CH644116A5 - Imidazolderivate. - Google Patents
Imidazolderivate. Download PDFInfo
- Publication number
- CH644116A5 CH644116A5 CH632180A CH632180A CH644116A5 CH 644116 A5 CH644116 A5 CH 644116A5 CH 632180 A CH632180 A CH 632180A CH 632180 A CH632180 A CH 632180A CH 644116 A5 CH644116 A5 CH 644116A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- pyridyl
- hydrogen
- thio
- melting point
- Prior art date
Links
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims description 66
- -1 alkooxyoxyalkyl Chemical group 0.000 claims description 44
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 230000027119 gastric acid secretion Effects 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 208000025865 Ulcer Diseases 0.000 claims description 5
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 231100000397 ulcer Toxicity 0.000 claims description 5
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 3
- KIKCSVMFMANYLK-UHFFFAOYSA-N 6-(pyridin-2-ylmethylsulfanyl)-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound N=1C2=CC=3OCOC=3C=C2NC=1SCC1=CC=CC=N1 KIKCSVMFMANYLK-UHFFFAOYSA-N 0.000 claims description 3
- 229930194542 Keto Natural products 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 125000005323 thioketone group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims 3
- JOOFUZFINOTQIW-UHFFFAOYSA-N 5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound C1=C2OCOC2=CC2=C1NC=N2 JOOFUZFINOTQIW-UHFFFAOYSA-N 0.000 claims 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- PGWHEHZFCSUEMH-UHFFFAOYSA-N 2-[(5-methylpyridin-2-yl)methylsulfanyl]-3,5,6,7-tetrahydrocyclopenta[f]benzimidazole Chemical compound N1=CC(C)=CC=C1CSC(NC1=C2)=NC1=CC1=C2CCC1 PGWHEHZFCSUEMH-UHFFFAOYSA-N 0.000 claims 1
- 239000003699 antiulcer agent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
- 238000002844 melting Methods 0.000 description 113
- 230000008018 melting Effects 0.000 description 113
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 95
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 91
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 57
- 239000000243 solution Substances 0.000 description 53
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 229960000583 acetic acid Drugs 0.000 description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 38
- 239000012362 glacial acetic acid Substances 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 34
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 28
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 238000010992 reflux Methods 0.000 description 27
- 238000006277 sulfonation reaction Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000012043 crude product Substances 0.000 description 19
- 239000013078 crystal Substances 0.000 description 19
- 238000001704 evaporation Methods 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000007935 neutral effect Effects 0.000 description 16
- 239000007858 starting material Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 239000007832 Na2SO4 Substances 0.000 description 13
- 239000007868 Raney catalyst Substances 0.000 description 13
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 13
- 229910000564 Raney nickel Inorganic materials 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- UCUJUFDOQOJLBE-UHFFFAOYSA-N [Cl].[Ca] Chemical compound [Cl].[Ca] UCUJUFDOQOJLBE-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- BZVHVHZQEDFKOZ-UHFFFAOYSA-N 2-methyl-6-nitro-1,3-benzodioxol-5-amine Chemical compound NC1=C([N+]([O-])=O)C=C2OC(C)OC2=C1 BZVHVHZQEDFKOZ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- MXOPKPMEGUYUCV-UHFFFAOYSA-N 2-(chloromethyl)-5-methylpyridine Chemical compound CC1=CC=C(CCl)N=C1 MXOPKPMEGUYUCV-UHFFFAOYSA-N 0.000 description 5
- XMYXMFFLLWMJTB-UHFFFAOYSA-N C1=C2N=CNC2=CC2=CC(=O)C=C21 Chemical compound C1=C2N=CNC2=CC2=CC(=O)C=C21 XMYXMFFLLWMJTB-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 230000000767 anti-ulcer Effects 0.000 description 5
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- BVJIXYJOFWYOBL-UHFFFAOYSA-N 2-(5-methyl-1h-imidazol-4-yl)ethanamine;dihydrochloride Chemical compound Cl.Cl.CC=1NC=NC=1CCN BVJIXYJOFWYOBL-UHFFFAOYSA-N 0.000 description 4
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- UGYXPZQILZRKJJ-UHFFFAOYSA-N 4-methylhistamine Chemical compound CC=1NC=NC=1CCN UGYXPZQILZRKJJ-UHFFFAOYSA-N 0.000 description 4
- STLBXFFFISDBMC-UHFFFAOYSA-N 5,5,7,7-tetramethyl-2-(pyridin-2-ylmethylsulfanyl)-3h-cyclopenta[f]benzimidazol-6-one Chemical compound N=1C=2C=C3C(C)(C)C(=O)C(C)(C)C3=CC=2NC=1SCC1=CC=CC=N1 STLBXFFFISDBMC-UHFFFAOYSA-N 0.000 description 4
- FTKQOUSCCFFFPQ-UHFFFAOYSA-N 6-[(5-methylpyridin-2-yl)methylsulfanyl]-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound N1=CC(C)=CC=C1CSC(NC1=C2)=NC1=CC1=C2OCO1 FTKQOUSCCFFFPQ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 3
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 3
- OIZYPQDTTQERGE-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-3,5,6,7-tetrahydrocyclopenta[f]benzimidazole Chemical compound N=1C2=CC=3CCCC=3C=C2NC=1SCC1=CC=CC=N1 OIZYPQDTTQERGE-UHFFFAOYSA-N 0.000 description 3
- SNWQAKNKGGOVMO-UHFFFAOYSA-N 5-nitro-1,3-benzodioxole Chemical compound [O-][N+](=O)C1=CC=C2OCOC2=C1 SNWQAKNKGGOVMO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 210000004051 gastric juice Anatomy 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- AIDIZEMTCCZDJJ-UHFFFAOYSA-N n-(5-nitro-4h-1,3-benzodioxin-6-yl)acetamide Chemical compound O1COCC2=C([N+]([O-])=O)C(NC(=O)C)=CC=C21 AIDIZEMTCCZDJJ-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XVZPKKJRSGUSNP-UHFFFAOYSA-N 1,1,4,4-tetramethyl-6,7-dinitro-2,3-dihydronaphthalene Chemical compound [O-][N+](=O)C1=C([N+]([O-])=O)C=C2C(C)(C)CCC(C)(C)C2=C1 XVZPKKJRSGUSNP-UHFFFAOYSA-N 0.000 description 2
- PMTXBVARJFBMAC-UHFFFAOYSA-N 1,3,6,7-tetrahydro-[1,4]dioxino[2,3-f]benzimidazole-2-thione Chemical compound O1CCOC2=C1C=C1NC(=S)NC1=C2 PMTXBVARJFBMAC-UHFFFAOYSA-N 0.000 description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
- YXEJRYIEFFUUID-UHFFFAOYSA-N 1,3-benzodioxole-5,6-diamine;dihydrochloride Chemical compound Cl.Cl.C1=C(N)C(N)=CC2=C1OCO2 YXEJRYIEFFUUID-UHFFFAOYSA-N 0.000 description 2
- DWYNRLSJJFFRGC-UHFFFAOYSA-N 1-benzothiophene-4,5-diamine Chemical compound NC1=CC=C2SC=CC2=C1N DWYNRLSJJFFRGC-UHFFFAOYSA-N 0.000 description 2
- BWBIFYYKIWPTRV-UHFFFAOYSA-N 2,2-dimethyl-1,3-benzodioxole Chemical compound C1=CC=C2OC(C)(C)OC2=C1 BWBIFYYKIWPTRV-UHFFFAOYSA-N 0.000 description 2
- HCTLMAMWVMRCKY-UHFFFAOYSA-N 2,2-dimethyl-6-[(5-methylpyridin-2-yl)methylsulfanyl]-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound N1=CC(C)=CC=C1CSC(NC1=C2)=NC1=CC1=C2OC(C)(C)O1 HCTLMAMWVMRCKY-UHFFFAOYSA-N 0.000 description 2
- IANVKUIMAHXNOX-UHFFFAOYSA-N 2,2-dimethyl-6-nitro-1,3-benzodioxol-5-amine Chemical compound NC1=C([N+]([O-])=O)C=C2OC(C)(C)OC2=C1 IANVKUIMAHXNOX-UHFFFAOYSA-N 0.000 description 2
- IQOUJLNQAHTBBG-UHFFFAOYSA-N 2,3-dihydro-1h-indene-5,6-diamine Chemical compound C1=C(N)C(N)=CC2=C1CCC2 IQOUJLNQAHTBBG-UHFFFAOYSA-N 0.000 description 2
- GZAQEHKYNRVURU-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-1,5,6,7-tetrahydropyrrolo[2,3-f]benzimidazole Chemical compound N=1C2=CC=3NCCC=3C=C2NC=1SCC1=CC=CC=N1 GZAQEHKYNRVURU-UHFFFAOYSA-N 0.000 description 2
- GXWZLQGMSSNNRS-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-6,7-dihydro-1h-[1,4]dioxino[2,3-f]benzimidazole Chemical compound N=1C2=CC=3OCCOC=3C=C2NC=1SCC1=CC=CC=N1 GXWZLQGMSSNNRS-UHFFFAOYSA-N 0.000 description 2
- VMKCNRXTVZFHOY-UHFFFAOYSA-N 2-[(5-methylpyridin-2-yl)methylsulfanyl]-1,5,6,7-tetrahydropyrrolo[2,3-f]benzimidazole Chemical compound N1=CC(C)=CC=C1CSC(NC1=C2)=NC1=CC1=C2CCN1 VMKCNRXTVZFHOY-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH632180A CH644116A5 (de) | 1980-08-21 | 1980-08-21 | Imidazolderivate. |
| DK300981A DK300981A (da) | 1980-08-21 | 1981-07-07 | Fremgangsmaade til fremstilling af imidazolderivater |
| PH26015A PH17937A (en) | 1980-08-21 | 1981-08-05 | Imidazole derivatives,their compositions and use thereof |
| NL8103690A NL8103690A (nl) | 1980-08-21 | 1981-08-05 | Imidazoolderivaten. |
| US06/290,032 US4435406A (en) | 1980-08-21 | 1981-08-05 | Imidazole derivatives |
| IL63576A IL63576A (en) | 1980-08-21 | 1981-08-14 | Tricyclic imidazolethio(sulfinyl)alkyl pyridine derivatives,their manufacture and pharmaceutical compositions containing them |
| ZA815633A ZA815633B (en) | 1980-08-21 | 1981-08-14 | Imidazole derivatives |
| NZ198047A NZ198047A (en) | 1980-08-21 | 1981-08-14 | Tricyclic imidazole derivatives carrying a pyrid-2-ylmethylthio substituent |
| AU74089/81A AU541834B2 (en) | 1980-08-21 | 1981-08-14 | Imidazole derivatives |
| IT23556/81A IT1138156B (it) | 1980-08-21 | 1981-08-18 | Immidazol-derivati |
| DE19813132613 DE3132613A1 (de) | 1980-08-21 | 1981-08-18 | Imidazolderivate |
| CA000384169A CA1134829A (en) | 1980-08-21 | 1981-08-19 | Imidazole derivatives |
| FR8115936A FR2488890A1 (fr) | 1980-08-21 | 1981-08-19 | Derives tricycliques de l'imidazole, leur preparation et leurs utilisations therapeutiques |
| GB8125486A GB2082580B (en) | 1980-08-21 | 1981-08-20 | Tricyclic imidazole derivatives |
| BE0/205721A BE890024A (fr) | 1980-08-21 | 1981-08-20 | Derives tricycliques de l'imidazole, leur preparation et leurs utilisations therapeutiques |
| JP56129475A JPS5770886A (en) | 1980-08-21 | 1981-08-20 | Imidazole derivative |
| AT0364381A AT376665B (de) | 1980-08-21 | 1981-08-20 | Verfahren zur herstellung von neuen imidazolderivaten und von deren saeureadditionssalzen |
| IE1912/81A IE51507B1 (en) | 1980-08-21 | 1981-08-20 | Tricyclic imidazole derivatives |
| LU83571A LU83571A1 (de) | 1980-08-21 | 1981-08-20 | Imidazolderivate |
| SE8104941A SE452765B (sv) | 1980-08-21 | 1981-08-20 | Tricykliska imidazolderivat, deras framstellning, farmaceutiska kompositioner och anvendning |
| US06/560,699 US4599347A (en) | 1980-08-21 | 1983-12-12 | Tetrahydro-naphth (2.3-d) imidazole derivatives |
| US06/560,698 US4554280A (en) | 1980-08-21 | 1983-12-12 | Pyridyl methyl thio or sulfinyl indeno(5,6-d)imidazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH632180A CH644116A5 (de) | 1980-08-21 | 1980-08-21 | Imidazolderivate. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH644116A5 true CH644116A5 (de) | 1984-07-13 |
Family
ID=4307711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH632180A CH644116A5 (de) | 1980-08-21 | 1980-08-21 | Imidazolderivate. |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US4435406A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5770886A (cg-RX-API-DMAC7.html) |
| AT (1) | AT376665B (cg-RX-API-DMAC7.html) |
| AU (1) | AU541834B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE890024A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1134829A (cg-RX-API-DMAC7.html) |
| CH (1) | CH644116A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3132613A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK300981A (cg-RX-API-DMAC7.html) |
| FR (1) | FR2488890A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2082580B (cg-RX-API-DMAC7.html) |
| IE (1) | IE51507B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL63576A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1138156B (cg-RX-API-DMAC7.html) |
| LU (1) | LU83571A1 (cg-RX-API-DMAC7.html) |
| NL (1) | NL8103690A (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ198047A (cg-RX-API-DMAC7.html) |
| PH (1) | PH17937A (cg-RX-API-DMAC7.html) |
| SE (1) | SE452765B (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA815633B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0221041A3 (en) * | 1985-10-29 | 1987-10-28 | Aktiebolaget Hässle | Benzimidazole derivatives, process for their preparation and their pharmaceutical use |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA825106B (en) * | 1981-08-13 | 1983-04-27 | Haessle Ab | Novel pharmaceutical compositions |
| DE3216843C2 (de) * | 1982-05-05 | 1986-10-23 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | 3-Thiomethyl-pyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| US4686232A (en) * | 1983-02-28 | 1987-08-11 | Sumitomo Chemical Company, Limited | Fungicidal aniline derivatives |
| HU191756B (en) * | 1983-05-03 | 1987-04-28 | Byk Gulden Lomberg Chem Fab | Process for preparing new fluoro-alkoxy-benzimidazole derivatives |
| 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 |
| ZW4585A1 (en) * | 1984-04-19 | 1985-11-20 | Hoffmann La Roche | Imidazole derivatives |
| PL144822B1 (en) * | 1984-05-12 | 1988-07-30 | Boehringer Mannheim Gmbh | Method of obtaining novel pyrolobenzimidazoles |
| 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 |
| IL76839A (en) * | 1984-10-31 | 1988-08-31 | Byk Gulden Lomberg Chem Fab | Picoline derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| GB8526154D0 (en) * | 1985-02-06 | 1985-11-27 | Kotobuki Seiyaku Co Ltd | 2-substituted cyclo-heptoimidazoles |
| DK337086A (da) * | 1985-08-12 | 1987-02-13 | Hoffmann La Roche | Benzimidazolderivater |
| WO1987005296A1 (en) * | 1986-03-07 | 1987-09-11 | Pfizer Inc. | 2-[(2-pyridyl)methylsulfinyl]thienoimidazoles and related compounds as antiulcer agents |
| SE8604566D0 (sv) * | 1986-10-27 | 1986-10-27 | Haessle Ab | Novel compunds |
| NZ234564A (en) | 1986-11-21 | 1991-04-26 | Haessle Ab | 1-substituted benzimidazoles and pharmaceutical compositions |
| SE8604998D0 (sv) | 1986-11-21 | 1986-11-21 | Haessle Ab | Novel pharmacological compounds |
| DE3701277A1 (de) * | 1987-01-17 | 1988-07-28 | Boehringer Mannheim Gmbh | Neue tricyclische benzimidazole, verfahren zu ihrer herstellung und verwendung als arzneimittel |
| FR2614618B1 (fr) * | 1987-04-30 | 1989-07-07 | Cird | Derives heterocycliques polycycliques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire |
| US5223515A (en) * | 1988-08-18 | 1993-06-29 | Takeda Chemical Industries, Ltd. | Injectable solution containing a pyridyl methylsulfinylbenzimidazole |
| US5175286A (en) * | 1988-09-20 | 1992-12-29 | Hisamitsu Pharmaceutical Co., Inc. | Dibenz[b,e]oxepin derivatives |
| IE64199B1 (en) * | 1988-12-22 | 1995-07-12 | Haessle Ab | Compound with gastric acid inhibitory effect and process for its preparation |
| SE8804629D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New therapeutically active compounds |
| SE8804628D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New compounds |
| US5274099A (en) * | 1989-12-20 | 1993-12-28 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| 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 |
| SE9002206D0 (sv) | 1990-06-20 | 1990-06-20 | Haessle Ab | New compounds |
| DE4027592A1 (de) * | 1990-08-31 | 1992-03-05 | Beiersdorf Ag | Neue pyrrolobenzimidazole, imidazobenzoxazinone und imidazochinolone, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen |
| US5395952A (en) * | 1991-06-03 | 1995-03-07 | Sumitomo Chemical Company, Limited | Benzimidazole derivatives agricultural and horticultural fungicides containing the same as an active ingredient and intermediate compounds thereof |
| US6207198B1 (en) * | 1995-09-21 | 2001-03-27 | Schwarz Pharma Ag | Composition containing an acid-labile omeprazole and process for its preparation |
| DE19745692A1 (de) * | 1997-07-24 | 1999-01-28 | Bayer Ag | Verfahren zur Herstellung von 2-Chlor-benzimidazol-Derivaten |
| AU753389C (en) * | 1997-12-31 | 2007-08-09 | Pfizer Products Inc. | Aryl fused azapolycyclic compounds |
| CN100349868C (zh) * | 2002-07-17 | 2007-11-21 | 京都药品工业株式会社 | 二氢吲哚化合物和其医药用途 |
| US20060024362A1 (en) | 2004-07-29 | 2006-02-02 | Pawan Seth | Composition comprising a benzimidazole and process for its manufacture |
| CN102140099A (zh) * | 2010-02-02 | 2011-08-03 | 山东轩竹医药科技有限公司 | 新的吡啶衍生物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE5129C1 (cg-RX-API-DMAC7.html) | 1894-05-19 | |||
| SE418966B (sv) * | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
| SE416649B (sv) * | 1974-05-16 | 1981-01-26 | Haessle Ab | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| IN148930B (cg-RX-API-DMAC7.html) * | 1977-09-19 | 1981-07-25 | Hoffmann La Roche | |
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
-
1980
- 1980-08-21 CH CH632180A patent/CH644116A5/de not_active IP Right Cessation
-
1981
- 1981-07-07 DK DK300981A patent/DK300981A/da not_active Application Discontinuation
- 1981-08-05 NL NL8103690A patent/NL8103690A/xx not_active Application Discontinuation
- 1981-08-05 PH PH26015A patent/PH17937A/en unknown
- 1981-08-05 US US06/290,032 patent/US4435406A/en not_active Expired - Fee Related
- 1981-08-14 NZ NZ198047A patent/NZ198047A/en unknown
- 1981-08-14 ZA ZA815633A patent/ZA815633B/xx unknown
- 1981-08-14 AU AU74089/81A patent/AU541834B2/en not_active Ceased
- 1981-08-14 IL IL63576A patent/IL63576A/xx unknown
- 1981-08-18 DE DE19813132613 patent/DE3132613A1/de not_active Withdrawn
- 1981-08-18 IT IT23556/81A patent/IT1138156B/it active
- 1981-08-19 FR FR8115936A patent/FR2488890A1/fr active Granted
- 1981-08-19 CA CA000384169A patent/CA1134829A/en not_active Expired
- 1981-08-20 GB GB8125486A patent/GB2082580B/en not_active Expired
- 1981-08-20 AT AT0364381A patent/AT376665B/de not_active IP Right Cessation
- 1981-08-20 BE BE0/205721A patent/BE890024A/fr not_active IP Right Cessation
- 1981-08-20 LU LU83571A patent/LU83571A1/de unknown
- 1981-08-20 SE SE8104941A patent/SE452765B/sv not_active IP Right Cessation
- 1981-08-20 IE IE1912/81A patent/IE51507B1/en unknown
- 1981-08-20 JP JP56129475A patent/JPS5770886A/ja active Pending
-
1983
- 1983-12-12 US US06/560,698 patent/US4554280A/en not_active Expired - Fee Related
- 1983-12-12 US US06/560,699 patent/US4599347A/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0221041A3 (en) * | 1985-10-29 | 1987-10-28 | Aktiebolaget Hässle | Benzimidazole derivatives, process for their preparation and their pharmaceutical use |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8104941L (sv) | 1982-02-22 |
| NZ198047A (en) | 1985-05-31 |
| FR2488890B1 (cg-RX-API-DMAC7.html) | 1985-01-11 |
| ATA364381A (de) | 1984-05-15 |
| AU7408981A (en) | 1982-02-25 |
| IE51507B1 (en) | 1987-01-07 |
| BE890024A (fr) | 1982-02-22 |
| NL8103690A (nl) | 1982-03-16 |
| GB2082580B (en) | 1984-03-07 |
| IL63576A0 (en) | 1981-11-30 |
| US4435406A (en) | 1984-03-06 |
| PH17937A (en) | 1985-02-05 |
| LU83571A1 (de) | 1983-06-08 |
| DE3132613A1 (de) | 1982-06-24 |
| FR2488890A1 (fr) | 1982-02-26 |
| US4554280A (en) | 1985-11-19 |
| SE452765B (sv) | 1987-12-14 |
| ZA815633B (en) | 1982-08-25 |
| IE811912L (en) | 1982-02-21 |
| IL63576A (en) | 1985-10-31 |
| IT8123556A0 (it) | 1981-08-18 |
| CA1134829A (en) | 1982-11-02 |
| AT376665B (de) | 1984-12-27 |
| IT1138156B (it) | 1986-09-17 |
| AU541834B2 (en) | 1985-01-24 |
| DK300981A (da) | 1982-02-22 |
| US4599347A (en) | 1986-07-08 |
| GB2082580A (en) | 1982-03-10 |
| JPS5770886A (en) | 1982-05-01 |
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| PL | Patent ceased | ||
| PL | Patent ceased |