SK12662003A3 - Arylsulfónamidy ako antivírusové činidlá - Google Patents
Arylsulfónamidy ako antivírusové činidlá Download PDFInfo
- Publication number
- SK12662003A3 SK12662003A3 SK1266-2003A SK12662003A SK12662003A3 SK 12662003 A3 SK12662003 A3 SK 12662003A3 SK 12662003 A SK12662003 A SK 12662003A SK 12662003 A3 SK12662003 A3 SK 12662003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- hydroxyl
- amino
- alkyl
- same
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- 239000003443 antiviral agent Substances 0.000 title abstract description 3
- 125000004421 aryl sulphonamide group Chemical group 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 94
- 125000001424 substituent group Chemical group 0.000 claims abstract description 79
- 241000701022 Cytomegalovirus Species 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- -1 (C 1 -C 6 -alkoxy Chemical group 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 112
- 229910052736 halogen Inorganic materials 0.000 claims description 61
- 150000002367 halogens Chemical class 0.000 claims description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 54
- 229910052760 oxygen Inorganic materials 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 52
- 239000001301 oxygen Chemical group 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 229910052717 sulfur Chemical group 0.000 claims description 44
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 42
- 239000011593 sulfur Chemical group 0.000 claims description 42
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 39
- 239000000460 chlorine Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 208000015181 infectious disease Diseases 0.000 claims description 12
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 10
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 238000011321 prophylaxis Methods 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 230000003612 virological effect Effects 0.000 claims description 4
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 239000004743 Polypropylene Chemical group 0.000 claims 3
- 230000008030 elimination Effects 0.000 claims 2
- 238000003379 elimination reaction Methods 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- 238000004128 high performance liquid chromatography Methods 0.000 description 93
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 86
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 65
- 239000000243 solution Substances 0.000 description 54
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 46
- 229920005989 resin Polymers 0.000 description 37
- 239000011347 resin Substances 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 230000002829 reductive effect Effects 0.000 description 31
- 239000002904 solvent Substances 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 16
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- 230000015572 biosynthetic process Effects 0.000 description 15
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- 241000701024 Human betaherpesvirus 5 Species 0.000 description 14
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- 239000000126 substance Substances 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 7
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- 239000012894 fetal calf serum Substances 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 206010011831 Cytomegalovirus infection Diseases 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000010933 acylation Effects 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
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- 229940028332 halog Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine group Chemical group NO AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
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- 231100000225 lethality Toxicity 0.000 description 1
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- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 229940098779 methanesulfonic acid Drugs 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
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- WFWOGSWDVKAEFL-UHFFFAOYSA-N n-[3-[(4-cyanophenyl)sulfonylamino]phenyl]-1-methylcyclopropane-1-carboxamide Chemical compound C=1C=CC(NS(=O)(=O)C=2C=CC(=CC=2)C#N)=CC=1NC(=O)C1(C)CC1 WFWOGSWDVKAEFL-UHFFFAOYSA-N 0.000 description 1
- MNMRSZIXNJOIDQ-UHFFFAOYSA-N n-[3-[[4-(n'-hydroxycarbamimidoyl)phenyl]sulfonylamino]phenyl]-1-methylcyclopropane-1-carboxamide Chemical compound C=1C=CC(NS(=O)(=O)C=2C=CC(=CC=2)C(N)=NO)=CC=1NC(=O)C1(C)CC1 MNMRSZIXNJOIDQ-UHFFFAOYSA-N 0.000 description 1
- IYDUJFGERAVGOK-UHFFFAOYSA-N n-[3-[[4-[5-(1,5-dimethylpyrazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]sulfonylamino]phenyl]-1-methylcyclopropane-1-carboxamide Chemical compound CN1C(C)=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)S(=O)(=O)NC=2C=C(NC(=O)C3(C)CC3)C=CC=2)=N1 IYDUJFGERAVGOK-UHFFFAOYSA-N 0.000 description 1
- HLBKOCDHHMBMFR-UHFFFAOYSA-N n-[3-[[4-[5-(2-amino-1,3-thiazol-4-yl)-1,2,4-oxadiazol-3-yl]phenyl]sulfonylamino]phenyl]-1-methylcyclopropane-1-carboxamide Chemical compound C=1C=CC(NS(=O)(=O)C=2C=CC(=CC=2)C=2N=C(ON=2)C=2N=C(N)SC=2)=CC=1NC(=O)C1(C)CC1 HLBKOCDHHMBMFR-UHFFFAOYSA-N 0.000 description 1
- WOSXSOKNYZFKDJ-UHFFFAOYSA-N n-[3-[[4-[5-(6-acetamidopyridin-2-yl)-1,2,4-oxadiazol-3-yl]phenyl]sulfonylamino]phenyl]-3-fluoro-2,2-dimethylpropanamide Chemical compound CC(=O)NC1=CC=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)S(=O)(=O)NC=2C=C(NC(=O)C(C)(C)CF)C=CC=2)=N1 WOSXSOKNYZFKDJ-UHFFFAOYSA-N 0.000 description 1
- IZLLPFAMSMETMN-UHFFFAOYSA-N n-[3-[[4-[5-[2-(aminomethyl)-1,3-thiazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]sulfonylamino]phenyl]-1-methylcyclopropane-1-carboxamide Chemical compound C=1C=CC(NS(=O)(=O)C=2C=CC(=CC=2)C=2N=C(ON=2)C=2N=C(CN)SC=2)=CC=1NC(=O)C1(C)CC1 IZLLPFAMSMETMN-UHFFFAOYSA-N 0.000 description 1
- BPJBULQLMZUOFP-UHFFFAOYSA-N n-[3-[[4-[5-[3-(dimethylamino)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]sulfonylamino]phenyl]-1-methylcyclopropane-1-carboxamide Chemical compound CN(C)C1=CC=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)S(=O)(=O)NC=2C=C(NC(=O)C3(C)CC3)C=CC=2)=C1 BPJBULQLMZUOFP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 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 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 239000003106 tissue adhesive Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 description 1
- 229950004616 tribromoethanol Drugs 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10119137 | 2001-04-19 | ||
| DE10148598A DE10148598A1 (de) | 2001-04-19 | 2001-10-02 | Neue Arylsulfonamide als antivirale Mittel |
| PCT/EP2002/003858 WO2002085869A1 (de) | 2001-04-19 | 2002-04-08 | Arylsulfonamide als antivirale mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK12662003A3 true SK12662003A3 (sk) | 2004-04-06 |
Family
ID=26009118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1266-2003A SK12662003A3 (sk) | 2001-04-19 | 2002-04-08 | Arylsulfónamidy ako antivírusové činidlá |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7115612B2 (enExample) |
| EP (1) | EP1383749B1 (enExample) |
| JP (1) | JP4480941B2 (enExample) |
| CN (1) | CN1516695A (enExample) |
| AT (1) | ATE308529T1 (enExample) |
| BG (1) | BG108272A (enExample) |
| BR (1) | BR0209054A (enExample) |
| CA (1) | CA2444123C (enExample) |
| DE (1) | DE50204780D1 (enExample) |
| EE (1) | EE200300515A (enExample) |
| ES (1) | ES2252455T3 (enExample) |
| HU (1) | HUP0303813A3 (enExample) |
| IL (1) | IL158324A0 (enExample) |
| MX (1) | MXPA03009548A (enExample) |
| NO (1) | NO20034667L (enExample) |
| PL (1) | PL363990A1 (enExample) |
| RU (1) | RU2003133750A (enExample) |
| SK (1) | SK12662003A3 (enExample) |
| UY (1) | UY27263A1 (enExample) |
| WO (1) | WO2002085869A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20050168A2 (en) * | 2002-08-23 | 2005-10-31 | Rigel Pharmaceuticals | Pyridyl substituted heterocycles useful for treating or preventing hcv infection |
| DE10319612A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Healthcare Ag | Substituierte Dihydrochinazoline |
| EP4101846B1 (en) | 2003-04-11 | 2023-08-02 | PTC Therapeutics, Inc. | 1,2,4-oxadiazole benzoic acid compounds and their use for nonsense suppression and the treatment of disease |
| DE102006009928A1 (de) * | 2006-03-03 | 2007-09-06 | Aicuris Gmbh & Co. Kg | Substituierte Arylsulfonamide |
| EP2387995A1 (en) | 2006-03-30 | 2011-11-23 | PTC Therapeutics, Inc. | Methods for the production of functional protein from DNA having a nonsense mutation and the treatment of disorders associated therewith |
| US20080255203A1 (en) * | 2007-04-12 | 2008-10-16 | Abbott Laboratories | Heterocyclic compounds and their methods of use |
| CA2692379A1 (en) * | 2007-07-02 | 2009-01-08 | Boehringer Ingelheim International Gmbh | Antiproliferative compounds based on 5-membered heterocycles |
| EP2177521A1 (en) * | 2008-10-14 | 2010-04-21 | Almirall, S.A. | New 2-Amidothiadiazole Derivatives |
| EP2202232A1 (en) * | 2008-12-26 | 2010-06-30 | Laboratorios Almirall, S.A. | 1,2,4-oxadiazole derivatives and their therapeutic use |
| CN103119036B (zh) * | 2010-06-28 | 2018-05-08 | 拜耳知识产权有限责任公司 | 作为杀虫剂的杂环化合物 |
| JP2013531687A (ja) | 2010-07-16 | 2013-08-08 | パーデュー、ファーマ、リミテッド、パートナーシップ | ナトリウムチャネル遮断剤としてのピリジン化合物 |
| WO2013136170A1 (en) | 2012-03-16 | 2013-09-19 | Purdue Pharma L.P. | Substituted pyridines as sodium channel blockers |
| US9284310B2 (en) | 2012-11-03 | 2016-03-15 | Boehringer Ingelheim International Gmbh | Inhibitors of cytomegalovirus |
| EP2914592B1 (en) | 2012-11-03 | 2017-10-11 | Boehringer Ingelheim International GmbH | Inhibitors of cytomegalovirus |
| EP2935257B1 (en) | 2012-12-20 | 2018-02-07 | Purdue Pharma LP | Cyclic sulfonamides as sodium channel blockers |
| WO2015134711A1 (en) | 2014-03-06 | 2015-09-11 | Ptc Therapeutics, Inc. | Pharmaceutical compositions and salts of a 1,2,4-oxadiazole benzoic acid |
| US10730866B2 (en) | 2014-04-07 | 2020-08-04 | Purdue Pharma L.P. | Indole derivatives and use thereof |
| EP3256461B1 (en) * | 2015-02-13 | 2023-09-13 | Azienda Ospedaliera Universitaria Senese | Urea and sulfonamide derivatives as human helicase ddx3 inhibitors useful in the treatment of viral diseases |
| TW201729807A (zh) | 2015-10-30 | 2017-09-01 | Ｐｔｃ治療公司 | 用於治療癲癇的方法 |
| EP3601274A1 (en) * | 2017-03-31 | 2020-02-05 | Perenna Pharmaceuticals, Inc. | Compounds useful as inhibitors of alcat 1 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19802437A1 (de) | 1998-01-23 | 1999-07-29 | Bayer Ag | Verwendung von substituierten Sulfonamiden als anitvirale Mittel und neue Stoffe |
| PL351374A1 (en) * | 1999-04-19 | 2003-04-07 | Shionogi & Co | Sulfonamide derivatives having oxadiazole rings |
-
2002
- 2002-04-08 BR BR0209054-6A patent/BR0209054A/pt not_active IP Right Cessation
- 2002-04-08 WO PCT/EP2002/003858 patent/WO2002085869A1/de not_active Ceased
- 2002-04-08 HU HU0303813A patent/HUP0303813A3/hu unknown
- 2002-04-08 SK SK1266-2003A patent/SK12662003A3/sk unknown
- 2002-04-08 DE DE50204780T patent/DE50204780D1/de not_active Expired - Lifetime
- 2002-04-08 US US10/474,916 patent/US7115612B2/en not_active Expired - Lifetime
- 2002-04-08 CA CA2444123A patent/CA2444123C/en not_active Expired - Lifetime
- 2002-04-08 CN CNA028121589A patent/CN1516695A/zh active Pending
- 2002-04-08 MX MXPA03009548A patent/MXPA03009548A/es unknown
- 2002-04-08 EE EEP200300515A patent/EE200300515A/xx unknown
- 2002-04-08 AT AT02730119T patent/ATE308529T1/de not_active IP Right Cessation
- 2002-04-08 IL IL15832402A patent/IL158324A0/xx unknown
- 2002-04-08 PL PL02363990A patent/PL363990A1/xx not_active Application Discontinuation
- 2002-04-08 EP EP02730119A patent/EP1383749B1/de not_active Expired - Lifetime
- 2002-04-08 JP JP2002583396A patent/JP4480941B2/ja not_active Expired - Lifetime
- 2002-04-08 ES ES02730119T patent/ES2252455T3/es not_active Expired - Lifetime
- 2002-04-08 RU RU2003133750/04A patent/RU2003133750A/ru not_active Application Discontinuation
- 2002-04-17 UY UY27263A patent/UY27263A1/es not_active Application Discontinuation
-
2003
- 2003-10-14 BG BG108272A patent/BG108272A/bg unknown
- 2003-10-17 NO NO20034667A patent/NO20034667L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| UY27263A1 (es) | 2002-11-29 |
| EP1383749B1 (de) | 2005-11-02 |
| DE50204780D1 (de) | 2005-12-08 |
| HUP0303813A3 (en) | 2005-05-30 |
| WO2002085869A1 (de) | 2002-10-31 |
| JP2004531536A (ja) | 2004-10-14 |
| JP4480941B2 (ja) | 2010-06-16 |
| RU2003133750A (ru) | 2005-05-10 |
| NO20034667D0 (no) | 2003-10-17 |
| ES2252455T3 (es) | 2006-05-16 |
| EP1383749A1 (de) | 2004-01-28 |
| CA2444123A1 (en) | 2002-10-31 |
| NO20034667L (no) | 2003-12-12 |
| US7115612B2 (en) | 2006-10-03 |
| CN1516695A (zh) | 2004-07-28 |
| HUP0303813A2 (hu) | 2004-03-29 |
| BR0209054A (pt) | 2004-04-20 |
| MXPA03009548A (es) | 2004-05-24 |
| BG108272A (bg) | 2004-10-29 |
| US20040176374A1 (en) | 2004-09-09 |
| ATE308529T1 (de) | 2005-11-15 |
| CA2444123C (en) | 2010-09-21 |
| PL363990A1 (en) | 2004-11-29 |
| EE200300515A (et) | 2004-02-16 |
| IL158324A0 (en) | 2004-05-12 |
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