CA2727607A1 - 2-pyridyl substituted imidazoles as alk5 and/or alk4 inhibitors - Google Patents

Info

Publication number

CA2727607A1

CA2727607A1 CA2727607A CA2727607A CA2727607A1 CA 2727607 A1 CA2727607 A1 CA 2727607A1 CA 2727607 A CA2727607 A CA 2727607A CA 2727607 A CA2727607 A CA 2727607A CA 2727607 A1 CA2727607 A1 CA 2727607A1

Authority

CA

Canada

Prior art keywords

imidazol

methylpyridin

quinoline

fluoro

methyl

Prior art date

2008-06-12

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

• 239000003112 inhibitor Substances 0.000 title abstract description 13
• 150000002460 imidazoles Chemical class 0.000 title description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 title description 3
• -1 2-pyridyl-substituted imidazoles Chemical class 0.000 claims abstract description 140
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
• 201000010099 disease Diseases 0.000 claims abstract description 14
• 230000001404 mediated effect Effects 0.000 claims abstract description 10
• 238000011282 treatment Methods 0.000 claims abstract description 6
• 150000001875 compounds Chemical class 0.000 claims description 75
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 125000004122 cyclic group Chemical group 0.000 claims description 26
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 25
• 238000000034 method Methods 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 22
• 101000799189 Homo sapiens Activin receptor type-1B Proteins 0.000 claims description 21
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 10
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
• FYNWYMYWFIXHNO-UHFFFAOYSA-N 2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(O)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 FYNWYMYWFIXHNO-UHFFFAOYSA-N 0.000 claims description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 8
• DISRINLOFKCEPS-UHFFFAOYSA-N 2-fluoro-n-(2-hydroxyethyl)-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]benzamide Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C(=O)NCCO)N2)C=2C=C3C=CC=NC3=CC=2)=N1 DISRINLOFKCEPS-UHFFFAOYSA-N 0.000 claims description 7
• 208000035475 disorder Diseases 0.000 claims description 7
• MELFLWJNWMRMJM-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCC(O)=O)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 MELFLWJNWMRMJM-UHFFFAOYSA-N 0.000 claims description 6
• CGFOUOBDUSKFJL-UHFFFAOYSA-N 6-[2-[(4-bromophenyl)methyl]-5-(6-methoxypyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound COC1=CC=CC(C2=C(N=C(CC=3C=CC(Br)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 CGFOUOBDUSKFJL-UHFFFAOYSA-N 0.000 claims description 6
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
• 208000032056 Radiation Fibrosis Syndrome Diseases 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 208000015181 infectious disease Diseases 0.000 claims description 6
• 230000037390 scarring Effects 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• PUGXCELHUHOMOZ-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]anilino]ethanol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(NCCO)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 PUGXCELHUHOMOZ-UHFFFAOYSA-N 0.000 claims description 5
• AQPOIBIHVYARJG-UHFFFAOYSA-N 6-[2-[(3-chloro-4-methoxyphenyl)methyl]-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoline 6-[5-(6-methylpyridin-2-yl)-2-[[4-(trifluoromethoxy)phenyl]methyl]-1H-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC=C(C=C1)OC(F)(F)F)C=1C=C2C=CC=NC2=CC1.ClC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1OC AQPOIBIHVYARJG-UHFFFAOYSA-N 0.000 claims description 5
• VQQKSXCXPRMTJB-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-2-[[4-(trifluoromethyl)phenyl]methyl]-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=CC(=CC=3)C(F)(F)F)N2)C=2C=C3C=CC=NC3=CC=2)=N1 VQQKSXCXPRMTJB-UHFFFAOYSA-N 0.000 claims description 5
• DOHITPBONVMFMD-UHFFFAOYSA-N BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC(=NC3=CC2)C)C2=NC(=CC=C2)Br)C=CC1.BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC(=NC2=CC1)C Chemical compound BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC(=NC3=CC2)C)C2=NC(=CC=C2)Br)C=CC1.BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC(=NC2=CC1)C DOHITPBONVMFMD-UHFFFAOYSA-N 0.000 claims description 5
• SUQSVSNGLCSZKN-UHFFFAOYSA-N ClC1=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC(=C1)Cl.ClC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1Cl Chemical compound ClC1=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC(=C1)Cl.ClC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1Cl SUQSVSNGLCSZKN-UHFFFAOYSA-N 0.000 claims description 5
• MMJDZFRHVFUFBV-UHFFFAOYSA-N ClC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)Cl)C=CC1.ClC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC=NC2=CC1 Chemical compound ClC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)Cl)C=CC1.ClC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC=NC2=CC1 MMJDZFRHVFUFBV-UHFFFAOYSA-N 0.000 claims description 5
• NPRQWFNBCJRQGM-UHFFFAOYSA-N FC1=C(N)C=C(C=C1)CC=1NC(=C(N1)C=1C=C2C=CC=NC2=CC1)C1=NC(=CC=C1)C.FC1=C(C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1)[N+](=O)[O-] Chemical compound FC1=C(N)C=C(C=C1)CC=1NC(=C(N1)C=1C=C2C=CC=NC2=CC1)C1=NC(=CC=C1)C.FC1=C(C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1)[N+](=O)[O-] NPRQWFNBCJRQGM-UHFFFAOYSA-N 0.000 claims description 5
• GRSMBGMVBMLADD-UHFFFAOYSA-N FC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC=NC2=CC1 Chemical compound FC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC=NC2=CC1 GRSMBGMVBMLADD-UHFFFAOYSA-N 0.000 claims description 5
• 208000025865 Ulcer Diseases 0.000 claims description 5
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 5
• 230000003176 fibrotic effect Effects 0.000 claims description 5
• 230000012010 growth Effects 0.000 claims description 5
• 208000017169 kidney disease Diseases 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 201000002793 renal fibrosis Diseases 0.000 claims description 5
• 231100000397 ulcer Toxicity 0.000 claims description 5
• HVPVJQMSTXTZLD-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]-n,n-dimethylethanamine Chemical compound C1=C(F)C(OCCN(C)C)=CC(CC=2NC(=C(N=2)C=2C=C3C=CC=NC3=CC=2)C=2N=C(C)C=CC=2)=C1 HVPVJQMSTXTZLD-UHFFFAOYSA-N 0.000 claims description 4
• 206010020772 Hypertension Diseases 0.000 claims description 4
• 206010027476 Metastases Diseases 0.000 claims description 4
• 208000007536 Thrombosis Diseases 0.000 claims description 4
• 229940079593 drug Drugs 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 230000009401 metastasis Effects 0.000 claims description 4
• 230000029663 wound healing Effects 0.000 claims description 4
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
• 201000003066 Diffuse Scleroderma Diseases 0.000 claims description 3
• 208000001708 Dupuytren contracture Diseases 0.000 claims description 3
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
• 206010019280 Heart failures Diseases 0.000 claims description 3
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 3
• 206010061216 Infarction Diseases 0.000 claims description 3
• 206010023421 Kidney fibrosis Diseases 0.000 claims description 3
• 208000005777 Lupus Nephritis Diseases 0.000 claims description 3
• 208000009525 Myocarditis Diseases 0.000 claims description 3
• 208000001132 Osteoporosis Diseases 0.000 claims description 3
• 208000002158 Proliferative Vitreoretinopathy Diseases 0.000 claims description 3
• 208000012322 Raynaud phenomenon Diseases 0.000 claims description 3
• 206010038934 Retinopathy proliferative Diseases 0.000 claims description 3
• 206010039710 Scleroderma Diseases 0.000 claims description 3
• 208000002847 Surgical Wound Diseases 0.000 claims description 3
• 201000009594 Systemic Scleroderma Diseases 0.000 claims description 3
• 206010042953 Systemic sclerosis Diseases 0.000 claims description 3
• 206010057469 Vascular stenosis Diseases 0.000 claims description 3
• 206010069351 acute lung injury Diseases 0.000 claims description 3
• 206010003246 arthritis Diseases 0.000 claims description 3
• 210000003445 biliary tract Anatomy 0.000 claims description 3
• 230000009787 cardiac fibrosis Effects 0.000 claims description 3
• 201000001981 dermatomyositis Diseases 0.000 claims description 3
• 210000004207 dermis Anatomy 0.000 claims description 3
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
• 208000027700 hepatic dysfunction Diseases 0.000 claims description 3
• 208000006454 hepatitis Diseases 0.000 claims description 3
• 231100000283 hepatitis Toxicity 0.000 claims description 3
• 230000001969 hypertrophic effect Effects 0.000 claims description 3
• 230000001771 impaired effect Effects 0.000 claims description 3
• 201000001881 impotence Diseases 0.000 claims description 3
• 239000012678 infectious agent Substances 0.000 claims description 3
• 230000002458 infectious effect Effects 0.000 claims description 3
• 208000014674 injury Diseases 0.000 claims description 3
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 3
• 208000011379 keloid formation Diseases 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 claims description 3
• 230000007658 neurological function Effects 0.000 claims description 3
• 208000005987 polymyositis Diseases 0.000 claims description 3
• 230000006785 proliferative vitreoretinopathy Effects 0.000 claims description 3
• 208000037803 restenosis Diseases 0.000 claims description 3
• 231100000241 scar Toxicity 0.000 claims description 3
• 231100000167 toxic agent Toxicity 0.000 claims description 3
• 239000003440 toxic substance Substances 0.000 claims description 3
• 230000008733 trauma Effects 0.000 claims description 3
• HRYBTWMYJRIINV-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C=CC=3)C(F)(F)F)N2)C=2C=CC(Cl)=CC=2)=N1 HRYBTWMYJRIINV-UHFFFAOYSA-N 0.000 claims description 2
• 208000007122 AIDS-Associated Nephropathy Diseases 0.000 claims description 2
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
• 206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 2
• 201000010046 Dilated cardiomyopathy Diseases 0.000 claims description 2
• 206010070737 HIV associated nephropathy Diseases 0.000 claims description 2
• 208000004362 Penile Induration Diseases 0.000 claims description 2
• 208000020758 Peyronie disease Diseases 0.000 claims description 2
• 208000003782 Raynaud disease Diseases 0.000 claims description 2
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 2
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• UWYYRRSLCUSOET-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCC(O)=O)C(F)=CC=3)N2)C=2C=C3N=CC=NC3=CC=2)=N1 UWYYRRSLCUSOET-UHFFFAOYSA-N 0.000 claims 4
• HHFOLCALAAIPPZ-UHFFFAOYSA-N 2-fluoro-n-(2-methoxyethyl)-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]benzamide Chemical compound C1=C(F)C(C(=O)NCCOC)=CC(CC=2NC(=C(N=2)C=2C=C3C=CC=NC3=CC=2)C=2N=C(C)C=CC=2)=C1 HHFOLCALAAIPPZ-UHFFFAOYSA-N 0.000 claims 4
• CGFBLQDLMVCSPT-UHFFFAOYSA-N 6-[2-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoxaline 6-[5-(6-methylpyridin-2-yl)-2-[[4-(trifluoromethyl)phenyl]methyl]-1H-imidazol-4-yl]quinoxaline Chemical compound FC(C=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C(C1)C(F)(F)F)(F)F.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC=C(C=C1)C(F)(F)F)C=1C=C2N=CC=NC2=CC1 CGFBLQDLMVCSPT-UHFFFAOYSA-N 0.000 claims 4
• BCGYYKZBQMKDRL-UHFFFAOYSA-N 6-[5-(6-bromopyridin-2-yl)-2-[(3-chlorophenyl)methyl]-1H-imidazol-4-yl]quinoline 2-methyl-6-[5-(6-methylpyridin-2-yl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1H-imidazol-4-yl]quinoline Chemical compound CC1=NC2=CC=C(C=C2C=C1)C=1N=C(NC1C1=NC(=CC=C1)C)CC1=CC(=CC=C1)C(F)(F)F.BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)Cl)C=1C=C2C=CC=NC2=CC1 BCGYYKZBQMKDRL-UHFFFAOYSA-N 0.000 claims 4
• WRMSWOPLPPJNBC-UHFFFAOYSA-N 6-[5-(6-bromopyridin-2-yl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1H-imidazol-4-yl]quinoline 6-[5-(6-methylpyridin-2-yl)-2-[(3-methylsulfonylphenyl)methyl]-1H-imidazol-4-yl]quinoline Chemical compound BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC=NC2=CC1.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)S(=O)(=O)C)C=1C=C2C=CC=NC2=CC1 WRMSWOPLPPJNBC-UHFFFAOYSA-N 0.000 claims 4
• SPDKJWOSWGZPTA-UHFFFAOYSA-N BrC1=CC=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC=CC=C2)C=C1.BrC1=CC=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1 Chemical compound BrC1=CC=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC=CC=C2)C=C1.BrC1=CC=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1 SPDKJWOSWGZPTA-UHFFFAOYSA-N 0.000 claims 4
• BSIRSUPRXMDVOT-UHFFFAOYSA-N BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)Br)C=CC1.BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)F)C=1C=C2C=CC=NC2=CC1 Chemical compound BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)Br)C=CC1.BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)F)C=1C=C2C=CC=NC2=CC1 BSIRSUPRXMDVOT-UHFFFAOYSA-N 0.000 claims 4
• FSYNQQNQWLHADA-UHFFFAOYSA-N CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=C(C=CC=C1)C(F)(F)F)C=1C=C2N=CC=NC2=CC1.FC1=C(C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1)C(F)(F)F Chemical compound CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=C(C=CC=C1)C(F)(F)F)C=1C=C2N=CC=NC2=CC1.FC1=C(C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1)C(F)(F)F FSYNQQNQWLHADA-UHFFFAOYSA-N 0.000 claims 4
• HCSZKQYKJFVQJL-UHFFFAOYSA-N CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC=C(C=C1)OC(F)(F)F)C=1C=C2N=CC=NC2=CC1.ClC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1OC Chemical compound CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC=C(C=C1)OC(F)(F)F)C=1C=C2N=CC=NC2=CC1.ClC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1OC HCSZKQYKJFVQJL-UHFFFAOYSA-N 0.000 claims 4
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