JP5512975B2 - タンパク質キナーゼ阻害薬 - Google Patents

Info

Publication number

JP5512975B2

JP5512975B2 JP2008548736A JP2008548736A JP5512975B2 JP 5512975 B2 JP5512975 B2 JP 5512975B2 JP 2008548736 A JP2008548736 A JP 2008548736A JP 2008548736 A JP2008548736 A JP 2008548736A JP 5512975 B2 JP5512975 B2 JP 5512975B2

Authority

JP

Japan

Prior art keywords

pyrazolo

benzimidazol

amine

trans

pyrimidin

Prior art date

2005-12-29

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.)

Expired - Fee Related

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• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
• 239000003909 protein kinase inhibitor Substances 0.000 title description 2
• -1 1H-benzo [d] imidazol-6-yl Chemical group 0.000 claims description 580
• 150000001875 compounds Chemical class 0.000 claims description 411
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 160
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 121
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 150000002390 heteroarenes Chemical class 0.000 claims description 51
• 150000001924 cycloalkanes Chemical class 0.000 claims description 40
• 150000001925 cycloalkenes Chemical class 0.000 claims description 40
• 125000001072 heteroaryl group Chemical group 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 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 31
• 125000003342 alkenyl group Chemical group 0.000 claims description 30
• 125000000304 alkynyl group Chemical group 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
• 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 15
• 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 claims description 13
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 9
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 8
• KALBSUQXUTZBAT-MEMLXQNLSA-N chembl400277 Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1N2)=CC=C1N=C2CC1=CC=CC=N1 KALBSUQXUTZBAT-MEMLXQNLSA-N 0.000 claims description 7
• 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 claims description 6
• 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 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 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 claims description 4
• 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 claims description 4
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• HPFNWFVCOUAOPL-IYARVYRRSA-N C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1N2)=CC=C1N=C2C1=CC=CC(F)=C1Cl Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1N2)=CC=C1N=C2C1=CC=CC(F)=C1Cl HPFNWFVCOUAOPL-IYARVYRRSA-N 0.000 claims description 3
• 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 claims description 3
• 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims description 3
• 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 claims description 2
• KGWWXFCXHGAZPD-UHFFFAOYSA-N 3-[4-[4-[4-amino-3-(2-benzyl-3h-benzimidazol-5-yl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]piperidin-1-yl]propan-1-ol Chemical compound C1=2C(N)=NC=NC=2N(C2CCN(CC2)C2CCN(CCCO)CC2)N=C1C(C=C1N2)=CC=C1N=C2CC1=CC=CC=C1 KGWWXFCXHGAZPD-UHFFFAOYSA-N 0.000 claims description 2
• UQQBTDMCOCASNB-UHFFFAOYSA-N 4-[4-amino-3-[2-[(2-methoxyphenyl)methyl]-3h-benzimidazol-5-yl]pyrazolo[3,4-d]pyrimidin-1-yl]cyclohexan-1-one Chemical compound COC1=CC=CC=C1CC1=NC2=CC=C(C=3C4=C(N)N=CN=C4N(C4CCC(=O)CC4)N=3)C=C2N1 UQQBTDMCOCASNB-UHFFFAOYSA-N 0.000 claims description 2
• LTSHKLNECMGZNT-MEMLXQNLSA-N C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1N2)=CC=C1N=C2CC1=CC=CN=C1 Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1N2)=CC=C1N=C2CC1=CC=CN=C1 LTSHKLNECMGZNT-MEMLXQNLSA-N 0.000 claims description 2
• VEYXXYCYTYQQRO-MEMLXQNLSA-N C1=CC(C)=CC=C1OC1=NC2=CC=C(C=3C4=C(N)N=CN=C4N([C@@H]4CC[C@H](CC4)N4CCOCC4)N=3)C=C2N1 Chemical compound C1=CC(C)=CC=C1OC1=NC2=CC=C(C=3C4=C(N)N=CN=C4N([C@@H]4CC[C@H](CC4)N4CCOCC4)N=3)C=C2N1 VEYXXYCYTYQQRO-MEMLXQNLSA-N 0.000 claims description 2
• XHJFUIHCYSUKSE-SOAUALDESA-N C1CN(CCCOC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC5CCCC5)=NC4=CC=3)=N2)CC1 Chemical compound C1CN(CCCOC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC5CCCC5)=NC4=CC=3)=N2)CC1 XHJFUIHCYSUKSE-SOAUALDESA-N 0.000 claims description 2
• CSQKVUZIDGFVNP-DIVCQZSQSA-N C1CN(CCCOC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC5CCCCC5)=NC4=CC=3)=N2)CC1 Chemical compound C1CN(CCCOC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC5CCCCC5)=NC4=CC=3)=N2)CC1 CSQKVUZIDGFVNP-DIVCQZSQSA-N 0.000 claims description 2
• GOWVWKPOHHRVSQ-YHBQERECSA-N C1CN(CCCOC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5SC=CC=5)=NC4=CC=3)=N2)CC1 Chemical compound C1CN(CCCOC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5SC=CC=5)=NC4=CC=3)=N2)CC1 GOWVWKPOHHRVSQ-YHBQERECSA-N 0.000 claims description 2
• DTYTZIRGKKFBHN-SOAUALDESA-N C1CN(CCOC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5C(=CC=CC=5)OC)=NC4=CC=3)=N2)CC1 Chemical compound C1CN(CCOC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5C(=CC=CC=5)OC)=NC4=CC=3)=N2)CC1 DTYTZIRGKKFBHN-SOAUALDESA-N 0.000 claims description 2
• DTYTZIRGKKFBHN-PLQXJYEYSA-N C1CN(CCOC)CCN1[C@@H]1CC[C@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5C(=CC=CC=5)OC)=NC4=CC=3)=N2)CC1 Chemical compound C1CN(CCOC)CCN1[C@@H]1CC[C@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5C(=CC=CC=5)OC)=NC4=CC=3)=N2)CC1 DTYTZIRGKKFBHN-PLQXJYEYSA-N 0.000 claims description 2
• DPNUXAYIITYJDV-RQNOJGIXSA-N C1CN(S(=O)(=O)CC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5C(=CC=CC=5)OC)=NC4=CC=3)=N2)CC1 Chemical compound C1CN(S(=O)(=O)CC)CCN1[C@@H]1CC[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5C(=CC=CC=5)OC)=NC4=CC=3)=N2)CC1 DPNUXAYIITYJDV-RQNOJGIXSA-N 0.000 claims description 2
• DPNUXAYIITYJDV-PSWAGMNNSA-N C1CN(S(=O)(=O)CC)CCN1[C@@H]1CC[C@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5C(=CC=CC=5)OC)=NC4=CC=3)=N2)CC1 Chemical compound C1CN(S(=O)(=O)CC)CCN1[C@@H]1CC[C@H](N2C3=NC=NC(N)=C3C(C=3C=C4NC(CC=5C(=CC=CC=5)OC)=NC4=CC=3)=N2)CC1 DPNUXAYIITYJDV-PSWAGMNNSA-N 0.000 claims description 2
• ZGKREEOKCDCIOB-FIARQXNZSA-N CC(c1nc2ccc(cc2[nH]1)-c1nn([C@H]2CC[C@@H](CC2)N2CCOCC2)c2ncnc(N)c12)c1ccccc1 Chemical class CC(c1nc2ccc(cc2[nH]1)-c1nn([C@H]2CC[C@@H](CC2)N2CCOCC2)c2ncnc(N)c12)c1ccccc1 ZGKREEOKCDCIOB-FIARQXNZSA-N 0.000 claims description 2
• LSVKEIXVYSICDV-MEMLXQNLSA-N CC1=CC=CC(OC=2NC3=CC(=CC=C3N=2)C=2C3=C(N)N=CN=C3N([C@@H]3CC[C@H](CC3)N3CCOCC3)N=2)=C1 Chemical compound CC1=CC=CC(OC=2NC3=CC(=CC=C3N=2)C=2C3=C(N)N=CN=C3N([C@@H]3CC[C@H](CC3)N3CCOCC3)N=2)=C1 LSVKEIXVYSICDV-MEMLXQNLSA-N 0.000 claims description 2
• IPWRIKHESARPTK-UHFFFAOYSA-N COC1=CC=CC(=C1)CC2=NC3=C(N2)C=C(C=C3)C4=C5C(=NC=NC5=NN4)N Chemical compound COC1=CC=CC(=C1)CC2=NC3=C(N2)C=C(C=C3)C4=C5C(=NC=NC5=NN4)N IPWRIKHESARPTK-UHFFFAOYSA-N 0.000 claims description 2
• BDSQKKKGSPCXRG-HZCBDIJESA-N COC1=CC=CC=C1CC1=NC2=CC=C(C=3C4=C(N)N=CN=C4N([C@@H]4CC[C@H](CC4)N4CC5=NC(=CN5CC4)C(F)(F)F)N=3)C=C2N1 Chemical compound COC1=CC=CC=C1CC1=NC2=CC=C(C=3C4=C(N)N=CN=C4N([C@@H]4CC[C@H](CC4)N4CC5=NC(=CN5CC4)C(F)(F)F)N=3)C=C2N1 BDSQKKKGSPCXRG-HZCBDIJESA-N 0.000 claims description 2
• LXXUWEXYIQNKJC-QVYRIUEQSA-N COC1=CC=CC=C1CC1=NC2=CC=C(C=3C4=C(N)N=CN=C4N([C@@H]4CC[C@H](CC4)N4CCN(CCOCCOCCN)CC4)N=3)C=C2N1 Chemical compound COC1=CC=CC=C1CC1=NC2=CC=C(C=3C4=C(N)N=CN=C4N([C@@H]4CC[C@H](CC4)N4CCN(CCOCCOCCN)CC4)N=3)C=C2N1 LXXUWEXYIQNKJC-QVYRIUEQSA-N 0.000 claims description 2
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• FHQQNAHMJMQUKJ-PSWAGMNNSA-N COC1=CC=CC=C1CC1=NC2=CC=C(C=3C4=C(N)N=CN=C4N([C@H]4CC[C@H](CC4)N4CCN(CC4)C(=O)N(C)C)N=3)C=C2N1 Chemical compound COC1=CC=CC=C1CC1=NC2=CC=C(C=3C4=C(N)N=CN=C4N([C@H]4CC[C@H](CC4)N4CCN(CC4)C(=O)N(C)C)N=3)C=C2N1 FHQQNAHMJMQUKJ-PSWAGMNNSA-N 0.000 claims description 2
• RLIIDDPVDHWIEM-MEMLXQNLSA-N COc1ccc(cc1)-c1nc2ccc(cc2[nH]1)-c1nn([C@H]2CC[C@@H](CC2)N2CCOCC2)c2ncnc(N)c12 Chemical class COc1ccc(cc1)-c1nc2ccc(cc2[nH]1)-c1nn([C@H]2CC[C@@H](CC2)N2CCOCC2)c2ncnc(N)c12 RLIIDDPVDHWIEM-MEMLXQNLSA-N 0.000 claims description 2
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• LUMJNLXVAUAKSQ-WGSAOQKQSA-N Nc1ncnc2n(nc(-c3ccc4nc([nH]c4c3)-c3ccc(Cl)c(Cl)c3)c12)[C@H]1CC[C@@H](CC1)N1CCOCC1 Chemical compound Nc1ncnc2n(nc(-c3ccc4nc([nH]c4c3)-c3ccc(Cl)c(Cl)c3)c12)[C@H]1CC[C@@H](CC1)N1CCOCC1 LUMJNLXVAUAKSQ-WGSAOQKQSA-N 0.000 claims description 2
• GQRGTHUCFJWAMN-MEMLXQNLSA-N Nc1ncnc2n(nc(-c3ccc4nc([nH]c4c3)-c3ccc(Cl)cc3)c12)[C@H]1CC[C@@H](CC1)N1CCOCC1 Chemical class Nc1ncnc2n(nc(-c3ccc4nc([nH]c4c3)-c3ccc(Cl)cc3)c12)[C@H]1CC[C@@H](CC1)N1CCOCC1 GQRGTHUCFJWAMN-MEMLXQNLSA-N 0.000 claims description 2
• FNIODIAGYLWZRY-WGSAOQKQSA-N chembl248877 Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1N2)=CC=C1N=C2CC1=CC=CS1 FNIODIAGYLWZRY-WGSAOQKQSA-N 0.000 claims description 2
• AJYKKQGFOFSZLL-MXVIHJGJSA-N chembl249082 Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CC[C@H](CC2)N2CCOCC2)N=C1C(C=C1N2)=CC=C1N=C2CC=1C=CSC=1 AJYKKQGFOFSZLL-MXVIHJGJSA-N 0.000 claims description 2
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