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
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- 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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| US9315517B2 (en) | 2012-11-16 | 2016-04-19 | Merck Patent Gmbh | Imidazol-piperidinyl derivatives as modulators of kinase activity |
| WO2014078637A1 (en) | 2012-11-16 | 2014-05-22 | Merck Patent Gmbh | Novel heterocyclic derivatives as modulators of kinase activity |
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