JP2009522284A5

JP2009522284A5 -

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Publication number: JP2009522284A5
Authority: JP; Japan
Prior art keywords: pyrazolo; amine; pyrimidin; benzimidazol; cyclohexyl
Prior art date: 2006-12-28
Legal status : Granted

Application number

JP2008548736A

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English (en)

Japanese (ja)

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JP5512975B2 (ja

JP2009522284A (ja

Filing date

2006-12-28

Publication date

2013-03-28

2006-12-28 Application filed filed Critical

2006-12-28 Priority claimed from PCT/US2006/049461 external-priority patent/WO2007079164A2/en

2009-06-11 Publication of JP2009522284A publication Critical patent/JP2009522284A/ja

2013-03-28 Publication of JP2009522284A5 publication Critical patent/JP2009522284A5/ja

2014-06-04 Application granted granted Critical

2014-06-04 Publication of JP5512975B2 publication Critical patent/JP5512975B2/ja

Status Expired - Fee Related legal-status Critical Current

2026-12-28 Anticipated expiration legal-status Critical

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-1 heterocyclic alkane Chemical class 0.000 description 125
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 79
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 34
150000002390 heteroarenes Chemical class 0.000 description 25
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 25
125000001072 heteroaryl group Chemical group 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
125000000217 alkyl group Chemical group 0.000 description 18
125000003342 alkenyl group Chemical group 0.000 description 16
125000000304 alkynyl group Chemical group 0.000 description 16
230000005494 condensation Effects 0.000 description 12
238000009833 condensation Methods 0.000 description 12
150000001924 cycloalkanes Chemical class 0.000 description 12
150000001925 cycloalkenes Chemical class 0.000 description 12
125000000753 cycloalkyl group Chemical group 0.000 description 12
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 12
125000000392 cycloalkenyl group Chemical group 0.000 description 8
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 7
125000004366 heterocycloalkenyl group Chemical group 0.000 description 6
150000001412 amines Chemical class 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
150000003857 carboxamides Chemical class 0.000 description 4
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
PLPCIOBQPVBKDV-UHFFFAOYSA-N COC1=C(CC2=NC(C=CC(C3=NNC4=NC=NC(N)=C34)=C3)=C3N2)C=CC=C1 Chemical compound COC1=C(CC2=NC(C=CC(C3=NNC4=NC=NC(N)=C34)=C3)=C3N2)C=CC=C1 PLPCIOBQPVBKDV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
125000005343 heterocyclic alkyl group Chemical group 0.000 description 3
TXCIGKDJGAWBID-UHFFFAOYSA-N 1-[4-[4-(3-methoxypropyl)piperazin-1-yl]cyclohexyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(CCCOC)CCN1C1CCC(N2C3=NC=NC(N)=C3C=N2)CC1 TXCIGKDJGAWBID-UHFFFAOYSA-N 0.000 description 2
ATNOPBHGQZPBLB-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-(1-methylsulfonylpiperidin-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(S(=O)(=O)C)CCC1N1C2=NC=NC(N)=C2C(C=2C=C3N=C(CC=4C=CC=CC=4)NC3=CC=2)=N1 ATNOPBHGQZPBLB-UHFFFAOYSA-N 0.000 description 2
JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 2
VOGNUMZKSDBTER-YHBQERECSA-N C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C12)=CC=C1C=NN2CC1=CC=CC=C1Cl Chemical class C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C12)=CC=C1C=NN2CC1=CC=CC=C1Cl VOGNUMZKSDBTER-YHBQERECSA-N 0.000 description 2
RSYZKMCJSXGEBF-SOAUALDESA-N C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1 Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1 RSYZKMCJSXGEBF-SOAUALDESA-N 0.000 description 2
YXOPZEOQJFWIOF-RQNOJGIXSA-N C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1Cl Chemical class C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1Cl YXOPZEOQJFWIOF-RQNOJGIXSA-N 0.000 description 2
HLNIMORQAKXZMA-UHFFFAOYSA-N C1=CC=C(C(=C1)CC2=NC3=C(N2)C=C(C=C3)C4=C5C(=NC=NC5=NN4)N)Cl Chemical compound C1=CC=C(C(=C1)CC2=NC3=C(N2)C=C(C=C3)C4=C5C(=NC=NC5=NN4)N)Cl HLNIMORQAKXZMA-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
ZFNFQLSYQAZYKN-PPNDLDFTSA-N (2R)-2-[[4-[4-amino-3-[1-[(2-fluorophenyl)methyl]indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexyl]amino]propanoic acid Chemical compound C1CC(N[C@H](C)C(O)=O)CCC1N1C2=NC=NC(N)=C2C(C=2C=C3C=CN(CC=4C(=CC=CC=4)F)C3=CC=2)=N1 ZFNFQLSYQAZYKN-PPNDLDFTSA-N 0.000 description 1
XSHZQWIYUHZNAL-IBGZPJMESA-N (2s)-1-[4-amino-3-(2-benzyl-3h-benzimidazol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]-3-morpholin-4-ylpropan-2-ol Chemical compound C([C@H](O)CN1C=2N=CN=C(C=2C(C=2C=C3N=C(CC=4C=CC=CC=4)NC3=CC=2)=N1)N)N1CCOCC1 XSHZQWIYUHZNAL-IBGZPJMESA-N 0.000 description 1
FFWQLZFIMNTUCZ-UHFFFAOYSA-N 1-(bromomethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CBr FFWQLZFIMNTUCZ-UHFFFAOYSA-N 0.000 description 1
SJXYIPGTQQKALM-UHFFFAOYSA-N 1-[(4-benzylmorpholin-2-yl)methyl]-3-[1-[(2-chlorophenyl)methyl]indol-5-yl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical class N1=C(C=2C=C3C=CN(CC=4C(=CC=CC=4)Cl)C3=CC=2)C=2C(N)=NC=NC=2N1CC(OCC1)CN1CC1=CC=CC=C1 SJXYIPGTQQKALM-UHFFFAOYSA-N 0.000 description 1
XJDYZNMQDUPIEN-UHFFFAOYSA-N 1-[4-[2-[2-(2-aminoethoxy)ethoxy]ethylamino]cyclohexyl]-3-[2-[(2-fluorophenyl)methyl]-1h-indol-5-yl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(NCCOCCOCCN)CCC1N1C2=NC=NC(N)=C2C(C=2C=C3C=C(CC=4C(=CC=CC=4)F)NC3=CC=2)=N1 XJDYZNMQDUPIEN-UHFFFAOYSA-N 0.000 description 1
PLZJRENWWIBHRM-UHFFFAOYSA-N 1-[4-[4-[4-amino-3-(2-benzyl-3h-benzimidazol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]but-2-ynyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC#CCN1C2=NC=NC(N)=C2C(C=2C=C3NC(CC=4C=CC=CC=4)=NC3=CC=2)=N1 PLZJRENWWIBHRM-UHFFFAOYSA-N 0.000 description 1
ZCPRWQKHTUIMMZ-UHFFFAOYSA-N 1-[4-[4-[4-amino-3-[1-[(2-chlorophenyl)methyl]indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]but-2-ynyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC#CCN1C2=NC=NC(N)=C2C(C=2C=C3C=CN(CC=4C(=CC=CC=4)Cl)C3=CC=2)=N1 ZCPRWQKHTUIMMZ-UHFFFAOYSA-N 0.000 description 1
ZGXFZODSNKIFTK-UHFFFAOYSA-N 1-[4-[4-amino-3-[2-[(2-fluorophenyl)methyl]-1H-indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexyl]piperidin-4-ol Chemical compound C1=2C(N)=NC=NC=2N(C2CCC(CC2)N2CCC(O)CC2)N=C1C(C=C1C=2)=CC=C1NC=2CC1=CC=CC=C1F ZGXFZODSNKIFTK-UHFFFAOYSA-N 0.000 description 1
JDIVGWYLJYZLGB-UHFFFAOYSA-N 1-[4-[4-amino-3-[2-[(2-methoxyphenyl)methyl]-3h-benzimidazol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexyl]piperidin-4-ol Chemical compound COC1=CC=CC=C1CC1=NC2=CC(C=3C4=C(N)N=CN=C4N(C4CCC(CC4)N4CCC(O)CC4)N=3)=CC=C2N1 JDIVGWYLJYZLGB-UHFFFAOYSA-N 0.000 description 1
JUNZDIBGMKANEG-UHFFFAOYSA-N 1-[4-[[4-[2-(1,3-dioxolan-2-yl)ethyl]piperazin-1-yl]methyl]phenyl]-3-[2-[(2-methoxyphenyl)methyl]-3h-benzimidazol-5-yl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1CC1=NC2=CC(C=3C4=C(N)N=CN=C4N(C=4C=CC(CN5CCN(CCC6OCCO6)CC5)=CC=4)N=3)=CC=C2N1 JUNZDIBGMKANEG-UHFFFAOYSA-N 0.000 description 1
XOTCCGLGOWKWCE-UHFFFAOYSA-N 2-[1-[4-[4-amino-3-[1-[(2-chlorophenyl)methyl]indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexyl]piperidin-4-yl]ethanol Chemical compound C1=2C(N)=NC=NC=2N(C2CCC(CC2)N2CCC(CCO)CC2)N=C1C(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1Cl XOTCCGLGOWKWCE-UHFFFAOYSA-N 0.000 description 1
MTJUWUQXNUOHLT-UHFFFAOYSA-N 2-[4-[4-[4-amino-3-(2-benzyl-3h-benzimidazol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]piperidin-1-yl]ethanol Chemical compound C1=2C(N)=NC=NC=2N(C2CCN(CC2)C2CCN(CCO)CC2)N=C1C(C=C1N2)=CC=C1N=C2CC1=CC=CC=C1 MTJUWUQXNUOHLT-UHFFFAOYSA-N 0.000 description 1
CJYXIDXTHXUNET-UHFFFAOYSA-N 2-[4-[4-[4-amino-3-[2-[(2,5-difluorophenyl)methyl]-1h-indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexyl]piperazin-1-yl]ethanol Chemical compound C1=2C(N)=NC=NC=2N(C2CCC(CC2)N2CCN(CCO)CC2)N=C1C(C=C1C=2)=CC=C1NC=2CC1=CC(F)=CC=C1F CJYXIDXTHXUNET-UHFFFAOYSA-N 0.000 description 1
JERRCYUEYRQEFW-UHFFFAOYSA-N 2-[4-[4-[4-amino-3-[2-[(2-fluorophenyl)methyl]-1h-indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexyl]piperazin-1-yl]ethanol Chemical compound C1=2C(N)=NC=NC=2N(C2CCC(CC2)N2CCN(CCO)CC2)N=C1C(C=C1C=2)=CC=C1NC=2CC1=CC=CC=C1F JERRCYUEYRQEFW-UHFFFAOYSA-N 0.000 description 1
UBCJMIBCFCCJHI-UHFFFAOYSA-N 2-[4-[4-[4-amino-3-[2-[(2-fluorophenyl)methyl]-1h-indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]piperidin-1-yl]ethanol Chemical compound C1=2C(N)=NC=NC=2N(C2CCN(CC2)C2CCN(CCO)CC2)N=C1C(C=C1C=2)=CC=C1NC=2CC1=CC=CC=C1F UBCJMIBCFCCJHI-UHFFFAOYSA-N 0.000 description 1
JJQLYXBKKRLPLC-UHFFFAOYSA-N 2-[4-[4-[4-amino-3-[3-[(2-fluorophenyl)methyl]-1h-indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexyl]piperazin-1-yl]ethanol Chemical compound C1=2C(N)=NC=NC=2N(C2CCC(CC2)N2CCN(CCO)CC2)N=C1C(C=C12)=CC=C1NC=C2CC1=CC=CC=C1F JJQLYXBKKRLPLC-UHFFFAOYSA-N 0.000 description 1
QYKIQMJHRHDWKV-UHFFFAOYSA-N 2-[[4-[4-amino-3-[1-[(2-fluorophenyl)methyl]indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexyl]-methylamino]acetic acid Chemical compound C1CC(N(CC(O)=O)C)CCC1N1C2=NC=NC(N)=C2C(C=2C=C3C=CN(CC=4C(=CC=CC=4)F)C3=CC=2)=N1 QYKIQMJHRHDWKV-UHFFFAOYSA-N 0.000 description 1
RIEKLHPBAKSJDI-UHFFFAOYSA-N 2-[[4-[4-amino-3-[1-[(2-fluorophenyl)methyl]indol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexyl]amino]ethanol Chemical compound C1=2C(N)=NC=NC=2N(C2CCC(CC2)NCCO)N=C1C(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1F RIEKLHPBAKSJDI-UHFFFAOYSA-N 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
HUVMQWBWYPQPHV-UHFFFAOYSA-N 3-(1-benzylbenzimidazol-5-yl)-1-(4-morpholin-4-ylcyclohexyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2N(C2CCC(CC2)N2CCOCC2)N=C1C(C=C1N=C2)=CC=C1N2CC1=CC=CC=C1 HUVMQWBWYPQPHV-UHFFFAOYSA-N 0.000 description 1
NAXRDSNBNWGDBU-UHFFFAOYSA-N 3-(2-benzyl-1h-indol-5-yl)-1-[4-[4-(3-methoxypropyl)piperazin-1-yl]cyclohexyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(CCCOC)CCN1C1CCC(N2C3=NC=NC(N)=C3C(C=3C=C4C=C(CC=5C=CC=CC=5)NC4=CC=3)=N2)CC1 NAXRDSNBNWGDBU-UHFFFAOYSA-N 0.000 description 1
FCWBGTDPWIOVQX-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-(1-benzylpiperidin-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2N(C2CCN(CC=3C=CC=CC=3)CC2)N=C1C(C=C1N2)=CC=C1N=C2CC1=CC=CC=C1 FCWBGTDPWIOVQX-UHFFFAOYSA-N 0.000 description 1
MBUIZDMZXKHIAX-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-(1-methylpiperidin-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCC1N1C2=NC=NC(N)=C2C(C=2C=C3N=C(CC=4C=CC=CC=4)NC3=CC=2)=N1 MBUIZDMZXKHIAX-UHFFFAOYSA-N 0.000 description 1
SDRSOMZJBWSSBP-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-(1-pyrimidin-2-ylpiperidin-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2N(C2CCN(CC2)C=2N=CC=CN=2)N=C1C(C=C1N2)=CC=C1N=C2CC1=CC=CC=C1 SDRSOMZJBWSSBP-UHFFFAOYSA-N 0.000 description 1
SMGSLFIQLGZLNH-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-(2-morpholin-4-ylethyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=C3NC(CC=4C=CC=CC=4)=NC3=CC=2)C=2C(N)=NC=NC=2N1CCN1CCOCC1 SMGSLFIQLGZLNH-UHFFFAOYSA-N 0.000 description 1
ZTMDGMZJSFCLTB-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-(3-methoxypropyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C12=C(N)N=CN=C2N(CCCOC)N=C1C(C=C1N=2)=CC=C1NC=2CC1=CC=CC=C1 ZTMDGMZJSFCLTB-UHFFFAOYSA-N 0.000 description 1
QWDPFKPMHKISLT-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-(3-pyridin-3-ylpropyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=C3NC(CC=4C=CC=CC=4)=NC3=CC=2)C=2C(N)=NC=NC=2N1CCCC1=CC=CN=C1 QWDPFKPMHKISLT-UHFFFAOYSA-N 0.000 description 1
UJMHBTHLBGVYQU-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-(4-morpholin-4-ylbut-2-ynyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=C3NC(CC=4C=CC=CC=4)=NC3=CC=2)C=2C(N)=NC=NC=2N1CC#CCN1CCOCC1 UJMHBTHLBGVYQU-UHFFFAOYSA-N 0.000 description 1
XPXCMZFYZLGSHU-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2N(C2CCOCC2)N=C1C(C=C1N=2)=CC=C1NC=2CC1=CC=CC=C1 XPXCMZFYZLGSHU-UHFFFAOYSA-N 0.000 description 1
DGPMIWIWSPAZLD-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-[(4-benzylmorpholin-2-yl)methyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=2C=C3NC(CC=4C=CC=CC=4)=NC3=CC=2)C=2C(N)=NC=NC=2N1CC(OCC1)CN1CC1=CC=CC=C1 DGPMIWIWSPAZLD-UHFFFAOYSA-N 0.000 description 1
INLPUMJQSSZMKO-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-[1-(2-methylsulfonylethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(CCS(=O)(=O)C)CCC1N1C2=NC=NC(N)=C2C(C=2C=C3N=C(CC=4C=CC=CC=4)NC3=CC=2)=N1 INLPUMJQSSZMKO-UHFFFAOYSA-N 0.000 description 1
MBCKKYIFWFFFBE-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-[1-(2-methylsulfonylethyl)pyrrolidin-3-yl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1N(CCS(=O)(=O)C)CCC1N1C2=NC=NC(N)=C2C(C=2C=C3N=C(CC=4C=CC=CC=4)NC3=CC=2)=N1 MBCKKYIFWFFFBE-UHFFFAOYSA-N 0.000 description 1
NTHKARDWBISXGI-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-[1-(3-methoxypropyl)pyrrolidin-3-yl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1N(CCCOC)CCC1N1C2=NC=NC(N)=C2C(C=2C=C3N=C(CC=4C=CC=CC=4)NC3=CC=2)=N1 NTHKARDWBISXGI-UHFFFAOYSA-N 0.000 description 1
SUAVUUQGNOGOCR-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-[1-(6-chloropyridazin-3-yl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2N(C2CCN(CC2)C=2N=NC(Cl)=CC=2)N=C1C(C=C1N2)=CC=C1N=C2CC1=CC=CC=C1 SUAVUUQGNOGOCR-UHFFFAOYSA-N 0.000 description 1
MNLWIQHDAXKQOL-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-[2-(4-methyl-1,3-thiazol-5-yl)ethyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=CSC(CCN2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5C=CC=CC=5)=NC4=CC=3)=N2)=C1C MNLWIQHDAXKQOL-UHFFFAOYSA-N 0.000 description 1
HQVGVOKCAIOTTD-UHFFFAOYSA-N 3-(2-benzyl-3h-benzimidazol-5-yl)-1-[3-(dimethylamino)propyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C12=C(N)N=CN=C2N(CCCN(C)C)N=C1C(C=C1N=2)=CC=C1NC=2CC1=CC=CC=C1 HQVGVOKCAIOTTD-UHFFFAOYSA-N 0.000 description 1
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JP2008548736A 2005-12-29 2006-12-28 タンパク質キナーゼ阻害薬 Expired - Fee Related JP5512975B2 (ja)