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.)
- Granted
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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 (enExample) | 2006-01-05 |
| JP4437270B2 JP4437270B2 (ja) | 2010-03-24 |
Family
ID=25542800
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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Families Citing this family (157)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69826695T2 (de) * | 1997-05-23 | 2006-02-02 | Bayer Pharmaceuticals Corp., West Haven | Arylharnstoffderivate zur behandlung von inflammatorischen oder immunomodulatorischen erkrankungen |
| US6291425B1 (en) * | 1999-09-01 | 2001-09-18 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage |
| AU739642B2 (en) * | 1997-12-22 | 2001-10-18 | Bayer Healthcare Llc | Inhibition of p38 kinase activity using substituted heterocyclic ureas |
| US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| DE1049664T1 (de) * | 1997-12-22 | 2001-05-03 | Bayer Corp., Pittsburgh | Hemmung der raf-kinase unter verwendung von symmetrisch und unsymmetrisch substituierten harnstoffen |
| US7329670B1 (en) | 1997-12-22 | 2008-02-12 | Bayer Pharmaceuticals Corporation | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
| EP1140840B1 (en) | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| ME00275B (me) | 1999-01-13 | 2011-02-10 | Bayer Corp | ω-KARBOKSIARIL SUPSTITUISANI DIFENIL KARBAMIDI KAO INHIBITORI RAF KINAZE |
| ES2384160T3 (es) | 1999-01-13 | 2012-07-02 | Bayer Healthcare Llc | Difenil ureas sustituidas con omega-carboxi arilo como agentes inhibidores de la cinasa p38 |
| UA73492C2 (en) | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| EP1157026A1 (en) | 1999-02-22 | 2001-11-28 | Boehringer Ingelheim Pharmaceuticals Inc. | Polycyclo heterocyclic derivatives as antiinflammatory agents |
| CA2360740A1 (en) | 1999-03-02 | 2000-09-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cathepsin s |
| CZ20013289A3 (cs) | 1999-03-12 | 2002-01-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Sloučeniny výhodné jako protizánětové prostředky |
| ATE309237T1 (de) | 1999-03-12 | 2005-11-15 | Boehringer Ingelheim Pharma | Aromatische heterozyklische verbindungen als antientzündungwirkstoffe |
| ATE312823T1 (de) | 1999-07-09 | 2005-12-15 | Boehringer Ingelheim Pharma | Verfahren zur herstellung heteroarylsubstituierter ureaverbindungen |
| US6420364B1 (en) | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
| US6492393B1 (en) | 1999-11-16 | 2002-12-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
| US6525046B1 (en) | 2000-01-18 | 2003-02-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as antiinflammatory agents |
| US6608052B2 (en) | 2000-02-16 | 2003-08-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
| FR2812633A1 (fr) * | 2000-08-04 | 2002-02-08 | Aventis Cropscience Sa | Derives de phenyl(thio)urees et phenyl(thio)carbamates fongicides |
| US6645990B2 (en) | 2000-08-15 | 2003-11-11 | Amgen Inc. | Thiazolyl urea compounds and methods of uses |
| US20020173507A1 (en) * | 2000-08-15 | 2002-11-21 | Vincent Santora | Urea compounds and methods of uses |
| CN1518543A (zh) * | 2000-08-31 | 2004-08-04 | �Ʒ� | 吡唑衍生物和它们作为蛋白激酶抑制剂的用途 |
| HU230302B1 (hu) | 2000-10-20 | 2015-12-28 | Eisai R&D Management Co., Ltd. | Nitrogéntartalmú aromás származékok és ezeket tartalmazó gyógyászati készítmények |
| AU2002232439A1 (en) | 2000-11-29 | 2002-06-11 | Glaxo Group Limited | Benzimidazole derivatives useful as tie-2 and/or vegfr-2 inhibitors |
| US7235576B1 (en) | 2001-01-12 | 2007-06-26 | Bayer Pharmaceuticals Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| CA2443950C (en) * | 2001-04-20 | 2011-10-18 | Bayer Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
| US7371763B2 (en) | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
| BRPI0209216B8 (pt) * | 2001-04-27 | 2021-05-25 | Kyowa Hakko Kirin Co Ltd | derivados de quinolina e de quinazolina, composições farmacêuticas compreendendo os mesmos e seus usos |
| CA2445003A1 (en) | 2001-05-16 | 2002-11-21 | Boehringer Ingelheim Pharmaceuticals, Inc. | Diarylurea derivatives useful as anti-inflammatory agents |
| JP2004531571A (ja) | 2001-05-25 | 2004-10-14 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | サイトカイン生産のインヒビターとしてのカルバメート及びオキサミド化合物 |
| WO2003007955A2 (en) * | 2001-07-20 | 2003-01-30 | Cancer Research Technology Limited | Biphenyl apurinic/apyrimidinic site endonuclease inhibitors to treat cancer |
| PT2305255E (pt) * | 2001-12-03 | 2012-09-04 | Bayer Healthcare Llc | Compostos de arilureia em combinação com outros agentes citostáticos ou citotóxicos para tratamento de cancros humanos |
| NZ532780A (en) * | 2001-12-21 | 2006-10-27 | Wellcome Trust | Isolated naturally occurring mutant human B-Raf polypeptides and nucleic acids encoding them |
| US8110587B2 (en) | 2002-02-11 | 2012-02-07 | Bayer Healthcare Llc | Aryl ureas as kinase inhibitors |
| US10653684B2 (en) | 2002-02-11 | 2020-05-19 | Bayer Healthcare Llc | Aryl ureas with angiogenisis inhibiting activity |
| EP1478358B1 (en) | 2002-02-11 | 2013-07-03 | Bayer HealthCare LLC | Sorafenib tosylate for the treatment of diseases characterized by abnormal angiogenesis |
| AU2003210969A1 (en) * | 2002-02-11 | 2003-09-04 | Bayer Corporation | Aryl ureas with raf kinase and angiogenesis inhibiting activity |
| CA2473634C (en) | 2002-02-25 | 2011-11-29 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1,4-disubstituted benzofused cycloalkyl urea compounds useful in treating cytokine mediated diseases |
| MY156407A (en) | 2002-02-28 | 2016-02-26 | Novartis Ag | 5-phenylthiazole derivatives and use as p13 kinase inhibitors |
| KR101124245B1 (ko) | 2002-06-27 | 2012-07-02 | 노보 노르디스크 에이/에스 | 치료제로서 아릴 카르보닐 유도체 |
| KR101116627B1 (ko) | 2002-06-27 | 2012-10-09 | 노보 노르디스크 에이/에스 | 치료제로서 아릴 카르보닐 유도체 |
| JP3763414B2 (ja) | 2002-10-21 | 2006-04-05 | 麒麟麦酒株式会社 | Ｎ−｛２−クロロ−４−［（６，７−ジメトキシ−４−キノリル）オキシ］フェニル｝−ｎ’−（５−メチル−３−イソキサゾリル）ウレアの塩の結晶形 |
| EP2426122A1 (en) * | 2002-10-24 | 2012-03-07 | Merck Patent GmbH | Methylene urea derivative as RAF kinasse inhibitors |
| US7144911B2 (en) | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US7202257B2 (en) | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| KR20050100615A (ko) * | 2003-01-14 | 2005-10-19 | 싸이토키네틱스, 인코포레이티드 | 화합물, 조성물 및 방법 |
| JP5229853B2 (ja) | 2003-02-28 | 2013-07-03 | ニッポネックス インコーポレイテッド | 癌その他の疾患の治療に有用な新規な二環尿素誘導体 |
| EP1599466B1 (en) * | 2003-02-28 | 2010-11-24 | Bayer HealthCare LLC | 2-oxo-1,3,5-perhydrotriazapine derivatives useful in the treatment of hyper-proliferative, angiogenesis, and inflammatrory disorders |
| US7557129B2 (en) | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
| WO2004085399A1 (en) * | 2003-03-24 | 2004-10-07 | Merck Patent Gmbh | Oxamide derivatives useful as raf-kinase inhibitors |
| MXPA05010496A (es) * | 2003-03-28 | 2005-11-16 | Pharmacia & Upjohn Co Llc | Moduladores alostericos positivos del receptor de acetilcolina nicotinico. |
| ATE534649T1 (de) | 2003-05-15 | 2011-12-15 | Arqule Inc | Imidazothiazole und imidazoxazolderivative als inhibitoren von p38 |
| DK1626714T3 (da) | 2003-05-20 | 2007-10-15 | Bayer Pharmaceuticals Corp | Dirarylurinstoffer mod sygdomme medieret af PDGFR |
| WO2005005389A2 (en) * | 2003-07-07 | 2005-01-20 | Merck Patent Gmbh | Malonamide derivatives |
| EA010485B1 (ru) | 2003-07-23 | 2008-10-30 | Байер Фамэсьютиклс Копэрейшн | Производное n,n'-дифенилмочевины, фармацевтическая композиция (варианты) и способ лечения и предупреждения заболеваний и состояний с его использованием (варианты) |
| CN101337930B (zh) | 2003-11-11 | 2010-09-08 | 卫材R&D管理有限公司 | 脲衍生物的制备方法 |
| US20050267182A1 (en) * | 2003-11-13 | 2005-12-01 | Ambit Biosciences Corporation | Urea derivatives as FLT-3 modulators |
| MXPA06007667A (es) | 2004-01-06 | 2006-09-01 | Novo Nordisk As | Heteroaril-ureas y su uso como activadores de glucocinasa. |
| TW200530236A (en) | 2004-02-23 | 2005-09-16 | Chugai Pharmaceutical Co Ltd | Heteroaryl phenylurea |
| US20060211752A1 (en) | 2004-03-16 | 2006-09-21 | Kohn Leonard D | Use of phenylmethimazoles, methimazole derivatives, and tautomeric cyclic thiones for the treatment of autoimmune/inflammatory diseases associated with toll-like receptor overexpression |
| JP2007532615A (ja) * | 2004-04-13 | 2007-11-15 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| EP1751139B1 (en) * | 2004-04-30 | 2011-07-27 | Bayer HealthCare LLC | Substituted pyrazolyl urea derivatives useful in the treatment of cancer |
| KR20070011475A (ko) * | 2004-05-12 | 2007-01-24 | 쉐링 코포레이션 | Ｃｘｃｒ1 및 ｃｘｃｒ2 케모카인 길항제 |
| KR20070032648A (ko) * | 2004-05-12 | 2007-03-22 | 브리스톨-마이어스 스큅 컴퍼니 | 혈전 상태의 치료에 유용한 ｐ２ｙ１ 수용체의 우레아길항제 |
| CA2570999C (en) | 2004-06-17 | 2014-01-07 | Cytokinetics, Inc. | Compounds, compositions and methods |
| US7829560B2 (en) | 2004-07-08 | 2010-11-09 | Arqule, Inc. | 1,4-disubstituted naphthalenes as inhibitors of P38 MAP kinase |
| WO2006018718A2 (en) | 2004-08-12 | 2006-02-23 | Pfizer Limited | Triazolopyridinylsulfanyl derivatives as p38 map kinase inhibitors |
| MY191349A (en) * | 2004-08-27 | 2022-06-17 | Bayer Pharmaceuticals Corp | New pharmaceutical compositions for the treatment of hyper-proliferative disorders |
| EP1797881B1 (en) | 2004-09-17 | 2009-04-15 | Eisai R&D Management Co., Ltd. | Medicinal composition with improved stability and reduced gelation properties |
| EP1645556A1 (en) * | 2004-10-07 | 2006-04-12 | Boehringer Ingelheim International GmbH | Arylpiperazine-benzoylamide derivatives useful as pharmaceutical agents |
| CA2584368A1 (en) | 2004-10-19 | 2006-04-27 | Arqule, Inc. | Synthesis of imidazooxazole and imidazothiazole inhibitors of p38 map kinase |
| NZ556433A (en) * | 2005-01-14 | 2010-10-29 | Cgi Pharmaceuticals Inc | 1, 3-diaryl substituted ureas as modulators of kinase activity |
| US7625931B2 (en) | 2005-01-14 | 2009-12-01 | Cgi Pharmaceuticals, Inc. | Certain substituted diphenyl ureas, as modulators of kinase activity |
| WO2006094626A1 (en) | 2005-03-07 | 2006-09-14 | Bayer Healthcare Ag | Pharmaceutical composition comprising an omega- carboxyaryl substituted diphenyl urea for the treatment of cancer |
| DE102005015253A1 (de) * | 2005-04-04 | 2006-10-05 | Merck Patent Gmbh | Pyrazolderivate |
| US7777040B2 (en) | 2005-05-03 | 2010-08-17 | Cgi Pharmaceuticals, Inc. | Certain substituted ureas, as modulators of kinase activity |
| WO2007015578A1 (ja) | 2005-08-02 | 2007-02-08 | Eisai R & D Management Co., Ltd. | 血管新生阻害物質の効果を検定する方法 |
| US7538223B2 (en) | 2005-08-04 | 2009-05-26 | Cytokinetics, Inc. | Compounds, compositions and methods |
| JP5072595B2 (ja) | 2005-08-05 | 2012-11-14 | 中外製薬株式会社 | マルチキナーゼ阻害剤 |
| DE102005037499A1 (de) | 2005-08-09 | 2007-02-15 | Merck Patent Gmbh | Pyrazolderivate |
| CA2629468A1 (en) * | 2005-11-15 | 2007-05-24 | Bayer Pharmaceuticals Corporation | Pyrazolyl urea derivatives useful in the treatment of cancer |
| MX2008006979A (es) * | 2005-12-01 | 2009-01-14 | Bayer Healthcare Llc | Compuestos de urea utiles en el tratamiento contra el cancer. |
| US7825120B2 (en) | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| TW200808321A (en) | 2005-12-15 | 2008-02-16 | Cytokinetics Inc | Certain chemical entities, compositions and methods |
| EP1959962A2 (en) | 2005-12-16 | 2008-08-27 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| US7989455B2 (en) | 2005-12-19 | 2011-08-02 | Cytokinetics, Inc. | Compounds, compositions and methods |
| US8580798B2 (en) | 2005-12-21 | 2013-11-12 | Bayer Intellectual Property Gmbh | Substituted pyrimidine derivatives useful in the treatment of cancer and other disorders |
| WO2007076460A2 (en) * | 2005-12-23 | 2007-07-05 | Kalypsys, Inc. | Substituted thiazole ureas useful as inhibitors of protein kinases |
| US7989461B2 (en) | 2005-12-23 | 2011-08-02 | Amgen Inc. | Substituted quinazolinamine compounds for the treatment of cancer |
| EP2001892B1 (en) | 2006-03-17 | 2013-04-24 | Ambit Biosciences Corporation | Imidazolothiazole compounds for the treatment of proliferative diseases |
| JP5328640B2 (ja) | 2006-04-19 | 2013-10-30 | ノバルティス アーゲー | ６−ｏ−置換ベンゾオキサゾールおよびベンゾチアゾール化合物ならびにｃｓｆ−１ｒシグナル伝達を阻害する方法 |
| ES2556173T3 (es) | 2006-05-18 | 2016-01-13 | Eisai R&D Management Co., Ltd. | Agente antitumoral para un cáncer de tiroides |
| JP2009538317A (ja) | 2006-05-26 | 2009-11-05 | バイエル ヘルスケア リミティド ライアビリティ カンパニー | 癌治療のための置換ジアリールウレアを用いた薬物の組み合わせ |
| DE102006029795A1 (de) * | 2006-06-27 | 2008-01-03 | Schebo Biotech Ag | Neue Harnstoff-Derivate und deren Verwendungen |
| CN101511793B (zh) | 2006-08-28 | 2011-08-03 | 卫材R&D管理有限公司 | 针对未分化型胃癌的抗肿瘤剂 |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| WO2008076883A2 (en) | 2006-12-15 | 2008-06-26 | Abraxis Bioscience, Inc. | Triazine derivatives and their therapeutical applications |
| EP2134677B1 (en) | 2006-12-20 | 2011-10-12 | Bayer HealthCare LLC | 4-{4-[({3-tert-butyl-1-[3-(hydroxymethyl)phenyl]-1h-pyrazol-5-yl}carbamoyl)-amino]-3-chlorophenoxy}-n-methylpyridine-2-carboxamide as an inhibitor of the vegfr kinase for the treatment of cancer |
| KR101445892B1 (ko) | 2007-01-29 | 2014-09-29 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 미분화형 위암 치료용 조성물 |
| US20080269267A1 (en) * | 2007-04-20 | 2008-10-30 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoprolific diseases and other proliferative diseases |
| WO2008153947A2 (en) | 2007-06-07 | 2008-12-18 | Amgen Inc. | Heterocyclic compounds as raf kinase modulators |
| CN101868465B (zh) | 2007-09-19 | 2013-12-25 | 埃姆比特生物科学公司 | 包含N-(5-叔丁基-异噁唑-3-基)-N’-{4-[7-(2-吗啉-4-基-乙氧基)咪唑并[2，1-b][1，3]苯并噻唑-2-基]苯基}脲的固体形式、其组合物及其应用 |
| CN101848895B (zh) | 2007-11-09 | 2013-10-23 | 卫材R&D管理有限公司 | 血管新生抑制物质和抗肿瘤性铂络合物的组合使用 |
| AR070535A1 (es) | 2008-02-29 | 2010-04-14 | Array Biopharma Inc | Compuestos inhibidores de raf y metodos para usarlos |
| US8394795B2 (en) | 2008-02-29 | 2013-03-12 | Array Biopharma Inc. | Pyrazole [3, 4-B] pyridine Raf inhibitors |
| BRPI0920707A2 (pt) | 2008-10-02 | 2015-12-29 | Respivert Ltd | compostos |
| US8299074B2 (en) * | 2008-12-11 | 2012-10-30 | Respivert Ltd. | P38 MAP kinase inhibitors |
| KR20170058465A (ko) | 2009-04-03 | 2017-05-26 | 에프. 호프만-라 로슈 아게 | 프로판-１-술폰산 ｛３-［５-（４-클로로-페닐）-１Ｈ-피롤로［２，３-ｂ］피리딘-３-카르보닐］-２，４-디플루오로-페닐｝-아미드 조성물 및 그의 용도 |
| GB0905955D0 (en) | 2009-04-06 | 2009-05-20 | Respivert Ltd | Novel compounds |
| CA2765044A1 (en) | 2009-06-09 | 2010-12-16 | California Capital Equity, Llc | Benzyl substituted triazine derivatives and their therapeutical applications |
| CN102573480B (zh) | 2009-06-09 | 2015-06-10 | 加利福尼亚资本权益有限责任公司 | 三嗪衍生物及其治疗应用 |
| AU2010315126B2 (en) | 2009-11-06 | 2015-06-25 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| US9260410B2 (en) | 2010-04-08 | 2016-02-16 | Respivert Ltd. | P38 MAP kinase inhibitors |
| CA2802644C (en) | 2010-06-25 | 2017-02-21 | Eisai R & D Management Co., Ltd. | Antitumor agent using compounds having kinase inhibitory effect in combination |
| KR20130091331A (ko) | 2010-07-16 | 2013-08-16 | 교와 핫꼬 기린 가부시키가이샤 | 함질소 방향족 복소환 유도체 |
| WO2012008564A1 (ja) * | 2010-07-16 | 2012-01-19 | 協和発酵キリン株式会社 | 含窒素芳香族複素環誘導体 |
| EP2595628A1 (en) | 2010-07-19 | 2013-05-29 | Bayer HealthCare LLC | Drug combinations with fluoro-substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions |
| WO2012109075A1 (en) | 2011-02-07 | 2012-08-16 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| RU2580609C2 (ru) | 2011-04-18 | 2016-04-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Противоопухолевое терапевтическое средство |
| EP3444363B1 (en) | 2011-06-03 | 2020-11-25 | Eisai R&D Management Co., Ltd. | Biomarkers for prediciting and assessing responsiveness of thyroid and kidney cancer subjects to lenvatinib compounds |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| CA2879431A1 (en) | 2012-07-17 | 2014-01-23 | Washington University | Anti-mucus drugs and uses therefor |
| AU2013364953A1 (en) | 2012-12-21 | 2015-04-30 | Eisai R&D Management Co., Ltd. | Amorphous form of quinoline derivative, and method for producing same |
| WO2014185540A1 (en) | 2013-05-14 | 2014-11-20 | Eisai R&D Management Co., Ltd. | Biomarkers for predicting and assessing responsiveness of endometrial cancer subjects to lenvatinib compounds |
| US9750723B2 (en) | 2013-10-31 | 2017-09-05 | Ohio University | Prevention and treatment of non-alcoholic fatty liver disease |
| US10023567B2 (en) | 2014-07-18 | 2018-07-17 | Ohio University | Imidazole and thiazole compositions for modifying biological signaling |
| JP6578349B2 (ja) | 2014-08-11 | 2019-09-18 | アンジオン バイオメディカ コーポレーション | チトクロームｐ４５０阻害剤およびその使用 |
| KR102329681B1 (ko) | 2014-08-28 | 2021-11-23 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 고순도의 퀴놀린 유도체 및 이를 제조하는 방법 |
| JP6538153B2 (ja) * | 2014-09-10 | 2019-07-03 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | Ｒｅａｒｒａｎｇｅｄ ｄｕｒｉｎｇ ｔｒａｎｓｆｅｃｔｉｏｎ（ｒｅｔ）阻害剤としての新規な化合物 |
| RS58813B1 (sr) | 2014-09-10 | 2019-07-31 | Glaxosmithkline Ip Dev Ltd | Piridonski derivati korišćeni kao inhibitori kinaze reorganizovane tokom transfekcije (ret) |
| US9638690B2 (en) | 2014-11-07 | 2017-05-02 | The University Of British Columbia | Compounds and compositions for use as alkylating agent sensors and methods of use thereof |
| CN107531631B (zh) | 2014-12-31 | 2021-09-03 | 安吉昂生物医药公司 | 用于治疗疾病的方法和药剂 |
| KR20250024102A (ko) | 2015-02-25 | 2025-02-18 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 퀴놀린 유도체의 고미 억제 방법 |
| AU2015384801B2 (en) | 2015-03-04 | 2022-01-06 | Eisai R&D Management Co., Ltd. | Combination of a PD-1 antagonist and a VEGFR/FGFR/RET tyrosine kinase inhibitor for treating cancer |
| ES2886107T3 (es) | 2015-06-16 | 2021-12-16 | Prism Biolab Co Ltd | Antineoplásico |
| SG11201801083UA (en) | 2015-08-20 | 2018-03-28 | Eisai R&D Man Co Ltd | Tumor therapeutic agent |
| CN110072526A (zh) * | 2016-08-17 | 2019-07-30 | 西奈山伊坎医学院 | 治疗癌症的激酶抑制剂化合物、组合物和方法 |
| CN106866571B (zh) * | 2017-01-20 | 2018-06-29 | 中国药科大学 | 杂环脲类化合物及其药物组合物和应用 |
| US12303505B2 (en) | 2017-02-08 | 2025-05-20 | Eisai R&D Management Co., Ltd. | Tumor-treating pharmaceutical composition |
| US20200197384A1 (en) | 2017-05-16 | 2020-06-25 | Eisai R&D Management Co., Ltd. | Treatment of hepatocellular carcinoma |
| CN118903436A (zh) | 2018-01-31 | 2024-11-08 | 德西费拉制药有限责任公司 | 治疗肥大细胞增多症的组合疗法 |
| JP2021512105A (ja) | 2018-01-31 | 2021-05-13 | デシフェラ・ファーマシューティカルズ，エルエルシー | 消化管間質腫瘍の治療のための併用療法 |
| EP4487909A3 (en) | 2018-06-12 | 2025-03-19 | vTv Therapeutics LLC | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
| CN110903245B (zh) * | 2018-09-17 | 2022-11-22 | 南京药石科技股份有限公司 | 一种合成1-烷基-2-三氟甲基-5-氨基-1h-咪唑的关键中间体及其制备方法 |
| CA3140017A1 (en) * | 2019-07-19 | 2021-01-28 | Aurore HICK | Polyaromatic urea derivatives and their use in the treatment of muscle diseases |
| NZ784949A (en) | 2019-08-12 | 2025-09-26 | Deciphera Pharmaceuticals Llc | Ripretinib for treating gastrointestinal stromal tumors |
| TWI878335B (zh) | 2019-08-12 | 2025-04-01 | 美商迪賽孚爾製藥有限公司 | 治療胃腸道基質瘤方法 |
| FI4084778T3 (fi) | 2019-12-30 | 2023-12-18 | Deciphera Pharmaceuticals Llc | Amorfisia kinaasi-inhibiittoriformulaatioita ja menetelmiä niiden käyttämiseksi |
| SMT202400484T1 (it) | 2019-12-30 | 2025-01-14 | Deciphera Pharmaceuticals Llc | Composizioni di 1-(4-bromo-5-(1-etil-7-(metilammino)-2-osso-1,2-diidro-1,6-naftiridin-3-il)-2-fluorofenil)-3-fenilurea |
| WO2021167840A1 (en) | 2020-02-18 | 2021-08-26 | Vtv Therapeutics Llc | Sulfoxide and sulfone glucokinase activators and methods of use thereof |
| WO2021180008A1 (zh) * | 2020-03-11 | 2021-09-16 | 暨南大学 | 含脲结构的三芳环化合物及其应用 |
| WO2022135442A1 (zh) * | 2020-12-22 | 2022-06-30 | 上海拓界生物医药科技有限公司 | Cdk2抑制剂及其制备方法 |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
| WO2024126777A1 (en) * | 2022-12-16 | 2024-06-20 | Astrazeneca Ab | Heteroaromatic compounds |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3754887A (en) * | 1969-05-05 | 1973-08-28 | Du Pont | Ureidopyrazoles defoliants |
| JPS5031039A (enExample) * | 1973-07-27 | 1975-03-27 | ||
| US3990879A (en) * | 1974-12-26 | 1976-11-09 | Eli Lilly And Company | Method of controlling aquatic weeds |
| US4183854A (en) * | 1976-11-10 | 1980-01-15 | John Wyeth & Brother Limited | Thiazole compound |
| US4042372A (en) * | 1976-11-19 | 1977-08-16 | Eli Lilly And Company | Substituted thiadiazolotriazinediones and method of preparation |
| JPS5386033A (en) * | 1977-10-20 | 1978-07-29 | Shionogi & Co Ltd | Herbicides |
| DE3612830A1 (de) * | 1986-04-16 | 1987-10-22 | Basf Ag | Thiadiazolylharnstoff enthaltendes mittel zur entblaetterung von pflanzen |
| FR2639636B1 (fr) * | 1988-11-30 | 1994-03-04 | Novapharme | Nouveaux composes heterocycliques a activite anticonvulsivante, procede de preparation et compositions therapeutiques les contenant |
| GB9000644D0 (en) * | 1990-01-11 | 1990-03-14 | Erba Carlo Spa | New ureido derivatives of poly-4-amino-2-carboxy-1-methyl compounds |
| KR930702334A (ko) * | 1990-09-13 | 1993-09-08 | 데이비드 로버트 | 5 하이드록시트립타민 수용체 길항제로서의 인돌우레아 |
| US5185358A (en) * | 1991-06-24 | 1993-02-09 | Warner-Lambert Co. | 3-heteroatom containing urea and thiourea ACAT inhibitors |
| US5162360A (en) * | 1991-06-24 | 1992-11-10 | Warner-Lambert Company | 2-heteroatom containing urea and thiourea ACAT inhibitors |
| US5508288A (en) * | 1992-03-12 | 1996-04-16 | Smithkline Beecham, P.L.C. | Indole derivatives as 5HT1C antagonists |
| WO1994014801A1 (en) * | 1992-12-29 | 1994-07-07 | Smithkline Beecham Plc | Heterocyclic urea derivatives as 5ht2c and 5ht2b antagonists |
| CA2200981A1 (en) * | 1994-10-04 | 1996-04-11 | Hisashi Takasugi | Urea derivatives and their use as acat-inhibitors |
| WO1996025157A1 (en) * | 1995-02-17 | 1996-08-22 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| US5814646A (en) * | 1995-03-02 | 1998-09-29 | Eli Lilly And Company | Inhibitors of amyloid beta-protein production |
| US5773459A (en) * | 1995-06-07 | 1998-06-30 | Sugen, Inc. | Urea- and thiourea-type compounds |
| AU723730B2 (en) * | 1996-04-23 | 2000-09-07 | Vertex Pharmaceuticals Incorporated | Urea derivatives as inhibitors of IMPDH enzyme |
| GB9623833D0 (en) * | 1996-11-16 | 1997-01-08 | Zeneca Ltd | Chemical compound |
| EP0986382B1 (en) * | 1997-05-23 | 2008-06-25 | Bayer Pharmaceuticals Corporation | Raf kinase inhibitors |
| GB9723789D0 (en) * | 1997-11-12 | 1998-01-07 | Zeneca Ltd | Chemical compounds |
| AU739642B2 (en) * | 1997-12-22 | 2001-10-18 | Bayer Healthcare Llc | Inhibition of p38 kinase activity using substituted heterocyclic ureas |
| PL341356A1 (en) * | 1997-12-22 | 2001-04-09 | Bayer Ag | Raf kinase inhibition employing aryl- and heteroaryl-substituted heterocyclic ureas |
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- 1998-12-22 KR KR1020007006929A patent/KR100571588B1/ko not_active Expired - Fee Related
- 1998-12-22 CN CNB988136236A patent/CN1149085C/zh not_active Expired - Fee Related
- 1998-12-22 TR TR2000/02618T patent/TR200002618T2/xx unknown
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- 1998-12-22 BR BRPI9814374-3B1A patent/BR9814374B1/pt not_active IP Right Cessation
- 1998-12-22 CA CA2315717A patent/CA2315717C/en not_active Expired - Fee Related
- 1998-12-22 DK DK98965981T patent/DK1047418T3/da active
- 1998-12-22 AU AU21989/99A patent/AU2198999A/en not_active Abandoned
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- 1998-12-22 WO PCT/US1998/026078 patent/WO1999032106A1/en not_active Ceased
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