学異性体用分離剤およびその製造法
JP2751004B2 (ja) 1993-09-22 1998-05-18 ダイセル化学工業株式会社 新規多糖誘導体，その製造法及びその用途
FR2714671B1 (fr) * 1994-01-05 1996-03-15 Conservatoire Nal Arts Metiers Nouveaux dérivés polysaccharidiques et leur emploi pour la préparation de phases stationnaires chirales utiles pour la séparation des isomères de composés chimiques.
JP3478595B2 (ja) * 1994-05-17 2003-12-15 ダイセル化学工業株式会社 光学異性体用分離剤
JP3181788B2 (ja) 1994-06-17 2001-07-03 株式会社ワイエムシィ クロマトグラフィ用の分離剤
KR0160399B1 (ko) * 1994-07-07 1999-05-01 고지마 아키로 분리제
TW362100B (en) 1995-07-21 1999-06-21 Novartis Ag The preparation and use of photochemically cross-linked polysaccharide derivatives having no photopolymerisable functional groups
JP4320068B2 (ja) * 1997-10-03 2009-08-26 ダイセル化学工業株式会社 光学異性体用分離剤及びその製造法
EP1422521A4 (fr) * 2001-06-15 2008-05-07 Daicel Chem Agent de separation pour isomere optique
JP2005017268A (ja) * 2003-05-30 2005-01-20 Daicel Chem Ind Ltd 光学異性体用分離剤、その製造方法、及び光学異性体用分離カラム
KR20060124720A (ko) * 2004-03-04 2006-12-05 다이셀 가가꾸 고교 가부시끼가이샤 광학 이성체용 분리제

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5679572A (en) * 1993-09-22 1997-10-21 Daicel Chemical Industries, Ltd. Separation of chiral compounds on polysaccharide supports
US5736259A (en) * 1994-03-17 1998-04-07 Daicel Chemical Industries, Ltd. Packing material for high-performance liquid chromatography and process for producing the same
US20030192829A1 (en) * 2002-04-12 2003-10-16 Atsushi Ohnishi Filler for separation of enantiomeric isomers in simulated moving bed chromatography

Also Published As

Publication number Publication date
EP1865313B1 (fr) 2015-03-25
EP1865313A1 (fr) 2007-12-12
JP4871861B2 (ja) 2012-02-08
US20110313146A1 (en) 2011-12-22
EP1865313A4 (fr) 2009-01-21
CN101151529A (zh) 2008-03-26
JPWO2006107081A1 (ja) 2008-09-25
US8679346B2 (en) 2014-03-25
EP1865313B8 (fr) 2015-05-27
CN101151529B (zh) 2011-12-07
WO2006107081A1 (fr) 2006-10-12

Similar Documents

Publication Publication Date Title
US5587467A (en) Separating agent for optical isomers and process for producing the same
EP0238044B1 (fr) Phénylcarbamate substitué par des groupes alcoyles, dérivé de polysaccharide
EP0957358B1 (fr) Remplissage de chromatographie liquide a haute performance
EP2113769A1 (fr) Charge de séparation d'isomère optique
JP4294028B2 (ja) 光学異性体用分離剤
US8679346B2 (en) Optical-isomer-separating agent
JPWO2002070123A1 (ja) 光学異性体用分離剤
US7740758B2 (en) Separating agent including polysaccharide derivative having a polycyclic structure
US5772876A (en) Separating agent
WO2012005245A1 (fr) Dérivé de polysaccharide, son procédé de fabrication et agent de séparation l'utilisant
JP3746315B2 (ja) 分離剤
JPH0475893B2 (fr)
JPH10185894A (ja) 高速液体クロマトグラフィ−用充填剤の製造法
JPH11255671A (ja) 光学異性体のクロマト分離法
US7258794B2 (en) Process for producing packing for resolving optical isomers
JPH10249191A (ja) 分離剤
JPH05240848A (ja) 分離剤

Legal Events

Date Code Title Description
AS Assignment

Owner name: DAICEL CHEMICAL INDUSTRIES, LTD.,JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:KAGAMIHARA, YASUHIRO;REEL/FRAME:024086/0362

Effective date: 20070726

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION