NO312727B1 - Tiopyridiner som bekjempelsesmiddel mot helicobacter- bakterier - Google Patents
Tiopyridiner som bekjempelsesmiddel mot helicobacter- bakterier Download PDFInfo
- Publication number
- NO312727B1 NO312727B1 NO19965161A NO965161A NO312727B1 NO 312727 B1 NO312727 B1 NO 312727B1 NO 19965161 A NO19965161 A NO 19965161A NO 965161 A NO965161 A NO 965161A NO 312727 B1 NO312727 B1 NO 312727B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- compounds
- formula
- hydrogen
- nitro
- Prior art date
Links
- 241000589989 Helicobacter Species 0.000 title claims abstract description 13
- 239000000575 pesticide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 150000002460 imidazoles Chemical class 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 150000003573 thiols Chemical class 0.000 claims description 5
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical class C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- YFDAYUXSRDTCHE-UHFFFAOYSA-N 2-[2-[[2-(1h-benzimidazol-2-yl)-1h-pyridin-2-yl]methylsulfanylmethyl]-1h-pyridin-2-yl]-1h-benzimidazole Chemical class N1C=CC=CC1(C=1NC2=CC=CC=C2N=1)CSCC1(C=2NC3=CC=CC=C3N=2)NC=CC=C1 YFDAYUXSRDTCHE-UHFFFAOYSA-N 0.000 claims description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001556 benzimidazoles Chemical class 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- -1 γ-chlorobutyryl residue Chemical group 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 230000027119 gastric acid secretion Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JBWDLHQKWNNDST-UHFFFAOYSA-N 2-(chloromethyl)-4-(furan-2-ylmethylsulfanyl)-3-methylpyridine;hydrochloride Chemical compound Cl.CC1=C(CCl)N=CC=C1SCC1=CC=CO1 JBWDLHQKWNNDST-UHFFFAOYSA-N 0.000 description 3
- VGKARAMUXSIZNJ-UHFFFAOYSA-N 5-[2-[2-(chloromethyl)-3-methylpyridin-4-yl]sulfanylethyl]-4-methyl-1,3-thiazole;hydrochloride Chemical compound Cl.N1=CSC(CCSC=2C(=C(CCl)N=CC=2)C)=C1C VGKARAMUXSIZNJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000590002 Helicobacter pylori Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- WAYMJCUZIDIUKC-UHFFFAOYSA-N [4-(furan-2-ylmethylsulfanyl)-3-methylpyridin-2-yl]methanol Chemical compound CC1=C(CO)N=CC=C1SCC1=CC=CO1 WAYMJCUZIDIUKC-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940037467 helicobacter pylori Drugs 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- BUVJHLBROXOPKN-UHFFFAOYSA-N 2-(chloromethyl)-4-(furan-2-ylmethylsulfanyl)-3-methoxypyridine;hydrochloride Chemical compound Cl.COC1=C(CCl)N=CC=C1SCC1=CC=CO1 BUVJHLBROXOPKN-UHFFFAOYSA-N 0.000 description 2
- MCUYHRNUDDANSO-UHFFFAOYSA-N 4-chloro-2,3-dimethyl-1-oxidopyridin-1-ium Chemical compound CC1=C(C)[N+]([O-])=CC=C1Cl MCUYHRNUDDANSO-UHFFFAOYSA-N 0.000 description 2
- NXONINNYCAGBLM-UHFFFAOYSA-N 5-[2-(2,3-dimethyl-1-oxidopyridin-1-ium-4-yl)sulfanylethyl]-4-methyl-1,3-thiazole Chemical compound N1=CSC(CCSC=2C(=C(C)[N+]([O-])=CC=2)C)=C1C NXONINNYCAGBLM-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BLEDVXIFEAMEFA-UHFFFAOYSA-N [4-(furan-2-ylmethylsulfanyl)-3-methylpyridin-2-yl]methyl acetate Chemical compound CC(=O)OCC1=NC=CC(SCC=2OC=CC=2)=C1C BLEDVXIFEAMEFA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- JAMBTIXVQPBCIP-UHFFFAOYSA-N 1-[5-[[2-(chloromethyl)-3-methylpyridin-4-yl]sulfanylmethyl]furan-2-yl]-n,n-dimethylmethanamine;dihydrochloride Chemical compound Cl.Cl.O1C(CN(C)C)=CC=C1CSC1=CC=NC(CCl)=C1C JAMBTIXVQPBCIP-UHFFFAOYSA-N 0.000 description 1
- JHDTWCNMVYCMPT-UHFFFAOYSA-N 1-[5-[[2-(chloromethyl)-3-methylpyridin-4-yl]sulfanylmethyl]furan-2-yl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.O1C(CN(C)C)=CC=C1CSC1=CC=NC(CCl)=C1C JHDTWCNMVYCMPT-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
- DHLKFLAPAAAFJT-UHFFFAOYSA-N 2-(4-methyl-1,3-thiazol-5-yl)ethanethiol Chemical compound CC=1N=CSC=1CCS DHLKFLAPAAAFJT-UHFFFAOYSA-N 0.000 description 1
- LBCBPCHZLNNQAN-UHFFFAOYSA-N 2-(chloromethyl)-3-methoxy-4-(thiophen-2-ylmethylsulfanyl)pyridine Chemical compound COC1=C(CCl)N=CC=C1SCC1=CC=CS1 LBCBPCHZLNNQAN-UHFFFAOYSA-N 0.000 description 1
- RNWXQBZLFNESGE-UHFFFAOYSA-N 2-(chloromethyl)-3-methyl-4-(1-pyridin-2-ylethylsulfanyl)pyridine Chemical compound C=1C=CC=NC=1C(C)SC1=CC=NC(CCl)=C1C RNWXQBZLFNESGE-UHFFFAOYSA-N 0.000 description 1
- SEYBWPNRZQYBMH-UHFFFAOYSA-N 2-(chloromethyl)-3-methyl-4-(thiophen-2-ylmethylsulfanyl)pyridine Chemical compound CC1=C(CCl)N=CC=C1SCC1=CC=CS1 SEYBWPNRZQYBMH-UHFFFAOYSA-N 0.000 description 1
- ZUIYLHROIHHUIS-UHFFFAOYSA-N 2-(chloromethyl)-3-methyl-4-(thiophen-3-ylmethylsulfanyl)pyridine Chemical compound CC1=C(CCl)N=CC=C1SCC1=CSC=C1 ZUIYLHROIHHUIS-UHFFFAOYSA-N 0.000 description 1
- GDSJBHLKCFMDQN-UHFFFAOYSA-N 2-(chloromethyl)-4-(furan-2-ylmethylsulfanyl)pyridine Chemical compound C1=NC(CCl)=CC(SCC=2OC=CC=2)=C1 GDSJBHLKCFMDQN-UHFFFAOYSA-N 0.000 description 1
- DZVPSYSXFNMNGC-UHFFFAOYSA-N 2-(chloromethyl)-4-(thiophen-2-ylmethylsulfanyl)pyridine Chemical compound C1=NC(CCl)=CC(SCC=2SC=CC=2)=C1 DZVPSYSXFNMNGC-UHFFFAOYSA-N 0.000 description 1
- JVJHOZRRVFRMTK-UHFFFAOYSA-N 2-(chloromethyl)-4-[(3,4-dimethoxypyridin-2-yl)methylsulfanyl]-3-methylpyridine Chemical compound COC1=CC=NC(CSC=2C(=C(CCl)N=CC=2)C)=C1OC JVJHOZRRVFRMTK-UHFFFAOYSA-N 0.000 description 1
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 1
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- TXFYIELBIOJDCQ-UHFFFAOYSA-N 2-[2-[[4-(furan-2-ylmethylsulfanyl)-3-methylpyridin-2-yl]methylsulfanyl]benzimidazol-1-yl]-n,n-dimethylethanamine Chemical compound N=1C2=CC=CC=C2N(CCN(C)C)C=1SCC(C=1C)=NC=CC=1SCC1=CC=CO1 TXFYIELBIOJDCQ-UHFFFAOYSA-N 0.000 description 1
- OAXZBCBXIXMZPF-UHFFFAOYSA-N 2-[[3-methyl-4-[3-(2-methyl-5-nitroimidazol-1-yl)propylsulfanyl]pyridin-2-yl]methylsulfanyl]-1h-benzimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCCSC1=CC=NC(CSC=2NC3=CC=CC=C3N=2)=C1C OAXZBCBXIXMZPF-UHFFFAOYSA-N 0.000 description 1
- KXXVTIPSJAUETA-UHFFFAOYSA-N 2-[[3-methyl-4-[3-(2-methyl-5-nitroimidazol-1-yl)propylsulfanyl]pyridin-2-yl]methylsulfinyl]-1h-benzimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCCSC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C KXXVTIPSJAUETA-UHFFFAOYSA-N 0.000 description 1
- KFUJMMHTNUEFCL-UHFFFAOYSA-N 2-[[4-(3-chloropropylsulfanyl)-3-methylpyridin-2-yl]methylsulfanyl]-1h-benzimidazole Chemical compound CC1=C(SCCCCl)C=CN=C1CSC1=NC2=CC=CC=C2N1 KFUJMMHTNUEFCL-UHFFFAOYSA-N 0.000 description 1
- SRIRRQVQJOMHOH-UHFFFAOYSA-N 2-[[4-(furan-2-ylmethylsulfanyl)-3-methylpyridin-2-yl]methylsulfanyl]-1h-benzimidazole Chemical compound C1=CN=C(CSC=2NC3=CC=CC=C3N=2)C(C)=C1SCC1=CC=CO1 SRIRRQVQJOMHOH-UHFFFAOYSA-N 0.000 description 1
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
- KKMOSYLWYLMHAL-UHFFFAOYSA-N 2-bromo-6-nitroaniline Chemical compound NC1=C(Br)C=CC=C1[N+]([O-])=O KKMOSYLWYLMHAL-UHFFFAOYSA-N 0.000 description 1
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
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- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
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- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH184694 | 1994-06-10 | ||
| PCT/EP1995/002236 WO1995034553A1 (de) | 1994-06-10 | 1995-06-09 | Thiopyridine zur bekämpfung von helicobacter-bakterien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO965161D0 NO965161D0 (no) | 1996-12-03 |
| NO965161L NO965161L (no) | 1997-02-05 |
| NO312727B1 true NO312727B1 (no) | 2002-06-24 |
Family
ID=4219985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19965161A NO312727B1 (no) | 1994-06-10 | 1996-12-03 | Tiopyridiner som bekjempelsesmiddel mot helicobacter- bakterier |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6107312A (xx) |
| EP (1) | EP0764160A1 (xx) |
| JP (1) | JPH10501253A (xx) |
| CN (1) | CN1070192C (xx) |
| AU (1) | AU698249B2 (xx) |
| CA (1) | CA2192206A1 (xx) |
| CZ (1) | CZ288278B6 (xx) |
| FI (1) | FI964908A0 (xx) |
| HU (1) | HUT76054A (xx) |
| MX (1) | MX9606295A (xx) |
| NO (1) | NO312727B1 (xx) |
| NZ (1) | NZ288608A (xx) |
| PL (1) | PL182517B1 (xx) |
| RU (1) | RU2142459C1 (xx) |
| SK (1) | SK283268B6 (xx) |
| WO (1) | WO1995034553A1 (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU781133B2 (en) * | 1999-02-26 | 2005-05-05 | Nicox S.A. | Nitrosated and nitrosylated proton pump inhibitors, compositions and methods of use |
| US7439367B2 (en) | 2003-01-15 | 2008-10-21 | Cipla Limited | Pharmaceutical process and compounds prepared thereby |
| EP2420500A4 (en) * | 2009-04-09 | 2012-09-05 | Arigen Pharmaceuticals Inc | PYRIDINTHIODERIVATE AND PHARMACEUTICAL COMPOSITION THEREOF AND WITH ANTI-HELIDOBACTER PYLORI EFFECT |
| RU2449805C1 (ru) | 2011-01-27 | 2012-05-10 | Общество С Ограниченной Ответственностью "Гармония" | Пептидная фармацевтическая композиция, средство на ее основе для лечения гастродуоденальных заболеваний, вызываемых helicobacter pylori, и способ его использования |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| US4575554A (en) * | 1983-12-05 | 1986-03-11 | The Upjohn Company | Substituted 2-pyridylmethylthio- and sulfinyl-benzimidazoles as gastric antisecretory agents |
| KR890000387B1 (ko) * | 1984-09-24 | 1989-03-16 | 디 엎존 캄파니 | 2-(피리딜알켄술 피닐)벤즈 이미드아졸류의 n-치환 유도체의 제조방법 |
| US5504082A (en) * | 1992-06-01 | 1996-04-02 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridine compound and pharmaceutical compostions |
| KR950701921A (ko) * | 1992-06-01 | 1995-05-17 | 고야 다다시 | 피리딘 화합물 및 이의 제약학적 용도(pyridine compound and medicinal use thereof) |
| JP2671717B2 (ja) * | 1992-06-25 | 1997-10-29 | 住友金属工業株式会社 | 方向性電磁鋼板の製造方法 |
| JPH06100449A (ja) * | 1992-09-18 | 1994-04-12 | Yoshitomi Pharmaceut Ind Ltd | 抗菌剤 |
| EP0673246A1 (de) * | 1992-12-10 | 1995-09-27 | Byk Gulden Lomberg Chemische Fabrik GmbH | Verwendung von alkylthiopyridinen zur bekämpfung von heliobacter-bakterien |
| AU674058B2 (en) * | 1993-02-17 | 1996-12-05 | Altana Pharma Ag | Substituted heteroarylalkylthiopyridines for controlling helicobacter bacteria |
-
1995
- 1995-06-09 NZ NZ288608A patent/NZ288608A/xx unknown
- 1995-06-09 PL PL95317615A patent/PL182517B1/pl unknown
- 1995-06-09 CN CN95194563A patent/CN1070192C/zh not_active Expired - Fee Related
- 1995-06-09 US US08/750,792 patent/US6107312A/en not_active Expired - Fee Related
- 1995-06-09 HU HU9603340A patent/HUT76054A/hu unknown
- 1995-06-09 RU RU97100643/04A patent/RU2142459C1/ru not_active IP Right Cessation
- 1995-06-09 WO PCT/EP1995/002236 patent/WO1995034553A1/de not_active Application Discontinuation
- 1995-06-09 JP JP8501597A patent/JPH10501253A/ja not_active Ceased
- 1995-06-09 CA CA002192206A patent/CA2192206A1/en not_active Abandoned
- 1995-06-09 AU AU27900/95A patent/AU698249B2/en not_active Ceased
- 1995-06-09 EP EP95923287A patent/EP0764160A1/de not_active Withdrawn
- 1995-06-09 CZ CZ19963625A patent/CZ288278B6/cs not_active IP Right Cessation
- 1995-06-09 SK SK1577-96A patent/SK283268B6/sk unknown
-
1996
- 1996-12-03 NO NO19965161A patent/NO312727B1/no unknown
- 1996-12-09 FI FI964908A patent/FI964908A0/fi unknown
- 1996-12-10 MX MX9606295A patent/MX9606295A/es not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI964908A (fi) | 1996-12-09 |
| PL182517B1 (pl) | 2002-01-31 |
| NZ288608A (en) | 1999-01-28 |
| CZ362596A3 (en) | 1997-10-15 |
| SK283268B6 (sk) | 2003-04-01 |
| HUT76054A (en) | 1997-06-30 |
| SK157796A3 (en) | 1997-07-09 |
| AU2790095A (en) | 1996-01-05 |
| CZ288278B6 (en) | 2001-05-16 |
| CA2192206A1 (en) | 1995-12-21 |
| CN1155284A (zh) | 1997-07-23 |
| WO1995034553A1 (de) | 1995-12-21 |
| RU2142459C1 (ru) | 1999-12-10 |
| CN1070192C (zh) | 2001-08-29 |
| US6107312A (en) | 2000-08-22 |
| HU9603340D0 (en) | 1997-02-28 |
| AU698249B2 (en) | 1998-10-29 |
| FI964908A0 (fi) | 1996-12-09 |
| JPH10501253A (ja) | 1998-02-03 |
| NO965161L (no) | 1997-02-05 |
| NO965161D0 (no) | 1996-12-03 |
| EP0764160A1 (de) | 1997-03-26 |
| MX9606295A (es) | 1998-06-30 |
| PL317615A1 (en) | 1997-04-14 |
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