SK3492002A3 - Benzisoxazolyl-, pyridoisoxazolyl- and benzthienyl-phenoxy derivatives useful as d4 antagonists - Google Patents
Benzisoxazolyl-, pyridoisoxazolyl- and benzthienyl-phenoxy derivatives useful as d4 antagonists Download PDFInfo
- Publication number
- SK3492002A3 SK3492002A3 SK349-2002A SK3492002A SK3492002A3 SK 3492002 A3 SK3492002 A3 SK 3492002A3 SK 3492002 A SK3492002 A SK 3492002A SK 3492002 A3 SK3492002 A3 SK 3492002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- phenoxy
- isoxazol
- fluorobenzo
- propan
- Prior art date
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- -1 Benzisoxazolyl- Chemical group 0.000 title claims abstract description 379
- 239000005557 antagonist Substances 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 627
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 24
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 18
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 13
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 13
- 201000009032 substance abuse Diseases 0.000 claims abstract description 11
- 231100000736 substance abuse Toxicity 0.000 claims abstract description 11
- 208000000323 Tourette Syndrome Diseases 0.000 claims abstract description 8
- 208000027089 Parkinsonian disease Diseases 0.000 claims abstract description 7
- 206010034010 Parkinsonism Diseases 0.000 claims abstract description 7
- 208000016620 Tourette disease Diseases 0.000 claims abstract description 7
- 201000006152 substance dependence Diseases 0.000 claims abstract description 7
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 190
- 125000004432 carbon atom Chemical group C* 0.000 claims description 103
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 94
- 229910052757 nitrogen Inorganic materials 0.000 claims description 88
- 238000000034 method Methods 0.000 claims description 81
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 67
- 229910052799 carbon Inorganic materials 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000002367 halogens Chemical group 0.000 claims description 58
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 57
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 53
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 229960003638 dopamine Drugs 0.000 claims description 39
- 239000001301 oxygen Substances 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000004076 pyridyl group Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000005605 benzo group Chemical group 0.000 claims description 29
- 230000000694 effects Effects 0.000 claims description 29
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 27
- 125000001544 thienyl group Chemical group 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000002757 morpholinyl group Chemical group 0.000 claims description 18
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 17
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 16
- 230000003542 behavioural effect Effects 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- LAKCEUAITGGEKD-UHFFFAOYSA-N 6-fluoro-3-[4-(3-piperidin-1-ylpropoxy)phenyl]-1,2-benzoxazole Chemical compound N=1OC2=CC(F)=CC=C2C=1C(C=C1)=CC=C1OCCCN1CCCCC1 LAKCEUAITGGEKD-UHFFFAOYSA-N 0.000 claims description 15
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 15
- 125000003725 azepanyl group Chemical group 0.000 claims description 15
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000002541 furyl group Chemical group 0.000 claims description 15
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 15
- 125000004193 piperazinyl group Chemical group 0.000 claims description 15
- 125000005936 piperidyl group Chemical group 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 125000001041 indolyl group Chemical group 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 230000001660 hyperkinetic effect Effects 0.000 claims description 7
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- SLAMLWHELXOEJZ-UHFFFAOYSA-M 2-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-M 0.000 claims description 4
- HCNSJWYUKDBQNO-UHFFFAOYSA-N 3-piperazin-1-yl-1h-indazole Chemical compound C1CNCCN1C1=NNC2=CC=CC=C12 HCNSJWYUKDBQNO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 4
- WSCBPJBTUWYTMD-HXUWFJFHSA-N (2r)-1-[3-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-(2-phenylethylamino)propan-2-ol Chemical compound C([C@@H](O)COC=1C=C(C=CC=1)C=1C2=CC=C(F)C=C2ON=1)NCCC1=CC=CC=C1 WSCBPJBTUWYTMD-HXUWFJFHSA-N 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 206010000117 Abnormal behaviour Diseases 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 3
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- AMLAOMUUJVKBSG-WWYLULBNSA-N (1r)-1-[[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-2-hydroxypropyl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound FC1=CC=C2C(C3=CC=C(C=C3)OCC(CN[C@@H]3C4=CC=CC=C4CC3O)O)=NOC2=C1 AMLAOMUUJVKBSG-WWYLULBNSA-N 0.000 claims description 2
- XESFUKKIHDHAHT-BSMLIHBTSA-N (2r)-1-(1-adamantylamino)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound FC1=CC=C2C(C3=CC=C(C=C3)OC[C@@H](CNC34CC5CC(CC(C5)C3)C4)O)=NOC2=C1 XESFUKKIHDHAHT-BSMLIHBTSA-N 0.000 claims description 2
- AOAQZLBMBNPGGG-HWYAHNCWSA-N (2r)-1-(2,3-dihydro-1h-inden-1-ylamino)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound FC1=CC=C2C(C3=CC=C(C=C3)OC[C@@H](CNC3C4=CC=CC=C4CC3)O)=NOC2=C1 AOAQZLBMBNPGGG-HWYAHNCWSA-N 0.000 claims description 2
- BNZMCDRKWFPLCY-OAQYLSRUSA-N (2r)-1-(2,3-dihydro-1h-inden-2-ylamino)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound FC1=CC=C2C(C3=CC=C(C=C3)OC[C@@H](CNC3CC4=CC=CC=C4C3)O)=NOC2=C1 BNZMCDRKWFPLCY-OAQYLSRUSA-N 0.000 claims description 2
- NLTBUKVHVIFWSR-OAQYLSRUSA-N (2r)-1-(3,4-dihydro-1h-isoquinolin-2-yl)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound C1CC2=CC=CC=C2CN1C[C@@H](O)COC1=CC=C(C=2C3=CC=C(F)C=C3ON=2)C=C1 NLTBUKVHVIFWSR-OAQYLSRUSA-N 0.000 claims description 2
- CLJPMBFBPFSLEB-XMMPIXPASA-N (2r)-1-(4-benzylpiperidin-1-yl)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound C([C@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N(CC1)CCC1CC1=CC=CC=C1 CLJPMBFBPFSLEB-XMMPIXPASA-N 0.000 claims description 2
- QLYBZSJIVDFZBA-LJQANCHMSA-N (2r)-1-(benzylamino)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)NCC1=CC=CC=C1 QLYBZSJIVDFZBA-LJQANCHMSA-N 0.000 claims description 2
- VELGTKHRAJJMJZ-MRXNPFEDSA-N (2r)-1-(diethylamino)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound C1=CC(OC[C@H](O)CN(CC)CC)=CC=C1C1=NOC2=CC(F)=CC=C12 VELGTKHRAJJMJZ-MRXNPFEDSA-N 0.000 claims description 2
- AFYAJMJEZHVTSM-MRXNPFEDSA-N (2r)-1-[(2,6-difluorophenyl)methylamino]-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)NCC1=C(F)C=CC=C1F AFYAJMJEZHVTSM-MRXNPFEDSA-N 0.000 claims description 2
- PUYYDFFAUSSJPW-LJQANCHMSA-N (2r)-1-[(4-chlorophenyl)methylamino]-3-[3-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C(C=CC=1)C=1C2=CC=C(F)C=C2ON=1)NCC1=CC=C(Cl)C=C1 PUYYDFFAUSSJPW-LJQANCHMSA-N 0.000 claims description 2
- AAZRVGLARQZLNR-HXUWFJFHSA-N (2r)-1-[2-(cyclohexen-1-yl)ethylamino]-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)NCCC1=CCCCC1 AAZRVGLARQZLNR-HXUWFJFHSA-N 0.000 claims description 2
- YFZWWVJMVNZCGB-LJQANCHMSA-N (2r)-1-[3-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-[(4-fluorophenyl)methylamino]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C(C=CC=1)C=1C2=CC=C(F)C=C2ON=1)NCC1=CC=C(F)C=C1 YFZWWVJMVNZCGB-LJQANCHMSA-N 0.000 claims description 2
- OWBNSRIYOIUQOS-HXUWFJFHSA-N (2r)-1-[3-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-[(4-methylphenyl)methylamino]propan-2-ol Chemical compound C1=CC(C)=CC=C1CNC[C@@H](O)COC1=CC=CC(C=2C3=CC=C(F)C=C3ON=2)=C1 OWBNSRIYOIUQOS-HXUWFJFHSA-N 0.000 claims description 2
- KGBJMUICUQBAST-VGOKPJQXSA-N (2r)-1-[4-(1-benzothiophen-3-yl)phenoxy]-3-(2,3-dihydro-1h-inden-1-ylamino)propan-2-ol Chemical compound C1=CC=C2C(C3=CC=C(C=C3)OC[C@@H](CNC3C4=CC=CC=C4CC3)O)=CSC2=C1 KGBJMUICUQBAST-VGOKPJQXSA-N 0.000 claims description 2
- UEMJPQIIYFKFEQ-QGZVFWFLSA-N (2r)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-(4-methylpiperazin-1-yl)propan-2-ol Chemical compound C1CN(C)CCN1C[C@@H](O)COC1=CC=C(C=2C3=CC=C(F)C=C3ON=2)C=C1 UEMJPQIIYFKFEQ-QGZVFWFLSA-N 0.000 claims description 2
- ACPMAXIPVPVDAG-JOCHJYFZSA-N (2r)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-(4-phenylpiperazin-1-yl)propan-2-ol Chemical compound C([C@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N(CC1)CCN1C1=CC=CC=C1 ACPMAXIPVPVDAG-JOCHJYFZSA-N 0.000 claims description 2
- YWFCYWGVJYPQGH-MRXNPFEDSA-N (2r)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-morpholin-4-ylpropan-2-ol Chemical compound C([C@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N1CCOCC1 YWFCYWGVJYPQGH-MRXNPFEDSA-N 0.000 claims description 2
- OOJFWBMXOBUONA-QGZVFWFLSA-N (2r)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N1CCCCC1 OOJFWBMXOBUONA-QGZVFWFLSA-N 0.000 claims description 2
- UTRAWWVCFCMAFH-LJQANCHMSA-N (2r)-1-[cyclohexyl(methyl)amino]-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)N(C)C1CCCCC1 UTRAWWVCFCMAFH-LJQANCHMSA-N 0.000 claims description 2
- ACPMAXIPVPVDAG-QFIPXVFZSA-N (2s)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-(4-phenylpiperazin-1-yl)propan-2-ol Chemical compound C([C@@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N(CC1)CCN1C1=CC=CC=C1 ACPMAXIPVPVDAG-QFIPXVFZSA-N 0.000 claims description 2
- MLXDTGLDYWMPKR-QHCPKHFHSA-N (2s)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-(4-phenylpiperidin-1-yl)propan-2-ol Chemical compound C([C@@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N(CC1)CCC1C1=CC=CC=C1 MLXDTGLDYWMPKR-QHCPKHFHSA-N 0.000 claims description 2
- XJNRQAORENAYKS-NRFANRHFSA-N (2s)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-[4-(4-fluorophenoxy)piperidin-1-yl]propan-2-ol Chemical compound C([C@@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N(CC1)CCC1OC1=CC=C(F)C=C1 XJNRQAORENAYKS-NRFANRHFSA-N 0.000 claims description 2
- NPGZDAXOABKHGB-NRFANRHFSA-N (2s)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-[methyl(2-phenylethyl)amino]propan-2-ol Chemical compound C([C@H](O)COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)N(C)CCC1=CC=CC=C1 NPGZDAXOABKHGB-NRFANRHFSA-N 0.000 claims description 2
- YWFCYWGVJYPQGH-INIZCTEOSA-N (2s)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-3-morpholin-4-ylpropan-2-ol Chemical compound C([C@@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N1CCOCC1 YWFCYWGVJYPQGH-INIZCTEOSA-N 0.000 claims description 2
- UVHIXFLHRSYNJH-QFIPXVFZSA-N 1-[(2s)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-2-hydroxypropyl]-4-phenylpiperidin-4-ol Chemical compound C([C@@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N(CC1)CCC1(O)C1=CC=CC=C1 UVHIXFLHRSYNJH-QFIPXVFZSA-N 0.000 claims description 2
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 2
- FIVGIVFRRDTEEF-JOCHJYFZSA-N 2-[4-[(2r)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-2-hydroxypropyl]piperazin-1-yl]benzonitrile Chemical compound C([C@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N(CC1)CCN1C1=CC=CC=C1C#N FIVGIVFRRDTEEF-JOCHJYFZSA-N 0.000 claims description 2
- FIVGIVFRRDTEEF-QFIPXVFZSA-N 2-[4-[(2s)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-2-hydroxypropyl]piperazin-1-yl]benzonitrile Chemical compound C([C@@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N(CC1)CCN1C1=CC=CC=C1C#N FIVGIVFRRDTEEF-QFIPXVFZSA-N 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- NSMKLESWDQYEII-UHFFFAOYSA-N 3-[4-[2-(3,4-dihydro-1h-isoquinolin-2-yl)ethoxy]phenyl]-6-fluoro-1,2-benzoxazole Chemical compound C1CC2=CC=CC=C2CN1CCOC(C=C1)=CC=C1C1=NOC2=CC(F)=CC=C21 NSMKLESWDQYEII-UHFFFAOYSA-N 0.000 claims description 2
- XMGOYRBXGQCBSW-JOCHJYFZSA-N 4-(4-chlorophenyl)-1-[(2r)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)phenoxy]-2-hydroxypropyl]piperidin-4-ol Chemical compound C([C@H](COC=1C=CC(=CC=1)C=1C2=CC=C(F)C=C2ON=1)O)N(CC1)CCC1(O)C1=CC=C(Cl)C=C1 XMGOYRBXGQCBSW-JOCHJYFZSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- IHCOITSCPBIHNI-UHFFFAOYSA-N 6-fluoro-3-[4-(2-piperidin-1-ylethoxy)phenyl]-1,2-benzoxazole Chemical compound N=1OC2=CC(F)=CC=C2C=1C(C=C1)=CC=C1OCCN1CCCCC1 IHCOITSCPBIHNI-UHFFFAOYSA-N 0.000 claims description 2
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- 230000003042 antagnostic effect Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 claims description 2
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- 239000012266 salt solution Substances 0.000 description 1
- 208000022610 schizoaffective disease Diseases 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000001103 thalamus Anatomy 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000001755 vocal effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P25/14—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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Addiction (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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US39593799A | 1999-09-14 | 1999-09-14 | |
PCT/US2000/024961 WO2001019821A1 (en) | 1999-09-14 | 2000-09-13 | Benzisoxazolyl-, pyridoisoxazolyl- and benzthienyl-phenoxy derivatives useful as d4 antagonists |
Publications (1)
Publication Number | Publication Date |
---|---|
SK3492002A3 true SK3492002A3 (en) | 2002-12-03 |
Family
ID=23565162
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK349-2002A SK3492002A3 (en) | 1999-09-14 | 2000-09-13 | Benzisoxazolyl-, pyridoisoxazolyl- and benzthienyl-phenoxy derivatives useful as d4 antagonists |
Country Status (24)
Country | Link |
---|---|
EP (1) | EP1216244B1 (hu) |
JP (1) | JP4806149B2 (hu) |
KR (1) | KR20020027648A (hu) |
AT (1) | ATE247110T1 (hu) |
AU (1) | AU7479400A (hu) |
BR (1) | BR0014000A (hu) |
CA (1) | CA2383332C (hu) |
CZ (1) | CZ2002898A3 (hu) |
DE (1) | DE60004543T2 (hu) |
DK (1) | DK1216244T3 (hu) |
EA (1) | EA200200356A1 (hu) |
EE (1) | EE200200134A (hu) |
ES (1) | ES2200934T3 (hu) |
HR (1) | HRP20020219A2 (hu) |
HU (1) | HUP0202706A3 (hu) |
IL (1) | IL148622A0 (hu) |
MX (1) | MXPA02002694A (hu) |
NO (1) | NO20021256L (hu) |
NZ (1) | NZ517516A (hu) |
PL (1) | PL354514A1 (hu) |
PT (1) | PT1216244E (hu) |
SK (1) | SK3492002A3 (hu) |
WO (1) | WO2001019821A1 (hu) |
ZA (1) | ZA200201757B (hu) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
GB201004311D0 (en) * | 2010-03-15 | 2010-04-28 | Proximagen Ltd | New enzyme inhibitor compounds |
AU2011376717A1 (en) | 2011-09-14 | 2014-03-20 | Proximagen Limited | New enzyme inhibitor compounds |
EP2935243B1 (en) | 2012-12-21 | 2018-03-14 | Epizyme, Inc. | Prmt5 inhibitors containing a dihydro- or tetrahydroisoquinoline and uses thereof |
US9611257B2 (en) | 2012-12-21 | 2017-04-04 | Epizyme, Inc. | PRMT5 inhibitors and uses thereof |
US9908887B2 (en) | 2012-12-21 | 2018-03-06 | Epizyme, Inc. | PRMT5 inhibitors and uses thereof |
US9221794B2 (en) | 2012-12-21 | 2015-12-29 | Epizyme, Inc. | PRMT5 inhibitors and uses thereof |
LT2935222T (lt) | 2012-12-21 | 2018-12-27 | Epizyme, Inc. | Prmt5 slopikliai ir jų panaudojimas |
WO2015200680A2 (en) * | 2014-06-25 | 2015-12-30 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
AU2015301196A1 (en) | 2014-08-04 | 2017-01-12 | Epizyme, Inc. | PRMT5 inhibitors and uses thereof |
WO2017205766A1 (en) | 2016-05-27 | 2017-11-30 | Pharmacyclics Llc | Inhibitors of interleukin-1 receptor-associated kinase |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5114936A (en) * | 1990-08-23 | 1992-05-19 | Hoechst-Roussel Pharmaceuticals Incorporated | 6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5h)-ones and -ols, compositions and pharmaceutical use |
US5147881A (en) * | 1990-11-14 | 1992-09-15 | Pfizer Inc | 4-(1,2-benzisoxazolyl)piperidine antipsychotic agents |
US5177088A (en) * | 1991-04-17 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 3-(pyridinylamino)-indoles |
US5225412A (en) * | 1991-04-29 | 1993-07-06 | Hoechst-Roussel Pharmaceuticals Incorporated | Benzoisothiazole-and benzisoxazole-3-carboxamides |
US5576319A (en) * | 1993-03-01 | 1996-11-19 | Merck, Sharp & Dohme Ltd. | Pyrrolo-pyridine derivatives |
HUP9900611A3 (en) * | 1995-12-21 | 2000-09-28 | Pfizer | 2,7-substituted octahydro-pyrrolo[1,2-a]pyrazine derivatives, pharmaceutical compositions containing them and intermediates for the preparation of the compounds |
ATE227278T1 (de) * | 1996-04-19 | 2002-11-15 | Akzo Nobel Nv | Substituierte benzylamine-derivate und ihre verwendung zur behandlung von depression |
FR2749304B1 (fr) * | 1996-06-04 | 1998-06-26 | Adir | Nouveaux derives du 3-(piperid-4-yl)1,2-benzisoxazole et du 3-(piperazin-4-yl)1,2-benzisoxazole, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
JPH1095770A (ja) * | 1996-09-20 | 1998-04-14 | Taisho Pharmaceut Co Ltd | 4−ベンジリデンピペリジン誘導体 |
PT1054885E (pt) * | 1998-02-09 | 2007-10-03 | Duphar Int Res | Derivativos de benzisoxazole tendo uma actividade d4-antagonista |
-
2000
- 2000-09-13 NZ NZ517516A patent/NZ517516A/en not_active Application Discontinuation
- 2000-09-13 DK DK00963370T patent/DK1216244T3/da active
- 2000-09-13 CA CA002383332A patent/CA2383332C/en not_active Expired - Fee Related
- 2000-09-13 ES ES00963370T patent/ES2200934T3/es not_active Expired - Lifetime
- 2000-09-13 EA EA200200356A patent/EA200200356A1/ru unknown
- 2000-09-13 SK SK349-2002A patent/SK3492002A3/sk unknown
- 2000-09-13 BR BR0014000-7A patent/BR0014000A/pt not_active IP Right Cessation
- 2000-09-13 IL IL14862200A patent/IL148622A0/xx unknown
- 2000-09-13 EP EP00963370A patent/EP1216244B1/en not_active Expired - Lifetime
- 2000-09-13 PT PT00963370T patent/PT1216244E/pt unknown
- 2000-09-13 CZ CZ2002898A patent/CZ2002898A3/cs unknown
- 2000-09-13 KR KR1020027003367A patent/KR20020027648A/ko not_active Application Discontinuation
- 2000-09-13 PL PL00354514A patent/PL354514A1/xx unknown
- 2000-09-13 JP JP2001523398A patent/JP4806149B2/ja not_active Expired - Fee Related
- 2000-09-13 AU AU74794/00A patent/AU7479400A/en not_active Abandoned
- 2000-09-13 WO PCT/US2000/024961 patent/WO2001019821A1/en not_active Application Discontinuation
- 2000-09-13 EE EEP200200134A patent/EE200200134A/xx unknown
- 2000-09-13 HU HU0202706A patent/HUP0202706A3/hu unknown
- 2000-09-13 DE DE60004543T patent/DE60004543T2/de not_active Expired - Lifetime
- 2000-09-13 MX MXPA02002694A patent/MXPA02002694A/es active IP Right Grant
- 2000-09-13 AT AT00963370T patent/ATE247110T1/de not_active IP Right Cessation
-
2002
- 2002-03-01 ZA ZA200201757A patent/ZA200201757B/xx unknown
- 2002-03-12 HR HR20020219A patent/HRP20020219A2/xx not_active Application Discontinuation
- 2002-03-13 NO NO20021256A patent/NO20021256L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
PT1216244E (pt) | 2003-12-31 |
AU7479400A (en) | 2001-04-17 |
DE60004543T2 (de) | 2004-06-17 |
EE200200134A (et) | 2003-04-15 |
NZ517516A (en) | 2003-11-28 |
ES2200934T3 (es) | 2004-03-16 |
EP1216244A1 (en) | 2002-06-26 |
PL354514A1 (en) | 2004-01-26 |
NO20021256D0 (no) | 2002-03-13 |
CA2383332C (en) | 2006-01-10 |
NO20021256L (no) | 2002-05-14 |
DK1216244T3 (da) | 2003-11-17 |
CZ2002898A3 (cs) | 2002-07-17 |
HRP20020219A2 (en) | 2004-04-30 |
KR20020027648A (ko) | 2002-04-13 |
BR0014000A (pt) | 2002-05-14 |
JP2003509421A (ja) | 2003-03-11 |
EA200200356A1 (ru) | 2002-10-31 |
ATE247110T1 (de) | 2003-08-15 |
WO2001019821A1 (en) | 2001-03-22 |
EP1216244B1 (en) | 2003-08-13 |
ZA200201757B (en) | 2003-08-27 |
IL148622A0 (en) | 2002-09-12 |
HUP0202706A2 (hu) | 2002-12-28 |
MXPA02002694A (es) | 2002-07-30 |
JP4806149B2 (ja) | 2011-11-02 |
CA2383332A1 (en) | 2001-03-22 |
DE60004543D1 (de) | 2003-09-18 |
HUP0202706A3 (en) | 2004-12-28 |
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