JP2006503081A5 - - Google Patents
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- Publication number
- JP2006503081A5 JP2006503081A5 JP2004543799A JP2004543799A JP2006503081A5 JP 2006503081 A5 JP2006503081 A5 JP 2006503081A5 JP 2004543799 A JP2004543799 A JP 2004543799A JP 2004543799 A JP2004543799 A JP 2004543799A JP 2006503081 A5 JP2006503081 A5 JP 2006503081A5
- Authority
- JP
- Japan
- Prior art keywords
- oxazol
- amine
- phenyl
- methoxyphenyl
- ethylsulfonyl
- 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.)
- Pending
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- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims 2
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims 2
- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims 2
- 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 claims 2
- 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 claims 2
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- QKSJQFXYMMEPRF-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(4-fluorophenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 QKSJQFXYMMEPRF-UHFFFAOYSA-N 0.000 claims 2
- QCQOWGLVUUYDQD-UHFFFAOYSA-N 1-[3-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenyl]ethanone Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C(C)=O)=C1 QCQOWGLVUUYDQD-UHFFFAOYSA-N 0.000 claims 1
- HUEHWEIRPBHLHX-UHFFFAOYSA-N 1-[4-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenyl]ethanone Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(=CC=2)C(C)=O)=C1 HUEHWEIRPBHLHX-UHFFFAOYSA-N 0.000 claims 1
- SYSHDKLDGMTHOH-UHFFFAOYSA-N 1-[4-methoxy-3-[(5-phenyl-1,3-oxazol-2-yl)amino]phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1NC1=NC=C(C=2C=CC=CC=2)O1 SYSHDKLDGMTHOH-UHFFFAOYSA-N 0.000 claims 1
- QPPUEUDEJHMPIO-UHFFFAOYSA-N 2,5-dimethoxy-4-[(5-phenyl-1,3-oxazol-2-yl)amino]benzenesulfonamide Chemical compound COC1=CC(S(N)(=O)=O)=C(OC)C=C1NC1=NC=C(C=2C=CC=CC=2)O1 QPPUEUDEJHMPIO-UHFFFAOYSA-N 0.000 claims 1
- XAEFWRBNZXZJIF-UHFFFAOYSA-N 2-[4-[(5-phenyl-1,3-oxazol-2-yl)amino]phenyl]ethanol Chemical compound C1=CC(CCO)=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 XAEFWRBNZXZJIF-UHFFFAOYSA-N 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- WHMNHVWUJKGKPY-UHFFFAOYSA-N 3-(2-anilino-1,3-oxazol-5-yl)phenol Chemical compound OC1=CC=CC(C=2OC(NC=3C=CC=CC=3)=NC=2)=C1 WHMNHVWUJKGKPY-UHFFFAOYSA-N 0.000 claims 1
- DJSGIVCMVJOHJB-UHFFFAOYSA-N 3-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]benzonitrile Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C#N)=C1 DJSGIVCMVJOHJB-UHFFFAOYSA-N 0.000 claims 1
- FOMXHAVRWBWUIE-UHFFFAOYSA-N 3-[2-(5-ethylsulfonyl-2-methylanilino)-1,3-oxazol-5-yl]phenol Chemical compound CCS(=O)(=O)C1=CC=C(C)C(NC=2OC(=CN=2)C=2C=C(O)C=CC=2)=C1 FOMXHAVRWBWUIE-UHFFFAOYSA-N 0.000 claims 1
- GAGRNTCIXGCREB-UHFFFAOYSA-N 3-[2-[4-(4-methylpiperazin-1-yl)anilino]-1,3-oxazol-5-yl]phenol Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C=C(O)C=CC=2)O1 GAGRNTCIXGCREB-UHFFFAOYSA-N 0.000 claims 1
- MWSLMWXIDNNHTJ-UHFFFAOYSA-N 3-[3-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenyl]benzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 MWSLMWXIDNNHTJ-UHFFFAOYSA-N 0.000 claims 1
- IRRDFCUOEMNUTK-UHFFFAOYSA-N 3-[3-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenyl]benzonitrile Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=C(C=CC=2)C#N)=C1 IRRDFCUOEMNUTK-UHFFFAOYSA-N 0.000 claims 1
- GMMJPPLCSIXDOK-UHFFFAOYSA-N 3-[[5-(3-bromophenyl)-1,3-oxazol-2-yl]amino]-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1NC1=NC=C(C=2C=C(Br)C=CC=2)O1 GMMJPPLCSIXDOK-UHFFFAOYSA-N 0.000 claims 1
- PXHMLYOXURSMFE-UHFFFAOYSA-N 3-[[5-(3-bromophenyl)-1,3-oxazol-2-yl]amino]-4-methoxybenzenesulfonyl fluoride Chemical compound COC1=CC=C(S(F)(=O)=O)C=C1NC1=NC=C(C=2C=C(Br)C=CC=2)O1 PXHMLYOXURSMFE-UHFFFAOYSA-N 0.000 claims 1
- SYSKKMKMUPOFLW-UHFFFAOYSA-N 3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxy-n,n-dimethylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1NC1=NC=C(C=2C=CC(F)=CC=2)O1 SYSKKMKMUPOFLW-UHFFFAOYSA-N 0.000 claims 1
- JJOMCUFQUAZMMM-UHFFFAOYSA-N 3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxy-n-(3-methoxypropyl)benzenesulfonamide Chemical compound COCCCNS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 JJOMCUFQUAZMMM-UHFFFAOYSA-N 0.000 claims 1
- KUEQMWMUVKZBMI-UHFFFAOYSA-N 3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxy-n-(3-pyrrolidin-1-ylpropyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NCCCN2CCCC2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 KUEQMWMUVKZBMI-UHFFFAOYSA-N 0.000 claims 1
- FZLALRGUGRTYMX-UHFFFAOYSA-N 3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxy-n-(pyridin-2-ylmethyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NCC=2N=CC=CC=2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 FZLALRGUGRTYMX-UHFFFAOYSA-N 0.000 claims 1
- SMNBHZUHDVJARM-UHFFFAOYSA-N 3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxy-n-(pyridin-3-ylmethyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NCC=2C=NC=CC=2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 SMNBHZUHDVJARM-UHFFFAOYSA-N 0.000 claims 1
- FGRFXUVAFDAGOV-UHFFFAOYSA-N 3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxy-n-(pyridin-4-ylmethyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NCC=2C=CN=CC=2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 FGRFXUVAFDAGOV-UHFFFAOYSA-N 0.000 claims 1
- ZKWZRWBHXVSOPL-UHFFFAOYSA-N 3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 ZKWZRWBHXVSOPL-UHFFFAOYSA-N 0.000 claims 1
- LQNHFLSSULSJTA-UHFFFAOYSA-N 3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1NC1=NC=C(C=2C=CC(F)=CC=2)O1 LQNHFLSSULSJTA-UHFFFAOYSA-N 0.000 claims 1
- RFBUOSRJQMTHCC-UHFFFAOYSA-N 3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-n-(3-imidazol-1-ylpropyl)-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NCCCN2C=NC=C2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 RFBUOSRJQMTHCC-UHFFFAOYSA-N 0.000 claims 1
- LZAXFXFRGXKTHI-UHFFFAOYSA-N 3-[[5-[3-(3-fluorophenyl)phenyl]-1,3-oxazol-2-yl]amino]-4-methoxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=C(F)C=CC=2)=C1 LZAXFXFRGXKTHI-UHFFFAOYSA-N 0.000 claims 1
- MRGJABCHCZPKRM-UHFFFAOYSA-N 3-[[5-[3-(3-fluorophenyl)phenyl]-1,3-oxazol-2-yl]amino]-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2C=C(F)C=CC=2)O1 MRGJABCHCZPKRM-UHFFFAOYSA-N 0.000 claims 1
- KIFVQRJLEAYODZ-UHFFFAOYSA-N 3-[[5-[3-(4-fluorophenyl)phenyl]-1,3-oxazol-2-yl]amino]-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2C=CC(F)=CC=2)O1 KIFVQRJLEAYODZ-UHFFFAOYSA-N 0.000 claims 1
- OMLTZDZAOCCSPT-UHFFFAOYSA-N 3-methyl-5-[(5-phenyl-1,3-oxazol-2-yl)amino]benzene-1,2-diol Chemical compound OC1=C(O)C(C)=CC(NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 OMLTZDZAOCCSPT-UHFFFAOYSA-N 0.000 claims 1
- QYKZROZZKQVCOO-UHFFFAOYSA-N 4-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]benzamide Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(=CC=2)C(N)=O)=C1 QYKZROZZKQVCOO-UHFFFAOYSA-N 0.000 claims 1
- JABBQOPTTSFZHZ-UHFFFAOYSA-N 4-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]benzonitrile Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(=CC=2)C#N)=C1 JABBQOPTTSFZHZ-UHFFFAOYSA-N 0.000 claims 1
- DDOIIJWKFFHMPD-UHFFFAOYSA-N 4-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenol Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(O)=CC=2)=C1 DDOIIJWKFFHMPD-UHFFFAOYSA-N 0.000 claims 1
- YKGBIPCGKKISFF-UHFFFAOYSA-N 4-[3-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenyl]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=CC(=CC=2)C(=O)NCCN2CCOCC2)=C1 YKGBIPCGKKISFF-UHFFFAOYSA-N 0.000 claims 1
- IBJKXGJRWRJXAH-UHFFFAOYSA-N 4-[3-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenyl]-n-[3-(4-methylpiperazin-1-yl)propyl]benzamide Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=CC(=CC=2)C(=O)NCCCN2CCN(C)CC2)=C1 IBJKXGJRWRJXAH-UHFFFAOYSA-N 0.000 claims 1
- JQYCSWPZBRRLIZ-UHFFFAOYSA-N 4-[3-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenyl]benzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=CC(=CC=2)C(O)=O)=C1 JQYCSWPZBRRLIZ-UHFFFAOYSA-N 0.000 claims 1
- NGXNBHLLGBWDSE-UHFFFAOYSA-N 4-[3-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenyl]benzonitrile Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=CC(=CC=2)C#N)=C1 NGXNBHLLGBWDSE-UHFFFAOYSA-N 0.000 claims 1
- AOEJEISVXQIJQC-UHFFFAOYSA-N 4-chloro-3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 AOEJEISVXQIJQC-UHFFFAOYSA-N 0.000 claims 1
- BOLMDKGWAYICKL-UHFFFAOYSA-N 4-chloro-n,n-diethyl-3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(Cl)C(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 BOLMDKGWAYICKL-UHFFFAOYSA-N 0.000 claims 1
- ZAWKTBHCMGEJHU-UHFFFAOYSA-N 4-ethylsulfonyl-2-[(5-phenyl-1,3-oxazol-2-yl)amino]phenol Chemical compound CCS(=O)(=O)C1=CC=C(O)C(NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 ZAWKTBHCMGEJHU-UHFFFAOYSA-N 0.000 claims 1
- RRMDUQTVDRZJEI-UHFFFAOYSA-N 4-methoxy-3-[[5-(3-phenylphenyl)-1,3-oxazol-2-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC(C)C)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2C=CC=CC=2)O1 RRMDUQTVDRZJEI-UHFFFAOYSA-N 0.000 claims 1
- HWHSKSBIGKWFLB-UHFFFAOYSA-N 4-methoxy-3-[[5-(3-phenylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2C=CC=CC=2)O1 HWHSKSBIGKWFLB-UHFFFAOYSA-N 0.000 claims 1
- JEFGZXCBLAWGIS-UHFFFAOYSA-N 4-methoxy-3-[[5-(3-phenylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonyl fluoride Chemical compound COC1=CC=C(S(F)(=O)=O)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2C=CC=CC=2)O1 JEFGZXCBLAWGIS-UHFFFAOYSA-N 0.000 claims 1
- KNGHRBLCQBOLGQ-UHFFFAOYSA-N 4-methoxy-3-[[5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2N=CC=CC=2)O1 KNGHRBLCQBOLGQ-UHFFFAOYSA-N 0.000 claims 1
- JWAXDRROMGERSL-UHFFFAOYSA-N 4-methoxy-3-[[5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonyl fluoride Chemical compound COC1=CC=C(S(F)(=O)=O)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2N=CC=CC=2)O1 JWAXDRROMGERSL-UHFFFAOYSA-N 0.000 claims 1
- FHRLNJWMTNVXHM-UHFFFAOYSA-N 4-methoxy-3-[[5-(3-pyridin-3-ylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2C=NC=CC=2)O1 FHRLNJWMTNVXHM-UHFFFAOYSA-N 0.000 claims 1
- QXZVBVVWCDTZEX-UHFFFAOYSA-N 4-methoxy-3-[[5-(3-pyridin-3-ylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonyl fluoride Chemical compound COC1=CC=C(S(F)(=O)=O)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2C=NC=CC=2)O1 QXZVBVVWCDTZEX-UHFFFAOYSA-N 0.000 claims 1
- YRLPGPBYYSASKZ-UHFFFAOYSA-N 4-methoxy-n,n-dimethyl-3-[[5-(3-phenylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2C=CC=CC=2)O1 YRLPGPBYYSASKZ-UHFFFAOYSA-N 0.000 claims 1
- QCPOCTLUQDBHTM-UHFFFAOYSA-N 4-methoxy-n-(2-morpholin-4-ylethyl)-3-[(5-phenyl-1,3-oxazol-2-yl)amino]benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NCCN2CCOCC2)C=C1NC(O1)=NC=C1C1=CC=CC=C1 QCPOCTLUQDBHTM-UHFFFAOYSA-N 0.000 claims 1
- DXRMBWUOKLOBAC-UHFFFAOYSA-N 4-methoxy-n-methyl-3-[[5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2N=CC=CC=2)=C1 DXRMBWUOKLOBAC-UHFFFAOYSA-N 0.000 claims 1
- SYXQSUJISRRFII-UHFFFAOYSA-N 5-(2,3-dihydro-1,4-benzodioxin-6-yl)-n-(5-ethylsulfonyl-2-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C3OCCOC3=CC=2)=C1 SYXQSUJISRRFII-UHFFFAOYSA-N 0.000 claims 1
- XBUAVUPPUQQFQI-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-n-(3,4-dimethoxyphenyl)-1,3-oxazol-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=2C=C(Cl)C(Cl)=CC=2)O1 XBUAVUPPUQQFQI-UHFFFAOYSA-N 0.000 claims 1
- YEVODOKKVSALMR-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-n-(5-ethylsulfonyl-2-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(Cl)C(Cl)=CC=2)=C1 YEVODOKKVSALMR-UHFFFAOYSA-N 0.000 claims 1
- CXTGDDCYVWDZKH-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-n-(5-ethylsulfonyl-2-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(F)C(F)=CC=2)=C1 CXTGDDCYVWDZKH-UHFFFAOYSA-N 0.000 claims 1
- GFSZFSMKTWDVST-UHFFFAOYSA-N 5-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)-n-(5-ethylsulfonyl-2-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C3OCCCOC3=CC=2)=C1 GFSZFSMKTWDVST-UHFFFAOYSA-N 0.000 claims 1
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- XSHQWUGMBNNILJ-UHFFFAOYSA-N 5-[4-(diethylamino)phenyl]-n-(3,4-dimethoxyphenyl)-1,3-oxazol-2-amine Chemical compound C1=CC(N(CC)CC)=CC=C1C(O1)=CN=C1NC1=CC=C(OC)C(OC)=C1 XSHQWUGMBNNILJ-UHFFFAOYSA-N 0.000 claims 1
- BIAJZIZAFJRRBE-UHFFFAOYSA-N 5-[5-(2,4-dichlorophenyl)furan-2-yl]-n-(5-ethylsulfonyl-2-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2OC(=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1 BIAJZIZAFJRRBE-UHFFFAOYSA-N 0.000 claims 1
- CKYLEUNHWFIYOR-UHFFFAOYSA-N 5-phenyl-n-(3,4,5-trimethoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 CKYLEUNHWFIYOR-UHFFFAOYSA-N 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- WTSNQZLKTLSHSD-UHFFFAOYSA-N [3-[(5-phenyl-1,3-oxazol-2-yl)amino]phenyl]methanol Chemical compound OCC1=CC=CC(NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 WTSNQZLKTLSHSD-UHFFFAOYSA-N 0.000 claims 1
- FNOSAYVNKHAANB-UHFFFAOYSA-N [4-[[5-(3-methoxyphenyl)-1,3-oxazol-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)C(=O)N3CCN(C)CC3)=NC=2)=C1 FNOSAYVNKHAANB-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- YGUVBHKKNQXNRE-UHFFFAOYSA-N methyl 3-[[5-(3-bromophenyl)-1,3-oxazol-2-yl]amino]-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(Br)C=CC=2)=C1 YGUVBHKKNQXNRE-UHFFFAOYSA-N 0.000 claims 1
- QWSCKFOQTBSYTE-UHFFFAOYSA-N methyl 4-[3-[2-(5-ethylsulfonyl-2-methoxyanilino)-1,3-oxazol-5-yl]phenyl]benzoate Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=CC(=CC=2)C(=O)OC)=C1 QWSCKFOQTBSYTE-UHFFFAOYSA-N 0.000 claims 1
- JPOAUVQWQBFJJC-UHFFFAOYSA-N methyl 4-methoxy-3-[[5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-yl]amino]benzoate Chemical compound COC(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2N=CC=CC=2)=C1 JPOAUVQWQBFJJC-UHFFFAOYSA-N 0.000 claims 1
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- PPTZTLLRWZONKV-UHFFFAOYSA-N n,n-diethyl-4-methoxy-3-[[5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2N=CC=CC=2)=C1 PPTZTLLRWZONKV-UHFFFAOYSA-N 0.000 claims 1
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- RFKWVPXBTNYTCJ-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)-5-phenyl-1,3-oxazol-2-amine Chemical compound COC1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 RFKWVPXBTNYTCJ-UHFFFAOYSA-N 0.000 claims 1
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- CEHMJOQKDKIIMZ-UHFFFAOYSA-N n-(2-ethoxyethyl)-3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxybenzenesulfonamide Chemical compound CCOCCNS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 CEHMJOQKDKIIMZ-UHFFFAOYSA-N 0.000 claims 1
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- HCBJVNGHOLHJAS-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(2-pyridin-2-ylethoxy)phenyl]-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(OCCC=3N=CC=CC=3)C=CC=2)=C1 HCBJVNGHOLHJAS-UHFFFAOYSA-N 0.000 claims 1
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- JXDFLWQCVJLLRK-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(5-methylthiophen-2-yl)phenyl]-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2SC(C)=CC=2)=C1 JXDFLWQCVJLLRK-UHFFFAOYSA-N 0.000 claims 1
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- AIQUXYYOZJSBGX-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(oxan-4-yloxy)phenyl]-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(OC3CCOCC3)C=CC=2)=C1 AIQUXYYOZJSBGX-UHFFFAOYSA-N 0.000 claims 1
- QRQKIEXBAGACTI-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(oxolan-3-yloxy)phenyl]-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(OC3COCC3)C=CC=2)=C1 QRQKIEXBAGACTI-UHFFFAOYSA-N 0.000 claims 1
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- ISZNYBDJSFECIV-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-[2-(propan-2-ylamino)pyrimidin-4-yl]phenyl]-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2N=C(NC(C)C)N=CC=2)=C1 ISZNYBDJSFECIV-UHFFFAOYSA-N 0.000 claims 1
- HFVNNSISRUUDKA-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[4-(trifluoromethyl)phenyl]-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 HFVNNSISRUUDKA-UHFFFAOYSA-N 0.000 claims 1
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- CTOOSUSBGOZQDM-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-methoxy-3-[[5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NCC2CC2)C=C1NC(O1)=NC=C1C(C=1)=CC=CC=1C1=CC=CC=N1 CTOOSUSBGOZQDM-UHFFFAOYSA-N 0.000 claims 1
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| JP4053073B2 (ja) * | 2003-07-11 | 2008-02-27 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 選択的ｃｄｋ４阻害剤のイセチオン酸塩 |
| EP1684750B1 (en) * | 2003-10-23 | 2010-04-28 | AB Science | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
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| WO2005102318A1 (en) * | 2004-04-20 | 2005-11-03 | Ab Science | Use of c-kit inhibitors for treating hiv related diseases |
| CA2566104A1 (en) * | 2004-05-18 | 2005-12-01 | Ab Science | Use of mast cells inhibitors for treating patients exposed to chemical or biological weapons |
| AU2005276974B2 (en) * | 2004-08-25 | 2012-08-02 | Targegen, Inc. | Heterocyclic compounds and methods of use |
| CA2603826C (en) | 2005-04-04 | 2013-03-12 | Ab Science | Substituted oxazole derivatives and their use as tyrosine kinase inhibitors |
| WO2007126957A2 (en) * | 2006-03-31 | 2007-11-08 | Novartis Ag | New compounds |
| CA2651663A1 (en) | 2006-05-30 | 2007-12-06 | Astrazeneca Ab | Chemical compounds |
| JP2010515708A (ja) | 2007-01-12 | 2010-05-13 | アブ サイエンス | 代謝拮抗薬およびチロシンキナーゼ阻害剤を用いた固形癌の併用治療 |
| NZ580671A (en) | 2007-04-16 | 2012-03-30 | Hutchison Medipharma Entpr Ltd | Pyrimidine derivatives |
| EP2231605A1 (en) * | 2007-12-05 | 2010-09-29 | Basf Se | Pyridylmethyl-sulfonamide compounds |
| CN101932562B (zh) | 2007-12-20 | 2013-06-12 | 阿斯利康(瑞典)有限公司 | 作为dgat1抑制剂190的氨基甲酰基化合物 |
| WO2009111502A2 (en) | 2008-03-03 | 2009-09-11 | University Of Notre Dame Du Lac | Anti-cancer compounds, synthesis thereof, and methods of using same |
| WO2010146395A1 (en) | 2009-06-19 | 2010-12-23 | Astrazeneca Ab | Pyrazine carboxamides as inhibitors of dgat1 |
| RU2018100142A (ru) | 2010-03-24 | 2019-02-20 | Амитек Терапетикс Солюшинс, Инк. | Гетероциклические соединения, эффективные для ингибирования киназы |
| EP2714667B1 (en) | 2011-05-27 | 2020-11-25 | Laxman S. DESAI | Aminooxazole inhibitors of cyclin dependent kinases |
| CN102757400B (zh) * | 2012-07-18 | 2014-08-06 | 贵州大学 | 2,5-取代基噁唑类衍生物及其应用 |
| CN104803921A (zh) * | 2015-03-14 | 2015-07-29 | 长沙深橙生物科技有限公司 | 一种苯取代嘧啶衍生物的制备方法 |
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2003
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- 2003-10-10 EP EP03781357A patent/EP1551813A4/en not_active Withdrawn
- 2003-10-10 AU AU2003287178A patent/AU2003287178A1/en not_active Abandoned
- 2003-10-10 JP JP2004543799A patent/JP2006503081A/ja active Pending
- 2003-10-10 WO PCT/US2003/033317 patent/WO2004032882A2/en not_active Ceased