JP2000204077A5 - - Google Patents
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- Publication number
- JP2000204077A5 JP2000204077A5 JP1999053564A JP5356499A JP2000204077A5 JP 2000204077 A5 JP2000204077 A5 JP 2000204077A5 JP 1999053564 A JP1999053564 A JP 1999053564A JP 5356499 A JP5356499 A JP 5356499A JP 2000204077 A5 JP2000204077 A5 JP 2000204077A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- iodo
- phenylamino
- difluoro
- 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 37
- 150000001875 compounds Chemical class 0.000 description 23
- ZZLTXWMPUKJTFS-UHFFFAOYSA-N 2-hydroxy-3h-oxadiazole Chemical compound ON1NC=CO1 ZZLTXWMPUKJTFS-UHFFFAOYSA-N 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229910004013 NO 2 Inorganic materials 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- NBNQOWVYEXFQJC-UHFFFAOYSA-N 2-sulfanyl-3h-thiadiazole Chemical compound SN1NC=CS1 NBNQOWVYEXFQJC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001424 substituent group Chemical group 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
- JCPNJTWIJHNAIN-UHFFFAOYSA-N 1-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]triazol-4-ol Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1N1N=NC(O)=C1 JCPNJTWIJHNAIN-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
- POSAFBNNUWKOOT-UHFFFAOYSA-N 1-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]triazol-4-ol Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1N1N=NC(O)=C1 POSAFBNNUWKOOT-UHFFFAOYSA-N 0.000 description 1
- UBJAZLPIPCIXCH-UHFFFAOYSA-N 1-methyl-4-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]tetrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1N1C(=O)N(C)N=N1 UBJAZLPIPCIXCH-UHFFFAOYSA-N 0.000 description 1
- WAUGGYPDCQZJKK-UHFFFAOYSA-N 1h-pyrrol-3-amine Chemical compound NC=1C=CNC=1 WAUGGYPDCQZJKK-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
- 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
- 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
- UPGDPKNDUGBHJO-UHFFFAOYSA-N 4-[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=CON=C1O UPGDPKNDUGBHJO-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
- 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
- XCEAAXNFYQTNRX-UHFFFAOYSA-N 4-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-thiazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=CSN=C1O XCEAAXNFYQTNRX-UHFFFAOYSA-N 0.000 description 1
- ATIIDUMSUKPVSW-UHFFFAOYSA-N 4-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-2-methyl-1h-pyrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=CN(C)N=C1O ATIIDUMSUKPVSW-UHFFFAOYSA-N 0.000 description 1
- FDKCGBRXTKECRT-UHFFFAOYSA-N 4-[4-fluoro-2-(4-iodo-2-methylanilino)phenyl]-4h-1,2-oxazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1C(=O)ON=C1 FDKCGBRXTKECRT-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
- 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
- BGKLFAQCHHCZRZ-UHFFFAOYSA-N 4-iodo-2-methylaniline Chemical compound CC1=CC(I)=CC=C1N BGKLFAQCHHCZRZ-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
- JBCJEIBYCOKDHF-UHFFFAOYSA-N 5-[3,4,5-trifluoro-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(F)C=C1C1=NN=C(O)N1 JBCJEIBYCOKDHF-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
- 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
- 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
- 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
- VTMWBHRBNZTMSE-UHFFFAOYSA-N 5-[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=CC(O)=NS1 VTMWBHRBNZTMSE-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
- 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
- PLHIYIVMGXBALK-UHFFFAOYSA-N 5-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]-3h-1,3,4-thiadiazol-2-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=NN=C(O)S1 PLHIYIVMGXBALK-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
- 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
- HCFIYGRTRUMJJH-UHFFFAOYSA-N 5-[5-bromo-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)=C(Br)C=C1C1=NN=C(S)N1 HCFIYGRTRUMJJH-UHFFFAOYSA-N 0.000 description 1
- QMZIHEDWFZAVQG-UHFFFAOYSA-N 5-[5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-1,2-dihydropyrazol-3-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=CC(O)=NN1 QMZIHEDWFZAVQG-UHFFFAOYSA-N 0.000 description 1
- DMJSTYIZGPMWRM-UHFFFAOYSA-N 5-[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=CC(O)=NS1 DMJSTYIZGPMWRM-UHFFFAOYSA-N 0.000 description 1
- KBNSOAVKWSDKLE-UHFFFAOYSA-N 5-[5-bromo-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)=C(Br)C=C1C1=NN=C(N)S1 KBNSOAVKWSDKLE-UHFFFAOYSA-N 0.000 description 1
- YJHSCIHOYYWCQW-UHFFFAOYSA-N 5-[5-bromo-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)=C(Br)C=C1C1=NN=C(N)N1 YJHSCIHOYYWCQW-UHFFFAOYSA-N 0.000 description 1
- HDNIRQUOIOKKRS-UHFFFAOYSA-N 5-[5-bromo-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)=C(Br)C=C1C1=NN=C(O)S1 HDNIRQUOIOKKRS-UHFFFAOYSA-N 0.000 description 1
- UAHQCZNAVYTCSC-UHFFFAOYSA-N 5-fluoro-n-(4-iodo-2-methylphenyl)-2-(2h-tetrazol-5-yl)aniline Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=NN=NN1 UAHQCZNAVYTCSC-UHFFFAOYSA-N 0.000 description 1
- IKCKSPFZYKIPEC-UHFFFAOYSA-N 5-fluoro-n-(4-iodo-2-methylphenyl)-4-nitro-2-(2h-tetrazol-5-yl)aniline Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=NN=NN1 IKCKSPFZYKIPEC-UHFFFAOYSA-N 0.000 description 1
- LQXJTBZNAMNDLE-UHFFFAOYSA-N 6-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-2,3,4-trifluoro-n-(4-iodo-2-methylphenyl)aniline Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=NC(C)(C)CO1 LQXJTBZNAMNDLE-UHFFFAOYSA-N 0.000 description 1
- AFYSJAXIQPATBO-UHFFFAOYSA-N 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)=CC=C1C1=NC(C)(C)CO1 AFYSJAXIQPATBO-UHFFFAOYSA-N 0.000 description 1
- IVEQTMOSBYJXPN-UHFFFAOYSA-N CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=C(O)N(C)N=C1 Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=C(O)N(C)N=C1 IVEQTMOSBYJXPN-UHFFFAOYSA-N 0.000 description 1
- ZROOXJUDUNBDMY-UHFFFAOYSA-N CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=C(O)N(C)N=N1 Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=C(O)N(C)N=N1 ZROOXJUDUNBDMY-UHFFFAOYSA-N 0.000 description 1
- PYGOPEBHZKRETO-UHFFFAOYSA-N CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=C(O)N(C)N=C1 Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=C(O)N(C)N=C1 PYGOPEBHZKRETO-UHFFFAOYSA-N 0.000 description 1
- NHOACUWHLVOOFZ-UHFFFAOYSA-N CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=C(O)N(C)N=N1 Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=C(O)N(C)N=N1 NHOACUWHLVOOFZ-UHFFFAOYSA-N 0.000 description 1
- BKIZNXZPDHMPNB-UHFFFAOYSA-N CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=C(O)N(C)N=C1 Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=C(O)N(C)N=C1 BKIZNXZPDHMPNB-UHFFFAOYSA-N 0.000 description 1
- JIPMATZRMPAVCO-UHFFFAOYSA-N CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=C(O)N(C)N=N1 Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=C(O)N(C)N=N1 JIPMATZRMPAVCO-UHFFFAOYSA-N 0.000 description 1
- QAXGSZGBWAPUIG-UHFFFAOYSA-N CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=C(O)N(C)N=N1 Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1C1=C(O)N(C)N=N1 QAXGSZGBWAPUIG-UHFFFAOYSA-N 0.000 description 1
- SZGAZIXGPNGOJI-UHFFFAOYSA-N CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=C(O)N(C)N=C1 Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=C(O)N(C)N=C1 SZGAZIXGPNGOJI-UHFFFAOYSA-N 0.000 description 1
- MGUKQXQTYXXBTF-UHFFFAOYSA-N CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=C(O)N(C)N=N1 Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C1=C(O)N(C)N=N1 MGUKQXQTYXXBTF-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11587599P | 1999-01-13 | 1999-01-13 | |
| US115875 | 1999-01-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000204077A JP2000204077A (ja) | 2000-07-25 |
| JP2000204077A5 true JP2000204077A5 (https=) | 2006-04-27 |
Family
ID=22363910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11053564A Abandoned JP2000204077A (ja) | 1999-01-13 | 1999-03-02 | ジアリ―ルアミン |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2000204077A (https=) |
| UA (1) | UA72239C2 (https=) |
| ZA (1) | ZA200105219B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE480527T1 (de) | 2001-12-11 | 2010-09-15 | Kyowa Hakko Kirin Co Ltd | Thiadiazolinderivate zur krebsbehandlung |
| SG2013013339A (en) | 2002-03-13 | 2014-12-30 | Array Biopharma Inc | N3 alkylated benzimidazole derivatives as mek inhibitors |
| CA2522594C (en) | 2003-04-18 | 2012-01-24 | Kyowa Hakko Kogyo Co., Ltd. | Mitotic kinesin inhibitor |
| EP1908755A4 (en) | 2005-06-24 | 2009-06-24 | Kyowa Hakko Kirin Co Ltd | THERAPEUTIC AGENT AGAINST RESTENOSIS |
| EP2370568B1 (en) | 2008-12-10 | 2017-07-19 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| 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 |
| BR112013027883A2 (pt) | 2011-04-27 | 2017-08-08 | Mochida Pharm Co Ltd | novo derivado de 1-óxido de 3-hidroxiisotiazol |
| 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 |
-
1999
- 1999-03-02 JP JP11053564A patent/JP2000204077A/ja not_active Abandoned
- 1999-12-21 UA UA2001085705A patent/UA72239C2/uk unknown
-
2001
- 2001-06-25 ZA ZA200105219A patent/ZA200105219B/en unknown
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