NO310289B1 - Heterocykliske azolonderivater med anti-Helicobacteraktivitet - Google Patents
Heterocykliske azolonderivater med anti-Helicobacteraktivitet Download PDFInfo
- Publication number
- NO310289B1 NO310289B1 NO19970086A NO970086A NO310289B1 NO 310289 B1 NO310289 B1 NO 310289B1 NO 19970086 A NO19970086 A NO 19970086A NO 970086 A NO970086 A NO 970086A NO 310289 B1 NO310289 B1 NO 310289B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- pyridinyl
- alkyl
- optionally substituted
- piperazinyl
- Prior art date
Links
- -1 Heterocyclic azolone derivatives Chemical class 0.000 title description 21
- 230000000694 effects Effects 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims description 85
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- SQEITUTYKRJYPN-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-oxobutan-2-yl]-4-[6-(4-pyridin-2-ylpiperazin-1-yl)pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2N=CC=CC=2)C(=O)N1C(CC)C(=O)C1=CC=C(Cl)C=C1 SQEITUTYKRJYPN-UHFFFAOYSA-N 0.000 claims description 3
- RFOLACYUXCSGKO-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-oxobutan-2-yl]-4-[6-(4-pyrimidin-2-ylpiperazin-1-yl)pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2N=CC=CN=2)C(=O)N1C(CC)C(=O)C1=CC=C(Cl)C=C1 RFOLACYUXCSGKO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 150000001622 bismuth compounds Chemical class 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- FTAHUNXAEHHYHD-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-hydroxybutan-2-yl]-4-[6-(4-pyridin-2-ylpiperazin-1-yl)pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2N=CC=CC=2)C(=O)N1C(CC)C(O)C1=CC=C(Cl)C=C1 FTAHUNXAEHHYHD-UHFFFAOYSA-N 0.000 claims description 2
- DERFDIXNNUPCIO-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-1-hydroxybutan-2-yl]-4-[6-[4-(1,3-thiazol-2-yl)piperazin-1-yl]pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=NC(=CC=2)N2CCN(CC2)C=2SC=CN=2)C(=O)N1C(CC)C(O)C1=CC=C(Cl)C=C1 DERFDIXNNUPCIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229940126409 proton pump inhibitor Drugs 0.000 claims description 2
- 239000000612 proton pump inhibitor Substances 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 62
- 239000000543 intermediate Substances 0.000 description 38
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
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- 239000002244 precipitate Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 15
- 229920000858 Cyclodextrin Polymers 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
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- 241000589989 Helicobacter Species 0.000 description 12
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- 239000003826 tablet Substances 0.000 description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241000590002 Helicobacter pylori Species 0.000 description 5
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- 230000037396 body weight Effects 0.000 description 5
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- 229940037467 helicobacter pylori Drugs 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- 239000007983 Tris buffer Substances 0.000 description 3
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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
- 239000004310 lactic acid Substances 0.000 description 1
- SIXIIKVOZAGHPV-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=C[CH]C2=N1 SIXIIKVOZAGHPV-UHFFFAOYSA-N 0.000 description 1
- 229960003174 lansoprazole Drugs 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229940098462 oral drops Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 229960005019 pantoprazole Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- JHPLCUCUCZYSFF-UHFFFAOYSA-N phenyl n-[4-[4-(5-methoxypyrimidin-2-yl)piperazin-1-yl]phenyl]carbamate Chemical compound N1=CC(OC)=CN=C1N1CCN(C=2C=CC(NC(=O)OC=3C=CC=CC=3)=CC=2)CC1 JHPLCUCUCZYSFF-UHFFFAOYSA-N 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP94202018 | 1994-07-12 | ||
| PCT/EP1995/002616 WO1996001821A1 (fr) | 1994-07-12 | 1995-07-05 | Derives heterocycliques anti-helicobacter d'azolones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO970086D0 NO970086D0 (no) | 1997-01-09 |
| NO970086L NO970086L (no) | 1997-03-10 |
| NO310289B1 true NO310289B1 (no) | 2001-06-18 |
Family
ID=8217031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19970086A NO310289B1 (no) | 1994-07-12 | 1997-01-09 | Heterocykliske azolonderivater med anti-Helicobacteraktivitet |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5607932A (fr) |
| EP (1) | EP0770073A1 (fr) |
| JP (1) | JPH10502383A (fr) |
| CN (1) | CN1067999C (fr) |
| AU (1) | AU684986B2 (fr) |
| BR (1) | BR9508380A (fr) |
| CA (1) | CA2194563A1 (fr) |
| CZ (1) | CZ2697A3 (fr) |
| FI (1) | FI970110A0 (fr) |
| HU (1) | HUT76641A (fr) |
| IL (1) | IL114534A (fr) |
| MX (1) | MX9700338A (fr) |
| MY (1) | MY131785A (fr) |
| NO (1) | NO310289B1 (fr) |
| NZ (1) | NZ290116A (fr) |
| PL (1) | PL318142A1 (fr) |
| RU (1) | RU2152940C1 (fr) |
| SK (1) | SK2197A3 (fr) |
| WO (1) | WO1996001821A1 (fr) |
| ZA (1) | ZA955753B (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100411190B1 (ko) * | 1995-12-26 | 2004-03-26 | 에스케이케미칼주식회사 | 에틸렌글리콜의회수방법 |
| EP0923577A2 (fr) * | 1996-06-25 | 1999-06-23 | Takeda Chemical Industries, Ltd. | Derives de l'oxazolone et leur utilisation en tant qu'agent anti-helicobacter pylori |
| US6169102B1 (en) | 1996-06-25 | 2001-01-02 | Takeda Chemical Industries, Ltd. | Oxazolone derivatives and their use as anti-Helicobacter pylori agent |
| TW200626139A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| BRPI0515488A (pt) | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados de heterocìclicos e seu uso como agentes terapêuticos |
| EP1814551A2 (fr) | 2004-09-20 | 2007-08-08 | Xenon Pharmaceuticals Inc. | Derives de pyridazine destines a l'inhibition du desaturase-coa-stearoyl de l'humain |
| TW200626572A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| MX2007003332A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de estearoil-coa-desaturasa. |
| BRPI0515483A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos para o tratamento de doenças mediadas por enzimas estearoil-coa desaturase |
| WO2006034440A2 (fr) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Derives heterocycliques et leur utilisation en tant qu'agents therapeutiques |
| EP2540296A1 (fr) | 2005-06-03 | 2013-01-02 | Xenon Pharmaceuticals Inc. | Dérivés d'arminothiazole utilisés comme inhibiteurs de la stéaroyl-coa désaturase humaine |
| US9187426B2 (en) | 2008-06-27 | 2015-11-17 | Novartis Ag | Organic compounds |
| WO2013175215A1 (fr) | 2012-05-22 | 2013-11-28 | Autifony Therapeutics Limited | Triazoles en tant qu'inhibiteurs de kv3 |
| ES2781309T3 (es) * | 2016-05-27 | 2020-09-01 | Bristol Myers Squibb Co | Triazolonas y tetrazolonas como inhibidores de ROCK |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4791111A (en) * | 1985-12-23 | 1988-12-13 | Janssen Pharmaceutica, N.V. | [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles having anti-microbial properties |
| CA1331757C (fr) * | 1988-02-29 | 1994-08-30 | Janssen Pharmaceutica Naamloze Vennootschap | 5-lipoxygenase inhibant les 4-(4-phenyl-1-piperazinyl)phenols |
| CA2076257A1 (fr) * | 1991-09-13 | 1993-03-14 | Jan Heeres | Derives de 4-{4-¬4-(4-hydroxyphenyl)-1-piperazinyl|phenyl}-5-methyl-3h-1,2,4-triazol-3-one |
| TW279864B (fr) * | 1993-02-19 | 1996-07-01 | Janssen Pharmaceutica Nv |
-
1995
- 1995-05-23 US US08/447,503 patent/US5607932A/en not_active Expired - Fee Related
- 1995-07-05 CZ CZ9726A patent/CZ2697A3/cs unknown
- 1995-07-05 AU AU30755/95A patent/AU684986B2/en not_active Ceased
- 1995-07-05 CN CN95194021A patent/CN1067999C/zh not_active Expired - Fee Related
- 1995-07-05 JP JP8504109A patent/JPH10502383A/ja active Pending
- 1995-07-05 RU RU97102151/04A patent/RU2152940C1/ru active
- 1995-07-05 HU HU9700077A patent/HUT76641A/hu unknown
- 1995-07-05 BR BR9508380A patent/BR9508380A/pt unknown
- 1995-07-05 NZ NZ290116A patent/NZ290116A/en unknown
- 1995-07-05 PL PL95318142A patent/PL318142A1/xx unknown
- 1995-07-05 EP EP95926390A patent/EP0770073A1/fr not_active Withdrawn
- 1995-07-05 SK SK21-97A patent/SK2197A3/sk unknown
- 1995-07-05 WO PCT/EP1995/002616 patent/WO1996001821A1/fr not_active Application Discontinuation
- 1995-07-05 CA CA002194563A patent/CA2194563A1/fr not_active Abandoned
- 1995-07-05 MX MX9700338A patent/MX9700338A/es unknown
- 1995-07-11 ZA ZA955753A patent/ZA955753B/xx unknown
- 1995-07-11 IL IL11453495A patent/IL114534A/xx active IP Right Grant
- 1995-07-12 MY MYPI95001962A patent/MY131785A/en unknown
-
1997
- 1997-01-09 NO NO19970086A patent/NO310289B1/no unknown
- 1997-01-10 FI FI970110A patent/FI970110A0/fi unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL318142A1 (en) | 1997-05-12 |
| IL114534A (en) | 1999-08-17 |
| US5607932A (en) | 1997-03-04 |
| FI970110A (fi) | 1997-01-10 |
| BR9508380A (pt) | 1997-12-23 |
| CN1152310A (zh) | 1997-06-18 |
| EP0770073A1 (fr) | 1997-05-02 |
| HUT76641A (en) | 1997-10-28 |
| FI970110A0 (fi) | 1997-01-10 |
| CN1067999C (zh) | 2001-07-04 |
| MY131785A (en) | 2007-08-30 |
| CA2194563A1 (fr) | 1996-01-25 |
| RU2152940C1 (ru) | 2000-07-20 |
| MX9700338A (es) | 1997-05-31 |
| NO970086L (no) | 1997-03-10 |
| JPH10502383A (ja) | 1998-03-03 |
| AU3075595A (en) | 1996-02-09 |
| NO970086D0 (no) | 1997-01-09 |
| SK2197A3 (en) | 1997-11-05 |
| NZ290116A (en) | 1997-11-24 |
| WO1996001821A1 (fr) | 1996-01-25 |
| HU9700077D0 (en) | 1997-02-28 |
| AU684986B2 (en) | 1998-01-08 |
| IL114534A0 (en) | 1995-11-27 |
| CZ2697A3 (en) | 1997-09-17 |
| ZA955753B (en) | 1997-01-11 |
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