NO820136L - Fremgangsmaate for fremstilling av forbedret antikoagulerende substans - Google Patents

Fremgangsmaate for fremstilling av forbedret antikoagulerende substans

Info

Publication number: NO820136L
Authority: NO; Norway
Prior art keywords: heparin; molecular weight; average molecular; acid; sodium chloride
Prior art date: 1980-05-19

Application number

NO820136A

Other languages

English (en)

Norwegian (no)

Inventor

William E Barnett

Original Assignee

Riker Laboratories 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.)

1980-05-19

Filing date

1982-01-18

Publication date

1982-01-18

1982-01-18 Application filed by Riker Laboratories Inc filed Critical Riker Laboratories Inc

1982-01-18 Publication of NO820136L publication Critical patent/NO820136L/no

Links

238000000034 method Methods 0.000 title claims description 35
239000000126 substance Substances 0.000 title claims description 6
230000002429 anti-coagulating effect Effects 0.000 title description 5
238000002360 preparation method Methods 0.000 title description 2
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 claims description 80
229920000669 heparin Polymers 0.000 claims description 80
229960002897 heparin Drugs 0.000 claims description 73
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 44
239000000243 solution Substances 0.000 claims description 31
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 22
229910017604 nitric acid Inorganic materials 0.000 claims description 22
239000011780 sodium chloride Substances 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 16
238000004128 high performance liquid chromatography Methods 0.000 claims description 15
229920002307 Dextran Polymers 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 7
238000012691 depolymerization reaction Methods 0.000 claims description 7
239000003055 low molecular weight heparin Substances 0.000 claims description 6
230000014759 maintenance of location Effects 0.000 claims description 6
IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 5
239000008280 blood Substances 0.000 claims description 3
210000004369 blood Anatomy 0.000 claims description 3
229940097043 glucuronic acid Drugs 0.000 claims description 3
230000002401 inhibitory effect Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims 1
AEMOLEFTQBMNLQ-HNFCZKTMSA-N L-idopyranuronic acid Chemical compound OC1O[C@@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-HNFCZKTMSA-N 0.000 claims 1
230000015271 coagulation Effects 0.000 claims 1
238000005345 coagulation Methods 0.000 claims 1
239000000047 product Substances 0.000 description 42
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 18
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 18
229920000642 polymer Polymers 0.000 description 16
230000000694 effects Effects 0.000 description 15
230000002785 anti-thrombosis Effects 0.000 description 14
239000003146 anticoagulant agent Substances 0.000 description 11
235000010288 sodium nitrite Nutrition 0.000 description 9
230000002008 hemorrhagic effect Effects 0.000 description 8
238000012360 testing method Methods 0.000 description 8
231100001274 therapeutic index Toxicity 0.000 description 8
238000002474 experimental method Methods 0.000 description 7
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 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
208000032843 Hemorrhage Diseases 0.000 description 5
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 5
-1 alkaline earth metal salt Chemical class 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
IAJILQKETJEXLJ-LECHCGJUSA-N iduronic acid Chemical compound O=C[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-LECHCGJUSA-N 0.000 description 5
229910052722 tritium Inorganic materials 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
229940127219 anticoagulant drug Drugs 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000000463 material Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000036961 partial effect Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
230000000740 bleeding effect Effects 0.000 description 3
230000008034 disappearance Effects 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
150000002772 monosaccharides Chemical group 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-KVTDHHQDSA-N 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
229920002683 Glycosaminoglycan Polymers 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
208000007536 Thrombosis Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 2
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
230000023555 blood coagulation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
238000005194 fractionation Methods 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
150000002301 glucosamine derivatives Chemical class 0.000 description 2
150000008273 hexosamines Chemical group 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
230000002265 prevention Effects 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
238000011282 treatment Methods 0.000 description 2
LKAPTZKZHMOIRE-KVTDHHQDSA-N (2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbaldehyde Chemical compound OC[C@H]1O[C@H](C=O)[C@@H](O)[C@@H]1O LKAPTZKZHMOIRE-KVTDHHQDSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000283153 Cetacea Species 0.000 description 1
108010022901 Heparin Lyase Proteins 0.000 description 1
229920001499 Heparinoid Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
241001494479 Pecora Species 0.000 description 1
241000282887 Suidae Species 0.000 description 1
206010047249 Venous thrombosis Diseases 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
239000001166 ammonium sulphate Substances 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
GJTDJAPHKDIQIQ-UHFFFAOYSA-L barium(2+);dinitrite Chemical compound [Ba+2].[O-]N=O.[O-]N=O GJTDJAPHKDIQIQ-UHFFFAOYSA-L 0.000 description 1
239000002585 base Substances 0.000 description 1
208000034158 bleeding Diseases 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
LKAPTZKZHMOIRE-UHFFFAOYSA-N chitose Natural products OCC1OC(C=O)C(O)C1O LKAPTZKZHMOIRE-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000002651 drug therapy Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000013100 final test Methods 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000004676 glycans Polymers 0.000 description 1
150000002337 glycosamines Chemical class 0.000 description 1
239000002565 heparin fraction Substances 0.000 description 1
239000002554 heparinoid Substances 0.000 description 1
229940025770 heparinoids Drugs 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
229950006780 n-acetylglucosamine Drugs 0.000 description 1
230000014508 negative regulation of coagulation Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
YBVAXJOZZAJCLA-UHFFFAOYSA-N nitric acid nitrous acid Chemical compound ON=O.O[N+]([O-])=O YBVAXJOZZAJCLA-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
150000004804 polysaccharides Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000005670 sulfation reaction Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005199 ultracentrifugation Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- 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

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Materials Engineering (AREA)
Epidemiology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Saccharide Compounds (AREA)

NO820136A 1980-05-19 1982-01-18 Fremgangsmaate for fremstilling av forbedret antikoagulerende substans NO820136L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/151,163 US4351938A (en)	1980-05-19	1980-05-19	Anticoagulant substance

Publications (1)

Publication Number	Publication Date
NO820136L true NO820136L (no)	1982-01-18

Family

ID=22537581

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO820136A NO820136L (no)	1980-05-19	1982-01-18	Fremgangsmaate for fremstilling av forbedret antikoagulerende substans

Country Status (9)

Country	Link
US (1)	US4351938A (da)
EP (1)	EP0053612A1 (da)
JP (1)	JPS57500612A (da)
BE (1)	BE888864A (da)
DK (1)	DK18982A (da)
IT (1)	IT1136601B (da)
NO (1)	NO820136L (da)
WO (1)	WO1981003276A1 (da)
ZA (1)	ZA813321B (da)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
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FR2440376A1 (fr) *	1978-11-06	1980-05-30	Choay Sa	Composition mucopolysaccharidique ayant une activite regulatrice de la coagulation, medicament la contenant et procede pour l'obtenir
US4500519A (en) *	1978-11-06	1985-02-19	Choay S.A.	Mucopolysaccharides having biological properties, preparation and method of use
FR2503714B1 (fr) *	1981-04-10	1986-11-21	Choay Sa	Procede d'obtention de mucopolysaccharides biologiquement actifs, de purete elevee, par depolymerisation de l'heparine
DE3265781D1 (en)	1981-05-21	1985-10-03	Akzo Nv	New anti-thromboticum based on polysacharides, method for its preparation and pharmaceutical compositions
US4539398A (en) *	1982-01-22	1985-09-03	Riker Laboratories, Inc.	Affinity fractionation of heparin on immobilized Concanavalin A
DE98814T1 (de)	1982-06-10	1984-06-20	Kabivitrum Ab, 11287 Stockholm	Antithrombin-heparin komplex.
IT1195497B (it) *	1983-03-08	1988-10-19	Opocrin Spa	Procedimento per la preparazione di frazioni oligosaccaridiche dotate di proprieta' farmacologiche per degradazione chimica di eparina
IT1169888B (it) *	1983-10-25	1987-06-03	Italfarmaco Spa	Glicosaminoglicani modificati dotati di attivita' antitrombotica
DK196886D0 (da) *	1986-04-30	1986-04-30	Novo Industri As	Fremstilling af polysaccharider
DK196986D0 (da) *	1986-04-30	1986-04-30	Novo Industri As	Fremstilling af polysaccharider
US4745106A (en) *	1986-08-20	1988-05-17	Griffin Charles C	Heparin derivatives having improved anti-Xa specificity
US4942156A (en) *	1986-08-20	1990-07-17	Hepar Industries, Inc.	Low molecular weight heparin derivatives having improved anti-Xa specificity
IT1213384B (it) *	1986-11-24	1989-12-20	Lab Derivati Organici Mediolan	Processo per la preparazione controllata di gilcosaminoglicani a basso peso molecolare.
EP0337327A1 (en) *	1988-04-09	1989-10-18	Bioiberica, S.A.	Process for the preparation of new oligosaccharide fractions by controlled chemical depolimerization of heparin
IT1230582B (it)	1988-10-21	1991-10-28	Opocrin S P A Lab Farmabiologi	Oliogosaccaridi di dermatan solfato ed eparina aventi attivita' antiaterosclerotica
JP2871822B2 (ja) *	1989-08-29	1999-03-17	玉造株式会社	末端に２，５―アンヒドロマンニトール基または２，５―アンヒドロマンノース基を有するキチン・キトサンオリゴマーおよびその製造方法
FR2663639B1 (fr) *	1990-06-26	1994-03-18	Rhone Poulenc Sante	Melanges de polysaccharides de bas poids moleculaires procede de preparation et utilisation.
USRE38743E1 (en)	1990-06-26	2005-06-14	Aventis Pharma S.A.	Mixtures of particular LMW heparinic polysaccharides for the prophylaxis/treatment of acute thrombotic events
DE4217917A1 (de) *	1992-05-30	1993-12-02	Job Prof Dr Med Harenberg	Immobilisation von chemisch kovalent gebundenem Heparin an Polymere mit Arylresten im Polymer
FR2704861B1 (fr) *	1993-05-07	1995-07-28	Sanofi Elf	Fractions d'héparine purifiées, procédé d'obtention et compositions pharmaceutiques les contenant.
US5744457A (en) *	1995-03-31	1998-04-28	Hamilton Civic Hospitals Research Development Inc.	Compositions and methods for inhibiting thrombogenesis
US5763427A (en) *	1995-03-31	1998-06-09	Hamilton Civic Hospitals Research Development Inc.	Compositions and methods for inhibiting thrombogenesis
US6001820A (en) *	1995-03-31	1999-12-14	Hamilton Civic Hospitals Research Development Inc.	Compositions and methods for inhibiting thrombogenesis
US5767269A (en) *	1996-10-01	1998-06-16	Hamilton Civic Hospitals Research Development Inc.	Processes for the preparation of low-affinity, low molecular weight heparins useful as antithrombotics
IL129877A (en) *	1996-11-27	2004-08-31	Aventis Pharm Prod Inc	A pharmaceutical preparation containing a component having an Xa antagonist activity and an antifouling agent
IT1312107B1 (it) *	1999-05-14	2002-04-04	Umberto Cornelli	Glicosaminoglicani aventi peso molecolare medio di 2400 d atti altrattamento della demenza senile
ITMI20031023A1 (it) *	2003-05-21	2004-11-22	Umberto Cornelli	Glicosaminoglicani aventi peso molecolare medio 2400 d atti al trattamento delle disfunzioni emozionali.
EP1582531A1 (en)	2004-03-24	2005-10-05	Aventis Pharma S.A.	Process for oxidizing unfractionated heparins and detecting presence or absence of glycoserine in heparin and heparin products
ITMO20040199A1 (it) *	2004-07-29	2004-10-29	Biofer Spa	Procedimento per la purificazione da gruppi e n no rsidui di eparine a basso peso molecolare ottentite tramite nitrosazione.
ES2292351B1 (es) *	2006-07-14	2009-03-01	Laboratorios Farmaceuticos Rovi, S.A.	Procedimiento nuevo de despolimerizacion de la heparina.
US20110112050A1 (en) *	2008-05-20	2011-05-12	Crystal Clear Partnership	Separation of polysaccharides by charge density gradient
CN103214591B (zh)	2013-04-12	2015-11-04	中国科学院昆明植物研究所	一种含末端2,5-脱水塔罗糖或其衍生物的低分子量糖胺聚糖衍生物
CN103315951B (zh) *	2013-07-17	2014-10-08	海南通用同盟药业有限公司	低分子肝素钙注射剂
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1980
- 1980-05-19 US US06/151,163 patent/US4351938A/en not_active Expired - Lifetime
1981
- 1981-04-17 JP JP56501646A patent/JPS57500612A/ja active Pending
- 1981-04-17 WO PCT/US1981/000519 patent/WO1981003276A1/en not_active Ceased
- 1981-04-17 EP EP81901249A patent/EP0053612A1/en not_active Withdrawn
- 1981-05-18 ZA ZA00813321A patent/ZA813321B/xx unknown
- 1981-05-18 IT IT21785/81A patent/IT1136601B/it active
- 1981-05-19 BE BE0/204833A patent/BE888864A/fr not_active IP Right Cessation
1982
- 1982-01-18 NO NO820136A patent/NO820136L/no unknown
- 1982-01-18 DK DK18982A patent/DK18982A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK18982A (da)	1982-01-18
US4351938A (en)	1982-09-28
IT8121785A0 (it)	1981-05-18
JPS57500612A (da)	1982-04-08
WO1981003276A1 (en)	1981-11-26
BE888864A (fr)	1981-11-19
IT1136601B (it)	1986-09-03
ZA813321B (en)	1982-05-26
EP0053612A1 (en)	1982-06-16

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