JPWO2020168149A5 - - Google Patents
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- JPWO2020168149A5 JPWO2020168149A5 JP2021547529A JP2021547529A JPWO2020168149A5 JP WO2020168149 A5 JPWO2020168149 A5 JP WO2020168149A5 JP 2021547529 A JP2021547529 A JP 2021547529A JP 2021547529 A JP2021547529 A JP 2021547529A JP WO2020168149 A5 JPWO2020168149 A5 JP WO2020168149A5
- Authority
- JP
- Japan
- Prior art keywords
- bicyclo
- methyl
- carboxamide
- octan
- oxadiazol
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 74
- 125000003545 alkoxy group Chemical group 0.000 claims 33
- -1 cyano, hydroxyl Chemical group 0.000 claims 32
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 24
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 239000012453 solvate Substances 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 125000004043 oxo group Chemical group O=* 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000004122 cyclic group Chemical group 0.000 claims 9
- 125000004452 carbocyclyl group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 6
- 239000004202 carbamide Substances 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 206010016654 Fibrosis Diseases 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 230000004761 fibrosis Effects 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 2
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims 2
- XJVCBQQIEWBUJL-UHFFFAOYSA-N 1,1-dioxothiane-4-carboxamide Chemical compound NC(=O)C1CCS(=O)(=O)CC1 XJVCBQQIEWBUJL-UHFFFAOYSA-N 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- GECCAWNXQGQNEC-UHFFFAOYSA-N methyl 3-[3-[cyclohexanecarbonyl-[[4-[4-(dimethylamino)phenyl]-1-bicyclo[2.2.2]octanyl]methyl]amino]phenyl]propanoate Chemical compound CN(C1=CC=C(C=C1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C=1C=C(C=CC=1)CCC(=O)OC)C GECCAWNXQGQNEC-UHFFFAOYSA-N 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- DGOYLVBDCVINQZ-UHFFFAOYSA-N oxane-4-carboxamide Chemical compound NC(=O)C1CCOCC1 DGOYLVBDCVINQZ-UHFFFAOYSA-N 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 claims 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 claims 1
- GBWHAHIRNVSSOB-UTTDKNERSA-N 1-(3-bromophenyl)-1-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-[(2S)-2-fluoro-3-hydroxy-3-methylbutyl]urea Chemical compound BrC=1C=C(C=CC=1)N(C(=O)NC[C@@H](C(C)(C)O)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F GBWHAHIRNVSSOB-UTTDKNERSA-N 0.000 claims 1
- LZNCBDSBQDTSTA-UHFFFAOYSA-N 1-(3-cyanophenyl)-1-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-(3-hydroxy-2,2-dimethylpropyl)urea Chemical compound C(#N)C=1C=C(C=CC=1)N(C(=O)NCC(CO)(C)C)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F LZNCBDSBQDTSTA-UHFFFAOYSA-N 0.000 claims 1
- OIZJYDDBJRWBNQ-UHFFFAOYSA-N 1-(3-cyanophenyl)-1-[[4-[5-(2-fluoropropan-2-yl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-(3-hydroxy-2,2-dimethylpropyl)urea Chemical compound C(#N)C=1C=C(C=CC=1)N(C(=O)NCC(CO)(C)C)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(C)F OIZJYDDBJRWBNQ-UHFFFAOYSA-N 0.000 claims 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 claims 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 claims 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 claims 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 claims 1
- UGZZEGBFHIPOHM-UHFFFAOYSA-N 3-[4-[(3-bromo-N-(3-fluorobicyclo[1.1.1]pentane-1-carbonyl)anilino)methyl]-1-bicyclo[2.2.2]octanyl]-1,2,4-oxadiazole-5-carboxamide Chemical compound BrC=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(=O)N UGZZEGBFHIPOHM-UHFFFAOYSA-N 0.000 claims 1
- PPMCBRCXGQGTNZ-UHFFFAOYSA-N 3-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl-(3-fluorobicyclo[1.1.1]pentane-1-carbonyl)amino]benzoic acid Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C=1C=C(C(=O)O)C=CC=1 PPMCBRCXGQGTNZ-UHFFFAOYSA-N 0.000 claims 1
- QQKZBEXAJYXJKN-UHFFFAOYSA-N 3-[cyclohexanecarbonyl-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]amino]-N-(1,3-thiazol-2-yl)benzamide Chemical compound CC1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C=1C=C(C(=O)NC=2SC=CN=2)C=CC=1 QQKZBEXAJYXJKN-UHFFFAOYSA-N 0.000 claims 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 claims 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- SSQVBQNUNXHHHU-UHFFFAOYSA-N N-(3-bromo-4-chlorophenyl)-N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound BrC=1C=C(C=CC=1Cl)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NC(=NO1)C(C)(C)C SSQVBQNUNXHHHU-UHFFFAOYSA-N 0.000 claims 1
- HSESCXOBDMFLHS-UHFFFAOYSA-N N-(3-bromophenyl)-3-fluoro-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]bicyclo[1.1.1]pentane-1-carboxamide Chemical compound BrC=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(F)(F)F HSESCXOBDMFLHS-UHFFFAOYSA-N 0.000 claims 1
- CCUGRWBRFQYSMJ-UHFFFAOYSA-N N-(3-bromophenyl)-N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.1]heptanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound BrC=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(C2)C1=NC(=NO1)C(C)(C)C CCUGRWBRFQYSMJ-UHFFFAOYSA-N 0.000 claims 1
- BKKSLUIWLNOKBI-UHFFFAOYSA-N N-(3-bromophenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-2,2-difluorocyclopropane-1-carboxamide Chemical compound BrC=1C=C(C=CC=1)N(C(=O)C1C(C1)(F)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F BKKSLUIWLNOKBI-UHFFFAOYSA-N 0.000 claims 1
- XLABGHDIGXUFAA-UHFFFAOYSA-N N-(3-bromophenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound BrC=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F XLABGHDIGXUFAA-UHFFFAOYSA-N 0.000 claims 1
- SETUBMTYGIZFPQ-UHFFFAOYSA-N N-(3-bromophenyl)-N-[[4-[5-(1,1-difluoroethyl)pyridin-2-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound BrC=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NC=C(C=C1)C(C)(F)F SETUBMTYGIZFPQ-UHFFFAOYSA-N 0.000 claims 1
- BQJSJDXTEYCDIS-UHFFFAOYSA-N N-(3-bromophenyl)-N-[[4-[5-(2-fluoropropan-2-yl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-(2-hydroxypropan-2-yl)bicyclo[1.1.1]pentane-1-carboxamide Chemical compound C1(Br)=CC(N(CC23CCC(C=4N=C(C(C)(F)C)ON=4)(CC2)CC3)C(=O)C23CC(C(O)(C)C)(C2)C3)=CC=C1 BQJSJDXTEYCDIS-UHFFFAOYSA-N 0.000 claims 1
- BRXHBOBIAPOTNQ-UHFFFAOYSA-N N-(3-carbamoylphenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(N)(=O)C=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F BRXHBOBIAPOTNQ-UHFFFAOYSA-N 0.000 claims 1
- GUYWKLDYKANEIH-UHFFFAOYSA-N N-(3-chlorophenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound ClC=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F GUYWKLDYKANEIH-UHFFFAOYSA-N 0.000 claims 1
- JQZCGAHDUXNWBR-UHFFFAOYSA-N N-(3-chlorophenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-hydroxy-3-(trifluoromethyl)cyclobutane-1-carboxamide Chemical compound ClC=1C=C(C=CC=1)N(C(=O)C1CC(C1)(C(F)(F)F)O)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F JQZCGAHDUXNWBR-UHFFFAOYSA-N 0.000 claims 1
- ZGPKMLAQGBLPEW-UHFFFAOYSA-N N-(3-chlorophenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound ClC=1C=C(C=CC=1)N(C(=O)C1CCC(CC1)(F)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F ZGPKMLAQGBLPEW-UHFFFAOYSA-N 0.000 claims 1
- SNOUTJYVYQVEOF-UHFFFAOYSA-N N-(3-cyano-5-fluorophenyl)-N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3,3-difluorocyclobutane-1-carboxamide Chemical compound C(#N)C=1C=C(C=C(C=1)F)N(C(=O)C1CC(C1)(F)F)CC12CCC(CC1)(CC2)C1=NC(=NO1)C1CC1 SNOUTJYVYQVEOF-UHFFFAOYSA-N 0.000 claims 1
- XHPMWNUKTFHATE-UHFFFAOYSA-N N-(3-cyano-5-fluorophenyl)-N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(#N)C=1C=C(C=C(C=1)F)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NC(=NO1)C1CC1 XHPMWNUKTFHATE-UHFFFAOYSA-N 0.000 claims 1
- FVMKYMFGKGBNRF-UHFFFAOYSA-N N-(3-cyano-5-fluorophenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-1,1-dioxothiane-4-carboxamide Chemical compound CC(C1=NC(=NO1)C23CCC(CC2)(CC3)CN(C4=CC(=CC(=C4)C#N)F)C(=O)C5CCS(=O)(=O)CC5)(F)F FVMKYMFGKGBNRF-UHFFFAOYSA-N 0.000 claims 1
- REUZZPDLQFIISE-UHFFFAOYSA-N N-(3-cyano-5-fluorophenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3,3-difluorocyclobutane-1-carboxamide Chemical compound C(#N)C=1C=C(C=C(C=1)F)N(C(=O)C1CC(C1)(F)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F REUZZPDLQFIISE-UHFFFAOYSA-N 0.000 claims 1
- XWWLRHBBHNPHCQ-UHFFFAOYSA-N N-(3-cyano-5-fluorophenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(#N)C=1C=C(C=C(C=1)F)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F XWWLRHBBHNPHCQ-UHFFFAOYSA-N 0.000 claims 1
- DLYYKJVATJGYMS-UHFFFAOYSA-N N-(3-cyanophenyl)-3-fluoro-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]bicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(F)(F)F DLYYKJVATJGYMS-UHFFFAOYSA-N 0.000 claims 1
- FAGOBWQTGRNMAG-UHFFFAOYSA-N N-(3-cyanophenyl)-N-[1-[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]ethyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)C(C)C12CCC(CC1)(CC2)C1=NC(=NO1)C1CC1 FAGOBWQTGRNMAG-UHFFFAOYSA-N 0.000 claims 1
- ZKQRBNSHAXTWNO-UHFFFAOYSA-N N-(3-cyanophenyl)-N-[[4-(5-cyclopropyl-2-methylpyrazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=CC(=NN1C)C1CC1 ZKQRBNSHAXTWNO-UHFFFAOYSA-N 0.000 claims 1
- LCAUWIAQITXDCI-UHFFFAOYSA-N N-(3-cyanophenyl)-N-[[4-(5-cyclopropyl-2-methylpyrazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)N(C(=O)C1CCC(CC1)(F)F)CC12CCC(CC1)(CC2)C1=CC(=NN1C)C1CC1 LCAUWIAQITXDCI-UHFFFAOYSA-N 0.000 claims 1
- CSKVOLQGSMAHCG-UHFFFAOYSA-N N-(3-cyanophenyl)-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)N(C(=O)C12CC(C1)(C2)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F CSKVOLQGSMAHCG-UHFFFAOYSA-N 0.000 claims 1
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- DLIYGCIBPVXCTQ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-ethoxyphenyl)-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)OCC DLIYGCIBPVXCTQ-UHFFFAOYSA-N 0.000 claims 1
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- MSBRACMGLWWITN-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-carbamoyl-4-fluorophenyl)-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=C(C=C1)F)C(N)=O MSBRACMGLWWITN-UHFFFAOYSA-N 0.000 claims 1
- JVFIGXOVCNLCCZ-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-cyanophenyl)-3,3-difluorocyclobutane-1-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CC(C1)(F)F)C1=CC(=CC=C1)C#N JVFIGXOVCNLCCZ-UHFFFAOYSA-N 0.000 claims 1
- GTVIUYHWPUILKR-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-cyanophenyl)-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)C#N GTVIUYHWPUILKR-UHFFFAOYSA-N 0.000 claims 1
- LGCWLMKSSSJLSK-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-cyanophenyl)-4,4-difluorocyclohexane-1-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C#N LGCWLMKSSSJLSK-UHFFFAOYSA-N 0.000 claims 1
- GMNHBBPNTFUYHT-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-dimethylphosphorylphenyl)-1,1-dioxothiane-4-carboxamide Chemical compound CC(C)(C)C1=NOC(=N1)C23CCC(CC2)(CC3)CN(C4=CC(=CC=C4)P(=O)(C)C)C(=O)C5CCS(=O)(=O)CC5 GMNHBBPNTFUYHT-UHFFFAOYSA-N 0.000 claims 1
- QAJIUMQRWZVHBL-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-dimethylphosphorylphenyl)-3,3-difluorocyclobutane-1-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CC(C1)(F)F)C1=CC(=CC=C1)P(=O)(C)C QAJIUMQRWZVHBL-UHFFFAOYSA-N 0.000 claims 1
- MIROSIURTZIDCA-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-dimethylphosphorylphenyl)-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)P(=O)(C)C MIROSIURTZIDCA-UHFFFAOYSA-N 0.000 claims 1
- AIMWKBVIZAIWIU-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-dimethylphosphorylphenyl)oxane-4-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)P(=O)(C)C AIMWKBVIZAIWIU-UHFFFAOYSA-N 0.000 claims 1
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- UPZZWOPNWYPRHI-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(4-ethoxyanilino)phenyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)NC1=CC=C(C=C1)OCC UPZZWOPNWYPRHI-UHFFFAOYSA-N 0.000 claims 1
- XFPDEGOJDJEWDR-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(ethylcarbamoyl)-4-fluorophenyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=C(C=C1)F)C(NCC)=O XFPDEGOJDJEWDR-UHFFFAOYSA-N 0.000 claims 1
- DQGDKSLYLFUQAW-UHFFFAOYSA-N N-[[4-(5-cyclopropyl-2-methylpyrazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3-fluoro-N-(3-methylsulfonylphenyl)bicyclo[1.1.1]pentane-1-carboxamide Chemical compound S(=O)(=O)(C1=CC(N(CC23CCC(C=4N(N=C(C=4)C4CC4)C)(CC2)CC3)C(=O)C23CC(C2)(F)C3)=CC=C1)C DQGDKSLYLFUQAW-UHFFFAOYSA-N 0.000 claims 1
- FQKWWKLKDXQUTJ-UHFFFAOYSA-N N-[[4-(5-cyclopropyl-2-methylpyrazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluoro-N-(3-methylsulfonylphenyl)cyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NN(C(=C1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)S(=O)(=O)C)C FQKWWKLKDXQUTJ-UHFFFAOYSA-N 0.000 claims 1
- HECPAVYKNFRKAM-UHFFFAOYSA-N N-[[4-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3-fluoro-N-(3-hydroxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)O HECPAVYKNFRKAM-UHFFFAOYSA-N 0.000 claims 1
- JAOXHPCIDRYJSJ-UHFFFAOYSA-N N-[[4-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3-fluoro-N-[3-(2-hydroxy-2-methylpropoxy)phenyl]bicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)OCC(C)(C)O JAOXHPCIDRYJSJ-UHFFFAOYSA-N 0.000 claims 1
- NFSSHCNRTWBMEN-UHFFFAOYSA-N N-[[4-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3-fluoro-N-[3-[4-(trifluoromethyl)anilino]phenyl]bicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)NC1=CC=C(C=C1)C(F)(F)F NFSSHCNRTWBMEN-UHFFFAOYSA-N 0.000 claims 1
- UDBGKCSRUSSIJZ-UHFFFAOYSA-N N-[[4-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(4-ethoxyanilino)phenyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)NC1=CC=C(C=C1)OCC UDBGKCSRUSSIJZ-UHFFFAOYSA-N 0.000 claims 1
- BYXFQLHABBOLSO-UHFFFAOYSA-N N-[[4-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(4-ethylanilino)phenyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)NC1=CC=C(C=C1)CC BYXFQLHABBOLSO-UHFFFAOYSA-N 0.000 claims 1
- HNWHTQWAOBXFNE-UHFFFAOYSA-N N-[[4-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(cyanomethoxy)phenyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)OCC#N HNWHTQWAOBXFNE-UHFFFAOYSA-N 0.000 claims 1
- RFUSEXUYEAUEON-UHFFFAOYSA-N N-[[4-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[(2-cyclopropylpyrimidin-5-yl)amino]phenyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)NC=1C=NC(=NC=1)C1CC1 RFUSEXUYEAUEON-UHFFFAOYSA-N 0.000 claims 1
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- CODQNFKGGDUJIH-UHFFFAOYSA-N N-[[4-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[5-(difluoromethoxy)pyrimidin-2-yl]oxyphenyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)OC1=NC=C(C=N1)OC(F)F CODQNFKGGDUJIH-UHFFFAOYSA-N 0.000 claims 1
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- NHLQJRGHCIPIQW-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-fluoro-N-(3-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)OC NHLQJRGHCIPIQW-UHFFFAOYSA-N 0.000 claims 1
- ZAULNUHJWZZNSF-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-fluoro-N-(3-propan-2-yloxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)OC(C)C ZAULNUHJWZZNSF-UHFFFAOYSA-N 0.000 claims 1
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- GTMZJQWAEOVIAM-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-fluoro-N-[3-(trifluoromethyl)phenyl]bicyclo[1.1.1]pentane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)C(F)(F)F GTMZJQWAEOVIAM-UHFFFAOYSA-N 0.000 claims 1
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- OAIJVCXNKPZMBY-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluoro-N-(3-fluorophenyl)cyclohexane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)F OAIJVCXNKPZMBY-UHFFFAOYSA-N 0.000 claims 1
- RJQQHGIGTYBCPK-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluoro-N-[3-(methylsulfamoyl)phenyl]cyclohexane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)S(NC)(=O)=O RJQQHGIGTYBCPK-UHFFFAOYSA-N 0.000 claims 1
- JDWOSRFIVRZSLS-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluoro-N-[3-(trifluoromethyl)phenyl]cyclohexane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C(F)(F)F JDWOSRFIVRZSLS-UHFFFAOYSA-N 0.000 claims 1
- QCEIUPUBRQZASN-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-N-(3,4-difluorophenyl)-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=C(C=C1)F)F QCEIUPUBRQZASN-UHFFFAOYSA-N 0.000 claims 1
- YVUUECKAJADIBW-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-N-(3,4-difluorophenyl)-4,4-difluorocyclohexane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=C(C=C1)F)F YVUUECKAJADIBW-UHFFFAOYSA-N 0.000 claims 1
- NRKRESBWFVSDBD-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-dimethylphosphorylphenyl)-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)P(=O)(C)C NRKRESBWFVSDBD-UHFFFAOYSA-N 0.000 claims 1
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- FLBCWOJCNRVLOJ-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-ethoxyphenyl)-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)OCC FLBCWOJCNRVLOJ-UHFFFAOYSA-N 0.000 claims 1
- OMUJNSAJUVZDRZ-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-N-(3-fluorophenyl)-3-hydroxy-3-(trifluoromethyl)cyclobutane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C1CC(C1)(C(F)(F)F)O)C1=CC(=CC=C1)F OMUJNSAJUVZDRZ-UHFFFAOYSA-N 0.000 claims 1
- AMRKBJFUUKSRPS-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(difluoromethoxy)phenyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)OC(F)F AMRKBJFUUKSRPS-UHFFFAOYSA-N 0.000 claims 1
- RAJWBNIRDBMLHD-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(difluoromethoxy)phenyl]-3-hydroxy-3-(trifluoromethyl)cyclobutane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C1CC(C1)(C(F)(F)F)O)C1=CC(=CC=C1)OC(F)F RAJWBNIRDBMLHD-UHFFFAOYSA-N 0.000 claims 1
- MYHVFNYARQFDDO-UHFFFAOYSA-N N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(ethylcarbamoyl)phenyl]-3-fluorobicyclo[1.1.1]pentane-1-carboxamide Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C1=CC(=CC=C1)C(NCC)=O MYHVFNYARQFDDO-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- AWXXNEOTLRMFKW-UHFFFAOYSA-N bicyclo[1.1.1]pentane-3-carboxamide Chemical compound C1C2CC1(C(=O)N)C2 AWXXNEOTLRMFKW-UHFFFAOYSA-N 0.000 claims 1
- 210000000013 bile duct Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000001587 cholestatic effect Effects 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
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- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000006419 fluorocyclopropyl group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- SVDTTZDWDHOLSE-UHFFFAOYSA-N methyl 2-[3-[[1-(1-methylindazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl]methyl-(oxane-4-carbonyl)amino]phenoxy]acetate Chemical compound CN1N=CC2=CC(=CC=C12)C12OCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C=1C=C(OCC(=O)OC)C=CC=1 SVDTTZDWDHOLSE-UHFFFAOYSA-N 0.000 claims 1
- XTQRSTWJSATPID-UHFFFAOYSA-N methyl 2-[3-[[4-[3-chloro-4-(dimethylamino)phenyl]-1-bicyclo[2.2.2]octanyl]methyl-(cyclohexanecarbonyl)amino]phenoxy]acetate Chemical compound ClC=1C=C(C=CC=1N(C)C)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C=1C=C(OCC(=O)OC)C=CC=1 XTQRSTWJSATPID-UHFFFAOYSA-N 0.000 claims 1
- FTTWQXXYSUXMNN-UHFFFAOYSA-N methyl 2-[3-[cyclohexanecarbonyl-[[4-[4-(dimethylamino)phenyl]-1-bicyclo[2.2.2]octanyl]methyl]amino]phenoxy]acetate Chemical compound CN(C1=CC=C(C=C1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C=1C=C(OCC(=O)OC)C=CC=1)C FTTWQXXYSUXMNN-UHFFFAOYSA-N 0.000 claims 1
- SYARPIYWAUALII-UHFFFAOYSA-N methyl 3-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl-(3-fluorobicyclo[1.1.1]pentane-1-carbonyl)amino]benzoate Chemical compound FC(C)(F)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C12CC(C1)(C2)F)C=1C=C(C(=O)OC)C=CC=1 SYARPIYWAUALII-UHFFFAOYSA-N 0.000 claims 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
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| AU2008223348A1 (en) | 2007-03-07 | 2008-09-12 | Alantos Pharmaceuticals Holding, Inc. | Metalloprotease inhibitors containing a heterocyclic moiety |
| MX2009013946A (es) | 2007-07-02 | 2010-03-10 | Glaxosmithkline Llc | Agonistas del receptor de farnesoide x. |
| WO2009009059A1 (en) | 2007-07-09 | 2009-01-15 | Biogen Idec Ma Inc. | Spiro compounds as antagonists of tgf-beta |
| TW200906823A (en) | 2007-07-16 | 2009-02-16 | Lilly Co Eli | Compounds and methods for modulating FXR |
| CN101910151A (zh) | 2007-10-22 | 2010-12-08 | 先灵公司 | 双环杂环衍生物及其作为gpr119活性调节剂的用途 |
| EP2128158A1 (en) | 2008-05-26 | 2009-12-02 | Phenex Pharmaceuticals AG | Heterocyclic cyclopropyl-substituted FXR binding compounds |
| US20110230493A1 (en) | 2008-11-21 | 2011-09-22 | Pfizer Inc. | 1-OXA-8-Azaspiro [4,5] Decabe-8-Carboxamide Compounds as FAAH Inhibitors |
| EP2454243A2 (en) | 2009-07-15 | 2012-05-23 | Merck Serono SA | Tetrazole derivatives |
| US8440710B2 (en) | 2009-10-15 | 2013-05-14 | Hoffmann-La Roche Inc. | HSL inhibitors useful in the treatment of diabetes |
| EP2655368A1 (en) | 2010-12-20 | 2013-10-30 | Irm Llc | Compositions and methods for modulating farnesoid x receptors |
| CU24152B1 (es) | 2010-12-20 | 2016-02-29 | Irm Llc | 1,2 oxazol-8-azabiciclo[3,2,1]octano 8 il como moduladores de fxr |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| IN2014DN09346A (https=) | 2012-06-13 | 2015-07-17 | Hoffmann La Roche | |
| EP2903985A1 (en) | 2012-10-03 | 2015-08-12 | Advinus Therapeutics Limited | Spirocyclic compounds, compositions and medicinal applications thereof |
| US9567301B2 (en) | 2012-11-02 | 2017-02-14 | Dana-Farber Cancer Institute, Inc. | Pyrrol-1-yl benzoic acid derivatives useful as myc inhibitors |
| WO2014113485A1 (en) | 2013-01-15 | 2014-07-24 | Intermune, Inc. | Lysophosphatidic acid receptor antagonists |
| JP6333372B2 (ja) | 2013-07-09 | 2018-05-30 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ型肝炎ウイルス阻害剤の組み合わせ |
| EP3116851B1 (en) * | 2014-03-13 | 2023-07-26 | Salk Institute for Biological Studies | Analogs of fexaramine and methods of making and using |
| WO2015172747A1 (en) | 2014-05-16 | 2015-11-19 | Zhaoyin Wang | Spirocyclic molecules as mth1 inhibitors |
| WO2016039734A1 (en) | 2014-09-10 | 2016-03-17 | Halliburton Energy Services, Inc. | Perforating gun with integrated retaining system |
| EP3034499A1 (en) | 2014-12-17 | 2016-06-22 | Gilead Sciences, Inc. | Novel FXR (NR1H4) modulating compounds |
| EP3034501A1 (en) | 2014-12-17 | 2016-06-22 | Gilead Sciences, Inc. | Hydroxy containing FXR (NR1H4) modulating compounds |
| MX2017008057A (es) | 2014-12-18 | 2017-09-28 | Novartis Ag | Derivados de azabiciclooctano como agonistas de fxr para el uso en el tratamiento de enfermedades hepaticas y gastrointestinales. |
| CN106146483A (zh) | 2015-04-23 | 2016-11-23 | 上海迪诺医药科技有限公司 | 杂环类法尼酯衍生物x受体调节剂 |
| US10703712B2 (en) * | 2015-09-16 | 2020-07-07 | Metacrine, Inc. | Farnesoid X receptor agonists and uses thereof |
| EP3350164A4 (en) | 2015-09-16 | 2019-03-27 | Metacrine, Inc. | FARNESOID-X RECEPTOR AGONISTS AND USES THEREOF |
| CN106946867B (zh) | 2016-01-06 | 2019-11-12 | 广州市恒诺康医药科技有限公司 | Fxr受体调节剂及其制备方法和用途 |
| CN107021958A (zh) | 2016-02-01 | 2017-08-08 | 山东轩竹医药科技有限公司 | Fxr受体激动剂 |
| WO2017133521A1 (zh) | 2016-02-01 | 2017-08-10 | 山东轩竹医药科技有限公司 | Fxr受体激动剂 |
| MX384205B (es) | 2016-02-22 | 2025-03-14 | Novartis Ag | Metodos para usar agonistas de fxr. |
| ES2862194T3 (es) | 2016-02-22 | 2021-10-07 | Novartis Ag | Métodos para usar agonistas del FXR |
| CN109640987B (zh) | 2016-03-16 | 2022-12-02 | 库拉肿瘤学公司 | Menin-mll的桥联双环抑制剂及使用方法 |
| WO2017189663A1 (en) | 2016-04-26 | 2017-11-02 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as fxr agonists and methods of use thereof |
| US10080741B2 (en) | 2016-04-26 | 2018-09-25 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as FXR agonists and methods of use thereof |
| WO2017189651A1 (en) | 2016-04-26 | 2017-11-02 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as fxr agonists and methods of use thereof |
| WO2017201155A1 (en) | 2016-05-18 | 2017-11-23 | Enanta Pharmaceuticals, Inc. | lSOXAZOLE DERIVATIVES AS FXR AGONISTS AND METHODS OF USE THEREOF |
| MX385718B (es) | 2016-06-13 | 2025-03-18 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4). |
| AR108711A1 (es) | 2016-06-13 | 2018-09-19 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4) |
| CN108430998B (zh) | 2016-09-28 | 2021-07-09 | 四川科伦博泰生物医药股份有限公司 | 氮杂双环衍生物及其制备方法和用途 |
| CN106632294A (zh) | 2016-12-15 | 2017-05-10 | 宁波百纳西药业有限公司 | 一种螺环化合物及其药物用途 |
| US20200131129A1 (en) * | 2017-03-15 | 2020-04-30 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| CA3055990A1 (en) * | 2017-03-15 | 2018-09-20 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| WO2018170165A1 (en) | 2017-03-15 | 2018-09-20 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| WO2018170167A1 (en) | 2017-03-15 | 2018-09-20 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| JP7258763B2 (ja) * | 2017-03-15 | 2023-04-17 | メタクリン，インク． | ファルネソイドｘ受容体アゴニストおよびその使用 |
| PE20201170A1 (es) | 2017-11-01 | 2020-10-28 | Bristol Myers Squibb Co | Compuestos biciclicos en puente como moduladores del receptor farnesoide x |
| EA202190661A1 (ru) | 2018-09-18 | 2021-08-13 | Метакрайн, Инк. | Агонисты фарнезоидного х-рецептора для лечения заболевания |
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2020
- 2020-02-14 CN CN202080028339.6A patent/CN113727973B/zh active Active
- 2020-02-14 WO PCT/US2020/018211 patent/WO2020168149A1/en not_active Ceased
- 2020-02-14 KR KR1020217029598A patent/KR20210129684A/ko not_active Ceased
- 2020-02-14 MX MX2021009424A patent/MX2021009424A/es unknown
- 2020-02-14 EA EA202192275A patent/EA202192275A1/ru unknown
- 2020-02-14 JP JP2021547529A patent/JP7550777B2/ja active Active
- 2020-02-14 EP EP20712112.0A patent/EP3924333A1/en active Pending
- 2020-02-14 CA CA3129851A patent/CA3129851A1/en active Pending
- 2020-02-14 US US17/430,903 patent/US12319676B2/en active Active
- 2020-02-14 AU AU2020223150A patent/AU2020223150A1/en not_active Abandoned
- 2020-02-14 BR BR112021015688-7A patent/BR112021015688A2/pt not_active Application Discontinuation
- 2020-02-14 SG SG11202108794RA patent/SG11202108794RA/en unknown
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2021
- 2021-08-10 IL IL285510A patent/IL285510A/en unknown
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