CA2205564C - Compositions pharmaceutiques comprenant des biopolymeres liberant de l'oxyde nitrique - Google Patents

Compositions pharmaceutiques comprenant des biopolymeres liberant de l'oxyde nitrique Download PDF

Info

Publication number: CA2205564C
Authority: CA; Canada
Prior art keywords: nitric oxide; polymeric agent; group; releasing; biopolymer
Prior art date: 1994-11-22
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.): Expired - Fee Related

Application number

CA 2205564

Other languages

English (en)

Other versions

CA2205564A1 (fr

Inventor

Joseph E. Saavedra

Larry K. Keefer

Peter P. Roller

Miki Akamatsu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

US Department of Health and Human Services

Original Assignee

US Department of Health and Human Services

Priority date (The priority date 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 date listed.)

1994-11-22

Filing date

1995-11-20

Publication date

2006-07-11

1994-11-22 Priority claimed from US08/344,157 external-priority patent/US5632981A/en

1995-11-20 Application filed by US Department of Health and Human Services filed Critical US Department of Health and Human Services

1996-05-30 Publication of CA2205564A1 publication Critical patent/CA2205564A1/fr

2006-07-11 Application granted granted Critical

2006-07-11 Publication of CA2205564C publication Critical patent/CA2205564C/fr

2015-11-20 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title claims abstract description 362
229920001222 biopolymer Polymers 0.000 title claims abstract description 91
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 20
239000000203 mixture Substances 0.000 claims abstract description 64
108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 23
230000001225 therapeutic effect Effects 0.000 claims abstract description 16
102000004169 proteins and genes Human genes 0.000 claims abstract description 15
108090000623 proteins and genes Proteins 0.000 claims abstract description 15
102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 14
229920001184 polypeptide Polymers 0.000 claims abstract description 10
108020004707 nucleic acids Proteins 0.000 claims abstract description 7
102000039446 nucleic acids Human genes 0.000 claims abstract description 7
150000007523 nucleic acids Chemical class 0.000 claims abstract description 7
230000004962 physiological condition Effects 0.000 claims abstract description 7
108091034117 Oligonucleotide Proteins 0.000 claims abstract description 6
239000003795 chemical substances by application Substances 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 23
229920000642 polymer Polymers 0.000 claims description 23
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
150000001768 cations Chemical class 0.000 claims description 17
-1 t-butoxycarbonyl Chemical group 0.000 claims description 17
241000124008 Mammalia Species 0.000 claims description 16
239000003937 drug carrier Substances 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 14
229910052751 metal Inorganic materials 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
125000004423 acyloxy group Chemical group 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
206010028980 Neoplasm Diseases 0.000 claims description 7
239000003446 ligand Substances 0.000 claims description 7
210000004881 tumor cell Anatomy 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
230000007935 neutral effect Effects 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 6
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 6
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 claims description 5
150000004676 glycans Chemical class 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
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239000005017 polysaccharide Substances 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
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239000005556 hormone Substances 0.000 claims description 3
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
230000000665 anti-chemotactic effect Effects 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
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125000000962 organic group Chemical group 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
XMPRFBUTGLVJQS-HTQCVBHVSA-N (E)-[(2S)-1-[[(E)-but-2-enoyl]amino]-3-methylbutan-2-yl]-hydroxyimino-oxidoazanium Chemical compound C\C=C\C(=O)NC[C@H](C(C)C)[N+](\[O-])=N/O XMPRFBUTGLVJQS-HTQCVBHVSA-N 0.000 claims 1
ZGNLFUXWZJGETL-YUSKDDKASA-N (Z)-[(2S)-2-amino-2-carboxyethyl]-hydroxyimino-oxidoazanium Chemical compound N[C@@H](C\[N+]([O-])=N\O)C(O)=O ZGNLFUXWZJGETL-YUSKDDKASA-N 0.000 claims 1
FJUBKTNNXRFHFD-WTSVBCDHSA-N Dopastin Natural products C\C=C\C(=O)NC[C@H](C(C)C)N(O)N=O FJUBKTNNXRFHFD-WTSVBCDHSA-N 0.000 claims 1
MLFKVJCWGUZWNV-UHFFFAOYSA-N L-alanosine Natural products OC(=O)C(N)CN(O)N=O MLFKVJCWGUZWNV-UHFFFAOYSA-N 0.000 claims 1
229950005033 alanosine Drugs 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
230000002349 favourable effect Effects 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
238000000034 method Methods 0.000 abstract description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
239000000243 solution Substances 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 19
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 19
239000012038 nucleophile Substances 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
235000018102 proteins Nutrition 0.000 description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 11
239000007787 solid Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000011734 sodium Substances 0.000 description 9
210000004027 cell Anatomy 0.000 description 7
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239000000047 product Substances 0.000 description 7
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
125000005647 linker group Chemical group 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000000066 endothelium dependent relaxing factor Substances 0.000 description 5
229960003711 glyceryl trinitrate Drugs 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
230000000269 nucleophilic effect Effects 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000009471 action Effects 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000003814 drug Substances 0.000 description 4
239000007943 implant Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
XQQUSYWGKLRJRA-RABCQHRBSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-6-amino-2-[[(2s,3s)-2-amino-3-methylpentanoyl]amino]hexanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]-3-methylbutanoic acid Chemical compound CC[C@H](C)[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(O)=O XQQUSYWGKLRJRA-RABCQHRBSA-N 0.000 description 3
241000220479 Acacia Species 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 3
235000010643 Leucaena leucocephala Nutrition 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 3
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XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 description 3
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NOOJLZTTWSNHOX-UWVGGRQHSA-N Melanostatin Chemical compound NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CCCN1 NOOJLZTTWSNHOX-UWVGGRQHSA-N 0.000 description 2
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XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 2
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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239000002253 acid Substances 0.000 description 2
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YEESUBCSWGVPCE-UHFFFAOYSA-N azanylidyneoxidanium iron(2+) pentacyanide Chemical compound [Fe++].[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.N#[O+] YEESUBCSWGVPCE-UHFFFAOYSA-N 0.000 description 2
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108010088381 isoleucyl-lysyl-valyl-alanyl-valine Proteins 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000002609 medium Substances 0.000 description 2
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UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 2
NODGJSNKUCVLNN-UHFFFAOYSA-N n-methyl-2-(methylamino)acetamide Chemical compound CNCC(=O)NC NODGJSNKUCVLNN-UHFFFAOYSA-N 0.000 description 2
229960002460 nitroprusside Drugs 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
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FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA 2205564 1994-11-22 1995-11-20 Compositions pharmaceutiques comprenant des biopolymeres liberant de l'oxyde nitrique Expired - Fee Related CA2205564C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/344,157 US5632981A (en)	1992-08-24	1994-11-22	Biopolymer-bound nitric oxide-releasing compositions, pharmaceutical compositions incorporating same and methods of treating biological disorders using same
US08/344,157		1994-11-22
PCT/US1995/015180 WO1996015797A1 (fr)	1994-11-22	1995-11-20	Compositions pharmaceutiques comprenant des biopolymeres liberant de l'oxyde nitrique

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CA2205564A1 CA2205564A1 (fr)	1996-05-30
CA2205564C true CA2205564C (fr)	2006-07-11

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US11026965B2 (en)	2018-03-06	2021-06-08	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing cyclodextrins as biodegradable antibacterial scaffolds and methods pertaining thereto
US11072668B2 (en)	2017-01-03	2021-07-27	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing alginates as biodegradable antibacterial scaffolds and methods pertaining thereto
US11186681B2 (en)	2016-10-07	2021-11-30	The University Of North Carolina At Chapel Hill	S-Nitrosothiol-mediated hyperbranched polyesters
US11421044B2 (en)	2018-12-28	2022-08-23	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing antibacterial polymers and scaffolds fabricated therefrom and methods pertaining thereto
US11723914B2 (en)	2017-03-28	2023-08-15	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing polyaminoglycosides as biodegradable antibacterial scaffolds and methods pertaining thereto
US12460050B2 (en)	2017-11-15	2025-11-04	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing hyperbranched compounds as antibacterial scaffolds and methods pertaining thereto

1995
- 1995-11-20 CA CA 2205564 patent/CA2205564C/fr not_active Expired - Fee Related

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US11072668B2 (en)	2017-01-03	2021-07-27	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing alginates as biodegradable antibacterial scaffolds and methods pertaining thereto
US11697693B2 (en)	2017-01-03	2023-07-11	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing alginates as biodegradable antibacterial scaffolds and methods pertaining thereto
US11723914B2 (en)	2017-03-28	2023-08-15	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing polyaminoglycosides as biodegradable antibacterial scaffolds and methods pertaining thereto
US12460050B2 (en)	2017-11-15	2025-11-04	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing hyperbranched compounds as antibacterial scaffolds and methods pertaining thereto
US11026965B2 (en)	2018-03-06	2021-06-08	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing cyclodextrins as biodegradable antibacterial scaffolds and methods pertaining thereto
US11672818B2 (en)	2018-03-06	2023-06-13	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing cyclodextrins as biodegradable antibacterial scaffolds and methods pertaining thereto
US11421044B2 (en)	2018-12-28	2022-08-23	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing antibacterial polymers and scaffolds fabricated therefrom and methods pertaining thereto
US12173090B2 (en)	2018-12-28	2024-12-24	The University Of North Carolina At Chapel Hill	Nitric oxide-releasing antibacterial polymers and scaffolds fabricated therefrom and methods pertaining thereto

Also Published As

Publication number	Publication date
CA2205564A1 (fr)	1996-05-30

Legal Events

Date	Code	Title	Description
1997-05-20	EEER	Examination request
2010-11-22	MKLA	Lapsed

Publication	Publication Date	Title
US6200558B1 (en)	2001-03-13	Biopolymer-bound nitric oxide-releasing compositions, pharmaceutical compositions incorporating same and methods of treating biological disorders using same
US5632981A (en)	1997-05-27	Biopolymer-bound nitric oxide-releasing compositions, pharmaceutical compositions incorporating same and methods of treating biological disorders using same
US5525357A (en)	1996-06-11	Polymer-bound nitric oxide/nucleophile adduct compositions, pharmaceutical compositions incorporating same and methods of treating biological disorders using same
CA2205555C (fr)	2001-08-21	Utilisation d'agents liberant de l'oxyde nitrique pour reduire les risques de metastase
US5676963A (en)	1997-10-14	Implants, prostheses, and stents comprising polymer-bound nitric oxide/nucleophile adducts capable of releasing nitric oxide
CA2216696C (fr)	2009-01-06	Produits d'addition bioxyde d'azote-nucleophiles lies a des polysaccharides
CA2185457C (fr)	2004-05-25	Utilisation de polymeres liberant de l'acide nitrique dans le but de traiter la restenose et des maladies apparentees
US6290981B1 (en)	2001-09-18	Use of nitric oxide-releasing agents to treat impotency
CA2106105C (fr)	2008-03-18	Compositions d'addition oxyde nitrique-agent polymerique liees par des polymeres, compositions pharmaceutiques incorporant ces produits et methodes pour le traitement de desordresbiologiques a l'aide de ceux-ci
CA2205564C (fr)	2006-07-11	Compositions pharmaceutiques comprenant des biopolymeres liberant de l'oxyde nitrique
AU695579C (en)	1999-06-24	Polysaccharide-bound nitric oxide-nucleophile adducts