JP2010077116A5 - - Google Patents

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Publication number: JP2010077116A5
Authority: JP; Japan
Prior art keywords: ethyl; phenyl; trifluoromethyl; group; methyl
Prior art date: 2009-08-24
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.): Granted

Application number

JP2009192755A

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English (en)

Japanese (ja)

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JP2010077116A (ja

JP5319457B2 (ja

Filing date

2009-08-24

Publication date

2011-04-07

2009-08-24 Application filed filed Critical

2009-08-24 Priority to JP2009192755A priority Critical patent/JP5319457B2/ja

2009-08-24 Priority claimed from JP2009192755A external-priority patent/JP5319457B2/ja

2010-04-08 Publication of JP2010077116A publication Critical patent/JP2010077116A/ja

2011-04-07 Publication of JP2010077116A5 publication Critical patent/JP2010077116A5/ja

2013-10-16 Application granted granted Critical

2013-10-16 Publication of JP5319457B2 publication Critical patent/JP5319457B2/ja

Status Expired - Fee Related legal-status Critical Current

2029-08-24 Anticipated expiration legal-status Critical

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125000003545 alkoxy group Chemical group 0.000 claims 47
125000005843 halogen group Chemical group 0.000 claims 41
125000000217 alkyl group Chemical group 0.000 claims 38
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 33
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 27
125000000753 cycloalkyl group Chemical group 0.000 claims 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 16
125000001424 substituent group Chemical group 0.000 claims 16
125000003282 alkyl amino group Chemical group 0.000 claims 14
125000003118 aryl group Chemical group 0.000 claims 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 10
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 10
125000004093 cyano group Chemical group *C#N 0.000 claims 10
229910052757 nitrogen Inorganic materials 0.000 claims 10
125000004433 nitrogen atom Chemical group N* 0.000 claims 10
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 9
-1 4-methylpiperidino Chemical group 0.000 claims 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 8
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 8
125000004414 alkyl thio group Chemical group 0.000 claims 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
125000000623 heterocyclic group Chemical group 0.000 claims 6
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 5
125000003277 amino group Chemical group 0.000 claims 5
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 5
239000008194 pharmaceutical composition Substances 0.000 claims 5
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 4
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
125000004663 dialkyl amino group Chemical group 0.000 claims 4
239000003814 drug Substances 0.000 claims 4
125000005842 heteroatom Chemical group 0.000 claims 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 3
VLASFLMPJOEVBB-UHFFFAOYSA-N 2-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl-[[2-[cyclopentylmethyl(ethyl)amino]-5-(trifluoromethyl)phenyl]methyl]amino]pyrimidin-5-ol Chemical compound C=1C=C(C(F)(F)F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(O)=CN=2)C=1N(CC)CC1CCCC1 VLASFLMPJOEVBB-UHFFFAOYSA-N 0.000 claims 2
LQMGJFOHDAPZHH-UHFFFAOYSA-N 2-[4-[[2-[[1-[3,5-bis(trifluoromethyl)phenyl]ethyl-[5-(2-methylsulfanylethoxy)pyrimidin-2-yl]amino]methyl]-n-ethyl-4-(trifluoromethyl)anilino]methyl]cyclohexyl]acetic acid Chemical compound C=1C=C(C(F)(F)F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCC(CC(O)=O)CC1 LQMGJFOHDAPZHH-UHFFFAOYSA-N 0.000 claims 2
JCFRJBWIPLVRAE-UHFFFAOYSA-N 3-[1-[[2-[cyclopentylmethyl(ethyl)amino]-5-(trifluoromethyl)phenyl]methyl-[5-(2-methylsulfanylethoxy)pyrimidin-2-yl]amino]ethyl]-5-(trifluoromethyl)benzonitrile Chemical compound C=1C=C(C(F)(F)F)C=C(CN(C(C)C=2C=C(C=C(C=2)C#N)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 JCFRJBWIPLVRAE-UHFFFAOYSA-N 0.000 claims 2
PMSQNIAPPXXYIE-UHFFFAOYSA-N 3-[1-[[2-[cyclopentylmethyl(ethyl)amino]-5-(trifluoromethyl)phenyl]methyl-[5-(2-methylsulfonylethoxy)pyrimidin-2-yl]amino]ethyl]-5-(trifluoromethyl)benzonitrile Chemical compound C=1C=C(C(F)(F)F)C=C(CN(C(C)C=2C=C(C=C(C=2)C#N)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 PMSQNIAPPXXYIE-UHFFFAOYSA-N 0.000 claims 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
206010003210 Arteriosclerosis Diseases 0.000 claims 2
201000001320 Atherosclerosis Diseases 0.000 claims 2
OJEOEGYBZNJVJL-XPUGBJAQSA-N CCN(C[C@H]1CC[C@H](CC(O)=O)CC1)C1=C(CN(C(C)C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)C(N=C2)=NC=C2O)C=C(C(F)(F)F)C=C1 Chemical compound CCN(C[C@H]1CC[C@H](CC(O)=O)CC1)C1=C(CN(C(C)C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)C(N=C2)=NC=C2O)C=C(C(F)(F)F)C=C1 OJEOEGYBZNJVJL-XPUGBJAQSA-N 0.000 claims 2
208000024172 Cardiovascular disease Diseases 0.000 claims 2
208000032928 Dyslipidaemia Diseases 0.000 claims 2
208000035150 Hypercholesterolemia Diseases 0.000 claims 2
208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims 2
206010020772 Hypertension Diseases 0.000 claims 2
208000017170 Lipid metabolism disease Diseases 0.000 claims 2
102100024640 Low-density lipoprotein receptor Human genes 0.000 claims 2
FWZLPWYLZJFOSP-UHFFFAOYSA-N N-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-N-[[2-[cyclopentylmethyl(ethyl)amino]-5-(trifluoromethyl)phenyl]methyl]-5-methoxypyrimidin-2-amine Chemical compound C=1C=C(C(F)(F)F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OC)=CN=2)C=1N(CC)CC1CCCC1 FWZLPWYLZJFOSP-UHFFFAOYSA-N 0.000 claims 2
208000018262 Peripheral vascular disease Diseases 0.000 claims 2
206010063837 Reperfusion injury Diseases 0.000 claims 2
208000007536 Thrombosis Diseases 0.000 claims 2
206010045261 Type IIa hyperlipidaemia Diseases 0.000 claims 2
125000004442 acylamino group Chemical group 0.000 claims 2
230000002491 angiogenic effect Effects 0.000 claims 2
208000011775 arteriosclerosis disease Diseases 0.000 claims 2
125000001769 aryl amino group Chemical group 0.000 claims 2
150000001875 compounds Chemical class 0.000 claims 2
201000001386 familial hypercholesterolemia Diseases 0.000 claims 2
208000019622 heart disease Diseases 0.000 claims 2
208000006575 hypertriglyceridemia Diseases 0.000 claims 2
208000028867 ischemia Diseases 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
239000000203 mixture Substances 0.000 claims 2
125000002757 morpholinyl group Chemical group 0.000 claims 2
208000010125 myocardial infarction Diseases 0.000 claims 2
208000031225 myocardial ischemia Diseases 0.000 claims 2
YMMZMFYHUZNYRV-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-5-(2-methylsulfanylethoxy)-n-[[2-morpholin-4-yl-5-(trifluoromethyl)phenyl]methyl]pyrimidin-2-amine Chemical compound N1=CC(OCCSC)=CN=C1N(C(C)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)CC1=CC(C(F)(F)F)=CC=C1N1CCOCC1 YMMZMFYHUZNYRV-UHFFFAOYSA-N 0.000 claims 2
VFPOBJSKKOSJFW-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-5-(2-methylsulfanylethoxy)-n-[[2-piperidin-1-yl-5-(trifluoromethyl)phenyl]methyl]pyrimidin-2-amine Chemical compound N1=CC(OCCSC)=CN=C1N(C(C)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)CC1=CC(C(F)(F)F)=CC=C1N1CCCCC1 VFPOBJSKKOSJFW-UHFFFAOYSA-N 0.000 claims 2
FRJZRZFWPOBHBF-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-5-(2-methylsulfonylethoxy)-n-[[2-piperidin-1-yl-5-(trifluoromethyl)phenyl]methyl]pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C=1N=CC(OCCS(C)(=O)=O)=CN=1)CC1=CC(C(F)(F)F)=CC=C1N1CCCCC1 FRJZRZFWPOBHBF-UHFFFAOYSA-N 0.000 claims 2
KSSKBGRZUJUAMI-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-(4-methylpiperidin-1-yl)-5-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C=1N=CC(OCCS(C)(=O)=O)=CN=1)CC1=CC(C(F)(F)F)=CC=C1N1CCC(C)CC1 KSSKBGRZUJUAMI-UHFFFAOYSA-N 0.000 claims 2
BXRXCJMEYIBUNT-YOFSQIOKSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[(2s,6r)-2,6-dimethylmorpholin-4-yl]-5-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound N1=CC(OCCSC)=CN=C1N(C(C)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)CC1=CC(C(F)(F)F)=CC=C1N1C[C@@H](C)O[C@@H](C)C1 BXRXCJMEYIBUNT-YOFSQIOKSA-N 0.000 claims 2
DIZVWHUOKWGEHK-YOFSQIOKSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[(2s,6r)-2,6-dimethylmorpholin-4-yl]-5-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C=1N=CC(OCCS(C)(=O)=O)=CN=1)CC1=CC(C(F)(F)F)=CC=C1N1C[C@H](C)O[C@H](C)C1 DIZVWHUOKWGEHK-YOFSQIOKSA-N 0.000 claims 2
ZPKQQHRGDRCUKS-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-3,5-difluorophenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound FC=1C=C(F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 ZPKQQHRGDRCUKS-UHFFFAOYSA-N 0.000 claims 2
XUXHGVJATJUGPM-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-3,5-difluorophenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound FC=1C=C(F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 XUXHGVJATJUGPM-UHFFFAOYSA-N 0.000 claims 2
RZOJMRMYVTXUOQ-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-4,5-difluorophenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C(F)=C(F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 RZOJMRMYVTXUOQ-UHFFFAOYSA-N 0.000 claims 2
IYFQLUQKBLAKEP-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-4,5-difluorophenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(F)=C(F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 IYFQLUQKBLAKEP-UHFFFAOYSA-N 0.000 claims 2
PEYRYGZSUFEIED-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-4-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 PEYRYGZSUFEIED-UHFFFAOYSA-N 0.000 claims 2
QXGPBTAEDPYBKG-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-4-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfinylethoxy)pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)=O)=CN=2)C=1N(CC)CC1CCCC1 QXGPBTAEDPYBKG-UHFFFAOYSA-N 0.000 claims 2
LXSLKNJYSCAGLC-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-4-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 LXSLKNJYSCAGLC-UHFFFAOYSA-N 0.000 claims 2
VAKNWVCVZTYJTF-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-4-fluorophenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C(F)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 VAKNWVCVZTYJTF-UHFFFAOYSA-N 0.000 claims 2
GPHULSIWVLRECU-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-4-fluorophenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(F)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 GPHULSIWVLRECU-UHFFFAOYSA-N 0.000 claims 2
HXKSJZMNHACCFV-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-4-methoxyphenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C(OC)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 HXKSJZMNHACCFV-UHFFFAOYSA-N 0.000 claims 2
URTKLLULRMHPIG-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-4-methoxyphenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(OC)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 URTKLLULRMHPIG-UHFFFAOYSA-N 0.000 claims 2
KBKALBBJWQBFAL-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(C(F)(F)F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 KBKALBBJWQBFAL-UHFFFAOYSA-N 0.000 claims 2
DSUYRUSFZDJTRZ-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfinylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(C(F)(F)F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)=O)=CN=2)C=1N(CC)CC1CCCC1 DSUYRUSFZDJTRZ-UHFFFAOYSA-N 0.000 claims 2
IPEQHQPRCFXTGK-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(C(F)(F)F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 IPEQHQPRCFXTGK-UHFFFAOYSA-N 0.000 claims 2
FJUQFAPVWMOSLJ-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-fluorophenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 FJUQFAPVWMOSLJ-UHFFFAOYSA-N 0.000 claims 2
MZMGQIJQXSRQRT-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-fluorophenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(F)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 MZMGQIJQXSRQRT-UHFFFAOYSA-N 0.000 claims 2
YUGYTHSZXXFKBF-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-methoxyphenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(OC)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 YUGYTHSZXXFKBF-UHFFFAOYSA-N 0.000 claims 2
XFNCNNMLOSGHPS-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-methoxyphenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(OC)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 XFNCNNMLOSGHPS-UHFFFAOYSA-N 0.000 claims 2
QNAHFSRCUABVCZ-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-methylphenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(C)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 QNAHFSRCUABVCZ-UHFFFAOYSA-N 0.000 claims 2
WEBUCQMISHWWHN-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-methylphenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(C)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 WEBUCQMISHWWHN-UHFFFAOYSA-N 0.000 claims 2
AZGBTOAHZJQDHM-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-chloro-6-[cyclopentylmethyl(ethyl)amino]-3-methylphenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(C)C(Cl)=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 AZGBTOAHZJQDHM-UHFFFAOYSA-N 0.000 claims 2
ZRCCFSZLKNSMSJ-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-chloro-6-[cyclopentylmethyl(ethyl)amino]-3-methylphenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(C)C(Cl)=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 ZRCCFSZLKNSMSJ-UHFFFAOYSA-N 0.000 claims 2
RRDVIDDHDOYURF-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[4-bromo-2-[cyclopentylmethyl(ethyl)amino]phenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C(Br)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 RRDVIDDHDOYURF-UHFFFAOYSA-N 0.000 claims 2
CWKNPEGWPPMUJS-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[4-bromo-2-[cyclopentylmethyl(ethyl)amino]phenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(Br)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 CWKNPEGWPPMUJS-UHFFFAOYSA-N 0.000 claims 2
XPENBVHNQUZSPO-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[4-chloro-2-[cyclopentylmethyl(ethyl)amino]phenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C(Cl)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 XPENBVHNQUZSPO-UHFFFAOYSA-N 0.000 claims 2
DYHJCTNSRNGSPY-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[4-chloro-2-[cyclopentylmethyl(ethyl)amino]phenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(Cl)=CC=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 DYHJCTNSRNGSPY-UHFFFAOYSA-N 0.000 claims 2
UXGCWPZHWFTYNJ-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[5-bromo-2-[cyclopentylmethyl(ethyl)amino]phenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(Br)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCSC)=CN=2)C=1N(CC)CC1CCCC1 UXGCWPZHWFTYNJ-UHFFFAOYSA-N 0.000 claims 2
FRLMQZNIBATFEK-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[5-bromo-2-[cyclopentylmethyl(ethyl)amino]phenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C=C(Br)C=C(CN(C(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2N=CC(OCCS(C)(=O)=O)=CN=2)C=1N(CC)CC1CCCC1 FRLMQZNIBATFEK-UHFFFAOYSA-N 0.000 claims 2
LHFYXXNGLLNRAU-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]propyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(CC)N(C=1N=CC(OCCSC)=CN=1)CC1=CC(C(F)(F)F)=CC=C1N(CC)CC1CCCC1 LHFYXXNGLLNRAU-UHFFFAOYSA-N 0.000 claims 2
NHROKXQQWPYZAN-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]propyl]-n-[[2-[cyclopentylmethyl(ethyl)amino]-5-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(CC)N(C=1N=CC(OCCS(C)(=O)=O)=CN=1)CC1=CC(C(F)(F)F)=CC=C1N(CC)CC1CCCC1 NHROKXQQWPYZAN-UHFFFAOYSA-N 0.000 claims 2
JYKVTJYWPKYZTI-UHFFFAOYSA-N n-[[2-[bis(cyclopropylmethyl)amino]-3,5-difluorophenyl]methyl]-n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound N1=CC(OCCSC)=CN=C1N(C(C)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)CC1=CC(F)=CC(F)=C1N(CC1CC1)CC1CC1 JYKVTJYWPKYZTI-UHFFFAOYSA-N 0.000 claims 2
AKBOQPXMDMTOFP-UHFFFAOYSA-N n-[[2-[bis(cyclopropylmethyl)amino]-3,5-difluorophenyl]methyl]-n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-5-(2-methylsulfonylethoxy)pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C=1N=CC(OCCS(C)(=O)=O)=CN=1)CC1=CC(F)=CC(F)=C1N(CC1CC1)CC1CC1 AKBOQPXMDMTOFP-UHFFFAOYSA-N 0.000 claims 2
125000004430 oxygen atom Chemical group O* 0.000 claims 2
125000003386 piperidinyl group Chemical group 0.000 claims 2
208000037803 restenosis Diseases 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
239000012453 solvate Substances 0.000 claims 2
125000003107 substituted aryl group Chemical group 0.000 claims 2
125000004434 sulfur atom Chemical group 0.000 claims 2
HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
230000006806 disease prevention Effects 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
JTFRFRCOURIFCF-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-5-(2-methylsulfonylethoxy)-n-[[2-morpholin-4-yl-5-(trifluoromethyl)phenyl]methyl]pyrimidin-2-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C=1N=CC(OCCS(C)(=O)=O)=CN=1)CC1=CC(C(F)(F)F)=CC=C1N1CCOCC1 JTFRFRCOURIFCF-UHFFFAOYSA-N 0.000 claims 1
LEGQTEYOASXMFK-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-[[2-(4-methylpiperidin-1-yl)-5-(trifluoromethyl)phenyl]methyl]-5-(2-methylsulfanylethoxy)pyrimidin-2-amine Chemical compound N1=CC(OCCSC)=CN=C1N(C(C)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)CC1=CC(C(F)(F)F)=CC=C1N1CCC(C)CC1 LEGQTEYOASXMFK-UHFFFAOYSA-N 0.000 claims 1
230000003449 preventive effect Effects 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1

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