CA2422787A1 - C-nitroso compounds and use thereof - Google Patents
C-nitroso compounds and use thereof Download PDFInfo
- Publication number
- CA2422787A1 CA2422787A1 CA002422787A CA2422787A CA2422787A1 CA 2422787 A1 CA2422787 A1 CA 2422787A1 CA 002422787 A CA002422787 A CA 002422787A CA 2422787 A CA2422787 A CA 2422787A CA 2422787 A1 CA2422787 A1 CA 2422787A1
- Authority
- CA
- Canada
- Prior art keywords
- nitroso
- compound
- nitroso compound
- carbon
- conventional drug
- 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
- 150000004006 C-nitroso compounds Chemical class 0.000 title claims abstract description 176
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 138
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 125
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 239000002253 acid Substances 0.000 claims abstract description 70
- 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 abstract description 40
- 230000009635 nitrosylation Effects 0.000 claims abstract description 32
- 108010024636 Glutathione Proteins 0.000 claims abstract description 20
- 229960003180 glutathione Drugs 0.000 claims abstract description 20
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims abstract description 14
- 229920000249 biocompatible polymer Polymers 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims description 66
- 229940079593 drug Drugs 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 35
- 230000015572 biosynthetic process Effects 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 30
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 22
- 150000001721 carbon Chemical group 0.000 claims description 20
- 229940111134 coxibs Drugs 0.000 claims description 20
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 229960001680 ibuprofen Drugs 0.000 claims description 13
- 150000002148 esters Chemical group 0.000 claims description 11
- 235000019260 propionic acid Nutrition 0.000 claims description 11
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- XGELWHWQKAMULX-UHFFFAOYSA-N CC(C)CC1=CC=C(C(C=O)(N=O)C(O)=O)C=C1 Chemical compound CC(C)CC1=CC=C(C(C=O)(N=O)C(O)=O)C=C1 XGELWHWQKAMULX-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 10
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 8
- 230000000326 anti-hypercholesterolaemic effect Effects 0.000 claims description 8
- 239000000480 calcium channel blocker Substances 0.000 claims description 8
- 230000015271 coagulation Effects 0.000 claims description 8
- 238000005345 coagulation Methods 0.000 claims description 8
- 230000001028 anti-proliverative effect Effects 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 229940124630 bronchodilator Drugs 0.000 claims description 7
- 239000002934 diuretic Substances 0.000 claims description 7
- 230000002757 inflammatory effect Effects 0.000 claims description 7
- 208000037803 restenosis Diseases 0.000 claims description 7
- 239000005541 ACE inhibitor Substances 0.000 claims description 6
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 6
- 229940069428 antacid Drugs 0.000 claims description 6
- 239000003159 antacid agent Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 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 5
- 208000007536 Thrombosis Diseases 0.000 claims description 5
- 102000004243 Tubulin Human genes 0.000 claims description 5
- 108090000704 Tubulin Proteins 0.000 claims description 5
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims description 5
- 239000003158 myorelaxant agent Substances 0.000 claims description 5
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 5
- 210000002027 skeletal muscle Anatomy 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 229940035676 analgesics Drugs 0.000 claims description 4
- 239000000730 antalgic agent Substances 0.000 claims description 4
- 230000001458 anti-acid effect Effects 0.000 claims description 4
- 238000006471 dimerization reaction Methods 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000003064 xanthine oxidase inhibitor Substances 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 239000004004 anti-anginal agent Substances 0.000 claims description 3
- 239000002220 antihypertensive agent Substances 0.000 claims description 3
- 229940127088 antihypertensive drug Drugs 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 3
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 210000001519 tissue Anatomy 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229940124976 antitubercular drug Drugs 0.000 claims 1
- 150000002832 nitroso derivatives Chemical class 0.000 claims 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 46
- 230000002040 relaxant effect Effects 0.000 abstract description 7
- 239000002840 nitric oxide donor Substances 0.000 abstract description 3
- 230000002792 vascular Effects 0.000 abstract 2
- -1 -COZMe Chemical group 0.000 description 50
- 125000003118 aryl group Chemical group 0.000 description 39
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 39
- 238000003786 synthesis reaction Methods 0.000 description 20
- 125000004429 atom Chemical group 0.000 description 17
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 16
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 16
- 230000008901 benefit Effects 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 13
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 13
- 239000000539 dimer Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 230000005764 inhibitory process Effects 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 206010002383 Angina Pectoris Diseases 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- 235000019647 acidic taste Nutrition 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Chemical group 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KEJOCWOXCDWNID-UHFFFAOYSA-N Nitrilooxonium Chemical compound [O+]#N KEJOCWOXCDWNID-UHFFFAOYSA-N 0.000 description 6
- 241001482237 Pica Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000003257 anti-anginal effect Effects 0.000 description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- 239000012634 fragment Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 230000001882 diuretic effect Effects 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 125000000468 ketone group Chemical group 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 239000011593 sulfur Chemical group 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 229910004373 HOAc Inorganic materials 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- 150000004009 O-nitroso compounds Chemical group 0.000 description 4
- 150000004007 S-nitroso compounds Chemical class 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 206010046543 Urinary incontinence Diseases 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Chemical group 0.000 description 4
- 229940047495 celebrex Drugs 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- HDUWKQUHMUSICC-UHFFFAOYSA-N n-[6-(2,4-difluorophenyl)sulfanyl-1-oxo-2,3-dihydroinden-5-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=2CCC(=O)C=2C=C1SC1=CC=C(F)C=C1F HDUWKQUHMUSICC-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RCINGEKPKJQCMO-UHFFFAOYSA-N 2-[4-(2-methylpropanoyl)phenyl]propanoic acid Chemical compound CC(C)C(=O)C1=CC=C(C(C)C(O)=O)C=C1 RCINGEKPKJQCMO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000006820 Arthralgia Diseases 0.000 description 3
- 229940124638 COX inhibitor Drugs 0.000 description 3
- 206010019280 Heart failures Diseases 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 238000000149 argon plasma sintering Methods 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
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- 230000002939 deleterious effect Effects 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 201000001881 impotence Diseases 0.000 description 3
- 229960001361 ipratropium bromide Drugs 0.000 description 3
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 3
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- LQQKDSXCDXHLLF-UHFFFAOYSA-N 1,3-dibromopropan-2-one Chemical class BrCC(=O)CBr LQQKDSXCDXHLLF-UHFFFAOYSA-N 0.000 description 2
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 2
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 description 2
- LUQZKEZPFQRRRK-UHFFFAOYSA-N 2-methyl-2-nitrosopropane Chemical compound CC(C)(C)N=O LUQZKEZPFQRRRK-UHFFFAOYSA-N 0.000 description 2
- UYWYAVSXVNXXKZ-UHFFFAOYSA-N 3-methyl-3-nitrosopentane-2,4-dione Chemical compound CC(=O)C(C)(N=O)C(C)=O UYWYAVSXVNXXKZ-UHFFFAOYSA-N 0.000 description 2
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
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- 0 CCC*C1CCCC1 Chemical compound CCC*C1CCCC1 0.000 description 2
- 241001327708 Coriaria sarmentosa Species 0.000 description 2
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- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 2
- 239000000006 Nitroglycerin Substances 0.000 description 2
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- CCAZWUJBLXKBAY-ULZPOIKGSA-N Tutin Chemical compound C([C@]12[C@@H]3O[C@@H]3[C@@]3(O)[C@H]4C(=O)O[C@@H]([C@H]([C@]32C)O)[C@H]4C(=C)C)O1 CCAZWUJBLXKBAY-ULZPOIKGSA-N 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 2
- 229960000528 amlodipine Drugs 0.000 description 2
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- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000000168 bronchodilator agent Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 2
- 230000003293 cardioprotective effect Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
- 229960001214 clofibrate Drugs 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
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- 239000000651 prodrug Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical group C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QULKDBMYSOOKMH-UHFFFAOYSA-N sulfo hydrogen carbonate Chemical group OC(=O)OS(O)(=O)=O QULKDBMYSOOKMH-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000006499 vasodilator function Effects 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C207/00—Compounds containing nitroso groups bound to a carbon skeleton
-
- 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
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Virology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/695,934 | 2000-10-26 | ||
| US09/695,934 US6359182B1 (en) | 2000-10-26 | 2000-10-26 | C-nitroso compounds and use thereof |
| PCT/US2001/027734 WO2002034705A2 (en) | 2000-10-26 | 2001-09-27 | C-nitroso compounds and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2422787A1 true CA2422787A1 (en) | 2002-05-02 |
Family
ID=24795034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002422787A Abandoned CA2422787A1 (en) | 2000-10-26 | 2001-09-27 | C-nitroso compounds and use thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US6359182B1 (enExample) |
| EP (1) | EP1330425B1 (enExample) |
| JP (1) | JP2004512318A (enExample) |
| AU (1) | AU2001292582A1 (enExample) |
| CA (1) | CA2422787A1 (enExample) |
| DE (1) | DE60128940T2 (enExample) |
| WO (1) | WO2002034705A2 (enExample) |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040072889A1 (en) * | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
| US20040122011A1 (en) * | 1998-12-23 | 2004-06-24 | Pharmacia Corporation | Method of using a COX-2 inhibitor and a TACE inhibitors as a combination therapy |
| AU2002211222B2 (en) | 2000-10-16 | 2006-02-09 | Duke University | Therapeutic use of aerosolized S-nitrosoglutathione in cystic fibrosis |
| US6359182B1 (en) * | 2000-10-26 | 2002-03-19 | Duke University | C-nitroso compounds and use thereof |
| US7049308B2 (en) * | 2000-10-26 | 2006-05-23 | Duke University | C-nitroso compounds and use thereof |
| US6627602B2 (en) | 2001-11-13 | 2003-09-30 | Duke University | Preventing desensitization of receptors |
| JP4563679B2 (ja) * | 2001-12-06 | 2010-10-13 | デューク ユニバーシティ | 形成外科における組織弁壊死の予防 |
| US20030212138A1 (en) * | 2002-01-14 | 2003-11-13 | Pharmacia Corporation | Combinations of peroxisome proliferator-activated receptor-alpha agonists and cyclooxygenase-2 selective inhibitors and therapeutic uses therefor |
| US20030220374A1 (en) * | 2002-01-14 | 2003-11-27 | Pharmacia Corporation | Compositions and methods of treatment involving peroxisome proliferator-activated receptor-gamma agonists and cyclooxygenase-2 selective inhibitors |
| US20040147581A1 (en) * | 2002-11-18 | 2004-07-29 | Pharmacia Corporation | Method of using a Cox-2 inhibitor and a 5-HT1A receptor modulator as a combination therapy |
| WO2004050639A2 (en) * | 2002-12-03 | 2004-06-17 | Epcellon, Inc. | 5-nitroso-6-piperazinyl-pyrimidine derivatives for treating ischemia |
| PT1572173E (pt) | 2002-12-13 | 2010-05-10 | Warner Lambert Co | Ligando alfa-2-delta para tratar sintomas do tracto urinário inferior |
| WO2004062598A2 (en) * | 2003-01-13 | 2004-07-29 | Beta Pharma, Inc. | Anti-inflammatory and anti-thrombotic compounds and their compositions |
| US20040220155A1 (en) * | 2003-03-28 | 2004-11-04 | Pharmacia Corporation | Method of providing a steroid-sparing benefit with a cyclooxygenase-2 inhibitor and compositions therewith |
| WO2005009342A2 (en) * | 2003-07-16 | 2005-02-03 | Pharmacia Corporation | Method for the treatment or prevention of dermatological disorders with a cyclooxygenase-2 inhibitor alone and in combination with a dermatological treatment agent and compositions therewith |
| US20050119262A1 (en) * | 2003-08-21 | 2005-06-02 | Pharmacia Corporation | Method for preventing or treating an optic neuropathy with a cox-2 inhibitor and an intraocular pressure reducing agent |
| US20050107350A1 (en) * | 2003-08-22 | 2005-05-19 | Pharmacia Corporation | Method for the treatment or prevention of bone disorders with a cyclooxygenase-2 inhibitor alone and in combination with a bone disorder treatment agent and compositions therewith |
| US20050187278A1 (en) * | 2003-08-28 | 2005-08-25 | Pharmacia Corporation | Treatment or prevention of vascular disorders with Cox-2 inhibitors in combination with cyclic AMP-specific phosphodiesterase inhibitors |
| WO2005023189A2 (en) * | 2003-09-03 | 2005-03-17 | Pharmacia Corporation | Method of cox-2 selective inhibitor and nitric oxide-donating agent |
| EP1708718A1 (en) | 2004-01-22 | 2006-10-11 | Pfizer Limited | Triazole derivatives which inhibit vasopressin antagonistic activity |
| US7829553B2 (en) * | 2004-02-09 | 2010-11-09 | Amulet Pharmaceuticals, Inc. | Nitric oxide-releasing polymers |
| US8470417B2 (en) | 2004-04-02 | 2013-06-25 | Curwood, Inc. | Packaging inserts with myoglobin blooming agents, packages and methods for packaging |
| US8053047B2 (en) | 2004-04-02 | 2011-11-08 | Curwood, Inc. | Packaging method that causes and maintains the preferred red color of fresh meat |
| US7867531B2 (en) | 2005-04-04 | 2011-01-11 | Curwood, Inc. | Myoglobin blooming agent containing shrink films, packages and methods for packaging |
| US8741402B2 (en) | 2004-04-02 | 2014-06-03 | Curwood, Inc. | Webs with synergists that promote or preserve the desirable color of meat |
| US8110259B2 (en) | 2004-04-02 | 2012-02-07 | Curwood, Inc. | Packaging articles, films and methods that promote or preserve the desirable color of meat |
| US8029893B2 (en) | 2004-04-02 | 2011-10-04 | Curwood, Inc. | Myoglobin blooming agent, films, packages and methods for packaging |
| US8545950B2 (en) | 2004-04-02 | 2013-10-01 | Curwood, Inc. | Method for distributing a myoglobin-containing food product |
| US7067659B2 (en) * | 2004-04-23 | 2006-06-27 | Duke University | Reactive oxygen generating enzyme inhibitor with nitric oxide bioactivity and uses thereof |
| US20070225333A1 (en) * | 2004-04-28 | 2007-09-27 | Bryans Justin S | 3-Heterocyclyl-4-Phenyl-Triazole Derivatives as Inhibitors of the Vasopressin Via Receptor |
| EP2669269B1 (en) | 2005-05-27 | 2019-05-22 | The University of North Carolina At Chapel Hill | Nitric oxide-releasing particles for nitric oxide therapeutics and biomedical applications |
| WO2007067477A1 (en) * | 2005-12-06 | 2007-06-14 | Amulet Pharmaceuticals, Inc. | Nitric oxide-releasing polymers |
| US7686448B2 (en) * | 2006-06-16 | 2010-03-30 | Marie Betts-Johnson | Eyeglass frames |
| US9259535B2 (en) | 2006-06-22 | 2016-02-16 | Excelsior Medical Corporation | Antiseptic cap equipped syringe |
| US11229746B2 (en) | 2006-06-22 | 2022-01-25 | Excelsior Medical Corporation | Antiseptic cap |
| US20080025972A1 (en) * | 2006-07-26 | 2008-01-31 | Duke University | Treating sex steriod responsive disorders |
| CN102058885B (zh) | 2006-12-22 | 2013-04-10 | 瑞蔻达蒂爱尔兰有限公司 | 采用α2δ配体和NSAID的下泌尿道疾病的联合治疗 |
| WO2008130566A1 (en) * | 2007-04-20 | 2008-10-30 | Duke University | Nitroxyl ion source with second order reaction nitroxyl release |
| WO2008130567A1 (en) * | 2007-04-20 | 2008-10-30 | Duke University | Stable neutral nitric oxide source |
| LT2318006T (lt) | 2008-08-15 | 2017-01-10 | Nivalis Therapeutics, Inc. | Nauji s-nitrozoglutationo reduktazės pirolo inhibitoriai, kaip terapiniai agentai |
| US8642628B2 (en) | 2008-08-15 | 2014-02-04 | N30 Pharmaceuticals, Inc. | Pyrrole inhibitors of S-nitrosoglutathione reductase |
| US20100098733A1 (en) * | 2008-10-16 | 2010-04-22 | Novan, Inc. | Nitric oxide releasing particles for oral care applications |
| US9078992B2 (en) | 2008-10-27 | 2015-07-14 | Pursuit Vascular, Inc. | Medical device for applying antimicrobial to proximal end of catheter |
| EP2467173B8 (en) | 2009-08-21 | 2019-06-19 | Novan, Inc. | Wound dressings, methods of using the same and methods of forming the same |
| WO2011022652A1 (en) | 2009-08-21 | 2011-02-24 | Novan, Inc. | Topical gels |
| WO2011038204A1 (en) | 2009-09-25 | 2011-03-31 | N30 Pharmaceuticals, Llc | Novel dihydropyrimidin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors |
| WO2011047013A1 (en) * | 2009-10-13 | 2011-04-21 | Novan, Inc. | Nitric oxide-releasing coatings |
| WO2011075478A1 (en) | 2009-12-16 | 2011-06-23 | N30 Pharmaceuticals, Llc | Novel thiophene inhibitors of s-nitrosoglutathione reductase |
| SI2533638T1 (sl) | 2010-02-12 | 2016-05-31 | Nivalis Therapeutics, Inc. | Novi inhibitorji S-nitrozoglutation reduktaze |
| ES2550939T3 (es) | 2010-07-16 | 2015-11-13 | Nivalis Therapeutics, Inc. | Nuevos compuestos de dihidropiridin-2-(1H)-ona como inhibidores de la S-nitrosoglutatión reductasa y antagonistas del receptor de la neurocinina-3 |
| ES2553771T3 (es) | 2010-10-08 | 2015-12-11 | Nivalis Therapeutics, Inc. | Nuevos compuestos de quinolina sustituidos como inhibidores de la S-nitrosoglutatión reductasa |
| EP2468269A1 (en) | 2010-11-26 | 2012-06-27 | Universitätsklinikum Münster | Nitric oxide donors in therapy of nitric oxide deficiency-induced disturbances of cerebral microcirculation |
| US8591876B2 (en) | 2010-12-15 | 2013-11-26 | Novan, Inc. | Methods of decreasing sebum production in the skin |
| JP5990187B2 (ja) | 2010-12-16 | 2016-09-07 | ニヴァリス・セラピューティクス・インコーポレーテッド | Ｓ−ニトロソグルタチオン還元酵素阻害薬としての新規な置換二環芳香族化合物 |
| WO2012118819A2 (en) | 2011-02-28 | 2012-09-07 | Novan, Inc. | Nitric oxide-releasing s-nitrosothiol-modified silica particles and methods of making the same |
| US10166381B2 (en) | 2011-05-23 | 2019-01-01 | Excelsior Medical Corporation | Antiseptic cap |
| CA2841832C (en) | 2011-07-12 | 2019-06-04 | Icu Medical, Inc. | Device for delivery of antimicrobial agent into a trans-dermal catheter |
| WO2013132497A1 (en) | 2012-03-07 | 2013-09-12 | Advanced Inhilation Therapies (Ait) Ltd. | Inhalation of nitric oxide for treating respiratory diseases |
| AU2015252808B2 (en) | 2014-05-02 | 2019-02-21 | Excelsior Medical Corporation | Strip package for antiseptic cap |
| EP3226859B1 (en) | 2014-12-05 | 2025-03-26 | Case Western Reserve University | Akr1a1 inhibitors for use in lowering cholesterol and modulate s-nitrosylation |
| AU2016262400B2 (en) | 2015-05-08 | 2021-01-21 | Icu Medical, Inc. | Medical connectors configured to receive emitters of therapeutic agents |
| EP4548975A3 (en) | 2015-09-09 | 2025-07-23 | Beyond Air Ltd | Nitric oxide inhalation therapy for infants with bronchiolitis |
| WO2018049027A1 (en) | 2016-09-07 | 2018-03-15 | Trustees Of Tufts College | Combination therapies using immuno-dash inhibitors and pge2 antagonists |
| CA3040277C (en) | 2016-10-14 | 2025-08-12 | Icu Medical, Inc. | DISINFECTANT CAPS FOR MEDICAL FITTINGS |
| WO2018204206A2 (en) | 2017-05-01 | 2018-11-08 | Icu Medical, Inc. | Medical fluid connectors and methods for providing additives in medical fluid lines |
| EP3765123B1 (en) | 2018-03-16 | 2026-07-15 | ICU Medical, Inc. | Sanitizing caps for medical connectors |
| US11541221B2 (en) | 2018-11-07 | 2023-01-03 | Icu Medical, Inc. | Tubing set with antimicrobial properties |
| US11541220B2 (en) | 2018-11-07 | 2023-01-03 | Icu Medical, Inc. | Needleless connector with antimicrobial properties |
| US11534595B2 (en) | 2018-11-07 | 2022-12-27 | Icu Medical, Inc. | Device for delivering an antimicrobial composition into an infusion device |
| US11517732B2 (en) | 2018-11-07 | 2022-12-06 | Icu Medical, Inc. | Syringe with antimicrobial properties |
| US11400195B2 (en) | 2018-11-07 | 2022-08-02 | Icu Medical, Inc. | Peritoneal dialysis transfer set with antimicrobial properties |
| EP3883638A1 (en) | 2018-11-21 | 2021-09-29 | ICU Medical, Inc. | Antimicrobial device comprising a cap with ring and insert |
| CN110396086B (zh) * | 2019-04-23 | 2023-03-24 | 天津国际生物医药联合研究院 | No供体类化合物、组合物、制备方法和及其应用 |
| JP7888563B2 (ja) | 2020-12-07 | 2026-07-13 | アイシーユー・メディカル・インコーポレーテッド | 医療用コネクタのためのキャップシステム、キャップと共に使用されるベース要素、及びベース要素上にキャップを保持するための方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9423868D0 (en) * | 1994-11-25 | 1995-01-11 | Wellcome Found | Compounds for use in medicine |
| GB9424694D0 (en) * | 1994-12-07 | 1995-02-01 | Wellcome Found | Compounds for use in medicine |
| EP1126838A4 (en) * | 1998-10-30 | 2005-02-16 | Nitromed Inc | NITROSIS AND NITROSYAL NON-STEROID ANTI-INFLAMMATORY COMPOUNDS, COMPOSITIONS AND METHODS OF USE |
| US6231894B1 (en) | 1999-10-21 | 2001-05-15 | Duke University | Treatments based on discovery that nitric oxide synthase is a paraquat diaphorase |
| US7049308B2 (en) * | 2000-10-26 | 2006-05-23 | Duke University | C-nitroso compounds and use thereof |
| US6359182B1 (en) * | 2000-10-26 | 2002-03-19 | Duke University | C-nitroso compounds and use thereof |
-
2000
- 2000-10-26 US US09/695,934 patent/US6359182B1/en not_active Expired - Fee Related
-
2001
- 2001-09-27 JP JP2002537699A patent/JP2004512318A/ja not_active Ceased
- 2001-09-27 AU AU2001292582A patent/AU2001292582A1/en not_active Abandoned
- 2001-09-27 DE DE60128940T patent/DE60128940T2/de not_active Expired - Lifetime
- 2001-09-27 EP EP01972952A patent/EP1330425B1/en not_active Expired - Lifetime
- 2001-09-27 WO PCT/US2001/027734 patent/WO2002034705A2/en not_active Ceased
- 2001-09-27 CA CA002422787A patent/CA2422787A1/en not_active Abandoned
- 2001-12-13 US US10/013,491 patent/US6538116B2/en not_active Expired - Fee Related
-
2003
- 2003-01-17 US US10/346,146 patent/US6887994B2/en not_active Expired - Fee Related
-
2005
- 2005-02-09 US US11/052,777 patent/US7030238B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1330425B1 (en) | 2007-06-13 |
| US20050203295A1 (en) | 2005-09-15 |
| US20020077506A1 (en) | 2002-06-20 |
| US6887994B2 (en) | 2005-05-03 |
| WO2002034705A2 (en) | 2002-05-02 |
| EP1330425A2 (en) | 2003-07-30 |
| DE60128940D1 (de) | 2007-07-26 |
| WO2002034705A3 (en) | 2002-07-11 |
| US6359182B1 (en) | 2002-03-19 |
| US6538116B2 (en) | 2003-03-25 |
| US20030176668A1 (en) | 2003-09-18 |
| DE60128940T2 (de) | 2008-02-21 |
| AU2001292582A1 (en) | 2002-05-06 |
| US7030238B2 (en) | 2006-04-18 |
| JP2004512318A (ja) | 2004-04-22 |
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