CA2711759A1 - Pyrazolopyrimidine pi3k inhibitor compounds and methods of use - Google Patents

Info

Publication number

CA2711759A1

CA2711759A1 CA2711759A CA2711759A CA2711759A1 CA 2711759 A1 CA2711759 A1 CA 2711759A1 CA 2711759 A CA2711759 A CA 2711759A CA 2711759 A CA2711759 A CA 2711759A CA 2711759 A1 CA2711759 A1 CA 2711759A1

Authority

CA

Canada

Prior art keywords

pyrazolo

methyl

indazol

pyrimidin

pyrimidine

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 241
• 238000000034 method Methods 0.000 title claims abstract description 212
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 3
• 239000012828 PI3K inhibitor Substances 0.000 title 1
• 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
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
• 238000011282 treatment Methods 0.000 claims abstract description 38
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 35
• 150000003839 salts Chemical class 0.000 claims abstract description 35
• 201000011510 cancer Diseases 0.000 claims abstract description 28
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 23
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 23
• 150000002632 lipids Chemical class 0.000 claims abstract description 12
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
• 230000001404 mediated effect Effects 0.000 claims abstract description 4
• -1 -CH2OH Chemical group 0.000 claims description 179
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 73
• 208000035475 disorder Diseases 0.000 claims description 31
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 241000124008 Mammalia Species 0.000 claims description 19
• 229910052740 iodine Inorganic materials 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 17
• 229910052794 bromium Inorganic materials 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 13
• 239000002246 antineoplastic agent Substances 0.000 claims description 13
• 229940127089 cytotoxic agent Drugs 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 230000003463 hyperproliferative effect Effects 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 230000001225 therapeutic effect Effects 0.000 claims description 12
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 125000002619 bicyclic group Chemical group 0.000 claims description 11
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 9
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 125000004419 alkynylene group Chemical group 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 5
• 210000000214 mouth Anatomy 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• 201000009030 Carcinoma Diseases 0.000 claims description 4
• 206010038389 Renal cancer Diseases 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 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 3
• QDCCNSAYVVKBDC-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(2-phenylethoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCCC1=CC=CC=C1 QDCCNSAYVVKBDC-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• XQXCNOGZCQMJTQ-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-4-[3-(methoxymethyl)phenyl]-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound COCC1=CC=CC(C=2C=3C=NN(C)C=3N=C(N=2)C=2C=3C=NNC=3C=CC=2)=C1 XQXCNOGZCQMJTQ-UHFFFAOYSA-N 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 3
• 210000004072 lung Anatomy 0.000 claims description 3
• 201000005249 lung adenocarcinoma Diseases 0.000 claims description 3
• 210000003800 pharynx Anatomy 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• RHAZVGSKLDZSDV-UHFFFAOYSA-N 1-[2-[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]oxyethyl]pyrrolidin-2-one Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCCN1CCCC1=O RHAZVGSKLDZSDV-UHFFFAOYSA-N 0.000 claims description 2
• DVFCXODQTMEIII-UHFFFAOYSA-N 1-[3-[[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]amino]propyl]pyrrolidin-2-one Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NCCCN1CCCC1=O DVFCXODQTMEIII-UHFFFAOYSA-N 0.000 claims description 2
• QLUFVMIFGUKVBT-UHFFFAOYSA-N 1-[4-[6-(1h-indazol-4-yl)-1-methylpyrazolo[3,4-d]pyrimidin-4-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1OC1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C QLUFVMIFGUKVBT-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
• PTRLDZJTEJANSK-UHFFFAOYSA-N 5-[4-(3-methoxyanilino)-1-methylpyrazolo[3,4-d]pyrimidin-6-yl]-1,3-dihydrobenzimidazol-2-one Chemical compound COC1=CC=CC(NC=2C=3C=NN(C)C=3N=C(N=2)C=2C=C3NC(=O)NC3=CC=2)=C1 PTRLDZJTEJANSK-UHFFFAOYSA-N 0.000 claims description 2
• HUXYCQILXQWXKD-UHFFFAOYSA-N 5-[4-(3-methoxyphenoxy)-1-methylpyrazolo[3,4-d]pyrimidin-6-yl]pyridin-2-amine Chemical compound COC1=CC=CC(OC=2C=3C=NN(C)C=3N=C(N=2)C=2C=NC(N)=CC=2)=C1 HUXYCQILXQWXKD-UHFFFAOYSA-N 0.000 claims description 2
• SLUQLSKOUMMSPH-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-n-(3-methoxyphenyl)-1-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(NC=2C=3C=NN(C)C=3N=C(N=2)C=2C=C3OCOC3=CC=2)=C1 SLUQLSKOUMMSPH-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
• PTMMPKIIPQPGJV-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-(3-pyridin-3-ylpropoxy)pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCCCC1=CC=CN=C1 PTMMPKIIPQPGJV-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
• YGBHIJBMKHSEHZ-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-4-[2-[3-(trifluoromethyl)phenyl]ethoxy]pyrazolo[3,4-d]pyrimidine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1OCCC1=CC=CC(C(F)(F)F)=C1 YGBHIJBMKHSEHZ-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
• RRMAFHAVOVQQDO-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-(1-methylpiperidin-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCC1NC1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C RRMAFHAVOVQQDO-UHFFFAOYSA-N 0.000 claims description 2
• IZQBLIGUUVAPLH-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-(2-phenoxyethyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NCCOC1=CC=CC=C1 IZQBLIGUUVAPLH-UHFFFAOYSA-N 0.000 claims description 2
• ACKXBNISFJKXCG-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-(2-pyridin-3-ylethyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NCCC1=CC=CN=C1 ACKXBNISFJKXCG-UHFFFAOYSA-N 0.000 claims description 2
• PCEWGMIVBMIERV-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-(3-morpholin-4-ylpropyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NCCCN1CCOCC1 PCEWGMIVBMIERV-UHFFFAOYSA-N 0.000 claims description 2
• IUFKDXWOBGFATJ-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-(3-pyrrolidin-1-ylpropyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NCCCN1CCCC1 IUFKDXWOBGFATJ-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
• QRIRVGYQBGTTQN-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NC1CCOCC1 QRIRVGYQBGTTQN-UHFFFAOYSA-N 0.000 claims description 2
• UYNAJCVTJYMAGG-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-(pyridin-3-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NCC1=CC=CN=C1 UYNAJCVTJYMAGG-UHFFFAOYSA-N 0.000 claims description 2
• TVGJYFHPPIGXTJ-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-[(3-methylsulfonylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2N(C)N=CC2=C1NCC1=CC=CC(S(C)(=O)=O)=C1 TVGJYFHPPIGXTJ-UHFFFAOYSA-N 0.000 claims description 2
• GVBAPIGTMDFKMU-UHFFFAOYSA-N 6-(1h-indazol-4-yl)-1-methyl-n-[3-(4-methylpiperazin-1-yl)propyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CCCNC1=NC(C=2C=3C=NNC=3C=CC=2)=NC2=C1C=NN2C GVBAPIGTMDFKMU-UHFFFAOYSA-N 0.000 claims description 2
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