JP2009530296A - ピラゾロ［１，５−ａ］ピリミジン誘導体およびその使用方法 - Google Patents

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Publication number

JP2009530296A

JP2009530296A JP2009500484A JP2009500484A JP2009530296A JP 2009530296 A JP2009530296 A JP 2009530296A JP 2009500484 A JP2009500484 A JP 2009500484A JP 2009500484 A JP2009500484 A JP 2009500484A JP 2009530296 A JP2009530296 A JP 2009530296A

Authority

JP

Japan

Prior art keywords

phenyl

trifluoromethyl

pyrazolo

pyrimidin

amino

Prior art date

2006-03-17

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.)

Withdrawn

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• 238000000034 method Methods 0.000 title claims abstract description 112
• LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title abstract description 11
• 239000000203 mixture Substances 0.000 claims abstract description 89
• 150000001875 compounds Chemical class 0.000 claims abstract description 48
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 22
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 201000011510 cancer Diseases 0.000 claims abstract description 14
• 229940002612 prodrug Drugs 0.000 claims abstract description 11
• 239000000651 prodrug Substances 0.000 claims abstract description 11
• -1 R 14 Chemical compound 0.000 claims description 270
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 214
• 125000004432 carbon atom Chemical group C* 0.000 claims description 175
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 171
• 125000000217 alkyl group Chemical group 0.000 claims description 113
• 125000001072 heteroaryl group Chemical group 0.000 claims description 113
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 109
• 125000000623 heterocyclic group Chemical group 0.000 claims description 98
• 125000003118 aryl group Chemical group 0.000 claims description 82
• AROHANMBFUDDHO-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[3-(3-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=CN=CC=2)=C1 AROHANMBFUDDHO-UHFFFAOYSA-N 0.000 claims description 62
• 125000001424 substituent group Chemical group 0.000 claims description 54
• 229910052760 oxygen Inorganic materials 0.000 claims description 43
• 125000005842 heteroatom Chemical group 0.000 claims description 41
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
• 125000000304 alkynyl group Chemical group 0.000 claims description 37
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 33
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 26
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 12
• 125000001246 bromo group Chemical group Br* 0.000 claims description 12
• YCAVTOUTYRMOGQ-UHFFFAOYSA-N ethyl 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 YCAVTOUTYRMOGQ-UHFFFAOYSA-N 0.000 claims description 12
• 125000002346 iodo group Chemical group I* 0.000 claims description 12
• 125000003107 substituted aryl group Chemical group 0.000 claims description 12
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 10
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 150000002825 nitriles Chemical class 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 9
• PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims description 8
• CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 claims description 7
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• RJBOSILTJMRENQ-UHFFFAOYSA-N 3-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=C1 RJBOSILTJMRENQ-UHFFFAOYSA-N 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 239000012535 impurity Substances 0.000 claims description 6
• MESKGDQSFWBJSN-UHFFFAOYSA-N n-[3-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C2=CNN=C2)=C1 MESKGDQSFWBJSN-UHFFFAOYSA-N 0.000 claims description 6
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
• ORONFVUZGBIKBG-UHFFFAOYSA-N 3,5-difluoro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound FC1=CC(F)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 ORONFVUZGBIKBG-UHFFFAOYSA-N 0.000 claims description 5
• WECFIEKJJIWRPR-UHFFFAOYSA-N ethyl 7-[3-[[3-[[2-(4-methylpiperazin-1-yl)acetyl]amino]-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1NC(=O)CN1CCN(C)CC1 WECFIEKJJIWRPR-UHFFFAOYSA-N 0.000 claims description 5
• LCMNWMABPDVIPG-UHFFFAOYSA-N n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 LCMNWMABPDVIPG-UHFFFAOYSA-N 0.000 claims description 5
• CGWKLERDKWLWBR-UHFFFAOYSA-N n-[3-(3-iodopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(I)=C3N=CC=2)=C1 CGWKLERDKWLWBR-UHFFFAOYSA-N 0.000 claims description 5
• NAYAJYZQGRWMAS-UHFFFAOYSA-N n-[3-[3-(2-methoxypyrimidin-5-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(OC)=NC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 NAYAJYZQGRWMAS-UHFFFAOYSA-N 0.000 claims description 5
• WQTMGJMCPIUINL-UHFFFAOYSA-N n-[3-[3-(5-formylfuran-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2OC(C=O)=CC=2)=C1 WQTMGJMCPIUINL-UHFFFAOYSA-N 0.000 claims description 5
• WRIGMPLUXZMKQQ-UHFFFAOYSA-N n-[4-fluoro-3-(3-iodopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N3N=CC(I)=C3N=CC=2)C(F)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 WRIGMPLUXZMKQQ-UHFFFAOYSA-N 0.000 claims description 5
• CIJPXTYYJNRMBN-UHFFFAOYSA-N n-benzyl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C(=O)NCC=2C=CC=CC=2)=C1 CIJPXTYYJNRMBN-UHFFFAOYSA-N 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• RYGBKRLKVUKFMD-UHFFFAOYSA-N 1-[3-(3-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=CN=CC=2)=C1 RYGBKRLKVUKFMD-UHFFFAOYSA-N 0.000 claims description 4
• WIXVPRYPNBQMHM-UHFFFAOYSA-N 3-(trifluoromethyl)-n-[3-[3-[2-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=C1 WIXVPRYPNBQMHM-UHFFFAOYSA-N 0.000 claims description 4
• GBUHDCIHESIIAG-UHFFFAOYSA-N 3-amino-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-5-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(N)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 GBUHDCIHESIIAG-UHFFFAOYSA-N 0.000 claims description 4
• HWIGPFREDJIWRN-UHFFFAOYSA-N 3-methyl-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound CC1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 HWIGPFREDJIWRN-UHFFFAOYSA-N 0.000 claims description 4
• TUKGPHASWNBAIB-UHFFFAOYSA-N 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-2-carboxylic acid Chemical compound N12N=C(C(=O)O)C=C2N=CC=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 TUKGPHASWNBAIB-UHFFFAOYSA-N 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• PGAQEDMHSNUNCD-UHFFFAOYSA-N ethyl 2-methyl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C(C)=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 PGAQEDMHSNUNCD-UHFFFAOYSA-N 0.000 claims description 4
• AJBLBPMFELDUQC-UHFFFAOYSA-N ethyl 7-[3-[[3-[(2-chloroacetyl)amino]-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC(NC(=O)CCl)=CC(C(F)(F)F)=C1 AJBLBPMFELDUQC-UHFFFAOYSA-N 0.000 claims description 4
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
• BMVFRDWYIBSEOB-UHFFFAOYSA-N n-(3-pyrazolo[1,5-a]pyrimidin-7-ylphenyl)-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC=C3N=CC=2)=C1 BMVFRDWYIBSEOB-UHFFFAOYSA-N 0.000 claims description 4
• IVFOMDILWVRNQN-UHFFFAOYSA-N n-[3-[2-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 IVFOMDILWVRNQN-UHFFFAOYSA-N 0.000 claims description 4
• VEMVDVZGXHINMW-UHFFFAOYSA-N n-[3-[2-(4-oxopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)N2CCC(=O)CC2)=C1 VEMVDVZGXHINMW-UHFFFAOYSA-N 0.000 claims description 4
• JJZOVOIIHBFRIW-UHFFFAOYSA-N n-[3-[2-[2-[3-(dimethylamino)propylamino]pyridin-4-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCCN(C)C)=CC(C2=NN3C(C=4C=C(NC(=O)C=5C=C(C=CC=5)C(F)(F)F)C=CC=4)=CC=NC3=C2)=C1 JJZOVOIIHBFRIW-UHFFFAOYSA-N 0.000 claims description 4
• MUTSDHQERKNLCA-UHFFFAOYSA-N n-[3-[3-(2-acetylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CC(=O)C1=CC=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 MUTSDHQERKNLCA-UHFFFAOYSA-N 0.000 claims description 4
• SSWCOMVKKKYWJH-UHFFFAOYSA-N n-[3-[3-(3,5-diformylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=C(C=O)C=C(C=O)C=2)=C1 SSWCOMVKKKYWJH-UHFFFAOYSA-N 0.000 claims description 4
• QWBVWBRORBKBFM-UHFFFAOYSA-N n-[3-[3-(3-acetylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CC(=O)C1=CC=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=C1 QWBVWBRORBKBFM-UHFFFAOYSA-N 0.000 claims description 4
• LIEUEJGSVLDELS-UHFFFAOYSA-N n-[3-[3-(3-aminophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound NC1=CC=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=C1 LIEUEJGSVLDELS-UHFFFAOYSA-N 0.000 claims description 4
• CNAMYLDNIIXYMW-UHFFFAOYSA-N n-[3-[3-[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C2=CN(CCN3CCCC3)N=C2)=C1 CNAMYLDNIIXYMW-UHFFFAOYSA-N 0.000 claims description 4
• XADBIUJSFGNLFR-UHFFFAOYSA-N n-[3-[3-[3-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound OCC1=CC=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=C1 XADBIUJSFGNLFR-UHFFFAOYSA-N 0.000 claims description 4
• APMUVXPIJNPXQE-UHFFFAOYSA-N n-[3-[3-[4-(pyrrolidin-1-ylmethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=CC(CN3CCCC3)=CC=2)=C1 APMUVXPIJNPXQE-UHFFFAOYSA-N 0.000 claims description 4
• QFKGZTAXDWUBSU-UHFFFAOYSA-N n-[3-[3-[5-(pyrrolidin-1-ylmethyl)furan-2-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2OC(CN3CCCC3)=CC=2)=C1 QFKGZTAXDWUBSU-UHFFFAOYSA-N 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• ZYQQKHGLXZARBT-UHFFFAOYSA-N tert-butyl 4-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazole-1-carboxylate Chemical compound C1=NN(C(=O)OC(C)(C)C)C=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 ZYQQKHGLXZARBT-UHFFFAOYSA-N 0.000 claims description 4
• SGIPRIGOGRAVTH-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 SGIPRIGOGRAVTH-UHFFFAOYSA-N 0.000 claims description 3
• JQRDVDGBAIMDCR-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-[3-(3-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=NC=CC=2)=C1 JQRDVDGBAIMDCR-UHFFFAOYSA-N 0.000 claims description 3
• YAKFYLCVVIORSY-UHFFFAOYSA-N 1-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 YAKFYLCVVIORSY-UHFFFAOYSA-N 0.000 claims description 3
• WNBQTJFNCXLQAW-UHFFFAOYSA-N 1-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(3,4-dichlorophenyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC(C=2N3N=CC(Br)=C3N=CC=2)=C1 WNBQTJFNCXLQAW-UHFFFAOYSA-N 0.000 claims description 3
• VVAUKFDARJPHOM-UHFFFAOYSA-N 1-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C=2N3N=CC(Br)=C3N=CC=2)=C1 VVAUKFDARJPHOM-UHFFFAOYSA-N 0.000 claims description 3
• GMKNYCDWPUZDMA-UHFFFAOYSA-N 1-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2C=C(C=CC=2)C=2N3N=CC(Br)=C3N=CC=2)=C1 GMKNYCDWPUZDMA-UHFFFAOYSA-N 0.000 claims description 3
• CLSWDIIXABACRD-UHFFFAOYSA-N 1-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-[4-fluoro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC1=CC=CC(C=2N3N=CC(Br)=C3N=CC=2)=C1 CLSWDIIXABACRD-UHFFFAOYSA-N 0.000 claims description 3
• CPOBILZHPNBNNG-UHFFFAOYSA-N 1-[3-(3-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=NC=CC=2)=C1 CPOBILZHPNBNNG-UHFFFAOYSA-N 0.000 claims description 3
• NPQUATBFRAARGO-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 NPQUATBFRAARGO-UHFFFAOYSA-N 0.000 claims description 3
• KZNGWXWPVOLSQU-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 KZNGWXWPVOLSQU-UHFFFAOYSA-N 0.000 claims description 3
• WCPSZEHHQUGYLS-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[3-(3-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=NC=CC=2)=C1 WCPSZEHHQUGYLS-UHFFFAOYSA-N 0.000 claims description 3
• WJOGTIKDIGOFES-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 WJOGTIKDIGOFES-UHFFFAOYSA-N 0.000 claims description 3
• ATGDMSGZVNIROG-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 ATGDMSGZVNIROG-UHFFFAOYSA-N 0.000 claims description 3
• QIWUSHRQVSSPQE-UHFFFAOYSA-N 1-methyl-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]indole-2-carboxamide Chemical compound C=1C2=CC=CC=C2N(C)C=1C(=O)NC(C=1)=CC=CC=1C(N1N=2)=CC=NC1=CC=2C1=CC=NC=C1 QIWUSHRQVSSPQE-UHFFFAOYSA-N 0.000 claims description 3
• UVTINTINTKLCRF-UHFFFAOYSA-N 1-methyl-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]pyrrole-2-carboxamide Chemical compound CN1C=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 UVTINTINTKLCRF-UHFFFAOYSA-N 0.000 claims description 3
• CYKSRYDSCLHTAL-UHFFFAOYSA-N 2,2,2-trifluoroethyl 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 CYKSRYDSCLHTAL-UHFFFAOYSA-N 0.000 claims description 3
• PWKVECBFGMGWLG-UHFFFAOYSA-N 2-(dimethylamino)ethyl 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCCN(C)C)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 PWKVECBFGMGWLG-UHFFFAOYSA-N 0.000 claims description 3
• ZYZBUXCTTHJEFN-UHFFFAOYSA-N 2-bromo-5-chloro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound ClC1=CC=C(Br)C(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 ZYZBUXCTTHJEFN-UHFFFAOYSA-N 0.000 claims description 3
• OPEUBBQIMNNLHZ-UHFFFAOYSA-N 2-chloro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound ClC1=CC=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 OPEUBBQIMNNLHZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• WAZLZOSWHWGHDO-UHFFFAOYSA-N 2-methoxyethyl 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCCOC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 WAZLZOSWHWGHDO-UHFFFAOYSA-N 0.000 claims description 3
• HABLFKHXAYKBRR-UHFFFAOYSA-N 3,3-dimethyl-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]butanamide Chemical compound CC(C)(C)CC(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 HABLFKHXAYKBRR-UHFFFAOYSA-N 0.000 claims description 3
• ANSYTWNVLCBDKD-UHFFFAOYSA-N 3,4-dichloro-n-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 ANSYTWNVLCBDKD-UHFFFAOYSA-N 0.000 claims description 3
• HZKVQTZSYHOKCL-UHFFFAOYSA-N 3,4-dichloro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 HZKVQTZSYHOKCL-UHFFFAOYSA-N 0.000 claims description 3
• CAINWFDOFYMJIN-UHFFFAOYSA-N 3-(difluoromethyl)-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound FC(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 CAINWFDOFYMJIN-UHFFFAOYSA-N 0.000 claims description 3
• WEKIKNDFSVCDIH-UHFFFAOYSA-N 3-(pyridin-1-ium-1-ylmethyl)-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide;chloride Chemical compound [Cl-].C=1C=CC(C[N+]=2C=CC=CC=2)=CC=1C(=O)NC(C=1)=CC=CC=1C(N1N=2)=CC=NC1=CC=2C1=CC=NC=C1 WEKIKNDFSVCDIH-UHFFFAOYSA-N 0.000 claims description 3
• FECZQYKCIHTMRD-UHFFFAOYSA-N 3-(trifluoromethyl)-n-[3-[2-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=C1 FECZQYKCIHTMRD-UHFFFAOYSA-N 0.000 claims description 3
• FVWVORIFZUWGHE-UHFFFAOYSA-N 3-(trifluoromethyl)-n-[3-[3-(2-trimethylsilylethynyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]benzamide Chemical compound C=1C=NC2=C(C#C[Si](C)(C)C)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 FVWVORIFZUWGHE-UHFFFAOYSA-N 0.000 claims description 3
• RGABHHPTURBLJU-UHFFFAOYSA-N 3-(trifluoromethyl)-n-[3-[3-[1-tri(propan-2-yl)silylpyrrol-3-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]benzamide Chemical compound CC(C)[Si](C(C)C)(C(C)C)N1C=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=C1 RGABHHPTURBLJU-UHFFFAOYSA-N 0.000 claims description 3
• KUWPCJGGDJLNRX-UHFFFAOYSA-N 3-(trifluoromethyl)-n-[3-[3-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=C1 KUWPCJGGDJLNRX-UHFFFAOYSA-N 0.000 claims description 3
• UWACYSKKHKUXMS-UHFFFAOYSA-N 3-(trifluoromethyl)-n-[3-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 UWACYSKKHKUXMS-UHFFFAOYSA-N 0.000 claims description 3
• WQPJGCOCRINZPY-UHFFFAOYSA-N 3-[(2-chloroacetyl)amino]-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-5-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(NC(=O)CCl)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 WQPJGCOCRINZPY-UHFFFAOYSA-N 0.000 claims description 3
• KFLUPBPVWWZJOE-UHFFFAOYSA-N 3-bromo-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound BrC1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 KFLUPBPVWWZJOE-UHFFFAOYSA-N 0.000 claims description 3
• XOPKUUJHGXTLIH-UHFFFAOYSA-N 3-chloro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound ClC1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 XOPKUUJHGXTLIH-UHFFFAOYSA-N 0.000 claims description 3
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• YVFZEXDTSJHDSK-UHFFFAOYSA-N 3-methoxy-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 YVFZEXDTSJHDSK-UHFFFAOYSA-N 0.000 claims description 3
• MZWHLWDVJXFUEJ-UHFFFAOYSA-N 4-chloro-n-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 MZWHLWDVJXFUEJ-UHFFFAOYSA-N 0.000 claims description 3
• NAZBCPATAWKFPO-UHFFFAOYSA-N 4-chloro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 NAZBCPATAWKFPO-UHFFFAOYSA-N 0.000 claims description 3
• FHISTFVUFJIYQP-UHFFFAOYSA-N 4-chloro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 FHISTFVUFJIYQP-UHFFFAOYSA-N 0.000 claims description 3
• TYYANJZGHQLNFR-UHFFFAOYSA-N 4-chloro-n-[3-(3-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=NC=CC=2)=C1 TYYANJZGHQLNFR-UHFFFAOYSA-N 0.000 claims description 3
• CRBODUGCYQALPN-UHFFFAOYSA-N 4-chloro-n-[3-(3-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=CN=CC=2)=C1 CRBODUGCYQALPN-UHFFFAOYSA-N 0.000 claims description 3
• ANVHGOJNAFPPHY-UHFFFAOYSA-N 4-fluoro-n-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 ANVHGOJNAFPPHY-UHFFFAOYSA-N 0.000 claims description 3
• JOOSHJACXWWUQI-UHFFFAOYSA-N 4-fluoro-n-[3-(3-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=NC=CC=2)=C1 JOOSHJACXWWUQI-UHFFFAOYSA-N 0.000 claims description 3
• JMZZXKZXYPPJJH-UHFFFAOYSA-N 4-fluoro-n-[3-(3-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=CN=CC=2)=C1 JMZZXKZXYPPJJH-UHFFFAOYSA-N 0.000 claims description 3
• CGUPVVQSCAXDNF-UHFFFAOYSA-N 4-methoxy-n-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 CGUPVVQSCAXDNF-UHFFFAOYSA-N 0.000 claims description 3
• UXVNLVYEZALVJD-UHFFFAOYSA-N 4-methoxy-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 UXVNLVYEZALVJD-UHFFFAOYSA-N 0.000 claims description 3
• JHXPLEAJSAZBCC-UHFFFAOYSA-N 4-methoxy-n-[3-(3-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=NC=CC=2)=C1 JHXPLEAJSAZBCC-UHFFFAOYSA-N 0.000 claims description 3
• VLAKNUROJQAYHV-UHFFFAOYSA-N 4-methoxy-n-[3-(3-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=CN=CC=2)=C1 VLAKNUROJQAYHV-UHFFFAOYSA-N 0.000 claims description 3
• FZMKZYUNNVVYBG-UHFFFAOYSA-N 4-methyl-n-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 FZMKZYUNNVVYBG-UHFFFAOYSA-N 0.000 claims description 3
• GLUSOUGUMGWOAO-UHFFFAOYSA-N 4-methyl-n-[3-(2-phenylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CC=CC=2)=C1 GLUSOUGUMGWOAO-UHFFFAOYSA-N 0.000 claims description 3
• DCXRIISUDLYMAE-UHFFFAOYSA-N 4-methyl-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 DCXRIISUDLYMAE-UHFFFAOYSA-N 0.000 claims description 3
• LHHJIYWIQYRNPZ-UHFFFAOYSA-N 4-methyl-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 LHHJIYWIQYRNPZ-UHFFFAOYSA-N 0.000 claims description 3
• DJYCSFJGLFPZRE-UHFFFAOYSA-N 4-methyl-n-[3-(3-pyridin-2-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2N=CC=CC=2)=C1 DJYCSFJGLFPZRE-UHFFFAOYSA-N 0.000 claims description 3
• QLJKMOXFJIOOEN-UHFFFAOYSA-N 4-methyl-n-[3-(3-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=NC=CC=2)=C1 QLJKMOXFJIOOEN-UHFFFAOYSA-N 0.000 claims description 3
• FASSYARADYBXEU-UHFFFAOYSA-N 4-methyl-n-[3-(3-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=CN=CC=2)=C1 FASSYARADYBXEU-UHFFFAOYSA-N 0.000 claims description 3
• JGJMNPYUYOAEEV-UHFFFAOYSA-N 4-methyl-n-[3-[3-(2h-tetrazol-5-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C2=NNN=N2)=C1 JGJMNPYUYOAEEV-UHFFFAOYSA-N 0.000 claims description 3
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• WOMLWFPGGVLXQL-UHFFFAOYSA-N 5-bromo-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]thiophene-2-carboxamide Chemical compound S1C(Br)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 WOMLWFPGGVLXQL-UHFFFAOYSA-N 0.000 claims description 3
• SAKKTHNFOONBJP-UHFFFAOYSA-N 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)N)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 SAKKTHNFOONBJP-UHFFFAOYSA-N 0.000 claims description 3
• RPHZLLIROXDHEW-UHFFFAOYSA-N 7-[3-[[4-methyl-3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C(N)=O)=C1 RPHZLLIROXDHEW-UHFFFAOYSA-N 0.000 claims description 3
• YWPMZLOGNDHZFS-UHFFFAOYSA-N ethyl 6-methyl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CC=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 YWPMZLOGNDHZFS-UHFFFAOYSA-N 0.000 claims description 3
• AJXNULFCPCGWFM-UHFFFAOYSA-N ethyl 7-[2-fluoro-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C(=CC=1)F)=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 AJXNULFCPCGWFM-UHFFFAOYSA-N 0.000 claims description 3
• BZMOHSVWVNQKKP-UHFFFAOYSA-N ethyl 7-[2-nitro-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C(=CC=1)[N+]([O-])=O)=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 BZMOHSVWVNQKKP-UHFFFAOYSA-N 0.000 claims description 3
• BSVZZQVVZVGYAA-UHFFFAOYSA-N ethyl 7-[3-[(2-bromo-5-chlorobenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC(Cl)=CC=C1Br BSVZZQVVZVGYAA-UHFFFAOYSA-N 0.000 claims description 3
• GRNRCYLMJBEEDM-UHFFFAOYSA-N ethyl 7-[3-[(3-bromobenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(Br)=C1 GRNRCYLMJBEEDM-UHFFFAOYSA-N 0.000 claims description 3
• PHDJVZCVXUWRGT-UHFFFAOYSA-N ethyl 7-[3-[(3-chloro-4-methoxybenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(OC)C(Cl)=C1 PHDJVZCVXUWRGT-UHFFFAOYSA-N 0.000 claims description 3
• GJFRNUBRALSFKT-UHFFFAOYSA-N ethyl 7-[3-[(3-chlorobenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(Cl)=C1 GJFRNUBRALSFKT-UHFFFAOYSA-N 0.000 claims description 3
• SLLCNVWKVGYCLX-UHFFFAOYSA-N ethyl 7-[3-[(3-cyanobenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C#N)=C1 SLLCNVWKVGYCLX-UHFFFAOYSA-N 0.000 claims description 3
• LVNMQZPNEQWUKM-UHFFFAOYSA-N ethyl 7-[3-[(3-methoxybenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(OC)=C1 LVNMQZPNEQWUKM-UHFFFAOYSA-N 0.000 claims description 3
• XFQHIUKTIWAPNS-UHFFFAOYSA-N ethyl 7-[3-[(3-methylbenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C)=C1 XFQHIUKTIWAPNS-UHFFFAOYSA-N 0.000 claims description 3
• SYNRSOLQMUBNAM-UHFFFAOYSA-N ethyl 7-[3-[(4-chloro-2,5-difluorobenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC(F)=C(Cl)C=C1F SYNRSOLQMUBNAM-UHFFFAOYSA-N 0.000 claims description 3
• DMZGVMBTFLAJRR-UHFFFAOYSA-N ethyl 7-[3-[(4-chlorobenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(Cl)C=C1 DMZGVMBTFLAJRR-UHFFFAOYSA-N 0.000 claims description 3
• CIIPGJWPWFJSJQ-UHFFFAOYSA-N ethyl 7-[3-[[2-methyl-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC(C(F)(F)F)=CC=C1C CIIPGJWPWFJSJQ-UHFFFAOYSA-N 0.000 claims description 3
• AQSLIIGESPZIFW-UHFFFAOYSA-N ethyl 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound N12N=C(C(=O)OCC)C=C2N=CC=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 AQSLIIGESPZIFW-UHFFFAOYSA-N 0.000 claims description 3
• WUHBRWQZRDNPIH-UHFFFAOYSA-N ethyl 7-[3-[[3-chloro-2-fluoro-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC(C(F)(F)F)=CC(Cl)=C1F WUHBRWQZRDNPIH-UHFFFAOYSA-N 0.000 claims description 3
• YEHBPXLAMKWGGY-UHFFFAOYSA-N ethyl 7-[3-[[3-fluoro-4-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(C(F)(F)F)C(F)=C1 YEHBPXLAMKWGGY-UHFFFAOYSA-N 0.000 claims description 3
• VZDYKWUFAPCQAS-UHFFFAOYSA-N ethyl 7-[3-[[3-fluoro-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC(F)=CC(C(F)(F)F)=C1 VZDYKWUFAPCQAS-UHFFFAOYSA-N 0.000 claims description 3
• JIVQWFZRSLHDMU-UHFFFAOYSA-N ethyl 7-[3-[[4-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(C(F)(F)F)C=C1 JIVQWFZRSLHDMU-UHFFFAOYSA-N 0.000 claims description 3
• KUNDZSRQVZNOAB-UHFFFAOYSA-N ethyl 7-[3-[[4-chloro-3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 KUNDZSRQVZNOAB-UHFFFAOYSA-N 0.000 claims description 3
• YARCJPSOEYYZMU-UHFFFAOYSA-N ethyl 7-[3-[[4-fluoro-2-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(F)C=C1C(F)(F)F YARCJPSOEYYZMU-UHFFFAOYSA-N 0.000 claims description 3
• JNMMAWCRPCMSMU-UHFFFAOYSA-N ethyl 7-[3-[[4-fluoro-3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(F)C(C(F)(F)F)=C1 JNMMAWCRPCMSMU-UHFFFAOYSA-N 0.000 claims description 3
• OQAJZRGPPOXKEL-UHFFFAOYSA-N ethyl 7-[3-[[4-methoxy-3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(OC)C(C(F)(F)F)=C1 OQAJZRGPPOXKEL-UHFFFAOYSA-N 0.000 claims description 3
• LNEZCTJJIDDWKC-UHFFFAOYSA-N ethyl 7-[3-[[4-methyl-3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(C)C(C(F)(F)F)=C1 LNEZCTJJIDDWKC-UHFFFAOYSA-N 0.000 claims description 3
• YZXXGHUTYZJYRE-UHFFFAOYSA-N ethyl 7-[4-chloro-3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=C(Cl)C=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 YZXXGHUTYZJYRE-UHFFFAOYSA-N 0.000 claims description 3
• BDLMYYOTEFQVSR-UHFFFAOYSA-N ethyl 7-[4-chloro-3-[[4-methyl-3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=C(Cl)C=1NC(=O)C1=CC=C(C)C(C(F)(F)F)=C1 BDLMYYOTEFQVSR-UHFFFAOYSA-N 0.000 claims description 3
• DGVSIFNNNYLXQS-UHFFFAOYSA-N ethyl 7-[4-fluoro-3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=C(F)C=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 DGVSIFNNNYLXQS-UHFFFAOYSA-N 0.000 claims description 3
• XRTOJDSIRNEALU-UHFFFAOYSA-N ethyl 7-[4-methoxy-3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=C(OC)C=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 XRTOJDSIRNEALU-UHFFFAOYSA-N 0.000 claims description 3
• YVUJGWRQLAFUBS-UHFFFAOYSA-N ethyl 7-[4-methoxy-3-[[4-methyl-3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=C(OC)C=1NC(=O)C1=CC=C(C)C(C(F)(F)F)=C1 YVUJGWRQLAFUBS-UHFFFAOYSA-N 0.000 claims description 3
• DKPQGFYCMFFIJU-UHFFFAOYSA-N ethyl 7-[5-[[4-methyl-3-(trifluoromethyl)benzoyl]amino]-2-nitrophenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C(=CC=1)[N+]([O-])=O)=CC=1NC(=O)C1=CC=C(C)C(C(F)(F)F)=C1 DKPQGFYCMFFIJU-UHFFFAOYSA-N 0.000 claims description 3
• 230000012010 growth Effects 0.000 claims description 3
• BMEFRHYUBNQXAU-UHFFFAOYSA-N methyl 3-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C2=NN3C(C=4C=C(NC(=O)C=5C=C(C=CC=5)C(F)(F)F)C=CC=4)=CC=NC3=C2)=C1 BMEFRHYUBNQXAU-UHFFFAOYSA-N 0.000 claims description 3
• PAHHPBIONVYDNI-UHFFFAOYSA-N methyl 3-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=C1 PAHHPBIONVYDNI-UHFFFAOYSA-N 0.000 claims description 3
• APAVJWIMYUTAQK-UHFFFAOYSA-N methyl 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 APAVJWIMYUTAQK-UHFFFAOYSA-N 0.000 claims description 3
• PTYYEWAEDVRVQR-UHFFFAOYSA-N n-(2-methoxyethyl)-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)NCCOC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 PTYYEWAEDVRVQR-UHFFFAOYSA-N 0.000 claims description 3
• YMPDSPYFMVDETC-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C(=O)NCCN2CCOCC2)=C1 YMPDSPYFMVDETC-UHFFFAOYSA-N 0.000 claims description 3
• KWNPEXKKOBBJEZ-UHFFFAOYSA-N n-(2-pyrrolidin-1-ylethyl)-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C(=O)NCCN2CCCC2)=C1 KWNPEXKKOBBJEZ-UHFFFAOYSA-N 0.000 claims description 3
• ZLBPZOCCRFOAAV-UHFFFAOYSA-N n-(3-methoxypropyl)-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)NCCCOC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 ZLBPZOCCRFOAAV-UHFFFAOYSA-N 0.000 claims description 3
• NYVNYZHCLXLDAB-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C(=O)NCCCN2CCOCC2)=C1 NYVNYZHCLXLDAB-UHFFFAOYSA-N 0.000 claims description 3
• LBIGLVUIRXGNOE-UHFFFAOYSA-N n-(4-chloro-3-pyrazolo[1,5-a]pyrimidin-7-ylphenyl)-4-(morpholin-4-ylmethyl)-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(C(=O)NC=2C=C(C(Cl)=CC=2)C=2N3N=CC=C3N=CC=2)=CC=C1CN1CCOCC1 LBIGLVUIRXGNOE-UHFFFAOYSA-N 0.000 claims description 3
• QOSBJBOZROPAKI-UHFFFAOYSA-N n-(4-fluoro-3-pyrazolo[1,5-a]pyrimidin-7-ylphenyl)-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N3N=CC=C3N=CC=2)C(F)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 QOSBJBOZROPAKI-UHFFFAOYSA-N 0.000 claims description 3
• KXBLSIYLDTVOJJ-UHFFFAOYSA-N n-[2-(1-methylpyrrolidin-2-yl)ethyl]-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CN1CCCC1CCNC(=O)C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 KXBLSIYLDTVOJJ-UHFFFAOYSA-N 0.000 claims description 3
• LBMOATDHLVFWMQ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)NCCN(C)C)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 LBMOATDHLVFWMQ-UHFFFAOYSA-N 0.000 claims description 3
• DEYGTHMVASZYAW-UHFFFAOYSA-N n-[3-(2-methylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound N12N=C(C)C=C2N=CC=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 DEYGTHMVASZYAW-UHFFFAOYSA-N 0.000 claims description 3
• CSBJRBYRFSOSAV-UHFFFAOYSA-N n-[3-(2-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)N2CCOCC2)=C1 CSBJRBYRFSOSAV-UHFFFAOYSA-N 0.000 claims description 3
• BYYUAHCUHJMTHJ-UHFFFAOYSA-N n-[3-(2-piperazin-1-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)N2CCNCC2)=C1 BYYUAHCUHJMTHJ-UHFFFAOYSA-N 0.000 claims description 3
• PNDYNOWGANKZQZ-UHFFFAOYSA-N n-[3-(2-pyridin-2-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2N=CC=CC=2)=C1 PNDYNOWGANKZQZ-UHFFFAOYSA-N 0.000 claims description 3
• HWXNOWYUIGQFRY-UHFFFAOYSA-N n-[3-(2-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=NC=CC=2)=C1 HWXNOWYUIGQFRY-UHFFFAOYSA-N 0.000 claims description 3
• ZICNAWJYTJVNBZ-UHFFFAOYSA-N n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1)=CC=CC=1C(N1N=2)=CC=NC1=CC=2C1=CC=NC=C1 ZICNAWJYTJVNBZ-UHFFFAOYSA-N 0.000 claims description 3
• XEIQOGUOFCEMTH-UHFFFAOYSA-N n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]isoquinoline-1-carboxamide Chemical compound N=1C=CC2=CC=CC=C2C=1C(=O)NC(C=1)=CC=CC=1C(N1N=2)=CC=NC1=CC=2C1=CC=NC=C1 XEIQOGUOFCEMTH-UHFFFAOYSA-N 0.000 claims description 3
• VMBHOJLLEGDUAC-UHFFFAOYSA-N n-[3-(2-tert-butylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound N12N=C(C(C)(C)C)C=C2N=CC=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 VMBHOJLLEGDUAC-UHFFFAOYSA-N 0.000 claims description 3
• XWEOGRVYIIHQGM-UHFFFAOYSA-N n-[3-(3-bromo-6-methylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound CC=1C=NC2=C(Br)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 XWEOGRVYIIHQGM-UHFFFAOYSA-N 0.000 claims description 3
• PCWQGROLOSUHDM-UHFFFAOYSA-N n-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)-4-chlorophenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C(Cl)=CC=2)C=2N3N=CC(Br)=C3N=CC=2)=C1 PCWQGROLOSUHDM-UHFFFAOYSA-N 0.000 claims description 3
• WKBRHZLKZYTDTJ-UHFFFAOYSA-N n-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-4-chloro-3-(trifluoromethyl)benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(Br)=C3N=CC=2)=C1 WKBRHZLKZYTDTJ-UHFFFAOYSA-N 0.000 claims description 3
• GBMFOQZMZBFTFC-UHFFFAOYSA-N n-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-4-fluoro-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(Br)=C3N=CC=2)=C1 GBMFOQZMZBFTFC-UHFFFAOYSA-N 0.000 claims description 3
• NASQIRGYUKFFKT-UHFFFAOYSA-N n-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-4-methoxy-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(Br)=C3N=CC=2)=C1 NASQIRGYUKFFKT-UHFFFAOYSA-N 0.000 claims description 3
• IMZPIZKPXXJZHQ-UHFFFAOYSA-N n-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-4-methyl-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(Br)=C3N=CC=2)=C1 IMZPIZKPXXJZHQ-UHFFFAOYSA-N 0.000 claims description 3
• LCPMYWMEUGYVMF-UHFFFAOYSA-N n-[3-(3-cyano-2-piperazin-1-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-4-methyl-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C(C#N)=C3N=CC=2)N2CCNCC2)=C1 LCPMYWMEUGYVMF-UHFFFAOYSA-N 0.000 claims description 3
• KLQVNFICRLTGGF-UHFFFAOYSA-N n-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C#N)=C1 KLQVNFICRLTGGF-UHFFFAOYSA-N 0.000 claims description 3
• FBWNYZPJQLWDNV-UHFFFAOYSA-N n-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-4-methyl-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 FBWNYZPJQLWDNV-UHFFFAOYSA-N 0.000 claims description 3
• KKBFLNJSPUXUMV-UHFFFAOYSA-N n-[3-(3-ethynylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C#C)=C1 KKBFLNJSPUXUMV-UHFFFAOYSA-N 0.000 claims description 3
• HZAKJPMNYCNPHY-UHFFFAOYSA-N n-[3-(3-pyridin-2-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2N=CC=CC=2)=C1 HZAKJPMNYCNPHY-UHFFFAOYSA-N 0.000 claims description 3
• UAQFLCCYSVWUFS-UHFFFAOYSA-N n-[3-(3-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=NC=CC=2)=C1 UAQFLCCYSVWUFS-UHFFFAOYSA-N 0.000 claims description 3
• BGPZJJPVZGELAE-UHFFFAOYSA-N n-[3-(3-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=CN=CC=2)=C1 BGPZJJPVZGELAE-UHFFFAOYSA-N 0.000 claims description 3
• GTRUKUUANNAZAA-UHFFFAOYSA-N n-[3-(5-methyl-2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound N12N=C(C=3C=CN=CC=3)C=C2N=C(C)C=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 GTRUKUUANNAZAA-UHFFFAOYSA-N 0.000 claims description 3
• HLJVSACRZHSKRN-UHFFFAOYSA-N n-[3-(6-methyl-2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound CC=1C=NC2=CC(C=3C=CN=CC=3)=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 HLJVSACRZHSKRN-UHFFFAOYSA-N 0.000 claims description 3
• PTJIJXMNTFVISO-UHFFFAOYSA-N n-[3-(6-methyl-3-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound CC=1C=NC2=C(C=3C=NC=CC=3)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 PTJIJXMNTFVISO-UHFFFAOYSA-N 0.000 claims description 3
• LCQRBHGZPAFKKF-UHFFFAOYSA-N n-[3-[2-(3-methylimidazol-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN1C=NC=C1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 LCQRBHGZPAFKKF-UHFFFAOYSA-N 0.000 claims description 3
• IPFKSOSHMLFTGG-UHFFFAOYSA-N n-[3-[2-(3-oxopiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)N2CC(=O)NCC2)=C1 IPFKSOSHMLFTGG-UHFFFAOYSA-N 0.000 claims description 3
• JXDAUCXDPPIVDU-UHFFFAOYSA-N n-[3-[2-(4-benzylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)N2CCN(CC=3C=CC=CC=3)CC2)=C1 JXDAUCXDPPIVDU-UHFFFAOYSA-N 0.000 claims description 3
• ULFKFUOMKLYUIE-UHFFFAOYSA-N n-[3-[2-(4-bromophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CC(Br)=CC=2)=C1 ULFKFUOMKLYUIE-UHFFFAOYSA-N 0.000 claims description 3
• FJERGDPEKMPNGF-UHFFFAOYSA-N n-[3-[2-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CC(Cl)=CC=2)=C1 FJERGDPEKMPNGF-UHFFFAOYSA-N 0.000 claims description 3
• PBXJORIFKHJVNR-UHFFFAOYSA-N n-[3-[2-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-4-methyl-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CC(Cl)=CC=2)=C1 PBXJORIFKHJVNR-UHFFFAOYSA-N 0.000 claims description 3
• FFRYUKILNALCFY-UHFFFAOYSA-N n-[3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(F)=CC=C1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 FFRYUKILNALCFY-UHFFFAOYSA-N 0.000 claims description 3
• FTGBLGHQTZGNMH-UHFFFAOYSA-N n-[3-[2-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(OC)=CC=C1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 FTGBLGHQTZGNMH-UHFFFAOYSA-N 0.000 claims description 3
• DERVVPCSMXZNRC-UHFFFAOYSA-N n-[3-[2-(dimethylamino)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound N12N=C(N(C)C)C=C2N=CC=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 DERVVPCSMXZNRC-UHFFFAOYSA-N 0.000 claims description 3
• CLWNNHIJLOVNCC-OAQYLSRUSA-N n-[3-[2-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound COC[C@H]1CCCN1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 CLWNNHIJLOVNCC-OAQYLSRUSA-N 0.000 claims description 3
• NCTQXVVMNWVNCT-UHFFFAOYSA-N n-[3-[2-[3-(dimethylamino)propyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound N12N=C(CCCN(C)C)C=C2N=CC=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 NCTQXVVMNWVNCT-UHFFFAOYSA-N 0.000 claims description 3
• ASDOANKAXIMVAX-UHFFFAOYSA-N n-[3-[2-[3-(dimethylamino)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1C(N(C)C)CCN1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 ASDOANKAXIMVAX-UHFFFAOYSA-N 0.000 claims description 3
• YEANJFLLVULMQN-UHFFFAOYSA-N n-[3-[2-[4-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(CO)=CC=C1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 YEANJFLLVULMQN-UHFFFAOYSA-N 0.000 claims description 3
• NWNZEVVTCAXRFX-UHFFFAOYSA-N n-[3-[3-(2-chloropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=C(Cl)N=CC=2)=C1 NWNZEVVTCAXRFX-UHFFFAOYSA-N 0.000 claims description 3
• LMEADLXFPWSABP-UHFFFAOYSA-N n-[3-[3-(2-cyanophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C(=CC=CC=2)C#N)=C1 LMEADLXFPWSABP-UHFFFAOYSA-N 0.000 claims description 3
• OTGOJTAPSQVOTA-UHFFFAOYSA-N n-[3-[3-(2-methylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 OTGOJTAPSQVOTA-UHFFFAOYSA-N 0.000 claims description 3
• VCDGKWNVDVWMTR-UHFFFAOYSA-N n-[3-[3-(2h-tetrazol-5-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C2=NNN=N2)=C1 VCDGKWNVDVWMTR-UHFFFAOYSA-N 0.000 claims description 3
• NSCRYVFCPUVFGN-UHFFFAOYSA-N n-[3-[3-(3-cyanophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=C(C=CC=2)C#N)=C1 NSCRYVFCPUVFGN-UHFFFAOYSA-N 0.000 claims description 3
• YJSCPQHEZYZVPZ-UHFFFAOYSA-N n-[3-[3-(3-cyanophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-4-methyl-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=C(C=CC=2)C#N)=C1 YJSCPQHEZYZVPZ-UHFFFAOYSA-N 0.000 claims description 3
• CEQLOINFWQECBA-UHFFFAOYSA-N n-[3-[3-(3-hydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-4-methyl-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=C(O)C=CC=2)=C1 CEQLOINFWQECBA-UHFFFAOYSA-N 0.000 claims description 3
• UALUSRAHZHGTJF-UHFFFAOYSA-N n-[3-[3-(4-acetylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(C(=O)C)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 UALUSRAHZHGTJF-UHFFFAOYSA-N 0.000 claims description 3
• BGFCIZBIINPPAQ-UHFFFAOYSA-N n-[3-[3-(4-aminophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-4-methyl-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C=2C=CC(N)=CC=2)=C1 BGFCIZBIINPPAQ-UHFFFAOYSA-N 0.000 claims description 3
• VLDLFFXGGUZBHC-UHFFFAOYSA-N n-[3-[3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=CC(Cl)=CC=2)=C1 VLDLFFXGGUZBHC-UHFFFAOYSA-N 0.000 claims description 3
• RPSASAUYSDWMKT-UHFFFAOYSA-N n-[3-[3-(4-cyanophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=CC(=CC=2)C#N)=C1 RPSASAUYSDWMKT-UHFFFAOYSA-N 0.000 claims description 3
• RHHTZZXBZWYHBO-UHFFFAOYSA-N n-[3-[3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(OC)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 RHHTZZXBZWYHBO-UHFFFAOYSA-N 0.000 claims description 3
• CUGAIFIDJYEYCR-UHFFFAOYSA-N n-[3-[3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(C)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 CUGAIFIDJYEYCR-UHFFFAOYSA-N 0.000 claims description 3
• WOJQXXRQZMATOI-UHFFFAOYSA-N n-[3-[3-(5-formylfuran-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=C(C=O)OC=2)=C1 WOJQXXRQZMATOI-UHFFFAOYSA-N 0.000 claims description 3
• UXQZKYRXGWLYAD-UHFFFAOYSA-N n-[3-[3-(6-aminopyridin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(N)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 UXQZKYRXGWLYAD-UHFFFAOYSA-N 0.000 claims description 3
• USXLIEZGQQSAGR-UHFFFAOYSA-N n-[3-[3-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(F)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 USXLIEZGQQSAGR-UHFFFAOYSA-N 0.000 claims description 3
• RMUORMGBCIMAAA-UHFFFAOYSA-N n-[3-[3-(6-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(OC)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 RMUORMGBCIMAAA-UHFFFAOYSA-N 0.000 claims description 3
• NVHFHQAYEVLOLL-UHFFFAOYSA-N n-[3-[3-[2-(1-hydroxyethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CC(O)C1=CC=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 NVHFHQAYEVLOLL-UHFFFAOYSA-N 0.000 claims description 3
• ZREJACCVQDDLSA-UHFFFAOYSA-N n-[3-[3-[2-[(dimethylamino)methyl]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN(C)CC1=CC=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 ZREJACCVQDDLSA-UHFFFAOYSA-N 0.000 claims description 3
• WJTUVBBDWNOHLW-UHFFFAOYSA-N n-[3-[3-[2-[2-(dimethylamino)ethyl]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN(C)CCC1=CC=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 WJTUVBBDWNOHLW-UHFFFAOYSA-N 0.000 claims description 3
• YNTFITDLPCWGGI-UHFFFAOYSA-N n-[3-[3-[3-[(dimethylamino)methyl]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN(C)CC1=CC=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=C1 YNTFITDLPCWGGI-UHFFFAOYSA-N 0.000 claims description 3
• VGHGSNOCPAQYIA-UHFFFAOYSA-N n-[3-[3-[3-[2-(dimethylamino)ethyl]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN(C)CCC1=CC=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=C1 VGHGSNOCPAQYIA-UHFFFAOYSA-N 0.000 claims description 3
• YTIMOEBDNVYIKL-UHFFFAOYSA-N n-[3-[3-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=CC=C(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)C=C1 YTIMOEBDNVYIKL-UHFFFAOYSA-N 0.000 claims description 3
• YXIQZCOQBFYLBY-UHFFFAOYSA-N n-[3-[3-[4-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(CO)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 YXIQZCOQBFYLBY-UHFFFAOYSA-N 0.000 claims description 3
• BUZOTBWJKYSTEL-UHFFFAOYSA-N n-[3-[3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CC1=CC=C(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)C=C1 BUZOTBWJKYSTEL-UHFFFAOYSA-N 0.000 claims description 3
• AIWJVLQNYNCDSL-UHFFFAOYSA-N n-[3-[3-[4-[(dimethylamino)methyl]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 AIWJVLQNYNCDSL-UHFFFAOYSA-N 0.000 claims description 3
• ADDMFZVXYOSSRB-UHFFFAOYSA-N n-[3-[3-[4-[2-(dimethylamino)ethyl]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(CCN(C)C)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 ADDMFZVXYOSSRB-UHFFFAOYSA-N 0.000 claims description 3
• DATHYHLOJYBUAS-UHFFFAOYSA-N n-[3-[3-[5-[(4-ethylpiperazin-1-yl)methyl]furan-3-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCN1CC1=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=CC=2)=CO1 DATHYHLOJYBUAS-UHFFFAOYSA-N 0.000 claims description 3
• DVVNYRUHJUIYRY-UHFFFAOYSA-N n-[3-[3-[6-(methylamino)pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NC)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 DVVNYRUHJUIYRY-UHFFFAOYSA-N 0.000 claims description 3
• SOMNTMFCUYIBSJ-UHFFFAOYSA-N n-[3-[3-[6-[2-(dimethylamino)ethylamino]pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCN(C)C)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 SOMNTMFCUYIBSJ-UHFFFAOYSA-N 0.000 claims description 3
• UVFNRSNYMHZTQN-UHFFFAOYSA-N n-[4-chloro-3-(3-iodopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C(Cl)=CC=2)C=2N3N=CC(I)=C3N=CC=2)=C1 UVFNRSNYMHZTQN-UHFFFAOYSA-N 0.000 claims description 3
• LUPKUUJEJNMUFB-UHFFFAOYSA-N n-[4-fluoro-3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)C(F)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 LUPKUUJEJNMUFB-UHFFFAOYSA-N 0.000 claims description 3
• UNDYKHPZSMWVQR-UHFFFAOYSA-N n-methyl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)NC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 UNDYKHPZSMWVQR-UHFFFAOYSA-N 0.000 claims description 3
• IUYWOWXZFPJKHI-UHFFFAOYSA-N n-propyl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)NCCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 IUYWOWXZFPJKHI-UHFFFAOYSA-N 0.000 claims description 3
• RJRFKVCYDRENAZ-UHFFFAOYSA-N n-pyridin-3-yl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C(=O)NC=2C=NC=CC=2)=C1 RJRFKVCYDRENAZ-UHFFFAOYSA-N 0.000 claims description 3
• XAIDCHTZHBMWEM-UHFFFAOYSA-N pyridin-3-yl 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C(=O)OC=2C=NC=CC=2)=C1 XAIDCHTZHBMWEM-UHFFFAOYSA-N 0.000 claims description 3
• IKZYZBMLMQANMK-UHFFFAOYSA-N tert-butyl 4-[7-[2-fluoro-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazole-1-carboxylate Chemical class C1=NN(C(=O)OC(C)(C)C)C=C1C1=C2N=CC=C(C=3C(=CC=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=3)F)N2N=C1 IKZYZBMLMQANMK-UHFFFAOYSA-N 0.000 claims description 3
• DYYJGTOTNMRNNH-UHFFFAOYSA-N tert-butyl 4-[7-[2-methoxy-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazole-1-carboxylate Chemical class C1=C(C=2N3N=CC(=C3N=CC=2)C2=CN(N=C2)C(=O)OC(C)(C)C)C(OC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 DYYJGTOTNMRNNH-UHFFFAOYSA-N 0.000 claims description 3
• IBQWZZDKHBJWEN-UHFFFAOYSA-N tert-butyl 4-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 IBQWZZDKHBJWEN-UHFFFAOYSA-N 0.000 claims description 3
• MJVDIICPSKNKLF-UHFFFAOYSA-N 1-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 MJVDIICPSKNKLF-UHFFFAOYSA-N 0.000 claims description 2
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
• SPZAQDKBFIVQRF-UHFFFAOYSA-N 3-(dimethylamino)-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound CN(C)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 SPZAQDKBFIVQRF-UHFFFAOYSA-N 0.000 claims description 2
• YWBIZOJRUPBZPZ-UHFFFAOYSA-N 3-cyano-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound C=1C=CC(C#N)=CC=1C(=O)NC(C=1)=CC=CC=1C(N1N=2)=CC=NC1=CC=2C1=CC=NC=C1 YWBIZOJRUPBZPZ-UHFFFAOYSA-N 0.000 claims description 2
• ILGMXGVFTIGXNK-UHFFFAOYSA-N 3-fluoro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-4-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(F)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 ILGMXGVFTIGXNK-UHFFFAOYSA-N 0.000 claims description 2
• HDBKBBJQCWULSU-UHFFFAOYSA-N 3-fluoro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 HDBKBBJQCWULSU-UHFFFAOYSA-N 0.000 claims description 2
• HYSZAKFHRGTLIS-UHFFFAOYSA-N 3-nitro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-5-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 HYSZAKFHRGTLIS-UHFFFAOYSA-N 0.000 claims description 2
• JFLJADZHWAFZDY-UHFFFAOYSA-N 3-nitro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 JFLJADZHWAFZDY-UHFFFAOYSA-N 0.000 claims description 2
• QJGRYHXXSXSXCH-UHFFFAOYSA-N 4-(methylaminomethyl)-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(CNC)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 QJGRYHXXSXSXCH-UHFFFAOYSA-N 0.000 claims description 2
• VGHCQUBQEDAUMR-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=CC=C1CN1CCOCC1 VGHCQUBQEDAUMR-UHFFFAOYSA-N 0.000 claims description 2
• OOEUPQMJEDEEHY-UHFFFAOYSA-N 4-bromo-3-methyl-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound C1=C(Br)C(C)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 OOEUPQMJEDEEHY-UHFFFAOYSA-N 0.000 claims description 2
• JIAUCSXJVNUVIC-UHFFFAOYSA-N 4-fluoro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 JIAUCSXJVNUVIC-UHFFFAOYSA-N 0.000 claims description 2
• PXRVMXDADLNRDG-UHFFFAOYSA-N 4-methyl-n-[3-(2-methylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound N12N=C(C)C=C2N=CC=C1C(C=1)=CC=CC=1NC(=O)C1=CC=C(C)C(C(F)(F)F)=C1 PXRVMXDADLNRDG-UHFFFAOYSA-N 0.000 claims description 2
• 208000026310 Breast neoplasm Diseases 0.000 claims description 2
• 206010009944 Colon cancer Diseases 0.000 claims description 2
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
• 208000003445 Mouth Neoplasms Diseases 0.000 claims description 2
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 229940007550 benzyl acetate Drugs 0.000 claims description 2
• QUKGYYKBILRGFE-UHFFFAOYSA-N benzyloxyacetoaldehyde Natural products CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 2
• LIPAUKCKCNPBQQ-UHFFFAOYSA-N chembl1089411 Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2NC=NC=2)=C1 LIPAUKCKCNPBQQ-UHFFFAOYSA-N 0.000 claims description 2
• 208000029742 colonic neoplasm Diseases 0.000 claims description 2
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
• HUTNEPTZCRFAHW-UHFFFAOYSA-N ethyl 2-methyl-7-[3-[[4-methyl-3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C(C)=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(C)C(C(F)(F)F)=C1 HUTNEPTZCRFAHW-UHFFFAOYSA-N 0.000 claims description 2
• SJCWJMORMRRCGT-UHFFFAOYSA-N ethyl 7-[2-methoxy-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C(=CC=1)OC)=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 SJCWJMORMRRCGT-UHFFFAOYSA-N 0.000 claims description 2
• NGEUMQOMYROEHK-UHFFFAOYSA-N ethyl 7-[3-[(3,4-dichlorobenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(Cl)C(Cl)=C1 NGEUMQOMYROEHK-UHFFFAOYSA-N 0.000 claims description 2
• ZHJLUUMEDYMPIE-UHFFFAOYSA-N ethyl 7-[3-[(3,5-dichlorobenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC(Cl)=CC(Cl)=C1 ZHJLUUMEDYMPIE-UHFFFAOYSA-N 0.000 claims description 2
• HHIARXWMNWOFMV-UHFFFAOYSA-N ethyl 7-[3-[(3-chlorophenyl)carbamoylamino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(Cl)=C1 HHIARXWMNWOFMV-UHFFFAOYSA-N 0.000 claims description 2
• MLVZYGLMGPHIKH-UHFFFAOYSA-N ethyl 7-[3-[[2-chloro-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC(C(F)(F)F)=CC=C1Cl MLVZYGLMGPHIKH-UHFFFAOYSA-N 0.000 claims description 2
• UJQMWDXTLBSHIG-UHFFFAOYSA-N ethyl 7-[3-[[3-(trifluoromethoxy)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(OC(F)(F)F)=C1 UJQMWDXTLBSHIG-UHFFFAOYSA-N 0.000 claims description 2
• QVIQDYNEWBVSGB-UHFFFAOYSA-N ethyl 7-[3-[[3-[(2-morpholin-4-ylacetyl)amino]-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1NC(=O)CN1CCOCC1 QVIQDYNEWBVSGB-UHFFFAOYSA-N 0.000 claims description 2
• FLXUCFRISKGEMV-UHFFFAOYSA-N ethyl 7-[3-[[3-[(2-pyrrolidin-1-ylacetyl)amino]-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1NC(=O)CN1CCCC1 FLXUCFRISKGEMV-UHFFFAOYSA-N 0.000 claims description 2
• FIRVDUDNAWBUAM-UHFFFAOYSA-N ethyl 7-[3-[[3-amino-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC(N)=CC(C(F)(F)F)=C1 FIRVDUDNAWBUAM-UHFFFAOYSA-N 0.000 claims description 2
• AOHITRYWMBYHJR-UHFFFAOYSA-N ethyl 7-[3-[[3-nitro-5-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC([N+]([O-])=O)=CC(C(F)(F)F)=C1 AOHITRYWMBYHJR-UHFFFAOYSA-N 0.000 claims description 2
• 206010023841 laryngeal neoplasm Diseases 0.000 claims description 2
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• 208000020816 lung neoplasm Diseases 0.000 claims description 2
• IJPNSQDYEXIHNQ-UHFFFAOYSA-N methyl 4-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 IJPNSQDYEXIHNQ-UHFFFAOYSA-N 0.000 claims description 2
• BCSHJTSQCSTUNG-UHFFFAOYSA-N methyl 7-[2-chloro-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OC)C=NN2C=1C(C(=CC=1)Cl)=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 BCSHJTSQCSTUNG-UHFFFAOYSA-N 0.000 claims description 2
• MVWRDEQIFWVXGU-UHFFFAOYSA-N n-(4-chloro-3-pyrazolo[1,5-a]pyrimidin-7-ylphenyl)-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C(Cl)=CC=2)C=2N3N=CC=C3N=CC=2)=C1 MVWRDEQIFWVXGU-UHFFFAOYSA-N 0.000 claims description 2
• PZIFCSCTAYMFLO-UHFFFAOYSA-N n-(4-methoxy-3-pyrazolo[1,5-a]pyrimidin-7-ylphenyl)-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N3N=CC=C3N=CC=2)C(OC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 PZIFCSCTAYMFLO-UHFFFAOYSA-N 0.000 claims description 2
• HUCREBOXJNRDJS-UHFFFAOYSA-N n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-1,3-benzodioxole-5-carboxamide Chemical compound C=1C=C2OCOC2=CC=1C(=O)NC(C=1)=CC=CC=1C(N1N=2)=CC=NC1=CC=2C1=CC=NC=C1 HUCREBOXJNRDJS-UHFFFAOYSA-N 0.000 claims description 2
• KWTBXNJMUQADIE-UHFFFAOYSA-N n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-2-[3-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(CC(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 KWTBXNJMUQADIE-UHFFFAOYSA-N 0.000 claims description 2
• ANKCPAJFKKGTCX-UHFFFAOYSA-N n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 ANKCPAJFKKGTCX-UHFFFAOYSA-N 0.000 claims description 2
• JMFJLJADHOCTIH-UHFFFAOYSA-N n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-[(2-pyrrolidin-1-ylacetyl)amino]-5-(trifluoromethyl)benzamide Chemical compound C=1C(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=CC(C(F)(F)F)=CC=1NC(=O)CN1CCCC1 JMFJLJADHOCTIH-UHFFFAOYSA-N 0.000 claims description 2
• HMZDJQZIFQIFMU-UHFFFAOYSA-N n-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3,4-dichlorobenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(Br)=C3N=CC=2)=C1 HMZDJQZIFQIFMU-UHFFFAOYSA-N 0.000 claims description 2
• WMANURRDEDFNQX-UHFFFAOYSA-N n-[3-(3-iodopyrazolo[1,5-a]pyrimidin-7-yl)-4-methoxyphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N3N=CC(I)=C3N=CC=2)C(OC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 WMANURRDEDFNQX-UHFFFAOYSA-N 0.000 claims description 2
• AKIJLJGSFCTILA-UHFFFAOYSA-N n-[3-(3-pyrimidin-5-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C=2C=NC=NC=2)=C1 AKIJLJGSFCTILA-UHFFFAOYSA-N 0.000 claims description 2
• SSSWSPAGLRTMIB-DEOSSOPVSA-N n-[3-[2-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)N2[C@@H](CCC2)CN2CCCC2)=C1 SSSWSPAGLRTMIB-DEOSSOPVSA-N 0.000 claims description 2
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