CA2247199A1 - Nonpolymeric epoxy compounds for cross-linking biological tissue and bioprosthetic grafts prepared thereby - Google Patents
Nonpolymeric epoxy compounds for cross-linking biological tissue and bioprosthetic grafts prepared thereby Download PDFInfo
- Publication number
- CA2247199A1 CA2247199A1 CA002247199A CA2247199A CA2247199A1 CA 2247199 A1 CA2247199 A1 CA 2247199A1 CA 002247199 A CA002247199 A CA 002247199A CA 2247199 A CA2247199 A CA 2247199A CA 2247199 A1 CA2247199 A1 CA 2247199A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- collagen
- general formula
- group
- containing tissue
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 79
- 238000004132 cross linking Methods 0.000 title claims abstract description 27
- 239000004593 Epoxy Substances 0.000 title abstract description 12
- 102000008186 Collagen Human genes 0.000 claims abstract description 58
- 108010035532 Collagen Proteins 0.000 claims abstract description 58
- 229920001436 collagen Polymers 0.000 claims abstract description 58
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 16
- 239000000039 congener Substances 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 11
- 125000003172 aldehyde group Chemical group 0.000 claims abstract description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 7
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 7
- 239000012535 impurity Substances 0.000 claims abstract description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 239000012634 fragment Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 15
- 210000003709 heart valve Anatomy 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 210000004204 blood vessel Anatomy 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 210000002435 tendon Anatomy 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- CQSITKXTEXZHKP-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)but-1-enoxymethyl]oxirane Chemical compound C1OC1COCCC=COCC1CO1 CQSITKXTEXZHKP-UHFFFAOYSA-N 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 abstract description 15
- -1 congeners Chemical class 0.000 abstract description 6
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 abstract 1
- 210000001519 tissue Anatomy 0.000 description 56
- 239000000126 substance Substances 0.000 description 22
- 239000000834 fixative Substances 0.000 description 16
- KATAXDCYPGGJNJ-UHFFFAOYSA-N 1,3-bis(oxiran-2-ylmethoxy)propan-2-ol Chemical compound C1OC1COCC(O)COCC1CO1 KATAXDCYPGGJNJ-UHFFFAOYSA-N 0.000 description 11
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 11
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 10
- 238000003556 assay Methods 0.000 description 9
- 238000002513 implantation Methods 0.000 description 9
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000002308 calcification Effects 0.000 description 5
- 210000002808 connective tissue Anatomy 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 210000003516 pericardium Anatomy 0.000 description 5
- 229920001184 polypeptide Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 102000004196 processed proteins & peptides Human genes 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 4
- 239000012620 biological material Substances 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 238000007792 addition Methods 0.000 description 3
- 230000004075 alteration Effects 0.000 description 3
- 238000010382 chemical cross-linking Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- 102000016942 Elastin Human genes 0.000 description 2
- 108010014258 Elastin Proteins 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000003872 anastomosis Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 238000012217 deletion Methods 0.000 description 2
- 230000037430 deletion Effects 0.000 description 2
- 229920002549 elastin Polymers 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical group CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920002085 Dialdehyde starch Polymers 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ISZIECUHZQGAPV-UHFFFAOYSA-N NP(O)(=O)OP(O)=O Chemical compound NP(O)(=O)OP(O)=O ISZIECUHZQGAPV-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 210000001765 aortic valve Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000001453 nonthrombogenic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000003319 supportive effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000003954 umbilical cord Anatomy 0.000 description 1
- 238000012800 visualization Methods 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/36—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix
- A61L27/3683—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix subjected to a specific treatment prior to implantation, e.g. decellularising, demineralising, grinding, cellular disruption/non-collagenous protein removal, anti-calcification, crosslinking, supercritical fluid extraction, enzyme treatment
- A61L27/3687—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix subjected to a specific treatment prior to implantation, e.g. decellularising, demineralising, grinding, cellular disruption/non-collagenous protein removal, anti-calcification, crosslinking, supercritical fluid extraction, enzyme treatment characterised by the use of chemical agents in the treatment, e.g. specific enzymes, detergents, capping agents, crosslinkers, anticalcification 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/22—Polypeptides or derivatives thereof, e.g. degradation products
- A61L27/24—Collagen
-
- 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
- A61L27/36—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix
- A61L27/3604—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix characterised by the human or animal origin of the biological material, e.g. hair, fascia, fish scales, silk, shellac, pericardium, pleura, renal tissue, amniotic membrane, parenchymal tissue, fetal tissue, muscle tissue, fat tissue, enamel
-
- 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
- A61L27/36—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix
- A61L27/3604—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix characterised by the human or animal origin of the biological material, e.g. hair, fascia, fish scales, silk, shellac, pericardium, pleura, renal tissue, amniotic membrane, parenchymal tissue, fetal tissue, muscle tissue, fat tissue, enamel
- A61L27/362—Skin, e.g. dermal papillae
-
- 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
- A61L27/36—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix
- A61L27/3604—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix characterised by the human or animal origin of the biological material, e.g. hair, fascia, fish scales, silk, shellac, pericardium, pleura, renal tissue, amniotic membrane, parenchymal tissue, fetal tissue, muscle tissue, fat tissue, enamel
- A61L27/3625—Vascular tissue, e.g. heart valves
-
- 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
- A61L27/36—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix
- A61L27/3641—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix characterised by the site of application in the body
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H1/00—Macromolecular products derived from proteins
- C08H1/06—Macromolecular products derived from proteins derived from horn, hoofs, hair, skin or leather
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2310/00—Prostheses classified in A61F2/28 or A61F2/30 - A61F2/44 being constructed from or coated with a particular material
- A61F2310/00005—The prosthesis being constructed from a particular material
- A61F2310/00365—Proteins; Polypeptides; Degradation products thereof
-
- 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
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/40—Preparation and treatment of biological tissue for implantation, e.g. decellularisation, cross-linking
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Transplantation (AREA)
- Dermatology (AREA)
- Botany (AREA)
- Molecular Biology (AREA)
- Zoology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60801496A | 1996-03-04 | 1996-03-04 | |
| US08/608,014 | 1996-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2247199A1 true CA2247199A1 (en) | 1997-09-12 |
Family
ID=24434668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002247199A Abandoned CA2247199A1 (en) | 1996-03-04 | 1997-03-03 | Nonpolymeric epoxy compounds for cross-linking biological tissue and bioprosthetic grafts prepared thereby |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5880242A (enExample) |
| EP (1) | EP0888142B1 (enExample) |
| JP (1) | JP2000506050A (enExample) |
| CA (1) | CA2247199A1 (enExample) |
| DE (1) | DE69722388T2 (enExample) |
| WO (1) | WO1997032615A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8901078B2 (en) | 2011-07-28 | 2014-12-02 | Harbor Medtech, Inc. | Crosslinked human or animal tissue products and their methods of manufacture and use |
| US12102731B2 (en) | 2020-05-01 | 2024-10-01 | Harbor Medtech, Inc. | Port-accessible multidirectional reinforced minimally invasive collagen device for soft tissue repair |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6254564B1 (en) | 1998-09-10 | 2001-07-03 | Percardia, Inc. | Left ventricular conduit with blood vessel graft |
| US6106555A (en) * | 1998-12-15 | 2000-08-22 | Av Healing Llc | Method for tissue fixation |
| DE10010074B4 (de) | 2000-02-28 | 2005-04-14 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Vorrichtung zur Befestigung und Verankerung von Herzklappenprothesen |
| DE10010073B4 (de) | 2000-02-28 | 2005-12-22 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verankerung für implantierbare Herzklappenprothesen |
| DE10060660A1 (de) * | 2000-12-06 | 2002-06-20 | Frey Rainer | Verfahren zur Konservierung von biologischen Prothesen, konservierte biologische Prothese und Konservierungslösung |
| US6468660B2 (en) | 2000-12-29 | 2002-10-22 | St. Jude Medical, Inc. | Biocompatible adhesives |
| US20020177223A1 (en) * | 2001-03-12 | 2002-11-28 | Ogle Mathew F. | Methods and compositions for crosslinking tissue |
| FR2828263B1 (fr) | 2001-08-03 | 2007-05-11 | Philipp Bonhoeffer | Dispositif d'implantation d'un implant et procede d'implantation du dispositif |
| US6761735B2 (en) * | 2002-04-25 | 2004-07-13 | Medtronic, Inc. | Heart valve fixation process and apparatus |
| FR2873927B1 (fr) * | 2004-08-05 | 2007-05-11 | Symatese Soc Par Actions Simpl | Procede de preparation de collagene reticule et substitut osseux comprenant ledit collagene ainsi reticule |
| DE102005003632A1 (de) | 2005-01-20 | 2006-08-17 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Katheter für die transvaskuläre Implantation von Herzklappenprothesen |
| ZA200800144B (en) * | 2005-06-10 | 2010-02-24 | Celgene Corp | Human placental collagen compositions, processes for their preparation, methods of their use and kits comprising the compositions |
| DE102005051849B4 (de) | 2005-10-28 | 2010-01-21 | JenaValve Technology Inc., Wilmington | Vorrichtung zur Implantation und Befestigung von Herzklappenprothesen |
| DE102005052628B4 (de) | 2005-11-04 | 2014-06-05 | Jenavalve Technology Inc. | Selbstexpandierendes, flexibles Drahtgeflecht mit integrierter Klappenprothese für den transvaskulären Herzklappenersatz und ein System mit einer solchen Vorrichtung und einem Einführkatheter |
| CN1986001B (zh) * | 2005-12-20 | 2011-09-14 | 广东冠昊生物科技股份有限公司 | 生物护创膜 |
| CN1986006A (zh) * | 2005-12-20 | 2007-06-27 | 广州知光生物科技有限公司 | 生物型神经导管 |
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- 1997-03-03 CA CA002247199A patent/CA2247199A1/en not_active Abandoned
- 1997-03-03 DE DE69722388T patent/DE69722388T2/de not_active Expired - Lifetime
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| US8901078B2 (en) | 2011-07-28 | 2014-12-02 | Harbor Medtech, Inc. | Crosslinked human or animal tissue products and their methods of manufacture and use |
| US9220808B2 (en) | 2011-07-28 | 2015-12-29 | Harbor Medtech, Inc. | Crosslinked human or animal tissue products and their methods of manufacture and use |
| US9399084B2 (en) | 2011-07-28 | 2016-07-26 | Harbor Medtech, Inc. | Crosslinked human or animal tissue products and their methods of manufacture and use |
| US9592320B2 (en) | 2011-07-28 | 2017-03-14 | Harbor Medtech, Inc. | Crosslinked human or animal tissue products and their methods of manufacture and use |
| US10611822B2 (en) | 2011-07-28 | 2020-04-07 | Harbor Medtech, Inc. | Crosslinked human or animal tissue products and their methods of manufacture and use |
| US12065480B2 (en) | 2011-07-28 | 2024-08-20 | Harbor Medtech, Inc. | Crosslinked human or animal tissue products and their methods of manufacture and use |
| US12102731B2 (en) | 2020-05-01 | 2024-10-01 | Harbor Medtech, Inc. | Port-accessible multidirectional reinforced minimally invasive collagen device for soft tissue repair |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1997032615A1 (en) | 1997-09-12 |
| EP0888142B1 (en) | 2003-05-28 |
| DE69722388D1 (de) | 2003-07-03 |
| EP0888142A1 (en) | 1999-01-07 |
| JP2000506050A (ja) | 2000-05-23 |
| US5880242A (en) | 1999-03-09 |
| DE69722388T2 (de) | 2004-04-22 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |