CA2643968A1 - Pyrazolo[1,5-a]pyrimidine derivatives and methods of use thereof - Google Patents

Info

Publication number

CA2643968A1

CA2643968A1 CA002643968A CA2643968A CA2643968A1 CA 2643968 A1 CA2643968 A1 CA 2643968A1 CA 002643968 A CA002643968 A CA 002643968A CA 2643968 A CA2643968 A CA 2643968A CA 2643968 A1 CA2643968 A1 CA 2643968A1

Authority

CA

Canada

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 114
• 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 94
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
• 201000011510 cancer Diseases 0.000 claims abstract description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 293
• 125000004432 carbon atom Chemical group C* 0.000 claims description 166
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 157
• -1 ethyl 7-{3-[(1-benzothien-2-ylcarbonyl)amino]phenyl}pyrazolo[1,5-a]pyrimidine-carboxylate Chemical compound 0.000 claims description 156
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 133
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 123
• 125000000217 alkyl group Chemical group 0.000 claims description 105
• 125000001072 heteroaryl group Chemical group 0.000 claims description 87
• 125000000623 heterocyclic group Chemical group 0.000 claims description 69
• 125000003118 aryl group Chemical group 0.000 claims description 67
• 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 55
• 150000001875 compounds Chemical class 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 47
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 42
• 125000005842 heteroatom Chemical group 0.000 claims description 39
• 125000000304 alkynyl group Chemical group 0.000 claims description 35
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 31
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 29
• 239000002253 acid Substances 0.000 claims description 28
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 27
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 24
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 125000001246 bromo group Chemical group Br* 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000002346 iodo group Chemical group I* 0.000 claims description 11
• 150000002825 nitriles Chemical class 0.000 claims description 10
• 229940002612 prodrug Drugs 0.000 claims description 10
• 239000000651 prodrug Substances 0.000 claims description 10
• 125000003107 substituted aryl group Chemical group 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 9
• 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 6
• KTELDMPKGBUYES-UHFFFAOYSA-N ethyl 7-[3-[[4-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]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(CN(C)C(=O)OC(C)(C)C)C(C(F)(F)F)=C1 KTELDMPKGBUYES-UHFFFAOYSA-N 0.000 claims description 6
• 239000012535 impurity Substances 0.000 claims description 6
• 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 6
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 6
• 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 5
• 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 5
• VAGVIWKTWXOXPO-UHFFFAOYSA-N 7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C=1C=NC2=C(C(=O)O)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 VAGVIWKTWXOXPO-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• LOHWARPDQXYUTI-UHFFFAOYSA-N ethyl 7-[2-chloro-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)Cl)=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 LOHWARPDQXYUTI-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
• 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 5
• 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 5
• 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 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
• 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 5
• 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 5
• ZKVNGIGDPAXTDD-UHFFFAOYSA-N n-[3-[2-[2-(2,2-dimethylpropanoylamino)pyridin-4-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NC(=O)C(C)(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 ZKVNGIGDPAXTDD-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 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 5
• 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 5
• 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 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
• 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 4
• 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 4
• 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
• 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 4
• 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 4
• 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 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
• 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 4
• 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 4
• 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 4
• 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 4
• FFRKRCSKTUIMKN-UHFFFAOYSA-N 4-methyl-n-[3-(2-thiophen-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=C(C=C3N=CC=2)C=2SC=CC=2)=C1 FFRKRCSKTUIMKN-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• FINWNCPABQONML-UHFFFAOYSA-N [4-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-2-yl]phenyl]methyl acetate Chemical compound C1=CC(COC(=O)C)=CC=C1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 FINWNCPABQONML-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• LAHQILMHFMHDNG-UHFFFAOYSA-N ethyl 7-[3-[(1-methylindole-2-carbonyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C1=CC=C2N(C)C(C(=O)NC=3C=CC=C(C=3)C=3N4N=CC(=C4N=CC=3)C(=O)OCC)=CC2=C1 LAHQILMHFMHDNG-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• HQMYQARGBOAGMF-UHFFFAOYSA-N ethyl 7-[3-[(3,4-dimethylphenyl)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=C(C)C(C)=C1 HQMYQARGBOAGMF-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• BFPXSAQZTZMLTR-UHFFFAOYSA-N ethyl 7-[3-[(3-chloro-4-fluorophenyl)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=C(F)C(Cl)=C1 BFPXSAQZTZMLTR-UHFFFAOYSA-N 0.000 claims description 4
• WIVMAWZHQGVOAJ-UHFFFAOYSA-N ethyl 7-[3-[(3-chloro-4-methoxyphenyl)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=C(OC)C(Cl)=C1 WIVMAWZHQGVOAJ-UHFFFAOYSA-N 0.000 claims description 4
• HTPQABGBZOKXJP-UHFFFAOYSA-N ethyl 7-[3-[(3-methyl-1,2-oxazol-5-yl)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(C)=NO1 HTPQABGBZOKXJP-UHFFFAOYSA-N 0.000 claims description 4
• KEUOPRFDUWZGJZ-UHFFFAOYSA-N ethyl 7-[3-[(5-bromothiophene-2-carbonyl)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(Br)S1 KEUOPRFDUWZGJZ-UHFFFAOYSA-N 0.000 claims description 4
• UPDWHMRHNNUOPD-UHFFFAOYSA-N ethyl 7-[3-[(5-tert-butyl-2-methylpyrazole-3-carbonyl)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)=NN1C UPDWHMRHNNUOPD-UHFFFAOYSA-N 0.000 claims description 4
• UPHDVXOLYAYRFB-UHFFFAOYSA-N ethyl 7-[3-[[2-(2,3,6-trifluorophenyl)acetyl]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)CC1=C(F)C=CC(F)=C1F UPHDVXOLYAYRFB-UHFFFAOYSA-N 0.000 claims description 4
• HNOFCJKUQYDTMS-UHFFFAOYSA-N ethyl 7-[3-[[2-(3-fluorophenyl)acetyl]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)CC1=CC=CC(F)=C1 HNOFCJKUQYDTMS-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• IEKDIFJIGVSECF-UHFFFAOYSA-N ethyl 7-[3-[[3,5-bis(trifluoromethyl)phenyl]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(C(F)(F)F)=CC(C(F)(F)F)=C1 IEKDIFJIGVSECF-UHFFFAOYSA-N 0.000 claims description 4
• VMKXUCRGLMAMIB-UHFFFAOYSA-N ethyl 7-[3-[[4-(trifluoromethylsulfanyl)phenyl]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=C(SC(F)(F)F)C=C1 VMKXUCRGLMAMIB-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• MTUGGKLZGIMXDF-UHFFFAOYSA-N n-[3-(3-cyano-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(C#N)=C3N=CC=2)N2CCNCC2)=C1 MTUGGKLZGIMXDF-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• GRTZEQJSRHJNGH-UHFFFAOYSA-N n-[3-[3-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 GRTZEQJSRHJNGH-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 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
• NNEDMQDONWATNK-UHFFFAOYSA-N n-[3-[3-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=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)=CC=N1 NNEDMQDONWATNK-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• RBGUOHBCKRTPMX-UHFFFAOYSA-N n-[3-[3-[4-(dimethylsulfamoyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(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 RBGUOHBCKRTPMX-UHFFFAOYSA-N 0.000 claims description 4
• UFELNXRWJPVQMY-UHFFFAOYSA-N n-[3-[3-[4-[[2-(2-methoxyethoxy)acetyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(NC(=O)COCCOC)=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 UFELNXRWJPVQMY-UHFFFAOYSA-N 0.000 claims description 4
• QSJNXXFITCOUPN-UHFFFAOYSA-N n-[3-[3-[4-[[2-(2h-tetrazol-5-yl)acetyl]amino]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(NC(=O)CC=3NN=NN=3)=CC=2)=C1 QSJNXXFITCOUPN-UHFFFAOYSA-N 0.000 claims description 4
• YIICPBQWCOBAJU-UHFFFAOYSA-N n-[3-[3-[5-(4-methylpiperazin-1-yl)pent-1-ynyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CCCC#CC1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 YIICPBQWCOBAJU-UHFFFAOYSA-N 0.000 claims description 4
• KZMLCIRUVXQMTF-UHFFFAOYSA-N n-[4-chloro-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(Cl)=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 KZMLCIRUVXQMTF-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• QEEYCINITWXPKV-UHFFFAOYSA-N n-[4-methoxy-3-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N3N=CC(=C3N=CC=2)C2=CNN=C2)C(OC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 QEEYCINITWXPKV-UHFFFAOYSA-N 0.000 claims description 4
• VDGZNGVEVHIGKZ-UHFFFAOYSA-N n-ethyl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)NCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 VDGZNGVEVHIGKZ-UHFFFAOYSA-N 0.000 claims description 4
• 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 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• CSYGIPIOQSVIRG-UHFFFAOYSA-N 3-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]benzamide Chemical compound NC(=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 CSYGIPIOQSVIRG-UHFFFAOYSA-N 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
• 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
• 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 3
• KLLPYYZIOZFGQS-UHFFFAOYSA-N 7-[3-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-n-(3-methoxypropyl)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)NC1=CC=C(Cl)C(C(F)(F)F)=C1 KLLPYYZIOZFGQS-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
• UBEQZZQUGLPEHV-UHFFFAOYSA-N ethyl 7-[3-(1,3-benzodioxol-5-ylcarbamoylamino)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C1=C2OCOC2=CC(NC(=O)NC=2C=CC=C(C=2)C=2N3N=CC(=C3N=CC=2)C(=O)OCC)=C1 UBEQZZQUGLPEHV-UHFFFAOYSA-N 0.000 claims description 3
• GFTOBTBFINIFGG-UHFFFAOYSA-N ethyl 7-[3-(isoquinoline-1-carbonylamino)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C1=CC=C2C(C(=O)NC=3C=CC=C(C=3)C=3N4N=CC(=C4N=CC=3)C(=O)OCC)=NC=CC2=C1 GFTOBTBFINIFGG-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
• ZHWIOHSXUVDSER-UHFFFAOYSA-N ethyl 7-[3-[(3-chloro-4-morpholin-4-ylphenyl)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)NC(C=C1Cl)=CC=C1N1CCOCC1 ZHWIOHSXUVDSER-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
• 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
• FOSPJNGQTCVTLJ-UHFFFAOYSA-N ethyl 7-[3-[(4-methylsulfanylphenyl)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=C(SC)C=C1 FOSPJNGQTCVTLJ-UHFFFAOYSA-N 0.000 claims description 3
• YEFXARGQOZIHOU-UHFFFAOYSA-N ethyl 7-[3-[(5-methylpyrazine-2-carbonyl)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=CN=C(C)C=N1 YEFXARGQOZIHOU-UHFFFAOYSA-N 0.000 claims description 3
• UPSQVVCQAUAYGI-UHFFFAOYSA-N ethyl 7-[3-[[2-(3-chlorophenyl)acetyl]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)CC1=CC=CC(Cl)=C1 UPSQVVCQAUAYGI-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
• 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 3
• 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 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
• 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 3
• RGHDOTKCOQTLRU-UHFFFAOYSA-N ethyl 7-[3-[[4-(methylaminomethyl)-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(CNC)C(C(F)(F)F)=C1 RGHDOTKCOQTLRU-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
• 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
• RIYWFOODHMUIJE-UHFFFAOYSA-N ethyl 7-[3-[[5-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophene-2-carbonyl]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(S1)=CC=C1C1=CC(C(F)(F)F)=NN1C RIYWFOODHMUIJE-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
• HYXFLEHYFSXFHF-UHFFFAOYSA-N ethyl 7-[4-phenylmethoxy-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=C1NC(=O)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1OCC1=CC=CC=C1 HYXFLEHYFSXFHF-UHFFFAOYSA-N 0.000 claims description 3
• 230000012010 growth Effects 0.000 claims description 3
• 210000003734 kidney Anatomy 0.000 claims description 3
• 210000004185 liver Anatomy 0.000 claims description 3
• XBPNKTNSDDVIRK-UHFFFAOYSA-N methyl 7-[2-fluoro-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)F)=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 XBPNKTNSDDVIRK-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
• 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 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
• 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
• XUWFFNMSAMZPGY-UHFFFAOYSA-N n-[3-(2-oxo-1h-pyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound N12N=C(O)C=C2N=CC=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 XUWFFNMSAMZPGY-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
• 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 3
• ARMKBDOVOBCACP-UHFFFAOYSA-N n-[3-(2-thiophen-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=2SC=CC=2)=C1 ARMKBDOVOBCACP-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
• 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
• 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
• 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 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
• 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
• 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
• 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 3
• KRJLGELNCAFZBC-UHFFFAOYSA-N n-[3-[2-[2-(3-imidazol-1-ylpropylamino)pyridin-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=C(C=C3N=CC=2)C=2C=C(NCCCN3C=NC=C3)N=CC=2)=C1 KRJLGELNCAFZBC-UHFFFAOYSA-N 0.000 claims description 3
• FJHJWHQDODDFAU-UHFFFAOYSA-N n-[3-[2-[2-(3-morpholin-4-ylpropylamino)pyridin-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=C(C=C3N=CC=2)C=2C=C(NCCCN3CCOCC3)N=CC=2)=C1 FJHJWHQDODDFAU-UHFFFAOYSA-N 0.000 claims description 3
• JIBSPSCUERJSQG-UHFFFAOYSA-N n-[3-[2-[2-(3-piperidin-1-ylpropylamino)pyridin-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=C(C=C3N=CC=2)C=2C=C(NCCCN3CCCCC3)N=CC=2)=C1 JIBSPSCUERJSQG-UHFFFAOYSA-N 0.000 claims description 3
• NRHIJVYWTBCVNR-UHFFFAOYSA-N n-[3-[2-[2-(3-pyrrolidin-1-ylpropylamino)pyridin-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=C(C=C3N=CC=2)C=2C=C(NCCCN3CCCC3)N=CC=2)=C1 NRHIJVYWTBCVNR-UHFFFAOYSA-N 0.000 claims description 3
• YAMWVJGVIAAELZ-UHFFFAOYSA-N n-[3-[2-[2-[3-(2-oxopyrrolidin-1-yl)propylamino]pyridin-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=C(C=C3N=CC=2)C=2C=C(NCCCN3C(CCC3)=O)N=CC=2)=C1 YAMWVJGVIAAELZ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• IHTDPGRVLGETGE-UHFFFAOYSA-N n-[3-[3-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NN(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 IHTDPGRVLGETGE-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
• MIEZHZIXKCLLLJ-UHFFFAOYSA-N n-[3-[3-(3,5-dimethyl-1,2-oxazol-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=NOC(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 MIEZHZIXKCLLLJ-UHFFFAOYSA-N 0.000 claims description 3
• TXIHKRVZVKHSAG-UHFFFAOYSA-N n-[3-[3-(3,5-dimethyl-1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]-4-fluorophenyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=NNC(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 TXIHKRVZVKHSAG-UHFFFAOYSA-N 0.000 claims description 3
• QJMIRKOWXSVBAF-UHFFFAOYSA-N n-[3-[3-(3,5-dimethyl-1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=NNC(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 QJMIRKOWXSVBAF-UHFFFAOYSA-N 0.000 claims description 3
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• 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
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• 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
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• 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 2
• 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 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
• 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 2
• 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 2
• 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 2
• 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 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
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• 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 2
• 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 2
• 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 2
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• PDULSKUEEJLRQZ-UHFFFAOYSA-N ethyl 7-[3-[(3,5-dichlorophenyl)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(Cl)=CC(Cl)=C1 PDULSKUEEJLRQZ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• MHBFQGGQNIYNSH-UHFFFAOYSA-N ethyl 7-[3-[(4-chloro-2-methylphenyl)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=C(Cl)C=C1C MHBFQGGQNIYNSH-UHFFFAOYSA-N 0.000 claims description 2
• BFQAVGNNZHPOKL-UHFFFAOYSA-N ethyl 7-[3-[(4-chloropyridine-2-carbonyl)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=N1 BFQAVGNNZHPOKL-UHFFFAOYSA-N 0.000 claims description 2
• GKBOFPYKIFTEEM-UHFFFAOYSA-N ethyl 7-[3-[(4-ethoxycarbonylphenyl)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=C(C(=O)OCC)C=C1 GKBOFPYKIFTEEM-UHFFFAOYSA-N 0.000 claims description 2
• GKQWEXXUDZATPR-UHFFFAOYSA-N ethyl 7-[3-[(4-propan-2-ylphenyl)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=C(C(C)C)C=C1 GKQWEXXUDZATPR-UHFFFAOYSA-N 0.000 claims description 2
• BBHPXCXJKWGJKJ-UHFFFAOYSA-N ethyl 7-[3-[(5-chlorothiophene-2-carbonyl)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)S1 BBHPXCXJKWGJKJ-UHFFFAOYSA-N 0.000 claims description 2
• YFSIZQBUVBFLOT-UHFFFAOYSA-N ethyl 7-[3-[(5-methyl-2-phenyltriazole-4-carbonyl)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(=N1)C)=NN1C1=CC=CC=C1 YFSIZQBUVBFLOT-UHFFFAOYSA-N 0.000 claims description 2
• UNCLXUUNVUMJNA-UHFFFAOYSA-N ethyl 7-[3-[(6-methoxy-1,3-benzothiazol-2-yl)carbamoylamino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C1=C(OC)C=C2SC(NC(=O)NC=3C=CC=C(C=3)C=3N4N=CC(=C4N=CC=3)C(=O)OCC)=NC2=C1 UNCLXUUNVUMJNA-UHFFFAOYSA-N 0.000 claims description 2
• CQDDXLGSASMZQD-UHFFFAOYSA-N ethyl 7-[3-[[2-(3-methoxyphenyl)acetyl]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)CC1=CC=CC(OC)=C1 CQDDXLGSASMZQD-UHFFFAOYSA-N 0.000 claims description 2
• LKMFZKZEVCUVMD-UHFFFAOYSA-N ethyl 7-[3-[[2-(4-methoxy-3-methylphenyl)acetyl]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)CC1=CC=C(OC)C(C)=C1 LKMFZKZEVCUVMD-UHFFFAOYSA-N 0.000 claims description 2
• LAWNIAKHSWIXMG-UHFFFAOYSA-N ethyl 7-[3-[[2-(trifluoromethyl)phenyl]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=C1C(F)(F)F LAWNIAKHSWIXMG-UHFFFAOYSA-N 0.000 claims description 2
• CVCWTRBKVXYCEI-UHFFFAOYSA-N ethyl 7-[3-[[2-[3,5-bis(trifluoromethyl)phenyl]acetyl]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)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CVCWTRBKVXYCEI-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
• 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
• ACOFGXALIWWGJI-UHFFFAOYSA-N ethyl 7-[3-[[4-methyl-3-(trifluoromethyl)benzoyl]amino]-4-phenylmethoxyphenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=C1NC(=O)C=2C=C(C(C)=CC=2)C(F)(F)F)=CC=C1OCC1=CC=CC=C1 ACOFGXALIWWGJI-UHFFFAOYSA-N 0.000 claims description 2
• IEAIPIYTZUFKAP-UHFFFAOYSA-N ethyl 7-[4-(2,6-dimethylmorpholin-4-yl)-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=C1NC(=O)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1N1CC(C)OC(C)C1 IEAIPIYTZUFKAP-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 230000002401 inhibitory effect Effects 0.000 claims description 2
• 210000000867 larynx Anatomy 0.000 claims description 2
• 210000004072 lung Anatomy 0.000 claims description 2
• 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 2
• 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 2
• 210000000214 mouth Anatomy 0.000 claims description 2
• 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 2
• 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 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
• 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
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• RVABYHFSBMVUBP-UHFFFAOYSA-N n-[3-[3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1N(C)CCC(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 RVABYHFSBMVUBP-UHFFFAOYSA-N 0.000 claims description 2
• ZKFBEBFIZLTOJC-UHFFFAOYSA-N n-[3-[3-(1h-pyrrol-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)C2=CNC=C2)=C1 ZKFBEBFIZLTOJC-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• FWKYWMAZZOANJT-UHFFFAOYSA-N n-[3-[3-(6-acetamidopyridin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NC(=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 FWKYWMAZZOANJT-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• ILAUOEJZERAVEH-UHFFFAOYSA-N n-[3-[3-[3-(1-hydroxyethyl)phenyl]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 ILAUOEJZERAVEH-UHFFFAOYSA-N 0.000 claims description 2
• BHZDZJAYOOQHPQ-UHFFFAOYSA-N n-[3-[3-[3-(dimethylcarbamoyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-4-methyl-3-(trifluoromethyl)benzamide Chemical compound CN(C)C(=O)C1=CC=CC(C2=C3N=CC=C(N3N=C2)C=2C=C(NC(=O)C=3C=C(C(C)=CC=3)C(F)(F)F)C=CC=2)=C1 BHZDZJAYOOQHPQ-UHFFFAOYSA-N 0.000 claims description 2
• SXRQXNQEJVKGDC-UHFFFAOYSA-N n-[3-[3-[4-(3-methoxypropanoylamino)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(NC(=O)CCOC)=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 SXRQXNQEJVKGDC-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• BIAGWLDERXRFAW-UHFFFAOYSA-N n-[3-[3-[4-[[2-(dimethylamino)acetyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(NC(=O)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 BIAGWLDERXRFAW-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• UXWQKBQYLIAPJN-UHFFFAOYSA-N n-[3-[3-[5-(pyrrolidin-1-ylmethyl)furan-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(CN3CCCC3)OC=2)=C1 UXWQKBQYLIAPJN-UHFFFAOYSA-N 0.000 claims description 2
• DNDVGFIEWOHGAH-UHFFFAOYSA-N n-[3-[3-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]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=N1 DNDVGFIEWOHGAH-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• PIGVLAUTQMIRBH-UHFFFAOYSA-N n-[4-fluoro-3-[3-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]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(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)F)C=N1 PIGVLAUTQMIRBH-UHFFFAOYSA-N 0.000 claims description 2
• 210000001672 ovary Anatomy 0.000 claims description 2
• 210000000496 pancreas Anatomy 0.000 claims description 2
• 210000002307 prostate Anatomy 0.000 claims description 2
• 210000003491 skin Anatomy 0.000 claims description 2
• 210000002784 stomach Anatomy 0.000 claims description 2
• PMIHAXFYVIYAGL-UHFFFAOYSA-N tert-butyl 2-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrrole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=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 PMIHAXFYVIYAGL-UHFFFAOYSA-N 0.000 claims description 2
• 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 compound 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 2
• 210000003932 urinary bladder Anatomy 0.000 claims description 2
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• HZCXTBDKCKRGHN-UHFFFAOYSA-N 3,4-difluoro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound C1=C(F)C(F)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 HZCXTBDKCKRGHN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
• FWFGUQBBFCETAJ-UHFFFAOYSA-N 7-[3-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-n-(2-morpholin-4-ylethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 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(=O)NCCN2CCOCC2)=C1 FWFGUQBBFCETAJ-UHFFFAOYSA-N 0.000 claims 1
• AVHUQQJMRCXJOK-UHFFFAOYSA-N 7-[3-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-n-(3-imidazol-1-ylpropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 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(=O)NCCCN2C=NC=C2)=C1 AVHUQQJMRCXJOK-UHFFFAOYSA-N 0.000 claims 1
• VWBONYFKEMSEAV-UHFFFAOYSA-N 7-[3-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-n-[2-(diethylamino)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)NCCN(CC)CC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 VWBONYFKEMSEAV-UHFFFAOYSA-N 0.000 claims 1
• 206010005003 Bladder cancer Diseases 0.000 claims 1
• 208000003174 Brain Neoplasms Diseases 0.000 claims 1
• 206010006187 Breast cancer Diseases 0.000 claims 1
• 208000026310 Breast neoplasm Diseases 0.000 claims 1
• 206010009944 Colon cancer Diseases 0.000 claims 1
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
• 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
• 206010023825 Laryngeal cancer Diseases 0.000 claims 1
• 206010061523 Lip and/or oral cavity cancer Diseases 0.000 claims 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
• 208000003445 Mouth Neoplasms Diseases 0.000 claims 1
• 206010033128 Ovarian cancer Diseases 0.000 claims 1
• 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
• 206010060862 Prostate cancer Diseases 0.000 claims 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
• 206010038389 Renal cancer Diseases 0.000 claims 1
• 208000000453 Skin Neoplasms Diseases 0.000 claims 1
• 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
• 208000029742 colonic neoplasm Diseases 0.000 claims 1
• 201000004101 esophageal cancer Diseases 0.000 claims 1
• 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 1
• PVDBTFNZPBYCIM-UHFFFAOYSA-N ethyl 7-[3-(3,5,5-trimethylhexanoylamino)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C1=CC=CC(NC(=O)CC(C)CC(C)(C)C)=C1 PVDBTFNZPBYCIM-UHFFFAOYSA-N 0.000 claims 1
• JAAPJFATKCADGC-UHFFFAOYSA-N ethyl 7-[3-(pyrazine-2-carbonylamino)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=CN=CC=N1 JAAPJFATKCADGC-UHFFFAOYSA-N 0.000 claims 1
• QNASHOSOJONDLX-UHFFFAOYSA-N ethyl 7-[3-(pyridine-3-carbonylamino)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=CN=C1 QNASHOSOJONDLX-UHFFFAOYSA-N 0.000 claims 1
• LUAIAQRVUPOAQL-UHFFFAOYSA-N ethyl 7-[3-[(3,5-ditert-butylbenzoyl)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)=CC(C(C)(C)C)=C1 LUAIAQRVUPOAQL-UHFFFAOYSA-N 0.000 claims 1
• OUXHBDMEUHVAED-UHFFFAOYSA-N ethyl 7-[3-[(3-chloro-4-methylphenyl)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=C(C)C(Cl)=C1 OUXHBDMEUHVAED-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• YMJLNPLRLDGKMX-UHFFFAOYSA-N ethyl 7-[3-[(4-bromo-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=C(Br)C(Cl)=C1 YMJLNPLRLDGKMX-UHFFFAOYSA-N 0.000 claims 1
• OOPLIUMLGDXKTR-UHFFFAOYSA-N ethyl 7-[3-[(4-bromophenyl)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=C(Br)C=C1 OOPLIUMLGDXKTR-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• QGRBMZNJQMZMRL-UHFFFAOYSA-N ethyl 7-[3-[(4-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=C(Cl)C=C1 QGRBMZNJQMZMRL-UHFFFAOYSA-N 0.000 claims 1
• BLWDTQKWQIFQGE-UHFFFAOYSA-N ethyl 7-[3-[(4-cyanophenyl)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=C(C#N)C=C1 BLWDTQKWQIFQGE-UHFFFAOYSA-N 0.000 claims 1
• BLZNSBOJQCFJBD-UHFFFAOYSA-N ethyl 7-[3-[(5-chloro-2-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(Cl)=CC=C1C BLZNSBOJQCFJBD-UHFFFAOYSA-N 0.000 claims 1
• FSRHFRQQMJGJQS-UHFFFAOYSA-N ethyl 7-[3-[(5-methyl-1,2-oxazol-3-yl)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)NC=1C=C(C)ON=1 FSRHFRQQMJGJQS-UHFFFAOYSA-N 0.000 claims 1
• HTHLWESSIHKNAE-UHFFFAOYSA-N ethyl 7-[3-[(5-methylthiophene-2-carbonyl)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)S1 HTHLWESSIHKNAE-UHFFFAOYSA-N 0.000 claims 1
• KDDKKHDPHJOLMP-UHFFFAOYSA-N ethyl 7-[3-[(6-chloro-1,3-benzothiazol-2-yl)carbamoylamino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C1=C(Cl)C=C2SC(NC(=O)NC=3C=CC=C(C=3)C=3N4N=CC(=C4N=CC=3)C(=O)OCC)=NC2=C1 KDDKKHDPHJOLMP-UHFFFAOYSA-N 0.000 claims 1
• VSPSGGGJVHZFQN-UHFFFAOYSA-N ethyl 7-[3-[[2-(3-bromophenyl)acetyl]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)CC1=CC=CC(Br)=C1 VSPSGGGJVHZFQN-UHFFFAOYSA-N 0.000 claims 1
• OZZVCFYMOOHRBI-UHFFFAOYSA-N ethyl 7-[3-[[2-(3-methylphenyl)acetyl]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)CC1=CC=CC(C)=C1 OZZVCFYMOOHRBI-UHFFFAOYSA-N 0.000 claims 1
• KCJJZTHVTKHLAH-UHFFFAOYSA-N ethyl 7-[3-[[2-[3-(trifluoromethyl)phenyl]acetyl]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)CC1=CC=CC(C(F)(F)F)=C1 KCJJZTHVTKHLAH-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• CZTSQNOAVFMDAC-UHFFFAOYSA-N ethyl 7-[3-[[3-(trifluoromethyl)phenyl]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(C(F)(F)F)=C1 CZTSQNOAVFMDAC-UHFFFAOYSA-N 0.000 claims 1
• PQILKXYJEJVKTN-UHFFFAOYSA-N ethyl 7-[3-[[3-(trifluoromethyl)phenyl]sulfonylamino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 PQILKXYJEJVKTN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• LWKFYYPFBKREFZ-UHFFFAOYSA-N ethyl 7-[3-[[4-(trifluoromethoxy)phenyl]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=C(OC(F)(F)F)C=C1 LWKFYYPFBKREFZ-UHFFFAOYSA-N 0.000 claims 1
• FIYJRDXUBRXNNM-UHFFFAOYSA-N ethyl 7-[3-[[4-(trifluoromethyl)phenyl]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=C(C(F)(F)F)C=C1 FIYJRDXUBRXNNM-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 206010017758 gastric cancer Diseases 0.000 claims 1
• 201000010982 kidney cancer Diseases 0.000 claims 1
• 206010023841 laryngeal neoplasm Diseases 0.000 claims 1
• 201000004962 larynx cancer Diseases 0.000 claims 1
• 201000007270 liver cancer Diseases 0.000 claims 1
• 208000014018 liver neoplasm Diseases 0.000 claims 1
• 201000005202 lung cancer Diseases 0.000 claims 1
• 208000020816 lung neoplasm Diseases 0.000 claims 1
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
• AJXYUSRHMOQXCV-UHFFFAOYSA-N n-(3-imidazol-1-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)NCCCN2C=NC=C2)=C1 AJXYUSRHMOQXCV-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• FLSPYKOEZRHJIT-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)propyl]-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CN(C)CCN1CCCNC(=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 FLSPYKOEZRHJIT-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• VVCVOOMWLIIDDQ-UHFFFAOYSA-N n-[3-[2-(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=C(C=C3N=CC=2)C=2OC=CC=2)=C1 VVCVOOMWLIIDDQ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• IQTMKKLAPIHCBO-UHFFFAOYSA-N n-[3-[2-[2-(2-pyrrolidin-1-ylethylamino)pyridin-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=C(C=C3N=CC=2)C=2C=C(NCCN3CCCC3)N=CC=2)=C1 IQTMKKLAPIHCBO-UHFFFAOYSA-N 0.000 claims 1
• YFNOMSLXULDYKN-UHFFFAOYSA-N n-[3-[2-[2-[2-(2-oxoimidazolidin-1-yl)ethylamino]pyridin-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=C(C=C3N=CC=2)C=2C=C(NCCN3C(NCC3)=O)N=CC=2)=C1 YFNOMSLXULDYKN-UHFFFAOYSA-N 0.000 claims 1
• VTMCXPIYMFDLKI-UHFFFAOYSA-N n-[3-[2-[2-[2-(4-hydroxypiperidin-1-yl)ethylamino]pyridin-4-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CC(O)CCN1CCNC1=CC(C2=NN3C(C=4C=C(NC(=O)C=5C=C(C=CC=5)C(F)(F)F)C=CC=4)=CC=NC3=C2)=CC=N1 VTMCXPIYMFDLKI-UHFFFAOYSA-N 0.000 claims 1
• JJZMISIQDYXLAI-UHFFFAOYSA-N n-[3-[2-[2-[2-(dimethylamino)ethylamino]pyridin-4-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCN(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 JJZMISIQDYXLAI-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• VHUJYLFUZCYLGJ-UHFFFAOYSA-N n-[3-[3-(2-oxo-3h-1,3,4-oxadiazol-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)C=2OC(=O)NN=2)=C1 VHUJYLFUZCYLGJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• QHSPCOXLMCFPRZ-UHFFFAOYSA-N n-[3-[3-[3,5-bis[(dimethylamino)methyl]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN(C)CC1=CC(CN(C)C)=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 QHSPCOXLMCFPRZ-UHFFFAOYSA-N 0.000 claims 1
• OZZKDFBCWKAAKR-UHFFFAOYSA-N n-[3-[3-[3-(3-methoxypropanoylamino)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound COCCC(=O)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 OZZKDFBCWKAAKR-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• QIUKGEZOMFOVMI-UHFFFAOYSA-N n-[3-[3-[3-[[2-(2h-tetrazol-5-yl)acetyl]amino]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=C(NC(=O)CC=3NN=NN=3)C=CC=2)=C1 QIUKGEZOMFOVMI-UHFFFAOYSA-N 0.000 claims 1
• FQOBSFOIGPCIHS-UHFFFAOYSA-N n-[3-[3-[3-[[2-(dimethylamino)acetyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN(C)CC(=O)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 FQOBSFOIGPCIHS-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• LBORYVQDGDVAMG-UHFFFAOYSA-N n-[3-[3-[4-(dimethylamino)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(N(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 LBORYVQDGDVAMG-UHFFFAOYSA-N 0.000 claims 1
• JSHPRVQWJPNDRH-UHFFFAOYSA-N n-[3-[3-[4-[4-(dimethylamino)butanoylamino]phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(NC(=O)CCCN(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 JSHPRVQWJPNDRH-UHFFFAOYSA-N 0.000 claims 1
• JEVVYCYEJYOCNU-UHFFFAOYSA-N n-[3-[3-[4-[[2-(1h-imidazol-5-yl)acetyl]amino]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(NC(=O)CC=3N=CNC=3)=CC=2)=C1 JEVVYCYEJYOCNU-UHFFFAOYSA-N 0.000 claims 1
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• VFKZERFKARMNTM-UHFFFAOYSA-N ethyl 7-[3-(naphthalen-2-ylcarbamoylamino)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C1=CC=CC2=CC(NC(=O)NC=3C=CC=C(C=3)C=3N4N=CC(=C4N=CC=3)C(=O)OCC)=CC=C21 VFKZERFKARMNTM-UHFFFAOYSA-N 0.000 description 2
• XEWOGOFQNVDJHK-UHFFFAOYSA-N ethyl 7-[3-[[2-(1,3-benzodioxol-5-yl)acetyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C1=C2OCOC2=CC(CC(=O)NC=2C=CC=C(C=2)C=2N3N=CC(=C3N=CC=2)C(=O)OCC)=C1 XEWOGOFQNVDJHK-UHFFFAOYSA-N 0.000 description 2
• MCUKRPGCBGERQL-UHFFFAOYSA-N ethyl 7-[3-[[3-methoxy-5-(trifluoromethyl)phenyl]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(OC)=CC(C(F)(F)F)=C1 MCUKRPGCBGERQL-UHFFFAOYSA-N 0.000 description 2
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
• OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
• 239000012442 inert solvent Substances 0.000 description 2
• 239000003112 inhibitor Substances 0.000 description 2
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• 238000000021 kinase assay Methods 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 229910001629 magnesium chloride Inorganic materials 0.000 description 2
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• CBVALRQTVTYRBD-UHFFFAOYSA-N methyl 4-[(2-methoxyethylamino)methyl]-3-(trifluoromethyl)benzoate Chemical compound COCCNCC1=CC=C(C(=O)OC)C=C1C(F)(F)F CBVALRQTVTYRBD-UHFFFAOYSA-N 0.000 description 2
• 244000005700 microbiome Species 0.000 description 2
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• ICLPJEBQRGFFEB-UHFFFAOYSA-N n-[3-[3-[2-(dimethylamino)pyrimidin-5-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(N(C)C)=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 ICLPJEBQRGFFEB-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• IQYKQKZPGRQPQD-UHFFFAOYSA-N n-[3-[3-[3-(dimethylamino)prop-1-ynyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C=1C=NC2=C(C#CCN(C)C)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 IQYKQKZPGRQPQD-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
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• KPHXXSKOCJTRBZ-UHFFFAOYSA-N n-[4-(3-amino-1h-pyrazol-5-yl)pyridin-2-yl]-2,2-dimethylpropanamide Chemical compound C1=NC(NC(=O)C(C)(C)C)=CC(C2=NNC(N)=C2)=C1 KPHXXSKOCJTRBZ-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• 150000002828 nitro derivatives Chemical class 0.000 description 2
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• 239000001301 oxygen Substances 0.000 description 2
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• AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
• 230000026731 phosphorylation Effects 0.000 description 2
• 238000006366 phosphorylation reaction Methods 0.000 description 2
• 102000020233 phosphotransferase Human genes 0.000 description 2
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• 239000000843 powder Substances 0.000 description 2
• 238000002953 preparative HPLC Methods 0.000 description 2
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• 238000001959 radiotherapy Methods 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 238000003860 storage Methods 0.000 description 2
• 125000005017 substituted alkenyl group Chemical group 0.000 description 2
• 125000000547 substituted alkyl group Chemical group 0.000 description 2
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• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
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• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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