JP6378759B2 - 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 - Google Patents

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Publication number

JP6378759B2

JP6378759B2 JP2016524326A JP2016524326A JP6378759B2 JP 6378759 B2 JP6378759 B2 JP 6378759B2 JP 2016524326 A JP2016524326 A JP 2016524326A JP 2016524326 A JP2016524326 A JP 2016524326A JP 6378759 B2 JP6378759 B2 JP 6378759B2

Authority

JP

Japan

Prior art keywords

amino

carbonyl

methylsulfamate

pyrimidin

pyrazol

Prior art date

2013-07-02

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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• 125000001072 heteroaryl group Chemical group 0.000 title claims 3
• 230000003213 activating effect Effects 0.000 title 1
• 239000002532 enzyme inhibitor Substances 0.000 title 1
• -1 chloro, bromo, fluoro, methyl Chemical group 0.000 claims 64
• 150000001875 compounds Chemical class 0.000 claims 33
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 27
• 229910052739 hydrogen Inorganic materials 0.000 claims 24
• 239000001257 hydrogen Substances 0.000 claims 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 17
• FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 claims 13
• 229910052757 nitrogen Inorganic materials 0.000 claims 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 11
• 125000005842 heteroatom Chemical group 0.000 claims 11
• 229910052760 oxygen Inorganic materials 0.000 claims 11
• 239000001301 oxygen Chemical group 0.000 claims 11
• 229910052717 sulfur Chemical group 0.000 claims 11
• 239000011593 sulfur Chemical group 0.000 claims 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
• 150000002431 hydrogen Chemical class 0.000 claims 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
• 150000003839 salts Chemical class 0.000 claims 8
• 125000002723 alicyclic group Chemical group 0.000 claims 7
• 125000001931 aliphatic group Chemical group 0.000 claims 7
• 125000000217 alkyl group Chemical group 0.000 claims 7
• 125000000623 heterocyclic group Chemical group 0.000 claims 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 5
• 206010028980 Neoplasm Diseases 0.000 claims 4
• 201000011510 cancer Diseases 0.000 claims 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 3
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
• 229910052736 halogen Inorganic materials 0.000 claims 3
• 150000002367 halogens Chemical class 0.000 claims 3
• 239000008194 pharmaceutical composition Substances 0.000 claims 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
• 206010006187 Breast cancer Diseases 0.000 claims 2
• 208000026310 Breast neoplasm Diseases 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 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
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 125000002947 alkylene group Chemical group 0.000 claims 2
• 125000003118 aryl group Chemical group 0.000 claims 2
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
• 201000009613 breast lymphoma Diseases 0.000 claims 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims 2
• 208000029742 colonic neoplasm Diseases 0.000 claims 2
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
• 239000003937 drug carrier Substances 0.000 claims 2
• 125000001153 fluoro group Chemical group F* 0.000 claims 2
• 125000002541 furyl group Chemical group 0.000 claims 2
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• LMSOGEMAAACOKL-IDCJVQTKSA-N CNS(O[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 Chemical compound CNS(O[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 LMSOGEMAAACOKL-IDCJVQTKSA-N 0.000 claims 1
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• WSCBNJDTYWUZHO-YYTDSSBASA-N 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)Cl)F)O)(=O)=O 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)Cl)F)O)(=O)=O WSCBNJDTYWUZHO-YYTDSSBASA-N 0.000 claims 1
• KZLMIKXVIIVXBD-NXLVEIQXSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=C(C=NC=C1)C(=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=C(C=NC=C1)C(=O)C1=NN(C=C1)CC1=CC(=CC=C1)Cl)F)O)(=O)=O KZLMIKXVIIVXBD-NXLVEIQXSA-N 0.000 claims 1
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• IHVYANJFHPIYNH-NXLVEIQXSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(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=CN(C(=C1)C)CC1=CC(=CC=C1)Br)F)O)(=O)=O IHVYANJFHPIYNH-NXLVEIQXSA-N 0.000 claims 1
• AFMRRRQOAFMDDL-YYTDSSBASA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C(=C1)CC)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=CN(C(=C1)CC)CC1=CC(=CC=C1)Br)F)O)(=O)=O AFMRRRQOAFMDDL-YYTDSSBASA-N 0.000 claims 1
• UMVCSOQTVLVCKT-VGUOSERISA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C(=C1)Cl)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=CN(C(=C1)Cl)CC1=CC(=C(C=C1)F)Br)F)O)(=O)=O UMVCSOQTVLVCKT-VGUOSERISA-N 0.000 claims 1
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• AGYRPLZEEZPWBJ-VGUOSERISA-N 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)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=CN(C(=C1)Cl)CC1=CC(=CC=C1)I)F)O)(=O)=O AGYRPLZEEZPWBJ-VGUOSERISA-N 0.000 claims 1
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• SQVOIOGBONYMHP-LUBSMZHTSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC=1SC2=C(C1)C=CC=C2)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)CC=1SC2=C(C1)C=CC=C2)F)O)(=O)=O SQVOIOGBONYMHP-LUBSMZHTSA-N 0.000 claims 1
• ODMNPIRTKMOJMA-NTWJOZFCSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C1=CN(C=C1)CC=1SC2=C(C1Cl)C=CC=C2)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)CC=1SC2=C(C1Cl)C=CC=C2)F)O)(=O)=O ODMNPIRTKMOJMA-NTWJOZFCSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 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
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
• 241000927721 Tritia Species 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 150000005350 bicyclononyls Chemical group 0.000 claims 1
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
• 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims 1
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims 1
• 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 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 1
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 1
• 125000000532 dioxanyl group Chemical group 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 125000002883 imidazolyl group Chemical group 0.000 claims 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
• 125000001041 indolyl group Chemical group 0.000 claims 1
• JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
• 125000005956 isoquinolyl group Chemical group 0.000 claims 1
• 125000001786 isothiazolyl group Chemical group 0.000 claims 1
• 125000000842 isoxazolyl group Chemical group 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 125000002757 morpholinyl group Chemical group 0.000 claims 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
• 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
• 125000002971 oxazolyl group Chemical group 0.000 claims 1
• 125000003566 oxetanyl group Chemical group 0.000 claims 1
• 125000005479 oxodihydropyridyl group Chemical group 0.000 claims 1
• 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
• 125000004193 piperazinyl group Chemical group 0.000 claims 1
• 125000003386 piperidinyl group Chemical group 0.000 claims 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
• 125000003226 pyrazolyl group Chemical group 0.000 claims 1
• 125000002098 pyridazinyl group Chemical group 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
• 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims 1
• 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
• 125000000168 pyrrolyl group Chemical group 0.000 claims 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
• 125000005493 quinolyl group Chemical group 0.000 claims 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 1
• 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
• 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 claims 1
• 125000000335 thiazolyl group Chemical group 0.000 claims 1
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
• 125000001425 triazolyl group Chemical group 0.000 claims 1