JPS6122079A - ジアルコキシピリジン及びそれを含有する薬剤 - Google Patents
ジアルコキシピリジン及びそれを含有する薬剤Info
- Publication number
- JPS6122079A JPS6122079A JP12918385A JP12918385A JPS6122079A JP S6122079 A JPS6122079 A JP S6122079A JP 12918385 A JP12918385 A JP 12918385A JP 12918385 A JP12918385 A JP 12918385A JP S6122079 A JPS6122079 A JP S6122079A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- benzimidazole
- dimethoxy
- fluorine
- 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.)
- Granted
Links
- 239000003814 drug Substances 0.000 title claims description 17
- 229940079593 drug Drugs 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 134
- -1 chlorotrifluoroethylenedioxy group Chemical group 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 239000011737 fluorine Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 230000027119 gastric acid secretion Effects 0.000 claims description 4
- 230000002496 gastric effect Effects 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 3
- CGQWZVMVSJLPKO-UHFFFAOYSA-N 2-methylpyridine-3-thiol Chemical compound CC1=NC=CC=C1S CGQWZVMVSJLPKO-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 150000004675 formic acid derivatives Chemical class 0.000 claims description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- PMPBIIJSWDDUHQ-UHFFFAOYSA-N 2-[(4,5-dimethoxy-3-methylpyridin-2-yl)methylsulfinyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound CC1=C(OC)C(OC)=CN=C1CS(=O)C1=NC2=CC(OC(F)(F)F)=CC=C2N1 PMPBIIJSWDDUHQ-UHFFFAOYSA-N 0.000 claims 1
- GTZJAVFSFKBXLB-UHFFFAOYSA-N 2-[(4,5-dimethoxypyridin-2-yl)methylsulfinyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound C1=C(OC)C(OC)=CN=C1CS(=O)C1=NC2=CC(OC(F)(F)C(F)F)=CC=C2N1 GTZJAVFSFKBXLB-UHFFFAOYSA-N 0.000 claims 1
- YFDAYUXSRDTCHE-UHFFFAOYSA-N 2-[2-[[2-(1h-benzimidazol-2-yl)-1h-pyridin-2-yl]methylsulfanylmethyl]-1h-pyridin-2-yl]-1h-benzimidazole Chemical compound 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 1
- NCPKETXRPZSZCJ-UHFFFAOYSA-N 6-[(4,5-dimethoxypyridin-2-yl)methylsulfanyl]-2,2-difluoro-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound C1=C(OC)C(OC)=CN=C1CSC(NC1=C2)=NC1=CC1=C2OC(F)(F)O1 NCPKETXRPZSZCJ-UHFFFAOYSA-N 0.000 claims 1
- 208000028774 intestinal disease Diseases 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 208000018556 stomach disease Diseases 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 135
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 108
- 239000000243 solution Substances 0.000 description 86
- 238000002844 melting Methods 0.000 description 74
- 230000008018 melting Effects 0.000 description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 239000000203 mixture Substances 0.000 description 36
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000003756 stirring Methods 0.000 description 29
- 238000000354 decomposition reaction Methods 0.000 description 28
- 238000000034 method Methods 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 229910017604 nitric acid Inorganic materials 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 17
- 239000012141 concentrate Substances 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- 238000007254 oxidation reaction Methods 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 229940060037 fluorine Drugs 0.000 description 8
- 235000019000 fluorine Nutrition 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 6
- 235000019345 sodium thiosulphate Nutrition 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000011343 solid material Substances 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- HAMUUCVAFXJSLN-UHFFFAOYSA-N 5-methoxy-2-methyl-1-oxidopyridin-1-ium Chemical compound COC1=CC=C(C)[N+]([O-])=C1 HAMUUCVAFXJSLN-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 150000002902 organometallic compounds Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229960003975 potassium Drugs 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- BEFVSXHBUPRUCQ-UHFFFAOYSA-N 2-(chloromethyl)-4,5-dimethoxypyridine;hydrochloride Chemical compound [Cl-].COC1=C[NH+]=C(CCl)C=C1OC BEFVSXHBUPRUCQ-UHFFFAOYSA-N 0.000 description 3
- LPVVVCBDJJRLHT-UHFFFAOYSA-N 5-methoxy-2-methylpyridine Chemical compound COC1=CC=C(C)N=C1 LPVVVCBDJJRLHT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 210000004211 gastric acid Anatomy 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- AMHBOGMTNCYBBP-UHFFFAOYSA-N 2-(chloromethyl)-4,5-dimethoxy-3-methylpyridine;hydrochloride Chemical compound [Cl-].COC1=C[NH+]=C(CCl)C(C)=C1OC AMHBOGMTNCYBBP-UHFFFAOYSA-N 0.000 description 2
- AQSRRZGQRFFFGS-UHFFFAOYSA-N 2-methylpyridin-3-ol Chemical compound CC1=NC=CC=C1O AQSRRZGQRFFFGS-UHFFFAOYSA-N 0.000 description 2
- QRCUQLANPHYVEH-UHFFFAOYSA-N 3-methoxy-2-methylpyridine Chemical compound COC1=CC=CN=C1C QRCUQLANPHYVEH-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- FNZBCXOEZCYHFI-UHFFFAOYSA-N 4-methoxy-5,6-dimethylpyridin-3-ol Chemical compound COC1=C(C)C(C)=NC=C1O FNZBCXOEZCYHFI-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000009858 acid secretion Effects 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229940049920 malate Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
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- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 230000002178 gastroprotective effect Effects 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- WKOOSDWVFMFRAU-UHFFFAOYSA-N n-(1,1,2,2-tetrafluoroethoxy)aniline Chemical compound FC(F)C(F)(F)ONC1=CC=CC=C1 WKOOSDWVFMFRAU-UHFFFAOYSA-N 0.000 description 1
- DENXIPOLEMAGBA-UHFFFAOYSA-N n-[4-(difluoromethoxy)-3-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OC(F)F)C(F)=C1 DENXIPOLEMAGBA-UHFFFAOYSA-N 0.000 description 1
- BBULBKJDQUAZLY-UHFFFAOYSA-N n-[5-(difluoromethoxy)-4-methoxy-2-nitrophenyl]acetamide Chemical compound COC1=CC([N+]([O-])=O)=C(NC(C)=O)C=C1OC(F)F BBULBKJDQUAZLY-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960002369 oxyphencyclimine Drugs 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- CFZKDDTWZYUZKS-UHFFFAOYSA-N picoline N-oxide Chemical compound CC1=CC=CC=[N+]1[O-] CFZKDDTWZYUZKS-UHFFFAOYSA-N 0.000 description 1
- 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
- 229960004633 pirenzepine Drugs 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 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
- 229960000620 ranitidine Drugs 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003452 sulfinic acid derivatives Chemical class 0.000 description 1
- 229940071103 sulfosalicylate Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 229950004351 telenzepine Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000007214 z medium Substances 0.000 description 1
- 229950004963 zolenzepine Drugs 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH289984 | 1984-06-16 | ||
| CH2901/84-4 | 1984-06-16 | ||
| CH2899/84-0 | 1984-06-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6122079A true JPS6122079A (ja) | 1986-01-30 |
| JPH0313234B2 JPH0313234B2 (enrdf_load_stackoverflow) | 1991-02-22 |
Family
ID=4244118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12918385A Granted JPS6122079A (ja) | 1984-06-16 | 1985-06-15 | ジアルコキシピリジン及びそれを含有する薬剤 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6122079A (enrdf_load_stackoverflow) |
| ZA (1) | ZA854287B (enrdf_load_stackoverflow) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6150979A (ja) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
| JPS62198678A (ja) * | 1986-02-25 | 1987-09-02 | バイエル・アクチエンゲゼルシヤフト | フルオル化された↓０−ジアミノベンゾ−１，４−ジオキセン類の製造法 |
| JPS635061A (ja) * | 1986-06-25 | 1988-01-11 | バイエル・アクチエンゲゼルシヤフト | フツ素含有↓０−フエニレンジアミン及び↓０−アミノフエノ−ル |
| WO1989000566A1 (en) * | 1987-07-21 | 1989-01-26 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridine compounds and medicinal use thereof |
| WO2000009472A1 (fr) * | 1998-08-12 | 2000-02-24 | Ihara Chemical Industry Co., Ltd. | N-cyclopropyl-2-difloromethoxy-3-halogeno-anilines et intermediaires utilises pour la preparation de ces composes |
| US6180652B1 (en) | 1998-11-16 | 2001-01-30 | Eisai Co., Ltd. | Sulfoxide compounds and acetone complexes, and a process for producing the same |
| JP2003531144A (ja) * | 2000-04-14 | 2003-10-21 | エスティーブ キミカ ソシエダッド アノニマ | ［［（ピリジル置換）メチル］チオ］ベンズイミダゾールの誘導体を得る方法 |
| US6884810B2 (en) | 2001-09-18 | 2005-04-26 | Zeria Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| WO2005077936A1 (en) | 2004-02-11 | 2005-08-25 | Ulkar Kimya Sanayii Ve Ticaret A.S. | Pyridine benzimidazole sulfoxides with high purity |
| JP2006515353A (ja) * | 2003-01-15 | 2006-05-25 | シプラ・リミテッド | 製薬的方法、及び該方法により製造された化合物 |
| JP2008524190A (ja) * | 2004-12-16 | 2008-07-10 | シプラ・リミテッド | パントプラゾールナトリウムの製造方法 |
| JP2009502872A (ja) * | 2005-07-26 | 2009-01-29 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 同位体置換されたパントプラゾール |
| EP2277510A2 (en) | 2002-10-16 | 2011-01-26 | Takeda Pharmaceutical Company Limited | Controlled release preparation |
| JP2013518826A (ja) * | 2010-02-02 | 2013-05-23 | シュエンジュウ・ファーマ・カンパニー・リミテッド | ベンズイミダゾール誘導体、並びにその医薬組成物及び使用 |
-
1985
- 1985-06-06 ZA ZA854287A patent/ZA854287B/xx unknown
- 1985-06-15 JP JP12918385A patent/JPS6122079A/ja active Granted
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6150979A (ja) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
| JPS62198678A (ja) * | 1986-02-25 | 1987-09-02 | バイエル・アクチエンゲゼルシヤフト | フルオル化された↓０−ジアミノベンゾ−１，４−ジオキセン類の製造法 |
| JPH0841047A (ja) * | 1986-02-25 | 1996-02-13 | Bayer Ag | 新規なフルオル化されたｏ−ジアミノベンゾ−１，４−ジオキセン |
| JPS635061A (ja) * | 1986-06-25 | 1988-01-11 | バイエル・アクチエンゲゼルシヤフト | フツ素含有↓０−フエニレンジアミン及び↓０−アミノフエノ−ル |
| WO1989000566A1 (en) * | 1987-07-21 | 1989-01-26 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridine compounds and medicinal use thereof |
| WO2000009472A1 (fr) * | 1998-08-12 | 2000-02-24 | Ihara Chemical Industry Co., Ltd. | N-cyclopropyl-2-difloromethoxy-3-halogeno-anilines et intermediaires utilises pour la preparation de ces composes |
| US6316658B1 (en) | 1998-08-12 | 2001-11-13 | Ihara Chemical Industry Co., Ltd. | N-cyclopropyl-2-difluoromethoxy-3-halogenoanilines and intermediates for the preparation thereof |
| US6180652B1 (en) | 1998-11-16 | 2001-01-30 | Eisai Co., Ltd. | Sulfoxide compounds and acetone complexes, and a process for producing the same |
| US6545024B1 (en) | 1998-11-16 | 2003-04-08 | Eisai Co., Ltd. | Sulfoxide compounds and acetone complexes, and a process for producing the same |
| JP2003531144A (ja) * | 2000-04-14 | 2003-10-21 | エスティーブ キミカ ソシエダッド アノニマ | ［［（ピリジル置換）メチル］チオ］ベンズイミダゾールの誘導体を得る方法 |
| US6884810B2 (en) | 2001-09-18 | 2005-04-26 | Zeria Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| EP2277510A2 (en) | 2002-10-16 | 2011-01-26 | Takeda Pharmaceutical Company Limited | Controlled release preparation |
| EP2283827A1 (en) | 2002-10-16 | 2011-02-16 | Takeda Pharmaceutical Company Limited | Controlled release preparation |
| JP2006515353A (ja) * | 2003-01-15 | 2006-05-25 | シプラ・リミテッド | 製薬的方法、及び該方法により製造された化合物 |
| WO2005077936A1 (en) | 2004-02-11 | 2005-08-25 | Ulkar Kimya Sanayii Ve Ticaret A.S. | Pyridine benzimidazole sulfoxides with high purity |
| JP2008524190A (ja) * | 2004-12-16 | 2008-07-10 | シプラ・リミテッド | パントプラゾールナトリウムの製造方法 |
| US8691995B2 (en) | 2004-12-16 | 2014-04-08 | Cipla Limited | Process |
| JP2009502872A (ja) * | 2005-07-26 | 2009-01-29 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 同位体置換されたパントプラゾール |
| JP2013518826A (ja) * | 2010-02-02 | 2013-05-23 | シュエンジュウ・ファーマ・カンパニー・リミテッド | ベンズイミダゾール誘導体、並びにその医薬組成物及び使用 |
| US9315513B2 (en) | 2010-02-02 | 2016-04-19 | Xuanzhu Pharma Co., Ltd. | Benzimidazole derivatives and their pharmaceutical compositions and uses |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA854287B (en) | 1986-02-26 |
| JPH0313234B2 (enrdf_load_stackoverflow) | 1991-02-22 |
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| Date | Code | Title | Description |
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| R250 | Receipt of annual fees |
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| EXPY | Cancellation because of completion of term |