EP2968687A1 - Revêtements adhésifs de tissu pour ballonnet de médicament - Google Patents
Revêtements adhésifs de tissu pour ballonnet de médicamentInfo
- Publication number
- EP2968687A1 EP2968687A1 EP13715068.6A EP13715068A EP2968687A1 EP 2968687 A1 EP2968687 A1 EP 2968687A1 EP 13715068 A EP13715068 A EP 13715068A EP 2968687 A1 EP2968687 A1 EP 2968687A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- poly
- optionally
- therapeutic agent
- balloon
- combinations
- 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.)
- Withdrawn
Links
- 239000003814 drug Substances 0.000 title claims abstract description 109
- 229940079593 drug Drugs 0.000 title description 47
- 238000000576 coating method Methods 0.000 title description 22
- 239000003106 tissue adhesive Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 99
- 238000009472 formulation Methods 0.000 claims abstract description 94
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 87
- 229940124597 therapeutic agent Drugs 0.000 claims abstract description 61
- 239000000654 additive Substances 0.000 claims abstract description 38
- 230000000996 additive effect Effects 0.000 claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- -1 poly(L- lysine) Polymers 0.000 claims description 246
- 229950009819 zotarolimus Drugs 0.000 claims description 38
- CGTADGCBEXYWNE-JUKNQOCSSA-N zotarolimus Chemical group N1([C@H]2CC[C@@H](C[C@@H](C)[C@H]3OC(=O)[C@@H]4CCCCN4C(=O)C(=O)[C@@]4(O)[C@H](C)CC[C@H](O4)C[C@@H](/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)C3)OC)C[C@H]2OC)C=NN=N1 CGTADGCBEXYWNE-JUKNQOCSSA-N 0.000 claims description 38
- 229930012538 Paclitaxel Natural products 0.000 claims description 35
- 229960001592 paclitaxel Drugs 0.000 claims description 35
- 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 35
- 239000000463 material Substances 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 28
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- 229920002643 polyglutamic acid Polymers 0.000 claims description 27
- 239000002874 hemostatic agent Substances 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 229920000831 ionic polymer Polymers 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 229920002851 polycationic polymer Polymers 0.000 claims description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 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 20
- 239000000824 cytostatic agent Substances 0.000 claims description 17
- 229950003499 fibrin Drugs 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 102000009123 Fibrin Human genes 0.000 claims description 15
- 108010073385 Fibrin Proteins 0.000 claims description 15
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 15
- 229920000729 poly(L-lysine) polymer Polymers 0.000 claims description 15
- 229920000447 polyanionic polymer Polymers 0.000 claims description 15
- 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 15
- 229960002930 sirolimus Drugs 0.000 claims description 15
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 14
- 208000007536 Thrombosis Diseases 0.000 claims description 13
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 13
- 229920001223 polyethylene glycol Polymers 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[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 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 12
- 238000002399 angioplasty Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229960005167 everolimus Drugs 0.000 claims description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 10
- 229960003638 dopamine Drugs 0.000 claims description 10
- 239000004014 plasticizer Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 9
- 159000000000 sodium salts Chemical class 0.000 claims description 9
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 8
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 8
- 150000003384 small molecules Chemical class 0.000 claims description 8
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 8
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 8
- 229920001661 Chitosan Polymers 0.000 claims description 7
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 7
- 208000031737 Tissue Adhesions Diseases 0.000 claims description 7
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 7
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 7
- 102000008186 Collagen Human genes 0.000 claims description 6
- 108010035532 Collagen Proteins 0.000 claims description 6
- 108010010803 Gelatin Proteins 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 6
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 229920001436 collagen Polymers 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 6
- 229920000159 gelatin Polymers 0.000 claims description 6
- 239000008273 gelatin Substances 0.000 claims description 6
- 235000019322 gelatine Nutrition 0.000 claims description 6
- 235000011852 gelatine desserts Nutrition 0.000 claims description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
- 229920000083 poly(allylamine) Polymers 0.000 claims description 6
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 6
- 229920000053 polysorbate 80 Polymers 0.000 claims description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 claims description 6
- 229960000401 tranexamic acid Drugs 0.000 claims description 6
- ZHYGVVKSAGDVDY-QQQXYHJWSA-N 7-o-demethyl cypher 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](O)/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 ZHYGVVKSAGDVDY-QQQXYHJWSA-N 0.000 claims description 5
- BUROJSBIWGDYCN-GAUTUEMISA-N AP 23573 Chemical compound C1C[C@@H](OP(C)(C)=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 BUROJSBIWGDYCN-GAUTUEMISA-N 0.000 claims description 5
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 5
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 5
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[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 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 claims description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 5
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 5
- 229960005330 pimecrolimus Drugs 0.000 claims description 5
- KASDHRXLYQOAKZ-ZPSXYTITSA-N pimecrolimus Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](Cl)[C@H](OC)C1 KASDHRXLYQOAKZ-ZPSXYTITSA-N 0.000 claims description 5
- 229920000723 poly(D-arginine) polymer Polymers 0.000 claims description 5
- 229920000740 poly(D-lysine) polymer Polymers 0.000 claims description 5
- 108010011110 polyarginine Proteins 0.000 claims description 5
- 229960001302 ridaforolimus Drugs 0.000 claims description 5
- 229960001967 tacrolimus Drugs 0.000 claims description 5
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims description 5
- 229960000235 temsirolimus Drugs 0.000 claims description 5
- QFJCIRLUMZQUOT-UHFFFAOYSA-N temsirolimus Natural products C1CC(O)C(OC)CC1CC(C)C1OC(=O)C2CCCCN2C(=O)C(=O)C(O)(O2)C(C)CCC2CC(OC)C(C)=CC=CC=CC(C)CC(C)C(=O)C(OC)C(O)C(C)=CC(C)C(=O)C1 QFJCIRLUMZQUOT-UHFFFAOYSA-N 0.000 claims description 5
- YYSFXUWWPNHNAZ-PKJQJFMNSA-N umirolimus Chemical compound C1[C@@H](OC)[C@H](OCCOCC)CC[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 YYSFXUWWPNHNAZ-PKJQJFMNSA-N 0.000 claims description 5
- 239000011592 zinc chloride Substances 0.000 claims description 5
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 4
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- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
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- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 3
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- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 3
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- 239000003995 emulsifying agent Substances 0.000 claims description 3
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- CRDNMYFJWFXOCH-UHFFFAOYSA-N isoindigotin Natural products N1C2=CC=CC=C2C(=O)C1=C1C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-UHFFFAOYSA-N 0.000 description 1
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- DKWNMCUOEDMMIN-PKOBYXMFSA-N melagatran Chemical compound C1=CC(C(=N)N)=CC=C1CNC(=O)[C@H]1N(C(=O)[C@H](NCC(O)=O)C2CCCCC2)CC1 DKWNMCUOEDMMIN-PKOBYXMFSA-N 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
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- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 description 1
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- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229950006344 nocodazole Drugs 0.000 description 1
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- 150000007523 nucleic acids Chemical group 0.000 description 1
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- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
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- 229960005489 paracetamol Drugs 0.000 description 1
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- 239000002798 polar solvent Substances 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
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- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
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- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
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- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
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- 150000008163 sugars Chemical class 0.000 description 1
- 229960000894 sulindac Drugs 0.000 description 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
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- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- COKMIXFXJJXBQG-NRFANRHFSA-N tirofiban Chemical compound C1=CC(C[C@H](NS(=O)(=O)CCCC)C(O)=O)=CC=C1OCCCCC1CCNCC1 COKMIXFXJJXBQG-NRFANRHFSA-N 0.000 description 1
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- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
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- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
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- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
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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
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
- A61L29/16—Biologically active materials, e.g. therapeutic substances
-
- 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
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
- A61L29/085—Macromolecular materials
-
- 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
- A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M25/00—Catheters; Hollow probes
- A61M25/10—Balloon catheters
- A61M2025/1043—Balloon catheters with special features or adapted for special applications
- A61M2025/105—Balloon catheters with special features or adapted for special applications having a balloon suitable for drug delivery, e.g. by using holes for delivery, drug coating or membranes
Definitions
- suitable polyanionic polymers include, without limitation, carboxymethyl cellulose, sodium carboxymethyl cellulose, carboxymethyl cellulose-cysteine, poly(acrylic acid). poly(methacrylic acid), poly(L-aspartic acid), poly(D-aspartic acid), poly(L-aspartic acid) sodium salt, poly(L-glutamic acid), poly(D-glutamic acid), poly(L-glutamic acid) sodium salt, or combinations thereof.
- a method for manufacturing a system for delivering a therapeutic agent to a vessel wall of a subject comprises providing a system comprising an expandable member having a distal end, a proximal end, and a working length therebetween; and disposing a therapeutic formulation to at least a portion of the working length of the expandable member.
- the formulation comprises a therapeutic agent and a polycationic polymer; wherein the polycationic polymer promotes fibrin formation that increases the residence time and transfer of the therapeutic agent into the vessel wall.
- Carboxymethyl cellulose is used in the approved products Nutropin Depot (Genentech) and Bicillin (Wyeth).
- Polyamino acids can have a favorable safety profile but are much more expensive to employ.
- Homopolymers of amino acids that are un-branched are generally regarded as nonimmunogenic.
- Poly(aspartic acid) and poly(glutamic acid) polymers have the requisite polyionic structural properties to be tissue adhesive, and both are commercially available in a range of molecular weights. Additionally, poly(aspartic acid) and poly(glutamic acid) polymers, which can be metabolized, can be used at a molecular weight above the 40K Dalton renal clearance threshold.
- the adhesive agent comprises a polycationic polymer.
- Polycationic polymers promote adhesion of the therapeutic formulation in part via relatively strong electrostatic interactions with the endothelial glycocalyx of the vessel surface, which is negatively charged (see Giantsos KM, et al. Biomaterials 30 (2009) 5885- 5891).
- the adhesive agent can be combined with dopamine to augment its tissue-adhesive properties.
- the dihydroxyphenol or catechol moiety found in dopamine provide adhesion to surfaces by hydrogen bonding and coordination mechanisms. Such moieties are ubiquitous in mussel and marine mollusk adhesive proteins.
- the adhesion additive can promote adhesion of the therapeutic formulation to the vessel wall by the promotion of fibrin and thrombus formation.
- the polycationic polymer can provide such thrombus- and fibrin-promoting effect.
- platelets are negatively charged (see Ong SY, et al.
- Platelets also have a net negative zeta potential, and accordingly are capable of aggregation in response to electrostatic forces.
- Polycationic polymers also encourage fibrin formation, so that the therapeutic formulation can adhere to the vessel wall via fibrin for a prolonged period of time.
- Polyethyeneimine is alcohol soluble rendering formulation with a therapeutic agent, e.g., zotarolimus, straightforward.
- Chitosan is used in a variety of hemostatic agents for medical and military use. Chitosan has strong adhesive effect to tissue, wounds, and blood.
- Poly-N- acetylglucosamine is a polycationic polysaccharide. Poly-N-acetylglucosamine is the main component of the SyvekPatch hemostat approved by the Food and Drug Administration for use in the local management of bleeding wounds, such as vascular site, percutaneous catheters or tubes, and surgical debridement.
- poly-N-acetyl glucosamine can be obtained from a marine microalgae.
- FIGURE 4 illustrates the mechanism of retention of paclitaxel on a vessel wall studied by Paccocath technology.
- Thrombolytic agents which can be defined as agents that help degrade thrombi (clots), can also be used as adjunctive agents, because the action of lysing a clot helps to disperse platelets trapped within the fibrin matrix of a thrombus.
- clots can also be used as adjunctive agents, because the action of lysing a clot helps to disperse platelets trapped within the fibrin matrix of a thrombus.
- thrombolytic agents include, but are not limited to, urokinase or recombinant urokinase, pro- urokinase or recombinant pro-urokinase, tissue plasminogen activator or its recombinant form, and streptokinase.
- the therapeutic formulation of the disclosed subject matter comprises zotarolimus and polyethyeneimine.
- the ratio of zotarolimus:polyethyeneimine is about 1: 1 by weight.
- the therapeutic formulation can further comprise zotarolimus and poly(L-lysine).
- the ratio of zotarolimus:poly(L- lysine) is about 1: 1 by weight.
- Polyionic polymers are highly polar and soluble in water or highly polar solvents, such as dimethysulfoxide (DMSO), Dimethylacetamide (DMAC), and ethanol. Due to their high polarity and hydrogen bonding, polyionic polymers have Tgs above ambient temperature in the dry state. Consequently, a dry coating of polyionic polymers can be brittle and may have poor coating integrity.
- a solution to provide for good coating integrity when dry is to plasticize the therapeutic formulation with an appropriate plasticizer. Suitable plasticizers are low molecular weight, and water soluble species that are essentially non- volatile.
- the therapeutic formulation further includes a solvent.
- the solvents include, for the purpose of illustration and without limitation, acetone, 2-butanone, cyclopentanone, cyclohexanone, diethyl ether, dipropyl ether, diisopropyl ether, methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tertiary-butanol, toluene, xylene, pentane, hexane, cyclohexane, heptane, dimethylformamide (DMF), dimethylacetamide (DMAC), and combinations thereof.
- DMF dimethylformamide
- DMAC dimethylacetamide
- the non-ionic polymers include, for the purpose of illustration and without limitation, PVP, silk-elastin like polymer, poly(vinyl alcohol), PEG, pluronics (PEO-PPO-PEO), poly(vinyl acetate), poly(ethylene oxide) (PEO), PVP-vinyl acetate (copovidone), polysorbate 80 (Tween 80), and polysorbate 20 (Tween 20), hydroxyl alkyl celluloses, and combinations thereof.
- the balloon is formed of a polyurethane material, such as TECOTHANE® (Thermedics).
- TECOTHANE® is a thermoplastic, aromatic, polyether polyurethane synthesized from methylene disocyanate (MDI), polytetramethylene ether glycol (PTMEG) and 1,4 butanediol chain extender.
- MDI methylene disocyanate
- PTMEG polytetramethylene ether glycol
- 1,4 butanediol chain extender 1,4 butanediol chain extender.
- TECOTHANE® grade 1065D is suitable in certain embodiments, and has a Shore durometer of 65D, an elongation at break of about 300%, and a high tensile strength at yield of about 10,000 psi.
- other suitable grades can be used, including TECOTHANE® 1075D, having a Shore D hardness of 75.
- the balloon is formed from a low tensile set polymer such as a silicone-polyurethane copolymer.
- the silicone-polyurethane is an ether urethane and more specifically an aliphatic ether urethane such as PURSIL AL 575A and PURSIL ALIO, (Polymer Technology Group), and ELAST-EON 3-70A, (Elastomedics), which are silicone polyether urethane copolymers, and more specifically, aliphatic ether urethane cosiloxanes.
- the low tensile set polymer is a diene polymer.
- diene polymers can be used such as but not limited to an isoprene such as an AB and ABA poly(styrene-block-isoprene), a neoprene, an AB and ABA poly(styrene-block- butadiene) such as styrene butadiene styrene (SBS) and styrene butadiene rubber (SBR), and 1,4- polybutadiene.
- the diene polymer is an isoprene including isoprene copolymers and isoprene block copolymers such as poly(styrene-block-isoprene).
- the balloon does not necessarily include a stent, e.g., is free of a stent.
- a stent can be mounted onto the coated balloon and can further promote uptake.
- the stent will not detrimentally affect coating integrity or drug delivery.
- the type of stent that can be used includes, but is not limited to, a bare metal stent, a balloon expandable stent, a self expanding stent, a drug eluting stent, a prohealing stent, and a self- expanding vulnerable plaque implant.
- the balloon can be coated independently of the stent or in conjunction with the stent coating process.
- the stent coating can contain the same or different therapeutic agents from the balloon catheter or expandable member. However, the particular coating on the balloon catheter or expandable member can have distinct release kinetics from the therapeutic coating on the stent.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Materials For Medical Uses (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne une préparation thérapeutique, pour un ballonnet d'administration de médicament qui comporte une préparation thérapeutique qui comprend un agent thérapeutique et un additif d'adhérence. L'additif d'adhérence favorise l'adhérence de la préparation thérapeutique à une paroi de vaisseau d'un sujet. L'invention concerne également un système et un procédé de fabrication d'un système comprenant un élément extensible ayant une longueur utile, la préparation thérapeutique étant disposée le long d'au moins une partie de la longueur utile.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2013/032570 WO2014143048A1 (fr) | 2013-03-15 | 2013-03-15 | Revêtements adhésifs de tissu pour ballonnet de médicament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2968687A1 true EP2968687A1 (fr) | 2016-01-20 |
Family
ID=48050936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP13715068.6A Withdrawn EP2968687A1 (fr) | 2013-03-15 | 2013-03-15 | Revêtements adhésifs de tissu pour ballonnet de médicament |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP2968687A1 (fr) |
| JP (1) | JP6147906B2 (fr) |
| CN (1) | CN105228664A (fr) |
| CR (1) | CR20150563A (fr) |
| WO (1) | WO2014143048A1 (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103736154B (zh) * | 2013-12-26 | 2015-06-17 | 先健科技(深圳)有限公司 | 药物涂层球囊导管 |
| US9675734B2 (en) * | 2014-08-29 | 2017-06-13 | Invatec S.P.A. | Medical balloon coated with therapeutic agent, carboxylic acid, and salt thereof |
| EP3868434A1 (fr) * | 2016-02-08 | 2021-08-25 | Orbusneich Medical Pte. Ltd | Ballonnet à élution de médicament |
| US10792477B2 (en) | 2016-02-08 | 2020-10-06 | Orbusneich Medical Pte. Ltd. | Drug eluting balloon |
| CN105903086A (zh) * | 2016-06-08 | 2016-08-31 | 葛晨亮 | 可预防血栓的中心静脉导管 |
| CN105943209A (zh) * | 2016-06-08 | 2016-09-21 | 葛晨亮 | 新型药物涂层球囊 |
| WO2018057788A1 (fr) * | 2016-09-22 | 2018-03-29 | Mercator Medsystems, Inc. | Traitement de la resténose par le temsirolimus |
| EP3558325A4 (fr) * | 2016-12-20 | 2020-08-05 | Innovative Nano & Micro Technologies Pvt Ltd (INM Technologies) | Compositions d'échafaudage pour réparation tissulaire |
| WO2019110600A1 (fr) * | 2017-12-06 | 2019-06-13 | Biotronik Ag | Substances et méthodes d'administration de médicament intracrânienne |
| CN109954198B (zh) * | 2017-12-25 | 2021-10-12 | 先健科技(深圳)有限公司 | 药物球囊及其制备方法 |
| EP3768338A4 (fr) * | 2018-03-21 | 2022-03-23 | Meril Life Sciences Pvt Ltd | Ballonnet revêtu de médicament |
| CN112739392A (zh) * | 2018-08-01 | 2021-04-30 | 波士顿科学国际有限公司 | 药物释放涂层组合物 |
| CN112867514A (zh) * | 2018-10-15 | 2021-05-28 | M.A.医学联合公司 | 提供药物微贮库的接触转移的管腔内可扩张导管的涂层 |
| CN111035813B (zh) * | 2018-10-15 | 2022-02-18 | 复旦大学附属中山医院 | 一种液体创可贴式冠脉带膜支架及其制作方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5304197A (en) | 1988-10-04 | 1994-04-19 | Cordis Corporation | Balloons for medical devices and fabrication thereof |
| JPH02249557A (ja) * | 1989-03-23 | 1990-10-05 | Sanyo Chem Ind Ltd | 外科手術用器具 |
| US5391183A (en) * | 1990-09-21 | 1995-02-21 | Datascope Investment Corp | Device and method sealing puncture wounds |
| US5324261A (en) * | 1991-01-04 | 1994-06-28 | Medtronic, Inc. | Drug delivery balloon catheter with line of weakness |
| US5102402A (en) * | 1991-01-04 | 1992-04-07 | Medtronic, Inc. | Releasable coatings on balloon catheters |
| US6406457B1 (en) | 1994-03-02 | 2002-06-18 | Scimed Life Systems, Inc. | Block copolymer elastomer catheter balloons |
| EP0980280B1 (fr) | 1997-10-01 | 2005-02-09 | Medtronic Ave, Inc. | Systeme de delivrance de medicament et de therapie genique |
| JP4198348B2 (ja) * | 2001-10-23 | 2008-12-17 | 満 明石 | 感温性高分子被覆層を有するバルーンカテーテル |
| US6991617B2 (en) | 2002-08-21 | 2006-01-31 | Hektner Thomas R | Vascular treatment method and device |
| US7273417B1 (en) | 2005-01-25 | 2007-09-25 | Lundquist Steven W | Golf practice aid |
| US8951595B2 (en) * | 2009-12-11 | 2015-02-10 | Abbott Cardiovascular Systems Inc. | Coatings with tunable molecular architecture for drug-coated balloon |
| US9295663B2 (en) * | 2010-07-14 | 2016-03-29 | Abbott Cardiovascular Systems Inc. | Drug coated balloon with in-situ formed drug containing microspheres |
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2013
- 2013-03-15 EP EP13715068.6A patent/EP2968687A1/fr not_active Withdrawn
- 2013-03-15 WO PCT/US2013/032570 patent/WO2014143048A1/fr not_active Ceased
- 2013-03-15 CN CN201380074680.5A patent/CN105228664A/zh active Pending
- 2013-03-15 JP JP2016500072A patent/JP6147906B2/ja not_active Expired - Fee Related
-
2015
- 2015-10-15 CR CR20150563A patent/CR20150563A/es unknown
Non-Patent Citations (2)
| Title |
|---|
| None * |
| See also references of WO2014143048A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014143048A1 (fr) | 2014-09-18 |
| JP2016517295A (ja) | 2016-06-16 |
| CN105228664A (zh) | 2016-01-06 |
| CR20150563A (es) | 2016-04-05 |
| JP6147906B2 (ja) | 2017-06-14 |
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