JP2013538811A5 - - Google Patents
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- Publication number
- JP2013538811A5 JP2013538811A5 JP2013527261A JP2013527261A JP2013538811A5 JP 2013538811 A5 JP2013538811 A5 JP 2013538811A5 JP 2013527261 A JP2013527261 A JP 2013527261A JP 2013527261 A JP2013527261 A JP 2013527261A JP 2013538811 A5 JP2013538811 A5 JP 2013538811A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- difluoro
- fluoropyridin
- pyrazol
- 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 65
- 125000005843 halogen group Chemical group 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 239000001257 hydrogen Substances 0.000 claims 31
- 125000001188 haloalkyl group Chemical group 0.000 claims 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000003545 alkoxy group Chemical group 0.000 claims 23
- 125000003342 alkenyl group Chemical group 0.000 claims 21
- 125000000304 alkynyl group Chemical group 0.000 claims 21
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- -1 deutero Chemical group 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 102000042838 JAK family Human genes 0.000 claims 3
- 108091082332 JAK family Proteins 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 230000001105 regulatory effect Effects 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- MCPUGZZCUANBFN-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)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=2N=CC(F)=CC=2)=N1 MCPUGZZCUANBFN-UHFFFAOYSA-N 0.000 claims 2
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 2
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- WJSZYWGOYIGLGU-UHFFFAOYSA-N (5-fluoropyridin-2-yl)-[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=2N=CC(F)=CC=2)=N1 WJSZYWGOYIGLGU-UHFFFAOYSA-N 0.000 claims 1
- XSAGVFXKVFDMTD-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-8-ol Chemical compound N1C(C)=CC(NC=2C3=CC=CC(O)=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 XSAGVFXKVFDMTD-UHFFFAOYSA-N 0.000 claims 1
- AKQURCCBNQDETN-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazoline-7-carbonitrile Chemical compound N1C(C)=CC(NC=2C3=CC=C(C=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)C#N)=N1 AKQURCCBNQDETN-UHFFFAOYSA-N 0.000 claims 1
- NTKQWKUTRQTFHU-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazoline-7-carboxamide Chemical compound N1C(C)=CC(NC=2C3=CC=C(C=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)C(N)=O)=N1 NTKQWKUTRQTFHU-UHFFFAOYSA-N 0.000 claims 1
- GRAFFBOCVCOJFB-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazoline-8-carbonitrile Chemical compound N1C(C)=CC(NC=2C3=CC=CC(=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)C#N)=N1 GRAFFBOCVCOJFB-UHFFFAOYSA-N 0.000 claims 1
- AFBDKDHZBJKSKU-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazoline-8-carboxamide Chemical compound N1C(C)=CC(NC=2C3=CC=CC(=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)C(N)=O)=N1 AFBDKDHZBJKSKU-UHFFFAOYSA-N 0.000 claims 1
- AZYCUZXYDSPFPA-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazoline-8-carboxylic acid Chemical compound N1C(C)=CC(NC=2C3=CC=CC(=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)C(O)=O)=N1 AZYCUZXYDSPFPA-UHFFFAOYSA-N 0.000 claims 1
- OYMYXSBBFUQPIL-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-n-(5-methyl-1h-pyrazol-3-yl)quinazoline-4,8-diamine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(N)=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 OYMYXSBBFUQPIL-UHFFFAOYSA-N 0.000 claims 1
- RCFRWCSGGDOFJU-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)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=2N=CC(F)=CC=2)=N1 RCFRWCSGGDOFJU-UHFFFAOYSA-N 0.000 claims 1
- GKEWJWUPVPYMLI-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-7-methoxy-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N=1C(C(F)(F)C=2N=CC(F)=CC=2)=NC2=CC(OC)=CC=C2C=1NC=1C=C(C)NN=1 GKEWJWUPVPYMLI-UHFFFAOYSA-N 0.000 claims 1
- OXJGKGUEVPDQCU-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)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=2N=CC(F)=CC=2)=N1 OXJGKGUEVPDQCU-UHFFFAOYSA-N 0.000 claims 1
- GRGVDWYUVCSJMX-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-8-ethyl-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1=C(C(F)(F)C=2N=CC(F)=CC=2)N=C2C(CC)=CC=CC2=C1NC=1C=C(C)NN=1 GRGVDWYUVCSJMX-UHFFFAOYSA-N 0.000 claims 1
- WQLBBCBDQAJOOC-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-8-fluoro-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1N=C(C)C=C1NC1=NC(C(F)(F)C=2N=CC(F)=CC=2)=NC2=C(F)C=CC=C12 WQLBBCBDQAJOOC-UHFFFAOYSA-N 0.000 claims 1
- IZHLPEWWMLJSNT-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-8-methoxy-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1=C(C(F)(F)C=2N=CC(F)=CC=2)N=C2C(OC)=CC=CC2=C1NC=1C=C(C)NN=1 IZHLPEWWMLJSNT-UHFFFAOYSA-N 0.000 claims 1
- VUVSRGDNNDBVMC-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-8-methyl-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(C)=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 VUVSRGDNNDBVMC-UHFFFAOYSA-N 0.000 claims 1
- OFSKVQPOFGIYDU-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(1h-1,2,4-triazol-5-yl)quinazolin-4-amine Chemical compound N1=CC(F)=CC=C1C(F)(F)C1=NC(NC2=NNC=N2)=C(C=CC=C2)C2=N1 OFSKVQPOFGIYDU-UHFFFAOYSA-N 0.000 claims 1
- VENZULZJTMPHNG-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(1h-pyrazol-5-yl)quinazolin-4-amine Chemical compound N1=CC(F)=CC=C1C(F)(F)C1=NC(NC2=NNC=C2)=C(C=CC=C2)C2=N1 VENZULZJTMPHNG-UHFFFAOYSA-N 0.000 claims 1
- LHLIXVZUNHDMSG-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(3-methoxy-1h-pyrazol-5-yl)quinazolin-4-amine Chemical compound N1C(OC)=CC(NC=2C3=CC=CC=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 LHLIXVZUNHDMSG-UHFFFAOYSA-N 0.000 claims 1
- HCSAVAZCQDKKPA-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)-7-methylsulfonylquinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=C(C=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)S(C)(=O)=O)=N1 HCSAVAZCQDKKPA-UHFFFAOYSA-N 0.000 claims 1
- DIGAICBRKCJUKN-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)-8-(trifluoromethoxy)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(OC(F)(F)F)=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 DIGAICBRKCJUKN-UHFFFAOYSA-N 0.000 claims 1
- XGQRMNKMJMRGFH-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)-8-(trifluoromethyl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)C(F)(F)F)=N1 XGQRMNKMJMRGFH-UHFFFAOYSA-N 0.000 claims 1
- UZAWFVAJUIRMHB-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)-8-methylsulfonylquinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)S(C)(=O)=O)=N1 UZAWFVAJUIRMHB-UHFFFAOYSA-N 0.000 claims 1
- QIQBBKOUAZIQLI-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)-8-nitroquinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)[N+]([O-])=O)=N1 QIQBBKOUAZIQLI-UHFFFAOYSA-N 0.000 claims 1
- OUKOVJNIVQXTTO-UHFFFAOYSA-N 2-[difluoro-(5-fluoropyrimidin-2-yl)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=2N=CC(F)=CN=2)=N1 OUKOVJNIVQXTTO-UHFFFAOYSA-N 0.000 claims 1
- ITGPPFYDRDMILH-UHFFFAOYSA-N 4-[2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-8-yl]morpholin-3-one Chemical compound N1C(C)=CC(NC=2C3=CC=CC(=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)N2C(COCC2)=O)=N1 ITGPPFYDRDMILH-UHFFFAOYSA-N 0.000 claims 1
- VEZOFKZEICNRLT-UHFFFAOYSA-N 7-bromo-2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=C(Br)C=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 VEZOFKZEICNRLT-UHFFFAOYSA-N 0.000 claims 1
- VCGNNBOHYVSYGP-UHFFFAOYSA-N 7-chloro-2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=C(Cl)C=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 VCGNNBOHYVSYGP-UHFFFAOYSA-N 0.000 claims 1
- KPLWMQFXJQFKCV-UHFFFAOYSA-N 7-cyclopropyl-2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=C(C=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)C2CC2)=N1 KPLWMQFXJQFKCV-UHFFFAOYSA-N 0.000 claims 1
- OTIYGQSDZBIJOQ-UHFFFAOYSA-N 8-bromo-2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(Br)=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 OTIYGQSDZBIJOQ-UHFFFAOYSA-N 0.000 claims 1
- RXZIVJQQEIEMRY-UHFFFAOYSA-N 8-chloro-2-[difluoro-(5-fluoropyridin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(Cl)=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 RXZIVJQQEIEMRY-UHFFFAOYSA-N 0.000 claims 1
- AVYNZYUHAHIQFN-UHFFFAOYSA-N 8-chloro-2-[difluoro-(5-fluoropyrimidin-2-yl)methyl]-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1C(C)=CC(NC=2C3=CC=CC(Cl)=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CN=2)=N1 AVYNZYUHAHIQFN-UHFFFAOYSA-N 0.000 claims 1
- GEADPOFVBCFLNQ-UHFFFAOYSA-N 8-cyclopropyl-2-[difluoro-(5-fluoropyridin-2-yl)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=2N=CC(F)=CC=2)C2CC2)=N1 GEADPOFVBCFLNQ-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 1
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000003943 azolyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005345 deuteroalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000003106 haloaryl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 230000001861 immunosuppressant effect Effects 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RVRNEQGLBYKMIT-UHFFFAOYSA-N methyl 2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazoline-8-carboxylate Chemical compound N1=C(C(F)(F)C=2N=CC(F)=CC=2)N=C2C(C(=O)OC)=CC=CC2=C1NC=1C=C(C)NN=1 RVRNEQGLBYKMIT-UHFFFAOYSA-N 0.000 claims 1
- QKGQVICNBSLZRB-UHFFFAOYSA-N n-[2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-8-yl]acetamide Chemical compound N1=C(C(F)(F)C=2N=CC(F)=CC=2)N=C2C(NC(=O)C)=CC=CC2=C1NC=1C=C(C)NN=1 QKGQVICNBSLZRB-UHFFFAOYSA-N 0.000 claims 1
- WUCMBDFBFRKMIA-UHFFFAOYSA-N n-[2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-8-yl]formamide Chemical compound N1C(C)=CC(NC=2C3=CC=CC(NC=O)=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 WUCMBDFBFRKMIA-UHFFFAOYSA-N 0.000 claims 1
- PDHQHMTWSXHWJT-UHFFFAOYSA-N n-[2-[difluoro-(5-fluoropyridin-2-yl)methyl]-4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-8-yl]methanesulfonamide Chemical compound N1C(C)=CC(NC=2C3=CC=CC(NS(C)(=O)=O)=C3N=C(N=2)C(F)(F)C=2N=CC(F)=CC=2)=N1 PDHQHMTWSXHWJT-UHFFFAOYSA-N 0.000 claims 1
- AOXNIUAQZPKOSC-UHFFFAOYSA-N n-[2-[difluoro-(5-fluoropyridin-2-yl)methyl]quinazolin-4-yl]-5-methyl-1,3-thiazol-2-amine Chemical compound S1C(C)=CN=C1NC1=NC(C(F)(F)C=2N=CC(F)=CC=2)=NC2=CC=CC=C12 AOXNIUAQZPKOSC-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 0 CN(C1N(*)c2n[n](*)c(*)c2)C(C(*)(*)C(*)=*IC=CC=C)=Nc2c1cccc2 Chemical compound CN(C1N(*)c2n[n](*)c(*)c2)C(C(*)(*)C(*)=*IC=CC=C)=Nc2c1cccc2 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37930910P | 2010-09-01 | 2010-09-01 | |
| US61/379,309 | 2010-09-01 | ||
| PCT/US2011/049950 WO2012030948A1 (en) | 2010-09-01 | 2011-08-31 | Quinazoline compounds and methods of use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013538811A JP2013538811A (ja) | 2013-10-17 |
| JP2013538811A5 true JP2013538811A5 (enExample) | 2014-10-09 |
| JP5901634B2 JP5901634B2 (ja) | 2016-04-13 |
Family
ID=44645826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013527261A Expired - Fee Related JP5901634B2 (ja) | 2010-09-01 | 2011-08-31 | キナゾリン化合物及びその使用方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8633207B2 (enExample) |
| EP (1) | EP2611789A1 (enExample) |
| JP (1) | JP5901634B2 (enExample) |
| KR (1) | KR20130102060A (enExample) |
| CN (1) | CN103298805A (enExample) |
| AU (1) | AU2011296024B2 (enExample) |
| CA (1) | CA2810024A1 (enExample) |
| MX (1) | MX2013002384A (enExample) |
| WO (1) | WO2012030948A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013135674A1 (en) * | 2012-03-12 | 2013-09-19 | Syngenta Participations Ag | Insecticidal 2-aryl-acetamide compounds |
| CN103301133B (zh) * | 2012-12-11 | 2014-09-17 | 中国药科大学 | 一类氨基喹唑啉表皮生长因子受体拮抗剂的抗肿瘤治疗用途 |
| WO2016049532A1 (en) | 2014-09-26 | 2016-03-31 | Unitract Syringe Pty Ltd | Sequential chamber drug delivery pumps for drug mixing and delivery |
| JP2018135268A (ja) * | 2015-06-05 | 2018-08-30 | 大日本住友製薬株式会社 | 新規ヘテロアリールアミノ−３−ピラゾール誘導体およびその薬理学上許容される塩 |
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- 2011-08-31 JP JP2013527261A patent/JP5901634B2/ja not_active Expired - Fee Related
- 2011-08-31 KR KR1020137007907A patent/KR20130102060A/ko not_active Ceased
- 2011-08-31 MX MX2013002384A patent/MX2013002384A/es not_active Application Discontinuation
- 2011-08-31 CN CN2011800527654A patent/CN103298805A/zh active Pending
- 2011-08-31 WO PCT/US2011/049950 patent/WO2012030948A1/en not_active Ceased
- 2011-08-31 AU AU2011296024A patent/AU2011296024B2/en not_active Ceased
- 2011-08-31 CA CA2810024A patent/CA2810024A1/en not_active Abandoned
- 2011-08-31 US US13/222,937 patent/US8633207B2/en not_active Expired - Fee Related
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