AU2004249675B2 - Indazole, benzisoxazole, and benzisothiazole kinase inhibitors - Google Patents
Indazole, benzisoxazole, and benzisothiazole kinase inhibitors Download PDFInfo
- Publication number
- AU2004249675B2 AU2004249675B2 AU2004249675A AU2004249675A AU2004249675B2 AU 2004249675 B2 AU2004249675 B2 AU 2004249675B2 AU 2004249675 A AU2004249675 A AU 2004249675A AU 2004249675 A AU2004249675 A AU 2004249675A AU 2004249675 B2 AU2004249675 B2 AU 2004249675B2
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- AU
- Australia
- Prior art keywords
- amino
- phenyl
- indazol
- urea
- fluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 229940043355 kinase inhibitor Drugs 0.000 title claims description 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 254
- 238000000034 method Methods 0.000 claims abstract description 37
- 238000011282 treatment Methods 0.000 claims abstract description 35
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims description 309
- 229910052739 hydrogen Inorganic materials 0.000 claims description 309
- 125000000217 alkyl group Chemical group 0.000 claims description 286
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 214
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 198
- 125000003545 alkoxy group Chemical group 0.000 claims description 142
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 109
- 150000002431 hydrogen Chemical class 0.000 claims description 108
- 125000001188 haloalkyl group Chemical group 0.000 claims description 92
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 90
- 125000000623 heterocyclic group Chemical group 0.000 claims description 89
- 125000004104 aryloxy group Chemical group 0.000 claims description 87
- 229910003827 NRaRb Inorganic materials 0.000 claims description 82
- -1 heterocyclylalkoxy Chemical group 0.000 claims description 82
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 65
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 64
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 64
- 125000003342 alkenyl group Chemical group 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 62
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 61
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 60
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 55
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 53
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 52
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 48
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 44
- 239000004202 carbamide Substances 0.000 claims description 42
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 229910052701 rubidium Inorganic materials 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 16
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000003944 tolyl group Chemical group 0.000 claims description 14
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 239000002246 antineoplastic agent Substances 0.000 claims description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 10
- 102000001253 Protein Kinase Human genes 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 9
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 9
- 108060006633 protein kinase Proteins 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 7
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- BMTADBMFDZSIJP-UHFFFAOYSA-N 1-[4-(3-amino-7-methyl-1h-indazol-4-yl)phenyl]-3-(3-chlorophenyl)urea Chemical compound C1=2C(N)=NNC=2C(C)=CC=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 BMTADBMFDZSIJP-UHFFFAOYSA-N 0.000 claims description 2
- PBSLJASXQKBHPI-UHFFFAOYSA-N 1-[4-(3-amino-7-methyl-1h-indazol-4-yl)phenyl]-3-(3-fluorophenyl)urea Chemical compound C1=2C(N)=NNC=2C(C)=CC=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 PBSLJASXQKBHPI-UHFFFAOYSA-N 0.000 claims description 2
- ZWWSNDNMPKVIRB-UHFFFAOYSA-N 1-[4-[3-amino-7-(2-morpholin-4-ylethoxy)-1h-indazol-4-yl]phenyl]-3-(3-chlorophenyl)urea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C=C(Cl)C=CC=3)=CC=2)=C2C(N)=NNC2=C1OCCN1CCOCC1 ZWWSNDNMPKVIRB-UHFFFAOYSA-N 0.000 claims description 2
- NCGUWOPKSVMWOW-UHFFFAOYSA-N 1-[4-[3-amino-7-[(4-chlorophenoxy)methyl]-1h-indazol-4-yl]phenyl]-3-(4-fluoro-3-methylphenyl)urea Chemical compound C1=C(F)C(C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NNC=3C(COC=3C=CC(Cl)=CC=3)=CC=2)=C1 NCGUWOPKSVMWOW-UHFFFAOYSA-N 0.000 claims description 2
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 15
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 14
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 3
- 239000003909 protein kinase inhibitor Substances 0.000 claims 2
- USPAHWKEPYXFBE-UHFFFAOYSA-N (2-fluoro-5-methylphenyl)urea Chemical compound CC1=CC=C(F)C(NC(N)=O)=C1 USPAHWKEPYXFBE-UHFFFAOYSA-N 0.000 claims 1
- NRNYBPSJGWZOBT-UHFFFAOYSA-N 1-[4-(1-acetyl-3-aminoindazol-4-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound C1=CC=C2N(C(=O)C)N=C(N)C2=C1C(C=C1)=CC=C1NC(=O)NC1=CC(C)=CC=C1F NRNYBPSJGWZOBT-UHFFFAOYSA-N 0.000 claims 1
- GDEJPGKNPRJNGE-UHFFFAOYSA-N 1-[4-(3-amino-1-methylindazol-4-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NN(C)C=3C=CC=2)=C1 GDEJPGKNPRJNGE-UHFFFAOYSA-N 0.000 claims 1
- SJLMWYBFMFKEOW-UHFFFAOYSA-N 1-[4-(3-amino-1-methylindazol-4-yl)phenyl]-3-(3-bromophenyl)urea Chemical compound C1=CC=C2N(C)N=C(N)C2=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Br)=C1 SJLMWYBFMFKEOW-UHFFFAOYSA-N 0.000 claims 1
- PTXJNQZOAPXYBW-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)-3-fluorophenyl]-3-(3-chlorophenyl)urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C(=C1)F)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 PTXJNQZOAPXYBW-UHFFFAOYSA-N 0.000 claims 1
- HQPNLIKXAPLWBQ-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-(4-fluoro-3-methylphenyl)urea Chemical compound C1=C(F)C(C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NNC=3C=CC=2)=C1 HQPNLIKXAPLWBQ-UHFFFAOYSA-N 0.000 claims 1
- OFPGICHPZXZMBC-UHFFFAOYSA-N 1-[4-(3-amino-4-bromo-1h-indazol-6-yl)phenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3NN=C(N)C3=C(Br)C=2)=C1 OFPGICHPZXZMBC-UHFFFAOYSA-N 0.000 claims 1
- NSWZDXUHTYWTTE-UHFFFAOYSA-N 1-[4-(3-amino-5-fluoro-1h-indazol-4-yl)phenyl]-3-(3-chlorophenyl)urea Chemical compound C=12C(N)=NNC2=CC=C(F)C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 NSWZDXUHTYWTTE-UHFFFAOYSA-N 0.000 claims 1
- DGJOGHHWHRLPAD-UHFFFAOYSA-N 1-[4-(3-amino-5-fluoro-1h-indazol-4-yl)phenyl]-3-[2-fluoro-3-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=CC=C(F)C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1F DGJOGHHWHRLPAD-UHFFFAOYSA-N 0.000 claims 1
- XEJQTYWCLUKANO-UHFFFAOYSA-N 1-[4-(3-amino-7-bromo-1h-indazol-4-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NNC=3C(Br)=CC=2)=C1 XEJQTYWCLUKANO-UHFFFAOYSA-N 0.000 claims 1
- KJIQOAPOQQAKNT-UHFFFAOYSA-N 1-[4-(3-amino-7-bromo-1h-indazol-4-yl)phenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NNC=3C(Br)=CC=2)=C1 KJIQOAPOQQAKNT-UHFFFAOYSA-N 0.000 claims 1
- IRFUEOONZLFXRE-UHFFFAOYSA-N 1-[4-(3-amino-7-fluoro-1h-indazol-4-yl)phenyl]-3-(3-chlorophenyl)urea Chemical compound C=12C(N)=NNC2=C(F)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 IRFUEOONZLFXRE-UHFFFAOYSA-N 0.000 claims 1
- YNNIFKGZQUXXEF-UHFFFAOYSA-N 1-[4-(3-amino-7-fluoro-1h-indazol-4-yl)phenyl]-3-phenylurea Chemical compound C=12C(N)=NNC2=C(F)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 YNNIFKGZQUXXEF-UHFFFAOYSA-N 0.000 claims 1
- DZXBFGNHDRDLHD-UHFFFAOYSA-N 1-[4-(3-amino-7-hydroxy-1h-indazol-4-yl)phenyl]-3-(3-chlorophenyl)urea Chemical compound C=12C(N)=NNC2=C(O)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 DZXBFGNHDRDLHD-UHFFFAOYSA-N 0.000 claims 1
- SGBWPSGQHRKBIC-UHFFFAOYSA-N 1-[4-(3-amino-7-hydroxy-1h-indazol-4-yl)phenyl]-3-(3-fluorophenyl)urea Chemical compound C=12C(N)=NNC2=C(O)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 SGBWPSGQHRKBIC-UHFFFAOYSA-N 0.000 claims 1
- OQXNZBNSZVBRKJ-UHFFFAOYSA-N 1-[4-(3-amino-7-hydroxy-1h-indazol-4-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=C(O)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 OQXNZBNSZVBRKJ-UHFFFAOYSA-N 0.000 claims 1
- IACQNCCUMQJMAL-UHFFFAOYSA-N 1-[4-(3-amino-7-hydroxy-1h-indazol-4-yl)phenyl]-3-[4-fluoro-3-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=C(O)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C(C(F)(F)F)=C1 IACQNCCUMQJMAL-UHFFFAOYSA-N 0.000 claims 1
- CEXZSMQLFAJQAA-UHFFFAOYSA-N 1-[4-(3-amino-7-methyl-1h-indazol-4-yl)phenyl]-3-(3-cyanophenyl)urea Chemical compound C1=2C(N)=NNC=2C(C)=CC=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C#N)=C1 CEXZSMQLFAJQAA-UHFFFAOYSA-N 0.000 claims 1
- XHKUDVBDHYZLDB-UHFFFAOYSA-N 1-[4-(3-amino-7-methyl-1h-indazol-4-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=2C(N)=NNC=2C(C)=CC=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 XHKUDVBDHYZLDB-UHFFFAOYSA-N 0.000 claims 1
- HDGYVRWVDXOBGT-UHFFFAOYSA-N 1-[4-(3-amino-7-pyridin-3-yl-1h-indazol-4-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=C(C=2C=NC=CC=2)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 HDGYVRWVDXOBGT-UHFFFAOYSA-N 0.000 claims 1
- GRWZZLSYMYWWDR-UHFFFAOYSA-N 1-[4-[3-amino-1-(2-hydroxyethyl)indazol-4-yl]phenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NN(CCO)C=3C=CC=2)=C1 GRWZZLSYMYWWDR-UHFFFAOYSA-N 0.000 claims 1
- IUNDWFIBDOEHTC-UHFFFAOYSA-N 1-[4-[3-amino-1-(2-morpholin-4-ylethyl)indazol-4-yl]phenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NN(CCN4CCOCC4)C=3C=CC=2)=C1 IUNDWFIBDOEHTC-UHFFFAOYSA-N 0.000 claims 1
- KETYRCNARHHEIG-UHFFFAOYSA-N 1-[4-[3-amino-1-(2-morpholin-4-ylethyl)indazol-4-yl]phenyl]-3-(3-chlorophenyl)urea Chemical compound C12=CC=CC(C=3C=CC(NC(=O)NC=4C=C(Cl)C=CC=4)=CC=3)=C2C(N)=NN1CCN1CCOCC1 KETYRCNARHHEIG-UHFFFAOYSA-N 0.000 claims 1
- CXYYJVILNUQYOM-UHFFFAOYSA-N 1-[4-[3-amino-1-(2-morpholin-4-ylethyl)indazol-4-yl]phenyl]-3-(3-fluorophenyl)urea Chemical compound C12=CC=CC(C=3C=CC(NC(=O)NC=4C=C(F)C=CC=4)=CC=3)=C2C(N)=NN1CCN1CCOCC1 CXYYJVILNUQYOM-UHFFFAOYSA-N 0.000 claims 1
- ZXUMETLBULTUGK-UHFFFAOYSA-N 1-[4-[3-amino-7-(2-methoxyethoxy)-1h-indazol-4-yl]phenyl]-3-(3-chlorophenyl)urea Chemical compound C1=2C(N)=NNC=2C(OCCOC)=CC=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 ZXUMETLBULTUGK-UHFFFAOYSA-N 0.000 claims 1
- SKJITDMEYJEWHI-UHFFFAOYSA-N 1-[4-[3-amino-7-(2-methoxyethoxy)-1h-indazol-4-yl]phenyl]-3-(3-fluorophenyl)urea Chemical compound C1=2C(N)=NNC=2C(OCCOC)=CC=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 SKJITDMEYJEWHI-UHFFFAOYSA-N 0.000 claims 1
- NLSKAPLJZPGWKI-UHFFFAOYSA-N 1-[4-[3-amino-7-(2-methoxyethoxy)-1h-indazol-4-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1=2C(N)=NNC=2C(OCCOC)=CC=C1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F NLSKAPLJZPGWKI-UHFFFAOYSA-N 0.000 claims 1
- OPCBBQWHBRRKFA-UHFFFAOYSA-N 1-[4-[3-amino-7-(2-morpholin-4-ylethoxy)-1h-indazol-4-yl]phenyl]-3-(3-bromophenyl)urea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C=C(Br)C=CC=3)=CC=2)=C2C(N)=NNC2=C1OCCN1CCOCC1 OPCBBQWHBRRKFA-UHFFFAOYSA-N 0.000 claims 1
- ZNJKQVREDDBPRP-UHFFFAOYSA-N 1-[4-[3-amino-7-(2-morpholin-4-ylethoxy)-1h-indazol-4-yl]phenyl]-3-(3-fluorophenyl)urea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C=C(F)C=CC=3)=CC=2)=C2C(N)=NNC2=C1OCCN1CCOCC1 ZNJKQVREDDBPRP-UHFFFAOYSA-N 0.000 claims 1
- DZJZLCRHDFXPCV-UHFFFAOYSA-N 1-[4-[3-amino-7-(2-morpholin-4-ylethoxy)-1h-indazol-4-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)F)=CC=2)=C2C(N)=NNC2=C1OCCN1CCOCC1 DZJZLCRHDFXPCV-UHFFFAOYSA-N 0.000 claims 1
- AXQKFSUUMUBLMG-UHFFFAOYSA-N 1-[4-[3-amino-7-(2-morpholin-4-ylethoxy)-1h-indazol-4-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C=C(C=CC=3)C(F)(F)F)=CC=2)=C2C(N)=NNC2=C1OCCN1CCOCC1 AXQKFSUUMUBLMG-UHFFFAOYSA-N 0.000 claims 1
- ZOHWWYAWGKBOLZ-UHFFFAOYSA-N 1-[4-[3-amino-7-(2-morpholin-4-ylethoxy)-1h-indazol-4-yl]phenyl]-3-phenylurea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=C2C(N)=NNC2=C1OCCN1CCOCC1 ZOHWWYAWGKBOLZ-UHFFFAOYSA-N 0.000 claims 1
- FBJIOFUYQMQBMY-UHFFFAOYSA-N 1-[4-[3-amino-7-(3-morpholin-4-ylpropoxy)-1h-indazol-4-yl]phenyl]-3-(3-bromophenyl)urea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C=C(Br)C=CC=3)=CC=2)=C2C(N)=NNC2=C1OCCCN1CCOCC1 FBJIOFUYQMQBMY-UHFFFAOYSA-N 0.000 claims 1
- RIXHTNUEGWELFG-UHFFFAOYSA-N 1-[4-[3-amino-7-(3-morpholin-4-ylpropoxy)-1h-indazol-4-yl]phenyl]-3-(3-fluorophenyl)urea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C=C(F)C=CC=3)=CC=2)=C2C(N)=NNC2=C1OCCCN1CCOCC1 RIXHTNUEGWELFG-UHFFFAOYSA-N 0.000 claims 1
- VELQIKWWKCBJNW-UHFFFAOYSA-N 1-[4-[3-amino-7-(3-morpholin-4-ylpropoxy)-1h-indazol-4-yl]phenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NNC=3C(OCCCN3CCOCC3)=CC=2)=C1 VELQIKWWKCBJNW-UHFFFAOYSA-N 0.000 claims 1
- FSRHCDQDKIDNKT-UHFFFAOYSA-N 1-[4-[3-amino-7-(3-morpholin-4-ylpropoxy)-1h-indazol-4-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)F)=CC=2)=C2C(N)=NNC2=C1OCCCN1CCOCC1 FSRHCDQDKIDNKT-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| AU2010202984A AU2010202984A1 (en) | 2003-05-22 | 2010-07-14 | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
Applications Claiming Priority (5)
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| US10/443,254 US20040235892A1 (en) | 2003-05-22 | 2003-05-22 | Indazole and benzisoxazole kinase inhibitors |
| US10/443,254 | 2003-05-22 | ||
| US10/842,292 US7297709B2 (en) | 2003-05-22 | 2004-05-10 | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
| US10/842,292 | 2004-05-10 | ||
| PCT/US2004/016166 WO2004113304A1 (en) | 2003-05-22 | 2004-05-21 | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
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| AU2010202984A Division AU2010202984A1 (en) | 2003-05-22 | 2010-07-14 | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
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| AU2004249675A1 AU2004249675A1 (en) | 2004-12-29 |
| AU2004249675B2 true AU2004249675B2 (en) | 2010-04-15 |
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| AU2010202984A Abandoned AU2010202984A1 (en) | 2003-05-22 | 2010-07-14 | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
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| Application Number | Title | Priority Date | Filing Date |
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| AU2010202984A Abandoned AU2010202984A1 (en) | 2003-05-22 | 2010-07-14 | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
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| FR2871158A1 (fr) * | 2004-06-04 | 2005-12-09 | Aventis Pharma Sa | Indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| DE102004028862A1 (de) * | 2004-06-15 | 2005-12-29 | Merck Patent Gmbh | 3-Aminoindazole |
| US20060045953A1 (en) * | 2004-08-06 | 2006-03-02 | Catherine Tachdjian | Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers |
| US7812166B2 (en) | 2004-10-29 | 2010-10-12 | Abbott Laboratories | Kinase inhibitors |
| PE20061119A1 (es) * | 2005-01-19 | 2006-11-27 | Aventis Pharma Sa | PIRAZOLO PIRIDINAS SUSTITUIDAS COMO INHIBIDORES DE CINASAS FAK, KDR Y Tie |
| US7842809B2 (en) | 2005-01-24 | 2010-11-30 | Bayer Schering Pharma Ag | Pyrazolopyridines and salts thereof, a pharmaceutical composition comprising said compounds, a method of preparing same and use of same |
| EP1683796A1 (en) * | 2005-01-24 | 2006-07-26 | Schering Aktiengesellschaft | Pyrazolopyridines, their preparation and their medical use |
| ES2373912T3 (es) * | 2005-01-28 | 2012-02-10 | Novartis Ag | Uso de pirimidilaminobenzamidas para el tratamiento de enfermedades que responden a la modulación de la actividad de quinasa tie-2. |
| MX2007009388A (es) | 2005-02-04 | 2007-09-25 | Senomyx Inc | Compuestos que comprenden porciones heteroarilo unidas y su uso como modificadores del sabor unami, saborizantes y mejoradores del sabor para composiciones comestibles. |
| TW200640443A (en) * | 2005-02-23 | 2006-12-01 | Alcon Inc | Methods for treating ocular angiogenesis, retinal edema, retinal ischemia, and diabetic retinopathy using selective RTK inhibitors |
| DE102005038947A1 (de) | 2005-05-18 | 2006-11-30 | Grünenthal GmbH | Substituierte Benzo[d]isoxazol-3-yl-amin-Verbindungen und deren Verwendung in Arzneimitteln |
| TW200715993A (en) | 2005-06-15 | 2007-05-01 | Senomyx Inc | Bis-aromatic amides and their uses as sweet flavor modifiers, tastants, and taste enhancers |
| WO2007050574A1 (en) * | 2005-10-25 | 2007-05-03 | Abbott Laboratories | Formulation comprising a drug of low water solubility and method of use thereof |
| US20070149480A1 (en) * | 2005-12-23 | 2007-06-28 | Alcon, Inc. | PHARMACEUTICAL COMPOSITION FOR DELIVERY OF RECEPTOR TYROSINE KINASE INHIBITING (RTKi) COMPOUNDS TO THE EYE |
| BRPI0709963A2 (pt) | 2006-04-14 | 2011-08-02 | Abbott Lab | processo para a preparação de indazolil uréias que inibem receptores de subtipo 1 de vanilóide (vr1) |
| KR101387563B1 (ko) | 2006-04-21 | 2014-04-25 | 세노믹스, 인코포레이티드 | 고효능의 조미용 향료를 포함하는 식품 조성물 및 이의 제조 방법 |
| TW200815437A (en) * | 2006-06-13 | 2008-04-01 | Bayer Schering Pharma Ag | Substituted aminopyrazolopyridines and salts thereof, pharmaceutical compositions comprising same, methods of preparing same and uses of same |
| EP1870410A1 (en) | 2006-06-13 | 2007-12-26 | Bayer Schering Pharma Aktiengesellschaft | Substituted arylpyrazolopyridines and salts thereof, pharmaceutical compositions comprising same, methods of preparing same and uses of same |
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