JP2005518447A5 - - Google Patents
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- JP2005518447A5 JP2005518447A5 JP2003571275A JP2003571275A JP2005518447A5 JP 2005518447 A5 JP2005518447 A5 JP 2005518447A5 JP 2003571275 A JP2003571275 A JP 2003571275A JP 2003571275 A JP2003571275 A JP 2003571275A JP 2005518447 A5 JP2005518447 A5 JP 2005518447A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- heteroaryl
- alkoxy
- partially
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 82
- -1 2,3-dihydrobenzo [1,4] oxazinyl Chemical group 0.000 claims 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 42
- 125000001072 heteroaryl group Chemical group 0.000 claims 32
- 125000003545 alkoxy group Chemical group 0.000 claims 31
- 125000000623 heterocyclic group Chemical group 0.000 claims 31
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 150000002367 halogens Chemical class 0.000 claims 22
- 125000001544 thienyl group Chemical group 0.000 claims 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 12
- 125000003386 piperidinyl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000002541 furyl group Chemical group 0.000 claims 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- 150000002825 nitriles Chemical class 0.000 claims 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 5
- 125000002252 acyl group Chemical group 0.000 claims 5
- 125000003435 aroyl group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims 4
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims 4
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 4
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 3
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- 229930192474 thiophene Natural products 0.000 claims 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 102000004127 Cytokines Human genes 0.000 claims 2
- 108090000695 Cytokines Proteins 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- GVBVCGXMMISBLL-UHFFFAOYSA-N 1-[4-[2-(2-benzylmorpholin-4-yl)ethoxy]naphthalen-1-yl]-3-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CC(CC=4C=CC=CC=4)OCC3)=CC=2)=CC(C(C)(C)C)=N1 GVBVCGXMMISBLL-UHFFFAOYSA-N 0.000 claims 1
- PECOQIDIDCMWMT-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(oxolan-2-ylmethylamino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NCC4OCCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 PECOQIDIDCMWMT-UHFFFAOYSA-N 0.000 claims 1
- NVIBGZFJFJNVSX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-[2-(1-phenylethylamino)pyrimidin-4-yl]ethoxy]naphthalen-1-yl]urea Chemical compound C=1C=CC=CC=1C(C)NC(N=1)=NC=CC=1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 NVIBGZFJFJNVSX-UHFFFAOYSA-N 0.000 claims 1
- QMEUJENVHAUGFR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-[2-(1-pyridin-2-ylethylamino)pyrimidin-4-yl]ethoxy]naphthalen-1-yl]urea Chemical compound C=1C=CC=NC=1C(C)NC(N=1)=NC=CC=1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 QMEUJENVHAUGFR-UHFFFAOYSA-N 0.000 claims 1
- WMFZUKOJQVIGPT-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]-3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]naphthalen-1-yl]urea Chemical compound C1=NC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3C4=CC=CC=C4OCC3)=CC=2)=CC(C(C)(C)C)=N1 WMFZUKOJQVIGPT-UHFFFAOYSA-N 0.000 claims 1
- HCUUNOIGGVSFNS-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]-3-[4-[2-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)ethoxy]naphthalen-1-yl]urea Chemical compound C1=NC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3C4CC(OC4)C3)=CC=2)=CC(C(C)(C)C)=N1 HCUUNOIGGVSFNS-UHFFFAOYSA-N 0.000 claims 1
- RXKJPQGZGDGTFG-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3C4=CC=CC=C4OCC3)=CC=2)=CC(C(C)(C)C)=N1 RXKJPQGZGDGTFG-UHFFFAOYSA-N 0.000 claims 1
- QBBAZGGEFIGFMK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]-3-[4-[2-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)ethoxy]naphthalen-1-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3C4CC(OC4)C3)=CC=2)=CC(C(C)(C)C)=N1 QBBAZGGEFIGFMK-UHFFFAOYSA-N 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
- DAWDQZGDDRJTKJ-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n,n-dimethylmorpholine-2-carboxamide Chemical compound C1COC(C(=O)N(C)C)CN1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 DAWDQZGDDRJTKJ-UHFFFAOYSA-N 0.000 claims 1
- GMZVYPPUEBUCLV-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n-ethylmorpholine-2-carboxamide Chemical compound C1COC(C(=O)NCC)CN1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 GMZVYPPUEBUCLV-UHFFFAOYSA-N 0.000 claims 1
- MDYOASQEMWCJAH-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n-ethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCC)=CC(CCOC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 MDYOASQEMWCJAH-UHFFFAOYSA-N 0.000 claims 1
- YENZHSZBUBCSMN-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n-methyl-n-phenylmorpholine-2-carboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C(OCC1)CN1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 YENZHSZBUBCSMN-UHFFFAOYSA-N 0.000 claims 1
- BQPYYUKNQCGFAW-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n-methylmorpholine-2-carboxamide Chemical compound C1COC(C(=O)NC)CN1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 BQPYYUKNQCGFAW-UHFFFAOYSA-N 0.000 claims 1
- VWGYUWQMLXDZBW-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n-phenylmorpholine-2-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CC(OCC3)C(=O)NC=3C=CC=CC=3)=CC=2)=CC(C(C)(C)C)=N1 VWGYUWQMLXDZBW-UHFFFAOYSA-N 0.000 claims 1
- KIEWNGKGWHQANG-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n,n-dimethylmorpholine-2-carboxamide Chemical compound C1COC(C(=O)N(C)C)CN1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 KIEWNGKGWHQANG-UHFFFAOYSA-N 0.000 claims 1
- GOGLWHHQNJYDHX-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n-methyl-n-phenylmorpholine-2-carboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C(OCC1)CN1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 GOGLWHHQNJYDHX-UHFFFAOYSA-N 0.000 claims 1
- HKNOZLWOFQMZEP-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n-methylmorpholine-2-carboxamide Chemical compound C1COC(C(=O)NC)CN1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 HKNOZLWOFQMZEP-UHFFFAOYSA-N 0.000 claims 1
- PGLGQQCYJKFCKQ-UHFFFAOYSA-N 4-[2-[4-[[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]-n-phenylmorpholine-2-carboxamide Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CC(OCC3)C(=O)NC=3C=CC=CC=3)=CC=2)=CC(C(C)(C)C)=N1 PGLGQQCYJKFCKQ-UHFFFAOYSA-N 0.000 claims 1
- RSXDKWNRYWQGPV-UHFFFAOYSA-N 4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxy-n,n-diethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(CC)CC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 RSXDKWNRYWQGPV-UHFFFAOYSA-N 0.000 claims 1
- IXJROPZKTIJILP-UHFFFAOYSA-N 4-[4-[[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxy-n-methyl-n-phenylpyridine-2-carboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C(N=CC=1)=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 IXJROPZKTIJILP-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 1
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 claims 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims 1
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| PCT/US2003/007268 WO2003072569A1 (en) | 2002-02-25 | 2003-02-19 | 1,4-disubstituted benzofused cycloalkyl urea compounds useful in treating cytokine mediated diseases |
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| CN102060806A (zh) | 2003-09-11 | 2011-05-18 | iTherX药品公司 | 细胞因子抑制剂 |
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| DE102005015253A1 (de) * | 2005-04-04 | 2006-10-05 | Merck Patent Gmbh | Pyrazolderivate |
| JP5131990B2 (ja) * | 2006-01-31 | 2013-01-30 | アレイ バイオファーマ、インコーポレイテッド | キナーゼ阻害剤およびその使用方法 |
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| US20110189167A1 (en) * | 2007-04-20 | 2011-08-04 | Flynn Daniel L | Methods and Compositions for the Treatment of Myeloproliferative Diseases and other Proliferative Diseases |
| GB0818033D0 (en) * | 2008-10-02 | 2008-11-05 | Respivert Ltd | Novel compound |
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| KR20110099687A (ko) * | 2008-10-29 | 2011-09-08 | 데시페라 파마슈티칼스, 엘엘씨. | 항-암과 항-증식성 활성을 나타내는 시클로프로판 아미드와 유사체 |
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| EP2578582A1 (en) * | 2011-10-03 | 2013-04-10 | Respivert Limited | 1-Pyrazolyl-3-(4-((2-anilinopyrimidin-4-yl)oxy)napththalen-1-yl)ureas as p38 MAP kinase inhibitors |
| UY34363A (es) * | 2011-10-03 | 2013-04-30 | Respivert Ltd | 1?(3?tert?BUTIL?1?P?TOLIL?1H?PIRAZOL?5?IL)?3?(4?(2?(FENILAMINO)PIRIMIDIN?4?ILOXI)NAFTALEN?1?IL)UREA COMO INHIBIDORES DE LA FAMILIA DE ENZIMAS DE PROTEÍNAS QUINASAS ACTIVADAS POR MITÓGENO p38 Y SUS USOS EN TERAPIA |
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| BR112015024678B1 (pt) | 2013-04-02 | 2023-02-23 | Oxular Acquisitions Limited | Composto inibidor da cinase, formulação farmacêutica que compreende o mesmo, seus usos, processo para sua preparação e intermediários |
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| JP6514703B2 (ja) | 2013-12-20 | 2019-05-15 | トピバート ファーマ リミテッド | キナーゼインヒビターとして有用な尿素誘導体 |
| TWI664967B (zh) | 2014-02-14 | 2019-07-11 | 英商瑞斯比維特有限公司 | 新穎化合物（一） |
| TR201908937T4 (tr) | 2014-08-29 | 2019-07-22 | Torrent Pharmaceuticals Ltd | P38 MAP kinazı inhibe eden indanil üre bileşikleri. |
| MA40775A (fr) | 2014-10-01 | 2017-08-08 | Respivert Ltd | Dérivé d'acide 4-(4-(4-phényluréido-naphtalén -1-yl) oxy-pyridin-2-yl) amino-benzoïque utilisé en tant qu'inhibiteur de la kinase p38 |
| CA3015978A1 (en) | 2016-04-06 | 2017-10-12 | Topivert Pharma Limited | Kinase inhibitors |
| EP3746060A1 (en) | 2018-01-31 | 2020-12-09 | Deciphera Pharmaceuticals, LLC | Combination therapy for the treatment of mastocytosis |
| BR112020015581A2 (pt) | 2018-01-31 | 2021-02-02 | Deciphera Pharmaceuticals, Llc | terapia de combinação para o tratamento de tumores estromais gastrointestinais |
| WO2021013712A1 (en) | 2019-07-19 | 2021-01-28 | Anagenesis Biotechnologies S.A.S. | Polyaromatic urea derivatives and their use in the treatment of muscle diseases |
| WO2021030405A1 (en) | 2019-08-12 | 2021-02-18 | Deciphera Pharmaceuticals, Llc | Ripretinib for treating gastrointestinal stromal tumors |
| KR20220045189A (ko) | 2019-08-12 | 2022-04-12 | 데시페라 파마슈티칼스, 엘엘씨. | 위장관 기질 종양을 치료하는 방법 |
| SMT202300467T1 (it) | 2019-12-30 | 2024-01-10 | Deciphera Pharmaceuticals Llc | Formulazioni di inibitori di chinasi amorfi e loro procedimenti d’uso |
| CN118948773A (zh) | 2019-12-30 | 2024-11-15 | 德西费拉制药有限责任公司 | 1-(4溴-5-(1乙基-7-(甲氨基)-2侧氧基-1,2-二氢-1,6-萘啶-3基)-2氟苯基)-3-苯基脲的组合物 |
| EP4029501A1 (en) | 2021-01-19 | 2022-07-20 | Anagenesis Biotechnologies | Combination of polyaromatic urea derivatives and glucocorticoid or hdac inhibitor for the treatment of diseases or conditions associated with muscle cells and/or satellite cells |
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- 2003-02-19 JP JP2003571275A patent/JP4629978B2/ja not_active Expired - Lifetime
- 2003-02-19 CA CA2473634A patent/CA2473634C/en not_active Expired - Lifetime
- 2003-02-19 AU AU2003213806A patent/AU2003213806A1/en not_active Abandoned
- 2003-02-19 DE DE60319066T patent/DE60319066T2/de not_active Expired - Lifetime
- 2003-02-19 AT AT03711498T patent/ATE386030T1/de active
- 2003-02-19 US US10/369,847 patent/US7041669B2/en not_active Expired - Lifetime
- 2003-02-19 ES ES03711498T patent/ES2299689T3/es not_active Expired - Lifetime
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