JP5608099B2 - ピラゾロピリミジンｐｉ３ｋ阻害剤化合物および使用方法 - Google Patents

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Publication number

JP5608099B2

JP5608099B2 JP2010545168A JP2010545168A JP5608099B2 JP 5608099 B2 JP5608099 B2 JP 5608099B2 JP 2010545168 A JP2010545168 A JP 2010545168A JP 2010545168 A JP2010545168 A JP 2010545168A JP 5608099 B2 JP5608099 B2 JP 5608099B2

Authority

JP

Japan

Prior art keywords

pyrazolo

methyl

indazol

pyrimidine

cancer

Prior art date

2008-01-30

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.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 203
• 238000000034 method Methods 0.000 title description 195
• 239000012828 PI3K inhibitor Substances 0.000 title description 5
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 5
• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 title 1
• 229910052739 hydrogen Inorganic materials 0.000 claims description 135
• -1 1H-indazol-4-yl Chemical group 0.000 claims description 129
• 239000000203 mixture Substances 0.000 claims description 129
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 47
• 206010028980 Neoplasm Diseases 0.000 claims description 44
• 150000003839 salts Chemical class 0.000 claims description 38
• 201000011510 cancer Diseases 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 36
• 239000003814 drug Substances 0.000 claims description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 28
• 208000035475 disorder Diseases 0.000 claims description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
• 241000124008 Mammalia Species 0.000 claims description 16
• 229940079593 drug Drugs 0.000 claims description 16
• 239000002246 antineoplastic agent Substances 0.000 claims description 15
• 230000000694 effects Effects 0.000 claims description 15
• 108091007960 PI3Ks Proteins 0.000 claims description 14
• 229940127089 cytotoxic agent Drugs 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 230000003463 hyperproliferative effect Effects 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 229910052740 iodine Inorganic materials 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 9
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• 230000002401 inhibitory effect Effects 0.000 claims description 7
• 150000002632 lipids Chemical class 0.000 claims description 7
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 6
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• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
• 108091000080 Phosphotransferase Proteins 0.000 claims description 5
• 208000029742 colonic neoplasm Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 102000020233 phosphotransferase Human genes 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 4
• 206010038389 Renal cancer Diseases 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 201000010982 kidney cancer Diseases 0.000 claims description 4
• 201000007270 liver cancer Diseases 0.000 claims description 4
• 208000014018 liver neoplasm Diseases 0.000 claims description 4
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 201000002528 pancreatic cancer Diseases 0.000 claims description 4
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
• 206010038038 rectal cancer Diseases 0.000 claims description 4
• 201000001275 rectum cancer Diseases 0.000 claims description 4
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 3
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• 206010006187 Breast cancer Diseases 0.000 claims description 3
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• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
• 201000010881 cervical cancer Diseases 0.000 claims description 3
• 206010017758 gastric cancer Diseases 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 3
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• 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
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
• 201000011549 stomach cancer Diseases 0.000 claims description 3
• 201000002510 thyroid cancer Diseases 0.000 claims description 3
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
• DEDPRRGCSNEHDQ-UHFFFAOYSA-N 1-ethyl-6-(1h-indazol-4-yl)-n-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(CC)N=CC2=C1NC1=CC=CC(OC)=C1 DEDPRRGCSNEHDQ-UHFFFAOYSA-N 0.000 claims description 2
• HLLGTZWOHBWWQI-UHFFFAOYSA-N 3-[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2C=3C=NN(C)C=3N=C(N=2)C=2C=3C=NNC=3C=CC=2)=C1 HLLGTZWOHBWWQI-UHFFFAOYSA-N 0.000 claims description 2
• NUENGAUDNBPWDC-UHFFFAOYSA-N 3-[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C=2C=3C=NN(C)C=3N=C(N=2)C=2C=3C=NNC=3C=CC=2)=C1 NUENGAUDNBPWDC-UHFFFAOYSA-N 0.000 claims description 2
• KHMPVRGJRVKOIJ-UHFFFAOYSA-N 3-[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]benzonitrile Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1C1=CC=CC(C#N)=C1 KHMPVRGJRVKOIJ-UHFFFAOYSA-N 0.000 claims description 2
• PFLATXJJUYDFEH-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound C1=C2OCOC2=CC(C2=C3C=NN(C3=NC(=N2)C=2C=3C=NNC=3C=CC=2)C)=C1 PFLATXJJUYDFEH-UHFFFAOYSA-N 0.000 claims description 2
• DWNFGXZXGXSEES-UHFFFAOYSA-N 4-(2-imidazol-1-ylethoxy)-6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCCN1C=CN=C1 DWNFGXZXGXSEES-UHFFFAOYSA-N 0.000 claims description 2
• NDLJCAYBHDOXCU-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1C1=CC=C(Cl)C(Cl)=C1 NDLJCAYBHDOXCU-UHFFFAOYSA-N 0.000 claims description 2
• VEXTWAAATYKSFQ-UHFFFAOYSA-N 4-(3,4-dimethoxyphenoxy)-6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1OC1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C VEXTWAAATYKSFQ-UHFFFAOYSA-N 0.000 claims description 2
• RSMOMDWEXXTNEX-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C RSMOMDWEXXTNEX-UHFFFAOYSA-N 0.000 claims description 2
• QWBNOTDPNUKLTF-UHFFFAOYSA-N 4-[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C QWBNOTDPNUKLTF-UHFFFAOYSA-N 0.000 claims description 2
• BUVYCBKUBWWEOR-UHFFFAOYSA-N 4-[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C BUVYCBKUBWWEOR-UHFFFAOYSA-N 0.000 claims description 2
• HCIQITHWTLRLNY-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(2-pyridin-2-ylethoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCCC1=CC=CC=N1 HCIQITHWTLRLNY-UHFFFAOYSA-N 0.000 claims description 2
• NOSPERVAVGZLTN-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(2-pyridin-3-ylethoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCCC1=CC=CN=C1 NOSPERVAVGZLTN-UHFFFAOYSA-N 0.000 claims description 2
• WYORVHQXYFUYRA-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(2-pyridin-4-ylethoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCCC1=CC=NC=C1 WYORVHQXYFUYRA-UHFFFAOYSA-N 0.000 claims description 2
• USXMUICUBARLIJ-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(3-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1C1=CC=CC(S(C)(=O)=O)=C1 USXMUICUBARLIJ-UHFFFAOYSA-N 0.000 claims description 2
• HXKHCVMHKQEPKI-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(3-pyridin-4-ylpropoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCCCC1=CC=NC=C1 HXKHCVMHKQEPKI-UHFFFAOYSA-N 0.000 claims description 2
• HEWYBIPBHBTKJO-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(4-methylpiperazin-1-yl)pyrazolo[3,4-d]pyrimidine Chemical compound C1CN(C)CCN1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C HEWYBIPBHBTKJO-UHFFFAOYSA-N 0.000 claims description 2
• OTOJYQAIMJBHSU-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(4-methylsulfonylphenoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OC1=CC=C(S(C)(=O)=O)C=C1 OTOJYQAIMJBHSU-UHFFFAOYSA-N 0.000 claims description 2
• FUWDYAAWQCXQKW-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1C1=CC=C(S(C)(=O)=O)C=C1 FUWDYAAWQCXQKW-UHFFFAOYSA-N 0.000 claims description 2
• XLZRJAWUWFSSAL-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(4-methylsulfonylpiperazin-1-yl)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1N1CCN(S(C)(=O)=O)CC1 XLZRJAWUWFSSAL-UHFFFAOYSA-N 0.000 claims description 2
• IQZVCECIMURBLM-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(pyridin-2-ylmethoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCC1=CC=CC=N1 IQZVCECIMURBLM-UHFFFAOYSA-N 0.000 claims description 2
• HNMXXYKEUSXMRK-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(pyridin-3-ylmethoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCC1=CC=CN=C1 HNMXXYKEUSXMRK-UHFFFAOYSA-N 0.000 claims description 2
• UMKDIFZGZXXFLM-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(pyridin-4-ylmethoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCC1=CC=NC=C1 UMKDIFZGZXXFLM-UHFFFAOYSA-N 0.000 claims description 2
• HBWRIMBTASRACT-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-[(4-methylsulfonylphenyl)methoxy]pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCC1=CC=C(S(C)(=O)=O)C=C1 HBWRIMBTASRACT-UHFFFAOYSA-N 0.000 claims description 2
• WRFJLOZPEJTSKV-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-phenylmethoxypyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCC1=CC=CC=C1 WRFJLOZPEJTSKV-UHFFFAOYSA-N 0.000 claims description 2
• VXFZHMRYVFEMNH-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-pyridin-3-yloxypyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OC1=CC=CN=C1 VXFZHMRYVFEMNH-UHFFFAOYSA-N 0.000 claims description 2
• UMAGBLRZYBDBEW-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-(4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NC1=CC=C(S(C)(=O)=O)C=C1 UMAGBLRZYBDBEW-UHFFFAOYSA-N 0.000 claims description 2
• GOEZWSQMGPZHIK-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-4-(2-methoxyethoxy)-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound N=1C=2N(C)N=CC=2C(OCCOC)=NC=1C1=CC=CC2=C1C=NN2 GOEZWSQMGPZHIK-UHFFFAOYSA-N 0.000 claims description 2
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• IZWKXYSNYMACSX-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-4-(4-methoxyphenyl)-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C IZWKXYSNYMACSX-UHFFFAOYSA-N 0.000 claims description 2
• UAIBQKCOMNFIAX-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-4-[(3-methoxyphenyl)methoxy]-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound COC1=CC=CC(COC=2C=3C=NN(C)C=3N=C(N=2)C=2C=3C=NNC=3C=CC=2)=C1 UAIBQKCOMNFIAX-UHFFFAOYSA-N 0.000 claims description 2
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• JUXOGGBJGKFDTQ-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-n-(3-methoxyphenyl)-1,3-dimethylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(NC=2C=3C(C)=NN(C)C=3N=C(N=2)C=2C=3C=NNC=3C=CC=2)=C1 JUXOGGBJGKFDTQ-UHFFFAOYSA-N 0.000 claims description 2
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• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
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