JP2010532312A5 - - Google Patents
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- 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- Withdrawn
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- -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
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- 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
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| WO2010106028A1 (en) * | 2009-03-20 | 2010-09-23 | Nerviano Medical Sciences S.R.L. | Use of a kinase inhibitor for the treatment of thymoma |
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| EA022120B1 (ru) * | 2009-10-20 | 2015-11-30 | Целльзом Лимитид | Аналоги гетероциклил пиразолопиримидина в качестве ингибиторов jak |
| EP4782062A2 (en) | 2009-12-01 | 2026-07-29 | AbbVie Inc. | Novel tricyclic compounds |
| JP2013512282A (ja) | 2009-12-01 | 2013-04-11 | アボット・ラボラトリーズ | 新規三環式化合物 |
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| WO2011156698A2 (en) * | 2010-06-11 | 2011-12-15 | Abbott Laboratories | NOVEL PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS |
| JP2013534233A (ja) * | 2010-08-20 | 2013-09-02 | セルゾーム リミティッド | 選択的ｊａｋ阻害剤としてのヘテロシクリルピラゾロピリミジン類似体 |
| KR20140009259A (ko) * | 2010-11-19 | 2014-01-22 | 에프. 호프만-라 로슈 아게 | 피라졸로피리딘 및 tyk2 억제제로서 이의 용도 |
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| WO2013017480A1 (en) * | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
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| NZ546611A (en) * | 2003-09-18 | 2010-02-26 | Conforma Therapeutics Corp | Novel heterocyclic compounds as HSP90-inhibitors |
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| ES2345997T3 (es) * | 2005-01-14 | 2010-10-07 | Janssen Pharmaceutica Nv | Pirazolopiramidinas como inhibidores de las quinasas del ciclo celular. |
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| AU2008211172A1 (en) * | 2007-01-30 | 2008-08-07 | Biogen Idec Ma Inc. | 1-H-pyrazolo(3,4B)pyrimidine derivatives and their use as modulators of mitotic kinases |
-
2008
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- 2008-01-30 EP EP08724974A patent/EP2108020A2/en not_active Withdrawn
- 2008-01-30 WO PCT/US2008/001230 patent/WO2008094602A2/en not_active Ceased
- 2008-01-30 JP JP2009548286A patent/JP2010516812A/ja not_active Withdrawn
- 2008-01-30 US US12/525,174 patent/US20110281821A9/en not_active Abandoned
- 2008-01-30 EP EP08724941A patent/EP2108019A2/en not_active Withdrawn
- 2008-01-30 CA CA002676658A patent/CA2676658A1/en not_active Abandoned
- 2008-01-30 AU AU2008211108A patent/AU2008211108A1/en not_active Abandoned
- 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 US US12/525,155 patent/US20100190787A1/en not_active Abandoned
- 2008-01-30 JP JP2009548293A patent/JP2010532312A/ja not_active Withdrawn
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