JP2002534515A5 - - Google Patents
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- Publication number
- JP2002534515A5 JP2002534515A5 JP2000593597A JP2000593597A JP2002534515A5 JP 2002534515 A5 JP2002534515 A5 JP 2002534515A5 JP 2000593597 A JP2000593597 A JP 2000593597A JP 2000593597 A JP2000593597 A JP 2000593597A JP 2002534515 A5 JP2002534515 A5 JP 2002534515A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- iodo
- phenylamino
- fluoro
- 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.)
- Abandoned
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- -1 (amino) sulfonyl Chemical group 0.000 description 34
- 150000001875 compounds Chemical class 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- ZZLTXWMPUKJTFS-UHFFFAOYSA-N 2-hydroxy-3h-oxadiazole Chemical compound ON1NC=CO1 ZZLTXWMPUKJTFS-UHFFFAOYSA-N 0.000 description 4
- 229910004013 NO 2 Inorganic materials 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 description 1
- WFDALXPULMQOGY-UHFFFAOYSA-N 1-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-4-methyltetrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1N1C(=O)N(C)N=N1 WFDALXPULMQOGY-UHFFFAOYSA-N 0.000 description 1
- VJRIPOXOZAXBJJ-UHFFFAOYSA-N 1-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]triazol-4-ol Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1N1N=NC(O)=C1 VJRIPOXOZAXBJJ-UHFFFAOYSA-N 0.000 description 1
- FVTJNFQCZSPAPJ-UHFFFAOYSA-N 1-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]-4-methyltetrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1N1C(=O)N(C)N=N1 FVTJNFQCZSPAPJ-UHFFFAOYSA-N 0.000 description 1
- COSUQWQBWJNFAU-UHFFFAOYSA-N 1-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]triazol-4-ol Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1N1N=NC(O)=C1 COSUQWQBWJNFAU-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- JXBKZAYVMSNKHA-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-olate Chemical compound OC=1N=NNN=1 JXBKZAYVMSNKHA-UHFFFAOYSA-N 0.000 description 1
- QGDAAPPGTYAIIW-UHFFFAOYSA-N 2,3,4-trifluoro-n-(4-iodo-2-methylphenyl)-6-(2h-tetrazol-5-yl)aniline Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=NN=NN1 QGDAAPPGTYAIIW-UHFFFAOYSA-N 0.000 description 1
- JVQDJRVZPPUWHQ-UHFFFAOYSA-N 2,3-difluoro-n-(4-iodo-2-methylphenyl)-6-(2h-tetrazol-5-yl)aniline Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=NN=NN1 JVQDJRVZPPUWHQ-UHFFFAOYSA-N 0.000 description 1
- XWZXFBYXIPRUSM-UHFFFAOYSA-N 2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-5-fluoro-n-(4-iodo-2-methylphenyl)-4-nitroaniline Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=NC(C)(C)CO1 XWZXFBYXIPRUSM-UHFFFAOYSA-N 0.000 description 1
- SOUZEYPLRWUWLG-UHFFFAOYSA-N 2-methyl-4-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-1h-pyrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=CN(C)N=C1O SOUZEYPLRWUWLG-UHFFFAOYSA-N 0.000 description 1
- FLWVAHBGRKYNEE-UHFFFAOYSA-N 2-sulfanyl-3h-oxadiazole Chemical compound SN1NC=CO1 FLWVAHBGRKYNEE-UHFFFAOYSA-N 0.000 description 1
- NBNQOWVYEXFQJC-UHFFFAOYSA-N 2-sulfanyl-3h-thiadiazole Chemical compound SN1NC=CS1 NBNQOWVYEXFQJC-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- OKWVBTUWSSEFQJ-UHFFFAOYSA-N 3-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-2h-1,2-oxazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=CC(=O)ON1 OKWVBTUWSSEFQJ-UHFFFAOYSA-N 0.000 description 1
- ZBHZDNXGSWNMOI-UHFFFAOYSA-N 3-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]-2h-1,2-oxazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=CC(=O)ON1 ZBHZDNXGSWNMOI-UHFFFAOYSA-N 0.000 description 1
- VIDTXRFNAHTNJK-UHFFFAOYSA-N 3-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-2h-1,2-oxazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=CC(=O)ON1 VIDTXRFNAHTNJK-UHFFFAOYSA-N 0.000 description 1
- WOLJKRQMWVGOCZ-UHFFFAOYSA-N 4-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-4h-1,2-oxazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1C(=O)ON=C1 WOLJKRQMWVGOCZ-UHFFFAOYSA-N 0.000 description 1
- BZHFBSLDGULCTM-UHFFFAOYSA-N 4-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-oxazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=CON=C1O BZHFBSLDGULCTM-UHFFFAOYSA-N 0.000 description 1
- VVPPJZLDNIBPQW-UHFFFAOYSA-N 4-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-thiazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=CSN=C1O VVPPJZLDNIBPQW-UHFFFAOYSA-N 0.000 description 1
- ZICMEXBGXFWOAD-UHFFFAOYSA-N 4-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-2-methyl-1h-pyrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=CN(C)N=C1O ZICMEXBGXFWOAD-UHFFFAOYSA-N 0.000 description 1
- JROAVHUBFWGXMF-UHFFFAOYSA-N 4-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-4h-1,2-oxazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1C(=O)ON=C1 JROAVHUBFWGXMF-UHFFFAOYSA-N 0.000 description 1
- GIGIQHHCOYTASR-UHFFFAOYSA-N 4-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]-1,2-oxazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=CON=C1O GIGIQHHCOYTASR-UHFFFAOYSA-N 0.000 description 1
- HHDMWXPOIBGYHM-UHFFFAOYSA-N 4-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]-1,2-thiazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=CSN=C1O HHDMWXPOIBGYHM-UHFFFAOYSA-N 0.000 description 1
- YZEHYLDQCQSQOE-UHFFFAOYSA-N 4-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]-2-methyl-1h-pyrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=CN(C)N=C1O YZEHYLDQCQSQOE-UHFFFAOYSA-N 0.000 description 1
- GKBNTEJRQLGWFH-UHFFFAOYSA-N 4-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-oxazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=CON=C1O GKBNTEJRQLGWFH-UHFFFAOYSA-N 0.000 description 1
- BYRWCWFJIUSCAW-UHFFFAOYSA-N 4-[5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-oxazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=CON=C1O BYRWCWFJIUSCAW-UHFFFAOYSA-N 0.000 description 1
- HTSYSXSLJHYHEG-UHFFFAOYSA-N 4-[5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-thiazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=CSN=C1O HTSYSXSLJHYHEG-UHFFFAOYSA-N 0.000 description 1
- ODMPNWXCSIYDGM-UHFFFAOYSA-N 4-[5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-2-methyl-1h-pyrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=CN(C)N=C1O ODMPNWXCSIYDGM-UHFFFAOYSA-N 0.000 description 1
- FJHIVVSXTRNKOO-UHFFFAOYSA-N 4-[5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-4h-1,2-oxazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1C(=O)ON=C1 FJHIVVSXTRNKOO-UHFFFAOYSA-N 0.000 description 1
- LKQJQXKFAZEKEK-UHFFFAOYSA-N 4-bromo-6-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-2,3-difluoro-n-(4-iodo-2-methylphenyl)aniline Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=NC(C)(C)CO1 LKQJQXKFAZEKEK-UHFFFAOYSA-N 0.000 description 1
- ODICWDLFZBBTMP-UHFFFAOYSA-N 5-[2-(2-amino-4-iodoanilino)-5-bromo-3,4-difluorophenyl]-1-methyltriazol-4-ol Chemical compound CN1N=NC(O)=C1C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1N ODICWDLFZBBTMP-UHFFFAOYSA-N 0.000 description 1
- ZKAUXPXXFYNVAF-UHFFFAOYSA-N 5-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=NN=C(S)N1 ZKAUXPXXFYNVAF-UHFFFAOYSA-N 0.000 description 1
- NWYZNCYPLDVQAW-UHFFFAOYSA-N 5-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-oxazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=CC(O)=NO1 NWYZNCYPLDVQAW-UHFFFAOYSA-N 0.000 description 1
- ZRJQUKGUSJAEQR-UHFFFAOYSA-N 5-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-thiazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=CC(O)=NS1 ZRJQUKGUSJAEQR-UHFFFAOYSA-N 0.000 description 1
- VUEDPIOQVJPKKV-UHFFFAOYSA-N 5-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-1,3,4-thiadiazol-2-amine Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=NN=C(N)S1 VUEDPIOQVJPKKV-UHFFFAOYSA-N 0.000 description 1
- IUPRGMLHKTURBG-UHFFFAOYSA-N 5-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-1h-1,2,4-triazol-3-amine Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=NN=C(N)N1 IUPRGMLHKTURBG-UHFFFAOYSA-N 0.000 description 1
- JFWLPLIRIUYILG-UHFFFAOYSA-N 5-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-3h-1,3,4-oxadiazole-2-thione Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=NN=C(S)O1 JFWLPLIRIUYILG-UHFFFAOYSA-N 0.000 description 1
- PAFBJOBUVMWSRW-UHFFFAOYSA-N 5-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-3h-1,3,4-thiadiazol-2-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=NN=C(O)S1 PAFBJOBUVMWSRW-UHFFFAOYSA-N 0.000 description 1
- JVDGOPGIZANNNS-UHFFFAOYSA-N 5-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=NN=C(S)S1 JVDGOPGIZANNNS-UHFFFAOYSA-N 0.000 description 1
- PWZDHDLDKBQMSH-UHFFFAOYSA-N 5-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=NN=C(O)N1 PWZDHDLDKBQMSH-UHFFFAOYSA-N 0.000 description 1
- QYIPXKFVULIACW-UHFFFAOYSA-N 5-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=NN=C(S)N1 QYIPXKFVULIACW-UHFFFAOYSA-N 0.000 description 1
- PWOCQFXWCJLJQA-UHFFFAOYSA-N 5-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-oxazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=CC(O)=NO1 PWOCQFXWCJLJQA-UHFFFAOYSA-N 0.000 description 1
- CFBVQEZLISVQOX-UHFFFAOYSA-N 5-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,3,4-oxadiazol-2-amine Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=NN=C(N)O1 CFBVQEZLISVQOX-UHFFFAOYSA-N 0.000 description 1
- KPGXOIWUBAUIQJ-UHFFFAOYSA-N 5-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,3,4-thiadiazol-2-amine Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=NN=C(N)S1 KPGXOIWUBAUIQJ-UHFFFAOYSA-N 0.000 description 1
- XECMFJLNUYXNMZ-UHFFFAOYSA-N 5-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1h-1,2,4-triazol-3-amine Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=NN=C(N)N1 XECMFJLNUYXNMZ-UHFFFAOYSA-N 0.000 description 1
- URUXUUSWKYMMRR-UHFFFAOYSA-N 5-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-3h-1,3,4-oxadiazole-2-thione Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=NN=C(S)O1 URUXUUSWKYMMRR-UHFFFAOYSA-N 0.000 description 1
- ICFOZMCFRHMZKD-UHFFFAOYSA-N 5-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-3h-1,3,4-thiadiazol-2-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=NN=C(O)S1 ICFOZMCFRHMZKD-UHFFFAOYSA-N 0.000 description 1
- KNMDLUPXTQDNHJ-UHFFFAOYSA-N 5-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=NN=C(S)S1 KNMDLUPXTQDNHJ-UHFFFAOYSA-N 0.000 description 1
- QVDLZEGBOGIZDG-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]-1,2-dihydropyrazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=CC(O)=NN1 QVDLZEGBOGIZDG-UHFFFAOYSA-N 0.000 description 1
- FLTOBUAOCWCIMO-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]-1,2-thiazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=CC(O)=NS1 FLTOBUAOCWCIMO-UHFFFAOYSA-N 0.000 description 1
- FNEGQYQGDVYILD-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=NN=C(O)N1 FNEGQYQGDVYILD-UHFFFAOYSA-N 0.000 description 1
- DKGBUVAKILBEQF-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-dihydropyrazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=CC(O)=NN1 DKGBUVAKILBEQF-UHFFFAOYSA-N 0.000 description 1
- YEPPKVMEYRBWMU-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-thiazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=CC(O)=NS1 YEPPKVMEYRBWMU-UHFFFAOYSA-N 0.000 description 1
- TZQHVGWTHYZJOI-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-1,3,4-thiadiazol-2-amine Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=NN=C(N)S1 TZQHVGWTHYZJOI-UHFFFAOYSA-N 0.000 description 1
- GVKKGNFBGDOOCY-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-3h-1,3,4-oxadiazole-2-thione Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=NN=C(S)O1 GVKKGNFBGDOOCY-UHFFFAOYSA-N 0.000 description 1
- TWCKPKFJGMRVNZ-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-3h-1,3,4-thiadiazol-2-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=NN=C(O)S1 TWCKPKFJGMRVNZ-UHFFFAOYSA-N 0.000 description 1
- HXERUZYXWJSQFS-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=NN=C(S)S1 HXERUZYXWJSQFS-UHFFFAOYSA-N 0.000 description 1
- JOBJXXCFSXRKRF-UHFFFAOYSA-N 5-[5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=NN=C(O)N1 JOBJXXCFSXRKRF-UHFFFAOYSA-N 0.000 description 1
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| PCT/US1999/030416 WO2000042029A1 (en) | 1999-01-13 | 1999-12-21 | 1-heterocycle substituted diarylamines |
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Families Citing this family (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1202732A2 (en) * | 1999-07-16 | 2002-05-08 | Warner-Lambert Company Llc | Method for treating chronic pain using mek inhibitors |
| ES2282235T3 (es) | 2000-01-31 | 2007-10-16 | Genaera Corporation | Inhibidores de la sintesis de la mucina. |
| US7345051B2 (en) | 2000-01-31 | 2008-03-18 | Genaera Corporation | Mucin synthesis inhibitors |
| EP1339702A1 (en) | 2000-03-15 | 2003-09-03 | Warner-Lambert Company | 5-amide substituted diarylamines as mek inhibitors |
| BR0109188A (pt) * | 2000-03-15 | 2003-03-18 | Warner Lambert Co | Diarilaminas 5-amida substituìdas como inibidores de mex |
| DE10017480A1 (de) * | 2000-04-07 | 2001-10-11 | Transmit Technologietransfer | Verwendung von Substanzen, die als MEK Inhibitor wirken, zur Herstellung eines Arneimittels gegen DNA- und RNA-Viren |
| AU8856201A (en) | 2000-09-01 | 2002-03-13 | Andel Inst Van | Inhibition of mitogen-activated protein kinase (mapk) pathway: a selective therapeutic strategy against melanoma |
| US7473691B2 (en) | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6613776B2 (en) | 2000-09-15 | 2003-09-02 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| EP1317450B1 (en) | 2000-09-15 | 2006-11-22 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| NZ526472A (en) | 2000-12-21 | 2004-04-30 | Vertex Pharma | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002076496A1 (en) * | 2001-03-22 | 2002-10-03 | Van Andel Institute | Anthrax lethal factor inhibits tumor growth and angiogenesis |
| EP1438295B1 (en) * | 2001-10-23 | 2012-08-15 | Merck Serono SA | Azole derivatives and pharmaceutical compositions containing them |
| ATE480527T1 (de) | 2001-12-11 | 2010-09-15 | Kyowa Hakko Kirin Co Ltd | Thiadiazolinderivate zur krebsbehandlung |
| US7235537B2 (en) * | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| SG2013013339A (en) | 2002-03-13 | 2014-12-30 | Array Biopharma Inc | N3 alkylated benzimidazole derivatives as mek inhibitors |
| MY141867A (en) | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| DK1532145T3 (da) | 2002-08-02 | 2007-01-15 | Vertex Pharma | Pyrazolpræparater der er anvendelige som inhibitorer af GSK-3 |
| US20050004186A1 (en) * | 2002-12-20 | 2005-01-06 | Pfizer Inc | MEK inhibiting compounds |
| CA2522594C (en) | 2003-04-18 | 2012-01-24 | Kyowa Hakko Kogyo Co., Ltd. | Mitotic kinesin inhibitor |
| DE10321297B4 (de) * | 2003-05-13 | 2005-11-10 | Clariant Gmbh | Flammwidrige duroplastische Massen, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
| US20070276017A1 (en) * | 2003-06-10 | 2007-11-29 | Chikara Murakata | Thiadiazoline Derivative |
| US7144907B2 (en) * | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| WO2005035512A1 (ja) * | 2003-10-10 | 2005-04-21 | Kyowa Hakko Kogyo Co., Ltd. | チアジアゾリン誘導体 |
| WO2005040098A1 (en) | 2003-10-21 | 2005-05-06 | Warner-Lambert Company Llc | Polymorphic form of n-[(r)-2,3-dihydroxy-propoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-benzamide |
| US7732616B2 (en) | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
| CA2546353A1 (en) * | 2003-11-19 | 2005-06-09 | Array Biopharma Inc. | Bicyclic inhibitors of mek and methods of use thereof |
| US7517994B2 (en) | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| CA2546754A1 (en) * | 2003-11-21 | 2005-06-09 | Array Biopharma Inc. | Akt protein kinase inhibitors |
| PL382308A1 (pl) * | 2004-08-25 | 2007-08-20 | Targegen, Inc. | Związki heterocykliczne i sposoby stosowania |
| US7449486B2 (en) * | 2004-10-19 | 2008-11-11 | Array Biopharma Inc. | Mitotic kinesin inhibitors and methods of use thereof |
| MX2007004781A (es) * | 2004-10-20 | 2007-05-11 | Applied Research Systems | Derivados de 3-arilamino piridina. |
| WO2006101102A1 (ja) * | 2005-03-22 | 2006-09-28 | Kyowa Hakko Kogyo Co., Ltd. | 固形腫瘍治療剤 |
| EP1870404A4 (en) * | 2005-03-22 | 2010-07-14 | Kyowa Hakko Kirin Co Ltd | MEANS FOR THE TREATMENT OF A HEMATOPOIETIC TUMOR |
| SG177981A1 (en) | 2005-05-18 | 2012-02-28 | Array Biopharma Inc | 4-(phenylamino)-6-oxo-1, 6-dihydropyridazine-3-carboxamide derivatives as mek inhibitors for the treatment of hyperproliferative diseases |
| EP1908755A4 (en) | 2005-06-24 | 2009-06-24 | Kyowa Hakko Kirin Co Ltd | THERAPEUTIC AGENT AGAINST RESTENOSIS |
| US8101799B2 (en) * | 2005-07-21 | 2012-01-24 | Ardea Biosciences | Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK |
| WO2009018233A1 (en) * | 2007-07-30 | 2009-02-05 | Ardea Biosciences, Inc. | Derivatives of n-(arylamino) sulfonamides including polymorphs as inhibitors of mek as well as compositions, methods of use and methods for preparing the same |
| US8053454B2 (en) * | 2005-10-06 | 2011-11-08 | Exelixis, Inc. | Pyridopyrimidinone inhibitors of PIM-1 and/or PIM-3 |
| HRP20110498T1 (hr) | 2005-10-07 | 2011-08-31 | Exelixis | Azetidini kao inhibitori mek za liječenje proliferativnih bolesti |
| EP1954277B1 (en) | 2005-11-03 | 2017-01-18 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| ZA200807263B (en) | 2006-04-19 | 2009-11-25 | Serono Lab | Novel heteroaryl-substituted arylaminopyrldine derivatives as MEK inhibitors |
| US7772233B2 (en) | 2006-04-19 | 2010-08-10 | Merck Serono, S.A. | Arylamino N-heteroaryl compounds as MEK inhibitors |
| WO2007132867A1 (ja) | 2006-05-15 | 2007-11-22 | Takeda Pharmaceutical Company Limited | 癌の予防及び治療剤 |
| ATE532789T1 (de) | 2006-07-06 | 2011-11-15 | Array Biopharma Inc | Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| US8329701B2 (en) | 2006-07-06 | 2012-12-11 | Array Biopharma Inc. | Dihydrofuro pyrimidines as AKT protein kinase inhibitors |
| EP2049500B1 (en) | 2006-07-06 | 2011-09-07 | Array Biopharma, Inc. | Cyclopenta [d] pyrimidines as akt protein kinase inhibitors |
| WO2008076415A1 (en) | 2006-12-14 | 2008-06-26 | Exelixis, Inc. | Methods of using mek inhibitors |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| CN101918373B (zh) | 2007-07-05 | 2013-06-05 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的嘧啶基环戊烷 |
| CN103396409B (zh) | 2007-07-05 | 2015-03-11 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的嘧啶基环戊烷 |
| UA99731C2 (ru) * | 2007-07-30 | 2012-09-25 | Ардеа Биосайенсис, Инк | Кристаллические полиморфные формы n-(ариламино)сульфонамидов как ингибиторы мэк, композиция (варианты) и применение |
| CN101790532B (zh) | 2007-07-31 | 2013-11-20 | 沃泰克斯药物股份有限公司 | 5-氟-1H-吡唑并[3，4-b]吡啶-3-胺及其衍生物的制备方法 |
| NZ586346A (en) | 2008-01-09 | 2012-02-24 | Array Biopharma Inc | Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| US8853216B2 (en) | 2008-01-09 | 2014-10-07 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentane as AKT protein kinase inhibitor |
| US8044240B2 (en) | 2008-03-06 | 2011-10-25 | Ardea Biosciences Inc. | Polymorphic form of N-(S)-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide and uses thereof |
| US8808742B2 (en) * | 2008-04-14 | 2014-08-19 | Ardea Biosciences, Inc. | Compositions and methods for preparing and using same |
| UA107183C2 (uk) | 2008-08-04 | 2014-12-10 | Феніламіно-ізонікотинамідні сполуки, їх застосування, фармацевтична композиція, що їх містить, та спосіб лікування гіперпроліферативних захворювань | |
| US8993630B2 (en) | 2008-11-10 | 2015-03-31 | Bayer Intellectual Property Gmbh | Substituted sulphonamido phenoxybenzamides |
| EP2370568B1 (en) | 2008-12-10 | 2017-07-19 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| US20120263714A1 (en) | 2009-10-21 | 2012-10-18 | Bayer Intellectual Property Gmbh | Substituted halophenoxybenzamide derivatives |
| EP2491015A1 (en) | 2009-10-21 | 2012-08-29 | Bayer Pharma Aktiengesellschaft | Substituted benzosulphonamides |
| US20120269803A1 (en) | 2009-10-21 | 2012-10-25 | Bayer Intellectual Property Gmbh | Substituted benzosulphonamides |
| JPWO2011052756A1 (ja) | 2009-10-30 | 2013-03-21 | 持田製薬株式会社 | 新規３−ヒドロキシ−５−アリールイソキサゾール誘導体 |
| US20110130415A1 (en) | 2009-12-01 | 2011-06-02 | Rajinder Singh | Protein kinase c inhibitors and uses thereof |
| NZ601408A (en) | 2009-12-25 | 2013-12-20 | Mochida Pharm Co Ltd | Novel 3-hydroxy-5-arylisothiazole derivative |
| EP3028699B1 (en) | 2010-02-25 | 2018-03-21 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| CN103038364A (zh) | 2010-03-09 | 2013-04-10 | 达纳－法伯癌症研究所公司 | 诊断和治疗具有或发展对于第一种癌症治疗的抗性的患者中的癌症的方法 |
| JP5809157B2 (ja) | 2010-10-08 | 2015-11-10 | 持田製薬株式会社 | 環状アミド誘導体 |
| CN103282351A (zh) | 2010-10-29 | 2013-09-04 | 拜耳知识产权有限责任公司 | 取代的苯氧基吡啶 |
| CN102020651B (zh) | 2010-11-02 | 2012-07-18 | 北京赛林泰医药技术有限公司 | 6-芳基氨基吡啶酮甲酰胺mek抑制剂 |
| TR201815685T4 (tr) | 2011-04-01 | 2018-11-21 | Genentech Inc | Kanser tedavisi için akt ve mek inhibe edici bileşiklerin kombinasyonları. |
| KR102021157B1 (ko) | 2011-04-01 | 2019-09-11 | 제넨테크, 인크. | Ａｋｔ 억제제 화합물 및 아비라테론의 조합물, 및 사용 방법 |
| BR112013027883A2 (pt) | 2011-04-27 | 2017-08-08 | Mochida Pharm Co Ltd | novo derivado de 1-óxido de 3-hidroxiisotiazol |
| AU2012248627A1 (en) | 2011-04-28 | 2013-11-14 | Mochida Pharmaceutical Co., Ltd. | Cyclic amide derivative |
| ES2597052T3 (es) | 2011-05-25 | 2017-01-13 | Université Paris Descartes | Inhibidores de ERK para su uso en el tratamiento de atrofia muscular espinal |
| CN103204827B (zh) | 2012-01-17 | 2014-12-03 | 上海科州药物研发有限公司 | 作为蛋白激酶抑制剂的苯并噻二唑化合物及其制备方法和用途 |
| US20150141470A1 (en) | 2012-05-08 | 2015-05-21 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| WO2013178320A1 (en) * | 2012-05-30 | 2013-12-05 | Merck Patent Gmbh | Solid state forms of n-((s)-2,3-dihydroxy-propyl)-3-(2-fluoro-4-iodo-phenylamino)-isonicotinamide |
| AU2013269809B2 (en) | 2012-05-31 | 2017-12-21 | Bayer Pharma Aktiengesellschaft | Biomarkers for determining effective response of treatments of Hepatocellular carcinoma (HCC) patients |
| MA38085B1 (fr) | 2012-10-12 | 2018-11-30 | Exelixis Inc | Nouveau procédé pour la production de composés à utiliser dans le traitement du cancer |
| JP2016501203A (ja) | 2012-11-20 | 2016-01-18 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インドールアミン２，３−ジオキシゲナーゼの阻害剤として有用な化合物 |
| EP3043822A1 (en) | 2013-09-11 | 2016-07-20 | The J. David Gladstone Institutes, A Testamentary Trust Established under The Will of J. David Gladstone | Compositions for preparing cardiomyocytes |
| CA2935804A1 (en) | 2014-01-14 | 2015-07-23 | Dana-Farber Cancer Institute, Inc. | Compositions and methods for identification, assessment, prevention, and treatment of melanoma using pd-l1 isoforms |
| AU2015328411C1 (en) | 2014-10-06 | 2022-03-03 | Dana-Farber Cancer Institute, Inc. | Angiopoietin-2 biomarkers predictive of anti-immune checkpoint response |
| MA41866A (fr) | 2015-03-31 | 2018-02-06 | Massachusetts Gen Hospital | Molécules à auto-assemblage pour l'administration ciblée de médicaments |
| WO2018204532A1 (en) | 2017-05-03 | 2018-11-08 | Vivace Therapeutics, Inc. | Non-fused tricyclic compounds |
| CA3073543A1 (en) | 2017-08-21 | 2019-02-28 | Vivace Therapeutics, Inc. | Benzosulfonyl compounds |
| US11524943B1 (en) | 2017-12-06 | 2022-12-13 | Vivace Therapeutics, Inc. | Benzocarbonyl compounds |
| EP3793551A4 (en) | 2018-05-16 | 2022-01-26 | Vivace Therapeutics, Inc. | OXADIAZOLE COMPOUNDS |
| CN113473986B (zh) | 2018-11-20 | 2024-10-11 | 恩福莱克逊治疗有限公司 | 用于治疗皮肤疾病萘啶酮苯胺化合物 |
| AU2019383311B2 (en) | 2018-11-20 | 2024-12-05 | Nflection Therapeutics, Inc. | Cyanoaryl-aniline compounds for treatment of dermal disorders |
| MA55143A (fr) * | 2018-11-20 | 2021-09-29 | H Lee Moffitt Cancer Center & Res Institute Inc | Composés aryl-aniline et hétéroaryl-aniline pour le traitement de cancers de la peau |
| US12466818B2 (en) | 2018-11-20 | 2025-11-11 | Nflection Therapeutics, Inc. | Thienyl-aniline compounds for treatment of dermal disorders |
| AU2020320008A1 (en) * | 2019-07-29 | 2022-03-17 | Basilea Pharmaceutica International AG | 1,2,4-oxadiazol-5-one derivatives for the treatment of cancer |
| CN114981298B (zh) | 2019-12-12 | 2024-08-20 | 听治疗有限责任公司 | 用于预防和治疗听力损失的组合物和方法 |
| KR20240125577A (ko) | 2021-11-23 | 2024-08-19 | 엔플렉션 테라퓨틱스, 인코포레이티드 | 피롤로피리딘-아닐린 화합물의 제형 |
| TW202342018A (zh) | 2022-03-04 | 2023-11-01 | 美商奇奈特生物製藥公司 | Mek激酶抑制劑 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH479599A (de) | 1965-04-12 | 1969-10-15 | Bristol Myers Co | Verfahren zur Herstellung von Verbindungen von Nitrilen mit Stickstoffwasserstoffsäure oder Aziden |
| US5525625A (en) | 1995-01-24 | 1996-06-11 | Warner-Lambert Company | 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran for treating proliferative disorders |
| WO1998037881A1 (en) | 1997-02-28 | 1998-09-03 | Warner Lambert Company | Method of treating or preventing septic shock by administering a mek inhibitor |
| NZ501276A (en) * | 1997-07-01 | 2000-10-27 | Warner Lambert Co | 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors in treating proliferative disorders |
| CA2290509A1 (en) * | 1997-07-01 | 1999-01-14 | Warner-Lambert Company | 2-(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as mek inhibitors |
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1999
- 1999-12-21 HU HU0105092A patent/HUP0105092A3/hu unknown
- 1999-12-21 SK SK982-2001A patent/SK9822001A3/sk unknown
- 1999-12-21 WO PCT/US1999/030416 patent/WO2000042029A1/en not_active Ceased
- 1999-12-21 DE DE69926914T patent/DE69926914T2/de not_active Expired - Fee Related
- 1999-12-21 EP EP99968150A patent/EP1144394B1/en not_active Expired - Lifetime
- 1999-12-21 KR KR1020017008828A patent/KR20010108093A/ko not_active Withdrawn
- 1999-12-21 HR HR20010525A patent/HRP20010525A2/hr not_active Application Discontinuation
- 1999-12-21 AU AU24827/00A patent/AU2482700A/en not_active Abandoned
- 1999-12-21 BR BR9916896-0A patent/BR9916896A/pt not_active Application Discontinuation
- 1999-12-21 CZ CZ20012528A patent/CZ20012528A3/cs unknown
- 1999-12-21 EA EA200100773A patent/EA200100773A1/ru unknown
- 1999-12-21 JP JP2000593597A patent/JP2002534515A/ja not_active Abandoned
- 1999-12-21 AT AT99968150T patent/ATE302761T1/de not_active IP Right Cessation
- 1999-12-21 ES ES99968150T patent/ES2249060T3/es not_active Expired - Lifetime
- 1999-12-21 EE EEP200100374A patent/EE200100374A/xx unknown
- 1999-12-21 GE GEAP19996049A patent/GEP20032999B/en unknown
- 1999-12-21 AP APAP/P/2001/002225A patent/AP2001002225A0/en unknown
- 1999-12-21 NZ NZ513432A patent/NZ513432A/xx unknown
- 1999-12-21 CA CA002355374A patent/CA2355374A1/en not_active Abandoned
- 1999-12-21 IL IL14421599A patent/IL144215A0/xx unknown
- 1999-12-21 US US09/889,104 patent/US6545030B1/en not_active Expired - Fee Related
- 1999-12-21 TR TR2001/02029T patent/TR200102029T2/xx unknown
- 1999-12-21 PL PL99348870A patent/PL348870A1/xx not_active Application Discontinuation
- 1999-12-21 OA OA1200100185A patent/OA11819A/en unknown
- 1999-12-21 CN CNB998156191A patent/CN1149204C/zh not_active Expired - Fee Related
-
2001
- 2001-06-22 IS IS5975A patent/IS5975A/is unknown
- 2001-07-12 NO NO20013451A patent/NO20013451D0/no not_active Application Discontinuation
- 2001-08-09 BG BG105801A patent/BG105801A/bg unknown
- 2001-08-10 MA MA26292A patent/MA26770A1/fr unknown
-
2002
- 2002-07-23 US US10/201,146 patent/US20030004193A1/en not_active Abandoned
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