NO312512B1 - Oksadiazoler, anvendelse derav, fremgangsmåte for deres fremstilling, samt farmasöytiske preparater - Google Patents
Oksadiazoler, anvendelse derav, fremgangsmåte for deres fremstilling, samt farmasöytiske preparater Download PDFInfo
- Publication number
- NO312512B1 NO312512B1 NO19991815A NO991815A NO312512B1 NO 312512 B1 NO312512 B1 NO 312512B1 NO 19991815 A NO19991815 A NO 19991815A NO 991815 A NO991815 A NO 991815A NO 312512 B1 NO312512 B1 NO 312512B1
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- NO
- Norway
- Prior art keywords
- formula
- group
- phenyl
- methyl
- optionally
- Prior art date
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- 150000004866 oxadiazoles Chemical class 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 72
- -1 N-morpholinyl Chemical group 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 43
- 239000001301 oxygen Substances 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- 239000011737 fluorine Substances 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000013543 active substance Substances 0.000 claims description 13
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 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 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 229930192474 thiophene Natural products 0.000 claims description 9
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
- 201000006474 Brain Ischemia Diseases 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 206010008118 cerebral infarction Diseases 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 4
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- PCFIPYFVXDCWBW-UHFFFAOYSA-N tricyclo[3.3.1.03,7]nonane Chemical compound C1C(C2)C3CC2CC1C3 PCFIPYFVXDCWBW-UHFFFAOYSA-N 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- YMEHWISYYMKMFO-WOMRJYOTSA-N methyl N-[(12E,15S)-15-[(4S)-4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2(7),3,5,12,16-hexaen-5-yl]carbamate Chemical compound COC(=O)Nc1ccc2-c3cnc([nH]3)[C@H](C\C=C\CCC(=O)Nc2c1)N1CC[C@@H](CC1=O)c1cccc(Cl)c1 YMEHWISYYMKMFO-WOMRJYOTSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
- 239000012312 sodium hydride Substances 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 235000015424 sodium Nutrition 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 206010021143 Hypoxia Diseases 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 235000001465 calcium Nutrition 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 208000028867 ischemia Diseases 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 235000001055 magnesium Nutrition 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 230000004770 neurodegeneration Effects 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 235000012222 talc Nutrition 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 208000013016 Hypoglycemia Diseases 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 150000001558 benzoic acid derivatives Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- VNCIJMRFIRKERM-UHFFFAOYSA-N chembl1876217 Chemical compound OC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NO1 VNCIJMRFIRKERM-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012039 electrophile Substances 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 108010085082 sigma receptors Proteins 0.000 description 4
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- VRYALKFFQXWPIH-PBXRRBTRSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-PBXRRBTRSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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
- 206010002660 Anoxia Diseases 0.000 description 3
- 241000976983 Anoxia Species 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Chemical group 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910000095 alkaline earth hydride Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- PMMURAAUARKVCB-UHFFFAOYSA-N alpha-D-ara-dHexp Natural products OCC1OC(O)CC(O)C1O PMMURAAUARKVCB-UHFFFAOYSA-N 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
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- 238000004587 chromatography analysis Methods 0.000 description 3
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- 238000001514 detection method Methods 0.000 description 3
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- 210000002569 neuron Anatomy 0.000 description 3
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
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- YYHIRPUVYUUCTJ-UHFFFAOYSA-N methyl 2-[2-(dimethylamino)ethoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCN(C)C YYHIRPUVYUUCTJ-UHFFFAOYSA-N 0.000 description 1
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- TVRQERDAIUFEKX-UHFFFAOYSA-N n,n-dimethyl-2-[2-(5-phenyl-1,2,4-oxadiazol-3-yl)phenoxy]ethanamine Chemical compound CN(C)CCOC1=CC=CC=C1C1=NOC(C=2C=CC=CC=2)=N1 TVRQERDAIUFEKX-UHFFFAOYSA-N 0.000 description 1
- RJQDCUPMSRESJF-UHFFFAOYSA-N n,n-dimethyl-2-[[2-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl]methoxy]ethanamine Chemical compound CN(C)CCOCC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NO1 RJQDCUPMSRESJF-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19643037A DE19643037A1 (de) | 1996-10-18 | 1996-10-18 | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| PCT/EP1997/005693 WO1998017652A1 (de) | 1996-10-18 | 1997-10-15 | Oxadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO991815L NO991815L (no) | 1999-04-16 |
| NO991815D0 NO991815D0 (no) | 1999-04-16 |
| NO312512B1 true NO312512B1 (no) | 2002-05-21 |
Family
ID=7809114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19991815A NO312512B1 (no) | 1996-10-18 | 1999-04-16 | Oksadiazoler, anvendelse derav, fremgangsmåte for deres fremstilling, samt farmasöytiske preparater |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6277872B1 (bg) |
| EP (1) | EP0934288B1 (bg) |
| JP (1) | JP3333523B2 (bg) |
| KR (1) | KR20000049253A (bg) |
| CN (1) | CN1086698C (bg) |
| AR (1) | AR008496A1 (bg) |
| AT (1) | ATE315034T1 (bg) |
| AU (1) | AU737552B2 (bg) |
| BG (1) | BG103251A (bg) |
| BR (1) | BR9714354A (bg) |
| CA (1) | CA2268954C (bg) |
| CO (1) | CO4920253A1 (bg) |
| CZ (1) | CZ138099A3 (bg) |
| DE (2) | DE19643037A1 (bg) |
| EE (1) | EE9900147A (bg) |
| ES (1) | ES2256880T3 (bg) |
| HK (1) | HK1020956A1 (bg) |
| HR (1) | HRP970553A2 (bg) |
| HU (1) | HUP0001652A3 (bg) |
| ID (1) | ID18613A (bg) |
| IL (1) | IL129315A0 (bg) |
| NO (1) | NO312512B1 (bg) |
| NZ (1) | NZ335598A (bg) |
| PE (1) | PE11199A1 (bg) |
| PL (1) | PL332432A1 (bg) |
| RU (1) | RU2182905C2 (bg) |
| SK (1) | SK49999A3 (bg) |
| TR (1) | TR199900848T2 (bg) |
| TW (1) | TW413678B (bg) |
| WO (1) | WO1998017652A1 (bg) |
| YU (1) | YU40997A (bg) |
| ZA (1) | ZA979220B (bg) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19816880A1 (de) | 1998-04-17 | 1999-10-21 | Boehringer Ingelheim Pharma | Neue Diphenyl-substituierte 5-Ring-Heterocyclen, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| IT1300056B1 (it) | 1998-04-17 | 2000-04-05 | Boehringer Ingelheim Italia | Eterocicli con anello a 6 termini difenil-sostituiti loro procedimento di preparazione e loro impiego come farmaci |
| US6107313A (en) * | 1998-10-02 | 2000-08-22 | Combichem, Inc. | Dopamine receptor antagonists |
| EP1153922B1 (en) | 1999-02-15 | 2006-04-26 | Eisai Co., Ltd. | Heterodiazinone derivatives |
| PT1070708E (pt) | 1999-07-21 | 2004-05-31 | Hoffmann La Roche | Derivados de triazol |
| CA2381975A1 (en) * | 1999-08-19 | 2001-02-22 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| US6660753B2 (en) | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| EP1582519A3 (en) * | 1999-08-19 | 2005-12-21 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| US6579880B2 (en) * | 2000-06-06 | 2003-06-17 | Ortho-Mcneil Pharmaceutical, Inc. | Isoxazoles and oxadiazoles as anti-inflammatory inhibitors of IL-8 |
| EP2177520A1 (en) | 2000-06-12 | 2010-04-21 | Eisai R&D Management Co., Ltd. | 1,5-Di(aryl or heteroaryl)-3-halo-2(1H)-pyridones as intermediates for the preparation of AMPA receptor inhibitors |
| WO2002022587A1 (fr) * | 2000-09-18 | 2002-03-21 | Eisai Co., Ltd. | Pyridazinones et triazinones ainsi que leur utilisation medicale |
| EP1679313A3 (en) * | 2001-02-21 | 2006-08-16 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| JP4303109B2 (ja) * | 2001-10-04 | 2009-07-29 | メルク エンド カムパニー インコーポレーテッド | 代謝共役型グルタミン酸受容体−５のヘテロアリール置換テトラゾール調節剤 |
| MY151199A (en) | 2001-11-02 | 2014-04-30 | Rigel Pharmaceuticals Inc | Substituted diphenyl heterocycles useful for treating hcv infection |
| GB0129260D0 (en) | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| AU2003262831A1 (en) | 2002-08-23 | 2004-03-11 | Rigel Pharmaceuticals, Inc. | Pyridyl substituted heterocycles useful for treating or preventing hcv infection |
| GB0303503D0 (en) * | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| WO2004099165A2 (en) | 2003-05-02 | 2004-11-18 | Rigel Pharmaceuticals, Inc. | Heterocyclic compounds and hydro isomers thereof |
| WO2004099164A1 (en) * | 2003-05-02 | 2004-11-18 | Rigel Pharmaceuticals, Inc. | Substituted diphenyl isoxazoles, pyrazoles and oxadiazoles useful for treating hcv infection |
| US7220745B2 (en) | 2003-05-15 | 2007-05-22 | Rigel Pharmaceuticals | Heterocyclic compounds useful to treat HCV |
| US7410979B2 (en) | 2003-11-19 | 2008-08-12 | Rigel Pharmaceuticals, Inc. | Synergistically effective combinations of dihaloacetamide compounds and interferon or ribavirin against HCV infections |
| AU2004303604B2 (en) | 2003-12-24 | 2011-03-24 | Prosidion Limited | Heterocyclic derivatives as GPCR receptor agonists |
| US7514434B2 (en) | 2004-02-23 | 2009-04-07 | Rigel Pharmaceuticals, Inc. | Heterocyclic compounds having an oxadiazole moiety and hydro isomers thereof |
| MY148809A (en) | 2004-07-06 | 2013-05-31 | Eisai R&D Man Co Ltd | Crystals of 1,2-dihydropyridine compound and their production process |
| JPWO2006109876A1 (ja) * | 2005-04-08 | 2008-11-20 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 不随意運動治療剤 |
| WO2007027230A2 (en) | 2005-05-02 | 2007-03-08 | Rigel Pharmaceuticals, Inc. | Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses |
| GB0510142D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| HUP0500920A2 (en) * | 2005-10-05 | 2007-07-30 | Richter Gedeon Nyrt | Oxadiazole derivatives, process for their preparation and their use |
| US20110207704A1 (en) * | 2006-12-15 | 2011-08-25 | Abbott Laboratories | Novel Oxadiazole Compounds |
| BRPI0720043A2 (pt) * | 2006-12-15 | 2014-01-07 | Abbott Lab | Composto oxadiazol |
| JO2701B1 (en) | 2006-12-21 | 2013-03-03 | جلاكسو جروب ليميتد | Vehicles |
| BRPI0817597A2 (pt) * | 2007-10-04 | 2015-04-07 | Merck Serono Sa | Compostos de diarila de oxadiazol, processo para sua preparação, composições farmacêuticas e kit compreendendo os mesmos, bem como seus usos |
| US9045442B2 (en) * | 2007-12-21 | 2015-06-02 | University Of Notre Dame Du Lac | Antibacterial compounds and methods of using same |
| KR101787112B1 (ko) | 2008-06-09 | 2017-11-15 | 루드비히-막시밀리안스-우니버지테트 뮌헨 | 신경변성 질환 및/또는 단백질 응집과 연관된 질환과 관련된 단백질의 응집을 억제하기 위한 신규 약물 |
| US9095596B2 (en) | 2009-10-15 | 2015-08-04 | Southern Research Institute | Treatment of neurodegenerative diseases, causation of memory enhancement, and assay for screening compounds for such |
| JP6219955B2 (ja) * | 2012-08-24 | 2017-10-25 | トレヴェンティス コーポレイションＴｒｅｖｅｎｔｉｓ Ｃｏｒｐｏｒａｔｉｏｎ | ベンゾフラザン抗アミロイド化合物および方法 |
| SI3110812T1 (sl) | 2014-02-27 | 2019-08-30 | Treventis Corporation | Anti-amiloidne spojine, ki vsebujejo benzofurazan |
| EP3135114B1 (en) | 2014-04-24 | 2019-03-20 | Sumitomo Chemical Company, Limited | Diaryl-azole compound |
| CA2962431A1 (en) | 2014-09-25 | 2016-03-31 | University Of Notre Dame Du Lac | Non-beta lactam antibiotics |
| CN107286174B (zh) * | 2016-04-11 | 2020-08-18 | 上海勋和医药科技有限公司 | 取代2,4-(1h,3h)嘧啶二酮作为parp抑制剂及其应用 |
| WO2018049404A1 (en) | 2016-09-12 | 2018-03-15 | University Of Notre Dame Du Lac | Compounds for the treatment of clostridium difficile infection |
| EP3634403A1 (en) | 2017-05-12 | 2020-04-15 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Phenyl-heterocycle-phenyl derivatives for use in the treatment or prevention of melanoma |
| US10676467B2 (en) | 2017-06-30 | 2020-06-09 | Washington University | Compositions for binding sphingosine-1-phosphate receptor 1 (S1P1), imaging of S1P1, and methods of use thereof |
| AU2019395288A1 (en) | 2018-12-14 | 2021-09-23 | Eisai R&D Management Co., Ltd. | Aqueous based pharmaceutical formulations of 1,2-dihydropyridine compounds |
| WO2023042888A1 (ja) | 2021-09-15 | 2023-03-23 | 国立大学法人 琉球大学 | 認知機能低下、または過体重もしくは肥満症を処置することに用いるための医薬組成物 |
| JPWO2023042887A1 (bg) | 2021-09-15 | 2023-03-23 | ||
| EP4173485A1 (en) | 2021-10-27 | 2023-05-03 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Protein aggregation inhibiting compounds for plant disease control |
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| US4003909A (en) * | 1974-07-22 | 1977-01-18 | E. R. Squibb & Sons, Inc. | [(1,2,4-Oxadiazol-3-yl)phenyl]carbamic or thiocarbamic acid esters |
| JPS52272A (en) * | 1975-10-17 | 1977-01-05 | Takeda Chem Ind Ltd | Process for preparing 1,2,4-oxadiazole derivatives |
| DE2801509A1 (de) * | 1978-01-12 | 1979-07-19 | Schering Ag | 1,2,4-oxadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| JPS58150576A (ja) * | 1982-03-03 | 1983-09-07 | Sumitomo Chem Co Ltd | 新規な１，２，４−オキサジアゾ−ル誘導体 |
| US4871753A (en) * | 1986-12-12 | 1989-10-03 | Ciba-Geigy Corporation | 3-Phenyl-5-trifluoromethyl-1,2,4-oxadiazole compounds which are useful pesticides |
| DE3905242A1 (de) * | 1989-02-21 | 1990-08-23 | Basf Ag | Verfahren zur herstellung von phenyloxdiazolylanilinen |
| JPH02250873A (ja) * | 1989-03-24 | 1990-10-08 | Mitsubishi Petrochem Co Ltd | １，２，４―オキサジアゾール誘導体及びそれを有効成分とする除草剤 |
| NZ234760A (en) * | 1989-08-18 | 1991-09-25 | Sterling Drug Inc | Antiviral oxazole compounds and compositions |
| DK443489D0 (da) * | 1989-09-08 | 1989-09-08 | Ferrosan As | Substituerede urinstofforbindelser, deres fremstilling og anvendelse |
| JPH04295470A (ja) * | 1991-03-22 | 1992-10-20 | Wakamoto Pharmaceut Co Ltd | モノアミンオキシダーゼ−ｂ酵素阻害活性を有する１，２，４−オキサジアゾール誘導体及びその製造法 |
| WO1993002677A1 (en) * | 1991-08-03 | 1993-02-18 | Smithkline Beecham Plc | 5-ht4 receptor antagonists |
| DE4401107A1 (de) * | 1994-01-17 | 1995-07-20 | Bayer Ag | 3-Aryl-alkenyl-1,2,4-oxadiazol-Derivate |
| DE4401108A1 (de) * | 1994-01-17 | 1995-07-20 | Bayer Ag | 1,2,4-Oxadiazol-Derivate |
| DE19528189A1 (de) * | 1995-08-01 | 1997-02-06 | Basf Ag | Benzolderivate mit einem heterocyclischen Rest |
-
1996
- 1996-10-18 DE DE19643037A patent/DE19643037A1/de not_active Withdrawn
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1997
- 1997-10-15 CA CA002268954A patent/CA2268954C/en not_active Expired - Fee Related
- 1997-10-15 RU RU99111781/04A patent/RU2182905C2/ru not_active IP Right Cessation
- 1997-10-15 NZ NZ335598A patent/NZ335598A/en unknown
- 1997-10-15 IL IL12931597A patent/IL129315A0/xx unknown
- 1997-10-15 PL PL97332432A patent/PL332432A1/xx unknown
- 1997-10-15 CN CN97198866A patent/CN1086698C/zh not_active Expired - Fee Related
- 1997-10-15 TR TR1999/00848T patent/TR199900848T2/xx unknown
- 1997-10-15 AU AU48676/97A patent/AU737552B2/en not_active Ceased
- 1997-10-15 US US09/284,382 patent/US6277872B1/en not_active Expired - Lifetime
- 1997-10-15 DE DE59712543T patent/DE59712543D1/de not_active Expired - Lifetime
- 1997-10-15 EE EEP199900147A patent/EE9900147A/xx unknown
- 1997-10-15 AT AT97911227T patent/ATE315034T1/de active
- 1997-10-15 CZ CZ991380A patent/CZ138099A3/cs unknown
- 1997-10-15 JP JP50563998A patent/JP3333523B2/ja not_active Expired - Lifetime
- 1997-10-15 HU HU0001652A patent/HUP0001652A3/hu unknown
- 1997-10-15 ES ES97911227T patent/ES2256880T3/es not_active Expired - Lifetime
- 1997-10-15 KR KR1019990703360A patent/KR20000049253A/ko not_active Application Discontinuation
- 1997-10-15 ZA ZA9709220A patent/ZA979220B/xx unknown
- 1997-10-15 EP EP97911227A patent/EP0934288B1/de not_active Expired - Lifetime
- 1997-10-15 PE PE1997000910A patent/PE11199A1/es not_active Application Discontinuation
- 1997-10-15 BR BR9714354-5A patent/BR9714354A/pt not_active IP Right Cessation
- 1997-10-15 SK SK499-99A patent/SK49999A3/sk unknown
- 1997-10-15 WO PCT/EP1997/005693 patent/WO1998017652A1/de active IP Right Grant
- 1997-10-16 HR HR19643037.2A patent/HRP970553A2/hr not_active Application Discontinuation
- 1997-10-16 ID IDP973449A patent/ID18613A/id unknown
- 1997-10-16 YU YU40997A patent/YU40997A/sh unknown
- 1997-10-17 AR ARP970104812A patent/AR008496A1/es not_active Application Discontinuation
- 1997-10-17 CO CO97061157A patent/CO4920253A1/es unknown
- 1997-10-18 TW TW086115386A patent/TW413678B/zh not_active IP Right Cessation
-
1999
- 1999-03-15 BG BG103251A patent/BG103251A/bg active Pending
- 1999-04-16 NO NO19991815A patent/NO312512B1/no not_active IP Right Cessation
- 1999-12-29 HK HK99106174A patent/HK1020956A1/xx not_active IP Right Cessation
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