JP2021501183A5 - - Google Patents
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- Publication number
- JP2021501183A5 JP2021501183A5 JP2020524177A JP2020524177A JP2021501183A5 JP 2021501183 A5 JP2021501183 A5 JP 2021501183A5 JP 2020524177 A JP2020524177 A JP 2020524177A JP 2020524177 A JP2020524177 A JP 2020524177A JP 2021501183 A5 JP2021501183 A5 JP 2021501183A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- dihydro
- fluoro
- triazole
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 10
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 208000002320 spinal muscular atrophy Diseases 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 206010033799 Paralysis Diseases 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims 4
- 208000021090 palsy Diseases 0.000 claims 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 230000000750 progressive effect Effects 0.000 claims 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 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 2
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 2
- 208000016192 Demyelinating disease Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 208000032843 Hemorrhage Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000032319 Primary lateral sclerosis Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000034799 Tauopathies Diseases 0.000 claims 2
- 206010046298 Upper motor neurone lesion Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 208000034158 bleeding Diseases 0.000 claims 2
- 230000000740 bleeding effect Effects 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000001054 cortical effect Effects 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- GFBLFDSCAKHHGX-UHFFFAOYSA-N cyclobutanecarbonitrile Chemical compound N#CC1CCC1 GFBLFDSCAKHHGX-UHFFFAOYSA-N 0.000 claims 2
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 230000007850 degeneration Effects 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000006419 fluorocyclopropyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 238000007917 intracranial administration Methods 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 201000010901 lateral sclerosis Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 208000005264 motor neuron disease Diseases 0.000 claims 2
- 201000000585 muscular atrophy Diseases 0.000 claims 2
- 201000006938 muscular dystrophy Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 201000008752 progressive muscular atrophy Diseases 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- HKXWWDZJUNBPRK-HTQZYQBOSA-N (5R,7R)-5-(2,3-difluorophenyl)-7-fluoro-2-(trifluoromethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1F)[C@H]1C[C@H](C=2N1N=C(N=2)S(=O)(=O)C(F)(F)F)F HKXWWDZJUNBPRK-HTQZYQBOSA-N 0.000 claims 1
- UAONBOVYJRVWMR-FPVGNUTFSA-N (5S)-2-[(R)-difluoromethylsulfinyl]-5-(3,5-difluorophenyl)-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)F)F UAONBOVYJRVWMR-FPVGNUTFSA-N 0.000 claims 1
- 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 1
- UAONBOVYJRVWMR-JLTPVHFHSA-N (5S)-2-[(S)-difluoromethylsulfinyl]-5-(3,5-difluorophenyl)-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)F)F UAONBOVYJRVWMR-JLTPVHFHSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- RLVPEWDNAJTHPG-UWVGGRQHSA-N (5S,7S)-2-(1,1-difluoroethylsulfonyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(C)(S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F RLVPEWDNAJTHPG-UWVGGRQHSA-N 0.000 claims 1
- VBCXAUDWTZKCRJ-RFMBEDMFSA-N (5S,7S)-2-(2,2-difluoro-1-methylcyclopropyl)sulfonyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1(C(C1)(C)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F VBCXAUDWTZKCRJ-RFMBEDMFSA-N 0.000 claims 1
- BGDZUFUIETXTSR-POFGUMTJSA-N (5S,7S)-2-(2,2-difluorocyclopropyl)sulfinyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1(C(C1)S(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F BGDZUFUIETXTSR-POFGUMTJSA-N 0.000 claims 1
- MAMPQXOYBIPBHM-XMCUXHSSSA-N (5S,7S)-2-(2,2-difluorocyclopropyl)sulfonyl-5-(2,3-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1(C(C1)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=C(C(=CC=C1)F)F)F MAMPQXOYBIPBHM-XMCUXHSSSA-N 0.000 claims 1
- DLKPEBBRYZMGPM-QRHSGQBVSA-N (5S,7S)-2-(2,2-difluorocyclopropyl)sulfonyl-5-(2,5-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1(C(C1)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=C(C=CC(=C1)F)F)F DLKPEBBRYZMGPM-QRHSGQBVSA-N 0.000 claims 1
- XFGLFTWQWQDZBQ-XMCUXHSSSA-N (5S,7S)-2-(2,2-difluorocyclopropyl)sulfonyl-5-(2,6-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1(C(C1)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=C(C=CC=C1F)F)F XFGLFTWQWQDZBQ-XMCUXHSSSA-N 0.000 claims 1
- IRAOKCYSKKTUAQ-QUOWQDAJSA-N (5S,7S)-2-(2,2-difluoroethylsulfinyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(CS(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F IRAOKCYSKKTUAQ-QUOWQDAJSA-N 0.000 claims 1
- AJXCFZGVPGVIOA-VELJJMKESA-N (5S,7S)-2-(3,3-difluorocyclobutyl)sulfinyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1(CC(C1)S(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F AJXCFZGVPGVIOA-VELJJMKESA-N 0.000 claims 1
- DQFOICQLOVNAEO-RYUDHWBXSA-N (5S,7S)-2-(3,3-difluorocyclobutyl)sulfonyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1(CC(C1)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F DQFOICQLOVNAEO-RYUDHWBXSA-N 0.000 claims 1
- LTEZZTGAECLDFU-IOTUWOHQSA-N (5S,7S)-2-(cyclopropylmethylsulfinyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1(CC1)CS(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1 LTEZZTGAECLDFU-IOTUWOHQSA-N 0.000 claims 1
- SFLYUWXLFMQZOO-STQMWFEESA-N (5S,7S)-2-(cyclopropylmethylsulfonyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1(CC1)CS(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1 SFLYUWXLFMQZOO-STQMWFEESA-N 0.000 claims 1
- DYWGGPMIIKDPOE-BPKJCTBOSA-N (5S,7S)-2-(difluoromethylsulfinyl)-7-fluoro-5-(3-fluorophenyl)-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)F DYWGGPMIIKDPOE-BPKJCTBOSA-N 0.000 claims 1
- MJALMXYHICUMPC-BPKJCTBOSA-N (5S,7S)-2-(difluoromethylsulfinyl)-7-fluoro-5-(4-fluorophenyl)-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=C(C=C1)F)F MJALMXYHICUMPC-BPKJCTBOSA-N 0.000 claims 1
- GCOSHJOKFXKVOW-YUMQZZPRSA-N (5S,7S)-2-(difluoromethylsulfonyl)-5-(2,3-difluorophenyl)-7-fluoro-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=C(C(=CC=C1)F)F)F GCOSHJOKFXKVOW-YUMQZZPRSA-N 0.000 claims 1
- OPCZKTFFXUKICW-IUCAKERBSA-N (5S,7S)-2-(difluoromethylsulfonyl)-5-(2,5-difluorophenyl)-7-fluoro-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=C(C=CC(=C1)F)F)F OPCZKTFFXUKICW-IUCAKERBSA-N 0.000 claims 1
- IAZASKAQKFYTDQ-YUMQZZPRSA-N (5S,7S)-2-(difluoromethylsulfonyl)-5-(2,6-difluorophenyl)-7-fluoro-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=C(C=CC=C1F)F)F IAZASKAQKFYTDQ-YUMQZZPRSA-N 0.000 claims 1
- OVKNTCLEUDPFGC-IUCAKERBSA-N (5S,7S)-2-(difluoromethylsulfonyl)-5-(3,4-difluorophenyl)-7-fluoro-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(=C(C=C1)F)F)F OVKNTCLEUDPFGC-IUCAKERBSA-N 0.000 claims 1
- SKZSKESYQAHYMQ-IUCAKERBSA-N (5S,7S)-2-(difluoromethylsulfonyl)-5-(3,5-difluorophenyl)-7-fluoro-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)F)F SKZSKESYQAHYMQ-IUCAKERBSA-N 0.000 claims 1
- SKQVLMXTEYROHN-YUMQZZPRSA-N (5S,7S)-2-(difluoromethylsulfonyl)-7-fluoro-5-(2,3,5-trifluorophenyl)-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=C(C(=CC(=C1)F)F)F)F SKQVLMXTEYROHN-YUMQZZPRSA-N 0.000 claims 1
- PZRCZUBDNGHQNS-BQBZGAKWSA-N (5S,7S)-2-(difluoromethylsulfonyl)-7-fluoro-5-(2,3,6-trifluorophenyl)-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=C(C(=CC=C1F)F)F)F PZRCZUBDNGHQNS-BQBZGAKWSA-N 0.000 claims 1
- GTCFOAFXDXCOLM-IUCAKERBSA-N (5S,7S)-2-(difluoromethylsulfonyl)-7-fluoro-5-(2-fluorophenyl)-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=C(C=CC=C1)F)F GTCFOAFXDXCOLM-IUCAKERBSA-N 0.000 claims 1
- QHJAJELJKZJDRG-IUCAKERBSA-N (5S,7S)-2-(difluoromethylsulfonyl)-7-fluoro-5-(3-fluorophenyl)-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)F QHJAJELJKZJDRG-IUCAKERBSA-N 0.000 claims 1
- ZKANETIPHXPOSV-IUCAKERBSA-N (5S,7S)-2-(difluoromethylsulfonyl)-7-fluoro-5-(4-fluorophenyl)-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=C(C=C1)F)F ZKANETIPHXPOSV-IUCAKERBSA-N 0.000 claims 1
- 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 1
- MAMPQXOYBIPBHM-LPEHRKFASA-N (5S,7S)-2-[(1R)-2,2-difluorocyclopropyl]sulfonyl-5-(2,3-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@H]1C(C1)(F)F)F MAMPQXOYBIPBHM-LPEHRKFASA-N 0.000 claims 1
- DLKPEBBRYZMGPM-GARJFASQSA-N (5S,7S)-2-[(1R)-2,2-difluorocyclopropyl]sulfonyl-5-(2,5-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@H]1C(C1)(F)F)F DLKPEBBRYZMGPM-GARJFASQSA-N 0.000 claims 1
- XDHPSLXMFRSYOO-GARJFASQSA-N (5S,7S)-2-[(1R)-2,2-difluorocyclopropyl]sulfonyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1([C@@H](C1)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F XDHPSLXMFRSYOO-GARJFASQSA-N 0.000 claims 1
- MAMPQXOYBIPBHM-GUBZILKMSA-N (5S,7S)-2-[(1S)-2,2-difluorocyclopropyl]sulfonyl-5-(2,3-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@@H]1C(C1)(F)F)F MAMPQXOYBIPBHM-GUBZILKMSA-N 0.000 claims 1
- DLKPEBBRYZMGPM-DCAQKATOSA-N (5S,7S)-2-[(1S)-2,2-difluorocyclopropyl]sulfonyl-5-(2,5-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@@H]1C(C1)(F)F)F DLKPEBBRYZMGPM-DCAQKATOSA-N 0.000 claims 1
- BCNBQPVHRPETEC-DCAQKATOSA-N (5S,7S)-2-[(1S)-2,2-difluorocyclopropyl]sulfonyl-7-fluoro-5-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)[C@@H]1C(C1)(F)F)C1=C(C=CC=C1)F BCNBQPVHRPETEC-DCAQKATOSA-N 0.000 claims 1
- XDHPSLXMFRSYOO-DCAQKATOSA-N (5S,7S)-2-[(1S)-2,2-difluorocyclopropyl]sulfonyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1([C@H](C1)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F XDHPSLXMFRSYOO-DCAQKATOSA-N 0.000 claims 1
- IKBHTYYYUCTDSO-JOOBJXAISA-N (5S,7S)-2-[(R)-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-JOOBJXAISA-N 0.000 claims 1
- WBNASADLNQWYLZ-SYLNSOGPSA-N (5S,7S)-2-[(R)-difluoromethylsulfinyl]-7-fluoro-5-(2-fluorophenyl)-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=C(C=CC=C1)F)F WBNASADLNQWYLZ-SYLNSOGPSA-N 0.000 claims 1
- 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 1
- IKBHTYYYUCTDSO-PVUDRZGPSA-N (5S,7S)-2-[(S)-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-PVUDRZGPSA-N 0.000 claims 1
- WBNASADLNQWYLZ-QJHLZDNFSA-N (5S,7S)-2-[(S)-difluoromethylsulfinyl]-7-fluoro-5-(2-fluorophenyl)-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=C(C=CC=C1)F)F WBNASADLNQWYLZ-QJHLZDNFSA-N 0.000 claims 1
- 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 1
- XMCRNHGTSWFING-QWRGUYRKSA-N (5S,7S)-2-[1-(difluoromethyl)cyclopropyl]sulfonyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(C1(CC1)S(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F XMCRNHGTSWFING-QWRGUYRKSA-N 0.000 claims 1
- ZZZKJXJGCSBTJJ-QWRGUYRKSA-N (5S,7S)-2-[2-(difluoromethoxy)ethylsulfonyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(OCCS(=O)(=O)C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)F ZZZKJXJGCSBTJJ-QWRGUYRKSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- JAVCKHCONFBHSN-QWRGUYRKSA-N (5S,7S)-2-cyclopropylsulfonyl-5-(2,3-difluorophenyl)-7-fluoro-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=C(C(=CC=C1)F)F JAVCKHCONFBHSN-QWRGUYRKSA-N 0.000 claims 1
- YAKYPXRYGUINDZ-RYUDHWBXSA-N (5S,7S)-2-cyclopropylsulfonyl-5-(2,5-difluorophenyl)-7-fluoro-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=C(C=CC(=C1)F)F YAKYPXRYGUINDZ-RYUDHWBXSA-N 0.000 claims 1
- BQTWJWUMHQWOAC-QWRGUYRKSA-N (5S,7S)-2-cyclopropylsulfonyl-5-(2,6-difluorophenyl)-7-fluoro-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=C(C=CC=C1F)F BQTWJWUMHQWOAC-QWRGUYRKSA-N 0.000 claims 1
- HETNFFQEPSLOCX-RYUDHWBXSA-N (5S,7S)-2-cyclopropylsulfonyl-5-(3,4-difluorophenyl)-7-fluoro-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(=C(C=C1)F)F HETNFFQEPSLOCX-RYUDHWBXSA-N 0.000 claims 1
- KMLXMJOVIIKXRV-RYUDHWBXSA-N (5S,7S)-2-cyclopropylsulfonyl-5-(3,5-difluorophenyl)-7-fluoro-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)F)F KMLXMJOVIIKXRV-RYUDHWBXSA-N 0.000 claims 1
- AJWLHLPPCBKKNM-UWVGGRQHSA-N (5S,7S)-2-cyclopropylsulfonyl-7-fluoro-5-(2,3,6-trifluorophenyl)-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=C(C(=CC=C1F)F)F AJWLHLPPCBKKNM-UWVGGRQHSA-N 0.000 claims 1
- SMJPUBQHBIUGIY-RYUDHWBXSA-N (5S,7S)-2-cyclopropylsulfonyl-7-fluoro-5-(2-fluorophenyl)-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=C(C=CC=C1)F SMJPUBQHBIUGIY-RYUDHWBXSA-N 0.000 claims 1
- ISGOMNHQIFUPAR-RYUDHWBXSA-N (5S,7S)-2-cyclopropylsulfonyl-7-fluoro-5-(3-fluorophenyl)-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)F ISGOMNHQIFUPAR-RYUDHWBXSA-N 0.000 claims 1
- QRRTXQJLFCESQP-RYUDHWBXSA-N (5S,7S)-2-cyclopropylsulfonyl-7-fluoro-5-(4-fluorophenyl)-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=C(C=C1)F QRRTXQJLFCESQP-RYUDHWBXSA-N 0.000 claims 1
- 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 1
- COQPEMYQZSJEBH-JDSCLEBSSA-N (5S,7S)-2-ethylsulfinyl-7-fluoro-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](C[C@@H]2F)C1=CC=CC=C1 COQPEMYQZSJEBH-JDSCLEBSSA-N 0.000 claims 1
- LDTDBOJTAATWGA-QWRGUYRKSA-N (5S,7S)-2-ethylsulfonyl-7-fluoro-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@@H](C[C@@H]2F)C1=CC=CC=C1 LDTDBOJTAATWGA-QWRGUYRKSA-N 0.000 claims 1
- 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 1
- 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 1
- HKXWWDZJUNBPRK-YUMQZZPRSA-N (5S,7S)-5-(2,3-difluorophenyl)-7-fluoro-2-(trifluoromethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C(F)(F)F)F HKXWWDZJUNBPRK-YUMQZZPRSA-N 0.000 claims 1
- MOIXFWMKMVSQHZ-VPOLOUISSA-N (5S,7S)-5-(2,3-difluorophenyl)-7-fluoro-2-[(1R,2R)-2-fluorocyclopropyl]sulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@H]1[C@@H](C1)F)F MOIXFWMKMVSQHZ-VPOLOUISSA-N 0.000 claims 1
- MOIXFWMKMVSQHZ-NAKRPEOUSA-N (5S,7S)-5-(2,3-difluorophenyl)-7-fluoro-2-[(1S,2S)-2-fluorocyclopropyl]sulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@@H]1[C@H](C1)F)F MOIXFWMKMVSQHZ-NAKRPEOUSA-N 0.000 claims 1
- KOYPBTOQXRFXMW-SYLNSOGPSA-N (5S,7S)-5-(2,3-difluorophenyl)-7-fluoro-2-[(R)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@@](=O)CF)F KOYPBTOQXRFXMW-SYLNSOGPSA-N 0.000 claims 1
- KOYPBTOQXRFXMW-QJHLZDNFSA-N (5S,7S)-5-(2,3-difluorophenyl)-7-fluoro-2-[(S)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@](=O)CF)F KOYPBTOQXRFXMW-QJHLZDNFSA-N 0.000 claims 1
- LOGSNHWSWZFAFQ-IUCAKERBSA-N (5S,7S)-5-(2,5-difluorophenyl)-7-fluoro-2-(trifluoromethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C(F)(F)F)F LOGSNHWSWZFAFQ-IUCAKERBSA-N 0.000 claims 1
- OKFORRGQJABJTJ-NOOOWODRSA-N (5S,7S)-5-(2,5-difluorophenyl)-7-fluoro-2-[(1R,2R)-2-fluorocyclopropyl]sulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@H]1[C@@H](C1)F)F OKFORRGQJABJTJ-NOOOWODRSA-N 0.000 claims 1
- OKFORRGQJABJTJ-BJDJZHNGSA-N (5S,7S)-5-(2,5-difluorophenyl)-7-fluoro-2-[(1S,2S)-2-fluorocyclopropyl]sulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@@H]1[C@H](C1)F)F OKFORRGQJABJTJ-BJDJZHNGSA-N 0.000 claims 1
- ATZYPWZPSFRECP-FRGLDACASA-N (5S,7S)-5-(2,5-difluorophenyl)-7-fluoro-2-[(R)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@@](=O)CF)F ATZYPWZPSFRECP-FRGLDACASA-N 0.000 claims 1
- ATZYPWZPSFRECP-SWHJWPDWSA-N (5S,7S)-5-(2,5-difluorophenyl)-7-fluoro-2-[(S)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@](=O)CF)F ATZYPWZPSFRECP-SWHJWPDWSA-N 0.000 claims 1
- KDUSWQMTYDYCCY-YUMQZZPRSA-N (5S,7S)-5-(2,6-difluorophenyl)-7-fluoro-2-(trifluoromethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C(=CC=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C(F)(F)F)F KDUSWQMTYDYCCY-YUMQZZPRSA-N 0.000 claims 1
- WHHQNZJBBBXDEV-SYLNSOGPSA-N (5S,7S)-5-(2,6-difluorophenyl)-7-fluoro-2-[(R)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C(=CC=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@@](=O)CF)F WHHQNZJBBBXDEV-SYLNSOGPSA-N 0.000 claims 1
- WHHQNZJBBBXDEV-QJHLZDNFSA-N (5S,7S)-5-(2,6-difluorophenyl)-7-fluoro-2-[(S)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C(=CC=C1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@](=O)CF)F WHHQNZJBBBXDEV-QJHLZDNFSA-N 0.000 claims 1
- XOBKUACWLRZXNM-YUMQZZPRSA-N (5S,7S)-5-(2-chloro-3-fluorophenyl)-2-(difluoromethylsulfonyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C(F)F)F XOBKUACWLRZXNM-YUMQZZPRSA-N 0.000 claims 1
- NQMFLMBNPIGFOW-QWRGUYRKSA-N (5S,7S)-5-(2-chloro-3-fluorophenyl)-2-cyclopropylsulfonyl-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C1CC1)F NQMFLMBNPIGFOW-QWRGUYRKSA-N 0.000 claims 1
- DWPLHAGMXOTVMH-RYUDHWBXSA-N (5S,7S)-5-(2-chlorophenyl)-2-cyclopropylsulfonyl-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C1CC1)F DWPLHAGMXOTVMH-RYUDHWBXSA-N 0.000 claims 1
- BGJQODCEVSKZJR-IUCAKERBSA-N (5S,7S)-5-(2-chlorophenyl)-7-fluoro-2-(trifluoromethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C(F)(F)F)F BGJQODCEVSKZJR-IUCAKERBSA-N 0.000 claims 1
- MCHJBVZXWQWPKL-VUPYVKPUSA-N (5S,7S)-5-(2-chlorophenyl)-7-fluoro-2-[(R)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@@](=O)CF)F MCHJBVZXWQWPKL-VUPYVKPUSA-N 0.000 claims 1
- MCHJBVZXWQWPKL-QDDONVENSA-N (5S,7S)-5-(2-chlorophenyl)-7-fluoro-2-[(S)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC1=C(C=CC=C1)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@](=O)CF)F MCHJBVZXWQWPKL-QDDONVENSA-N 0.000 claims 1
- LSPKVAJMIUZHOI-NOOOWODRSA-N (5S,7S)-5-(3,4-difluorophenyl)-7-fluoro-2-[(1R,2R)-2-fluorocyclopropyl]sulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC=1C=C(C=CC=1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@H]1[C@@H](C1)F)F LSPKVAJMIUZHOI-NOOOWODRSA-N 0.000 claims 1
- LSPKVAJMIUZHOI-BJDJZHNGSA-N (5S,7S)-5-(3,4-difluorophenyl)-7-fluoro-2-[(1S,2S)-2-fluorocyclopropyl]sulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC=1C=C(C=CC=1F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@@H]1[C@H](C1)F)F LSPKVAJMIUZHOI-BJDJZHNGSA-N 0.000 claims 1
- QTLLEXNZYPDNET-FRGLDACASA-N (5S,7S)-5-(3,5-difluorophenyl)-7-fluoro-2-[(R)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@@](=O)CF)F QTLLEXNZYPDNET-FRGLDACASA-N 0.000 claims 1
- QTLLEXNZYPDNET-SWHJWPDWSA-N (5S,7S)-5-(3,5-difluorophenyl)-7-fluoro-2-[(S)-fluoromethylsulfinyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@](=O)CF)F QTLLEXNZYPDNET-SWHJWPDWSA-N 0.000 claims 1
- 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 1
- XQNCGBNJEDAEKI-VPOLOUISSA-N (5S,7S)-5-(3-chloro-2-fluorophenyl)-7-fluoro-2-[(1R,2R)-2-fluorocyclopropyl]sulfonyl-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@H]1[C@@H](C1)F)F)F XQNCGBNJEDAEKI-VPOLOUISSA-N 0.000 claims 1
- XQNCGBNJEDAEKI-NAKRPEOUSA-N (5S,7S)-5-(3-chloro-2-fluorophenyl)-7-fluoro-2-[(1S,2S)-2-fluorocyclopropyl]sulfonyl-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@@H]1[C@H](C1)F)F)F XQNCGBNJEDAEKI-NAKRPEOUSA-N 0.000 claims 1
- YNJOWNMFVIZSNB-IUCAKERBSA-N (5S,7S)-5-(3-chloro-5-fluorophenyl)-2-(difluoromethylsulfonyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC=1C=C(C=C(C=1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C(F)F)F YNJOWNMFVIZSNB-IUCAKERBSA-N 0.000 claims 1
- LMEAJKCANYDVFC-RYUDHWBXSA-N (5S,7S)-5-(3-chloro-5-fluorophenyl)-2-cyclopropylsulfonyl-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC=1C=C(C=C(C=1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)C1CC1)F LMEAJKCANYDVFC-RYUDHWBXSA-N 0.000 claims 1
- ZZUUQDKDHVZSSQ-NOOOWODRSA-N (5S,7S)-5-(3-chloro-5-fluorophenyl)-7-fluoro-2-[(1R,2R)-2-fluorocyclopropyl]sulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC=1C=C(C=C(C=1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@H]1[C@@H](C1)F)F ZZUUQDKDHVZSSQ-NOOOWODRSA-N 0.000 claims 1
- ZZUUQDKDHVZSSQ-BJDJZHNGSA-N (5S,7S)-5-(3-chloro-5-fluorophenyl)-7-fluoro-2-[(1S,2S)-2-fluorocyclopropyl]sulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound ClC=1C=C(C=C(C=1)F)[C@@H]1C[C@@H](C=2N1N=C(N=2)S(=O)(=O)[C@@H]1[C@H](C1)F)F ZZUUQDKDHVZSSQ-BJDJZHNGSA-N 0.000 claims 1
- 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 1
- HTZORYQSILBFAI-IUCAKERBSA-N (5S,7S)-5-(5-chloro-2-fluorophenyl)-2-(difluoromethylsulfonyl)-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)C(F)F)F)F HTZORYQSILBFAI-IUCAKERBSA-N 0.000 claims 1
- 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 1
- PIRKIOOKMGWRCQ-NOOOWODRSA-N (5S,7S)-5-(5-chloro-2-fluorophenyl)-7-fluoro-2-[(1R,2R)-2-fluorocyclopropyl]sulfonyl-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)[C@H]1[C@@H](C1)F)F)F PIRKIOOKMGWRCQ-NOOOWODRSA-N 0.000 claims 1
- PIRKIOOKMGWRCQ-BJDJZHNGSA-N (5S,7S)-5-(5-chloro-2-fluorophenyl)-7-fluoro-2-[(1S,2S)-2-fluorocyclopropyl]sulfonyl-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)[C@@H]1[C@H](C1)F)F)F PIRKIOOKMGWRCQ-BJDJZHNGSA-N 0.000 claims 1
- NOUKPAIFEWNYBL-DWBHSIJVSA-N (5S,7S)-7-fluoro-2-(1,1,2,2,2-pentafluoroethylsulfinyl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)C(C(F)(F)F)(F)F)C1=CC=CC=C1 NOUKPAIFEWNYBL-DWBHSIJVSA-N 0.000 claims 1
- UWTUBMJYUVVFGR-QWRGUYRKSA-N (5S,7S)-7-fluoro-2-(1-fluorocyclopropyl)sulfonyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C1(CC1)F)C1=CC=CC=C1 UWTUBMJYUVVFGR-QWRGUYRKSA-N 0.000 claims 1
- KKGXYNJIRVRDBX-CSUXEGHOSA-N (5S,7S)-7-fluoro-2-(1-fluoroethylsulfonyl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C(C)F)C1=CC=CC=C1 KKGXYNJIRVRDBX-CSUXEGHOSA-N 0.000 claims 1
- KROCDBNABRFDEW-RYUDHWBXSA-N (5S,7S)-7-fluoro-2-(1-methylcyclopropyl)sulfonyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C1(CC1)C)C1=CC=CC=C1 KROCDBNABRFDEW-RYUDHWBXSA-N 0.000 claims 1
- WLFUXCIQUYNQFM-RYUDHWBXSA-N (5S,7S)-7-fluoro-2-(2-methoxyethylsulfonyl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)CCOC)C1=CC=CC=C1 WLFUXCIQUYNQFM-RYUDHWBXSA-N 0.000 claims 1
- XUHIHSAHKAOGSJ-FHQIDYJMSA-N (5S,7S)-7-fluoro-2-(2-methylcyclopropyl)sulfonyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C1C(C1)C)C1=CC=CC=C1 XUHIHSAHKAOGSJ-FHQIDYJMSA-N 0.000 claims 1
- ONQRLIVJSSITSB-TYUFSLCMSA-N (5S,7S)-7-fluoro-2-(3-fluorocyclobutyl)sulfonyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1CC(C1)S(=O)(=O)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 ONQRLIVJSSITSB-TYUFSLCMSA-N 0.000 claims 1
- MZYPOUSUNXQOIH-UWVGGRQHSA-N (5S,7S)-7-fluoro-2-(fluoromethylsulfonyl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)CF)C1=CC=CC=C1 MZYPOUSUNXQOIH-UWVGGRQHSA-N 0.000 claims 1
- SOTUZIZRGFLKEV-VZZBYVJKSA-N (5S,7S)-7-fluoro-2-(methoxymethylsulfinyl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)COC)C1=CC=CC=C1 SOTUZIZRGFLKEV-VZZBYVJKSA-N 0.000 claims 1
- PTIOKLCLTIZNEB-QWRGUYRKSA-N (5S,7S)-7-fluoro-2-(methoxymethylsulfonyl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)COC)C1=CC=CC=C1 PTIOKLCLTIZNEB-QWRGUYRKSA-N 0.000 claims 1
- VZVOHFJXERROCW-RYUDHWBXSA-N (5S,7S)-7-fluoro-2-(oxetan-3-ylsulfonyl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C1COC1)C1=CC=CC=C1 VZVOHFJXERROCW-RYUDHWBXSA-N 0.000 claims 1
- QPBUNBZCFAHNJD-SPOOISQMSA-N (5S,7S)-7-fluoro-2-(oxolan-3-ylsulfonyl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C1COCC1)C1=CC=CC=C1 QPBUNBZCFAHNJD-SPOOISQMSA-N 0.000 claims 1
- YTOOUILGLSGLER-NOOOWODRSA-N (5S,7S)-7-fluoro-2-[(1R,2R)-2-fluorocyclopropyl]sulfonyl-5-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)[C@H]1[C@@H](C1)F)C1=C(C=CC=C1)F YTOOUILGLSGLER-NOOOWODRSA-N 0.000 claims 1
- PZKUEQFIFDQILA-NOOOWODRSA-N (5S,7S)-7-fluoro-2-[(1R,2R)-2-fluorocyclopropyl]sulfonyl-5-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)[C@H]1[C@@H](C1)F)C1=CC=C(C=C1)F PZKUEQFIFDQILA-NOOOWODRSA-N 0.000 claims 1
- GIHAZBYNTROGPU-NOOOWODRSA-N (5S,7S)-7-fluoro-2-[(1R,2R)-2-fluorocyclopropyl]sulfonyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)[C@H]1[C@@H](C1)F)C1=CC=CC=C1 GIHAZBYNTROGPU-NOOOWODRSA-N 0.000 claims 1
- YTOOUILGLSGLER-BJDJZHNGSA-N (5S,7S)-7-fluoro-2-[(1S,2S)-2-fluorocyclopropyl]sulfonyl-5-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)[C@@H]1[C@H](C1)F)C1=C(C=CC=C1)F YTOOUILGLSGLER-BJDJZHNGSA-N 0.000 claims 1
- MUXDQHYTBGMDRV-BJDJZHNGSA-N (5S,7S)-7-fluoro-2-[(1S,2S)-2-fluorocyclopropyl]sulfonyl-5-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)[C@@H]1[C@H](C1)F)C1=CC(=CC=C1)F MUXDQHYTBGMDRV-BJDJZHNGSA-N 0.000 claims 1
- PZKUEQFIFDQILA-BJDJZHNGSA-N (5S,7S)-7-fluoro-2-[(1S,2S)-2-fluorocyclopropyl]sulfonyl-5-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)[C@@H]1[C@H](C1)F)C1=CC=C(C=C1)F PZKUEQFIFDQILA-BJDJZHNGSA-N 0.000 claims 1
- AGMNPPOTEVNNSG-VUPYVKPUSA-N (5S,7S)-7-fluoro-2-[(R)-fluoromethylsulfinyl]-5-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)[S@@](=O)CF)C1=C(C=CC=C1)F AGMNPPOTEVNNSG-VUPYVKPUSA-N 0.000 claims 1
- UZSIRKXJUACKLT-VUPYVKPUSA-N (5S,7S)-7-fluoro-2-[(R)-fluoromethylsulfinyl]-5-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)[S@@](=O)CF)C1=CC(=CC=C1)F UZSIRKXJUACKLT-VUPYVKPUSA-N 0.000 claims 1
- TVWAKDKIJBAIGC-GJPGNPISSA-N (5S,7S)-7-fluoro-2-[(R)-fluoromethylsulfinyl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)[S@@](=O)CF)C1=CC=CC=C1 TVWAKDKIJBAIGC-GJPGNPISSA-N 0.000 claims 1
- UZSIRKXJUACKLT-QDDONVENSA-N (5S,7S)-7-fluoro-2-[(S)-fluoromethylsulfinyl]-5-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)[S@](=O)CF)C1=CC(=CC=C1)F UZSIRKXJUACKLT-QDDONVENSA-N 0.000 claims 1
- TVWAKDKIJBAIGC-ZPEMSAPTSA-N (5S,7S)-7-fluoro-2-[(S)-fluoromethylsulfinyl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)[S@](=O)CF)C1=CC=CC=C1 TVWAKDKIJBAIGC-ZPEMSAPTSA-N 0.000 claims 1
- VXNRCMIUTFDJFT-SKHBRDHGSA-N (5S,7S)-7-fluoro-2-methylsulfinyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)C)C1=CC=CC=C1 VXNRCMIUTFDJFT-SKHBRDHGSA-N 0.000 claims 1
- YBHFFGLVXGVDMS-UWVGGRQHSA-N (5S,7S)-7-fluoro-2-methylsulfonyl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C)C1=CC=CC=C1 YBHFFGLVXGVDMS-UWVGGRQHSA-N 0.000 claims 1
- XLRXEXLLZKMONQ-IUCAKERBSA-N (5S,7S)-7-fluoro-5-(2-fluorophenyl)-2-(trifluoromethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C(F)(F)F)C1=C(C=CC=C1)F XLRXEXLLZKMONQ-IUCAKERBSA-N 0.000 claims 1
- UQENDGLAMXNKCI-IUCAKERBSA-N (5S,7S)-7-fluoro-5-(3-fluorophenyl)-2-(trifluoromethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C(F)(F)F)C1=CC(=CC=C1)F UQENDGLAMXNKCI-IUCAKERBSA-N 0.000 claims 1
- MXRYQPXBRBPBDB-UZQUJWDPSA-N (5S,7S)-7-fluoro-5-phenyl-2-(2,2,2-trifluoroethylsulfinyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)CC(F)(F)F)C1=CC=CC=C1 MXRYQPXBRBPBDB-UZQUJWDPSA-N 0.000 claims 1
- UMXVZZOGMGERCU-UWVGGRQHSA-N (5S,7S)-7-fluoro-5-phenyl-2-(2,2,2-trifluoroethylsulfonyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)CC(F)(F)F)C1=CC=CC=C1 UMXVZZOGMGERCU-UWVGGRQHSA-N 0.000 claims 1
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- IMVJCYDRFQSDTF-RYUDHWBXSA-N (5S,7S)-7-fluoro-5-phenyl-2-propan-2-ylsulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C(C)C)C1=CC=CC=C1 IMVJCYDRFQSDTF-RYUDHWBXSA-N 0.000 claims 1
- SYSAHDZQTVQFRN-RYUDHWBXSA-N (5S,7S)-7-fluoro-5-phenyl-2-propylsulfonyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)CCC)C1=CC=CC=C1 SYSAHDZQTVQFRN-RYUDHWBXSA-N 0.000 claims 1
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- UAONBOVYJRVWMR-UHFFFAOYSA-N 2-(difluoromethylsulfinyl)-5-(3,5-difluorophenyl)-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)F)F)F UAONBOVYJRVWMR-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
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- FXBJPNPXXGGFBH-BJFPOWJFSA-N 2-[(S)-[(5R,7R)-5-(2-chlorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]sulfinyl]acetonitrile Chemical compound ClC1=C(C=CC=C1)[C@H]1C[C@H](C=2N1N=C(N=2)[S@@](=O)CC#N)F FXBJPNPXXGGFBH-BJFPOWJFSA-N 0.000 claims 1
- FXBJPNPXXGGFBH-HJTOQOCKSA-N 2-[(S)-[(5S,7S)-5-(2-chlorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]sulfinyl]acetonitrile Chemical compound ClC1=C(C=CC=C1)[C@@H]1C[C@@H](C=2N1N=C(N=2)[S@@](=O)CC#N)F FXBJPNPXXGGFBH-HJTOQOCKSA-N 0.000 claims 1
- ZCECZRFLCYCOBT-HJTOQOCKSA-N 2-[(S)-[(5S,7S)-7-fluoro-5-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]sulfinyl]acetonitrile Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)[S@@](=O)CC#N)C1=C(C=CC=C1)F ZCECZRFLCYCOBT-HJTOQOCKSA-N 0.000 claims 1
- MTYSZHDWEMTFTG-HJTOQOCKSA-N 2-[(S)-[(5S,7S)-7-fluoro-5-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]sulfinyl]acetonitrile Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)[S@@](=O)CC#N)C1=CC(=CC=C1)F MTYSZHDWEMTFTG-HJTOQOCKSA-N 0.000 claims 1
- FRWORNHIXQNMHG-HJTOQOCKSA-N 2-[(S)-[(5S,7S)-7-fluoro-5-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]sulfinyl]acetonitrile Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)[S@@](=O)CC#N)C1=CC=C(C=C1)F FRWORNHIXQNMHG-HJTOQOCKSA-N 0.000 claims 1
- DYWGGPMIIKDPOE-CCKQJUEOSA-N 2-[(S)-difluoromethylsulfinyl]-7-fluoro-5-(3-fluorophenyl)-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)F DYWGGPMIIKDPOE-CCKQJUEOSA-N 0.000 claims 1
- MLXOSLNKFNXBCM-QWRGUYRKSA-N 2-[[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]sulfanyl]acetonitrile Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)SCC#N)C1=CC=CC=C1 MLXOSLNKFNXBCM-QWRGUYRKSA-N 0.000 claims 1
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- QGRZYAJQDASFTK-VZZBYVJKSA-N 2-[[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]sulfinyl]acetonitrile Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)CC#N)C1=CC=CC=C1 QGRZYAJQDASFTK-VZZBYVJKSA-N 0.000 claims 1
- WBJBXWLZDZNZJW-RYUDHWBXSA-N 2-[[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]sulfonyl]-2-methylpropanenitrile Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)S(=O)(=O)C(C#N)(C)C)C1=CC=CC=C1 WBJBXWLZDZNZJW-RYUDHWBXSA-N 0.000 claims 1
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| EA032357B1 (ru) | 2014-03-26 | 2019-05-31 | Ф. Хоффманн-Ля Рош Аг | Конденсированные [1,4]диазепиновые соединения в качестве ингибиторов продукции аутотаксина (atx) и лизофосфатидиловой кислоты (lpa) |
| CN106573006A (zh) | 2014-08-21 | 2017-04-19 | 葛兰素史密斯克莱知识产权发展有限公司 | 作为药物的rip1激酶抑制剂杂环酰胺 |
| CN107406462B (zh) | 2015-03-09 | 2020-11-10 | 豪夫迈·罗氏有限公司 | 三环dlk抑制剂及其用途 |
| TWI730959B (zh) | 2015-05-19 | 2021-06-21 | 英商葛蘭素史克智慧財產發展有限公司 | 作為激酶抑制劑之雜環醯胺 |
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| US10751444B2 (en) | 2015-08-07 | 2020-08-25 | Victor Matthew Phillips | Flowable hemostatic gel composition and its methods of use |
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| US10961258B2 (en) | 2015-12-21 | 2021-03-30 | Glaxosmithkline Intellectual Property Development Limited | Heterocyclic amides as kinase inhibitors |
| IL287136B2 (en) * | 2016-02-05 | 2023-09-01 | Denali Therapeutics Inc | Receptor inhibitors - interacting with protein kinase 1 |
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| US11071721B2 (en) | 2016-12-02 | 2021-07-27 | Genentech, Inc. | Bicyclic amide compounds and methods of use thereof |
| US11072607B2 (en) | 2016-12-16 | 2021-07-27 | Genentech, Inc. | Inhibitors of RIP1 kinase and methods of use thereof |
| BR112020000771A2 (pt) | 2017-07-14 | 2020-07-14 | F. Hoffmann-La Roche Ag | compostos de cetona bicíclica e métodos de uso dos mesmos |
| RU2020114670A (ru) | 2017-10-11 | 2021-11-12 | Ф. Хоффманн-Ля Рош Аг | Бициклические соединения для применения в качестве ингибиторов rip1 киназы |
| AR113811A1 (es) | 2017-10-31 | 2020-06-10 | Hoffmann La Roche | Sulfonas y sulfóxidos bicíclicos y métodos de uso de los mismos |
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2018
- 2018-10-30 AR ARP180103157A patent/AR113811A1/es unknown
- 2018-10-30 CR CR20200168A patent/CR20200168A/es unknown
- 2018-10-30 SG SG11202002877RA patent/SG11202002877RA/en unknown
- 2018-10-30 EP EP18796020.8A patent/EP3704097B1/en active Active
- 2018-10-30 RU RU2020115915A patent/RU2020115915A/ru unknown
- 2018-10-30 KR KR1020207015138A patent/KR20200083515A/ko not_active Ceased
- 2018-10-30 TW TW107138469A patent/TW201922748A/zh unknown
- 2018-10-30 MX MX2020003451A patent/MX2020003451A/es unknown
- 2018-10-30 JP JP2020524177A patent/JP2021501183A/ja active Pending
- 2018-10-30 BR BR112020008446-8A patent/BR112020008446A2/pt not_active Application Discontinuation
- 2018-10-30 PE PE2020000353A patent/PE20211247A1/es unknown
- 2018-10-30 CA CA3078688A patent/CA3078688A1/en active Pending
- 2018-10-30 AU AU2018360270A patent/AU2018360270A1/en not_active Abandoned
- 2018-10-30 CN CN201880070578.0A patent/CN111278809B/zh active Active
- 2018-10-30 US US16/175,206 patent/US11072617B2/en active Active
- 2018-10-30 MA MA050503A patent/MA50503A/fr unknown
- 2018-10-30 WO PCT/EP2018/079772 patent/WO2019086494A1/en not_active Ceased
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2020
- 2020-03-25 CO CONC2020/0003475A patent/CO2020003475A2/es unknown
- 2020-04-06 IL IL273847A patent/IL273847A/en unknown
- 2020-04-20 CL CL2020001062A patent/CL2020001062A1/es unknown
- 2020-04-30 PH PH12020550537A patent/PH12020550537A1/en unknown
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2021
- 2021-06-06 US US17/340,082 patent/US12338241B2/en active Active
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