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- Withdrawn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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| 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 |
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| AU (2) | AU2008211172A1 (https=) |
| CA (2) | CA2676658A1 (https=) |
| WO (2) | WO2008094575A2 (https=) |
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| EP2108019A2 (en) * | 2007-01-30 | 2009-10-14 | Biogen Idec MA, Inc. | 1-h-pyrazolo[3,4b]pyrimidine derivatives and their use as 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 |
| JP5748659B2 (ja) | 2008-06-10 | 2015-07-15 | アッヴィ・インコーポレイテッド | 新規な三環式化合物 |
| JP5650193B2 (ja) * | 2009-03-20 | 2015-01-07 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | 胸腺腫の治療のためのキナーゼ阻害剤の使用 |
| TW201100441A (en) | 2009-06-01 | 2011-01-01 | Osi Pharm Inc | Amino pyrimidine anticancer compounds |
| US9242987B2 (en) | 2009-10-20 | 2016-01-26 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as JAK inhibitors |
| KR20120102724A (ko) | 2009-12-01 | 2012-09-18 | 아보트 러보러터리즈 | 신규한 트리사이클릭 화합물 |
| PE20121336A1 (es) * | 2009-12-01 | 2012-11-03 | Abbvie Inc | Nuevos compuestos triciclicos |
| BR112012027803A2 (pt) | 2010-04-30 | 2016-08-09 | Cellzome Ltd | compostos de pirazol como inibidores de jak |
| US8637529B2 (en) | 2010-06-11 | 2014-01-28 | AbbYie Inc. | Pyrazolo[3,4-d]pyrimidine compounds |
| US9040545B2 (en) | 2010-08-20 | 2015-05-26 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as selective JAK inhibitors |
| MX2013005445A (es) * | 2010-11-19 | 2013-07-29 | Hoffmann La Roche | Pirazolopiridinas y el uso de pirazolopiridinas como inhibidores de tirosina cinasa 2 (tyk2). |
| US9133224B2 (en) | 2010-11-29 | 2015-09-15 | 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 |
| RU2014121984A (ru) | 2011-10-31 | 2015-12-10 | Ксенон Фармасьютикалз Инк. | Бензолсульфонамидные соединения и их применение в качестве терапевтических средств |
| 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 |
| JP6114820B2 (ja) * | 2012-05-14 | 2017-04-12 | イースト チャイナ ユニバーシティ オブ サイエンス アンド テクノロジー | プテリジノン誘導体およびｅｇｆｒ、ｂｌｋ、ｆｌｔ３の阻害剤としての応用 |
| CN104718188B (zh) | 2012-05-22 | 2018-08-21 | 基因泰克公司 | N-取代的苯甲酰胺类及其在治疗疼痛中的用途 |
| KR101663436B1 (ko) | 2012-07-06 | 2016-10-06 | 제넨테크, 인크. | N-치환된 벤즈아미드 및 이의 사용 방법 |
| CA2890002A1 (en) * | 2012-11-05 | 2014-05-08 | Nant Holdings Ip, Llc | Cyclic sulfonamide containing derivatives as inhibitors of hedgehog signaling pathway |
| RU2015143906A (ru) | 2013-03-14 | 2017-04-18 | Дженентек, Инк. | Замещенные триазолопиридины и способы их применения |
| BR112015023397A2 (pt) | 2013-03-15 | 2017-07-18 | Genentech Inc | benzoxazois substituídos e métodos de uso dos mesmos |
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| JP2017525677A (ja) | 2014-07-07 | 2017-09-07 | ジェネンテック， インコーポレイテッド | 治療用化合物及びその使用方法 |
| WO2016049500A1 (en) | 2014-09-25 | 2016-03-31 | Duke University | Kinase inhibitors and related methods of use |
| US10253028B2 (en) | 2015-01-23 | 2019-04-09 | Glaxosmithkline Intellectual Property Development Limited | Pyrazolo[3,4-D]pyrimidin derivative and its use for the treatment of leishmaniasis |
| GB201501115D0 (en) | 2015-01-23 | 2015-03-11 | Univ Dundee | Compounds |
| HK1252567A1 (zh) | 2015-05-22 | 2019-05-31 | 基因泰克公司 | 被取代的苯甲酰胺和其使用方法 |
| JP2018526371A (ja) | 2015-08-27 | 2018-09-13 | ジェネンテック， インコーポレイテッド | 治療化合物及びその使用方法 |
| CA2999769A1 (en) | 2015-09-28 | 2017-04-06 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
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| 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 |
| 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 |
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| 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 |
| 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 |
| US11780848B2 (en) | 2015-10-16 | 2023-10-10 | 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 |
| EP3380466A1 (en) | 2015-11-25 | 2018-10-03 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| EP3436432B1 (en) | 2016-03-30 | 2021-01-27 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
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| 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 |
| RU2020118594A (ru) | 2017-11-06 | 2021-12-09 | Рапт Терапьютикс, Инк. | Противораковые агенты |
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| JP7617030B2 (ja) | 2019-05-08 | 2025-01-17 | ビマラン バイオサイエンシーズ，インク． | Ｊａｋ阻害剤 |
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| KR20220051351A (ko) * | 2019-08-08 | 2022-04-26 | 비말란 바이오사이언스즈, 인크. | Jak 억제제 |
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| KR20230098186A (ko) * | 2020-10-30 | 2023-07-03 | 케이에스큐 세러퓨틱스 인코포레이티드 | 치환된 피라졸로피리미딘의 고체 상태 형태 및 이의 용도 |
| JP2024520969A (ja) * | 2021-05-28 | 2024-05-28 | 江蘇天士力帝益薬業有限公司 | Ｗｅｅ１阻害剤とその用途 |
| WO2023107705A1 (en) | 2021-12-10 | 2023-06-15 | 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 |
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| KR20060070572A (ko) * | 2003-09-18 | 2006-06-23 | 콘포마 세러퓨틱스 코포레이션 | Ｈｓｐ90-저해제로서의 신규 헤테로시클릭 화합물 |
| 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 |
| DE602006014502D1 (de) * | 2005-01-14 | 2010-07-08 | Janssen Pharmaceutica Nv | Pyrazolopyrimidine als zellzyklus-kinasehemmer |
| EP1846408B1 (en) * | 2005-01-14 | 2013-03-20 | Janssen Pharmaceutica NV | 5-membered annelated heterocyclic pyrimidines as kinase inhibitors |
| WO2006091737A1 (en) * | 2005-02-24 | 2006-08-31 | Kemia, Inc. | Modulators of gsk-3 activity |
| EP2108019A2 (en) * | 2007-01-30 | 2009-10-14 | Biogen Idec MA, Inc. | 1-h-pyrazolo[3,4b]pyrimidine derivatives and their use as modulators of mitotic kinases |
-
2008
- 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 JP JP2009548286A patent/JP2010516812A/ja not_active Withdrawn
- 2008-01-30 AU AU2008211172A patent/AU2008211172A1/en not_active Abandoned
- 2008-01-30 EP EP08724974A patent/EP2108020A2/en not_active Withdrawn
- 2008-01-30 US US12/525,155 patent/US20100190787A1/en not_active Abandoned
- 2008-01-30 JP JP2009548293A patent/JP2010532312A/ja not_active Withdrawn
- 2008-01-30 WO PCT/US2008/001195 patent/WO2008094575A2/en not_active Ceased
- 2008-01-30 CA CA002676665A patent/CA2676665A1/en not_active Abandoned
- 2008-01-30 WO PCT/US2008/001230 patent/WO2008094602A2/en not_active Ceased
- 2008-01-30 US US12/525,174 patent/US20110281821A9/en not_active Abandoned
- 2008-01-30 AU AU2008211108A patent/AU2008211108A1/en not_active Abandoned
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