JP5976778B2 - キナーゼ阻害剤としてのピラゾリル−ピリミジン誘導体 - Google Patents

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Publication number

JP5976778B2

JP5976778B2 JP2014504251A JP2014504251A JP5976778B2 JP 5976778 B2 JP5976778 B2 JP 5976778B2 JP 2014504251 A JP2014504251 A JP 2014504251A JP 2014504251 A JP2014504251 A JP 2014504251A JP 5976778 B2 JP5976778 B2 JP 5976778B2

Authority

JP

Japan

Prior art keywords

pyrazole

carboxamide

formula

compound

pyrimidin

Prior art date

2011-04-11

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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• BWIHJLOBZMKPKS-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)pyrimidine Chemical class N1C=CC(C=2N=CC=CN=2)=N1 BWIHJLOBZMKPKS-UHFFFAOYSA-N 0.000 title description 4
• 229940043355 kinase inhibitor Drugs 0.000 title description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 357
• 238000000034 method Methods 0.000 claims description 132
• -1 methylenedioxy Chemical group 0.000 claims description 123
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 62
• 125000003118 aryl group Chemical group 0.000 claims description 62
• 239000001257 hydrogen Substances 0.000 claims description 61
• 229910052739 hydrogen Inorganic materials 0.000 claims description 61
• 125000000623 heterocyclic group Chemical group 0.000 claims description 54
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 45
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 43
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 41
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 34
• 238000002360 preparation method Methods 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 102000001253 Protein Kinase Human genes 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 108060006633 protein kinase Proteins 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical group 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 108090000623 proteins and genes Proteins 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 102000004169 proteins and genes Human genes 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 6
• 125000001769 aryl amino group Chemical group 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• RFJQYCNMCJJJSG-UHFFFAOYSA-N 1-tert-butyl-5-(2-methylsulfanylpyrimidin-4-yl)pyrazole-3-carboxamide Chemical compound CSC1=NC=CC(C=2N(N=C(C=2)C(N)=O)C(C)(C)C)=N1 RFJQYCNMCJJJSG-UHFFFAOYSA-N 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000004104 aryloxy group Chemical group 0.000 claims description 5
• 229940127089 cytotoxic agent Drugs 0.000 claims description 5
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 5
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• SAZWNKNJUWDIKE-UHFFFAOYSA-N 3-(2-methylsulfanylpyrimidin-4-yl)-1h-pyrazole-5-carboxamide Chemical compound CSC1=NC=CC(C=2NN=C(C=2)C(N)=O)=N1 SAZWNKNJUWDIKE-UHFFFAOYSA-N 0.000 claims description 4
• WBRIZQWMKIXWSK-UHFFFAOYSA-N 5-[2-(4-bromo-2-methoxyanilino)pyrimidin-4-yl]-n-(2,6-diethylphenyl)-1-methylpyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NN(C)C(C=2N=C(NC=3C(=CC(Br)=CC=3)OC)N=CC=2)=C1 WBRIZQWMKIXWSK-UHFFFAOYSA-N 0.000 claims description 4
• SIYHLKJVZNBAAO-UHFFFAOYSA-N 5-[2-(4-bromo-2-methoxyanilino)pyrimidin-4-yl]-n-(2,6-diethylphenyl)-2-methylpyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=CC(C=2N=C(NC=3C(=CC(Br)=CC=3)OC)N=CC=2)=NN1C SIYHLKJVZNBAAO-UHFFFAOYSA-N 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
• 125000005600 alkyl phosphonate group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 4
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
• 125000005110 aryl thio group Chemical group 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 4
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
• 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
• 238000000338 in vitro Methods 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• YFPXKALYLATDPX-UHFFFAOYSA-N n-(2,6-diethylphenyl)-5-[2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]-2-methylpyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=CC(C=2N=C(NC=3C(=CC(=CC=3)N3CCN(C)CC3)OC)N=CC=2)=NN1C YFPXKALYLATDPX-UHFFFAOYSA-N 0.000 claims description 4
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• YIGPUXRGBBZKJW-UHFFFAOYSA-N 1-tert-butyl-5-(2-methoxypyrimidin-4-yl)pyrazole-3-carboxamide Chemical compound COC1=NC=CC(C=2N(N=C(C=2)C(N)=O)C(C)(C)C)=N1 YIGPUXRGBBZKJW-UHFFFAOYSA-N 0.000 claims description 3
• NPAPHHQDTZZLSK-UHFFFAOYSA-N 1-tert-butyl-5-(2-morpholin-4-ylpyrimidin-4-yl)-n-phenylpyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NC=2C=CC=CC=2)C=C1C(N=1)=CC=NC=1N1CCOCC1 NPAPHHQDTZZLSK-UHFFFAOYSA-N 0.000 claims description 3
• LLSIYQYYVAAHEN-UHFFFAOYSA-N 1-tert-butyl-5-(2-phenoxypyrimidin-4-yl)-n-phenylpyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NC=2C=CC=CC=2)C=C1C(N=1)=CC=NC=1OC1=CC=CC=C1 LLSIYQYYVAAHEN-UHFFFAOYSA-N 0.000 claims description 3
• VZYACGCYABUZMD-UHFFFAOYSA-N 1-tert-butyl-5-(2-phenoxypyrimidin-4-yl)-n-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NC(C)C)C=C1C1=CC=NC(OC=2C=CC=CC=2)=N1 VZYACGCYABUZMD-UHFFFAOYSA-N 0.000 claims description 3
• NXUZHSNCDIAGAY-UHFFFAOYSA-N 1-tert-butyl-5-[2-(4-cyanophenoxy)pyrimidin-4-yl]-n-methylpyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NC)C=C1C1=CC=NC(OC=2C=CC(=CC=2)C#N)=N1 NXUZHSNCDIAGAY-UHFFFAOYSA-N 0.000 claims description 3
• DMLNFHDCCVVACO-UHFFFAOYSA-N 1-tert-butyl-5-[2-(4-cyanophenoxy)pyrimidin-4-yl]-n-phenylpyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NC=2C=CC=CC=2)C=C1C(N=1)=CC=NC=1OC1=CC=C(C#N)C=C1 DMLNFHDCCVVACO-UHFFFAOYSA-N 0.000 claims description 3
• GLOLZXJNFUHZRR-UHFFFAOYSA-N 1-tert-butyl-5-[2-(4-cyanophenoxy)pyrimidin-4-yl]-n-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NC(C)C)C=C1C1=CC=NC(OC=2C=CC(=CC=2)C#N)=N1 GLOLZXJNFUHZRR-UHFFFAOYSA-N 0.000 claims description 3
• AXRBYRBXIFSKIF-UHFFFAOYSA-N 1-tert-butyl-5-[2-(4-piperazin-1-ylphenoxy)pyrimidin-4-yl]pyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(N)=O)C=C1C1=CC=NC(OC=2C=CC(=CC=2)N2CCNCC2)=N1 AXRBYRBXIFSKIF-UHFFFAOYSA-N 0.000 claims description 3
• JPXVJHYKCAPQRA-UHFFFAOYSA-N 1-tert-butyl-5-[2-(dimethylamino)pyrimidin-4-yl]-n-methylpyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NC)C=C1C1=CC=NC(N(C)C)=N1 JPXVJHYKCAPQRA-UHFFFAOYSA-N 0.000 claims description 3
• JGLZQEWJZMTROM-UHFFFAOYSA-N 1-tert-butyl-5-[2-(dimethylamino)pyrimidin-4-yl]-n-phenylpyrazole-3-carboxamide Chemical compound CN(C)C1=NC=CC(C=2N(N=C(C=2)C(=O)NC=2C=CC=CC=2)C(C)(C)C)=N1 JGLZQEWJZMTROM-UHFFFAOYSA-N 0.000 claims description 3
• KHJXLLUKAIABND-UHFFFAOYSA-N 1-tert-butyl-5-[2-(dimethylamino)pyrimidin-4-yl]-n-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NC(C)C)C=C1C1=CC=NC(N(C)C)=N1 KHJXLLUKAIABND-UHFFFAOYSA-N 0.000 claims description 3
• STVXWMPMCBWAQK-UHFFFAOYSA-N 1-tert-butyl-5-[2-(dimethylamino)pyrimidin-4-yl]pyrazole-3-carboxamide Chemical compound CN(C)C1=NC=CC(C=2N(N=C(C=2)C(N)=O)C(C)(C)C)=N1 STVXWMPMCBWAQK-UHFFFAOYSA-N 0.000 claims description 3
• NWLNDDCQBDCBGL-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-5-(2-methylpyrimidin-4-yl)pyrazole-3-carboxamide Chemical compound COC1=CC=CC(CN2C(=CC(=N2)C=2N=C(C)N=CC=2)C(N)=O)=C1 NWLNDDCQBDCBGL-UHFFFAOYSA-N 0.000 claims description 3
• GNDPCMBWJSMFDH-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-5-(2-oxo-1h-pyrimidin-6-yl)pyrazole-3-carboxamide Chemical compound COC1=CC=CC(CN2C(=CC(=N2)C=2N=C(O)N=CC=2)C(N)=O)=C1 GNDPCMBWJSMFDH-UHFFFAOYSA-N 0.000 claims description 3
• LXAHIOJOUKGSMV-UHFFFAOYSA-N 5-[2-(4-bromo-2-methoxyanilino)pyrimidin-4-yl]-n-(2,6-diethylphenyl)-1-[(4-methoxyphenyl)methyl]pyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NN(CC=2C=CC(OC)=CC=2)C(C=2N=C(NC=3C(=CC(Br)=CC=3)OC)N=CC=2)=C1 LXAHIOJOUKGSMV-UHFFFAOYSA-N 0.000 claims description 3
• SXSDYPDWRFRBOK-UHFFFAOYSA-N 5-[2-(4-bromo-2-methoxyanilino)pyrimidin-4-yl]-n-(2,6-diethylphenyl)-2-[(4-methoxyphenyl)methyl]pyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=CC(C=2N=C(NC=3C(=CC(Br)=CC=3)OC)N=CC=2)=NN1CC1=CC=C(OC)C=C1 SXSDYPDWRFRBOK-UHFFFAOYSA-N 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• JPKZTKMCHHNHCK-UHFFFAOYSA-N N-hydroxy-3-(2-methylsulfanylpyrimidin-4-yl)-1H-pyrazole-5-carboxamide Chemical compound CSC1=NC=CC(C=2NN=C(C=2)C(=O)NO)=N1 JPKZTKMCHHNHCK-UHFFFAOYSA-N 0.000 claims description 3
• 230000001093 anti-cancer Effects 0.000 claims description 3
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
• 125000004986 diarylamino group Chemical group 0.000 claims description 3
• ANWOMOBMTBNCGP-UHFFFAOYSA-N n-(2,6-diethylphenyl)-3-[2-(2-methoxyanilino)pyrimidin-4-yl]-1h-pyrazole-5-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NNC(C=2N=C(NC=3C(=CC=CC=3)OC)N=CC=2)=C1 ANWOMOBMTBNCGP-UHFFFAOYSA-N 0.000 claims description 3
• GXEHCAYTZFZPQF-UHFFFAOYSA-N n-(2,6-diethylphenyl)-3-[2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]-1h-pyrazole-5-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NNC(C=2N=C(NC=3C(=CC(=CC=3)N3CCN(C)CC3)OC)N=CC=2)=C1 GXEHCAYTZFZPQF-UHFFFAOYSA-N 0.000 claims description 3
• UTWAVTYOSXACBH-UHFFFAOYSA-N n-(2,6-diethylphenyl)-5-[2-(2-methoxyanilino)pyrimidin-4-yl]-1-[(4-methoxyphenyl)methyl]pyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NN(CC=2C=CC(OC)=CC=2)C(C=2N=C(NC=3C(=CC=CC=3)OC)N=CC=2)=C1 UTWAVTYOSXACBH-UHFFFAOYSA-N 0.000 claims description 3
• HVTSGLCSESUTKX-UHFFFAOYSA-N n-(2,6-diethylphenyl)-5-[2-(2-methoxyanilino)pyrimidin-4-yl]-1-methylpyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NN(C)C(C=2N=C(NC=3C(=CC=CC=3)OC)N=CC=2)=C1 HVTSGLCSESUTKX-UHFFFAOYSA-N 0.000 claims description 3
• AIXGHQIUKRVEAX-UHFFFAOYSA-N n-(2,6-diethylphenyl)-5-[2-(2-methoxyanilino)pyrimidin-4-yl]-2-[(4-methoxyphenyl)methyl]pyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=CC(C=2N=C(NC=3C(=CC=CC=3)OC)N=CC=2)=NN1CC1=CC=C(OC)C=C1 AIXGHQIUKRVEAX-UHFFFAOYSA-N 0.000 claims description 3
• LPNFVFRZLDAJHS-UHFFFAOYSA-N n-(2,6-diethylphenyl)-5-[2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]-1-[(4-methoxyphenyl)methyl]pyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NN(CC=2C=CC(OC)=CC=2)C(C=2N=C(NC=3C(=CC(=CC=3)N3CCN(C)CC3)OC)N=CC=2)=C1 LPNFVFRZLDAJHS-UHFFFAOYSA-N 0.000 claims description 3
• WZKSKKZREXLPGE-UHFFFAOYSA-N n-(2,6-diethylphenyl)-5-[2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]-1-methylpyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NN(C)C(C=2N=C(NC=3C(=CC(=CC=3)N3CCN(C)CC3)OC)N=CC=2)=C1 WZKSKKZREXLPGE-UHFFFAOYSA-N 0.000 claims description 3
• ZFRAYIYRRCRCJI-UHFFFAOYSA-N n-(2,6-diethylphenyl)-5-[2-[4-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]-1-methylpyrazole-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NN(C)C(C=2N=C(NC=3C(=CC(=CC=3)N3CCN(CCO)CC3)OC)N=CC=2)=C1 ZFRAYIYRRCRCJI-UHFFFAOYSA-N 0.000 claims description 3
• WYBUJUAJMUSILH-UHFFFAOYSA-N n-benzyl-1-tert-butyl-5-(2-phenoxypyrimidin-4-yl)pyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NCC=2C=CC=CC=2)C=C1C(N=1)=CC=NC=1OC1=CC=CC=C1 WYBUJUAJMUSILH-UHFFFAOYSA-N 0.000 claims description 3
• IUPQGRJRSIZORG-UHFFFAOYSA-N n-benzyl-1-tert-butyl-5-[2-(4-cyanophenoxy)pyrimidin-4-yl]pyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NCC=2C=CC=CC=2)C=C1C(N=1)=CC=NC=1OC1=CC=C(C#N)C=C1 IUPQGRJRSIZORG-UHFFFAOYSA-N 0.000 claims description 3
• KXJJQDWQTVXFCT-UHFFFAOYSA-N n-benzyl-1-tert-butyl-5-[2-(dimethylamino)pyrimidin-4-yl]pyrazole-3-carboxamide Chemical compound CN(C)C1=NC=CC(C=2N(N=C(C=2)C(=O)NCC=2C=CC=CC=2)C(C)(C)C)=N1 KXJJQDWQTVXFCT-UHFFFAOYSA-N 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
• YNJNLGYPTQPTPW-UHFFFAOYSA-N 1-(6-methoxypyridin-3-yl)-5-pyrimidin-4-ylpyrazole-3-carboxylic acid Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CN=CC=2)=CC(C(O)=O)=N1 YNJNLGYPTQPTPW-UHFFFAOYSA-N 0.000 claims description 2
• XWSQCSJHYIBIPB-UHFFFAOYSA-N 1-tert-butyl-5-(2-phenylpyrimidin-4-yl)pyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(N)=O)C=C1C1=CC=NC(C=2C=CC=CC=2)=N1 XWSQCSJHYIBIPB-UHFFFAOYSA-N 0.000 claims description 2
• PMVLFBLYAWKVTH-UHFFFAOYSA-N 1-tert-butyl-n-methyl-5-(2-phenoxypyrimidin-4-yl)pyrazole-3-carboxamide Chemical compound CC(C)(C)N1N=C(C(=O)NC)C=C1C1=CC=NC(OC=2C=CC=CC=2)=N1 PMVLFBLYAWKVTH-UHFFFAOYSA-N 0.000 claims description 2
• LPPNOCWWUZTIKG-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-1-(5-chloro-2-ethylphenyl)pyrazole-3-carboxamide Chemical compound CCC1=CC=C(Cl)C=C1N1C(C=2N=C(N)N=CC=2)=CC(C(N)=O)=N1 LPPNOCWWUZTIKG-UHFFFAOYSA-N 0.000 claims description 2
• HOURAQDXNPRUJS-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-1-(5-chloro-2-methylphenyl)pyrazole-3-carboxamide Chemical compound CC1=CC=C(Cl)C=C1N1C(C=2N=C(N)N=CC=2)=CC(C(N)=O)=N1 HOURAQDXNPRUJS-UHFFFAOYSA-N 0.000 claims description 2
• ZYDBWXADPWQAMI-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-ethylphenyl)pyrazole-3-carboxamide Chemical compound CCC1=CC=C(Cl)C=C1N1C(C(N)=O)=CC(C=2N=C(N)N=CC=2)=N1 ZYDBWXADPWQAMI-UHFFFAOYSA-N 0.000 claims description 2
• MGCJYRVJINHYAP-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)pyrazole-3-carboxamide Chemical compound CC1=CC=C(Cl)C=C1N1C(C(N)=O)=CC(C=2N=C(N)N=CC=2)=N1 MGCJYRVJINHYAP-UHFFFAOYSA-N 0.000 claims description 2
• IFXSYLKWEVEJIA-UHFFFAOYSA-N 5-(2-methylsulfanylpyrimidin-4-yl)-1-piperidin-4-ylpyrazole-3-carboxamide Chemical compound CSC1=NC=CC(C=2N(N=C(C=2)C(N)=O)C2CCNCC2)=N1 IFXSYLKWEVEJIA-UHFFFAOYSA-N 0.000 claims description 2
• OHTRSASACJDQCI-UHFFFAOYSA-N 5-(2-methylsulfanylpyrimidin-4-yl)-2-piperidin-4-ylpyrazole-3-carboxamide Chemical compound CSC1=NC=CC(C2=NN(C(C(N)=O)=C2)C2CCNCC2)=N1 OHTRSASACJDQCI-UHFFFAOYSA-N 0.000 claims description 2
• YNEYAILCVWIGMT-UHFFFAOYSA-N [1-(6-methoxypyridin-3-yl)-5-pyrimidin-4-ylpyrazol-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1=NC(OC)=CC=C1N1C(C=2N=CN=CC=2)=CC(C(=O)N2CCN(C)CC2)=N1 YNEYAILCVWIGMT-UHFFFAOYSA-N 0.000 claims description 2
• 238000011319 anticancer therapy Methods 0.000 claims description 2
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• NPDWZVIWNJMPPR-UHFFFAOYSA-N methyl 1-(6-methoxypyridin-3-yl)-5-pyrimidin-4-ylpyrazole-3-carboxylate Chemical compound C=1C=C(OC)N=CC=1N1N=C(C(=O)OC)C=C1C1=CC=NC=N1 NPDWZVIWNJMPPR-UHFFFAOYSA-N 0.000 claims description 2
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