JP2016523925A5

JP2016523925A5 -

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Publication number: JP2016523925A5
Authority: JP; Japan
Prior art keywords: amino; carbonyl; methylsulfamate; pyrimidin; pyrazol
Prior art date: 2014-07-01
Legal status : Granted

Application number

JP2016524326A

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English (en)

Japanese (ja)

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JP2016523925A (ja

JP6378759B2 (ja

Filing date

2014-07-01

Publication date

2017-08-10

2014-07-01 Application filed filed Critical

2014-07-01 Priority claimed from PCT/US2014/045129 external-priority patent/WO2015002994A2/en

2016-08-12 Publication of JP2016523925A publication Critical patent/JP2016523925A/ja

2017-08-10 Publication of JP2016523925A5 publication Critical patent/JP2016523925A5/ja

2018-08-22 Application granted granted Critical

2018-08-22 Publication of JP6378759B2 publication Critical patent/JP6378759B2/ja

Status Expired - Fee Related legal-status Critical Current

2034-07-01 Anticipated expiration legal-status Critical

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-1 chloro, bromo, fluoro, methyl Chemical group 0.000 claims description 118
150000001875 compounds Chemical class 0.000 claims description 68
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
229910052739 hydrogen Inorganic materials 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 48
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 claims description 25
229910052757 nitrogen Inorganic materials 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
125000005842 heteroatom Chemical group 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 22
239000001301 oxygen Chemical group 0.000 claims description 22
229910052717 sulfur Chemical group 0.000 claims description 22
239000011593 sulfur Chemical group 0.000 claims description 22
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
150000002431 hydrogen Chemical class 0.000 claims description 19
125000001931 aliphatic group Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
125000002723 alicyclic group Chemical group 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 10
206010028980 Neoplasm Diseases 0.000 claims description 9
201000011510 cancer Diseases 0.000 claims description 9
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
CUIKBCRNTKLWBN-HMGXFRNOSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@@H](C)C1=CC=CC=C1)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@@H](C)C1=CC=CC=C1)O)O)(=O)=O CUIKBCRNTKLWBN-HMGXFRNOSA-N 0.000 claims description 4
CUIKBCRNTKLWBN-ALAPKIMRSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@H](C)C1=CC=CC=C1)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@H](C)C1=CC=CC=C1)O)O)(=O)=O CUIKBCRNTKLWBN-ALAPKIMRSA-N 0.000 claims description 4
RDEIPCANAWMDQG-NGVUMRSOSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@H]1CCC2=CC=CC=C12)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@H]1CCC2=CC=CC=C12)O)O)(=O)=O RDEIPCANAWMDQG-NGVUMRSOSA-N 0.000 claims description 4
MVVWBVVFMKXRKL-QUUBWDHISA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C)[C@@H](C)C1=CC(=CC=C1)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C)[C@@H](C)C1=CC(=CC=C1)Cl)O)(=O)=O MVVWBVVFMKXRKL-QUUBWDHISA-N 0.000 claims description 4
GRXXGSZIFOLCNC-HOWVWPRWSA-N CNS(O[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)C#C)O)(=O)=O Chemical compound CNS(O[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)C#C)O)(=O)=O GRXXGSZIFOLCNC-HOWVWPRWSA-N 0.000 claims description 4
WWMKMIZXRDIITF-LVFOSTPZSA-N CNS(O[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)Cl)O)(=O)=O Chemical compound CNS(O[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)Cl)O)(=O)=O WWMKMIZXRDIITF-LVFOSTPZSA-N 0.000 claims description 4
DSWHRNMNCRYCHH-IUPKNAOTSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@@H](C)C=1OC(=CC1)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@@H](C)C=1OC(=CC1)Cl)O)(=O)=O DSWHRNMNCRYCHH-IUPKNAOTSA-N 0.000 claims description 4
MVIXBPLQUHOPLV-LONLNUGOSA-N CNS(O[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 Chemical compound CNS(O[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 MVIXBPLQUHOPLV-LONLNUGOSA-N 0.000 claims description 4
GRXXGSZIFOLCNC-IODINVCISA-N CNS(O[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)C#C)O)(=O)=O Chemical compound CNS(O[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)C#C)O)(=O)=O GRXXGSZIFOLCNC-IODINVCISA-N 0.000 claims description 4
WWMKMIZXRDIITF-LONLNUGOSA-N CNS(O[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)Cl)O)(=O)=O Chemical compound CNS(O[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)Cl)O)(=O)=O WWMKMIZXRDIITF-LONLNUGOSA-N 0.000 claims description 4
SQVLDYGFAZYURS-COCCGSRQSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@H](C)C1=NC(=CC=C1)Br)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@H](C)C1=NC(=CC=C1)Br)O)(=O)=O SQVLDYGFAZYURS-COCCGSRQSA-N 0.000 claims description 4
DSWHRNMNCRYCHH-BKBUGSPTSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@H](C)C=1OC(=CC1)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)[C@H](C)C=1OC(=CC1)Cl)O)(=O)=O DSWHRNMNCRYCHH-BKBUGSPTSA-N 0.000 claims description 4
FIRBSZKYRAKVNL-VXQXKNFASA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)C[C@@H]1[C@H](C1)C1=CC=CC=C1)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)C[C@@H]1[C@H](C1)C1=CC=CC=C1)F)O)(=O)=O FIRBSZKYRAKVNL-VXQXKNFASA-N 0.000 claims description 4
FIRBSZKYRAKVNL-GYMGFVCNSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)C[C@H]1[C@@H](C1)C1=CC=CC=C1)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)C[C@H]1[C@@H](C1)C1=CC=CC=C1)F)O)(=O)=O FIRBSZKYRAKVNL-GYMGFVCNSA-N 0.000 claims description 4
RYEIXLDXQJAHCK-ZWJZGKHJSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@@H](C)C1=CC(=CC=C1)Br)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@@H](C)C1=CC(=CC=C1)Br)F)O)(=O)=O RYEIXLDXQJAHCK-ZWJZGKHJSA-N 0.000 claims description 4
NIYDCXRHINGXIJ-CDHYSNCASA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@@H](C)C=1OC(=CC1)Cl)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@@H](C)C=1OC(=CC1)Cl)F)O)(=O)=O NIYDCXRHINGXIJ-CDHYSNCASA-N 0.000 claims description 4
IMOWXKHERQECRZ-AIDNLNPPSA-N CNS(O[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 Chemical compound CNS(O[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 IMOWXKHERQECRZ-AIDNLNPPSA-N 0.000 claims description 4
RYEIXLDXQJAHCK-MUXJXQBTSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@H](C)C1=CC(=CC=C1)Br)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@H](C)C1=CC(=CC=C1)Br)F)O)(=O)=O RYEIXLDXQJAHCK-MUXJXQBTSA-N 0.000 claims description 4
NIYDCXRHINGXIJ-ZNMJVABOSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@H](C)C=1OC(=CC1)Cl)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@H](C)C=1OC(=CC1)Cl)F)O)(=O)=O NIYDCXRHINGXIJ-ZNMJVABOSA-N 0.000 claims description 4
IMOWXKHERQECRZ-XARADAHVSA-N CNS(O[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 Chemical compound CNS(O[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 IMOWXKHERQECRZ-XARADAHVSA-N 0.000 claims description 4
AGPXRKVCXFBWJK-ZNMJVABOSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[1-[(1R)-1-[5-(trifluoromethyl)furan-2-yl]ethyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@H](C)C=1OC(=CC1)C(F)(F)F)F)O)(=O)=O AGPXRKVCXFBWJK-ZNMJVABOSA-N 0.000 claims description 4
AGPXRKVCXFBWJK-CDHYSNCASA-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] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)[C@@H](C)C=1OC(=CC1)C(F)(F)F)F)O)(=O)=O AGPXRKVCXFBWJK-CDHYSNCASA-N 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
JFIAZDSNIQHTEL-SOAMZJECSA-N CNS(=O)(=O)O[C@@H]1C[C@H]([C@H]([C@@H]1O)F)NC2=NC=NC=C2C(=O)C3=NN(C=C3)CC4=CC=CC=C4 Chemical compound CNS(=O)(=O)O[C@@H]1C[C@H]([C@H]([C@@H]1O)F)NC2=NC=NC=C2C(=O)C3=NN(C=C3)CC4=CC=CC=C4 JFIAZDSNIQHTEL-SOAMZJECSA-N 0.000 claims description 3
SYOLZSFZUGZJBE-YZGWKJHDSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC=CC=C1)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC=CC=C1)O)(=O)=O SYOLZSFZUGZJBE-YZGWKJHDSA-N 0.000 claims description 3
FKWCMFSOBUASDA-FHLIZLRMSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC#CC1CC1)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC#CC1CC1)O)(=O)=O FKWCMFSOBUASDA-FHLIZLRMSA-N 0.000 claims description 3
XJXWYFAXQLQFIE-AYOQOUSVSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC=CC=C1)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC=CC=C1)O)(=O)=O XJXWYFAXQLQFIE-AYOQOUSVSA-N 0.000 claims description 3
LUJJTPMVZSWUTL-XOKHGSTOSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=NC(=CC=C1)Br)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=NC(=CC=C1)Br)O)(=O)=O LUJJTPMVZSWUTL-XOKHGSTOSA-N 0.000 claims description 3
RKNUXLLPDOCUMS-XOKHGSTOSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=NC(=CC=C1)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=NC(=CC=C1)Cl)O)(=O)=O RKNUXLLPDOCUMS-XOKHGSTOSA-N 0.000 claims description 3
QBHXHGBWECTDIO-XFBWCDHKSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC=1OC(=CC1)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC=1OC(=CC1)Cl)O)(=O)=O QBHXHGBWECTDIO-XFBWCDHKSA-N 0.000 claims description 3
JFIAZDSNIQHTEL-FTEYMNFISA-N CNS(O[C@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC=CC=C1)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC=CC=C1)F)O)(=O)=O JFIAZDSNIQHTEL-FTEYMNFISA-N 0.000 claims description 3
KEVRRPYGQQZVDZ-ZHALLVOQSA-N [(1R,2R,4R)-4-[[5-(1-benzylpyrazole-3-carbonyl)pyrimidin-4-yl]amino]-3,3-difluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC=CC=C1)(F)F)O)(=O)=O KEVRRPYGQQZVDZ-ZHALLVOQSA-N 0.000 claims description 3
CBIYHIJFYNCWRH-MDASCCDHSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[3-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)OC(F)(F)F)O)(=O)=O CBIYHIJFYNCWRH-MDASCCDHSA-N 0.000 claims description 3
IEQLJJPHOPKRLL-AYOQOUSVSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)C(F)(F)F)O)(=O)=O IEQLJJPHOPKRLL-AYOQOUSVSA-N 0.000 claims description 3
PZCKLTWSXFDLLP-OGWOLHLISA-N [(1r,2s,4r)-4-[[5-[1-[(3-bromophenyl)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(Br)C=CC=2)C=C1 PZCKLTWSXFDLLP-OGWOLHLISA-N 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000004306 triazinyl group Chemical group 0.000 claims description 3
ZDIVCNVAGGHVFE-UHFFFAOYSA-N 1-(difluoromethoxy)-2-(trifluoromethoxy)ethyne Chemical compound FC(OC#COC(F)(F)F)F ZDIVCNVAGGHVFE-UHFFFAOYSA-N 0.000 claims description 2
BQIWIEMVBMKLJE-JZURDYQRSA-N 5-[1-[(3-chlorophenyl)methyl]pyrazole-3-carbonyl]-4-[[(1R,2S,3R,4R)-2,3-dihydroxy-4-[(sulfamoylamino)methyl]cyclopentyl]amino]pyrimidine Chemical compound ClC=1C=C(CN2N=C(C=C2)C(=O)C=2C(=NC=NC=2)N[C@H]2[C@@H]([C@@H]([C@H](C2)CNS(N)(=O)=O)O)O)C=CC=1 BQIWIEMVBMKLJE-JZURDYQRSA-N 0.000 claims description 2
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YOMXDZOEQCHOOR-NXLVEIQXSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CCC1=CC(=CC=C1)Br)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CCC1=CC(=CC=C1)Br)F)O)(=O)=O YOMXDZOEQCHOOR-NXLVEIQXSA-N 0.000 claims description 2
UBCZPFZWZIKOHV-JQLJIJSLSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)C[C@@H]1OC(CC1)(C)C)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)C[C@@H]1OC(CC1)(C)C)F)O)(=O)=O UBCZPFZWZIKOHV-JQLJIJSLSA-N 0.000 claims description 2
UBCZPFZWZIKOHV-ZQAQGDRJSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)C[C@H]1OC(CC1)(C)C)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)C[C@H]1OC(CC1)(C)C)F)O)(=O)=O UBCZPFZWZIKOHV-ZQAQGDRJSA-N 0.000 claims description 2
OYRDYIZKEYSERY-XLBJILASSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C)CC1=CC(=CC=C1)Br)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C)CC1=CC(=CC=C1)Br)F)O)(=O)=O OYRDYIZKEYSERY-XLBJILASSA-N 0.000 claims description 2
CEAUYSVPGRCYFP-XLBJILASSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C)CC1=CC(=CC=C1)I)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C)CC1=CC(=CC=C1)I)F)O)(=O)=O CEAUYSVPGRCYFP-XLBJILASSA-N 0.000 claims description 2
BGVYARSOCDHCRK-FXRXJOCMSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC(N1CCCC1)=O)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC(N1CCCC1)=O)F)O)(=O)=O BGVYARSOCDHCRK-FXRXJOCMSA-N 0.000 claims description 2
AYLKRSHHHJFBRA-QQTQMKHKSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C(=CC=C1)Br)F)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C(=CC=C1)Br)F)F)O)(=O)=O AYLKRSHHHJFBRA-QQTQMKHKSA-N 0.000 claims description 2
ZUAQEJYZQRVWHW-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)Br)Cl)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)Br)Cl)F)O)(=O)=O ZUAQEJYZQRVWHW-SOAMZJECSA-N 0.000 claims description 2
OYODIYYQEDCCKP-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)Cl)Cl)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)Cl)Cl)F)O)(=O)=O OYODIYYQEDCCKP-SOAMZJECSA-N 0.000 claims description 2
PUTZGOUFMVVCPH-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)Br)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)Br)F)O)(=O)=O PUTZGOUFMVVCPH-SOAMZJECSA-N 0.000 claims description 2
XNDNVDKWDWOJOV-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)Cl)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)Cl)F)O)(=O)=O XNDNVDKWDWOJOV-SOAMZJECSA-N 0.000 claims description 2
LWCIUZATCCRXDX-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)F)Br)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)F)Br)F)O)(=O)=O LWCIUZATCCRXDX-SOAMZJECSA-N 0.000 claims description 2
KABSWPIWRGYPKT-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)F)Cl)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)F)Cl)F)O)(=O)=O KABSWPIWRGYPKT-SOAMZJECSA-N 0.000 claims description 2
KJOQPXNIDCPYEN-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)F)I)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)F)I)F)O)(=O)=O KJOQPXNIDCPYEN-SOAMZJECSA-N 0.000 claims description 2
UGUZMDYNCZOUTF-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)Br)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)Br)F)O)(=O)=O UGUZMDYNCZOUTF-SOAMZJECSA-N 0.000 claims description 2
SQQANJOXIAGGIS-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)Cl)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)Cl)F)O)(=O)=O SQQANJOXIAGGIS-SOAMZJECSA-N 0.000 claims description 2
HIPAZJXGQKGAIB-SOAMZJECSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)I)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)I)F)O)(=O)=O HIPAZJXGQKGAIB-SOAMZJECSA-N 0.000 claims description 2
DCRIEAUXIQSONG-QVHJCDIPSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)N(C)C(C=C)=O)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)N(C)C(C=C)=O)F)O)(=O)=O DCRIEAUXIQSONG-QVHJCDIPSA-N 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
MSFYOCVNPNQPGM-YYTDSSBASA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[3-[1-[[3-(trifluoromethoxy)phenyl]methyl]pyrrole-3-carbonyl]pyridin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=C(C=NC=C1)C(=O)C1=CN(C=C1)CC1=CC(=CC=C1)OC(F)(F)F)F)O)(=O)=O MSFYOCVNPNQPGM-YYTDSSBASA-N 0.000 claims description 2
PRBUDYVDKSHYSJ-SOAMZJECSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[1-[[3-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)OC(F)(F)F)F)O)(=O)=O PRBUDYVDKSHYSJ-SOAMZJECSA-N 0.000 claims description 2
QZOMRDZIYTYGDA-ANTGDGSKSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[1-[[3-(trifluoromethoxy)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC(=CC=C1)OC(F)(F)F)F)O)(=O)=O QZOMRDZIYTYGDA-ANTGDGSKSA-N 0.000 claims description 2
SHSOCALGPBTFLE-SOAMZJECSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)C(F)(F)F)F)O)(=O)=O SHSOCALGPBTFLE-SOAMZJECSA-N 0.000 claims description 2
VTYCGLOBMUSRIJ-ANTGDGSKSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC(=CC=C1)C(F)(F)F)F)O)(=O)=O VTYCGLOBMUSRIJ-ANTGDGSKSA-N 0.000 claims description 2
AUZLPTVRNOJMIC-YWTNHNAXSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[1-[[4-(trifluoromethyl)furan-2-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC=1OC=C(C1)C(F)(F)F)F)O)(=O)=O AUZLPTVRNOJMIC-YWTNHNAXSA-N 0.000 claims description 2
CMLBOQMFHMANLK-FXRXJOCMSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[1-[[5-(trifluoromethyl)furan-2-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC=1OC(=CC1)C(F)(F)F)F)O)(=O)=O CMLBOQMFHMANLK-FXRXJOCMSA-N 0.000 claims description 2
AOMCTCPKUUKGFW-FXRXJOCMSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[1-[[5-(trifluoromethyl)thiophen-2-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC=1SC(=CC1)C(F)(F)F)F)O)(=O)=O AOMCTCPKUUKGFW-FXRXJOCMSA-N 0.000 claims description 2
MUXHFTABBKTLQB-LRCYWBKYSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[5-methyl-1-[[5-(trifluoromethyl)furan-2-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C)CC=1OC(=CC1)C(F)(F)F)F)O)(=O)=O MUXHFTABBKTLQB-LRCYWBKYSA-N 0.000 claims description 2
GXQLIIHHEYLOFD-QSFMABPGSA-N [(1R,2R,3R,4R)-4-[[5-[1-[(3-chlorophenyl)methyl]-5-(trifluoromethyl)pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C(F)(F)F)CC1=CC(=CC=C1)Cl)F)O)(=O)=O GXQLIIHHEYLOFD-QSFMABPGSA-N 0.000 claims description 2
RUHDUVVNKMSPBL-SOAMZJECSA-N [(1R,2R,3R,4R)-4-[[5-[1-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)C(F)(F)F)Cl)F)O)(=O)=O RUHDUVVNKMSPBL-SOAMZJECSA-N 0.000 claims description 2
IZQLENMNZGAPQS-SOAMZJECSA-N [(1R,2R,3R,4R)-4-[[5-[1-[[3-(difluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)OC(F)F)F)O)(=O)=O IZQLENMNZGAPQS-SOAMZJECSA-N 0.000 claims description 2
RVGLTSRIACMROV-ANTGDGSKSA-N [(1R,2R,3R,4R)-4-[[5-[1-[[3-(difluoromethoxy)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC(=CC=C1)OC(F)F)F)O)(=O)=O RVGLTSRIACMROV-ANTGDGSKSA-N 0.000 claims description 2
FBSRQNAFRMGWPG-DLVXIWMQSA-N [(1R,2R,3R,4R)-4-[[5-[1-[[4-chloro-3-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)OC(F)(F)F)F)O)(=O)=O FBSRQNAFRMGWPG-DLVXIWMQSA-N 0.000 claims description 2
JNJRALPLTZRKMP-SOAMZJECSA-N [(1R,2R,3R,4R)-4-[[5-[1-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)C(F)(F)F)F)O)(=O)=O JNJRALPLTZRKMP-SOAMZJECSA-N 0.000 claims description 2
SMJVNCUWAOXFGR-KLICCBINSA-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] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC=1OC(=CC1)C(F)F)F)O)(=O)=O SMJVNCUWAOXFGR-KLICCBINSA-N 0.000 claims description 2
PWJCZVKJFPHNOR-VGUOSERISA-N [(1R,2R,3R,4R)-4-[[5-[1-benzyl-5-(trifluoromethyl)pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C(=C1)C(F)(F)F)CC1=CC=CC=C1)F)O)(=O)=O PWJCZVKJFPHNOR-VGUOSERISA-N 0.000 claims description 2
VTDBKYCNSYRRCK-VGUOSERISA-N [(1R,2R,3R,4R)-4-[[5-[5-chloro-1-[[3-(trifluoromethyl)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C(=C1)Cl)CC1=CC(=CC=C1)C(F)(F)F)F)O)(=O)=O VTDBKYCNSYRRCK-VGUOSERISA-N 0.000 claims description 2
KCEKHQXDJSHLGD-ZHCAMHROSA-N [(1R,2R,3R,4R)-4-[[5-[5-chloro-1-[[5-(trifluoromethyl)-1,2-oxazol-3-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C(=C1)Cl)CC1=NOC(=C1)C(F)(F)F)F)O)(=O)=O KCEKHQXDJSHLGD-ZHCAMHROSA-N 0.000 claims description 2
JVHIVHSCXDAKRY-BCXHYRKLSA-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] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C(=C1)Cl)CC=1OC(=CC1)C(F)(F)F)F)O)(=O)=O JVHIVHSCXDAKRY-BCXHYRKLSA-N 0.000 claims description 2
GRHWJUXYVDQRLX-BEKAIBRUSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-[1-[[2-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC=C1)OC(F)(F)F)O)O)(=O)=O GRHWJUXYVDQRLX-BEKAIBRUSA-N 0.000 claims description 2
SGMXXQVHIHRXJF-JYBIWHBTSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-[1-[[2-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC=C1)C(F)(F)F)O)O)(=O)=O SGMXXQVHIHRXJF-JYBIWHBTSA-N 0.000 claims description 2
OZFXKPJHUAZUSY-JYBIWHBTSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-[1-[[3-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)OC(F)(F)F)O)O)(=O)=O OZFXKPJHUAZUSY-JYBIWHBTSA-N 0.000 claims description 2
CFEWGJYUPJHEBD-JYBIWHBTSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)C(F)(F)F)O)O)(=O)=O CFEWGJYUPJHEBD-JYBIWHBTSA-N 0.000 claims description 2
XLISCIUDFINHDF-JYBIWHBTSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-[1-[[4-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC=C(C=C1)OC(F)(F)F)O)O)(=O)=O XLISCIUDFINHDF-JYBIWHBTSA-N 0.000 claims description 2
DEAVNKUNMBCMRD-JYBIWHBTSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-[1-[[4-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC=C(C=C1)C(F)(F)F)O)O)(=O)=O DEAVNKUNMBCMRD-JYBIWHBTSA-N 0.000 claims description 2
WZUAJCLULDMBBF-KNCCTNLNSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-[1-[[5-(trifluoromethyl)furan-2-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC=1OC(=CC1)C(F)(F)F)O)O)(=O)=O WZUAJCLULDMBBF-KNCCTNLNSA-N 0.000 claims description 2
KHOAOXFKFDMTQL-MDUILUSMSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-[5-methyl-1-[[5-(trifluoromethyl)furan-2-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C)CC=1OC(=CC1)C(F)(F)F)O)O)(=O)=O KHOAOXFKFDMTQL-MDUILUSMSA-N 0.000 claims description 2
UJLSHBISOYBVLA-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[2,4-bis(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=C(C=C1)C(F)(F)F)C(F)(F)F)O)O)(=O)=O UJLSHBISOYBVLA-JYBIWHBTSA-N 0.000 claims description 2
JANQDTLQYOQEHH-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[2,5-bis(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)C(F)(F)F)C(F)(F)F)O)O)(=O)=O JANQDTLQYOQEHH-JYBIWHBTSA-N 0.000 claims description 2
GSRACBBPTQFZCF-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)C(F)(F)F)Cl)O)O)(=O)=O GSRACBBPTQFZCF-JYBIWHBTSA-N 0.000 claims description 2
ZXAISCVWVFXKLB-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)C(F)(F)F)F)O)O)(=O)=O ZXAISCVWVFXKLB-JYBIWHBTSA-N 0.000 claims description 2
CIVUONMHJBLSTC-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O)O)(=O)=O CIVUONMHJBLSTC-JYBIWHBTSA-N 0.000 claims description 2
IUJQIQGTWXHEMG-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[3-(difluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)OC(F)F)O)O)(=O)=O IUJQIQGTWXHEMG-JYBIWHBTSA-N 0.000 claims description 2
IIEDKIDZMXAGEC-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)C(F)(F)F)F)O)O)(=O)=O IIEDKIDZMXAGEC-JYBIWHBTSA-N 0.000 claims description 2
SCRTXZNIDUYQLU-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC(=C1)C(F)(F)F)F)O)O)(=O)=O SCRTXZNIDUYQLU-JYBIWHBTSA-N 0.000 claims description 2
FRQJNUIWQDRWID-BEKAIBRUSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[4-chloro-3-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)OC(F)(F)F)O)O)(=O)=O FRQJNUIWQDRWID-BEKAIBRUSA-N 0.000 claims description 2
QUXFQSYAEDAIMZ-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)C(F)(F)F)O)O)(=O)=O QUXFQSYAEDAIMZ-JYBIWHBTSA-N 0.000 claims description 2
FRVBSLRAOBHLRN-YKCBXCCJSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[4-chloro-3-(trifluoromethylsulfanyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)SC(F)(F)F)O)O)(=O)=O FRVBSLRAOBHLRN-YKCBXCCJSA-N 0.000 claims description 2
VWNJUDDAQGIDOP-JYBIWHBTSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[4-fluoro-2-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=C(C=C1)F)C(F)(F)F)O)O)(=O)=O VWNJUDDAQGIDOP-JYBIWHBTSA-N 0.000 claims description 2
LTBYKLSORIHBCN-BEKAIBRUSA-N [(1R,2R,3S,4R)-4-[[5-[1-[[4-fluoro-3-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)F)OC(F)(F)F)O)O)(=O)=O LTBYKLSORIHBCN-BEKAIBRUSA-N 0.000 claims description 2
KGTUIAYUSBJENB-GQWLDOHISA-N [(1R,2S,4R)-2-hydroxy-4-[[3-[1-[[3-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyridin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=C(C=NC=C1)C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)OC(F)(F)F)O)(=O)=O KGTUIAYUSBJENB-GQWLDOHISA-N 0.000 claims description 2
PFCQTWFLHAVBGT-VOQZNFBZSA-N [(1R,2S,4R)-2-hydroxy-4-[[3-[1-[[3-(trifluoromethoxy)phenyl]methyl]pyrrole-3-carbonyl]pyridin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=C(C=NC=C1)C(=O)C1=CN(C=C1)CC1=CC(=CC=C1)OC(F)(F)F)O)(=O)=O PFCQTWFLHAVBGT-VOQZNFBZSA-N 0.000 claims description 2
GPBFBYPZULFAQW-TYCQWZJGSA-N [(1R,2S,4R)-2-hydroxy-4-[[3-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyridin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=C(C=NC=C1)C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)C(F)(F)F)O)(=O)=O GPBFBYPZULFAQW-TYCQWZJGSA-N 0.000 claims description 2
FVGDOPQFPYAJLD-XOKHGSTOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=NN(C(=C1)C(F)(F)F)C)O)(=O)=O FVGDOPQFPYAJLD-XOKHGSTOSA-N 0.000 claims description 2
VRSOXCASUSVOEV-DKSSEZFCSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[2-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC=C1)OC(F)(F)F)O)(=O)=O VRSOXCASUSVOEV-DKSSEZFCSA-N 0.000 claims description 2
PJQSUZGMONYFAL-UHOFOFEASA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[2-(trifluoromethyl)-1,3-thiazol-5-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CN=C(S1)C(F)(F)F)O)(=O)=O PJQSUZGMONYFAL-UHOFOFEASA-N 0.000 claims description 2
LYZDRYUZUGVAKH-MDASCCDHSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[2-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC=C1)C(F)(F)F)O)(=O)=O LYZDRYUZUGVAKH-MDASCCDHSA-N 0.000 claims description 2
QCMSYDPWXYPOFS-XOKHGSTOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[2-(trifluoromethyl)pyridin-4-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=NC=C1)C(F)(F)F)O)(=O)=O QCMSYDPWXYPOFS-XOKHGSTOSA-N 0.000 claims description 2
TVGGSRRDOPJVJZ-XOKHGSTOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC(=NN1C)C(F)(F)F)O)(=O)=O TVGGSRRDOPJVJZ-XOKHGSTOSA-N 0.000 claims description 2
VDRDHVTWEQWQKN-LSTHTHJFSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[3-(trifluoromethoxy)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC1=CC(=CC=C1)OC(F)(F)F)O)(=O)=O VDRDHVTWEQWQKN-LSTHTHJFSA-N 0.000 claims description 2
GXDNBUAJKSZPIE-YZGWKJHDSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[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)O)(=O)=O GXDNBUAJKSZPIE-YZGWKJHDSA-N 0.000 claims description 2
QNSWRMGKJAEZTF-MDASCCDHSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[4-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC=C(C=C1)OC(F)(F)F)O)(=O)=O QNSWRMGKJAEZTF-MDASCCDHSA-N 0.000 claims description 2
JFTCHYDNELZMEO-AYOQOUSVSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[4-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC=C(C=C1)C(F)(F)F)O)(=O)=O JFTCHYDNELZMEO-AYOQOUSVSA-N 0.000 claims description 2
XGRLNPUCXUQBAB-XFBWCDHKSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[5-(trifluoromethyl)furan-2-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC=1OC(=CC1)C(F)(F)F)O)(=O)=O XGRLNPUCXUQBAB-XFBWCDHKSA-N 0.000 claims description 2
XKWAXHDXUVIEKK-XOKHGSTOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[5-(trifluoromethyl)furan-2-yl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC=1OC(=CC1)C(F)(F)F)O)(=O)=O XKWAXHDXUVIEKK-XOKHGSTOSA-N 0.000 claims description 2
WAPBZNDQBDOAPB-XFBWCDHKSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[5-(trifluoromethyl)thiophen-2-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC=1SC(=CC1)C(F)(F)F)O)(=O)=O WAPBZNDQBDOAPB-XFBWCDHKSA-N 0.000 claims description 2
UKOHXTACTSKVNL-XOKHGSTOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[1-[[6-(trifluoromethyl)pyridin-2-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=NC(=CC=C1)C(F)(F)F)O)(=O)=O UKOHXTACTSKVNL-XOKHGSTOSA-N 0.000 claims description 2
IAKJATLNODFCSU-GQWLDOHISA-N [(1R,2S,4R)-4-[[3-[1-[[3-(difluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyridin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=C(C=NC=C1)C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)OC(F)F)O)(=O)=O IAKJATLNODFCSU-GQWLDOHISA-N 0.000 claims description 2
IJSWAORZAHOXSD-PUCZYUMASA-N [(1R,2S,4R)-4-[[3-[1-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyridin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=C(C=NC=C1)C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)C(F)(F)F)O)(=O)=O IJSWAORZAHOXSD-PUCZYUMASA-N 0.000 claims description 2
PMTKYVZHSZXOLY-PUCZYUMASA-N [(1R,2S,4R)-4-[[3-[1-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyridin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=C(C=NC=C1)C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)F)C(F)(F)F)O)(=O)=O PMTKYVZHSZXOLY-PUCZYUMASA-N 0.000 claims description 2
ZUYCYPFMQHPQPH-FHLIZLRMSA-N [(1R,2S,4R)-4-[[5-[1-[(3-chlorophenyl)methyl]-5-(trifluoromethyl)pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C(=C1)C(F)(F)F)CC1=CC(=CC=C1)Cl)O)(=O)=O ZUYCYPFMQHPQPH-FHLIZLRMSA-N 0.000 claims description 2
PWQBGLPSXLRNHB-MDASCCDHSA-N [(1R,2S,4R)-4-[[5-[1-[[2,4-bis(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=C(C=C1)C(F)(F)F)C(F)(F)F)O)(=O)=O PWQBGLPSXLRNHB-MDASCCDHSA-N 0.000 claims description 2
PCGLOVAIWRKVOG-MDASCCDHSA-N [(1R,2S,4R)-4-[[5-[1-[[2,5-bis(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)C(F)(F)F)C(F)(F)F)O)(=O)=O PCGLOVAIWRKVOG-MDASCCDHSA-N 0.000 claims description 2
LJTQBDUEWMXWCC-MDASCCDHSA-N [(1R,2S,4R)-4-[[5-[1-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=CC(=C1)C(F)(F)F)Cl)O)(=O)=O LJTQBDUEWMXWCC-MDASCCDHSA-N 0.000 claims description 2
OGEJLIDPMRJOJY-YZGWKJHDSA-N [(1R,2S,4R)-4-[[5-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[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 OGEJLIDPMRJOJY-YZGWKJHDSA-N 0.000 claims description 2
SZGIRYYSAJKNLF-MDASCCDHSA-N [(1R,2S,4R)-4-[[5-[1-[[3-(difluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)OC(F)F)O)(=O)=O SZGIRYYSAJKNLF-MDASCCDHSA-N 0.000 claims description 2
LELDVRJOYPLAOZ-YZGWKJHDSA-N [(1R,2S,4R)-4-[[5-[1-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[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 LELDVRJOYPLAOZ-YZGWKJHDSA-N 0.000 claims description 2
MDQUOMKSFAODKJ-XVGQJIODSA-N [(1R,2S,4R)-4-[[5-[1-[[4-chloro-3-(trifluoromethoxy)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)OC(F)(F)F)O)(=O)=O MDQUOMKSFAODKJ-XVGQJIODSA-N 0.000 claims description 2
GHYXCJYGPIOKHE-ZNZDAUKMSA-N [(1R,2S,4R)-4-[[5-[1-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=CC(=C(C=C1)Cl)C(F)(F)F)O)(=O)=O GHYXCJYGPIOKHE-ZNZDAUKMSA-N 0.000 claims description 2
ZZQVMWUNPFCZLF-MDASCCDHSA-N [(1R,2S,4R)-4-[[5-[1-[[4-fluoro-2-(trifluoromethyl)phenyl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C1=NN(C=C1)CC1=C(C=C(C=C1)F)C(F)(F)F)O)(=O)=O ZZQVMWUNPFCZLF-MDASCCDHSA-N 0.000 claims description 2
NULJBUKFKGHRNB-MOXGXCLJSA-N [(1R,2S,4R)-4-[[5-[1-[[4-fluoro-3-(trifluoromethoxy)phenyl]methyl]pyrrole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[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 NULJBUKFKGHRNB-MOXGXCLJSA-N 0.000 claims description 2
MGEVTDJFBSPXRP-XQAQDONZSA-N [(1R,2S,4R)-4-[[5-[1-[[5-(difluoromethyl)furan-2-yl]methyl]pyrazole-3-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[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 MGEVTDJFBSPXRP-XQAQDONZSA-N 0.000 claims description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
150000005350 bicyclononyls Chemical group 0.000 claims description 2
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 2
125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 2
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 2
125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 2
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 2
125000000532 dioxanyl group Chemical group 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
125000005956 isoquinolyl group Chemical group 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000003566 oxetanyl group Chemical group 0.000 claims description 2
125000005479 oxodihydropyridyl group Chemical group 0.000 claims description 2
125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 2
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims description 2
125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
125000005493 quinolyl group Chemical group 0.000 claims description 2
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 2
125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
206010006187 Breast cancer Diseases 0.000 claims 2
208000026310 Breast neoplasm Diseases 0.000 claims 2
206010009944 Colon cancer Diseases 0.000 claims 2
206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
206010033128 Ovarian cancer Diseases 0.000 claims 2
206010061535 Ovarian neoplasm Diseases 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 2
201000009613 breast lymphoma Diseases 0.000 claims 2
208000029742 colonic neoplasm Diseases 0.000 claims 2
125000001072 heteroaryl group Chemical group 0.000 claims 2
201000005202 lung cancer Diseases 0.000 claims 2
208000020816 lung neoplasm Diseases 0.000 claims 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
ULIGWSYQCJIIGH-TYCQWZJGSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=C(C=NC=C1)C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=C(C=NC=C1)C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)Cl)O)(=O)=O ULIGWSYQCJIIGH-TYCQWZJGSA-N 0.000 claims 1
RQAOVVKSNGLLEG-UHFFFAOYSA-N N'-[2-(difluoromethoxy)-2-(trifluoromethoxy)-2-(trifluoromethylsulfanyl)ethyl]-N'-ethyl-N,N-dimethylethyne-1,2-diamine Chemical compound FC(OC(CN(CC)C#CN(C)C)(SC(F)(F)F)OC(F)(F)F)F RQAOVVKSNGLLEG-UHFFFAOYSA-N 0.000 claims 1
241000927721 Tritia Species 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
125000001041 indolyl group Chemical group 0.000 claims 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
125000000160 oxazolidinyl group Chemical group 0.000 description 2
NQMPRNKNAURMEN-UHFFFAOYSA-N N',N'-diethyl-N,N-dimethylethyne-1,2-diamine Chemical compound CN(C)C#CN(CC)CC NQMPRNKNAURMEN-UHFFFAOYSA-N 0.000 description 1
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 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
125000005945 imidazopyridyl group Chemical group 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
238000000034 method Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1

JP2016524326A 2013-07-02 2014-07-01 Ｓｕｍｏ活性化酵素阻害剤として有用なヘテロアリール化合物 Expired - Fee Related JP6378759B2 (ja)