BR112020008446A2 - Sulfonas e sulfóxidos bicíclicos e seus métodos de uso - Google Patents

Info

Publication number

BR112020008446A2

BR112020008446A2 BR112020008446-8A BR112020008446A BR112020008446A2 BR 112020008446 A2 BR112020008446 A2 BR 112020008446A2 BR 112020008446 A BR112020008446 A BR 112020008446A BR 112020008446 A2 BR112020008446 A2 BR 112020008446A2

Authority

BR

Brazil

Prior art keywords

dihydro

triazole

phenyl

pyrrolo

pyrrole

Prior art date

2017-10-31

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 115
• 150000001875 compounds Chemical class 0.000 claims abstract description 204
• 238000011282 treatment Methods 0.000 claims abstract description 32
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 5
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 5
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 342
• -1 difluoro (phenyl) methyl Chemical group 0.000 claims description 258
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 168
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 143
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 105
• 125000001072 heteroaryl group Chemical group 0.000 claims description 72
• 201000010099 disease Diseases 0.000 claims description 71
• 208000035475 disorder Diseases 0.000 claims description 71
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 62
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 48
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 48
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
• 229910052731 fluorine Inorganic materials 0.000 claims description 48
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 44
• 239000011737 fluorine Substances 0.000 claims description 43
• 125000000623 heterocyclic group Chemical group 0.000 claims description 43
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 42
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 34
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 34
• 150000003852 triazoles Chemical class 0.000 claims description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
• 229910052801 chlorine Inorganic materials 0.000 claims description 33
• 239000000460 chlorine Chemical group 0.000 claims description 33
• 229910052717 sulfur Inorganic materials 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 101001109145 Homo sapiens Receptor-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims description 28
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
• 229910052805 deuterium Inorganic materials 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000004001 thioalkyl group Chemical group 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• 208000002320 spinal muscular atrophy Diseases 0.000 claims description 23
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 21
• 125000004429 atom Chemical group 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 20
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 19
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 150000002431 hydrogen Chemical group 0.000 claims description 18
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 16
• 208000011580 syndromic disease Diseases 0.000 claims description 16
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 15
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 15
• 208000006011 Stroke Diseases 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000004434 sulfur atom Chemical group 0.000 claims description 14
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 13
• 208000024827 Alzheimer disease Diseases 0.000 claims description 13
• 101000643956 Homo sapiens Cytochrome b-c1 complex subunit Rieske, mitochondrial Proteins 0.000 claims description 13
• 101001099199 Homo sapiens RalA-binding protein 1 Proteins 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 239000001301 oxygen Chemical group 0.000 claims description 13
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
• 208000023105 Huntington disease Diseases 0.000 claims description 12
• 208000018737 Parkinson disease Diseases 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 239000011593 sulfur Chemical group 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 230000000750 progressive effect Effects 0.000 claims description 10
• 208000016192 Demyelinating disease Diseases 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
• 208000028867 ischemia Diseases 0.000 claims description 9
• 201000000585 muscular atrophy Diseases 0.000 claims description 9
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
• 125000001188 haloalkyl group Chemical group 0.000 claims description 8
• 201000006417 multiple sclerosis Diseases 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 7
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 7
• 206010018985 Haemorrhage intracranial Diseases 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 208000008574 Intracranial Hemorrhages Diseases 0.000 claims description 7
• 201000002832 Lewy body dementia Diseases 0.000 claims description 7
• 208000001089 Multiple system atrophy Diseases 0.000 claims description 7
• 206010028289 Muscle atrophy Diseases 0.000 claims description 7
• 208000032319 Primary lateral sclerosis Diseases 0.000 claims description 7
• 206010046298 Upper motor neurone lesion Diseases 0.000 claims description 7
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
• 201000010901 lateral sclerosis Diseases 0.000 claims description 7
• 208000005264 motor neuron disease Diseases 0.000 claims description 7
• 230000020763 muscle atrophy Effects 0.000 claims description 7
• 201000006938 muscular dystrophy Diseases 0.000 claims description 7
• 208000027232 peripheral nervous system disease Diseases 0.000 claims description 7
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 7
• 201000002241 progressive bulbar palsy Diseases 0.000 claims description 7
• 201000000196 pseudobulbar palsy Diseases 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 206010006542 Bulbar palsy Diseases 0.000 claims description 6
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 6
• 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 5
• 208000013044 corticobasal degeneration disease Diseases 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• VJWMTJHXXQBLMY-NXEZZACHSA-N (4R,6R)-2-(difluoromethylsulfonyl)-4-fluoro-6-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole Chemical compound FC(S(=O)(=O)C=1C=C2N(N=1)[C@H](C[C@H]2F)C1=CC=CC=C1)F VJWMTJHXXQBLMY-NXEZZACHSA-N 0.000 claims description 4
• FLALVOMOETWGRS-NSHDSACASA-N (5S)-2-ethylsulfonyl-5-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C(C)S(=O)(=O)C=1N=C2N(N=1)[C@@H](CC2)C1=C(C=CC=C1)F FLALVOMOETWGRS-NSHDSACASA-N 0.000 claims description 4
• YAOPMPMOGSDDNA-VIFPVBQESA-N (5S)-5-(2-chlorophenyl)-2-(difluoromethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1)[C@@H]1CCC=2N1N=C(N=2)S(=O)(=O)C(F)F YAOPMPMOGSDDNA-VIFPVBQESA-N 0.000 claims description 4
• XZIWMVMNBIEQNV-UHFFFAOYSA-N 2-[difluoro(phenyl)methyl]sulfinyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(S(=O)C=1N=C2N(N=1)C(CC2)C1=CC=CC=C1)(C1=CC=CC=C1)F XZIWMVMNBIEQNV-UHFFFAOYSA-N 0.000 claims description 4
• HWBKEGBYQFSIKV-UHFFFAOYSA-N 2-[difluoro(phenyl)methyl]sulfonyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(S(=O)(=O)C=1N=C2N(N=1)C(CC2)C1=CC=CC=C1)(C1=CC=CC=C1)F HWBKEGBYQFSIKV-UHFFFAOYSA-N 0.000 claims description 4
• MHEHTWKWEKZSFB-UHFFFAOYSA-N 2-ethylsulfonyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C(C)S(=O)(=O)C=1N=C2N(N=1)C(CC2)C1=CC=CC=C1 MHEHTWKWEKZSFB-UHFFFAOYSA-N 0.000 claims description 4
• SVQGZJHPWYVIRZ-UHFFFAOYSA-N 5-phenyl-2-(trifluoromethylsulfinyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1(=CC=CC=C1)C1CCC=2N1N=C(N=2)S(=O)C(F)(F)F SVQGZJHPWYVIRZ-UHFFFAOYSA-N 0.000 claims description 4
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
• 239000013543 active substance Substances 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
• 125000006419 fluorocyclopropyl group Chemical group 0.000 claims description 4
• 201000008752 progressive muscular atrophy Diseases 0.000 claims description 4
• HHINLZLVFLEJQI-STQMWFEESA-N (4S,6S)-2-cyclopropylsulfonyl-4-fluoro-6-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole Chemical compound C1(CC1)S(=O)(=O)C=1C=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1 HHINLZLVFLEJQI-STQMWFEESA-N 0.000 claims description 3
• DQUMLGFARKITLM-VXGBXAGGSA-N (5R,7R)-2-cyclopropylsulfonyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1(CC1)S(=O)(=O)C=1N=C2N(N=1)[C@H](C[C@H]2F)C1=CC=CC=C1 DQUMLGFARKITLM-VXGBXAGGSA-N 0.000 claims description 3
• XEBQBVUSFRZGJR-VOJFVSQTSA-N (5S)-2-[(S)-ethylsulfinyl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C(C)[S@](=O)C=1N=C2N(N=1)[C@@H](CC2)C1=CC=CC=C1 XEBQBVUSFRZGJR-VOJFVSQTSA-N 0.000 claims description 3
• QGUWTUFGVPQCQV-GWNMQOMSSA-N (5S)-5-(2-chlorophenyl)-2-[(S)-difluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1)[C@@H]1CCC=2N1N=C(N=2)[S@](=O)C(F)F QGUWTUFGVPQCQV-GWNMQOMSSA-N 0.000 claims description 3
• KNHQFFKMMQEAQC-JTQLQIEISA-N (5S)-5-(2-fluorophenyl)-2-methylsulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1)[C@@H]1CCC=2N1N=C(N=2)S(=O)(=O)C KNHQFFKMMQEAQC-JTQLQIEISA-N 0.000 claims description 3
• GJVQNJMKUPXZBB-IUCAKERBSA-N (5S,7S)-2-(difluoromethylsulfonyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F GJVQNJMKUPXZBB-IUCAKERBSA-N 0.000 claims description 3
• YLRKXPGENSDCSP-MMXNHZJYSA-N (5S,7S)-2-[(S)-difluoromethylsulfinyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC([S@@](=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F YLRKXPGENSDCSP-MMXNHZJYSA-N 0.000 claims description 3
• FIVNABNNUSVPPX-MXQSDKMXSA-N (5S,7S)-2-benzylsulfinyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C(C1=CC=CC=C1)S(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1 FIVNABNNUSVPPX-MXQSDKMXSA-N 0.000 claims description 3
• MWGGBZPAGIKAMH-QZSHFQNPSA-N (5S,7S)-2-tert-butylsulfinyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C(C)(C)(C)S(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1 MWGGBZPAGIKAMH-QZSHFQNPSA-N 0.000 claims description 3
• FZSXZEKVNHPNGT-RYUDHWBXSA-N (5S,7S)-2-tert-butylsulfonyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C(C)(C)(C)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1 FZSXZEKVNHPNGT-RYUDHWBXSA-N 0.000 claims description 3
• ZFTBGQRZRZHYQE-IUCAKERBSA-N (5S,7S)-5-(3-chlorophenyl)-2-(difluoromethylsulfonyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC=1C=C(C=CC=1)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C(F)F)F ZFTBGQRZRZHYQE-IUCAKERBSA-N 0.000 claims description 3
• XKLZUFWDFSHHNZ-RYUDHWBXSA-N (5S,7S)-5-(3-chlorophenyl)-2-cyclopropylsulfonyl-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC=1C=C(C=CC=1)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C1CC1)F XKLZUFWDFSHHNZ-RYUDHWBXSA-N 0.000 claims description 3
• AQGFAEIJLCECGE-RYUDHWBXSA-N (5S,7S)-5-(5-chloro-2-fluorophenyl)-2-cyclopropylsulfonyl-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC=1C=CC(=C(C=1)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C1CC1)F)F AQGFAEIJLCECGE-RYUDHWBXSA-N 0.000 claims description 3
• YLRKXPGENSDCSP-UHFFFAOYSA-N 2-(difluoromethylsulfinyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(S(=O)C=1N=C2N(N=1)C(CC2F)C1=CC=CC=C1)F YLRKXPGENSDCSP-UHFFFAOYSA-N 0.000 claims description 3
• YKCWWULWZZZLTK-UHFFFAOYSA-N 2-(difluoromethylsulfonyl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(S(=O)(=O)C=1N=C2N(N=1)C(CC2)C1=CC=CC=C1)F YKCWWULWZZZLTK-UHFFFAOYSA-N 0.000 claims description 3
• HQLOEKQOWQSDAA-UHFFFAOYSA-N 2-methylsulfonyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CS(=O)(=O)C=1N=C2N(N=1)C(CC2)C1=CC=CC=C1 HQLOEKQOWQSDAA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004965 chloroalkyl group Chemical group 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• YAOPMPMOGSDDNA-SECBINFHSA-N (5R)-5-(2-chlorophenyl)-2-(difluoromethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1)[C@H]1CCC=2N1N=C(N=2)S(=O)(=O)C(F)F YAOPMPMOGSDDNA-SECBINFHSA-N 0.000 claims description 2
• TUIFRWUZECYERG-UGZDLDLSSA-N (5S)-2-[(R)-difluoromethylsulfinyl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC([S@](=O)C=1N=C2N(N=1)[C@@H](CC2)C1=CC=CC=C1)F TUIFRWUZECYERG-UGZDLDLSSA-N 0.000 claims description 2
• TUIFRWUZECYERG-ZRNGKTOUSA-N (5S)-2-[(S)-difluoromethylsulfinyl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC([S@@](=O)C=1N=C2N(N=1)[C@@H](CC2)C1=CC=CC=C1)F TUIFRWUZECYERG-ZRNGKTOUSA-N 0.000 claims description 2
• QGUWTUFGVPQCQV-LXGOIASLSA-N (5S)-5-(2-chlorophenyl)-2-[(R)-difluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1)[C@@H]1CCC=2N1N=C(N=2)[S@@](=O)C(F)F QGUWTUFGVPQCQV-LXGOIASLSA-N 0.000 claims description 2
• YLRKXPGENSDCSP-FRUKKLPWSA-N (5S,7S)-2-[(R)-difluoromethylsulfinyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC([S@](=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F YLRKXPGENSDCSP-FRUKKLPWSA-N 0.000 claims description 2
• FFTYPTIQUXWZBE-HOTGVXAUSA-N (5S,7S)-2-benzylsulfonyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C(C1=CC=CC=C1)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1 FFTYPTIQUXWZBE-HOTGVXAUSA-N 0.000 claims description 2
• IKBHTYYYUCTDSO-AHWMOBJXSA-N (5S,7S)-2-cyclopropylsulfinyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1(CC1)S(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1 IKBHTYYYUCTDSO-AHWMOBJXSA-N 0.000 claims description 2
• DQUMLGFARKITLM-RYUDHWBXSA-N (5S,7S)-2-cyclopropylsulfonyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1(CC1)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1 DQUMLGFARKITLM-RYUDHWBXSA-N 0.000 claims description 2
• LVHCMWUMCDUIHW-QWRGUYRKSA-N (5S,7S)-5-(3-chloro-2-fluorophenyl)-2-cyclopropylsulfonyl-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC=1C(=C(C=CC=1)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C1CC1)F)F LVHCMWUMCDUIHW-QWRGUYRKSA-N 0.000 claims description 2
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