JP2005524609A5 - - Google Patents
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- JP2005524609A5 JP2005524609A5 JP2003552768A JP2003552768A JP2005524609A5 JP 2005524609 A5 JP2005524609 A5 JP 2005524609A5 JP 2003552768 A JP2003552768 A JP 2003552768A JP 2003552768 A JP2003552768 A JP 2003552768A JP 2005524609 A5 JP2005524609 A5 JP 2005524609A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridazin
- pyrazolo
- pyrimidinamine
- alkyl
- hydrogen
- 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.)
- Pending
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- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- -1 6-chloro-1H-benzoimidazol-2-yl Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- GBRORGYPYNNDGL-UHFFFAOYSA-N 1-(dimethylamino)-3-[4-[[4-(6-morpholin-4-ylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-yl]amino]phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CN(C)C)=CC=C1NC1=NC=CC(C2=C3C=CC(=NN3N=C2)N2CCOCC2)=N1 GBRORGYPYNNDGL-UHFFFAOYSA-N 0.000 claims 1
- PSTOACKLPREGGX-UHFFFAOYSA-N 1-[3-[(4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-yl)amino]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCNC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 PSTOACKLPREGGX-UHFFFAOYSA-N 0.000 claims 1
- CWRTWFWDDAJOMG-UHFFFAOYSA-N 3-[(4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-yl)amino]benzonitrile Chemical compound N#CC1=CC=CC(NC=2N=C(C=CN=2)C2=C3C=CC=NN3N=C2)=C1 CWRTWFWDDAJOMG-UHFFFAOYSA-N 0.000 claims 1
- XKYJKKJKDAGKNZ-UHFFFAOYSA-N 3-[2-(cyclopropylamino)pyrimidin-4-yl]-7h-pyrazolo[1,5-b]pyridazin-6-one Chemical compound C1=NN2N=C(O)C=CC2=C1C(N=1)=CC=NC=1NC1CC1 XKYJKKJKDAGKNZ-UHFFFAOYSA-N 0.000 claims 1
- FLUPOKVTJQLXSE-UHFFFAOYSA-N 4-(2-butylpyrazolo[1,5-b]pyridazin-3-yl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidin-2-amine Chemical compound CCCCC1=NN2N=CC=CC2=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 FLUPOKVTJQLXSE-UHFFFAOYSA-N 0.000 claims 1
- DKXUHTCPDJKABE-UHFFFAOYSA-N 4-(2-butylpyrazolo[1,5-b]pyridazin-3-yl)-n-cyclopropylpyrimidin-2-amine Chemical compound CCCCC1=NN2N=CC=CC2=C1C(N=1)=CC=NC=1NC1CC1 DKXUHTCPDJKABE-UHFFFAOYSA-N 0.000 claims 1
- RBIONWHBBUZDRJ-UHFFFAOYSA-N 4-(2-ethylpyrazolo[1,5-b]pyridazin-3-yl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidin-2-amine Chemical compound CCC1=NN2N=CC=CC2=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 RBIONWHBBUZDRJ-UHFFFAOYSA-N 0.000 claims 1
- CEOSCLCDTBXJBH-UHFFFAOYSA-N 4-(6-methoxypyrazolo[1,5-b]pyridazin-3-yl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidin-2-amine Chemical compound C1=NN2N=C(OC)C=CC2=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 CEOSCLCDTBXJBH-UHFFFAOYSA-N 0.000 claims 1
- QKNZQSYOXRAXPX-UHFFFAOYSA-N 4-[(4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-yl)amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 QKNZQSYOXRAXPX-UHFFFAOYSA-N 0.000 claims 1
- VSZVMUGJWVQEOS-UHFFFAOYSA-N 4-[(4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 VSZVMUGJWVQEOS-UHFFFAOYSA-N 0.000 claims 1
- YRSCDRTXWYUNBB-UHFFFAOYSA-N 4-[(4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-yl)amino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 YRSCDRTXWYUNBB-UHFFFAOYSA-N 0.000 claims 1
- NZEMZNIMMYPXRT-UHFFFAOYSA-N 4-[6-(2-chlorophenyl)pyrazolo[1,5-b]pyridazin-3-yl]-n-cyclopropylpyrimidin-2-amine Chemical compound ClC1=CC=CC=C1C1=NN2N=CC(C=3N=C(NC4CC4)N=CC=3)=C2C=C1 NZEMZNIMMYPXRT-UHFFFAOYSA-N 0.000 claims 1
- VHNFQSZQXINXSV-UHFFFAOYSA-N 4-[6-(4-fluorophenyl)pyrazolo[1,5-b]pyridazin-3-yl]-n-(4-methoxyphenyl)pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=CC(C2=C3C=CC(=NN3N=C2)C=2C=CC(F)=CC=2)=N1 VHNFQSZQXINXSV-UHFFFAOYSA-N 0.000 claims 1
- AKAGBRZFDUGGEX-UHFFFAOYSA-N 4-[6-(4-fluorophenyl)pyrazolo[1,5-b]pyridazin-3-yl]-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=CC(C2=C3C=CC(=NN3N=C2)C=2C=CC(F)=CC=2)=N1 AKAGBRZFDUGGEX-UHFFFAOYSA-N 0.000 claims 1
- QTYPVJBVNHCPHH-UHFFFAOYSA-N 4-n,4-n-dimethyl-1-n-[4-(6-morpholin-4-ylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-yl]benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC=CC(C2=C3C=CC(=NN3N=C2)N2CCOCC2)=N1 QTYPVJBVNHCPHH-UHFFFAOYSA-N 0.000 claims 1
- JOSDAWJORYYQIX-UHFFFAOYSA-N 4-pyrazolo[1,5-b]pyridazin-3-yl-n-(2,2,2-trifluoroethyl)pyrimidin-2-amine Chemical compound FC(F)(F)CNC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 JOSDAWJORYYQIX-UHFFFAOYSA-N 0.000 claims 1
- BVUVQUIZCFRPJG-UHFFFAOYSA-N 4-pyrazolo[1,5-b]pyridazin-3-yl-n-(3,4,5-trimethoxyphenyl)pyrimidin-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C=CN=2)C2=C3C=CC=NN3N=C2)=C1 BVUVQUIZCFRPJG-UHFFFAOYSA-N 0.000 claims 1
- VKVKUKGJNTVGRG-UHFFFAOYSA-N 4-pyrazolo[1,5-b]pyridazin-3-yl-n-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound FC(F)(F)C1=CC=CC(NC=2N=C(C=CN=2)C2=C3C=CC=NN3N=C2)=C1 VKVKUKGJNTVGRG-UHFFFAOYSA-N 0.000 claims 1
- DWCXDNWLEOSGIS-UHFFFAOYSA-N CS(=O)(=O)O.CC(CCNC1=NC=CC(=N1)C=1C=NN2N=CC=CC21)NC Chemical compound CS(=O)(=O)O.CC(CCNC1=NC=CC(=N1)C=1C=NN2N=CC=CC21)NC DWCXDNWLEOSGIS-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229940034982 antineoplastic agent Drugs 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 1
- 231100000433 cytotoxic Toxicity 0.000 claims 1
- 230000001472 cytotoxic effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 208000037888 epithelial cell injury Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- QGMKFIGNGWVOSE-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1=NN2N=CC=CC2=C1C1=NC(NC2=CC=C3OCOC3=C2)=NC=C1 QGMKFIGNGWVOSE-UHFFFAOYSA-N 0.000 claims 1
- WIIIHAKKVLVGJX-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1=NN2N=CC=CC2=C1C1=NC(NC=2C=C3OCCOC3=CC=2)=NC=C1 WIIIHAKKVLVGJX-UHFFFAOYSA-N 0.000 claims 1
- MYOUKRZQKNFETG-UHFFFAOYSA-N n-(2-chlorophenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound ClC1=CC=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 MYOUKRZQKNFETG-UHFFFAOYSA-N 0.000 claims 1
- WKITVSVNTNNVLF-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound CC1=CC(C)=CC(NC=2N=C(C=CN=2)C2=C3C=CC=NN3N=C2)=C1 WKITVSVNTNNVLF-UHFFFAOYSA-N 0.000 claims 1
- XQCOGMDQGWFCGL-UHFFFAOYSA-N n-(3-chloro-4-morpholin-4-ylphenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound ClC1=CC(NC=2N=C(C=CN=2)C2=C3C=CC=NN3N=C2)=CC=C1N1CCOCC1 XQCOGMDQGWFCGL-UHFFFAOYSA-N 0.000 claims 1
- GBNWWXHUOVAUHT-UHFFFAOYSA-N n-(3-methoxyphenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound COC1=CC=CC(NC=2N=C(C=CN=2)C2=C3C=CC=NN3N=C2)=C1 GBNWWXHUOVAUHT-UHFFFAOYSA-N 0.000 claims 1
- ZRWNCIWVANTRGL-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound N=1C=CC(C2=C3C=CC=NN3N=C2)=NC=1NCCCN1CCOCC1 ZRWNCIWVANTRGL-UHFFFAOYSA-N 0.000 claims 1
- DENIPLMYQYHPPA-UHFFFAOYSA-N n-(3-nitrophenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound [O-][N+](=O)C1=CC=CC(NC=2N=C(C=CN=2)C2=C3C=CC=NN3N=C2)=C1 DENIPLMYQYHPPA-UHFFFAOYSA-N 0.000 claims 1
- ONTYJGWYVMEOIF-UHFFFAOYSA-N n-(4-chlorophenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 ONTYJGWYVMEOIF-UHFFFAOYSA-N 0.000 claims 1
- SPYYDYXTVMRMEZ-UHFFFAOYSA-N n-(4-fluorophenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 SPYYDYXTVMRMEZ-UHFFFAOYSA-N 0.000 claims 1
- WPYZRTGDEWJZIP-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 WPYZRTGDEWJZIP-UHFFFAOYSA-N 0.000 claims 1
- ZGPQUFZDMCAFGN-UHFFFAOYSA-N n-(4-methylsulfonylphenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 ZGPQUFZDMCAFGN-UHFFFAOYSA-N 0.000 claims 1
- RVBOIHXTZQGXRV-UHFFFAOYSA-N n-(4-nitrophenyl)-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 RVBOIHXTZQGXRV-UHFFFAOYSA-N 0.000 claims 1
- PBWVSMSYTVNKEU-UHFFFAOYSA-N n-(4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-yl)-1,3-benzoxazol-2-amine Chemical compound C1=NN2N=CC=CC2=C1C1=NC(NC=2OC3=CC=CC=C3N=2)=NC=C1 PBWVSMSYTVNKEU-UHFFFAOYSA-N 0.000 claims 1
- IWGZWYKKIFMJCQ-UHFFFAOYSA-N n-(4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-yl)-3h-benzimidazol-5-amine Chemical compound C1=NN2N=CC=CC2=C1C1=NC(NC=2C=C3NC=NC3=CC=2)=NC=C1 IWGZWYKKIFMJCQ-UHFFFAOYSA-N 0.000 claims 1
- NEWXQDRWGLAOAY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1=CC(Cl)=CC=C1CNC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 NEWXQDRWGLAOAY-UHFFFAOYSA-N 0.000 claims 1
- SYAYIIIJZNUJPQ-UHFFFAOYSA-N n-[3-(1,3-oxazol-5-yl)phenyl]-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound N=1C=CC(C2=C3C=CC=NN3N=C2)=NC=1NC(C=1)=CC=CC=1C1=CN=CO1 SYAYIIIJZNUJPQ-UHFFFAOYSA-N 0.000 claims 1
- PWQDMUJHLRNRTQ-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)propyl]-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1CN(C)CCN1CCCNC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 PWQDMUJHLRNRTQ-UHFFFAOYSA-N 0.000 claims 1
- NKEZMLRTYBINTC-UHFFFAOYSA-N n-[3-chloro-4-(4-methylpiperazin-1-yl)phenyl]-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1CN(C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 NKEZMLRTYBINTC-UHFFFAOYSA-N 0.000 claims 1
- GBYZMXCPDFNNOB-UHFFFAOYSA-N n-[3-methoxy-5-(trifluoromethyl)phenyl]-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound FC(F)(F)C1=CC(OC)=CC(NC=2N=C(C=CN=2)C2=C3C=CC=NN3N=C2)=C1 GBYZMXCPDFNNOB-UHFFFAOYSA-N 0.000 claims 1
- AJAGHHORROJWRU-UHFFFAOYSA-N n-[3-methyl-4-(4-methylpiperazin-1-yl)phenyl]-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1CN(C)CCN1C(C(=C1)C)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 AJAGHHORROJWRU-UHFFFAOYSA-N 0.000 claims 1
- ZOTNSCLLJKXGSD-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1CN(C)CCN1C(C(=C1)C(F)(F)F)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 ZOTNSCLLJKXGSD-UHFFFAOYSA-N 0.000 claims 1
- RRUGSPOGOGBMMW-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-4-(2-methylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2C)=N1 RRUGSPOGOGBMMW-UHFFFAOYSA-N 0.000 claims 1
- AUAUBVTWWCYNPP-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 AUAUBVTWWCYNPP-UHFFFAOYSA-N 0.000 claims 1
- DQKZVZRKPRQVEU-UHFFFAOYSA-N n-[4-(diethylaminomethyl)phenyl]-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1=CC(CN(CC)CC)=CC=C1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 DQKZVZRKPRQVEU-UHFFFAOYSA-N 0.000 claims 1
- LTNXNHHGQLANQP-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopropylamino)pyrimidin-4-yl]pyrazolo[1,5-b]pyridazin-6-amine Chemical compound C1CC1NC1=NC=CC(C2=C3C=CC(NC4CCCC4)=NN3N=C2)=N1 LTNXNHHGQLANQP-UHFFFAOYSA-N 0.000 claims 1
- RPRZAINAFJBVOV-UHFFFAOYSA-N n-cyclopropyl-4-(2-ethylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound CCC1=NN2N=CC=CC2=C1C(N=1)=CC=NC=1NC1CC1 RPRZAINAFJBVOV-UHFFFAOYSA-N 0.000 claims 1
- FAGYWTJBSZCMQC-UHFFFAOYSA-N n-cyclopropyl-4-(2-methylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound CC1=NN2N=CC=CC2=C1C(N=1)=CC=NC=1NC1CC1 FAGYWTJBSZCMQC-UHFFFAOYSA-N 0.000 claims 1
- RNTPQNNOOQMIBD-UHFFFAOYSA-N n-cyclopropyl-4-(6-ethenylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound C1=NN2N=C(C=C)C=CC2=C1C(N=1)=CC=NC=1NC1CC1 RNTPQNNOOQMIBD-UHFFFAOYSA-N 0.000 claims 1
- OJNPXUBDVGTOJJ-UHFFFAOYSA-N n-cyclopropyl-4-(6-methoxypyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound C1=NN2N=C(OC)C=CC2=C1C(N=1)=CC=NC=1NC1CC1 OJNPXUBDVGTOJJ-UHFFFAOYSA-N 0.000 claims 1
- RLKIXFRFDGFKOP-UHFFFAOYSA-N n-cyclopropyl-4-(6-morpholin-4-ylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound C1CC1NC1=NC=CC(C2=C3C=CC(=NN3N=C2)N2CCOCC2)=N1 RLKIXFRFDGFKOP-UHFFFAOYSA-N 0.000 claims 1
- PTXSJBYEFKLJDV-UHFFFAOYSA-N n-cyclopropyl-4-(6-phenylsulfanylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound C1CC1NC1=NC=CC(C2=C3C=CC(SC=4C=CC=CC=4)=NN3N=C2)=N1 PTXSJBYEFKLJDV-UHFFFAOYSA-N 0.000 claims 1
- MFBCYZQBHGCRST-UHFFFAOYSA-N n-cyclopropyl-4-(6-propan-2-yloxypyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound C1=NN2N=C(OC(C)C)C=CC2=C1C(N=1)=CC=NC=1NC1CC1 MFBCYZQBHGCRST-UHFFFAOYSA-N 0.000 claims 1
- DVNFZJOHZGRBGM-UHFFFAOYSA-N n-cyclopropyl-4-(6-pyrrolidin-1-ylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound C1CC1NC1=NC=CC(C2=C3C=CC(=NN3N=C2)N2CCCC2)=N1 DVNFZJOHZGRBGM-UHFFFAOYSA-N 0.000 claims 1
- ULKTXVYWINYRCP-UHFFFAOYSA-N n-cyclopropyl-4-(6-thiophen-2-ylpyrazolo[1,5-b]pyridazin-3-yl)pyrimidin-2-amine Chemical compound C1CC1NC1=NC=CC(C2=C3C=CC(=NN3N=C2)C=2SC=CC=2)=N1 ULKTXVYWINYRCP-UHFFFAOYSA-N 0.000 claims 1
- URAYKDQWSJUBED-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoropyridin-4-yl)pyrazolo[1,5-b]pyridazin-3-yl]pyrimidin-2-amine Chemical compound C1=NC(F)=CC(C2=NN3N=CC(=C3C=C2)C=2N=C(NC3CC3)N=CC=2)=C1 URAYKDQWSJUBED-UHFFFAOYSA-N 0.000 claims 1
- RVSCHTJBVVTPSV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)pyrazolo[1,5-b]pyridazin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NN2N=CC(C=3N=C(NC4CC4)N=CC=3)=C2C=C1 RVSCHTJBVVTPSV-UHFFFAOYSA-N 0.000 claims 1
- CAGHIASAHLPQMS-UHFFFAOYSA-N n-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound C1CC1NC1=NC=CC(C2=C3C=CC=NN3N=C2)=N1 CAGHIASAHLPQMS-UHFFFAOYSA-N 0.000 claims 1
- OAIXSJCARVACKE-UHFFFAOYSA-N n-cyclopropyl-n-methyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound N=1C=CC(C2=C3C=CC=NN3N=C2)=NC=1N(C)C1CC1 OAIXSJCARVACKE-UHFFFAOYSA-N 0.000 claims 1
- LIYXXFOSHNQSRD-UHFFFAOYSA-N n-phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine Chemical compound N=1C=CC(C2=C3C=CC=NN3N=C2)=NC=1NC1=CC=CC=C1 LIYXXFOSHNQSRD-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- XNSUDGUHSLGJCZ-UHFFFAOYSA-N pyrazolo[1,5-b]pyridazin-6-yl trifluoromethanesulfonate Chemical compound N1=CC=C2N1N=C(C=C2)OS(=O)(=O)C(F)(F)F XNSUDGUHSLGJCZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 1
- 0 C1N*C=CC(Nc2nccc(-c(cn3)c4[n]3nccc4)n2)=C1 Chemical compound C1N*C=CC(Nc2nccc(-c(cn3)c4[n]3nccc4)n2)=C1 0.000 description 2
- CQCMHIBXMLRGNH-UHFFFAOYSA-N CC1=CC2C=NNC2C=C1 Chemical compound CC1=CC2C=NNC2C=C1 CQCMHIBXMLRGNH-UHFFFAOYSA-N 0.000 description 1
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| ES2251677T3 (es) | 2002-01-22 | 2006-05-01 | Warner-Lambert Company Llc | 2-(piridin-2-ilamino)-pirido(2,3-d)pirimidin-7-onas. |
| EP1551842A1 (en) * | 2002-10-15 | 2005-07-13 | Smithkline Beecham Corporation | Pyradazine compounds as gsk-3 inhibitors |
| ATE412650T1 (de) * | 2003-07-11 | 2008-11-15 | Warner Lambert Co | Isethionat salz eines selektiven cdk4 inhibitors |
| DE10344223A1 (de) * | 2003-09-24 | 2005-04-21 | Merck Patent Gmbh | 1,3-Benzoxazolylderivate als Kinase-Inhibitoren |
| US7855205B2 (en) | 2004-10-29 | 2010-12-21 | Janssen Pharmaceutica Nv | Pyrimidinyl substituted fused-pyrrolyl compounds useful in treating kinase disorders |
| US7709468B2 (en) | 2005-09-02 | 2010-05-04 | Abbott Laboratories | Imidazo based heterocycles |
| CN101547917A (zh) * | 2006-12-08 | 2009-09-30 | 霍夫曼-拉罗奇有限公司 | 用作jnk调节剂的取代的嘧啶类化合物及它们的应用 |
| CA2707989A1 (en) | 2007-12-07 | 2009-06-11 | Novartis Ag | Pyrazole derivatives and use thereof as inhibitors of cyclin dependent kinases |
| US8309566B2 (en) | 2008-02-15 | 2012-11-13 | Rigel Pharmaceuticals, Inc. | Pyrimidine-2-amine compounds and their use as inhibitors of JAK kinases |
| CN102137672B (zh) * | 2008-06-30 | 2014-03-26 | 詹森药业有限公司 | 取代的嘧啶衍生物的制备方法 |
| AR074870A1 (es) * | 2008-12-24 | 2011-02-16 | Palau Pharma Sa | Derivados de pirazolo (1,5-a ) piridina |
| JP5959537B2 (ja) * | 2011-01-28 | 2016-08-02 | 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 | 置換ピリジニル−ピリミジン及び医薬としてのその使用 |
| US20150203812A1 (en) * | 2014-01-20 | 2015-07-23 | Francesco Tombola | Inhibitors of Voltage Gated Ion Channels |
| GB201605126D0 (en) * | 2016-03-24 | 2016-05-11 | Univ Nottingham | Inhibitors and their uses |
| CN106699608A (zh) * | 2016-12-26 | 2017-05-24 | 常州大学 | 一种含有强吸电子基团的苯胍及其盐的制备方法 |
| GB201715342D0 (en) * | 2017-09-22 | 2017-11-08 | Univ Nottingham | Compounds |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| WO2020180959A1 (en) | 2019-03-05 | 2020-09-10 | Incyte Corporation | Pyrazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| US11440914B2 (en) | 2019-05-01 | 2022-09-13 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| WO2020223558A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| CN114269742B (zh) * | 2019-07-10 | 2024-07-16 | 常州千红生化制药股份有限公司 | 作为治疗剂的4-(咪唑并[1,2-a]吡啶-3-基)-N-(吡啶基)嘧啶-2-胺的衍生物 |
| TW202115024A (zh) | 2019-08-14 | 2021-04-16 | 美商英塞特公司 | 作為cdk2 抑制劑之咪唑基嘧啶基胺化合物 |
| AU2020364007A1 (en) | 2019-10-11 | 2022-04-28 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| WO2023107705A1 (en) | 2021-12-10 | 2023-06-15 | Incyte Corporation | Bicyclic amines as cdk12 inhibitors |
| CN118005948B (zh) * | 2024-04-09 | 2024-06-28 | 蓝固(湖州)新能源科技有限公司 | 一种电解液添加剂及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU622330B2 (en) | 1989-06-23 | 1992-04-02 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides |
| CA2291709A1 (en) * | 1997-05-30 | 1998-12-03 | Merck & Co., Inc. | Novel angiogenesis inhibitors |
| ES2256817T3 (es) * | 1997-09-05 | 2006-07-16 | Glaxo Group Limited | Composiciones farmaceuticas que comprenden derivados de 2,3-diaril-pirazolo(1,5-b)piridazina. |
| AU3352899A (en) | 1997-12-11 | 1999-07-12 | American Home Products Corporation | 2,4,6-trisubstituted pyridines with estrogenic activity and methods for the solid phase synthesis thereof |
| GB9919778D0 (en) * | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| DE60018037T2 (de) | 1999-11-10 | 2006-01-12 | Ortho-Mcneil Pharmaceutical, Inc. | Substituierte 2-aryl-3-(heteroaryl)-imidazo[1,2-alpha]pyrimidine und ihren verwandten arzneimittel und verfahren |
| EP1317450B1 (en) | 2000-09-15 | 2006-11-22 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
-
2002
- 2002-12-11 AT AT02805104T patent/ATE323706T1/de not_active IP Right Cessation
- 2002-12-11 EP EP02805104A patent/EP1463730B1/en not_active Expired - Lifetime
- 2002-12-11 ES ES02805104T patent/ES2262899T3/es not_active Expired - Lifetime
- 2002-12-11 WO PCT/US2002/039672 patent/WO2003051886A1/en not_active Ceased
- 2002-12-11 US US10/499,179 patent/US7279473B2/en not_active Expired - Fee Related
- 2002-12-11 AU AU2002357164A patent/AU2002357164A1/en not_active Abandoned
- 2002-12-11 JP JP2003552768A patent/JP2005524609A/ja active Pending
- 2002-12-11 DE DE60210819T patent/DE60210819T2/de not_active Expired - Fee Related
- 2002-12-13 AR ARP020104845A patent/AR037826A1/es unknown
- 2002-12-13 TW TW091136132A patent/TW200301119A/zh unknown
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