RU2623427C2 - Гетероциклические соединения и их применение в качестве ингибиторов киназы-3 гликогенсинтазы - Google Patents

Info

Publication number

RU2623427C2

RU2623427C2 RU2013135477A RU2013135477A RU2623427C2 RU 2623427 C2 RU2623427 C2 RU 2623427C2 RU 2013135477 A RU2013135477 A RU 2013135477A RU 2013135477 A RU2013135477 A RU 2013135477A RU 2623427 C2 RU2623427 C2 RU 2623427C2

Authority

RU

Russia

Prior art keywords

urea

pyridin

quinolin

pyran

fluoroquinolin

Prior art date

2010-12-30

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• 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 31
• 239000003572 glycogen synthase kinase 3 inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 331
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 60
• 239000001257 hydrogen Substances 0.000 claims abstract description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 38
• 238000000034 method Methods 0.000 claims abstract description 35
• 238000011282 treatment Methods 0.000 claims abstract description 35
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
• 230000000694 effects Effects 0.000 claims abstract description 26
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 24
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
• 150000002367 halogens Chemical class 0.000 claims abstract description 20
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
• 125000001424 substituent group Chemical group 0.000 claims abstract description 19
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
• 108091007911 GSKs Proteins 0.000 claims abstract description 10
• 102000004103 Glycogen Synthase Kinases Human genes 0.000 claims abstract description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 5
• 229910052727 yttrium Inorganic materials 0.000 claims abstract description 3
• -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 267
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 150000002431 hydrogen Chemical class 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 17
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• PYOMPXLAYCWFPK-UHFFFAOYSA-N 1-(6-bromoquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(Br)=CC=C3N=CC=2)=N1 PYOMPXLAYCWFPK-UHFFFAOYSA-N 0.000 claims description 12
• RMWWSSJQQBSPNH-UHFFFAOYSA-N 1-[6-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C=2CCNCC=2)=N1 RMWWSSJQQBSPNH-UHFFFAOYSA-N 0.000 claims description 11
• 239000004202 carbamide Substances 0.000 claims description 11
• 208000035475 disorder Diseases 0.000 claims description 11
• MIBNRIDIGPQNKR-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-(6-piperidin-4-ylpyridin-2-yl)urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCNCC1 MIBNRIDIGPQNKR-UHFFFAOYSA-N 0.000 claims description 9
• BYKSEVADXIBXTH-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)pyridin-2-yl]-3-(8-fluoroquinolin-4-yl)urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1=CCOCC1 BYKSEVADXIBXTH-UHFFFAOYSA-N 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 9
• YEJAFXVKMRTNJM-UHFFFAOYSA-N tert-butyl 4-[4-[[6-(trifluoromethyl)pyridin-2-yl]carbamoylamino]quinolin-6-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=C3C(NC(=O)NC=4N=C(C=CC=4)C(F)(F)F)=CC=NC3=CC=2)=C1 YEJAFXVKMRTNJM-UHFFFAOYSA-N 0.000 claims description 9
• 108010001483 Glycogen Synthase Proteins 0.000 claims description 8
• GWCWCWXMAZCRIV-UHFFFAOYSA-N 1-[6-(3,4-dihydro-2h-pyran-5-yl)pyridin-2-yl]-3-(8-fluoroquinolin-4-yl)urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1=COCCC1 GWCWCWXMAZCRIV-UHFFFAOYSA-N 0.000 claims description 7
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• JDLZNEXCJIZHBW-UHFFFAOYSA-N 1-(6-piperidin-4-ylquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C2CCNCC2)=N1 JDLZNEXCJIZHBW-UHFFFAOYSA-N 0.000 claims description 5
• LMBZXVCPBNGXGR-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 LMBZXVCPBNGXGR-UHFFFAOYSA-N 0.000 claims description 5
• 208000006011 Stroke Diseases 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• PKQSFTTUFQKADK-UHFFFAOYSA-N tert-butyl 4-[6-[(8-fluoroquinolin-4-yl)carbamoylamino]pyridin-2-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2N=C(NC(=O)NC=3C4=CC=CC(F)=C4N=CC=3)C=CC=2)=C1 PKQSFTTUFQKADK-UHFFFAOYSA-N 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• RISTYTNTGUCKRV-UHFFFAOYSA-N 1-(6-piperidin-4-ylquinolin-4-yl)-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC=C(C3CCNCC3)C=C2C=1NC(=O)NC1=CN=CC=N1 RISTYTNTGUCKRV-UHFFFAOYSA-N 0.000 claims description 4
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
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• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• ZERCZJXRIJFBEL-UHFFFAOYSA-N tert-butyl 4-[4-[(6-cyclopropylpyrazin-2-yl)carbamoylamino]quinolin-6-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=C3C(NC(=O)NC=4N=C(C=NC=4)C4CC4)=CC=NC3=CC=2)=C1 ZERCZJXRIJFBEL-UHFFFAOYSA-N 0.000 claims description 4
• HXBDFOQTPGIDNA-UHFFFAOYSA-N 1-(6-cyclopropylpyrazin-2-yl)-3-(6-piperidin-4-ylquinolin-4-yl)urea Chemical compound C=1C=NC2=CC=C(C3CCNCC3)C=C2C=1NC(=O)NC(N=1)=CN=CC=1C1CC1 HXBDFOQTPGIDNA-UHFFFAOYSA-N 0.000 claims description 3
• VDEZAETUSYBUSQ-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-[6-(oxan-3-yl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1CCCOC1 VDEZAETUSYBUSQ-UHFFFAOYSA-N 0.000 claims description 3
• VQPBIJGXSXEOCU-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC1=CC=CC(C(F)(F)F)=N1 VQPBIJGXSXEOCU-UHFFFAOYSA-N 0.000 claims description 3
• WSNGAJHTEQWBIM-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[5-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=C1)=CC=C1C1CCOCC1 WSNGAJHTEQWBIM-UHFFFAOYSA-N 0.000 claims description 3
• YCEGRQBTGLDCDA-UHFFFAOYSA-N 1-[6-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1N(C)CCC(C=2C=C3C(NC(=O)NC=4N=C(C=CC=4)C(F)(F)F)=CC=NC3=CC=2)=C1 YCEGRQBTGLDCDA-UHFFFAOYSA-N 0.000 claims description 3
• DSWADQAUCOSMPB-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)pyridin-2-yl]-3-(1,5-naphthyridin-4-yl)urea Chemical compound C=1C=NC2=CC=CN=C2C=1NC(=O)NC(N=1)=CC=CC=1C1=CCOCC1 DSWADQAUCOSMPB-UHFFFAOYSA-N 0.000 claims description 3
• TVXURCBJJQDUAY-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC=C(C=3CCOCC=3)C=C2C=1NC(=O)NC1=CN=CC=N1 TVXURCBJJQDUAY-UHFFFAOYSA-N 0.000 claims description 3
• COCKHBFAABWZBN-UHFFFAOYSA-N 1-pyrazin-2-yl-3-[6-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl]urea Chemical compound C=1C=NC2=CC=C(C=3CCNCC=3)C=C2C=1NC(=O)NC1=CN=CC=N1 COCKHBFAABWZBN-UHFFFAOYSA-N 0.000 claims description 3
• 208000020925 Bipolar disease Diseases 0.000 claims description 3
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• 208000002193 Pain Diseases 0.000 claims description 3
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• 206010038923 Retinopathy Diseases 0.000 claims description 3
• 201000004810 Vascular dementia Diseases 0.000 claims description 3
• 201000008482 osteoarthritis Diseases 0.000 claims description 3
• 208000027232 peripheral nervous system disease Diseases 0.000 claims description 3
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 201000000980 schizophrenia Diseases 0.000 claims description 3
• 239000010802 sludge Substances 0.000 claims description 3
• YCACGYUSNVXULM-UHFFFAOYSA-N tert-butyl 3-[4-(pyrazin-2-ylcarbamoylamino)quinolin-6-yl]-2,5-dihydropyrrole-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC=C1C1=CC=C(N=CC=C2NC(=O)NC=3N=CC=NC=3)C2=C1 YCACGYUSNVXULM-UHFFFAOYSA-N 0.000 claims description 3
• GBJYNPNJPWTFLR-UHFFFAOYSA-N tert-butyl 3-[4-[[6-(trifluoromethyl)pyridin-2-yl]carbamoylamino]quinolin-6-yl]-2,5-dihydropyrrole-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC=C1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 GBJYNPNJPWTFLR-UHFFFAOYSA-N 0.000 claims description 3
• HJULFMJNYVIQIN-UHFFFAOYSA-N tert-butyl 4-[4-(pyrazin-2-ylcarbamoylamino)quinolin-6-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=C3C(NC(=O)NC=4N=CC=NC=4)=CC=NC3=CC=2)=C1 HJULFMJNYVIQIN-UHFFFAOYSA-N 0.000 claims description 3
• VQXPGDQCCCDBMS-UHFFFAOYSA-N tert-butyl 4-[6-[(8-fluoroquinolin-4-yl)carbamoylamino]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC(NC(=O)NC=2C3=CC=CC(F)=C3N=CC=2)=N1 VQXPGDQCCCDBMS-UHFFFAOYSA-N 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 230000008736 traumatic injury Effects 0.000 claims description 3
• HUIGDQIGGTVHLC-UHFFFAOYSA-N 1-(1,5-naphthyridin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC=CN=C2C=1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 HUIGDQIGGTVHLC-UHFFFAOYSA-N 0.000 claims description 2
• NUVBOUNAXOEMGL-UHFFFAOYSA-N 1-(5,8-difluoroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=C(F)C2=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 NUVBOUNAXOEMGL-UHFFFAOYSA-N 0.000 claims description 2
• KJDGNNMYOYVDES-UHFFFAOYSA-N 1-(6,8-dichloroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(Cl)=CC(Cl)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 KJDGNNMYOYVDES-UHFFFAOYSA-N 0.000 claims description 2
• YVCQZVBSYKUTNJ-UHFFFAOYSA-N 1-(6,8-difluoroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(F)=CC(F)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 YVCQZVBSYKUTNJ-UHFFFAOYSA-N 0.000 claims description 2
• AUBIMDGQGZMWTM-UHFFFAOYSA-N 1-(6,8-difluoroquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C12=CC(F)=CC(F)=C2N=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=N1 AUBIMDGQGZMWTM-UHFFFAOYSA-N 0.000 claims description 2
• OKGRTJOEILSKSR-UHFFFAOYSA-N 1-(6-cyclopropylpyrazin-2-yl)-3-[6-(1-methylpiperidin-4-yl)quinolin-4-yl]urea Chemical compound C1CN(C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=NC=3)C3CC3)C2=C1 OKGRTJOEILSKSR-UHFFFAOYSA-N 0.000 claims description 2
• YYJKBJITPDPGDD-UHFFFAOYSA-N 1-(7-bromoquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=C(Br)C=C3N=CC=2)=N1 YYJKBJITPDPGDD-UHFFFAOYSA-N 0.000 claims description 2
• OVIADVAXXQTSSR-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 OVIADVAXXQTSSR-UHFFFAOYSA-N 0.000 claims description 2
• OHHJJQZGSOYSCF-UHFFFAOYSA-N 1-(8-chloro-6-methylquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(C)=CC(Cl)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 OHHJJQZGSOYSCF-UHFFFAOYSA-N 0.000 claims description 2
• CINSMAXRSWIPNW-UHFFFAOYSA-N 1-(8-chloroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(Cl)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 CINSMAXRSWIPNW-UHFFFAOYSA-N 0.000 claims description 2
• WMDXIIORGIWVQV-UHFFFAOYSA-N 1-(8-fluoro-6-methoxyquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(OC)=CC(F)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 WMDXIIORGIWVQV-UHFFFAOYSA-N 0.000 claims description 2
• XGYJOSADRJVTBY-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[6-(oxan-3-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCCOC1 XGYJOSADRJVTBY-UHFFFAOYSA-N 0.000 claims description 2
• CCABGQQISWNPAY-UHFFFAOYSA-N 1-(8-iodoquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=CC(I)=C3N=CC=2)=N1 CCABGQQISWNPAY-UHFFFAOYSA-N 0.000 claims description 2
• VHYMKHPSLVPMPC-UHFFFAOYSA-N 1-[6-(1-methylpiperidin-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1CN(C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 VHYMKHPSLVPMPC-UHFFFAOYSA-N 0.000 claims description 2
• FQVMTXVNXUTWIN-UHFFFAOYSA-N 1-[6-(1-methylpiperidin-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C1CN(C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=CC=NC=3)C2=C1 FQVMTXVNXUTWIN-UHFFFAOYSA-N 0.000 claims description 2
• QFLPJUZAYALTDE-UHFFFAOYSA-N 1-[6-(2,5-dihydro-1h-pyrrol-3-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C=2CNCC=2)=N1 QFLPJUZAYALTDE-UHFFFAOYSA-N 0.000 claims description 2
• HDQBKWBMALHQDI-UHFFFAOYSA-N 1-[6-(3,4-dihydro-2h-pyran-5-yl)pyridin-2-yl]-3-(7-methoxyquinolin-4-yl)urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1=COCCC1 HDQBKWBMALHQDI-UHFFFAOYSA-N 0.000 claims description 2
• DPEJUTFDLXESIT-UHFFFAOYSA-N 1-[6-(3,4-dihydro-2h-pyran-5-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C=2CCCOC=2)=N1 DPEJUTFDLXESIT-UHFFFAOYSA-N 0.000 claims description 2
• RVFDHEQGKBMEMP-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)pyridin-2-yl]-3-(7-methoxyquinolin-4-yl)urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1=CCOCC1 RVFDHEQGKBMEMP-UHFFFAOYSA-N 0.000 claims description 2
• VXQWZNGQNKCLKD-UHFFFAOYSA-N 1-[6-(oxan-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C2CCOCC2)=N1 VXQWZNGQNKCLKD-UHFFFAOYSA-N 0.000 claims description 2
• XFRYMFRHCLWJQY-UHFFFAOYSA-N 1-[6-(trifluoromethyl)pyridin-2-yl]-3-[7-(trifluoromethyl)quinolin-4-yl]urea Chemical compound C=1C=NC2=CC(C(F)(F)F)=CC=C2C=1NC(=O)NC1=CC=CC(C(F)(F)F)=N1 XFRYMFRHCLWJQY-UHFFFAOYSA-N 0.000 claims description 2
• FBWWNLBZZFVRQY-UHFFFAOYSA-N 1-[6-(trifluoromethyl)pyridin-2-yl]-3-[8-(trifluoromethyl)quinolin-4-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=N1 FBWWNLBZZFVRQY-UHFFFAOYSA-N 0.000 claims description 2
• VBISSAFCYVKVAC-UHFFFAOYSA-N 1-[6-[1-(2,2-difluoroethyl)piperidin-4-yl]pyridin-2-yl]-3-(8-fluoroquinolin-4-yl)urea Chemical compound C1CN(CC(F)F)CCC1C1=CC=CC(NC(=O)NC=2C3=CC=CC(F)=C3N=CC=2)=N1 VBISSAFCYVKVAC-UHFFFAOYSA-N 0.000 claims description 2
• DCHDMOPFMYEBSB-UHFFFAOYSA-N 1-[6-[1-(2,2-difluoroethyl)piperidin-4-yl]quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1CN(CC(F)F)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 DCHDMOPFMYEBSB-UHFFFAOYSA-N 0.000 claims description 2
• HEFHJWMRPPVCTR-UHFFFAOYSA-N 1-[6-[1-(2-fluoroethyl)piperidin-4-yl]quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1CN(CCF)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 HEFHJWMRPPVCTR-UHFFFAOYSA-N 0.000 claims description 2
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