CA2909069C - Coatings for controlled release of highly water soluble drugs - Google Patents
Coatings for controlled release of highly water soluble drugs Download PDFInfo
- Publication number
- CA2909069C CA2909069C CA2909069A CA2909069A CA2909069C CA 2909069 C CA2909069 C CA 2909069C CA 2909069 A CA2909069 A CA 2909069A CA 2909069 A CA2909069 A CA 2909069A CA 2909069 C CA2909069 C CA 2909069C
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- CA
- Canada
- Prior art keywords
- drug
- layer
- water soluble
- polymer
- encasing
- 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.)
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- 229940079593 drug Drugs 0.000 title claims abstract description 250
- 239000003814 drug Substances 0.000 title claims abstract description 250
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 111
- 238000000576 coating method Methods 0.000 title claims abstract description 106
- 238000013270 controlled release Methods 0.000 title claims abstract description 16
- 239000011248 coating agent Substances 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 40
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- 229920000642 polymer Polymers 0.000 claims description 91
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 89
- 239000000758 substrate Substances 0.000 claims description 87
- 125000005647 linker group Chemical group 0.000 claims description 39
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 27
- 239000007864 aqueous solution Substances 0.000 claims description 25
- 239000011230 binding agent Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 claims description 19
- 229960003333 chlorhexidine gluconate Drugs 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
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- ZDEIQGWACCNREP-UHFFFAOYSA-N 1-azido-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(N=[N+]=[N-])C(F)=C1F ZDEIQGWACCNREP-UHFFFAOYSA-N 0.000 description 3
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 238000006116 polymerization reaction Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
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- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,4-dimethylpentane Chemical compound CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
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- 229920005603 alternating copolymer Polymers 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 2
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- 238000003618 dip coating Methods 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Heart & Thoracic Surgery (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Materials For Medical Uses (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Laminated Bodies (AREA)
- Polymers & Plastics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361815910P | 2013-04-25 | 2013-04-25 | |
| US61/815,910 | 2013-04-25 | ||
| PCT/US2014/035527 WO2014176545A1 (en) | 2013-04-25 | 2014-04-25 | Coatings for controlled release of highly water soluble drugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2909069A1 CA2909069A1 (en) | 2014-10-30 |
| CA2909069C true CA2909069C (en) | 2018-10-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2909069A Active CA2909069C (en) | 2013-04-25 | 2014-04-25 | Coatings for controlled release of highly water soluble drugs |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9814805B2 (enExample) |
| EP (1) | EP2988730A4 (enExample) |
| JP (1) | JP6255483B2 (enExample) |
| CN (1) | CN105283169B (enExample) |
| AU (1) | AU2014256955B2 (enExample) |
| CA (1) | CA2909069C (enExample) |
| WO (1) | WO2014176545A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2909069C (en) * | 2013-04-25 | 2018-10-16 | Innovative Surface Technologies, Inc. | Coatings for controlled release of highly water soluble drugs |
| WO2017147521A1 (en) * | 2016-02-24 | 2017-08-31 | Innovative Surface Technologies, Inc. | Crystallization inhibitor compositions for implantable urological devices |
| US10450119B2 (en) | 2017-06-22 | 2019-10-22 | The Procter & Gamble Company | Films including a water-soluble layer and a vapor-deposited inorganic coating |
| US11192139B2 (en) * | 2017-06-22 | 2021-12-07 | The Procter & Gamble Company | Films including a water-soluble layer and a vapor-deposited organic coating |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5002582A (en) | 1982-09-29 | 1991-03-26 | Bio-Metric Systems, Inc. | Preparation of polymeric surfaces via covalently attaching polymers |
| US5271945A (en) | 1988-07-05 | 1993-12-21 | Takeda Chemical Industries, Ltd. | Sustained release microcapsule for water soluble drug |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| US6120536A (en) | 1995-04-19 | 2000-09-19 | Schneider (Usa) Inc. | Medical devices with long term non-thrombogenic coatings |
| US5714360A (en) | 1995-11-03 | 1998-02-03 | Bsi Corporation | Photoactivatable water soluble cross-linking agents containing an onium group |
| US5980972A (en) * | 1996-12-20 | 1999-11-09 | Schneider (Usa) Inc | Method of applying drug-release coatings |
| US7682647B2 (en) | 1999-09-03 | 2010-03-23 | Advanced Cardiovascular Systems, Inc. | Thermal treatment of a drug eluting implantable medical device |
| US6790228B2 (en) * | 1999-12-23 | 2004-09-14 | Advanced Cardiovascular Systems, Inc. | Coating for implantable devices and a method of forming the same |
| US6278018B1 (en) | 1999-12-14 | 2001-08-21 | Surmodics, Inc. | Surface coating agents |
| EP1531875B1 (en) * | 2002-08-13 | 2010-03-03 | Medtronic, Inc. | Active agent delivery system including a poly(ethylene-co-(meth)acrylate), medical device, and method |
| EP1567207A1 (en) | 2002-11-08 | 2005-08-31 | Conor Medsystems, Inc. | Method and apparatus for treating vulnerable artherosclerotic plaque |
| EP1633320A2 (en) | 2003-05-02 | 2006-03-15 | SurModics, Inc. | Implantable controlled release bioactive agent delivery device |
| US7811274B2 (en) | 2003-05-07 | 2010-10-12 | Portaero, Inc. | Method for treating chronic obstructive pulmonary disease |
| US20050100577A1 (en) | 2003-11-10 | 2005-05-12 | Parker Theodore L. | Expandable medical device with beneficial agent matrix formed by a multi solvent system |
| CA2563069A1 (en) | 2004-04-06 | 2005-10-27 | Surmodics, Inc. | Coating compositions for bioactive agents |
| US7901451B2 (en) * | 2004-09-24 | 2011-03-08 | Biosensors International Group, Ltd. | Drug-delivery endovascular stent and method for treating restenosis |
| WO2008039749A2 (en) | 2006-09-25 | 2008-04-03 | Surmodics, Inc. | Multi-layered coatings and methods for controlling elution of active agents |
| US8163034B2 (en) | 2007-05-11 | 2012-04-24 | Portaero, Inc. | Methods and devices to create a chemically and/or mechanically localized pleurodesis |
| WO2013033159A1 (en) * | 2011-08-31 | 2013-03-07 | The Trustees Of Columbia University In The City Of New York | Reduction of biofilms on medical devices |
| CN102112139A (zh) | 2007-10-30 | 2011-06-29 | 乌第有限合伙公司 | 用于持续释放硬化剂的方法和系统 |
| WO2009128944A2 (en) | 2008-04-18 | 2009-10-22 | Surmodics, Inc. | Coating systems for the controlled delivery of hydrophilic bioactive agents |
| AU2009293445A1 (en) | 2008-09-19 | 2010-03-25 | Innovative Surface Technologies, Inc. | Drug eluting superhydrophobic coatings |
| JP2013514841A (ja) * | 2009-12-21 | 2013-05-02 | イノベイティブ サーフェイス テクノロジーズ， インコーポレイテッド | コーティング剤およびコーティングされた物品 |
| US20110159072A1 (en) | 2009-12-30 | 2011-06-30 | Surmodics, Inc. | Controlled release matrix |
| US20120100187A1 (en) | 2010-10-26 | 2012-04-26 | Surmodics, Inc. | Coatings and methods for controlled elution of hydrophilic active agents |
| US20120302950A1 (en) | 2011-05-26 | 2012-11-29 | Carefusion 2200, Inc. | Active pleurodesis catheter |
| US8697112B2 (en) * | 2011-07-08 | 2014-04-15 | Covalon Technologies | Method for treating a surface with a coating comprising a microencapsulated therapeutic agent and device with treated surface |
| CA2909069C (en) * | 2013-04-25 | 2018-10-16 | Innovative Surface Technologies, Inc. | Coatings for controlled release of highly water soluble drugs |
-
2014
- 2014-04-25 CA CA2909069A patent/CA2909069C/en active Active
- 2014-04-25 WO PCT/US2014/035527 patent/WO2014176545A1/en not_active Ceased
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- 2014-04-25 CN CN201480028712.2A patent/CN105283169B/zh not_active Expired - Fee Related
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2017
- 2017-10-11 US US15/730,006 patent/US10098989B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US10098989B2 (en) | 2018-10-16 |
| JP2016517870A (ja) | 2016-06-20 |
| CN105283169A (zh) | 2016-01-27 |
| US20180043063A1 (en) | 2018-02-15 |
| WO2014176545A1 (en) | 2014-10-30 |
| AU2014256955B2 (en) | 2018-02-22 |
| US20160067385A1 (en) | 2016-03-10 |
| JP6255483B2 (ja) | 2017-12-27 |
| CN105283169B (zh) | 2018-11-30 |
| AU2014256955A1 (en) | 2015-12-03 |
| EP2988730A4 (en) | 2017-03-29 |
| US9814805B2 (en) | 2017-11-14 |
| CA2909069A1 (en) | 2014-10-30 |
| EP2988730A1 (en) | 2016-03-02 |
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