JP2006503081A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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
- ZOSHIGGISWSKRT-UHFFFAOYSA-N 5-(3,5-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=C(F)C=2)=C1 ZOSHIGGISWSKRT-UHFFFAOYSA-N 0.000 claims 1
- NJVLKBBBWXZCIY-UHFFFAOYSA-N 5-(3-bromophenyl)-n-(2-methoxy-5-propan-2-ylsulfonylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)C(C)C)C=C1NC1=NC=C(C=2C=C(Br)C=CC=2)O1 NJVLKBBBWXZCIY-UHFFFAOYSA-N 0.000 claims 1
- YCPFZEWZPRYJHP-UHFFFAOYSA-N 5-(3-bromophenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC(=CN=2)C=2C=C(Br)C=CC=2)=C1 YCPFZEWZPRYJHP-UHFFFAOYSA-N 0.000 claims 1
- YTDXSGPRJHKBRV-UHFFFAOYSA-N 5-(3-bromophenyl)-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(Br)C=CC=2)=C1 YTDXSGPRJHKBRV-UHFFFAOYSA-N 0.000 claims 1
- UGZBGPPRPUXPMK-UHFFFAOYSA-N 5-(3-bromophenyl)-n-[2-methoxy-5-[2-(4-methyl-1,3-thiazol-5-yl)ethylsulfonyl]phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CCC2=C(N=CS2)C)C=C1NC(O1)=NC=C1C1=CC=CC(Br)=C1 UGZBGPPRPUXPMK-UHFFFAOYSA-N 0.000 claims 1
- XAUYGSXCTBSCOT-UHFFFAOYSA-N 5-(3-butoxyphenyl)-n-(5-ethylsulfonyl-2-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCCCOC1=CC=CC(C=2OC(NC=3C(=CC=C(C=3)S(=O)(=O)CC)OC)=NC=2)=C1 XAUYGSXCTBSCOT-UHFFFAOYSA-N 0.000 claims 1
- LBKSEXFJQLMCIG-UHFFFAOYSA-N 5-(3-chlorophenyl)-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=CC=2)=C1 LBKSEXFJQLMCIG-UHFFFAOYSA-N 0.000 claims 1
- JZZFSOPHITWWJQ-UHFFFAOYSA-N 5-(3-cyclohexyloxyphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C=C(OC3CCCCC3)C=CC=2)O1 JZZFSOPHITWWJQ-UHFFFAOYSA-N 0.000 claims 1
- BZCYIFAKTOUWNG-UHFFFAOYSA-N 5-(3-cyclopentyloxyphenyl)-n-(4-thiomorpholin-4-ylphenyl)-1,3-oxazol-2-amine Chemical compound C1CCCC1OC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)N3CCSCC3)=NC=2)=C1 BZCYIFAKTOUWNG-UHFFFAOYSA-N 0.000 claims 1
- QHQFHOAGURHSOM-UHFFFAOYSA-N 5-(3-cyclopentyloxyphenyl)-n-[3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC=C(C=2C=C(OC3CCCC3)C=CC=2)O1 QHQFHOAGURHSOM-UHFFFAOYSA-N 0.000 claims 1
- FZNPNATVHXFTEZ-UHFFFAOYSA-N 5-(3-cyclopentyloxyphenyl)-n-[3-methyl-4-(4-methylpiperazin-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C(=C1)C)=CC=C1NC1=NC=C(C=2C=C(OC3CCCC3)C=CC=2)O1 FZNPNATVHXFTEZ-UHFFFAOYSA-N 0.000 claims 1
- LXNGFJMYUNSKLL-UHFFFAOYSA-N 5-(3-cyclopentyloxyphenyl)-n-[4-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C(=C1)C(F)(F)F)=CC=C1NC1=NC=C(C=2C=C(OC3CCCC3)C=CC=2)O1 LXNGFJMYUNSKLL-UHFFFAOYSA-N 0.000 claims 1
- YJHJMFYNSWQRTC-UHFFFAOYSA-N 5-(3-cyclopentyloxyphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C=C(OC3CCCC3)C=CC=2)O1 YJHJMFYNSWQRTC-UHFFFAOYSA-N 0.000 claims 1
- ZVZJIKOVDRUPFM-UHFFFAOYSA-N 5-(3-cyclopentyloxyphenyl)-n-[4-[(dimethylamino)methyl]phenyl]-1,3-oxazol-2-amine Chemical compound C1=CC(CN(C)C)=CC=C1NC1=NC=C(C=2C=C(OC3CCCC3)C=CC=2)O1 ZVZJIKOVDRUPFM-UHFFFAOYSA-N 0.000 claims 1
- ICAOLCQPOWAEOF-UHFFFAOYSA-N 5-(3-cyclopentyloxyphenyl)-n-[5-methyl-6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C(=C1)C)=NC=C1NC1=NC=C(C=2C=C(OC3CCCC3)C=CC=2)O1 ICAOLCQPOWAEOF-UHFFFAOYSA-N 0.000 claims 1
- ASRWTJKYQQFPJR-UHFFFAOYSA-N 5-(3-cyclopentyloxyphenyl)-n-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=2C=C(OC3CCCC3)C=CC=2)O1 ASRWTJKYQQFPJR-UHFFFAOYSA-N 0.000 claims 1
- UQSLBXUSMGWOGW-UHFFFAOYSA-N 5-(3-ethenylphenyl)-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(C=C)C=CC=2)=C1 UQSLBXUSMGWOGW-UHFFFAOYSA-N 0.000 claims 1
- ZPUBTWVZPOGOKS-UHFFFAOYSA-N 5-(3-ethoxyphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound CCOC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=2)=C1 ZPUBTWVZPOGOKS-UHFFFAOYSA-N 0.000 claims 1
- OWRNZCGLKGYOBT-UHFFFAOYSA-N 5-(3-ethylphenyl)-n-(5-ethylsulfonyl-2-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCC1=CC=CC(C=2OC(NC=3C(=CC=C(C=3)S(=O)(=O)CC)OC)=NC=2)=C1 OWRNZCGLKGYOBT-UHFFFAOYSA-N 0.000 claims 1
- WVFBJYJMHLQAAJ-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-(4-morpholin-4-ylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=2)=C1 WVFBJYJMHLQAAJ-UHFFFAOYSA-N 0.000 claims 1
- ZRAGJNCJAXADAG-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-(4-piperidin-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=2)=C1 ZRAGJNCJAXADAG-UHFFFAOYSA-N 0.000 claims 1
- ZQEGMFTWRAQKQL-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-(6-piperidin-1-ylpyridin-3-yl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=NC(=CC=3)N3CCCCC3)=NC=2)=C1 ZQEGMFTWRAQKQL-UHFFFAOYSA-N 0.000 claims 1
- UMOXSLJXVYSULL-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[2-methyl-4-(4-methylpiperazin-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C(=CC(=CC=3)N3CCN(C)CC3)C)=NC=2)=C1 UMOXSLJXVYSULL-UHFFFAOYSA-N 0.000 claims 1
- ACJFBVXJJZWLFO-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[3-methyl-4-(4-methylpiperazin-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=C(C)C(N4CCN(C)CC4)=CC=3)=NC=2)=C1 ACJFBVXJJZWLFO-UHFFFAOYSA-N 0.000 claims 1
- DSLJXUQVRNMTHW-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[4-(1-propylpiperidin-4-yl)-1,3-thiazol-2-yl]-1,3-oxazol-2-amine Chemical compound C1CN(CCC)CCC1C1=CSC(NC=2OC(=CN=2)C=2C=C(OC)C=CC=2)=N1 DSLJXUQVRNMTHW-UHFFFAOYSA-N 0.000 claims 1
- CJTFYFIIHQOUKH-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[4-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=C(C(N4CCN(C)CC4)=CC=3)C(F)(F)F)=NC=2)=C1 CJTFYFIIHQOUKH-UHFFFAOYSA-N 0.000 claims 1
- NOVTWAUKHUUJDY-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=2)=C1 NOVTWAUKHUUJDY-UHFFFAOYSA-N 0.000 claims 1
- QDVPGCDPRORGQJ-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[4-(morpholin-4-ylmethyl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(CN4CCOCC4)=CC=3)=NC=2)=C1 QDVPGCDPRORGQJ-UHFFFAOYSA-N 0.000 claims 1
- IGQAOQPUAGXVCJ-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[4-(piperidin-1-ylmethyl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(CN4CCCCC4)=CC=3)=NC=2)=C1 IGQAOQPUAGXVCJ-UHFFFAOYSA-N 0.000 claims 1
- ARDUHLPVYOKBKY-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(CN4CCCC4)=CC=3)=NC=2)=C1 ARDUHLPVYOKBKY-UHFFFAOYSA-N 0.000 claims 1
- KNSYLEHGHDXZKL-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(CN4CCN(C)CC4)=CC=3)=NC=2)=C1 KNSYLEHGHDXZKL-UHFFFAOYSA-N 0.000 claims 1
- YHFQRUIZMYVWDJ-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=NC(=CC=3)N3CCN(C)CC3)=NC=2)=C1 YHFQRUIZMYVWDJ-UHFFFAOYSA-N 0.000 claims 1
- RJVZASZFMXCEGR-UHFFFAOYSA-N 5-(3-methoxyphenyl)-n-phenyl-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC=CC=3)=NC=2)=C1 RJVZASZFMXCEGR-UHFFFAOYSA-N 0.000 claims 1
- RYNSVQQNZSSFJN-UHFFFAOYSA-N 5-(3-phenylphenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 RYNSVQQNZSSFJN-UHFFFAOYSA-N 0.000 claims 1
- CKOFDCHGDOIUIJ-UHFFFAOYSA-N 5-(4-bromophenyl)-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=CC(Br)=CC=2)=C1 CKOFDCHGDOIUIJ-UHFFFAOYSA-N 0.000 claims 1
- ANEMGGRRZMSEAG-UHFFFAOYSA-N 5-(4-chloro-3-methylphenyl)-n-(3,4-dimethoxyphenyl)-1,3-oxazol-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=2C=C(C)C(Cl)=CC=2)O1 ANEMGGRRZMSEAG-UHFFFAOYSA-N 0.000 claims 1
- YLOPCBYGMQPYRV-UHFFFAOYSA-N 5-(4-chloro-3-methylphenyl)-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(C)C(Cl)=CC=2)=C1 YLOPCBYGMQPYRV-UHFFFAOYSA-N 0.000 claims 1
- ZAEZEADQIGFKLO-UHFFFAOYSA-N 5-(4-chlorophenyl)-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=CC(Cl)=CC=2)=C1 ZAEZEADQIGFKLO-UHFFFAOYSA-N 0.000 claims 1
- DMIMYOORUWSUDI-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(2-methoxy-5-methylsulfonylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1NC1=NC=C(C=2C=CC(F)=CC=2)O1 DMIMYOORUWSUDI-UHFFFAOYSA-N 0.000 claims 1
- NQZXDGCXUZOCRI-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(2-methoxy-5-morpholin-4-ylsulfonylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)N2CCOCC2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 NQZXDGCXUZOCRI-UHFFFAOYSA-N 0.000 claims 1
- QFVOZCSTTFBOOJ-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(2-methoxy-5-pentan-3-ylsulfonylphenyl)-1,3-oxazol-2-amine Chemical compound CCC(CC)S(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 QFVOZCSTTFBOOJ-UHFFFAOYSA-N 0.000 claims 1
- JEHSTHBNVAFEPC-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(2-methoxy-5-propan-2-ylsulfonylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)C(C)C)C=C1NC1=NC=C(C=2C=CC(F)=CC=2)O1 JEHSTHBNVAFEPC-UHFFFAOYSA-N 0.000 claims 1
- VDOOJROEQANSTE-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(2-methoxy-5-thiomorpholin-4-ylsulfonylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)N2CCSCC2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 VDOOJROEQANSTE-UHFFFAOYSA-N 0.000 claims 1
- XCTGUJIFCXYXLN-UHFFFAOYSA-N 5-(4-fluorophenyl)-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(F)=CC=2)=C1 XCTGUJIFCXYXLN-UHFFFAOYSA-N 0.000 claims 1
- RIMLBMSBXVRCKX-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(3-methylsulfonylphenyl)-1,3-oxazol-2-amine Chemical compound CS(=O)(=O)C1=CC=CC(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 RIMLBMSBXVRCKX-UHFFFAOYSA-N 0.000 claims 1
- JCHXUTFAZSIAIM-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-methoxy-5-(2-methylpropylsulfonyl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CC(C)C)C=C1NC1=NC=C(C=2C=CC(F)=CC=2)O1 JCHXUTFAZSIAIM-UHFFFAOYSA-N 0.000 claims 1
- GIXYMJYMJLIHFE-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-methoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)N2CCN(C)CC2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 GIXYMJYMJLIHFE-UHFFFAOYSA-N 0.000 claims 1
- WRVLCLMTOLDFKI-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-methoxy-5-(methylsulfonylmethyl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=C(CS(C)(=O)=O)C=C1NC1=NC=C(C=2C=CC(F)=CC=2)O1 WRVLCLMTOLDFKI-UHFFFAOYSA-N 0.000 claims 1
- QLBVNQMJVRAWJK-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-methoxy-5-(oxolan-2-ylmethylsulfonyl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CC2OCCC2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 QLBVNQMJVRAWJK-UHFFFAOYSA-N 0.000 claims 1
- REDVXFOZNNTELU-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-methoxy-5-(oxolan-3-ylsulfonyl)phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)C2COCC2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 REDVXFOZNNTELU-UHFFFAOYSA-N 0.000 claims 1
- WKZGWYCSJHZJFM-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-methoxy-5-[(5-methyl-1,2-oxazol-3-yl)methylsulfonyl]phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CC2=NOC(C)=C2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 WKZGWYCSJHZJFM-UHFFFAOYSA-N 0.000 claims 1
- QUMJQKAQGRKROF-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-methoxy-5-[2-(4-methyl-1,3-thiazol-5-yl)ethylsulfonyl]phenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CCC2=C(N=CS2)C)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 QUMJQKAQGRKROF-UHFFFAOYSA-N 0.000 claims 1
- GOHFRUCEWZGSAD-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[5-(2-imidazol-1-ylethylsulfonyl)-2-methoxyphenyl]-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CCN2C=NC=C2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 GOHFRUCEWZGSAD-UHFFFAOYSA-N 0.000 claims 1
- WYERNLHOPPHRDM-UHFFFAOYSA-N 5-(5-chlorothiophen-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=2SC(Cl)=CC=2)=C1 WYERNLHOPPHRDM-UHFFFAOYSA-N 0.000 claims 1
- PQAJYOLOSADJGB-UHFFFAOYSA-N 5-[3-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-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(C=CC=2)C=2C=C3CCOC3=CC=2)=C1 PQAJYOLOSADJGB-UHFFFAOYSA-N 0.000 claims 1
- VDHBAAXTLJWVLI-UHFFFAOYSA-N 5-[3-(2-chlorophenyl)phenyl]-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(C=CC=2)C=2C(=CC=CC=2)Cl)=C1 VDHBAAXTLJWVLI-UHFFFAOYSA-N 0.000 claims 1
- ACTDJHRFZZJXMS-UHFFFAOYSA-N 5-[3-(2-chloropyrimidin-4-yl)oxyphenyl]-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(OC=3N=C(Cl)N=CC=3)C=CC=2)=C1 ACTDJHRFZZJXMS-UHFFFAOYSA-N 0.000 claims 1
- STGDLDUMBXBRPO-UHFFFAOYSA-N 5-[3-(2-tert-butylpyrimidin-4-yl)phenyl]-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(C=CC=2)C=2N=C(N=CC=2)C(C)(C)C)=C1 STGDLDUMBXBRPO-UHFFFAOYSA-N 0.000 claims 1
- WQOHOHJWHPHKCU-UHFFFAOYSA-N 5-[3-(3,5-difluorophenyl)phenyl]-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(C=CC=2)C=2C=C(F)C=C(F)C=2)=C1 WQOHOHJWHPHKCU-UHFFFAOYSA-N 0.000 claims 1
- SMQHYHBQZOQRHF-UHFFFAOYSA-N 5-[3-(cyclopropylmethoxy)phenyl]-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(OCC3CC3)C=CC=2)=C1 SMQHYHBQZOQRHF-UHFFFAOYSA-N 0.000 claims 1
- BRIFZLSYKRIGOZ-UHFFFAOYSA-N 5-[3-[(2,3-dimethoxyphenyl)methoxy]phenyl]-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(OCC=3C(=C(OC)C=CC=3)OC)C=CC=2)=C1 BRIFZLSYKRIGOZ-UHFFFAOYSA-N 0.000 claims 1
- 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
- HFICAVMUTYFODG-UHFFFAOYSA-N n,5-diphenyl-1,3-oxazol-2-amine Chemical compound C=1C=CC=CC=1NC(O1)=NC=C1C1=CC=CC=C1 HFICAVMUTYFODG-UHFFFAOYSA-N 0.000 claims 1
- KOWGFCOWEPMYGC-UHFFFAOYSA-N n,n-diethyl-4-[(5-phenyl-1,3-oxazol-2-yl)amino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 KOWGFCOWEPMYGC-UHFFFAOYSA-N 0.000 claims 1
- IXAUVBHKVRFJHO-UHFFFAOYSA-N n,n-diethyl-4-methoxy-3-[(5-phenyl-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=CC=CC=2)=C1 IXAUVBHKVRFJHO-UHFFFAOYSA-N 0.000 claims 1
- GJKVLIMXXVGURU-UHFFFAOYSA-N n,n-diethyl-4-methoxy-3-[[5-(3-phenylphenyl)-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=2C=CC=CC=2)=C1 GJKVLIMXXVGURU-UHFFFAOYSA-N 0.000 claims 1
- 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
- FINBGMFTXPKRQT-UHFFFAOYSA-N n,n-dimethyl-4-[(5-phenyl-1,3-oxazol-2-yl)amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 FINBGMFTXPKRQT-UHFFFAOYSA-N 0.000 claims 1
- 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
- MZTVDCWVRMCOQU-UHFFFAOYSA-N n-(2-chloro-5-ethylsulfonylphenyl)-5-(4-fluorophenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(Cl)C(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 MZTVDCWVRMCOQU-UHFFFAOYSA-N 0.000 claims 1
- PHZDEDGNAXPHCM-UHFFFAOYSA-N n-(2-chloro-5-methylsulfonylphenyl)-5-(4-fluorophenyl)-1,3-oxazol-2-amine Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 PHZDEDGNAXPHCM-UHFFFAOYSA-N 0.000 claims 1
- 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
- LGHFQXKZMIHBLB-UHFFFAOYSA-N n-(2-ethoxyphenyl)-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCOC1=CC=CC=C1NC1=NC=C(C=2C=C(OC)C=CC=2)O1 LGHFQXKZMIHBLB-UHFFFAOYSA-N 0.000 claims 1
- OGBLNRKFQWTUFD-UHFFFAOYSA-N n-(2-methoxy-5-nitrophenyl)-5-phenyl-1,3-oxazol-2-amine Chemical compound COC1=CC=C([N+]([O-])=O)C=C1NC1=NC=C(C=2C=CC=CC=2)O1 OGBLNRKFQWTUFD-UHFFFAOYSA-N 0.000 claims 1
- AGVJGGOWJKCBKY-UHFFFAOYSA-N n-(2-methoxy-5-pentan-3-ylsulfonylphenyl)-5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-amine Chemical compound CCC(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 AGVJGGOWJKCBKY-UHFFFAOYSA-N 0.000 claims 1
- FLEGUMUEFROASN-UHFFFAOYSA-N n-(2-methoxy-5-propan-2-ylsulfonylphenyl)-5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)C(C)C)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2N=CC=CC=2)O1 FLEGUMUEFROASN-UHFFFAOYSA-N 0.000 claims 1
- DLHCYJIQXKETIN-UHFFFAOYSA-N n-(2-methoxyphenyl)-5-phenyl-1,3-oxazol-2-amine Chemical compound COC1=CC=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 DLHCYJIQXKETIN-UHFFFAOYSA-N 0.000 claims 1
- QRNGLFDTZRELIW-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=C(OC)C(OC)=CC=3)=NC=2)=C1 QRNGLFDTZRELIW-UHFFFAOYSA-N 0.000 claims 1
- SNIMAGPDEBBOCW-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-5-(4-fluorophenyl)-1,3-oxazol-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=2C=CC(F)=CC=2)O1 SNIMAGPDEBBOCW-UHFFFAOYSA-N 0.000 claims 1
- YPCNLBKNWQGREW-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-5-(4-methylphenyl)-1,3-oxazol-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=2C=CC(C)=CC=2)O1 YPCNLBKNWQGREW-UHFFFAOYSA-N 0.000 claims 1
- BTALXHSRAPGDGP-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-5-phenyl-1,3-oxazol-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 BTALXHSRAPGDGP-UHFFFAOYSA-N 0.000 claims 1
- RKNRDRPDYXCRPG-UHFFFAOYSA-N n-(3,5-dimethoxyphenyl)-5-phenyl-1,3-oxazol-2-amine Chemical compound COC1=CC(OC)=CC(NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 RKNRDRPDYXCRPG-UHFFFAOYSA-N 0.000 claims 1
- NFUAZIAKHDCKGA-UHFFFAOYSA-N n-(3-ethylsulfonylphenyl)-5-(4-fluorophenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=CC(NC=2OC(=CN=2)C=2C=CC(F)=CC=2)=C1 NFUAZIAKHDCKGA-UHFFFAOYSA-N 0.000 claims 1
- XLGKHWGSIZWZNN-UHFFFAOYSA-N n-(3-methylphenyl)-5-phenyl-1,3-oxazol-2-amine Chemical compound CC1=CC=CC(NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 XLGKHWGSIZWZNN-UHFFFAOYSA-N 0.000 claims 1
- VKLQCYYJIRWXHJ-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-fluorophenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(F)C=CC=2)=C1 VKLQCYYJIRWXHJ-UHFFFAOYSA-N 0.000 claims 1
- GOGIUMBXFRNDRK-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(OC)C=CC=2)=C1 GOGIUMBXFRNDRK-UHFFFAOYSA-N 0.000 claims 1
- AWTKNWMTMOUAOO-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-methyl-1-benzothiophen-2-yl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C2=C(C3=CC=CC=C3S2)C)=C1 AWTKNWMTMOUAOO-UHFFFAOYSA-N 0.000 claims 1
- GWODCOXHFBKWOT-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-phenoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(OC=3C=CC=CC=3)C=CC=2)=C1 GWODCOXHFBKWOT-UHFFFAOYSA-N 0.000 claims 1
- AEUNWHRZTQUUSY-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-phenylmethoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 AEUNWHRZTQUUSY-UHFFFAOYSA-N 0.000 claims 1
- PKUDAUZYOFHVDW-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-phenylphenyl)-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=2C=CC=CC=2)=C1 PKUDAUZYOFHVDW-UHFFFAOYSA-N 0.000 claims 1
- KDPPCIPRWNKEMI-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-pyrazin-2-ylphenyl)-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=CC=NC=2)=C1 KDPPCIPRWNKEMI-UHFFFAOYSA-N 0.000 claims 1
- BKGWUUYFDIOKHW-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-pyridin-3-ylphenyl)-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=2C=NC=CC=2)=C1 BKGWUUYFDIOKHW-UHFFFAOYSA-N 0.000 claims 1
- QFOCOODPWRLBNO-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-pyridin-4-ylphenyl)-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=2C=CN=CC=2)=C1 QFOCOODPWRLBNO-UHFFFAOYSA-N 0.000 claims 1
- KLOIDRPIGIEADK-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-quinolin-3-ylphenyl)-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=2C=C3C=CC=CC3=NC=2)=C1 KLOIDRPIGIEADK-UHFFFAOYSA-N 0.000 claims 1
- KOJNZGHIASJHCV-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-thiophen-2-ylphenyl)-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=CC=2)=C1 KOJNZGHIASJHCV-UHFFFAOYSA-N 0.000 claims 1
- GJIVVHLMOZQKEB-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-thiophen-3-ylphenyl)-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)C2=CSC=C2)=C1 GJIVVHLMOZQKEB-UHFFFAOYSA-N 0.000 claims 1
- MTOCSIVGNRDGEF-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(4-methylsulfonylphenyl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 MTOCSIVGNRDGEF-UHFFFAOYSA-N 0.000 claims 1
- IFBOUPMOUHQNQL-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)=C1 IFBOUPMOUHQNQL-UHFFFAOYSA-N 0.000 claims 1
- MOAFNJLQVPXLRD-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(1,3-thiazol-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=CN=2)=C1 MOAFNJLQVPXLRD-UHFFFAOYSA-N 0.000 claims 1
- SNJAEDIYEOTMNR-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(1-pyridin-4-ylethoxy)phenyl]-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(OC(C)C=3C=CN=CC=3)C=CC=2)=C1 SNJAEDIYEOTMNR-UHFFFAOYSA-N 0.000 claims 1
- OIMTZGYBKVUJIY-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(1h-indol-5-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=2C=C3C=CNC3=CC=2)=C1 OIMTZGYBKVUJIY-UHFFFAOYSA-N 0.000 claims 1
- DOKIBWCVABZHOH-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(2-fluorophenyl)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=2C(=CC=CC=2)F)=C1 DOKIBWCVABZHOH-UHFFFAOYSA-N 0.000 claims 1
- CBTKMRAJHDYYKF-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(2-phenylpyrimidin-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(N=CC=2)C=2C=CC=CC=2)=C1 CBTKMRAJHDYYKF-UHFFFAOYSA-N 0.000 claims 1
- JMHZLKXLZXIGLS-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(2-propan-2-ylpyrimidin-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(N=CC=2)C(C)C)=C1 JMHZLKXLZXIGLS-UHFFFAOYSA-N 0.000 claims 1
- 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
- KNEFNELZBQZOLB-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(3-fluorophenyl)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=2C=C(F)C=CC=2)=C1 KNEFNELZBQZOLB-UHFFFAOYSA-N 0.000 claims 1
- PQZKVWILKSYPCO-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(3-methylimidazol-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=2)C)=C1 PQZKVWILKSYPCO-UHFFFAOYSA-N 0.000 claims 1
- FUNNIDYDUXOFSE-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(4-fluorophenyl)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=2C=CC(F)=CC=2)=C1 FUNNIDYDUXOFSE-UHFFFAOYSA-N 0.000 claims 1
- 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
- QQJQRIWRNDWLKJ-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(furan-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=2OC=CC=2)=C1 QQJQRIWRNDWLKJ-UHFFFAOYSA-N 0.000 claims 1
- 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
- VKHWZMHURFIFFI-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(pyridin-2-ylmethoxy)phenyl]-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(OCC=3N=CC=CC=3)C=CC=2)=C1 VKHWZMHURFIFFI-UHFFFAOYSA-N 0.000 claims 1
- SZKANUNLEFEHAH-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-(trifluoromethyl)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(F)(F)F)=C1 SZKANUNLEFEHAH-UHFFFAOYSA-N 0.000 claims 1
- BIRCSCIWRDIBQZ-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-[3-[2-(propan-2-ylamino)pyrimidin-4-yl]oxyphenyl]-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(OC=3N=C(NC(C)C)N=CC=3)C=CC=2)=C1 BIRCSCIWRDIBQZ-UHFFFAOYSA-N 0.000 claims 1
- 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
- WMCCERKNYDEEPA-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-naphthalen-2-yl-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C3C=CC=CC3=CC=2)=C1 WMCCERKNYDEEPA-UHFFFAOYSA-N 0.000 claims 1
- ODGMIRDHEZREOW-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-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)=C1 ODGMIRDHEZREOW-UHFFFAOYSA-N 0.000 claims 1
- GHWNNNJSJAYUPF-UHFFFAOYSA-N n-(5-ethylsulfonyl-2-methoxyphenyl)-5-pyridin-3-yl-1,3-oxazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 GHWNNNJSJAYUPF-UHFFFAOYSA-N 0.000 claims 1
- NHHXVXXNXLBOCG-UHFFFAOYSA-N n-(6-imidazol-1-ylpyridin-3-yl)-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=NC(=CC=3)N3C=NC=C3)=NC=2)=C1 NHHXVXXNXLBOCG-UHFFFAOYSA-N 0.000 claims 1
- LRZQPHLESMVISV-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]amino]-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NCC2CC2)C=C1NC(O1)=NC=C1C1=CC=C(F)C=C1 LRZQPHLESMVISV-UHFFFAOYSA-N 0.000 claims 1
- 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
- JBPCVDQZFFPCFJ-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-4-[[5-(3-methoxyphenyl)-1,3-oxazol-2-yl]amino]benzamide Chemical compound C1=CC(C(=O)NCCN(CC)CC)=CC=C1NC1=NC=C(C=2C=C(OC)C=CC=2)O1 JBPCVDQZFFPCFJ-UHFFFAOYSA-N 0.000 claims 1
- DCXPNECEKCWSDD-UHFFFAOYSA-N n-[2-methoxy-5-(1-pyridin-4-ylethylsulfonyl)phenyl]-5-(3-phenylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)C(C)C=2C=CN=CC=2)C=C1NC(O1)=NC=C1C(C=1)=CC=CC=1C1=CC=CC=C1 DCXPNECEKCWSDD-UHFFFAOYSA-N 0.000 claims 1
- YJSVQOYIPFVHCP-UHFFFAOYSA-N n-[2-methoxy-5-(2-methylpropylsulfonyl)phenyl]-5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CC(C)C)C=C1NC1=NC=C(C=2C=C(C=CC=2)C=2N=CC=CC=2)O1 YJSVQOYIPFVHCP-UHFFFAOYSA-N 0.000 claims 1
- NPNPSEHDPJYXHQ-UHFFFAOYSA-N n-[2-methoxy-5-(2-pyridin-2-ylethylsulfonyl)phenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CCC=2N=CC=CC=2)C=C1NC(O1)=NC=C1C1=CC=CC=C1 NPNPSEHDPJYXHQ-UHFFFAOYSA-N 0.000 claims 1
- OWHSBBNNGDOFCA-UHFFFAOYSA-N n-[2-methoxy-5-(oxolan-2-ylmethylsulfonyl)phenyl]-5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CC2OCCC2)C=C1NC(O1)=NC=C1C(C=1)=CC=CC=1C1=CC=CC=N1 OWHSBBNNGDOFCA-UHFFFAOYSA-N 0.000 claims 1
- FTKXYZYYJUPERX-UHFFFAOYSA-N n-[2-methoxy-5-(oxolan-3-ylsulfonyl)phenyl]-5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)C2COCC2)C=C1NC(O1)=NC=C1C(C=1)=CC=CC=1C1=CC=CC=N1 FTKXYZYYJUPERX-UHFFFAOYSA-N 0.000 claims 1
- FDJHGZLDILTSCS-UHFFFAOYSA-N n-[2-methoxy-5-[2-(4-methyl-1,3-thiazol-5-yl)ethylsulfonyl]phenyl]-5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CCC2=C(N=CS2)C)C=C1NC(O1)=NC=C1C(C=1)=CC=CC=1C1=CC=CC=N1 FDJHGZLDILTSCS-UHFFFAOYSA-N 0.000 claims 1
- NTCVWOMBPGHYBN-UHFFFAOYSA-N n-[3-(2-imidazol-1-ylethoxy)-4-methoxyphenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound C1=C(OCCN2C=NC=C2)C(OC)=CC=C1NC(O1)=NC=C1C1=CC=CC=C1 NTCVWOMBPGHYBN-UHFFFAOYSA-N 0.000 claims 1
- NBHKYMAFRHRCPQ-UHFFFAOYSA-N n-[3-(benzenesulfonyl)phenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound C=1C=CC(NC=2OC(=CN=2)C=2C=CC=CC=2)=CC=1S(=O)(=O)C1=CC=CC=C1 NBHKYMAFRHRCPQ-UHFFFAOYSA-N 0.000 claims 1
- ZYZDEEIHTRPKEF-UHFFFAOYSA-N n-[3-chloro-4-(4-methylpiperazin-1-yl)phenyl]-5-(3-cyclopentyloxyphenyl)-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C(C=2C=C(OC3CCCC3)C=CC=2)O1 ZYZDEEIHTRPKEF-UHFFFAOYSA-N 0.000 claims 1
- DKDUVEYDFUCYMT-UHFFFAOYSA-N n-[3-chloro-4-(4-methylpiperazin-1-yl)phenyl]-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=C(Cl)C(N4CCN(C)CC4)=CC=3)=NC=2)=C1 DKDUVEYDFUCYMT-UHFFFAOYSA-N 0.000 claims 1
- DPOOSZZMGPGRHE-UHFFFAOYSA-N n-[3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=C(F)C(N4CCN(C)CC4)=CC=3)=NC=2)=C1 DPOOSZZMGPGRHE-UHFFFAOYSA-N 0.000 claims 1
- LGSOZUHSMDQCJG-UHFFFAOYSA-N n-[4-(2-imidazol-1-ylethoxy)-3-methoxyphenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound C=1C=C(OCCN2C=NC=C2)C(OC)=CC=1NC(O1)=NC=C1C1=CC=CC=C1 LGSOZUHSMDQCJG-UHFFFAOYSA-N 0.000 claims 1
- QHAROKNTCUEBHN-UHFFFAOYSA-N n-[4-(3,5-dimethylpiperazin-1-yl)phenyl]-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)N3CC(C)NC(C)C3)=NC=2)=C1 QHAROKNTCUEBHN-UHFFFAOYSA-N 0.000 claims 1
- RPFKNCXERXITCX-UHFFFAOYSA-N n-[4-(4-ethylpiperazin-1-yl)phenyl]-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C=C(OC)C=CC=2)O1 RPFKNCXERXITCX-UHFFFAOYSA-N 0.000 claims 1
- OWJDDZUHWVRKBY-UHFFFAOYSA-N n-[4-(4-ethylpiperazin-1-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 OWJDDZUHWVRKBY-UHFFFAOYSA-N 0.000 claims 1
- HTEINPYAXRWKIU-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-5-(3-phenylmethoxyphenyl)-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)O1 HTEINPYAXRWKIU-UHFFFAOYSA-N 0.000 claims 1
- KRZMEEJYLVOCAY-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-5-(3-propan-2-yloxyphenyl)-1,3-oxazol-2-amine Chemical compound CC(C)OC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=2)=C1 KRZMEEJYLVOCAY-UHFFFAOYSA-N 0.000 claims 1
- LPHFJICAYYGKTA-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-5-(3-propoxyphenyl)-1,3-oxazol-2-amine Chemical compound CCCOC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=2)=C1 LPHFJICAYYGKTA-UHFFFAOYSA-N 0.000 claims 1
- UOCJXFJGVJXOCA-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-5-[3-(2-methylprop-2-enoxy)phenyl]-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C=C(OCC(C)=C)C=CC=2)O1 UOCJXFJGVJXOCA-UHFFFAOYSA-N 0.000 claims 1
- BSQXLWDBXSCKRO-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-5-[3-(2-methylpropoxy)phenyl]-1,3-oxazol-2-amine Chemical compound CC(C)COC1=CC=CC(C=2OC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=2)=C1 BSQXLWDBXSCKRO-UHFFFAOYSA-N 0.000 claims 1
- AWDVWHKNVNBBLG-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 AWDVWHKNVNBBLG-UHFFFAOYSA-N 0.000 claims 1
- DOVCZNQJKYPTEP-UHFFFAOYSA-N n-[4-(diethylaminomethyl)phenyl]-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound C1=CC(CN(CC)CC)=CC=C1NC1=NC=C(C=2C=C(OC)C=CC=2)O1 DOVCZNQJKYPTEP-UHFFFAOYSA-N 0.000 claims 1
- BCMSOSAVZJMGFH-UHFFFAOYSA-N n-[4-(methylsulfonylmethyl)phenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound C1=CC(CS(=O)(=O)C)=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 BCMSOSAVZJMGFH-UHFFFAOYSA-N 0.000 claims 1
- XCEQKKMIVXEOBI-UHFFFAOYSA-N n-[4-(morpholin-4-ylmethyl)phenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound C=1C=C(NC=2OC(=CN=2)C=2C=CC=CC=2)C=CC=1CN1CCOCC1 XCEQKKMIVXEOBI-UHFFFAOYSA-N 0.000 claims 1
- YOZAPDVBJIMQAT-UHFFFAOYSA-N n-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 YOZAPDVBJIMQAT-UHFFFAOYSA-N 0.000 claims 1
- YCJNCHPDUDGHPX-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]phenyl]-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(CN(C)C)=CC=3)=NC=2)=C1 YCJNCHPDUDGHPX-UHFFFAOYSA-N 0.000 claims 1
- YDLYERHZKHINAD-UHFFFAOYSA-N n-[4-[2-(dimethylamino)ethyl]phenyl]-5-(3-methoxyphenyl)-1,3-oxazol-2-amine Chemical compound COC1=CC=CC(C=2OC(NC=3C=CC(CCN(C)C)=CC=3)=NC=2)=C1 YDLYERHZKHINAD-UHFFFAOYSA-N 0.000 claims 1
- HTIZPBXCJPQDEM-UHFFFAOYSA-N n-[5-(ethylsulfonyl)-2-methoxyphenyl]-5-[3-(2-pyridinyl)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=CC=CC=2)=C1 HTIZPBXCJPQDEM-UHFFFAOYSA-N 0.000 claims 1
- MOLNDTKRPCNAPU-UHFFFAOYSA-N n-[5-[[5-(3-iodophenyl)-1,3-oxazol-2-yl]amino]-2-methylphenyl]methanesulfonamide Chemical compound C1=C(NS(C)(=O)=O)C(C)=CC=C1NC1=NC=C(C=2C=C(I)C=CC=2)O1 MOLNDTKRPCNAPU-UHFFFAOYSA-N 0.000 claims 1
- JMDOCQUQRQDCDY-UHFFFAOYSA-N n-[5-ethylsulfonyl-2-(2-imidazol-1-ylethoxy)phenyl]-5-(4-fluorophenyl)-1,3-oxazol-2-amine Chemical compound N=1C=C(C=2C=CC(F)=CC=2)OC=1NC1=CC(S(=O)(=O)CC)=CC=C1OCCN1C=CN=C1 JMDOCQUQRQDCDY-UHFFFAOYSA-N 0.000 claims 1
- ITLQWZNMOFAXKV-UHFFFAOYSA-N n-[5-ethylsulfonyl-2-(2-pyridin-2-ylethoxy)phenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound N=1C=C(C=2C=CC=CC=2)OC=1NC1=CC(S(=O)(=O)CC)=CC=C1OCCC1=CC=CC=N1 ITLQWZNMOFAXKV-UHFFFAOYSA-N 0.000 claims 1
- MQOWMHDYMDSXQS-UHFFFAOYSA-N n-[5-ethylsulfonyl-2-[2-(triazol-1-yl)ethoxy]phenyl]-5-phenyl-1,3-oxazol-2-amine Chemical compound N=1C=C(C=2C=CC=CC=2)OC=1NC1=CC(S(=O)(=O)CC)=CC=C1OCCN1C=CN=N1 MQOWMHDYMDSXQS-UHFFFAOYSA-N 0.000 claims 1
- KGFODVQTJGAARF-UHFFFAOYSA-N n-butyl-3-[(5-phenyl-1,3-oxazol-2-yl)amino]benzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC(NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 KGFODVQTJGAARF-UHFFFAOYSA-N 0.000 claims 1
- JNAQKROXJHPGSI-UHFFFAOYSA-N n-butyl-4-methoxy-3-[(5-phenyl-1,3-oxazol-2-yl)amino]benzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 JNAQKROXJHPGSI-UHFFFAOYSA-N 0.000 claims 1
- PDHHWBBHYLSDNJ-UHFFFAOYSA-N n-butyl-4-methoxy-3-[[5-(3-phenylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 PDHHWBBHYLSDNJ-UHFFFAOYSA-N 0.000 claims 1
- BNVFEFWZSJFWDJ-UHFFFAOYSA-N n-cyclopropyl-4-methoxy-3-[[5-(3-phenylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC2CC2)C=C1NC(O1)=NC=C1C(C=1)=CC=CC=1C1=CC=CC=C1 BNVFEFWZSJFWDJ-UHFFFAOYSA-N 0.000 claims 1
- QXTAZFLGCLFKID-UHFFFAOYSA-N n-ethyl-4-methoxy-3-[[5-(3-pyridin-2-ylphenyl)-1,3-oxazol-2-yl]amino]benzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=C(OC)C(NC=2OC(=CN=2)C=2C=C(C=CC=2)C=2N=CC=CC=2)=C1 QXTAZFLGCLFKID-UHFFFAOYSA-N 0.000 claims 1
- YBFMWHXUZIXNGN-UHFFFAOYSA-N n-methyl-1-[4-[(5-phenyl-1,3-oxazol-2-yl)amino]phenyl]methanesulfonamide Chemical compound C1=CC(CS(=O)(=O)NC)=CC=C1NC1=NC=C(C=2C=CC=CC=2)O1 YBFMWHXUZIXNGN-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41754802P | 2002-10-10 | 2002-10-10 | |
| PCT/US2003/033317 WO2004032882A2 (en) | 2002-10-10 | 2003-10-10 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006503081A JP2006503081A (ja) | 2006-01-26 |
| JP2006503081A5 true JP2006503081A5 (https=) | 2006-11-24 |
Family
ID=32094036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004543799A Pending JP2006503081A (ja) | 2002-10-10 | 2003-10-10 | 化学化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7189712B2 (https=) |
| EP (1) | EP1551813A4 (https=) |
| JP (1) | JP2006503081A (https=) |
| AU (1) | AU2003287178A1 (https=) |
| WO (1) | WO2004032882A2 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA04005939A (es) | 2002-01-22 | 2005-01-25 | Warner Lambert Co | 2-(piridin-2-ilamino)-pirido[2,3-d]pirimidin-7-onas. |
| AU2004255934B2 (en) * | 2003-07-11 | 2010-02-25 | Warner-Lambert Company Llc | Isethionate salt of a selective CDK4 inhibitor |
| EP1684750B1 (en) * | 2003-10-23 | 2010-04-28 | AB Science | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
| EP2543376A1 (en) | 2004-04-08 | 2013-01-09 | Targegen, Inc. | Benzotriazine inhibitors of kinases |
| WO2005102318A1 (en) * | 2004-04-20 | 2005-11-03 | Ab Science | Use of c-kit inhibitors for treating hiv related diseases |
| JP2007538064A (ja) * | 2004-05-18 | 2007-12-27 | アブ サイエンス | 化学または生物兵器に曝露された患者を処置するための肥満細胞阻害剤の使用法 |
| US7652051B2 (en) | 2004-08-25 | 2010-01-26 | Targegen, Inc. | Heterocyclic compounds and methods of use |
| WO2006106437A2 (en) * | 2005-04-04 | 2006-10-12 | Ab Science | Substituted oxazole derivatives and their use as tyrosine kinase inhibitors |
| EP2418202B1 (en) | 2006-03-31 | 2014-01-29 | Novartis AG | (4-[4-[5-(substituted amino)-pyridin-2-yl]phenyl]-cyclohexyl)-acetic acid derivatives as DGAT inhibitors |
| CN101460470B (zh) | 2006-05-30 | 2011-05-18 | 阿斯利康(瑞典)有限公司 | 作为dgat1抑制剂的1,3,4-二唑衍生物 |
| ES2606505T3 (es) * | 2007-01-12 | 2017-03-24 | Ab Science | Tratamiento de combinación de cánceres sólidos con antimetabolitos e inhibidores de tirosina quinasa |
| WO2008128231A1 (en) | 2007-04-16 | 2008-10-23 | Hutchison Medipharma Enterprises Limited | Pyrimidine derivatives |
| CN101888999B (zh) * | 2007-12-05 | 2013-12-11 | 巴斯夫欧洲公司 | 吡啶基甲基磺酰胺化合物 |
| NZ586104A (en) | 2007-12-20 | 2012-02-24 | Astrazeneca Ab | Carbamoyl compounds as dgat1 inhibitors 190 |
| WO2009111502A2 (en) | 2008-03-03 | 2009-09-11 | University Of Notre Dame Du Lac | Anti-cancer compounds, synthesis thereof, and methods of using same |
| TW201103895A (en) | 2009-06-19 | 2011-02-01 | Astrazeneca Ab | Chemical compounds |
| US8957216B2 (en) * | 2010-03-24 | 2015-02-17 | Amitech Therapeutic Solutions, Inc. | Heterocyclic compounds useful for kinase inhibition |
| 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 |
| CN104744376A (zh) * | 2015-03-14 | 2015-07-01 | 长沙深橙生物科技有限公司 | 一种2-异丙基嘧啶衍生物的制备方法 |
| KR101713027B1 (ko) * | 2015-12-23 | 2017-03-07 | 한국원자력의학원 | 페닐옥사졸계 유도체를 포함하는 암 예방 또는 치료용 조성물 |
| KR101948555B1 (ko) * | 2017-08-03 | 2019-02-15 | 한국원자력의학원 | 수용체 티로신 키나아제 저해제를 유효성분으로 함유하는 암 예방 또는 치료용 약학조성물 |
| US12274703B2 (en) | 2017-12-21 | 2025-04-15 | Gliapharm Sa | Compositions and methods of treatment for neurological disorders comprising a dementia |
| US12310967B2 (en) | 2017-12-21 | 2025-05-27 | Gliapharm Sa | Compositions and methods of treatment for neurological disorders comprising motor neuron diseases |
| WO2019164996A1 (en) * | 2018-02-21 | 2019-08-29 | Southern Research Institute | 2-aminoaryl-5-aryloxazole analogs for the treatment of neurodegenerative diseases |
| WO2020132378A2 (en) | 2018-12-22 | 2020-06-25 | Gliapharm Sa | Compositions and methods of treatment for neurological disorders comprising depression |
| AR118050A1 (es) | 2019-02-15 | 2021-09-15 | Bristol Myers Squibb Co | Compuestos bicíclicos sustituidos como moduladores del receptor farnesoide x |
| AU2020221370A1 (en) | 2019-02-15 | 2021-10-07 | Bristol-Myers Squibb Company | Substituted bicyclic compounds as farnesoid x receptor modulators |
| KR20240020735A (ko) | 2021-05-07 | 2024-02-15 | 카이메라 쎄라퓨틱스 인코포레이티드 | Cdk2 분해제 및 그 용도 |
| US12084453B2 (en) | 2021-12-10 | 2024-09-10 | Incyte Corporation | Bicyclic amines as CDK12 inhibitors |
| KR20250144817A (ko) * | 2024-03-27 | 2025-10-13 | 동국대학교 산학협력단 | 신규 옥사다이아졸 유도체 및 이를 포함하는 암 예방 또는 치료용 조성물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3092946B2 (ja) * | 1995-12-14 | 2000-09-25 | メルク エンド カンパニー インコーポレーテッド | ゴナドトロピン放出ホルモン拮抗剤 |
| WO2000025780A1 (en) * | 1998-10-29 | 2000-05-11 | Bristol-Myers Squibb Company | Compounds derived from an amine nucleus that are inhibitors of impdh enzyme |
| BR0116452A (pt) * | 2000-12-21 | 2003-09-30 | Glaxo Group Ltd | Composto, composição farmacêutica, uso de um composto |
| WO2005004818A2 (en) * | 2003-07-09 | 2005-01-20 | Imclone Systems Incorporated | Heterocyclic compounds and their use as anticancer agents |
-
2003
- 2003-10-10 US US10/530,810 patent/US7189712B2/en not_active Expired - Fee Related
- 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006503081A5 (https=) | ||
| RU2489426C2 (ru) | Производные аминопиразола | |
| JP2010533158A5 (https=) | ||
| JP2007516173A5 (https=) | ||
| JP2019517455A5 (https=) | ||
| JP2015533157A5 (https=) | ||
| JP2018535999A5 (https=) | ||
| JP2009537543A5 (https=) | ||
| JP2013519680A5 (https=) | ||
| JP2007530690A5 (https=) | ||
| JP2005538955A5 (https=) | ||
| IL303196A (en) | Heteroaryl-substituted pyridines and methods of use | |
| RU2012132692A (ru) | Новые ингибиторы s-нитрозоглутатионредуктазы | |
| RU2012116207A (ru) | Производные индола в качестве модуляторов crac | |
| JP2023506642A5 (https=) | ||
| RU2006133909A (ru) | Производные азабицикло {3. 1. 0}гексана, применимые в качестве модуляторов допаминовых рецепторов d3 | |
| JP2007523208A5 (https=) | ||
| RU2004121029A (ru) | Производные пиримидина в качестве модуляторов рецептора инсулинподобного фактора роста 1 (igf-1) | |
| HRP20191327T1 (hr) | 4-hidroksi-3-(heteroaril)piridin-2-on apj agonisti za primjenju u liječenju kardiovaskularnih poremećaja | |
| JP2007508346A5 (https=) | ||
| JP2010540452A5 (https=) | ||
| JP2006524686A5 (https=) | ||
| JP2009525340A5 (https=) | ||
| JP2018507234A5 (https=) | ||
| RU2016111138A (ru) | Гетероциклические соединения и способы их применения |