JP2009530296A5 - - Google Patents
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- JP2009530296A5 JP2009530296A5 JP2009500484A JP2009500484A JP2009530296A5 JP 2009530296 A5 JP2009530296 A5 JP 2009530296A5 JP 2009500484 A JP2009500484 A JP 2009500484A JP 2009500484 A JP2009500484 A JP 2009500484A JP 2009530296 A5 JP2009530296 A5 JP 2009530296A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- trifluoromethyl
- pyrazolo
- pyrimidin
- amino
- Prior art date
- 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.)
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- 125000004432 carbon atom Chemical group C* 0.000 claims 77
- -1 R 14 Chemical compound 0.000 claims 71
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 71
- 125000000217 alkyl group Chemical group 0.000 claims 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 47
- 125000001072 heteroaryl group Chemical group 0.000 claims 44
- 125000000623 heterocyclic group Chemical group 0.000 claims 37
- 125000003118 aryl group Chemical group 0.000 claims 32
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 125000005842 heteroatom Chemical group 0.000 claims 18
- 125000000304 alkynyl group Chemical group 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 8
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims 5
- 150000002825 nitriles Chemical class 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims 4
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000002346 iodo group Chemical group I* 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 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
- 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 1
- 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 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
- 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 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
- 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 1
- 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 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
- 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 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
- 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 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
- 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 1
- 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 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
- 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 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 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
- 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 1
- 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 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 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 1
- 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 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
- ORONFVUZGBIKBG-UHFFFAOYSA-N 3,5-difluoro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound FC1=CC(F)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 ORONFVUZGBIKBG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- FVWVORIFZUWGHE-UHFFFAOYSA-N 3-(trifluoromethyl)-n-[3-[3-(2-trimethylsilylethynyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]benzamide Chemical compound C=1C=NC2=C(C#C[Si](C)(C)C)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 FVWVORIFZUWGHE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- GBUHDCIHESIIAG-UHFFFAOYSA-N 3-amino-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-5-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(N)=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 GBUHDCIHESIIAG-UHFFFAOYSA-N 0.000 claims 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
- 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 1
- 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 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
- HDBKBBJQCWULSU-UHFFFAOYSA-N 3-fluoro-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 HDBKBBJQCWULSU-UHFFFAOYSA-N 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
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- JGJMNPYUYOAEEV-UHFFFAOYSA-N 4-methyl-n-[3-[3-(2h-tetrazol-5-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1C(=O)NC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C2=NNN=N2)=C1 JGJMNPYUYOAEEV-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- WOMLWFPGGVLXQL-UHFFFAOYSA-N 5-bromo-n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]thiophene-2-carboxamide Chemical compound S1C(Br)=CC=C1C(=O)NC1=CC=CC(C=2N3N=C(C=C3N=CC=2)C=2C=CN=CC=2)=C1 WOMLWFPGGVLXQL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 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
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000003445 Mouth Neoplasms Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma 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
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 229940007550 benzyl acetate Drugs 0.000 claims 1
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyloxyacetoaldehyde Natural products CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims 1
- 208000035269 cancer or benign tumor Diseases 0.000 claims 1
- LIPAUKCKCNPBQQ-UHFFFAOYSA-N chembl1089411 Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=C(C=C3N=CC=2)C=2NC=NC=2)=C1 LIPAUKCKCNPBQQ-UHFFFAOYSA-N 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
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- 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 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
- 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 1
- 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 1
- 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 1
- SJCWJMORMRRCGT-UHFFFAOYSA-N ethyl 7-[2-methoxy-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C(=CC=1)OC)=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 SJCWJMORMRRCGT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- NGEUMQOMYROEHK-UHFFFAOYSA-N ethyl 7-[3-[(3,4-dichlorobenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(Cl)C(Cl)=C1 NGEUMQOMYROEHK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- PHDJVZCVXUWRGT-UHFFFAOYSA-N ethyl 7-[3-[(3-chloro-4-methoxybenzoyl)amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(OC)C(Cl)=C1 PHDJVZCVXUWRGT-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 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 1
- 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 1
- 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 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
- 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- JIVQWFZRSLHDMU-UHFFFAOYSA-N ethyl 7-[3-[[4-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C=1C=NC2=C(C(=O)OCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(C(F)(F)F)C=C1 JIVQWFZRSLHDMU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 1
- 208000012987 lip and oral cavity carcinoma 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- 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 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
- 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 1
- 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 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
- 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 1
- 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 1
- 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 1
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- 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
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- 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 1
- ZICNAWJYTJVNBZ-UHFFFAOYSA-N n-[3-(2-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1)=CC=CC=1C(N1N=2)=CC=NC1=CC=2C1=CC=NC=C1 ZICNAWJYTJVNBZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
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- 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
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- 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 1
- 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 1
- 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 1
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- 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 1
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- 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 1
- 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 1
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- 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 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
- 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 1
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- 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 1
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- 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 1
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- 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 1
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- 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 1
- 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 1
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- 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 1
- 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 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
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- QKFNOCRNIKWHQY-UHFFFAOYSA-N n-[3-[3-(2-morpholin-4-ylpyrimidin-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=2C=NC(=NC=2)N2CCOCC2)=C1 QKFNOCRNIKWHQY-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
- 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 1
- 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 1
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- DVVNYRUHJUIYRY-UHFFFAOYSA-N n-[3-[3-[6-(methylamino)pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NC)=CC=C1C1=C2N=CC=C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)N2N=C1 DVVNYRUHJUIYRY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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- RQGLQNLOJSOQJU-UHFFFAOYSA-N n-[4-chloro-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(Cl)=CC=2)C=2N3N=CC(=C3N=CC=2)C2=CNN=C2)=C1 RQGLQNLOJSOQJU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- CIJPXTYYJNRMBN-UHFFFAOYSA-N n-benzyl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C(=O)NCC=2C=CC=CC=2)=C1 CIJPXTYYJNRMBN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- IUYWOWXZFPJKHI-UHFFFAOYSA-N n-propyl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)NCCC)C=NN2C=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1 IUYWOWXZFPJKHI-UHFFFAOYSA-N 0.000 claims 1
- RJRFKVCYDRENAZ-UHFFFAOYSA-N n-pyridin-3-yl-7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C=2N3N=CC(=C3N=CC=2)C(=O)NC=2C=NC=CC=2)=C1 RJRFKVCYDRENAZ-UHFFFAOYSA-N 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 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 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 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 1
- IKZYZBMLMQANMK-UHFFFAOYSA-N tert-butyl 4-[7-[2-fluoro-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazole-1-carboxylate Chemical class C1=NN(C(=O)OC(C)(C)C)C=C1C1=C2N=CC=C(C=3C(=CC=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=3)F)N2N=C1 IKZYZBMLMQANMK-UHFFFAOYSA-N 0.000 claims 1
- DYYJGTOTNMRNNH-UHFFFAOYSA-N tert-butyl 4-[7-[2-methoxy-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazole-1-carboxylate Chemical class C1=C(C=2N3N=CC(=C3N=CC=2)C2=CN(N=C2)C(=O)OC(C)(C)C)C(OC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 DYYJGTOTNMRNNH-UHFFFAOYSA-N 0.000 claims 1
- IBQWZZDKHBJWEN-UHFFFAOYSA-N tert-butyl 4-[7-[3-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyrimidin-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NN2C(C=3C=C(NC(=O)C=4C=C(C=CC=4)C(F)(F)F)C=CC=3)=CC=NC2=C1 IBQWZZDKHBJWEN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- DGJQKQVVEMCYSW-UHFFFAOYSA-N Cc1ccc2O[CH]Oc2c1 Chemical compound Cc1ccc2O[CH]Oc2c1 DGJQKQVVEMCYSW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78363106P | 2006-03-17 | 2006-03-17 | |
| PCT/US2007/006539 WO2007109093A2 (en) | 2006-03-17 | 2007-03-15 | Pyrazolo[1,5-a]pyrimidine derivatives and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009530296A JP2009530296A (ja) | 2009-08-27 |
| JP2009530296A5 true JP2009530296A5 (https=) | 2011-05-19 |
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Country Status (9)
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| US (1) | US20070219186A1 (https=) |
| EP (1) | EP1996594A2 (https=) |
| JP (1) | JP2009530296A (https=) |
| CN (1) | CN101405289A (https=) |
| AU (1) | AU2007227557A1 (https=) |
| BR (1) | BRPI0708813A2 (https=) |
| CA (1) | CA2643968A1 (https=) |
| MX (1) | MX2008011853A (https=) |
| WO (1) | WO2007109093A2 (https=) |
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| WO2009108827A1 (en) * | 2008-02-29 | 2009-09-03 | Wyeth | Fused tricyclic pyrazolo[1, 5-a]pyrimidines, methods for preparation and uses thereof |
| US20100029657A1 (en) * | 2008-02-29 | 2010-02-04 | Wyeth | Bridged, Bicyclic Heterocyclic or Spiro Bicyclic Heterocyclic Derivatives of Pyrazolo[1, 5-A]Pyrimidines, Methods for Preparation and Uses Thereof |
| EP2346335B1 (en) * | 2008-09-24 | 2018-11-14 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| CA2763589A1 (en) * | 2009-05-28 | 2010-12-02 | President And Fellows Of Harvard College | N,n'-diarylurea compounds and n,n'-diarylthiourea compounds as inhibitors of translation initiation |
| WO2014111037A1 (zh) * | 2013-01-18 | 2014-07-24 | 上海昀怡健康管理咨询有限公司 | 五元并六元杂环化合物、其制备方法、药物组合物和应用 |
| US9242969B2 (en) * | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
| JP6832430B2 (ja) | 2016-08-31 | 2021-02-24 | アジオス ファーマシューティカルズ， インコーポレイテッド | 細胞代謝過程の阻害剤 |
| CN111542515B (zh) * | 2017-10-30 | 2023-12-05 | 科罗拉多州立大学董事会法人团体 | Toll样受体8(tlr8)特异性拮抗剂及其制备方法和用途 |
Family Cites Families (12)
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|---|---|---|---|---|
| US4626538A (en) * | 1983-06-23 | 1986-12-02 | American Cyanamid Company | [7-(3-disubstituted amino)phenyl]pyrazolo[1,5-a]pyrimidines |
| US5219857A (en) * | 1986-10-16 | 1993-06-15 | American Cyanamid Company | Method of treating cognitive and related neural behavioral problems |
| US5126340A (en) * | 1986-10-16 | 1992-06-30 | American Cyanamid Company | 4-[(substituted)alkylcarbonyl]-4,5-dihydro and -4,5,6,7-tetrahydro-7-[(substituted)-phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitriles |
| US4963553A (en) * | 1986-10-16 | 1990-10-16 | American Cyanamid Co. | 4-[(substituted) alkylcarbonyl]-4,5-dihydro- and -4,5,6,7-tetrahydro-7-[(substituted)phenyl]pyrazolo[1,5-a]pyrimidines |
| US4847256A (en) * | 1986-10-16 | 1989-07-11 | American Cyanamid Company | 4,5-dihydro and 4,5,6,7-tetrahydropyrazolo(1,5-A)-pyrimidines |
| US5013737A (en) * | 1988-02-22 | 1991-05-07 | American Cyanamid Company | 2,4,8-Trisubstituted-3H,6H-1,4,5A,8A-tetraazaacenaphtylene-3,5-(4H)-diones and 2,4-8-trisubstituted-4,5-dihydro-5-thioxo-3H,6H-1,4,5A,8A-tetrazaacenaphthylen-3-ones |
| US4916137A (en) * | 1988-02-22 | 1990-04-10 | American Cyanamid Company | 5-(Substituted-amino)-8-(phenyl or substituted-phenyl)-3H,6H-1,4,5A,8A-tetraazaacenaphthylen-3-ones and treatment of neural behavior disorders |
| US20070179161A1 (en) * | 2003-03-31 | 2007-08-02 | Vernalis (Cambridge) Limited. | Pyrazolopyrimidine compounds and their use in medicine |
| ES2222813B1 (es) * | 2003-07-24 | 2005-12-16 | Ferrer Internacional, S.A. | N-(3-(3-sustituidas-pirazolo(1,5-a)pirimidin-7-il)-fenil)-sulfonamidas y composiciones y metodos relacionados. |
| WO2006033796A1 (en) * | 2004-09-17 | 2006-03-30 | Wyeth | SUBSTITUTED PYRAZOLO [1,5-a] PYRIMIDINES AND PROCESS FOR MAKING SAME |
| WO2006033795A2 (en) * | 2004-09-17 | 2006-03-30 | Wyeth | Substituted pyrazolo [1, 5-a] pyrimidines for inhibiting abnormal cell growth |
| EP1736475A1 (en) * | 2005-06-21 | 2006-12-27 | Ferrer Internacional, S.A. | Halogenated pyrazolo[1,5-a]pyrimidines, processes, uses, compositions and intermediates |
-
2007
- 2007-03-15 JP JP2009500484A patent/JP2009530296A/ja not_active Withdrawn
- 2007-03-15 CN CNA2007800095014A patent/CN101405289A/zh active Pending
- 2007-03-15 WO PCT/US2007/006539 patent/WO2007109093A2/en not_active Ceased
- 2007-03-15 CA CA002643968A patent/CA2643968A1/en not_active Abandoned
- 2007-03-15 BR BRPI0708813-2A patent/BRPI0708813A2/pt not_active Application Discontinuation
- 2007-03-15 MX MX2008011853A patent/MX2008011853A/es unknown
- 2007-03-15 EP EP07753186A patent/EP1996594A2/en not_active Withdrawn
- 2007-03-15 AU AU2007227557A patent/AU2007227557A1/en not_active Abandoned
- 2007-03-15 US US11/724,689 patent/US20070219186A1/en not_active Abandoned
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