CA2599082A1 - Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds - Google Patents
Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds Download PDFInfo
- Publication number
- CA2599082A1 CA2599082A1 CA002599082A CA2599082A CA2599082A1 CA 2599082 A1 CA2599082 A1 CA 2599082A1 CA 002599082 A CA002599082 A CA 002599082A CA 2599082 A CA2599082 A CA 2599082A CA 2599082 A1 CA2599082 A1 CA 2599082A1
- Authority
- CA
- Canada
- Prior art keywords
- glu
- poly
- cys
- maleic anhydride
- supramacromolecular
- 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.)
- Abandoned
Links
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 206010052428 Wound Diseases 0.000 title claims abstract description 18
- 208000027418 Wounds and injury Diseases 0.000 title claims abstract description 18
- 230000035876 healing Effects 0.000 title claims abstract description 12
- 229920000642 polymer Polymers 0.000 title claims description 38
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000000227 bioadhesive Substances 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 125000000524 functional group Chemical group 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 208000015181 infectious disease Diseases 0.000 claims abstract description 6
- 125000005647 linker group Chemical group 0.000 claims abstract description 5
- 150000001408 amides Chemical class 0.000 claims abstract description 4
- 150000001335 aliphatic alkanes Chemical group 0.000 claims abstract 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- -1 poly(methyl vinyl Chemical group 0.000 claims description 68
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 31
- HYHSBSXUHZOYLX-WDSKDSINSA-N S-nitrosoglutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O HYHSBSXUHZOYLX-WDSKDSINSA-N 0.000 claims description 27
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 26
- 229920001223 polyethylene glycol Polymers 0.000 claims description 19
- 239000002202 Polyethylene glycol Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 12
- 239000011976 maleic acid Substances 0.000 claims description 11
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 11
- 229920002732 Polyanhydride Polymers 0.000 claims description 10
- 229960003180 glutathione Drugs 0.000 claims description 10
- 239000002840 nitric oxide donor Substances 0.000 claims description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 108010024636 Glutathione Proteins 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
- 230000002209 hydrophobic effect Effects 0.000 claims description 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
- 229920001983 poloxamer Polymers 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- OJGVRWVZHGUOLY-BQBZGAKWSA-N (2s)-5-[[(2r)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-2-(hydroxymethylamino)-5-oxopentanoic acid Chemical compound OCN[C@H](C(O)=O)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O OJGVRWVZHGUOLY-BQBZGAKWSA-N 0.000 claims description 6
- HKBNQXMLSMKLJV-BQBZGAKWSA-N L-gamma-glutamyl-L-cysteinyl-beta-alanine Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCCC(O)=O HKBNQXMLSMKLJV-BQBZGAKWSA-N 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 6
- 229920001400 block copolymer Polymers 0.000 claims description 6
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 6
- 235000018417 cysteine Nutrition 0.000 claims description 6
- HKBNQXMLSMKLJV-UHFFFAOYSA-N gamma-L-glutamyl-L-cysteinyl-beta-alanine Natural products OC(=O)C(N)CCC(=O)NC(CS)C(=O)NCCC(O)=O HKBNQXMLSMKLJV-UHFFFAOYSA-N 0.000 claims description 6
- 108700020537 homoglutathione Proteins 0.000 claims description 6
- 229940074982 poly(vinylpyrrolidone-co-vinyl-acetate) Drugs 0.000 claims description 6
- 229920000573 polyethylene Polymers 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 6
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 150000004007 S-nitroso compounds Chemical class 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000029663 wound healing Effects 0.000 claims description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 206010072170 Skin wound Diseases 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 230000002708 enhancing effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical group CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229920000141 poly(maleic anhydride) Polymers 0.000 claims description 4
- 206010040872 skin infection Diseases 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical group 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 150000002191 fatty alcohols Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- ICRHORQIUXBEPA-UHFFFAOYSA-N thionitrous acid Chemical compound SN=O ICRHORQIUXBEPA-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- WKRBZXGRENYWJO-USPAICOZSA-M C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N.N(=O)[O-].[Na+] Chemical compound C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N.N(=O)[O-].[Na+] WKRBZXGRENYWJO-USPAICOZSA-M 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 108010001742 S-Nitrosoglutathione Proteins 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000005102 attenuated total reflection Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QCZAWDGAVJMPTA-RNFRBKRXSA-N ClC1=CC=CC(=N1)C1=NC(=NC(=N1)N[C@@H](C(F)(F)F)C)N[C@@H](C(F)(F)F)C Chemical compound ClC1=CC=CC(=N1)C1=NC(=NC(=N1)N[C@@H](C(F)(F)F)C)N[C@@H](C(F)(F)F)C QCZAWDGAVJMPTA-RNFRBKRXSA-N 0.000 description 1
- 206010056340 Diabetic ulcer Diseases 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 102400001368 Epidermal growth factor Human genes 0.000 description 1
- 101800003838 Epidermal growth factor Proteins 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000021164 cell adhesion Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 229940116977 epidermal growth factor Drugs 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 230000008215 regulation of wound healing Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000936 topical exposure Toxicity 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
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- A—HUMAN NECESSITIES
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- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/44—Medicaments
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- A—HUMAN NECESSITIES
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- 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
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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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08L39/08—Homopolymers or copolymers of vinyl-pyridine
-
- 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
- A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
- A61L2300/114—Nitric oxide, i.e. NO
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/02—Homopolymers or copolymers of esters
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Materials Engineering (AREA)
- Heart & Thoracic Surgery (AREA)
- Polymers & Plastics (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002599082A CA2599082A1 (en) | 2007-08-27 | 2007-08-27 | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
| PCT/CA2008/001484 WO2009026680A1 (en) | 2007-08-27 | 2008-08-20 | Supramacrqmolecular polymer complexes providing controlled nitric oxide release for healing wounds |
| EP08783394A EP2201077A4 (en) | 2007-08-27 | 2008-08-20 | ULTRAHOLE-MOLECULAR POLYMER COMPLEXES TARGETED WITH ADJUSTABLE NITROGEN MONOXIDE FOR WOUND HEALING |
| JP2010522143A JP5346340B2 (ja) | 2007-08-27 | 2008-08-20 | 創傷を治癒するため制御された酸化窒素放出を提供する超高分子ポリマー複合体 |
| US12/675,498 US8992945B2 (en) | 2007-08-27 | 2008-08-20 | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
| CA2697862A CA2697862A1 (en) | 2007-08-27 | 2008-08-20 | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002599082A CA2599082A1 (en) | 2007-08-27 | 2007-08-27 | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2599082A1 true CA2599082A1 (en) | 2009-02-27 |
Family
ID=40385170
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002599082A Abandoned CA2599082A1 (en) | 2007-08-27 | 2007-08-27 | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
| CA2697862A Abandoned CA2697862A1 (en) | 2007-08-27 | 2008-08-20 | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2697862A Abandoned CA2697862A1 (en) | 2007-08-27 | 2008-08-20 | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8992945B2 (enExample) |
| EP (1) | EP2201077A4 (enExample) |
| JP (1) | JP5346340B2 (enExample) |
| CA (2) | CA2599082A1 (enExample) |
| WO (1) | WO2009026680A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019137414A1 (en) * | 2018-01-12 | 2019-07-18 | Beijing Universal Likang Technology Co., Ltd. | Method for treating active bleeding using biocompatible hemostatic and sealant compositions |
| US11213615B2 (en) | 2017-02-28 | 2022-01-04 | EndoClot Plus Co.. Ltd | Composition for submucosal injection, reagent combination, and applications thereof |
| CN114146880A (zh) * | 2021-12-06 | 2022-03-08 | 中国石油大学(华东) | 一种超声雾化辅助层层自组装制备氢气阻隔涂层的方法 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090214618A1 (en) | 2005-05-27 | 2009-08-27 | Schoenfisch Mark H | Nitric oxide-releasing particles for nitric oxide therapeutics and biomedical applications |
| CA2671595A1 (en) * | 2009-07-09 | 2011-01-09 | Ping I. Lee | Controlled nitric oxide delivery from aqueous s-nitrosothiol conjugated polymers and their complexes |
| EP2467173B8 (en) | 2009-08-21 | 2019-06-19 | Novan, Inc. | Wound dressings, methods of using the same and methods of forming the same |
| BR112012003792B1 (pt) | 2009-08-21 | 2020-05-19 | Novan Inc | composição tópica, e, uso da composição tópica |
| US8591876B2 (en) | 2010-12-15 | 2013-11-26 | Novan, Inc. | Methods of decreasing sebum production in the skin |
| WO2012118829A2 (en) | 2011-02-28 | 2012-09-07 | Novan, Inc. | Tertiary s-nitrosothiol-modified nitricoxide-releasing xerogels and methods of using the same |
| AU2013300035A1 (en) * | 2012-08-06 | 2015-02-26 | South Dakota Board Of Regents | Directional eluting implantable medical device |
| WO2014046671A1 (en) * | 2012-09-21 | 2014-03-27 | Michigan Technological University | No-releasing polymers and uses thereof |
| WO2014124125A2 (en) | 2013-02-07 | 2014-08-14 | The Regents Of The University Of Michigan | Thromboresistant/bactericidal s-nitroso-n-acetylpenicillamine (snap)-doped nitric oxide release polymers with enhanced stability |
| WO2015003155A1 (en) * | 2013-07-03 | 2015-01-08 | The American University In Cairo | Bio-compatible apitherapeutic nanofibers |
| JP6357156B2 (ja) * | 2013-09-02 | 2018-07-11 | テルモ株式会社 | 医療用具およびその製造方法 |
| WO2015170327A1 (en) | 2014-05-05 | 2015-11-12 | Sealantis Ltd. | Biological adhesives and sealants and methods of using the same |
| EP3180366B1 (en) * | 2014-08-14 | 2018-09-26 | Rohm and Haas Company | Polymer with releasable gas |
| GB201506236D0 (en) * | 2015-04-13 | 2015-05-27 | Jellagen Pty Ltd | Modified collagen, methods of manufacture thereof |
| CN105568401A (zh) * | 2015-12-12 | 2016-05-11 | 大连理工大学 | 一种超声雾化辅助静电纺丝技术 |
| US11111362B2 (en) | 2016-09-26 | 2021-09-07 | Becton, Dickinson And Company | Breathable films with microbial barrier properties |
| EP3570927A4 (en) | 2017-01-21 | 2020-12-23 | Biocrede Inc. | MEDICAL PRODUCTS AND METHODS FOR THE CONTROLLED RELEASE OF NITROGEN OXIDE |
| EP3395377A1 (en) * | 2017-04-28 | 2018-10-31 | Borealis AG | Soft polypropylene composition with improved properties |
| CN109694887A (zh) * | 2017-10-24 | 2019-04-30 | 朱一民 | 重组酵母菌及其用于制造生物质酒精的用途 |
| CN110284263B (zh) * | 2019-06-13 | 2022-03-08 | 上海交通大学 | 叠层复合纳米纤维的制备方法 |
| US11814519B2 (en) * | 2020-03-26 | 2023-11-14 | Virginia Commonwealth University | Nitric oxide-releasing 3D-printing compositions and uses thereof |
| CN115125669B (zh) * | 2022-07-15 | 2023-08-11 | 华中科技大学同济医学院附属协和医院 | 一种超声响应性释放一氧化氮电纺膜及其制备方法 |
| DE102024102999A1 (de) * | 2024-02-02 | 2025-08-07 | Acandis Gmbh | Liner für einen medizinischen Katheter; Medizinischer Katheter mit einem Liner; Verfahren zur Herstellung eines Liners für einen medizinischen Katheter |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61186309A (ja) * | 1985-02-13 | 1986-08-20 | Toyobo Co Ltd | 口腔粘膜適用組成物 |
| US6255277B1 (en) * | 1993-09-17 | 2001-07-03 | Brigham And Women's Hospital | Localized use of nitric oxide-adducts to prevent internal tissue damage |
| US5770645A (en) * | 1996-08-02 | 1998-06-23 | Duke University Medical Center | Polymers for delivering nitric oxide in vivo |
| US6221425B1 (en) * | 1998-01-30 | 2001-04-24 | Advanced Cardiovascular Systems, Inc. | Lubricious hydrophilic coating for an intracorporeal medical device |
| IT1303793B1 (it) * | 1998-11-27 | 2001-02-23 | Promefarm S R L | "composizione farmaceutica comprendente un composto organico donatoredi ossido nitrico (no)" |
| US6706274B2 (en) * | 2001-01-18 | 2004-03-16 | Scimed Life Systems, Inc. | Differential delivery of nitric oxide |
| US20050113510A1 (en) * | 2001-05-01 | 2005-05-26 | Feldstein Mikhail M. | Method of preparing polymeric adhesive compositions utilizing the mechanism of interaction between the polymer components |
| JP2004528337A (ja) * | 2001-05-02 | 2004-09-16 | ニトロメド インコーポレーテッド | ニトロソ化およびニトロシル化ネビボロール、ならびにその代謝産物、組成物、および使用方法 |
| GB0125222D0 (en) * | 2001-10-19 | 2001-12-12 | Barts & London Nhs Trust | Composition for the treatment of microbial infections |
| JP2005533774A (ja) * | 2002-06-07 | 2005-11-10 | ランバクシー ラボラトリーズ リミテッド | ジバルプロエクスソジウムの放出遅延剤 |
| US8211455B2 (en) | 2002-06-19 | 2012-07-03 | Boston Scientific Scimed, Inc. | Implantable or insertable medical devices for controlled delivery of a therapeutic agent |
| US20060240065A1 (en) * | 2005-04-26 | 2006-10-26 | Yung-Ming Chen | Compositions for medical devices containing agent combinations in controlled volumes |
| ES2540929T3 (es) * | 2005-02-01 | 2015-07-14 | Emisphere Technologies, Inc. | Sistema de administración de retención gástrica y liberación controlada |
| GB0505035D0 (en) * | 2005-03-11 | 2005-04-20 | Insense Ltd | Improvements relating to skin dressings |
| US7517914B2 (en) * | 2005-04-04 | 2009-04-14 | Boston Scientificscimed, Inc. | Controlled degradation materials for therapeutic agent delivery |
| BRPI0503201B8 (pt) * | 2005-07-28 | 2021-05-25 | Sci Tech Produtos Medicos Ltda | stents revestidos com blendas poliméricas hidrofílicas, eluidoras de óxido nítrico e s-nitrosotióis |
| JP4812394B2 (ja) * | 2005-10-19 | 2011-11-09 | 扶桑薬品工業株式会社 | 鎮痛用組成物 |
-
2007
- 2007-08-27 CA CA002599082A patent/CA2599082A1/en not_active Abandoned
-
2008
- 2008-08-20 CA CA2697862A patent/CA2697862A1/en not_active Abandoned
- 2008-08-20 EP EP08783394A patent/EP2201077A4/en not_active Withdrawn
- 2008-08-20 WO PCT/CA2008/001484 patent/WO2009026680A1/en not_active Ceased
- 2008-08-20 JP JP2010522143A patent/JP5346340B2/ja not_active Expired - Fee Related
- 2008-08-20 US US12/675,498 patent/US8992945B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11213615B2 (en) | 2017-02-28 | 2022-01-04 | EndoClot Plus Co.. Ltd | Composition for submucosal injection, reagent combination, and applications thereof |
| WO2019137414A1 (en) * | 2018-01-12 | 2019-07-18 | Beijing Universal Likang Technology Co., Ltd. | Method for treating active bleeding using biocompatible hemostatic and sealant compositions |
| US11998653B2 (en) | 2018-01-12 | 2024-06-04 | Beijing Universal Likang Technology Co., Ltd. | Method for treating active bleeding by sequentially applying a biocompatible hemostatic composition and a sealant composition |
| CN114146880A (zh) * | 2021-12-06 | 2022-03-08 | 中国石油大学(华东) | 一种超声雾化辅助层层自组装制备氢气阻隔涂层的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2697862A1 (en) | 2009-03-05 |
| JP2010537008A (ja) | 2010-12-02 |
| US20100303891A1 (en) | 2010-12-02 |
| JP5346340B2 (ja) | 2013-11-20 |
| US8992945B2 (en) | 2015-03-31 |
| EP2201077A1 (en) | 2010-06-30 |
| EP2201077A4 (en) | 2013-01-09 |
| WO2009026680A1 (en) | 2009-03-05 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |