CA2264085C - Hyaluronic acid esters, threads and biomaterials containing them, and their use in surgery - Google Patents
Hyaluronic acid esters, threads and biomaterials containing them, and their use in surgery Download PDFInfo
- Publication number
- CA2264085C CA2264085C CA002264085A CA2264085A CA2264085C CA 2264085 C CA2264085 C CA 2264085C CA 002264085 A CA002264085 A CA 002264085A CA 2264085 A CA2264085 A CA 2264085A CA 2264085 C CA2264085 C CA 2264085C
- Authority
- CA
- Canada
- Prior art keywords
- hyaluronic acid
- alcohol
- esterified
- carboxylic functions
- ester derivatives
- 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 - Fee Related
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 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 abstract description 46
- 238000001356 surgical procedure Methods 0.000 title claims abstract description 13
- 239000012620 biological material Substances 0.000 title claims description 5
- -1 aliphatic alcohols Chemical class 0.000 claims abstract description 36
- 229920002674 hyaluronan Polymers 0.000 claims abstract description 30
- 229960003160 hyaluronic acid Drugs 0.000 claims abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 21
- 150000002148 esters Chemical class 0.000 claims abstract description 20
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 49
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 claims description 21
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 15
- GLDOVTGHNKAZLK-UHFFFAOYSA-N n-octadecyl alcohol Natural products CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 14
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- LQZZUXJYWNFBMV-UHFFFAOYSA-N ethyl butylhexanol Natural products CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 10
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 9
- 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 description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosanyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 238000002316 cosmetic surgery Methods 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000004745 nonwoven fabric Substances 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N n-decyl alcohol Natural products CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims 2
- 238000002682 general surgery Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 239000000463 material Substances 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 150000002632 lipids Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000002729 catgut Substances 0.000 description 7
- 239000007943 implant Substances 0.000 description 6
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 3
- 229940032094 squalane Drugs 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 229920000954 Polyglycolide Polymers 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000013060 biological fluid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 239000004633 polyglycolic acid Substances 0.000 description 2
- 229950008885 polyglycolic acid Drugs 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 210000004872 soft tissue Anatomy 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- QYOXLKAKUAASNA-UHFFFAOYSA-N 1-bromodocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCBr QYOXLKAKUAASNA-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- CZASMUMJSKOHFJ-UHFFFAOYSA-N 1-bromoicosane Chemical compound CCCCCCCCCCCCCCCCCCCCBr CZASMUMJSKOHFJ-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 208000034693 Laceration Diseases 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 210000003815 abdominal wall Anatomy 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229920000704 biodegradable plastic Polymers 0.000 description 1
- 238000013130 cardiovascular surgery Methods 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 210000001520 comb Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229950004297 lauril Drugs 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000003356 suture material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000001635 urinary tract Anatomy 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
- A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
- A61L17/06—At least partially resorbable materials
- A61L17/10—At least partially resorbable materials containing macromolecular materials
- A61L17/105—Polyesters not covered by A61L17/12
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Vascular Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Surgery (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Materials For Medical Uses (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITPD96A000207 | 1996-08-29 | ||
| IT96PD000207A IT1287698B1 (it) | 1996-08-29 | 1996-08-29 | Fili da sutura essenzialmente costituiti da derivati esterei dello acido ialuronico |
| PCT/EP1997/004684 WO1998008876A1 (en) | 1996-08-29 | 1997-08-28 | Hyaluronic acid esters, threads and biomaterials containing them, and their use in surgery |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2264085A1 CA2264085A1 (en) | 1998-03-05 |
| CA2264085C true CA2264085C (en) | 2006-10-03 |
Family
ID=11391508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002264085A Expired - Fee Related CA2264085C (en) | 1996-08-29 | 1997-08-28 | Hyaluronic acid esters, threads and biomaterials containing them, and their use in surgery |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20010008937A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP0922060B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4221734B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE226961T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU722586B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2264085C (cg-RX-API-DMAC7.html) |
| DE (1) | DE69716745T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2185991T3 (cg-RX-API-DMAC7.html) |
| IT (1) | IT1287698B1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO1998008876A1 (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9228027B2 (en) | 2008-09-02 | 2016-01-05 | Allergan Holdings France S.A.S. | Threads of Hyaluronic acid and/or derivatives thereof, methods of making thereof and uses thereof |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6632802B2 (en) * | 1996-08-29 | 2003-10-14 | Fidia Advanced Biopolymers S.R.L. | Hyaluronic acid esters, threads and biomaterials containing them, and their use in surgery |
| IT1294797B1 (it) | 1997-07-28 | 1999-04-15 | Fidia Advanced Biopolymers Srl | Uso dei derivati dell'acido ialuronico nella preparazione di biomateriali aventi attivita' emostatica fisica e tamponante |
| IT1306644B1 (it) | 1999-04-08 | 2001-10-02 | Fidia Advanced Biopolymers Srl | Strutture tridimensionali comprendenti derivati dell'acido ialuronicoottenibili mediante la tecnica antisolvente supercritico. |
| IT1306643B1 (it) * | 1999-04-08 | 2001-10-02 | Fidia Advanced Biopolymers Srl | Processo per la preparazione dei composti autoreticolati dell'acidoialuronico e dei suoi derivati ottenibili mediante la tecnica |
| DE10226396B4 (de) * | 2002-06-13 | 2004-12-09 | Siemens Ag | Modulares Kommunikationsgerät |
| US7816316B2 (en) | 2002-11-21 | 2010-10-19 | Chugai Seiyaku Kabushiki Kaisha | Sustained release drug carrier |
| DE202006008868U1 (de) * | 2006-06-06 | 2006-08-03 | Sefar Ag | Gewebe, insbesondere für textile Bauten und/oder Abdeckungen |
| KR20100094982A (ko) | 2007-11-13 | 2010-08-27 | 바이오-테크널러지 제너럴 (이스라엘) 리미티드 | 점탄성 바이오폴리머의 희석식 여과 멸균 방법 |
| JP5676858B2 (ja) | 2008-06-19 | 2015-02-25 | キヤノン株式会社 | 記録装置 |
| DK2384210T3 (da) | 2008-12-02 | 2017-11-27 | Allergan Inc | Injektionsanordning |
| CZ302503B6 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace |
| CZ302504B6 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace |
| CZ20101001A3 (cs) | 2010-12-31 | 2012-02-08 | Cpn S.R.O. | Hyaluronová vlákna, zpusob jejich prípravy a použití |
| CZ303879B6 (cs) | 2012-02-28 | 2013-06-05 | Contipro Biotech S.R.O. | Deriváty na bázi kyseliny hyaluronové schopné tvorit hydrogely, zpusob jejich prípravy, hydrogely na bázi techto derivátu, zpusob jejich prípravy a pouzití |
| CZ304512B6 (cs) | 2012-08-08 | 2014-06-11 | Contipro Biotech S.R.O. | Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití |
| CZ2012841A3 (cs) | 2012-11-27 | 2014-02-19 | Contipro Biotech S.R.O. | Vlákna založená na hydrofobizovaném hyaluronanu, způsob jejich přípravy a použití, textilie na jejich bázi a použití |
| CZ304266B6 (cs) | 2012-11-27 | 2014-02-05 | Contipro Biotech S.R.O. | Nekonečná vlákna na bázi hyaluronanu selektivně oxidovaného v poloze 6 N-acetyl-D-glukosaminové části, jejich příprava, použití, nitě, střiže, příze, textilie a způsob jejich úpravy |
| CZ2012842A3 (cs) | 2012-11-27 | 2014-08-20 | Contipro Biotech S.R.O. | Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití |
| RU2520599C1 (ru) * | 2013-02-21 | 2014-06-27 | Общество с ограниченной ответственностью "ДЖИ-Групп" | Способ эндоскопической биопластики гастродуоденальных язв комплексным биопластическим материалом |
| US20140350518A1 (en) | 2013-05-23 | 2014-11-27 | Allergan, Inc. | Syringe extrusion accessory |
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| US10258447B2 (en) | 2017-01-24 | 2019-04-16 | Allergan Industrie Sas | Thread insertion devices |
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Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4851521A (en) * | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
| JPH0625306A (ja) * | 1992-04-21 | 1994-02-01 | Shiseido Co Ltd | 溶媒不溶化ヒアルロン酸及びその製造方法 |
| IT1268955B1 (it) * | 1994-03-11 | 1997-03-18 | Fidia Advanced Biopolymers Srl | Esteri attivi di polisaccaridi carbossilici |
| BR9610996A (pt) * | 1995-08-29 | 1999-07-13 | Fidia Advanced Biopolymers Srl | Biomateriais para prevenção de ades es pós-cirúrgicas compreendendo derivados de ácidos hialurônico |
-
1996
- 1996-08-29 IT IT96PD000207A patent/IT1287698B1/it active IP Right Grant
-
1997
- 1997-08-28 AU AU42080/97A patent/AU722586B2/en not_active Ceased
- 1997-08-28 AT AT97940137T patent/ATE226961T1/de not_active IP Right Cessation
- 1997-08-28 EP EP97940137A patent/EP0922060B1/en not_active Expired - Lifetime
- 1997-08-28 ES ES97940137T patent/ES2185991T3/es not_active Expired - Lifetime
- 1997-08-28 JP JP51129098A patent/JP4221734B2/ja not_active Expired - Fee Related
- 1997-08-28 DE DE69716745T patent/DE69716745T2/de not_active Expired - Lifetime
- 1997-08-28 WO PCT/EP1997/004684 patent/WO1998008876A1/en not_active Ceased
- 1997-08-28 CA CA002264085A patent/CA2264085C/en not_active Expired - Fee Related
-
1999
- 1999-01-25 US US09/236,958 patent/US20010008937A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9228027B2 (en) | 2008-09-02 | 2016-01-05 | Allergan Holdings France S.A.S. | Threads of Hyaluronic acid and/or derivatives thereof, methods of making thereof and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998008876A1 (en) | 1998-03-05 |
| IT1287698B1 (it) | 1998-08-18 |
| ITPD960207A1 (it) | 1998-03-01 |
| AU722586B2 (en) | 2000-08-10 |
| DE69716745T2 (de) | 2004-04-15 |
| EP0922060A1 (en) | 1999-06-16 |
| ES2185991T3 (es) | 2003-05-01 |
| JP2000516978A (ja) | 2000-12-19 |
| JP4221734B2 (ja) | 2009-02-12 |
| EP0922060B1 (en) | 2002-10-30 |
| ATE226961T1 (de) | 2002-11-15 |
| AU4208097A (en) | 1998-03-19 |
| US20010008937A1 (en) | 2001-07-19 |
| CA2264085A1 (en) | 1998-03-05 |
| DE69716745D1 (de) | 2002-12-05 |
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