WO2005097228A2 - Coating compositions for bioactive agents - Google Patents
Coating compositions for bioactive agents Download PDFInfo
- Publication number
- WO2005097228A2 WO2005097228A2 PCT/US2005/011655 US2005011655W WO2005097228A2 WO 2005097228 A2 WO2005097228 A2 WO 2005097228A2 US 2005011655 W US2005011655 W US 2005011655W WO 2005097228 A2 WO2005097228 A2 WO 2005097228A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- poly
- group
- meth
- bioactive agent
- composition
- Prior art date
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- 239000012867 bioactive agent Substances 0.000 title claims abstract description 226
- 239000008199 coating composition Substances 0.000 title claims abstract description 63
- 229920000642 polymer Polymers 0.000 claims abstract description 393
- 239000000203 mixture Substances 0.000 claims abstract description 263
- 238000000576 coating method Methods 0.000 claims abstract description 135
- 239000011248 coating agent Substances 0.000 claims abstract description 127
- 238000000034 method Methods 0.000 claims abstract description 75
- 238000001727 in vivo Methods 0.000 claims abstract description 34
- -1 poly(n-butyl methacrylate) Polymers 0.000 claims description 235
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 119
- 125000003118 aryl group Chemical group 0.000 claims description 105
- 229920001577 copolymer Polymers 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 50
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims description 47
- 229920001083 polybutene Polymers 0.000 claims description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
- 125000002947 alkylene group Chemical group 0.000 claims description 42
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 claims description 41
- 239000000178 monomer Substances 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 37
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 35
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 34
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 32
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims description 32
- 229960002930 sirolimus Drugs 0.000 claims description 32
- 229920000052 poly(p-xylylene) Polymers 0.000 claims description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 19
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 16
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- 239000000654 additive Substances 0.000 claims description 16
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 15
- 150000001282 organosilanes Chemical class 0.000 claims description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 14
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 11
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- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 10
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003508 Dilauryl thiodipropionate Substances 0.000 claims description 10
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 10
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- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 10
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 claims description 10
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 10
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 10
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 9
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- 229960005309 estradiol Drugs 0.000 claims description 9
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 9
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- CPPDFKVVKLWZHE-UHFFFAOYSA-N 2-methylprop-2-enoic acid;phenoxybenzene Chemical compound CC(=C)C(O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 CPPDFKVVKLWZHE-UHFFFAOYSA-N 0.000 claims description 5
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- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
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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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/42—Anti-thrombotic agents, anticoagulants, anti-platelet 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/43—Hormones, e.g. dexamethasone
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/602—Type of release, e.g. controlled, sustained, slow
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/606—Coatings
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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CA002563150A CA2563150A1 (en) | 2004-04-06 | 2005-04-06 | Coating compositions for bioactive agents |
JP2007507470A JP2007532197A (en) | 2004-04-06 | 2005-04-06 | Coating composition for bioactive substances |
EP05763613A EP1740236A2 (en) | 2004-04-06 | 2005-04-06 | Coating compositions for bioactive agents |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US55982104P | 2004-04-06 | 2004-04-06 | |
US60/559,821 | 2004-04-06 |
Publications (2)
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WO2005097228A2 true WO2005097228A2 (en) | 2005-10-20 |
WO2005097228A3 WO2005097228A3 (en) | 2005-12-15 |
Family
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Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2005/011406 WO2005099786A1 (en) | 2004-04-06 | 2005-04-06 | Coating compositions for bioactive agents |
PCT/US2005/011792 WO2005099787A1 (en) | 2004-04-06 | 2005-04-06 | Coating compositions for bioactive agents |
PCT/US2005/011655 WO2005097228A2 (en) | 2004-04-06 | 2005-04-06 | Coating compositions for bioactive agents |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2005/011406 WO2005099786A1 (en) | 2004-04-06 | 2005-04-06 | Coating compositions for bioactive agents |
PCT/US2005/011792 WO2005099787A1 (en) | 2004-04-06 | 2005-04-06 | Coating compositions for bioactive agents |
Country Status (7)
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US (6) | US20050220841A1 (en) |
EP (2) | EP1740235B1 (en) |
JP (2) | JP2007532187A (en) |
CN (2) | CN1964748A (en) |
CA (2) | CA2563069A1 (en) |
DE (1) | DE602005015564D1 (en) |
WO (3) | WO2005099786A1 (en) |
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- 2005-04-06 DE DE602005015564T patent/DE602005015564D1/en not_active Expired - Fee Related
- 2005-04-06 EP EP05763613A patent/EP1740236A2/en not_active Withdrawn
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Also Published As
Publication number | Publication date |
---|---|
EP1740235A1 (en) | 2007-01-10 |
CN1964749A (en) | 2007-05-16 |
US20050220841A1 (en) | 2005-10-06 |
US20050220840A1 (en) | 2005-10-06 |
US7544673B2 (en) | 2009-06-09 |
JP2007532187A (en) | 2007-11-15 |
CN1964748A (en) | 2007-05-16 |
EP1740235B1 (en) | 2009-07-22 |
WO2005097228A3 (en) | 2005-12-15 |
CA2563069A1 (en) | 2005-10-27 |
EP1740236A2 (en) | 2007-01-10 |
US20050220842A1 (en) | 2005-10-06 |
US20050220839A1 (en) | 2005-10-06 |
DE602005015564D1 (en) | 2009-09-03 |
US7541048B2 (en) | 2009-06-02 |
CA2563150A1 (en) | 2005-10-20 |
US20050220843A1 (en) | 2005-10-06 |
US20050244459A1 (en) | 2005-11-03 |
WO2005099787A1 (en) | 2005-10-27 |
WO2005099786A1 (en) | 2005-10-27 |
JP2007532197A (en) | 2007-11-15 |
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