DE19816880A1 - Neue Diphenyl-substituierte 5-Ring-Heterocyclen, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel - Google Patents
Neue Diphenyl-substituierte 5-Ring-Heterocyclen, Verfahren zu ihrer Herstellung sowie deren Verwendung als ArzneimittelInfo
- Publication number
- DE19816880A1 DE19816880A1 DE19816880A DE19816880A DE19816880A1 DE 19816880 A1 DE19816880 A1 DE 19816880A1 DE 19816880 A DE19816880 A DE 19816880A DE 19816880 A DE19816880 A DE 19816880A DE 19816880 A1 DE19816880 A1 DE 19816880A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- optionally
- phenyl
- hydrogen
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 diaryl substituted heterocyclic compounds Chemical class 0.000 title claims abstract description 59
- 208000015122 neurodegenerative disease Diseases 0.000 title claims description 8
- 201000006474 Brain Ischemia Diseases 0.000 title claims description 7
- 206010008120 Cerebral ischaemia Diseases 0.000 title description 2
- 206010008118 cerebral infarction Diseases 0.000 title description 2
- 229940098747 AMPA receptor antagonist Drugs 0.000 title 1
- 239000000775 AMPA receptor antagonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 53
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 49
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 43
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 42
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 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 abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 150000002431 hydrogen Chemical class 0.000 claims description 44
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 42
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 42
- 239000000460 chlorine Substances 0.000 claims description 41
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 239000011737 fluorine Substances 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 9
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 9
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 9
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 150000001204 N-oxides Chemical class 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000004770 neurodegeneration Effects 0.000 claims description 7
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 6
- 150000003852 triazoles Chemical class 0.000 claims description 6
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 5
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 5
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 4
- JKNSMBZZZFGYCB-UHFFFAOYSA-N 4,5-dihydrooxadiazole Chemical compound C1CN=NO1 JKNSMBZZZFGYCB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
- UUZJJNBYJDFQHL-UHFFFAOYSA-N 1,2,3-triazolidine Chemical compound C1CNNN1 UUZJJNBYJDFQHL-UHFFFAOYSA-N 0.000 claims description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000012039 electrophile Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000324 neuroprotective effect Effects 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 5
- 229910006069 SO3H Inorganic materials 0.000 abstract 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000002904 solvent Substances 0.000 description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- 239000012074 organic phase Substances 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 239000000741 silica gel Substances 0.000 description 25
- 229910002027 silica gel Inorganic materials 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000010992 reflux Methods 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 238000000746 purification Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 229920002261 Corn starch Polymers 0.000 description 7
- 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 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 239000008120 corn starch Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 206010021143 Hypoxia Diseases 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 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
- ZJABPUSDYOXUKS-UHFFFAOYSA-N 1-(2-phenylmethoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 ZJABPUSDYOXUKS-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
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000000546 pharmaceutical excipient 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
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZYDSBZHDRVWPKC-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-phenyl-1,2,4-triazole Chemical compound COC1=CC=CC=C1N1N=C(C=2C=CC=CC=2)N=C1 ZYDSBZHDRVWPKC-UHFFFAOYSA-N 0.000 description 3
- MHSHMGJHXSPXDH-UHFFFAOYSA-N 2-bromo-1-(2-phenylmethoxyphenyl)ethanone Chemical compound BrCC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 MHSHMGJHXSPXDH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 3
- 102000003678 AMPA Receptors Human genes 0.000 description 3
- 108090000078 AMPA Receptors Proteins 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
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 229930195712 glutamate Natural products 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 230000000302 ischemic effect Effects 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 235000015424 sodium Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 2
- ZHFSNPDZPPTJAU-UHFFFAOYSA-N 1,3-diphenyl-1,2,4-triazole Chemical compound C1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 ZHFSNPDZPPTJAU-UHFFFAOYSA-N 0.000 description 2
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 2
- WGCNTPLHNJZGKA-UHFFFAOYSA-N 2-(1-phenyl-1,2,4-triazol-3-yl)phenol Chemical compound OC1=CC=CC=C1C1=NN(C=2C=CC=CC=2)C=N1 WGCNTPLHNJZGKA-UHFFFAOYSA-N 0.000 description 2
- XKJNWCYKCIEFOO-UHFFFAOYSA-N 2-(2-phenyl-1,3-oxazol-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=COC(C=2C=CC=CC=2)=N1 XKJNWCYKCIEFOO-UHFFFAOYSA-N 0.000 description 2
- ZUIWWDMDVBYWHG-UHFFFAOYSA-N 2-(2-phenyl-1,3-oxazol-5-yl)phenol Chemical compound OC1=CC=CC=C1C1=CN=C(C=2C=CC=CC=2)O1 ZUIWWDMDVBYWHG-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- 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
- 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
- C07D231/14—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
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)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19816880A DE19816880A1 (de) | 1998-04-17 | 1998-04-17 | Neue Diphenyl-substituierte 5-Ring-Heterocyclen, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| IT98MI000818A IT1300055B1 (it) | 1998-04-17 | 1998-04-17 | Eterocicli con anello a 5 termini difenil-sostituiti loro procedimento di preparazione e loro impiego come farmici |
| US09/290,931 US6255327B1 (en) | 1998-02-01 | 1999-04-13 | Diphenyl-substituted heterocycles, processes for preparing them and their use as pharmaceutical compositions |
| JP2000544653A JP4589531B2 (ja) | 1998-04-17 | 1999-04-14 | 新規ジフェニル置換５員環複素環化合物、それらの製造方法及び薬物としてのそれらの使用 |
| DE59909917T DE59909917D1 (de) | 1998-04-17 | 1999-04-14 | Diphenyl-substituierte 5-ring-heterocyclen, verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel |
| ES99920661T ES2224652T3 (es) | 1998-04-17 | 1999-04-14 | Heterociclos de 5 anillos sustituidos con difenilo, procedimiento para su preparacion, asi como su empleo como medicamentos. |
| CA002322195A CA2322195C (en) | 1998-04-17 | 1999-04-14 | Novel diphenyl-substituted 5-ring-heterocycles, method for producing them and their use as medicaments |
| PCT/EP1999/002496 WO1999054314A1 (de) | 1998-04-17 | 1999-04-14 | Neue diphenyl-substituierte 5-ring-heterocyclen, verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel |
| AT99920661T ATE270665T1 (de) | 1998-04-17 | 1999-04-14 | Diphenyl-substituierte 5-ring-heterocyclen, verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel |
| MXPA00009474A MXPA00009474A (es) | 1998-04-17 | 1999-04-14 | Nuevos heterociclos de 5 anillos sustituidos con difenilo, procedimientos para su preparacion, asi como su empleo como medicamentos. |
| EP99920661A EP1071670B1 (de) | 1998-04-17 | 1999-04-14 | Diphenyl-substituierte 5-ring-heterocyclen, verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19816880A DE19816880A1 (de) | 1998-04-17 | 1998-04-17 | Neue Diphenyl-substituierte 5-Ring-Heterocyclen, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| IT98MI000818A IT1300055B1 (it) | 1998-04-17 | 1998-04-17 | Eterocicli con anello a 5 termini difenil-sostituiti loro procedimento di preparazione e loro impiego come farmici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19816880A1 true DE19816880A1 (de) | 1999-10-21 |
Family
ID=26045525
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19816880A Withdrawn DE19816880A1 (de) | 1998-02-01 | 1998-04-17 | Neue Diphenyl-substituierte 5-Ring-Heterocyclen, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| DE59909917T Expired - Lifetime DE59909917D1 (de) | 1998-04-17 | 1999-04-14 | Diphenyl-substituierte 5-ring-heterocyclen, verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59909917T Expired - Lifetime DE59909917D1 (de) | 1998-04-17 | 1999-04-14 | Diphenyl-substituierte 5-ring-heterocyclen, verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6255327B1 (enExample) |
| EP (1) | EP1071670B1 (enExample) |
| JP (1) | JP4589531B2 (enExample) |
| AT (1) | ATE270665T1 (enExample) |
| CA (1) | CA2322195C (enExample) |
| DE (2) | DE19816880A1 (enExample) |
| ES (1) | ES2224652T3 (enExample) |
| IT (1) | IT1300055B1 (enExample) |
| MX (1) | MXPA00009474A (enExample) |
| WO (1) | WO1999054314A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1070708B1 (en) * | 1999-07-21 | 2004-01-14 | F. Hoffmann-La Roche Ag | Triazole derivatives |
| US6579880B2 (en) * | 2000-06-06 | 2003-06-17 | Ortho-Mcneil Pharmaceutical, Inc. | Isoxazoles and oxadiazoles as anti-inflammatory inhibitors of IL-8 |
| US6610723B2 (en) * | 2001-01-29 | 2003-08-26 | Hoffmann-La Roche Inc. | Imidazole derivatives |
| US8829198B2 (en) * | 2007-10-31 | 2014-09-09 | Proteotech Inc | Compounds, compositions and methods for the treatment of beta-amyloid diseases and synucleinopathies |
| GB0303503D0 (en) * | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| AU2004289694B2 (en) * | 2003-11-10 | 2010-05-13 | Merck Sharp & Dohme Corp. | Substituted triazoles as sodium channel blockers |
| JP2007527917A (ja) * | 2004-03-08 | 2007-10-04 | ワイス | イオンチャンネルモジュレーター |
| DOP2005000123A (es) * | 2004-07-02 | 2011-07-15 | Merck Sharp & Dohme | Inhibidores de cetp |
| EP1815206B1 (en) | 2004-10-13 | 2016-04-06 | PTC Therapeutics, Inc. | Compounds for nonsense suppression, and methods for their use |
| WO2008131148A1 (en) * | 2007-04-19 | 2008-10-30 | The Trustees Of The University Of Pennsylvania | Diphenyl-heteroaryl derivatives and their use for binding and imaging amyloid plaques |
| WO2009111611A2 (en) | 2008-03-05 | 2009-09-11 | Proteotech Inc. | Compounds, compositions and methods for the treatment of islet amyloid polypeptide (iapp) accumulation in diabetes |
| CN102060798A (zh) * | 2011-01-04 | 2011-05-18 | 复旦大学 | 2-(1-氢-4-四唑)-4′- 甲基联苯及其衍生物的合成方法 |
| US8865754B2 (en) | 2011-03-03 | 2014-10-21 | Proteotech Inc. | Compounds for the treatment of neurodegenerative diseases |
| WO2016024587A1 (ja) * | 2014-08-13 | 2016-02-18 | 日本曹達株式会社 | ジアリールイミダゾール化合物および有害生物防除剤 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5305E (fr) * | 1905-06-17 | 1906-02-22 | Edouard Pellorce | Appareil électrique pour l'allumage des moteurs à explosion |
| DE1545806A1 (de) * | 1951-01-28 | 1969-11-27 | Hoechst Ag | Verfahren zur Herstellung von heterocyclischen Verbindungen |
| FR1356901A (fr) * | 1958-03-13 | 1964-04-03 | Nouveaux aminoétheroxydes, aminothioéthers et aminoesters dérivés du pyrrole, etleur procédé de préparation | |
| FR2152345A1 (en) * | 1971-09-06 | 1973-04-27 | Roussel Uclaf | Alpha-(2-thiazolyl)oxyalkanoic acids and derivatives - - with analgesic,antiinflammatory and antipyretic activity |
| FR2244462A1 (en) * | 1973-09-25 | 1975-04-18 | Delalande Sa | Antihypertensive, 5-hydroxy methyl 1,2,4-triazoles - prepd. from aniline and a hydroxy methyl 1,3,4-oxadiazole |
| SU753084A1 (ru) * | 1979-03-23 | 1983-01-23 | Ростовский Ордена Трудового Красного Знамени Государственный Университет | Способ получени 1-[2-алкил(аралкил)аминоарил -4-арилимидазолов общей формулы |
| US4370336A (en) * | 1979-06-11 | 1983-01-25 | Gruppo Lepetit S.P.A. | 3,5-Disubstituted-1H-1,2,4-triazole derivatives as antifertility agents |
| US4379155A (en) * | 1979-06-11 | 1983-04-05 | Gruppo Lepetit S.P.A. | 3,5-Disubstituted-1H-1,2,4-triazole derivatives |
| US4826868A (en) * | 1986-05-29 | 1989-05-02 | Ortho Pharmaceutical Corporation | 1,5-Diaryl-3-substituted pyrazoles pharmaceutical compositions and use |
| JP2928307B2 (ja) * | 1989-02-03 | 1999-08-03 | エーザイ株式会社 | ピロリジン誘導体 |
| CA2074933C (en) * | 1990-11-30 | 2002-12-03 | Masatoshi Chihiro | Thiazole derivatives as active superoxide radical inhibitors |
| FR2678938B1 (fr) * | 1991-07-10 | 1993-10-08 | Rhone Poulenc Rorer Sa | Derives de pyrrolidine, leur preparation et les medicaments les contenant. |
| IL104311A (en) * | 1992-02-05 | 1997-07-13 | Fujisawa Pharmaceutical Co | Pyrazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5411977A (en) * | 1993-03-31 | 1995-05-02 | The Dupont Merck Pharmaceutical Company | Substituted 2,5-diaryl-4-isothiazolin-3-ones as antiinflammatory and antithrombotic agents |
| DE19528189A1 (de) * | 1995-08-01 | 1997-02-06 | Basf Ag | Benzolderivate mit einem heterocyclischen Rest |
| ATE240728T1 (de) * | 1996-10-07 | 2003-06-15 | Lilly Co Eli | Neue verbindungen nutlich als neuroschützende mittel |
| DE19643037A1 (de) | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| WO1998027108A2 (en) * | 1996-12-16 | 1998-06-25 | Fujisawa Pharmaceutical Co., Ltd. | New amide compounds and their use as nitric oxide synthase inhibitors |
-
1998
- 1998-04-17 DE DE19816880A patent/DE19816880A1/de not_active Withdrawn
- 1998-04-17 IT IT98MI000818A patent/IT1300055B1/it active IP Right Grant
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1999
- 1999-04-13 US US09/290,931 patent/US6255327B1/en not_active Expired - Lifetime
- 1999-04-14 MX MXPA00009474A patent/MXPA00009474A/es active IP Right Grant
- 1999-04-14 WO PCT/EP1999/002496 patent/WO1999054314A1/de not_active Ceased
- 1999-04-14 JP JP2000544653A patent/JP4589531B2/ja not_active Expired - Fee Related
- 1999-04-14 DE DE59909917T patent/DE59909917D1/de not_active Expired - Lifetime
- 1999-04-14 AT AT99920661T patent/ATE270665T1/de active
- 1999-04-14 CA CA002322195A patent/CA2322195C/en not_active Expired - Fee Related
- 1999-04-14 EP EP99920661A patent/EP1071670B1/de not_active Expired - Lifetime
- 1999-04-14 ES ES99920661T patent/ES2224652T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999054314A1 (de) | 1999-10-28 |
| CA2322195C (en) | 2008-02-26 |
| CA2322195A1 (en) | 1999-10-28 |
| ITMI980818A1 (it) | 1999-10-17 |
| JP2002512235A (ja) | 2002-04-23 |
| US6255327B1 (en) | 2001-07-03 |
| ATE270665T1 (de) | 2004-07-15 |
| EP1071670B1 (de) | 2004-07-07 |
| JP4589531B2 (ja) | 2010-12-01 |
| IT1300055B1 (it) | 2000-04-05 |
| EP1071670A1 (de) | 2001-01-31 |
| MXPA00009474A (es) | 2002-08-12 |
| ES2224652T3 (es) | 2005-03-01 |
| DE59909917D1 (de) | 2004-08-12 |
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