JP2010532312A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010532312A5 JP2010532312A5 JP2009548293A JP2009548293A JP2010532312A5 JP 2010532312 A5 JP2010532312 A5 JP 2010532312A5 JP 2009548293 A JP2009548293 A JP 2009548293A JP 2009548293 A JP2009548293 A JP 2009548293A JP 2010532312 A5 JP2010532312 A5 JP 2010532312A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrazolo
- pyrimidin
- phenyl
- ylamino
- Prior art date
- 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- Withdrawn
Links
- -1 guanidinyl group Chemical group 0.000 claims description 448
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000005518 carboxamido group Chemical group 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 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
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 5
- NTNDIJQLWSJGSJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C2C=N1 NTNDIJQLWSJGSJ-UHFFFAOYSA-N 0.000 claims description 4
- SSWQBXSNHDXNJR-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=N1 SSWQBXSNHDXNJR-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- LKSCRRBMTYKEAT-UHFFFAOYSA-N 1-cycloheptyl-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CNCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 LKSCRRBMTYKEAT-UHFFFAOYSA-N 0.000 claims description 4
- MSIUDSLIFBLRLA-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CCCCCC1N1C2=NC(NC=3C=CC(=CC=3)C=3NN=NN=3)=NC=C2C=N1 MSIUDSLIFBLRLA-UHFFFAOYSA-N 0.000 claims description 4
- BIDHRJUVEKTJKT-UHFFFAOYSA-N 2-methoxy-5-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C(O)C(OC)=CC=4)=NC=C3C=N2)=C1 BIDHRJUVEKTJKT-UHFFFAOYSA-N 0.000 claims description 4
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- JYKBEZSKNYJRGG-UHFFFAOYSA-N 4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 JYKBEZSKNYJRGG-UHFFFAOYSA-N 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- RUUWHQJRWMWXOZ-UHFFFAOYSA-N COC1=CC=CC(=C1)N2C3=NC(=NC=C3C=N2)C4(CC=C(C=C4)N)N Chemical compound COC1=CC=CC(=C1)N2C3=NC(=NC=C3C=N2)C4(CC=C(C=C4)N)N RUUWHQJRWMWXOZ-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- DMMWKWROYMBMDS-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-(pyridin-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=CC2=CN=C(NC=3C=CC(=CC=3)N3CCOCC3)N=C2N1CC1=CC=CC=N1 DMMWKWROYMBMDS-UHFFFAOYSA-N 0.000 claims description 4
- BOVLFNSGFMRUHI-UHFFFAOYSA-N n-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 BOVLFNSGFMRUHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- LRBWSVUGCRFEBL-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=1C=CC=CC=1CN(CC1)CCC1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 LRBWSVUGCRFEBL-UHFFFAOYSA-N 0.000 claims description 3
- XCYBMRJTKDZSBM-UHFFFAOYSA-N 1-(cyclopentylmethyl)-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C2N1CC1CCCC1 XCYBMRJTKDZSBM-UHFFFAOYSA-N 0.000 claims description 3
- NPBPEVPENRPELD-UHFFFAOYSA-N 1-cycloheptyl-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=NN2C3CCCCCC3)C2=N1 NPBPEVPENRPELD-UHFFFAOYSA-N 0.000 claims description 3
- QCQZVTRSTWAIOF-UHFFFAOYSA-N 2-methoxy-5-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(O)C(OC)=CC=3)=NC=C2C=N1 QCQZVTRSTWAIOF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
- SMXRCJBCWRHDJE-UHFFFAOYSA-N 7-deaza-8-aza-2-aminopurine Chemical compound NC1=NC=C2C=NNC2=N1 SMXRCJBCWRHDJE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- MFCAMGOTCXUILT-UHFFFAOYSA-N n-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(NS(C)(=O)=O)=CC=3)=NC=C2C=N1 MFCAMGOTCXUILT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- LOGAFLFGWNBIIG-UHFFFAOYSA-N pyridin-3-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CN=C1 LOGAFLFGWNBIIG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- XQEMZJJTVBNDOF-UHFFFAOYSA-N 1-(2-phenylphenyl)-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N=1C=C2C=NN(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=NC=1NC(C=C1)=CC=C1C1=NN=NN1 XQEMZJJTVBNDOF-UHFFFAOYSA-N 0.000 claims description 2
- LRWSKWAKMANXPV-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C5OCCOCCOCCOCCOC5=CC=4)=NC=C3C=N2)=C1 LRWSKWAKMANXPV-UHFFFAOYSA-N 0.000 claims description 2
- JIWHVEKKCGYCKC-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)N4CCOCC4)=NC=C3C=N2)=C1 JIWHVEKKCGYCKC-UHFFFAOYSA-N 0.000 claims description 2
- GTHKIIRCEUCXJH-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)N4CCNCC4)=NC=C3C=N2)=C1 GTHKIIRCEUCXJH-UHFFFAOYSA-N 0.000 claims description 2
- MFHNGCQLTIZJLF-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)C=4NN=NN=4)=NC=C3C=N2)=C1 MFHNGCQLTIZJLF-UHFFFAOYSA-N 0.000 claims description 2
- CIOYAVYPXDDWOJ-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)N4CCN(CC4)S(C)(=O)=O)=NC=C3C=N2)=C1 CIOYAVYPXDDWOJ-UHFFFAOYSA-N 0.000 claims description 2
- ZRLRPHMIYBFLMQ-UHFFFAOYSA-N 1-(4-iodophenyl)-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(I)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=N1 ZRLRPHMIYBFLMQ-UHFFFAOYSA-N 0.000 claims description 2
- PYKBWGLGDQWXLV-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C4OCCOCCOCCOCCOC4=CC=3)=NC=C2C=N1 PYKBWGLGDQWXLV-UHFFFAOYSA-N 0.000 claims description 2
- YRVUWBVQVHUVOX-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(3,4,5-trimethoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(OC)C(OC)=C(OC)C=3)=NC=C2C=N1 YRVUWBVQVHUVOX-UHFFFAOYSA-N 0.000 claims description 2
- IKFSCGNSSUVZBN-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)S(C)(=O)=O)=NC=C2C=N1 IKFSCGNSSUVZBN-UHFFFAOYSA-N 0.000 claims description 2
- IEHNIMGOGYPUFD-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=N1 IEHNIMGOGYPUFD-UHFFFAOYSA-N 0.000 claims description 2
- HWFPYNTWTBFJRZ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[3-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(C=CC=3)N3CCN(C)CC3)=NC=C2C=N1 HWFPYNTWTBFJRZ-UHFFFAOYSA-N 0.000 claims description 2
- WGHXFMZWZMSQMT-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[4-(1,2,4-triazol-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3N=CN=C3)=NC=C2C=N1 WGHXFMZWZMSQMT-UHFFFAOYSA-N 0.000 claims description 2
- NVGFVCHSJMXOJQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C=3NN=NN=3)=NC=C2C=N1 NVGFVCHSJMXOJQ-UHFFFAOYSA-N 0.000 claims description 2
- PRQIXWUKPMJIJW-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCN(CC3)S(C)(=O)=O)=NC=C2C=N1 PRQIXWUKPMJIJW-UHFFFAOYSA-N 0.000 claims description 2
- AFVHDTGRLLQRQU-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C4=CC=CC=C4C=CC=3)=NC=C2C=N1 AFVHDTGRLLQRQU-UHFFFAOYSA-N 0.000 claims description 2
- MMLBTCRYWOMKMZ-UHFFFAOYSA-N 1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(N)=NC=C2C=N1 MMLBTCRYWOMKMZ-UHFFFAOYSA-N 0.000 claims description 2
- JERQSOGSLYNKSN-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1CN1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C=N1 JERQSOGSLYNKSN-UHFFFAOYSA-N 0.000 claims description 2
- UCMHHGHSKZGGKC-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(CN2C3=NC(NC=4C=CC(=CC=4)N4CCNCC4)=NC=C3C=N2)=C1 UCMHHGHSKZGGKC-UHFFFAOYSA-N 0.000 claims description 2
- ZVPPZUMHXCGRGD-UHFFFAOYSA-N 1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=C(C)C=NC(CN2C3=NC(NC=4C=CC(=CC=4)N4CCOCC4)=NC=C3C=N2)=C1C ZVPPZUMHXCGRGD-UHFFFAOYSA-N 0.000 claims description 2
- RWLCTZUSLUIIRR-UHFFFAOYSA-N 1-[3-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]ethanol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(C=CC=3)C(C)O)=NC=C2C=N1 RWLCTZUSLUIIRR-UHFFFAOYSA-N 0.000 claims description 2
- MWBDIIOUUDTETI-UHFFFAOYSA-N 1-benzyl-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C2N1CC1=CC=CC=C1 MWBDIIOUUDTETI-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
- JZWWOVYCDFKCTQ-UHFFFAOYSA-N 1-cycloheptyl-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 JZWWOVYCDFKCTQ-UHFFFAOYSA-N 0.000 claims description 2
- OHAYHVBBKFKPGX-UHFFFAOYSA-N 1-cycloheptyl-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 OHAYHVBBKFKPGX-UHFFFAOYSA-N 0.000 claims description 2
- LJFXJAGGDZXRQX-UHFFFAOYSA-N 1-cycloheptyl-n-(4-pyrazol-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CCCCCC1N1C2=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=N1 LJFXJAGGDZXRQX-UHFFFAOYSA-N 0.000 claims description 2
- UCEFGXSILYUJIE-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(1-methyltetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CN1N=NN=C1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 UCEFGXSILYUJIE-UHFFFAOYSA-N 0.000 claims description 2
- IPBRJZXTSCTAAI-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(2-morpholin-4-ylethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=1C=C(NC=2N=C3N(C4CCCCCC4)N=CC3=CN=2)C=CC=1OCCN1CCOCC1 IPBRJZXTSCTAAI-UHFFFAOYSA-N 0.000 claims description 2
- VQQWSSDIJAORSU-UHFFFAOYSA-N 1-cycloheptyl-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=NN2C3CCCCCC3)C2=N1 VQQWSSDIJAORSU-UHFFFAOYSA-N 0.000 claims description 2
- UUQKTIWWHSBBGI-UHFFFAOYSA-N 1-cycloheptyl-n-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 UUQKTIWWHSBBGI-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
- CVYJQYKYFZIBCG-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-2-methyl-1-(4-methylpiperazin-1-yl)propan-1-one Chemical compound C1CN(C)CCN1C(=O)C(C)(C)C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 CVYJQYKYFZIBCG-UHFFFAOYSA-N 0.000 claims description 2
- GNOXGRKHNMFNLZ-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-2-methylpropanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 GNOXGRKHNMFNLZ-UHFFFAOYSA-N 0.000 claims description 2
- NROOCSOXUCZDGS-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-n-propan-2-ylacetamide Chemical compound C1=CC(CC(=O)NC(C)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 NROOCSOXUCZDGS-UHFFFAOYSA-N 0.000 claims description 2
- AMSCDMMOZIJNEF-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]ethanol Chemical compound C1=CC(CCO)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 AMSCDMMOZIJNEF-UHFFFAOYSA-N 0.000 claims description 2
- YFWUKRYNTIIIAA-UHFFFAOYSA-N 2-ethoxy-5-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=C(O)C(OCC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(OC)=CC=3)C2=N1 YFWUKRYNTIIIAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- GLNFNQVQAATIJH-UHFFFAOYSA-N 2-methoxy-5-[[1-(2-phenylphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=N1 GLNFNQVQAATIJH-UHFFFAOYSA-N 0.000 claims description 2
- NHRIKAFOXFZKQA-UHFFFAOYSA-N 3-[6-(4-aminoanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenol Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C=3C=C(O)C=CC=3)C2=N1 NHRIKAFOXFZKQA-UHFFFAOYSA-N 0.000 claims description 2
- SOIGDEMQRVPBLK-UHFFFAOYSA-N 3-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(O)C=CC=3)=NC=C2C=N1 SOIGDEMQRVPBLK-UHFFFAOYSA-N 0.000 claims description 2
- GTKQJYUCWRMVEV-UHFFFAOYSA-N 4-[4-[6-(3,4-dimethoxyanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenyl]but-3-yn-1-ol Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(=CC=3)C#CCCO)C2=N1 GTKQJYUCWRMVEV-UHFFFAOYSA-N 0.000 claims description 2
- UUTJIZAMHZENAQ-UHFFFAOYSA-N 4-[4-[6-(4-aminoanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenyl]but-3-yn-1-ol Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C=3C=CC(=CC=3)C#CCCO)C2=N1 UUTJIZAMHZENAQ-UHFFFAOYSA-N 0.000 claims description 2
- IPPJIWCVXZIHDK-UHFFFAOYSA-N 4-[6-(4-morpholin-4-ylanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenol Chemical compound C1=CC(O)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C2C=N1 IPPJIWCVXZIHDK-UHFFFAOYSA-N 0.000 claims description 2
- JMKYNBJGIUXATL-UHFFFAOYSA-N 4-[[1-(2-phenylphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=N1 JMKYNBJGIUXATL-UHFFFAOYSA-N 0.000 claims description 2
- ZAMPQPZOSFLZIW-UHFFFAOYSA-N 4-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)C(O)=O)=NC=C3C=N2)=C1 ZAMPQPZOSFLZIW-UHFFFAOYSA-N 0.000 claims description 2
- TZNKPZOESHQVKX-UHFFFAOYSA-N 4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]-2-methylphenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(C)C(O)=CC=3)=NC=C2C=N1 TZNKPZOESHQVKX-UHFFFAOYSA-N 0.000 claims description 2
- XFKALRRMCCCGFK-UHFFFAOYSA-N 4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C(O)=O)=NC=C2C=N1 XFKALRRMCCCGFK-UHFFFAOYSA-N 0.000 claims description 2
- IMNSQKHQDGNNLX-UHFFFAOYSA-N 4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(O)=CC=3)=NC=C2C=N1 IMNSQKHQDGNNLX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- CAOCEOAUKSPUPN-UHFFFAOYSA-N 4-ethylpiperazine-1-carbaldehyde Chemical compound CCN1CCN(C=O)CC1 CAOCEOAUKSPUPN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- WMQFRHKLXUDUGC-UHFFFAOYSA-N 5-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 WMQFRHKLXUDUGC-UHFFFAOYSA-N 0.000 claims description 2
- OBXLLSUUUPFEJN-UHFFFAOYSA-N 5-[[1-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=C(O)C=CC=3)C2=N1 OBXLLSUUUPFEJN-UHFFFAOYSA-N 0.000 claims description 2
- JJIHWSUUDQCEGB-UHFFFAOYSA-N 5-[[1-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(O)=CC=3)C2=N1 JJIHWSUUDQCEGB-UHFFFAOYSA-N 0.000 claims description 2
- YCVFIKVKPPNWMD-UHFFFAOYSA-N 5-[[1-(4-iodophenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(I)=CC=3)C2=N1 YCVFIKVKPPNWMD-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 102000003989 Aurora kinases Human genes 0.000 claims description 2
- 108090000433 Aurora kinases Proteins 0.000 claims description 2
- 206010005949 Bone cancer Diseases 0.000 claims description 2
- 208000018084 Bone neoplasm Diseases 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
- QVPBQCLIHFTOIZ-UHFFFAOYSA-N C1CN(CCN1)C2=CC=C(C=C2)NC3=NN(C4=NC=NC=C34)C5=CC=CC=C5C6=CC=CC=C6 Chemical compound C1CN(CCN1)C2=CC=C(C=C2)NC3=NN(C4=NC=NC=C34)C5=CC=CC=C5C6=CC=CC=C6 QVPBQCLIHFTOIZ-UHFFFAOYSA-N 0.000 claims description 2
- TXNWYFLWPOLOLJ-UHFFFAOYSA-N CS(N(CCN1CCOCC1)C(N=C1)=NC=C1NC1=NC=C(C=NN2OC(NC3=NC=CC=C3)=O)C2=N1)(=O)=O Chemical compound CS(N(CCN1CCOCC1)C(N=C1)=NC=C1NC1=NC=C(C=NN2OC(NC3=NC=CC=C3)=O)C2=N1)(=O)=O TXNWYFLWPOLOLJ-UHFFFAOYSA-N 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 2
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 102000001253 Protein Kinase Human genes 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
- CKTDDBSAWWUOFZ-UHFFFAOYSA-N [2-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]anilino]-2-oxoethyl] acetate Chemical compound C(C)(=O)OCC(=O)NC1=CC=C(C=C1)NC1=NC=C2C(=N1)N(N=C2)C1=CC=C(C=C1)OC CKTDDBSAWWUOFZ-UHFFFAOYSA-N 0.000 claims description 2
- CAHBGWMUUOOJGM-UHFFFAOYSA-N [4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C(NC=2N=C3N(C4CCCCCC4)N=CC3=CN=2)C=CC=1C(=O)N1CCOCC1 CAHBGWMUUOOJGM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 208000025997 central nervous system neoplasm Diseases 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- IKOKFZXHPKMJDJ-UHFFFAOYSA-N ethyl 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-2-methylpropanoate Chemical compound C1=CC(C(C)(C)C(=O)OCC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 IKOKFZXHPKMJDJ-UHFFFAOYSA-N 0.000 claims description 2
- QSFFWWWRDDNJTK-UHFFFAOYSA-N ethyl 2-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OCC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(OC)=CC=3)C2=N1 QSFFWWWRDDNJTK-UHFFFAOYSA-N 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
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000029559 malignant endocrine neoplasm Diseases 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- CTAFNJPQTPFBDJ-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C5OCOC5=CC=4)=NC=C3C=N2)=C1 CTAFNJPQTPFBDJ-UHFFFAOYSA-N 0.000 claims description 2
- RUEKWHWBQAROJT-UHFFFAOYSA-N n-(2,2-dimethyl-1,3-benzodioxol-5-yl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C4OC(C)(C)OC4=CC=3)=NC=C2C=N1 RUEKWHWBQAROJT-UHFFFAOYSA-N 0.000 claims description 2
- VTCCBKSDGJNVLI-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C4OCCOC4=CC=3)=NC=C2C=N1 VTCCBKSDGJNVLI-UHFFFAOYSA-N 0.000 claims description 2
- OATKTTPFFACPRZ-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C(=CC(OC)=CC=4)OC)=NC=C3C=N2)=C1 OATKTTPFFACPRZ-UHFFFAOYSA-N 0.000 claims description 2
- UQDVTFIYKOXMHK-UHFFFAOYSA-N n-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C4OCCCOC4=CC=3)=NC=C2C=N1 UQDVTFIYKOXMHK-UHFFFAOYSA-N 0.000 claims description 2
- XYMUWFMXHZWFDH-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C(OC)C(OC)=CC=4)=NC=C3C=N2)=C1 XYMUWFMXHZWFDH-UHFFFAOYSA-N 0.000 claims description 2
- BVHBUYVDFKRVFF-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-1-(4-iodophenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(I)=CC=3)C2=N1 BVHBUYVDFKRVFF-UHFFFAOYSA-N 0.000 claims description 2
- NRJALDGHSKBUCL-UHFFFAOYSA-N n-(3-methoxyphenyl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(OC)C=CC=3)=NC=C2C=N1 NRJALDGHSKBUCL-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
- WDOLOEKDCMUNER-UHFFFAOYSA-N n-[3-chloro-4-(methylsulfonylmethyl)phenyl]-1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(Cl)C(CS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 WDOLOEKDCMUNER-UHFFFAOYSA-N 0.000 claims description 2
- SAUVANXMDWCHCE-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-1-(2-phenylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=N1 SAUVANXMDWCHCE-UHFFFAOYSA-N 0.000 claims description 2
- DRDUZQHVFDFHIY-UHFFFAOYSA-N n-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-n-propan-2-ylmethanesulfonamide Chemical compound C1=CC(N(C(C)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 DRDUZQHVFDFHIY-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- GHFQOHGVZJRMQN-UHFFFAOYSA-N n-[4-[2-(2-chloroethyl)tetrazol-5-yl]phenyl]-1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound ClCCN1N=NC(C=2C=CC(NC=3N=C4N(C5CCCCCC5)N=CC4=CN=3)=CC=2)=N1 GHFQOHGVZJRMQN-UHFFFAOYSA-N 0.000 claims description 2
- PEVOFSWKTNCOEO-UHFFFAOYSA-N n-[4-[[1-(2-phenylphenyl)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(=CC=CC=3)C=3C=CC=CC=3)C2=N1 PEVOFSWKTNCOEO-UHFFFAOYSA-N 0.000 claims description 2
- HTQCIAXTJMTNNY-UHFFFAOYSA-N n-[4-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(NS(C)(=O)=O)=CC=4)=NC=C3C=N2)=C1 HTQCIAXTJMTNNY-UHFFFAOYSA-N 0.000 claims description 2
- IKIGJRNWZVIPEQ-UHFFFAOYSA-N n-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylmethanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N(C)S(C)(=O)=O)=NC=C2C=N1 IKIGJRNWZVIPEQ-UHFFFAOYSA-N 0.000 claims description 2
- MPWWQOGTWUNDHR-UHFFFAOYSA-N n-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]cyclopropanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(NS(=O)(=O)C4CC4)=CC=3)=NC=C2C=N1 MPWWQOGTWUNDHR-UHFFFAOYSA-N 0.000 claims description 2
- GCCCTCJFSDCQKO-UHFFFAOYSA-N n-[5-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]pyrimidin-2-yl]methanesulfonamide Chemical compound C1=NC(NS(=O)(=O)C)=NC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 GCCCTCJFSDCQKO-UHFFFAOYSA-N 0.000 claims description 2
- FTKQHVSXQJAEOW-UHFFFAOYSA-N n-[5-[[1-[(3-hydroxyphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyridin-2-yl]methanesulfonamide Chemical compound C1=NC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2CC=3C=C(O)C=CC=3)C2=N1 FTKQHVSXQJAEOW-UHFFFAOYSA-N 0.000 claims description 2
- 201000008106 ocular cancer Diseases 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229940049953 phenylacetate Drugs 0.000 claims description 2
- 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 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 108060006633 protein kinase Proteins 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 230000002485 urinary effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- GLQSIADXDPOALK-KRWDZBQOSA-N n-(4-morpholin-4-ylphenyl)-1-[(1s)-1-phenylethyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1([C@H](C)N2C3=NC(NC=4C=CC(=CC=4)N4CCOCC4)=NC=C3C=N2)=CC=CC=C1 GLQSIADXDPOALK-KRWDZBQOSA-N 0.000 claims 2
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 claims 1
- SLWXRUGEEGKHRS-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-n-(4-methylsulfanylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(SC)=CC=3)=NC=C2C=N1 SLWXRUGEEGKHRS-UHFFFAOYSA-N 0.000 claims 1
- YIWQBKPKRBUMCW-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=N1 YIWQBKPKRBUMCW-UHFFFAOYSA-N 0.000 claims 1
- RLLTZIQOXRLOKD-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-n-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(OC(F)(F)F)=CC=3)=NC=C2C=N1 RLLTZIQOXRLOKD-UHFFFAOYSA-N 0.000 claims 1
- CUGFPQWKFARRJQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(4-methylsulfanylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(SC)=CC=3)=NC=C2C=N1 CUGFPQWKFARRJQ-UHFFFAOYSA-N 0.000 claims 1
- SOMQXJCZKFSGHR-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C=N1 SOMQXJCZKFSGHR-UHFFFAOYSA-N 0.000 claims 1
- ZLQISKMDKDTLHV-UHFFFAOYSA-N 1-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 ZLQISKMDKDTLHV-UHFFFAOYSA-N 0.000 claims 1
- CZQHHUQMWBAGCO-UHFFFAOYSA-N 1-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 CZQHHUQMWBAGCO-UHFFFAOYSA-N 0.000 claims 1
- SUHFWBWUWZPUAT-UHFFFAOYSA-N 1-cycloheptyl-n-(4-thiomorpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CSCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 SUHFWBWUWZPUAT-UHFFFAOYSA-N 0.000 claims 1
- AOQAAVXIWZSHIB-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(2-methyltetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CN1N=NC(C=2C=CC(NC=3N=C4N(C5CCCCCC5)N=CC4=CN=3)=CC=2)=N1 AOQAAVXIWZSHIB-UHFFFAOYSA-N 0.000 claims 1
- FOCNLUQWJYCAKS-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(methylsulfonylmethyl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(CS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 FOCNLUQWJYCAKS-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- CJSBUFUIJSGDQF-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-1-(4-ethylpiperazin-1-yl)ethanone Chemical compound C1CN(CC)CCN1C(=O)CC(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 CJSBUFUIJSGDQF-UHFFFAOYSA-N 0.000 claims 1
- IHLCIFVPIGSHHS-UHFFFAOYSA-N 2-methoxy-4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(OC)C(O)=CC=3)=NC=C2C=N1 IHLCIFVPIGSHHS-UHFFFAOYSA-N 0.000 claims 1
- JIZINHLGUOALGX-UHFFFAOYSA-N 2-methoxy-5-[[1-(4-methoxy-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(O)C(OC)=CC=3)=NC=C2C=N1 JIZINHLGUOALGX-UHFFFAOYSA-N 0.000 claims 1
- LTUNEEBTZOCCDO-UHFFFAOYSA-N 3-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C(O)C=CC=4)=NC=C3C=N2)=C1 LTUNEEBTZOCCDO-UHFFFAOYSA-N 0.000 claims 1
- NPTJPXPAMQOJML-UHFFFAOYSA-N 4-methoxy-1-n-[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]benzene-1,3-diamine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(N)C(OC)=CC=3)=NC=C2C=N1 NPTJPXPAMQOJML-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 102000016736 Cyclin Human genes 0.000 claims 1
- 108050006400 Cyclin Proteins 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims 1
- HWPGNNZUONMINL-UHFFFAOYSA-N methyl 3-[4-[[1-(4-methoxyphenyl)pyrazolo[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=3C=CC(OC)=CC=3)C2=N1 HWPGNNZUONMINL-UHFFFAOYSA-N 0.000 claims 1
- QGGYIEQRZQXKMP-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)methanesulfonamide Chemical group CS(=O)(=O)NCCN1CCOCC1 QGGYIEQRZQXKMP-UHFFFAOYSA-N 0.000 claims 1
- DCNAEEPZTJYBNZ-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1h-pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2)C2=N1 DCNAEEPZTJYBNZ-UHFFFAOYSA-N 0.000 claims 1
- FGZOFXYEPAPOMM-UHFFFAOYSA-N n-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)NC(C=C1)=CC=C1NC(N=C12)=NC=C1C=NN2C1CCCCCC1 FGZOFXYEPAPOMM-UHFFFAOYSA-N 0.000 claims 1
- CGEKMFYYLMQCKN-UHFFFAOYSA-N n-[4-[[1-(4-methoxy-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(NS(C)(=O)=O)=CC=3)=NC=C2C=N1 CGEKMFYYLMQCKN-UHFFFAOYSA-N 0.000 claims 1
- MUJPXGWSJHJOJE-UHFFFAOYSA-N n-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(NC(C)=O)=CC=3)=NC=C2C=N1 MUJPXGWSJHJOJE-UHFFFAOYSA-N 0.000 claims 1
- XDIIJQFNVMXIJQ-UHFFFAOYSA-N n-methylacetohydrazide Chemical compound CN(N)C(C)=O XDIIJQFNVMXIJQ-UHFFFAOYSA-N 0.000 claims 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- HHVIWHSLTBBAGK-UHFFFAOYSA-N piperazin-1-ylphosphonic acid Chemical compound OP(O)(=O)N1CCNCC1 HHVIWHSLTBBAGK-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 208000037964 urogenital cancer Diseases 0.000 claims 1
- ILJNKUSQFWZNCT-UHFFFAOYSA-N 1-(furan-2-ylmethyl)-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=CC2=CN=C(NC=3C=CC(=CC=3)N3CCNCC3)N=C2N1CC1=CC=CO1 ILJNKUSQFWZNCT-UHFFFAOYSA-N 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- ZMINETKADICQPZ-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)N4CCN(C)CC4)=NC=C3C=N2)=C1 ZMINETKADICQPZ-UHFFFAOYSA-N 0.000 description 1
- CZYXHXGZCOOFJN-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-n-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=NN2C=3C(=CC(OC)=CC=3)C)C2=N1 CZYXHXGZCOOFJN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- HWRHBUPIPIHFPC-FQEVSTJZSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-[2-(4-nitrophenyl)ethyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1CCNC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 HWRHBUPIPIHFPC-FQEVSTJZSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- GSFBKTFJGAQAHB-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(2-ethenyltetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=CN1N=NC(C=2C=CC(NC=3N=C4N(C5CCCCCC5)N=CC4=CN=3)=CC=2)=N1 GSFBKTFJGAQAHB-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- KIPQPQGBKAPXGZ-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-n-methylacetamide Chemical compound C1=CC(CC(=O)NC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 KIPQPQGBKAPXGZ-UHFFFAOYSA-N 0.000 description 1
- TYFBSIQEIUWHAG-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 TYFBSIQEIUWHAG-UHFFFAOYSA-N 0.000 description 1
- ZDBMVTIWOSBGMD-UHFFFAOYSA-N 2-[4-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 ZDBMVTIWOSBGMD-UHFFFAOYSA-N 0.000 description 1
- DINXLRXOTQBCNI-UHFFFAOYSA-N 2-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]ethanol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(CCO)=CC=3)=NC=C2C=N1 DINXLRXOTQBCNI-UHFFFAOYSA-N 0.000 description 1
- IOAMCESAONAQEV-UHFFFAOYSA-N 2-methoxy-4-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C(OC)C(O)=CC=4)=NC=C3C=N2)=C1 IOAMCESAONAQEV-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- QLGVACCKJRKICA-UHFFFAOYSA-N 4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 QLGVACCKJRKICA-UHFFFAOYSA-N 0.000 description 1
- GVOXMLRIPSSWTB-UHFFFAOYSA-N 4-[6-(4-aminoanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenol Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C=3C=CC(O)=CC=3)C2=N1 GVOXMLRIPSSWTB-UHFFFAOYSA-N 0.000 description 1
- MKVMQIFACXQHDI-SFHVURJKSA-N 4-[[1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-n'-hydroxybenzenecarboximidamide Chemical compound C1=CC(C(=N/O)/N)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 MKVMQIFACXQHDI-SFHVURJKSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- SVNGUXYXAAIQLJ-UHFFFAOYSA-N C1CC2=C(C=CC=C2C1N3C4=NC(=NC=C4C=N3)NC5=CC=C(C=C5)N)C6=CC=CC=C6C(=O)O Chemical compound C1CC2=C(C=CC=C2C1N3C4=NC(=NC=C4C=N3)NC5=CC=C(C=C5)N)C6=CC=CC=C6C(=O)O SVNGUXYXAAIQLJ-UHFFFAOYSA-N 0.000 description 1
- FFSNZQAMGPMHQO-UHFFFAOYSA-N CN1CCN(CC1)C2=CC=C(C=C2)NC3=NC=C4C=NN(C4=N3)C5CCC6=C(C=CC=C56)C7=CC=CC=C7C(=O)O Chemical compound CN1CCN(CC1)C2=CC=C(C=C2)NC3=NC=C4C=NN(C4=N3)C5CCC6=C(C=CC=C56)C7=CC=CC=C7C(=O)O FFSNZQAMGPMHQO-UHFFFAOYSA-N 0.000 description 1
- PHASHKHNXXSYJE-UHFFFAOYSA-N CS(=O)(=O)N(C1=CC=C(C=C1)NC2=NC=C3C=NN(C3=N2)C4CCC5=C(C=CC=C45)C6=CC=CC=C6C(=O)O)S(=O)(=O)C Chemical compound CS(=O)(=O)N(C1=CC=C(C=C1)NC2=NC=C3C=NN(C3=N2)C4CCC5=C(C=CC=C45)C6=CC=CC=C6C(=O)O)S(=O)(=O)C PHASHKHNXXSYJE-UHFFFAOYSA-N 0.000 description 1
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 1
- YAUNIGRRZBDFJH-UHFFFAOYSA-N [1-[6-[4-[bis(methylsulfonyl)amino]anilino]pyrazolo[3,4-d]pyrimidin-1-yl]-2,3-dihydro-1H-inden-4-yl] ditert-butyl phosphate Chemical compound CC(C)(C)OP(=O)(Oc1cccc2C(CCc12)n1ncc2cnc(Nc3ccc(cc3)N(S(C)(=O)=O)S(C)(=O)=O)nc12)OC(C)(C)C YAUNIGRRZBDFJH-UHFFFAOYSA-N 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 208000024519 eye neoplasm Diseases 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- GJKRIXGECJEURU-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C2OCOC2=CC=C1NC(N=C12)=NC=C1C=NN2C1CCCCCC1 GJKRIXGECJEURU-UHFFFAOYSA-N 0.000 description 1
- QBMAGORLPVPXCO-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(OC)C(OC)=CC=3)=NC=C2C=N1 QBMAGORLPVPXCO-UHFFFAOYSA-N 0.000 description 1
- ICSYRROXXVMJEA-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-(2-phenylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=N1 ICSYRROXXVMJEA-UHFFFAOYSA-N 0.000 description 1
- FTXZNUXMOADWHI-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-(naphthalen-1-ylmethyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 FTXZNUXMOADWHI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- VQLBPSKCCYEXFF-FQEVSTJZSA-N n-[2-(4-aminophenyl)ethyl]-1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(N)=CC=C1CCNC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 VQLBPSKCCYEXFF-FQEVSTJZSA-N 0.000 description 1
- RPQLNPIJBWIIHD-UHFFFAOYSA-N n-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 RPQLNPIJBWIIHD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- PARUULGUCQEWNM-UHFFFAOYSA-N n-[5-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]pyridin-2-yl]methanesulfonamide Chemical compound C1=NC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 PARUULGUCQEWNM-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- LMQGGWATBUQBNT-UHFFFAOYSA-N tert-butyl 7-methyl-4-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrazolo[3,4-d]pyrimidin-1-yl]indole-1-carboxylate Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C=4C=CN(C=4C(C)=CC=3)C(=O)OC(C)(C)C)C2=N1 LMQGGWATBUQBNT-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89838207P | 2007-01-30 | 2007-01-30 | |
| US89830007P | 2007-01-30 | 2007-01-30 | |
| PCT/US2008/001230 WO2008094602A2 (en) | 2007-01-30 | 2008-01-30 | 1-h-pyrazolo (3,4b) pyrimidine derivatives and their use as modulators of mitotic kinases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010532312A JP2010532312A (ja) | 2010-10-07 |
| JP2010532312A5 true JP2010532312A5 (https=) | 2012-04-05 |
Family
ID=39469519
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009548293A Withdrawn JP2010532312A (ja) | 2007-01-30 | 2008-01-30 | １−ｈ−ピラゾロ（３，４ｂ）ピリミジン誘導体および有糸分裂キナーゼの調節剤としてのその使用 |
| JP2009548286A Withdrawn JP2010516812A (ja) | 2007-01-30 | 2008-01-30 | 有糸分裂キナーゼの調節剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009548286A Withdrawn JP2010516812A (ja) | 2007-01-30 | 2008-01-30 | 有糸分裂キナーゼの調節剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20110281821A9 (https=) |
| EP (2) | EP2108020A2 (https=) |
| JP (2) | JP2010532312A (https=) |
| AU (2) | AU2008211172A1 (https=) |
| CA (2) | CA2676665A1 (https=) |
| WO (2) | WO2008094575A2 (https=) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2676665A1 (en) * | 2007-01-30 | 2008-08-07 | Biogen Idec Ma Inc. | Modulators of mitotic kinases |
| TWI490214B (zh) | 2008-05-30 | 2015-07-01 | 艾德克 上野股份有限公司 | 苯或噻吩衍生物及該等作為ｖａｐ－１抑制劑之用途 |
| CN104592231A (zh) | 2008-06-10 | 2015-05-06 | Abbvie公司 | 新的三环化合物 |
| CN102356083B (zh) * | 2009-03-20 | 2014-10-15 | 内尔维阿诺医学科学有限公司 | 用于胸腺瘤治疗的激酶抑制剂的用途 |
| TW201100441A (en) | 2009-06-01 | 2011-01-01 | Osi Pharm Inc | Amino pyrimidine anticancer compounds |
| CA2775009A1 (en) * | 2009-10-20 | 2011-04-28 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as jak inhibitors |
| PH12012501000A1 (en) | 2009-12-01 | 2013-02-11 | Abbvie Inc | Novel tricyclic compounds |
| RU2711869C3 (ru) | 2009-12-01 | 2022-02-02 | Эббви Инк. | Имидазопирролопиразиновые производные, полезные для лечения заболеваний, вызванных аномальной активностью протеинкиназ Jak1, Jak3 или Syk |
| WO2011134831A1 (en) | 2010-04-30 | 2011-11-03 | Cellzome Limited | Pyrazole compounds as jak inhibitors |
| WO2011156698A2 (en) * | 2010-06-11 | 2011-12-15 | Abbott Laboratories | NOVEL PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS |
| US9040545B2 (en) | 2010-08-20 | 2015-05-26 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as selective JAK inhibitors |
| BR112013011520A2 (pt) * | 2010-11-19 | 2019-09-24 | Hoffmann La Roche | pirazolo piridinas e pirazolo piridinas e seu uso como inibidores de tyk2 |
| EP2646448B1 (en) | 2010-11-29 | 2017-08-30 | OSI Pharmaceuticals, LLC | Macrocyclic kinase inhibitors |
| WO2012143320A1 (en) | 2011-04-18 | 2012-10-26 | Cellzome Limited | (7h-pyrrolo[2,3-d]pyrimidin-2-yl)amine compounds as jak3 inhibitors |
| WO2013017480A1 (en) * | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
| WO2013017479A1 (en) * | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
| JP6014155B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドＸｅｎｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| US9630929B2 (en) | 2011-10-31 | 2017-04-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| US9670213B2 (en) * | 2012-05-14 | 2017-06-06 | East China University Of Science And Technology | Pteridine ketone derivative and applications thereof as EGFR, BLK, and FLT3 inhibitor |
| SG11201408284VA (en) * | 2012-05-22 | 2015-02-27 | Xenon Pharmaceuticals Inc | N-substituted benzamides and their use in the treatment of pain |
| US10071957B2 (en) | 2012-07-06 | 2018-09-11 | Genentech, Inc. | N-substituted benzamides and methods of use thereof |
| EP2914253B1 (en) * | 2012-11-05 | 2018-01-03 | NantBioScience, Inc. | Cyclic sulfonamide containing derivatives as inhibitors of hedgehog signaling pathway |
| US9550775B2 (en) | 2013-03-14 | 2017-01-24 | Genentech, Inc. | Substituted triazolopyridines and methods of use thereof |
| MX2015010775A (es) | 2013-03-15 | 2016-04-25 | Genentech Inc | Benzoxazoles sustituidos y metodos para usarlos. |
| CR20160296A (es) | 2013-11-27 | 2016-09-20 | Genentech Inc | Benzamidas sustituidas y métodos para usarlas |
| CN106715418A (zh) | 2014-07-07 | 2017-05-24 | 基因泰克公司 | 治疗化合物及其使用方法 |
| US10934291B2 (en) | 2014-09-25 | 2021-03-02 | Duke University | Kinase inhibitors and related methods of use |
| GB201501115D0 (en) | 2015-01-23 | 2015-03-11 | Univ Dundee | Compounds |
| TWI726861B (zh) | 2015-01-23 | 2021-05-11 | 英商葛蘭素史克智慧財產發展有限公司 | 吡唑并-嘧啶化合物、其鹽及其用途 |
| JP2018520107A (ja) | 2015-05-22 | 2018-07-26 | ジェネンテック， インコーポレイテッド | 置換ベンズアミド及びその使用方法 |
| EP3341353A1 (en) | 2015-08-27 | 2018-07-04 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| CN108290881B (zh) | 2015-09-28 | 2021-12-07 | 健泰科生物技术公司 | 治疗性化合物和其使用方法 |
| SG10201913990RA (en) | 2015-10-16 | 2020-03-30 | Abbvie Inc | PROCESSES FOR THE PREPARATION OF (3S,4R)-3-ETHYL-4-(3H-IMIDAZO[1,2-a]PYRROLO[2,3-e]-PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)PYRROLIDINE-1-CARBOXAMIDE AND SOLID STATE FORMS THEREOF |
| US11512092B2 (en) | 2015-10-16 | 2022-11-29 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US11365198B2 (en) | 2015-10-16 | 2022-06-21 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US12365689B2 (en) | 2015-10-16 | 2025-07-22 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US10550126B2 (en) | 2015-10-16 | 2020-02-04 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-A]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US11524964B2 (en) | 2015-10-16 | 2022-12-13 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US11773106B2 (en) | 2015-10-16 | 2023-10-03 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US10899732B2 (en) | 2015-11-25 | 2021-01-26 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| EP3854782A1 (en) | 2016-03-30 | 2021-07-28 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| US20190152992A1 (en) | 2016-06-29 | 2019-05-23 | Orion Corporation | Benzodioxane derivatives and their pharmaceutical use |
| AU2017347549A1 (en) | 2016-10-17 | 2019-05-02 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| JP2020511511A (ja) | 2017-03-24 | 2020-04-16 | ジェネンテック， インコーポレイテッド | ナトリウムチャネル阻害剤としての４−ピペリジン−ｎ−（ピリミジン−４−イル）クロマン−７−スルホンアミド誘導体 |
| EP3706750A1 (en) | 2017-11-06 | 2020-09-16 | RAPT Therapeutics, Inc. | Chemokine receptor modulators for treatment of epstein barr virus positive cancer |
| AR114263A1 (es) | 2018-02-26 | 2020-08-12 | Genentech Inc | Compuestos terapéuticos y métodos para utilizarlos |
| WO2019191702A1 (en) | 2018-03-30 | 2019-10-03 | F. Hoffmann-La Roche Ag | Substituted hydro-pyrido-azines as sodium channel inhibitors |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
| EP3802544A1 (en) * | 2018-06-05 | 2021-04-14 | RAPT Therapeutics, Inc. | Pyrazolo-pyrimidin-amino-cycloalkyl compounds and their therapeutic uses |
| CA3139277A1 (en) | 2019-05-08 | 2020-11-12 | Vimalan Biosciences, Inc. | Jak inhibitors |
| PH12021552998A1 (en) * | 2019-06-18 | 2023-08-14 | Hoffmann La Roche | Pyrazolopyrimidine sulfone inhibitors of jak kinases and uses thereof |
| MX2022001702A (es) | 2019-08-08 | 2022-04-20 | Vimalan Biosciences Inc | Inhibidores de jak. |
| US20230065636A1 (en) * | 2020-01-15 | 2023-03-02 | KSQ Therapeutics, Inc. | Compositions of substituted pyrazolopyrimidines and uses thereof |
| KR20230098186A (ko) | 2020-10-30 | 2023-07-03 | 케이에스큐 세러퓨틱스 인코포레이티드 | 치환된 피라졸로피리미딘의 고체 상태 형태 및 이의 용도 |
| EP4349838A4 (en) * | 2021-05-28 | 2025-08-13 | Jiangsu Tasly Diyi Pharmaceutical Co Ltd | WEE1 INHIBITOR AND ITS USE |
| US12084453B2 (en) | 2021-12-10 | 2024-09-10 | Incyte Corporation | Bicyclic amines as CDK12 inhibitors |
| CN118126043B (zh) * | 2022-12-02 | 2025-01-28 | 沈阳药科大学 | 一种高选择性的plk4抑制剂及制备方法和应用 |
| WO2024238570A1 (en) * | 2023-05-15 | 2024-11-21 | Aleksia Therapeutics, Inc. | Cdk2 inhibitor pyrazolopyrimidine compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA06002997A (es) * | 2003-09-18 | 2007-02-08 | Conforma Therapeutics Corp | Novedosos compuestos heterociclicos como inhibidores- hsp90. |
| JP2008513463A (ja) * | 2004-09-15 | 2008-05-01 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | チアゾロピリジンキナーゼ阻害剤 |
| EP1846408B1 (en) * | 2005-01-14 | 2013-03-20 | Janssen Pharmaceutica NV | 5-membered annelated heterocyclic pyrimidines as kinase inhibitors |
| WO2006074984A1 (en) * | 2005-01-14 | 2006-07-20 | Janssen Pharmaceutica N.V. | Pyrazolopyrimidines as cell cycle kinase inhibitors |
| WO2006091737A1 (en) * | 2005-02-24 | 2006-08-31 | Kemia, Inc. | Modulators of gsk-3 activity |
| CA2676665A1 (en) * | 2007-01-30 | 2008-08-07 | Biogen Idec Ma Inc. | Modulators of mitotic kinases |
-
2008
- 2008-01-30 CA CA002676665A patent/CA2676665A1/en not_active Abandoned
- 2008-01-30 WO PCT/US2008/001195 patent/WO2008094575A2/en not_active Ceased
- 2008-01-30 WO PCT/US2008/001230 patent/WO2008094602A2/en not_active Ceased
- 2008-01-30 EP EP08724974A patent/EP2108020A2/en not_active Withdrawn
- 2008-01-30 US US12/525,174 patent/US20110281821A9/en not_active Abandoned
- 2008-01-30 US US12/525,155 patent/US20100190787A1/en not_active Abandoned
- 2008-01-30 CA CA002676658A patent/CA2676658A1/en not_active Abandoned
- 2008-01-30 AU AU2008211172A patent/AU2008211172A1/en not_active Abandoned
- 2008-01-30 JP JP2009548293A patent/JP2010532312A/ja not_active Withdrawn
- 2008-01-30 AU AU2008211108A patent/AU2008211108A1/en not_active Abandoned
- 2008-01-30 EP EP08724941A patent/EP2108019A2/en not_active Withdrawn
- 2008-01-30 JP JP2009548286A patent/JP2010516812A/ja not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010532312A5 (https=) | ||
| JP2010516812A5 (https=) | ||
| JP2010532312A (ja) | １−ｈ−ピラゾロ（３，４ｂ）ピリミジン誘導体および有糸分裂キナーゼの調節剤としてのその使用 | |
| CN104327084B (zh) | Bcr‑abl的小分子豆蔻酸酯抑制剂及其使用方法 | |
| PT2316831E (pt) | 2-(morfolin-4-il)pirimidinas como inibidores da fosfatidilinositol (pi) quinase e a sua utilização no tratamento do cancro | |
| AU2014373773C1 (en) | Compounds and methods of use | |
| JP5656874B2 (ja) | Ｐｄｅ９阻害剤として使用されるアミノヘテロ環化合物 | |
| RU2004106783A (ru) | Производные 4-амино-6-фенилпирроло[2, 3] пиримидина | |
| JP5602729B2 (ja) | キナゾリン化合物、同化合物を含む医薬組成物及び同化合物を含む治療薬 | |
| JP2005514398A5 (https=) | ||
| RU2437888C2 (ru) | Ингибиторы фосфоинозитид-3-киназы и содержащие их фармацевтические композиции | |
| TWI487701B (zh) | 作為蛋白質激酶抑制劑之化合物及組合物 | |
| JP2011502996A (ja) | サイトカインインヒビター | |
| AU2018271284A1 (en) | Pyrimidine FGFR4 inhibitors | |
| JP2017125037A (ja) | イミダゾピロリジノン化合物 | |
| ZA200502873B (en) | Substituted piperazines (1,4) diaszepines, and 2,5-diazabicyclo (2.2.1) heptanes as histamine H1 and/or H3 antagonists or histamine H3 reverse antagonists | |
| ES2759277T3 (es) | Cromeno y 1,1a,2,7b-tetrahidrociclopropa[c]cromeno piridopiracinadionionas como moduladores de gamma-secretasa | |
| RU2011114559A (ru) | Триазин, пиримидин, аналоги пиридина и их применение в качестве терапевтических агентов и диагностических проб | |
| JP2011510995A5 (https=) | ||
| CN102947305A (zh) | 用于激酶调节的化合物和方法及其适应症 | |
| BG106853A (bg) | Антагонисти на кортикотропин освобождаващ фактор | |
| RU99128111A (ru) | Новые соединения | |
| HRP20130106T1 (hr) | Imidazotriazini i imidazopirimidini kao inhibitori kinaze | |
| JP2009519979A5 (https=) | ||
| JP2007514759A (ja) | キナーゼ阻害剤 |