CH634840A5 - 2-oxo-2,3-dihydro-benzo(b)thiophen-verbindung und daraus hergestellte pharmazeutische praeparate. - Google Patents
2-oxo-2,3-dihydro-benzo(b)thiophen-verbindung und daraus hergestellte pharmazeutische praeparate. Download PDFInfo
- Publication number
- CH634840A5 CH634840A5 CH710378A CH710378A CH634840A5 CH 634840 A5 CH634840 A5 CH 634840A5 CH 710378 A CH710378 A CH 710378A CH 710378 A CH710378 A CH 710378A CH 634840 A5 CH634840 A5 CH 634840A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- formula
- salt
- benzo
- salts
- Prior art date
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- -1 2-OXO-2,3-DIHYDRO-BENZO (B) THIOPHENE COMPOUND Chemical class 0.000 title claims description 26
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- ZEXIVBYDDCIOKA-UHFFFAOYSA-N 1-benzothiophen-2-ol Chemical group C1=CC=C2SC(O)=CC2=C1 ZEXIVBYDDCIOKA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical compound C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 229920002472 Starch Polymers 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- JMHWGALERUDWIC-UHFFFAOYSA-N 2-oxo-n-thiophen-2-yl-3h-1-benzothiophene-3-carboxamide Chemical compound O=C1SC2=CC=CC=C2C1C(=O)NC1=CC=CS1 JMHWGALERUDWIC-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
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- 229910052801 chlorine Inorganic materials 0.000 description 5
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- 229920000159 gelatin Polymers 0.000 description 5
- 229940014259 gelatin Drugs 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
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- 235000012222 talc Nutrition 0.000 description 5
- 229940100445 wheat starch Drugs 0.000 description 5
- 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 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000007530 organic bases Chemical group 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 2
- ARTAFUJPRUWRJK-UHFFFAOYSA-N 3h-1-benzothiophen-2-one Chemical compound C1=CC=C2SC(=O)CC2=C1 ARTAFUJPRUWRJK-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 239000000205 acacia gum Substances 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
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- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000005910 alkyl carbonate group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- WGCLTXICCZSHJG-UHFFFAOYSA-N ethyl 2-oxo-3h-1-benzothiophene-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)C(=O)SC2=C1 WGCLTXICCZSHJG-UHFFFAOYSA-N 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 230000004054 inflammatory process Effects 0.000 description 2
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- 150000007529 inorganic bases Chemical class 0.000 description 2
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- 239000000314 lubricant Substances 0.000 description 2
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 2
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- 230000002537 thrombolytic effect Effects 0.000 description 2
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 230000003424 uricosuric effect Effects 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- QUCMZSJETXEAMC-UHFFFAOYSA-N 2-(2-sulfanylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1S QUCMZSJETXEAMC-UHFFFAOYSA-N 0.000 description 1
- VSQIVTQJBJNQBS-UHFFFAOYSA-N 2-acetamido-1-benzothiophene-3-carboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(NC(=O)C)SC2=C1 VSQIVTQJBJNQBS-UHFFFAOYSA-N 0.000 description 1
- NWCAGVPQJOBBQN-UHFFFAOYSA-N 2-acetamido-n-thiophen-2-yl-1-benzothiophene-3-carboxamide Chemical compound CC(=O)NC=1SC2=CC=CC=C2C=1C(=O)NC1=CC=CS1 NWCAGVPQJOBBQN-UHFFFAOYSA-N 0.000 description 1
- WYOLDVOOOYZSJM-UHFFFAOYSA-N 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound C1CCCC2=C1SC(N)=C2C(O)=O WYOLDVOOOYZSJM-UHFFFAOYSA-N 0.000 description 1
- QVLWPBIUVXZGRK-UHFFFAOYSA-N 2-isocyanatothiophene Chemical compound O=C=NC1=CC=CS1 QVLWPBIUVXZGRK-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- NMCTUHZAVTWCQR-UHFFFAOYSA-N phenyl n-thiophen-2-ylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC=CS1 NMCTUHZAVTWCQR-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 235000009566 rice Nutrition 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
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- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- DAUYIKBTMNZABP-UHFFFAOYSA-N thiophene-3-carboxamide Chemical compound NC(=O)C=1C=CSC=1 DAUYIKBTMNZABP-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (36)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT66412A PT66412B (en) | 1976-04-09 | 1977-04-07 | Process for the manufacture of new oxothia compounds |
| CH710378A CH634840A5 (de) | 1978-06-29 | 1978-06-29 | 2-oxo-2,3-dihydro-benzo(b)thiophen-verbindung und daraus hergestellte pharmazeutische praeparate. |
| PL21637679A PL216376A3 (enrdf_load_stackoverflow) | 1978-06-29 | 1979-06-16 | |
| PL21637779A PL216377A3 (enrdf_load_stackoverflow) | 1978-06-29 | 1979-06-16 | |
| PL21637879A PL216378A3 (enrdf_load_stackoverflow) | 1978-06-29 | 1979-06-16 | |
| DE19792924496 DE2924496A1 (de) | 1978-06-29 | 1979-06-18 | Neue oxathiaverbindungen, verfahren zu ihrer herstellung, diese enthaltende pharmazeutische praeparate und ihre verwendung als arzneimittelwirkstoff |
| CY1288A CY1288A (en) | 1978-06-29 | 1979-06-22 | Oxothia compounds processes for their preparation pharmaceutical preparations containing these compounds and their use as a medicinal active compound |
| GB7921851A GB2024220B (en) | 1978-06-29 | 1979-06-22 | Oxothia compounds processes for their preparation pharmaceutical preparations containing these compounds and their uas a medicinal active compound |
| FI792011A FI792011A7 (fi) | 1978-06-29 | 1979-06-25 | Menetelmä uusien oksatiayhdisteiden valmistamiseksi. |
| ES481936A ES481936A2 (es) | 1978-06-29 | 1979-06-26 | Mejoras introducidas en la patente principal: procedimiento para la obtencion de compuestos oxotio. |
| CA330,705A CA1125761A (en) | 1978-06-29 | 1979-06-27 | Process for the manufacture of novel oxothia compounds |
| IT49562/79A IT1164125B (it) | 1978-06-29 | 1979-06-27 | Ossotiacomposti e procedimento per la loro produzione ed impiego in preparati farmaceutici |
| DD79213935A DD144544A6 (de) | 1978-06-29 | 1979-06-27 | Verfahren zur herstellung neuer oxathiaverbindungen |
| SE7905631A SE445737B (sv) | 1978-06-29 | 1979-06-27 | Forfarande for framstellning av n-(2-tienyl)-2-oxo-2,3-dihydro-benso/b/tiofen-3-karboxamid |
| GR59451A GR82335B (enrdf_load_stackoverflow) | 1978-06-29 | 1979-06-27 | |
| FR7916603A FR2429792A2 (fr) | 1978-06-29 | 1979-06-27 | Nouveaux composes oxothia, leur preparation et leur application en tant que substances actives medicamenteuses |
| NZ190868A NZ190868A (en) | 1977-03-31 | 1979-06-28 | N-heterocyclyl-2-oxo-2 3-dihydro-benzo(b) thiophen-3-carboxamides pharmaceutical compositions |
| AT0451679A AT373597B (de) | 1978-06-29 | 1979-06-28 | Verfahren zur herstellung einer neuen oxathiaverbindung und ihrer salze |
| AT0451779A AT373598B (de) | 1978-06-29 | 1979-06-28 | Verfahren zur herstellung einer neuen oxathiaverbindung und ihrer salze |
| AT0451579A AT374199B (de) | 1978-06-29 | 1979-06-28 | Verfahren zur herstellung einer neuen oxathiaverbindung und ihrer salze |
| NO792178A NO151323C (no) | 1978-06-29 | 1979-06-28 | Analogifremgangsmaate til fremstilling av et terapeutisk aktivt n-(2-tienyl)-2-okso-2,3-dihydro-benzo(b)tiofen-3-karboksamid |
| DK274279A DK152047C (da) | 1978-06-29 | 1979-06-28 | Analogifremgangsmaade til fremstilling af n-(2-thienyl)-2-oxo-2,3-dihydro-benzo(b)thiophen-3-carboxamid eller salte deraf med baser |
| HU79CI1943A HU181663B (en) | 1978-06-29 | 1979-06-28 | Process for preparing n-/2-thienyl/-2-oxo-2,3-dihydro-benzo/b/-thiophene-3-carboxamide and salts thereof |
| BE0/196017A BE877339R (fr) | 1978-06-29 | 1979-06-28 | Nouveaux composes oxathia, leur preparation et leur application en tant que medicaments |
| IL5768479A IL57684A (en) | 1977-04-08 | 1979-06-28 | 2,3-dihydro-2-oxo-benzo(b)thiophen-2-carboxamide,its manufacture and pharmaceutical compositions containing it |
| ZA793230A ZA793230B (en) | 1978-06-29 | 1979-06-28 | Novel oxothia compounds,processes for their preparation,pharmaceutical preparations containing these compounds and their use as a medicinal active compound |
| AU48509/79A AU531535B2 (en) | 1978-06-29 | 1979-06-28 | Oxothia compounds |
| JP8154679A JPS559075A (en) | 1978-06-29 | 1979-06-29 | Novel oxothia compound*its manufacture*drug composition containing it and use as medical material |
| NL7905084A NL7905084A (nl) | 1978-06-29 | 1979-06-29 | Oxothiaverbindingen, werkwijzen voor de bereiding daar- van, farmaceutische preparaten die de verbindingen bevatten en de toepassing daarvan in farmaceutische preparaten als werkzame verbinding. |
| AR277124A AR231540A1 (es) | 1978-06-29 | 1979-06-29 | Procedimiento para la elaboracion de derivados de 2-oxo-3-n-2,3-dihidro b-tiofeno y sus sales |
| IE1205/79A IE48767B1 (en) | 1978-06-29 | 1979-08-08 | Novel oxothia compounds,processes for their preparation,pharmaceutical preparations containing these compounds and such compounds for therapeutic use |
| US06/204,747 US4396621A (en) | 1976-04-09 | 1980-11-07 | Certain 2-oxo-2,3-dihydro-3-benzothiophene-carboxamides and their pharmaceutical compositions |
| AT171483A AT392787B (de) | 1978-06-29 | 1983-05-10 | Verfahren zur herstellung des neuen n-(2-thienyl)-2-oxo-2,3-dihydro-benzo(b)thiophen-3-carboxamids |
| SG159/85A SG15985G (en) | 1978-06-29 | 1985-03-01 | Novel oxothia compounds,processes for their preparation,pharmaceutical preparations containing these compounds and such compounds for therapeutic use |
| HK425/85A HK42585A (en) | 1978-06-29 | 1985-05-30 | Novel oxothia compounds,processes for their preparation,pharmaceutical preparations containing these compounds and such compounds for therapeutic use |
| MY212/85A MY8500212A (en) | 1978-06-29 | 1985-12-30 | Novel oxothia compounds processes for their preparation,pharmaceutical preparations containing these compounds and their use as a medicinal active compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH710378A CH634840A5 (de) | 1978-06-29 | 1978-06-29 | 2-oxo-2,3-dihydro-benzo(b)thiophen-verbindung und daraus hergestellte pharmazeutische praeparate. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH634840A5 true CH634840A5 (de) | 1983-02-28 |
Family
ID=4320005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH710378A CH634840A5 (de) | 1976-04-09 | 1978-06-29 | 2-oxo-2,3-dihydro-benzo(b)thiophen-verbindung und daraus hergestellte pharmazeutische praeparate. |
Country Status (26)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4800211A (en) * | 1986-08-18 | 1989-01-24 | Merck & Co., Inc. | 5-methylthio-3-hydroxybenzo [b]thiophene-2-carboxamide derivatives as cyclooxygenase and lipoxygenase inhibitors |
| JP2004501910A (ja) * | 2000-06-28 | 2004-01-22 | イーライ・リリー・アンド・カンパニー | 新規なｓＰＬＡ２インヒビター |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2713584C2 (de) * | 1976-04-09 | 1986-09-04 | Ciba-Geigy Ag, Basel | Benzo[b]thiophencarboxamide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
| JPS6218556A (ja) * | 1985-07-18 | 1987-01-27 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
-
1978
- 1978-06-29 CH CH710378A patent/CH634840A5/de not_active IP Right Cessation
-
1979
- 1979-06-16 PL PL21637879A patent/PL216378A3/xx unknown
- 1979-06-16 PL PL21637679A patent/PL216376A3/xx unknown
- 1979-06-16 PL PL21637779A patent/PL216377A3/xx unknown
- 1979-06-18 DE DE19792924496 patent/DE2924496A1/de active Granted
- 1979-06-22 CY CY1288A patent/CY1288A/en unknown
- 1979-06-22 GB GB7921851A patent/GB2024220B/en not_active Expired
- 1979-06-25 FI FI792011A patent/FI792011A7/fi not_active Application Discontinuation
- 1979-06-26 ES ES481936A patent/ES481936A2/es not_active Expired
- 1979-06-27 SE SE7905631A patent/SE445737B/sv not_active IP Right Cessation
- 1979-06-27 DD DD79213935A patent/DD144544A6/de unknown
- 1979-06-27 GR GR59451A patent/GR82335B/el unknown
- 1979-06-27 FR FR7916603A patent/FR2429792A2/fr active Granted
- 1979-06-27 CA CA330,705A patent/CA1125761A/en not_active Expired
- 1979-06-28 BE BE0/196017A patent/BE877339R/xx not_active IP Right Cessation
- 1979-06-28 DK DK274279A patent/DK152047C/da not_active IP Right Cessation
- 1979-06-28 AT AT0451679A patent/AT373597B/de not_active IP Right Cessation
- 1979-06-28 AT AT0451579A patent/AT374199B/de not_active IP Right Cessation
- 1979-06-28 HU HU79CI1943A patent/HU181663B/hu unknown
- 1979-06-28 NO NO792178A patent/NO151323C/no unknown
- 1979-06-28 AT AT0451779A patent/AT373598B/de not_active IP Right Cessation
- 1979-06-28 AU AU48509/79A patent/AU531535B2/en not_active Expired
- 1979-06-28 ZA ZA793230A patent/ZA793230B/xx unknown
- 1979-06-29 NL NL7905084A patent/NL7905084A/nl not_active Application Discontinuation
- 1979-06-29 AR AR277124A patent/AR231540A1/es active
- 1979-06-29 JP JP8154679A patent/JPS559075A/ja active Granted
- 1979-08-08 IE IE1205/79A patent/IE48767B1/en unknown
-
1985
- 1985-03-01 SG SG159/85A patent/SG15985G/en unknown
- 1985-05-30 HK HK425/85A patent/HK42585A/xx unknown
- 1985-12-30 MY MY212/85A patent/MY8500212A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |