JP5711537B2 - ピリミジン−２−アミン化合物およびｊａｋキナーゼの阻害剤としてのその使用 - Google Patents

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Publication number

JP5711537B2

JP5711537B2 JP2010546945A JP2010546945A JP5711537B2 JP 5711537 B2 JP5711537 B2 JP 5711537B2 JP 2010546945 A JP2010546945 A JP 2010546945A JP 2010546945 A JP2010546945 A JP 2010546945A JP 5711537 B2 JP5711537 B2 JP 5711537B2

Authority

JP

Japan

Prior art keywords

optionally substituted

group

heterocyclyl

heteroaryl

alkyl

Prior art date

2008-02-15

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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• 125000000217 alkyl group Chemical group 0.000 claims description 347
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• 125000001188 haloalkyl group Chemical group 0.000 claims description 220
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 179
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 174
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• 125000003107 substituted aryl group Chemical group 0.000 claims description 146
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• 125000005983 2,5-diazabicyclo[2.2.1]heptan-2-yl group Chemical group 0.000 description 1
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• WOMRICQVWOZPAD-VXKWHMMOSA-N 4-[2-[3-fluoro-4-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]anilino]pyrimidin-4-yl]-n-pyridin-2-ylbenzamide Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C(C(=C1)F)=CC=C1NC(N=1)=NC=CC=1C(C=C1)=CC=C1C(=O)NC1=CC=CC=N1 WOMRICQVWOZPAD-VXKWHMMOSA-N 0.000 description 1
• PSRXJWAGLBWGAN-UHFFFAOYSA-N 4-[2-[3-methyl-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)anilino]pyrimidin-4-yl]-n-pyridin-2-ylbenzamide Chemical compound CN1CC2CC1CN2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=C1)=CC=C1C(=O)NC1=CC=CC=N1 PSRXJWAGLBWGAN-UHFFFAOYSA-N 0.000 description 1
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• QJYWBYJKAGZNBY-UHFFFAOYSA-N 4-[4-(1-ethoxyethyl)phenyl]-n-[3-fluoro-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl]pyrimidin-2-amine Chemical compound C1=CC(C(C)OCC)=CC=C1C1=CC=NC(NC=2C=C(F)C(N3C4CC(N(C4)C)C3)=CC=2)=N1 QJYWBYJKAGZNBY-UHFFFAOYSA-N 0.000 description 1
• QJYWBYJKAGZNBY-VNQANMTISA-N 4-[4-(1-ethoxyethyl)phenyl]-n-[3-fluoro-4-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]phenyl]pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C(C(=C1)F)=CC=C1NC(N=1)=NC=CC=1C1=CC=C(C(C)OCC)C=C1 QJYWBYJKAGZNBY-VNQANMTISA-N 0.000 description 1
• ZYASQUHVSPBEOE-UHFFFAOYSA-N 4-[4-(1-ethoxyethyl)phenyl]-n-[3-methyl-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl]pyrimidin-2-amine Chemical compound C1=CC(C(C)OCC)=CC=C1C1=CC=NC(NC=2C=C(C)C(N3C4CC(N(C4)C)C3)=CC=2)=N1 ZYASQUHVSPBEOE-UHFFFAOYSA-N 0.000 description 1
• ZYASQUHVSPBEOE-SXZQLXHWSA-N 4-[4-(1-ethoxyethyl)phenyl]-n-[3-methyl-4-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]phenyl]pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C1=CC=C(C(C)OCC)C=C1 ZYASQUHVSPBEOE-SXZQLXHWSA-N 0.000 description 1
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• RKGWXNGTANWSPN-PMACEKPBSA-N 4-[4-(dimethylamino)phenyl]-n-[3-fluoro-4-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]phenyl]pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C(C(=C1)F)=CC=C1NC(N=1)=NC=CC=1C1=CC=C(N(C)C)C=C1 RKGWXNGTANWSPN-PMACEKPBSA-N 0.000 description 1
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• BCWLQVZMCYXGHO-VMPREFPWSA-N 4-[4-[5-[4-(dimethylamino)phenyl]-1,3-oxazol-2-yl]phenyl]-n-[3-methyl-4-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]phenyl]pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=C1)=CC=C1C(O1)=NC=C1C1=CC=C(N(C)C)C=C1 BCWLQVZMCYXGHO-VMPREFPWSA-N 0.000 description 1
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• SALLHIYTXMERKD-PMACEKPBSA-N 4-[6-(2-methoxyethyl)-2-(methylamino)pyridin-3-yl]-n-[3-methyl-4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]phenyl]pyrimidin-2-amine Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C1=CC=C(CCOC)N=C1NC SALLHIYTXMERKD-PMACEKPBSA-N 0.000 description 1
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• ISFRTJWMTGWOSR-UHFFFAOYSA-N 4-[6-(3,3-dimethylbutylamino)pyridin-3-yl]-n-[3-methyl-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl]pyrimidin-2-amine Chemical compound CN1CC2CC1CN2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C1=CC=C(NCCC(C)(C)C)N=C1 ISFRTJWMTGWOSR-UHFFFAOYSA-N 0.000 description 1
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• SLGUZPFETXFORM-VXKWHMMOSA-N 4-[6-(3-ethoxypropylamino)pyridin-3-yl]-n-[3-methyl-4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]phenyl]pyrimidin-2-amine Chemical group C([C@]1(OC[C@]2([H])C1)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C1=CC=C(NCCCOCC)N=C1 SLGUZPFETXFORM-VXKWHMMOSA-N 0.000 description 1
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• FUIQAWPXDWNPLZ-GOTSBHOMSA-N 4-[6-(benzylamino)pyridin-3-yl]-n-[3-fluoro-4-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]phenyl]pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C(C(=C1)F)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1NCC1=CC=CC=C1 FUIQAWPXDWNPLZ-GOTSBHOMSA-N 0.000 description 1
• MVAMDQHCQHNGOU-DQEYMECFSA-N 4-[6-(benzylamino)pyridin-3-yl]-n-[3-methyl-4-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]phenyl]pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1NCC1=CC=CC=C1 MVAMDQHCQHNGOU-DQEYMECFSA-N 0.000 description 1
• OEBUWFUQJAEJRT-UHFFFAOYSA-N 4-[6-(cyclohexylamino)pyridin-3-yl]-n-[3-fluoro-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl]pyrimidin-2-amine Chemical compound CN1CC2CC1CN2C(C(=C1)F)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1NC1CCCCC1 OEBUWFUQJAEJRT-UHFFFAOYSA-N 0.000 description 1
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• NYHOUBXBDPFTKU-UHFFFAOYSA-N 4-[6-(cyclohexylamino)pyridin-3-yl]-n-[4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound CN1CC2CC1CN2C(C(=C1)C(F)(F)F)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1NC1CCCCC1 NYHOUBXBDPFTKU-UHFFFAOYSA-N 0.000 description 1
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• RQTRXGDBCYRHGR-UHFFFAOYSA-N n-[3-methyl-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl]-4-[6-(1,4-oxazepan-4-yl)pyridin-3-yl]pyrimidin-2-amine Chemical compound CN1CC2CC1CN2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1N1CCCOCC1 RQTRXGDBCYRHGR-UHFFFAOYSA-N 0.000 description 1
• JPGGYYOMVXKXLI-UHFFFAOYSA-N n-[3-methyl-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl]-4-[6-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)pyridin-3-yl]pyrimidin-2-amine Chemical compound CN1CC2CC1CN2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1N1C(CO2)CC2C1 JPGGYYOMVXKXLI-UHFFFAOYSA-N 0.000 description 1
• BQVYGZUAULILLS-UHFFFAOYSA-N n-[3-methyl-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl]-4-[6-(2h-tetrazol-5-yl)pyridin-3-yl]pyrimidin-2-amine Chemical compound CN1CC2CC1CN2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1C1=NN=NN1 BQVYGZUAULILLS-UHFFFAOYSA-N 0.000 description 1
• APQYCXZPJAVTBZ-UHFFFAOYSA-N n-[3-methyl-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl]-4-[6-(oxan-4-yloxy)pyridin-3-yl]pyrimidin-2-amine Chemical compound CN1CC2CC1CN2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1OC1CCOCC1 APQYCXZPJAVTBZ-UHFFFAOYSA-N 0.000 description 1
• MHHXKRIZMNEWEH-UHFFFAOYSA-N n-[3-methyl-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl]-4-[6-(propylamino)pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=NC(NCCC)=CC=C1C1=CC=NC(NC=2C=C(C)C(N3C4CC(N(C4)C)C3)=CC=2)=N1 MHHXKRIZMNEWEH-UHFFFAOYSA-N 0.000 description 1
• GFPWLHOZZRCNLM-UHFFFAOYSA-N n-[3-methyl-4-(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)phenyl]-4-(6-morpholin-4-ylpyridin-3-yl)pyrimidin-2-amine Chemical compound CN1C(C2)CCC1CN2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1N1CCOCC1 GFPWLHOZZRCNLM-UHFFFAOYSA-N 0.000 description 1
• CUSMGHDDGROBCF-FGZHOGPDSA-N n-[3-methyl-4-[(1r,4r)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]phenyl]-4-(6-morpholin-4-ylpyridin-3-yl)pyrimidin-2-amine Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1N1CCOCC1 CUSMGHDDGROBCF-FGZHOGPDSA-N 0.000 description 1
• MGMHXQYXHNPHTH-VXKWHMMOSA-N n-[3-methyl-4-[(1s,4s)-2-methylsulfonyl-2,5-diazabicyclo[2.2.1]heptan-5-yl]phenyl]-4-(6-morpholin-4-ylpyridin-3-yl)pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@@]2(C1)[H])S(C)(=O)=O)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1N1CCOCC1 MGMHXQYXHNPHTH-VXKWHMMOSA-N 0.000 description 1
• FINLQJXRZOGZLB-SFTDATJTSA-N n-[3-methyl-4-[(1s,4s)-2-methylsulfonyl-2,5-diazabicyclo[2.2.1]heptan-5-yl]phenyl]-4-[6-(propylamino)pyridin-3-yl]pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@@]2(C1)[H])S(C)(=O)=O)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C1=CC=C(NCCC)N=C1 FINLQJXRZOGZLB-SFTDATJTSA-N 0.000 description 1
• XLFOQKDCWACNAL-MLCQCVOFSA-N n-[3-methyl-4-[(1s,4s)-2-methylsulfonyl-2,5-diazabicyclo[2.2.1]heptan-5-yl]phenyl]-4-[6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyridin-3-yl]pyrimidin-2-amine Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(N=C1)=CC=C1C(N=1)=CC=NC=1NC(C=C1C)=CC=C1N1[C@@](CN2S(C)(=O)=O)([H])C[C@@]2([H])C1 XLFOQKDCWACNAL-MLCQCVOFSA-N 0.000 description 1
• PWKUJECNAVTLOL-OALUTQOASA-N n-[3-methyl-4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]phenyl]-4-(1h-pyrrolo[2,3-b]pyridin-5-yl)pyrimidin-2-amine Chemical group N1=C2NC=CC2=CC(C=2C=CN=C(N=2)NC2=CC=C(C(=C2)C)N2C[C@]3(OC[C@]2([H])C3)[H])=C1 PWKUJECNAVTLOL-OALUTQOASA-N 0.000 description 1
• NNZZTUSEJJHFDQ-PMACEKPBSA-N n-[3-methyl-4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]phenyl]-4-(2-morpholin-4-ylpyrimidin-5-yl)pyrimidin-2-amine Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CN=C1N1CCOCC1 NNZZTUSEJJHFDQ-PMACEKPBSA-N 0.000 description 1
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• WWQUPCOABZKKEU-PMACEKPBSA-N n-[3-methyl-4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]phenyl]-4-[6-(propylamino)pyridin-3-yl]pyrimidin-2-amine Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C1=CC=C(NCCC)N=C1 WWQUPCOABZKKEU-PMACEKPBSA-N 0.000 description 1
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• GFUINYIZGJTXLW-VXKWHMMOSA-N n-[3-methyl-4-[(1s,4s)-5-(2,2,2-trifluoroethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]phenyl]-4-(6-morpholin-4-ylpyridin-3-yl)pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@]2([H])C1)CC(F)(F)F)[H])N2C(C(=C1)C)=CC=C1NC(N=1)=NC=CC=1C(C=N1)=CC=C1N1CCOCC1 GFUINYIZGJTXLW-VXKWHMMOSA-N 0.000 description 1
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