NZ198047A - Tricyclic imidazole derivatives carrying a pyrid-2-ylmethylthio substituent - Google Patents
Tricyclic imidazole derivatives carrying a pyrid-2-ylmethylthio substituentInfo
- Publication number
- NZ198047A NZ198047A NZ198047A NZ19804781A NZ198047A NZ 198047 A NZ198047 A NZ 198047A NZ 198047 A NZ198047 A NZ 198047A NZ 19804781 A NZ19804781 A NZ 19804781A NZ 198047 A NZ198047 A NZ 198047A
- Authority
- NZ
- New Zealand
- Prior art keywords
- methyl
- thio
- pyridyl
- signifies
- benzimidazole
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title claims description 13
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 30
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- -1 5-methyl-2-pyridyl Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 208000025865 Ulcer Diseases 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 231100000397 ulcer Toxicity 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 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 claims description 5
- 229920002261 Corn starch Polymers 0.000 claims description 5
- 235000019759 Maize starch Nutrition 0.000 claims description 5
- 230000000767 anti-ulcer Effects 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 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 4
- 239000012458 free base Substances 0.000 claims description 4
- 230000027119 gastric acid secretion Effects 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 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 claims description 3
- 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 description 3
- MVJBGBUFNZREPM-UHFFFAOYSA-N 2-methyl-6-(pyridin-2-ylmethylsulfanyl)-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound N1C=2C=C3OC(C)OC3=CC=2N=C1SCC1=CC=CC=N1 MVJBGBUFNZREPM-UHFFFAOYSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000008101 lactose Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- VPKORXOFBXCKFT-UHFFFAOYSA-N 2,2-dimethyl-6-(pyridin-2-ylmethylsulfanyl)-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound N1C=2C=C3OC(C)(C)OC3=CC=2N=C1SCC1=CC=CC=N1 VPKORXOFBXCKFT-UHFFFAOYSA-N 0.000 claims description 2
- RHSOHYZDJPLTMG-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-1,6,7,8-tetrahydro-[1,4]dioxepino[2,3-f]benzimidazole Chemical compound N=1C2=CC=3OCCCOC=3C=C2NC=1SCC1=CC=CC=N1 RHSOHYZDJPLTMG-UHFFFAOYSA-N 0.000 claims description 2
- NAXGITXFEJXOJH-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-1,8-dihydro-[1,3]dioxino[4,5-f]benzimidazole Chemical compound N=1C2=CC=3OCOCC=3C=C2NC=1SCC1=CC=CC=N1 NAXGITXFEJXOJH-UHFFFAOYSA-N 0.000 claims description 2
- KIFJUFOPFYTLMH-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-3,5,6,7-tetrahydrocyclopenta[f]benzimidazole Chemical compound N=1C2=CC=3CCCC=3C=C2NC=1S(=O)CC1=CC=CC=N1 KIFJUFOPFYTLMH-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- ZPYHTFXRIXQUKW-UHFFFAOYSA-N 4-methyl-2-(1-pyridin-2-ylethylsulfanyl)-1h-benzo[f]benzimidazole Chemical compound N=1C2=C(C)C3=CC=CC=C3C=C2NC=1SC(C)C1=CC=CC=N1 ZPYHTFXRIXQUKW-UHFFFAOYSA-N 0.000 claims description 2
- YSAYNIAFDHHTBU-UHFFFAOYSA-N 4-methyl-2-(pyridin-2-ylmethylsulfanyl)-1h-benzo[f]benzimidazole Chemical compound N1C2=CC3=CC=CC=C3C(C)=C2N=C1SCC1=CC=CC=N1 YSAYNIAFDHHTBU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 4
- 235000019359 magnesium stearate Nutrition 0.000 claims 2
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- BPTYXPRKVDLUKZ-UHFFFAOYSA-N 2-[(5-methylpyridin-2-yl)methylsulfanyl]-6,7-dihydro-1h-[1,4]dioxino[2,3-f]benzimidazole Chemical compound N1=CC(C)=CC=C1CSC(NC1=C2)=NC1=CC1=C2OCCO1 BPTYXPRKVDLUKZ-UHFFFAOYSA-N 0.000 claims 1
- ILARJSUUFDQPSN-UHFFFAOYSA-N 5,5,7,7-tetramethyl-2-[(5-methylpyridin-2-yl)methylsulfanyl]-3h-cyclopenta[f]benzimidazol-6-one Chemical compound N1=CC(C)=CC=C1CSC1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 ILARJSUUFDQPSN-UHFFFAOYSA-N 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- 238000002844 melting Methods 0.000 description 92
- 230000008018 melting Effects 0.000 description 92
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 76
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 74
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 239000000243 solution Substances 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 229960000583 acetic acid Drugs 0.000 description 36
- 238000010992 reflux Methods 0.000 description 35
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- 239000012362 glacial acetic acid Substances 0.000 description 32
- 229940093499 ethyl acetate Drugs 0.000 description 30
- 235000019439 ethyl acetate Nutrition 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 239000012043 crude product Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- 230000007935 neutral effect Effects 0.000 description 17
- 239000013078 crystal Substances 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 239000007868 Raney catalyst Substances 0.000 description 10
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 10
- 229910000564 Raney nickel Inorganic materials 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000001110 calcium chloride Substances 0.000 description 7
- 229910001628 calcium chloride Inorganic materials 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- OXXWQLSFICBOMG-UHFFFAOYSA-N 2-(chloromethyl)-5-methylpyridin-1-ium;chloride Chemical compound Cl.CC1=CC=C(CCl)N=C1 OXXWQLSFICBOMG-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- IAOGWYABFHUNKI-UHFFFAOYSA-N 1h-imidazole;dihydrochloride Chemical compound Cl.[Cl-].C1=C[NH+]=CN1 IAOGWYABFHUNKI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 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
- 239000008298 dragée Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 210000004051 gastric juice Anatomy 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
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- TZDYCSBHGZQZFW-UHFFFAOYSA-N 1,1,3,3-tetramethyl-5,6-dinitroinden-2-one Chemical compound [O-][N+](=O)C1=C([N+]([O-])=O)C=C2C(C)(C)C(=O)C(C)(C)C2=C1 TZDYCSBHGZQZFW-UHFFFAOYSA-N 0.000 description 2
- KBFUPRLHCWUTGK-UHFFFAOYSA-N 1,1,3,3-tetramethylinden-2-one Chemical compound C1=CC=C2C(C)(C)C(=O)C(C)(C)C2=C1 KBFUPRLHCWUTGK-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
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-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
- DGKPGLRTGFHYDF-UHFFFAOYSA-N 2,3-dihydro-1h-indole-5,6-diamine;dihydrochloride Chemical compound Cl.Cl.C1=C(N)C(N)=CC2=C1NCC2 DGKPGLRTGFHYDF-UHFFFAOYSA-N 0.000 description 2
- HONJWUZXQQEEHP-UHFFFAOYSA-N 2,3-dihydroxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(O)C(O)=CC2=C1 HONJWUZXQQEEHP-UHFFFAOYSA-N 0.000 description 2
- QAILLLXJRCXXGS-UHFFFAOYSA-N 3,8-dihydro-1h-[1,3]dioxino[4,5-f]benzimidazole-2-thione Chemical compound O1COCC2=C1C=C1N=C(S)NC1=C2 QAILLLXJRCXXGS-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- UGYXPZQILZRKJJ-UHFFFAOYSA-N 4-methylhistamine Chemical compound CC=1NC=NC=1CCN UGYXPZQILZRKJJ-UHFFFAOYSA-N 0.000 description 2
- ZOJQYQPBBUPJAK-UHFFFAOYSA-N 4h-1,3-benzodioxine-6,7-diamine Chemical compound C1OCOC2=C1C=C(N)C(N)=C2 ZOJQYQPBBUPJAK-UHFFFAOYSA-N 0.000 description 2
- KOAOPAQODUPDDV-UHFFFAOYSA-N 6-[(5-methylpyridin-2-yl)methylsulfinyl]-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound N1=CC(C)=CC=C1CS(=O)C(NC1=C2)=NC1=CC1=C2OCO1 KOAOPAQODUPDDV-UHFFFAOYSA-N 0.000 description 2
- HLUYEDQKIFUIIP-UHFFFAOYSA-N 6-nitro-2,3-dihydro-1h-inden-5-amine Chemical compound C1=C([N+]([O-])=O)C(N)=CC2=C1CCC2 HLUYEDQKIFUIIP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WOYOJAPRKMBKEU-UHFFFAOYSA-N N1-(2,3-Dihydro-1H-inden-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2CCCC2=C1 WOYOJAPRKMBKEU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 2
- 229960004484 carbachol Drugs 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
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- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 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
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
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Classifications
-
- 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)
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 |
|---|---|
| NZ198047A true NZ198047A (en) | 1985-05-31 |
Family
ID=4307711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ198047A NZ198047A (en) | 1980-08-21 | 1981-08-14 | Tricyclic imidazole derivatives carrying a pyrid-2-ylmethylthio substituent |
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) |
Families Citing this family (36)
| 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 |
| SE8505112D0 (sv) * | 1985-10-29 | 1985-10-29 | Haessle Ab | Novel pharmacological compounds |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| SE8104941L (sv) | 1982-02-22 |
| 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 |
| CH644116A5 (de) | 1984-07-13 |
| 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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