SU1507211A3 - Способ получени производных пиридина - Google Patents
Способ получени производных пиридина Download PDFInfo
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- SU1507211A3 SU1507211A3 SU3947161A SU3947161A SU1507211A3 SU 1507211 A3 SU1507211 A3 SU 1507211A3 SU 3947161 A SU3947161 A SU 3947161A SU 3947161 A SU3947161 A SU 3947161A SU 1507211 A3 SU1507211 A3 SU 1507211A3
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- USSR - Soviet Union
- Prior art keywords
- formula
- compound
- compounds
- mixture
- reaction
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- 238000000034 method Methods 0.000 title claims description 5
- 150000003222 pyridines Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 241000700159 Rattus Species 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 2
- 238000001228 spectrum Methods 0.000 claims 2
- 238000005361 D2 NMR spectroscopy Methods 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 231100000636 lethal dose Toxicity 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 abstract description 5
- 231100000397 ulcer Toxicity 0.000 abstract description 5
- 208000007882 Gastritis Diseases 0.000 abstract description 3
- 230000001079 digestive effect Effects 0.000 abstract description 3
- 208000007107 Stomach Ulcer Diseases 0.000 abstract description 2
- 208000000718 duodenal ulcer Diseases 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 201000005917 gastric ulcer Diseases 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 210000002784 stomach Anatomy 0.000 description 13
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 210000001198 duodenum Anatomy 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- -1 for example Inorganic materials 0.000 description 5
- 229960000905 indomethacin Drugs 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 206010052428 Wound Diseases 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 230000000767 anti-ulcer Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 210000003238 esophagus Anatomy 0.000 description 4
- 210000001156 gastric mucosa Anatomy 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- FLZQTXOQTMOUEX-UHFFFAOYSA-N 3,5-dimethyl-1-oxido-4-(2,2,3,3,3-pentafluoropropoxy)pyridin-1-ium Chemical compound CC1=C[N+]([O-])=CC(C)=C1OCC(F)(F)C(F)(F)F FLZQTXOQTMOUEX-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 239000004160 Ammonium persulphate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- YNGLZRLOOHDZKH-UHFFFAOYSA-N Cl.CC=1C(=NC=CC1OCC(F)(F)F)CS Chemical compound Cl.CC=1C(=NC=CC1OCC(F)(F)F)CS YNGLZRLOOHDZKH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 235000019395 ammonium persulphate Nutrition 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 210000004211 gastric acid Anatomy 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 229940093956 potassium carbonate Drugs 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- LLTGBQQTRVVISK-UHFFFAOYSA-N (3-methylpyridin-2-yl) acetate Chemical class CC(=O)OC1=NC=CC=C1C LLTGBQQTRVVISK-UHFFFAOYSA-N 0.000 description 1
- DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- YWSPNEMTARSIKW-UHFFFAOYSA-N 1-sulfidopyridin-1-ium Chemical class [S-][N+]1=CC=CC=C1 YWSPNEMTARSIKW-UHFFFAOYSA-N 0.000 description 1
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 1
- ZXZMHWHCGQSLEI-UHFFFAOYSA-N 2,3-dimethyl-1-oxido-4-(2,2,3,3,3-pentafluoropropoxy)pyridin-1-ium Chemical compound CC1=C(C)[N+]([O-])=CC=C1OCC(F)(F)C(F)(F)F ZXZMHWHCGQSLEI-UHFFFAOYSA-N 0.000 description 1
- OZSLAMRGQOKODZ-UHFFFAOYSA-N 2,3-dimethyl-1-oxido-4-(2,2,3,3-tetrafluoropropoxy)pyridin-1-ium Chemical compound CC1=C(C)[N+]([O-])=CC=C1OCC(F)(F)C(F)F OZSLAMRGQOKODZ-UHFFFAOYSA-N 0.000 description 1
- CFMTVTYBZMKULI-UHFFFAOYSA-N 2,3-dimethyl-4-nitro-1-oxidopyridin-1-ium Chemical compound CC1=C(C)[N+]([O-])=CC=C1[N+]([O-])=O CFMTVTYBZMKULI-UHFFFAOYSA-N 0.000 description 1
- AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- DBPSVFRRAOJDIY-UHFFFAOYSA-N 2-sulfinyl-1h-pyridine Chemical class O=S=C1C=CC=CN1 DBPSVFRRAOJDIY-UHFFFAOYSA-N 0.000 description 1
- VLKVMXPKEDVNBO-UHFFFAOYSA-N 3,5-dimethyl-4-nitro-1-oxidopyridin-1-ium Chemical compound CC1=C[N+]([O-])=CC(C)=C1[N+]([O-])=O VLKVMXPKEDVNBO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000725101 Clea Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- 241000699670 Mus sp. Species 0.000 description 1
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- PCYNWQAEWNLOQJ-UHFFFAOYSA-N [3,5-dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl]methanol Chemical compound CC1=CN=C(CO)C(C)=C1OCC(F)(F)C(F)(F)F PCYNWQAEWNLOQJ-UHFFFAOYSA-N 0.000 description 1
- IRNCLLHJFZDETF-UHFFFAOYSA-N [3-methyl-4-(2,2,3,3-tetrafluoropropoxy)pyridin-2-yl]methanol Chemical compound CC1=C(OCC(F)(F)C(F)F)C=CN=C1CO IRNCLLHJFZDETF-UHFFFAOYSA-N 0.000 description 1
- KALPHRBHKDXGQH-UHFFFAOYSA-N [4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanol Chemical compound OCC1=CC(OCC(F)(F)F)=CC=N1 KALPHRBHKDXGQH-UHFFFAOYSA-N 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
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- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- 239000003699 antiulcer agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
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- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
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- 239000003937 drug carrier Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical class OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 102200014657 rs121434437 Human genes 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
-
- 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
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LV920583A LV5091A3 (lv) | 1984-08-16 | 1992-12-30 | Piridina atvasinajumu iegusanas metode |
| LTRP440A LT2118B (lt) | 1984-08-16 | 1993-03-19 | Piridino dariniu gavimo budas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59171069A JPS6150978A (ja) | 1984-08-16 | 1984-08-16 | ピリジン誘導体およびその製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1507211A3 true SU1507211A3 (ru) | 1989-09-07 |
Family
ID=15916456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU3947161A SU1507211A3 (ru) | 1984-08-16 | 1985-08-14 | Способ получени производных пиридина |
Country Status (23)
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|---|---|
| US (2) | US4628098A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0174726B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS6150978A (cg-RX-API-DMAC10.html) |
| KR (1) | KR920002128B1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU570130B2 (cg-RX-API-DMAC10.html) |
| BG (1) | BG60415B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA1255314A (cg-RX-API-DMAC10.html) |
| DE (3) | DE19975017I2 (cg-RX-API-DMAC10.html) |
| DK (1) | DK171340B1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES8607288A1 (cg-RX-API-DMAC10.html) |
| GE (1) | GEP19960313B (cg-RX-API-DMAC10.html) |
| GR (1) | GR851981B (cg-RX-API-DMAC10.html) |
| HK (1) | HK4792A (cg-RX-API-DMAC10.html) |
| HU (1) | HU195210B (cg-RX-API-DMAC10.html) |
| IE (1) | IE58363B1 (cg-RX-API-DMAC10.html) |
| MX (1) | MX9203043A (cg-RX-API-DMAC10.html) |
| NL (1) | NL930109I2 (cg-RX-API-DMAC10.html) |
| NO (2) | NO163131C (cg-RX-API-DMAC10.html) |
| PH (1) | PH20946A (cg-RX-API-DMAC10.html) |
| SG (1) | SG103291G (cg-RX-API-DMAC10.html) |
| SU (1) | SU1507211A3 (cg-RX-API-DMAC10.html) |
| UA (1) | UA7140A1 (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA856117B (cg-RX-API-DMAC10.html) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2142459C1 (ru) * | 1994-06-10 | 1999-12-10 | Бык Гульден Ломберг Хемише Фабрик Гмбх | Тиопиридины для борьбы с бактериями helicobakter |
| RU2144031C1 (ru) * | 1995-07-03 | 2000-01-10 | Астра Актиеболаг | Способ оптической очистки энантиомерно обогащенных производных бензимидазола |
| RU2154062C2 (ru) * | 1993-06-29 | 2000-08-10 | Бик Гульден Ломберг Хемише Фабрик Гмбх. | Замещенные арилтиоалкилтиопиридины, способ их получения, лекарственное средство на их основе и способ получения лекарственного средства. |
| RU2157806C2 (ru) * | 1994-07-15 | 2000-10-20 | Астра Актиеболаг | Способы синтеза замещенных сульфоксидов |
| RU2215739C1 (ru) * | 2002-04-03 | 2003-11-10 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Способ получения 5-метокси-2-(4-метокси-3,5-диметил-2-пиридилметилтио)бензимидазола |
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| EP0174717B1 (en) | 1984-07-06 | 1992-01-22 | FISONS plc | Benzimidazoles, and their production formulation and use as gastric acid secretion inhibitors |
| CA1327010C (en) * | 1986-02-13 | 1994-02-15 | Tadashi Makino | Stabilized solid pharmaceutical composition containing antiulcer benzimidazole compound and its production |
| CA1276017C (en) * | 1986-02-13 | 1990-11-06 | Takeda Chemical Industries, Ltd. | Sulfenamide derivatives and their production |
| US6749864B2 (en) * | 1986-02-13 | 2004-06-15 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
| US5433959A (en) * | 1986-02-13 | 1995-07-18 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
| DK171989B1 (da) * | 1987-08-04 | 1997-09-08 | Takeda Chemical Industries Ltd | Fremgangsmåde til fremstilling af 2-(2-pyridylmethylsulfinyl)-benzimidazoler |
| JPH03504497A (ja) * | 1988-05-25 | 1991-10-03 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 新規フルオルアルコキシ化合物 |
| JP2536173B2 (ja) * | 1988-08-18 | 1996-09-18 | 武田薬品工業株式会社 | 注射剤 |
| US5223515A (en) * | 1988-08-18 | 1993-06-29 | Takeda Chemical Industries, Ltd. | Injectable solution containing a pyridyl methylsulfinylbenzimidazole |
| AT391693B (de) * | 1988-11-15 | 1990-11-12 | Cl Pharma | Verfahren zur herstellung von 3-5-dimethyl-4methoxypyridinderivaten sowie neues zwischenprodukt hierfuer |
| IE64199B1 (en) * | 1988-12-22 | 1995-07-12 | Haessle Ab | Compound with gastric acid inhibitory effect and process for its preparation |
| SE8804628D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New compounds |
| SE8804629D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New therapeutically active compounds |
| ATE114114T1 (de) * | 1989-02-10 | 1994-12-15 | Takeda Chemical Industries Ltd | Verwendung von benzimidazol-derivaten als antibakterielle mittel. |
| US5049674A (en) * | 1989-12-20 | 1991-09-17 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| US4965269A (en) * | 1989-12-20 | 1990-10-23 | Ab Hassle | Therapeutically active chloro substituted benzimidazoles |
| US5274099A (en) * | 1989-12-20 | 1993-12-28 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| EP0481764B1 (en) | 1990-10-17 | 2000-03-29 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, their production and use |
| TW209174B (cg-RX-API-DMAC10.html) | 1991-04-19 | 1993-07-11 | Takeda Pharm Industry Co Ltd | |
| WO1993006097A1 (en) * | 1991-09-20 | 1993-04-01 | Merck & Co., Inc. | Novel process for the preparation of anti-ulcer agents |
| ES2036948B1 (es) * | 1991-11-21 | 1994-09-01 | Genesis Para La Investigacion | Procedimiento de obtencion de compuestos derivados de piridina. |
| RU95105442A (ru) * | 1992-07-08 | 1997-02-20 | Монсанто Компани (US) | Способ лечения язвы желудка у свиней, изделие для лечения язвы желудка у свиней |
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| DK0683776T3 (da) * | 1993-02-17 | 1999-10-18 | Byk Gulden Lomberg Chem Fab | Substituerede heteroarylalkylthiopyridiner til bekæmpelse af Helicobacter-bakterier |
| ES2060541B1 (es) * | 1993-02-26 | 1995-11-16 | Vinas Lab | Nuevo procedimiento para la sintesis de un derivado de 2-(2-piridilmetilsufinil) bencimidazol, y nuevos productos intermedios obtenidos con el mismo. |
| ES2063705B1 (es) * | 1993-06-14 | 1995-07-16 | S A L V A T Lab Sa | Intermedio para la sintesis de lansoprazol y su procedimiento de obtencion. |
| TW280770B (cg-RX-API-DMAC10.html) | 1993-10-15 | 1996-07-11 | Takeda Pharm Industry Co Ltd | |
| US5374730A (en) * | 1993-11-04 | 1994-12-20 | Torcan Chemical Ltd. | Preparation of omeprazole and lansoprazole |
| US5502195A (en) * | 1993-11-04 | 1996-03-26 | Slemon; Clarke | Sulfoxide-carboxylate intermediates of omeprazole and lansoprazole |
| CN1048980C (zh) * | 1994-03-29 | 2000-02-02 | 广东汕头鮀滨化学药业总公司 | 一种新的吡啶衍生物及其制备方法和应用 |
| SE9402431D0 (sv) * | 1994-07-08 | 1994-07-08 | Astra Ab | New tablet formulation |
| GB9423968D0 (en) * | 1994-11-28 | 1995-01-11 | Astra Ab | Resolution |
| SE9500422D0 (sv) * | 1995-02-06 | 1995-02-06 | Astra Ab | New oral pharmaceutical dosage forms |
| SE9500478D0 (sv) * | 1995-02-09 | 1995-02-09 | Astra Ab | New pharmaceutical formulation and process |
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| CN107365300B (zh) * | 2017-07-26 | 2019-08-02 | 桂林华信制药有限公司 | 一种有效去除兰索拉唑粗品中杂质的方法 |
| EP3824296A4 (en) | 2018-07-20 | 2022-04-27 | Lipocine Inc. | LIVER DISEASE |
| CN114163419A (zh) * | 2021-12-24 | 2022-03-11 | 辰欣药业股份有限公司 | 一种兰索拉唑的制备方法 |
| JP2025532389A (ja) | 2022-10-04 | 2025-09-29 | ザビリュク，アルセニー | 大動脈弁の石灰化の抑制 |
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| SE416649B (sv) * | 1974-05-16 | 1981-01-26 | Haessle Ab | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| US4359465A (en) * | 1980-07-28 | 1982-11-16 | The Upjohn Company | Methods for treating gastrointestinal inflammation |
| IL66340A (en) * | 1981-08-13 | 1986-08-31 | Haessle Ab | Pharmaceutical compositions comprising pyridylmethyl-thiobenzimidazole derivatives,certain such novel derivatives and their preparation |
| US4472409A (en) * | 1981-11-05 | 1984-09-18 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft Mit Beschrankter Haftung | 2-Pyridylmethyl thio(sulfinyl)benzimidazoles with gastric acid secretion inhibiting effects |
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| HU195220B (en) * | 1983-05-03 | 1988-04-28 | Byk Gulden Lomberg Chem Fqb | Process for production of new fluor-alkoxi-benzimidasole-derivatives and medical compositions containig them |
| US4575554A (en) * | 1983-12-05 | 1986-03-11 | The Upjohn Company | Substituted 2-pyridylmethylthio- and sulfinyl-benzimidazoles as gastric antisecretory agents |
| IL75400A (en) * | 1984-06-16 | 1988-10-31 | Byk Gulden Lomberg Chem Fab | Dialkoxypyridine methyl(sulfinyl or sulfonyl)benzimidazoles,processes for the preparation thereof and pharmaceutical compositions containing the same |
| GB8417171D0 (en) * | 1984-07-05 | 1984-08-08 | Beecham Group Plc | Compounds |
| SE8404065D0 (sv) * | 1984-08-10 | 1984-08-10 | Haessle Ab | Novel biologically active compounds |
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1984
- 1984-08-16 JP JP59171069A patent/JPS6150978A/ja active Granted
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1985
- 1985-07-29 US US06/760,568 patent/US4628098A/en not_active Expired - Lifetime
- 1985-07-31 DE DE19975017C patent/DE19975017I2/de active Active
- 1985-07-31 DE DE19975020C patent/DE19975020I2/de active Active
- 1985-07-31 EP EP19850305458 patent/EP0174726B1/en not_active Expired
- 1985-07-31 DE DE8585305458T patent/DE3569736D1/de not_active Expired
- 1985-08-06 DK DK356485A patent/DK171340B1/da active Protection Beyond IP Right Term
- 1985-08-07 AU AU45895/85A patent/AU570130B2/en not_active Expired
- 1985-08-09 IE IE197685A patent/IE58363B1/en not_active IP Right Cessation
- 1985-08-13 ZA ZA856117A patent/ZA856117B/xx unknown
- 1985-08-13 GR GR851981A patent/GR851981B/el unknown
- 1985-08-13 PH PH32628A patent/PH20946A/en unknown
- 1985-08-14 CA CA000488662A patent/CA1255314A/en not_active Expired
- 1985-08-14 UA UA3947161A patent/UA7140A1/uk unknown
- 1985-08-14 KR KR1019850005863A patent/KR920002128B1/ko not_active Expired
- 1985-08-14 ES ES546152A patent/ES8607288A1/es not_active Expired
- 1985-08-14 SU SU3947161A patent/SU1507211A3/ru active
- 1985-08-15 HU HU853151A patent/HU195210B/hu unknown
- 1985-08-15 NO NO853226A patent/NO163131C/no not_active IP Right Cessation
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1986
- 1986-12-02 US US06/937,193 patent/US4689333A/en not_active Expired - Lifetime
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- 1991-12-04 SG SG1032/91A patent/SG103291G/en unknown
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1992
- 1992-01-16 HK HK47/92A patent/HK4792A/en not_active IP Right Cessation
- 1992-06-19 MX MX9203043A patent/MX9203043A/es unknown
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1993
- 1993-03-11 GE GEAP1993601A patent/GEP19960313B/en unknown
- 1993-06-29 NL NL930109C patent/NL930109I2/nl unknown
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1994
- 1994-02-11 BG BG098459A patent/BG60415B2/bg unknown
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1995
- 1995-03-31 NO NO1995002C patent/NO1995002I1/no unknown
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2154062C2 (ru) * | 1993-06-29 | 2000-08-10 | Бик Гульден Ломберг Хемише Фабрик Гмбх. | Замещенные арилтиоалкилтиопиридины, способ их получения, лекарственное средство на их основе и способ получения лекарственного средства. |
| RU2142459C1 (ru) * | 1994-06-10 | 1999-12-10 | Бык Гульден Ломберг Хемише Фабрик Гмбх | Тиопиридины для борьбы с бактериями helicobakter |
| RU2157806C2 (ru) * | 1994-07-15 | 2000-10-20 | Астра Актиеболаг | Способы синтеза замещенных сульфоксидов |
| RU2144031C1 (ru) * | 1995-07-03 | 2000-01-10 | Астра Актиеболаг | Способ оптической очистки энантиомерно обогащенных производных бензимидазола |
| RU2215739C1 (ru) * | 2002-04-03 | 2003-11-10 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Способ получения 5-метокси-2-(4-метокси-3,5-диметил-2-пиридилметилтио)бензимидазола |
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