JP2010516812A - 有糸分裂キナーゼの調節剤 - Google Patents

Info

Publication number

JP2010516812A

JP2010516812A JP2009548286A JP2009548286A JP2010516812A JP 2010516812 A JP2010516812 A JP 2010516812A JP 2009548286 A JP2009548286 A JP 2009548286A JP 2009548286 A JP2009548286 A JP 2009548286A JP 2010516812 A JP2010516812 A JP 2010516812A

Authority

JP

Japan

Prior art keywords

group

pyrazolo

pyrimidin

phenyl

dihydro

Prior art date

2007-01-30

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Withdrawn

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• 108091000080 Phosphotransferase Proteins 0.000 title abstract description 12
• 230000000394 mitotic effect Effects 0.000 title abstract description 12
• 102000020233 phosphotransferase Human genes 0.000 title abstract description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 269
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 47
• 201000011510 cancer Diseases 0.000 claims abstract description 20
• 230000011278 mitosis Effects 0.000 claims abstract description 17
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
• 150000003839 salts Chemical class 0.000 claims abstract description 11
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 8
• 108060006633 protein kinase Proteins 0.000 claims abstract description 8
• 229940002612 prodrug Drugs 0.000 claims abstract description 7
• 239000000651 prodrug Substances 0.000 claims abstract description 7
• 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 abstract description 4
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 3
• 239000012453 solvate Substances 0.000 claims abstract 2
• -1 (methanesulfonyl) aminophenyl group Chemical group 0.000 claims description 449
• 125000001072 heteroaryl group Chemical group 0.000 claims description 164
• 125000003118 aryl group Chemical group 0.000 claims description 156
• 125000000217 alkyl group Chemical group 0.000 claims description 136
• 238000000034 method Methods 0.000 claims description 109
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 97
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 91
• 125000001424 substituent group Chemical group 0.000 claims description 84
• 229910052739 hydrogen Inorganic materials 0.000 claims description 71
• 239000001257 hydrogen Substances 0.000 claims description 71
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 64
• 150000002431 hydrogen Chemical class 0.000 claims description 53
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 49
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 40
• 125000003342 alkenyl group Chemical group 0.000 claims description 38
• 125000000304 alkynyl group Chemical group 0.000 claims description 34
• 125000003277 amino group Chemical group 0.000 claims description 32
• 125000005843 halogen group Chemical group 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
• 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 20
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
• 125000004043 oxo group Chemical group O=* 0.000 claims description 20
• 125000006413 ring segment Chemical group 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 16
• 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 15
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 15
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 14
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
• 125000001624 naphthyl group Chemical group 0.000 claims description 12
• 102000003989 Aurora kinases Human genes 0.000 claims description 11
• 108090000433 Aurora kinases Proteins 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 11
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 11
• 238000011282 treatment Methods 0.000 claims description 11
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 10
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 10
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• 125000004001 thioalkyl group Chemical group 0.000 claims description 9
• 101000582926 Dictyostelium discoideum Probable serine/threonine-protein kinase PLK Proteins 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 7
• 108091005804 Peptidases Proteins 0.000 claims description 7
• 239000004365 Protease Substances 0.000 claims description 7
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
• 208000032839 leukemia Diseases 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 239000005711 Benzoic acid Substances 0.000 claims description 6
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000001041 indolyl group Chemical group 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
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 230000003834 intracellular effect Effects 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
• 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 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
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 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
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
• OWAQOFGRPRMDRC-UHFFFAOYSA-N 1-(1,2-dihydroacenaphthylen-1-yl)-n-(4-morpholin-4-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=C1N1CCOCC1 OWAQOFGRPRMDRC-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 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 3
• 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
• 206010009944 Colon cancer Diseases 0.000 claims description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
• 201000005202 lung cancer Diseases 0.000 claims description 3
• 208000020816 lung neoplasm Diseases 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• SMIKNYWLKWJEOC-UHFFFAOYSA-N n-[4-[(1-phenanthren-4-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C=3C4=C5C=CC=CC5=CC=C4C=CC=3)C2=N1 SMIKNYWLKWJEOC-UHFFFAOYSA-N 0.000 claims description 3
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 3
• 201000000849 skin cancer Diseases 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
• 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
• ZJIJSTNBCKPMOY-UHFFFAOYSA-N 1-(1h-indol-4-yl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C=4C=CNC=4C=CC=3)C2=N1 ZJIJSTNBCKPMOY-UHFFFAOYSA-N 0.000 claims description 2
• JZZRFGFZNCMSEW-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)-n-(3-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CC2=CC=CC=C2C1N(C1=N2)N=CC1=CN=C2NC(C=1)=CC=CC=1N1CCNCC1 JZZRFGFZNCMSEW-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
• 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
• DVEWUYYKNPUDCY-QHCPKHFHSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 DVEWUYYKNPUDCY-QHCPKHFHSA-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
• OYFXQQXMGDPNIR-UHFFFAOYSA-N 1-[6-(4-aminoanilino)pyrazolo[3,4-d]pyrimidin-1-yl]-2,3-dihydro-1h-inden-4-ol Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=C4)O)CC3)C2=N1 OYFXQQXMGDPNIR-UHFFFAOYSA-N 0.000 claims description 2
• DUYVDLCXTYYWPT-UHFFFAOYSA-N 1-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrazolo[3,4-d]pyrimidin-1-yl]-2,3-dihydro-1h-inden-4-ol Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=C4)O)CC3)C2=N1 DUYVDLCXTYYWPT-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
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
• HCIUUKLTOVMGFV-UHFFFAOYSA-N 4-[6-(4-morpholin-4-ylanilino)pyrazolo[3,4-d]pyrimidin-1-yl]-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1=2CCCCC=2C(O)=CC=C1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 HCIUUKLTOVMGFV-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
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