JP2013520466A - 二量体ｉａｐ阻害剤 - Google Patents

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Publication number

JP2013520466A

JP2013520466A JP2012554332A JP2012554332A JP2013520466A JP 2013520466 A JP2013520466 A JP 2013520466A JP 2012554332 A JP2012554332 A JP 2012554332A JP 2012554332 A JP2012554332 A JP 2012554332A JP 2013520466 A JP2013520466 A JP 2013520466A

Authority

JP

Japan

Prior art keywords

alkyl

alkylene

pyridin

pyrrolidin

oxo

Prior art date

2010-02-25

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.)

Pending

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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 109
• 150000003839 salts Chemical class 0.000 claims description 88
• 229910052757 nitrogen Inorganic materials 0.000 claims description 71
• 125000002947 alkylene group Chemical group 0.000 claims description 66
• 238000000034 method Methods 0.000 claims description 61
• 229910052717 sulfur Inorganic materials 0.000 claims description 59
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 58
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• 125000005842 heteroatom Chemical group 0.000 claims description 55
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• 229910052760 oxygen Inorganic materials 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
• 239000000203 mixture Substances 0.000 claims description 33
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• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 27
• 229930012538 Paclitaxel Natural products 0.000 claims description 26
• 125000004450 alkenylene group Chemical group 0.000 claims description 26
• 229960001592 paclitaxel Drugs 0.000 claims description 26
• 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 24
• 206010028980 Neoplasm Diseases 0.000 claims description 23
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• 125000005549 heteroarylene group Chemical group 0.000 claims description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims description 22
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• 125000002993 cycloalkylene group Chemical group 0.000 claims description 21
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• 125000004043 oxo group Chemical group O=* 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 239000012828 PI3K inhibitor Substances 0.000 claims description 10
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• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
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• 125000005647 linker group Chemical group 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical class 0.000 claims description 8
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• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
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• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 6
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• 125000004069 aziridinyl group Chemical group 0.000 claims description 5
• RMVIHZORKYEQIR-RFAGEVQHSA-N n,n'-bis[(5s)-6-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-5-[[(2s)-2-(methylamino)propanoyl]amino]-6-oxohexyl]nonanediamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CCCCNC(=O)CCCCCCCC(=O)NCCCC[C@H](NC(=O)[C@H](C)NC)C(=O)N2[C@@H](CCC2)C=2C=C(C=NC=2)C(=O)C=2C=CC(F)=CC=2)=CN=CC=1C(=O)C1=CC=C(F)C=C1 RMVIHZORKYEQIR-RFAGEVQHSA-N 0.000 claims description 5
• XKJHTKTZGFFEKP-ZEYHMCSCSA-N n,n'-bis[4-[(2s)-3-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-2-[[(2s)-2-(methylamino)propanoyl]amino]-3-oxopropyl]phenyl]heptanediamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CC2=CC=C(C=C2)NC(=O)CCCCCC(=O)NC2=CC=C(C=C2)C[C@H](NC(=O)[C@H](C)NC)C(=O)N2[C@@H](CCC2)C=2C=C(C=NC=2)C(=O)C=2C=CC(F)=CC=2)=CN=CC=1C(=O)C1=CC=C(F)C=C1 XKJHTKTZGFFEKP-ZEYHMCSCSA-N 0.000 claims description 5
• LXVDXQJERJIFJQ-HNWXVATNSA-N n,n'-bis[4-[(2s)-3-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-2-[[(2s)-2-(methylamino)propanoyl]amino]-3-oxopropyl]phenyl]nonanediamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CC2=CC=C(C=C2)NC(=O)CCCCCCCC(=O)NC2=CC=C(C=C2)C[C@H](NC(=O)[C@H](C)NC)C(=O)N2[C@@H](CCC2)C=2C=C(C=NC=2)C(=O)C=2C=CC(F)=CC=2)=CN=CC=1C(=O)C1=CC=C(F)C=C1 LXVDXQJERJIFJQ-HNWXVATNSA-N 0.000 claims description 5
• KLADKEUPPHQHDN-HDUJCMOOSA-N n-[(5s)-6-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-5-[[(2s)-2-(methylamino)propanoyl]amino]-6-oxohexyl]-4-[4-[[(5s)-6-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-5-[[(2s)-2-(methylamino)propanoyl]amino]-6-oxohexyl]carbamoyl] Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CCCCNC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)NCCCC[C@H](NC(=O)[C@H](C)NC)C(=O)N2[C@@H](CCC2)C=2C=C(C=NC=2)C(=O)C=2C=CC(F)=CC=2)=CN=CC=1C(=O)C1=CC=C(F)C=C1 KLADKEUPPHQHDN-HDUJCMOOSA-N 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
• UDSAJFSYJMHNFI-UHFFFAOYSA-N 2,6-diazaspiro[3.3]heptane Chemical compound C1NCC11CNC1 UDSAJFSYJMHNFI-UHFFFAOYSA-N 0.000 claims description 4
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
• 239000000654 additive Substances 0.000 claims description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
• 125000005567 fluorenylene group Chemical group 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• XWPQDZHURSCQNV-BMFARTNFSA-N (2s)-n-[(2s)-6-[[4-[4-[[(5s)-5-[[(2s)-azetidine-2-carbonyl]amino]-6-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-6-oxohexyl]carbamoyl]phenyl]benzoyl]amino]-1-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-1-oxohexan-2-yl]azetidine- Chemical compound C1=CC(F)=CC=C1C(=O)C1=CN=CC([C@H]2N(CCC2)C(=O)[C@H](CCCCNC(=O)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(=O)NCCCC[C@H](NC(=O)[C@H]2NCC2)C(=O)N2[C@@H](CCC2)C=2C=C(C=NC=2)C(=O)C=2C=CC(F)=CC=2)NC(=O)[C@H]2NCC2)=C1 XWPQDZHURSCQNV-BMFARTNFSA-N 0.000 claims description 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
• 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
• TVQGQDPHQNIVPP-ANQDZLGGSA-N 1-n,3-n-bis[(5s)-6-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-5-[[(2s)-2-(methylamino)propanoyl]amino]-6-oxohexyl]benzene-1,3-dicarboxamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CCCCNC(=O)C=2C=CC=C(C=2)C(=O)NCCCC[C@H](NC(=O)[C@H](C)NC)C(=O)N2[C@@H](CCC2)C=2C=C(C=NC=2)C(=O)C=2C=CC(F)=CC=2)=CN=CC=1C(=O)C1=CC=C(F)C=C1 TVQGQDPHQNIVPP-ANQDZLGGSA-N 0.000 claims description 3
• KPOLERISENSJJN-ANQDZLGGSA-N 1-n,4-n-bis[(5s)-6-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-5-[[(2s)-2-(methylamino)propanoyl]amino]-6-oxohexyl]benzene-1,4-dicarboxamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CCCCNC(=O)C2=CC=C(C=C2)C(=O)NCCCC[C@H](NC(=O)[C@H](C)NC)C(=O)N2[C@@H](CCC2)C=2C=C(C=NC=2)C(=O)C=2C=CC(F)=CC=2)=CN=CC=1C(=O)C1=CC=C(F)C=C1 KPOLERISENSJJN-ANQDZLGGSA-N 0.000 claims description 3
• 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
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• 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 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
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