NO811631L - Heparinestere og deres fremstilling. - Google Patents
Heparinestere og deres fremstilling.Info
- Publication number
- NO811631L NO811631L NO811631A NO811631A NO811631L NO 811631 L NO811631 L NO 811631L NO 811631 A NO811631 A NO 811631A NO 811631 A NO811631 A NO 811631A NO 811631 L NO811631 L NO 811631L
- Authority
- NO
- Norway
- Prior art keywords
- heparin
- esters
- quaternary ammonium
- salt
- carboxyl groups
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 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 abstract description 106
- 229920000669 heparin Polymers 0.000 claims abstract description 97
- 229960002897 heparin Drugs 0.000 claims abstract description 80
- -1 phenyl- Chemical group 0.000 claims abstract description 53
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 41
- 150000002148 esters Chemical class 0.000 claims abstract description 37
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 26
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 18
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 15
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 230000032050 esterification Effects 0.000 claims abstract description 13
- 238000005886 esterification reaction Methods 0.000 claims abstract description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 12
- 239000011777 magnesium Substances 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 239000007864 aqueous solution Substances 0.000 claims description 28
- SIYLLGKDQZGJHK-UHFFFAOYSA-N dimethyl-(phenylmethyl)-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethyl]ammonium Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 SIYLLGKDQZGJHK-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 18
- 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 14
- 239000002253 acid Substances 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 14
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 6
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000001718 carbodiimides Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- AEMOLEFTQBMNLQ-CLQWQSTFSA-N l-iduronic acid Chemical class O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O AEMOLEFTQBMNLQ-CLQWQSTFSA-N 0.000 claims description 4
- 159000000003 magnesium salts Chemical class 0.000 claims description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- 239000000243 solution Substances 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 25
- 159000000000 sodium salts Chemical class 0.000 description 21
- 238000001914 filtration Methods 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- 229960003872 benzethonium Drugs 0.000 description 16
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 14
- 239000001632 sodium acetate Substances 0.000 description 14
- 235000017281 sodium acetate Nutrition 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 230000014508 negative regulation of coagulation Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 229960001950 benzethonium chloride Drugs 0.000 description 2
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 210000003097 mucus Anatomy 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 210000001835 viscera Anatomy 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical class CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 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
-
- 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)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8010792A FR2482603A1 (fr) | 1980-05-14 | 1980-05-14 | Nouveaux esters d'heparine utilisables pour la preparation de medicaments, et procedes pour leur preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO811631L true NO811631L (no) | 1981-11-16 |
Family
ID=9241966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811631A NO811631L (no) | 1980-05-14 | 1981-05-13 | Heparinestere og deres fremstilling. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4440926A (pt) |
| EP (1) | EP0044228B1 (pt) |
| JP (1) | JPS5952163B2 (pt) |
| KR (1) | KR840000724B1 (pt) |
| AU (1) | AU543032B2 (pt) |
| CA (1) | CA1183132A (pt) |
| DE (1) | DE3168868D1 (pt) |
| DK (1) | DK189581A (pt) |
| ES (1) | ES8206556A1 (pt) |
| FI (1) | FI811470L (pt) |
| FR (1) | FR2482603A1 (pt) |
| GR (1) | GR73918B (pt) |
| IE (1) | IE51348B1 (pt) |
| IL (1) | IL62850A (pt) |
| IN (1) | IN153355B (pt) |
| MA (1) | MA19144A1 (pt) |
| NO (1) | NO811631L (pt) |
| NZ (1) | NZ197021A (pt) |
| PT (1) | PT72995B (pt) |
| ZA (1) | ZA813175B (pt) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4851521A (en) * | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
| US5202431A (en) * | 1985-07-08 | 1993-04-13 | Fidia, S.P.A. | Partial esters of hyaluronic acid |
| US4871357A (en) * | 1986-01-21 | 1989-10-03 | Baxter International Inc. | Ionic heparin coating |
| IT1203814B (it) * | 1986-06-30 | 1989-02-23 | Fidia Farmaceutici | Esteri dell'acido alginico |
| US5147861A (en) * | 1986-06-30 | 1992-09-15 | Fidia S.P.A. | Esters of alginic acid |
| US4745108A (en) * | 1986-08-20 | 1988-05-17 | Foley Kevin M | Heparin derivatives having decreased anti-Xa specificity |
| US4745106A (en) * | 1986-08-20 | 1988-05-17 | Griffin Charles C | Heparin derivatives having improved anti-Xa specificity |
| US4745105A (en) * | 1986-08-20 | 1988-05-17 | Griffin Charles C | Low molecular weight heparin derivatives with improved permeability |
| US4745107A (en) * | 1986-08-20 | 1988-05-17 | Foley Kevin M | Heparin derivatives with improved permeability |
| IT1198449B (it) * | 1986-10-13 | 1988-12-21 | F I D I Farmaceutici Italiani | Esteri di alcoli polivalenti di acido ialuronico |
| US5047020A (en) * | 1987-09-14 | 1991-09-10 | Baxter International Inc. | Ionic heparin coating |
| 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 |
| US4981955A (en) * | 1988-06-28 | 1991-01-01 | Lopez Lorenzo L | Depolymerization method 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 |
| 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 |
| IT1243300B (it) * | 1990-12-20 | 1994-05-26 | Fidia Spa | Derivati dell'eparina |
| US5922690A (en) * | 1996-04-25 | 1999-07-13 | Van Gorp; Cornelius L. | Dermatan disulfate, an inhibitor of thrombin generation and activation |
| US6409987B1 (en) | 1999-04-07 | 2002-06-25 | Intimax Corporation | Targeted agents useful for diagnostic and therapeutic applications |
| US6969705B2 (en) * | 2000-07-21 | 2005-11-29 | Aventis Pharma S.A. | Compositions of polysaccharides derived from heparin, their preparation and pharmaceutical compositions containing them |
| US20030236221A1 (en) * | 2002-06-20 | 2003-12-25 | Chemi Spa | Process for the preparation of esters of heparin |
| ATE356150T1 (de) * | 2002-06-20 | 2007-03-15 | Chemi Spa | Verfahren zur herstellung von heparinestern |
| US20040171819A1 (en) * | 2002-10-10 | 2004-09-02 | Aventis Pharma S.A. | Mixtures of polysaccharides derived from heparin, their preparation and pharmaceutical compositions containing them |
| US7956046B2 (en) * | 2003-07-24 | 2011-06-07 | Aventis Pharma S.A. | Oligosaccharide mixtures derived from heparin, preparation thereof and pharmaceutical compositions containing them |
| US7563780B1 (en) * | 2004-06-18 | 2009-07-21 | Advanced Cardiovascular Systems, Inc. | Heparin prodrugs and drug delivery stents formed therefrom |
| EP2283045A1 (en) * | 2008-05-20 | 2011-02-16 | Crystal Clear Partnership | Separation of polysaccharides by charge density gradient |
| CN101825379A (zh) * | 2010-03-30 | 2010-09-08 | 德华科电器科技(安徽)有限公司 | 一种热泵双回路循环系统 |
| CA2974062C (en) * | 2010-09-14 | 2018-07-17 | Fuso Pharmaceutical Industries, Ltd. | High purity heparin and production method therefor |
| ES2357601B1 (es) | 2011-01-26 | 2012-03-21 | Laboratorios Farmacéuticos Rovi, S.A. | Procedimiento de preparación de derivados de glicosaminoglicanos donadores de óxido n�?trico y su uso en tratamiento de úlceras crónicas. |
| CN105418804B (zh) * | 2015-12-01 | 2018-08-10 | 蚌埠医学院 | 一种疏水化低抗凝血性肝素及其制备方法和应用 |
| BR112022000255A8 (pt) | 2019-07-09 | 2022-03-22 | Optimvia Llc | Métodos para sintetizar polissacarídeos anticoagulantes |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB863235A (en) * | 1958-07-05 | 1961-03-22 | Roussel Uclaf | Improvements in or relating to organic compounds related to heparin |
| FR1363866A (fr) * | 1960-06-21 | 1964-06-19 | Roussel Uclaf | Nouveaux dérivés de l'héparine et procédé de préparation |
| DK108622C (da) * | 1963-01-18 | 1968-01-15 | Roussel Uclaf | Fremgangsmåde til fremstilling af benzylheparinat eller dets alkalimetalsalte. |
| US3506642A (en) * | 1967-07-03 | 1970-04-14 | Canada Packers Ltd | Stable orally active heparinoid complexes |
| FR2100735B1 (pt) * | 1970-06-08 | 1974-08-30 | Mar Pha Etu Expl Marques | |
| GB1399824A (en) * | 1971-08-16 | 1975-07-02 | Mar Pha Etu Expl Marques | Heparin esters |
| GB1501095A (en) * | 1974-04-11 | 1978-02-15 | Mar Pha Etu Expl Marques | Heparin derivatives |
| US4331697A (en) * | 1980-09-02 | 1982-05-25 | Teijin Limited | Novel heparin derivative, method for production thereof, and method for rendering biomedical materials antithrombotic by use of the novel heparin derivative |
-
1980
- 1980-05-14 FR FR8010792A patent/FR2482603A1/fr active Granted
-
1981
- 1981-04-20 GR GR64748A patent/GR73918B/el unknown
- 1981-04-29 DK DK189581A patent/DK189581A/da not_active Application Discontinuation
- 1981-04-29 US US06/258,811 patent/US4440926A/en not_active Expired - Fee Related
- 1981-05-04 KR KR1019810001530A patent/KR840000724B1/ko active
- 1981-05-07 NZ NZ197021A patent/NZ197021A/en unknown
- 1981-05-07 PT PT72995A patent/PT72995B/pt unknown
- 1981-05-08 EP EP81400727A patent/EP0044228B1/fr not_active Expired
- 1981-05-08 DE DE8181400727T patent/DE3168868D1/de not_active Expired
- 1981-05-11 MA MA19353A patent/MA19144A1/fr unknown
- 1981-05-12 IL IL62850A patent/IL62850A/xx unknown
- 1981-05-12 CA CA000377351A patent/CA1183132A/fr not_active Expired
- 1981-05-13 JP JP56072082A patent/JPS5952163B2/ja not_active Expired
- 1981-05-13 FI FI811470A patent/FI811470L/fi not_active Application Discontinuation
- 1981-05-13 ES ES502200A patent/ES8206556A1/es not_active Expired
- 1981-05-13 ZA ZA00813175A patent/ZA813175B/xx unknown
- 1981-05-13 NO NO811631A patent/NO811631L/no unknown
- 1981-05-13 IE IE1073/81A patent/IE51348B1/en unknown
- 1981-05-13 AU AU70520/81A patent/AU543032B2/en not_active Ceased
- 1981-05-14 IN IN512/CAL/81A patent/IN153355B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ197021A (en) | 1984-07-06 |
| PT72995B (fr) | 1982-07-01 |
| US4440926A (en) | 1984-04-03 |
| JPS578201A (en) | 1982-01-16 |
| KR830006332A (ko) | 1983-09-24 |
| EP0044228A3 (en) | 1982-02-17 |
| AU7052081A (en) | 1981-11-19 |
| IL62850A0 (en) | 1981-07-31 |
| GR73918B (pt) | 1984-05-22 |
| FR2482603A1 (fr) | 1981-11-20 |
| EP0044228A2 (fr) | 1982-01-20 |
| ZA813175B (en) | 1982-05-26 |
| PT72995A (fr) | 1981-06-01 |
| FR2482603B1 (pt) | 1982-04-30 |
| DE3168868D1 (en) | 1985-03-28 |
| CA1183132A (fr) | 1985-02-26 |
| MA19144A1 (fr) | 1981-12-31 |
| IL62850A (en) | 1984-06-29 |
| JPS5952163B2 (ja) | 1984-12-18 |
| DK189581A (da) | 1981-11-15 |
| KR840000724B1 (ko) | 1984-05-24 |
| EP0044228B1 (fr) | 1985-02-13 |
| IN153355B (pt) | 1984-07-07 |
| ES502200A0 (es) | 1982-08-16 |
| AU543032B2 (en) | 1985-03-28 |
| IE51348B1 (en) | 1986-12-10 |
| FI811470L (fi) | 1981-11-15 |
| IE811073L (en) | 1981-11-14 |
| ES8206556A1 (es) | 1982-08-16 |
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