MXPA06005701A

MXPA06005701A - Derivados de 1h-imidazo[4,5-c)quinolina en el tratamiento de enfermedades dependientes de quinasa de proteina.

Derivados de 1h-imidazo[4,5-c)quinolina en el tratamiento de enfermedades dependientes de quinasa de proteina.

Info

Publication number: MXPA06005701A
Authority: MX; Mexico
Prior art keywords: phenyl; imidazo; quinolin; pyridin; methyl
Prior art date: 2003-11-21

Application number

MXPA06005701A

Other languages

English (en)

Spanish (es)

Inventor

Frederic Stauffer

Original Assignee

Novartis Ag

Priority date

2003-11-21

Filing date

2004-11-19

Publication date

2006-08-17

2004-11-19 Application filed by Novartis Ag filed Critical Novartis Ag

2006-08-17 Publication of MXPA06005701A publication Critical patent/MXPA06005701A/es

Links

208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 91
201000010099 disease Diseases 0.000 title claims abstract description 90
238000011282 treatment Methods 0.000 title claims abstract description 64
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 81
241001465754 Metazoa Species 0.000 claims abstract description 21
238000004519 manufacturing process Methods 0.000 claims abstract description 21
238000002360 preparation method Methods 0.000 claims abstract description 19
150000001875 compounds Chemical class 0.000 claims description 439
-1 cyano-methyl Chemical group 0.000 claims description 313
125000000217 alkyl group Chemical group 0.000 claims description 202
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 88
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 68
125000001424 substituent group Chemical group 0.000 claims description 66
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 62
229910052736 halogen Inorganic materials 0.000 claims description 61
150000002367 halogens Chemical class 0.000 claims description 61
229910052757 nitrogen Inorganic materials 0.000 claims description 61
125000004432 carbon atom Chemical group C* 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
239000000203 mixture Substances 0.000 claims description 43
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 39
229910052731 fluorine Inorganic materials 0.000 claims description 39
125000000753 cycloalkyl group Chemical group 0.000 claims description 38
229910052760 oxygen Inorganic materials 0.000 claims description 36
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
239000000460 chlorine Substances 0.000 claims description 33
239000001301 oxygen Substances 0.000 claims description 33
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
125000004193 piperazinyl group Chemical group 0.000 claims description 30
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
206010028980 Neoplasm Diseases 0.000 claims description 28
229910052801 chlorine Inorganic materials 0.000 claims description 28
125000000623 heterocyclic group Chemical group 0.000 claims description 28
125000002393 azetidinyl group Chemical group 0.000 claims description 27
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 26
239000011737 fluorine Substances 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 25
239000008194 pharmaceutical composition Substances 0.000 claims description 24
125000002636 imidazolinyl group Chemical group 0.000 claims description 23
125000004076 pyridyl group Chemical group 0.000 claims description 23
125000004434 sulfur atom Chemical group 0.000 claims description 23
125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
125000004414 alkyl thio group Chemical group 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
230000009021 linear effect Effects 0.000 claims description 17
150000003254 radicals Chemical class 0.000 claims description 17
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125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
125000004450 alkenylene group Chemical group 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000003277 amino group Chemical group 0.000 claims description 14
125000004419 alkynylene group Chemical class 0.000 claims description 13
125000004122 cyclic group Chemical group 0.000 claims description 12
125000002883 imidazolyl group Chemical group 0.000 claims description 11
230000002062 proliferating effect Effects 0.000 claims description 11
230000001225 therapeutic 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
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 10
239000000463 material Substances 0.000 claims description 10
125000002757 morpholinyl group Chemical group 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 8
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 8
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 7
210000004072 lung Anatomy 0.000 claims description 7
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 7
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims description 6
201000004681 Psoriasis Diseases 0.000 claims description 6
201000008275 breast carcinoma Diseases 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
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
125000004103 aminoalkyl group Chemical group 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
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
206010009944 Colon cancer Diseases 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
210000004556 brain Anatomy 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 4
210000002307 prostate Anatomy 0.000 claims description 4
210000003932 urinary bladder Anatomy 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
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
201000007815 Bannayan-Riley-Ruvalcaba syndrome Diseases 0.000 claims description 3
208000012609 Cowden disease Diseases 0.000 claims description 3
201000002847 Cowden syndrome Diseases 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
239000005977 Ethylene Substances 0.000 claims description 3
206010061968 Gastric neoplasm 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
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 3
210000004100 adrenal gland Anatomy 0.000 claims description 3
210000000481 breast Anatomy 0.000 claims description 3
208000035269 cancer or benign tumor Diseases 0.000 claims description 3
210000001072 colon Anatomy 0.000 claims description 3
201000002758 colorectal adenoma Diseases 0.000 claims description 3
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 3
208000005017 glioblastoma Diseases 0.000 claims description 3
206010020718 hyperplasia Diseases 0.000 claims description 3
210000004185 liver Anatomy 0.000 claims description 3
210000001672 ovary Anatomy 0.000 claims description 3
210000000496 pancreas Anatomy 0.000 claims description 3
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
210000002784 stomach Anatomy 0.000 claims description 3
230000001131 transforming effect Effects 0.000 claims description 3
210000001215 vagina Anatomy 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 2
206010038389 Renal cancer Diseases 0.000 claims description 2
208000025440 neoplasm of neck Diseases 0.000 claims description 2
210000000664 rectum Anatomy 0.000 claims description 2
210000001685 thyroid gland Anatomy 0.000 claims description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 2
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 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
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
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 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
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
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
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
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
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
ROPWJVBPRDGMAM-UHFFFAOYSA-N 2-[2-chloro-4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]acetonitrile Chemical compound C1=C(CC#N)C(Cl)=CC(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)=C1 ROPWJVBPRDGMAM-UHFFFAOYSA-N 0.000 claims 1
PWRCFINNJLQRSR-UHFFFAOYSA-N 2-[2-methyl-4-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]acetonitrile Chemical compound C1=C(CC#N)C(C)=CC(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)=C1 PWRCFINNJLQRSR-UHFFFAOYSA-N 0.000 claims 1
PWURTKWIWSYWMI-UHFFFAOYSA-N 2-[3-[8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]acetonitrile Chemical compound N#CCC1=CC=CC(N2C3=C4C=C(C=CC4=NC=C3N=C2)C#CC=2C=NC=CC=2)=C1 PWURTKWIWSYWMI-UHFFFAOYSA-N 0.000 claims 1
MWOGOMAHUFHDRI-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]-2-fluorophenyl]acetonitrile Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CC#N)C(F)=C1 MWOGOMAHUFHDRI-UHFFFAOYSA-N 0.000 claims 1
BIGTZTAYYDVSJN-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]acetonitrile Chemical compound CN(C)C1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CC#N)C=C1 BIGTZTAYYDVSJN-UHFFFAOYSA-N 0.000 claims 1
BJDMYXFWDKNPRE-UHFFFAOYSA-N 2-[4-[2-cyclopropyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1N1C2=C3C=C(C#CC=4C=NC=CC=4)C=CC3=NC=C2N=C1C1CC1 BJDMYXFWDKNPRE-UHFFFAOYSA-N 0.000 claims 1
GXHUXKJJDQZOKT-UHFFFAOYSA-N 2-[4-[2-ethyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]ethanamine Chemical compound CCC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CCN)C=C1 GXHUXKJJDQZOKT-UHFFFAOYSA-N 0.000 claims 1
MVTWCHNACQODRH-UHFFFAOYSA-N 2-[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=C1 MVTWCHNACQODRH-UHFFFAOYSA-N 0.000 claims 1
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 1
RQKHFSJUFRSGMA-UHFFFAOYSA-N 2-[4-[2-methyl-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]ethanamine Chemical compound CC1=NC2=CN=C3C=CC(C#CC=4C=NC=CC=4)=CC3=C2N1C1=CC=C(CCN)C=C1 RQKHFSJUFRSGMA-UHFFFAOYSA-N 0.000 claims 1
RVVWWSGDRUTHGH-UHFFFAOYSA-N 2-[4-[7-chloro-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1N1C2=C3C=C(C#CC=4C=NC=CC=4)C(Cl)=CC3=NC=C2N=C1 RVVWWSGDRUTHGH-UHFFFAOYSA-N 0.000 claims 1
GUURXBUWFNOOKT-UHFFFAOYSA-N 2-[4-[7-fluoro-8-(2-pyridin-3-ylethynyl)imidazo[4,5-c]quinolin-1-yl]phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1N1C2=C3C=C(C#CC=4C=NC=CC=4)C(F)=CC3=NC=C2N=C1 GUURXBUWFNOOKT-UHFFFAOYSA-N 0.000 claims 1
NPGMFTZPULRBEL-UHFFFAOYSA-N 2-[4-[8-[2-(1,3-benzodioxol-5-yl)ethynyl]-7-fluoroimidazo[4,5-c]quinolin-1-yl]phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1N1C2=C3C=C(C#CC=4C=C5OCOC5=CC=4)C(F)=CC3=NC=C2N=C1 NPGMFTZPULRBEL-UHFFFAOYSA-N 0.000 claims 1
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
GVPAGJWVBUZHNQ-UHFFFAOYSA-N 2-methyl-2-[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(C(C)(C)C#N)C=C1 GVPAGJWVBUZHNQ-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
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