JP2012517470A5 - - Google Patents
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- Publication number
- JP2012517470A5 JP2012517470A5 JP2011550122A JP2011550122A JP2012517470A5 JP 2012517470 A5 JP2012517470 A5 JP 2012517470A5 JP 2011550122 A JP2011550122 A JP 2011550122A JP 2011550122 A JP2011550122 A JP 2011550122A JP 2012517470 A5 JP2012517470 A5 JP 2012517470A5
- Authority
- JP
- Japan
- Prior art keywords
- quinazoline
- carboxylic acid
- phenyl
- acid amide
- ethylamino
- 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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- -1 methoxy, ethoxy Chemical group 0.000 claims 38
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 7
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- UFMCGKYLIYMLOY-CQSZACIVSA-N 4-[[(1s)-2-amino-1-phenylethyl]amino]quinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)CN)=CC=CC=C1 UFMCGKYLIYMLOY-CQSZACIVSA-N 0.000 claims 2
- UALHJBCHHRMERK-UHFFFAOYSA-N 4-[[2-amino-1-(3,4-dichlorophenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN)C1=CC=C(Cl)C(Cl)=C1 UALHJBCHHRMERK-UHFFFAOYSA-N 0.000 claims 2
- SGZFLJKVODZGJM-UHFFFAOYSA-N 4-[[2-amino-1-(3,4-dimethoxyphenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CN)NC1=NC=NC2=C(C(N)=O)C=CC=C12 SGZFLJKVODZGJM-UHFFFAOYSA-N 0.000 claims 2
- IKONXWFEIGCAGN-UHFFFAOYSA-N 4-[[2-amino-1-(3-fluorophenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN)C1=CC=CC(F)=C1 IKONXWFEIGCAGN-UHFFFAOYSA-N 0.000 claims 2
- PRHCRPUDJXUXCO-UHFFFAOYSA-N 4-[[2-amino-1-(4-methoxyphenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound C1=CC(OC)=CC=C1C(CN)NC1=NC=NC2=C(C(N)=O)C=CC=C12 PRHCRPUDJXUXCO-UHFFFAOYSA-N 0.000 claims 2
- QVHGKNYBLQTWEC-UHFFFAOYSA-N 4-[[2-amino-1-(4-methylphenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound C1=CC(C)=CC=C1C(CN)NC1=NC=NC2=C(C(N)=O)C=CC=C12 QVHGKNYBLQTWEC-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- XMZNZUXMEXIQDA-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)methylamino]quinazoline-8-carboxamide Chemical compound N1=CN=C2C(C(=O)N)=CC=CC2=C1NCC1=CC=C(Cl)C(Cl)=C1 XMZNZUXMEXIQDA-UHFFFAOYSA-N 0.000 claims 1
- CKSGWNWLYXUENQ-UHFFFAOYSA-N 4-[(3,4-dimethylphenyl)methylamino]quinazoline-8-carboxamide Chemical compound C1=C(C)C(C)=CC=C1CNC1=NC=NC2=C(C(N)=O)C=CC=C12 CKSGWNWLYXUENQ-UHFFFAOYSA-N 0.000 claims 1
- YNPQIFHMRSVLHW-UHFFFAOYSA-N 4-[1-[3-(1,3-benzodioxole-5-carbonylamino)phenyl]ethylamino]quinazoline-8-carboxamide Chemical compound C1=C2OCOC2=CC(C(=O)NC=2C=CC=C(C=2)C(NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=C1 YNPQIFHMRSVLHW-UHFFFAOYSA-N 0.000 claims 1
- BZNBBOLMYRXASK-UHFFFAOYSA-N 4-[1-[3-[(3-fluoro-4-methylbenzoyl)amino]phenyl]ethylamino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(C)C(C=1)=CC=CC=1NC(=O)C1=CC=C(C)C(F)=C1 BZNBBOLMYRXASK-UHFFFAOYSA-N 0.000 claims 1
- QBWMPYZCKOEWSU-UHFFFAOYSA-N 4-[1-[3-[(4-bromobenzoyl)amino]phenyl]ethylamino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(C)C(C=1)=CC=CC=1NC(=O)C1=CC=C(Br)C=C1 QBWMPYZCKOEWSU-UHFFFAOYSA-N 0.000 claims 1
- SICPNVSSMIOAEC-UHFFFAOYSA-N 4-[1-[3-[(4-fluoro-3-hydroxybenzoyl)amino]phenyl]ethylamino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(C)C(C=1)=CC=CC=1NC(=O)C1=CC=C(F)C(O)=C1 SICPNVSSMIOAEC-UHFFFAOYSA-N 0.000 claims 1
- SRJJNRIRROSSLD-UHFFFAOYSA-N 4-[1-[3-[(5-tert-butyl-1h-pyrazole-3-carbonyl)amino]phenyl]ethylamino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(C)C(C=1)=CC=CC=1NC(=O)C1=CC(C(C)(C)C)=NN1 SRJJNRIRROSSLD-UHFFFAOYSA-N 0.000 claims 1
- POBKWGYBFDTZBY-UHFFFAOYSA-N 4-[1-[3-[(6-methoxypyridine-3-carbonyl)amino]phenyl]propylamino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CC)C(C=1)=CC=CC=1NC(=O)C1=CC=C(OC)N=C1 POBKWGYBFDTZBY-UHFFFAOYSA-N 0.000 claims 1
- KQPMGHOTWSCTSB-UHFFFAOYSA-N 4-[2-(1h-indol-3-yl)ethylamino]quinazoline-8-carboxamide Chemical compound C1=CC=C2C(CCNC3=C4C=CC=C(C4=NC=N3)C(=O)N)=CNC2=C1 KQPMGHOTWSCTSB-UHFFFAOYSA-N 0.000 claims 1
- YNPQIFHMRSVLHW-CQSZACIVSA-N 4-[[(1r)-1-[3-(1,3-benzodioxole-5-carbonylamino)phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C1=C2OCOC2=CC(C(=O)NC=2C=CC=C(C=2)[C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=C1 YNPQIFHMRSVLHW-CQSZACIVSA-N 0.000 claims 1
- VQTZMSIOEYJERT-ZVDHGWRTSA-N 4-[[(1r)-1-[3-[(2,2-difluorocyclopropanecarbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C=1C([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=CC=CC=1NC(=O)C1CC1(F)F VQTZMSIOEYJERT-ZVDHGWRTSA-N 0.000 claims 1
- NXUJCUODKLXIPE-CQSZACIVSA-N 4-[[(1r)-1-[3-[(2-methoxypyridine-4-carbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C1=NC(OC)=CC(C(=O)NC=2C=C(C=CC=2)[C@@H](C)NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)=C1 NXUJCUODKLXIPE-CQSZACIVSA-N 0.000 claims 1
- KWBXLLQBOZJIAV-QGZVFWFLSA-N 4-[[(1r)-1-[3-[(3,4-dimethylbenzoyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C=1C([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=CC=CC=1NC(=O)C1=CC=C(C)C(C)=C1 KWBXLLQBOZJIAV-QGZVFWFLSA-N 0.000 claims 1
- CVCLGNCOASWGPB-OAHLLOKOSA-N 4-[[(1r)-1-[3-[(4-chloro-3-methylbenzoyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C=1C([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=CC=CC=1NC(=O)C1=CC=C(Cl)C(C)=C1 CVCLGNCOASWGPB-OAHLLOKOSA-N 0.000 claims 1
- ZSTHXAKLQBVNDX-CQSZACIVSA-N 4-[[(1r)-1-[3-[(5,6-dimethoxypyridine-3-carbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound N1=C(OC)C(OC)=CC(C(=O)NC=2C=C(C=CC=2)[C@@H](C)NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)=C1 ZSTHXAKLQBVNDX-CQSZACIVSA-N 0.000 claims 1
- SHFIJZVQMKWQNN-CYBMUJFWSA-N 4-[[(1r)-1-[3-[(5-chloro-6-methoxypyridine-3-carbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C1=C(Cl)C(OC)=NC=C1C(=O)NC1=CC=CC([C@@H](C)NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)=C1 SHFIJZVQMKWQNN-CYBMUJFWSA-N 0.000 claims 1
- TUVCZMWCKOCSGF-CQSZACIVSA-N 4-[[(1r)-1-[3-[(5-propan-2-yl-1h-pyrazole-3-carbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound N1C(C(C)C)=CC(C(=O)NC=2C=C(C=CC=2)[C@@H](C)NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)=N1 TUVCZMWCKOCSGF-CQSZACIVSA-N 0.000 claims 1
- SRJJNRIRROSSLD-CQSZACIVSA-N 4-[[(1r)-1-[3-[(5-tert-butyl-1h-pyrazole-3-carbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C=1C([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=CC=CC=1NC(=O)C1=CC(C(C)(C)C)=NN1 SRJJNRIRROSSLD-CQSZACIVSA-N 0.000 claims 1
- GLMIBJBCEWSYSZ-CQSZACIVSA-N 4-[[(1r)-1-[3-[(6-cyanopyridine-3-carbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C=1C([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=CC=CC=1NC(=O)C1=CC=C(C#N)N=C1 GLMIBJBCEWSYSZ-CQSZACIVSA-N 0.000 claims 1
- GTUAZZUFAUMXII-CQSZACIVSA-N 4-[[(1r)-1-[3-[(6-methoxypyridine-3-carbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C1=NC(OC)=CC=C1C(=O)NC1=CC=CC([C@@H](C)NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)=C1 GTUAZZUFAUMXII-CQSZACIVSA-N 0.000 claims 1
- JMHMGIHHTONCMK-OAHLLOKOSA-N 4-[[(1r)-1-[3-[(6-methylpyridine-3-carbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C=1C([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=CC=CC=1NC(=O)C1=CC=C(C)N=C1 JMHMGIHHTONCMK-OAHLLOKOSA-N 0.000 claims 1
- RWBMPHFTXFAKIZ-CYBMUJFWSA-N 4-[[(1r)-1-[3-[[2-fluoro-4-(trifluoromethyl)benzoyl]amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C=1C([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=CC=CC=1NC(=O)C1=CC=C(C(F)(F)F)C=C1F RWBMPHFTXFAKIZ-CYBMUJFWSA-N 0.000 claims 1
- PELODSQJHQJMMD-CYBMUJFWSA-N 4-[[(1r)-1-[3-[[2-fluoro-5-(trifluoromethyl)benzoyl]amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C=1C([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)C)=CC=CC=1NC(=O)C1=CC(C(F)(F)F)=CC=C1F PELODSQJHQJMMD-CYBMUJFWSA-N 0.000 claims 1
- KFUGVCOVSKGHMS-HNNXBMFYSA-N 4-[[(1r)-2-(methylamino)-1-phenylethyl]amino]quinazoline-8-carboxamide Chemical compound C1([C@@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)CNC)=CC=CC=C1 KFUGVCOVSKGHMS-HNNXBMFYSA-N 0.000 claims 1
- KTEVQEUEMLYYMP-MRXNPFEDSA-N 4-[[(1s)-1-(3-chlorophenyl)-2-(methylamino)ethyl]amino]-6-methoxyquinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC(OC)=CC(=C3N=CN=2)C(N)=O)CNC)=CC=CC(Cl)=C1 KTEVQEUEMLYYMP-MRXNPFEDSA-N 0.000 claims 1
- XQZHZCUJORPEOS-MRXNPFEDSA-N 4-[[(1s)-1-(3-fluorophenyl)-2-(methylamino)ethyl]amino]-6-methoxyquinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC(OC)=CC(=C3N=CN=2)C(N)=O)CNC)=CC=CC(F)=C1 XQZHZCUJORPEOS-MRXNPFEDSA-N 0.000 claims 1
- RBMOLIOJAWRTIV-OAHLLOKOSA-N 4-[[(1s)-1-(3-fluorophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)CNC)=CC=CC(F)=C1 RBMOLIOJAWRTIV-OAHLLOKOSA-N 0.000 claims 1
- BFLHCYRERXMTKZ-QGZVFWFLSA-N 4-[[(1s)-2-(dimethylamino)-1-(3-fluorophenyl)ethyl]amino]-6-methoxyquinazoline-8-carboxamide Chemical compound C1([C@@H](CN(C)C)NC2=NC=NC3=C(C(N)=O)C=C(C=C32)OC)=CC=CC(F)=C1 BFLHCYRERXMTKZ-QGZVFWFLSA-N 0.000 claims 1
- GEECDZLHNUPFCU-MRXNPFEDSA-N 4-[[(1s)-2-(ethylamino)-1-(3-fluorophenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)CNCC)=CC=CC(F)=C1 GEECDZLHNUPFCU-MRXNPFEDSA-N 0.000 claims 1
- XAVPWAIYBBCDNE-QGZVFWFLSA-N 4-[[(1s)-2-(ethylamino)-1-phenylethyl]amino]-6-methoxyquinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC(OC)=CC(=C3N=CN=2)C(N)=O)CNCC)=CC=CC=C1 XAVPWAIYBBCDNE-QGZVFWFLSA-N 0.000 claims 1
- HITVHYHCWXALKZ-MRXNPFEDSA-N 4-[[(1s)-2-(ethylamino)-1-phenylethyl]amino]quinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)CNCC)=CC=CC=C1 HITVHYHCWXALKZ-MRXNPFEDSA-N 0.000 claims 1
- HNAFGFOVDGEYQN-OAHLLOKOSA-N 4-[[(1s)-2-amino-1-phenylethyl]amino]-6-methoxyquinazoline-8-carboxamide Chemical compound C1([C@@H](CN)NC2=NC=NC3=C(C(N)=O)C=C(C=C32)OC)=CC=CC=C1 HNAFGFOVDGEYQN-OAHLLOKOSA-N 0.000 claims 1
- CHKCVVJJVFZWOP-KXCGHJCSSA-N 4-[[(3r,4e)-1-amino-4-ethenylhepta-4,6-dien-3-yl]amino]quinazoline-8-carboxamide Chemical compound C1=CC=C2C(N[C@H](CCN)C(\C=C)=C\C=C)=NC=NC2=C1C(N)=O CHKCVVJJVFZWOP-KXCGHJCSSA-N 0.000 claims 1
- AGDQZNITYJKXQO-UHFFFAOYSA-N 4-[[1-(3,4-dichlorophenyl)-2-(dimethylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN(C)C)C1=CC=C(Cl)C(Cl)=C1 AGDQZNITYJKXQO-UHFFFAOYSA-N 0.000 claims 1
- BYUUFRNHCFTPTI-UHFFFAOYSA-N 4-[[1-(3,4-dichlorophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C1=CC=C(Cl)C(Cl)=C1 BYUUFRNHCFTPTI-UHFFFAOYSA-N 0.000 claims 1
- HZCSYARAUKXOFF-UHFFFAOYSA-N 4-[[1-(3-benzamidophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1 HZCSYARAUKXOFF-UHFFFAOYSA-N 0.000 claims 1
- QZMSENZZQWAYFQ-UHFFFAOYSA-N 4-[[1-(3-bromophenyl)-2-(dimethylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN(C)C)C1=CC=CC(Br)=C1 QZMSENZZQWAYFQ-UHFFFAOYSA-N 0.000 claims 1
- ODIBHBBABRKJIO-UHFFFAOYSA-N 4-[[1-(3-chlorophenyl)-2-(dimethylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN(C)C)C1=CC=CC(Cl)=C1 ODIBHBBABRKJIO-UHFFFAOYSA-N 0.000 claims 1
- KTEVQEUEMLYYMP-UHFFFAOYSA-N 4-[[1-(3-chlorophenyl)-2-(methylamino)ethyl]amino]-6-methoxyquinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=C(OC)C=C2C=1NC(CNC)C1=CC=CC(Cl)=C1 KTEVQEUEMLYYMP-UHFFFAOYSA-N 0.000 claims 1
- OPYPJZSJHHSMJL-UHFFFAOYSA-N 4-[[1-(3-chlorophenyl)-2-(methylamino)ethyl]amino]-6-phenylmethoxyquinazoline-8-carboxamide Chemical compound C=1C=CC(Cl)=CC=1C(CNC)NC(C1=C2)=NC=NC1=C(C(N)=O)C=C2OCC1=CC=CC=C1 OPYPJZSJHHSMJL-UHFFFAOYSA-N 0.000 claims 1
- LAJUPICIRDRINN-UHFFFAOYSA-N 4-[[1-(3-chlorophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C1=CC=CC(Cl)=C1 LAJUPICIRDRINN-UHFFFAOYSA-N 0.000 claims 1
- XQZHZCUJORPEOS-UHFFFAOYSA-N 4-[[1-(3-fluorophenyl)-2-(methylamino)ethyl]amino]-6-methoxyquinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=C(OC)C=C2C=1NC(CNC)C1=CC=CC(F)=C1 XQZHZCUJORPEOS-UHFFFAOYSA-N 0.000 claims 1
- RBMOLIOJAWRTIV-UHFFFAOYSA-N 4-[[1-(3-fluorophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C1=CC=CC(F)=C1 RBMOLIOJAWRTIV-UHFFFAOYSA-N 0.000 claims 1
- CJAKBHSFDAWLEM-UHFFFAOYSA-N 4-[[1-(4-chlorophenyl)-2-(dimethylamino)ethyl]amino]-6-methoxyquinazoline-8-carboxamide Chemical compound C12=CC(OC)=CC(C(N)=O)=C2N=CN=C1NC(CN(C)C)C1=CC=C(Cl)C=C1 CJAKBHSFDAWLEM-UHFFFAOYSA-N 0.000 claims 1
- ZJKRQNYRWHKMJV-UHFFFAOYSA-N 4-[[1-(4-methoxyphenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C1=CC=C(OC)C=C1 ZJKRQNYRWHKMJV-UHFFFAOYSA-N 0.000 claims 1
- MFRRIEBIBJQMAF-UHFFFAOYSA-N 4-[[1-[3-[(2,4-difluorobenzoyl)amino]phenyl]-3-(dimethylamino)propyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CCN(C)C)C(C=1)=CC=CC=1NC(=O)C1=CC=C(F)C=C1F MFRRIEBIBJQMAF-UHFFFAOYSA-N 0.000 claims 1
- NOOJGWFQMPPHRX-UHFFFAOYSA-N 4-[[1-[3-[(2,4-difluorobenzoyl)amino]phenyl]-3-methoxypropyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CCOC)C(C=1)=CC=CC=1NC(=O)C1=CC=C(F)C=C1F NOOJGWFQMPPHRX-UHFFFAOYSA-N 0.000 claims 1
- JKUFJTIKVQADGJ-UHFFFAOYSA-N 4-[[1-[3-[(2,6-difluorobenzoyl)amino]phenyl]-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C(C=1)=CC=CC=1NC(=O)C1=C(F)C=CC=C1F JKUFJTIKVQADGJ-UHFFFAOYSA-N 0.000 claims 1
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| US9321760B2 (en) | 2011-09-12 | 2016-04-26 | Merck Patent Gmbh | Aminopyrimidine derivatives for use as modulators of kinase activity |
| PT2755965T (pt) | 2011-09-12 | 2017-11-02 | Merck Patent Gmbh | Novas imidazol aminas como moduladores da atividade quinase |
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| US9580443B2 (en) | 2012-11-16 | 2017-02-28 | Merck Patent Gmbh | Heterocyclic derivatives as modulators of kinase activity |
| EP2920154B1 (en) | 2012-11-16 | 2017-10-11 | Merck Patent GmbH | Novel imidazol-piperidinyl derivatives as modulators of kinase activity |
| NZ706418A (en) * | 2012-11-29 | 2019-09-27 | Merck Patent Gmbh | Azaquinazoline carboxamide derivatives |
| WO2014120995A2 (en) | 2013-02-01 | 2014-08-07 | Wellstat Therapeutics Corporation | Amine compounds having anti-inflammatory, antifungal, antiparasitic and anticancer activity |
| AR095202A1 (es) | 2013-03-11 | 2015-09-30 | Merck Patent Gmbh | Heterociclos como moduladores de la actividad quinasa |
| GB201317609D0 (en) | 2013-10-04 | 2013-11-20 | Cancer Rec Tech Ltd | Inhibitor compounds |
| EP3125935B1 (en) | 2014-04-03 | 2019-10-23 | Merck Patent GmbH | Combinations of cancer therapeutics |
| CN104292170B (zh) * | 2014-09-22 | 2016-06-29 | 广西师范大学 | 具有抗肿瘤作用的喹唑啉-芳基脲衍生物及其应用 |
| AU2015335980A1 (en) * | 2014-10-22 | 2017-05-18 | Guangzhou Institutes Of Biomedicine And Health, Chinese Academy Of Sciences | Small-molecule inhibitors targeting discoidin domain receptor 1 and uses thereof |
| GB201505658D0 (en) | 2015-04-01 | 2015-05-13 | Cancer Rec Tech Ltd | Inhibitor compounds |
| GB201617103D0 (en) | 2016-10-07 | 2016-11-23 | Cancer Research Technology Limited | Compound |
| FR3066761B1 (fr) * | 2017-05-23 | 2020-10-30 | Centre Nat Rech Scient | Nouveaux composes inhibiteurs des canaux ioniques |
| US11254654B2 (en) * | 2017-06-30 | 2022-02-22 | The University Of North Carolina At Chapel Hill | Heterochromatin gene repression inhibitors |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| TWI853814B (zh) | 2018-05-31 | 2024-09-01 | 南韓商Ｃ＆Ｃ新藥研究所 | 雜環衍生物及其用途 |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| CN109369634B (zh) * | 2018-12-19 | 2021-07-27 | 陕西国际商贸学院 | 具有抗肿瘤活性的2-甲氧基烟酰胺衍生物制备方法及用途 |
| RU2723481C1 (ru) * | 2019-10-03 | 2020-06-11 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ УНИТАРНОЕ ПРЕДПРИЯТИЕ "ИНСТИТУТ ХИМИЧЕСКИХ РЕАКТИВОВ И ОСОБО ЧИСТЫХ ХИМИЧЕСКИХ ВЕЩЕСТВ НАЦИОНАЛЬНОГО ИССЛЕДОВАТЕЛЬСКОГО ЦЕНТРА "КУРЧАТОВСКИЙ ИНСТИТУТ" (НИЦ "Курчатовский институт - ИРЕА) | 4-[метил 4-(аминометил)циклогексанкарбоксилат]хиназолин и способ его получения |
| AU2020372700A1 (en) | 2019-11-01 | 2022-05-12 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
| CN112778217B (zh) * | 2019-11-08 | 2024-01-26 | 沈阳化工研究院有限公司 | 一种喹唑啉类化合物及其应用 |
| WO2022101459A1 (en) | 2020-11-16 | 2022-05-19 | Merck Patent Gmbh | Kinase inhibitor combinations for cancer treatment |
| KR20240021198A (ko) * | 2021-06-11 | 2024-02-16 | 오츠카 세이야쿠 가부시키가이샤 | Erk 억제제의 제조 방법 |
| KR20240024926A (ko) | 2021-06-24 | 2024-02-26 | 신젠타 크롭 프로텍션 아게 | 살충제로서의 2-[3-[1[(퀴나졸린-4-일)아미노]에틸]피라진-2-일]티아졸-5-카르보니트릴 유도체 및 유사한 화합물 |
| TW202345806A (zh) | 2022-03-31 | 2023-12-01 | 美商艾伯維有限公司 | 噻唑并〔５，４－ｂ〕吡啶ｍａｌｔ－１抑制劑 |
| CA3245810A1 (en) * | 2022-04-11 | 2023-10-19 | Merck Patent Gmbh | PYRIDO[3,2-D]PYRIMIDINS USED AS HPK1 INHIBITORS |
| JP2025520650A (ja) | 2022-06-21 | 2025-07-03 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に活性な縮合二環式芳香族複素環式化合物 |
| CN115521474B (zh) * | 2022-09-30 | 2023-08-22 | 陕西科技大学 | 一种基于五重互穿氢键有机框架材料及其制备方法和应用 |
| WO2025228828A1 (en) * | 2024-04-29 | 2025-11-06 | Merck Patent Gmbh | Carboxamide compounds for the treatment and prevention of viral diseases |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU534608B2 (en) * | 1979-09-14 | 1984-02-09 | Warner-Lambert Corporation | Compounds having antitumour properties |
| GB8804445D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| AR016817A1 (es) * | 1997-08-14 | 2001-08-01 | Smithkline Beecham Plc | Derivados de fenilurea o feniltiourea, procedimiento para su preparacion, coleccion de compuestos, compuestos intermediarios, composicion farmaceutica,metodo de tratamiento y uso de dichos compuestos para la manufactura de un medicamento |
| CA2384291A1 (en) | 1999-09-21 | 2001-03-29 | Astrazeneca Ab | Quinazoline derivatives and their use as pharmaceuticals |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| KR100774855B1 (ko) * | 2000-04-27 | 2007-11-08 | 아스텔라스세이야쿠 가부시키가이샤 | 축합 헤테로아릴 유도체 |
| IL153246A0 (en) * | 2000-06-28 | 2003-07-06 | Astrazeneca Ab | Substituted quinazoline derivatives and their use as inhibitors |
| WO2003055491A1 (en) * | 2001-12-24 | 2003-07-10 | Astrazeneca Ab | Substituted quinazoline derivatives as inhibitors of aurora kinases |
| TW200306819A (en) | 2002-01-25 | 2003-12-01 | Vertex Pharma | Indazole compounds useful as protein kinase inhibitors |
| AU2004230841A1 (en) | 2003-04-03 | 2004-10-28 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| EP1670771A4 (en) | 2003-09-30 | 2010-09-01 | Irm Llc | COMPOUNDS AND COMPOSITIONS INHIBITING PROTEIN-KINASES |
| WO2005039506A2 (en) | 2003-10-24 | 2005-05-06 | Exelixis, Inc. | P70s6 kinase modulators and method of use |
| PT1687305E (pt) | 2003-11-21 | 2008-10-17 | Novartis Ag | Derivados de 1h-imidazoquinolina como inibidores de proteína quinase |
| ATE447957T1 (de) | 2003-12-09 | 2009-11-15 | Us Gov Health & Human Serv | Verfahren zur unterdrückung einer immunantwort oder zur behandlung von proliferativen erkrankungen |
| WO2005117909A2 (en) | 2004-04-23 | 2005-12-15 | Exelixis, Inc. | Kinase modulators and methods of use |
| JP5274842B2 (ja) | 2004-12-28 | 2013-08-28 | エグゼリクシス， インコーポレイテッド | 免疫疾患、炎症疾患および増殖疾患の処置のためのセリン−スレオニンキナーゼモジュレーター（ｐ７０Ｓ６Ｋ、Ａｋｔ−１およびＡｋｔ−２）としての［１Ｈ−ピペラゾ［３，４−ｄ］ピリミジン−４−イル］−ピペラジンまたは［１Ｈ−ピペラゾ［３，４−ｄ］ピリミジン−４−イル］−ピペラジン化合物 |
| GB0501999D0 (en) | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| US8343953B2 (en) | 2005-06-22 | 2013-01-01 | Astex Therapeutics Limited | Pharmaceutical compounds |
| WO2007015569A1 (ja) * | 2005-08-01 | 2007-02-08 | Eisai R & D Management Co., Ltd. | 血管新生阻害物質の効果を予測する方法 |
| TW200825054A (en) * | 2006-10-18 | 2008-06-16 | Wyeth Corp | Quinoline compounds |
| US7776857B2 (en) * | 2007-04-05 | 2010-08-17 | Amgen Inc. | Aurora kinase modulators and method of use |
| UA99284C2 (ru) | 2007-05-11 | 2012-08-10 | Елі Ліллі Енд Компані | ИНГИБИТОРЫ р70 S6-КИНАЗЫ |
| US7829574B2 (en) * | 2008-05-09 | 2010-11-09 | Hutchison Medipharma Enterprises Limited | Substituted quinazoline compounds and their use in treating angiogenesis-related diseases |
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