JP2016514001A5 - - Google Patents
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- JP2016514001A5 JP2016514001A5 JP2015561873A JP2015561873A JP2016514001A5 JP 2016514001 A5 JP2016514001 A5 JP 2016514001A5 JP 2015561873 A JP2015561873 A JP 2015561873A JP 2015561873 A JP2015561873 A JP 2015561873A JP 2016514001 A5 JP2016514001 A5 JP 2016514001A5
- Authority
- JP
- Japan
- Prior art keywords
- bio
- link
- article
- formula
- biologically active
- 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.)
- Granted
Links
- 239000013543 active substance Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 230000003115 biocidal effect Effects 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- 229960003405 ciprofloxacin Drugs 0.000 claims description 10
- 239000004599 antimicrobial Substances 0.000 claims description 9
- -1 carbonate diols Carbonate diamine Chemical class 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 230000000399 orthopedic effect Effects 0.000 claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000007943 implant Substances 0.000 claims description 6
- 230000002792 vascular Effects 0.000 claims description 6
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 239000003306 quinoline derived antiinfective agent Substances 0.000 claims description 5
- XUBOMFCQGDBHNK-JTQLQIEISA-N (S)-gatifloxacin Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CCN[C@@H](C)C1 XUBOMFCQGDBHNK-JTQLQIEISA-N 0.000 claims description 4
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims description 4
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 229920002988 biodegradable polymer Polymers 0.000 claims description 4
- 239000004621 biodegradable polymer Substances 0.000 claims description 4
- 230000004071 biological effect Effects 0.000 claims description 4
- 229960003923 gatifloxacin Drugs 0.000 claims description 4
- 210000003709 heart valve Anatomy 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- 229960003376 levofloxacin Drugs 0.000 claims description 4
- 229960003702 moxifloxacin Drugs 0.000 claims description 4
- FABPRXSRWADJSP-MEDUHNTESA-N moxifloxacin Chemical compound COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 FABPRXSRWADJSP-MEDUHNTESA-N 0.000 claims description 4
- 229960001180 norfloxacin Drugs 0.000 claims description 4
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 claims description 4
- 229960001699 ofloxacin Drugs 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- OPCJOXGBLDJWRM-UHFFFAOYSA-N 1,2-diamino-2-methylpropane Chemical compound CC(C)(N)CN OPCJOXGBLDJWRM-UHFFFAOYSA-N 0.000 claims description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 2
- 241001631457 Cannula Species 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 206010019909 Hernia Diseases 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical group [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 239000002473 artificial blood Substances 0.000 claims description 2
- 229920005601 base polymer Polymers 0.000 claims description 2
- 210000004204 blood vessel Anatomy 0.000 claims description 2
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims description 2
- 239000004053 dental implant Substances 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 claims description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 210000003041 ligament Anatomy 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 239000004626 polylactic acid Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 210000003491 skin Anatomy 0.000 claims description 2
- 210000001562 sternum Anatomy 0.000 claims description 2
- 210000002435 tendon Anatomy 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000029663 wound healing Effects 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims 2
- 230000001954 sterilising effect Effects 0.000 claims 2
- 238000004659 sterilization and disinfection Methods 0.000 claims 2
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims 1
- 239000005700 Putrescine Substances 0.000 claims 1
- 229960003260 chlorhexidine Drugs 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- 239000003146 anticoagulant agent Substances 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000000227 bioadhesive Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361799859P | 2013-03-15 | 2013-03-15 | |
| US61/799,859 | 2013-03-15 | ||
| PCT/CA2014/050284 WO2014139033A1 (en) | 2013-03-15 | 2014-03-17 | Compounds and compositions for drug release |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018167744A Division JP2019030671A (ja) | 2013-03-15 | 2018-09-07 | 薬物放出のための化合物及び組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016514001A JP2016514001A (ja) | 2016-05-19 |
| JP2016514001A5 true JP2016514001A5 (https=) | 2017-02-09 |
| JP6518198B2 JP6518198B2 (ja) | 2019-05-22 |
Family
ID=51535750
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015561873A Active JP6518198B2 (ja) | 2013-03-15 | 2014-03-17 | 薬物放出のための化合物及び組成物 |
| JP2018167744A Pending JP2019030671A (ja) | 2013-03-15 | 2018-09-07 | 薬物放出のための化合物及び組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018167744A Pending JP2019030671A (ja) | 2013-03-15 | 2018-09-07 | 薬物放出のための化合物及び組成物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20160038651A1 (https=) |
| EP (2) | EP3357522B1 (https=) |
| JP (2) | JP6518198B2 (https=) |
| CN (1) | CN105377319B (https=) |
| CA (1) | CA2906238A1 (https=) |
| DK (1) | DK3357522T3 (https=) |
| ES (2) | ES2665425T3 (https=) |
| WO (1) | WO2014139033A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111971292B (zh) | 2018-02-02 | 2024-12-13 | 波纹疗法公司 | 包含类固醇二聚体的玻璃制剂及其用途 |
| EP3796948A4 (en) * | 2018-05-22 | 2022-03-02 | Interface Biologics Inc. | COMPOSITIONS AND METHODS FOR ADMINISTRATION OF MEDICATIONS TO A VESSEL WALL |
| CN108774315A (zh) * | 2018-06-27 | 2018-11-09 | 湖南华腾制药有限公司 | Peg化诺氟沙星及其抑菌应用 |
| WO2020154815A1 (en) | 2019-02-01 | 2020-08-06 | Ripple Therapeutics Corporation | Crystalline forms of dexamethasone dimers and uses thereof |
| CN114599406A (zh) * | 2019-07-10 | 2022-06-07 | 波纹疗法公司 | 包含二聚类固醇前药的表面涂层和可植入装置及其用途 |
| JP2022541341A (ja) * | 2019-07-25 | 2022-09-22 | リップル セラピューティクス コーポレーション | ステロイド二量体を含む物品と治療剤の送達におけるそれらの使用 |
| WO2021024041A1 (en) | 2019-08-07 | 2021-02-11 | Ripple Therapeutics Corporation | Controlled release drug dimers |
| MX2022013665A (es) | 2020-05-01 | 2022-11-30 | Ripple Therapeutics Corp | Composiciones y metodos heterodimeros para el tratamiento de trastornos oculares. |
| CN116763993B (zh) * | 2023-07-04 | 2024-10-08 | 四川大学 | 一种由炎症微环境介导的药物响应释放仿生心脏瓣膜及其制备方法和用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1768345B2 (de) * | 1968-05-03 | 1976-12-02 | Hoechst Ag, 6000 Frankfurt | Dimere steroid-21-alkylcarbonate und verfahren zu ihrer herstellung |
| US5217493A (en) * | 1992-03-11 | 1993-06-08 | Board Of Regents, The University Of Texas System | Antibacterial coated medical implants |
| DE19521642C2 (de) * | 1995-06-14 | 2000-11-09 | Aesculap Ag & Co Kg | Implantat, seine Verwendung in der Chirurgie und Verfahren zu seiner Herstellung |
| KR0176334B1 (ko) * | 1996-08-19 | 1999-04-01 | 박원훈 | 내인체 감염성 삽입금속표면의 코팅방법 및 그 치료기술 |
| WO2002087586A1 (en) * | 2001-04-26 | 2002-11-07 | Control Delivery Systems, Inc. | Sustained release drug delivery system containing codrugs |
| AUPR879601A0 (en) * | 2001-11-09 | 2001-12-06 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
| US20050220841A1 (en) * | 2004-04-06 | 2005-10-06 | Dewitt David M | Coating compositions for bioactive agents |
| CA2571320C (en) * | 2004-05-14 | 2016-05-10 | Paul J. Santerre | Polymeric coupling agents and pharmaceutically-active polymers made therefrom |
| WO2005110485A1 (en) * | 2004-05-14 | 2005-11-24 | Interface Biologics Inc. | Polymeric coupling agents and pharmaceutically-active polymers made therefrom |
| CA2467321A1 (en) * | 2004-05-14 | 2005-11-14 | Paul J. Santerre | Polymeric coupling agents and pharmaceutically-active polymers made therefrom |
| US8414909B2 (en) * | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8357385B2 (en) * | 2008-04-07 | 2013-01-22 | Interface Biologics Inc. | Combination therapy for the treatment of bacterial infections |
| MY155629A (en) * | 2008-10-10 | 2015-11-13 | Polyactiva Pty Ltd | Biodegradable polymer-bioactive moiety conjugates |
-
2014
- 2014-03-17 DK DK17206101.2T patent/DK3357522T3/da active
- 2014-03-17 EP EP17206101.2A patent/EP3357522B1/en active Active
- 2014-03-17 ES ES14764271.4T patent/ES2665425T3/es active Active
- 2014-03-17 JP JP2015561873A patent/JP6518198B2/ja active Active
- 2014-03-17 ES ES17206101T patent/ES2773179T3/es active Active
- 2014-03-17 US US14/776,903 patent/US20160038651A1/en not_active Abandoned
- 2014-03-17 EP EP14764271.4A patent/EP2968698B1/en not_active Not-in-force
- 2014-03-17 CN CN201480027630.6A patent/CN105377319B/zh active Active
- 2014-03-17 CA CA2906238A patent/CA2906238A1/en not_active Abandoned
- 2014-03-17 WO PCT/CA2014/050284 patent/WO2014139033A1/en not_active Ceased
-
2018
- 2018-09-07 JP JP2018167744A patent/JP2019030671A/ja active Pending
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