JP2010516812A5 - - Google Patents
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- JP2010516812A5 JP2010516812A5 JP2009548286A JP2009548286A JP2010516812A5 JP 2010516812 A5 JP2010516812 A5 JP 2010516812A5 JP 2009548286 A JP2009548286 A JP 2009548286A JP 2009548286 A JP2009548286 A JP 2009548286A JP 2010516812 A5 JP2010516812 A5 JP 2010516812A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrazolo
- pyrimidin
- phenyl
- dihydro
- 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.)
- Withdrawn
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- -1 (methanesulfonyl) aminophenyl group Chemical group 0.000 claims description 307
- 150000001875 compounds Chemical class 0.000 claims description 108
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- 125000001072 heteroaryl group Chemical group 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 59
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 41
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 21
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 6
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 5
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- ZLFXBFWABAYPOQ-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CC2=CC=CC=C2C1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 ZLFXBFWABAYPOQ-UHFFFAOYSA-N 0.000 claims description 4
- IQAZMZNTCHBNLU-SFHVURJKSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@@H]3C4=CC=CC=C4CC3)N=CC2=CN=C1NC(C=C1)=CC=C1C1=NN=NN1 IQAZMZNTCHBNLU-SFHVURJKSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- YWWDYBTVVGBFFA-UHFFFAOYSA-N 4-[[1-(2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2C3C4=CC=CC=C4CC3)C2=N1 YWWDYBTVVGBFFA-UHFFFAOYSA-N 0.000 claims description 4
- IKFLZSZJGQUIPF-SFHVURJKSA-N 4-n-[1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 IKFLZSZJGQUIPF-SFHVURJKSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 4
- YWWDYBTVVGBFFA-SFHVURJKSA-N 4-[[1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 YWWDYBTVVGBFFA-SFHVURJKSA-N 0.000 claims description 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 102000001253 Protein Kinase Human genes 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical group C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 108060006633 protein kinase Proteins 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 2
- USLFQACRTBOMHH-UHFFFAOYSA-N 1-(1,2-dihydroacenaphthylen-1-yl)-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=12C3=CC=CC2=CC=CC=1CC3N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCNCC1 USLFQACRTBOMHH-UHFFFAOYSA-N 0.000 claims description 2
- YVDUPENJMTVWOZ-UHFFFAOYSA-N 1-(1,2-dihydroacenaphthylen-1-yl)-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=12C3=CC=CC2=CC=CC=1CC3N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1C1=NN=NN1 YVDUPENJMTVWOZ-UHFFFAOYSA-N 0.000 claims description 2
- ZCYWQIOEYYLIAJ-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CC2=CC=CC=C2C1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCNCC1 ZCYWQIOEYYLIAJ-UHFFFAOYSA-N 0.000 claims description 2
- IQAZMZNTCHBNLU-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CC2=CC=CC=C2C1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1C1=NN=NN1 IQAZMZNTCHBNLU-UHFFFAOYSA-N 0.000 claims description 2
- CMZPOHZDPDVHJR-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)-n-[4-[4-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]piperazin-1-yl]phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=C(C)C=NC(CN2CCN(CC2)C=2C=CC(NC=3N=C4N(C5C6=CC=CC=C6CC5)N=CC4=CN=3)=CC=2)=C1C CMZPOHZDPDVHJR-UHFFFAOYSA-N 0.000 claims description 2
- ZDYSIKQIHZXLNG-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1C2=CC=CC=C2CC1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 ZDYSIKQIHZXLNG-UHFFFAOYSA-N 0.000 claims description 2
- OWAQOFGRPRMDRC-XMMPIXPASA-N 1-[(1r)-1,2-dihydroacenaphthylen-1-yl]-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@@H]3CC=4C=CC=C5C=CC=C3C=45)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCOCC1 OWAQOFGRPRMDRC-XMMPIXPASA-N 0.000 claims description 2
- USLFQACRTBOMHH-XMMPIXPASA-N 1-[(1r)-1,2-dihydroacenaphthylen-1-yl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@@H]3CC=4C=CC=C5C=CC=C3C=45)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 USLFQACRTBOMHH-XMMPIXPASA-N 0.000 claims description 2
- ZCYWQIOEYYLIAJ-JOCHJYFZSA-N 1-[(1r)-2,3-dihydro-1h-inden-1-yl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@H]3C4=CC=CC=C4CC3)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 ZCYWQIOEYYLIAJ-JOCHJYFZSA-N 0.000 claims description 2
- IQAZMZNTCHBNLU-GOSISDBHSA-N 1-[(1r)-2,3-dihydro-1h-inden-1-yl]-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@H]3C4=CC=CC=C4CC3)N=CC2=CN=C1NC(C=C1)=CC=C1C1=NN=NN1 IQAZMZNTCHBNLU-GOSISDBHSA-N 0.000 claims description 2
- OWAQOFGRPRMDRC-DEOSSOPVSA-N 1-[(1s)-1,2-dihydroacenaphthylen-1-yl]-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@H]3CC=4C=CC=C5C=CC=C3C=45)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCOCC1 OWAQOFGRPRMDRC-DEOSSOPVSA-N 0.000 claims description 2
- USLFQACRTBOMHH-DEOSSOPVSA-N 1-[(1s)-1,2-dihydroacenaphthylen-1-yl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@H]3CC=4C=CC=C5C=CC=C3C=45)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 USLFQACRTBOMHH-DEOSSOPVSA-N 0.000 claims description 2
- ZLFXBFWABAYPOQ-QFIPXVFZSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@@H]3C4=CC=CC=C4CC3)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCOCC1 ZLFXBFWABAYPOQ-QFIPXVFZSA-N 0.000 claims description 2
- ZCYWQIOEYYLIAJ-QFIPXVFZSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@@H]3C4=CC=CC=C4CC3)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 ZCYWQIOEYYLIAJ-QFIPXVFZSA-N 0.000 claims description 2
- JDETXPDWBDCORH-VWLOTQADSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-[4-(4-propylsulfonylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(S(=O)(=O)CCC)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 JDETXPDWBDCORH-VWLOTQADSA-N 0.000 claims description 2
- ZUFKTYQSDJJFFZ-UHFFFAOYSA-N 1-[(6-fluoro-4h-1,3-benzodioxin-8-yl)methyl]-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=12OCOCC2=CC(F)=CC=1CN(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 ZUFKTYQSDJJFFZ-UHFFFAOYSA-N 0.000 claims description 2
- HTJZFHBHAKJNOX-UHFFFAOYSA-N 1-butyl-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N(CCCC)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 HTJZFHBHAKJNOX-UHFFFAOYSA-N 0.000 claims description 2
- ZKWBELIXZBEOLR-UHFFFAOYSA-N 1-methyl-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N(C)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 ZKWBELIXZBEOLR-UHFFFAOYSA-N 0.000 claims description 2
- ATCDJGOFGGIRGG-UHFFFAOYSA-N 1-naphthalen-1-yl-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N=1C=C2C=NN(C=3C4=CC=CC=C4C=CC=3)C2=NC=1NC(C=C1)=CC=C1C1=NN=NN1 ATCDJGOFGGIRGG-UHFFFAOYSA-N 0.000 claims description 2
- HBVZBYWIUNKDRD-UHFFFAOYSA-N 1-phenanthren-4-yl-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CNCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C4=C5C=CC=CC5=CC=C4C=CC=3)C2=N1 HBVZBYWIUNKDRD-UHFFFAOYSA-N 0.000 claims description 2
- RJVPRLSIBVLWLG-UHFFFAOYSA-N 1-phenanthren-4-yl-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N=1C=C2C=NN(C=3C4=C5C=CC=CC5=CC=C4C=CC=3)C2=NC=1NC(C=C1)=CC=C1C1=NN=NN1 RJVPRLSIBVLWLG-UHFFFAOYSA-N 0.000 claims description 2
- KZPFALGZBYHLEY-UHFFFAOYSA-N 2-methoxy-5-[(1-phenanthren-4-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C4=C5C=CC=CC5=CC=C4C=CC=3)C2=N1 KZPFALGZBYHLEY-UHFFFAOYSA-N 0.000 claims description 2
- SIGLJPGAPRIORG-UHFFFAOYSA-N 4-[(1-phenanthren-4-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2C=3C4=C5C=CC=CC5=CC=C4C=CC=3)C2=N1 SIGLJPGAPRIORG-UHFFFAOYSA-N 0.000 claims description 2
- STOCEKHCEZQVGG-UHFFFAOYSA-N 4-[[1-(1,2-dihydroacenaphthylen-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2C3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 STOCEKHCEZQVGG-UHFFFAOYSA-N 0.000 claims description 2
- DAPXDFMIJAUHPV-UHFFFAOYSA-N 4-[[1-(1,2-dihydroacenaphthylen-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NC1=NC=C(C=NN2C3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 DAPXDFMIJAUHPV-UHFFFAOYSA-N 0.000 claims description 2
- STOCEKHCEZQVGG-HXUWFJFHSA-N 4-[[1-[(1r)-1,2-dihydroacenaphthylen-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2[C@H]3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 STOCEKHCEZQVGG-HXUWFJFHSA-N 0.000 claims description 2
- YWWDYBTVVGBFFA-GOSISDBHSA-N 4-[[1-[(1r)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2[C@H]3C4=CC=CC=C4CC3)C2=N1 YWWDYBTVVGBFFA-GOSISDBHSA-N 0.000 claims description 2
- STOCEKHCEZQVGG-FQEVSTJZSA-N 4-[[1-[(1s)-1,2-dihydroacenaphthylen-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2[C@@H]3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 STOCEKHCEZQVGG-FQEVSTJZSA-N 0.000 claims description 2
- KREJOEYOMRAHHD-IBGZPJMESA-N 4-[[1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 KREJOEYOMRAHHD-IBGZPJMESA-N 0.000 claims description 2
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| CN118126043B (zh) * | 2022-12-02 | 2025-01-28 | 沈阳药科大学 | 一种高选择性的plk4抑制剂及制备方法和应用 |
| WO2024238570A1 (en) * | 2023-05-15 | 2024-11-21 | Aleksia Therapeutics, Inc. | Cdk2 inhibitor pyrazolopyrimidine compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA010160B1 (ru) * | 2003-09-18 | 2008-06-30 | Конформа Терапьютикс Корпорейшн | Новые гетероциклические соединения - ингибиторы hsp90 и способы их получения |
| JP2008513463A (ja) * | 2004-09-15 | 2008-05-01 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | チアゾロピリジンキナーゼ阻害剤 |
| ES2345997T3 (es) * | 2005-01-14 | 2010-10-07 | Janssen Pharmaceutica Nv | Pirazolopiramidinas como inhibidores de las quinasas del ciclo celular. |
| AU2006205851A1 (en) * | 2005-01-14 | 2006-07-20 | Janssen Pharmaceutica N.V. | 5-membered annelated heterocyclic pyrimidines as kinase inhibitors |
| WO2006091737A1 (en) * | 2005-02-24 | 2006-08-31 | Kemia, Inc. | Modulators of gsk-3 activity |
| WO2008094575A2 (en) * | 2007-01-30 | 2008-08-07 | Biogen Idec Ma Inc. | 1-h-pyrazolo(3,4b)pyrimidine derivatives and their use as modulators of mitotic kinases |
-
2008
- 2008-01-30 WO PCT/US2008/001195 patent/WO2008094575A2/en not_active Ceased
- 2008-01-30 JP JP2009548293A patent/JP2010532312A/ja not_active Withdrawn
- 2008-01-30 US US12/525,174 patent/US20110281821A9/en not_active Abandoned
- 2008-01-30 JP JP2009548286A patent/JP2010516812A/ja not_active Withdrawn
- 2008-01-30 WO PCT/US2008/001230 patent/WO2008094602A2/en not_active Ceased
- 2008-01-30 AU AU2008211172A patent/AU2008211172A1/en not_active Abandoned
- 2008-01-30 EP EP08724974A patent/EP2108020A2/en not_active Withdrawn
- 2008-01-30 US US12/525,155 patent/US20100190787A1/en not_active Abandoned
- 2008-01-30 CA CA002676658A patent/CA2676658A1/en not_active Abandoned
- 2008-01-30 EP EP08724941A patent/EP2108019A2/en not_active Withdrawn
- 2008-01-30 CA CA002676665A patent/CA2676665A1/en not_active Abandoned
- 2008-01-30 AU AU2008211108A patent/AU2008211108A1/en not_active Abandoned
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