DE2708331C2 - - Google Patents
Info
- Publication number
- DE2708331C2 DE2708331C2 DE2708331A DE2708331A DE2708331C2 DE 2708331 C2 DE2708331 C2 DE 2708331C2 DE 2708331 A DE2708331 A DE 2708331A DE 2708331 A DE2708331 A DE 2708331A DE 2708331 C2 DE2708331 C2 DE 2708331C2
- Authority
- DE
- Germany
- Prior art keywords
- pyridinium
- mol
- bis
- pyridine
- dibromide
- 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 - Lifetime
Links
- -1 substituted-amino Chemical group 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 20
- 150000001450 anions Chemical class 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 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
- 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 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 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
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 207
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 117
- 239000000243 solution Substances 0.000 description 98
- 239000007787 solid Substances 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 69
- 230000002829 reductive effect Effects 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
- 238000001914 filtration Methods 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- 239000000706 filtrate Substances 0.000 description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 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 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 230000000844 anti-bacterial effect Effects 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- OZFGBTUVLHXPFW-UHFFFAOYSA-N n-heptylpyridin-4-amine Chemical compound CCCCCCCNC1=CC=NC=C1 OZFGBTUVLHXPFW-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- YHQCHZODALNVAE-UHFFFAOYSA-N n-(2-ethylhexyl)pyridin-4-amine Chemical compound CCCCC(CC)CNC1=CC=NC=C1 YHQCHZODALNVAE-UHFFFAOYSA-N 0.000 description 12
- SGZWATMDTXEATH-UHFFFAOYSA-N n-hexylpyridin-4-amine Chemical compound CCCCCCNC1=CC=NC=C1 SGZWATMDTXEATH-UHFFFAOYSA-N 0.000 description 12
- RHDWCSIBVZKRRU-UHFFFAOYSA-N n-octylpyridin-4-amine Chemical compound CCCCCCCCNC1=CC=NC=C1 RHDWCSIBVZKRRU-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 10
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 9
- LVWSZGCVEZRFBT-UHFFFAOYSA-N 1,7-dibromoheptane Chemical compound BrCCCCCCCBr LVWSZGCVEZRFBT-UHFFFAOYSA-N 0.000 description 9
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 9
- WGAXVZXBFBHLMC-UHFFFAOYSA-N 1,9-dibromononane Chemical compound BrCCCCCCCCCBr WGAXVZXBFBHLMC-UHFFFAOYSA-N 0.000 description 9
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 9
- 208000002064 Dental Plaque Diseases 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000002026 chloroform extract Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- LBUMIVUAXZFMCR-UHFFFAOYSA-N n-nonylpyridin-4-amine Chemical compound CCCCCCCCCNC1=CC=NC=C1 LBUMIVUAXZFMCR-UHFFFAOYSA-N 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 8
- 229960004979 fampridine Drugs 0.000 description 8
- 238000010186 staining Methods 0.000 description 8
- ZJJATABWMGVVRZ-UHFFFAOYSA-N 1,12-dibromododecane Chemical compound BrCCCCCCCCCCCCBr ZJJATABWMGVVRZ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- TUHMQDODLHWPCC-UHFFFAOYSA-N formyl cyanide Chemical compound O=CC#N TUHMQDODLHWPCC-UHFFFAOYSA-N 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- WDRQQCOWXCWKGZ-UHFFFAOYSA-N n-cyclohexylpyridin-4-amine Chemical compound C1CCCCC1NC1=CC=NC=C1 WDRQQCOWXCWKGZ-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 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 6
- XMONRBOPIGIIMR-UHFFFAOYSA-N n-decylpyridin-4-amine Chemical compound CCCCCCCCCCNC1=CC=NC=C1 XMONRBOPIGIIMR-UHFFFAOYSA-N 0.000 description 6
- LYYSOBGOHUNXCU-UHFFFAOYSA-N n-dodecylpyridin-4-amine Chemical compound CCCCCCCCCCCCNC1=CC=NC=C1 LYYSOBGOHUNXCU-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- 241000194019 Streptococcus mutans Species 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- 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 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 230000003253 viricidal effect Effects 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000002421 anti-septic effect Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012456 homogeneous solution Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 241000894007 species Species 0.000 description 4
- SDENLXLNLFKRAR-UHFFFAOYSA-N 1,14-dibromotetradecane Chemical compound BrCCCCCCCCCCCCCCBr SDENLXLNLFKRAR-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- 239000000654 additive Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 235000013372 meat Nutrition 0.000 description 3
- OQMPQSNPSZLEKX-UHFFFAOYSA-N n-heptyl-1-[10-[4-(heptylamino)pyridin-1-ium-1-yl]decyl]pyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C1=CC(NCCCCCCC)=CC=[N+]1CCCCCCCCCC[N+]1=CC=C(NCCCCCCC)C=C1 OQMPQSNPSZLEKX-UHFFFAOYSA-N 0.000 description 3
- 230000007505 plaque formation Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- RBBNTRDPSVZESY-UHFFFAOYSA-N 1,10-dichlorodecane Chemical compound ClCCCCCCCCCCCl RBBNTRDPSVZESY-UHFFFAOYSA-N 0.000 description 2
- RNXPZVYZVHJVHM-UHFFFAOYSA-N 1,12-dichlorododecane Chemical compound ClCCCCCCCCCCCCCl RNXPZVYZVHJVHM-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 2
- MPZMVUQGXAOJIK-UHFFFAOYSA-N 4-bromopyridine;hydron;chloride Chemical compound Cl.BrC1=CC=NC=C1 MPZMVUQGXAOJIK-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
- 241000894006 Bacteria Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- FKCBLVCOSCZFHV-UHFFFAOYSA-N acetonitrile;ethanol Chemical compound CCO.CC#N FKCBLVCOSCZFHV-UHFFFAOYSA-N 0.000 description 2
- GPEHQHXBPDGGDP-UHFFFAOYSA-N acetonitrile;propan-2-one Chemical compound CC#N.CC(C)=O GPEHQHXBPDGGDP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000551 dentifrice 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
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- SRUKOJDGOUUFRB-UHFFFAOYSA-N heptylazanium;chloride Chemical compound Cl.CCCCCCCN SRUKOJDGOUUFRB-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- XKDUZXVNQOZCFC-UHFFFAOYSA-N hexan-1-amine;hydron;chloride Chemical compound Cl.CCCCCCN XKDUZXVNQOZCFC-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- VBGWTAGNJZKBOV-UHFFFAOYSA-N n-(2-ethylhexyl)-1-[12-[4-(2-ethylhexylimino)pyridin-1-yl]dodecyl]pyridin-4-imine;dihydrobromide Chemical compound [Br-].[Br-].C1=CC(NCC(CC)CCCC)=CC=[N+]1CCCCCCCCCCCC[N+]1=CC=C(NCC(CC)CCCC)C=C1 VBGWTAGNJZKBOV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UJRNRQQQVKXGQR-UHFFFAOYSA-N n-hexyl-1-[14-[4-(hexylamino)pyridin-1-ium-1-yl]tetradecyl]pyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C1=CC(NCCCCCC)=CC=[N+]1CCCCCCCCCCCCCC[N+]1=CC=C(NCCCCCC)C=C1 UJRNRQQQVKXGQR-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
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- 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 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
- HDMPTQLOGALKJL-UHFFFAOYSA-N n-(3-fluorophenyl)pyridin-4-amine Chemical compound FC1=CC=CC(NC=2C=CN=CC=2)=C1 HDMPTQLOGALKJL-UHFFFAOYSA-N 0.000 description 1
- UCGFZFFKJRXDQN-UHFFFAOYSA-N n-(4-bromophenyl)pyridin-4-amine Chemical compound C1=CC(Br)=CC=C1NC1=CC=NC=C1 UCGFZFFKJRXDQN-UHFFFAOYSA-N 0.000 description 1
- PSJJUCAJICGYRO-UHFFFAOYSA-N n-(5-ethyl-6-methylheptan-2-yl)pyridin-4-amine Chemical compound CCC(C(C)C)CCC(C)NC1=CC=NC=C1 PSJJUCAJICGYRO-UHFFFAOYSA-N 0.000 description 1
- RVBFXHGLQBAIEU-UHFFFAOYSA-N n-(5-methylhexan-2-yl)pyridin-4-amine Chemical compound CC(C)CCC(C)NC1=CC=NC=C1 RVBFXHGLQBAIEU-UHFFFAOYSA-N 0.000 description 1
- NBVKVYKUEHBBHZ-UHFFFAOYSA-N n-cycloheptylpyridin-4-amine Chemical compound C1CCCCCC1NC1=CC=NC=C1 NBVKVYKUEHBBHZ-UHFFFAOYSA-N 0.000 description 1
- ZYPKTMZFRMKZMM-UHFFFAOYSA-N n-cyclopentylpyridin-4-amine Chemical compound C1CCCC1NC1=CC=NC=C1 ZYPKTMZFRMKZMM-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
- OKIDQCNCGHERRL-UHFFFAOYSA-N n-heptyl-1-[14-(4-heptyliminopyridin-1-yl)tetradecyl]pyridin-4-imine;dihydrochloride Chemical compound [Cl-].[Cl-].C1=CC(NCCCCCCC)=CC=[N+]1CCCCCCCCCCCCCC[N+]1=CC=C(NCCCCCCC)C=C1 OKIDQCNCGHERRL-UHFFFAOYSA-N 0.000 description 1
- MUADDYCRJOWPFP-UHFFFAOYSA-N n-heptyl-1-[9-[4-(heptylamino)pyridin-1-ium-1-yl]nonyl]pyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C1=CC(NCCCCCCC)=CC=[N+]1CCCCCCCCC[N+]1=CC=C(NCCCCCCC)C=C1 MUADDYCRJOWPFP-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- ADNNMLLTNLEDOK-UHFFFAOYSA-N n-octadecylpyridin-4-amine Chemical compound CCCCCCCCCCCCCCCCCCNC1=CC=NC=C1 ADNNMLLTNLEDOK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- MRXDWLZIBLDFKG-UHFFFAOYSA-N n-propylpyridin-4-amine Chemical compound CCCNC1=CC=NC=C1 MRXDWLZIBLDFKG-UHFFFAOYSA-N 0.000 description 1
- PCTDQUFOMUYCAJ-UHFFFAOYSA-N n-tetradecylpyridin-4-amine Chemical compound CCCCCCCCCCCCCCNC1=CC=NC=C1 PCTDQUFOMUYCAJ-UHFFFAOYSA-N 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
- 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
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 1
- 229940071462 oralone Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 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
- 229910052763 palladium Inorganic materials 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
- 239000002304 perfume Substances 0.000 description 1
- 239000008180 pharmaceutical surfactant 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 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
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 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
- 229940071089 sarcosinate Drugs 0.000 description 1
- 108700004121 sarkosyl Proteins 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
- 238000002791 soaking Methods 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
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 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
- 239000008247 solid mixture Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 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
- 210000002784 stomach Anatomy 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
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 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
- 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
- 230000036344 tooth staining Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66112876A | 1976-02-25 | 1976-02-25 | |
| US66110176A | 1976-02-25 | 1976-02-25 | |
| US72131576A | 1976-09-07 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2708331A1 DE2708331A1 (de) | 1977-09-08 |
| DE2708331C2 true DE2708331C2 (en, 2012) | 1991-03-21 |
Family
ID=27505307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772708331 Granted DE2708331A1 (de) | 1976-02-25 | 1977-02-25 | Antimikrobielle bis-pyridinium-verbindungen |
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) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007031519A2 (en) | 2005-09-15 | 2007-03-22 | Air Liquide Sante (International) | Antimicrobial preparations having a content of octenidine dihydrochloride encapsulated in liposomes |
| WO2008052912A1 (en) | 2006-10-31 | 2008-05-08 | Air Liquide Sante (International) | Antimicrobially active composition having a content of bispyridinium alkane (octenidine dihydrochloride) |
| WO2009106467A2 (en) | 2008-02-28 | 2009-09-03 | Air Liquide Sante (International) | Stabilized, antimicrobially effective composition with a content of bispyridinium alkane |
| EP2311456A1 (en) | 2009-10-15 | 2011-04-20 | L'AIR LIQUIDE, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Wound and mucous membrane antiseptic based on bispyridiniumalkanes |
| DE202010007433U1 (de) | 2010-04-20 | 2011-06-01 | Klosterfrau Berlin GmbH, 12277 | Gel, insbesondere Gleitgel |
| EP2401914A1 (en) | 2010-07-02 | 2012-01-04 | L'AIR LIQUIDE, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Antiseptic based on bispyridinium alkanes |
| EP2702983A1 (en) | 2012-08-31 | 2014-03-05 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Process for the preparation of a bispyridiniumalkane-containing semisolid preparation |
| DE102013223657A1 (de) | 2013-11-20 | 2015-05-21 | Schülke & Mayr GmbH | Kit für die Erzeugung von Bispyridiniumalkan enthaltenden Schäumen |
| DE102014107413A1 (de) | 2014-05-26 | 2015-11-26 | Schülke & Mayr GmbH | Kit für das Einfärben von desinfizierten Bereichen einer Oberfläche |
| EP2949345A1 (en) | 2014-05-26 | 2015-12-02 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Coloured disinfectant preparation based on bispyridiniumalkane |
| DE102014115080A1 (de) | 2014-10-16 | 2016-04-21 | Schülke & Mayr GmbH | Verwendung von Fettsäureester zur Verbesserung der antimikrobiellen Wirksamkeit eines alkoholischen Desinfektionsmittels |
Families Citing this family (28)
| 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 |
| 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 |
| DE102005048132A1 (de) * | 2005-10-06 | 2007-04-12 | Bayer Innovation Gmbh | Verfahren zur Herstellung antimikrobieller Kunststoffzusammensetzungen |
| DE102006012991A1 (de) | 2006-03-22 | 2007-10-11 | Bayer Innovation Gmbh | Verfahren und Vorrichtung zum optischen Auslesen von Informationen |
| 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 |
| EP2384733B1 (de) * | 2010-05-07 | 2016-07-27 | Ivoclar Vivadent AG | Antimikrobielle Dentalwerkstoffe |
| DE102011077432A1 (de) * | 2011-06-10 | 2012-12-13 | Schülke & Mayr GmbH | Verwendung von Bispyridiniumalkanen zur Abtötung von Sporen |
| WO2019038669A1 (en) * | 2017-08-21 | 2019-02-28 | Dishman Carbogen Amcis Ltd. | OCTENIDINE-BASED COMPOUNDS |
| EP3771741A1 (en) | 2019-07-29 | 2021-02-03 | The Procter & Gamble Company | Fabric treatment |
| 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 |
-
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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| DE102008011691A1 (de) | 2008-02-28 | 2009-09-10 | Schülke & Mayr GmbH | Stabilisierte, antimikrobiell wirksame Zusammensetzung mit einem Gehalt an Bispyridiniumalkan |
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| EP2311456A1 (en) | 2009-10-15 | 2011-04-20 | L'AIR LIQUIDE, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Wound and mucous membrane antiseptic based on bispyridiniumalkanes |
| DE102009049504A1 (de) | 2009-10-15 | 2011-04-21 | Schülke & Mayr GmbH | Wund- und Schleimhautantiseptikum auf der Basis von Bispyridiniumalkanen |
| EP2716289A1 (en) | 2009-10-15 | 2014-04-09 | L'AIR LIQUIDE, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Wound and mucous membrane antiseptic based on Bispyridiniumalkanes |
| DE202010007433U1 (de) | 2010-04-20 | 2011-06-01 | Klosterfrau Berlin GmbH, 12277 | Gel, insbesondere Gleitgel |
| DE102010022367A1 (de) | 2010-04-20 | 2011-10-20 | Klosterfrau Berlin Gmbh | Gel, insbesondere Gleitgel, und seine Verwendung |
| EP2401914A1 (en) | 2010-07-02 | 2012-01-04 | L'AIR LIQUIDE, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Antiseptic based on bispyridinium alkanes |
| DE102010025932A1 (de) | 2010-07-02 | 2012-01-05 | Schülke & Mayr GmbH | Antiseptikum auf der Basis von Bispyridiniumalkanen |
| DE102012215511A1 (de) | 2012-08-31 | 2014-06-12 | Schülke & Mayr GmbH | Verfahren zur Herstellung einer Bispyridiniumalkan enthaltenden halbfesten Zubereitung |
| EP2702983A1 (en) | 2012-08-31 | 2014-03-05 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Process for the preparation of a bispyridiniumalkane-containing semisolid preparation |
| DE102013223657A1 (de) | 2013-11-20 | 2015-05-21 | Schülke & Mayr GmbH | Kit für die Erzeugung von Bispyridiniumalkan enthaltenden Schäumen |
| EP2875804A1 (en) | 2013-11-20 | 2015-05-27 | L'Air Liquide Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Kit for producing foams containing bispyridinium alkane |
| US9770019B2 (en) | 2013-11-20 | 2017-09-26 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Kit for producing foams containing bispyridinium alkane |
| EP2949345A1 (en) | 2014-05-26 | 2015-12-02 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Coloured disinfectant preparation based on bispyridiniumalkane |
| DE102014107412A1 (de) | 2014-05-26 | 2015-12-17 | Schülke & Mayr GmbH | Gefärbte desinfizierende Zubereitung auf Basis von Bispyridiniumalkan |
| EP2952213A1 (en) | 2014-05-26 | 2015-12-09 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Kit for colouring disinfected regions of a surface |
| 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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