ES2404580T3

ES2404580T3 - Novedosos inhibidores de la ehs y uso de los mismos

Novedosos inhibidores de la ehs y uso de los mismos

Info

Publication number: ES2404580T3
Authority: ES; Spain
Prior art keywords: methyl; phenyl; triazin; trifluoromethyl; methylamino
Prior art date: 2007-10-11
Legal status : Active

Application number

ES08837991T

Other languages

English (en)

Spanish (es)

Inventor

Yun Ding

Reema K. Thalji

Joseph Paul Marino, Jr.

Current Assignee

GlaxoSmithKline LLC

Original Assignee

GlaxoSmithKline LLC

Priority date

2007-10-11

Filing date

2008-10-10

Publication date

2013-05-28

2008-10-10 Application filed by GlaxoSmithKline LLC filed Critical GlaxoSmithKline LLC

2013-05-28 Application granted granted Critical

2013-05-28 Publication of ES2404580T3 publication Critical patent/ES2404580T3/es

Status Active legal-status Critical Current

2028-10-10 Anticipated expiration legal-status Critical

Links

239000003112 inhibitor Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 173
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
229910052705 radium Inorganic materials 0.000 claims abstract description 19
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims description 49
150000003839 salts Chemical class 0.000 claims description 45
-1 4-methyl-1-piperazinyl Chemical group 0.000 claims description 37
125000004429 atom Chemical group 0.000 claims description 37
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 36
125000005843 halogen group Chemical group 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 22
239000000546 pharmaceutical excipient Substances 0.000 claims description 20
239000008194 pharmaceutical composition Substances 0.000 claims description 18
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
125000001188 haloalkyl group Chemical group 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
206010020772 Hypertension Diseases 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
241000282414 Homo sapiens Species 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000002950 monocyclic group Chemical group 0.000 claims description 8
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 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 7
125000001544 thienyl group Chemical group 0.000 claims description 7
125000000171 (C1-C6) haloalkyl group Chemical group 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
206010019280 Heart failures Diseases 0.000 claims description 6
208000010125 myocardial infarction Diseases 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
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 5
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 5
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 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
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
JXPKVUBSJSCTLI-UHFFFAOYSA-N 1-[4-(methylamino)-6-(4-methylpiperazin-1-yl)-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=1N1CCN(C)CC1 JXPKVUBSJSCTLI-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
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
LDLCYNLUPWEAFH-UHFFFAOYSA-N 4-[4-(methylamino)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxamide Chemical compound N=1C(NC)=NC(N2CCN(C)CC2)=NC=1N(CC1)CCN1C(=O)NCC1=CC=CC=C1C(F)(F)F LDLCYNLUPWEAFH-UHFFFAOYSA-N 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
IIXRCKOAGLIBTC-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)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(Cl)=CC=2)Cl)=NC=1N1CCN(C)CC1 IIXRCKOAGLIBTC-UHFFFAOYSA-N 0.000 claims description 4
OFIHLVMWXMTGLI-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-[4-(methylamino)-6-phenyl-1,3,5-triazin-2-yl]piperidine-4-carboxamide Chemical compound N=1C(NC)=NC(N2CCC(CC2)C(=O)NCC=2C=CC(Cl)=CC=2)=NC=1C1=CC=CC=C1 OFIHLVMWXMTGLI-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
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
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 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
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 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
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 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
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
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 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
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 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
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
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 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
QMGKSUFFKIWPIH-UHFFFAOYSA-N 1-[4-(methylamino)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]-n-[[2-(trifluoromethoxy)phenyl]methyl]piperidine-3-carboxamide Chemical compound N=1C(NC)=NC(N2CCN(C)CC2)=NC=1N(C1)CCCC1C(=O)NCC1=CC=CC=C1OC(F)(F)F QMGKSUFFKIWPIH-UHFFFAOYSA-N 0.000 claims description 3
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