JP2002539275A5 - - Google Patents
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- Publication number
- JP2002539275A5 JP2002539275A5 JP2000543082A JP2000543082A JP2002539275A5 JP 2002539275 A5 JP2002539275 A5 JP 2002539275A5 JP 2000543082 A JP2000543082 A JP 2000543082A JP 2000543082 A JP2000543082 A JP 2000543082A JP 2002539275 A5 JP2002539275 A5 JP 2002539275A5
- Authority
- JP
- Japan
- Prior art keywords
- poly
- composition
- fumarate
- average molecular
- molecular weight
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 description 13
- 229920001299 polypropylene fumarate Polymers 0.000 description 11
- 239000002516 radical scavenger Substances 0.000 description 7
- CTEFDDZVRLFMNT-NSCUHMNNSA-N (e)-4-(3-hydroxypropoxy)-4-oxobut-2-enoic acid Chemical compound OCCCOC(=O)\C=C\C(O)=O CTEFDDZVRLFMNT-NSCUHMNNSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 3
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- -1 alkaline earth metal carbonate Chemical class 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical group [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8140598P | 1998-04-10 | 1998-04-10 | |
| US8130898P | 1998-04-10 | 1998-04-10 | |
| US60/081,405 | 1998-04-10 | ||
| US60/081,308 | 1998-04-10 | ||
| US8218298P | 1998-04-16 | 1998-04-16 | |
| US60/082,182 | 1998-04-16 | ||
| PCT/US1999/007912 WO1999052469A1 (en) | 1998-04-10 | 1999-04-09 | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002539275A JP2002539275A (ja) | 2002-11-19 |
| JP2002539275A5 true JP2002539275A5 (enExample) | 2006-06-15 |
Family
ID=27373944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000543082A Pending JP2002539275A (ja) | 1998-04-10 | 1999-04-09 | プロトンスカベンジャの存在下でのプロピレングリコールのアシル化によるポリ（プロピレンフマラート）の合成 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6124373A (enExample) |
| EP (1) | EP1079869B1 (enExample) |
| JP (1) | JP2002539275A (enExample) |
| AT (1) | ATE291444T1 (enExample) |
| CA (1) | CA2327730A1 (enExample) |
| DE (1) | DE69924369D1 (enExample) |
| WO (1) | WO1999052469A1 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6486232B1 (en) * | 1997-04-18 | 2002-11-26 | Cambridge Scientific, Inc. | Bioerodible polymeric semi-interpenetrating network alloys for internal fixation devices and bone cements |
| ATE291444T1 (de) | 1998-04-10 | 2005-04-15 | Univ Wm Marsh Rice | Synthese von poly(propylenfumarat)durch azetylierung von propylenglykol in anwesenheit eines protonenfängers |
| KR100696407B1 (ko) * | 1999-04-16 | 2007-03-19 | 더블유엠. 마쉬 라이스 유니버시티 | 폴리(프로필렌 푸마레이트)-디아크릴레이트 마크로머와가교결합된 생분해성 폴리(프로필렌 푸마레이트) 네트워크 |
| US6884778B2 (en) * | 2000-04-14 | 2005-04-26 | William Marsh Rice University | Biocompatible macromers |
| DE10032220A1 (de) | 2000-07-03 | 2002-01-24 | Sanatis Gmbh | Magnesium-ammonium-phosphat-Zemente, deren Herstellung und Verwendung |
| US6849223B2 (en) * | 2001-04-19 | 2005-02-01 | Case Western Reserve University | Fabrication of a polymeric prosthetic implant |
| DE60226242T2 (de) * | 2001-06-28 | 2009-05-28 | William Marsh Rice University, Houston | Photoquervernetzung von biologischen materialien aus fumarsäurediethylester/poly(propylenfumarat) |
| US7629388B2 (en) | 2001-11-20 | 2009-12-08 | William Marsh Rice University | Synthesis and characterization of biodegradable cationic poly(propylene fumarate-co-ethylene glycol) copolymer hydrogels modified with agmatine for enhanced cell adhesion |
| CA2475110C (en) * | 2002-02-05 | 2010-03-23 | Cambridge Scientific, Inc. | Bioresorbable osteoconductive compositions for bone regeneration |
| US6884432B2 (en) * | 2002-04-25 | 2005-04-26 | Mayo Foundation For Medical Education And Research | Blend, cross-linkable poly(propylene fumarate) for immobilization and controlled drug delivery |
| US7273523B2 (en) | 2002-06-07 | 2007-09-25 | Kyphon Inc. | Strontium-apatite-cement-preparations, cements formed therefrom, and uses thereof |
| US20070065652A1 (en) * | 2003-03-13 | 2007-03-22 | Willaim Marsh Rice University | Composite injectable and pre-fabricated bone replacement material and method for the production of such bone replacement material |
| WO2004080357A1 (es) | 2003-03-14 | 2004-09-23 | Ferreyro Irigoyen Roque Humber | Dispositivo hidraulico de inyección de cemento oseo en la vertebroplastiá percutánea |
| US8066713B2 (en) | 2003-03-31 | 2011-11-29 | Depuy Spine, Inc. | Remotely-activated vertebroplasty injection device |
| WO2006011152A2 (en) * | 2004-06-17 | 2006-02-02 | Disc-O-Tech Medical Technologies, Ltd. | Methods for treating bone and other tissue |
| US8415407B2 (en) | 2004-03-21 | 2013-04-09 | Depuy Spine, Inc. | Methods, materials, and apparatus for treating bone and other tissue |
| CA2528150A1 (en) * | 2003-07-01 | 2005-01-20 | Mayo Foundation For Medical Education And Research | Self-crosslinkable poly(caprolactone fumarate) |
| US7252686B2 (en) * | 2003-08-13 | 2007-08-07 | Boston Scientific Scimed | Methods for reducing bone compression fractures using wedges |
| WO2005030034A2 (en) | 2003-09-26 | 2005-04-07 | Depuy Spine, Inc. | Device for delivering viscous material |
| US20060018949A1 (en) * | 2004-04-07 | 2006-01-26 | Bausch & Lomb Incorporated | Injectable biodegradable drug delivery system |
| CN1988923B (zh) | 2004-04-27 | 2012-10-03 | 凯丰有限责任公司 | 骨替代组合物及其使用方法 |
| EP1809678B1 (en) * | 2004-11-12 | 2013-05-22 | Mayo Foundation for Medical Education and Research | Photocrosslinkable poly(caprolactone fumarate) |
| EP1812481B1 (en) * | 2004-11-18 | 2012-01-11 | Mayo Foundation for Medical Education and Research | Block copolymers of polycaprolactone and poly (propylene fumarate) |
| ATE511439T1 (de) * | 2005-04-29 | 2011-06-15 | Mayo Foundation | Hydrophile/hydrophobe polymernetze auf der basis von poly(caprolactonfumarat), poly(ethylenglycolfumarat) und copolymere davon |
| US9381024B2 (en) | 2005-07-31 | 2016-07-05 | DePuy Synthes Products, Inc. | Marked tools |
| US9918767B2 (en) | 2005-08-01 | 2018-03-20 | DePuy Synthes Products, Inc. | Temperature control system |
| US7651701B2 (en) * | 2005-08-29 | 2010-01-26 | Sanatis Gmbh | Bone cement composition and method of making the same |
| US8360629B2 (en) | 2005-11-22 | 2013-01-29 | Depuy Spine, Inc. | Mixing apparatus having central and planetary mixing elements |
| US7754005B2 (en) * | 2006-05-02 | 2010-07-13 | Kyphon Sarl | Bone cement compositions comprising an indicator agent and related methods thereof |
| US7507286B2 (en) * | 2006-06-08 | 2009-03-24 | Sanatis Gmbh | Self-foaming cement for void filling and/or delivery systems |
| EP2032191B1 (en) * | 2006-06-29 | 2015-08-12 | Depuy Spine Inc. | Integrated bone biopsy and therapy apparatus |
| AU2007297097A1 (en) | 2006-09-14 | 2008-03-20 | Depuy Spine, Inc. | Bone cement and methods of use thereof |
| AU2007300585A1 (en) * | 2006-09-21 | 2008-04-03 | Kyphon Sarl | Diammonium phosphate and other ammonium salts and their use in preventing clotting |
| CA2747850C (en) * | 2006-10-19 | 2013-05-14 | Depuy Spine, Inc. | Fluid delivery system |
| US20080195223A1 (en) * | 2006-11-03 | 2008-08-14 | Avram Allan Eddin | Materials and Methods and Systems for Delivering Localized Medical Treatments |
| DK2022446T3 (da) * | 2007-07-30 | 2012-07-23 | Purzer Pharmaceutical Co Ltd | Biologisk nedbrydeligt knoglecement og fremgangsmåde til fremstilling deraf |
| US20090286907A1 (en) * | 2008-01-23 | 2009-11-19 | Beltz Mark W | Fumaric Acid/Diol Polyesters and Their Manufacture and Use |
| US7968616B2 (en) * | 2008-04-22 | 2011-06-28 | Kyphon Sarl | Bone cement composition and method |
| CA2804842A1 (en) | 2010-07-09 | 2012-01-12 | Board Of Regents Of The University Of Texas System | Biodegradable scaffolds |
| MX366709B (es) | 2010-08-20 | 2019-07-22 | Rice Univ Star | Fabricación de implantes mediante aditivo de procesamiento de luz digital continuo. |
| US11865785B2 (en) | 2010-08-20 | 2024-01-09 | H. David Dean | Continuous digital light processing additive manufacturing of implants |
| AU2015257289B2 (en) | 2014-05-05 | 2020-10-01 | Advanced Medical Solutions Israel (Sealantis) Ltd | Biological adhesives and sealants and methods of using the same |
| EP3221379A1 (en) * | 2014-11-18 | 2017-09-27 | The University of Akron | Well-defined degradable poly(propylene fumarate) polymers and scalable methods for the synthesis thereof |
| KR20190112100A (ko) | 2017-02-02 | 2019-10-02 | 더 유니버시티 오브 아크론 | 마그네슘 촉매를 사용하는 개환 중합에 의해 제조된 작용화된 폴리(프로필렌 푸마레이트) 중합체 |
| GB2594243A (en) * | 2020-04-15 | 2021-10-27 | Arterius Ltd | A bone cement |
| WO2022015989A1 (en) * | 2020-07-15 | 2022-01-20 | The University Of Akron | Synthesis of poly (propylene maleate-co-succinate) by the time-dependent reduction of poly (propylene maleate) double bonds mediated by zinc and acetic acid |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3701748A (en) | 1966-07-20 | 1972-10-31 | Rohm & Haas | Unsaturated polyester resinous compositions |
| DE1770548A1 (de) * | 1967-06-02 | 1972-02-10 | Gen Tire & Rubber Co | Polyester und ihre Herstellung |
| US5286763A (en) * | 1983-03-22 | 1994-02-15 | Massachusetts Institute Of Technology | Bioerodible polymers for drug delivery in bone |
| US4722948A (en) * | 1984-03-16 | 1988-02-02 | Dynatech Corporation | Bone replacement and repair putty material from unsaturated polyester resin and vinyl pyrrolidone |
| US5989579A (en) | 1986-10-02 | 1999-11-23 | Escalon Medical Corp. | Ocular insert with anchoring protrusions |
| US4843112A (en) * | 1987-03-12 | 1989-06-27 | The Beth Israel Hospital Association | Bioerodable implant composition |
| US4888413A (en) | 1988-01-11 | 1989-12-19 | Domb Abraham J | Poly(propylene glycol fumarate) compositions for biomedical applications |
| FI904598A7 (fi) | 1989-10-10 | 1991-04-11 | Wrigley W M Jun Co | Kuidunkehruutekniikalla valmistetut ainetta vähitellen vapauttavat rakenteet |
| FR2661682B1 (fr) | 1990-05-04 | 1993-12-10 | Norsolor | Nouvelles compositions resineuses a base de resines polyesters non saturees et de nouveaux additifs anti-retrait. |
| NZ249770A (en) | 1992-02-28 | 1996-09-25 | Univ Texas | Biodegradable, polymerisable, substantially water soluble macromer comprising at least one water soluble region, at least one degradable region and at least two free radical polymerisable regions separated by at least one degradable region |
| US5733951A (en) * | 1994-04-28 | 1998-03-31 | Yaszemski; Michael J. | Poly(propylene fumarate) |
| US5527864A (en) * | 1995-08-08 | 1996-06-18 | Suggs; Laura J. | Poly(propylene fumarate-co-ethylene oxide) |
| DE69615811T2 (de) | 1995-12-25 | 2002-04-04 | Sharp K.K., Osaka | Abbildungssystem |
| US5998362A (en) | 1996-09-12 | 1999-12-07 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US6071982A (en) | 1997-04-18 | 2000-06-06 | Cambridge Scientific, Inc. | Bioerodible polymeric semi-interpenetrating network alloys for surgical plates and bone cements, and method for making same |
| US5854382A (en) | 1997-08-18 | 1998-12-29 | Meadox Medicals, Inc. | Bioresorbable compositions for implantable prostheses |
| ATE291444T1 (de) | 1998-04-10 | 2005-04-15 | Univ Wm Marsh Rice | Synthese von poly(propylenfumarat)durch azetylierung von propylenglykol in anwesenheit eines protonenfängers |
-
1999
- 1999-04-09 AT AT99915349T patent/ATE291444T1/de not_active IP Right Cessation
- 1999-04-09 DE DE69924369T patent/DE69924369D1/de not_active Expired - Fee Related
- 1999-04-09 EP EP99915349A patent/EP1079869B1/en not_active Expired - Lifetime
- 1999-04-09 WO PCT/US1999/007912 patent/WO1999052469A1/en not_active Ceased
- 1999-04-09 CA CA002327730A patent/CA2327730A1/en not_active Abandoned
- 1999-04-09 US US09/289,361 patent/US6124373A/en not_active Expired - Lifetime
- 1999-04-09 JP JP2000543082A patent/JP2002539275A/ja active Pending
-
2000
- 2000-10-04 US US09/678,816 patent/US6355755B1/en not_active Expired - Lifetime
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