JP7362600B2 - Ｒｉｐ１キナーゼ阻害剤として使用するための二環式化合物 - Google Patents

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Publication number

JP7362600B2

JP7362600B2 JP2020520532A JP2020520532A JP7362600B2 JP 7362600 B2 JP7362600 B2 JP 7362600B2 JP 2020520532 A JP2020520532 A JP 2020520532A JP 2020520532 A JP2020520532 A JP 2020520532A JP 7362600 B2 JP7362600 B2 JP 7362600B2

Authority

JP

Japan

Prior art keywords

fluoro

phenyl

pyrrolo

dihydro

triazole

Prior art date

2017-10-11

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.)

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• 101001109145 Homo sapiens Receptor-interacting serine/threonine-protein kinase 1 Proteins 0.000 title claims 2
• 229940043355 kinase inhibitor Drugs 0.000 title description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
• 125000002619 bicyclic group Chemical group 0.000 title description 3
• 102100021009 Cytochrome b-c1 complex subunit Rieske, mitochondrial Human genes 0.000 title 1
• 101000643956 Homo sapiens Cytochrome b-c1 complex subunit Rieske, mitochondrial Proteins 0.000 title 1
• 101001099199 Homo sapiens RalA-binding protein 1 Proteins 0.000 title 1
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 582
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 185
• 150000001875 compounds Chemical class 0.000 claims description 162
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 133
• 201000010099 disease Diseases 0.000 claims description 67
• 208000035475 disorder Diseases 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 50
• 229910052739 hydrogen Inorganic materials 0.000 claims description 47
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 37
• 125000001153 fluoro group Chemical group F* 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 30
• 239000008194 pharmaceutical composition Substances 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 21
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 208000002320 spinal muscular atrophy Diseases 0.000 claims description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 15
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 150000003852 triazoles Chemical class 0.000 claims description 15
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
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• 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
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• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
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• MUJRUMLHIAZTAZ-XEZLXBQYSA-N (5S,7S)-7-fluoro-2-[(1R,2R)-2-methylcyclopropyl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C[C@@H]1C[C@H]1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 MUJRUMLHIAZTAZ-XEZLXBQYSA-N 0.000 claims description 6
• 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 6
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• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
• TZJYCNIDUFJHMJ-ZLHQZALHSA-N (5S,7S)-2-[cyclopropyl(deuterio)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound [2H]C(C1CC1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 TZJYCNIDUFJHMJ-ZLHQZALHSA-N 0.000 claims description 5
• JEGJYXYMPWLQOO-RYUDHWBXSA-N (5S,7S)-2-[cyclopropyl(difluoro)methyl]-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=C12)C(F)(F)C1CC1)C1=C(F)C=CC=C1 JEGJYXYMPWLQOO-RYUDHWBXSA-N 0.000 claims description 5
• SLXJOSCDZNONEQ-RYUDHWBXSA-N (5S,7S)-2-[difluoro-(3-methyloxetan-3-yl)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC1(COC1)C(F)(F)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 SLXJOSCDZNONEQ-RYUDHWBXSA-N 0.000 claims description 5
• MUJRUMLHIAZTAZ-BQUFFADESA-N (5S,7S)-7-fluoro-2-[(1S,2S)-2-methylcyclopropyl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C[C@H]1C[C@@H]1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 MUJRUMLHIAZTAZ-BQUFFADESA-N 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 239000013543 active substance Substances 0.000 claims description 5
• 230000006378 damage Effects 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• JCPPXNOEDKUSMA-LBPRGKRZSA-N (5S)-5-(2-fluorophenyl)-2-propyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CCCC1=NN2[C@@H](CCC2=N1)C1=C(F)C=CC=C1 JCPPXNOEDKUSMA-LBPRGKRZSA-N 0.000 claims description 4
• NROHODVQFPILMY-QWRGUYRKSA-N (5S,7S)-2-(3,3-difluoropropyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(F)CCC1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 NROHODVQFPILMY-QWRGUYRKSA-N 0.000 claims description 4
• ALCTUKGOYARRNH-RWMBFGLXSA-N (5S,7S)-2-[(R)-cyclopropyl(fluoro)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H](C1CC1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 ALCTUKGOYARRNH-RWMBFGLXSA-N 0.000 claims description 4
• ALCTUKGOYARRNH-AVGNSLFASA-N (5S,7S)-2-[(S)-cyclopropyl(fluoro)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@@H](C1CC1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 ALCTUKGOYARRNH-AVGNSLFASA-N 0.000 claims description 4
• LTFXUKMFJNTABL-STQMWFEESA-N (5S,7S)-2-but-1-en-2-yl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CCC(=C)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 LTFXUKMFJNTABL-STQMWFEESA-N 0.000 claims description 4
• NUZSTKOHEMQTRQ-QWRGUYRKSA-N (5S,7S)-2-ethenyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(C=C)N=C12)C1=CC=CC=C1 NUZSTKOHEMQTRQ-QWRGUYRKSA-N 0.000 claims description 4
• QHBDKUZEAPMVTE-SLEUVZQESA-N (5S,7S)-7-fluoro-2-[(2R)-2-fluorobutan-2-yl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC[C@@](C)(F)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 QHBDKUZEAPMVTE-SLEUVZQESA-N 0.000 claims description 4
• QHBDKUZEAPMVTE-HUBLWGQQSA-N (5S,7S)-7-fluoro-2-[(2S)-2-fluorobutan-2-yl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC[C@](C)(F)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 QHBDKUZEAPMVTE-HUBLWGQQSA-N 0.000 claims description 4
• DNXGDPNXQYDKTQ-HOAMVYINSA-N (5S,7S)-7-fluoro-2-[2-(methoxymethyl)cyclopropyl]-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)C1C(C1)COC)C1=CC=CC=C1 DNXGDPNXQYDKTQ-HOAMVYINSA-N 0.000 claims description 4
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
• UGOJIEZBRQLYGD-AVGNSLFASA-N (R)-[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]-(1-methylcyclopropyl)methanol Chemical compound CC1(CC1)[C@@H](O)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 UGOJIEZBRQLYGD-AVGNSLFASA-N 0.000 claims description 4
• SAQMQGKIKVSNOD-UHFFFAOYSA-N 2-(7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl)acetonitrile Chemical compound FC1CC(c2ccccc2)n2nc(CC#N)nc12 SAQMQGKIKVSNOD-UHFFFAOYSA-N 0.000 claims description 4
• MESPBSCMVDRXIP-RYUDHWBXSA-N 3-[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]propanenitrile Chemical compound F[C@H]1C[C@H](N2N=C(CCC#N)N=C12)C1=CC=CC=C1 MESPBSCMVDRXIP-RYUDHWBXSA-N 0.000 claims description 4
• 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 4
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 4
• 206010018985 Haemorrhage intracranial Diseases 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 208000008574 Intracranial Hemorrhages Diseases 0.000 claims description 4
• 208000009829 Lewy Body Disease Diseases 0.000 claims description 4
• 201000002832 Lewy body dementia Diseases 0.000 claims description 4
• 208000001089 Multiple system atrophy Diseases 0.000 claims description 4
• 206010033645 Pancreatitis Diseases 0.000 claims description 4
• 208000032319 Primary lateral sclerosis Diseases 0.000 claims description 4
• 208000007014 Retinitis pigmentosa Diseases 0.000 claims description 4
• 206010040047 Sepsis Diseases 0.000 claims description 4
• 206010046298 Upper motor neurone lesion Diseases 0.000 claims description 4
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 4
• 229960004316 cisplatin Drugs 0.000 claims description 4
• PKBCTTLHTSLUQX-HOAMVYINSA-N ethyl 2-[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]cyclopropane-1-carboxylate Chemical compound F[C@H]1C[C@H](N2N=C(N=C21)C1C(C1)C(=O)OCC)C1=CC=CC=C1 PKBCTTLHTSLUQX-HOAMVYINSA-N 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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• 201000000585 muscular atrophy Diseases 0.000 claims description 4
• 201000006938 muscular dystrophy Diseases 0.000 claims description 4
• 201000002241 progressive bulbar palsy Diseases 0.000 claims description 4
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• 201000000196 pseudobulbar palsy Diseases 0.000 claims description 4
• WDRYHJYWUJHCFD-RNJOBUHISA-N (1R,2R)-2-[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]cyclopropane-1-carbonitrile Chemical compound F[C@H]1C[C@@H](c2ccccc2)n2nc(nc12)[C@@H]1C[C@H]1C#N WDRYHJYWUJHCFD-RNJOBUHISA-N 0.000 claims description 3
• VBFUHRXFACWWGQ-DVRYWGNFSA-N (5S,7S)-2-(2,2-difluorocyclopropyl)-7-fluoro-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=C12)C1CC1(F)F)C1=CC=CC=C1 VBFUHRXFACWWGQ-DVRYWGNFSA-N 0.000 claims description 3
• WLVQXZPCKIROOP-SPOOISQMSA-N (5S,7S)-2-(2,2-dimethylcyclopropyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC1(C)CC1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 WLVQXZPCKIROOP-SPOOISQMSA-N 0.000 claims description 3
• KPKUNSHYTZNQGB-STQMWFEESA-N (5S,7S)-2-(2-ethoxyethyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CCOCCC1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 KPKUNSHYTZNQGB-STQMWFEESA-N 0.000 claims description 3
• IOASJLGDLUGRAU-KBPBESRZSA-N (5S,7S)-2-(cyclobutylmethyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(CC3CCC3)N=C12)C1=CC=CC=C1 IOASJLGDLUGRAU-KBPBESRZSA-N 0.000 claims description 3
• ALCTUKGOYARRNH-WPNOJFKCSA-N (5S,7S)-2-(cyclopropyl-deuterio-fluoromethyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound [2H]C(F)(C1CC1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 ALCTUKGOYARRNH-WPNOJFKCSA-N 0.000 claims description 3
• YASNUJHAYIJJNC-RAMGSTBQSA-N (5S,7S)-2-[(2,2-difluorocyclopropyl)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(CC3CC3(F)F)N=C12)C1=CC=CC=C1 YASNUJHAYIJJNC-RAMGSTBQSA-N 0.000 claims description 3
• ALCTUKGOYARRNH-HBYHVEIASA-N (5S,7S)-2-[(R)-cyclopropyl-deuterio-fluoromethyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound [2H][C@@](F)(C1CC1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 ALCTUKGOYARRNH-HBYHVEIASA-N 0.000 claims description 3
• ALCTUKGOYARRNH-YIFXQUHMSA-N (5S,7S)-2-[(S)-cyclopropyl-deuterio-fluoromethyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound [2H][C@](F)(C1CC1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 ALCTUKGOYARRNH-YIFXQUHMSA-N 0.000 claims description 3
• UHAUTGSTWXFJTQ-YWGVVOLTSA-N (5S,7S)-2-[1-bicyclo[1.1.1]pentanyl(difluoro)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1=CC=CC=C1[C@H]1N2C([C@H](C1)F)=NC(C(C13CC(C1)C3)(F)F)=N2 UHAUTGSTWXFJTQ-YWGVVOLTSA-N 0.000 claims description 3
• PPXSGFWZQJTMHF-QQFIATSDSA-N (5S,7S)-2-[difluoro-(2-fluorocyclopropyl)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(C=1N=C2N(N=1)[C@@H](C[C@@H]2F)C1=CC=CC=C1)(C1C(C1)F)F PPXSGFWZQJTMHF-QQFIATSDSA-N 0.000 claims description 3
• OTBMKSWOSBUXIR-AAEUAGOBSA-N (5S,7S)-7-fluoro-2-(1-methylpyrazol-3-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CN1C=CC(=N1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 OTBMKSWOSBUXIR-AAEUAGOBSA-N 0.000 claims description 3
• RGTCHMJHRGZKQJ-STQMWFEESA-N (5S,7S)-7-fluoro-2-(5-methylpyrazol-1-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC1=CC=NN1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 RGTCHMJHRGZKQJ-STQMWFEESA-N 0.000 claims description 3
• UNGACTKJXUJRLY-QWRGUYRKSA-N (5S,7S)-7-fluoro-5-phenyl-2-(3,3,3-trifluoropropyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(CCC(F)(F)F)N=C12)C1=CC=CC=C1 UNGACTKJXUJRLY-QWRGUYRKSA-N 0.000 claims description 3
• PCHGYNYQBVSCGW-GJZGRUSLSA-N (5S,7S)-7-fluoro-5-phenyl-2-(4-propan-2-ylpyrazol-1-yl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC(C)C1=CN(N=C1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 PCHGYNYQBVSCGW-GJZGRUSLSA-N 0.000 claims description 3
• RXUYYIANSGIRBA-STQMWFEESA-N (5S,7S)-7-fluoro-5-phenyl-2-(propan-2-yloxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC(C)OCC1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 RXUYYIANSGIRBA-STQMWFEESA-N 0.000 claims description 3
• UBRCRPXDHQXFBT-QQFIATSDSA-N (5S,7S)-7-fluoro-5-phenyl-2-[2-(trifluoromethyl)cyclopropyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C1CC1C(F)(F)F)C1=CC=CC=C1 UBRCRPXDHQXFBT-QQFIATSDSA-N 0.000 claims description 3
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 3
• 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• DMAYXWLZZCHGOM-RWMBFGLXSA-N (R)-cyclopropyl-[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]methanol Chemical compound O[C@H](C1CC1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 DMAYXWLZZCHGOM-RWMBFGLXSA-N 0.000 claims description 3
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