CA2779989A1 - Quinazoline compounds - Google Patents
Quinazoline compounds Download PDFInfo
- Publication number
- CA2779989A1 CA2779989A1 CA2779989A CA2779989A CA2779989A1 CA 2779989 A1 CA2779989 A1 CA 2779989A1 CA 2779989 A CA2779989 A CA 2779989A CA 2779989 A CA2779989 A CA 2779989A CA 2779989 A1 CA2779989 A1 CA 2779989A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- methyl
- quinazolinyl
- methyloxy
- alkyl
- 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.)
- Abandoned
Links
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 238000000034 method Methods 0.000 claims abstract description 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 230
- -1 nitro, amino Chemical group 0.000 claims description 172
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 77
- 229910052736 halogen Inorganic materials 0.000 claims description 59
- 150000002367 halogens Chemical class 0.000 claims description 59
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 49
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 229910052717 sulfur Chemical group 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 206010019280 Heart failures Diseases 0.000 claims description 27
- 125000003282 alkyl amino group Chemical group 0.000 claims description 25
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 22
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000003386 piperidinyl group Chemical group 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 16
- 125000002757 morpholinyl group Chemical group 0.000 claims description 16
- 239000001301 oxygen Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 239000011593 sulfur Chemical group 0.000 claims description 13
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 12
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 11
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
- 101000662993 Homo sapiens Serine/threonine-protein kinase TNNI3K Proteins 0.000 claims description 7
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- OQHRVARQAYXXKB-UHFFFAOYSA-N 3-[(6-aminoquinazolin-4-yl)amino]-4-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2C3=CC(N)=CC=C3N=CN=2)=C1 OQHRVARQAYXXKB-UHFFFAOYSA-N 0.000 claims description 5
- 102100037670 Serine/threonine-protein kinase TNNI3K Human genes 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 4
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- IAWACGQFSRGVHG-UHFFFAOYSA-N 3-[(5,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2C3=C(OC)C=C(OC)C=C3N=CN=2)=C1 IAWACGQFSRGVHG-UHFFFAOYSA-N 0.000 claims description 3
- YUSROMRPOFFTMX-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-4-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 YUSROMRPOFFTMX-UHFFFAOYSA-N 0.000 claims description 3
- PNEYRCXCZRJLTK-UHFFFAOYSA-N 3-[(6-methoxy-7-propan-2-yloxyquinazolin-4-yl)amino]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(NC=2C3=CC(OC)=C(OC(C)C)C=C3N=CN=2)=C1 PNEYRCXCZRJLTK-UHFFFAOYSA-N 0.000 claims description 3
- TUINBAPNAKPWHO-UHFFFAOYSA-N 3-[[7-(3-methoxypropoxy)quinazolin-4-yl]amino]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(NC=2C3=CC=C(OCCCOC)C=C3N=CN=2)=C1 TUINBAPNAKPWHO-UHFFFAOYSA-N 0.000 claims description 3
- XBOGVIDEPXMHTN-UHFFFAOYSA-N 4-(dimethylamino)-3-[[6-(dimethylamino)quinazolin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2C3=CC(=CC=C3N=CN=2)N(C)C)=C1 XBOGVIDEPXMHTN-UHFFFAOYSA-N 0.000 claims description 3
- HSXXPAFGNVISQH-UHFFFAOYSA-N 4-(dimethylamino)-n-methyl-3-[[6-(methylamino)quinazolin-4-yl]amino]benzenesulfonamide Chemical compound C12=CC(NC)=CC=C2N=CN=C1NC1=CC(S(=O)(=O)NC)=CC=C1N(C)C HSXXPAFGNVISQH-UHFFFAOYSA-N 0.000 claims description 3
- YIHUHJGDULXMLF-UHFFFAOYSA-N 2-fluoro-n-methyl-4-(2,2,2-trifluoroethoxy)-5-[(5,6,7-trimethoxyquinazolin-4-yl)amino]benzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)NC)=CC(NC=2C3=C(OC)C(OC)=C(OC)C=C3N=CN=2)=C1OCC(F)(F)F YIHUHJGDULXMLF-UHFFFAOYSA-N 0.000 claims description 2
- JHLYWKKKYYQEPH-UHFFFAOYSA-N 3-(7,8-dihydro-[1,4]dioxino[2,3-g]quinazolin-4-ylamino)-4-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2C3=CC=4OCCOC=4C=C3N=CN=2)=C1 JHLYWKKKYYQEPH-UHFFFAOYSA-N 0.000 claims description 2
- KFBXNJYHMZCVDH-UHFFFAOYSA-N 3-[(5,7-dimethoxyquinazolin-4-yl)amino]-4-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2C3=C(OC)C=C(OC)C=C3N=CN=2)=C1 KFBXNJYHMZCVDH-UHFFFAOYSA-N 0.000 claims description 2
- RJSKVBNUBJSMHI-UHFFFAOYSA-N 3-[(5,7-dimethoxyquinazolin-4-yl)amino]-4-fluoro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(F)C(NC=2C3=C(OC)C=C(OC)C=C3N=CN=2)=C1 RJSKVBNUBJSMHI-UHFFFAOYSA-N 0.000 claims description 2
- DUKKDKHUSSZCIU-UHFFFAOYSA-N 3-[(5,7-dimethoxyquinazolin-4-yl)amino]-4-methoxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC)C(NC=2C3=C(OC)C=C(OC)C=C3N=CN=2)=C1 DUKKDKHUSSZCIU-UHFFFAOYSA-N 0.000 claims description 2
- CUEQUMNPZOWSNT-UHFFFAOYSA-N 3-[(5,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-[methyl(2,2,2-trifluoroethyl)amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)CC(F)(F)F)C(NC=2C3=C(OC)C=C(OC)C=C3N=CN=2)=C1 CUEQUMNPZOWSNT-UHFFFAOYSA-N 0.000 claims description 2
- YZXJNXXOESJUDW-UHFFFAOYSA-N 3-[(5,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-methylsulfonylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C(NC=2C3=C(OC)C=C(OC)C=C3N=CN=2)=C1 YZXJNXXOESJUDW-UHFFFAOYSA-N 0.000 claims description 2
- OBQJMFWNEPIQKM-UHFFFAOYSA-N 3-[(5,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-morpholin-4-ylbenzenesulfonamide Chemical compound N=1C=NC2=CC(OC)=CC(OC)=C2C=1NC1=CC(S(=O)(=O)NC)=CC=C1N1CCOCC1 OBQJMFWNEPIQKM-UHFFFAOYSA-N 0.000 claims description 2
- DNRQPIJNEGGAAA-UHFFFAOYSA-N 3-[(5,7-dimethoxyquinazolin-4-yl)amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2C3=C(OC)C=C(OC)C=C3N=CN=2)=C1 DNRQPIJNEGGAAA-UHFFFAOYSA-N 0.000 claims description 2
- WSNMNKYBSOWHFZ-UHFFFAOYSA-N 3-[(5-chloro-6,7-dimethoxyquinazolin-4-yl)amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2C3=C(Cl)C(OC)=C(OC)C=C3N=CN=2)=C1 WSNMNKYBSOWHFZ-UHFFFAOYSA-N 0.000 claims description 2
- OBHNJQYLPQMMJS-UHFFFAOYSA-N 3-[(5-ethoxy-7-methoxyquinazolin-4-yl)amino]-n-methyl-4-(1,1,1-trifluoropropan-2-yloxy)benzenesulfonamide Chemical compound C=12C(OCC)=CC(OC)=CC2=NC=NC=1NC1=CC(S(=O)(=O)NC)=CC=C1OC(C)C(F)(F)F OBHNJQYLPQMMJS-UHFFFAOYSA-N 0.000 claims description 2
- SLWXWVRNVKDGNM-UHFFFAOYSA-N 3-[(5-ethoxy-7-methoxyquinazolin-4-yl)amino]-n-methyl-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C=12C(OCC)=CC(OC)=CC2=NC=NC=1NC1=CC(S(=O)(=O)NC)=CC=C1OC(F)(F)F SLWXWVRNVKDGNM-UHFFFAOYSA-N 0.000 claims description 2
- OLSJRINRIBWJFA-UHFFFAOYSA-N 3-[(6,7-diethoxyquinazolin-4-yl)amino]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=NC=1NC1=CC(S(=O)(=O)NC)=CC=C1OCC(F)(F)F OLSJRINRIBWJFA-UHFFFAOYSA-N 0.000 claims description 2
- MVOYMLQGDVPZJA-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-4-[ethyl(methyl)amino]-n-methylbenzenesulfonamide Chemical compound CCN(C)C1=CC=C(S(=O)(=O)NC)C=C1NC1=NC=NC2=CC(OC)=C(OC)C=C12 MVOYMLQGDVPZJA-UHFFFAOYSA-N 0.000 claims description 2
- TUSITRBRNZHFMX-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-4-methoxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC)C(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 TUSITRBRNZHFMX-UHFFFAOYSA-N 0.000 claims description 2
- JQQPJAQDAUBSJJ-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-(1,1,1-trifluoropropan-2-yloxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(C)C(F)(F)F)C(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 JQQPJAQDAUBSJJ-UHFFFAOYSA-N 0.000 claims description 2
- QWUCNVDERBNALL-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-(2,2,2-trifluoroethylsulfanyl)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SCC(F)(F)F)C(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 QWUCNVDERBNALL-UHFFFAOYSA-N 0.000 claims description 2
- KYOYDUMRZOHKKQ-HXUWFJFHSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-[(2r)-2-(trifluoromethyl)pyrrolidin-1-yl]benzenesulfonamide Chemical compound N=1C=NC2=CC(OC)=C(OC)C=C2C=1NC1=CC(S(=O)(=O)NC)=CC=C1N1CCC[C@@H]1C(F)(F)F KYOYDUMRZOHKKQ-HXUWFJFHSA-N 0.000 claims description 2
- FHMGNHOMVMUVSO-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-[methyl(2,2,2-trifluoroethyl)amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)CC(F)(F)F)C(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 FHMGNHOMVMUVSO-UHFFFAOYSA-N 0.000 claims description 2
- DMNHYDHDZWJZMB-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 DMNHYDHDZWJZMB-UHFFFAOYSA-N 0.000 claims description 2
- LMHKYZSAOCJQOU-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-methylsulfonylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 LMHKYZSAOCJQOU-UHFFFAOYSA-N 0.000 claims description 2
- LNRBCVJBFACPLQ-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-morpholin-4-ylbenzenesulfonamide Chemical compound N=1C=NC2=CC(OC)=C(OC)C=C2C=1NC1=CC(S(=O)(=O)NC)=CC=C1N1CCOCC1 LNRBCVJBFACPLQ-UHFFFAOYSA-N 0.000 claims description 2
- PAZABHJZVINCPU-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-piperidin-1-ylbenzenesulfonamide Chemical compound N=1C=NC2=CC(OC)=C(OC)C=C2C=1NC1=CC(S(=O)(=O)NC)=CC=C1N1CCCCC1 PAZABHJZVINCPU-UHFFFAOYSA-N 0.000 claims description 2
- CZTAUKHLISFCPJ-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methyl-4-propan-2-yloxybenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(C)C)C(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 CZTAUKHLISFCPJ-UHFFFAOYSA-N 0.000 claims description 2
- HJWJQWGYZYLMGV-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2C3=CC(OC)=C(OC)C=C3N=CN=2)=C1 HJWJQWGYZYLMGV-UHFFFAOYSA-N 0.000 claims description 2
- BWUYSVPJNQGHBZ-GOSISDBHSA-N 3-[(6-chloroquinazolin-4-yl)amino]-n-methyl-4-[(2r)-2-(trifluoromethyl)pyrrolidin-1-yl]benzenesulfonamide Chemical compound N=1C=NC2=CC=C(Cl)C=C2C=1NC1=CC(S(=O)(=O)NC)=CC=C1N1CCC[C@@H]1C(F)(F)F BWUYSVPJNQGHBZ-GOSISDBHSA-N 0.000 claims description 2
- WNFCKMNVCNNTHE-UHFFFAOYSA-N 3-[(6-chloroquinazolin-4-yl)amino]-n-methyl-4-piperidin-1-ylbenzenesulfonamide Chemical compound N=1C=NC2=CC=C(Cl)C=C2C=1NC1=CC(S(=O)(=O)NC)=CC=C1N1CCCCC1 WNFCKMNVCNNTHE-UHFFFAOYSA-N 0.000 claims description 2
- NZGQZHSAVLWQJD-UHFFFAOYSA-N 3-[(6-iodo-7-methoxyquinazolin-4-yl)amino]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(NC=2C3=CC(I)=C(OC)C=C3N=CN=2)=C1 NZGQZHSAVLWQJD-UHFFFAOYSA-N 0.000 claims description 2
- LVRXFIZRHGNOHR-UHFFFAOYSA-N 3-[(7-aminoquinazolin-4-yl)amino]-4-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2C3=CC=C(N)C=C3N=CN=2)=C1 LVRXFIZRHGNOHR-UHFFFAOYSA-N 0.000 claims description 2
- SWLMPOQQJCLDHU-UHFFFAOYSA-N 3-[(7-hydroxy-6-methoxyquinazolin-4-yl)amino]-N-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(NC=2C3=CC(OC)=C(O)C=C3N=CN=2)=C1 SWLMPOQQJCLDHU-UHFFFAOYSA-N 0.000 claims description 2
- POKHOZHYJRLTBV-UHFFFAOYSA-N 3-[(7-methoxy-5-propan-2-yloxyquinazolin-4-yl)amino]-n-methyl-4-(1,1,1-trifluoropropan-2-yloxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(C)C(F)(F)F)C(NC=2C3=C(OC(C)C)C=C(OC)C=C3N=CN=2)=C1 POKHOZHYJRLTBV-UHFFFAOYSA-N 0.000 claims description 2
- UBPZKGHCYGZUKO-UHFFFAOYSA-N 3-[(7-methoxy-5-propan-2-yloxyquinazolin-4-yl)amino]-n-methyl-4-(trifluoromethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(F)(F)F)C(NC=2C3=C(OC(C)C)C=C(OC)C=C3N=CN=2)=C1 UBPZKGHCYGZUKO-UHFFFAOYSA-N 0.000 claims description 2
- DUTAWJOHYORMCO-UHFFFAOYSA-N 3-[[7-(3-chloropropoxy)quinazolin-4-yl]amino]-4-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2C3=CC=C(OCCCCl)C=C3N=CN=2)=C1 DUTAWJOHYORMCO-UHFFFAOYSA-N 0.000 claims description 2
- UIBXYETWZDSJHG-UHFFFAOYSA-N 3-[[7-(3-chloropropoxy)quinazolin-4-yl]amino]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(NC=2C3=CC=C(OCCCCl)C=C3N=CN=2)=C1 UIBXYETWZDSJHG-UHFFFAOYSA-N 0.000 claims description 2
- KQJGPSROODLVCR-UHFFFAOYSA-N 3-[[7-methoxy-5-(oxan-4-yloxy)quinazolin-4-yl]amino]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(NC=2C3=C(OC4CCOCC4)C=C(OC)C=C3N=CN=2)=C1 KQJGPSROODLVCR-UHFFFAOYSA-N 0.000 claims description 2
- DETZHDXVQPOGQN-UHFFFAOYSA-N 4-(4,4-difluoropiperidin-1-yl)-3-[(6,7-dimethoxyquinazolin-4-yl)amino]-n-methylbenzenesulfonamide Chemical compound N=1C=NC2=CC(OC)=C(OC)C=C2C=1NC1=CC(S(=O)(=O)NC)=CC=C1N1CCC(F)(F)CC1 DETZHDXVQPOGQN-UHFFFAOYSA-N 0.000 claims description 2
- IYTSEGRKCOLUOI-UHFFFAOYSA-N 4-(dimethylamino)-3-[[7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2C3=CC(OCCCN4CCOCC4)=C(OC)C=C3N=CN=2)=C1 IYTSEGRKCOLUOI-UHFFFAOYSA-N 0.000 claims description 2
- GXUZZZRWJPJLHA-UHFFFAOYSA-N 4-(dimethylamino)-n-methyl-3-(quinazolin-4-ylamino)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2C3=CC=CC=C3N=CN=2)=C1 GXUZZZRWJPJLHA-UHFFFAOYSA-N 0.000 claims description 2
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- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
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- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
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- FIQOFIRCTOWDOW-BJLQDIEVSA-N temocapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C[C@H](SC1)C=1SC=CC=1)=O)CC1=CC=CC=C1 FIQOFIRCTOWDOW-BJLQDIEVSA-N 0.000 description 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- PHCBRBWANGJMHS-UHFFFAOYSA-J tetrasodium;disulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PHCBRBWANGJMHS-UHFFFAOYSA-J 0.000 description 1
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- BAVYZALUXZFZLV-FIBGUPNXSA-N trideuteriomethanamine Chemical compound [2H]C([2H])([2H])N BAVYZALUXZFZLV-FIBGUPNXSA-N 0.000 description 1
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25764609P | 2009-11-03 | 2009-11-03 | |
| US61/257,646 | 2009-11-03 | ||
| PCT/US2010/054927 WO2011056740A1 (en) | 2009-11-03 | 2010-11-01 | Quinazoline compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2779989A1 true CA2779989A1 (en) | 2011-05-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2779989A Abandoned CA2779989A1 (en) | 2009-11-03 | 2010-11-01 | Quinazoline compounds |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8859571B2 (enExample) |
| EP (1) | EP2501233B1 (enExample) |
| JP (1) | JP5836963B2 (enExample) |
| KR (1) | KR101736521B1 (enExample) |
| CN (1) | CN102711474B (enExample) |
| AU (1) | AU2010315361B2 (enExample) |
| BR (1) | BR112012010524A2 (enExample) |
| CA (1) | CA2779989A1 (enExample) |
| EA (1) | EA021439B1 (enExample) |
| ES (1) | ES2523465T3 (enExample) |
| IL (1) | IL219504A (enExample) |
| MX (1) | MX2012005155A (enExample) |
| WO (1) | WO2011056740A1 (enExample) |
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| US8569316B2 (en) * | 2009-02-17 | 2013-10-29 | Boehringer Ingelheim International Gmbh | Pyrimido [5,4-D] pyrimidine derivatives for the inhibition of tyrosine kinases |
| CN103159685A (zh) * | 2013-04-11 | 2013-06-19 | 苏州立新制药有限公司 | 4-氯-6，7-二(2-甲氧基乙氧基)喹唑啉的制备方法 |
| CN105916506B (zh) * | 2013-11-20 | 2020-01-07 | 圣诺康生命科学公司 | 作为tam家族激酶抑制剂的喹唑啉衍生物 |
| JP6386562B2 (ja) | 2013-12-26 | 2018-09-05 | エクソンモービル リサーチ アンド エンジニアリング カンパニーＥｘｘｏｎ Ｒｅｓｅａｒｃｈ Ａｎｄ Ｅｎｇｉｎｅｅｒｉｎｇ Ｃｏｍｐａｎｙ | Ｚｓｍ−４８結晶の合成 |
| US20200290978A1 (en) * | 2017-09-26 | 2020-09-17 | The Regents Of The University Of California | Compositions and methods for treating cancer |
| CN114521196A (zh) | 2019-09-16 | 2022-05-20 | 诺华股份有限公司 | 双官能团降解剂及其使用方法 |
| EP4405360A4 (en) | 2021-09-23 | 2025-08-20 | Erasca Inc | POLYMORPHIC FORMS OF EGFR INHIBITOR |
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|---|---|---|---|---|
| GB9508565D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quiazoline derivative |
| CA2744997A1 (en) * | 2003-09-26 | 2005-04-07 | Exelixis, Inc. | C-met modulators and method of use |
| US7528143B2 (en) * | 2005-11-01 | 2009-05-05 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
-
2010
- 2010-11-01 EP EP10828947.1A patent/EP2501233B1/en active Active
- 2010-11-01 KR KR1020127014231A patent/KR101736521B1/ko not_active Expired - Fee Related
- 2010-11-01 AU AU2010315361A patent/AU2010315361B2/en not_active Ceased
- 2010-11-01 US US13/505,324 patent/US8859571B2/en not_active Expired - Fee Related
- 2010-11-01 ES ES10828947.1T patent/ES2523465T3/es active Active
- 2010-11-01 MX MX2012005155A patent/MX2012005155A/es active IP Right Grant
- 2010-11-01 JP JP2012537925A patent/JP5836963B2/ja not_active Expired - Fee Related
- 2010-11-01 CA CA2779989A patent/CA2779989A1/en not_active Abandoned
- 2010-11-01 CN CN201080060451.4A patent/CN102711474B/zh not_active Expired - Fee Related
- 2010-11-01 BR BR112012010524A patent/BR112012010524A2/pt not_active IP Right Cessation
- 2010-11-01 EA EA201290243A patent/EA021439B1/ru not_active IP Right Cessation
- 2010-11-01 WO PCT/US2010/054927 patent/WO2011056740A1/en not_active Ceased
-
2012
- 2012-04-30 IL IL219504A patent/IL219504A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2523465T3 (es) | 2014-11-26 |
| IL219504A (en) | 2016-09-29 |
| EP2501233A1 (en) | 2012-09-26 |
| KR101736521B1 (ko) | 2017-05-16 |
| EP2501233A4 (en) | 2013-06-19 |
| KR20120112441A (ko) | 2012-10-11 |
| IL219504A0 (en) | 2012-06-28 |
| EA021439B1 (ru) | 2015-06-30 |
| EP2501233B1 (en) | 2014-09-24 |
| US8859571B2 (en) | 2014-10-14 |
| JP2013510155A (ja) | 2013-03-21 |
| CN102711474A (zh) | 2012-10-03 |
| EA201290243A1 (ru) | 2012-12-28 |
| AU2010315361A1 (en) | 2012-05-24 |
| WO2011056740A1 (en) | 2011-05-12 |
| MX2012005155A (es) | 2012-08-31 |
| JP5836963B2 (ja) | 2015-12-24 |
| US20120220588A1 (en) | 2012-08-30 |
| CN102711474B (zh) | 2014-09-10 |
| AU2010315361B2 (en) | 2014-06-12 |
| BR112012010524A2 (pt) | 2017-12-12 |
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| EEER | Examination request |
Effective date: 20150916 |
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| FZDE | Discontinued |
Effective date: 20190517 |