CA2449964A1 - Crosslinkable macromers - Google Patents
Crosslinkable macromers Download PDFInfo
- Publication number
- CA2449964A1 CA2449964A1 CA002449964A CA2449964A CA2449964A1 CA 2449964 A1 CA2449964 A1 CA 2449964A1 CA 002449964 A CA002449964 A CA 002449964A CA 2449964 A CA2449964 A CA 2449964A CA 2449964 A1 CA2449964 A1 CA 2449964A1
- Authority
- CA
- Canada
- Prior art keywords
- groups
- group
- polymer
- tissue
- macromer
- 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.)
- Abandoned
Links
- 239000003999 initiator Substances 0.000 claims abstract description 97
- 229920000642 polymer Polymers 0.000 claims abstract description 75
- 239000007943 implant Substances 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 50
- 239000011159 matrix material Substances 0.000 claims abstract description 49
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000004676 glycans Chemical class 0.000 claims abstract description 10
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 10
- 239000005017 polysaccharide Substances 0.000 claims abstract description 10
- 230000008467 tissue growth Effects 0.000 claims abstract description 4
- 210000001519 tissue Anatomy 0.000 claims description 108
- 238000006116 polymerization reaction Methods 0.000 claims description 32
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- 108010035532 Collagen Proteins 0.000 claims description 29
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- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 24
- 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 claims description 23
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- -1 benzoin ethers Chemical class 0.000 claims description 9
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- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 8
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 claims description 8
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 7
- 239000012965 benzophenone Substances 0.000 claims description 7
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 7
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 claims description 6
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- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 5
- 229960002086 dextran Drugs 0.000 claims description 5
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 claims description 5
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- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 claims description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical group OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 5
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- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 claims description 5
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical group CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 claims description 4
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 4
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 4
- 229920001661 Chitosan Polymers 0.000 claims description 4
- 229920001287 Chondroitin sulfate Polymers 0.000 claims description 4
- 229920000045 Dermatan sulfate Polymers 0.000 claims description 4
- 102000016942 Elastin Human genes 0.000 claims description 4
- 108010014258 Elastin Proteins 0.000 claims description 4
- 102000016359 Fibronectins Human genes 0.000 claims description 4
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- 102000007547 Laminin Human genes 0.000 claims description 4
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- 229920002472 Starch Polymers 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
- LBSPZZSGTIBOFG-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;dihydrochloride Chemical compound Cl.Cl.N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LBSPZZSGTIBOFG-UHFFFAOYSA-N 0.000 claims description 4
- 229940045110 chitosan Drugs 0.000 claims description 4
- 229940059329 chondroitin sulfate Drugs 0.000 claims description 4
- 229940051593 dermatan sulfate Drugs 0.000 claims description 4
- AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 claims description 4
- 229960000633 dextran sulfate Drugs 0.000 claims description 4
- 229920002549 elastin Polymers 0.000 claims description 4
- UKZQEOHHLOYJLY-UHFFFAOYSA-M ethyl eosin Chemical compound [K+].CCOC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 UKZQEOHHLOYJLY-UHFFFAOYSA-M 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
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- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 claims 3
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- KXCLCNHUUKTANI-RBIYJLQWSA-N keratan Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H]([C@@H](COS(O)(=O)=O)O[C@@H](O)[C@@H]3O)O)[C@H](NC(C)=O)[C@H]2O)COS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@@H]1O KXCLCNHUUKTANI-RBIYJLQWSA-N 0.000 claims 3
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- 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
- A61L31/08—Materials for coatings
- A61L31/10—Macromolecular materials
-
- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
- A61L24/0031—Hydrogels or hydrocolloids
-
- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/28—Materials for coating prostheses
- A61L27/34—Macromolecular materials
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Surgery (AREA)
- Transplantation (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Materials Engineering (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Materials For Medical Uses (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2001/018345 WO2002100453A1 (en) | 2001-06-07 | 2001-06-07 | Crosslinkable macromers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2449964A1 true CA2449964A1 (en) | 2002-12-19 |
Family
ID=21742629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002449964A Abandoned CA2449964A1 (en) | 2001-06-07 | 2001-06-07 | Crosslinkable macromers |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1395301A1 (enExample) |
| JP (1) | JP2005508663A (enExample) |
| CA (1) | CA2449964A1 (enExample) |
| MX (1) | MXPA03011263A (enExample) |
| WO (1) | WO2002100453A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004208821B2 (en) * | 2003-01-31 | 2009-01-15 | Zimmer Orthobiologics Inc. | Hydrogel compositions comprising nucleus pulposus tissue |
| WO2004076511A2 (en) * | 2003-02-21 | 2004-09-10 | Ciphergen Biosystems, Inc. | Photocrosslinked hydrogel surface coatings |
| US7169404B2 (en) | 2003-07-30 | 2007-01-30 | Advanced Cardiovasular Systems, Inc. | Biologically absorbable coatings for implantable devices and methods for fabricating the same |
| US8202833B2 (en) * | 2003-11-26 | 2012-06-19 | Surmodics, Inc. | Composition containing biocompatible polymerization accelerator and polymerizable material |
| DE102004011497B4 (de) * | 2004-03-09 | 2008-05-21 | Ivoclar Vivadent Ag | Dentalwerkstoffe mit verbesserter Verträglichkeit |
| EP1807133B1 (en) | 2004-10-28 | 2013-12-11 | SurModics, Inc. | Pro-fibrotic coatings |
| WO2006138542A2 (en) * | 2005-06-15 | 2006-12-28 | Surmodics, Inc. | Macromer composition including light activated initiator |
| WO2007040557A1 (en) * | 2005-09-21 | 2007-04-12 | Surmodics, Inc. | Coatings and articles including natural biodegradable polysaccharides |
| US8999377B2 (en) * | 2007-09-19 | 2015-04-07 | Surmodics, Inc. | System for forming a biocompatible foam using polymerizable alpha(1-4)glucopyranose polymers and gas-producing component |
| US8283384B2 (en) * | 2008-01-24 | 2012-10-09 | University Of Utah Research Foundation | Adhesive complex coacervates and methods of making and using thereof |
| BRPI0822229A2 (pt) | 2008-01-24 | 2015-06-23 | Univ Utah Res Foudation | Coacervados de complexos adesivo e métodos de fabricação e uso dos mesmos |
| US8916188B2 (en) | 2008-04-18 | 2014-12-23 | Abbott Cardiovascular Systems Inc. | Block copolymer comprising at least one polyester block and a poly (ethylene glycol) block |
| JP2012506478A (ja) * | 2008-10-22 | 2012-03-15 | サーモディクス，インコーポレイティド | 膨潤性および生分解性を有するポリマーマトリクス並びにその製造方法 |
| CN103025360A (zh) | 2010-05-24 | 2013-04-03 | 犹他大学研究基金会 | 增强的粘合剂复合物凝聚层和其制备和使用方法 |
| WO2012065148A2 (en) | 2010-11-12 | 2012-05-18 | University Of Utah Research Foundation | Simple adhesive coacervates and methods of making and using thereof |
| WO2014123665A1 (en) | 2013-02-06 | 2014-08-14 | Kci Licensing, Inc. | Polymers, preparation and use thereof |
| EP2958947B1 (en) * | 2013-02-20 | 2019-08-14 | The University of Queensland | Conjugate compound and uses of same |
| JP6742297B2 (ja) | 2014-07-14 | 2020-08-19 | ユニヴァーシティ オブ ユタ リサーチ ファンデーション | その場凝固複合コアセルベートならびにその製造および使用方法 |
| AU2019212513B2 (en) | 2018-01-26 | 2024-10-31 | Fluidx Medical Technology, Llc | Apparatus and method of using in situ solidifying complex coacervates for vascular occlusion |
| BR112020025527B1 (pt) * | 2018-06-11 | 2023-10-03 | Universidade De Coimbra | Formulações de copolímero biodegradável fotopolimerizado para aplicações biomédicas |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0169001A3 (en) * | 1984-07-17 | 1987-11-25 | Collagen Corporation | Collagen coated bone implants |
| US5529914A (en) * | 1990-10-15 | 1996-06-25 | The Board Of Regents The Univeristy Of Texas System | Gels for encapsulation of biological materials |
| JP2000503053A (ja) * | 1995-12-29 | 2000-03-14 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | ポリマー先駆物質の光反応性側鎖部分を使用して親水性感圧接着剤配合物を製造する方法 |
| US6007833A (en) * | 1998-03-19 | 1999-12-28 | Surmodics, Inc. | Crosslinkable macromers bearing initiator groups |
-
2001
- 2001-06-07 CA CA002449964A patent/CA2449964A1/en not_active Abandoned
- 2001-06-07 EP EP01942016A patent/EP1395301A1/en not_active Withdrawn
- 2001-06-07 JP JP2003503270A patent/JP2005508663A/ja active Pending
- 2001-06-07 MX MXPA03011263A patent/MXPA03011263A/es not_active Application Discontinuation
- 2001-06-07 WO PCT/US2001/018345 patent/WO2002100453A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1395301A1 (en) | 2004-03-10 |
| JP2005508663A (ja) | 2005-04-07 |
| MXPA03011263A (es) | 2004-02-26 |
| WO2002100453A1 (en) | 2002-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |