JP2007511576A - タンパク質キナーゼ依存性疾患の処置における、１Ｈ−イミダゾ［４，５−ｃ］キノリン誘導体 - Google Patents

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Publication number

JP2007511576A

JP2007511576A JP2006540348A JP2006540348A JP2007511576A JP 2007511576 A JP2007511576 A JP 2007511576A JP 2006540348 A JP2006540348 A JP 2006540348A JP 2006540348 A JP2006540348 A JP 2006540348A JP 2007511576 A JP2007511576 A JP 2007511576A

Authority

JP

Japan

Prior art keywords

phenyl

imidazo

quinolin

ylethynyl

pyridin

Prior art date

2003-11-21

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.)

Pending

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• 201000010099 disease Diseases 0.000 title claims abstract description 81
• 238000011282 treatment Methods 0.000 title claims abstract description 81
• 102000001253 Protein Kinase Human genes 0.000 title claims abstract description 44
• 230000001419 dependent effect Effects 0.000 title claims abstract description 44
• 108060006633 protein kinase Proteins 0.000 title claims abstract description 44
• ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 title 1
• 150000003839 salts Chemical class 0.000 claims abstract description 78
• 238000000034 method Methods 0.000 claims abstract description 36
• 238000004519 manufacturing process Methods 0.000 claims abstract description 31
• 241001465754 Metazoa Species 0.000 claims abstract description 20
• 150000001875 compounds Chemical class 0.000 claims description 416
• 125000000217 alkyl group Chemical group 0.000 claims description 212
• -1 cyanomethyl Chemical group 0.000 claims description 207
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 103
• 229910052739 hydrogen Inorganic materials 0.000 claims description 79
• 239000001257 hydrogen Substances 0.000 claims description 76
• 125000003545 alkoxy group Chemical group 0.000 claims description 71
• 125000001424 substituent group Chemical group 0.000 claims description 69
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 67
• 229910052757 nitrogen Inorganic materials 0.000 claims description 61
• 125000005843 halogen group Chemical group 0.000 claims description 51
• 229910052760 oxygen Inorganic materials 0.000 claims description 47
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
• 125000000962 organic group Chemical group 0.000 claims description 40
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 239000000203 mixture Substances 0.000 claims description 33
• 239000001301 oxygen Substances 0.000 claims description 33
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 33
• 125000002393 azetidinyl group Chemical group 0.000 claims description 32
• 239000008194 pharmaceutical composition Substances 0.000 claims description 32
• 125000004076 pyridyl group Chemical group 0.000 claims description 32
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• 125000004193 piperazinyl group Chemical group 0.000 claims description 29
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 27
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
• 125000001153 fluoro group Chemical group F* 0.000 claims description 26
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 26
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
• 125000004434 sulfur atom Chemical group 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• 201000011510 cancer Diseases 0.000 claims description 15
• 125000004450 alkenylene group Chemical group 0.000 claims description 14
• 125000004419 alkynylene group Chemical group 0.000 claims description 14
• 125000001246 bromo group Chemical group Br* 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 13
• 125000003277 amino group Chemical group 0.000 claims description 12
• 125000001905 inorganic group Chemical group 0.000 claims description 12
• 230000002062 proliferating effect Effects 0.000 claims description 12
• 125000005605 benzo group Chemical group 0.000 claims description 11
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 10
• 150000001204 N-oxides Chemical class 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 10
• 125000002883 imidazolyl group Chemical group 0.000 claims description 10
• 125000002757 morpholinyl group Chemical group 0.000 claims description 10
• 230000001225 therapeutic effect Effects 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 6
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• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 210000004072 lung Anatomy 0.000 claims description 6
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• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
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• 208000032839 leukemia Diseases 0.000 claims description 5
• 239000000463 material Substances 0.000 claims description 5
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
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• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 4
• GQMQFPJCJCXLIK-UHFFFAOYSA-N 2-[4-[8-(2-phenylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1N1C2=C3C=C(C#CC=4C=CC=CC=4)C=CC3=NC=C2N=C1 GQMQFPJCJCXLIK-UHFFFAOYSA-N 0.000 claims description 3
• 201000007815 Bannayan-Riley-Ruvalcaba syndrome Diseases 0.000 claims description 3
• 206010061968 Gastric neoplasm Diseases 0.000 claims description 3
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 3
• 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims description 3
• 208000034578 Multiple myelomas Diseases 0.000 claims description 3
• 206010033128 Ovarian cancer Diseases 0.000 claims description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 208000033781 Thyroid carcinoma Diseases 0.000 claims description 3
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
• 210000004100 adrenal gland Anatomy 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 201000002758 colorectal adenoma Diseases 0.000 claims description 3
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
• 206010020718 hyperplasia Diseases 0.000 claims description 3
• 210000003734 kidney Anatomy 0.000 claims description 3
• 210000004185 liver Anatomy 0.000 claims description 3
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• 210000000664 rectum Anatomy 0.000 claims description 3
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• 210000003932 urinary bladder Anatomy 0.000 claims description 3
• MPYWCTSYTBGDCY-UHFFFAOYSA-N 1-(3-fluoro-4-piperazin-1-ylphenyl)-2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinoline Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCNCC1 MPYWCTSYTBGDCY-UHFFFAOYSA-N 0.000 claims description 2
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
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• 210000001215 vagina Anatomy 0.000 claims description 2
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
• PKGHWDSSIRJBIV-UHFFFAOYSA-N 1-[2-fluoro-4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidine-2,5-dione Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1C(=O)CCC1=O PKGHWDSSIRJBIV-UHFFFAOYSA-N 0.000 claims 2
• ZVRVFWZZQBFPPR-UHFFFAOYSA-N 1-[2-fluoro-4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidine-2,5-dione Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1C(=O)CCC1=O ZVRVFWZZQBFPPR-UHFFFAOYSA-N 0.000 claims 2
• ZHRIIWTULLKLOZ-UHFFFAOYSA-N 1-[2-fluoro-4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidine-2,5-dione Chemical compound FC1=CC(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)=CC=C1N1C(=O)CCC1=O ZHRIIWTULLKLOZ-UHFFFAOYSA-N 0.000 claims 2
• LHSCHOOVTKCKFQ-UHFFFAOYSA-N 2-[4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]ethanamine Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CCN)C=C1 LHSCHOOVTKCKFQ-UHFFFAOYSA-N 0.000 claims 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
• OPKIAWSENCRPIV-UHFFFAOYSA-N 1-(3-fluoro-4-piperazin-1-ylphenyl)-3-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C)C2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCNCC1 OPKIAWSENCRPIV-UHFFFAOYSA-N 0.000 claims 1
• NLUPUSNFCXCEOO-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-2-one Chemical compound COC1=CC=CC(N2C(N(C)C3=C2C2=CC(=CC=C2N=C3)C#CC=2C=NC=CC=2)=O)=C1 NLUPUSNFCXCEOO-UHFFFAOYSA-N 0.000 claims 1
• MFEMGSVIYPDPEM-UHFFFAOYSA-N 1-(4-ethylphenyl)-3-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=CC(CC)=CC=C1N1C(=O)N(C)C2=C1C1=CC(C#CC=3C=NC=CC=3)=CC=C1N=C2 MFEMGSVIYPDPEM-UHFFFAOYSA-N 0.000 claims 1
• BVDPVTMCKJGRMH-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C)C2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(F)C=C1 BVDPVTMCKJGRMH-UHFFFAOYSA-N 0.000 claims 1
• JCRXOXKXCTUSKL-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C)C2=C1C1=CC(C#CC=3C=NC=CC=3)=CC=C1N=C2 JCRXOXKXCTUSKL-UHFFFAOYSA-N 0.000 claims 1
• ARWAHLLZIPCUGB-UHFFFAOYSA-N 1-[2-fluoro-4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidin-2-one Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCCC1=O ARWAHLLZIPCUGB-UHFFFAOYSA-N 0.000 claims 1
• YHGLMXVUBDXLFV-UHFFFAOYSA-N 1-[2-fluoro-4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidin-2-one Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCCC1=O YHGLMXVUBDXLFV-UHFFFAOYSA-N 0.000 claims 1
• AWJWRIBNZJLBEA-UHFFFAOYSA-N 1-[2-fluoro-4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidin-2-one Chemical compound FC1=CC(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)=CC=C1N1CCCC1=O AWJWRIBNZJLBEA-UHFFFAOYSA-N 0.000 claims 1
• LRQNPTNNOXGJHS-UHFFFAOYSA-N 1-[3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinoline Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCN(C)CC1 LRQNPTNNOXGJHS-UHFFFAOYSA-N 0.000 claims 1
• GHBAXDJNWWIHMR-UHFFFAOYSA-N 1-[3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinoline Chemical compound C1CN(C)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2C)C#CC=2C=NC=CC=2)C=C1F GHBAXDJNWWIHMR-UHFFFAOYSA-N 0.000 claims 1
• CSDZDJKBTIQZIH-UHFFFAOYSA-N 1-[3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinoline Chemical compound C1CN(C)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1F CSDZDJKBTIQZIH-UHFFFAOYSA-N 0.000 claims 1
• VMVRKNCPNQPHPY-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinoline Chemical compound C1CN(C)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1 VMVRKNCPNQPHPY-UHFFFAOYSA-N 0.000 claims 1
• LUSWYHFSMIDVHD-UHFFFAOYSA-N 1-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinoline Chemical compound C1CN(C)CCN1CC1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1 LUSWYHFSMIDVHD-UHFFFAOYSA-N 0.000 claims 1
• VIEXSJPLENBNFA-UHFFFAOYSA-N 1-[4-[2-(azetidin-1-yl)ethyl]phenyl]-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinoline Chemical compound C1CCN1CCC(C=C1)=CC=C1N(C1=C2C=3)C=NC1=CN=C2C=CC=3C#CC1=CC=CN=C1 VIEXSJPLENBNFA-UHFFFAOYSA-N 0.000 claims 1
• URQPRWLSOMXIRF-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-fluorophenyl]pyrrolidin-2-one Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCCC1=O URQPRWLSOMXIRF-UHFFFAOYSA-N 0.000 claims 1
• IYIAMENZDUWUJX-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-fluorophenyl]pyrrolidine-2,5-dione Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1C(=O)CCC1=O IYIAMENZDUWUJX-UHFFFAOYSA-N 0.000 claims 1
• YDTYZCVMNBCHEK-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidin-2-one Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1)=CC=C1N1CCCC1=O YDTYZCVMNBCHEK-UHFFFAOYSA-N 0.000 claims 1
• BTWXMBDRCBAIRA-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethyl]phenyl]-n,n-dimethyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-2-amine Chemical compound C1=CC(CCN(C)C)=CC=C1N1C2=C3C=C(C#CC=4C=NC=CC=4)C=CC3=NC=C2N=C1N(C)C BTWXMBDRCBAIRA-UHFFFAOYSA-N 0.000 claims 1
• MHVCIMKWCFFZFP-UHFFFAOYSA-N 1-[4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidin-2-one Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1)=CC=C1N1CCCC1=O MHVCIMKWCFFZFP-UHFFFAOYSA-N 0.000 claims 1
• GNCVDXQGLPXERK-UHFFFAOYSA-N 1-[4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidin-2-one Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1)=CC=C1N1CCCC1=O GNCVDXQGLPXERK-UHFFFAOYSA-N 0.000 claims 1
• YFSPRBVHNZCSLU-UHFFFAOYSA-N 1-[4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1 YFSPRBVHNZCSLU-UHFFFAOYSA-N 0.000 claims 1
• VOCYESNTCNPCGM-UHFFFAOYSA-N 1-[4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1 VOCYESNTCNPCGM-UHFFFAOYSA-N 0.000 claims 1
• NCKUSFQXIZDSDM-UHFFFAOYSA-N 1-ethyl-4-[2-fluoro-4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]piperazin-2-one Chemical compound C1C(=O)N(CC)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2C)C#CC=2C=NC=CC=2)C=C1F NCKUSFQXIZDSDM-UHFFFAOYSA-N 0.000 claims 1
• CIYPTZCEFUKEEC-UHFFFAOYSA-N 1-ethyl-4-[2-fluoro-4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]piperazin-2-one Chemical compound C1C(=O)N(CC)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1F CIYPTZCEFUKEEC-UHFFFAOYSA-N 0.000 claims 1
• SOXZDSRRXSONHS-UHFFFAOYSA-N 2-(2-cyanopropan-2-yl)-5-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(C(C)(C)C#N)C(C#N)=C1 SOXZDSRRXSONHS-UHFFFAOYSA-N 0.000 claims 1
• KPRDRXAJNJDZPM-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)-5-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound O=C1CCCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1C#N KPRDRXAJNJDZPM-UHFFFAOYSA-N 0.000 claims 1
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• GYXFYZGQILYACC-UHFFFAOYSA-N 2-[4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-2-methylpropanenitrile Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(C(C)(C)C#N)C=C1 GYXFYZGQILYACC-UHFFFAOYSA-N 0.000 claims 1
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• DFPPOOUJNBFPOL-UHFFFAOYSA-N 2-[4-[8-[2-(6-morpholin-4-ylpyridin-3-yl)ethynyl]imidazo[4,5-c]quinolin-1-yl]phenyl]acetonitrile Chemical compound C1=CC(CC#N)=CC=C1N1C2=C3C=C(C#CC=4C=NC(=CC=4)N4CCOCC4)C=CC3=NC=C2N=C1 DFPPOOUJNBFPOL-UHFFFAOYSA-N 0.000 claims 1
• XIAGGYZUTHUJMO-UHFFFAOYSA-N 2-[4-[8-[2-(6-morpholin-4-ylpyridin-3-yl)ethynyl]imidazo[4,5-c]quinolin-1-yl]phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1N1C2=C3C=C(C#CC=4C=NC(=CC=4)N4CCOCC4)C=CC3=NC=C2N=C1 XIAGGYZUTHUJMO-UHFFFAOYSA-N 0.000 claims 1
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• ISHNPDWTQUXPSY-UHFFFAOYSA-N 2-methyl-2-[4-[3-methyl-2-oxo-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propanenitrile Chemical compound O=C1N(C)C2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(C(C)(C)C#N)C=C1 ISHNPDWTQUXPSY-UHFFFAOYSA-N 0.000 claims 1
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• NHXNSLAPIMAEMQ-UHFFFAOYSA-N 2-piperazin-1-yl-5-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound N#CC1=CC(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)=CC=C1N1CCNCC1 NHXNSLAPIMAEMQ-UHFFFAOYSA-N 0.000 claims 1
• GJVRMBKDYSEJIQ-UHFFFAOYSA-N 3-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=CC(C#N)=C1 GJVRMBKDYSEJIQ-UHFFFAOYSA-N 0.000 claims 1
• HIMUKZCTGJZXTR-UHFFFAOYSA-N 3-[2-fluoro-4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCOC1=O HIMUKZCTGJZXTR-UHFFFAOYSA-N 0.000 claims 1
• IZBZMLBDVWEBRA-UHFFFAOYSA-N 3-[2-fluoro-4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCOC1=O IZBZMLBDVWEBRA-UHFFFAOYSA-N 0.000 claims 1
• OQHKDHKEVXRDCM-UHFFFAOYSA-N 3-[2-fluoro-4-[3-methyl-2-oxo-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1N(C)C2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCOC1=O OQHKDHKEVXRDCM-UHFFFAOYSA-N 0.000 claims 1
• ZEWDYANFQIGMMM-UHFFFAOYSA-N 3-[2-fluoro-4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound FC1=CC(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)=CC=C1N1CCOC1=O ZEWDYANFQIGMMM-UHFFFAOYSA-N 0.000 claims 1
• MANWPKZTAGERSX-UHFFFAOYSA-N 3-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=CC(C#N)=C1 MANWPKZTAGERSX-UHFFFAOYSA-N 0.000 claims 1
• OWDMZSGMRJQZTK-UHFFFAOYSA-N 3-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=CC(C#N)=C1 OWDMZSGMRJQZTK-UHFFFAOYSA-N 0.000 claims 1
• HDAKXVWWLXPCQV-UHFFFAOYSA-N 3-[4-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-fluorophenyl]-1,3-oxazolidin-2-one Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1F)=CC=C1N1CCOC1=O HDAKXVWWLXPCQV-UHFFFAOYSA-N 0.000 claims 1
• JSUNQFHLLPUKID-UHFFFAOYSA-N 3-[4-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propanenitrile Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CCC#N)C=C1 JSUNQFHLLPUKID-UHFFFAOYSA-N 0.000 claims 1
• INAUXOVQEVRWRA-UHFFFAOYSA-N 3-[4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1)=CC=C1N1CCOC1=O INAUXOVQEVRWRA-UHFFFAOYSA-N 0.000 claims 1
• BNLFEJCZBYYGFA-UHFFFAOYSA-N 3-[4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propanenitrile Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CCC#N)C=C1 BNLFEJCZBYYGFA-UHFFFAOYSA-N 0.000 claims 1
• KHCSPNIHKFAHFN-UHFFFAOYSA-N 3-[4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1)=CC=C1N1CCOC1=O KHCSPNIHKFAHFN-UHFFFAOYSA-N 0.000 claims 1
• OCCJXNOZISGUGT-UHFFFAOYSA-N 3-[4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propanenitrile Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CCC#N)C=C1 OCCJXNOZISGUGT-UHFFFAOYSA-N 0.000 claims 1
• JQSGDPGTIVOOBZ-UHFFFAOYSA-N 3-[4-[3-methyl-2-oxo-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1N(C)C2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1)=CC=C1N1CCOC1=O JQSGDPGTIVOOBZ-UHFFFAOYSA-N 0.000 claims 1
• WINZLARFVWRTMW-UHFFFAOYSA-N 3-[4-[7-chloro-8-(2-phenylethenyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound C1=CC(CCCN)=CC=C1N1C2=C3C=C(C=CC=4C=CC=CC=4)C(Cl)=CC3=NC=C2N=C1 WINZLARFVWRTMW-UHFFFAOYSA-N 0.000 claims 1
• DLMZDQHKROUAPM-UHFFFAOYSA-N 3-[4-[7-chloro-8-(2-phenylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound C1=CC(CCCN)=CC=C1N1C2=C3C=C(C#CC=4C=CC=CC=4)C(Cl)=CC3=NC=C2N=C1 DLMZDQHKROUAPM-UHFFFAOYSA-N 0.000 claims 1
• AIEQSQGQFXNLCJ-UHFFFAOYSA-N 3-[4-[7-chloro-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound C1=CC(CCCN)=CC=C1N1C2=C3C=C(C#CC=4C=NC=CC=4)C(Cl)=CC3=NC=C2N=C1 AIEQSQGQFXNLCJ-UHFFFAOYSA-N 0.000 claims 1
• LDKJRBUCWUKJFV-UHFFFAOYSA-N 3-[4-[7-chloro-8-[2-(3-methoxyphenyl)ethynyl]imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound COC1=CC=CC(C#CC=2C(=CC3=NC=C4N=CN(C4=C3C=2)C=2C=CC(CCCN)=CC=2)Cl)=C1 LDKJRBUCWUKJFV-UHFFFAOYSA-N 0.000 claims 1
• PKPPJCLPTITMCS-UHFFFAOYSA-N 3-[4-[7-chloro-8-[2-(4-methoxyphenyl)ethynyl]imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound C1=CC(OC)=CC=C1C#CC1=CC2=C(N(C=N3)C=4C=CC(CCCN)=CC=4)C3=CN=C2C=C1Cl PKPPJCLPTITMCS-UHFFFAOYSA-N 0.000 claims 1
• KLUBHJPGLMCWAS-UHFFFAOYSA-N 3-[4-[8-(2-phenylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound C1=CC(CCCN)=CC=C1N1C2=C3C=C(C#CC=4C=CC=CC=4)C=CC3=NC=C2N=C1 KLUBHJPGLMCWAS-UHFFFAOYSA-N 0.000 claims 1
• FQOLWDWXFYABJY-UHFFFAOYSA-N 3-[4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1 FQOLWDWXFYABJY-UHFFFAOYSA-N 0.000 claims 1
• HLKANOLKPOWIFP-UHFFFAOYSA-N 3-[4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound C1=CC(CCCN)=CC=C1N1C2=C3C=C(C#CC=4C=NC=CC=4)C=CC3=NC=C2N=C1 HLKANOLKPOWIFP-UHFFFAOYSA-N 0.000 claims 1
• AMLIJMXPKGPRDE-UHFFFAOYSA-N 3-[4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]propanenitrile Chemical compound C1=CC(CCC#N)=CC=C1N1C2=C3C=C(C#CC=4C=NC=CC=4)C=CC3=NC=C2N=C1 AMLIJMXPKGPRDE-UHFFFAOYSA-N 0.000 claims 1
• BCZJJNAZRVQBJK-UHFFFAOYSA-N 3-[4-[8-[2-(1,3-benzodioxol-5-yl)ethynyl]-7-chloroimidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound C1=CC(CCCN)=CC=C1N1C2=C3C=C(C#CC=4C=C5OCOC5=CC=4)C(Cl)=CC3=NC=C2N=C1 BCZJJNAZRVQBJK-UHFFFAOYSA-N 0.000 claims 1
• UUTQGUOPKUPMBP-UHFFFAOYSA-N 3-[4-[8-[2-(1,3-benzodioxol-5-yl)ethynyl]imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound C1=CC(CCCN)=CC=C1N1C2=C3C=C(C#CC=4C=C5OCOC5=CC=4)C=CC3=NC=C2N=C1 UUTQGUOPKUPMBP-UHFFFAOYSA-N 0.000 claims 1
• QKLKCMPBSWZESH-UHFFFAOYSA-N 3-[4-[8-[2-(3-methoxyphenyl)ethynyl]imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound COC1=CC=CC(C#CC=2C=C3C=4N(C=5C=CC(CCCN)=CC=5)C=NC=4C=NC3=CC=2)=C1 QKLKCMPBSWZESH-UHFFFAOYSA-N 0.000 claims 1
• OYYTVRBZDDQJRT-UHFFFAOYSA-N 3-[4-[8-[2-(4-methoxyphenyl)ethynyl]imidazo[4,5-c]quinolin-1-yl]phenyl]propan-1-amine Chemical compound C1=CC(OC)=CC=C1C#CC1=CC=C(N=CC2=C3N(C=4C=CC(CCCN)=CC=4)C=N2)C3=C1 OYYTVRBZDDQJRT-UHFFFAOYSA-N 0.000 claims 1
• JMHUIBMRXCTUGG-UHFFFAOYSA-N 3-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)=C1 JMHUIBMRXCTUGG-UHFFFAOYSA-N 0.000 claims 1
• HOMLYFMOMUXLJL-UHFFFAOYSA-N 3-methyl-1-(4-piperazin-1-ylphenyl)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-2-one Chemical compound O=C1N(C)C2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1)=CC=C1N1CCNCC1 HOMLYFMOMUXLJL-UHFFFAOYSA-N 0.000 claims 1
• BZMWREOIGPDKIP-UHFFFAOYSA-N 3-methyl-1-[4-(methylamino)phenyl]-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-2-one Chemical compound C1=CC(NC)=CC=C1N1C(=O)N(C)C2=C1C1=CC(C#CC=3C=NC=CC=3)=CC=C1N=C2 BZMWREOIGPDKIP-UHFFFAOYSA-N 0.000 claims 1
• NPHTVUPPKOGOJF-UHFFFAOYSA-N 3-methyl-8-(2-pyridin-3-ylethynyl)-1-(3,4,5-trimethoxyphenyl)imidazo[4,5-c]quinolin-2-one Chemical compound COC1=C(OC)C(OC)=CC(N2C(N(C)C3=C2C2=CC(=CC=C2N=C3)C#CC=2C=NC=CC=2)=O)=C1 NPHTVUPPKOGOJF-UHFFFAOYSA-N 0.000 claims 1
• QYXFTIUIFIVLQI-UHFFFAOYSA-N 4-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(C#N)C=C1 QYXFTIUIFIVLQI-UHFFFAOYSA-N 0.000 claims 1
• LDEVQPBVPLVWDD-UHFFFAOYSA-N 4-[2-[1-[4-(2-aminoethyl)phenyl]-7-chloroimidazo[4,5-c]quinolin-8-yl]ethynyl]benzenesulfonamide Chemical compound C1=CC(CCN)=CC=C1N1C2=C3C=C(C#CC=4C=CC(=CC=4)S(N)(=O)=O)C(Cl)=CC3=NC=C2N=C1 LDEVQPBVPLVWDD-UHFFFAOYSA-N 0.000 claims 1
• ZRBAORUKXGLQEB-UHFFFAOYSA-N 4-[2-[1-[4-(2-aminoethyl)phenyl]-7-fluoroimidazo[4,5-c]quinolin-8-yl]ethynyl]benzenesulfonamide Chemical compound C1=CC(CCN)=CC=C1N1C2=C3C=C(C#CC=4C=CC(=CC=4)S(N)(=O)=O)C(F)=CC3=NC=C2N=C1 ZRBAORUKXGLQEB-UHFFFAOYSA-N 0.000 claims 1
• CMRUTKOTCDEPQV-UHFFFAOYSA-N 4-[2-[1-[4-(2-aminoethyl)phenyl]imidazo[4,5-c]quinolin-8-yl]ethynyl]benzenesulfonamide Chemical compound C1=CC(CCN)=CC=C1N1C2=C3C=C(C#CC=4C=CC(=CC=4)S(N)(=O)=O)C=CC3=NC=C2N=C1 CMRUTKOTCDEPQV-UHFFFAOYSA-N 0.000 claims 1
• VYEBPNGHDHNFKH-UHFFFAOYSA-N 4-[2-[1-[4-(3-aminopropyl)phenyl]-7-chloroimidazo[4,5-c]quinolin-8-yl]ethynyl]benzenesulfonamide Chemical compound C1=CC(CCCN)=CC=C1N1C2=C3C=C(C#CC=4C=CC(=CC=4)S(N)(=O)=O)C(Cl)=CC3=NC=C2N=C1 VYEBPNGHDHNFKH-UHFFFAOYSA-N 0.000 claims 1
• YWOBOLQSRQBTGI-UHFFFAOYSA-N 4-[2-[1-[4-(3-aminopropyl)phenyl]imidazo[4,5-c]quinolin-8-yl]ethynyl]benzenesulfonamide Chemical compound C1=CC(CCCN)=CC=C1N1C2=C3C=C(C#CC=4C=CC(=CC=4)S(N)(=O)=O)C=CC3=NC=C2N=C1 YWOBOLQSRQBTGI-UHFFFAOYSA-N 0.000 claims 1
• HNMAKLCYWJNOQU-UHFFFAOYSA-N 4-[2-fluoro-4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2C)C#CC=2C=NC=CC=2)C=C1F HNMAKLCYWJNOQU-UHFFFAOYSA-N 0.000 claims 1
• FQSAMJXHJGRJFM-UHFFFAOYSA-N 4-[2-fluoro-4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1F FQSAMJXHJGRJFM-UHFFFAOYSA-N 0.000 claims 1
• PBISFMKEDIRQEW-UHFFFAOYSA-N 4-[2-fluoro-4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]piperazin-2-one Chemical compound FC1=CC(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)=CC=C1N1CCNC(=O)C1 PBISFMKEDIRQEW-UHFFFAOYSA-N 0.000 claims 1
• DNLUVZFMNAQCGT-UHFFFAOYSA-N 4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(C#N)C=C1 DNLUVZFMNAQCGT-UHFFFAOYSA-N 0.000 claims 1
• PKWYPQLJZSIHNK-UHFFFAOYSA-N 4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(C#N)C=C1 PKWYPQLJZSIHNK-UHFFFAOYSA-N 0.000 claims 1
• IFMBPMXEHFFGDK-UHFFFAOYSA-N 4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1N1C2=C3C=C(C#CC=4C=NC=CC=4)C=CC3=NC=C2N=C1 IFMBPMXEHFFGDK-UHFFFAOYSA-N 0.000 claims 1
• NUSVXJWRGBIIKB-UHFFFAOYSA-N 5-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-(2-oxopyrrolidin-1-yl)benzonitrile Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1C#N)=CC=C1N1CCCC1=O NUSVXJWRGBIIKB-UHFFFAOYSA-N 0.000 claims 1
• YXATVHGVNCXMQF-UHFFFAOYSA-N 5-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-(4-methylpiperazin-1-yl)benzonitrile Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1C#N)=CC=C1N1CCN(C)CC1 YXATVHGVNCXMQF-UHFFFAOYSA-N 0.000 claims 1
• IWMPPMHIRAVZIL-UHFFFAOYSA-N 5-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-piperazin-1-ylbenzonitrile Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1C#N)=CC=C1N1CCNCC1 IWMPPMHIRAVZIL-UHFFFAOYSA-N 0.000 claims 1
• KHBVAPOSMWSRCM-UHFFFAOYSA-N 5-[2-[1-[4-(2-aminoethyl)phenyl]imidazo[4,5-c]quinolin-8-yl]ethynyl]-n,n-dimethylpyridin-2-amine Chemical compound C1=NC(N(C)C)=CC=C1C#CC1=CC=C(N=CC2=C3N(C=4C=CC(CCN)=CC=4)C=N2)C3=C1 KHBVAPOSMWSRCM-UHFFFAOYSA-N 0.000 claims 1
• TULPSYVPDGACPC-UHFFFAOYSA-N 5-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-(2-oxopyrrolidin-1-yl)benzonitrile Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1C#N)=CC=C1N1CCCC1=O TULPSYVPDGACPC-UHFFFAOYSA-N 0.000 claims 1
• VGONDVFECSYQOX-UHFFFAOYSA-N 5-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-(4-methylpiperazin-1-yl)benzonitrile Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1C#N)=CC=C1N1CCN(C)CC1 VGONDVFECSYQOX-UHFFFAOYSA-N 0.000 claims 1
• RLACWGWRUKOXDK-UHFFFAOYSA-N 5-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-piperazin-1-ylbenzonitrile Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1C#N)=CC=C1N1CCNCC1 RLACWGWRUKOXDK-UHFFFAOYSA-N 0.000 claims 1
• RZRSFUKSUJNGCN-UHFFFAOYSA-N 5-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-(2-oxopyrrolidin-1-yl)benzonitrile Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C(C=C1C#N)=CC=C1N1CCCC1=O RZRSFUKSUJNGCN-UHFFFAOYSA-N 0.000 claims 1
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