BE1000118A6 - Depolymerisation de macromolecules naturelles. - Google Patents

Depolymerisation de macromolecules naturelles. Download PDF

Info

Publication number: BE1000118A6
Authority: BE; Belgium
Prior art keywords: sep; process according; depolymerization; polyanions; free radicals
Prior art date: 1986-08-05

Application number

BE8700861A

Other languages

English (en)

French (fr)

Original Assignee

Ajorca Sa

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.)

1986-08-05

Filing date

1987-08-04

Publication date

1988-04-05

1987-08-04 Application filed by Ajorca Sa filed Critical Ajorca Sa

1988-04-05 Application granted granted Critical

1988-04-05 Publication of BE1000118A6 publication Critical patent/BE1000118A6/fr

Links

229920002521 macromolecule Polymers 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 27
229920000447 polyanionic polymer Polymers 0.000 claims abstract description 14
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 12
238000006243 chemical reaction Methods 0.000 claims abstract description 7
229920002683 Glycosaminoglycan Polymers 0.000 claims abstract description 5
102000039446 nucleic acids Human genes 0.000 claims abstract description 5
108020004707 nucleic acids Proteins 0.000 claims abstract description 5
150000007523 nucleic acids Chemical class 0.000 claims abstract description 4
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims abstract description 3
230000015572 biosynthetic process Effects 0.000 claims abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
230000002378 acidificating effect Effects 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
159000000014 iron salts Chemical class 0.000 claims 1
150000002978 peroxides Chemical class 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 6
239000005445 natural material Substances 0.000 abstract 1
230000001225 therapeutic effect Effects 0.000 abstract 1
229920000669 heparin Polymers 0.000 description 14
229960002897 heparin Drugs 0.000 description 12
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
150000003254 radicals Chemical class 0.000 description 5
KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229920002674 hyaluronan Polymers 0.000 description 4
229960003160 hyaluronic acid Drugs 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229940088598 enzyme Drugs 0.000 description 3
230000010494 opalescence Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
108010014173 Factor X Proteins 0.000 description 2
108010074864 Factor XI Proteins 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003146 anticoagulant agent Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 2
-1 heparin and DS Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 1
208000002177 Cataract Diseases 0.000 description 1
102100022641 Coagulation factor IX Human genes 0.000 description 1
108010076282 Factor IX Proteins 0.000 description 1
108010080865 Factor XII Proteins 0.000 description 1
102000000429 Factor XII Human genes 0.000 description 1
108010024636 Glutathione Proteins 0.000 description 1
208000032843 Hemorrhage Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010061216 Infarction Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
108090000190 Thrombin Proteins 0.000 description 1
206010047249 Venous thrombosis Diseases 0.000 description 1
108010093894 Xanthine oxidase Proteins 0.000 description 1
102100033220 Xanthine oxidase Human genes 0.000 description 1
JNWFIPVDEINBAI-UHFFFAOYSA-N [5-hydroxy-4-[4-(1-methylindol-5-yl)-5-oxo-1H-1,2,4-triazol-3-yl]-2-propan-2-ylphenyl] dihydrogen phosphate Chemical compound C1=C(OP(O)(O)=O)C(C(C)C)=CC(C=2N(C(=O)NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O JNWFIPVDEINBAI-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
238000005273 aeration Methods 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
229940127090 anticoagulant agent Drugs 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
208000034158 bleeding Diseases 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
230000023555 blood coagulation Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000000845 cartilage Anatomy 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000013043 chemical agent Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
229960002433 cysteine Drugs 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
229960004120 defibrotide Drugs 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
125000000600 disaccharide group Chemical group 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
229960004222 factor ix Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
229960003180 glutathione Drugs 0.000 description 1
235000003969 glutathione Nutrition 0.000 description 1
239000002565 heparin fraction Substances 0.000 description 1
229960001008 heparin sodium Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000000988 hyperfibrinolytic effect Effects 0.000 description 1
230000003308 immunostimulating effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000007574 infarction Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
229940127215 low-molecular weight heparin Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229940124276 oligodeoxyribonucleotide Drugs 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006479 redox reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
229960004072 thrombin Drugs 0.000 description 1
206010043554 thrombocytopenia Diseases 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000011282 treatment Methods 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
210000004127 vitreous body Anatomy 0.000 description 1
229940075420 xanthine Drugs 0.000 description 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
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
- C08B37/0078—Degradation products

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

BE8700861A 1986-08-05 1987-08-04 Depolymerisation de macromolecules naturelles. BE1000118A6 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AR86304799A AR243540A1 (es)	1986-08-05	1986-08-05	Procedimiento quimico para la depolimerizacion controlada de polianiones naturales y productos asi obtenidos, excluidos sus usos farmaceuticos.

Publications (1)

Publication Number	Publication Date
BE1000118A6 true BE1000118A6 (fr)	1988-04-05

Family

ID=3478429

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE8700861A BE1000118A6 (fr)	1986-08-05	1987-08-04	Depolymerisation de macromolecules naturelles.

Country Status (7)

Country	Link
CN (1)	CN87105497A (it)
AR (1)	AR243540A1 (it)
BE (1)	BE1000118A6 (it)
CH (1)	CH678326A5 (it)
ES (1)	ES2007373A6 (it)
IT (1)	IT1224260B (it)
SU (1)	SU1639432A3 (it)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1993007178A1 (fr) *	1991-10-10	1993-04-15	Pasteur Merieux Serums Et Vaccins	Oligoside derive d'un polyoside antigenique issu d'un agent pathogene

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7700764B2 (en)	2005-06-28	2010-04-20	Akzo Nobel N.V.	Method of preparing microfibrillar polysaccharide
RU2404194C2 (ru) *	2005-06-28	2010-11-20	Акцо Нобель Н.В.	Способ получения микроволокнистого полисахарида
IT202000004564A1 (it)	2020-03-04	2021-09-04	Lesaffre & Cie	Processo per la solfatazione diretta di polisaccaridi in solvente ecologicamente accettabile
CN115583998B (zh) *	2022-09-23	2023-08-01	江苏蓝果临床营养科技有限公司	一种低分子量硫酸软骨素-铁的制备方法

1986
- 1986-08-05 AR AR86304799A patent/AR243540A1/es active
1987
- 1987-07-24 ES ES8702175A patent/ES2007373A6/es not_active Expired
- 1987-07-30 IT IT48253/87A patent/IT1224260B/it active
- 1987-07-31 CH CH2953/87A patent/CH678326A5/it not_active IP Right Cessation
- 1987-08-03 SU SU874203197A patent/SU1639432A3/ru active
- 1987-08-04 BE BE8700861A patent/BE1000118A6/fr not_active IP Right Cessation
- 1987-08-05 CN CN198787105497A patent/CN87105497A/zh active Pending

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1993007178A1 (fr) *	1991-10-10	1993-04-15	Pasteur Merieux Serums Et Vaccins	Oligoside derive d'un polyoside antigenique issu d'un agent pathogene
FR2682388A1 (fr) *	1991-10-10	1993-04-16	Pasteur Merieux Serums Vacc	Procede de preparation d'un oligoside par depolymerisation d'un polyoside issu d'un agent pathogene, oligoside ainsi obtenu et son utilisation notamment comme agent vaccinal.
US6045805A (en) *	1991-10-10	2000-04-04	Pasteur Merieux Serums Et Vaccines	Oligosaccharide derived from an antigenic polysaccharide obtained from a pathogenic agent

Also Published As

Publication number	Publication date
SU1639432A3 (ru)	1991-03-30
CH678326A5 (en)	1991-08-30
ES2007373A6 (es)	1989-06-16
IT1224260B (it)	1990-10-04
CN87105497A (zh)	1988-04-13
IT8748253A0 (it)	1987-07-30
AR243540A1 (es)	1993-08-31

Legal Events

Date

Code

Title

Description

1993-01-01

RE20

Patent expired

Owner name: S.A. AJORCA

Effective date: 19930804

Publication	Publication Date	Title
FR2474508A1 (fr)	1981-07-31	Procede pour obtenir des heparines de bas poids moleculaire ayant des proprietes pharmacologiques remarquables et produit ainsi obtenu
CA2416673C (fr)	2011-06-14	Melanges de polysaccharides derives d'heparine, leur preparation et les compositions pharmaceutiques les contenant
CA2501546C (fr)	2012-04-03	Melanges de polysaccharides derives d'heparine, leur preparation et les compositions pharmaceutiques les contenant
CA1327968C (fr)	1994-03-22	Heparines de bas poids moleculaire, a structure reguliere leur preparation et leurs applications biologiques
EP0116801B1 (fr)	1987-04-01	Héparine dépolymérisée et supersulfatée, procédé pour sa préparation et compositions pharmaceutiques en contenant
JP3287363B2 (ja)	2002-06-04	低分子量多糖類の混合物、及びその製造と利用
Novosel'Skaya et al.	2000	Trends in the science and applications of pectins
EP0037319B1 (fr)	1987-04-08	Mucopolysaccharides possédant des propriétés biologiques, leur préparation et leur application en tant que médicaments
BE1000118A6 (fr)	1988-04-05	Depolymerisation de macromolecules naturelles.
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CA2914256C (en)	2021-03-02	New processes for the production of chemically-modified heparins
CN101475969A (zh)	2009-07-08	木瓜蛋白酶降解壳聚糖的方法
Chatzigeorgiou et al.	2023	Preparation of hyaluronan oligosaccharides by a prokaryotic beta-glucuronidase: Characterization of free and immobilized forms of the enzyme
EP0101141A2 (en)	1984-02-22	Process for manufacturing low molecular weight heparins by depolymerization of normal heparin
CN1246338C (zh)	2006-03-22	琼胶多糖的降解方法
CA2533555A1 (fr)	2005-02-03	Melanges d'oligosaccharides derives d'heparine, leur preparation et les compositions pharmaceutiques les contenant
TW200838552A (en)	2008-10-01	Methyl esters of hyaluronic acid
EP4360638B1 (en)	2025-11-12	Application of sulfate gluco-galacto-oligosaccharide in preparation of anticoagulant and/or antithrombotic drug
WO1990008784A1 (fr)	1990-08-09	Nouveau polysaccharide sulfate, ses sels pharmaceutiquement acceptables, sa preparation, et medicament le contenant a titre d'ingredient actif
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US3141014A (en)	1964-07-14	Sodium and potassium salts of the dextran sulphuric acid ester having substantially no anticoagulant activity but having lipolytic activity and the method of preparation thereof
JPH0128044B2 (it)	1989-05-31
FR3047179A1 (fr)	2017-08-04	Ulvanes sulfates et utilisation dans la regulation des troubles de la coagulation
JPH0552841B2 (it)	1993-08-06
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