AU749627B2 - Use of hyaluronic acid derivatives in the preparation of biomaterials with a physical haemostatic and plugging activity and a preventive activity in the formation of adhesions following anastomosis - Google Patents
Use of hyaluronic acid derivatives in the preparation of biomaterials with a physical haemostatic and plugging activity and a preventive activity in the formation of adhesions following anastomosis Download PDFInfo
- Publication number
- AU749627B2 AU749627B2 AU92555/98A AU9255598A AU749627B2 AU 749627 B2 AU749627 B2 AU 749627B2 AU 92555/98 A AU92555/98 A AU 92555/98A AU 9255598 A AU9255598 A AU 9255598A AU 749627 B2 AU749627 B2 AU 749627B2
- Authority
- AU
- Australia
- Prior art keywords
- hyaluronic acid
- derivative
- biomaterials
- acid
- solution
- 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.)
- Ceased
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- 239000012620 biological material Substances 0.000 title claims abstract description 43
- 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 class 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 description 163
- 229940030225 antihemorrhagics Drugs 0.000 title claims description 14
- 230000000025 haemostatic effect Effects 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title abstract description 28
- 230000003872 anastomosis Effects 0.000 title abstract description 22
- 230000015572 biosynthetic process Effects 0.000 title abstract description 11
- 230000000694 effects Effects 0.000 title description 6
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- 230000004888 barrier function Effects 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 136
- 229920002674 hyaluronan Polymers 0.000 claims description 135
- 229960003160 hyaluronic acid Drugs 0.000 claims description 133
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 54
- -1 aliphatic alcohols Chemical class 0.000 claims description 49
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
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- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 6
- 229920001817 Agar Polymers 0.000 claims description 6
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- 239000001814 pectin Substances 0.000 claims description 6
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical class O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 4
- 229920002230 Pectic acid Polymers 0.000 claims description 4
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- 239000000783 alginic acid Substances 0.000 claims description 4
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- 150000004781 alginic acids Chemical class 0.000 claims description 4
- 239000003242 anti bacterial agent Substances 0.000 claims description 4
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- 239000012528 membrane Substances 0.000 claims description 4
- 239000004745 nonwoven fabric Substances 0.000 claims description 4
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 claims description 4
- 229920003175 pectinic acid Polymers 0.000 claims description 4
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 4
- 239000010318 polygalacturonic acid Substances 0.000 claims description 4
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- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 4
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- 125000006850 spacer group Chemical group 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 108010049003 Fibrinogen Proteins 0.000 claims description 3
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- 150000004985 diamines Chemical class 0.000 claims description 3
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- 239000003102 growth factor Substances 0.000 claims description 3
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- 239000004005 microsphere Substances 0.000 claims description 3
- 229920005615 natural polymer Polymers 0.000 claims description 3
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 3
- 229920002492 poly(sulfone) Polymers 0.000 claims description 3
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- 239000002243 precursor Substances 0.000 claims description 3
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- 229960004072 thrombin Drugs 0.000 claims description 3
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- 241000722985 Fidia Species 0.000 claims 1
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- 230000002792 vascular Effects 0.000 abstract description 10
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- 231100000241 scar Toxicity 0.000 abstract description 2
- 230000002439 hemostatic effect Effects 0.000 abstract 2
- 230000009772 tissue formation Effects 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 178
- 239000000243 solution Substances 0.000 description 130
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- 235000019441 ethanol Nutrition 0.000 description 55
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 43
- 239000012153 distilled water Substances 0.000 description 42
- 238000005670 sulfation reaction Methods 0.000 description 39
- 239000002244 precipitate Substances 0.000 description 38
- 230000019635 sulfation Effects 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 27
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 15
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 15
- 210000003462 vein Anatomy 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000005119 centrifugation Methods 0.000 description 14
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 13
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 13
- 125000004494 ethyl ester group Chemical group 0.000 description 13
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 13
- 229940014800 succinic anhydride Drugs 0.000 description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 12
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- 239000003153 chemical reaction reagent Substances 0.000 description 12
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 12
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
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- 229910052709 silver Inorganic materials 0.000 description 10
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- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 10
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- 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
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- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 150000003657 tungsten Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 235000019143 vitamin K2 Nutrition 0.000 description 1
- 239000011728 vitamin K2 Substances 0.000 description 1
- 239000003357 wound healing promoting agent Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/041—Mixtures of macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/042—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/418—Agents promoting blood coagulation, blood-clotting agents, embolising agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/04—Materials for stopping bleeding
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITPD97A000170 | 1997-07-28 | ||
| IT97PD000170A IT1294797B1 (it) | 1997-07-28 | 1997-07-28 | Uso dei derivati dell'acido ialuronico nella preparazione di biomateriali aventi attivita' emostatica fisica e tamponante |
| PCT/EP1998/004716 WO1999004828A2 (en) | 1997-07-28 | 1998-07-28 | Use of hyaluronic acid derivatives in the preparation of biomaterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU9255598A AU9255598A (en) | 1999-02-16 |
| AU749627B2 true AU749627B2 (en) | 2002-06-27 |
Family
ID=11391877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU92555/98A Ceased AU749627B2 (en) | 1997-07-28 | 1998-07-28 | Use of hyaluronic acid derivatives in the preparation of biomaterials with a physical haemostatic and plugging activity and a preventive activity in the formation of adhesions following anastomosis |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7202230B2 (https=) |
| EP (1) | EP0999859B1 (https=) |
| JP (1) | JP4417547B2 (https=) |
| AT (1) | ATE311208T1 (https=) |
| AU (1) | AU749627B2 (https=) |
| CA (1) | CA2298733C (https=) |
| DE (1) | DE69832616T2 (https=) |
| DK (1) | DK0999859T3 (https=) |
| ES (1) | ES2253827T3 (https=) |
| IL (2) | IL134140A0 (https=) |
| IT (1) | IT1294797B1 (https=) |
| WO (1) | WO1999004828A2 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1306679B1 (it) * | 1999-06-29 | 2001-10-02 | Fidia Advanced Biopolymers Srl | Uso dei derivati dell'acido ialuronico per la preparazione dicomposizoni farmaceutiche e biomateriali per la prevenzione della |
| AU2001266926A1 (en) * | 2000-06-16 | 2002-01-02 | University Of Medicine And Dentistry Of New Jersey | Hemostatic compositions, devices and methods |
| US7094428B2 (en) | 2000-06-16 | 2006-08-22 | The University Of Medicine And Dentistry Of New Jersey | Hemostatic compositions, devices and methods |
| US6235796B1 (en) * | 2000-06-26 | 2001-05-22 | Sarfaraz K. Niazi | Use of fluorocarbons for the prevention of surgical adhesions |
| WO2005010080A1 (ja) * | 2003-07-28 | 2005-02-03 | Teijin Limited | 温度応答性ハイドロゲル |
| DE10349722A1 (de) * | 2003-10-23 | 2005-06-16 | Beschorner, Katharina, Dr. | Zusammensetzung zur Arthrose-/Arthritisbehandlung, insbesondere von Gelenken |
| KR20070046093A (ko) * | 2004-07-09 | 2007-05-02 | 훼로산 아크티에 셀스카브 | 히알루론산을 포함하는 지혈 조성물 |
| ITPD20040245A1 (it) | 2004-10-08 | 2005-01-08 | Fidia Advanced Biopolymers Srl | Biomateriali costituiti da acido ialuronico solfatato e gellano utilizzabili nella prevenzione delle adesioni spinali |
| US20080220053A1 (en) * | 2004-12-14 | 2008-09-11 | Fidia Advanced Biopolymers S.R.L. | Process for the Preparation of Two and Three Dimensional Polymer Scaffolds |
| ITPD20040312A1 (it) * | 2004-12-15 | 2005-03-15 | Fidia Advanced Biopolymers Srl | Protesi e o supporto per la sostituzione, riparazione, rigenerazione del menisco |
| ITPD20050206A1 (it) | 2005-07-07 | 2007-01-08 | Fidia Advanced Biopolymers Srl | Biomateriali in forma di fibra da impiegarsi come dispositivi medici nel trattamento delle ferite e loro processi di produzione |
| ITMI20051415A1 (it) * | 2005-07-22 | 2007-01-23 | Fidia Advanced Biopolymers Srl | Biomateriali a base di corbossimetilcellulosa salificata con zinco associata a derivati dell'acido ialuronico da impiegarsi come dispositivi medici con attivita' antimicrobica ed antifungina e loro processo di produzione |
| EP1996115B1 (en) * | 2006-03-07 | 2014-11-26 | Axle International | Bioactive scaffold for therapeutic and adhesion prevention applications |
| ITPD20060219A1 (it) | 2006-05-31 | 2007-12-01 | Fidia Farmaceutici | Composizioni farmaceutiche contenenti acido ialuronico solfatato nel trattamento dell'osteoartrosi |
| CA2716872C (en) | 2008-02-29 | 2015-02-10 | Ferrosan Medical Devices A/S | Device for promotion of hemostasis and/or wound healing |
| US8343942B2 (en) | 2008-04-04 | 2013-01-01 | University Of Utah Research Foundation | Methods for treating interstitial cystitis |
| AU2009231634B2 (en) * | 2008-04-04 | 2014-05-15 | University Of Utah Research Foundation | Alkylated semi-synthetic glycosaminoglycosan ethers, and methods for making and using thereof |
| AU2009288118B2 (en) | 2008-09-02 | 2014-12-11 | Allergan, Inc. | Threads of hyaluronic acid and/or derivatives thereof, methods of making thereof and uses thereof |
| TWI458833B (zh) * | 2010-05-11 | 2014-11-01 | Univ China Medical | 奈米金屬分散液及其製法 |
| CA2830933A1 (en) | 2011-03-23 | 2012-09-27 | University Of Utah Research Foundation | Methods for treating or preventing urological inflammation |
| CN104159527B (zh) | 2012-03-06 | 2017-04-12 | 弗罗桑医疗设备公司 | 包含止血糊剂的压力容器 |
| RU2636240C2 (ru) | 2012-06-12 | 2017-11-21 | Ферросан Медикал Дивайсиз А/С | Сухая гемостатическая композиция |
| JP6390873B2 (ja) | 2013-06-21 | 2018-09-19 | フェッローサン メディカル ディバイス エー／エス | 減圧膨張させた乾燥組成物およびそれを保持するためのシリンジ |
| BR112016013322B1 (pt) | 2013-12-11 | 2020-07-21 | Ferrosan Medical Devices A/S | métodos para preparação de uma composição seca e para reconstituir uma composição seca, composição seca, uso de uma composição seca, e, kit |
| HRP20220176T1 (hr) * | 2014-02-27 | 2022-04-29 | Synartro Ab | Konjugati hijaluronana s farmaceutski aktivnim tvarima, postupci i pripravci |
| BR112017007466B1 (pt) | 2014-10-13 | 2021-03-02 | Ferrosan Medical Devices A/S | método para preparar uma composição seca, método para reconstituir a composição seca, pasta, composição seca, recipiente, kit homeostático, e, uso de uma composição seca |
| RU2705905C2 (ru) | 2014-12-24 | 2019-11-12 | Ферросан Медикал Дивайсиз А/С | Шприц для удерживания и смешивания первого и второго веществ |
| CA2986981A1 (en) | 2015-07-03 | 2017-01-12 | Ferrosan Medical Devices A/S | Syringe for mixing two components and for retaining a vacuum in a storage condition |
| KR20180027126A (ko) * | 2016-09-06 | 2018-03-14 | (주)한국비엠아이 | 가교화 히알루론산 유도체 매트릭스가 포함된 지혈 조성물 |
| US11337994B2 (en) | 2016-09-15 | 2022-05-24 | University Of Utah Research Foundation | In situ gelling compositions for the treatment or prevention of inflammation and tissue damage |
| EP4321182A3 (en) | 2018-05-09 | 2024-05-29 | Ferrosan Medical Devices A/S | Method for preparing a haemostatic composition |
| CN111228653A (zh) | 2018-11-13 | 2020-06-05 | 格莱科米拉治疗公司 | 用电离辐射加强癌症治疗的方法 |
| KR101980063B1 (ko) * | 2019-01-25 | 2019-05-17 | 주식회사 휴메딕스 | 히알루론산을 포함하는 스펀지형 생분해성 지혈제 조성물 |
| CN113754795B (zh) * | 2021-10-19 | 2023-03-10 | 澳门大学 | 磺酸化透明质酸类化合物、其制备方法及其应用 |
| CN116688216A (zh) * | 2023-05-26 | 2023-09-05 | 北京福爱乐科技发展有限公司 | 一种生物可降解医用凝胶及其制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992020349A1 (en) * | 1991-05-20 | 1992-11-26 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| WO1995025751A1 (en) * | 1994-03-23 | 1995-09-28 | Fidia Advanced Biopolymers Srl | Novel heparin-like sulfated polysaccharides |
| WO1997007833A2 (en) * | 1995-08-29 | 1997-03-06 | Fidia Advanced Biopolymers, S.R.L. | Biomaterials for preventing post-surgical adhesions comprised of hyaluronic acid derivatives |
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| 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 |
| IT1203814B (it) | 1986-06-30 | 1989-02-23 | Fidia Farmaceutici | Esteri dell'acido alginico |
| IT1198449B (it) | 1986-10-13 | 1988-12-21 | F I D I Farmaceutici Italiani | Esteri di alcoli polivalenti di acido ialuronico |
| IT1219587B (it) * | 1988-05-13 | 1990-05-18 | Fidia Farmaceutici | Polisaccaridi carbossiilici autoreticolati |
| GB8911177D0 (en) * | 1989-05-16 | 1989-07-05 | Vilain Jean | Alginate gel pharmaceutical product |
| IT1247157B (it) | 1991-02-11 | 1994-12-12 | Fidia Spa | Canali di guida biodegradabili e bioassorbibili da impiegare per la rigenerazione nervosa. |
| ES2087471T3 (es) | 1991-02-11 | 1996-07-16 | Fidia Spa | Esteres gelan. |
| GB9109367D0 (en) * | 1991-05-01 | 1991-06-26 | Merck Sharp & Dohme | Surgical dressing |
| IT1247472B (it) | 1991-05-31 | 1994-12-17 | Fidia Spa | Processo per la preparazione di microsfere contenenti componenti biologicamente attivi. |
| IT1254704B (it) | 1991-12-18 | 1995-10-09 | Mini Ricerca Scient Tecnolog | Tessuto non tessuto essenzialmente costituito da derivati dell'acido ialuronico |
| IT1264322B (it) | 1992-07-30 | 1996-09-23 | Lanfranco Callegaro | Esteri di gellano autoreticolato, procedimento di preparazione e loro applicazioni farmaceutiche e biomedico-sanitarie |
| IT1259141B (it) | 1992-08-03 | 1996-03-11 | Fidia Spa | Canali di guida biodegradabili e bioriassorbibili da impiegare per la riparazione tissutale come adiuvante in interventi chirurgici |
| FR2723847A1 (fr) * | 1994-08-29 | 1996-03-01 | Debiopharm Sa | Compositions antithrombotiques et non hemorragiques a base d'heparine, procede pour leur preparation et applications therapeutiques. |
| IT1281877B1 (it) * | 1995-05-10 | 1998-03-03 | Fidia Advanced Biopolymers Srl | Sali di metalli pesanti di succinil derivati dell'acido ialuronico e loro impiego come potenziali agenti terapeutici |
| GB9514361D0 (en) * | 1995-07-13 | 1995-09-13 | Bristol Myers Squibb Co | A film for topical use in the treatment of wounds |
| IT1282994B1 (it) * | 1996-05-10 | 1998-04-03 | Inalco Spa | Derivati del polisaccaride k5 aventi elevata attivita' anticoagulante |
| IT1287698B1 (it) | 1996-08-29 | 1998-08-18 | Fidia Advanced Biopolymers Srl | Fili da sutura essenzialmente costituiti da derivati esterei dello acido ialuronico |
-
1997
- 1997-07-28 IT IT97PD000170A patent/IT1294797B1/it active IP Right Grant
-
1998
- 1998-07-28 EP EP98945104A patent/EP0999859B1/en not_active Expired - Lifetime
- 1998-07-28 DE DE69832616T patent/DE69832616T2/de not_active Expired - Lifetime
- 1998-07-28 CA CA002298733A patent/CA2298733C/en not_active Expired - Lifetime
- 1998-07-28 AT AT98945104T patent/ATE311208T1/de active
- 1998-07-28 IL IL13414098A patent/IL134140A0/xx active IP Right Grant
- 1998-07-28 DK DK98945104T patent/DK0999859T3/da active
- 1998-07-28 WO PCT/EP1998/004716 patent/WO1999004828A2/en not_active Ceased
- 1998-07-28 ES ES98945104T patent/ES2253827T3/es not_active Expired - Lifetime
- 1998-07-28 AU AU92555/98A patent/AU749627B2/en not_active Ceased
- 1998-07-28 JP JP2000503879A patent/JP4417547B2/ja not_active Expired - Fee Related
-
2000
- 2000-01-20 IL IL134140A patent/IL134140A/en not_active IP Right Cessation
-
2002
- 2002-05-07 US US10/139,878 patent/US7202230B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992020349A1 (en) * | 1991-05-20 | 1992-11-26 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| WO1995025751A1 (en) * | 1994-03-23 | 1995-09-28 | Fidia Advanced Biopolymers Srl | Novel heparin-like sulfated polysaccharides |
| WO1997007833A2 (en) * | 1995-08-29 | 1997-03-06 | Fidia Advanced Biopolymers, S.R.L. | Biomaterials for preventing post-surgical adhesions comprised of hyaluronic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2298733A1 (en) | 1999-02-04 |
| US7202230B2 (en) | 2007-04-10 |
| DK0999859T3 (da) | 2006-03-27 |
| EP0999859B1 (en) | 2005-11-30 |
| US20030060448A1 (en) | 2003-03-27 |
| DE69832616D1 (de) | 2006-01-05 |
| IT1294797B1 (it) | 1999-04-15 |
| HK1028210A1 (en) | 2001-02-09 |
| IL134140A (en) | 2006-08-20 |
| ES2253827T3 (es) | 2006-06-01 |
| IL134140A0 (en) | 2001-04-30 |
| ITPD970170A1 (it) | 1999-01-28 |
| EP0999859A2 (en) | 2000-05-17 |
| AU9255598A (en) | 1999-02-16 |
| WO1999004828A3 (en) | 1999-06-10 |
| WO1999004828A2 (en) | 1999-02-04 |
| ATE311208T1 (de) | 2005-12-15 |
| CA2298733C (en) | 2009-09-01 |
| JP2001510713A (ja) | 2001-08-07 |
| JP4417547B2 (ja) | 2010-02-17 |
| DE69832616T2 (de) | 2006-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |