AU2008211172A1 - 1-H-pyrazolo(3,4B)pyrimidine derivatives and their use as modulators of mitotic kinases - Google Patents

Info

Publication number

AU2008211172A1

AU2008211172A1 AU2008211172A AU2008211172A AU2008211172A1 AU 2008211172 A1 AU2008211172 A1 AU 2008211172A1 AU 2008211172 A AU2008211172 A AU 2008211172A AU 2008211172 A AU2008211172 A AU 2008211172A AU 2008211172 A1 AU2008211172 A1 AU 2008211172A1

Authority

AU

Australia

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
• Discuss

• 108091000080 Phosphotransferase Proteins 0.000 title description 16
• 102000020233 phosphotransferase Human genes 0.000 title description 16
• 230000000394 mitotic effect Effects 0.000 title description 12
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
• 150000003230 pyrimidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 268
• -1 amino, hydroxy Chemical group 0.000 claims description 261
• 125000001072 heteroaryl group Chemical group 0.000 claims description 155
• 125000003118 aryl group Chemical group 0.000 claims description 153
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 147
• 125000000217 alkyl group Chemical group 0.000 claims description 137
• 238000000034 method Methods 0.000 claims description 110
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 90
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 89
• 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
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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 28
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 21
• SMXRCJBCWRHDJE-UHFFFAOYSA-N 7-deaza-8-aza-2-aminopurine Chemical compound NC1=NC=C2C=NNC2=N1 SMXRCJBCWRHDJE-UHFFFAOYSA-N 0.000 claims description 20
• 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 20
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
• 239000005711 Benzoic acid Substances 0.000 claims description 18
• 229960004365 benzoic acid Drugs 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
• 235000010233 benzoic acid Nutrition 0.000 claims description 16
• 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
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 13
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
• 101000582926 Dictyostelium discoideum Probable serine/threonine-protein kinase PLK Proteins 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 230000011278 mitosis Effects 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
• 150000003839 salts Chemical class 0.000 claims description 11
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 10
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• 125000004001 thioalkyl group Chemical group 0.000 claims description 9
• 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
• 102000001253 Protein Kinase Human genes 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
• 125000004435 hydrogen atom Chemical group [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
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 6
• BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 6
• 108060006633 protein kinase Proteins 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
• 229940050390 benzoate Drugs 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
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 208000032839 leukemia Diseases 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
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 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
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• 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 3
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
• DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 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
• 150000001204 N-oxides Chemical class 0.000 claims description 3
• WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 claims description 3
• HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 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
• 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
• 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
• 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
• 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
• YVDUPENJMTVWOZ-FQEVSTJZSA-N 1-[(1s)-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-FQEVSTJZSA-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
• 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
• GNLYDYBTNQWAIR-QHCPKHFHSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 GNLYDYBTNQWAIR-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
• 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
• 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
• 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
• VJASYXGEGDPVHV-UHFFFAOYSA-N 1-methylsulfonyl-n-[4-[(1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 VJASYXGEGDPVHV-UHFFFAOYSA-N 0.000 claims description 2
• LVMUIDNHXZXROD-UHFFFAOYSA-N 1-naphthalen-1-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=CC=CC=C4C=CC=3)C2=N1 LVMUIDNHXZXROD-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
• 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 2
• BWIGEIUCPNBEOP-UHFFFAOYSA-N 2-[4-[4-[[1-(2,3-dihydro-1H-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]piperazin-1-yl]ethyl acetate Chemical compound C1(CCC2=CC=CC=C12)N1N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)CCOC(C)=O BWIGEIUCPNBEOP-UHFFFAOYSA-N 0.000 claims description 2
• UATSFHUDDGSGJO-UHFFFAOYSA-N 2-[4-[4-[[1-(2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3C4=CC=CC=C4CC3)C2=N1 UATSFHUDDGSGJO-UHFFFAOYSA-N 0.000 claims description 2
• DZENZZYVIHNKLP-UHFFFAOYSA-N 3,3,3-trifluoro-n-[4-[(1-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]propane-1-sulfonamide Chemical compound C1=CC(NS(=O)(=O)CCC(F)(F)F)=CC=C1NC1=NC=C(C=NN2C=3C4=CC=CC=C4C=CC=3)C2=N1 DZENZZYVIHNKLP-UHFFFAOYSA-N 0.000 claims description 2
• RUBKIXUFDOQFDV-UHFFFAOYSA-N 3-[4-[4-[[1-(2,3-dihydro-1H-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]piperazin-1-yl]propyl acetate Chemical compound C1(CCC2=CC=CC=C12)N1N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)CCCOC(C)=O RUBKIXUFDOQFDV-UHFFFAOYSA-N 0.000 claims description 2
• MUIFRJGRMPFECO-UHFFFAOYSA-N 3-[4-[4-[[1-(2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]piperazin-1-yl]propan-1-ol Chemical compound C1CN(CCCO)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3C4=CC=CC=C4CC3)C2=N1 MUIFRJGRMPFECO-UHFFFAOYSA-N 0.000 claims description 2
• OAKURXIZZOAYBC-UHFFFAOYSA-M 3-oxopropanoate Chemical compound [O-]C(=O)CC=O OAKURXIZZOAYBC-UHFFFAOYSA-M 0.000 claims description 2
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• 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 2
• 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 2
• DZIDCCMIUKYXBQ-LJQANCHMSA-N 5-[[1-[(1r)-1,2-dihydroacenaphthylen-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]3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 DZIDCCMIUKYXBQ-LJQANCHMSA-N 0.000 claims description 2
• DZIDCCMIUKYXBQ-IBGZPJMESA-N 5-[[1-[(1s)-1,2-dihydroacenaphthylen-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]3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 DZIDCCMIUKYXBQ-IBGZPJMESA-N 0.000 claims description 2
• 206010005949 Bone cancer Diseases 0.000 claims description 2
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• 206010009944 Colon cancer Diseases 0.000 claims description 2
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 2
• 206010025323 Lymphomas Diseases 0.000 claims description 2
• 206010039491 Sarcoma Diseases 0.000 claims description 2
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
• 208000021712 Soft tissue sarcoma Diseases 0.000 claims description 2
• 208000008385 Urogenital Neoplasms Diseases 0.000 claims description 2
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