JPWO2020168148A5 - - Google Patents
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- JPWO2020168148A5 JPWO2020168148A5 JP2021547477A JP2021547477A JPWO2020168148A5 JP WO2020168148 A5 JPWO2020168148 A5 JP WO2020168148A5 JP 2021547477 A JP2021547477 A JP 2021547477A JP 2021547477 A JP2021547477 A JP 2021547477A JP WO2020168148 A5 JPWO2020168148 A5 JP WO2020168148A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxadiazol
- bicyclo
- octan
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 76
- 125000003545 alkoxy group Chemical group 0.000 claims 33
- -1 cyano, hydroxyl Chemical group 0.000 claims 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 28
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000004043 oxo group Chemical group O=* 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- 206010016654 Fibrosis Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims 4
- 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 4
- 230000004761 fibrosis Effects 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) 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
- WXPJGTUVBMLPRN-UHFFFAOYSA-N N-[3-(4-methoxyphenyl)phenyl]-N-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]cyclohexanecarboxamide Chemical compound COC1=CC=C(C=C1)C1=CC(=CC=C1)N(C(=O)C1CCCCC1)CC12CCC(CC1)(CC2)C1=NC(=NO1)C WXPJGTUVBMLPRN-UHFFFAOYSA-N 0.000 claims 2
- JWWVWKYHYJKREU-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]oxane-4-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 JWWVWKYHYJKREU-UHFFFAOYSA-N 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
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 2
- 238000002560 therapeutic procedure Methods 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
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 claims 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-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
- 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
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 claims 1
- QPRLAZSMVXBKJI-UHFFFAOYSA-N 4,4-difluoro-N-[3-(2-methoxypyridin-4-yl)phenyl]-N-[[4-(5-methyl-1,3,4-thiadiazol-2-yl)-1-bicyclo[2.2.2]octanyl]methyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N(CC12CCC(CC1)(CC2)C=1SC(=NN=1)C)C1=CC(=CC=C1)C1=CC(=NC=C1)OC)F QPRLAZSMVXBKJI-UHFFFAOYSA-N 0.000 claims 1
- GHAXFQOTTMSPGE-UHFFFAOYSA-N 4-(difluoromethoxy)-N-[3-(2-ethoxypyrimidin-5-yl)phenyl]-N-[[4-[5-(2-fluoropropan-2-yl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]benzamide Chemical compound FC(OC1=CC=C(C(=O)N(CC23CCC(CC2)(CC3)C2=NOC(=N2)C(C)(C)F)C2=CC(=CC=C2)C=2C=NC(=NC=2)OCC)C=C1)F GHAXFQOTTMSPGE-UHFFFAOYSA-N 0.000 claims 1
- GMMSZHFGGVUNPI-UHFFFAOYSA-N 4-[[N-(cyclohexanecarbonyl)-3-(2-methoxypyridin-4-yl)anilino]methyl]-N-cyclopropylbicyclo[2.2.2]octane-1-carboxamide Chemical compound C1(CC1)NC(=O)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CC(=NC=C1)OC GMMSZHFGGVUNPI-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
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 claims 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-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
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 claims 1
- GOVBRCUVEFCHCH-UHFFFAOYSA-N N-[(4-cyano-1-bicyclo[2.2.2]octanyl)methyl]-N-[3-(2-methoxypyridin-4-yl)phenyl]cyclohexanecarboxamide Chemical compound C(#N)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CC(=NC=C1)OC GOVBRCUVEFCHCH-UHFFFAOYSA-N 0.000 claims 1
- GSOVGUORYLEBGQ-UHFFFAOYSA-N N-[3-(2-cyclopropyl-1-methylimidazol-4-yl)phenyl]-N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]oxane-3-carboxamide Chemical class C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1COCCC1)C1=CC(=CC=C1)C=1N=C(N(C=1)C)C1CC1 GSOVGUORYLEBGQ-UHFFFAOYSA-N 0.000 claims 1
- FDANABWPDRKTHB-UHFFFAOYSA-N N-[3-(2-cyclopropylpyrimidin-5-yl)phenyl]-4,4-difluoro-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]cyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NC=C(C=N1)C=1C=C(C=CC=1)N(C(=O)C1CCC(CC1)(F)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(F)(F)F FDANABWPDRKTHB-UHFFFAOYSA-N 0.000 claims 1
- LSRPKTGOWBTRBO-UHFFFAOYSA-N N-[3-(2-ethoxy-1,3-oxazol-5-yl)phenyl]-N-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]cyclohexanecarboxamide Chemical compound C(C)OC=1OC(=CN=1)C=1C=C(C=CC=1)N(C(=O)C1CCCCC1)CC12CCC(CC1)(CC2)C1=NC(=NO1)C LSRPKTGOWBTRBO-UHFFFAOYSA-N 0.000 claims 1
- YDGDIHJSHUQXJN-UHFFFAOYSA-N N-[3-(2-ethoxypyrimidin-5-yl)phenyl]-N-[[4-[5-(2-fluoropropan-2-yl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-4-methoxybenzamide Chemical compound C(C)OC1=NC=C(C=N1)C=1C=C(C=CC=1)N(C(C1=CC=C(C=C1)OC)=O)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(C)F YDGDIHJSHUQXJN-UHFFFAOYSA-N 0.000 claims 1
- LCCYZGJSTOUKQE-UHFFFAOYSA-N N-[3-(2-methoxy-1,3-oxazol-5-yl)phenyl]-N-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]cyclohexanecarboxamide Chemical compound COC=1OC(=CN=1)C=1C=C(C=CC=1)N(C(=O)C1CCCCC1)CC12CCC(CC1)(CC2)C1=NC(=NO1)C LCCYZGJSTOUKQE-UHFFFAOYSA-N 0.000 claims 1
- OJVDSIOMWRUSTQ-UHFFFAOYSA-N N-[3-(2-methoxypyridin-4-yl)phenyl]-N-[[3-[3-(oxan-4-yl)-1,2,4-oxadiazol-5-yl]-1-bicyclo[1.1.1]pentanyl]methyl]cyclohexanecarboxamide Chemical compound COC1=NC=CC(=C1)C=1C=C(C=CC=1)N(C(=O)C1CCCCC1)CC12CC(C1)(C2)C1=NC(=NO1)C1CCOCC1 OJVDSIOMWRUSTQ-UHFFFAOYSA-N 0.000 claims 1
- HUPFVOAJSVXGPX-UHFFFAOYSA-N N-[3-(2-methoxypyridin-4-yl)phenyl]-N-[[4-(1-methyltetrazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]cyclohexanecarboxamide Chemical compound COC1=NC=CC(=C1)C=1C=C(C=CC=1)N(C(=O)C1CCCCC1)CC12CCC(CC1)(CC2)C1=NN=NN1C HUPFVOAJSVXGPX-UHFFFAOYSA-N 0.000 claims 1
- TXLSLZGWXYAXES-UHFFFAOYSA-N N-[3-(2-methoxypyridin-4-yl)phenyl]-N-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]cyclohexanecarboxamide Chemical compound COC1=NC=CC(=C1)C=1C=C(C=CC=1)N(C(=O)C1CCCCC1)CC12CCC(CC1)(CC2)C1=NC(=NO1)C TXLSLZGWXYAXES-UHFFFAOYSA-N 0.000 claims 1
- QWNDSRJACMWMNP-UHFFFAOYSA-N N-[3-(2-methoxypyridin-4-yl)phenyl]-N-[[4-(5-methyl-1,3,4-thiadiazol-2-yl)-1-bicyclo[2.2.2]octanyl]methyl]cyclohexanecarboxamide Chemical compound COC1=NC=CC(=C1)C=1C=C(C=CC=1)N(C(=O)C1CCCCC1)CC12CCC(CC1)(CC2)C=1SC(=NN=1)C QWNDSRJACMWMNP-UHFFFAOYSA-N 0.000 claims 1
- XMFBLCBOXDHSMW-UHFFFAOYSA-N N-[3-(2-methoxypyridin-4-yl)phenyl]-N-[[4-(5-methyl-1,3,4-thiadiazol-2-yl)-1-bicyclo[2.2.2]octanyl]methyl]oxane-4-carboxamide Chemical compound COC1=NC=CC(=C1)C=1C=C(C=CC=1)N(C(=O)C1CCOCC1)CC12CCC(CC1)(CC2)C=1SC(=NN=1)C XMFBLCBOXDHSMW-UHFFFAOYSA-N 0.000 claims 1
- MVXADEXUBDJICV-UHFFFAOYSA-N N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-N-[[4-(4-cyclopropyl-1,3-thiazol-2-yl)-1-bicyclo[2.2.2]octanyl]methyl]oxane-3-carboxamide Chemical class C1(CC1)C1=NOC(=N1)C=1C=C(C=CC=1)N(C(=O)C1COCCC1)CC12CCC(CC1)(CC2)C=1SC=C(N=1)C1CC1 MVXADEXUBDJICV-UHFFFAOYSA-N 0.000 claims 1
- QTERZLVURZPGRS-UHFFFAOYSA-N N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-N-[[4-(5-methyl-1,3-oxazol-2-yl)-1-bicyclo[2.2.2]octanyl]methyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C=1C=C(C=CC=1)N(C(=O)C1CCCCC1)CC12CCC(CC1)(CC2)C=1OC(=CN=1)C QTERZLVURZPGRS-UHFFFAOYSA-N 0.000 claims 1
- YSTQZGVOGODIIU-UHFFFAOYSA-N N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-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 C1(CC1)C1=NOC(=N1)C=1C=C(C=CC=1)N(C(=O)C1CCC(CC1)(F)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F YSTQZGVOGODIIU-UHFFFAOYSA-N 0.000 claims 1
- IAGYPTSPCASXQM-UHFFFAOYSA-N N-[3-(3-cyclopropyl-1,2-oxazol-5-yl)phenyl]-4,4-difluoro-N-[[4-[5-[1-(trifluoromethyl)cyclopropyl]-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]cyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=C1)C=1C=C(C=CC=1)N(C(=O)C1CCC(CC1)(F)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C1(CC1)C(F)(F)F IAGYPTSPCASXQM-UHFFFAOYSA-N 0.000 claims 1
- RLZYXHIKBCUPCK-UHFFFAOYSA-N N-[3-(3-cyclopropyl-1,2-oxazol-5-yl)phenyl]-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 C1(CC1)C1=NOC(=C1)C=1C=C(C=CC=1)N(C(=O)C1CCC(CC1)(F)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F RLZYXHIKBCUPCK-UHFFFAOYSA-N 0.000 claims 1
- GKOXLDTWZDMTNZ-UHFFFAOYSA-N N-[3-(3-ethyl-1,2,4-oxadiazol-5-yl)phenyl]-N-[1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]ethyl]cyclohexanecarboxamide Chemical compound C(C)C1=NOC(=N1)C=1C=C(C=CC=1)N(C(=O)C1CCCCC1)C(C)C12CCC(CC1)(CC2)C1=NC(=NO1)C GKOXLDTWZDMTNZ-UHFFFAOYSA-N 0.000 claims 1
- CDQDLYURVPMYBZ-UHFFFAOYSA-N N-[3-(3-methoxyphenyl)phenyl]-N-[1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]ethyl]cyclohexanecarboxamide Chemical compound COC=1C=C(C=CC=1)C1=CC(=CC=C1)N(C(=O)C1CCCCC1)C(C)C12CCC(CC1)(CC2)C1=NC(=NO1)C CDQDLYURVPMYBZ-UHFFFAOYSA-N 0.000 claims 1
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- IXSDCHGJPVVHOK-UHFFFAOYSA-N N-[3-(5-cyclopropyl-1,2-oxazol-3-yl)phenyl]-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 C1(CC1)C1=CC(=NO1)C=1C=C(C=CC=1)N(C(=O)C1CCS(CC1)(=O)=O)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F IXSDCHGJPVVHOK-UHFFFAOYSA-N 0.000 claims 1
- QWHGMABCAJZEOM-UHFFFAOYSA-N N-[3-(5-cyclopropyl-1,2-oxazol-3-yl)phenyl]-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 C1(CC1)C1=CC(=NO1)C=1C=C(C=CC=1)N(C(=O)C1CCC(CC1)(F)F)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F QWHGMABCAJZEOM-UHFFFAOYSA-N 0.000 claims 1
- OOYDNYJCFZPYCB-UHFFFAOYSA-N N-[3-(5-cyclopropyl-1,2-oxazol-3-yl)phenyl]-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-4-hydroxy-4-(trifluoromethyl)cyclohexane-1-carboxamide Chemical compound C1(CC1)C1=CC(=NO1)C=1C=C(C=CC=1)N(C(=O)C1CCC(CC1)(C(F)(F)F)O)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F OOYDNYJCFZPYCB-UHFFFAOYSA-N 0.000 claims 1
- OJRQEDCQYFHCFK-UHFFFAOYSA-N N-[3-(5-cyclopropyl-1,2-oxazol-3-yl)phenyl]-N-[[4-[5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=CC(=NO1)C=1C=C(C=CC=1)N(C(=O)C1CCOCC1)CC12CCC(CC1)(CC2)C1=NOC(=N1)C(C)(F)F OJRQEDCQYFHCFK-UHFFFAOYSA-N 0.000 claims 1
- YYTZXCLVXISDFL-UHFFFAOYSA-N N-[3-(5-cyclopropyl-1-methylpyrazol-3-yl)phenyl]-N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=NN(C(=C1)C1CC1)C YYTZXCLVXISDFL-UHFFFAOYSA-N 0.000 claims 1
- DMDJZYLMQSHNBX-UHFFFAOYSA-N N-[3-(5-methoxy-1,2-oxazol-3-yl)phenyl]-N-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]cyclohexanecarboxamide Chemical compound COC1=CC(=NO1)C=1C=C(C=CC=1)N(C(=O)C1CCCCC1)CC12CCC(CC1)(CC2)C1=NC(=NO1)C DMDJZYLMQSHNBX-UHFFFAOYSA-N 0.000 claims 1
- ZTLQEKZHPCLTOA-UHFFFAOYSA-N N-[3-[3-(cyclopropylmethyl)-1,2,4-oxadiazol-5-yl]phenyl]-N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C1=NC(=NO1)CC1CC1 ZTLQEKZHPCLTOA-UHFFFAOYSA-N 0.000 claims 1
- YJAYSNDSJHVPTF-UHFFFAOYSA-N N-[3-[3-(cyclopropylmethyl)-1,2,4-oxadiazol-5-yl]phenyl]-N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=NC(=NO1)CC1CC1 YJAYSNDSJHVPTF-UHFFFAOYSA-N 0.000 claims 1
- FNKNYZNPERKMOS-UHFFFAOYSA-N N-[[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[1.1.1]pentanyl]methyl]-N-[3-(2-methoxypyridin-4-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CC(C1)(C2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CC(=NC=C1)OC FNKNYZNPERKMOS-UHFFFAOYSA-N 0.000 claims 1
- DCIHEWZKVXZLKW-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluoro-N-[3-(2-methoxypyrimidin-4-yl)phenyl]cyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C1=NC(=NC=C1)OC DCIHEWZKVXZLKW-UHFFFAOYSA-N 0.000 claims 1
- GAVLMYVYEXSSKY-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluoro-N-[3-(5-fluoro-1,3-benzoxazol-2-yl)phenyl]cyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)F GAVLMYVYEXSSKY-UHFFFAOYSA-N 0.000 claims 1
- IBMQZLASGUVKSW-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-cyclopropyl-1,3-oxazol-5-yl)phenyl]-1-methylpiperidine-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCN(CC1)C)C1=CC(=CC=C1)C1=CN=C(O1)C1CC1 IBMQZLASGUVKSW-UHFFFAOYSA-N 0.000 claims 1
- MUABQGQAGPEDRH-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-cyclopropyl-1,3-oxazol-5-yl)phenyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C1=CN=C(O1)C1CC1 MUABQGQAGPEDRH-UHFFFAOYSA-N 0.000 claims 1
- XDOPHOVEJBTING-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-cyclopropyl-1,3-oxazol-5-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CN=C(O1)C1CC1 XDOPHOVEJBTING-UHFFFAOYSA-N 0.000 claims 1
- GSZPKPXBQYMXEY-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-cyclopropyl-1,3-oxazol-5-yl)phenyl]oxane-3-carboxamide Chemical class C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1COCCC1)C1=CC(=CC=C1)C1=CN=C(O1)C1CC1 GSZPKPXBQYMXEY-UHFFFAOYSA-N 0.000 claims 1
- UYBUYBZWNFYNGP-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-cyclopropyl-1,3-oxazol-5-yl)phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=CN=C(O1)C1CC1 UYBUYBZWNFYNGP-UHFFFAOYSA-N 0.000 claims 1
- XHUUZIARMOYRRG-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-cyclopropyloxypyrimidin-4-yl)phenyl]oxane-4-carboxamide Chemical compound C1(CC1)OC1=NC=CC(=N1)C=1C=C(C=CC=1)N(C(=O)C1CCOCC1)CC12CCC(CC1)(CC2)C1=NC(=NO1)C1CC1 XHUUZIARMOYRRG-UHFFFAOYSA-N 0.000 claims 1
- GZUCEMQLYQNXOZ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-ethoxy-1,3-oxazol-5-yl)phenyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C1=CN=C(O1)OCC GZUCEMQLYQNXOZ-UHFFFAOYSA-N 0.000 claims 1
- ARJMKKAGCAEYES-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-ethoxy-1,3-oxazol-5-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CN=C(O1)OCC ARJMKKAGCAEYES-UHFFFAOYSA-N 0.000 claims 1
- ILDBSPNGSKBTII-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-ethoxypyridin-4-yl)phenyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C1=CC(=NC=C1)OCC ILDBSPNGSKBTII-UHFFFAOYSA-N 0.000 claims 1
- PXBIHZACDYFZFI-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-ethoxypyridin-4-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CC(=NC=C1)OCC PXBIHZACDYFZFI-UHFFFAOYSA-N 0.000 claims 1
- UEBRHTGSJOTQAT-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-methoxy-1,3-oxazol-5-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CN=C(O1)OC UEBRHTGSJOTQAT-UHFFFAOYSA-N 0.000 claims 1
- CMWKIZCTJVNUGN-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-methoxypyridin-4-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CC(=NC=C1)OC CMWKIZCTJVNUGN-UHFFFAOYSA-N 0.000 claims 1
- MCJRAOYCVFEZGY-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-methoxypyridin-4-yl)phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=CC(=NC=C1)OC MCJRAOYCVFEZGY-UHFFFAOYSA-N 0.000 claims 1
- PRHOMOIRWNRVJH-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-methoxypyrimidin-4-yl)phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=NC(=NC=C1)OC PRHOMOIRWNRVJH-UHFFFAOYSA-N 0.000 claims 1
- OMPDMJHNPNCTJW-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-methyl-1,3-benzothiazol-6-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CC2=C(N=C(S2)C)C=C1 OMPDMJHNPNCTJW-UHFFFAOYSA-N 0.000 claims 1
- CWVOIAFLCCUXDY-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-methyl-1,3-benzothiazol-6-yl)phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=CC2=C(N=C(S2)C)C=C1 CWVOIAFLCCUXDY-UHFFFAOYSA-N 0.000 claims 1
- NSSXKVVZRNIEEY-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-propyl-1,3-oxazol-5-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CN=C(O1)CCC NSSXKVVZRNIEEY-UHFFFAOYSA-N 0.000 claims 1
- ZDRCPFLLFDKVKG-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-propyl-1,3-oxazol-5-yl)phenyl]oxane-3-carboxamide Chemical class C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1COCCC1)C1=CC(=CC=C1)C1=CN=C(O1)CCC ZDRCPFLLFDKVKG-UHFFFAOYSA-N 0.000 claims 1
- ZWXZHHATEIMUIK-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-propyl-1,3-oxazol-5-yl)phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=CN=C(O1)CCC ZWXZHHATEIMUIK-UHFFFAOYSA-N 0.000 claims 1
- ARAGAGXUWLVCPT-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-1,1-dioxothiane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCS(CC1)(=O)=O)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 ARAGAGXUWLVCPT-UHFFFAOYSA-N 0.000 claims 1
- KUTWRPJPBIBXQX-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-1-methylpiperidine-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCN(CC1)C)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 KUTWRPJPBIBXQX-UHFFFAOYSA-N 0.000 claims 1
- NIMZSZYKXGPFBB-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-2,6-dimethylmorpholine-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)N1CC(OC(C1)C)C)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 NIMZSZYKXGPFBB-UHFFFAOYSA-N 0.000 claims 1
- PZQPCBPFEGUBSJ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-3,3-dimethylpiperidine-1-carboxamide Chemical class C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)N1CC(CCC1)(C)C)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 PZQPCBPFEGUBSJ-UHFFFAOYSA-N 0.000 claims 1
- XHYCPJFYVQGYCW-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-3-(hydroxymethyl)piperidine-1-carboxamide Chemical class C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)N1CC(CCC1)CO)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 XHYCPJFYVQGYCW-UHFFFAOYSA-N 0.000 claims 1
- SZMLNRVSTUBLHZ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 SZMLNRVSTUBLHZ-UHFFFAOYSA-N 0.000 claims 1
- AFERFUPVMXVRDZ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-4,4-difluoropiperidine-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)N1CCC(CC1)(F)F)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 AFERFUPVMXVRDZ-UHFFFAOYSA-N 0.000 claims 1
- HVDLKJWMINAHHX-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-4-hydroxypiperidine-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)N1CCC(CC1)O)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 HVDLKJWMINAHHX-UHFFFAOYSA-N 0.000 claims 1
- SAXSQOASFSTGQE-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-4-methylpiperazine-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)N1CCN(CC1)C)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 SAXSQOASFSTGQE-UHFFFAOYSA-N 0.000 claims 1
- CGKVDQFIRPRKAH-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-4-methylpiperidine-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)N1CCC(CC1)C)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 CGKVDQFIRPRKAH-UHFFFAOYSA-N 0.000 claims 1
- NBWFUWHSHXBEJT-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-4-piperidin-1-ylpiperidine-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)N1CCC(CC1)N1CCCCC1)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 NBWFUWHSHXBEJT-UHFFFAOYSA-N 0.000 claims 1
- LCXAXLLXBJPQFP-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 LCXAXLLXBJPQFP-UHFFFAOYSA-N 0.000 claims 1
- OSLHJWJYFYDGAY-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]morpholine-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)N1CCOCC1)C1=CC(=CC=C1)C1=NC(=NO1)C1CC1 OSLHJWJYFYDGAY-UHFFFAOYSA-N 0.000 claims 1
- WCMZMEVJAKUNJW-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]oxane-3-carboxamide Chemical class C1CC(COC1)C(=O)N(CC23CCC(CC2)(CC3)C4=NC(=NO4)C5CC5)C6=CC=CC(=C6)C7=NC(=NO7)C8CC8 WCMZMEVJAKUNJW-UHFFFAOYSA-N 0.000 claims 1
- VOXSAHXZYHFEFQ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]oxane-4-carboxamide Chemical compound C1CC1C2=NOC(=N2)C3=CC(=CC=C3)N(CC45CCC(CC4)(CC5)C6=NC(=NO6)C7CC7)C(=O)C8CCOCC8 VOXSAHXZYHFEFQ-UHFFFAOYSA-N 0.000 claims 1
- KHTHUUZASANXOT-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]piperidine-1-carboxamide Chemical compound C1CCN(CC1)C(=O)N(CC23CCC(CC2)(CC3)C4=NC(=NO4)C5CC5)C6=CC=CC(=C6)C7=NC(=NO7)C8CC8 KHTHUUZASANXOT-UHFFFAOYSA-N 0.000 claims 1
- PSUWMVDUWYKOBR-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2-oxazol-5-yl)phenyl]-1,1-dioxothiane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCS(CC1)(=O)=O)C1=CC(=CC=C1)C1=CC(=NO1)C1CC1 PSUWMVDUWYKOBR-UHFFFAOYSA-N 0.000 claims 1
- GQBMZIADESAPOM-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2-oxazol-5-yl)phenyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C1=CC(=NO1)C1CC1 GQBMZIADESAPOM-UHFFFAOYSA-N 0.000 claims 1
- OKDDRVAGJWDETJ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2-oxazol-5-yl)phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=CC(=NO1)C1CC1 OKDDRVAGJWDETJ-UHFFFAOYSA-N 0.000 claims 1
- WISWDXFCZDFQNU-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-ethyl-1,2,4-oxadiazol-5-yl)phenyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C1=NC(=NO1)CC WISWDXFCZDFQNU-UHFFFAOYSA-N 0.000 claims 1
- XDGHQIRUTAMJLM-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-ethyl-1,2,4-oxadiazol-5-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=NC(=NO1)CC XDGHQIRUTAMJLM-UHFFFAOYSA-N 0.000 claims 1
- YXPYODMNTOANHI-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-ethyl-2-oxo-1,3-oxazol-5-yl)phenyl]oxane-3-carboxamide Chemical class CCN1C=C(OC1=O)C2=CC(=CC=C2)N(CC34CCC(CC3)(CC4)C5=NC(=NO5)C6CC6)C(=O)C7CCCOC7 YXPYODMNTOANHI-UHFFFAOYSA-N 0.000 claims 1
- BMJCAPSFAXHVTB-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-methoxyphenyl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C=1C=C(C=CC=1)C1=CC(=CC=C1)OC BMJCAPSFAXHVTB-UHFFFAOYSA-N 0.000 claims 1
- XEVICJMNDHWAQO-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(4-ethoxypyridin-2-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=NC=CC(=C1)OCC XEVICJMNDHWAQO-UHFFFAOYSA-N 0.000 claims 1
- GMNFPUOTHDJZNJ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(5-cyclopropyl-1,2-oxazol-3-yl)phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C1=NOC(=C1)C1CC1 GMNFPUOTHDJZNJ-UHFFFAOYSA-N 0.000 claims 1
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- KXRSAEAUOUBYFC-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(5-ethoxy-1,2-oxazol-3-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=NOC(=C1)OCC KXRSAEAUOUBYFC-UHFFFAOYSA-N 0.000 claims 1
- RJUVGIMEGSIFNO-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(5-ethoxy-1,3,4-oxadiazol-2-yl)phenyl]-4,4-difluorocyclohexane-1-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(F)F)C1=CC(=CC=C1)C=1OC(=NN=1)OCC RJUVGIMEGSIFNO-UHFFFAOYSA-N 0.000 claims 1
- AIRKYNHXPBOLPB-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(5-fluoro-1,3-benzoxazol-2-yl)phenyl]oxane-3-carboxamide Chemical class C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1COCCC1)C1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)F AIRKYNHXPBOLPB-UHFFFAOYSA-N 0.000 claims 1
- DJYSJQGENJQDRN-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(5-methoxy-1,2-oxazol-3-yl)phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=NOC(=C1)OC DJYSJQGENJQDRN-UHFFFAOYSA-N 0.000 claims 1
- HDTJMJDDXDYYJL-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[2-(2-hydroxypropan-2-yl)-1,3-thiazol-4-yl]phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C=1N=C(SC=1)C(C)(C)O HDTJMJDDXDYYJL-UHFFFAOYSA-N 0.000 claims 1
- GWUNLSLSRQZPRW-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[2-(methoxymethyl)-1,3-thiazol-4-yl]phenyl]cyclohexanecarboxamide Chemical compound COCC1=NC(=CS1)C2=CC(=CC=C2)N(CC34CCC(CC3)(CC4)C5=NC(=NO5)C6CC6)C(=O)C7CCCCC7 GWUNLSLSRQZPRW-UHFFFAOYSA-N 0.000 claims 1
- IZOYPVJUHCUDAQ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[2-(methoxymethyl)-1,3-thiazol-4-yl]phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C=1N=C(SC=1)COC IZOYPVJUHCUDAQ-UHFFFAOYSA-N 0.000 claims 1
- DWKYPFSEIOJZNE-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[2-(oxan-4-yl)-1,3-oxazol-5-yl]phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CN=C(O1)C1CCOCC1 DWKYPFSEIOJZNE-UHFFFAOYSA-N 0.000 claims 1
- LXLAWGOQKYCGHP-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[4-(2-hydroxypropan-2-yl)-1,3-oxazol-2-yl]phenyl]cyclohexanecarboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C=1OC=C(N=1)C(C)(C)O LXLAWGOQKYCGHP-UHFFFAOYSA-N 0.000 claims 1
- POUVHUUKOWVHPF-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[4-(difluoromethyl)-1,3-oxazol-2-yl]phenyl]cyclohexanecarboxamide Chemical compound C1CCC(CC1)C(=O)N(CC23CCC(CC2)(CC3)C4=NC(=NO4)C5CC5)C6=CC=CC(=C6)C7=NC(=CO7)C(F)F POUVHUUKOWVHPF-UHFFFAOYSA-N 0.000 claims 1
- MCZRPSNTOJCLAJ-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[4-(difluoromethyl)-1,3-oxazol-2-yl]phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C=1OC=C(N=1)C(F)F MCZRPSNTOJCLAJ-UHFFFAOYSA-N 0.000 claims 1
- SHMRWOHPZPYQKR-UHFFFAOYSA-N N-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[4-(methoxymethyl)-1,3-oxazol-2-yl]phenyl]oxane-4-carboxamide Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C=1OC=C(N=1)COC SHMRWOHPZPYQKR-UHFFFAOYSA-N 0.000 claims 1
- QTZUPWYJNZKNPG-UHFFFAOYSA-N N-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]cyclohexanecarboxamide Chemical compound CC1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=NC(=NO1)C QTZUPWYJNZKNPG-UHFFFAOYSA-N 0.000 claims 1
- HBUKJMYKLPQWGT-UHFFFAOYSA-N N-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-[2-(oxan-4-yl)-1,3-oxazol-5-yl]phenyl]cyclohexanecarboxamide Chemical compound CC1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C1=CC(=CC=C1)C1=CN=C(O1)C1CCOCC1 HBUKJMYKLPQWGT-UHFFFAOYSA-N 0.000 claims 1
- UTIJGQFAZMWRGN-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3,5-dichloro-N-[3-(2-ethoxypyrimidin-5-yl)phenyl]benzamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(C1=CC(=CC(=C1)Cl)Cl)=O)C1=CC(=CC=C1)C=1C=NC(=NC=1)OCC UTIJGQFAZMWRGN-UHFFFAOYSA-N 0.000 claims 1
- XSMOVHNWSKVNJC-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-3-chloro-N-[3-(2-ethoxypyrimidin-5-yl)phenyl]benzamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(C1=CC(=CC=C1)Cl)=O)C1=CC(=CC=C1)C=1C=NC(=NC=1)OCC XSMOVHNWSKVNJC-UHFFFAOYSA-N 0.000 claims 1
- NPPJVYNJPOZSAU-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluoro-N-[3-(4-methylimidazol-1-yl)phenyl]cyclohexane-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)N1C=NC(=C1)C NPPJVYNJPOZSAU-UHFFFAOYSA-N 0.000 claims 1
- HWVLSWLKLXPHLZ-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-4,4-difluoro-N-[3-(6-oxo-1H-pyridazin-4-yl)phenyl]cyclohexane-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=1C=NNC(C=1)=O HWVLSWLKLXPHLZ-UHFFFAOYSA-N 0.000 claims 1
- NCIOYQRTBWZIKQ-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(2-ethoxypyrimidin-5-yl)phenyl]oxane-4-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C=1C=NC(=NC=1)OCC NCIOYQRTBWZIKQ-UHFFFAOYSA-N 0.000 claims 1
- PRTBURIFXQSCLE-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-fluorophenyl]-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)F)C1=NC(=NO1)C1CC1 PRTBURIFXQSCLE-UHFFFAOYSA-N 0.000 claims 1
- USYVHHNHLUZBPE-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-fluorophenyl]oxane-4-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC(=C1)F)C1=NC(=NO1)C1CC1 USYVHHNHLUZBPE-UHFFFAOYSA-N 0.000 claims 1
- VUAISOVYOXSITO-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)phenyl]-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)C1=NC(=NO1)C1CC1 VUAISOVYOXSITO-UHFFFAOYSA-N 0.000 claims 1
- URPRLGWMXWXBSO-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(3-cyclopropyl-1,2-oxazol-5-yl)phenyl]-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)C1=CC(=NO1)C1CC1 URPRLGWMXWXBSO-UHFFFAOYSA-N 0.000 claims 1
- ULWRECXDMYEJIF-UHFFFAOYSA-N N-[[4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(4-ethoxyphenyl)-4-fluorophenyl]-4-hydroxy-4-methylcyclohexane-1-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCC(CC1)(C)O)C=1C=C(C(=CC=1)F)C1=CC=C(C=C1)OCC ULWRECXDMYEJIF-UHFFFAOYSA-N 0.000 claims 1
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- QBAJISRRSIZSEO-UHFFFAOYSA-N N-[[4-[5-(2-fluoropropan-2-yl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-N-[3-(6-oxo-1H-pyridazin-4-yl)phenyl]oxane-4-carboxamide Chemical compound FC(C)(C)C1=NC(=NO1)C12CCC(CC1)(CC2)CN(C(=O)C1CCOCC1)C1=CC(=CC=C1)C=1C=NNC(C=1)=O QBAJISRRSIZSEO-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 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
- 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
- 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
- 239000003937 drug carrier Substances 0.000 claims 1
- VZOGLRQCMUERGU-UHFFFAOYSA-N ethyl 2-[3-[cyclohexanecarbonyl-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]amino]phenyl]-1,3-oxazole-4-carboxylate Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C=1C=C(C=CC=1)C=1OC=C(N=1)C(=O)OCC VZOGLRQCMUERGU-UHFFFAOYSA-N 0.000 claims 1
- HESOEIFBFGIYEQ-UHFFFAOYSA-N ethyl 4-[3-[cyclohexanecarbonyl-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]amino]phenyl]-1,3-thiazole-2-carboxylate Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C=1C=C(C=CC=1)C=1N=C(SC=1)C(=O)OCC HESOEIFBFGIYEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- CULOFCBEYHIGQM-UHFFFAOYSA-N methyl 5-[3-[cyclohexanecarbonyl-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl]amino]phenyl]-1,2,4-oxadiazole-3-carboxylate Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCCCC1)C=1C=C(C=CC=1)C1=NC(=NO1)C(=O)OC CULOFCBEYHIGQM-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 claims 1
- 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
- CAXIBTNWWXEYCG-UHFFFAOYSA-N tert-butyl 4-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl-[3-[2-(methoxymethyl)-1,3-thiazol-4-yl]phenyl]carbamoyl]piperidine-1-carboxylate Chemical compound C1(CC1)C1=NOC(=N1)C12CCC(CC1)(CC2)CN(C(=O)C1CCN(CC1)C(=O)OC(C)(C)C)C1=CC(=CC=C1)C=1N=C(SC=1)COC CAXIBTNWWXEYCG-UHFFFAOYSA-N 0.000 claims 1
- CGYUJSKXHDMDIG-UHFFFAOYSA-N tert-butyl 4-[[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-bicyclo[2.2.2]octanyl]methyl-[3-[4-(difluoromethyl)-1,3-oxazol-2-yl]phenyl]carbamoyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)C(=O)N(CC23CCC(CC2)(CC3)C4=NC(=NO4)C5CC5)C6=CC=CC(=C6)C7=NC(=CO7)C(F)F CGYUJSKXHDMDIG-UHFFFAOYSA-N 0.000 claims 1
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| PCT/US2020/018210 WO2020168148A1 (en) | 2019-02-15 | 2020-02-14 | Substituted bicyclic compounds as farnesoid x receptor modulators |
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| JP2022521895A JP2022521895A (ja) | 2022-04-13 |
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| WO2015138969A1 (en) * | 2014-03-13 | 2015-09-17 | Salk Institute For Biological Studies | Analogs of fexaramine and methods of making and using |
| US10703712B2 (en) * | 2015-09-16 | 2020-07-07 | 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 |
| WO2018170166A1 (en) * | 2017-03-15 | 2018-09-20 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| US20200131129A1 (en) * | 2017-03-15 | 2020-04-30 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| CA3056019A1 (en) * | 2017-03-15 | 2018-09-20 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| WO2020061118A1 (en) * | 2018-09-18 | 2020-03-26 | Metacrine, Inc. | Farnesoid x receptor agonists and uses thereof |
| SG11202108798XA (en) * | 2019-02-15 | 2021-09-29 | Bristol Myers Squibb Co | Substituted amide compounds useful as farnesoid x receptor modulators |
| AR118050A1 (es) * | 2019-02-15 | 2021-09-15 | Bristol Myers Squibb Co | Compuestos bicíclicos sustituidos como moduladores del receptor farnesoide x |
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