JP2008519790A5 - - Google Patents
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- JP2008519790A5 JP2008519790A5 JP2007540577A JP2007540577A JP2008519790A5 JP 2008519790 A5 JP2008519790 A5 JP 2008519790A5 JP 2007540577 A JP2007540577 A JP 2007540577A JP 2007540577 A JP2007540577 A JP 2007540577A JP 2008519790 A5 JP2008519790 A5 JP 2008519790A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyrazolo
- amine
- pyrimidin
- methyl
- 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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- -1 (5-fluoro-2-methyl-phenyl)-[1- ( 4-methoxy - phenyl) -1H- pyrazolo [3,4-d] pyrimidin-4-yl] Chemical class 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 12
- 150000002431 hydrogen Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 125000003107 substituted aryl group Chemical group 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 102000050554 Eph Family Receptors Human genes 0.000 claims 2
- 108091008815 Eph receptors Proteins 0.000 claims 2
- 102000001253 Protein Kinase Human genes 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
- 108060006633 protein kinase Proteins 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- PTAVYJBCZAPEBZ-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-(2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)=C1 PTAVYJBCZAPEBZ-UHFFFAOYSA-N 0.000 claims 1
- LXHHJLJPJDCURN-UHFFFAOYSA-N 1-(4-bromophenyl)-n-(2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC=C1NC1=NC=NC2=C1C=NN2C1=CC=C(Br)C=C1 LXHHJLJPJDCURN-UHFFFAOYSA-N 0.000 claims 1
- NEVKWSNYPQZDQX-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC=NC(NC=3C(=CC=CC=3)C)=C2C=N1 NEVKWSNYPQZDQX-UHFFFAOYSA-N 0.000 claims 1
- PLCARNJOQDDPQG-UHFFFAOYSA-N 1-[4-(4-methyl-1,4-diazepan-1-yl)phenyl]-n-(2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=C1 PLCARNJOQDDPQG-UHFFFAOYSA-N 0.000 claims 1
- KYWKYEDMARGTEE-HXUWFJFHSA-N 1-[4-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]-n-(2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=C1 KYWKYEDMARGTEE-HXUWFJFHSA-N 0.000 claims 1
- TVWFORVJOUCMDU-OAQYLSRUSA-N 1-[4-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]-n-(4-fluoro-2,6-dimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4C)C)=C3C=N2)C=C1 TVWFORVJOUCMDU-OAQYLSRUSA-N 0.000 claims 1
- QPKJZZHUKMYDIO-HXUWFJFHSA-N 1-[4-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]-n-(4-fluoro-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4)C)=C3C=N2)C=C1 QPKJZZHUKMYDIO-HXUWFJFHSA-N 0.000 claims 1
- XOPGFBHSOGPXQT-HXUWFJFHSA-N 1-[4-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]-n-(5-fluoro-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=C(F)C=4)C)=C3C=N2)C=C1 XOPGFBHSOGPXQT-HXUWFJFHSA-N 0.000 claims 1
- KYWKYEDMARGTEE-FQEVSTJZSA-N 1-[4-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]-n-(2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=C1 KYWKYEDMARGTEE-FQEVSTJZSA-N 0.000 claims 1
- TVWFORVJOUCMDU-NRFANRHFSA-N 1-[4-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]-n-(4-fluoro-2,6-dimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4C)C)=C3C=N2)C=C1 TVWFORVJOUCMDU-NRFANRHFSA-N 0.000 claims 1
- QPKJZZHUKMYDIO-FQEVSTJZSA-N 1-[4-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]-n-(4-fluoro-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4)C)=C3C=N2)C=C1 QPKJZZHUKMYDIO-FQEVSTJZSA-N 0.000 claims 1
- XOPGFBHSOGPXQT-FQEVSTJZSA-N 1-[4-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]-n-(5-fluoro-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=C(F)C=4)C)=C3C=N2)C=C1 XOPGFBHSOGPXQT-FQEVSTJZSA-N 0.000 claims 1
- FKRGQBZIHSRPKD-UHFFFAOYSA-N 1-[4-[4-(diethylamino)piperidin-1-yl]phenyl]-n-(2,6-dimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(N(CC)CC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4C)C)=C3C=N2)C=C1 FKRGQBZIHSRPKD-UHFFFAOYSA-N 0.000 claims 1
- NKNNXEPJAFOPLG-UHFFFAOYSA-N 1-[4-[4-(diethylamino)piperidin-1-yl]phenyl]-n-(2-methylphenyl)-6-phenylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(N(CC)CC)CCN1C1=CC=C(N2C3=NC(=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=2C=CC=CC=2)C=C1 NKNNXEPJAFOPLG-UHFFFAOYSA-N 0.000 claims 1
- STTLIMCCZAVEAI-UHFFFAOYSA-N 1-[4-[4-(diethylamino)piperidin-1-yl]phenyl]-n-(2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(N(CC)CC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=C1 STTLIMCCZAVEAI-UHFFFAOYSA-N 0.000 claims 1
- VVPCINGESYBUDF-UHFFFAOYSA-N 1-[4-[4-(diethylamino)piperidin-1-yl]phenyl]-n-(4-fluoro-2,6-dimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(N(CC)CC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4C)C)=C3C=N2)C=C1 VVPCINGESYBUDF-UHFFFAOYSA-N 0.000 claims 1
- NUKNJGLEYMGNLO-UHFFFAOYSA-N 1-[4-[4-(diethylamino)piperidin-1-yl]phenyl]-n-(4-fluoro-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical class C1CC(N(CC)CC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4)C)=C3C=N2)C=C1 NUKNJGLEYMGNLO-UHFFFAOYSA-N 0.000 claims 1
- RAIDNOWHKFNFBB-UHFFFAOYSA-N 1-[4-[4-(diethylamino)piperidin-1-yl]phenyl]-n-(5-fluoro-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical class C1CC(N(CC)CC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=C(F)C=4)C)=C3C=N2)C=C1 RAIDNOWHKFNFBB-UHFFFAOYSA-N 0.000 claims 1
- XVUXZMNJKZLDKD-UHFFFAOYSA-N 1-[4-[4-(dipropylamino)piperidin-1-yl]phenyl]-n-(2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(N(CCC)CCC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=C1 XVUXZMNJKZLDKD-UHFFFAOYSA-N 0.000 claims 1
- KYOZWCSXZJWVLH-UHFFFAOYSA-N 1-[4-[4-(dipropylamino)piperidin-1-yl]phenyl]-n-(4-fluoro-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(N(CCC)CCC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4)C)=C3C=N2)C=C1 KYOZWCSXZJWVLH-UHFFFAOYSA-N 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical class NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- PECBBVVSFRZZQH-UHFFFAOYSA-N 6-[3-(dimethylamino)propyl]-n-(2,6-dimethylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=12C=NN(C=3C=CC=CC=3)C2=NC(CCCN(C)C)=NC=1NC1=C(C)C=CC=C1C PECBBVVSFRZZQH-UHFFFAOYSA-N 0.000 claims 1
- SWJUELRUGYLLPX-UHFFFAOYSA-N 6-[3-(dimethylamino)propyl]-n-(2-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=12C=NN(C=3C=CC=CC=3)C2=NC(CCCN(C)C)=NC=1NC1=CC=CC=C1C SWJUELRUGYLLPX-UHFFFAOYSA-N 0.000 claims 1
- LRSPQPJJXJVMGW-UHFFFAOYSA-N 6-methyl-n-(2-methylphenyl)-1-[3-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC=CC(N2C3=NC(C)=NC(NC=4C(=CC=CC=4)C)=C3C=N2)=C1 LRSPQPJJXJVMGW-UHFFFAOYSA-N 0.000 claims 1
- CMNDCBIFZSELPL-UHFFFAOYSA-N 6-methyl-n-(2-methylphenyl)-1-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC=C(N2C3=NC(C)=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=C1 CMNDCBIFZSELPL-UHFFFAOYSA-N 0.000 claims 1
- NGDTXTYEHLAOFU-UHFFFAOYSA-N 6-methyl-n-(2-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC=C1NC1=NC(C)=NC2=C1C=NN2C1=CC=CC=C1 NGDTXTYEHLAOFU-UHFFFAOYSA-N 0.000 claims 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 241000023320 Luma <angiosperm> Species 0.000 claims 1
- 108700020796 Oncogene Proteins 0.000 claims 1
- 108010058765 Oncogene Protein pp60(v-src) Proteins 0.000 claims 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 1
- 108700020978 Proto-Oncogene Proteins 0.000 claims 1
- 102000052575 Proto-Oncogene Human genes 0.000 claims 1
- 102000001332 SRC Human genes 0.000 claims 1
- 108060006706 SRC Proteins 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- HSQBWCUIAJYDBO-UHFFFAOYSA-N n',n'-dimethyl-n-[4-[4-(2-methylanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenyl]ethane-1,2-diamine Chemical compound C1=CC(NCCN(C)C)=CC=C1N1C2=NC=NC(NC=3C(=CC=CC=3)C)=C2C=N1 HSQBWCUIAJYDBO-UHFFFAOYSA-N 0.000 claims 1
- UJABTMNLNHAXGJ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(N2C3=NC=NC(NC=4C(=CC=CC=4C)C)=C3C=N2)=C1 UJABTMNLNHAXGJ-UHFFFAOYSA-N 0.000 claims 1
- YCVUOIXNXLTWDT-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC=NC(NC=3C(=CC=CC=3C)C)=C2C=N1 YCVUOIXNXLTWDT-UHFFFAOYSA-N 0.000 claims 1
- ANYQRKAGBILOFB-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-[3-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC=CC(N2C3=NC=NC(NC=4C(=CC=CC=4C)C)=C3C=N2)=C1 ANYQRKAGBILOFB-UHFFFAOYSA-N 0.000 claims 1
- UYZYWKQEPGKFSS-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4C)C)=C3C=N2)C=C1 UYZYWKQEPGKFSS-UHFFFAOYSA-N 0.000 claims 1
- YZSCAIVAROZMMD-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-[4-(4-morpholin-4-ylpiperidin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(C)=C1NC1=NC=NC2=C1C=NN2C1=CC=C(N2CCC(CC2)N2CCOCC2)C=C1 YZSCAIVAROZMMD-UHFFFAOYSA-N 0.000 claims 1
- YHOOFFGHGKFSSD-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-[4-(4-pyrrolidin-1-ylpiperidin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(C)=C1NC1=NC=NC2=C1C=NN2C1=CC=C(N2CCC(CC2)N2CCCC2)C=C1 YHOOFFGHGKFSSD-UHFFFAOYSA-N 0.000 claims 1
- VBPYYEWVIMVIDY-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-[4-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCC1N1CCN(C=2C=CC(=CC=2)N2C3=NC=NC(NC=4C(=CC=CC=4C)C)=C3C=N2)CC1 VBPYYEWVIMVIDY-UHFFFAOYSA-N 0.000 claims 1
- UFRSWHYPQXDDPS-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(=CC=2)N2C3=NC=NC(NC=4C(=CC=CC=4C)C)=C3C=N2)CC1 UFRSWHYPQXDDPS-UHFFFAOYSA-N 0.000 claims 1
- QOBJRAZZQPHTOL-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-[4-[4-(dipropylamino)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical class C1CC(N(CCC)CCC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4C)C)=C3C=N2)C=C1 QOBJRAZZQPHTOL-UHFFFAOYSA-N 0.000 claims 1
- FVWWCUNNHUPEJA-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)-1-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical class C1CN(C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3C=N2)C=C1 FVWWCUNNHUPEJA-UHFFFAOYSA-N 0.000 claims 1
- UTRRBNFCMUJPQL-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)-1-[4-(4-pyrrolidin-1-ylpiperidin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound ClC1=CC(F)=CC=C1NC1=NC=NC2=C1C=NN2C1=CC=C(N2CCC(CC2)N2CCCC2)C=C1 UTRRBNFCMUJPQL-UHFFFAOYSA-N 0.000 claims 1
- RZBHKDAWWCLQPS-GOSISDBHSA-N n-(2-chloro-4-fluorophenyl)-1-[4-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3C=N2)C=C1 RZBHKDAWWCLQPS-GOSISDBHSA-N 0.000 claims 1
- RZBHKDAWWCLQPS-SFHVURJKSA-N n-(2-chloro-4-fluorophenyl)-1-[4-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3C=N2)C=C1 RZBHKDAWWCLQPS-SFHVURJKSA-N 0.000 claims 1
- NAFKUFNOOOUZBN-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)-1-[4-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCC1N1CCN(C=2C=CC(=CC=2)N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3C=N2)CC1 NAFKUFNOOOUZBN-UHFFFAOYSA-N 0.000 claims 1
- YEUDAUHMFOJYLH-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)-1-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(=CC=2)N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3C=N2)CC1 YEUDAUHMFOJYLH-UHFFFAOYSA-N 0.000 claims 1
- BKWVXGSPYTVBRY-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)-1-[4-[4-(diethylamino)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical class C1CC(N(CC)CC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3C=N2)C=C1 BKWVXGSPYTVBRY-UHFFFAOYSA-N 0.000 claims 1
- SGPGVTVJNXCJCB-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)-1-[4-[4-(dipropylamino)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(N(CCC)CCC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3C=N2)C=C1 SGPGVTVJNXCJCB-UHFFFAOYSA-N 0.000 claims 1
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- ZUJDUUOCTNUSJL-UHFFFAOYSA-N n-(2-chlorophenyl)-1-[4-(4-pyrrolidin-1-ylpiperidin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical class ClC1=CC=CC=C1NC1=NC=NC2=C1C=NN2C1=CC=C(N2CCC(CC2)N2CCCC2)C=C1 ZUJDUUOCTNUSJL-UHFFFAOYSA-N 0.000 claims 1
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- XNKULWFUYYBOLC-UHFFFAOYSA-N n-(2-chlorophenyl)-1-[4-[4-(diethylamino)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(N(CC)CC)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4)Cl)=C3C=N2)C=C1 XNKULWFUYYBOLC-UHFFFAOYSA-N 0.000 claims 1
- RDGQWIAJWKAICW-UHFFFAOYSA-N n-(2-chlorophenyl)-6-[3-(dimethylamino)propyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=12C=NN(C=3C=CC=CC=3)C2=NC(CCCN(C)C)=NC=1NC1=CC=CC=C1Cl RDGQWIAJWKAICW-UHFFFAOYSA-N 0.000 claims 1
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- VLHYAENDGCNZES-UHFFFAOYSA-N n-(2-methylphenyl)-1-[3-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC=CC(N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)=C1 VLHYAENDGCNZES-UHFFFAOYSA-N 0.000 claims 1
- QCTWASNVDUUTSQ-UHFFFAOYSA-N n-(2-methylphenyl)-1-[3-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=C(C=CC=2)N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)CC1 QCTWASNVDUUTSQ-UHFFFAOYSA-N 0.000 claims 1
- YCSPLANNUDMEGK-UHFFFAOYSA-N n-(2-methylphenyl)-1-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC=C(N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=C1 YCSPLANNUDMEGK-UHFFFAOYSA-N 0.000 claims 1
- ZRLPORAOJNMUPC-UHFFFAOYSA-N n-(2-methylphenyl)-1-[4-(4-morpholin-4-ylpiperidin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC=C1NC1=NC=NC2=C1C=NN2C1=CC=C(N2CCC(CC2)N2CCOCC2)C=C1 ZRLPORAOJNMUPC-UHFFFAOYSA-N 0.000 claims 1
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- RLYARYDCULMKSD-UHFFFAOYSA-N n-(2-methylphenyl)-1-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-6-pyridin-2-ylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(=CC=2)N2C3=NC(=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=2N=CC=CC=2)CC1 RLYARYDCULMKSD-UHFFFAOYSA-N 0.000 claims 1
- GVLORRVCMXALGM-UHFFFAOYSA-N n-(2-methylphenyl)-1-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-6-pyridin-3-ylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(=CC=2)N2C3=NC(=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=2C=NC=CC=2)CC1 GVLORRVCMXALGM-UHFFFAOYSA-N 0.000 claims 1
- ZSTLFNOOIQTRNB-UHFFFAOYSA-N n-(2-methylphenyl)-1-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-6-pyridin-4-ylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(=CC=2)N2C3=NC(=NC(NC=4C(=CC=CC=4)C)=C3C=N2)C=2C=CN=CC=2)CC1 ZSTLFNOOIQTRNB-UHFFFAOYSA-N 0.000 claims 1
- YSUBOPZXMFDLMU-UHFFFAOYSA-N n-(2-methylphenyl)-1-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(=CC=2)N2C3=NC=NC(NC=4C(=CC=CC=4)C)=C3C=N2)CC1 YSUBOPZXMFDLMU-UHFFFAOYSA-N 0.000 claims 1
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- ZZGIVWGKIJQGHA-UHFFFAOYSA-N n-(4-fluoro-2,6-dimethylphenyl)-1-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(=CC=2)N2C3=NC=NC(NC=4C(=CC(F)=CC=4C)C)=C3C=N2)CC1 ZZGIVWGKIJQGHA-UHFFFAOYSA-N 0.000 claims 1
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- LZNTVOYYLFPVBT-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-1-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(=CC=2)N2C3=NC=NC(NC=4C(=CC(F)=CC=4)C)=C3C=N2)CC1 LZNTVOYYLFPVBT-UHFFFAOYSA-N 0.000 claims 1
- JZIPHIZYKZEJPD-UHFFFAOYSA-N n-(5-fluoro-2-methylphenyl)-1-[4-(4-pyrrolidin-1-ylpiperidin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=C(F)C=C1NC1=NC=NC2=C1C=NN2C1=CC=C(N2CCC(CC2)N2CCCC2)C=C1 JZIPHIZYKZEJPD-UHFFFAOYSA-N 0.000 claims 1
- RJXCZVROVZWQDA-UHFFFAOYSA-N n-(5-fluoro-2-methylphenyl)-1-[4-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCC1N1CCN(C=2C=CC(=CC=2)N2C3=NC=NC(NC=4C(=CC=C(F)C=4)C)=C3C=N2)CC1 RJXCZVROVZWQDA-UHFFFAOYSA-N 0.000 claims 1
- FFAHMHOPDUXBCP-UHFFFAOYSA-N n-(5-fluoro-2-methylphenyl)-1-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(=CC=2)N2C3=NC=NC(NC=4C(=CC=C(F)C=4)C)=C3C=N2)CC1 FFAHMHOPDUXBCP-UHFFFAOYSA-N 0.000 claims 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200400034A (en) * | 2002-05-20 | 2004-01-01 | Bristol Myers Squibb Co | Pyrazolo-pyrimidine aniline compounds useful as kinase inhibitors |
| EP1523314A2 (en) * | 2002-07-23 | 2005-04-20 | SmithKline Beecham Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| JP2007210887A (ja) * | 2004-06-21 | 2007-08-23 | Astellas Pharma Inc | 縮合二環性ピリミジン誘導体 |
-
2004
- 2004-11-12 GB GB0425035A patent/GB0425035D0/en not_active Ceased
-
2005
- 2005-11-08 GT GT200500325A patent/GT200500325A/es unknown
- 2005-11-10 CN CNA2005800464109A patent/CN101098873A/zh active Pending
- 2005-11-10 US US11/718,730 patent/US20080096868A1/en not_active Abandoned
- 2005-11-10 RU RU2007121846/04A patent/RU2007121846A/ru not_active Application Discontinuation
- 2005-11-10 MX MX2007005644A patent/MX2007005644A/es not_active Application Discontinuation
- 2005-11-10 WO PCT/EP2005/012045 patent/WO2006050946A1/en not_active Ceased
- 2005-11-10 AU AU2005303965A patent/AU2005303965A1/en not_active Abandoned
- 2005-11-10 BR BRPI0517803-7A patent/BRPI0517803A/pt not_active IP Right Cessation
- 2005-11-10 EP EP05819276A patent/EP1812441A1/en not_active Withdrawn
- 2005-11-10 KR KR1020077010778A patent/KR20070084191A/ko not_active Withdrawn
- 2005-11-10 JP JP2007540577A patent/JP2008519790A/ja active Pending
- 2005-11-10 CA CA002585660A patent/CA2585660A1/en not_active Abandoned
- 2005-11-11 TW TW094139701A patent/TW200621783A/zh unknown
- 2005-11-11 AR ARP050104725A patent/AR051485A1/es not_active Application Discontinuation
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