JP2001526220A5 - - Google Patents
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- JP2001526220A5 JP2001526220A5 JP2000525097A JP2000525097A JP2001526220A5 JP 2001526220 A5 JP2001526220 A5 JP 2001526220A5 JP 2000525097 A JP2000525097 A JP 2000525097A JP 2000525097 A JP2000525097 A JP 2000525097A JP 2001526220 A5 JP2001526220 A5 JP 2001526220A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- urea
- butyl
- group
- tert
- 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.)
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- 238000006467 substitution reaction Methods 0.000 description 182
- 125000003118 aryl group Chemical group 0.000 description 121
- 229910052736 halogen Inorganic materials 0.000 description 105
- 150000002367 halogens Chemical class 0.000 description 105
- -1 1-methyl-3-tert-butyl-5-pyrazolyl Chemical group 0.000 description 56
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 55
- 239000004202 carbamide Substances 0.000 description 55
- 150000001875 compounds Chemical class 0.000 description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 46
- 125000000753 cycloalkyl group Chemical group 0.000 description 38
- 125000004076 pyridyl group Chemical group 0.000 description 38
- 125000000217 alkyl group Chemical group 0.000 description 28
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- 239000001257 hydrogen Substances 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
- 125000002877 alkyl aryl group Chemical group 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 229910052760 oxygen Inorganic materials 0.000 description 20
- 229910052717 sulfur Chemical group 0.000 description 20
- 150000002431 hydrogen Chemical class 0.000 description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 16
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 16
- 239000003814 drug Substances 0.000 description 15
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Chemical group 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000011593 sulfur Chemical group 0.000 description 10
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- MQQZEXCPOASVFI-UHFFFAOYSA-N 1-(5-tert-butyl-1h-pyrazol-3-yl)-3-(3-pyridin-4-ylsulfanylphenyl)urea Chemical compound N1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=CC(SC=2C=CN=CC=2)=C1 MQQZEXCPOASVFI-UHFFFAOYSA-N 0.000 description 4
- UDYOWLBACWDBNL-UHFFFAOYSA-N 1-(5-tert-butyl-1h-pyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 UDYOWLBACWDBNL-UHFFFAOYSA-N 0.000 description 4
- NISMKTLRQBAMPS-UHFFFAOYSA-N 1-(5-tert-butyl-1h-pyrazol-3-yl)-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound N1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(SC=3C=CN=CC=3)=CC=2)=N1 NISMKTLRQBAMPS-UHFFFAOYSA-N 0.000 description 4
- NIQFSOWYCXNLNI-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(3-pyridin-4-ylsulfanylphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=CC(SC=2C=CN=CC=2)=C1 NIQFSOWYCXNLNI-UHFFFAOYSA-N 0.000 description 4
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 description 4
- FDHKHZIFBOZGKU-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1SC1=CC=NC=C1 FDHKHZIFBOZGKU-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- MTTAQONWKYZSGQ-UHFFFAOYSA-N 1-(3-benzoylphenyl)-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=C(C=CC=2)C(=O)C=2C=CC=CC=2)=N1 MTTAQONWKYZSGQ-UHFFFAOYSA-N 0.000 description 2
- NNGZTFCLDJGBAR-UHFFFAOYSA-N 1-(3-propan-2-yl-1,2-oxazol-5-yl)-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound O1N=C(C(C)C)C=C1NC(=O)NC(C=C1)=CC=C1SC1=CC=NC=C1 NNGZTFCLDJGBAR-UHFFFAOYSA-N 0.000 description 2
- ZLRZULLSROJBLS-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-(3-pyridin-4-ylsulfanylphenyl)urea Chemical compound O1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=CC(SC=2C=CN=CC=2)=C1 ZLRZULLSROJBLS-UHFFFAOYSA-N 0.000 description 2
- ORIFMUAUSBIDGC-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound O1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 ORIFMUAUSBIDGC-UHFFFAOYSA-N 0.000 description 2
- YSOLQZIGFKVUPX-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound O1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1SC1=CC=NC=C1 YSOLQZIGFKVUPX-UHFFFAOYSA-N 0.000 description 2
- QNPSZGWMKYQMSH-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-(4-methoxyphenoxy)phenyl]urea Chemical compound C1=CC(OC)=CC=C1OC(C=C1)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NO1 QNPSZGWMKYQMSH-UHFFFAOYSA-N 0.000 description 2
- KDXIBGWSUXXMBV-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-(4-methylpyridin-3-yl)oxyphenyl]urea Chemical compound CC1=CC=NC=C1OC(C=C1)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NO1 KDXIBGWSUXXMBV-UHFFFAOYSA-N 0.000 description 2
- KXEOEENRCKNIJO-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-(pyridin-4-ylmethyl)phenyl]urea Chemical compound O1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1CC1=CC=NC=C1 KXEOEENRCKNIJO-UHFFFAOYSA-N 0.000 description 2
- RBTTWKACKBLWGC-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(3-pyridin-4-yloxyphenyl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=C(OC=3C=CN=CC=3)C=CC=2)=N1 RBTTWKACKBLWGC-UHFFFAOYSA-N 0.000 description 2
- BWYIEKUXLAWWDO-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(3-pyridin-4-ylsulfanylphenyl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=C(SC=3C=CN=CC=3)C=CC=2)=N1 BWYIEKUXLAWWDO-UHFFFAOYSA-N 0.000 description 2
- ANWRKPQVLGBTCG-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(4-phenoxyphenyl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 ANWRKPQVLGBTCG-UHFFFAOYSA-N 0.000 description 2
- XIGJMGPUXKZADA-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(4-pyridin-3-yloxyphenyl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(OC=3C=NC=CC=3)=CC=2)=N1 XIGJMGPUXKZADA-UHFFFAOYSA-N 0.000 description 2
- XKNAGLMNQADBQE-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(OC=3C=CN=CC=3)=CC=2)=N1 XKNAGLMNQADBQE-UHFFFAOYSA-N 0.000 description 2
- MBPSLEWGDKMGQY-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(SC=3C=CN=CC=3)=CC=2)=N1 MBPSLEWGDKMGQY-UHFFFAOYSA-N 0.000 description 2
- OCVLLNOZMGLZMR-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[3-(3-methylpyridin-4-yl)oxyphenyl]urea Chemical compound CC1=CN=CC=C1OC1=CC=CC(NC(=O)NC2=NOC(=C2)C(C)(C)C)=C1 OCVLLNOZMGLZMR-UHFFFAOYSA-N 0.000 description 2
- RVAHNWTXRHZRLG-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[3-(3-methylpyridin-4-yl)sulfanylphenyl]urea Chemical compound CC1=CN=CC=C1SC1=CC=CC(NC(=O)NC2=NOC(=C2)C(C)(C)C)=C1 RVAHNWTXRHZRLG-UHFFFAOYSA-N 0.000 description 2
- RQOXVIHEZQVYGS-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[3-(4-methylpyridin-3-yl)oxyphenyl]urea Chemical compound CC1=CC=NC=C1OC1=CC=CC(NC(=O)NC2=NOC(=C2)C(C)(C)C)=C1 RQOXVIHEZQVYGS-UHFFFAOYSA-N 0.000 description 2
- ZNHFSYPNHIOTRT-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-(3-hydroxyphenoxy)phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(OC=3C=C(O)C=CC=3)=CC=2)=N1 ZNHFSYPNHIOTRT-UHFFFAOYSA-N 0.000 description 2
- VJWFZMSZAJHSFF-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-(3-methylpyridin-4-yl)oxyphenyl]urea Chemical compound CC1=CN=CC=C1OC(C=C1)=CC=C1NC(=O)NC1=NOC(C(C)(C)C)=C1 VJWFZMSZAJHSFF-UHFFFAOYSA-N 0.000 description 2
- WFBGXNIMCQEGOX-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-(3-methylpyridin-4-yl)sulfanylphenyl]urea Chemical compound CC1=CN=CC=C1SC(C=C1)=CC=C1NC(=O)NC1=NOC(C(C)(C)C)=C1 WFBGXNIMCQEGOX-UHFFFAOYSA-N 0.000 description 2
- DMQFIGFOGVTSFP-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-(4-hydroxyphenoxy)phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(OC=3C=CC(O)=CC=3)=CC=2)=N1 DMQFIGFOGVTSFP-UHFFFAOYSA-N 0.000 description 2
- CJUNRHGYKDHACB-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-(pyridin-4-ylmethyl)phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(CC=3C=CN=CC=3)=CC=2)=N1 CJUNRHGYKDHACB-UHFFFAOYSA-N 0.000 description 2
- PXMZWZHOSUYALM-UHFFFAOYSA-N 1-(5-tert-butyl-1h-pyrazol-3-yl)-3-(3-pyridin-4-yloxyphenyl)urea Chemical compound N1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=CC(OC=2C=CN=CC=2)=C1 PXMZWZHOSUYALM-UHFFFAOYSA-N 0.000 description 2
- MSMDSZZGUDIFPB-UHFFFAOYSA-N 1-(5-tert-butyl-1h-pyrazol-3-yl)-3-(4-phenoxyphenyl)urea Chemical compound N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 MSMDSZZGUDIFPB-UHFFFAOYSA-N 0.000 description 2
- VWBAHTCOVBWTMX-UHFFFAOYSA-N 1-(5-tert-butyl-1h-pyrazol-3-yl)-3-[4-(pyridin-4-ylmethyl)phenyl]urea Chemical compound N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1CC1=CC=NC=C1 VWBAHTCOVBWTMX-UHFFFAOYSA-N 0.000 description 2
- JDKYGCYHGTVUOU-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(3-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=CC(OC=2C=CN=CC=2)=C1 JDKYGCYHGTVUOU-UHFFFAOYSA-N 0.000 description 2
- HFVZEWHYOCNZGL-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-phenoxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 HFVZEWHYOCNZGL-UHFFFAOYSA-N 0.000 description 2
- UYYMFPJGZUWZKS-UHFFFAOYSA-N 1-(5-tert-butylthiophen-3-yl)-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(SC=3C=CN=CC=3)=CC=2)=C1 UYYMFPJGZUWZKS-UHFFFAOYSA-N 0.000 description 2
- WKAIPJMBCLQCSX-UHFFFAOYSA-N 1-(5-tert-butylthiophen-3-yl)-3-[4-(3-methylphenoxy)phenyl]urea Chemical compound CC1=CC=CC(OC=2C=CC(NC(=O)NC=3C=C(SC=3)C(C)(C)C)=CC=2)=C1 WKAIPJMBCLQCSX-UHFFFAOYSA-N 0.000 description 2
- KUMIMKXLYUJKTQ-UHFFFAOYSA-N 1-(5-tert-butylthiophen-3-yl)-3-[4-(4-hydroxyphenoxy)phenyl]urea Chemical compound S1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(OC=3C=CC(O)=CC=3)=CC=2)=C1 KUMIMKXLYUJKTQ-UHFFFAOYSA-N 0.000 description 2
- TXGSEPBWHRRHQE-UHFFFAOYSA-N 1-(5-tert-butylthiophen-3-yl)-3-[4-(4-methoxyphenoxy)phenyl]urea Chemical compound C1=CC(OC)=CC=C1OC(C=C1)=CC=C1NC(=O)NC1=CSC(C(C)(C)C)=C1 TXGSEPBWHRRHQE-UHFFFAOYSA-N 0.000 description 2
- RAAIQRXSFVOCHG-UHFFFAOYSA-N 1-[3-(1,3-benzothiazol-2-yloxy)phenyl]-3-(3-tert-butyl-1,2-oxazol-5-yl)urea Chemical compound O1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=CC(OC=2SC3=CC=CC=C3N=2)=C1 RAAIQRXSFVOCHG-UHFFFAOYSA-N 0.000 description 2
- XHWVFNIWFYIPIZ-UHFFFAOYSA-N 1-[3-(1,3-benzothiazol-2-yloxy)phenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=C(OC=3SC4=CC=CC=C4N=3)C=CC=2)=N1 XHWVFNIWFYIPIZ-UHFFFAOYSA-N 0.000 description 2
- RHSMGLCDPGODHW-UHFFFAOYSA-N 1-[3-(1,3-benzothiazol-2-yloxy)phenyl]-3-(5-tert-butyl-2-methylpyrazol-3-yl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=CC(OC=2SC3=CC=CC=C3N=2)=C1 RHSMGLCDPGODHW-UHFFFAOYSA-N 0.000 description 2
- RMNIXRMFHYBQQB-UHFFFAOYSA-N 1-[3-(2-methylbutan-2-yl)-1,2-oxazol-5-yl]-3-(3-pyridin-4-ylsulfanylphenyl)urea Chemical compound O1N=C(C(C)(C)CC)C=C1NC(=O)NC1=CC=CC(SC=2C=CN=CC=2)=C1 RMNIXRMFHYBQQB-UHFFFAOYSA-N 0.000 description 2
- OLAYKASHGVRXIZ-UHFFFAOYSA-N 1-[3-(2-methylbutan-2-yl)-1,2-oxazol-5-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound O1N=C(C(C)(C)CC)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 OLAYKASHGVRXIZ-UHFFFAOYSA-N 0.000 description 2
- JYGHRSVBJYNRTB-UHFFFAOYSA-N 1-[3-(2-methylbutan-2-yl)-1,2-oxazol-5-yl]-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound O1N=C(C(C)(C)CC)C=C1NC(=O)NC(C=C1)=CC=C1SC1=CC=NC=C1 JYGHRSVBJYNRTB-UHFFFAOYSA-N 0.000 description 2
- JBQPNUNIDPHVFQ-UHFFFAOYSA-N 1-[3-(2-methylbutan-2-yl)-1,2-oxazol-5-yl]-3-[4-(4-methylphenoxy)phenyl]urea Chemical compound O1N=C(C(C)(C)CC)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=C(C)C=C1 JBQPNUNIDPHVFQ-UHFFFAOYSA-N 0.000 description 2
- GCBVDYBTNTVVOV-UHFFFAOYSA-N 1-[3-(3-methylpentan-3-yl)-1,2-oxazol-5-yl]-3-(3-pyridin-4-ylsulfanylphenyl)urea Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)NC1=CC=CC(SC=2C=CN=CC=2)=C1 GCBVDYBTNTVVOV-UHFFFAOYSA-N 0.000 description 2
- HCQRNJBKBZFSAB-UHFFFAOYSA-N 1-[3-(3-methylpentan-3-yl)-1,2-oxazol-5-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 HCQRNJBKBZFSAB-UHFFFAOYSA-N 0.000 description 2
- VZQCQRSYTUIZKV-UHFFFAOYSA-N 1-[4-(4-acetylphenoxy)phenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound C1=CC(C(=O)C)=CC=C1OC(C=C1)=CC=C1NC(=O)NC1=NOC(C(C)(C)C)=C1 VZQCQRSYTUIZKV-UHFFFAOYSA-N 0.000 description 2
- JTOAETRLMJYYMY-UHFFFAOYSA-N 1-[4-(7ah-1,3-benzodioxol-3a-yloxy)phenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(OC34C(OCO3)C=CC=C4)=CC=2)=N1 JTOAETRLMJYYMY-UHFFFAOYSA-N 0.000 description 2
- WGTGBBYSTFTSFN-UHFFFAOYSA-N 3-[3-[(5-tert-butyl-1h-pyrazol-3-yl)carbamoylamino]phenoxy]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(OC=2C=C(NC(=O)NC=3NN=C(C=3)C(C)(C)C)C=CC=2)=C1 WGTGBBYSTFTSFN-UHFFFAOYSA-N 0.000 description 2
- YRVHIOAIPPJICO-UHFFFAOYSA-N 3-[4-[(5-tert-butyl-1,2-oxazol-3-yl)carbamoylamino]phenyl]sulfanyl-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(SC=2C=CC(NC(=O)NC3=NOC(=C3)C(C)(C)C)=CC=2)=C1 YRVHIOAIPPJICO-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 102000009929 raf Kinases Human genes 0.000 description 1
- 108010077182 raf Kinases Proteins 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99634397A | 1997-12-22 | 1997-12-22 | |
| US08/996,343 | 1997-12-22 | ||
| PCT/US1998/026078 WO1999032106A1 (en) | 1997-12-22 | 1998-12-22 | Inhibition of raf kinase using substituted heterocyclic ureas |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009237895A Division JP2010065041A (ja) | 1997-12-22 | 2009-10-15 | 置換複素環式尿素を用いたｒａｆキナーゼの阻害 |
| JP2009237917A Division JP2010065042A (ja) | 1997-12-22 | 2009-10-15 | 置換複素環式尿素を用いたｒａｆキナーゼの阻害 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001526220A JP2001526220A (ja) | 2001-12-18 |
| JP2001526220A5 true JP2001526220A5 (https=) | 2006-01-05 |
| JP4437270B2 JP4437270B2 (ja) | 2010-03-24 |
Family
ID=25542800
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000525097A Expired - Fee Related JP4437270B2 (ja) | 1997-12-22 | 1998-12-22 | 置換複素環式尿素を用いたｒａｆキナーゼの阻害 |
| JP2009237917A Pending JP2010065042A (ja) | 1997-12-22 | 2009-10-15 | 置換複素環式尿素を用いたｒａｆキナーゼの阻害 |
| JP2009237895A Pending JP2010065041A (ja) | 1997-12-22 | 2009-10-15 | 置換複素環式尿素を用いたｒａｆキナーゼの阻害 |
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| JP2009237917A Pending JP2010065042A (ja) | 1997-12-22 | 2009-10-15 | 置換複素環式尿素を用いたｒａｆキナーゼの阻害 |
| JP2009237895A Pending JP2010065041A (ja) | 1997-12-22 | 2009-10-15 | 置換複素環式尿素を用いたｒａｆキナーゼの阻害 |
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| JP (3) | JP4437270B2 (https=) |
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| BG (1) | BG64984B1 (https=) |
| BR (1) | BR9814374B1 (https=) |
| CA (1) | CA2315717C (https=) |
| CU (1) | CU23126A3 (https=) |
| CZ (1) | CZ299156B6 (https=) |
| DE (2) | DE69831013T2 (https=) |
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| HU (1) | HUP0101704A3 (https=) |
| ID (1) | ID26620A (https=) |
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| PL (1) | PL205321B1 (https=) |
| RU (1) | RU2232015C2 (https=) |
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| TR (1) | TR200002618T2 (https=) |
| UA (1) | UA71904C2 (https=) |
| WO (1) | WO1999032106A1 (https=) |
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1998
- 1998-12-22 DE DE69831013T patent/DE69831013T2/de not_active Expired - Lifetime
- 1998-12-22 EP EP98965981A patent/EP1047418B1/en not_active Expired - Lifetime
- 1998-12-22 KR KR1020007006929A patent/KR100571588B1/ko not_active Expired - Fee Related
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- 1998-12-22 CZ CZ20002350A patent/CZ299156B6/cs not_active IP Right Cessation
- 1998-12-22 WO PCT/US1998/026078 patent/WO1999032106A1/en not_active Ceased
- 1998-12-22 DK DK98965981T patent/DK1047418T3/da active
- 1998-12-22 ES ES98965981T patent/ES2153340T3/es not_active Expired - Lifetime
- 1998-12-22 CN CNB2004100286556A patent/CN100360507C/zh not_active Expired - Fee Related
- 1998-12-22 DE DE1047418T patent/DE1047418T1/de active Pending
- 1998-12-22 RU RU2000120184/15A patent/RU2232015C2/ru not_active IP Right Cessation
- 1998-12-22 UA UA2000074352A patent/UA71904C2/uk unknown
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- 1998-12-22 SK SK963-2000A patent/SK286213B6/sk not_active IP Right Cessation
- 1998-12-22 AT AT98965981T patent/ATE300299T1/de active
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