WO2011071890A1 - Methods for purifying monosaccharide mixtures containing ionic impurities - Google Patents

Methods for purifying monosaccharide mixtures containing ionic impurities Download PDF

Info

Publication number
WO2011071890A1
WO2011071890A1 PCT/US2010/059244 US2010059244W WO2011071890A1 WO 2011071890 A1 WO2011071890 A1 WO 2011071890A1 US 2010059244 W US2010059244 W US 2010059244W WO 2011071890 A1 WO2011071890 A1 WO 2011071890A1
Authority
WO
WIPO (PCT)
Prior art keywords
glucose
monosaccharide
stream
process stream
exclusion resin
Prior art date
Application number
PCT/US2010/059244
Other languages
English (en)
French (fr)
Inventor
Edward Delaney
Anil Oroskar
Original Assignee
Axcan Pharma Inc.
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
Priority to BR112012013679A priority Critical patent/BR112012013679A8/pt
Priority to MX2012006453A priority patent/MX2012006453A/es
Priority to AU2010328366A priority patent/AU2010328366A1/en
Priority to JP2012542243A priority patent/JP2013512931A/ja
Priority to SG2012039988A priority patent/SG181150A1/en
Priority to RU2012125189/04A priority patent/RU2012125189A/ru
Application filed by Axcan Pharma Inc. filed Critical Axcan Pharma Inc.
Priority to EP10795131A priority patent/EP2509695A1/en
Priority to CA2783198A priority patent/CA2783198A1/en
Priority to CN2010800609503A priority patent/CN102725042A/zh
Publication of WO2011071890A1 publication Critical patent/WO2011071890A1/en
Priority to IL220226A priority patent/IL220226A0/en
Priority to US13/735,805 priority patent/US20130338086A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/10—Laxatives
    • 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
    • B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • 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
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • 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
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
    • B01D15/1814—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns recycling of the fraction to be distributed
    • B01D15/1821—Simulated moving beds
    • B01D15/185—Simulated moving beds characterized by the components to be separated
    • 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
    • B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
    • B01D15/365—Ion-exclusion
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/02—Monosaccharides
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
    • C13B20/00—Purification of sugar juices
    • C13B20/14—Purification of sugar juices using ion-exchange materials
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K1/00—Glucose; Glucose-containing syrups

Definitions

  • compositions include plural referents unless the context clearly dictates otherwise.
  • reference to “a composition” includes mixtures of two or more of the disclosed compounds, the disclosed compounds in combination with other pharmaceutically active compounds, or the disclosed compounds, solvates or diluents of the compounds as defined herein with other pharmaceutically acceptable ingredients.
  • Ion exclusion systems may employ similar resins used in ion exchange systems, but differ in that the ionic functionality of the resin is the same as that of the electrolyte and, therefore, there is little to no net exchange of ions.
  • the ion exclusion resin does not contain a mixture of strongly acidic resin (e.g., a resin bearing sulfonic acid residues) and weakly basic resin (e.g., a resin bearing tertiary amine groups); for instance, in one aspect, the ion exclusion resin does not include a "mixed bed.”
  • the ion exclusion resin can comprise a sulfonated polymer, for example, a sulfonated polystyrene with divinylbenzene (DVB) cross-linking which imparts physical stability to the resin polymer.
  • VVB divinylbenzene
  • a mixture comprising L- mannose and L-glucose can be subjected to simulated moving bed chromatography as disclosed herein. Initially, the mixture comprises L-mannose and L-glucose and the following ionic impurities: a.
  • L-mannose is removed or substantially removed from the mixture after SMB chromatography is performed. While the ion exclusion resin within the SMB unit is continuously contacted with the mixture and eluted with water, a continuous stream containing the deionized monosaccharides is produced along with a second stream containing the ionic by-products.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Emergency Medicine (AREA)
  • Sustainable Development (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Saccharide Compounds (AREA)
PCT/US2010/059244 2009-12-07 2010-12-07 Methods for purifying monosaccharide mixtures containing ionic impurities WO2011071890A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
MX2012006453A MX2012006453A (es) 2009-12-07 2010-12-07 Metodos para purificar mezclas de monosacaridos que contienen impurezas ionicas.
AU2010328366A AU2010328366A1 (en) 2009-12-07 2010-12-07 Methods for purifying monosaccharide mixtures containing ionic impurities
JP2012542243A JP2013512931A (ja) 2009-12-07 2010-12-07 イオン性不純物を含有する単糖混合物を精製する方法
SG2012039988A SG181150A1 (en) 2009-12-07 2010-12-07 Methods for purifying monosaccharide mixtures containing ionic impurities
RU2012125189/04A RU2012125189A (ru) 2009-12-07 2010-12-07 Способ очистки смесей моносахаридов, содержащих ионные примеси
BR112012013679A BR112012013679A8 (pt) 2009-12-07 2010-12-07 Método de separação de uma impureza iônica de uma corrente de processo contendo monossacarídeos, método de separação de uma impureza iônica de uma corrente de processo contendo sacarídeos, método contínuo de separação de impurezas catiônicas e aniônicas de uma corrente de processo contendo l-monossacarídeos, l-glicose possuindo uma pureza de pelo menos 98%, composição farmacêutica e método para preparo do cólon
EP10795131A EP2509695A1 (en) 2009-12-07 2010-12-07 Methods for purifying monosaccharide mixtures containing ionic impurities
CA2783198A CA2783198A1 (en) 2009-12-07 2010-12-07 Methods for purifying monosaccharide mixtures containing ionic impurities
CN2010800609503A CN102725042A (zh) 2009-12-07 2010-12-07 包含离子杂质的单糖混合物的纯化方法
IL220226A IL220226A0 (en) 2009-12-07 2012-06-07 Methods for purifying monosaccharide mixtures containing ionic impurities
US13/735,805 US20130338086A1 (en) 2009-12-07 2013-01-07 Methods for purifying monosaccharide mixtures containing ionic impurities

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26712709P 2009-12-07 2009-12-07
US61/267,127 2009-12-07

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US201213481447A Continuation 2009-12-07 2012-05-25

Publications (1)

Publication Number Publication Date
WO2011071890A1 true WO2011071890A1 (en) 2011-06-16

Family

ID=43708865

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/059244 WO2011071890A1 (en) 2009-12-07 2010-12-07 Methods for purifying monosaccharide mixtures containing ionic impurities

Country Status (14)

Country Link
US (1) US20130338086A1 (pt)
EP (1) EP2509695A1 (pt)
JP (1) JP2013512931A (pt)
KR (1) KR20120112518A (pt)
CN (1) CN102725042A (pt)
AU (1) AU2010328366A1 (pt)
BR (1) BR112012013679A8 (pt)
CA (1) CA2783198A1 (pt)
CL (1) CL2012001488A1 (pt)
IL (1) IL220226A0 (pt)
MX (1) MX2012006453A (pt)
RU (1) RU2012125189A (pt)
SG (1) SG181150A1 (pt)
WO (1) WO2011071890A1 (pt)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3082756A1 (fr) * 2018-06-26 2019-12-27 Seprosys Procede de separation de molecules ionisees dans une solution en contenant
US10543460B2 (en) 2013-03-08 2020-01-28 Xyleco, Inc. Upgrading process streams

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US556707A (en) 1896-03-17 steahan
US4522726A (en) 1984-07-30 1985-06-11 Progress Equities Incorporated Advanced separation device and method
US4581447A (en) 1984-08-13 1986-04-08 Uop Inc. Process for making a mixture of L-glucose and L-mannose
US4764276A (en) 1984-07-30 1988-08-16 Advanced Separation Technologies Incorporated Device for continuous contacting of fluids and solids
US4970302A (en) 1989-04-27 1990-11-13 Allied-Signal Inc. Selective catalytic conversion of cyanohydrins to their corresponding aldehydes without concurrent amine formation
US5538637A (en) 1993-09-29 1996-07-23 Tennessee Valley Authority Process for separating acid-sugar mixtures using ion exclusion chromatography
US5547817A (en) 1994-10-20 1996-08-20 Fuji Photo Film Co., Ltd. Photographic processing using a novel chelating complex
US5667693A (en) * 1995-02-02 1997-09-16 Tennessee Valley Authority Exclusion chromatographic separation of ionic from nonionic solutes
US5928429A (en) * 1997-10-31 1999-07-27 Imperial Holly Corporation Process for the enhancement of recovery of sugar
US5968362A (en) 1997-08-04 1999-10-19 Controlled Enviromental Systems Corporation Method for the separation of acid from sugars
JP2004236623A (ja) * 2003-02-07 2004-08-26 Kagawa Univ Ｌ−グルコースの製造方法
US20050244934A1 (en) * 2004-04-13 2005-11-03 Brian Foody Recovery of inorganic salt during processing of lignocellulosic feedstocks
WO2006007691A1 (en) * 2004-07-16 2006-01-26 Iogen Energy Corporation Method of obtaining a product sugar stream from cellulosic biomass
US20080041366A1 (en) 2006-08-18 2008-02-21 Iogen Energy Corporation Method of obtaining an organic salt or acid from an aqueous sugar stream

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0409104D0 (en) * 2004-04-23 2004-05-26 Norgine Europe Bv Compressed pharmaceutical compositions

Patent Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US556707A (en) 1896-03-17 steahan
US4522726A (en) 1984-07-30 1985-06-11 Progress Equities Incorporated Advanced separation device and method
US4764276A (en) 1984-07-30 1988-08-16 Advanced Separation Technologies Incorporated Device for continuous contacting of fluids and solids
US4581447A (en) 1984-08-13 1986-04-08 Uop Inc. Process for making a mixture of L-glucose and L-mannose
US4970302A (en) 1989-04-27 1990-11-13 Allied-Signal Inc. Selective catalytic conversion of cyanohydrins to their corresponding aldehydes without concurrent amine formation
US5538637A (en) 1993-09-29 1996-07-23 Tennessee Valley Authority Process for separating acid-sugar mixtures using ion exclusion chromatography
US5628907A (en) * 1993-09-29 1997-05-13 Tennessee Valley Authority Process for separating acid-sugar mixtures using ion exclusion chromatography
US5547817A (en) 1994-10-20 1996-08-20 Fuji Photo Film Co., Ltd. Photographic processing using a novel chelating complex
US5667693A (en) * 1995-02-02 1997-09-16 Tennessee Valley Authority Exclusion chromatographic separation of ionic from nonionic solutes
US5968362A (en) 1997-08-04 1999-10-19 Controlled Enviromental Systems Corporation Method for the separation of acid from sugars
US6391204B1 (en) 1997-08-04 2002-05-21 Controlled Environmental Systems Corporation Method for the separation of acid from sugars
US6419828B1 (en) * 1997-08-04 2002-07-16 Controlled Environmental Systems Corporation Method for the separation of acid from sugars
US5928429A (en) * 1997-10-31 1999-07-27 Imperial Holly Corporation Process for the enhancement of recovery of sugar
JP2004236623A (ja) * 2003-02-07 2004-08-26 Kagawa Univ Ｌ−グルコースの製造方法
US20050244934A1 (en) * 2004-04-13 2005-11-03 Brian Foody Recovery of inorganic salt during processing of lignocellulosic feedstocks
WO2006007691A1 (en) * 2004-07-16 2006-01-26 Iogen Energy Corporation Method of obtaining a product sugar stream from cellulosic biomass
US20080041366A1 (en) 2006-08-18 2008-02-21 Iogen Energy Corporation Method of obtaining an organic salt or acid from an aqueous sugar stream

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
NEUMAN R P ET AL: "Sulfuric acid-sugar separation by ion exclusion", REACTIVE POLYMERS, ION EXCHANGERS, SORBENTS, ELSEVIER, vol. 5, no. 1, 1 January 1987 (1987-01-01), pages 55 - 61, XP024146177, ISSN: 0167-6989, [retrieved on 19870101], DOI: DOI:10.1016/0167-6989(87)90165-6 *
R. A. MEYERS: "Handbook of Petroleum Refining Processes", 1986, MCGRAW-HILL BOOK COMPANY, pages: 8.85 - 8.87
RAYMER G S ET AL: "An open-label trial of L-glucose as a colon-cleansing agent before colonoscopy", GASTROINTESTINAL ENDOSCOPY, ELSEVIER, NL, vol. 58, no. 1, 1 July 2003 (2003-07-01), pages 30 - 35, XP004855636, ISSN: 0016-5107, DOI: DOI:10.1067/MGE.2003.293 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10543460B2 (en) 2013-03-08 2020-01-28 Xyleco, Inc. Upgrading process streams
FR3082756A1 (fr) * 2018-06-26 2019-12-27 Seprosys Procede de separation de molecules ionisees dans une solution en contenant

Also Published As

Publication number Publication date
SG181150A1 (en) 2012-07-30
IL220226A0 (en) 2012-09-24
MX2012006453A (es) 2012-11-23
KR20120112518A (ko) 2012-10-11
CN102725042A (zh) 2012-10-10
BR112012013679A8 (pt) 2016-09-06
AU2010328366A1 (en) 2012-06-21
CA2783198A1 (en) 2011-06-16
CL2012001488A1 (es) 2012-10-12
BR112012013679A2 (pt) 2016-08-16
RU2012125189A (ru) 2014-01-20
JP2013512931A (ja) 2013-04-18
EP2509695A1 (en) 2012-10-17
US20130338086A1 (en) 2013-12-19

Similar Documents

Publication Publication Date Title
EP2401048B1 (en) Separation process
EP1341935B1 (en) Recovering a monosaccharide from a solution using a weakly acid cation exchange resin for the chromatographic separation
EP1106602B1 (en) Simulated moving bed chromatographic purification of amino acids
JP6303017B2 (ja) 芳香族アミノ酸を精製する方法
KR100372962B1 (ko) 용액의분별방법
US8802843B2 (en) Tagatose production using simulated moving bed separation
US5482631A (en) Separation of inositols from sugars and sugar alcohols
EP1490521B1 (en) Separation of sugars, sugar alcohols, carbohydrates and mixtures thereof
EP3041961B1 (en) Chromatographic separation of sugars using blend of cation exchange resins
AU2018343981A1 (en) Process for the purification of a neutral human milk oligosaccharide (HMO) from microbial fermentation
EP2918574A1 (en) Purification of succinic acid from the fermentation broth containing ammonium succinate
WO2014025560A1 (en) Mannose production from palm kernel meal using simulated moving bed separation
US20130338086A1 (en) Methods for purifying monosaccharide mixtures containing ionic impurities
WO2014200942A1 (en) Tagatose production from deproteinized whey and purification by continuous chromatography
Shuey Ion-exchange processes
Janakievski et al. Simulated moving bed chromatography in food processing
WO2024086623A1 (en) Salt and sugar separation process
US20140275518A1 (en) L-glucose production from l-glusose/l-mannose mixtures using simulated moving bed separation
Silva et al. Use of ion exchange resins in continuous chromatography for sugar processing
Heinonen Chromatographic recovery of chemicals from acidic biomass hydrolysates
CN116583339A (zh) 带电荷的寡糖的分离
JPH06253879A (ja) グルクロン酸結合オリゴ糖の分離方法
Wrzosek et al. Chromatography
GrambliCka et al. 7 Chromatography
Dechow 2.12 Industrial Ion Exchange Chromatography

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201080060950.3

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10795131

Country of ref document: EP

Kind code of ref document: A1

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10795131

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2010328366

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 2012542243

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: MX/A/2012/006453

Country of ref document: MX

ENP Entry into the national phase

Ref document number: 2783198

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 12095680

Country of ref document: CO

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2010795131

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 2010328366

Country of ref document: AU

Date of ref document: 20101207

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 5900/CHENP/2012

Country of ref document: IN

ENP Entry into the national phase

Ref document number: 20127017570

Country of ref document: KR

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 2012125189

Country of ref document: RU

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112012013679

Country of ref document: BR

ENP Entry into the national phase

Ref document number: 112012013679

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20120606