CA2790302A1 - Dimeric iap inhibitors - Google Patents
Dimeric iap inhibitors Download PDFInfo
- Publication number
- CA2790302A1 CA2790302A1 CA2790302A CA2790302A CA2790302A1 CA 2790302 A1 CA2790302 A1 CA 2790302A1 CA 2790302 A CA2790302 A CA 2790302A CA 2790302 A CA2790302 A CA 2790302A CA 2790302 A1 CA2790302 A1 CA 2790302A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkylene
- pyrrolidin
- pyridin
- oxo
- 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.)
- Abandoned
Links
- 239000003112 inhibitor Substances 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 230000006907 apoptotic process Effects 0.000 claims abstract description 14
- -1 1H-dihydroimidazolyl Chemical group 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 84
- 125000002947 alkylene group Chemical group 0.000 claims description 81
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 62
- 229910052757 nitrogen Inorganic materials 0.000 claims description 61
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
- 125000005842 heteroatom Chemical group 0.000 claims description 56
- 229910052717 sulfur Inorganic materials 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 50
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 46
- 229910052739 hydrogen Chemical group 0.000 claims description 39
- 239000001257 hydrogen Chemical group 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
- 108091007065 BIRCs Proteins 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 201000010099 disease Diseases 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- 238000011282 treatment Methods 0.000 claims description 31
- 239000008177 pharmaceutical agent Substances 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 208000035475 disorder Diseases 0.000 claims description 27
- 125000004450 alkenylene group Chemical group 0.000 claims description 26
- 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 26
- 229930012538 Paclitaxel Natural products 0.000 claims description 25
- 229960001592 paclitaxel Drugs 0.000 claims description 25
- 206010028980 Neoplasm Diseases 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 125000005549 heteroarylene group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 101100369993 Mus musculus Tnfsf10 gene Proteins 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 230000001404 mediated effect Effects 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 14
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 13
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 229940123369 TRAIL receptor agonist Drugs 0.000 claims description 8
- 125000004419 alkynylene group Chemical group 0.000 claims description 8
- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 229940044693 topoisomerase inhibitor Drugs 0.000 claims description 8
- 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
- NAEDVTLYYRRDTF-XIYFKRPFSA-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]decanediamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CCCCNC(=O)CCCCCCCCC(=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 NAEDVTLYYRRDTF-XIYFKRPFSA-N 0.000 claims description 7
- TWRJLKDJHRWECB-UYNGVSIFSA-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]decanediamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CC2=CC=C(C=C2)NC(=O)CCCCCCCCC(=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 TWRJLKDJHRWECB-UYNGVSIFSA-N 0.000 claims description 7
- 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 7
- 230000002018 overexpression Effects 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical class 0.000 claims description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 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 6
- 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 6
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 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 5
- 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 5
- 125000004069 aziridinyl group Chemical group 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
- 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 4
- UDSAJFSYJMHNFI-UHFFFAOYSA-N 2,6-diazaspiro[3.3]heptane Chemical compound C1NCC11CNC1 UDSAJFSYJMHNFI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000001313 C5-C10 heteroaryl group Chemical group 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
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000001939 inductive effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- MFWKSSPEWCJQJK-GSBNDYOUSA-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]heptanediamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CCCCNC(=O)CCCCCC(=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 MFWKSSPEWCJQJK-GSBNDYOUSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- DGYDDYXFCQZXIE-BQDLXYDNSA-N 1-n,3-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]benzene-1,3-dicarboxamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CC2=CC=C(C=C2)NC(=O)C=2C=CC=C(C=2)C(=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 DGYDDYXFCQZXIE-BQDLXYDNSA-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
- 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
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- PNBHWOVWFRZWCV-SHGOGIJKSA-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]hexanediamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CC2=CC=C(C=C2)NC(=O)CCCCC(=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 PNBHWOVWFRZWCV-SHGOGIJKSA-N 0.000 claims description 3
- PFXHMWKREFIWAE-HKGOYKQQSA-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]pentanediamide Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](C)NC)CC2=CC=C(C=C2)NC(=O)CCCC(=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 PFXHMWKREFIWAE-HKGOYKQQSA-N 0.000 claims description 3
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 3
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 14
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 102000046283 TNF-Related Apoptosis-Inducing Ligand Human genes 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
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- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 8
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 8
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- BZPITRBIKDZMBJ-ZAQUEYBZSA-N tert-butyl n-[(2s)-3-[4-(9h-fluoren-9-ylmethoxycarbonylamino)phenyl]-1-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamate Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@H](CC=2C=CC(NC(=O)OCC3C4=CC=CC=C4C4=CC=CC=C43)=CC=2)NC(=O)OC(C)(C)C)=CN=CC=1C(=O)C1=CC=C(F)C=C1 BZPITRBIKDZMBJ-ZAQUEYBZSA-N 0.000 description 1
- UEJQBVABYTZJLX-BCRBLDSWSA-N tert-butyl n-[(2s)-6-(9h-fluoren-9-ylmethoxycarbonylamino)-1-[(2s)-2-[5-(4-fluorobenzoyl)pyridin-3-yl]pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamate Chemical compound C=1C([C@@H]2CCCN2C(=O)[C@H](CCCCNC(=O)OCC2C3=CC=CC=C3C3=CC=CC=C32)NC(=O)OC(C)(C)C)=CN=CC=1C(=O)C1=CC=C(F)C=C1 UEJQBVABYTZJLX-BCRBLDSWSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- UCRQTPGCFCBLOX-UHFFFAOYSA-N thiophene-2,5-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)S1 UCRQTPGCFCBLOX-UHFFFAOYSA-N 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940035307 toposar Drugs 0.000 description 1
- 229960002190 topotecan hydrochloride Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940066958 treanda Drugs 0.000 description 1
- 229950007217 tremelimumab Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- INQOMBQAUSQDDS-FIBGUPNXSA-N trideuterio(iodo)methane Chemical compound [2H]C([2H])([2H])I INQOMBQAUSQDDS-FIBGUPNXSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 229950008737 vadimezan Drugs 0.000 description 1
- 239000004066 vascular targeting agent Substances 0.000 description 1
- 229940099039 velcade Drugs 0.000 description 1
- 229960004982 vinblastine sulfate Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960002110 vincristine sulfate Drugs 0.000 description 1
- GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 1
- 229940069559 votrient Drugs 0.000 description 1
- 229950003511 votumumab Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940053867 xeloda Drugs 0.000 description 1
- 229950008250 zalutumumab Drugs 0.000 description 1
- 229940053890 zanosar Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940061261 zolinza Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30811410P | 2010-02-25 | 2010-02-25 | |
| US61/308,114 | 2010-02-25 | ||
| US33392710P | 2010-05-12 | 2010-05-12 | |
| US61/333,927 | 2010-05-12 | ||
| US38841010P | 2010-09-30 | 2010-09-30 | |
| US61/388,410 | 2010-09-30 | ||
| PCT/EP2011/052662 WO2011104266A1 (en) | 2010-02-25 | 2011-02-23 | Dimeric iap inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2790302A1 true CA2790302A1 (en) | 2011-09-01 |
Family
ID=44476672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2790302A Abandoned CA2790302A1 (en) | 2010-02-25 | 2011-02-23 | Dimeric iap inhibitors |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8445440B2 (enExample) |
| EP (1) | EP2539333A1 (enExample) |
| JP (1) | JP2013520466A (enExample) |
| KR (1) | KR20130010894A (enExample) |
| CN (1) | CN102834389A (enExample) |
| AR (1) | AR080253A1 (enExample) |
| BR (1) | BR112012021291A2 (enExample) |
| CA (1) | CA2790302A1 (enExample) |
| EA (1) | EA201201177A1 (enExample) |
| MX (1) | MX2012009894A (enExample) |
| TW (1) | TW201141846A (enExample) |
| UY (1) | UY33236A (enExample) |
| WO (1) | WO2011104266A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100317593A1 (en) * | 2009-06-12 | 2010-12-16 | Astrazeneca Ab | 2,3-dihydro-1h-indene compounds |
| UY33794A (es) * | 2010-12-13 | 2012-07-31 | Novartis Ag | Inhibidores diméricos de las iap |
| US20140243276A1 (en) | 2011-09-30 | 2014-08-28 | Tetralogic Pharmaceuticals Corporation | Smac mimetic (birinapant) for use in the treatment of proliferative diseases (cancer) |
| US9453048B2 (en) | 2012-08-09 | 2016-09-27 | Bristol-Myers Squibb Company | IAP antagonists |
| EP2917218B1 (en) * | 2012-11-09 | 2017-01-04 | Ensemble Therapeutics Corporation | Macrocyclic compounds for inhibition of inhibitors of apoptosis |
| ES2982449T3 (es) | 2013-06-25 | 2024-10-16 | Walter & Eliza Hall Inst Medical Res | Miméticos Smac para su uso en el tratamiento de una infección persistente por VIH |
| WO2016079527A1 (en) | 2014-11-19 | 2016-05-26 | Tetralogic Birinapant Uk Ltd | Combination therapy |
| WO2016097773A1 (en) | 2014-12-19 | 2016-06-23 | Children's Cancer Institute | Therapeutic iap antagonists for treating proliferative disorders |
| CN109705191B (zh) * | 2017-10-25 | 2022-04-29 | 广东东阳光药业有限公司 | Iap抑制剂及其在药物中的应用 |
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| JPS6041077B2 (ja) | 1976-09-06 | 1985-09-13 | 喜徳 喜谷 | １，２‐ジアミノシクロヘキサン異性体のシス白金（２）錯体 |
| US5281620A (en) | 1986-12-23 | 1994-01-25 | Cancer Research Campaign Technology Limited | Compounds having antitumor and antibacterial properties |
| PE20010306A1 (es) | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
| GB0018891D0 (en) | 2000-08-01 | 2000-09-20 | Novartis Ag | Organic compounds |
| JP2002037626A (ja) | 2000-07-27 | 2002-02-06 | Internatl Superconductivity Technology Center | ビスマス系高温超電導体の製造方法。 |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| US6995162B2 (en) | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
| TWI275390B (en) | 2002-04-30 | 2007-03-11 | Wyeth Corp | Process for the preparation of 7-substituted-3- quinolinecarbonitriles |
| DE60334247D1 (de) | 2002-11-27 | 2010-10-28 | Irm Llc | Verfahren und zusammensetzungen zur apoptoseinduktion in krebszellen |
| CA2514733A1 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| JP2007520522A (ja) | 2004-02-05 | 2007-07-26 | ノバルティス アクチエンゲゼルシャフト | （ａ）ＤＮＡトポイソメラーゼ阻害剤および（ｂ）ＩＡＰ阻害剤の組み合わせ剤 |
| AU2005218555B2 (en) * | 2004-03-01 | 2008-01-03 | Board Of Regents, The University Of Texas System | Dimeric small molecule potentiators of apoptosis |
| JP5230865B2 (ja) | 2004-07-15 | 2013-07-10 | テトラロジック ファーマシューティカルズ コーポレーション | Ｉａｐ結合性化合物 |
| DK1851200T3 (da) | 2005-02-25 | 2014-04-14 | Tetralogic Pharm Corp | Dimere iap-inhibitorer |
| CA2607940C (en) | 2005-05-18 | 2009-12-15 | Aegera Therapeutics Inc. | Bir domain binding compounds |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| AU2006279929A1 (en) | 2005-08-09 | 2007-02-22 | Tetralogic Pharmaceuticals Corporation | Treatment of proliferative disorders |
| WO2007048224A1 (en) * | 2005-10-25 | 2007-05-03 | Aegera Therapeutics Inc. | Iap bir domain binding compounds |
| CN101340947B (zh) * | 2005-12-20 | 2012-09-05 | 诺瓦提斯公司 | Iap-抑制剂和紫杉烷7的组合 |
| TWI543988B (zh) | 2006-03-16 | 2016-08-01 | 科學製藥股份有限公司 | 結合於細胞凋亡抑制蛋白（ｉａｐ）之桿狀病毒ｉａｐ重複序列（ｂｉｒ）區域之化合物 |
| BRPI0708942A2 (pt) | 2006-03-21 | 2011-06-14 | Joyant Pharmaceuticals Inc | composto promotor de apoptose, uso e mÉtodo de produÇço do mesmo e composiÇço farmacÊutica |
| US8202902B2 (en) * | 2006-05-05 | 2012-06-19 | The Regents Of The University Of Michigan | Bivalent SMAC mimetics and the uses thereof |
| MY159563A (en) * | 2006-05-16 | 2017-01-13 | Pharmascience Inc | Iap bir domain binding compounds |
| WO2008014238A2 (en) | 2006-07-24 | 2008-01-31 | Tetralogic Pharmaceuticals Corporation | Dimeric iap inhibitors |
| JP5452223B2 (ja) * | 2006-07-24 | 2014-03-26 | テトラロジック ファーマシューティカルズ コーポレーション | Ｉａｐ阻害剤 |
| US20100113326A1 (en) | 2006-07-24 | 2010-05-06 | Tetralogic Pharmaceuticals Corporation | Dimeric iap inhibitors |
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| EP2049563B1 (en) | 2006-07-24 | 2014-03-12 | Tetralogic Pharmaceuticals Corporation | Dimeric iap antagonists |
| PE20110224A1 (es) * | 2006-08-02 | 2011-04-05 | Novartis Ag | PROCEDIMIENTO PARA LA SINTESIS DE UN PEPTIDOMIMETICO DE Smac INHIBIDOR DE IAP, Y COMPUESTOS INTERMEDIARIOS PARA LA SINTESIS DEL MISMO |
| KR20090082221A (ko) * | 2006-10-19 | 2009-07-29 | 노파르티스 아게 | 유기 화합물 |
| MX2009005551A (es) | 2006-11-28 | 2009-06-08 | Novartis Ag | Uso de inhibidores de iap para el tratamiento de leucemia mieloide aguda. |
| WO2008066854A2 (en) | 2006-11-28 | 2008-06-05 | Novartis Ag | Methods and compositions for inducing apoptosis in cancer cells |
| KR101149449B1 (ko) | 2007-03-20 | 2012-05-25 | 삼성전자주식회사 | 오디오 신호의 인코딩 방법 및 장치, 그리고 오디오 신호의디코딩 방법 및 장치 |
| EP2079309B1 (en) * | 2007-04-12 | 2015-11-11 | Joyant Pharmaceuticals Inc | SMAC MIMEE DIMERS AND TRIMERS USEFUL AS ANTICANCER AGENTS |
| AR066348A1 (es) | 2007-04-30 | 2009-08-12 | Genentech Inc | Inhibidores de las iap |
| JP2010528587A (ja) | 2007-05-07 | 2010-08-26 | テトラロジック ファーマシューティカルズ コーポレーション | アポトーシス阻害タンパク質のアンタゴニストに対する感受性のバイオマーカーとしてＴＮＦα遺伝子の発現を用いる方法 |
| TWI471134B (zh) | 2007-09-12 | 2015-02-01 | Genentech Inc | 肌醇磷脂３－激酶抑制劑化合物及化療劑之組合及使用方法 |
| CA2701292C (en) | 2007-10-25 | 2015-03-24 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| EP2058312A1 (en) | 2007-11-09 | 2009-05-13 | Universita' degli Studi di Milano | SMAC mimetic compounds as apoptosis inducers |
| PL2240506T3 (pl) | 2008-01-11 | 2013-05-31 | Genentech Inc | Inhibitory IAP |
| BRPI0906785A2 (pt) | 2008-01-24 | 2015-07-14 | Tetralogic Pharm Corp | Composto, composição farmacêutica, e, métodos para induzir a apoptose em uma célula, para tratar câncer e uma doença autoimune |
| WO2009136290A1 (en) | 2008-05-05 | 2009-11-12 | Aegera Therapeutics, Inc. | Functionalized pyrrolidines and use thereof as iap inhibitors |
| US8168784B2 (en) | 2008-06-20 | 2012-05-01 | Abbott Laboratories | Processes to make apoptosis promoters |
| EP2310402A1 (en) | 2008-06-27 | 2011-04-20 | Aegera Therapeutics Inc. | Bridged secondary amines and use thereof as iap bir domain binding compounds |
| NZ590550A (en) | 2008-08-02 | 2013-05-31 | Genentech Inc | Inhibitors of Apoptosis (IAP) for treating cancer |
| WO2010015090A1 (en) | 2008-08-07 | 2010-02-11 | Aegera Therapeutics Inc. | Functionalized pyrrolidines and use thereof as iap inhibitors |
| AU2009293403A1 (en) | 2008-09-17 | 2010-03-25 | Tetralogic Pharmaceuticals Corp. | IAP inhibitors |
| JP2012502994A (ja) | 2008-09-22 | 2012-02-02 | アムジエン・インコーポレーテツド | 治療方法 |
| US8283372B2 (en) * | 2009-07-02 | 2012-10-09 | Tetralogic Pharmaceuticals Corp. | 2-(1H-indol-3-ylmethyl)-pyrrolidine dimer as a SMAC mimetic |
-
2011
- 2011-02-21 UY UY0001033236A patent/UY33236A/es not_active Application Discontinuation
- 2011-02-23 CA CA2790302A patent/CA2790302A1/en not_active Abandoned
- 2011-02-23 US US13/033,463 patent/US8445440B2/en not_active Expired - Fee Related
- 2011-02-23 EP EP11705532A patent/EP2539333A1/en not_active Withdrawn
- 2011-02-23 BR BR112012021291A patent/BR112012021291A2/pt not_active IP Right Cessation
- 2011-02-23 CN CN2011800177078A patent/CN102834389A/zh active Pending
- 2011-02-23 KR KR1020127024875A patent/KR20130010894A/ko not_active Withdrawn
- 2011-02-23 EA EA201201177A patent/EA201201177A1/ru unknown
- 2011-02-23 MX MX2012009894A patent/MX2012009894A/es active IP Right Grant
- 2011-02-23 JP JP2012554332A patent/JP2013520466A/ja active Pending
- 2011-02-23 AR ARP110100547A patent/AR080253A1/es unknown
- 2011-02-23 WO PCT/EP2011/052662 patent/WO2011104266A1/en not_active Ceased
- 2011-02-24 TW TW100106289A patent/TW201141846A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| UY33236A (es) | 2011-09-30 |
| KR20130010894A (ko) | 2013-01-29 |
| US20110206690A1 (en) | 2011-08-25 |
| BR112012021291A2 (pt) | 2016-10-25 |
| US8445440B2 (en) | 2013-05-21 |
| MX2012009894A (es) | 2012-09-12 |
| WO2011104266A1 (en) | 2011-09-01 |
| AR080253A1 (es) | 2012-03-21 |
| JP2013520466A (ja) | 2013-06-06 |
| AU2011219862A1 (en) | 2012-09-06 |
| TW201141846A (en) | 2011-12-01 |
| EA201201177A1 (ru) | 2013-04-30 |
| EP2539333A1 (en) | 2013-01-02 |
| CN102834389A (zh) | 2012-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20160223 |