CA2464757A1 - Selective antibacterial agents - Google Patents
Selective antibacterial agents Download PDFInfo
- Publication number
- CA2464757A1 CA2464757A1 CA002464757A CA2464757A CA2464757A1 CA 2464757 A1 CA2464757 A1 CA 2464757A1 CA 002464757 A CA002464757 A CA 002464757A CA 2464757 A CA2464757 A CA 2464757A CA 2464757 A1 CA2464757 A1 CA 2464757A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- hydrazide
- group
- aryl
- chz
- 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
- 239000003242 anti bacterial agent Substances 0.000 title claims description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 160
- 125000003118 aryl group Chemical group 0.000 claims abstract description 93
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 84
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 67
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 51
- 230000018612 quorum sensing Effects 0.000 claims abstract description 41
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 33
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 32
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 32
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims abstract description 32
- 125000001424 substituent group Chemical group 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical class 0.000 claims abstract description 23
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 12
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 claims abstract description 11
- VKVJIWVUYNTBEZ-UHFFFAOYSA-N 1,3-bis(3,5-dichlorophenyl)urea Chemical compound ClC1=CC(Cl)=CC(NC(=O)NC=2C=C(Cl)C=C(Cl)C=2)=C1 VKVJIWVUYNTBEZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 244000005700 microbiome Species 0.000 claims abstract description 10
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 10
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 9
- 230000033228 biological regulation Effects 0.000 claims abstract description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract 4
- -1 -NR4R5 Chemical group 0.000 claims description 123
- 238000011282 treatment Methods 0.000 claims description 40
- 230000032770 biofilm formation Effects 0.000 claims description 34
- 230000002401 inhibitory effect Effects 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 24
- 241000894006 Bacteria Species 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 230000001580 bacterial effect Effects 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 11
- 230000014509 gene expression Effects 0.000 claims description 10
- 241000589513 Burkholderia cepacia Species 0.000 claims description 9
- 230000003373 anti-fouling effect Effects 0.000 claims description 9
- 230000006378 damage Effects 0.000 claims description 8
- 230000007613 environmental effect Effects 0.000 claims description 8
- 239000000304 virulence factor Substances 0.000 claims description 8
- 230000007923 virulence factor Effects 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 7
- 230000001419 dependent effect Effects 0.000 claims description 7
- 239000000645 desinfectant Substances 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 4
- ZPRYNXKSYQQKEN-UHFFFAOYSA-N 3-chloro-4-methyl-n'-(thiophene-2-carbonyl)thiophene-2-carbohydrazide Chemical compound CC1=CSC(C(=O)NNC(=O)C=2SC=CC=2)=C1Cl ZPRYNXKSYQQKEN-UHFFFAOYSA-N 0.000 claims description 3
- VJIOMBMUZCYCMZ-UHFFFAOYSA-N 3-chloro-n'-(thiophene-2-carbonyl)thiophene-2-carbohydrazide Chemical compound C1=CSC(C(=O)NNC(=O)C=2SC=CC=2)=C1Cl VJIOMBMUZCYCMZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 238000009826 distribution Methods 0.000 claims description 3
- KCYCNAKUKAQKKO-UHFFFAOYSA-N n'-(thiophene-2-carbonyl)furan-2-carbohydrazide Chemical compound C=1C=COC=1C(=O)NNC(=O)C1=CC=CS1 KCYCNAKUKAQKKO-UHFFFAOYSA-N 0.000 claims description 3
- FBOFFEXPCHQWDX-UHFFFAOYSA-N n'-(thiophene-2-carbonyl)thiophene-2-carbohydrazide Chemical compound C=1C=CSC=1C(=O)NNC(=O)C1=CC=CS1 FBOFFEXPCHQWDX-UHFFFAOYSA-N 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- WYDHONZWGITXDK-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(thiophene-2-carbonylamino)urea Chemical compound ClC1=CC=CC(NC(=O)NNC(=O)C=2SC=CC=2)=C1 WYDHONZWGITXDK-UHFFFAOYSA-N 0.000 claims description 2
- IGEWYPDRERTIJP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(thiophene-2-carbonylamino)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NNC(=O)C1=CC=CS1 IGEWYPDRERTIJP-UHFFFAOYSA-N 0.000 claims description 2
- ZHTLSBATHZSNQU-UHFFFAOYSA-N 1-(4-methylphenyl)-3-(thiophene-2-carbonylamino)urea Chemical compound C1=CC(C)=CC=C1NC(=O)NNC(=O)C1=CC=CS1 ZHTLSBATHZSNQU-UHFFFAOYSA-N 0.000 claims description 2
- VHPVACPJTROCHA-UHFFFAOYSA-N 1-phenyl-3-(thiophene-2-carbonylamino)urea Chemical compound C=1C=CC=CC=1NC(=O)NNC(=O)C1=CC=CS1 VHPVACPJTROCHA-UHFFFAOYSA-N 0.000 claims description 2
- YRUVNMHNVOFZTM-UHFFFAOYSA-N 4-butyl-n'-(4-butylthiophene-2-carbonyl)thiophene-2-carbohydrazide Chemical compound CCCCC1=CSC(C(=O)NNC(=O)C=2SC=C(CCCC)C=2)=C1 YRUVNMHNVOFZTM-UHFFFAOYSA-N 0.000 claims description 2
- SUJPOGCFLVSXOZ-UHFFFAOYSA-N 5-bromo-n'-(thiophene-2-carbonyl)furan-2-carbohydrazide Chemical compound O1C(Br)=CC=C1C(=O)NNC(=O)C1=CC=CS1 SUJPOGCFLVSXOZ-UHFFFAOYSA-N 0.000 claims description 2
- XVPVQUGDFAWLKO-UHFFFAOYSA-N 5-bromo-n'-(thiophene-2-carbonyl)thiophene-2-carbohydrazide Chemical compound S1C(Br)=CC=C1C(=O)NNC(=O)C1=CC=CS1 XVPVQUGDFAWLKO-UHFFFAOYSA-N 0.000 claims description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- FYWKMBRPROCTTO-UHFFFAOYSA-N CC1(CC(=CC=C1Cl)NC(=O)NNC(=O)C=1SC=CC1)Cl Chemical compound CC1(CC(=CC=C1Cl)NC(=O)NNC(=O)C=1SC=CC1)Cl FYWKMBRPROCTTO-UHFFFAOYSA-N 0.000 claims description 2
- KCFVMGQTUAWANB-UHFFFAOYSA-N n'-(thiophene-2-carbonyl)-1h-pyrrole-2-carbohydrazide Chemical compound C=1C=CNC=1C(=O)NNC(=O)C1=CC=CS1 KCFVMGQTUAWANB-UHFFFAOYSA-N 0.000 claims description 2
- OZEVAFWEKPJYRC-UHFFFAOYSA-N n'-[5-[[4-methyl-6-(trifluoromethyl)pyrimidin-2-yl]sulfanylmethyl]thiophene-2-carbonyl]furan-2-carbohydrazide Chemical compound CC1=CC(C(F)(F)F)=NC(SCC=2SC(=CC=2)C(=O)NNC(=O)C=2OC=CC=2)=N1 OZEVAFWEKPJYRC-UHFFFAOYSA-N 0.000 claims description 2
- YNIKVCVLZNDSLU-UHFFFAOYSA-N n-methyl-n'-(thiophene-2-carbonyl)-1h-pyrazole-5-carbohydrazide Chemical compound C=1C=NNC=1C(=O)N(C)NC(=O)C1=CC=CS1 YNIKVCVLZNDSLU-UHFFFAOYSA-N 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 4
- 239000000498 cooling water Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- SDWZNSDRIKUBDL-UHFFFAOYSA-N 2-ethyl-5-methyl-n-(2-methylpyrazol-3-yl)-4-nitropyrazole-3-carboxamide Chemical compound CCN1N=C(C)C([N+]([O-])=O)=C1C(=O)NC1=CC=NN1C SDWZNSDRIKUBDL-UHFFFAOYSA-N 0.000 claims 1
- PULQQRHHMZFIQG-UHFFFAOYSA-N 5-nitro-n'-(thiophene-2-carbonyl)thiophene-2-carbohydrazide Chemical compound S1C([N+](=O)[O-])=CC=C1C(=O)NNC(=O)C1=CC=CS1 PULQQRHHMZFIQG-UHFFFAOYSA-N 0.000 claims 1
- ISMJKPKPXKXKLQ-UHFFFAOYSA-N n'-(4-bromo-5-methylthiophene-2-carbonyl)-n-methyl-1h-pyrazole-5-carbohydrazide Chemical compound C1=CNN=C1C(=O)N(C)NC(=O)C1=CC(Br)=C(C)S1 ISMJKPKPXKXKLQ-UHFFFAOYSA-N 0.000 claims 1
- IQXBKZZSCIJSEJ-UHFFFAOYSA-N n-(2-methylpyrazol-3-yl)pyrazole-1-carboxamide Chemical compound CN1N=CC=C1NC(=O)N1N=CC=C1 IQXBKZZSCIJSEJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 215
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 65
- 125000006519 CCH3 Chemical group 0.000 description 44
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 37
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 34
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 32
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 32
- 238000000034 method Methods 0.000 description 31
- QJPWUUJVYOJNMH-UHFFFAOYSA-N homoserine lactone Chemical compound NC1CCOC1=O QJPWUUJVYOJNMH-UHFFFAOYSA-N 0.000 description 30
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 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 16
- 239000000203 mixture Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 15
- 108090000623 proteins and genes Proteins 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000002820 allylidene group Chemical group [H]C(=[*])C([H])=C([H])[H] 0.000 description 12
- 108091005804 Peptidases Proteins 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 229910052740 iodine Inorganic materials 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 230000001018 virulence Effects 0.000 description 11
- 239000004365 Protease Substances 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 230000012010 growth Effects 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 230000011664 signaling Effects 0.000 description 10
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 9
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229940088710 antibiotic agent Drugs 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 230000001105 regulatory effect Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000001308 synthesis method Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000012746 preparative thin layer chromatography Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000004599 antimicrobial Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical class 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 6
- 244000052769 pathogen Species 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 5
- 208000035143 Bacterial infection Diseases 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 241000282414 Homo sapiens Species 0.000 description 5
- 241000589516 Pseudomonas Species 0.000 description 5
- 208000022362 bacterial infectious disease Diseases 0.000 description 5
- 238000005415 bioluminescence Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 5
- 125000004519 1,2,5-thiadiazol-4-yl group Chemical group S1N=CC(=N1)* 0.000 description 4
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 241000607620 Aliivibrio fischeri Species 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 230000029918 bioluminescence Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- YNCMLFHHXWETLD-UHFFFAOYSA-N pyocyanin Chemical compound CN1C2=CC=CC=C2N=C2C1=CC=CC2=O YNCMLFHHXWETLD-UHFFFAOYSA-N 0.000 description 4
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 4
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 230000005174 swarming motility Effects 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 4
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 4
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 3
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 3
- 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 3
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 3
- 125000004507 1,2,5-oxadiazol-3-yl group Chemical group O1N=C(C=N1)* 0.000 description 3
- 125000004518 1,2,5-thiadiazol-3-yl group Chemical group S1N=C(C=N1)* 0.000 description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 201000003883 Cystic fibrosis Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- QJPWUUJVYOJNMH-VKHMYHEASA-N L-homoserine lactone Chemical group N[C@H]1CCOC1=O QJPWUUJVYOJNMH-VKHMYHEASA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- YRYOXRMDHALAFL-QMMMGPOBSA-N N-(3-oxohexanoyl)-L-homoserine lactone Chemical compound CCCC(=O)CC(=O)N[C@H]1CCOC1=O YRYOXRMDHALAFL-QMMMGPOBSA-N 0.000 description 3
- 241000588701 Pectobacterium carotovorum Species 0.000 description 3
- 206010040047 Sepsis Diseases 0.000 description 3
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Classifications
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
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- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medical Preparation Storing Or Oral Administration Devices (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- External Artificial Organs (AREA)
- Surgical Instruments (AREA)
- Detergent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Infusion, Injection, And Reservoir Apparatuses (AREA)
- Cosmetics (AREA)
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- Furan Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2001/012875 WO2003039529A1 (en) | 2001-11-07 | 2001-11-07 | Selective antibacterial agents |
| EPPCT/EP01/12875 | 2001-11-07 | ||
| US10/094,301 | 2002-03-08 | ||
| US10/094,301 US20030105143A1 (en) | 2001-11-07 | 2002-03-08 | Selective antibacterial agents |
| PCT/EP2002/011760 WO2003039549A2 (en) | 2001-11-07 | 2002-10-21 | Selective antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
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| CA2464757A1 true CA2464757A1 (en) | 2003-05-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002464757A Abandoned CA2464757A1 (en) | 2001-11-07 | 2002-10-21 | Selective antibacterial agents |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1478364B1 (enExample) |
| JP (1) | JP2005517635A (enExample) |
| CA (1) | CA2464757A1 (enExample) |
| WO (1) | WO2003039549A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1475092A1 (en) * | 2003-05-06 | 2004-11-10 | 4Sc Ag | Blockers of the quorum sensing system of Gram-negative bacteria |
| US7338969B2 (en) | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
| US7335779B2 (en) | 2002-03-08 | 2008-02-26 | Quonova, Llc | Modulation of pathogenicity |
| BR0215767A (pt) * | 2002-07-04 | 2005-03-15 | Aventis Pharma Sa | Novos derivados acil hidrazino de tiofeno, o repectivo processo de preparação, a respectiva aplicação a tìtulo de medicamentos, composições farmacêuticas e nova utilização |
| EP1667983A4 (en) * | 2003-09-23 | 2010-07-21 | Merck Sharp & Dohme | PYRAZOL MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS |
| TW200633998A (en) * | 2004-12-08 | 2006-10-01 | Nissan Chemical Ind Ltd | Substituted heterocyclic compounds and thrombopoietin receptor activators |
| CN101801449B (zh) * | 2007-07-16 | 2013-09-18 | Cr巴德公司 | 具有无菌屏障的福利导尿管 |
| WO2010150784A1 (ja) | 2009-06-22 | 2010-12-29 | 住友重機械工業株式会社 | 微生物活性向上剤、微生物活性向上方法及び生物学的廃棄物処理方法 |
| US8624063B2 (en) | 2009-06-30 | 2014-01-07 | Wisconsin Alumni Research Foundation | Non-lactone carbocyclic and heterocyclic antagonists and agonists of bacterial quorum sensing |
| US8579964B2 (en) | 2010-05-05 | 2013-11-12 | Neovasc Inc. | Transcatheter mitral valve prosthesis |
| US9554897B2 (en) | 2011-04-28 | 2017-01-31 | Neovasc Tiara Inc. | Methods and apparatus for engaging a valve prosthesis with tissue |
| US9308087B2 (en) | 2011-04-28 | 2016-04-12 | Neovasc Tiara Inc. | Sequentially deployed transcatheter mitral valve prosthesis |
| US9345573B2 (en) | 2012-05-30 | 2016-05-24 | Neovasc Tiara Inc. | Methods and apparatus for loading a prosthesis onto a delivery system |
| US9572665B2 (en) | 2013-04-04 | 2017-02-21 | Neovasc Tiara Inc. | Methods and apparatus for delivering a prosthetic valve to a beating heart |
| US10631984B2 (en) | 2015-12-15 | 2020-04-28 | Neovasc Tiara Inc. | Transseptal delivery system |
| CN108882981B (zh) | 2016-01-29 | 2021-08-10 | 内奥瓦斯克迪亚拉公司 | 用于防止流出阻塞的假体瓣膜 |
| AU2017361296B2 (en) | 2016-11-21 | 2022-09-29 | Neovasc Tiara Inc. | Methods and systems for rapid retraction of a transcatheter heart valve delivery system |
| EP3672530A4 (en) | 2017-08-25 | 2021-04-14 | Neovasc Tiara Inc. | SEQUENTIALLY INSERTED TRANSCATHETER MITRAL VALVE PROSTHESIS |
| US10526278B2 (en) | 2017-10-19 | 2020-01-07 | Wisconsin Alumni Research Foundation | Inhibitors of quorum sensing receptor LasR |
| AU2019374743B2 (en) | 2018-11-08 | 2022-03-03 | Neovasc Tiara Inc. | Ventricular deployment of a transcatheter mitral valve prosthesis |
| CN113747863B (zh) | 2019-03-08 | 2024-11-08 | 内奥瓦斯克迪亚拉公司 | 可取回假体递送系统 |
| EP4659710A2 (en) | 2019-04-01 | 2025-12-10 | Neovasc Tiara Inc. | Controllably deployable prosthetic valve |
| AU2020271896B2 (en) | 2019-04-10 | 2022-10-13 | Neovasc Tiara Inc. | Prosthetic valve with natural blood flow |
| US11779742B2 (en) | 2019-05-20 | 2023-10-10 | Neovasc Tiara Inc. | Introducer with hemostasis mechanism |
| US11311376B2 (en) | 2019-06-20 | 2022-04-26 | Neovase Tiara Inc. | Low profile prosthetic mitral valve |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE342661T1 (de) | 1997-06-18 | 2006-11-15 | Univ Montana State | Homoserinlactone zum regulieren von biofilmen und methoden zur anwendung |
| GB9725599D0 (en) | 1997-12-04 | 1998-02-04 | Univ Nottingham | Control of biofilm formation |
| US6559176B1 (en) | 2000-05-10 | 2003-05-06 | Princeton University | Compounds and methods for regulating bacterial growth and pathogenesis |
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2002
- 2002-10-21 EP EP02802626A patent/EP1478364B1/en not_active Expired - Lifetime
- 2002-10-21 WO PCT/EP2002/011760 patent/WO2003039549A2/en not_active Ceased
- 2002-10-21 JP JP2003541840A patent/JP2005517635A/ja active Pending
- 2002-10-21 CA CA002464757A patent/CA2464757A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003039549A2 (en) | 2003-05-15 |
| EP1478364B1 (en) | 2009-09-16 |
| JP2005517635A (ja) | 2005-06-16 |
| WO2003039549A3 (en) | 2004-05-27 |
| WO2003039549A8 (en) | 2004-02-26 |
| EP1478364A2 (en) | 2004-11-24 |
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