NO301327B1 - Tienocyklopentanonoksimetere, og farmasöytiske blandinger som inneholder dem - Google Patents
Tienocyklopentanonoksimetere, og farmasöytiske blandinger som inneholder dem Download PDFInfo
- Publication number
- NO301327B1 NO301327B1 NO923720A NO923720A NO301327B1 NO 301327 B1 NO301327 B1 NO 301327B1 NO 923720 A NO923720 A NO 923720A NO 923720 A NO923720 A NO 923720A NO 301327 B1 NO301327 B1 NO 301327B1
- Authority
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- Norway
- Prior art keywords
- formula
- alkyl
- acid
- thiophene
- ether
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 64
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 21
- 229930192474 thiophene Natural products 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- -1 pyridylethyl Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003544 oxime group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 98
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- 239000003921 oil Substances 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 19
- 150000002576 ketones Chemical class 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000155 melt Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 150000002923 oximes Chemical class 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- ZYQZCLMECLFQGS-UHFFFAOYSA-N n-[4-(2-chlorophenyl)-4,5-dihydrocyclopenta[b]thiophen-6-ylidene]hydroxylamine Chemical compound C1=2C=CSC=2C(=NO)CC1C1=CC=CC=C1Cl ZYQZCLMECLFQGS-UHFFFAOYSA-N 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 229940076279 serotonin Drugs 0.000 description 10
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 229920000137 polyphosphoric acid Polymers 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 102000035037 5-HT3 receptors Human genes 0.000 description 5
- 108091005477 5-HT3 receptors Proteins 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 5
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 5
- 235000005513 chalcones Nutrition 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001789 chalcones Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 4
- 229960003708 sumatriptan Drugs 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VJFIKJAVIOUTJF-UHFFFAOYSA-N C1C(=NO)C=2SC=CC=2C1(C)C1=CC=CC=C1 Chemical compound C1C(=NO)C=2SC=CC=2C1(C)C1=CC=CC=C1 VJFIKJAVIOUTJF-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 101100321769 Takifugu rubripes htr1d gene Proteins 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QBELEDRHMPMKHP-UHFFFAOYSA-N 1-bromo-2-chlorobenzene Chemical compound ClC1=CC=CC=C1Br QBELEDRHMPMKHP-UHFFFAOYSA-N 0.000 description 2
- OCWDBKQNNKCYCJ-UHFFFAOYSA-N 2-(2-bromoethoxy)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(OCCBr)C(=O)C2=C1 OCWDBKQNNKCYCJ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- OUQWQGRWZXKIFA-UHFFFAOYSA-N 3-(2-chlorophenyl)-3-thiophen-3-ylbutanoic acid Chemical compound C=1C=CC=C(Cl)C=1C(CC(O)=O)(C)C=1C=CSC=1 OUQWQGRWZXKIFA-UHFFFAOYSA-N 0.000 description 2
- NZNFXNFHUHGWMW-UHFFFAOYSA-N 4-(2-chlorophenyl)-4,5-dihydrocyclopenta[b]thiophen-6-one Chemical compound ClC1=CC=CC=C1C1C(C=CS2)=C2C(=O)C1 NZNFXNFHUHGWMW-UHFFFAOYSA-N 0.000 description 2
- DXJUVXMGPQMHSS-UHFFFAOYSA-N 4-(2-chlorophenyl)-4-methyl-5h-cyclopenta[b]thiophen-6-one Chemical compound C1C(=O)C=2SC=CC=2C1(C)C1=CC=CC=C1Cl DXJUVXMGPQMHSS-UHFFFAOYSA-N 0.000 description 2
- 101710138068 5-hydroxytryptamine receptor 1D Proteins 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 239000005695 Ammonium acetate Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
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- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- 230000001430 anti-depressive effect Effects 0.000 description 2
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- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 2
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- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
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- FYCFQDDCKKIWFG-UHFFFAOYSA-N ethyl 3-(2-chlorophenyl)-2-cyano-3-thiophen-3-ylbutanoate Chemical compound C=1C=CC=C(Cl)C=1C(C)(C(C#N)C(=O)OCC)C=1C=CSC=1 FYCFQDDCKKIWFG-UHFFFAOYSA-N 0.000 description 2
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
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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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C07D333/10—Thiophene
-
- 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
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (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)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9111822 | 1991-09-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO923720D0 NO923720D0 (no) | 1992-09-24 |
| NO923720L NO923720L (no) | 1993-03-26 |
| NO301327B1 true NO301327B1 (no) | 1997-10-13 |
Family
ID=9417295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO923720A NO301327B1 (no) | 1991-09-25 | 1992-09-24 | Tienocyklopentanonoksimetere, og farmasöytiske blandinger som inneholder dem |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5252749A (fi) |
| EP (1) | EP0534856B1 (fi) |
| JP (1) | JP3162822B2 (fi) |
| KR (1) | KR100199848B1 (fi) |
| AR (1) | AR248275A1 (fi) |
| AT (1) | ATE157360T1 (fi) |
| AU (1) | AU652072B2 (fi) |
| BR (1) | BR9203744A (fi) |
| CA (1) | CA2079016A1 (fi) |
| CZ (1) | CZ281936B6 (fi) |
| DE (1) | DE69221802T2 (fi) |
| DK (1) | DK0534856T3 (fi) |
| ES (1) | ES2108098T3 (fi) |
| FI (1) | FI106458B (fi) |
| GR (1) | GR3025335T3 (fi) |
| HU (1) | HU218204B (fi) |
| IL (1) | IL103106A (fi) |
| MX (1) | MX9205390A (fi) |
| NO (1) | NO301327B1 (fi) |
| NZ (1) | NZ244452A (fi) |
| PH (1) | PH30225A (fi) |
| RU (1) | RU2060253C1 (fi) |
| ZA (1) | ZA927318B (fi) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997044062A1 (en) * | 1996-05-23 | 1997-11-27 | Alcon Laboratories, Inc. | The use of 5-ht1b/1d agonists to treat ocular pain |
| EP1412347B1 (en) * | 2001-08-01 | 2006-01-11 | Basell Polyolefine GmbH | Process for the preparation of heterocyclic pentalene derivatives |
| US7432328B2 (en) * | 2005-06-14 | 2008-10-07 | Univation Technologies, Llc | Enhanced ESCR bimodal HDPE for blow molding applications |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE371190B (fi) * | 1972-03-24 | 1974-11-11 | Kabi Ab | |
| US3301874A (en) * | 1963-12-26 | 1967-01-31 | Sam Joseph | Thienocyclopentanone antibacterial agents |
| SE371193B (fi) * | 1972-03-24 | 1974-11-11 | Kabi Ab | |
| US4154740A (en) * | 1976-03-23 | 1979-05-15 | American Cyanamid Company | Substituted tetrahydrobenzothiophenes and method of preparation thereof |
| FR2471980A1 (fr) * | 1979-12-21 | 1981-06-26 | Sanofi Sa | Nouveaux derives de l'amino-1 propanol-2, leur procede de preparation et leur application therapeutique |
| FR2567125B1 (fr) * | 1984-07-09 | 1986-12-05 | Lipha | Acides dihydro-5,6-4h-cyclopenta (b) thiophenecarboxylique-6, procedes de preparation et medicaments les contenant |
| FR2639942B1 (fr) * | 1988-12-02 | 1991-03-29 | Sanofi Sa | Ethers oximes de propenone, procede pour leur preparation et compositions pharmaceutiques les contenant |
-
1992
- 1992-09-08 IL IL103106A patent/IL103106A/en not_active IP Right Cessation
- 1992-09-09 PH PH44908A patent/PH30225A/en unknown
- 1992-09-16 AU AU24548/92A patent/AU652072B2/en not_active Ceased
- 1992-09-22 AR AR92323223A patent/AR248275A1/es active
- 1992-09-23 NZ NZ244452A patent/NZ244452A/en unknown
- 1992-09-23 CZ CS922918A patent/CZ281936B6/cs not_active IP Right Cessation
- 1992-09-23 MX MX9205390A patent/MX9205390A/es not_active IP Right Cessation
- 1992-09-23 US US07/954,530 patent/US5252749A/en not_active Expired - Fee Related
- 1992-09-24 DE DE69221802T patent/DE69221802T2/de not_active Expired - Fee Related
- 1992-09-24 EP EP92402627A patent/EP0534856B1/fr not_active Expired - Lifetime
- 1992-09-24 RU SU925052821A patent/RU2060253C1/ru active
- 1992-09-24 NO NO923720A patent/NO301327B1/no not_active IP Right Cessation
- 1992-09-24 DK DK92402627.1T patent/DK0534856T3/da active
- 1992-09-24 AT AT92402627T patent/ATE157360T1/de not_active IP Right Cessation
- 1992-09-24 CA CA002079016A patent/CA2079016A1/en not_active Abandoned
- 1992-09-24 FI FI924281A patent/FI106458B/fi active
- 1992-09-24 ES ES92402627T patent/ES2108098T3/es not_active Expired - Lifetime
- 1992-09-24 HU HU9203050A patent/HU218204B/hu not_active IP Right Cessation
- 1992-09-24 JP JP25506992A patent/JP3162822B2/ja not_active Expired - Fee Related
- 1992-09-24 ZA ZA927318A patent/ZA927318B/xx unknown
- 1992-09-25 BR BR9203744A patent/BR9203744A/pt not_active Application Discontinuation
- 1992-09-25 KR KR1019920017585A patent/KR100199848B1/ko not_active IP Right Cessation
-
1997
- 1997-11-11 GR GR970402977T patent/GR3025335T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2108098T3 (es) | 1997-12-16 |
| ATE157360T1 (de) | 1997-09-15 |
| FI924281A (fi) | 1993-03-26 |
| IL103106A (en) | 1998-06-15 |
| KR930006001A (ko) | 1993-04-20 |
| BR9203744A (pt) | 1994-03-29 |
| AU652072B2 (en) | 1994-08-11 |
| CZ281936B6 (cs) | 1997-04-16 |
| HU218204B (hu) | 2000-06-28 |
| GR3025335T3 (en) | 1998-02-27 |
| AU2454892A (en) | 1993-04-01 |
| KR100199848B1 (ko) | 1999-06-15 |
| FI106458B (fi) | 2001-02-15 |
| NO923720L (no) | 1993-03-26 |
| PH30225A (en) | 1997-02-05 |
| FI924281A0 (fi) | 1992-09-24 |
| NZ244452A (en) | 1994-08-26 |
| NO923720D0 (no) | 1992-09-24 |
| JPH05213932A (ja) | 1993-08-24 |
| RU2060253C1 (ru) | 1996-05-20 |
| US5252749A (en) | 1993-10-12 |
| DE69221802T2 (de) | 1998-04-02 |
| DE69221802D1 (de) | 1997-10-02 |
| CA2079016A1 (en) | 1993-03-26 |
| IL103106A0 (en) | 1993-02-21 |
| EP0534856B1 (fr) | 1997-08-27 |
| HUT62876A (en) | 1993-06-28 |
| HU9203050D0 (en) | 1992-12-28 |
| MX9205390A (es) | 1993-05-01 |
| CZ291892A3 (en) | 1993-04-14 |
| DK0534856T3 (da) | 1998-04-20 |
| AR248275A1 (es) | 1995-07-12 |
| EP0534856A1 (fr) | 1993-03-31 |
| JP3162822B2 (ja) | 2001-05-08 |
| ZA927318B (en) | 1994-03-24 |
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Legal Events
| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN MARCH 2002 |