JP5411867B2 - 新規ｓＥＨ阻害剤およびそれらの使用 - Google Patents

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Publication number

JP5411867B2

JP5411867B2 JP2010529085A JP2010529085A JP5411867B2 JP 5411867 B2 JP5411867 B2 JP 5411867B2 JP 2010529085 A JP2010529085 A JP 2010529085A JP 2010529085 A JP2010529085 A JP 2010529085A JP 5411867 B2 JP5411867 B2 JP 5411867B2

Authority

JP

Japan

Prior art keywords

methyl

phenyl

triazin

trifluoromethyl

methylamino

Prior art date

2007-10-11

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.)

Expired - Fee Related

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• 239000003112 inhibitor Substances 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims description 162
• 125000001424 substituent group Chemical group 0.000 claims description 49
• -1 4-methyl-1-piperazinyl Chemical group 0.000 claims description 41
• 150000003839 salts Chemical class 0.000 claims description 37
• 125000004429 atom Chemical group 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 125000005843 halogen group Chemical group 0.000 claims description 33
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 23
• 125000001188 haloalkyl group Chemical group 0.000 claims description 18
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• 229910052705 radium Inorganic materials 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 208000024891 symptom Diseases 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• RFPSCZCSLQIARP-UHFFFAOYSA-N 1-[4-(3-methoxyphenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC(OC)=C1 RFPSCZCSLQIARP-UHFFFAOYSA-N 0.000 claims description 7
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 239000001257 hydrogen Substances 0.000 claims description 7
• BZDZBNJTTXUXLB-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)methyl]-1-[4-(2-hydroxyethylamino)-6-methyl-1,3,5-triazin-2-yl]piperidine-4-carboxamide Chemical compound CC1=NC(NCCO)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC(Cl)=CC=2)Cl)=N1 BZDZBNJTTXUXLB-UHFFFAOYSA-N 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• LYHGCBNWFVVDGY-UHFFFAOYSA-N 1-[4-(4-ethoxyphenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1=CC(OCC)=CC=C1C1=NC(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 LYHGCBNWFVVDGY-UHFFFAOYSA-N 0.000 claims description 6
• NSXBHYNKGMGSHU-UHFFFAOYSA-N 1-[4-(methylamino)-6-[3-(trifluoromethoxy)phenyl]-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC(OC(F)(F)F)=C1 NSXBHYNKGMGSHU-UHFFFAOYSA-N 0.000 claims description 6
• DAZRSYPRBIQZFC-UHFFFAOYSA-N 1-[4-(methylamino)-6-[4-(trifluoromethoxy)phenyl]-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=C(OC(F)(F)F)C=C1 DAZRSYPRBIQZFC-UHFFFAOYSA-N 0.000 claims description 6
• VGXDUSLCTRMEOY-UHFFFAOYSA-N 1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethylsulfanyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound CNC1=NC(C)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)SC(F)(F)F)=N1 VGXDUSLCTRMEOY-UHFFFAOYSA-N 0.000 claims description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
• 239000000470 constituent Substances 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• BVLOUYJPSWSJRI-UHFFFAOYSA-N n-[[4-cyano-2-(trifluoromethyl)phenyl]methyl]-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]piperidine-4-carboxamide Chemical compound CNC1=NC(C)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC(=CC=2)C#N)C(F)(F)F)=N1 BVLOUYJPSWSJRI-UHFFFAOYSA-N 0.000 claims description 5
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
• SSSMBRIPSWIFFF-UHFFFAOYSA-N 1-(4-amino-6-methyl-1,3,5-triazin-2-yl)-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound CC1=NC(N)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 SSSMBRIPSWIFFF-UHFFFAOYSA-N 0.000 claims description 4
• PRSUVYWGNNZIPY-UHFFFAOYSA-N 1-(4-amino-6-propan-2-yl-1,3,5-triazin-2-yl)-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound CC(C)C1=NC(N)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 PRSUVYWGNNZIPY-UHFFFAOYSA-N 0.000 claims description 4
• JCXUYFPEIYQWEL-DQEYMECFSA-N 1-[4,6-bis[[(2r)-2-phenylpropyl]amino]-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1([C@@H](C)CNC=2N=C(N=C(N=2)N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)NC[C@H](C)C=2C=CC=CC=2)=CC=CC=C1 JCXUYFPEIYQWEL-DQEYMECFSA-N 0.000 claims description 4
• KODGHYKBXRRGHF-UHFFFAOYSA-N 1-[4-(3-chlorophenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC(Cl)=C1 KODGHYKBXRRGHF-UHFFFAOYSA-N 0.000 claims description 4
• RGWZZYDTHHIICR-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC(F)=C1 RGWZZYDTHHIICR-UHFFFAOYSA-N 0.000 claims description 4
• NFXIVBBZMSWUES-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)-6-(propan-2-ylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC(C)C)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1N1CCN(C)CC1 NFXIVBBZMSWUES-UHFFFAOYSA-N 0.000 claims description 4
• QFPLPEBGZRMKKH-UHFFFAOYSA-N 1-[4-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound CNC1=NC=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 QFPLPEBGZRMKKH-UHFFFAOYSA-N 0.000 claims description 4
• VXEBYYIBCRVIML-UHFFFAOYSA-N 1-[4-(methylamino)-6-phenyl-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC=C1 VXEBYYIBCRVIML-UHFFFAOYSA-N 0.000 claims description 4
• QYHOENLKCBLSHF-UHFFFAOYSA-N 1-[4-[3-(dimethylamino)phenyl]-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC(N(C)C)=C1 QYHOENLKCBLSHF-UHFFFAOYSA-N 0.000 claims description 4
• KERHCUOJIGXADF-UHFFFAOYSA-N 1-[4-amino-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1CN(C)CCN1C1=NC(N)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 KERHCUOJIGXADF-UHFFFAOYSA-N 0.000 claims description 4
• BUWQYHYHSQTERY-UHFFFAOYSA-N 1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound CNC1=NC(C)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 BUWQYHYHSQTERY-UHFFFAOYSA-N 0.000 claims description 4
• DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• IVKOIAGIGKQVPW-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-1-[4-(methylamino)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)Cl)=NC=1N1CCN(C)CC1 IVKOIAGIGKQVPW-UHFFFAOYSA-N 0.000 claims description 4
• PVTFEAGMCGMRRS-UHFFFAOYSA-N n-[[4-bromo-2-(trifluoromethoxy)phenyl]methyl]-1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]piperidine-4-carboxamide Chemical compound CNC1=NC(C)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC(Br)=CC=2)OC(F)(F)F)=N1 PVTFEAGMCGMRRS-UHFFFAOYSA-N 0.000 claims description 4
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
• IPIPCVQDQUJNCG-UHFFFAOYSA-N 1-(4-amino-6-ethyl-1,3,5-triazin-2-yl)-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound CCC1=NC(N)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 IPIPCVQDQUJNCG-UHFFFAOYSA-N 0.000 claims description 3
• ORBMSKPWIBNAOY-UHFFFAOYSA-N 1-(4-amino-6-phenyl-1,3,5-triazin-2-yl)-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(N)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC=C1 ORBMSKPWIBNAOY-UHFFFAOYSA-N 0.000 claims description 3
• YCCQSHIFMLVJSA-UHFFFAOYSA-N 1-(4-ethyl-6-morpholin-4-yl-1,3,5-triazin-2-yl)-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(CC)=NC(N2CCOCC2)=NC=1N(CC1)CCC1C(=O)NCC1=CC=CC=C1C(F)(F)F YCCQSHIFMLVJSA-UHFFFAOYSA-N 0.000 claims description 3
• XMZDPSHBSJKCMY-UHFFFAOYSA-N 1-(4-morpholin-4-yl-1,3,5-triazin-2-yl)-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1CNC(=O)C1CCN(C=2N=C(N=CN=2)N2CCOCC2)CC1 XMZDPSHBSJKCMY-UHFFFAOYSA-N 0.000 claims description 3
• MSJLFAOUMMTBHX-UHFFFAOYSA-N 1-[4,6-bis(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1CN(C)CCN1C1=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC(N2CCN(C)CC2)=N1 MSJLFAOUMMTBHX-UHFFFAOYSA-N 0.000 claims description 3
• CLYKSKCSUKISLN-UHFFFAOYSA-N 1-[4,6-bis(azepan-1-yl)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1CNC(=O)C1CCN(C=2N=C(N=C(N=2)N2CCCCCC2)N2CCCCCC2)CC1 CLYKSKCSUKISLN-UHFFFAOYSA-N 0.000 claims description 3
• NISUNIYWKLJOMA-UHFFFAOYSA-N 1-[4,6-bis(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound CNC1=NC(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 NISUNIYWKLJOMA-UHFFFAOYSA-N 0.000 claims description 3
• SLUCETGZCRENEH-UHFFFAOYSA-N 1-[4,6-bis[2-(dimethylamino)ethyl-methylamino]-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound CN(C)CCN(C)C1=NC(N(C)CCN(C)C)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 SLUCETGZCRENEH-UHFFFAOYSA-N 0.000 claims description 3
• MPMFWKBJZMHJRK-UHFFFAOYSA-N 1-[4-(2,6-dimethylphenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=C(C)C=CC=C1C MPMFWKBJZMHJRK-UHFFFAOYSA-N 0.000 claims description 3
• DQNPXNNMYPVWAX-UHFFFAOYSA-N 1-[4-(2-benzylsulfanylethylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1CNC(=O)C1CCN(C=2N=C(NCCSCC=3C=CC=CC=3)N=CN=2)CC1 DQNPXNNMYPVWAX-UHFFFAOYSA-N 0.000 claims description 3
• JSJTVRNGAMWWAT-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC=C1Cl JSJTVRNGAMWWAT-UHFFFAOYSA-N 0.000 claims description 3
• UKWRREKQQAFITE-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC=C1F UKWRREKQQAFITE-UHFFFAOYSA-N 0.000 claims description 3
• BWAYGMJMNFGICM-UHFFFAOYSA-N 1-[4-(2-methoxyphenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC=C1OC BWAYGMJMNFGICM-UHFFFAOYSA-N 0.000 claims description 3
• VOHKAUWSMHYZKM-UHFFFAOYSA-N 1-[4-(3-chloro-4-ethoxyphenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1=C(Cl)C(OCC)=CC=C1C1=NC(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 VOHKAUWSMHYZKM-UHFFFAOYSA-N 0.000 claims description 3
• ZANDDEMFPVFSRH-UHFFFAOYSA-N 1-[4-(3-cyanophenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC(C#N)=C1 ZANDDEMFPVFSRH-UHFFFAOYSA-N 0.000 claims description 3
• SBWKMJRCLMQSHL-UHFFFAOYSA-N 1-[4-(4-acetamidophenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=C(NC(C)=O)C=C1 SBWKMJRCLMQSHL-UHFFFAOYSA-N 0.000 claims description 3
• JDBVVPYHVXZMEH-UHFFFAOYSA-N 1-[4-(4-cyanophenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=C(C#N)C=C1 JDBVVPYHVXZMEH-UHFFFAOYSA-N 0.000 claims description 3
• WYXSMZBHOJDNKG-UHFFFAOYSA-N 1-[4-(4-ethylsulfonylphenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=NC(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 WYXSMZBHOJDNKG-UHFFFAOYSA-N 0.000 claims description 3
• HBDUKAHOAWAPBH-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=C(F)C=C1 HBDUKAHOAWAPBH-UHFFFAOYSA-N 0.000 claims description 3
• CSNHOXQLYJMZLY-UHFFFAOYSA-N 1-[4-(4-methoxyphenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=C(OC)C=C1 CSNHOXQLYJMZLY-UHFFFAOYSA-N 0.000 claims description 3
• AIHJZLHJLDCPAM-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1CN(C)CCN1C1=NC=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=N1 AIHJZLHJLDCPAM-UHFFFAOYSA-N 0.000 claims description 3
• VNJVGFMPTUFDAJ-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)-6-methylsulfanyl-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(SC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1N1CCN(C)CC1 VNJVGFMPTUFDAJ-UHFFFAOYSA-N 0.000 claims description 3
• FKRRTLJZJRLBID-UHFFFAOYSA-N 1-[4-(4-tert-butylphenyl)-6-(methylamino)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=C(C(C)(C)C)C=C1 FKRRTLJZJRLBID-UHFFFAOYSA-N 0.000 claims description 3
• DSJFHOVEICCTQA-UHFFFAOYSA-N 1-[4-(methylamino)-6-(2-methylphenyl)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C(=CC=CC=2)C(F)(F)F)=NC=1C1=CC=CC=C1C DSJFHOVEICCTQA-UHFFFAOYSA-N 0.000 claims description 3
• SDDQIJHFKNZXRJ-UHFFFAOYSA-N 1-[4-(methylamino)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]-n-(pyridin-2-ylmethyl)piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2N=CC=CC=2)=NC=1N1CCN(C)CC1 SDDQIJHFKNZXRJ-UHFFFAOYSA-N 0.000 claims description 3
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