JP2020526549A5 - - Google Patents
Download PDFInfo
- 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 (OSRAM) | 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 (OSRAM) |
| EP (2) | EP3652178B1 (OSRAM) |
| JP (2) | JP7258843B2 (OSRAM) |
| KR (2) | KR102664604B1 (OSRAM) |
| CN (2) | CN119613408A (OSRAM) |
| AR (1) | AR112274A1 (OSRAM) |
| AU (3) | AU2018300043B2 (OSRAM) |
| BR (1) | BR112020000771A2 (OSRAM) |
| CA (2) | CA3067944C (OSRAM) |
| CL (1) | CL2020000101A1 (OSRAM) |
| CO (1) | CO2020000134A2 (OSRAM) |
| CR (1) | CR20200002A (OSRAM) |
| DK (1) | DK3652178T3 (OSRAM) |
| ES (1) | ES2973661T3 (OSRAM) |
| FI (1) | FI3652178T3 (OSRAM) |
| HR (1) | HRP20240354T1 (OSRAM) |
| HU (1) | HUE065793T2 (OSRAM) |
| IL (2) | IL271981B (OSRAM) |
| LT (1) | LT3652178T (OSRAM) |
| MA (1) | MA49560B1 (OSRAM) |
| PE (1) | PE20200793A1 (OSRAM) |
| PH (1) | PH12020500105A1 (OSRAM) |
| PL (1) | PL3652178T3 (OSRAM) |
| PT (1) | PT3652178T (OSRAM) |
| RS (1) | RS65308B1 (OSRAM) |
| SG (1) | SG11202000333UA (OSRAM) |
| SI (1) | SI3652178T1 (OSRAM) |
| TW (1) | TWI805595B (OSRAM) |
| UA (1) | UA125448C2 (OSRAM) |
| WO (1) | WO2019012063A1 (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201831478A (zh) | 2016-12-02 | 2018-09-01 | 瑞士商赫孚孟拉羅股份公司 | 雙環醯胺化合物及其使用方法 |
| KR102664604B1 (ko) | 2017-07-14 | 2024-05-14 | 에프. 호프만-라 로슈 아게 | 이환형 케톤 화합물 및 이의 사용 방법 |
| AU2018360270A1 (en) | 2017-10-31 | 2020-03-26 | F. Hoffmann-La Roche Ag | Bicyclic sulfones and sulfoxides and methods of use thereof |
| CN113302193A (zh) * | 2019-01-11 | 2021-08-24 | 豪夫迈·罗氏有限公司 | 双环吡咯并三唑酮化合物及其使用方法 |
| WO2021198981A1 (en) | 2020-04-01 | 2021-10-07 | Janssen Biopharma, Inc. | Antiviral compounds and uses thereof |
| TWI879949B (zh) * | 2020-04-27 | 2025-04-11 | 南韓商奧土擇破利悟股份有限公司 | 用於ｕｂｒ盒結構域配體之化合物、組成物以及醫藥組成物 |
| JP2024513394A (ja) | 2021-04-02 | 2024-03-25 | ジェネンテック， インコーポレイテッド | 二環式ケトン化合物を作製するための方法 |
| WO2023039795A1 (zh) * | 2021-09-16 | 2023-03-23 | 维泰瑞隆（北京）生物科技有限公司 | Rip1激酶抑制剂及其用途 |
| GEAP202516658A (en) * | 2022-05-19 | 2025-03-25 | Merck Sharp & Dohme Llc | Ripk1 inhibitors and methods of use |
| WO2024260932A2 (en) * | 2023-06-19 | 2024-12-26 | F. Hoffmann-La Roche Ag | Process for the preparation of a chiral pyrrolo triazole alcohol |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1620508A1 (de) | 1965-07-23 | 1969-09-18 | Thomae Gmbh Dr K | Verfahren zur Herstellung neuer 4,5,6,7-Tetrahydrothiazolo-[5,4-c]-pyridine |
| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| US3948903A (en) | 1972-12-15 | 1976-04-06 | Parke, Davis & Company | Substituted N-(1,2-dihydro-2-oxonicotinyl)-cephalexins and -cephaloglycins |
| US4485045A (en) | 1981-07-06 | 1984-11-27 | Research Corporation | Synthetic phosphatidyl cholines useful in forming liposomes |
| EP0102324A3 (de) | 1982-07-29 | 1984-11-07 | Ciba-Geigy Ag | Lipide und Tenside in wässriger Phase |
| US4544545A (en) | 1983-06-20 | 1985-10-01 | Trustees University Of Massachusetts | Liposomes containing modified cholesterol for organ targeting |
| HUT35524A (en) | 1983-08-02 | 1985-07-29 | Hoechst Ag | Process for preparing pharmaceutical compositions containing regulatory /regulative/ peptides providing for the retarded release of the active substance |
| GB8610530D0 (en) | 1986-04-30 | 1986-06-04 | Fbc Ltd | Herbicides |
| US5004697A (en) | 1987-08-17 | 1991-04-02 | Univ. Of Ca | Cationized antibodies for delivery through the blood-brain barrier |
| US5268164A (en) | 1990-04-23 | 1993-12-07 | Alkermes, Inc. | Increasing blood-brain barrier permeability with permeabilizer peptides |
| US5112596A (en) | 1990-04-23 | 1992-05-12 | Alkermes, Inc. | Method for increasing blood-brain barrier permeability by administering a bradykinin agonist of blood-brain barrier permeability |
| AU677216B2 (en) | 1992-07-27 | 1997-04-17 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | Targeting of liposomes to the blood-brain barrier |
| US6080772A (en) | 1995-06-07 | 2000-06-27 | Sugen, Inc. | Thiazole compounds and methods of modulating signal transduction |
| AU8071698A (en) | 1997-06-13 | 1998-12-30 | Sugen, Inc. | Novel heteroaryl compounds for the modulation of protein tyrosine enzyme relatedcellular signal transduction |
| US6653304B2 (en) * | 2000-02-11 | 2003-11-25 | Bristol-Myers Squibb Co. | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases |
| US6514221B2 (en) | 2000-07-27 | 2003-02-04 | Brigham And Women's Hospital, Inc. | Blood-brain barrier opening |
| AU2001286930A1 (en) | 2000-08-30 | 2002-03-13 | The Board Of Trustees Of The Leland Stanford Junior University | Glucocorticoid blocking agents for increasing blood-brain barrier permeability |
| US7034036B2 (en) | 2000-10-30 | 2006-04-25 | Pain Therapeutics, Inc. | Inhibitors of ABC drug transporters at the blood-brain barrier |
| DE10121982B4 (de) | 2001-05-05 | 2008-01-24 | Lts Lohmann Therapie-Systeme Ag | Nanopartikel aus Protein mit gekoppeltem Apolipoprotein E zur Überwindung der Blut-Hirn-Schranke und Verfahren zu ihrer Herstellung |
| US20030129186A1 (en) | 2001-07-25 | 2003-07-10 | Biomarin Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| US20030162695A1 (en) | 2002-02-27 | 2003-08-28 | Schatzberg Alan F. | Glucocorticoid blocking agents for increasing blood-brain barrier permeability |
| AU2003265585B2 (en) | 2002-08-26 | 2008-07-03 | Takeda Pharmaceutical Company Limited | Calcium receptor modulating compound and use thereof |
| CA2791165C (en) | 2002-12-03 | 2015-02-24 | Blanchette Rockefeller Neurosciences Institute | A conjugate comprising cholesterol linked to tetracycline |
| EP1633348B1 (en) | 2003-05-02 | 2008-10-08 | Elan Pharmaceuticals, Inc. | 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE - 3 - CARBOXYLIC ACID AMIDE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ B sb 1 /sb RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES |
| JP2007505142A (ja) | 2003-09-10 | 2007-03-08 | セダーズ−シナイ メディカル センター | 血液脳関門を通過する薬剤のカリウムチャネル媒介性送達 |
| EP1877399A1 (en) | 2005-04-26 | 2008-01-16 | Pfizer Limited | Triazole derivatives as vasopressin antagonists |
| EP2083009A1 (de) | 2008-01-22 | 2009-07-29 | Grünenthal GmbH | Substituierte Tethrahydroimidazopyridin-Verbindungen und deren Verwendung in Arzneimitteln |
| US8299077B2 (en) | 2009-03-02 | 2012-10-30 | Roche Palo Alto Llc | Inhibitors of Bruton's tyrosine kinase |
| CN101824036A (zh) | 2009-03-05 | 2010-09-08 | 上海恒瑞医药有限公司 | 四氢咪唑并[1，5-a]吡嗪衍生物的盐,其制备方法及其在医药上的应用 |
| JO3156B1 (ar) | 2009-07-09 | 2017-09-20 | Novartis Ag | ايميدازولات مدمجة والتركيبات التي تشملها لعلاج الأمراض الطفيلية على مثال الملاريا |
| US8722676B2 (en) | 2011-11-03 | 2014-05-13 | Genentech, Inc. | Bicyclic piperazine compounds |
| MX2014013407A (es) | 2012-05-22 | 2014-11-26 | Hoffmann La Roche | Dipiridilaminas sustituidas y uso de las mismas. |
| BR112015016395A2 (pt) | 2013-01-18 | 2017-07-11 | Hoffmann La Roche | pirazóis 3-substituídos e uso como inibidores de dlk |
| TWI638815B (zh) * | 2013-02-15 | 2018-10-21 | 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類（一） |
| KR20160002850A (ko) | 2013-05-01 | 2016-01-08 | 에프. 호프만-라 로슈 아게 | C-연결된 헤테로사이클로알킬 치환된 피리미딘 및 이의 용도 |
| MA42164B1 (fr) | 2013-05-01 | 2019-12-31 | Hoffmann La Roche | Composes biheteroaryle et leurs utilisations |
| CN105473554B (zh) | 2013-07-10 | 2019-08-13 | 沃泰克斯药物股份有限公司 | 作为离子通道调节剂的稠合的哌啶酰胺类 |
| MX2016008110A (es) | 2013-12-20 | 2016-08-19 | Hoffmann La Roche | Derivados de pirazol como inhibidores de la cinasa de cremallera de leucina dual (dlk) y usos de los mismos. |
| JP6554481B2 (ja) | 2014-03-26 | 2019-07-31 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | オートタキシン（ａｔｘ）及びリゾホスファチジン酸（ｌｐａ）産生の阻害剤としての縮合［１，４］ジアゼピン化合物 |
| RU2017109122A (ru) | 2014-08-21 | 2018-09-21 | Глэксосмитклайн Интеллекчуал Проперти Дивелопмент Лимитед | Способы лечения с использованием гетероциклических амидов в качестве ингибиторов киназы |
| WO2016128908A1 (en) * | 2015-02-12 | 2016-08-18 | Advinus Therapeutics Limited | Bicyclic compounds, compositions and medicinal applications thereof |
| JP6701225B2 (ja) | 2015-03-09 | 2020-05-27 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 三環式ｄｌｋ阻害剤及びその使用 |
| SG10201913880XA (en) | 2015-07-02 | 2020-03-30 | Hoffmann La Roche | Bicyclic lactams and methods of use thereof |
| CN108602809B (zh) | 2015-12-04 | 2022-09-30 | 戴纳立制药公司 | 异噁唑烷衍生的受体相互作用蛋白激酶1(ripk 1)的抑制剂 |
| WO2017109724A1 (en) | 2015-12-21 | 2017-06-29 | Glaxosmithkline Intellectual Property Development Limited | Heterocyclic amides as kinase inhibitors |
| TWI781920B (zh) | 2016-02-05 | 2022-11-01 | 美商戴納立製藥公司 | 化合物、組合物及方法 |
| TW201831478A (zh) | 2016-12-02 | 2018-09-01 | 瑞士商赫孚孟拉羅股份公司 | 雙環醯胺化合物及其使用方法 |
| US11072607B2 (en) | 2016-12-16 | 2021-07-27 | Genentech, Inc. | Inhibitors of RIP1 kinase and methods of use thereof |
| CN110169087B (zh) | 2017-01-05 | 2021-04-20 | 微软技术许可有限责任公司 | 重定向音频输出 |
| KR102664604B1 (ko) | 2017-07-14 | 2024-05-14 | 에프. 호프만-라 로슈 아게 | 이환형 케톤 화합물 및 이의 사용 방법 |
| EP3694858B1 (en) | 2017-10-11 | 2023-01-11 | F. Hoffmann-La Roche AG | Bicyclic compounds for use as rip1 kinase inhibitors |
| AU2018360270A1 (en) | 2017-10-31 | 2020-03-26 | F. Hoffmann-La Roche Ag | Bicyclic sulfones and sulfoxides and methods of use thereof |
-
2018
- 2018-07-12 KR KR1020207004030A patent/KR102664604B1/ko active Active
- 2018-07-12 EP EP18740815.8A patent/EP3652178B1/en active Active
- 2018-07-12 WO PCT/EP2018/068998 patent/WO2019012063A1/en not_active Ceased
- 2018-07-12 FI FIEP18740815.8T patent/FI3652178T3/fi active
- 2018-07-12 SI SI201831080T patent/SI3652178T1/sl unknown
- 2018-07-12 AU AU2018300043A patent/AU2018300043B2/en active Active
- 2018-07-12 PL PL18740815.8T patent/PL3652178T3/pl unknown
- 2018-07-12 LT LTEPPCT/EP2018/068998T patent/LT3652178T/lt unknown
- 2018-07-12 DK DK18740815.8T patent/DK3652178T3/da active
- 2018-07-12 CR CR20200002A patent/CR20200002A/es unknown
- 2018-07-12 HR HRP20240354TT patent/HRP20240354T1/hr unknown
- 2018-07-12 CA CA3067944A patent/CA3067944C/en active Active
- 2018-07-12 IL IL271981A patent/IL271981B/en unknown
- 2018-07-12 SG SG11202000333UA patent/SG11202000333UA/en unknown
- 2018-07-12 EP EP24152498.2A patent/EP4397309A3/en active Pending
- 2018-07-12 HU HUE18740815A patent/HUE065793T2/hu unknown
- 2018-07-12 AR ARP180101941 patent/AR112274A1/es active IP Right Grant
- 2018-07-12 CA CA3185865A patent/CA3185865A1/en active Pending
- 2018-07-12 PE PE2020000027A patent/PE20200793A1/es unknown
- 2018-07-12 BR BR112020000771-4A patent/BR112020000771A2/pt unknown
- 2018-07-12 CN CN202411725301.0A patent/CN119613408A/zh active Pending
- 2018-07-12 MA MA49560A patent/MA49560B1/fr unknown
- 2018-07-12 ES ES18740815T patent/ES2973661T3/es active Active
- 2018-07-12 PT PT187408158T patent/PT3652178T/pt unknown
- 2018-07-12 JP JP2020501256A patent/JP7258843B2/ja active Active
- 2018-07-12 US US16/034,207 patent/US11098058B2/en active Active
- 2018-07-12 IL IL294961A patent/IL294961A/en unknown
- 2018-07-12 RS RS20240314A patent/RS65308B1/sr unknown
- 2018-07-12 TW TW107124048A patent/TWI805595B/zh active
- 2018-07-12 KR KR1020247014915A patent/KR20240065201A/ko active Pending
- 2018-07-12 UA UAA202000831A patent/UA125448C2/uk unknown
- 2018-07-12 CN CN201880046714.2A patent/CN110914271B/zh active Active
-
2020
- 2020-01-08 CO CONC2020/0000134A patent/CO2020000134A2/es unknown
- 2020-01-13 CL CL2020000101A patent/CL2020000101A1/es unknown
- 2020-01-14 PH PH12020500105A patent/PH12020500105A1/en unknown
-
2021
- 2021-01-12 US US17/147,449 patent/US11834461B2/en active Active
- 2021-06-26 AU AU2021204369A patent/AU2021204369A1/en not_active Abandoned
-
2023
- 2023-04-05 JP JP2023061174A patent/JP7734163B2/ja active Active
- 2023-05-25 AU AU2023203292A patent/AU2023203292B2/en active Active
- 2023-11-21 US US18/516,014 patent/US20240300974A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2020526549A5 (OSRAM) | ||
| JP7398391B2 (ja) | Ｎ－［４－オキソ－２，３－ジヒドロ－１，５－ベンズオキサゼピン－３－イル］－５，６－ジヒドロ－４Ｈ－ピロロ［１，２－ｂ］ピラゾール－２－カルボキサミド誘導体及び例えば過敏性腸症候群（ＩＢＳ）を処置するためのＲＩＰ１キナーゼ阻害剤としての関連化合物 | |
| JP2024532734A (ja) | 複素環式化合物及び使用方法 | |
| CN107531690B (zh) | 用作CBP和/或EP300抑制剂的4,5,6,7-四氢-1H-吡唑并[4,3-c]吡啶-3-胺化合物 | |
| TWI572606B (zh) | 四氫吡唑并嘧啶化合物 | |
| JP7734163B2 (ja) | 二環式ケトン化合物及びその使用方法 | |
| JP2013523884A5 (OSRAM) | ||
| CN117263942A (zh) | Shp2磷酸酶抑制剂及其使用方法 | |
| JP2019516759A (ja) | がんの処置のためのピラゾロピリジン誘導体 | |
| JP2020515603A (ja) | Ｈｐｋ１阻害剤としてのイソキノリン | |
| TW201514145A (zh) | 作為ｂｔｋ抑制劑的初級甲醯胺 | |
| JPWO2020005873A5 (OSRAM) | ||
| EP3218376A1 (en) | Bromodomain inhibitors and uses thereof | |
| JP2017511365A (ja) | 複素環キナーゼ阻害薬 | |
| CN107108512A (zh) | 治疗性化合物及其用途 | |
| TW201706258A (zh) | 作為ｔｎｆ信號傳遞調節劑之吲唑酮 | |
| AU2023356614A1 (en) | Heterocyclic inhibitors of kras g12c mutant proteins and uses thereof | |
| JP2020536915A5 (OSRAM) | ||
| KR102598203B1 (ko) | 델타-5 불포화효소 억제제로서의 헤테로시클릭 화합물 및 사용 방법 | |
| KR20250130621A (ko) | 치환된 디하이드로피롤로[3,4-d]피리미딘 화합물 및 의학적 병태 치료에서의 이의 용도 | |
| JP2023537055A (ja) | Ａｔｒ阻害剤およびその使用 | |
| JP2013518823A5 (OSRAM) | ||
| JP2009500366A5 (OSRAM) | ||
| JP2015528435A5 (OSRAM) | ||
| NZ760749B2 (en) | Bicyclic ketone compounds and methods of use thereof |