JPS6033108B2 - 抗微生物ビス↓−ピリジニウム化合物 - Google Patents
抗微生物ビス↓−ピリジニウム化合物Info
- Publication number
- JPS6033108B2 JPS6033108B2 JP52020130A JP2013077A JPS6033108B2 JP S6033108 B2 JPS6033108 B2 JP S6033108B2 JP 52020130 A JP52020130 A JP 52020130A JP 2013077 A JP2013077 A JP 2013077A JP S6033108 B2 JPS6033108 B2 JP S6033108B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- pyridinium
- bis
- mol
- carbon atoms
- 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.)
- Expired
Links
- 230000000845 anti-microbial effect Effects 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 74
- -1 chloro, bromo, iodo, methanesulfonyloxy, ethanesulfonyloxy, benzenesulfonyloxy Chemical group 0.000 claims description 56
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 42
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000001450 anions Chemical class 0.000 claims description 17
- 230000000844 anti-bacterial effect Effects 0.000 claims description 14
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- 230000000843 anti-fungal effect Effects 0.000 claims description 7
- 229940121375 antifungal agent Drugs 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 5
- 230000003253 viricidal effect Effects 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- BABOCLFOOQFQSH-UHFFFAOYSA-N n-(2-ethylhexyl)-1-[10-[4-(2-ethylhexylimino)pyridin-1-yl]decyl]pyridin-4-imine;dihydrobromide Chemical compound [Br-].[Br-].C1=CC(NCC(CC)CCCC)=CC=[N+]1CCCCCCCCCC[N+]1=CC=C(NCC(CC)CCCC)C=C1 BABOCLFOOQFQSH-UHFFFAOYSA-N 0.000 claims description 3
- VXSRIICRQMLBQG-UHFFFAOYSA-N n-heptyl-1-[12-(4-heptyliminopyridin-1-yl)dodecyl]pyridin-4-imine;dihydrochloride Chemical compound [Cl-].[Cl-].C1=CC(NCCCCCCC)=CC=[N+]1CCCCCCCCCCCC[N+]1=CC=C(NCCCCCCC)C=C1 VXSRIICRQMLBQG-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 230000002882 anti-plaque Effects 0.000 claims description 2
- ASCUDKJLTKXHGJ-UHFFFAOYSA-N n-octyl-1-[8-[4-(octylamino)pyridin-1-ium-1-yl]octyl]pyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C1=CC(NCCCCCCCC)=CC=[N+]1CCCCCCCC[N+]1=CC=C(NCCCCCCCC)C=C1 ASCUDKJLTKXHGJ-UHFFFAOYSA-N 0.000 claims description 2
- FGPMBSMFNGGVIT-UHFFFAOYSA-N n-octyl-1-[9-[4-(octylamino)pyridin-1-ium-1-yl]nonyl]pyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C1=CC(NCCCCCCCC)=CC=[N+]1CCCCCCCCC[N+]1=CC=C(NCCCCCCCC)C=C1 FGPMBSMFNGGVIT-UHFFFAOYSA-N 0.000 claims description 2
- SMGTYJPMKXNQFY-UHFFFAOYSA-N octenidine dihydrochloride Chemical compound Cl.Cl.C1=CC(=NCCCCCCCC)C=CN1CCCCCCCCCCN1C=CC(=NCCCCCCCC)C=C1 SMGTYJPMKXNQFY-UHFFFAOYSA-N 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 238000004140 cleaning Methods 0.000 claims 1
- 230000000249 desinfective effect Effects 0.000 claims 1
- UVKYQBWVUOZNSN-UHFFFAOYSA-N n-octyl-1-[10-[4-(octylamino)pyridin-1-ium-1-yl]decyl]pyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C1=CC(NCCCCCCCC)=CC=[N+]1CCCCCCCCCC[N+]1=CC=C(NCCCCCCCC)C=C1 UVKYQBWVUOZNSN-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 206
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 121
- 239000000243 solution Substances 0.000 description 106
- 238000000034 method Methods 0.000 description 82
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 239000007787 solid Substances 0.000 description 71
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 68
- 230000002829 reductive effect Effects 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 40
- 239000000047 product Substances 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- 239000003610 charcoal Substances 0.000 description 27
- 238000010992 reflux Methods 0.000 description 19
- OXUCOTSGWGNWGC-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2-] OXUCOTSGWGNWGC-UHFFFAOYSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- SXQMONVCMHFPDA-UHFFFAOYSA-N nonane Chemical compound CCCCCCCC[CH2-] SXQMONVCMHFPDA-UHFFFAOYSA-N 0.000 description 12
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 12
- OZFGBTUVLHXPFW-UHFFFAOYSA-N n-heptylpyridin-4-amine Chemical compound CCCCCCCNC1=CC=NC=C1 OZFGBTUVLHXPFW-UHFFFAOYSA-N 0.000 description 11
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002026 chloroform extract Substances 0.000 description 9
- 229960004979 fampridine Drugs 0.000 description 9
- YHQCHZODALNVAE-UHFFFAOYSA-N n-(2-ethylhexyl)pyridin-4-amine Chemical compound CCCCC(CC)CNC1=CC=NC=C1 YHQCHZODALNVAE-UHFFFAOYSA-N 0.000 description 9
- SGZWATMDTXEATH-UHFFFAOYSA-N n-hexylpyridin-4-amine Chemical compound CCCCCCNC1=CC=NC=C1 SGZWATMDTXEATH-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- XMONRBOPIGIIMR-UHFFFAOYSA-N n-decylpyridin-4-amine Chemical compound CCCCCCCCCCNC1=CC=NC=C1 XMONRBOPIGIIMR-UHFFFAOYSA-N 0.000 description 8
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- TUHMQDODLHWPCC-UHFFFAOYSA-N formyl cyanide Chemical compound O=CC#N TUHMQDODLHWPCC-UHFFFAOYSA-N 0.000 description 7
- WDRQQCOWXCWKGZ-UHFFFAOYSA-N n-cyclohexylpyridin-4-amine Chemical compound C1CCCCC1NC1=CC=NC=C1 WDRQQCOWXCWKGZ-UHFFFAOYSA-N 0.000 description 7
- RHDWCSIBVZKRRU-UHFFFAOYSA-N n-octylpyridin-4-amine Chemical compound CCCCCCCCNC1=CC=NC=C1 RHDWCSIBVZKRRU-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- QZOFFMRDIRXGKJ-UHFFFAOYSA-M hydron;4-pyridin-1-ium-1-ylpyridine;dichloride Chemical compound Cl.[Cl-].C1=CC=CC=[N+]1C1=CC=NC=C1 QZOFFMRDIRXGKJ-UHFFFAOYSA-M 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 6
- LBUMIVUAXZFMCR-UHFFFAOYSA-N n-nonylpyridin-4-amine Chemical compound CCCCCCCCCNC1=CC=NC=C1 LBUMIVUAXZFMCR-UHFFFAOYSA-N 0.000 description 6
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000001273 butane Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 4
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 4
- 235000011613 Pinus brutia Nutrition 0.000 description 4
- 241000018646 Pinus brutia Species 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000003306 harvesting Methods 0.000 description 4
- 239000012456 homogeneous solution Substances 0.000 description 4
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 4
- DNZPRDQJUNLFCS-UHFFFAOYSA-N n-(4-chlorophenyl)pyridin-4-amine Chemical compound C1=CC(Cl)=CC=C1NC1=CC=NC=C1 DNZPRDQJUNLFCS-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 4
- 230000007505 plaque formation Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- LVWSZGCVEZRFBT-UHFFFAOYSA-N 1,7-dibromoheptane Chemical compound BrCCCCCCCBr LVWSZGCVEZRFBT-UHFFFAOYSA-N 0.000 description 3
- WGAXVZXBFBHLMC-UHFFFAOYSA-N 1,9-dibromononane Chemical compound BrCCCCCCCCCBr WGAXVZXBFBHLMC-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 244000241257 Cucumis melo Species 0.000 description 3
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
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- 229930195733 hydrocarbon Natural products 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
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- 238000010186 staining Methods 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- 150000003738 xylenes Chemical class 0.000 description 3
- RNXPZVYZVHJVHM-UHFFFAOYSA-N 1,12-dichlorododecane Chemical compound ClCCCCCCCCCCCCCl RNXPZVYZVHJVHM-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- WGFUAJNREFNKPN-UHFFFAOYSA-N 5-chlorothiadiazole-4-carboxamide Chemical compound NC(=O)C=1N=NSC=1Cl WGFUAJNREFNKPN-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
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- 241000238631 Hexapoda Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- 241000194019 Streptococcus mutans Species 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
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- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940074371 monofluorophosphate Drugs 0.000 description 1
- UTTVXKGNTWZECK-UHFFFAOYSA-N n,n-dimethyloctadecan-1-amine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)[O-] UTTVXKGNTWZECK-UHFFFAOYSA-N 0.000 description 1
- CCRCJZORJCTGDL-UHFFFAOYSA-N n-(2-ethylhexyl)-1-[10-[4-(2-ethylhexylamino)pyridin-1-ium-1-yl]decyl]pyridin-1-ium-4-amine;dichloride Chemical compound [Cl-].[Cl-].C1=CC(NCC(CC)CCCC)=CC=[N+]1CCCCCCCCCC[N+]1=CC=C(NCC(CC)CCCC)C=C1 CCRCJZORJCTGDL-UHFFFAOYSA-N 0.000 description 1
- HZIZESPPYQZSDH-UHFFFAOYSA-N n-(2-ethylhexyl)-1-[8-[4-(2-ethylhexylimino)pyridin-1-yl]octyl]pyridin-4-imine;dihydrobromide Chemical compound [Br-].[Br-].C1=CC(NCC(CC)CCCC)=CC=[N+]1CCCCCCCC[N+]1=CC=C(NCC(CC)CCCC)C=C1 HZIZESPPYQZSDH-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
- SVNPVKIONFWLJU-UHFFFAOYSA-N n-decylpyridin-2-amine Chemical compound CCCCCCCCCCNC1=CC=CC=N1 SVNPVKIONFWLJU-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HRJSPFXYRFKEFM-UHFFFAOYSA-N n-heptyl-1-[12-[4-(heptylamino)pyridin-1-ium-1-yl]dodecyl]pyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C1=CC(NCCCCCCC)=CC=[N+]1CCCCCCCCCCCC[N+]1=CC=C(NCCCCCCC)C=C1 HRJSPFXYRFKEFM-UHFFFAOYSA-N 0.000 description 1
- CUSSEAQMJSVNHQ-UHFFFAOYSA-N n-heptyl-1-[14-[4-(heptylamino)pyridin-1-ium-1-yl]tetradecyl]pyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C1=CC(NCCCCCCC)=CC=[N+]1CCCCCCCCCCCCCC[N+]1=CC=C(NCCCCCCC)C=C1 CUSSEAQMJSVNHQ-UHFFFAOYSA-N 0.000 description 1
- GAPSFCQYFJNXJE-UHFFFAOYSA-N n-heptyl-1-[9-[4-(heptylamino)pyridin-1-ium-1-yl]nonyl]pyridin-1-ium-4-amine;dichloride Chemical compound [Cl-].[Cl-].C1=CC(NCCCCCCC)=CC=[N+]1CCCCCCCCC[N+]1=CC=C(NCCCCCCC)C=C1 GAPSFCQYFJNXJE-UHFFFAOYSA-N 0.000 description 1
- IVCDYLIODNNGLA-UHFFFAOYSA-N n-heptylpyridin-2-amine Chemical compound CCCCCCCNC1=CC=CC=N1 IVCDYLIODNNGLA-UHFFFAOYSA-N 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
- 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
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- IMGHCWMUWVHYCO-UHFFFAOYSA-N nonan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCC[NH3+] IMGHCWMUWVHYCO-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- MHEMSXNXRWNGKW-UHFFFAOYSA-N tetradecane dihydrobromide Chemical compound Br.Br.CCCCCCCCCCCCCC MHEMSXNXRWNGKW-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940118827 zinc phenolsulfonate Drugs 0.000 description 1
- BOVNWDGXGNVNQD-UHFFFAOYSA-L zinc;2-hydroxybenzenesulfonate Chemical compound [Zn+2].OC1=CC=CC=C1S([O-])(=O)=O.OC1=CC=CC=C1S([O-])(=O)=O BOVNWDGXGNVNQD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
- A61P31/10—Antimycotics
-
- 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
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66112876A | 1976-02-25 | 1976-02-25 | |
| US66110176A | 1976-02-25 | 1976-02-25 | |
| US661128 | 1976-02-25 | ||
| US72131576A | 1976-09-07 | 1976-09-07 | |
| US721315 | 1976-09-07 | ||
| US05/734,729 US4107313A (en) | 1976-02-25 | 1976-10-22 | α,α-Bis-[4-(R-amino)-1-pyridinium]xylenes and antibacterial and antifungal uses |
| US661101 | 1984-10-15 | ||
| US734729 | 1991-07-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52105228A JPS52105228A (en) | 1977-09-03 |
| JPS6033108B2 true JPS6033108B2 (ja) | 1985-08-01 |
Family
ID=27505307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52020130A Expired JPS6033108B2 (ja) | 1976-02-25 | 1977-02-25 | 抗微生物ビス↓−ピリジニウム化合物 |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS6033108B2 (en, 2012) |
| AR (2) | AR214876A1 (en, 2012) |
| AT (1) | AT355571B (en, 2012) |
| AU (1) | AU510149B2 (en, 2012) |
| BE (1) | BE851807A (en, 2012) |
| CA (1) | CA1073911A (en, 2012) |
| CH (1) | CH620907A5 (en, 2012) |
| DE (1) | DE2708331A1 (en, 2012) |
| DK (1) | DK147638C (en, 2012) |
| ES (1) | ES456252A1 (en, 2012) |
| FI (1) | FI66850C (en, 2012) |
| FR (1) | FR2342286A1 (en, 2012) |
| GB (1) | GB1533952A (en, 2012) |
| HK (1) | HK67484A (en, 2012) |
| IE (1) | IE45336B1 (en, 2012) |
| IL (1) | IL51520A (en, 2012) |
| LU (1) | LU76837A1 (en, 2012) |
| MX (1) | MX5132E (en, 2012) |
| NL (1) | NL186086C (en, 2012) |
| NO (2) | NO148779C (en, 2012) |
| PH (2) | PH22315A (en, 2012) |
| PT (1) | PT66224B (en, 2012) |
| SE (1) | SE432421B (en, 2012) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE32300E (en) * | 1979-08-13 | 1986-12-02 | Sterling Drug Inc. | Basic amino or ammonium antimicrobial agent-polyethylene glycol ester surfactant-betaine and/or amine oxide surfactant compositions and method of use thereof |
| US4420484A (en) | 1979-08-13 | 1983-12-13 | Sterling Drug Inc. | Basic amino or ammonium antimicrobial agent-polyethylene glycol ester surfactant-betaine and/or amine oxide surfactant compositions and method of use therof |
| DE19647402A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Schering Agrevo Gmbh | Substituierte Stickstoff-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| DE19647413A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Schering Agrevo Gmbh | Substituierte Stickstoff-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| DE19647317A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Schering Agrevo Gmbh | Substituierte Stickstoff-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| DE10005853C1 (de) * | 2000-02-10 | 2002-02-07 | Schuelke & Mayr Gmbh | Verfahren zur Herstellung von Bis-(4-amino-1-pyridinium)-alkanen |
| DE10205883A1 (de) * | 2002-02-13 | 2003-08-21 | Schuelke & Mayr Gmbh | Wässriges Antiseptikum auf Basis von Bispyridiniumalkanen |
| TWI278315B (en) * | 2003-06-13 | 2007-04-11 | Ind Tech Res Inst | A compound having anti-virus activity |
| ES2237332B1 (es) * | 2004-01-14 | 2006-11-01 | Consejo Sup. Investig. Cientificas | Derivados de piridinio y quinolinio. |
| DE102005002643B4 (de) * | 2005-01-19 | 2007-11-22 | Schülke & Mayr GmbH | Zusammensetzungen für die hygienische Händedesinfektion und die desinfizierende Händewaschung |
| DE102005002644A1 (de) * | 2005-01-19 | 2006-07-20 | Schülke & Mayr GmbH | Zusammensetzungen für die hygienische Händedesinfektion und die desinfizierende Händewaschung |
| DE102005002645A1 (de) | 2005-01-19 | 2006-07-20 | Schülke & Mayr GmbH | Alkoholische Zusammensetzungen für die Desinfektion |
| DE102005063375A1 (de) * | 2005-09-15 | 2007-04-19 | Schülke & Mayr GmbH | Antimikrobielle Zubereitungen mit einem Gehalt an Octenidindihydrochlorid verkapselt in Liposomen |
| DE102005045145A1 (de) | 2005-09-15 | 2007-03-29 | Schülke & Mayr GmbH | Verwendung von Octenidindihydrochlorid in halbfesten Zubereitungen |
| DE102005048131A1 (de) * | 2005-10-06 | 2007-04-12 | Bayer Innovation Gmbh | Antimikrobielle Kunststoffzusammensetzung mit niedriger Elutionsrate und langer Wirksamkeit |
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| DE102006012991A1 (de) | 2006-03-22 | 2007-10-11 | Bayer Innovation Gmbh | Verfahren und Vorrichtung zum optischen Auslesen von Informationen |
| DE102006051891A1 (de) * | 2006-10-31 | 2008-05-08 | Schülke & Mayr GmbH | Antimikrobiell wirksame Zusammensetzung mit einem Gehalt an Bispyridiniumalkan |
| RU2345068C2 (ru) * | 2006-12-12 | 2009-01-27 | Некоммерческая организация Учреждение Институт проблем химической физики Российской академии наук (статус государственного учреждения) (ИПХФ РАН) | Способ получения 4-(алкиламино) пиридина |
| DE102008011691A1 (de) | 2008-02-28 | 2009-09-10 | Schülke & Mayr GmbH | Stabilisierte, antimikrobiell wirksame Zusammensetzung mit einem Gehalt an Bispyridiniumalkan |
| DE102009049504A1 (de) | 2009-10-15 | 2011-04-21 | Schülke & Mayr GmbH | Wund- und Schleimhautantiseptikum auf der Basis von Bispyridiniumalkanen |
| DE202010007433U1 (de) | 2010-04-20 | 2011-06-01 | Klosterfrau Berlin GmbH, 12277 | Gel, insbesondere Gleitgel |
| EP2384733B1 (de) * | 2010-05-07 | 2016-07-27 | Ivoclar Vivadent AG | Antimikrobielle Dentalwerkstoffe |
| DE102010025932A1 (de) | 2010-07-02 | 2012-01-05 | Schülke & Mayr GmbH | Antiseptikum auf der Basis von Bispyridiniumalkanen |
| DE102011077432A1 (de) * | 2011-06-10 | 2012-12-13 | Schülke & Mayr GmbH | Verwendung von Bispyridiniumalkanen zur Abtötung von Sporen |
| DE102012215511A1 (de) | 2012-08-31 | 2014-06-12 | Schülke & Mayr GmbH | Verfahren zur Herstellung einer Bispyridiniumalkan enthaltenden halbfesten Zubereitung |
| DE102013223657A1 (de) | 2013-11-20 | 2015-05-21 | Schülke & Mayr GmbH | Kit für die Erzeugung von Bispyridiniumalkan enthaltenden Schäumen |
| DE102014107412A1 (de) | 2014-05-26 | 2015-12-17 | Schülke & Mayr GmbH | Gefärbte desinfizierende Zubereitung auf Basis von Bispyridiniumalkan |
| DE102014107413A1 (de) | 2014-05-26 | 2015-11-26 | Schülke & Mayr GmbH | Kit für das Einfärben von desinfizierten Bereichen einer Oberfläche |
| DE102014115080A1 (de) | 2014-10-16 | 2016-04-21 | Schülke & Mayr GmbH | Verwendung von Fettsäureester zur Verbesserung der antimikrobiellen Wirksamkeit eines alkoholischen Desinfektionsmittels |
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| EP3771770B1 (en) | 2019-07-29 | 2025-04-09 | The Procter & Gamble Company | Antimicrobial freshening compositions |
| EP3771339A1 (en) | 2019-07-29 | 2021-02-03 | The Procter & Gamble Company | Disinfectant composition |
| EP3771338A1 (en) | 2019-07-29 | 2021-02-03 | The Procter & Gamble Company | Acidic antimicrobial composition |
| EP3771337A1 (en) | 2019-07-29 | 2021-02-03 | The Procter & Gamble Company | Antimicrobial composition |
| EP3816272B1 (en) | 2019-10-31 | 2023-11-01 | The Procter & Gamble Company | Fabric care composition |
| CN114989076A (zh) * | 2022-06-07 | 2022-09-02 | 八叶草健康产业研究院(厦门)有限公司 | 一种奥替尼啶碱的制备方法 |
| CZ202458A3 (cs) * | 2024-02-20 | 2025-08-06 | Fakultní nemocnice Hradec Králové | Kvartérní amoniová sůl s širokým antimikrobním spektrem, způsob její přípravy, dezinfekční kompozice a jejich použití |
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1977
- 1977-02-11 GB GB5784/77A patent/GB1533952A/en not_active Expired
- 1977-02-21 PH PH19473A patent/PH22315A/en unknown
- 1977-02-22 IL IL51520A patent/IL51520A/xx unknown
- 1977-02-23 PT PT66224A patent/PT66224B/pt unknown
- 1977-02-23 MX MX775459U patent/MX5132E/es unknown
- 1977-02-23 AU AU22582/77A patent/AU510149B2/en not_active Expired
- 1977-02-23 IE IE386/77A patent/IE45336B1/en unknown
- 1977-02-23 NL NLAANVRAGE7701965,A patent/NL186086C/xx not_active IP Right Cessation
- 1977-02-23 FI FI770593A patent/FI66850C/fi not_active IP Right Cessation
- 1977-02-24 NO NO770631A patent/NO148779C/no unknown
- 1977-02-24 SE SE7702072A patent/SE432421B/xx not_active IP Right Cessation
- 1977-02-24 ES ES456252A patent/ES456252A1/es not_active Expired
- 1977-02-24 AR AR266668A patent/AR214876A1/es active
- 1977-02-24 CA CA272,596A patent/CA1073911A/en not_active Expired
- 1977-02-24 CH CH233677A patent/CH620907A5/fr not_active IP Right Cessation
- 1977-02-24 LU LU76837A patent/LU76837A1/xx unknown
- 1977-02-24 DK DK81277A patent/DK147638C/da not_active IP Right Cessation
- 1977-02-25 BE BE1007973A patent/BE851807A/xx not_active IP Right Cessation
- 1977-02-25 FR FR7705621A patent/FR2342286A1/fr active Granted
- 1977-02-25 AT AT129777A patent/AT355571B/de not_active IP Right Cessation
- 1977-02-25 DE DE19772708331 patent/DE2708331A1/de active Granted
- 1977-02-25 JP JP52020130A patent/JPS6033108B2/ja not_active Expired
- 1977-11-11 PH PH20428A patent/PH25097A/en unknown
-
1978
- 1978-01-04 AR AR270629A patent/AR218052A1/es active
-
1982
- 1982-09-28 NO NO823274A patent/NO150758C/no unknown
-
1984
- 1984-08-30 HK HK674/84A patent/HK67484A/xx unknown
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