JP2012519179A5 - - Google Patents
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- Publication number
- JP2012519179A5 JP2012519179A5 JP2011552171A JP2011552171A JP2012519179A5 JP 2012519179 A5 JP2012519179 A5 JP 2012519179A5 JP 2011552171 A JP2011552171 A JP 2011552171A JP 2011552171 A JP2011552171 A JP 2011552171A JP 2012519179 A5 JP2012519179 A5 JP 2012519179A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- pyrazol
- quinazolin
- fluorophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 78
- 229910052739 hydrogen Inorganic materials 0.000 claims 45
- 239000001257 hydrogen Substances 0.000 claims 45
- 125000005843 halogen group Chemical group 0.000 claims 35
- 150000002431 hydrogen Chemical class 0.000 claims 32
- 125000003342 alkenyl group Chemical group 0.000 claims 31
- 125000000304 alkynyl group Chemical group 0.000 claims 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims 28
- 125000001188 haloalkyl group Chemical group 0.000 claims 28
- 125000000623 heterocyclic group Chemical group 0.000 claims 25
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- -1 methoxy, amino Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000003106 haloaryl group Chemical group 0.000 claims 3
- 125000004001 thioalkyl group Chemical group 0.000 claims 3
- YVZZPKZLECIEKD-UHFFFAOYSA-N 2-[2-[(4-fluorophenyl)-hydroxymethyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-7-yl]oxyacetic acid Chemical compound N1C(C)=CC(NC=2C3=CC=C(OCC(O)=O)C=C3N=C(N=2)C(O)C=2C=CC(F)=CC=2)=N1 YVZZPKZLECIEKD-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 2
- 102000042838 JAK family Human genes 0.000 claims 2
- 108091082332 JAK family Proteins 0.000 claims 2
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- WWGPZLMMSYEULM-UHFFFAOYSA-N (2-methoxyphenyl)-[4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)C1=NC(NC2=NNC=C2)=C(C=CC=C2)C2=N1 WWGPZLMMSYEULM-UHFFFAOYSA-N 0.000 claims 1
- SOSNHEBNCWAGHI-UHFFFAOYSA-N (2-methoxyphenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound COC1=CC=CC=C1C(O)C1=NC(NC2=NNC(C)=C2)=C(C=CC=C2)C2=N1 SOSNHEBNCWAGHI-UHFFFAOYSA-N 0.000 claims 1
- VYPWEQVKLSNGTK-UHFFFAOYSA-N (2-methoxyphenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)C1=NC(NC2=NNC(C)=C2)=C(C=CC=C2)C2=N1 VYPWEQVKLSNGTK-UHFFFAOYSA-N 0.000 claims 1
- QEYNJNMWBYIISD-UHFFFAOYSA-N (3,4-difluorophenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(O)C=2C=C(F)C(F)=CC=2)=N1 QEYNJNMWBYIISD-UHFFFAOYSA-N 0.000 claims 1
- PQFUPUORCKGLGB-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(O)C=2C=C(Cl)C(F)=CC=2)=N1 PQFUPUORCKGLGB-UHFFFAOYSA-N 0.000 claims 1
- MWPIZTHMLQBCGZ-UHFFFAOYSA-N (3-fluorophenyl)-[4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanone Chemical compound FC1=CC=CC(C(=O)C=2N=C3C=CC=CC3=C(NC3=NNC=C3)N=2)=C1 MWPIZTHMLQBCGZ-UHFFFAOYSA-N 0.000 claims 1
- OBAVDZKJVZNVFX-UHFFFAOYSA-N (3-fluorophenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(O)C=2C=C(F)C=CC=2)=N1 OBAVDZKJVZNVFX-UHFFFAOYSA-N 0.000 claims 1
- RBCVCULSNWELTJ-UHFFFAOYSA-N (4-chloroquinazolin-2-yl)-(3-fluorophenyl)methanone Chemical compound FC1=CC=CC(C(=O)C=2N=C3C=CC=CC3=C(Cl)N=2)=C1 RBCVCULSNWELTJ-UHFFFAOYSA-N 0.000 claims 1
- RNGXYFNCFJJJOW-UHFFFAOYSA-N (4-fluoro-3-hydroxyphenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanone Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(=O)C=2C=C(O)C(F)=CC=2)=N1 RNGXYFNCFJJJOW-UHFFFAOYSA-N 0.000 claims 1
- WKBROLVQJKXPSJ-UHFFFAOYSA-N (4-fluoro-3-methoxyphenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanone Chemical compound C1=C(F)C(OC)=CC(C(=O)C=2N=C3C=CC=CC3=C(NC3=NNC(C)=C3)N=2)=C1 WKBROLVQJKXPSJ-UHFFFAOYSA-N 0.000 claims 1
- YQRUVPUESDISNB-UHFFFAOYSA-N (4-fluorophenyl)-[4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanol Chemical compound N=1C(NC2=NNC=C2)=C2C=CC=CC2=NC=1C(O)C1=CC=C(F)C=C1 YQRUVPUESDISNB-UHFFFAOYSA-N 0.000 claims 1
- JTPFIHSODZOSJS-UHFFFAOYSA-N (4-fluorophenyl)-[4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=NC(NC2=NNC=C2)=C(C=CC=C2)C2=N1 JTPFIHSODZOSJS-UHFFFAOYSA-N 0.000 claims 1
- SFWBOERZDHHBAG-UHFFFAOYSA-N (4-fluorophenyl)-[4-[(3-methoxy-1h-pyrazol-5-yl)amino]quinazolin-2-yl]methanol Chemical compound N1C(OC)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(O)C=2C=CC(F)=CC=2)=N1 SFWBOERZDHHBAG-UHFFFAOYSA-N 0.000 claims 1
- PQCLPDNSOKDOKS-UHFFFAOYSA-N (4-fluorophenyl)-[4-[(3-methoxy-1h-pyrazol-5-yl)amino]quinazolin-2-yl]methanone Chemical compound N1C(OC)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(=O)C=2C=CC(F)=CC=2)=N1 PQCLPDNSOKDOKS-UHFFFAOYSA-N 0.000 claims 1
- UIIWMTOLAIKZED-UHFFFAOYSA-N (4-fluorophenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]-7-(trifluoromethyl)quinazolin-2-yl]methanone Chemical compound N1C(C)=CC(NC=2C3=CC=C(C=C3N=C(N=2)C(=O)C=2C=CC(F)=CC=2)C(F)(F)F)=N1 UIIWMTOLAIKZED-UHFFFAOYSA-N 0.000 claims 1
- WVFVINBDEBXHDC-UHFFFAOYSA-N (4-fluorophenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]-7-piperidin-4-yloxyquinazolin-2-yl]methanol Chemical compound N1C(C)=CC(NC=2C3=CC=C(OC4CCNCC4)C=C3N=C(N=2)C(O)C=2C=CC(F)=CC=2)=N1 WVFVINBDEBXHDC-UHFFFAOYSA-N 0.000 claims 1
- DCRWIATZWHLIPN-UHFFFAOYSA-N (4-fluorophenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(O)C=2C=CC(F)=CC=2)=N1 DCRWIATZWHLIPN-UHFFFAOYSA-N 0.000 claims 1
- OGWVFYOLYMSTEP-UHFFFAOYSA-N (4-fluorophenyl)-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanone Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(=O)C=2C=CC(F)=CC=2)=N1 OGWVFYOLYMSTEP-UHFFFAOYSA-N 0.000 claims 1
- HHHKIALCECKFKO-UHFFFAOYSA-N (4-fluorophenyl)-[6-fluoro-4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanol Chemical compound N=1C(NC2=NNC=C2)=C2C=C(F)C=CC2=NC=1C(O)C1=CC=C(F)C=C1 HHHKIALCECKFKO-UHFFFAOYSA-N 0.000 claims 1
- QGNJFSFVXIVLHZ-UHFFFAOYSA-N (4-fluorophenyl)-[7-(2-methoxyethoxy)-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound N=1C(C(O)C=2C=CC(F)=CC=2)=NC2=CC(OCCOC)=CC=C2C=1NC=1C=C(C)NN=1 QGNJFSFVXIVLHZ-UHFFFAOYSA-N 0.000 claims 1
- DITQZSHEFAYSMO-UHFFFAOYSA-N (4-fluorophenyl)-[7-hydroxy-4-[(5-methyl-1H-pyrazol-3-yl)amino]quinazolin-2-yl]methanone Chemical compound N1C(C)=CC(NC=2C3=CC=C(O)C=C3N=C(N=2)C(=O)C=2C=CC(F)=CC=2)=N1 DITQZSHEFAYSMO-UHFFFAOYSA-N 0.000 claims 1
- SQVBXMYNFQUJRH-UHFFFAOYSA-N (4-fluorophenyl)-[7-iodo-4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanol Chemical compound N=1C(NC2=NNC=C2)=C2C=CC(I)=CC2=NC=1C(O)C1=CC=C(F)C=C1 SQVBXMYNFQUJRH-UHFFFAOYSA-N 0.000 claims 1
- ROHSAMWCRJZMQA-UHFFFAOYSA-N (4-fluorophenyl)-[7-iodo-4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=NC(NC2=NNC=C2)=C(C=CC(I)=C2)C2=N1 ROHSAMWCRJZMQA-UHFFFAOYSA-N 0.000 claims 1
- UPRWKGBNOOHRJA-UHFFFAOYSA-N (4-fluorophenyl)-[7-methoxy-4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanol Chemical compound N=1C(C(O)C=2C=CC(F)=CC=2)=NC2=CC(OC)=CC=C2C=1NC=1C=CNN=1 UPRWKGBNOOHRJA-UHFFFAOYSA-N 0.000 claims 1
- OVACRGMYYKAKQY-UHFFFAOYSA-N (4-fluorophenyl)-[7-methoxy-4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanone Chemical compound N=1C(C(=O)C=2C=CC(F)=CC=2)=NC2=CC(OC)=CC=C2C=1NC=1C=CNN=1 OVACRGMYYKAKQY-UHFFFAOYSA-N 0.000 claims 1
- WGZQRZRIWKCCTJ-UHFFFAOYSA-N (4-fluorophenyl)-[7-methoxy-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound N=1C(C(O)C=2C=CC(F)=CC=2)=NC2=CC(OC)=CC=C2C=1NC=1C=C(C)NN=1 WGZQRZRIWKCCTJ-UHFFFAOYSA-N 0.000 claims 1
- QCDJKUBCYHHJOQ-UHFFFAOYSA-N (4-fluorophenyl)-[7-methoxy-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanone Chemical compound N=1C(C(=O)C=2C=CC(F)=CC=2)=NC2=CC(OC)=CC=C2C=1NC=1C=C(C)NN=1 QCDJKUBCYHHJOQ-UHFFFAOYSA-N 0.000 claims 1
- STYMTGZEUILXLE-UHFFFAOYSA-N (4-fluorophenyl)-[7-methyl-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound N1C(C)=CC(NC=2C3=CC=C(C)C=C3N=C(N=2)C(O)C=2C=CC(F)=CC=2)=N1 STYMTGZEUILXLE-UHFFFAOYSA-N 0.000 claims 1
- QONHGMYSPIRWPW-UHFFFAOYSA-N (4-fluorophenyl)-[7-methyl-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanone Chemical compound N1C(C)=CC(NC=2C3=CC=C(C)C=C3N=C(N=2)C(=O)C=2C=CC(F)=CC=2)=N1 QONHGMYSPIRWPW-UHFFFAOYSA-N 0.000 claims 1
- XQPDWKAYEWFSEZ-UHFFFAOYSA-N (4-fluorophenyl)-[8-methoxy-4-(1h-pyrazol-5-ylamino)quinazolin-2-yl]methanone Chemical compound N1=C(C(=O)C=2C=CC(F)=CC=2)N=C2C(OC)=CC=CC2=C1NC=1C=CNN=1 XQPDWKAYEWFSEZ-UHFFFAOYSA-N 0.000 claims 1
- PJAWNYWCXOYJEO-UHFFFAOYSA-N (4-fluorophenyl)-[8-methyl-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]methanol Chemical compound N1C(C)=CC(NC=2C3=CC=CC(C)=C3N=C(N=2)C(O)C=2C=CC(F)=CC=2)=N1 PJAWNYWCXOYJEO-UHFFFAOYSA-N 0.000 claims 1
- SBHIIJXTBCZPAS-UHFFFAOYSA-N 2-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine Chemical compound CC1=CC(=NN1)C1=NC2=CC=CC=C2C(=N1)N SBHIIJXTBCZPAS-UHFFFAOYSA-N 0.000 claims 1
- AXVRJAHNPYGDTN-UHFFFAOYSA-N 2-[(4-fluorophenyl)-methoxymethyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N=1C(NC2=NNC(C)=C2)=C2C=CC=CC2=NC=1C(OC)C1=CC=C(F)C=C1 AXVRJAHNPYGDTN-UHFFFAOYSA-N 0.000 claims 1
- YDPLCXFVJWEDTQ-UHFFFAOYSA-N 2-[(cyclopropylamino)-(4-fluorophenyl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(NC2CC2)C=2C=CC(F)=CC=2)=N1 YDPLCXFVJWEDTQ-UHFFFAOYSA-N 0.000 claims 1
- ZCLGMXDYLYISFF-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)-2-methylsulfonylethyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(CS(C)(=O)=O)C=2C=CC(F)=CC=2)=N1 ZCLGMXDYLYISFF-UHFFFAOYSA-N 0.000 claims 1
- SPPOVXXZQZOWKR-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C2(OCCO2)C=2C=CC(F)=CC=2)=N1 SPPOVXXZQZOWKR-UHFFFAOYSA-N 0.000 claims 1
- QYDKGHMKDIESLK-UHFFFAOYSA-N 2-[3-amino-1-(4-fluorophenyl)propyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(CCN)C=2C=CC(F)=CC=2)=N1 QYDKGHMKDIESLK-UHFFFAOYSA-N 0.000 claims 1
- HFDBIAWVUBWFSI-UHFFFAOYSA-N 2-[amino-(4-fluorophenyl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(N)C=2C=CC(F)=CC=2)=N1 HFDBIAWVUBWFSI-UHFFFAOYSA-N 0.000 claims 1
- JCCOPWNQYVDVBP-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-7-(ethoxymethyl)-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N=1C(C(F)(F)C=2C=CC(F)=CC=2)=NC2=CC(COCC)=CC=C2C=1NC=1C=C(C)NN=1 JCCOPWNQYVDVBP-UHFFFAOYSA-N 0.000 claims 1
- UUMBEIABKIAYAZ-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-7-fluoro-n-(1h-pyrazol-5-yl)quinazolin-4-amine Chemical compound C1=CC(F)=CC=C1C(F)(F)C1=NC(NC2=NNC=C2)=C(C=CC(F)=C2)C2=N1 UUMBEIABKIAYAZ-UHFFFAOYSA-N 0.000 claims 1
- WAWHJPBPCDUITB-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-7-fluoro-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=C(F)C=C3N=C(N=2)C(F)(F)C=2C=CC(F)=CC=2)=N1 WAWHJPBPCDUITB-UHFFFAOYSA-N 0.000 claims 1
- VPLZCGCBZAHCAW-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-7-methoxy-n-(1h-pyrazol-5-yl)quinazolin-4-amine Chemical compound N=1C(C(F)(F)C=2C=CC(F)=CC=2)=NC2=CC(OC)=CC=C2C=1NC=1C=CNN=1 VPLZCGCBZAHCAW-UHFFFAOYSA-N 0.000 claims 1
- IOQKEIRPQIRFKA-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-7-methyl-n-(1h-pyrazol-5-yl)quinazolin-4-amine Chemical compound N=1C(C(F)(F)C=2C=CC(F)=CC=2)=NC2=CC(C)=CC=C2C=1NC=1C=CNN=1 IOQKEIRPQIRFKA-UHFFFAOYSA-N 0.000 claims 1
- ODNHUUGWUYJVSK-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-7-methyl-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=C(C)C=C3N=C(N=2)C(F)(F)C=2C=CC(F)=CC=2)=N1 ODNHUUGWUYJVSK-UHFFFAOYSA-N 0.000 claims 1
- ULJKQIJZCOWPPT-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-8-fluoro-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(F)=C3N=C(N=2)C(F)(F)C=2C=CC(F)=CC=2)=N1 ULJKQIJZCOWPPT-UHFFFAOYSA-N 0.000 claims 1
- ZXBVDKMUNSPYDV-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-n-(1h-pyrazol-5-yl)quinazolin-4-amine Chemical compound C1=CC(F)=CC=C1C(F)(F)C1=NC(NC2=NNC=C2)=C(C=CC=C2)C2=N1 ZXBVDKMUNSPYDV-UHFFFAOYSA-N 0.000 claims 1
- XOLFTTVBGFSCAC-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)-7-(methylsulfonylmethyl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=C(CS(C)(=O)=O)C=C3N=C(N=2)C(F)(F)C=2C=CC(F)=CC=2)=N1 XOLFTTVBGFSCAC-UHFFFAOYSA-N 0.000 claims 1
- BKEDFHAGAQRGMQ-UHFFFAOYSA-N 2-[difluoro-(4-fluorophenyl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(F)(F)C=2C=CC(F)=CC=2)=N1 BKEDFHAGAQRGMQ-UHFFFAOYSA-N 0.000 claims 1
- INSNIJBXCLHEOP-UHFFFAOYSA-N 2-[fluoro-(4-fluorophenyl)methyl]-n-(1h-pyrazol-5-yl)quinazolin-4-amine Chemical compound N=1C(NC2=NNC=C2)=C2C=CC=CC2=NC=1C(F)C1=CC=C(F)C=C1 INSNIJBXCLHEOP-UHFFFAOYSA-N 0.000 claims 1
- FJOXYCLDYGDGHA-UHFFFAOYSA-N 3-(4-fluorophenyl)-3-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]propanenitrile Chemical compound N1C(C)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(CC#N)C=2C=CC(F)=CC=2)=N1 FJOXYCLDYGDGHA-UHFFFAOYSA-N 0.000 claims 1
- IOVKBTAXXPMNKH-UHFFFAOYSA-N 3-[2-[(4-fluorophenyl)-hydroxymethyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-7-yl]oxypropan-1-ol Chemical compound N1C(C)=CC(NC=2C3=CC=C(OCCCO)C=C3N=C(N=2)C(O)C=2C=CC(F)=CC=2)=N1 IOVKBTAXXPMNKH-UHFFFAOYSA-N 0.000 claims 1
- QPEIZOYLBDRKID-UHFFFAOYSA-N 3-[[2-(4-fluorobenzoyl)quinazolin-4-yl]amino]-1h-pyrazole-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C(=O)C1=NC(NC2=NNC(=C2)C#N)=C(C=CC=C2)C2=N1 QPEIZOYLBDRKID-UHFFFAOYSA-N 0.000 claims 1
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