CA1238043A - Water insoluble preparations of hyaluronic acid and processes therefor - Google Patents
Water insoluble preparations of hyaluronic acid and processes thereforInfo
- Publication number
- CA1238043A CA1238043A CA000460460A CA460460A CA1238043A CA 1238043 A CA1238043 A CA 1238043A CA 000460460 A CA000460460 A CA 000460460A CA 460460 A CA460460 A CA 460460A CA 1238043 A CA1238043 A CA 1238043A
- Authority
- CA
- Canada
- Prior art keywords
- hyaluronic acid
- cross
- treatment
- effected
- linking agent
- 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
- 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 title claims abstract description 32
- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 32
- 229960003160 hyaluronic acid Drugs 0.000 title claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 16
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 239000000499 gel Substances 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 5
- 229920002873 Polyethylenimine Polymers 0.000 claims description 3
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000010408 film Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229920001228 polyisocyanate Polymers 0.000 claims 2
- 239000005056 polyisocyanate Substances 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 235000015110 jellies Nutrition 0.000 claims 1
- 239000008274 jelly Substances 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 230000008961 swelling Effects 0.000 description 12
- 229920002385 Sodium hyaluronate Polymers 0.000 description 8
- 229940010747 sodium hyaluronate Drugs 0.000 description 8
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(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- Chemical compound [Na+].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 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- 108090000190 Thrombin Proteins 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- -1 aziridine compound Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940014041 hyaluronate Drugs 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 210000004623 platelet-rich plasma Anatomy 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 229960004072 thrombin Drugs 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 241000505673 Scintilla Species 0.000 description 1
- 241001417495 Serranidae Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000002011 beta-particle spectroscopy Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000405 serological effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
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)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56181883A | 1983-12-15 | 1983-12-15 | |
| US561,818 | 1983-12-15 | ||
| US59807184A | 1984-04-09 | 1984-04-09 | |
| US598,071 | 1984-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1238043A true CA1238043A (en) | 1988-06-14 |
Family
ID=27072762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000460460A Expired CA1238043A (en) | 1983-12-15 | 1984-08-07 | Water insoluble preparations of hyaluronic acid and processes therefor |
Country Status (6)
| Country | Link |
|---|---|
| AU (1) | AU551628B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1238043A (enrdf_load_stackoverflow) |
| DE (1) | DE3434104A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2556728B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2151244B (enrdf_load_stackoverflow) |
| IT (1) | IT1178588B (enrdf_load_stackoverflow) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4582865A (en) * | 1984-12-06 | 1986-04-15 | Biomatrix, Inc. | Cross-linked gels of hyaluronic acid and products containing such gels |
| US4713448A (en) * | 1985-03-12 | 1987-12-15 | Biomatrix, Inc. | Chemically modified hyaluronic acid preparation and method of recovery thereof from animal tissues |
| US5202431A (en) * | 1985-07-08 | 1993-04-13 | Fidia, S.P.A. | Partial esters of hyaluronic acid |
| US4851521A (en) * | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
| IT1198449B (it) * | 1986-10-13 | 1988-12-21 | F I D I Farmaceutici Italiani | Esteri di alcoli polivalenti di acido ialuronico |
| US5017229A (en) * | 1990-06-25 | 1991-05-21 | Genzyme Corporation | Water insoluble derivatives of hyaluronic acid |
| US6610669B1 (en) | 1987-09-18 | 2003-08-26 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| US4937270A (en) * | 1987-09-18 | 1990-06-26 | Genzyme Corporation | Water insoluble derivatives of hyaluronic acid |
| US5527893A (en) * | 1987-09-18 | 1996-06-18 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| US6174999B1 (en) | 1987-09-18 | 2001-01-16 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| AU619760B2 (en) * | 1987-12-10 | 1992-02-06 | Genzyme Biosurgery Corporation | Hylan preparation and method of recovery thereof from animal tissues |
| US4888016A (en) * | 1988-02-10 | 1989-12-19 | Langerman David W | "Spare parts" for use in ophthalmic surgical procedures |
| EP0407517B1 (en) * | 1988-12-29 | 1995-08-09 | Chang, Ann Lois | Diaphragm pump |
| IT1260154B (it) * | 1992-07-03 | 1996-03-28 | Lanfranco Callegaro | Acido ialuronico e suoi derivati in polimeri interpenetranti (ipn) |
| US5550112A (en) * | 1992-12-30 | 1996-08-27 | Patent Biopharmaceutics, Inc. | Hyaluronic acid-urea pharmaceutical compositions and uses |
| US5529987A (en) * | 1993-08-04 | 1996-06-25 | Patent Biopharmaceutics, Inc. | Hyaluronic acid-urea pharmaceutical compositions and uses |
| US5531716A (en) * | 1993-09-29 | 1996-07-02 | Hercules Incorporated | Medical devices subject to triggered disintegration |
| US6294202B1 (en) | 1994-10-06 | 2001-09-25 | Genzyme Corporation | Compositions containing polyanionic polysaccharides and hydrophobic bioabsorbable polymers |
| US6214331B1 (en) | 1995-06-06 | 2001-04-10 | C. R. Bard, Inc. | Process for the preparation of aqueous dispersions of particles of water-soluble polymers and the particles obtained |
| ES2248817T3 (es) * | 1995-06-06 | 2006-03-16 | C.R. Bard, Inc. | Procedimiento de preparacion de particulas reticuladas de polimeros hidrosolubles, las particulas obtenidas y su utilizacion. |
| US6060534A (en) | 1996-07-11 | 2000-05-09 | Scimed Life Systems, Inc. | Medical devices comprising ionically and non-ionically crosslinked polymer hydrogels having improved mechanical properties |
| US6368356B1 (en) | 1996-07-11 | 2002-04-09 | Scimed Life Systems, Inc. | Medical devices comprising hydrogel polymers having improved mechanical properties |
| ES2217496T3 (es) * | 1998-02-27 | 2004-11-01 | Stichting Hippomedics | Proceso para producir acido hialuronico reticulado. |
| GB9902652D0 (en) * | 1999-02-05 | 1999-03-31 | Fermentech Med Ltd | Process |
| US6521223B1 (en) | 2000-02-14 | 2003-02-18 | Genzyme Corporation | Single phase gels for the prevention of adhesions |
| WO2003089476A1 (en) * | 2002-04-17 | 2003-10-30 | Genzyme Corporation | Cross-linked hyaluronate compounds |
| AU2003234140A1 (en) | 2002-04-17 | 2003-11-03 | Genzyme Corporation | Aziridine compounds and their use in medical devices |
| AU2003901834A0 (en) * | 2003-04-17 | 2003-05-01 | Clearcoll Pty Ltd | Cross-linked polysaccharide compositions |
| GB2408741B (en) | 2003-12-04 | 2008-06-18 | Ind Tech Res Inst | Hyaluronic acid derivative with urethane linkage |
| US8313765B2 (en) | 2003-12-04 | 2012-11-20 | Industrial Technology Research Institute | Biodegradable hyaluronic acid derivative, biodegradable polymeric micelle composition and pharmaceutical or bioactive composition |
| AU2005223678B2 (en) | 2004-03-17 | 2010-08-26 | Genzyme Corporation | Anti-adhesion spraying |
| US7858107B2 (en) | 2004-09-10 | 2010-12-28 | Medtronic Xomed, Inc. | Flexible bioresorbable hemostatic packing and stent having a preselectable in-vivo residence time |
| GB2423252B (en) * | 2005-02-18 | 2007-10-17 | Engelhard Lyon | Cross-linked polymer of carbohydrate, notably based on polysaccharides, and/or on oligosaccharides and/or on polyols |
| FR2882366B1 (fr) | 2005-02-18 | 2008-04-18 | Coletica Sa | Polymere reticule de carbohydrate, notamment a base de polysaccharides et/ou de polyols |
| CA2618253C (en) | 2005-08-04 | 2013-05-28 | Teijin Limited | Cellulose derivative |
| FR2918377B1 (fr) | 2007-07-05 | 2010-10-08 | Estelle Piron | Gel co-reticule de polysaccharides |
| KR100990301B1 (ko) | 2007-09-28 | 2010-10-26 | 가부시키가이샤 시세이도 | 팽윤성 가교 히알루론산 분말과 그 제조 방법 |
| FR2924615B1 (fr) | 2007-12-07 | 2010-01-22 | Vivacy Lab | Hydrogel cohesif biodegradable. |
| IN2014DN07588A (enrdf_load_stackoverflow) * | 2012-03-12 | 2015-04-24 | Univ Colorado State Res Found | |
| US10266684B2 (en) | 2012-03-12 | 2019-04-23 | Colorado State University Research Foundation | Glycosaminoglycan and synthetic polymer materials for blood-contacting applications |
| ITMI20131193A1 (it) * | 2013-07-16 | 2015-01-17 | Ira Srl | Acido ialuronico reticolato, processo per la sua preparazione ed applicazioni in ambito estetico |
| ITUA20161822A1 (it) * | 2016-03-18 | 2017-09-18 | Indena Spa | Composizioni utili nella prevenzione e/o nel trattamento di patologie del cavo orale, delle prime vie aeree e dell’esofago |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE361320B (enrdf_load_stackoverflow) * | 1972-03-14 | 1973-10-29 | Exploaterings Ab Tbf | |
| US4152170A (en) * | 1975-06-18 | 1979-05-01 | Sumitomo Chemical Company, Ltd. | Cross-linked pullulan |
| GB1515963A (en) * | 1975-07-15 | 1978-06-28 | Massachusetts Inst Technology | Crosslinked collagen-mucopolysaccharide composite materials |
-
1984
- 1984-08-07 CA CA000460460A patent/CA1238043A/en not_active Expired
- 1984-08-13 GB GB08420560A patent/GB2151244B/en not_active Expired
- 1984-09-17 DE DE19843434104 patent/DE3434104A1/de active Granted
- 1984-09-21 AU AU33379/84A patent/AU551628B2/en not_active Expired
- 1984-10-18 IT IT23225/84A patent/IT1178588B/it active
- 1984-11-26 FR FR8417956A patent/FR2556728B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB8420560D0 (en) | 1984-09-19 |
| DE3434104C2 (enrdf_load_stackoverflow) | 1991-06-20 |
| GB2151244A (en) | 1985-07-17 |
| GB2151244B (en) | 1987-01-07 |
| AU3337984A (en) | 1985-06-20 |
| DE3434104A1 (de) | 1985-08-29 |
| FR2556728B1 (fr) | 1987-06-26 |
| FR2556728A1 (fr) | 1985-06-21 |
| IT8423225A1 (it) | 1986-04-18 |
| AU551628B2 (en) | 1986-05-08 |
| IT1178588B (it) | 1987-09-09 |
| IT8423225A0 (it) | 1984-10-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1238043A (en) | Water insoluble preparations of hyaluronic acid and processes therefor | |
| US4500676A (en) | Hyaluronate modified polymeric articles | |
| US4487865A (en) | Polymeric articles modified with hyaluronate | |
| US4755379A (en) | Polymers substituted by groups conferring anti-coagulant properties on them, process for their preparation, articles and compositions made therefrom and uses thereof | |
| EP0200574B1 (en) | A biomaterial comprising a composite material of chitosan derivative and collagen and a process for the production of the same | |
| Ratner et al. | Cell adhesion to polymeric materials: implications with respect to biocompatibility | |
| FI103381B (fi) | Hyaluronihapon veteen liukenemattomia geelejä ja menetelmä sen valmist amiseksi | |
| US4871357A (en) | Ionic heparin coating | |
| Miyara et al. | A new antithrombogenic heparinized polymer | |
| GB2150833A (en) | Proteolytic wounds dressing | |
| US3717502A (en) | Method for providing anticoagulant surfaces onto articles | |
| HK1011502A1 (en) | Biocompatible viscoelastic gel slurries, their preparation and use | |
| KR20080062092A (ko) | 세포전달체로서의 히알루론산 유도체 및 이의 제조 방법 | |
| US7345117B1 (en) | Sulphated hyaluronic acid and sulphated derivatives thereof covalently bound to polyurethanes, and the process for their preparation | |
| AU2004303599B2 (en) | Compositions of semi-interpenetrating polymer network | |
| US3865723A (en) | Method to form stable complexes of polyanions occurring in biological liquids | |
| US4082727A (en) | Method for manufacture of non-coagulative organosilicone polymer | |
| JPS60130601A (ja) | ヒアルロン酸水不溶性組成物の製法 | |
| Raghunath et al. | Some characteristics of collagen‐heparin complex | |
| JPS61130301A (ja) | 抗凝血活性を有する硫酸化キシロフラナン及びその製造法 | |
| Kashiwagi et al. | Non-thrombogenicity of organic polymers by blending with alkylamine-heparin complexes | |
| US2729633A (en) | Sulfated pectic acid blood anticoagulant | |
| Dincer et al. | Covalent immobilization of heparin on polymethylacrylate surfaces | |
| Avramoglou et al. | Blood-contacting polymers | |
| Hoffman et al. | Method for preparation of biocompatible and biofunctional materials and product thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |