CA2541691A1 - 1h-imidazo[4,5-c]quinoline derivatives in the treatment of protein kinase dependent diseases - Google Patents

Info

Publication number

CA2541691A1

CA2541691A1 CA002541691A CA2541691A CA2541691A1 CA 2541691 A1 CA2541691 A1 CA 2541691A1 CA 002541691 A CA002541691 A CA 002541691A CA 2541691 A CA2541691 A CA 2541691A CA 2541691 A1 CA2541691 A1 CA 2541691A1

Authority

CA

Canada

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 93
• 201000010099 disease Diseases 0.000 title claims abstract description 89
• 238000011282 treatment Methods 0.000 title claims abstract description 86
• 102000001253 Protein Kinase Human genes 0.000 title claims abstract description 44
• 108060006633 protein kinase Proteins 0.000 title claims abstract description 44
• 230000001419 dependent effect Effects 0.000 title claims abstract description 41
• 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 description 5
• 150000003839 salts Chemical class 0.000 claims abstract description 77
• 238000000034 method Methods 0.000 claims abstract description 40
• 241001465754 Metazoa Species 0.000 claims abstract description 22
• 230000008569 process Effects 0.000 claims abstract description 18
• 238000002360 preparation method Methods 0.000 claims abstract description 15
• 150000001875 compounds Chemical class 0.000 claims description 467
• 125000000217 alkyl group Chemical group 0.000 claims description 209
• -1 cyanomethyl Chemical group 0.000 claims description 190
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 87
• 239000001257 hydrogen Substances 0.000 claims description 76
• 229910052739 hydrogen Inorganic materials 0.000 claims description 76
• 125000003545 alkoxy group Chemical group 0.000 claims description 71
• 125000001424 substituent group Chemical group 0.000 claims description 70
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
• 229910052757 nitrogen Inorganic materials 0.000 claims description 58
• 125000005843 halogen group Chemical group 0.000 claims description 55
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
• 229910052760 oxygen Inorganic materials 0.000 claims description 45
• 239000000203 mixture Substances 0.000 claims description 44
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
• 125000004076 pyridyl group Chemical group 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000004434 sulfur atom Chemical group 0.000 claims description 31
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 30
• 206010028980 Neoplasm Diseases 0.000 claims description 30
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
• 125000004193 piperazinyl group Chemical group 0.000 claims description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 28
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
• 125000001153 fluoro group Chemical group F* 0.000 claims description 26
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 23
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
• 125000004414 alkyl thio group Chemical group 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
• 125000004419 alkynylene group Chemical group 0.000 claims description 14
• 125000003277 amino group Chemical group 0.000 claims description 14
• 201000011510 cancer Diseases 0.000 claims description 14
• 125000004450 alkenylene group Chemical group 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 125000001246 bromo group Chemical group Br* 0.000 claims description 13
• 125000004122 cyclic group Chemical group 0.000 claims description 12
• 230000001225 therapeutic effect Effects 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 11
• 125000002757 morpholinyl group Chemical group 0.000 claims description 11
• 230000002062 proliferating effect Effects 0.000 claims description 11
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 10
• 125000005605 benzo group Chemical group 0.000 claims description 10
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 10
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 150000001204 N-oxides Chemical class 0.000 claims description 8
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 8
• 210000002307 prostate Anatomy 0.000 claims description 7
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 7
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 201000008275 breast carcinoma Diseases 0.000 claims description 6
• 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 6
• 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 6
• 230000009826 neoplastic cell growth Effects 0.000 claims description 6
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 210000004072 lung Anatomy 0.000 claims description 5
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• 208000005017 glioblastoma Diseases 0.000 claims description 4
• 206010020718 hyperplasia Diseases 0.000 claims description 4
• 239000000463 material Substances 0.000 claims description 4
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 4
• 230000001131 transforming effect Effects 0.000 claims description 4
• 201000009030 Carcinoma Diseases 0.000 claims description 3
• 208000012609 Cowden disease Diseases 0.000 claims description 3
• 201000002847 Cowden 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
• 208000034578 Multiple myelomas Diseases 0.000 claims description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 210000004100 adrenal gland Anatomy 0.000 claims description 3
• 210000000481 breast Anatomy 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 201000002758 colorectal adenoma Diseases 0.000 claims description 3
• 210000003734 kidney Anatomy 0.000 claims description 3
• 210000004185 liver Anatomy 0.000 claims description 3
• 208000025440 neoplasm of neck Diseases 0.000 claims description 3
• 210000001672 ovary Anatomy 0.000 claims description 3
• 210000000496 pancreas Anatomy 0.000 claims description 3
• 210000000664 rectum Anatomy 0.000 claims description 3
• 210000002784 stomach Anatomy 0.000 claims description 3
• 210000001685 thyroid gland Anatomy 0.000 claims description 3
• 210000003932 urinary bladder Anatomy 0.000 claims description 3
• 210000001215 vagina Anatomy 0.000 claims description 3
• 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 2
• 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 description 2
• FSQRRJDBAPWDTN-UHFFFAOYSA-N n-methyl-n-[4-[3-methyl-2-oxo-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]acetamide Chemical compound C1=CC(N(C(C)=O)C)=CC=C1N1C(=O)N(C)C2=C1C1=CC(C#CC=3C=NC=CC=3)=CC=C1N=C2 FSQRRJDBAPWDTN-UHFFFAOYSA-N 0.000 claims description 2
• 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
• 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 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
• 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 1
• 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
• 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
• 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
• 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
• 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
• 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
• FDLDKCFSMXRNFW-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-5-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound C1CN(C)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2C)C#CC=2C=NC=CC=2)C=C1C#N FDLDKCFSMXRNFW-UHFFFAOYSA-N 0.000 claims 1
• ZXKGSJAYTVILQV-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-5-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]benzonitrile Chemical compound C1CN(C)CCN1C1=CC=C(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)C=C1C#N ZXKGSJAYTVILQV-UHFFFAOYSA-N 0.000 claims 1
• DTCRGHNEKMCSIL-UHFFFAOYSA-N 2-(cyanomethyl)-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(CC#N)C(C#N)=C1 DTCRGHNEKMCSIL-UHFFFAOYSA-N 0.000 claims 1
• PWMOOUOVIZJFEW-UHFFFAOYSA-N 2-[2-fluoro-4-[2-methoxy-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]acetonitrile Chemical compound COC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CC#N)C(F)=C1 PWMOOUOVIZJFEW-UHFFFAOYSA-N 0.000 claims 1
• RRLZMJLHTFKNAN-UHFFFAOYSA-N 2-[2-fluoro-4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]-2-methylpropanenitrile Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(C(C)(C)C#N)C(F)=C1 RRLZMJLHTFKNAN-UHFFFAOYSA-N 0.000 claims 1
• RPAMXVWTLSJNDT-UHFFFAOYSA-N 2-[2-fluoro-4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]acetonitrile Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CC#N)C(F)=C1 RPAMXVWTLSJNDT-UHFFFAOYSA-N 0.000 claims 1
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