CA2916468C - Heteroaryl compounds useful as inhibitors of sumo activating enzyme - Google Patents
Heteroaryl compounds useful as inhibitors of sumo activating enzyme Download PDFInfo
- Publication number
- CA2916468C CA2916468C CA2916468A CA2916468A CA2916468C CA 2916468 C CA2916468 C CA 2916468C CA 2916468 A CA2916468 A CA 2916468A CA 2916468 A CA2916468 A CA 2916468A CA 2916468 C CA2916468 C CA 2916468C
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- CA
- Canada
- Prior art keywords
- compound
- amino
- carbonyl
- pyrimidin
- pharmaceutically acceptable
- 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.)
- Expired - Fee Related
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- 102000004190 Enzymes Human genes 0.000 title claims abstract description 13
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 13
- 230000003213 activating effect Effects 0.000 title claims abstract description 5
- 239000003112 inhibitor Substances 0.000 title abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 title description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 1053
- 150000003839 salts Chemical class 0.000 claims abstract description 447
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 455
- FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 claims description 281
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 195
- -1 chloro, bromo, fluoro, methyl Chemical group 0.000 claims description 182
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 162
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 91
- 239000001257 hydrogen Substances 0.000 claims description 90
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
- 229910052757 nitrogen Inorganic materials 0.000 claims description 80
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 69
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 64
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 53
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 50
- 125000001931 aliphatic group Chemical group 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 229910052717 sulfur Chemical group 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 41
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 40
- 239000011593 sulfur Chemical group 0.000 claims description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 39
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 239000001301 oxygen Chemical group 0.000 claims description 39
- 206010028980 Neoplasm Diseases 0.000 claims description 37
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 33
- 201000011510 cancer Diseases 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 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 10
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims description 7
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 201000005202 lung cancer Diseases 0.000 claims description 7
- 208000020816 lung neoplasm Diseases 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 206010033128 Ovarian cancer Diseases 0.000 claims description 6
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- ZDIVCNVAGGHVFE-UHFFFAOYSA-N 1-(difluoromethoxy)-2-(trifluoromethoxy)ethyne Chemical group FC(OC#COC(F)(F)F)F ZDIVCNVAGGHVFE-UHFFFAOYSA-N 0.000 claims description 4
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims description 3
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 3
- 125000000532 dioxanyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 3
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- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- RQAOVVKSNGLLEG-UHFFFAOYSA-N N'-[2-(difluoromethoxy)-2-(trifluoromethoxy)-2-(trifluoromethylsulfanyl)ethyl]-N'-ethyl-N,N-dimethylethyne-1,2-diamine Chemical group FC(OC(CN(CC)C#CN(C)C)(SC(F)(F)F)OC(F)(F)F)F RQAOVVKSNGLLEG-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
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- 238000000338 in vitro Methods 0.000 claims description 2
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- RUBLBDFVWYCFMM-DWIQEWEKSA-N NS(=O)(=O)OC[C@H]1C[C@@H](Nc2ncncc2C(=O)c2ccn(Cc3ccccc3)c2)[C@H](O)[C@@H]1O Chemical compound NS(=O)(=O)OC[C@H]1C[C@@H](Nc2ncncc2C(=O)c2ccn(Cc3ccccc3)c2)[C@H](O)[C@@H]1O RUBLBDFVWYCFMM-DWIQEWEKSA-N 0.000 claims 2
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- RILOPYUGSDZNCX-PUJDYFOHSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[1-[(1S)-1-[5-(trifluoromethyl)furan-2-yl]ethyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@@H](C)C=1OC(=CC=1)C(F)(F)F)F)O)(=O)=O RILOPYUGSDZNCX-PUJDYFOHSA-N 0.000 claims 2
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- XCGPZFIZIUAYIL-JTLUYSSBSA-N [(1R,2R,3R,4R)-4-[[5-[1-[(1S)-1-(3-bromophenyl)propyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@@H](CC)C1=CC(=CC=C1)Br)F)O)(=O)=O XCGPZFIZIUAYIL-JTLUYSSBSA-N 0.000 claims 2
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- NFDGXIKUNYAZAU-FCFFQYRPSA-N [(1R,2R,3R,4R)-4-[[5-[1-[[5-(difluoromethyl)furan-2-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC=1OC(=CC=1)C(F)F)F)O)(=O)=O NFDGXIKUNYAZAU-FCFFQYRPSA-N 0.000 claims 1
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- HEZBNIJCLWTRKC-GJTYKATRSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[(1S,2S)-2-phenylcyclopropyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CN(C[C@H]2C[C@@H]2C2=CC=CC=C2)C=C1 HEZBNIJCLWTRKC-GJTYKATRSA-N 0.000 claims 1
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- SAXDYRZUFZGBBW-WVZRYYJFSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[(2S)-oxolan-2-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)C[C@H]1OCCC1)O)(=O)=O SAXDYRZUFZGBBW-WVZRYYJFSA-N 0.000 claims 1
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- YTWZDUVRCPQGED-MDZRGWNJSA-N [(1R,2S,4R)-4-[[5-[1-(cyclohexen-1-ylmethyl)pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CCCCC1)O)(=O)=O YTWZDUVRCPQGED-MDZRGWNJSA-N 0.000 claims 1
- JFNIVURHLJTVGR-PCFVDWANSA-N [(1R,2S,4R)-4-[[5-[1-[(1R)-1-(3-bromophenyl)ethyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound C[C@H](c1cccc(Br)c1)n1ccc(n1)C(=O)c1cncnc1N[C@H]1C[C@H](O)[C@@H](COS(N)(=O)=O)C1 JFNIVURHLJTVGR-PCFVDWANSA-N 0.000 claims 1
- JFNIVURHLJTVGR-XEQBAVFLSA-N [(1R,2S,4R)-4-[[5-[1-[(1S)-1-(3-bromophenyl)ethyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@@H](C)C1=CC(=CC=C1)Br)O)(=O)=O JFNIVURHLJTVGR-XEQBAVFLSA-N 0.000 claims 1
- SIFDLJDTHZDERK-VLXAULBPSA-N [(1R,2S,4R)-4-[[5-[1-[(1S)-1-(5-chlorofuran-2-yl)ethyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@@H](C)C=1OC(=CC=1)Cl)O)(=O)=O SIFDLJDTHZDERK-VLXAULBPSA-N 0.000 claims 1
- BFYHGGPVIRAPLC-ADAWSYLGSA-N [(1R,2S,4R)-4-[[5-[1-[(1S)-cyclohex-2-en-1-yl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@@H]1C=CCCC1)O)(=O)=O BFYHGGPVIRAPLC-ADAWSYLGSA-N 0.000 claims 1
- VCPNVGLQZZHOCR-LPMFXHHGSA-N [(1R,2S,4R)-4-[[5-[1-[(3-bromo-4-chlorophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)Br)O)(=O)=O VCPNVGLQZZHOCR-LPMFXHHGSA-N 0.000 claims 1
- JOGRSHJMHIESQC-QINHECLXSA-N [(1R,2S,4R)-4-[[5-[1-[(3-bromo-4-chlorophenyl)methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC(=C(C=C1)Cl)Br)O)(=O)=O JOGRSHJMHIESQC-QINHECLXSA-N 0.000 claims 1
- YRQACTWBEKROCI-HSMVNMDESA-N [(1R,2S,4R)-4-[[5-[1-[(3-chlorothiophen-2-yl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC=1SC=CC=1Cl)O)(=O)=O YRQACTWBEKROCI-HSMVNMDESA-N 0.000 claims 1
- IPYJACPIBJKRBU-MUKKUYKPSA-N [(1R,2S,4R)-4-[[5-[1-[(5-bromo-2-fluorophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)Br)F)O)(=O)=O IPYJACPIBJKRBU-MUKKUYKPSA-N 0.000 claims 1
- XIVQHVRBRVBRKR-FPDPHYFHSA-N [(1R,2S,4R)-4-[[5-[1-[(5-chloro-1-benzothiophen-3-yl)methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)Nc1ncncc1C(=O)c1ccn(Cc2csc3ccc(Cl)cc23)c1 XIVQHVRBRVBRKR-FPDPHYFHSA-N 0.000 claims 1
- IVSLHGICWXDVDJ-SIIHOXLZSA-N [(1R,2S,4R)-4-[[5-[1-[(6-bromopyridin-2-yl)methyl]-5-methylpyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C)CC1=NC(=CC=C1)Br)O)(=O)=O IVSLHGICWXDVDJ-SIIHOXLZSA-N 0.000 claims 1
- ZENMINREHDUSPY-DWWQWDFOSA-N [(1R,2S,4R)-4-[[5-[1-[(E)-but-2-enyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)C\C=C\C)O)(=O)=O ZENMINREHDUSPY-DWWQWDFOSA-N 0.000 claims 1
- IVTOOLGDXCILOG-CLCXKQKWSA-N [(1R,2S,4R)-4-[[5-[1-[3-(furan-2-yl)prop-2-ynyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC#CC=1OC=CC=1)O)(=O)=O IVTOOLGDXCILOG-CLCXKQKWSA-N 0.000 claims 1
- ORGUEKFCMCWTKG-ZTNFWEORSA-N [(1R,2S,4R)-4-[[5-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O)(=O)=O ORGUEKFCMCWTKG-ZTNFWEORSA-N 0.000 claims 1
- DRMMOHYDUWMEOD-ZTNFWEORSA-N [(1R,2S,4R)-4-[[5-[1-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC(=CC(=C1)C(F)(F)F)F)O)(=O)=O DRMMOHYDUWMEOD-ZTNFWEORSA-N 0.000 claims 1
- JHNOAOXUMSZQDY-MDZRGWNJSA-N [(1R,2S,4R)-4-[[5-[1-[[4-fluoro-3-(trifluoromethoxy)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC(=C(C=C1)F)OC(F)(F)F)O)(=O)=O JHNOAOXUMSZQDY-MDZRGWNJSA-N 0.000 claims 1
- GBVCFMUXBIKASV-HSMVNMDESA-N [(1R,2S,4R)-4-[[5-[1-[[5-(difluoromethyl)furan-2-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC=1OC(=CC1)C(F)F)O)(=O)=O GBVCFMUXBIKASV-HSMVNMDESA-N 0.000 claims 1
- DYAQTVPOHPTMAO-BYNBJNPRSA-N [(1r,2r,3r,4r)-3-fluoro-2-hydroxy-4-[[5-[1-[(3-iodophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(I)C=CC=2)C=C1 DYAQTVPOHPTMAO-BYNBJNPRSA-N 0.000 claims 1
- MZXRISJHGBBLPV-OBZYLPMUSA-N [(1r,2r,3r,4r)-3-fluoro-2-hydroxy-4-[[5-[1-[(3-iodophenyl)methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=CN(CC=2C=C(I)C=CC=2)C=C1 MZXRISJHGBBLPV-OBZYLPMUSA-N 0.000 claims 1
- HPJOHDBEYLZRBS-ZPFMKOPRSA-N [(1r,2r,3r,4r)-3-fluoro-4-[[5-[1-[(4-fluoro-3-methoxyphenyl)methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound C1=C(F)C(OC)=CC(CN2C=C(C=C2)C(=O)C=2C(=NC=NC=2)N[C@H]2[C@H]([C@H](O)[C@@H](COS(N)(=O)=O)C2)F)=C1 HPJOHDBEYLZRBS-ZPFMKOPRSA-N 0.000 claims 1
- DIQBNAPWUMUDOS-DLVXIWMQSA-N [(1r,2r,3r,4r)-4-[[5-[1-(3,6-dihydro-2h-pyran-4-ylmethyl)pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=CN(CC=2CCOCC=2)C=C1 DIQBNAPWUMUDOS-DLVXIWMQSA-N 0.000 claims 1
- HGCJOAUZJXWDPX-ZFTZQBIMSA-N [(1r,2r,3r,4r)-4-[[5-[1-[(1r)-1-(3-bromophenyl)ethyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound C1([C@@H](C)N2C=C(C=C2)C(=O)C=2C(=NC=NC=2)N[C@H]2[C@H]([C@H](O)[C@@H](COS(N)(=O)=O)C2)F)=CC=CC(Br)=C1 HGCJOAUZJXWDPX-ZFTZQBIMSA-N 0.000 claims 1
- QOALAEKBYOIOHN-BYNBJNPRSA-N [(1r,2r,3r,4r)-4-[[5-[1-[(3-bromophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(Br)C=CC=2)C=C1 QOALAEKBYOIOHN-BYNBJNPRSA-N 0.000 claims 1
- RUWZGFAAALXKHT-PJPYQEIOSA-N [(1r,2r,3r,4r)-4-[[5-[1-[(3-chloro-1-benzothiophen-2-yl)methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=CN(CC2=C(C3=CC=CC=C3S2)Cl)C=C1 RUWZGFAAALXKHT-PJPYQEIOSA-N 0.000 claims 1
- VDYJDWGIQIWPMS-FCFFQYRPSA-N [(1r,2r,3r,4r)-4-[[5-[1-[(5-bromofuran-2-yl)methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=CN(CC=2OC(Br)=CC=2)C=C1 VDYJDWGIQIWPMS-FCFFQYRPSA-N 0.000 claims 1
- RLWULVBBIXLOOU-SIKWWSQNSA-N [(1r,2r,3r,4r)-4-[[5-[1-[(6-chloropyridin-2-yl)methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=CN(CC=2N=C(Cl)C=CC=2)C=C1 RLWULVBBIXLOOU-SIKWWSQNSA-N 0.000 claims 1
- KJPGWGWLGDNZLC-STQYRHOTSA-N [(1r,2r,3r,4r)-4-[[5-[1-benzyl-5-(trifluoromethyl)pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=CN(CC=2C=CC=CC=2)C(C(F)(F)F)=C1 KJPGWGWLGDNZLC-STQYRHOTSA-N 0.000 claims 1
- ZQXMXTSGCKMYLI-ROZLJVEFSA-N [(1r,2r,3r,4r)-4-[[5-[5-chloro-1-[(3-chlorophenyl)methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=CN(CC=2C=C(Cl)C=CC=2)C(Cl)=C1 ZQXMXTSGCKMYLI-ROZLJVEFSA-N 0.000 claims 1
- HZKFKGVABBBABY-MWKWTDJYSA-N [(1r,2r,3r,4r)-4-[[5-[5-chloro-1-[[5-(trifluoromethyl)furan-2-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound F[C@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=CN(CC=2OC(=CC=2)C(F)(F)F)C(Cl)=C1 HZKFKGVABBBABY-MWKWTDJYSA-N 0.000 claims 1
- UDAHXLBENPNMPY-TWMCMTRYSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[5-[1-[(2,4,6-trifluorophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C(=CC(F)=CC=2F)F)C=C1 UDAHXLBENPNMPY-TWMCMTRYSA-N 0.000 claims 1
- DEOCHGPMCNMQLJ-JZURDYQRSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[5-[1-[(4-methylpyridin-2-yl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound CC1=CC=NC(CN2N=C(C=C2)C(=O)C=2C(=NC=NC=2)N[C@H]2[C@@H]([C@H](O)[C@@H](COS(N)(=O)=O)C2)O)=C1 DEOCHGPMCNMQLJ-JZURDYQRSA-N 0.000 claims 1
- KPRMFGLNOGQJIE-QUIPCFFLSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[5-[1-[2-(3-methylpyrazol-1-yl)ethyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound N1=C(C)C=CN1CCN1N=C(C(=O)C=2C(=NC=NC=2)N[C@H]2[C@@H]([C@H](O)[C@@H](COS(N)(=O)=O)C2)O)C=C1 KPRMFGLNOGQJIE-QUIPCFFLSA-N 0.000 claims 1
- UUFPOMDEUFSGOL-CODKJTEISA-N [(1r,2r,3s,4r)-3-amino-4-[[5-[1-[(3-bromophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound C1[C@H](COS(N)(=O)=O)[C@@H](O)[C@@H](N)[C@@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(Br)C=CC=2)C=C1 UUFPOMDEUFSGOL-CODKJTEISA-N 0.000 claims 1
- CDVCWMAZHRHXNE-XVJMICLVSA-N [(1r,2r,3s,4r)-4-[[3-(1-benzylpyrazole-3-carbonyl)pyridin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC=C1C(=O)C1=NN(CC=2C=CC=CC=2)C=C1 CDVCWMAZHRHXNE-XVJMICLVSA-N 0.000 claims 1
- ZDIJULRXRMOSCP-GCPGGVOISA-N [(1r,2r,3s,4r)-4-[[3-[1-[(3-chlorophenyl)methyl]pyrazole-3-carbonyl]pyridin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC=C1C(=O)C1=NN(CC=2C=C(Cl)C=CC=2)C=C1 ZDIJULRXRMOSCP-GCPGGVOISA-N 0.000 claims 1
- HDDAOTGBTKDSHW-OLJVKKBNSA-N [(1r,2r,3s,4r)-4-[[5-[1-(3-bromophenyl)sulfonylpyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(S(=O)(=O)C=2C=C(Br)C=CC=2)C=C1 HDDAOTGBTKDSHW-OLJVKKBNSA-N 0.000 claims 1
- PGYBDJDBHGLMJQ-ZHKFALCXSA-N [(1r,2r,3s,4r)-4-[[5-[1-[(3-chloro-4-fluorophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(Cl)C(F)=CC=2)C=C1 PGYBDJDBHGLMJQ-ZHKFALCXSA-N 0.000 claims 1
- FZHDYJCMFZPCHD-JZURDYQRSA-N [(1r,2r,3s,4r)-4-[[5-[1-[(3-chlorophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(Cl)C=CC=2)C=C1 FZHDYJCMFZPCHD-JZURDYQRSA-N 0.000 claims 1
- DLBGTOJZFSANBA-FEGHXTNJSA-N [(1r,2r,3s,4r)-4-[[5-[1-[(3-cyanophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(C=CC=2)C#N)C=C1 DLBGTOJZFSANBA-FEGHXTNJSA-N 0.000 claims 1
- IYHLKUSCDRIOFT-OLJVKKBNSA-N [(1r,2r,3s,4r)-4-[[5-[1-[(4-chloropyridin-2-yl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2N=CC=C(Cl)C=2)C=C1 IYHLKUSCDRIOFT-OLJVKKBNSA-N 0.000 claims 1
- TWBPBWYLPUMCOW-DIKXZXNQSA-N [(1r,2r,3s,4r)-4-[[5-[1-[[3-[(s)-ethenylsulfinyl]phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(C=CC=2)[S@@](=O)C=C)C=C1 TWBPBWYLPUMCOW-DIKXZXNQSA-N 0.000 claims 1
- HDJNUKBEURNLBT-ZHKFALCXSA-N [(1r,2r,3s,4r)-4-[[5-[1-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(F)C(=CC=2)C(F)(F)F)C=C1 HDJNUKBEURNLBT-ZHKFALCXSA-N 0.000 claims 1
- PJRCTZBKHXJXRQ-ZHKFALCXSA-N [(1r,2r,3s,4r)-4-[[5-[1-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(C(Cl)=CC=2)C(F)(F)F)C=C1 PJRCTZBKHXJXRQ-ZHKFALCXSA-N 0.000 claims 1
- DGJMSWPZLCCSBO-JMSVASOKSA-N [(1r,2s,4r)-2-hydroxy-4-[[5-[1-(2-methylsulfanylethyl)pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound CSCCN1C=CC(C(=O)C=2C(=NC=NC=2)N[C@@H]2C[C@H](COS(N)(=O)=O)[C@@H](O)C2)=N1 DGJMSWPZLCCSBO-JMSVASOKSA-N 0.000 claims 1
- HIGPIECYSQVQPZ-VIZSFHNOSA-N [(1r,2s,4r)-2-hydroxy-4-[[5-[1-(naphthalen-2-ylmethyl)pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound C1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C3C=CC=CC3=CC=2)C=C1 HIGPIECYSQVQPZ-VIZSFHNOSA-N 0.000 claims 1
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- COQNMURTWPVPGH-CFAJVAMVSA-N [(1r,2s,4r)-2-hydroxy-4-[[5-[1-[(2s)-pent-3-yn-2-yl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound CC#C[C@H](C)N1C=CC(C(=O)C=2C(=NC=NC=2)N[C@@H]2C[C@H](COS(N)(=O)=O)[C@@H](O)C2)=N1 COQNMURTWPVPGH-CFAJVAMVSA-N 0.000 claims 1
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- WDYCQTFSEKORTR-LPMFXHHGSA-N [(1r,2s,4r)-4-[[5-[1-[(3,4-dichlorophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound C1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=C(Cl)C(Cl)=CC=2)C=C1 WDYCQTFSEKORTR-LPMFXHHGSA-N 0.000 claims 1
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- JSUHULTVIFQOTG-JQVVKUFUSA-N [(1r,2s,4r)-4-[[5-[1-[(3-bromophenyl)methyl]-5-[(1s)-1-methoxyethyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CO[C@@H](C)C1=CC(C(=O)C=2C(=NC=NC=2)N[C@@H]2C[C@H](COS(N)(=O)=O)[C@@H](O)C2)=NN1CC1=CC=CC(Br)=C1 JSUHULTVIFQOTG-JQVVKUFUSA-N 0.000 claims 1
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- LCCVIPVYENVOLZ-OGWOLHLISA-N [(1r,2s,4r)-4-[[5-[1-[(4-chlorophenyl)methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound C1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=NC=NC=C1C(=O)C1=NN(CC=2C=CC(Cl)=CC=2)C=C1 LCCVIPVYENVOLZ-OGWOLHLISA-N 0.000 claims 1
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- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- 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
- C07D401/02—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 two hetero rings
- C07D401/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361842097P | 2013-07-02 | 2013-07-02 | |
| US61/842,097 | 2013-07-02 | ||
| PCT/US2014/045129 WO2015002994A2 (en) | 2013-07-02 | 2014-07-01 | Heteroaryl compounds useful as inhibitors of sumo activating enzyme |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2916468A1 CA2916468A1 (en) | 2015-01-08 |
| CA2916468C true CA2916468C (en) | 2019-07-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2916468A Expired - Fee Related CA2916468C (en) | 2013-07-02 | 2014-07-01 | Heteroaryl compounds useful as inhibitors of sumo activating enzyme |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9695154B2 (enExample) |
| EP (1) | EP3016934B1 (enExample) |
| JP (1) | JP6378759B2 (enExample) |
| CN (1) | CN105492429A (enExample) |
| BR (1) | BR112015032902A8 (enExample) |
| CA (1) | CA2916468C (enExample) |
| EA (1) | EA032577B1 (enExample) |
| WO (1) | WO2015002994A2 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8008307B2 (en) | 2006-08-08 | 2011-08-30 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of E1 activating enzymes |
| UA116534C2 (uk) | 2012-02-17 | 2018-04-10 | Мілленніум Фармасьютікалз, Інк. | Піразолопіримідинілові інгібітори убіквітинактивуючого ферменту |
| CN104684559A (zh) | 2012-08-03 | 2015-06-03 | 米伦纽姆医药公司 | 针对Uba6的吲哚取代的吡咯并嘧啶基抑制剂 |
| WO2015002994A2 (en) | 2013-07-02 | 2015-01-08 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of sumo activating enzyme |
| BR112016030787B1 (pt) | 2014-07-01 | 2022-12-20 | Takeda Pharmaceutical Company Limited | Entidade química, composição farmacêutica e seu uso |
| WO2017183927A1 (ko) * | 2016-04-20 | 2017-10-26 | 한국화학연구원 | 신규한 헤테로고리 화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 암의 예방 또는 치료용 약학적 조성물 |
| CN105670066A (zh) * | 2016-04-22 | 2016-06-15 | 宁波硫华聚合物有限公司 | 橡胶促进剂活性剂氧化镁母胶粒及其制备方法 |
| CN107586315B (zh) * | 2016-07-08 | 2020-03-31 | 成都海创药业有限公司 | 一种嵌合分子 |
| US10875834B2 (en) | 2016-07-22 | 2020-12-29 | Virginia Commonwealth University | Prodrug and protected forms of 5-hydroxymethylfurfuranal (5-HMF) and its derivatives |
| US12097199B2 (en) | 2018-07-09 | 2024-09-24 | Takeda Pharmaceutical Company Limited | Administration of SUMO-activating enzyme inhibitor and anti-CD20 antibodies |
| AU2019312296B2 (en) | 2018-07-27 | 2025-05-29 | Arcus Biosciences, Inc. | Pyridone A2R antagonists |
| US11578079B2 (en) | 2018-07-31 | 2023-02-14 | City Of Hope | SUMO inhibitor compounds and uses thereof |
| US12419890B2 (en) | 2019-02-27 | 2025-09-23 | Takeda Pharmaceutical Company Limited | Administration of sumo-activating enzyme inhibitor and checkpoint inhibitors |
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| EP3016934A2 (en) | 2016-05-11 |
| JP2016523925A (ja) | 2016-08-12 |
| JP6378759B2 (ja) | 2018-08-22 |
| EA032577B1 (ru) | 2019-06-28 |
| CA2916468A1 (en) | 2015-01-08 |
| EP3016934B1 (en) | 2018-01-10 |
| WO2015002994A3 (en) | 2015-05-28 |
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