GB854715A - Process for the manufacture of hydrophilic high molecular weight substances from dextran substances - Google Patents
Process for the manufacture of hydrophilic high molecular weight substances from dextran substancesInfo
- Publication number
- GB854715A GB854715A GB188359A GB188359A GB854715A GB 854715 A GB854715 A GB 854715A GB 188359 A GB188359 A GB 188359A GB 188359 A GB188359 A GB 188359A GB 854715 A GB854715 A GB 854715A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dextran
- products
- substances
- ether
- substance
- 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.)
- Expired
Links
- 229920002307 Dextran Polymers 0.000 title abstract 14
- 239000000126 substance Substances 0.000 title abstract 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 abstract 11
- 239000000047 product Substances 0.000 abstract 6
- -1 dextran glycerine glycoside Chemical class 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 230000001588 bifunctional effect Effects 0.000 abstract 2
- 229930182470 glycoside Natural products 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 abstract 1
- AZUXKVXMJOIAOF-UHFFFAOYSA-N 1-(2-hydroxypropoxy)propan-2-ol Chemical class CC(O)COCC(C)O AZUXKVXMJOIAOF-UHFFFAOYSA-N 0.000 abstract 1
- LSTZTHCEEPHCNQ-UHFFFAOYSA-N 3-(2,5-dioxabicyclo[2.1.0]pentan-3-yloxy)-2,5-dioxabicyclo[2.1.0]pentane Chemical compound C1(C2C(O2)O1)OC1C2C(O2)O1 LSTZTHCEEPHCNQ-UHFFFAOYSA-N 0.000 abstract 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 150000007824 aliphatic compounds Chemical class 0.000 abstract 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000000502 dialysis Methods 0.000 abstract 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 abstract 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000000499 gel Substances 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000001802 infusion Methods 0.000 abstract 1
- 238000010253 intravenous injection Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003058 plasma substitute Substances 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 230000008961 swelling Effects 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
-
- 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
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/22—Cellulose or wood; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
High molecular weight hydrophilic substances from dextran are obtained by reacting a hydroxyl group containing dextran substance with a bifunctional aliphatic compound containing from 1 to 10 carbon atoms, the chain of carbon atoms of which may be interrupted by ether groups and containing halogen and/or epoxy groups at the ends of the chain, which react with the hydroxyl groups of the dextran with formation of linkages of ether type, so that a polymerization product containing at least 2 of the molecules of the dextran substance bound together by ether bridges is obtained. The "dextran substances" include native or partially depolymerized dextran, ethyl, hydroxyethyl or 2-hydroxypropyl ethers of dextran, dextran glycerine glycoside, hydrodextran, or dextrans containing carboxyl, sulphonic or amino groups. Suitable bifunctional compounds are epichlorohydrin, dichlorohydrin, epibromohydrin, dibromohydrin, 1, 2, 3, 4-diepoxybutane, diepoxypropyl ether, diepoxypropyl ethers of ethylene glycol, propylene glycol and polyethylene glycols. The reaction may be effected in the presence of water or an organic solvent such as dimethylformamide, and an alkaline reacting substance such as alkali metal or alkaline earth metal hydroxides, or tertiary and quaternary amines. The temperature may vary widely but is preferably between room temperature and a temperature of 60-90 DEG C. The products obtained may be water-soluble and may be purified by precipitation with alcohols or ketones, extraction with water containing non-solvents, using ion exchangers or by dialysis. The products may also be gels which are insoluble but capable of absorbing solvent with swelling and may be purified by washing with water or solvents. The products may be subjected to partial depolymerization for correcting the average molecular weight, such as by mild hydrolysis with an acid, or alcoholysis. The products may be used for theropeutic and pharmaceutical purposes.ALSO:Hydrophilic polymerization products containing at least 2 molecules of dextran substance (i.e. native dextran, partially depolymerized dextran or derivatives thereof such as ethers glycosides or hydrodextran) bound together with ether bridges via an aliphatic radical containing 1 to 10 carbon atoms are used as plasma substitute and as disintegrating agents for tablets. In an example, a colloidal infusion for intravenous injection comprises 6% of a fraction obtained from the reaction product of dextran and epichlorohydrin, and 0,9% sodium chloride. For preparation of the polymers see Group IV(a).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE245258A SE169293C1 (en) | 1958-03-13 | 1958-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB854715A true GB854715A (en) | 1960-11-23 |
Family
ID=20259979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB188359A Expired GB854715A (en) | 1958-03-13 | 1959-01-19 | Process for the manufacture of hydrophilic high molecular weight substances from dextran substances |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE576522A (en) |
| CH (1) | CH413811A (en) |
| DE (1) | DE1418013A1 (en) |
| GB (1) | GB854715A (en) |
| SE (1) | SE169293C1 (en) |
Cited By (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3208994A (en) * | 1961-10-25 | 1965-09-28 | Pharmacia Ab | Process for preparing hydrophilic copolymerization and product obtained thereby |
| DE2403269A1 (en) * | 1973-01-29 | 1974-08-08 | Pharmacia Ab | PRODUCTS FOR CLEANING LIQUID SKIN SURFACES, WOUNDS AND MUCCOUS |
| DE3033885A1 (en) * | 1979-09-12 | 1981-04-02 | Pharmacia Fine Chemicals AB, Uppsala | METHOD FOR BREEDING CELLS |
| US4470975A (en) * | 1977-10-21 | 1984-09-11 | The Johns Hopkins University | Method and composition for the elimination of water from an animal body |
| US4537767A (en) * | 1973-01-29 | 1985-08-27 | Pharmacia Aktiebolag | Method for cleansing fluid discharging skin surfaces, wounds and mucous membranes and means for carrying out the method |
| JPH0669490B2 (en) * | 1984-07-23 | 1994-09-07 | カビ・フアーマシア・アー・ベー | Implant for preventing adhesion between body tissues and method for producing the same |
| US5585007A (en) * | 1994-12-07 | 1996-12-17 | Plasmaseal Corporation | Plasma concentrate and tissue sealant methods and apparatuses for making concentrated plasma and/or tissue sealant |
| WO2001017571A1 (en) * | 1999-09-03 | 2001-03-15 | Sulzer Vascutek Limited | Sealant for vascular prostheses |
| US7101862B2 (en) | 2001-12-31 | 2006-09-05 | Area Laboratories, Llc | Hemostatic compositions and methods for controlling bleeding |
| US7374678B2 (en) | 2002-05-24 | 2008-05-20 | Biomet Biologics, Inc. | Apparatus and method for separating and concentrating fluids containing multiple components |
| US7470371B2 (en) | 2002-05-03 | 2008-12-30 | Hanuman Llc | Methods and apparatus for isolating platelets from blood |
| US7708152B2 (en) | 2005-02-07 | 2010-05-04 | Hanuman Llc | Method and apparatus for preparing platelet rich plasma and concentrates thereof |
| US7780860B2 (en) | 2002-05-24 | 2010-08-24 | Biomet Biologics, Llc | Apparatus and method for separating and concentrating fluids containing multiple components |
| US7806276B2 (en) | 2007-04-12 | 2010-10-05 | Hanuman, Llc | Buoy suspension fractionation system |
| US7824559B2 (en) | 2005-02-07 | 2010-11-02 | Hanumann, LLC | Apparatus and method for preparing platelet rich plasma and concentrates thereof |
| US7832566B2 (en) | 2002-05-24 | 2010-11-16 | Biomet Biologics, Llc | Method and apparatus for separating and concentrating a component from a multi-component material including macroparticles |
| US7845499B2 (en) | 2002-05-24 | 2010-12-07 | Biomet Biologics, Llc | Apparatus and method for separating and concentrating fluids containing multiple components |
| US7866485B2 (en) | 2005-02-07 | 2011-01-11 | Hanuman, Llc | Apparatus and method for preparing platelet rich plasma and concentrates thereof |
| US7992725B2 (en) | 2002-05-03 | 2011-08-09 | Biomet Biologics, Llc | Buoy suspension fractionation system |
| US8012077B2 (en) | 2008-05-23 | 2011-09-06 | Biomet Biologics, Llc | Blood separating device |
| US8187475B2 (en) | 2009-03-06 | 2012-05-29 | Biomet Biologics, Llc | Method and apparatus for producing autologous thrombin |
| US8313954B2 (en) | 2009-04-03 | 2012-11-20 | Biomet Biologics, Llc | All-in-one means of separating blood components |
| US8328024B2 (en) | 2007-04-12 | 2012-12-11 | Hanuman, Llc | Buoy suspension fractionation system |
| US8337711B2 (en) | 2008-02-29 | 2012-12-25 | Biomet Biologics, Llc | System and process for separating a material |
| WO2013019891A1 (en) | 2011-08-01 | 2013-02-07 | St. Hill Pharmaceutical Corporation | Non-digestible capsules for the delivery of fluid absorbing materials |
| US8567609B2 (en) | 2006-05-25 | 2013-10-29 | Biomet Biologics, Llc | Apparatus and method for separating and concentrating fluids containing multiple components |
| US8591391B2 (en) | 2010-04-12 | 2013-11-26 | Biomet Biologics, Llc | Method and apparatus for separating a material |
| US9011800B2 (en) | 2009-07-16 | 2015-04-21 | Biomet Biologics, Llc | Method and apparatus for separating biological materials |
| US9556243B2 (en) | 2013-03-15 | 2017-01-31 | Biomet Biologies, LLC | Methods for making cytokine compositions from tissues using non-centrifugal methods |
| US9642956B2 (en) | 2012-08-27 | 2017-05-09 | Biomet Biologics, Llc | Apparatus and method for separating and concentrating fluids containing multiple components |
| US9701728B2 (en) | 2008-02-27 | 2017-07-11 | Biomet Biologics, Llc | Methods and compositions for delivering interleukin-1 receptor antagonist |
| US9713810B2 (en) | 2015-03-30 | 2017-07-25 | Biomet Biologics, Llc | Cell washing plunger using centrifugal force |
| US9757721B2 (en) | 2015-05-11 | 2017-09-12 | Biomet Biologics, Llc | Cell washing plunger using centrifugal force |
| US9897589B2 (en) | 2002-05-24 | 2018-02-20 | Biomet Biologics, Llc | Apparatus and method for separating and concentrating fluids containing multiple components |
| US9895418B2 (en) | 2013-03-15 | 2018-02-20 | Biomet Biologics, Llc | Treatment of peripheral vascular disease using protein solutions |
| US9950035B2 (en) | 2013-03-15 | 2018-04-24 | Biomet Biologics, Llc | Methods and non-immunogenic compositions for treating inflammatory disorders |
| US10143725B2 (en) | 2013-03-15 | 2018-12-04 | Biomet Biologics, Llc | Treatment of pain using protein solutions |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE452469B (en) * | 1986-06-18 | 1987-11-30 | Pharmacia Ab | MATERIALS CONSISTING OF A CROSS-BONDED CARBOXYL-GROUPED POLYSACCHARIDE AND PROCEDURE IN THE PREPARATION OF THE SAME |
-
1958
- 1958-03-13 SE SE245258A patent/SE169293C1/xx unknown
-
1959
- 1959-01-19 GB GB188359A patent/GB854715A/en not_active Expired
- 1959-03-10 BE BE576522A patent/BE576522A/en unknown
- 1959-03-12 DE DE19591418013 patent/DE1418013A1/en active Pending
- 1959-03-12 CH CH7074659A patent/CH413811A/en unknown
Cited By (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3208994A (en) * | 1961-10-25 | 1965-09-28 | Pharmacia Ab | Process for preparing hydrophilic copolymerization and product obtained thereby |
| DE2403269A1 (en) * | 1973-01-29 | 1974-08-08 | Pharmacia Ab | PRODUCTS FOR CLEANING LIQUID SKIN SURFACES, WOUNDS AND MUCCOUS |
| US4537767A (en) * | 1973-01-29 | 1985-08-27 | Pharmacia Aktiebolag | Method for cleansing fluid discharging skin surfaces, wounds and mucous membranes and means for carrying out the method |
| US4470975A (en) * | 1977-10-21 | 1984-09-11 | The Johns Hopkins University | Method and composition for the elimination of water from an animal body |
| DE3033885A1 (en) * | 1979-09-12 | 1981-04-02 | Pharmacia Fine Chemicals AB, Uppsala | METHOD FOR BREEDING CELLS |
| JPH0669490B2 (en) * | 1984-07-23 | 1994-09-07 | カビ・フアーマシア・アー・ベー | Implant for preventing adhesion between body tissues and method for producing the same |
| US5585007A (en) * | 1994-12-07 | 1996-12-17 | Plasmaseal Corporation | Plasma concentrate and tissue sealant methods and apparatuses for making concentrated plasma and/or tissue sealant |
| US6214338B1 (en) | 1994-12-07 | 2001-04-10 | Plasmaseal Llc | Plasma concentrate and method of processing blood for same |
| WO2001017571A1 (en) * | 1999-09-03 | 2001-03-15 | Sulzer Vascutek Limited | Sealant for vascular prostheses |
| US7101862B2 (en) | 2001-12-31 | 2006-09-05 | Area Laboratories, Llc | Hemostatic compositions and methods for controlling bleeding |
| US7992725B2 (en) | 2002-05-03 | 2011-08-09 | Biomet Biologics, Llc | Buoy suspension fractionation system |
| US7837884B2 (en) | 2002-05-03 | 2010-11-23 | Hanuman, Llc | Methods and apparatus for isolating platelets from blood |
| US8950586B2 (en) | 2002-05-03 | 2015-02-10 | Hanuman Llc | Methods and apparatus for isolating platelets from blood |
| US8187477B2 (en) | 2002-05-03 | 2012-05-29 | Hanuman, Llc | Methods and apparatus for isolating platelets from blood |
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| US8603346B2 (en) | 2002-05-24 | 2013-12-10 | Biomet Biologics, Llc | Apparatus and method for separating and concentrating fluids containing multiple components |
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Also Published As
| Publication number | Publication date |
|---|---|
| DE1418013A1 (en) | 1968-10-17 |
| SE169293C1 (en) | 1959-11-10 |
| BE576522A (en) | 1959-09-10 |
| CH413811A (en) | 1966-05-31 |
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