HRP20120577T1 - 3,4-diarilpirazoli kao inhibitori proteinskih kinaza - Google Patents
3,4-diarilpirazoli kao inhibitori proteinskih kinaza Download PDFInfo
- Publication number
- HRP20120577T1 HRP20120577T1 HRP20120577AT HRP20120577T HRP20120577T1 HR P20120577 T1 HRP20120577 T1 HR P20120577T1 HR P20120577A T HRP20120577A T HR P20120577AT HR P20120577 T HRP20120577 T HR P20120577T HR P20120577 T1 HRP20120577 T1 HR P20120577T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrazol
- pyridin
- phenyl
- trifluoromethylphenyl
- optionally substituted
- Prior art date
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- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title 1
- 239000003909 protein kinase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 238000000034 method Methods 0.000 claims abstract 3
- 206010028980 Neoplasm Diseases 0.000 claims abstract 2
- 201000011510 cancer Diseases 0.000 claims abstract 2
- 230000000694 effects Effects 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- JCBBNKICBRGKBF-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 JCBBNKICBRGKBF-UHFFFAOYSA-N 0.000 claims 1
- WQGDVIJDJJYGIP-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 WQGDVIJDJJYGIP-UHFFFAOYSA-N 0.000 claims 1
- WKPFZFPXHYUWFF-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-3-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]urea Chemical compound C1=CC(C(C)(C)C)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 WKPFZFPXHYUWFF-UHFFFAOYSA-N 0.000 claims 1
- ZHFIADHEZMVEMS-UHFFFAOYSA-N 1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]urea Chemical compound FC1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 ZHFIADHEZMVEMS-UHFFFAOYSA-N 0.000 claims 1
- OEZDGCAUNKLHNK-UHFFFAOYSA-N 1-[2-fluoro-5-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound FC1=CC=C(C=2C(=CNN=2)C=2C=CN=CC=2)C=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 OEZDGCAUNKLHNK-UHFFFAOYSA-N 0.000 claims 1
- YJCHLIACYSUBJS-UHFFFAOYSA-N 1-[3-(1-butyl-4-pyridin-4-ylpyrazol-3-yl)phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1N(CCCC)C=C(C=2C=CN=CC=2)C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 YJCHLIACYSUBJS-UHFFFAOYSA-N 0.000 claims 1
- RSDHVUATLFFELX-UHFFFAOYSA-N 1-[3-(1-ethyl-4-pyridin-4-ylpyrazol-3-yl)phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1N(CC)C=C(C=2C=CN=CC=2)C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 RSDHVUATLFFELX-UHFFFAOYSA-N 0.000 claims 1
- BXJZUPBGKXOOFV-UHFFFAOYSA-N 1-[3-(1-methyl-4-pyridin-4-ylpyrazol-3-yl)phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1N(C)C=C(C=2C=CN=CC=2)C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 BXJZUPBGKXOOFV-UHFFFAOYSA-N 0.000 claims 1
- LRFHFNFRSOKIDY-UHFFFAOYSA-N 1-[3-(1-piperidin-4-yl-4-pyridin-4-ylpyrazol-3-yl)phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CN(N=2)C2CCNCC2)C=2C=CN=CC=2)=C1 LRFHFNFRSOKIDY-UHFFFAOYSA-N 0.000 claims 1
- KYJAOHDKHQLOEU-UHFFFAOYSA-N 1-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 KYJAOHDKHQLOEU-UHFFFAOYSA-N 0.000 claims 1
- DVCVWWXZOQNVET-UHFFFAOYSA-N 1-[3-(4-pyrimidin-4-yl-1h-pyrazol-5-yl)phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CNN=2)C=2N=CN=CC=2)=C1 DVCVWWXZOQNVET-UHFFFAOYSA-N 0.000 claims 1
- MKMPKVXBQQQQCF-UHFFFAOYSA-N 1-[3-[1-(2-fluoroethyl)-4-pyridin-4-ylpyrazol-3-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1N(CCF)C=C(C=2C=CN=CC=2)C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 MKMPKVXBQQQQCF-UHFFFAOYSA-N 0.000 claims 1
- KALJYGUVRZHUJM-UHFFFAOYSA-N 1-[3-[1-(2-hydroxyethyl)-4-pyridin-4-ylpyrazol-3-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1N(CCO)C=C(C=2C=CN=CC=2)C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 KALJYGUVRZHUJM-UHFFFAOYSA-N 0.000 claims 1
- ZLCDEIADBTWXQR-UHFFFAOYSA-N 1-[3-[1-(2-methylpropyl)-4-pyridin-4-ylpyrazol-3-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1N(CC(C)C)C=C(C=2C=CN=CC=2)C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 ZLCDEIADBTWXQR-UHFFFAOYSA-N 0.000 claims 1
- ZKPGUEVFQSXHDP-UHFFFAOYSA-N 1-[3-[1-(cyanomethyl)-4-pyridin-4-ylpyrazol-3-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CN(CC#N)N=2)C=2C=CN=CC=2)=C1 ZKPGUEVFQSXHDP-UHFFFAOYSA-N 0.000 claims 1
- HXLAXJCJDNMZJU-UHFFFAOYSA-N 1-[3-[4-(2-aminopyridin-4-yl)-1h-pyrazol-5-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=NC(N)=CC(C=2C(=NNC=2)C=2C=C(NC(=O)NC=3C=CC(=CC=3)C(F)(F)F)C=CC=2)=C1 HXLAXJCJDNMZJU-UHFFFAOYSA-N 0.000 claims 1
- HNVBXPKTFPJDRC-UHFFFAOYSA-N 1-[3-[4-(2-aminopyrimidin-4-yl)-1h-pyrazol-5-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound NC1=NC=CC(C=2C(=NNC=2)C=2C=C(NC(=O)NC=3C=CC(=CC=3)C(F)(F)F)C=CC=2)=N1 HNVBXPKTFPJDRC-UHFFFAOYSA-N 0.000 claims 1
- GHIHVDGRKXEXDM-UHFFFAOYSA-N 1-[4-(2-cyanopropan-2-yl)phenyl]-3-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]urea Chemical compound C1=CC(C(C)(C#N)C)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 GHIHVDGRKXEXDM-UHFFFAOYSA-N 0.000 claims 1
- CVHCTIFNAGQLFO-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[3-[1-(2-fluoroethyl)-4-pyridin-4-ylpyrazol-3-yl]phenyl]urea Chemical compound N=1N(CCF)C=C(C=2C=CN=CC=2)C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 CVHCTIFNAGQLFO-UHFFFAOYSA-N 0.000 claims 1
- CEJMDAGZFHVMIC-UHFFFAOYSA-N 2,5-difluoro-n-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]benzenesulfonamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC=2C=C(C=CC=2)C=2C(=CNN=2)C=2C=CN=CC=2)=C1 CEJMDAGZFHVMIC-UHFFFAOYSA-N 0.000 claims 1
- GWTHTMJASIXFRM-UHFFFAOYSA-N 2,5-difluoro-n-[3-(4-pyrimidin-4-yl-1h-pyrazol-5-yl)phenyl]benzenesulfonamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC=2C=C(C=CC=2)C=2C(=CNN=2)C=2N=CN=CC=2)=C1 GWTHTMJASIXFRM-UHFFFAOYSA-N 0.000 claims 1
- QJRXVENVVKLKCZ-UHFFFAOYSA-N 2-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]-n-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)CC1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 QJRXVENVVKLKCZ-UHFFFAOYSA-N 0.000 claims 1
- XGRLLWKBKBGELE-UHFFFAOYSA-N 2-methyl-n-[4-[5-[3-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrazol-4-yl]pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)C(C)C)=CC(C=2C(=NNC=2)C=2C=C(NC(=O)NC=3C=CC(=CC=3)C(F)(F)F)C=CC=2)=C1 XGRLLWKBKBGELE-UHFFFAOYSA-N 0.000 claims 1
- WIACXVZBFLZNBM-UHFFFAOYSA-N 3-(4-pyridin-4-yl-1h-pyrazol-5-yl)-n-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 WIACXVZBFLZNBM-UHFFFAOYSA-N 0.000 claims 1
- ICYLXOYZNVSEDG-UHFFFAOYSA-N 4-[3-[3-[(2,5-difluorophenyl)methoxy]-2,6-difluorophenyl]-1-ethylpyrazol-4-yl]pyridine Chemical compound N=1N(CC)C=C(C=2C=CN=CC=2)C=1C(C=1F)=C(F)C=CC=1OCC1=CC(F)=CC=C1F ICYLXOYZNVSEDG-UHFFFAOYSA-N 0.000 claims 1
- XFCXFXIRKWGFFY-UHFFFAOYSA-N 4-hydroxy-n-[4-[5-[3-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrazol-4-yl]pyridin-2-yl]butanamide Chemical compound C1=NC(NC(=O)CCCO)=CC(C=2C(=NNC=2)C=2C=C(NC(=O)NC=3C=CC(=CC=3)C(F)(F)F)C=CC=2)=C1 XFCXFXIRKWGFFY-UHFFFAOYSA-N 0.000 claims 1
- 102000042888 RAF family Human genes 0.000 claims 1
- 108091082327 RAF family Proteins 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 238000011319 anticancer therapy Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- FWBSIGJSPJUDCO-UHFFFAOYSA-N ethyl 4-pyridin-4-yl-3-[3-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]pyrazole-1-carboxylate Chemical compound N=1N(C(=O)OCC)C=C(C=2C=CN=CC=2)C=1C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 FWBSIGJSPJUDCO-UHFFFAOYSA-N 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- SICSAKKTOFFGFL-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 SICSAKKTOFFGFL-UHFFFAOYSA-N 0.000 claims 1
- KJQVIMVTKPUCLW-UHFFFAOYSA-N n-(4-tert-butylphenyl)-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 KJQVIMVTKPUCLW-UHFFFAOYSA-N 0.000 claims 1
- BYBCHAAFNHSCQN-UHFFFAOYSA-N n-[(2,5-difluorophenyl)methyl]-3-(1-ethyl-4-pyridin-4-ylpyrazol-3-yl)-2,4-difluoroaniline Chemical compound N=1N(CC)C=C(C=2C=CN=CC=2)C=1C(C=1F)=C(F)C=CC=1NCC1=CC(F)=CC=C1F BYBCHAAFNHSCQN-UHFFFAOYSA-N 0.000 claims 1
- UFIBKLWJXAXMTJ-UHFFFAOYSA-N n-[2,4-difluoro-3-(1-methyl-4-pyridin-4-ylpyrazol-3-yl)phenyl]-2,5-difluorobenzenesulfonamide Chemical compound N=1N(C)C=C(C=2C=CN=CC=2)C=1C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC(F)=CC=C1F UFIBKLWJXAXMTJ-UHFFFAOYSA-N 0.000 claims 1
- SYNHUOSXPJPDOA-UHFFFAOYSA-N n-[2,4-difluoro-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound FC1=CC=C(NS(=O)(=O)C(F)(F)F)C(F)=C1C1=NNC=C1C1=CC=NC=C1 SYNHUOSXPJPDOA-UHFFFAOYSA-N 0.000 claims 1
- DLSVZLPXKZKAPK-UHFFFAOYSA-N n-[2,4-difluoro-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]-2,2,2-trifluoroethanesulfonamide Chemical compound FC1=CC=C(NS(=O)(=O)CC(F)(F)F)C(F)=C1C1=NNC=C1C1=CC=NC=C1 DLSVZLPXKZKAPK-UHFFFAOYSA-N 0.000 claims 1
- RNSZSVGEXQQZQN-UHFFFAOYSA-N n-[2,4-difluoro-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]-2,5-difluorobenzenesulfonamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC=2C(=C(C=3C(=CNN=3)C=3C=CN=CC=3)C(F)=CC=2)F)=C1 RNSZSVGEXQQZQN-UHFFFAOYSA-N 0.000 claims 1
- HSBFGEIBBXVEGW-UHFFFAOYSA-N n-[2,4-difluoro-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]cyclohexanesulfonamide Chemical compound FC1=C(C=2C(=CNN=2)C=2C=CN=CC=2)C(F)=CC=C1NS(=O)(=O)C1CCCCC1 HSBFGEIBBXVEGW-UHFFFAOYSA-N 0.000 claims 1
- BVINNXAWANKLLY-UHFFFAOYSA-N n-[2,4-difluoro-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]cyclopropanesulfonamide Chemical compound FC1=C(C=2C(=CNN=2)C=2C=CN=CC=2)C(F)=CC=C1NS(=O)(=O)C1CC1 BVINNXAWANKLLY-UHFFFAOYSA-N 0.000 claims 1
- ATCMHZNUBBEKJQ-UHFFFAOYSA-N n-[2,4-difluoro-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]furan-2-sulfonamide Chemical compound FC1=C(C=2C(=CNN=2)C=2C=CN=CC=2)C(F)=CC=C1NS(=O)(=O)C1=CC=CO1 ATCMHZNUBBEKJQ-UHFFFAOYSA-N 0.000 claims 1
- LREVYMAUBGSYHP-UHFFFAOYSA-N n-[2,4-difluoro-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C=2C(=CNN=2)C=2C=CN=CC=2)=C1F LREVYMAUBGSYHP-UHFFFAOYSA-N 0.000 claims 1
- IOYMJLUOIVBAOG-UHFFFAOYSA-N n-[2,4-difluoro-3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]thiophene-3-sulfonamide Chemical compound FC1=C(C=2C(=CNN=2)C=2C=CN=CC=2)C(F)=CC=C1NS(=O)(=O)C=1C=CSC=1 IOYMJLUOIVBAOG-UHFFFAOYSA-N 0.000 claims 1
- LTEAPHVMAVHLOJ-UHFFFAOYSA-N n-[2,4-difluoro-3-(4-pyrimidin-4-yl-1h-pyrazol-5-yl)phenyl]-2,5-difluorobenzenesulfonamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC=2C(=C(C=3C(=CNN=3)C=3N=CN=CC=3)C(F)=CC=2)F)=C1 LTEAPHVMAVHLOJ-UHFFFAOYSA-N 0.000 claims 1
- FPAWFGCEVNXWPZ-UHFFFAOYSA-N n-[2,4-difluoro-3-[1-(2-methylpropyl)-4-pyridin-4-ylpyrazol-3-yl]phenyl]-2,5-difluorobenzenesulfonamide Chemical compound N=1N(CC(C)C)C=C(C=2C=CN=CC=2)C=1C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC(F)=CC=C1F FPAWFGCEVNXWPZ-UHFFFAOYSA-N 0.000 claims 1
- JFIJCAZHHGEQOQ-UHFFFAOYSA-N n-[2,4-difluoro-3-[1-(2-morpholin-4-ylethyl)-4-pyridin-4-ylpyrazol-3-yl]phenyl]-2,5-difluorobenzenesulfonamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC=2C(=C(C=3C(=CN(CCN4CCOCC4)N=3)C=3C=CN=CC=3)C(F)=CC=2)F)=C1 JFIJCAZHHGEQOQ-UHFFFAOYSA-N 0.000 claims 1
- ZRCMFTHNPAWNBV-UHFFFAOYSA-N n-[2,4-difluoro-3-[1-(2-piperidin-1-ylethyl)-4-pyridin-4-ylpyrazol-3-yl]phenyl]-2,5-difluorobenzenesulfonamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC=2C(=C(C=3C(=CN(CCN4CCCCC4)N=3)C=3C=CN=CC=3)C(F)=CC=2)F)=C1 ZRCMFTHNPAWNBV-UHFFFAOYSA-N 0.000 claims 1
- BWBFTIVWOSMIQS-UHFFFAOYSA-N n-[2,4-difluoro-3-[1-[2-(4-methylpiperazin-1-yl)ethyl]-4-pyridin-4-ylpyrazol-3-yl]phenyl]-2,5-difluorobenzenesulfonamide Chemical compound C1CN(C)CCN1CCN1N=C(C=2C(=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2F)F)C(C=2C=CN=CC=2)=C1 BWBFTIVWOSMIQS-UHFFFAOYSA-N 0.000 claims 1
- IEYSMIAHSDZOQV-UHFFFAOYSA-N n-[2,4-difluoro-3-[4-[2-(methylamino)pyridin-4-yl]-1h-pyrazol-5-yl]phenyl]-2,5-difluorobenzenesulfonamide Chemical compound C1=NC(NC)=CC(C=2C(=NNC=2)C=2C(=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2F)F)=C1 IEYSMIAHSDZOQV-UHFFFAOYSA-N 0.000 claims 1
- GDMUNKBRWNCHTD-UHFFFAOYSA-N n-[3-(1-ethyl-4-pyridin-4-ylpyrazol-3-yl)-2,4-difluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound N=1N(CC)C=C(C=2C=CN=CC=2)C=1C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC(F)=CC=C1F GDMUNKBRWNCHTD-UHFFFAOYSA-N 0.000 claims 1
- FTZMICJMLOEONC-UHFFFAOYSA-N n-[3-(1-ethyl-4-pyridin-4-ylpyrazol-3-yl)-2,4-difluorophenyl]-2-fluorobenzenesulfonamide Chemical compound N=1N(CC)C=C(C=2C=CN=CC=2)C=1C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC=C1F FTZMICJMLOEONC-UHFFFAOYSA-N 0.000 claims 1
- LKLMZETVFVOPBO-UHFFFAOYSA-N n-[3-(1-ethyl-4-pyridin-4-ylpyrazol-3-yl)-2,4-difluorophenyl]-3-fluorobenzenesulfonamide Chemical compound N=1N(CC)C=C(C=2C=CN=CC=2)C=1C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 LKLMZETVFVOPBO-UHFFFAOYSA-N 0.000 claims 1
- FQQBBPOYEJWYMH-UHFFFAOYSA-N n-[3-(1-ethyl-4-pyridin-4-ylpyrazol-3-yl)-2-fluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound N=1N(CC)C=C(C=2C=CN=CC=2)C=1C(C=1F)=CC=CC=1NS(=O)(=O)C1=CC(F)=CC=C1F FQQBBPOYEJWYMH-UHFFFAOYSA-N 0.000 claims 1
- POXYFOLISOZSGM-UHFFFAOYSA-N n-[3-(1-ethyl-4-pyridin-4-ylpyrazol-3-yl)-4-fluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound N=1N(CC)C=C(C=2C=CN=CC=2)C=1C(C(=CC=1)F)=CC=1NS(=O)(=O)C1=CC(F)=CC=C1F POXYFOLISOZSGM-UHFFFAOYSA-N 0.000 claims 1
- XEDFKFUJISMVCO-UHFFFAOYSA-N n-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CC(=O)NC1=CC=CC(C=2C(=CNN=2)C=2C=CN=CC=2)=C1 XEDFKFUJISMVCO-UHFFFAOYSA-N 0.000 claims 1
- MKHROVCIWDCFCI-UHFFFAOYSA-N n-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]furan-2-sulfonamide Chemical compound C=1C=COC=1S(=O)(=O)NC(C=1)=CC=CC=1C1=NNC=C1C1=CC=NC=C1 MKHROVCIWDCFCI-UHFFFAOYSA-N 0.000 claims 1
- FORHKERWLJVZBL-UHFFFAOYSA-N n-[3-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]thiophene-3-sulfonamide Chemical compound C1=CSC=C1S(=O)(=O)NC(C=1)=CC=CC=1C1=NNC=C1C1=CC=NC=C1 FORHKERWLJVZBL-UHFFFAOYSA-N 0.000 claims 1
- MPXFMPQKEAXHTG-UHFFFAOYSA-N n-[3-[1-[2-(dimethylamino)ethyl]-4-pyridin-4-ylpyrazol-3-yl]-2,4-difluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound N=1N(CCN(C)C)C=C(C=2C=CN=CC=2)C=1C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC(F)=CC=C1F MPXFMPQKEAXHTG-UHFFFAOYSA-N 0.000 claims 1
- PGDSPLXMPXRRLH-UHFFFAOYSA-N n-[3-[4-(2-aminopyridin-4-yl)-1-ethylpyrazol-3-yl]-2,4-difluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound N=1N(CC)C=C(C=2C=C(N)N=CC=2)C=1C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC(F)=CC=C1F PGDSPLXMPXRRLH-UHFFFAOYSA-N 0.000 claims 1
- KBDCMASAAJFRCN-UHFFFAOYSA-N n-[3-[4-(2-aminopyrimidin-4-yl)-1-ethylpyrazol-3-yl]-2,4-difluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound N=1N(CC)C=C(C=2N=C(N)N=CC=2)C=1C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC(F)=CC=C1F KBDCMASAAJFRCN-UHFFFAOYSA-N 0.000 claims 1
- QHLYGDBGQPUINJ-UHFFFAOYSA-N n-[3-[4-(2-aminopyrimidin-4-yl)-1h-pyrazol-5-yl]-2,4-difluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound NC1=NC=CC(C=2C(=NNC=2)C=2C(=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2F)F)=N1 QHLYGDBGQPUINJ-UHFFFAOYSA-N 0.000 claims 1
- WZHUFSLYUSWOGO-UHFFFAOYSA-N n-[3-[4-(2-aminopyrimidin-4-yl)-1h-pyrazol-5-yl]phenyl]-2,5-difluorobenzenesulfonamide Chemical compound NC1=NC=CC(C=2C(=NNC=2)C=2C=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2)=N1 WZHUFSLYUSWOGO-UHFFFAOYSA-N 0.000 claims 1
- YCKQTXGXPQDECM-UHFFFAOYSA-N n-[3-[4-[2-(ethylamino)pyridin-4-yl]-1h-pyrazol-5-yl]-2,4-difluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound C1=NC(NCC)=CC(C=2C(=NNC=2)C=2C(=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2F)F)=C1 YCKQTXGXPQDECM-UHFFFAOYSA-N 0.000 claims 1
- NGFLGYPWDYVXFI-UHFFFAOYSA-N n-[3-[4-[2-(ethylamino)pyrimidin-4-yl]-1h-pyrazol-5-yl]phenyl]-2,5-difluorobenzenesulfonamide Chemical compound CCNC1=NC=CC(C=2C(=NNC=2)C=2C=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2)=N1 NGFLGYPWDYVXFI-UHFFFAOYSA-N 0.000 claims 1
- UWSJKBQWDONEEJ-UHFFFAOYSA-N n-[4-[5-[3-[(2,5-difluorophenyl)sulfonylamino]-2,6-difluorophenyl]-1h-pyrazol-4-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C(=NNC=2)C=2C(=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2F)F)=C1 UWSJKBQWDONEEJ-UHFFFAOYSA-N 0.000 claims 1
- VWBHHBMXXMSAAQ-UHFFFAOYSA-N n-[4-[5-[3-[(2,5-difluorophenyl)sulfonylamino]-2,6-difluorophenyl]-1h-pyrazol-4-yl]pyrimidin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(C=2C(=NNC=2)C=2C(=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2F)F)=N1 VWBHHBMXXMSAAQ-UHFFFAOYSA-N 0.000 claims 1
- XXZJENNAYRRMGY-UHFFFAOYSA-N n-[4-[5-[3-[(2,5-difluorophenyl)sulfonylamino]phenyl]-1h-pyrazol-4-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C(=NNC=2)C=2C=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2)=C1 XXZJENNAYRRMGY-UHFFFAOYSA-N 0.000 claims 1
- YKDRRCBYPSMTMM-UHFFFAOYSA-N n-[4-[5-[3-[(2,5-difluorophenyl)sulfonylamino]phenyl]-1h-pyrazol-4-yl]pyrimidin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(C=2C(=NNC=2)C=2C=C(NS(=O)(=O)C=3C(=CC=C(F)C=3)F)C=CC=2)=N1 YKDRRCBYPSMTMM-UHFFFAOYSA-N 0.000 claims 1
- LUSQEYUJOTWBPQ-UHFFFAOYSA-N n-[4-[5-[3-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrazol-4-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C(=NNC=2)C=2C=C(NC(=O)NC=3C=CC(=CC=3)C(F)(F)F)C=CC=2)=C1 LUSQEYUJOTWBPQ-UHFFFAOYSA-N 0.000 claims 1
- KLBPEORUBNFFCR-UHFFFAOYSA-N n-[4-[5-[3-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrazol-4-yl]pyridin-2-yl]cyclopentanecarboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC(C=2C(=CNN=2)C=2C=C(NC(=O)C3CCCC3)N=CC=2)=C1 KLBPEORUBNFFCR-UHFFFAOYSA-N 0.000 claims 1
- ZTXAMHYDBFLQEE-UHFFFAOYSA-N n-[4-[5-[3-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrazol-4-yl]pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)CC)=CC(C=2C(=NNC=2)C=2C=C(NC(=O)NC=3C=CC(=CC=3)C(F)(F)F)C=CC=2)=C1 ZTXAMHYDBFLQEE-UHFFFAOYSA-N 0.000 claims 1
- RJGPDAAWHIVGLJ-UHFFFAOYSA-N n-[4-[5-[3-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrazol-4-yl]pyrimidin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(C=2C(=NNC=2)C=2C=C(NC(=O)NC=3C=CC(=CC=3)C(F)(F)F)C=CC=2)=N1 RJGPDAAWHIVGLJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 108060006633 protein kinase Proteins 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
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EP08161076 | 2008-07-24 | ||
PCT/EP2009/059506 WO2010010154A1 (en) | 2008-07-24 | 2009-07-23 | 3,4-diarylpyrazoles as protein kinase inhibitors |
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HRP20120577AT HRP20120577T1 (hr) | 2008-07-24 | 2012-07-12 | 3,4-diarilpirazoli kao inhibitori proteinskih kinaza |
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US (2) | US8541575B2 (xx) |
EP (1) | EP2324008B1 (xx) |
JP (1) | JP5385382B2 (xx) |
CN (1) | CN102105459B (xx) |
AT (1) | ATE557015T1 (xx) |
AU (1) | AU2009273197B2 (xx) |
BR (1) | BRPI0916356B1 (xx) |
CA (1) | CA2731146C (xx) |
CL (1) | CL2011000124A1 (xx) |
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HK (1) | HK1157337A1 (xx) |
HR (1) | HRP20120577T1 (xx) |
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PT (1) | PT2324008E (xx) |
SI (1) | SI2324008T1 (xx) |
WO (1) | WO2010010154A1 (xx) |
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CL2008001943A1 (es) | 2007-07-02 | 2009-09-11 | Boehringer Ingelheim Int | Compuestos derivados de fenil-triazol, inhibidores de enzimas de señales especificas que participan del control de la proliferacion celular; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar cancer, infecciones, enfermedades inflamatorias y autoinmunes. |
UA103319C2 (xx) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Сполуки бензенсульфонамідтіазолу та -оксазолу$соединения бензенсульфонамидтиазола и -оксазола |
SI2324008T1 (sl) * | 2008-07-24 | 2012-08-31 | Nerviano Medical Sciences Srl | 3,4-diarilpirazoli kot protein-kinazni inhibitorji |
US8778929B2 (en) | 2008-09-29 | 2014-07-15 | Boehringer Ingelheim International Gmbh | Substituted heteroaryl inhibitors of B-RAF |
JP2011057661A (ja) * | 2009-08-14 | 2011-03-24 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
US8242260B2 (en) | 2009-08-28 | 2012-08-14 | Novartis Ag | Compounds and compositions as protein kinase inhibitors |
JO3002B1 (ar) | 2009-08-28 | 2016-09-05 | Irm Llc | مركبات و تركيبات كمثبطات كيناز بروتين |
WO2011092088A1 (en) | 2010-01-27 | 2011-08-04 | Nerviano Medical Sciences S.R.L. | Sulfonamido derivatives of 3,4-diarylpyrazoles as protein kinase inhibitors |
WO2011117381A1 (en) | 2010-03-26 | 2011-09-29 | Boehringer Ingelheim International Gmbh | B-raf kinase inhibitors |
JP5871897B2 (ja) | 2010-03-26 | 2016-03-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ピリジルトリアゾール |
AR081810A1 (es) | 2010-04-07 | 2012-10-24 | Bayer Cropscience Ag | Piridinilpirazoles biciclicos |
KR20140117684A (ko) * | 2010-06-25 | 2014-10-07 | 노파르티스 아게 | 단백질 키나제 억제제로서의 헤테로아릴 화합물 및 조성물 |
US9114137B2 (en) | 2010-08-03 | 2015-08-25 | Nerviano Medical Sciences S.R.L. | Derivatives of pyrazolophenyl-benzenesulfonamide compounds and use thereof as antitumor agents |
TWI480276B (zh) * | 2010-08-27 | 2015-04-11 | Irm Llc | 作為蛋白質激酶抑制劑之化合物及組合物 |
US8710055B2 (en) | 2010-12-21 | 2014-04-29 | Boehringer Ingelheim International Gmbh | Triazolylphenyl sulfonamides as serine/threonine kinase inhibitors |
SG192126A1 (en) * | 2011-01-25 | 2013-09-30 | Univ Michigan | Bcl-2/bcl-xl inhibitors and therapeutic methods using the same |
WO2012113774A1 (en) | 2011-02-24 | 2012-08-30 | Nerviano Medical Sciences S.R.L. | Thiazolylphenyl-benzenesulfonamido derivatives as kinase inhibitors |
KR101298651B1 (ko) * | 2011-03-16 | 2013-08-21 | 연세대학교 산학협력단 | 효능이 강화된 혈관신생 억제용 약제학적 조성물 |
CA2851142A1 (en) | 2011-10-06 | 2013-04-11 | Bayer Intellectual Property Gmbh | Heterocyclylpyri (mi) dinylpyrazole as fungicidals |
KR20140072177A (ko) | 2011-10-06 | 2014-06-12 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 헤테로사이클릴피리(미)디닐피라졸 |
CN108542906A (zh) | 2011-11-11 | 2018-09-18 | 诺华股份有限公司 | 治疗增生性疾病的方法 |
CN103945831A (zh) | 2011-11-23 | 2014-07-23 | 诺华股份有限公司 | 医药制剂 |
ES2625944T3 (es) | 2012-11-02 | 2017-07-21 | Pfizer Inc. | Inhibidores de tirosina cinasa de Bruton |
US9096625B2 (en) | 2013-01-16 | 2015-08-04 | The Regents Of The University Of Michigan | BCL-2/BCL-XL inhibitors and therapeutic methods using the same |
US9242969B2 (en) | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
GB201410430D0 (en) | 2014-06-11 | 2014-07-23 | Redx Pharma Ltd | Compounds |
UY36294A (es) | 2014-09-12 | 2016-04-29 | Novartis Ag | Compuestos y composiciones como inhibidores de quinasa |
ES2918924T3 (es) | 2015-04-01 | 2022-07-21 | Rigel Pharmaceuticals Inc | Inhibidores de TGF-beta |
PE20180686A1 (es) * | 2015-08-03 | 2018-04-23 | Glenmark Pharmaceuticals Sa | Compuestos nuevos como moduladores de ror gamma |
EP4116303A1 (en) | 2015-09-16 | 2023-01-11 | Loxo Oncology, Inc. | Pyrazolopyrimidine derivatives as btk inhibitors for the treatment of cancer |
PE20220507A1 (es) * | 2015-12-16 | 2022-04-07 | Loxo Oncology Inc | Compuestos utiles como inhibidores de cinasa |
CR20190002A (es) | 2016-06-03 | 2019-06-10 | Zhu Alexander Cao | Combinaciones farmacéuticas |
CN106883266B (zh) * | 2017-01-23 | 2020-03-17 | 江苏七洲绿色化工股份有限公司 | 一种1-(4-氯苯基)-2-环丙基-1-丙酮的制备方法及其中间体 |
WO2019081485A1 (de) | 2017-10-26 | 2019-05-02 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2019081477A1 (de) | 2017-10-26 | 2019-05-02 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
US11053221B2 (en) * | 2018-10-26 | 2021-07-06 | Arrien Pharmaceuticals Llc | Substituted pyrimidines for inhibiting embryonic leucine zipper kinase activity |
WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
TW202100520A (zh) | 2019-03-05 | 2021-01-01 | 美商英塞特公司 | 作為cdk2 抑制劑之吡唑基嘧啶基胺化合物 |
US11919904B2 (en) | 2019-03-29 | 2024-03-05 | Incyte Corporation | Sulfonylamide compounds as CDK2 inhibitors |
US11447494B2 (en) | 2019-05-01 | 2022-09-20 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
US11440914B2 (en) | 2019-05-01 | 2022-09-13 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
MX2021014794A (es) | 2019-06-03 | 2022-01-18 | Bayer Ag | Acidos 1-fenil-5-azinilpirazolil-3-oxialquilicos y su uso para combatir el crecimiento no deseado de plantas. |
MX2022001940A (es) | 2019-08-14 | 2022-05-10 | Incyte Corp | Compuestos de imidazolil pirimidinilamina como inhibidores de cdk2. |
PE20221905A1 (es) | 2019-10-11 | 2022-12-23 | Incyte Corp | Aminas biciclicas como inhibidoras de la cdk2 |
KR102323820B1 (ko) * | 2019-10-31 | 2021-11-08 | 한국화학연구원 | 돌연변이형 idh 억제제, 이의 제조방법 및 이를 유효성분으로 함유하는 약학적 조성물 |
CN112979613B (zh) * | 2019-12-16 | 2022-04-26 | 四川大学华西医院 | 2-(1h-吡唑-3-基)吡啶衍生物及其制备方法和用途 |
BR112022011766A2 (pt) | 2019-12-19 | 2022-08-30 | Bayer Ag | Ácidos de 1,5-difenilpirazolil-3-oxialquila e ácidos de 1-fenil-5-tienilpirazolil-3-oxialquila e uso dos mesmos para controle de crescimento indesejado de planta |
WO2021120890A1 (en) * | 2019-12-20 | 2021-06-24 | Novartis Ag | Pyrazolyl derivatives useful as anti-cancer agents |
US20230126893A1 (en) | 2020-01-31 | 2023-04-27 | Bayer Aktiengesellschaft | [(1,4,5-trisubstituted-1h-pyrazol-3-yl)sulfanyl]acetic acid derivatives, salts thereof, and use thereof as active herbicidal ingredients |
TW202204354A (zh) * | 2020-04-02 | 2022-02-01 | 美商普雷辛肯公司 | 用於csk調節之化合物及方法以及其說明 |
BR112022021901A2 (pt) | 2020-04-29 | 2023-01-17 | Bayer Ag | Ácidos de 1-pirazinilpirazolil-3-oxialquila e seus derivados e seu uso para controle de crescimento indesejado de planta |
AU2021367046A1 (en) | 2020-10-23 | 2023-06-08 | Bayer Aktiengesellschaft | 1-(pyridyl)-5-azinylpyrazole derivatives, and their use for control of undesired plant growth |
TW202233607A (zh) * | 2020-10-30 | 2022-09-01 | 瑞士商諾華公司 | Kras g12c抑制劑化合物之新結晶形式 |
AU2022296784A1 (en) | 2021-06-25 | 2024-01-18 | Bayer Aktiengesellschaft | (1,4,5-trisubstituted-1h-pyrazole-3-yl)oxy-2-alkoxy alkyl acids and their derivatives, their salts and their use as herbicidal agents |
WO2023091873A1 (en) * | 2021-11-19 | 2023-05-25 | The Board Of Trustees Of The University Of Illinois | Gram-negative specific antibiotics sparing effect on gut microbiome |
WO2023099381A1 (de) | 2021-12-01 | 2023-06-08 | Bayer Aktiengesellschaft | (1,4,5-trisubstituierte-1h-pyrazol-3-yl)oxy-2-alkylthio-alkylsäuren und -alkylsäure-derivate, deren salze und ihre verwendung als herbizide wirkstoffe |
US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
WO2024078871A1 (de) | 2022-10-14 | 2024-04-18 | Bayer Aktiengesellschaft | 1-pyridyl-5-phenylpyrazolyl-3-oxy- und -3-thioalkylsäuren und derivate und deren verwendung zur bekämpfung unerwünschten pflanzenwachstums |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EA003925B1 (ru) | 1997-05-22 | 2003-10-30 | Дж.Д.Сирл Энд Ко | ЗАМЕЩЕННЫЕ ПИРАЗОЛЫ, КАК ИНГИБИТОРЫ p 38 КИНАЗЫ |
US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
AU2002356301A1 (en) | 2001-12-21 | 2003-07-15 | Cancer Research Technology Ltd. | 3,4-diarylpyrazoles and their use in the therapy of cancer |
US20090149469A1 (en) * | 2004-01-09 | 2009-06-11 | Carlos Garcia-Echeverria | Phenyl-[4-(3-phenyl-1h-pyrazol-4-yl)-pyrimidin-2-yl]-amine derivatives as igf-ir inhibitors |
US20080242667A1 (en) | 2005-08-26 | 2008-10-02 | Smithkline Beecham Corporation | Pyrimidinyl-Pyrazole Inhibitors of Aurora Kinases |
EP2024353A2 (en) * | 2006-03-16 | 2009-02-18 | Pfizer Products Inc. | Pyrazole compounds |
WO2008042639A1 (en) * | 2006-10-02 | 2008-04-10 | Irm Llc | Compounds and compositions as protein kinase inhibitors |
SI2324008T1 (sl) * | 2008-07-24 | 2012-08-31 | Nerviano Medical Sciences Srl | 3,4-diarilpirazoli kot protein-kinazni inhibitorji |
WO2011092088A1 (en) * | 2010-01-27 | 2011-08-04 | Nerviano Medical Sciences S.R.L. | Sulfonamido derivatives of 3,4-diarylpyrazoles as protein kinase inhibitors |
US9114137B2 (en) | 2010-08-03 | 2015-08-25 | Nerviano Medical Sciences S.R.L. | Derivatives of pyrazolophenyl-benzenesulfonamide compounds and use thereof as antitumor agents |
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AU2009273197A2 (en) | 2011-03-10 |
WO2010010154A1 (en) | 2010-01-28 |
US8946250B2 (en) | 2015-02-03 |
CN102105459A (zh) | 2011-06-22 |
CN102105459B (zh) | 2014-09-10 |
PL2324008T3 (pl) | 2012-09-28 |
EA019722B1 (ru) | 2014-05-30 |
EA201170249A1 (ru) | 2011-10-31 |
CA2731146C (en) | 2016-05-03 |
US20110144068A1 (en) | 2011-06-16 |
AU2009273197A1 (en) | 2010-01-28 |
PT2324008E (pt) | 2012-06-25 |
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AU2009273197B2 (en) | 2014-01-16 |
CL2011000124A1 (es) | 2011-05-06 |
HK1157337A1 (xx) | 2012-06-29 |
US8541575B2 (en) | 2013-09-24 |
EP2324008A1 (en) | 2011-05-25 |
BRPI0916356B1 (pt) | 2022-08-23 |
ATE557015T1 (de) | 2012-05-15 |
US20140005150A1 (en) | 2014-01-02 |
CY1117667T1 (el) | 2017-05-17 |
BRPI0916356A2 (xx) | 2018-08-21 |
ES2386408T3 (es) | 2012-08-20 |
EP2324008B1 (en) | 2012-05-09 |
JP5385382B2 (ja) | 2014-01-08 |
JP2011528698A (ja) | 2011-11-24 |
CA2731146A1 (en) | 2010-01-28 |
MX2011000738A (es) | 2011-02-23 |
SI2324008T1 (sl) | 2012-08-31 |
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