JP2020526549A5 - - Google Patents
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- Publication number
- JP2020526549A5 JP2020526549A5 JP2020501256A JP2020501256A JP2020526549A5 JP 2020526549 A5 JP2020526549 A5 JP 2020526549A5 JP 2020501256 A JP2020501256 A JP 2020501256A JP 2020501256 A JP2020501256 A JP 2020501256A JP 2020526549 A5 JP2020526549 A5 JP 2020526549A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- triazole
- pyrrolo
- phenyl
- fluoro
- 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.)
- Granted
Links
- -1 C 1- C 6 alkoxy Chemical group 0.000 claims 106
- 150000001875 compounds Chemical class 0.000 claims 35
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 18
- 229910052799 carbon Inorganic materials 0.000 claims 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 15
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 12
- 229910052801 chlorine Inorganic materials 0.000 claims 12
- 229910052731 fluorine Inorganic materials 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- HVKYUNYBFWMKPT-UHFFFAOYSA-N FC1CC(N2N=C(N=C21)C(CC)=O)C1=CC=CC=C1 Chemical compound FC1CC(N2N=C(N=C21)C(CC)=O)C1=CC=CC=C1 HVKYUNYBFWMKPT-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- ADFFEHJDGDXCFG-UWVGGRQHSA-N (5S,7S)-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=CN=C21)C2=CC=CC=C2 ADFFEHJDGDXCFG-UWVGGRQHSA-N 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- HKTIIUVJXGYOGD-UHFFFAOYSA-N OC(C(=O)C=1N=C2N(N=1)C(CC2F)C1=CC=CC=C1)(C)C Chemical compound OC(C(=O)C=1N=C2N(N=1)C(CC2F)C1=CC=CC=C1)(C)C HKTIIUVJXGYOGD-UHFFFAOYSA-N 0.000 claims 3
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 208000002320 spinal muscular atrophy Diseases 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- MMAQBOVBDLUDFG-UHFFFAOYSA-N 1-(4-phenyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)propan-1-one Chemical compound CCC(=O)c1cc2C(OCCn2n1)c1ccccc1 MMAQBOVBDLUDFG-UHFFFAOYSA-N 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- JLUSKXSRUBDULB-UHFFFAOYSA-N CCC(=O)C1=NN2CCOC(C2=C1)C1=C(F)C=CC=C1 Chemical compound CCC(=O)C1=NN2CCOC(C2=C1)C1=C(F)C=CC=C1 JLUSKXSRUBDULB-UHFFFAOYSA-N 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 claims 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 2
- 125000004212 difluorophenyl group Chemical group 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- QAPYHKXOTXWXPZ-UHFFFAOYSA-N 1-(5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl)propan-1-one Chemical compound CCC(=O)c1nc2CCC(c3ccccc3)n2n1 QAPYHKXOTXWXPZ-UHFFFAOYSA-N 0.000 claims 1
- DOJZSEYEQKWUSI-UHFFFAOYSA-N 1-methylcyclopropane-1-carbaldehyde Chemical compound O=CC1(C)CC1 DOJZSEYEQKWUSI-UHFFFAOYSA-N 0.000 claims 1
- ASISMDYYMIKZLM-STQMWFEESA-N 2-[1-[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole-2-carbonyl]cyclopropyl]acetonitrile Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1(CC#N)CC1)C1=CC=CC=C1 ASISMDYYMIKZLM-STQMWFEESA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- TUQCZDPZDKQRTM-UHFFFAOYSA-N 3,3,3-trifluoro-1-(7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl)-2-hydroxypropan-1-one Chemical compound OC(C(=O)c1nc2C(F)CC(c3ccccc3)n2n1)C(F)(F)F TUQCZDPZDKQRTM-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- YPYQCUPKRSMMSN-UHFFFAOYSA-N C1(CC1)C(=O)C=1N=C2N(N=1)C(CC2)C1=C(C=CC=C1)F Chemical compound C1(CC1)C(=O)C=1N=C2N(N=1)C(CC2)C1=C(C=CC=C1)F YPYQCUPKRSMMSN-UHFFFAOYSA-N 0.000 claims 1
- AVFXGWVZFIBROG-UHFFFAOYSA-N CC(C(=O)C=1N=C2N(N=1)C(CC2F)C1=CC=CC=C1)(C)C Chemical compound CC(C(=O)C=1N=C2N(N=1)C(CC2F)C1=CC=CC=C1)(C)C AVFXGWVZFIBROG-UHFFFAOYSA-N 0.000 claims 1
- QRRBMFKBYJOWCZ-UHFFFAOYSA-N CCC(=O)C1=CN2CCC(C2=N1)C1=CC=CC=C1 Chemical compound CCC(=O)C1=CN2CCC(C2=N1)C1=CC=CC=C1 QRRBMFKBYJOWCZ-UHFFFAOYSA-N 0.000 claims 1
- AGSMIAAEYRCJOK-UHFFFAOYSA-N CCC(=O)C1=NN2C(CCC2=C1)C1=CC=CC=C1 Chemical compound CCC(=O)C1=NN2C(CCC2=C1)C1=CC=CC=C1 AGSMIAAEYRCJOK-UHFFFAOYSA-N 0.000 claims 1
- CACYSZKERVAHES-GFCCVEGCSA-N CCC(=O)C1=NN2CC[C@@H](C2=C1)C1=CC=CC=C1 Chemical compound CCC(=O)C1=NN2CC[C@@H](C2=C1)C1=CC=CC=C1 CACYSZKERVAHES-GFCCVEGCSA-N 0.000 claims 1
- CACYSZKERVAHES-LBPRGKRZSA-N CCC(=O)C1=NN2CC[C@H](C2=C1)C1=CC=CC=C1 Chemical compound CCC(=O)C1=NN2CC[C@H](C2=C1)C1=CC=CC=C1 CACYSZKERVAHES-LBPRGKRZSA-N 0.000 claims 1
- VCCSKRSVEIVDEZ-NSHDSACASA-N CCC(=O)C1=NN2[C@@H](CCC2=N1)C1=C(Cl)C=CC=C1 Chemical compound CCC(=O)C1=NN2[C@@H](CCC2=N1)C1=C(Cl)C=CC=C1 VCCSKRSVEIVDEZ-NSHDSACASA-N 0.000 claims 1
- XWXHREDCBIXXKX-UHFFFAOYSA-N COCC(C)(C)C(=O)c1nc2C(F)CC(c3ccccc3)n2n1 Chemical compound COCC(C)(C)C(=O)c1nc2C(F)CC(c3ccccc3)n2n1 XWXHREDCBIXXKX-UHFFFAOYSA-N 0.000 claims 1
- GAQSYSQXWLHJRU-STQMWFEESA-N CO[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=CC=CC=C1 Chemical compound CO[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=CC=CC=C1 GAQSYSQXWLHJRU-STQMWFEESA-N 0.000 claims 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
- WCIMAPFKNYRSNQ-LBPRGKRZSA-N ClC1=C(C=CC=C1)[C@@H]1CCC2=NC(=NN12)C(=O)C1CC1 Chemical compound ClC1=C(C=CC=C1)[C@@H]1CCC2=NC(=NN12)C(=O)C1CC1 WCIMAPFKNYRSNQ-LBPRGKRZSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- UUKABJSQKLKQPC-UHFFFAOYSA-N FC(CC(=O)C=1N=C2N(N=1)C(CC2F)C1=CC=CC=C1)(F)F Chemical compound FC(CC(=O)C=1N=C2N(N=1)C(CC2F)C1=CC=CC=C1)(F)F UUKABJSQKLKQPC-UHFFFAOYSA-N 0.000 claims 1
- FWMNSADKMMIUCS-UHFFFAOYSA-N FC1CC(N2N=C(N=C21)C(=O)C1C(C1)F)C1=CC=CC=C1 Chemical compound FC1CC(N2N=C(N=C21)C(=O)C1C(C1)F)C1=CC=CC=C1 FWMNSADKMMIUCS-UHFFFAOYSA-N 0.000 claims 1
- UCXDFPTUDIFBRI-UHFFFAOYSA-N FC1CC(N2N=C(N=C21)C(C(C#N)(C)C)=O)C1=CC=CC=C1 Chemical compound FC1CC(N2N=C(N=C21)C(C(C#N)(C)C)=O)C1=CC=CC=C1 UCXDFPTUDIFBRI-UHFFFAOYSA-N 0.000 claims 1
- CWYDYRVJFUPUBS-UHFFFAOYSA-N FC1CC(N2N=C(N=C21)C(C(C)C)=O)C1=CC=CC=C1 Chemical compound FC1CC(N2N=C(N=C21)C(C(C)C)=O)C1=CC=CC=C1 CWYDYRVJFUPUBS-UHFFFAOYSA-N 0.000 claims 1
- BUBIYRFXUZVIIH-UHFFFAOYSA-N FC1CC=2N(N=C(N=2)C(CC)=O)C1C1=CC=CC=C1 Chemical compound FC1CC=2N(N=C(N=2)C(CC)=O)C1C1=CC=CC=C1 BUBIYRFXUZVIIH-UHFFFAOYSA-N 0.000 claims 1
- KCBMPSFKYINJNM-IUCAKERBSA-N F[C@H]1C[C@@H](C2CC2)N2N=C(N=C12)C(=O)C1CC1 Chemical compound F[C@H]1C[C@@H](C2CC2)N2N=C(N=C12)C(=O)C1CC1 KCBMPSFKYINJNM-IUCAKERBSA-N 0.000 claims 1
- QAWQWMLTJDTQKR-RYUDHWBXSA-N F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1(CC1)C#N)C1=CC=CC=C1 Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1(CC1)C#N)C1=CC=CC=C1 QAWQWMLTJDTQKR-RYUDHWBXSA-N 0.000 claims 1
- DUECLJOPMDGAGH-STQMWFEESA-N F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=C(C=CC=C1)C#N Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=C(C=CC=C1)C#N DUECLJOPMDGAGH-STQMWFEESA-N 0.000 claims 1
- GJYUASQMOUKESY-SPOOISQMSA-N F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC11CC1)C1=CC=CC=C1 Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC11CC1)C1=CC=CC=C1 GJYUASQMOUKESY-SPOOISQMSA-N 0.000 claims 1
- WECQKSNRWLFCOH-TTZKSVMKSA-N F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC11CCC1)C1=CC=CC=C1 Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC11CCC1)C1=CC=CC=C1 WECQKSNRWLFCOH-TTZKSVMKSA-N 0.000 claims 1
- NYCYJFQDSUGKHT-TYUFSLCMSA-N F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1C#N)C1=CC=CC=C1 Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1C#N)C1=CC=CC=C1 NYCYJFQDSUGKHT-TYUFSLCMSA-N 0.000 claims 1
- ADBUKDYDZJSPOU-KBPBESRZSA-N F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC2(CC2)C1)C1=CC=CC=C1 Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC2(CC2)C1)C1=CC=CC=C1 ADBUKDYDZJSPOU-KBPBESRZSA-N 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000032843 Hemorrhage Diseases 0.000 claims 1
- 101001109145 Homo sapiens Receptor-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 208000001089 Multiple system atrophy Diseases 0.000 claims 1
- KEIDENYTGJNIMO-UHFFFAOYSA-N O=C(C1=NN2C(CCC2=N1)C1=CC=CC=C1)C1(CN2C=CC=N2)CC1 Chemical compound O=C(C1=NN2C(CCC2=N1)C1=CC=CC=C1)C1(CN2C=CC=N2)CC1 KEIDENYTGJNIMO-UHFFFAOYSA-N 0.000 claims 1
- HAMZRZRYHAYBEL-NWDGAFQWSA-N O[C@@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=CC=CC=C1 Chemical compound O[C@@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=CC=CC=C1 HAMZRZRYHAYBEL-NWDGAFQWSA-N 0.000 claims 1
- HAMZRZRYHAYBEL-RYUDHWBXSA-N O[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=CC=CC=C1 Chemical compound O[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=CC=CC=C1 HAMZRZRYHAYBEL-RYUDHWBXSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000032319 Primary lateral sclerosis Diseases 0.000 claims 1
- 206010061481 Renal injury Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 206010053879 Sepsis syndrome Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010048327 Supranuclear palsy Diseases 0.000 claims 1
- 208000034799 Tauopathies Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046298 Upper motor neurone lesion Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000034158 bleeding Diseases 0.000 claims 1
- 230000000740 bleeding effect Effects 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 230000001054 cortical effect Effects 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 229910052805 deuterium Inorganic materials 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 238000007917 intracranial administration Methods 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 1
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 1
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 201000000585 muscular atrophy Diseases 0.000 claims 1
- 201000006938 muscular dystrophy Diseases 0.000 claims 1
- 230000003589 nefrotoxic effect Effects 0.000 claims 1
- 201000008383 nephritis Diseases 0.000 claims 1
- 231100000381 nephrotoxic Toxicity 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 210000004738 parenchymal cell Anatomy 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 201000002241 progressive bulbar palsy Diseases 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 201000008752 progressive muscular atrophy Diseases 0.000 claims 1
- 201000000196 pseudobulbar palsy Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000002123 temporal effect Effects 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023061174A JP7734163B2 (ja) | 2017-07-14 | 2023-04-05 | 二環式ケトン化合物及びその使用方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762532767P | 2017-07-14 | 2017-07-14 | |
| US62/532,767 | 2017-07-14 | ||
| PCT/EP2018/068998 WO2019012063A1 (en) | 2017-07-14 | 2018-07-12 | BICYCLIC KETONIC COMPOUNDS AND METHODS OF USE |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023061174A Division JP7734163B2 (ja) | 2017-07-14 | 2023-04-05 | 二環式ケトン化合物及びその使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020526549A JP2020526549A (ja) | 2020-08-31 |
| JP2020526549A5 true JP2020526549A5 (https=) | 2021-08-19 |
| JP7258843B2 JP7258843B2 (ja) | 2023-04-17 |
Family
ID=62916677
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020501256A Active JP7258843B2 (ja) | 2017-07-14 | 2018-07-12 | 二環式ケトン化合物及びその使用方法 |
| JP2023061174A Active JP7734163B2 (ja) | 2017-07-14 | 2023-04-05 | 二環式ケトン化合物及びその使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023061174A Active JP7734163B2 (ja) | 2017-07-14 | 2023-04-05 | 二環式ケトン化合物及びその使用方法 |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US11098058B2 (https=) |
| EP (2) | EP4397309A3 (https=) |
| JP (2) | JP7258843B2 (https=) |
| KR (2) | KR102664604B1 (https=) |
| CN (2) | CN119613408A (https=) |
| AR (1) | AR112274A1 (https=) |
| AU (3) | AU2018300043B2 (https=) |
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