CA2676658A1 - Modulators of mitotic kinases - Google Patents

Info

Publication number

CA2676658A1

CA2676658A1 CA002676658A CA2676658A CA2676658A1 CA 2676658 A1 CA2676658 A1 CA 2676658A1 CA 002676658 A CA002676658 A CA 002676658A CA 2676658 A CA2676658 A CA 2676658A CA 2676658 A1 CA2676658 A1 CA 2676658A1

Authority

CA

Canada

Prior art keywords

pyrazolo

pyrimidin

phenyl

dihydro

ylamino

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 108091000080 Phosphotransferase Proteins 0.000 title description 15
• 102000020233 phosphotransferase Human genes 0.000 title description 15
• 230000000394 mitotic effect Effects 0.000 title description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 268
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
• 230000011278 mitosis Effects 0.000 claims abstract description 13
• 150000003839 salts Chemical class 0.000 claims abstract description 12
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 8
• 108060006633 protein kinase Proteins 0.000 claims abstract description 7
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 4
• 239000012453 solvate Substances 0.000 claims abstract description 3
• -1 amino, hydroxy Chemical group 0.000 claims description 280
• 125000001072 heteroaryl group Chemical group 0.000 claims description 154
• 125000003118 aryl group Chemical group 0.000 claims description 152
• 125000000217 alkyl group Chemical group 0.000 claims description 129
• 238000000034 method Methods 0.000 claims description 110
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 89
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 89
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
• 125000001424 substituent group Chemical group 0.000 claims description 75
• 229910052739 hydrogen Inorganic materials 0.000 claims description 73
• 239000001257 hydrogen Substances 0.000 claims description 73
• 150000002431 hydrogen Chemical class 0.000 claims description 53
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 48
• 206010028980 Neoplasm Diseases 0.000 claims description 40
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 39
• 125000003342 alkenyl group Chemical group 0.000 claims description 37
• 125000000304 alkynyl group Chemical group 0.000 claims description 34
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 21
• 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 20
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000006413 ring segment Chemical group 0.000 claims description 18
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 15
• 201000011510 cancer Diseases 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 14
• 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 13
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 13
• 101000582926 Dictyostelium discoideum Probable serine/threonine-protein kinase PLK Proteins 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
• 201000010099 disease Diseases 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000000392 cycloalkenyl group Chemical group 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
• 239000005711 Benzoic acid Substances 0.000 claims description 8
• 229960004365 benzoic acid Drugs 0.000 claims description 8
• 125000004366 heterocycloalkenyl group Chemical group 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
• 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
• 229940002612 prodrug Drugs 0.000 claims description 7
• 239000000651 prodrug Substances 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
• 235000010233 benzoic acid Nutrition 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
• 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
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 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 4
• 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
• 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
• 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 4
• SKGSQBQCAXCKMQ-UHFFFAOYSA-N 4-n-(1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 SKGSQBQCAXCKMQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 208000032839 leukemia Diseases 0.000 claims description 4
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• ZZOBDJYOOUOHAJ-UHFFFAOYSA-N n-[4-[[1-(1,2-dihydroacenaphthylen-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 ZZOBDJYOOUOHAJ-UHFFFAOYSA-N 0.000 claims description 4
• QXEHIYNVSKICIT-UHFFFAOYSA-N n-[4-[[1-(2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=CC=CC=C4CC3)C2=N1 QXEHIYNVSKICIT-UHFFFAOYSA-N 0.000 claims description 4
• DUDXVUVSQOFKMJ-FQEVSTJZSA-N n-[4-[[1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 DUDXVUVSQOFKMJ-FQEVSTJZSA-N 0.000 claims description 4
• REVKUCDZNKPRTC-UHFFFAOYSA-N n-methyl-n-[4-[(1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]methanesulfonamide Chemical compound C1=CC(N(C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 REVKUCDZNKPRTC-UHFFFAOYSA-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
• 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-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
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-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
• UFHZUUWMQXZORL-UHFFFAOYSA-N 4-n-[1-(1,2-dihydroacenaphthylen-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 UFHZUUWMQXZORL-UHFFFAOYSA-N 0.000 claims description 3
• IKFLZSZJGQUIPF-UHFFFAOYSA-N 4-n-[1-(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=NN2C3C4=CC=CC=C4CC3)C2=N1 IKFLZSZJGQUIPF-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• BKCXYALESKTFTD-KRWDZBQOSA-N 5-[[1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 BKCXYALESKTFTD-KRWDZBQOSA-N 0.000 claims description 3
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
• 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 201000005202 lung cancer Diseases 0.000 claims description 3
• 208000020816 lung neoplasm Diseases 0.000 claims description 3
• 208000029559 malignant endocrine neoplasm Diseases 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• QBECDZFLAGRGKR-UHFFFAOYSA-N n-methylsulfonyl-n-[4-[(1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]methanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 QBECDZFLAGRGKR-UHFFFAOYSA-N 0.000 claims description 3
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 3
• DWGYXMNXEFQAJG-UHFFFAOYSA-N 1-(1,2-dihydroacenaphthylen-1-yl)-n-[4-(2-trimethylstannyltetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C[Sn](C)(C)N1N=NC(C=2C=CC(NC=3N=C4N(C5C=6C=CC=C7C=CC=C(C=67)C5)N=CC4=CN=3)=CC=2)=N1 DWGYXMNXEFQAJG-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
• GOSVAUXUVQRGFY-UHFFFAOYSA-N 1-(1,2-dihydroacenaphthylen-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=NN2C3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 GOSVAUXUVQRGFY-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
• 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 2
• JDETXPDWBDCORH-UHFFFAOYSA-N 1-(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=NN2C3C4=CC=CC=C4CC3)C2=N1 JDETXPDWBDCORH-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
• NYVOBTUFNXUIBR-UHFFFAOYSA-N 1-(7-methyl-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(C)=CC=3)C2=N1 NYVOBTUFNXUIBR-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
• YVDUPENJMTVWOZ-HXUWFJFHSA-N 1-[(1r)-1,2-dihydroacenaphthylen-1-yl]-n-[4-(2h-tetrazol-5-yl)phenyl]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=C1C1=NN=NN1 YVDUPENJMTVWOZ-HXUWFJFHSA-N 0.000 claims description 2
• ZLFXBFWABAYPOQ-JOCHJYFZSA-N 1-[(1r)-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-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
• 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
• CSHMUOIYRRXBTL-URLMMPGGSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-[3-[1-[(1r)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]oxy-4-methoxyphenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CC2=CC=CC=C2[C@@H]1N(C1=N2)N=CC1=CN=C2OC1=CC(NC=2N=C3N([C@@H]4C5=CC=CC=C5CC4)N=CC3=CN=2)=CC=C1OC CSHMUOIYRRXBTL-URLMMPGGSA-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
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• BKMZSODKONWOJO-FQEVSTJZSA-N ethyl 4-[[1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 BKMZSODKONWOJO-FQEVSTJZSA-N 0.000 claims description 2
• BLINRMNNGNVPKT-UHFFFAOYSA-N ethyl n-[2-hydroxy-4-[(1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]carbamate Chemical compound C1=C(O)C(NC(=O)OCC)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 BLINRMNNGNVPKT-UHFFFAOYSA-N 0.000 claims description 2
• 208000024519 eye neoplasm Diseases 0.000 claims description 2
• 201000010536 head and neck cancer Diseases 0.000 claims description 2
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 2
• 208000016847 malignant urinary system neoplasm Diseases 0.000 claims description 2
• JZPPTXPTUAQCIX-UHFFFAOYSA-N methyl 3-[4-[(1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]anilino]-3-oxopropanoate Chemical compound C1=CC(NC(=O)CC(=O)OC)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 JZPPTXPTUAQCIX-UHFFFAOYSA-N 0.000 claims description 2
• KTXXRMMDOYLINK-UHFFFAOYSA-N methyl n-[4-[(1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 KTXXRMMDOYLINK-UHFFFAOYSA-N 0.000 claims description 2
• NXDRWKBUNYUSTJ-UHFFFAOYSA-N n-(2,3-dihydroxypropyl)-n-[5-[[1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyridin-2-yl]methanesulfonamide Chemical compound C1=NC(N(CC(O)CO)S(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=C4)O)CC3)C2=N1 NXDRWKBUNYUSTJ-UHFFFAOYSA-N 0.000 claims description 2
• NODBUXQIICRXEG-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-[4-[[1-(1-oxo-2,5,6,7-tetrahydrocyclopenta[c]pyridin-5-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(N(CCO)S(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=NC=C4)O)CC3)C2=N1 NODBUXQIICRXEG-UHFFFAOYSA-N 0.000 claims description 2
• RCZSIPRVXRTYQB-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-[4-[[1-(4-oxo-1,5,6,7-tetrahydrocyclopenta[b]pyridin-7-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(N(CCO)S(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=N4)O)CC3)C2=N1 RCZSIPRVXRTYQB-UHFFFAOYSA-N 0.000 claims description 2
• RYHWNCZNHCXYGY-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-n-[4-[[1-(1-oxo-2,5,6,7-tetrahydrocyclopenta[c]pyridin-5-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=C(NC=2N=C3N(C4C5=C(C(=NC=C5)O)CC4)N=CC3=CN=2)C=CC=1N(S(=O)(=O)C)CCN1CCOCC1 RYHWNCZNHCXYGY-UHFFFAOYSA-N 0.000 claims description 2
• LSFUHROVZWQHOA-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-n-[4-[[1-(4-oxo-1,5,6,7-tetrahydrocyclopenta[b]pyridin-7-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=C(NC=2N=C3N(C4C5=C(C(=CC=N5)O)CC4)N=CC3=CN=2)C=CC=1N(S(=O)(=O)C)CCN1CCOCC1 LSFUHROVZWQHOA-UHFFFAOYSA-N 0.000 claims description 2
• AUSZITCAJHBIAE-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 AUSZITCAJHBIAE-UHFFFAOYSA-N 0.000 claims description 2
• BUGMTSLWJAFSOV-UHFFFAOYSA-N n-(4-ethoxyphenyl)-1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OCC)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 BUGMTSLWJAFSOV-UHFFFAOYSA-N 0.000 claims description 2
• HROXXJGEUNLQNN-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C12=CC=CC=C2CCCC1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 HROXXJGEUNLQNN-UHFFFAOYSA-N 0.000 claims description 2
• QGADHEZNVGFZAR-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-(4-phenylmethoxy-5,6,7,8-tetrahydronaphthalen-1-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=1C=CC=CC=1COC(C=1CCCCC=11)=CC=C1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 QGADHEZNVGFZAR-UHFFFAOYSA-N 0.000 claims description 2
• PDDYITDAGXQLFZ-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 PDDYITDAGXQLFZ-UHFFFAOYSA-N 0.000 claims description 2
• RCMJHHVMQLVCIW-UHFFFAOYSA-N n-(4-piperidin-1-ylphenyl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N(C(C)C)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 RCMJHHVMQLVCIW-UHFFFAOYSA-N 0.000 claims description 2
• XOKYMERVEDOZSB-UHFFFAOYSA-N n-[1-[6-(4-aminoanilino)pyrazolo[3,4-d]pyrimidin-1-yl]-2,3-dihydro-1h-inden-5-yl]acetamide Chemical compound C1CC2=CC(NC(=O)C)=CC=C2C1N(C1=N2)N=CC1=CN=C2NC1=CC=C(N)C=C1 XOKYMERVEDOZSB-UHFFFAOYSA-N 0.000 claims description 2
• NDFDIONLUXHRRA-UHFFFAOYSA-N n-[1-[6-[4-[bis(methylsulfonyl)amino]anilino]pyrazolo[3,4-d]pyrimidin-1-yl]-2,3-dihydro-1h-inden-5-yl]acetamide Chemical compound C1CC2=CC(NC(=O)C)=CC=C2C1N(C1=N2)N=CC1=CN=C2NC1=CC=C(N(S(C)(=O)=O)S(C)(=O)=O)C=C1 NDFDIONLUXHRRA-UHFFFAOYSA-N 0.000 claims description 2
• XUKIAIZOXXRZAH-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-1-(4-phenylmethoxy-5,6,7,8-tetrahydronaphthalen-1-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C=4CCCCC=4C(OCC=4C=CC=CC=4)=CC=3)C2=N1 XUKIAIZOXXRZAH-UHFFFAOYSA-N 0.000 claims description 2
• NOVDWFZWJJMAGN-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 NOVDWFZWJJMAGN-UHFFFAOYSA-N 0.000 claims description 2
• WRNQONBRKRYHAA-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-1-naphthalen-2-ylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C=C4C=CC=CC4=CC=3)C2=N1 WRNQONBRKRYHAA-UHFFFAOYSA-N 0.000 claims description 2
• VHUXPMUCLXDCMG-UHFFFAOYSA-N n-[4-[(1-butylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound N1=C2N(CCCC)N=CC2=CN=C1NC1=CC=C(N(S(C)(=O)=O)S(C)(=O)=O)C=C1 VHUXPMUCLXDCMG-UHFFFAOYSA-N 0.000 claims description 2
• RTOSOGNLCXVILM-UHFFFAOYSA-N n-[4-[(1-ethylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound N1=C2N(CC)N=CC2=CN=C1NC1=CC=C(N(S(C)(=O)=O)S(C)(=O)=O)C=C1 RTOSOGNLCXVILM-UHFFFAOYSA-N 0.000 claims description 2
• VDRCUJYKXVHTRT-UHFFFAOYSA-N n-[4-[(1-methylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound N1=C2N(C)N=CC2=CN=C1NC1=CC=C(N(S(C)(=O)=O)S(C)(=O)=O)C=C1 VDRCUJYKXVHTRT-UHFFFAOYSA-N 0.000 claims description 2
• DJABCDSXUGZODL-UHFFFAOYSA-N n-[4-[(1-naphthalen-2-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C=3C=C4C=CC=CC4=CC=3)C2=N1 DJABCDSXUGZODL-UHFFFAOYSA-N 0.000 claims description 2
• UDOGMZACLBZDIX-UHFFFAOYSA-N n-[4-[[1-(1-methylindol-5-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C=1C=C2N(C)C=CC2=CC=1N(C1=N2)N=CC1=CN=C2NC1=CC=C(N(S(C)(=O)=O)S(C)(=O)=O)C=C1 UDOGMZACLBZDIX-UHFFFAOYSA-N 0.000 claims description 2
• AWVFCIOMPWNSPV-UHFFFAOYSA-N n-[4-[[1-(1h-indol-4-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C=3C=4C=CNC=4C=CC=3)C2=N1 AWVFCIOMPWNSPV-UHFFFAOYSA-N 0.000 claims description 2
• SBXVPXHLPAJYLF-UHFFFAOYSA-N n-[4-[[1-(1h-indol-5-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C=3C=C4C=CNC4=CC=3)C2=N1 SBXVPXHLPAJYLF-UHFFFAOYSA-N 0.000 claims description 2
• GTZDEMJMHLWQCT-UHFFFAOYSA-N n-[4-[[1-(1h-indol-6-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C=3C=C4NC=CC4=CC=3)C2=N1 GTZDEMJMHLWQCT-UHFFFAOYSA-N 0.000 claims description 2
• DUDXVUVSQOFKMJ-UHFFFAOYSA-N n-[4-[[1-(2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C3C4=CC=CC=C4CC3)C2=N1 DUDXVUVSQOFKMJ-UHFFFAOYSA-N 0.000 claims description 2
• BAGFSFOMGKNCPD-UHFFFAOYSA-N n-[4-[[1-(2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]benzamide Chemical compound C=1C=C(NC=2N=C3N(C4C5=CC=CC=C5CC4)N=CC3=CN=2)C=CC=1NC(=O)C1=CC=CC=C1 BAGFSFOMGKNCPD-UHFFFAOYSA-N 0.000 claims description 2
• ZODXXBYLDOSLHH-UHFFFAOYSA-N n-[4-[[1-(3-aminopropyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2CCCN)C2=N1 ZODXXBYLDOSLHH-UHFFFAOYSA-N 0.000 claims description 2
• QPOGQNLTAFXSAY-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-(2-hydroxyethyl)methanesulfonamide Chemical compound C1=CC(N(CCO)S(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=C4)O)CC3)C2=N1 QPOGQNLTAFXSAY-UHFFFAOYSA-N 0.000 claims description 2
• JFCFKBKMBHZOFA-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-(2-morpholin-4-ylethyl)methanesulfonamide Chemical compound C=1C=C(NC=2N=C3N(C4C5=C(C(=CC=C5)O)CC4)N=CC3=CN=2)C=CC=1N(S(=O)(=O)C)CCN1CCOCC1 JFCFKBKMBHZOFA-UHFFFAOYSA-N 0.000 claims description 2
• MIXZFVRNFNTJKW-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-(3-hydroxypropyl)methanesulfonamide Chemical compound C1=CC(N(CCCO)S(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=C4)O)CC3)C2=N1 MIXZFVRNFNTJKW-UHFFFAOYSA-N 0.000 claims description 2
• AUKMWEJWPOAKQC-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=C4)O)CC3)C2=N1 AUKMWEJWPOAKQC-UHFFFAOYSA-N 0.000 claims description 2
• ZDAPKQDOWXAPLV-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=C4)O)CC3)C2=N1 ZDAPKQDOWXAPLV-UHFFFAOYSA-N 0.000 claims description 2
• SHILZUNOBICHMV-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C=3C=4CCCCC=4C(O)=CC=3)C2=N1 SHILZUNOBICHMV-UHFFFAOYSA-N 0.000 claims description 2
• XMEDVJHVGRTXHS-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C=3C=4CCCCC=4C(O)=CC=3)C2=N1 XMEDVJHVGRTXHS-UHFFFAOYSA-N 0.000 claims description 2
• WVBAPAMTZRGBCW-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-(2-hydroxyethyl)methanesulfonamide Chemical compound C1=CC(N(CCO)S(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CN=C4)O)CC3)C2=N1 WVBAPAMTZRGBCW-UHFFFAOYSA-N 0.000 claims description 2
• TZCZGWMDLOQSHQ-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-(2-morpholin-4-ylethyl)methanesulfonamide Chemical compound C=1C=C(NC=2N=C3N(C4C5=C(C(=CN=C5)O)CC4)N=CC3=CN=2)C=CC=1N(S(=O)(=O)C)CCN1CCOCC1 TZCZGWMDLOQSHQ-UHFFFAOYSA-N 0.000 claims description 2
• NDRBKOBCSQJRNV-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CN=C4)O)CC3)C2=N1 NDRBKOBCSQJRNV-UHFFFAOYSA-N 0.000 claims description 2
• PLRFDIJVDOSNLI-UHFFFAOYSA-N n-[4-[[1-(4-hydroxybutyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2CCCCO)C2=N1 PLRFDIJVDOSNLI-UHFFFAOYSA-N 0.000 claims description 2
• ONQSADOYZKQNBZ-UHFFFAOYSA-N n-[4-[[1-(4-oxo-1,5,6,7-tetrahydrocyclopenta[b]pyridin-7-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=N4)O)CC3)C2=N1 ONQSADOYZKQNBZ-UHFFFAOYSA-N 0.000 claims description 2
• DWIAPUWBZVABKW-UHFFFAOYSA-N n-[4-[[1-(4-phenylmethoxy-5,6,7,8-tetrahydronaphthalen-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C=3C=4CCCCC=4C(OCC=4C=CC=CC=4)=CC=3)C2=N1 DWIAPUWBZVABKW-UHFFFAOYSA-N 0.000 claims description 2
• UKTSYKPSNIIODJ-UHFFFAOYSA-N n-[4-[[1-(5-methoxy-2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1CC2=CC(OC)=CC=C2C1N(C1=N2)N=CC1=CN=C2NC1=CC=C(N(S(C)(=O)=O)S(C)(=O)=O)C=C1 UKTSYKPSNIIODJ-UHFFFAOYSA-N 0.000 claims description 2
• JYELTDAQWBBMMY-UHFFFAOYSA-N n-[4-[[1-(6,7-dihydro-5h-cyclopenta[f][1,3]benzodioxol-7-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C3C4=CC=5OCOC=5C=C4CC3)C2=N1 JYELTDAQWBBMMY-UHFFFAOYSA-N 0.000 claims description 2
• DUDXVUVSQOFKMJ-HXUWFJFHSA-N n-[4-[[1-[(1r)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2[C@H]3C4=CC=CC=C4CC3)C2=N1 DUDXVUVSQOFKMJ-HXUWFJFHSA-N 0.000 claims description 2
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