HRP20000079A2 - Heterocyclic vinylethers against neurological disorders - Google Patents
Heterocyclic vinylethers against neurological disorders Download PDFInfo
- Publication number
- HRP20000079A2 HRP20000079A2 HR20000079A HRP20000079A HRP20000079A2 HR P20000079 A2 HRP20000079 A2 HR P20000079A2 HR 20000079 A HR20000079 A HR 20000079A HR P20000079 A HRP20000079 A HR P20000079A HR P20000079 A2 HRP20000079 A2 HR P20000079A2
- Authority
- HR
- Croatia
- Prior art keywords
- vinyl
- compounds
- phenyl
- triazole
- dichlorophenyl
- Prior art date
Links
- 208000012902 Nervous system disease Diseases 0.000 title claims description 6
- 208000025966 Neurological disease Diseases 0.000 title claims description 6
- -1 Heterocyclic vinylethers Chemical class 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- WTPIKODEIQEHHW-UHFFFAOYSA-N 1-[2-butoxy-2-(4-chlorophenyl)ethenyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=CC=1C(OCCCC)=CN1C=NC=N1 WTPIKODEIQEHHW-UHFFFAOYSA-N 0.000 claims description 6
- SKAYRDVTMVVMKL-UHFFFAOYSA-N 1-[2-cyclohexyloxy-2-(2,4-dichlorophenyl)ethenyl]-1,2,4-triazole Chemical compound ClC1=CC(Cl)=CC=C1C(OC1CCCCC1)=CN1N=CN=C1 SKAYRDVTMVVMKL-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- ABVXVPZILYLGMQ-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-phenylmethoxyethenyl]tetrazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C=CC=CC=1)=CN1N=NN=C1 ABVXVPZILYLGMQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000006806 disease prevention Effects 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- OYEKXPUKWPBDPH-UHFFFAOYSA-N 1-[2-butoxy-2-(2,6-dichlorophenyl)ethenyl]-1,2,4-triazole Chemical compound ClC=1C=CC=C(Cl)C=1C(OCCCC)=CN1C=NC=N1 OYEKXPUKWPBDPH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- KUVSMUPNINYCGZ-UHFFFAOYSA-N 2-[2-butoxy-2-(4-chlorophenyl)ethenyl]tetrazole Chemical compound C=1C=C(Cl)C=CC=1C(OCCCC)=CN1N=CN=N1 KUVSMUPNINYCGZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 230000001629 suppression Effects 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 description 9
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- OLNGHNMEXQKLJP-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(tetrazol-2-yl)ethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)CN1N=NC=N1 OLNGHNMEXQKLJP-UHFFFAOYSA-N 0.000 description 7
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- XOHMICFWUQPTNP-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)CN1N=CN=C1 XOHMICFWUQPTNP-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 5
- 239000007903 gelatin capsule Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YFYNOWXBIBKGHB-FFWSUHOLSA-N (1s,3s)-1-aminocyclopentane-1,3-dicarboxylic acid Chemical compound OC(=O)[C@]1(N)CC[C@H](C(O)=O)C1 YFYNOWXBIBKGHB-FFWSUHOLSA-N 0.000 description 4
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- ROKJHWJMTXQYJD-UHFFFAOYSA-N 1-[1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethenyl]cyclopropane-1-carboxylic acid Chemical compound C1=NC=NN1C=C(C=1C(=CC(Cl)=CC=1)Cl)C1(C(=O)O)CC1 ROKJHWJMTXQYJD-UHFFFAOYSA-N 0.000 description 3
- IPJOWHRNDGGEAE-UHFFFAOYSA-N 1-[2-(4-methylphenyl)-2-propan-2-yloxyethenyl]-1,2,4-triazole Chemical compound C=1C=C(C)C=CC=1C(OC(C)C)=CN1C=NC=N1 IPJOWHRNDGGEAE-UHFFFAOYSA-N 0.000 description 3
- WSOAIAJKFKYATC-UHFFFAOYSA-N 1-[2-butoxy-2-(2,4-dichlorophenyl)ethenyl]imidazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OCCCC)=CN1C=CN=C1 WSOAIAJKFKYATC-UHFFFAOYSA-N 0.000 description 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 3
- VYWPPRLJNVHPEU-UHFFFAOYSA-N 2-chloro-1-(2,4-dichlorophenyl)ethanone Chemical compound ClCC(=O)C1=CC=C(Cl)C=C1Cl VYWPPRLJNVHPEU-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 2
- SOUVGVXCDDQYCI-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-phenylmethoxyethenyl]-1,2,4-triazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C=CC=CC=1)=CN1N=CN=C1 SOUVGVXCDDQYCI-UHFFFAOYSA-N 0.000 description 2
- HVPOYWGCWYAXMX-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-propan-2-yloxyethenyl]imidazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OC(C)C)=CN1C=CN=C1 HVPOYWGCWYAXMX-UHFFFAOYSA-N 0.000 description 2
- RUPAZAIKPULYKU-UHFFFAOYSA-N 1-[2-(2,6-dichlorophenyl)-2-phenylmethoxyethenyl]-1,2,4-triazole Chemical compound ClC1=CC=CC(Cl)=C1C(OCC=1C=CC=CC=1)=CN1N=CN=C1 RUPAZAIKPULYKU-UHFFFAOYSA-N 0.000 description 2
- AQFXIWDRLHRFIC-UHFFFAOYSA-N 1-[5-phenyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical compound CC(=O)N1N=C(C(F)(F)F)C=C1C1=CC=CC=C1 AQFXIWDRLHRFIC-UHFFFAOYSA-N 0.000 description 2
- PWSQTUCTQFOJKU-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)-2-[(4-methoxyphenyl)methoxy]ethenyl]tetrazole Chemical compound C1=CC(OC)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)=CN1N=NC=N1 PWSQTUCTQFOJKU-UHFFFAOYSA-N 0.000 description 2
- MQHOMRXROQFFSU-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)-2-propan-2-yloxyethenyl]tetrazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OC(C)C)=CN1N=CN=N1 MQHOMRXROQFFSU-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VEZNCHDBSQWUHQ-UHFFFAOYSA-N chlorocyclopropane Chemical compound ClC1CC1 VEZNCHDBSQWUHQ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- VHLRUGZSAQKKLU-UHFFFAOYSA-N cyclohexyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1CCCCC1 VHLRUGZSAQKKLU-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 229940049906 glutamate Drugs 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- NDJBHBQUEAGIOB-UHFFFAOYSA-N propan-2-yl trifluoromethanesulfonate Chemical compound CC(C)OS(=O)(=O)C(F)(F)F NDJBHBQUEAGIOB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003536 tetrazoles Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RGYIISVBVGLAPZ-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)CN1N=CN=C1 RGYIISVBVGLAPZ-UHFFFAOYSA-N 0.000 description 1
- FMECXELZNVDTPS-UHFFFAOYSA-N 1-(2-phenyl-2-propan-2-yloxyethenyl)-1,2,4-triazole Chemical compound C=1C=CC=CC=1C(OC(C)C)=CN1C=NC=N1 FMECXELZNVDTPS-UHFFFAOYSA-N 0.000 description 1
- ZFWAVFITNQYLMB-UHFFFAOYSA-N 1-(4-methylphenyl)-2-(1,2,4-triazol-1-yl)ethanone Chemical compound C1=CC(C)=CC=C1C(=O)CN1N=CN=C1 ZFWAVFITNQYLMB-UHFFFAOYSA-N 0.000 description 1
- YASHINYHANEEFV-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-(2-methylpropoxy)ethenyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OCC(C)C)=CN1C=NC=N1 YASHINYHANEEFV-UHFFFAOYSA-N 0.000 description 1
- QQTYGKIZIDPGRU-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-methoxyethenyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OC)=CN1C=NC=N1 QQTYGKIZIDPGRU-UHFFFAOYSA-N 0.000 description 1
- AZGZZCSYRASLDM-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-propan-2-yloxyethenyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OC(C)C)=CN1C=NC=N1 AZGZZCSYRASLDM-UHFFFAOYSA-N 0.000 description 1
- KWUUCSRHZCDZDO-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-propan-2-yloxyethenyl]tetrazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OC(C)C)=CN1C=NN=N1 KWUUCSRHZCDZDO-UHFFFAOYSA-N 0.000 description 1
- WMEPIKCVGRXWLS-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)ethenyl]-2-phenylmethoxy-3H-1,2,4-triazole Chemical compound ClC1=C(C=CC(=C1)Cl)C=CN1N(CN=C1)OCC1=CC=CC=C1 WMEPIKCVGRXWLS-UHFFFAOYSA-N 0.000 description 1
- DOPSRBWGGYPQNB-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)-2-propan-2-yloxyethenyl]-1,2,4-triazole Chemical compound C=1C=C(F)C=C(F)C=1C(OC(C)C)=CN1C=NC=N1 DOPSRBWGGYPQNB-UHFFFAOYSA-N 0.000 description 1
- GOXGOXAFQGUKBA-UHFFFAOYSA-N 1-[2-(4-bromophenyl)-2-butoxyethenyl]-1,2,4-triazole Chemical compound C=1C=C(Br)C=CC=1C(OCCCC)=CN1C=NC=N1 GOXGOXAFQGUKBA-UHFFFAOYSA-N 0.000 description 1
- KXUBKOIRGILENJ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-2-propan-2-yloxyethenyl]-1,2,4-triazole Chemical compound C=1C=C(F)C=CC=1C(OC(C)C)=CN1C=NC=N1 KXUBKOIRGILENJ-UHFFFAOYSA-N 0.000 description 1
- XLJAVQLWVBPOAU-UHFFFAOYSA-N 1-[2-propan-2-yloxy-2-(2,4,6-trichlorophenyl)ethenyl]-1,2,4-triazole Chemical compound ClC=1C=C(Cl)C=C(Cl)C=1C(OC(C)C)=CN1C=NC=N1 XLJAVQLWVBPOAU-UHFFFAOYSA-N 0.000 description 1
- AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 1
- FNOGEZGAOZSVPP-UHFFFAOYSA-N 2-[2-butoxy-2-(2,4-dichlorophenyl)ethenyl]tetrazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OCCCC)=CN1N=CN=N1 FNOGEZGAOZSVPP-UHFFFAOYSA-N 0.000 description 1
- TVBKZSJFNJEZNI-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-yl)but-3-enoic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CC(=O)O)=CN1C=NC=N1 TVBKZSJFNJEZNI-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010065040 AIDS dementia complex Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000012661 Dyskinesia Diseases 0.000 description 1
- 208000020564 Eye injury Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 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 1
- 108090000543 Ligand-Gated Ion Channels Proteins 0.000 description 1
- 102000004086 Ligand-Gated Ion Channels Human genes 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 1
- 102100036834 Metabotropic glutamate receptor 1 Human genes 0.000 description 1
- 102100036837 Metabotropic glutamate receptor 2 Human genes 0.000 description 1
- 102100038352 Metabotropic glutamate receptor 3 Human genes 0.000 description 1
- 102100038354 Metabotropic glutamate receptor 4 Human genes 0.000 description 1
- 102100038357 Metabotropic glutamate receptor 5 Human genes 0.000 description 1
- 102100038300 Metabotropic glutamate receptor 6 Human genes 0.000 description 1
- 102100038294 Metabotropic glutamate receptor 7 Human genes 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 101001071458 Rattus norvegicus Metabotropic glutamate receptor 2 Proteins 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000003925 brain function Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000003823 glutamate receptor agonist Substances 0.000 description 1
- 239000003825 glutamate receptor antagonist Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 230000000873 masking effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 108010038421 metabotropic glutamate receptor 2 Proteins 0.000 description 1
- 108010038445 metabotropic glutamate receptor 3 Proteins 0.000 description 1
- 108010038422 metabotropic glutamate receptor 4 Proteins 0.000 description 1
- 108010038450 metabotropic glutamate receptor 6 Proteins 0.000 description 1
- 108010038449 metabotropic glutamate receptor 7 Proteins 0.000 description 1
- 108010014719 metabotropic glutamate receptor type 1 Proteins 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 210000002265 sensory receptor cell Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (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 |
|---|---|---|---|
| EP97114065 | 1997-08-14 | ||
| PCT/EP1998/004890 WO1999008678A1 (en) | 1997-08-14 | 1998-08-06 | Heterocyclic vinylethers against neurological disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20000079A2 true HRP20000079A2 (en) | 2000-12-31 |
Family
ID=8227219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20000079A HRP20000079A2 (en) | 1997-08-14 | 2000-02-11 | Heterocyclic vinylethers against neurological disorders |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US6054588A (ru) |
| EP (1) | EP1003505B1 (ru) |
| JP (1) | JP3593031B2 (ru) |
| KR (1) | KR100357650B1 (ru) |
| CN (1) | CN1154489C (ru) |
| AR (1) | AR016604A1 (ru) |
| AT (1) | ATE262331T1 (ru) |
| AU (1) | AU741532B2 (ru) |
| BR (1) | BR9811933A (ru) |
| CA (1) | CA2297732C (ru) |
| DE (1) | DE69822638T2 (ru) |
| ES (1) | ES2216305T3 (ru) |
| HR (1) | HRP20000079A2 (ru) |
| HU (1) | HUP0004412A3 (ru) |
| ID (1) | ID28529A (ru) |
| IL (1) | IL134168A0 (ru) |
| NO (1) | NO20000738L (ru) |
| NZ (1) | NZ502463A (ru) |
| PL (1) | PL192029B1 (ru) |
| RU (1) | RU2218919C2 (ru) |
| TR (1) | TR200000405T2 (ru) |
| WO (1) | WO1999008678A1 (ru) |
| YU (1) | YU6100A (ru) |
| ZA (1) | ZA987145B (ru) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0115871A (pt) | 2000-12-04 | 2003-10-28 | Hoffmann La Roche | Derivados de feniletenila ou feniletinila como antagonistas de receptores de glutamato |
| JP2005502618A (ja) * | 2001-06-04 | 2005-01-27 | ザ・ジェネラル・ホスピタル・コーポレイション | 光力学的化合物を用いて脆弱なプラークを検出および治療する方法 |
| DE10205057A1 (de) * | 2002-02-07 | 2003-08-14 | Bayer Cropscience Ag | Substituierte 4-Hetaryl-pyrazoline |
| WO2004078715A1 (ja) | 2003-03-07 | 2004-09-16 | Astellas Pharma Inc. | ２，６－ジ置換スチリルを有する含窒素へテロ環誘導体 |
| TWI292318B (en) | 2003-03-10 | 2008-01-11 | Hoffmann La Roche | Imidazol-4-yl-ethynyl-pyridine derivatives |
| KR100907108B1 (ko) | 2004-06-01 | 2009-07-09 | 에프. 호프만-라 로슈 아게 | Ｍｇｌｕ5 수용체 길항제로서 피리딘-4-일-에틴일-이미다졸및 피라졸 |
| ITVA20050050A1 (it) * | 2005-08-05 | 2007-02-06 | Lamberti Spa | Sistemi fotopolimerizzabili contenenti coiniziatori fotoreticolabili a bassa estraibilita' e volatilita' |
| TWI417095B (zh) * | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| LT2083811T (lt) | 2006-11-22 | 2017-01-25 | Clinical Research Associates, Llc | Dauno sindromo, trapiosios x chromosomos sindromo ir autizmo gydymo būdai |
| CN101568531B (zh) | 2006-12-21 | 2013-11-13 | 弗·哈夫曼-拉罗切有限公司 | Mglur5受体拮抗剂的多晶型物 |
| TW200845978A (en) * | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| PT2200985E (pt) | 2007-09-14 | 2011-07-21 | Ortho Mcneil Janssen Pharm | 4-(aril-x-fenil)-1h-piridin-2-onas 1,3-dissubstituídas |
| JP5433579B2 (ja) * | 2007-09-14 | 2014-03-05 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | １，３−二置換−４−フェニル−１ｈ−ピリジン−２−オン |
| UA100126C2 (en) | 2007-09-14 | 2012-11-26 | Аддекс Фарма С.А. | 1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h, 1'h-[1, 4'] bipyridinyl-2'-ones |
| CN101861316B (zh) * | 2007-11-14 | 2013-08-21 | 奥梅-杨森制药有限公司 | 咪唑并[1,2-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| AU2009289784B2 (en) | 2008-09-02 | 2012-03-22 | Addex Pharma S.A. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| RU2517181C2 (ru) | 2008-10-16 | 2014-05-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Производные индола и бензоморфолина в качестве модулятора метаботропных глутаматных рецепторов |
| BRPI0921333A2 (pt) | 2008-11-28 | 2015-12-29 | Addex Pharmaceuticals Sa | derivados de indol e benzoxazina como moduladores de receptores de glutamato metabotrópicos |
| KR101753826B1 (ko) | 2009-05-12 | 2017-07-04 | 얀센 파마슈티칼즈, 인코포레이티드 | 1,２,４―트리아졸로［４,３―ａ］피리딘 유도체 및 신경정신 질환의 치료 또는 예방을 위한 이들의 용도 |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| BRPI1010831A2 (pt) | 2009-05-12 | 2016-04-05 | Addex Pharmaceuticals Sa | derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2 |
| EP2544688B1 (en) | 2010-03-02 | 2016-09-07 | President and Fellows of Harvard College | Methods and compositions for treatment of angelman syndrome |
| WO2011150380A1 (en) | 2010-05-28 | 2011-12-01 | Xenoport, Inc. | Methods of treatment of fragile x syndrome, down's syndrome, autism and related disorders |
| US20120016021A1 (en) | 2010-07-15 | 2012-01-19 | Xenoport, Inc. | Methods of treating fragile x syndrome, down's syndrome, autism and related disorders |
| EP2649069B1 (en) | 2010-11-08 | 2015-08-26 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| AU2011328203B2 (en) | 2010-11-08 | 2015-03-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| ES2536433T3 (es) | 2010-11-08 | 2015-05-25 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2 |
| CN102506473B (zh) * | 2011-10-18 | 2014-06-11 | 江苏七彩科技有限公司 | 直接蒸发式冰蓄冷制冷系统及其制冷方法 |
| CN102690240B (zh) * | 2012-06-07 | 2014-09-10 | 郑州大学 | 三氮唑烯醚类、肟醚类化合物及其制备方法与应用 |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| MX2016009471A (es) | 2014-01-21 | 2016-10-13 | Janssen Pharmaceutica Nv | Combinaciones que comprenden agonistas ortostericos o moduladores alostericos positivos del receptor glutamatergico metabotropico de subtipo 2 y su uso. |
| HUE045610T2 (hu) | 2014-01-21 | 2020-01-28 | Janssen Pharmaceutica Nv | 2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait vagy ortosztérikus agonistáit tartalmazó kombinációk és alkalmazásuk |
| CN106279038A (zh) * | 2016-08-16 | 2017-01-04 | 湖南中威制药有限公司 | 一种硝酸奥昔康唑原料药的合成方法 |
| KR102635936B1 (ko) | 2016-12-14 | 2024-02-13 | 에스케이바이오팜 주식회사 | 탈수초성 질환의 예방, 경감 또는 치료를 위한 카바메이트 화합물의 용도 |
| AU2017374458B2 (en) * | 2016-12-14 | 2023-03-02 | Sk Biopharmaceuticals Co., Ltd. | Use of carbamate compounds for prevention, alleviation or treatment of bipolar disorder |
| KR20230066244A (ko) | 2021-11-06 | 2023-05-15 | 김경민 | 점선식 포장지 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4330545A (en) | 1977-02-21 | 1982-05-18 | Siegfried Aktiengesellschaft | Heterocyclic imidazolyl vinyl ethers and use of same as fungicides or bactericides |
| DE2839388A1 (de) | 1978-09-11 | 1980-03-27 | Siegfried Ag | Imidazolylvinylaether und deren verwendung |
| CH648552A5 (de) * | 1981-01-23 | 1985-03-29 | Siegfried Ag | Verfahren zur herstellung von imidazolylvinylethern. |
| EP0079856A1 (de) * | 1981-11-12 | 1983-05-25 | Ciba-Geigy Ag | Mikrobizide Triazolyl-vinyläther |
| DE3417468A1 (de) * | 1984-05-11 | 1985-11-14 | Bayer Ag, 5090 Leverkusen | Azolylvinylether |
| US5658943A (en) * | 1995-01-05 | 1997-08-19 | Warner-Lambert Company | Phenylalanine derivatives as endothelin antagonists |
-
1998
- 1998-08-06 YU YU6100A patent/YU6100A/sh unknown
- 1998-08-06 RU RU2000106044/14A patent/RU2218919C2/ru not_active IP Right Cessation
- 1998-08-06 AU AU91593/98A patent/AU741532B2/en not_active Ceased
- 1998-08-06 ES ES98943851T patent/ES2216305T3/es not_active Expired - Lifetime
- 1998-08-06 KR KR1020007001480A patent/KR100357650B1/ko not_active IP Right Cessation
- 1998-08-06 CN CNB988079917A patent/CN1154489C/zh not_active Expired - Fee Related
- 1998-08-06 NZ NZ502463A patent/NZ502463A/en unknown
- 1998-08-06 HU HU0004412A patent/HUP0004412A3/hu unknown
- 1998-08-06 EP EP98943851A patent/EP1003505B1/en not_active Expired - Lifetime
- 1998-08-06 AT AT98943851T patent/ATE262331T1/de not_active IP Right Cessation
- 1998-08-06 CA CA002297732A patent/CA2297732C/en not_active Expired - Fee Related
- 1998-08-06 BR BR9811933-8A patent/BR9811933A/pt not_active Application Discontinuation
- 1998-08-06 PL PL338637A patent/PL192029B1/pl unknown
- 1998-08-06 WO PCT/EP1998/004890 patent/WO1999008678A1/en not_active Application Discontinuation
- 1998-08-06 JP JP2000509418A patent/JP3593031B2/ja not_active Expired - Fee Related
- 1998-08-06 IL IL13416898A patent/IL134168A0/xx unknown
- 1998-08-06 ID IDW20000212A patent/ID28529A/id unknown
- 1998-08-06 TR TR2000/00405T patent/TR200000405T2/xx unknown
- 1998-08-06 DE DE69822638T patent/DE69822638T2/de not_active Expired - Fee Related
- 1998-08-07 ZA ZA987145A patent/ZA987145B/xx unknown
- 1998-08-12 AR ARP980103977A patent/AR016604A1/es not_active Application Discontinuation
-
1999
- 1999-05-04 US US09/304,624 patent/US6054588A/en not_active Expired - Fee Related
- 1999-05-04 US US09/304,909 patent/US6248901B1/en not_active Expired - Fee Related
-
2000
- 2000-02-11 HR HR20000079A patent/HRP20000079A2/hr not_active Application Discontinuation
- 2000-02-14 NO NO20000738A patent/NO20000738L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU741532B2 (en) | 2001-12-06 |
| IL134168A0 (en) | 2001-04-30 |
| HUP0004412A2 (hu) | 2001-07-30 |
| ATE262331T1 (de) | 2004-04-15 |
| KR100357650B1 (ko) | 2002-10-25 |
| NO20000738D0 (no) | 2000-02-14 |
| PL338637A1 (en) | 2000-11-06 |
| PL192029B1 (pl) | 2006-08-31 |
| US6248901B1 (en) | 2001-06-19 |
| ZA987145B (en) | 1999-02-15 |
| EP1003505B1 (en) | 2004-03-24 |
| ES2216305T3 (es) | 2004-10-16 |
| NO20000738L (no) | 2000-04-11 |
| DE69822638D1 (de) | 2004-04-29 |
| NZ502463A (en) | 2002-05-31 |
| YU6100A (sh) | 2002-10-18 |
| CA2297732C (en) | 2008-04-29 |
| CN1266368A (zh) | 2000-09-13 |
| AU9159398A (en) | 1999-03-08 |
| TR200000405T2 (tr) | 2000-08-21 |
| WO1999008678A1 (en) | 1999-02-25 |
| JP2001515037A (ja) | 2001-09-18 |
| KR20010022877A (ko) | 2001-03-26 |
| AR016604A1 (es) | 2001-07-25 |
| RU2218919C2 (ru) | 2003-12-20 |
| ID28529A (id) | 2001-05-31 |
| CN1154489C (zh) | 2004-06-23 |
| DE69822638T2 (de) | 2005-02-24 |
| BR9811933A (pt) | 2000-09-05 |
| US6054588A (en) | 2000-04-25 |
| HUP0004412A3 (en) | 2003-06-30 |
| EP1003505A1 (en) | 2000-05-31 |
| CA2297732A1 (en) | 1999-02-25 |
| JP3593031B2 (ja) | 2004-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20000079A2 (en) | Heterocyclic vinylethers against neurological disorders | |
| US6706707B2 (en) | Phenylethynyl and styryl derivatives of imidazole and fused ring heterocycles | |
| AU2002229567A1 (en) | Phenylethenyl or phenylethinyl derivatives as glutamate receptor antagonists | |
| JP4177435B2 (ja) | 治療薬 | |
| PT1438296E (pt) | Derivados de 1h-imidazol possuindo actividade agonística cb1, antagonista parcial cb1 ou antagonista cb1 | |
| MXPA02006872A (es) | Nuevos derivados de imidazol. | |
| MXPA00001528A (en) | Heterocyclic vinylethers against neurological disorders | |
| RU2126403C1 (ru) | Производные фенилимидазолидинона и фармацевтическая композиция на их основе | |
| HUT61730A (en) | Process for producing 2-(imidazol-1-yl)-2-benzylethylidene aminoxy alkanecarboxylic acid derivatives and pharmaceutical compositions comprising same | |
| CZ2000460A3 (cs) | Heterocyklické vinylethery proti neurologickým chorobám | |
| HU195655B (en) | Process for producing 8-beta-ergolinyl-methyl derivatives and pharmaceutical compositions containing them | |
| CZ48094A3 (cs) | Pyrazolové deriváty, způsob jejich výroby a farmaceutické prostředky s jejich obsahem |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
| OBST | Application withdrawn |